Download - Dyes Classified by Intermediates

D Y E S C L A S S I F I E I

B Y I N T E R M E D I A T E !

D y e s t abu l a r ly a r r a n g e d u n d e r e a c h

in te rmedia te , w i t h s ta t i s t ica l a n d o t h e r

d a t a for b o t h dyes a n d i n t e r m e d i a t e s .

Glossary of D y e a n d I n t e r m e d i a t e

n a m e s a l p h a b e t i c a l l y a r r a n g e d .

BY

R. X O R R I S S H R E V EConsulting Chemist

EN" COLLABORATION WITH

WARREN N. WATSON

AND

A. R. WILLISChemists, U. S. Tariff Commission

BOOK DEPARTMENT

The CHEMICAL CATALOG CCttBPANY, Inc.ONE MADISON AVKNUJS, NEW YORK, TJ. 8. A.

COPYRIGHT, 1922, BY

The CHEMICAL CATALOG COMPANY, Inc.All Rights Reserved

Press ofJ. J. Little & Ives Company

New York, U. S. A.

T A B L E OF C O N T E X T SPAGE

PREFACE 3

ABBREVIATION'S 5

INTRODUCTION 7

PART I. INTERMEDIATES AND DYE TABLES . . . 17

KEY TO PART I 18

INTERMEDIATES WITH DYE TABLES. THE ARRANGEMENT OF INTER-MEDL^TE NAMES 15 ALPHABETICAL AND INCLUDES CHEMICAL ANDCOMMON OR TRIVIAL- NAMES 19

FORMULA INDEX OF INTERMEDIATES 581

PAET II. DYE NAMES 587

GLOSSARY OF DYE NAMES 589

PAGE INDEX OF SCHULTZ NUMBERS FOR DYES 625

P R E F A C E

Experience in the manufacture of dyes indicates that the properviewpoint for a correct technical program is from the intermediate side.This is a direct corollary of the fact that the intermediates are thematerials out of which dyes are fabricated. Furthermore, the tremen-dous complexity of the dye industry, the interrelationship of one dye toanother or of one intermediate to another, as well as the relationship ofdyes and intermediates to the whole organic chemical industry, allrequire that there be available tables showing the commercial dyesderived from each important intermediate. To give this is the primeobject of this work.

I t is believed that this book will be of service not only to manufac-turers in looking for uses of any intermediate, but to research chemistsand to students. Since the tables give the various outlets and thepoundage imported and manufactured, the book will aid the merchantin the buying or selling of dyes and intermediates. The very com-plete glossary of names, both of dyes and intermediates, will help inmany directions, especially as the intermediate part includes theso-called common or trivial names. This feature will be of greatservice in reading the older literature and patents.

The intermediate names are alphabetically arranged. Under eachprincipal name is given the synonyms, which are also cross-indexed intheir alphabetical order. A special feature is the giving of the nameused by Chemical Abstracts; this, together with the listing of the prin-cipal formulas, will aid in the use of the Chemical Abstracts by the DyeChemist.

A Formula Index to the names of the intermediates and to the pagesis given following the main part of this book containing the alphabeticaltreatment of the intermediates. Here the formulas of the intermediatesare listed in an alphabetical order as in a dictionary, except that CHcomes first; and in this way a 5-atom formula may precede a 3-atomone. This is similar to the excellent formula index of the 1920 ChemicalAbstracts.

After the writer had been engaged for some time in the preparationof this book, he was informed of a somewhat similar classificationundertaken by Messrs. Warren N. Watson and A. R. Willis of theTariff Commission, Washington, D.C. It was deemed fair to cooper-

Z

4 PREFACE

ate and to associate the two works by the mutual use of the other namesas " collaborators/7 Messrs. Watson and Willis have published a partof their work, comprising about a third of the Schultz dyes, in theColor Trade Journal serially from May to September during 1921.This serial publication by Messrs. Watson and Willis and this book bythe writer are separate and independent productions. The writer,however, takes this occasion to express his appreciation for advice andhelp to Messrs. Watson and Willis.

I t is a pleasure to acknowledge help from Dr. Austin M. Pattersonon the Chemical Abstracts nomenclature. Aid has also been renderedby J. R. Minevitch, M. N. Conklin and Oscar Newman. The statisticaldata are taken from the yearly Census of Dyes and Coal Tar Chemicalscompiled by the U. S. Tariff Commission, and from Artificial DyestuffsUsed in the United States by Thomas H. Norton.

R. NORKIS SHREVE.NEW YORK CITY

December, 1921.

A B B R E V I A T I O N S

Dye Application ColumnA Acid dyeACr Acid chrome dyeB Basic dyeCL Color lakeD Direct dyeMF Color made on fiberM Mordant dyeS Sulfur dyess Spirit soluble dyeV Vat dye

Statistics ColumnI '14 Imports, Fiscal Year 1914 (year ending

June 30, 1914)I '20 Imports, Calendar Year 1920M717M'18M'19

Manufactured in Calendar Year1917, 1918, 1919, or 1920

M'20

Literature ReferencesBARNETT, ANTHRACENE AND ANTURAQUINONE

E. de Barry Barnct t , Anthracene and Anthraquinone, 1921.

D . Van Nostrand & Co.

B E I L .

Beilstcin, Handbuch clcr organischen Chemie (3rd Ed . ) .

B E R .

Berichte dcr Deutschen Chcmischen Gesellschaft.

C A I N , INTERMEDIATE PRODUCTS

J. C. Cain, The Manufacture of In te rmedia te Products for Dyes,

Second Edition 1919, Macmillan & Co.

F R D L .

P . Friedlacnder, Fortschrit te dcr Teerfarbcnfabrikation, 1877-1916,12 vols., Julius Springer.

5

6 ABBREVIATIONS

GREEN, ORGANIC COLORING MATTERS

A. G. Green, A Systematic Survey of the Organic Colouring Matters,1908 Edition, Macmillan & Co.

GEORGIEVICS AND GRANDMOUGIN, DYE CHEMISTRY

G. von Georgievics and E. Grandmougin, translated by F. A.Mason. A Textbook of Dye Chemistry, 1920. Scott Green-wood & Son.

HEUMANN, ANILINFARBEN

K. Heumann (Fourth part edited by G. Schultz), Die Anilinfarbenund ihre Fabrikation, Four Parts, 1888-1906, Friedrich Viewig.

LANGE, SCHWEPELFARBSTOFFE

Otto Lange, Die Schwefelfarbstoffe, ihre Herstellung und Verwen-dung, 1912, Otto Spamer.

LANGE, ZWISCHENPRODTJKTE

Otto Lange, Die Zwischenprodukte der Teerfarbenfabrikation,1920, Otto Spamer.

THORPE, Die. CHEMISTRY

Edw. Thorpe, A Dictionary of Applied Chemistry, First Edition,Longmans Green & Co.

ULLMANN, ENZY. TECH. CHEMIE

Enzyklopaedie der technischen Chemie, Edited by Dr. Fritz Ull-rnann, 1914. Urban & Schwarzenberg.

Miscellaneouso orthom metap paraa alpha/3 betaN Nitrogen (signifies nitrogen attachment

of radical)C. A. nomen. . . Chemical Abstracts nomenclature(mols) MoleculesSchultz Number . Number for dye as given in Schultz,

Farbstofftabellen, 1914 Edition.

I N T R O D U C T I O N

The contents of this book fall into two parts: first, an alphabeticallist of intermediates with their data and dye tables, and second, anaphabetical list of dye names referring to their Schultz numbers whenknown, by which any dye here classified can be found in the tables bylooking in the "Page Index of Schultz Numbers" at the end of the bookfor the appropriate pages.

Often an intermediate is known by as many as half a dozen names,and each one is listed in its alphabetical order, but the synonyms allrefer to one name under which are arranged the tables and other da ta .Thus the book is a glossary of intermediate names. In selecting thename given at the head of the data for a certain intermediate, thewriter was influenced first by considerations of clearness and thenof custom and usage. For a full discussion of this important nomen-clature question, reference is made to the nomenclature section of thisintroduction.

Following the synonyms, is given the structural formula, the empiricalformula, and the molecular weight. It is the emphatic opinion of thewriter that the indexing of organic compounds by their formulas is thesimplest, the most universal, and the clearest. Chemical Abstracts,starting with 1920, has inserted a formula index, and it is believed t h a tchemists can find a given intermediate quicker and more surely inChemical Abstracts by the use of this formula index than by the ordinarysubject index. The formulas given here will be an aid in this direction.Furthermore a formula index is included in this book.

Under each intermediate there is listed a short description of methodsof Formation followed by Literature References. These are not exhaustivein any sense, but the aim has been to give the usual commercial prepa-ration together with several references to the literature for any one whodesires more details. The references to Lange, Zwischcnproduklo,cover the German patents.

In order to give some basis for judging the extent to which a dye oran intermediate is used, the statistical data for importation and manu-facture in the United States is given under Statistics, These data aretaken from the following government reports: Census of Dyes and Coal-Tar Chemicals, by U. S. Tariff Commission; Artificial Dyestujfs Used inthe U. S.9 by Thomas H. Norton, and Chemicals and Allied Products

7

8 INTRODUCTION

Used in the U. S. by E. R. Pickrell. The Imports 1914 both under inter-mediates and under dyes refer to the imports for the fiscal year endingJune 30, 1914. Otherwise the imports, and always the amounts manu-factured, refer to the calendar year marked. It is believed that theaddition of these statistical data to the tables will be of much service inpointing out forcibly the relative commercial importance of the dyesand intermediates, and will help to complete development of the dyeindustry in America. In considering these statistics, it must be bornein mind that since 1914 the United States has been endeavoring tofully supply her own needs, and proceeded naturally along the lines ofleast resistance, so that often a dye was manufactured because of itscomparative simplicity, to be later superseded by a more suitable dyeof more complexity. The Imports for 1914 (fiscal year ending June30, 1914) are "normal" except that Vat Dyes were not imported asheavily that year as had been the usual case.

The statistics of import of a dye, especially for the fiscal year endingJune 30, 1914, often include a number of very similar though notidentical dyes. These statistics were obtained by adding together theindividual dye weights as listed by Norton under a given Schultznumber.

Where Tlh M'19, Manufactured 1919, etc., are given followed by aquestion mark, it indicates that the dye or intermediate was importedor manufactured for the year marked but in amounts that have notbeen disclosed by the U. S. Government.

When a figure is given for imports or manufactures of dyes or inter-mediates, this figure always refers to pounds.

The tables proper give for any intermediate all the dyes listed inSchultz, Farbstofftabellen, 1914 Edition, that are derived from thisintermediate. This includes practically all of the important dyesexcept a few of the newer ones of undisclosed constitution. Thus agiven dye is separately arranged under each of its intermediates. Asthere is named in a special column the Other Intermediates constitutinga dye besides the one at the head of each table, the intermediate rela-tionship is clearly stated.

The following dyes listed in Schultz, Farbstofftabellen (1914), arenot classified, on account of lack of information as to their composition-

30 Radial Yellow G 706 Cachou de Laval87 Peri Wool Blue 707 Sulfine Brown

608 Euchrysine 708 Sulfaniline Brown609 Homophosphine G 744 Sulfo Black B, 2B

INTRODUCTION 0

751 Krygene Brown RB 756 Kryogene Black TGO752 Kryogene Direct Blue GO 757 Sulfogcnc Brown G, D753 Kryogene Direct Blue B 863 Anthraquinone Blue Green B XO754 Kryogene Direct Blue 3B 871 Indanthrcne Violet RN Extra755 Kryogene Black BNX

In very many cases, the writer has supplemented the informationin Schultz, Farbstofflabellen, as to composition of dyes, and hence hasbeen able to classify many dyes whose composition is indefinite in thisbook. In a number of instances when Schultz refers the dyes to com-plex intermediates, these have been split into simpler components, andthe components as well as the complex parent compound have all beenindexed. Also certain obvious errors in Schultz, Farbstofftabcllen, havebeen corrected, as for example, where in //182, reference is made toL-amino-4-naphthol-sulfonic acids which the patent refers to ar.a-rsulfonic acids (l-amino-8-naphthol-sulfonic acids) and specifically namesH acid in the example given.

When the patents describing a dye list a number of intermediates,then those listed under Example I of the patent are chosen for classifica-tion unless, of course, Schultz, Farbstofftabdlen, gives definite composi-tion to the dye. Quite often intermediates arc indexed even thoughnot a component part of the final dye, provided they were necessaryto its manufacture, e.g. benzoic acid in the manufacture of certain ofthe Triphenyl-methane Dyes as Diphenylamine Blue and Aniline Blue.

All possible intermediates for any given dye are not indexed, but itis hoped to extend the present classification at a later date. Previoustables resembling those given here, but along much less extensive lines,are to be found in Heumann, Die Anilinfarben und ihre FabricationIV, II , 2, pages 1943-2013, and Lefevre, Traite des Matures Coloranlca(1896), pages 140-407.

In the column in the tables headed Other Intermediates Used andNotes, there is given first the intermediates other than the one at thehead of the table, which compose the dye in question. Unless other-wise marked, it is to be understood that one molecule of an intermediateis used. When more than one molecule is employed, of the intermediateheading the table, then the name of this intermediate is also given inthe Other Intermediates column followed by the number of molecules(mols) that are used in the dye.

The notes are in brackets, and are mostly self-explanatory, and referchiefly to constituents, such as sulfur (S), sodium sulfide (Na2S), andthe like, which enter into the formation of the dye. Such steps op

10 INTRODUCTION

Sulfonation, Bromination, and Chlorination are given, but Couplingby Diazotization and Condensation are to be understood.

Under notes is generally listed the name of a given dye if it is a stepin the preparation of the dye classified in the table, but this componentdye is not used as the index or heading for any of the dye classificationtables, and this fact is indicated by placing the name of the componentdye in a bracket.

Indigo is an exception, and the dyes based on it are tabulated there-under as well as under the various component intermediates.

The last column in the tables classifies the dyes by their usual methodof application as indicated by the following abbreviations.

A Acid dyeACr Acid chrome dyeB Basic dyeCL Color lakeD Direct dyeM F Color made on fiberM Mordant dyeS Sulfur dyess Spirit soluble dyeV Vat dye

A classification of this kind is not very exact in certain cases wherea dye is susceptible of several different methods of application. Theaim has been to give the mode of application most generally employed.

Regarding the naming of the dyes, there is used in the tables thatname first given in Schultz, Farbstojftabellen (1914), followed by asecond name in those cases where the second name is more generallyused in the United States than the first Schultz name.

A glossary of the ordinary German and Swiss names, together withmany of the American and English names, is given in the back of thebook. I t would have been very helpful to have added to this list allthe current American and English marks, but in the present develop-ment stage of the American dye industry, this turned out to be im-practical. The list as given includes those listed and classified byNorton in Artificial Dyestuffs Used in U. £., with various correctionsand a considerable number of additions. These names refer to "Schultz"numbers where known, and as the last few pages of the book give a listof the pages on which occur references to any "Schultz" number, theplace of any dye of known constitution can be readily found, togetherwith the data regarding that dye.

INTRODUCTION 11

In the tables, the dyes are classified under the usual constitutionalheadings, which are here grouped in the following list:

Nitroso DyesNitro DyesStilbcne DyesPyrazolone DyesMonoazo DyesDisazo DyesTrisazo DyesTetrakisazo DyesAuramincsTriphenyl-methane DyesDiphenyl-naphihyl-mcthane DyesXanthone DyesAcridine DyesQuinoline DyesThiobcnzcnyl DyesIndophcnolOxazinc DyesThiazinc DyesAzinc DyesSulfur DyesAnthraquinone and Allied DyesIndigo Group DyesAniline Black Group

NOMENCLATURE

The scientific naming of intermediates has indeed been confused,and in many instances a number of names have been used for the samecompound, or the same name for several different compounds. I t hasbeen the aim of this book to give the various names met with in theliterature for the intermediates, and to cross-index these names in thealphabetical arrangement,—thus giving a glossary of intermediatenames for all those common intermediates here considered. Further-more the common or trivial names are listed in a very complete mannerand include the trivial names for many intermediates not speciallyconsidered here. As mentioned before, there has been chosen for theprincipal name from among the various synonyms that name which isclear and which is sanctioned by custom. In so choosing, the tendencyhas been to adopt a few of the well-known trivial or common names,

12 INTRODUCTION

such as H Acid and Nevile-Winther's Acid, in place of the strictlychemical names; for the writer's experience is that dye men, whetherin the research laboratory, the factory, or the office, speak of H Acid forexample, and not l~amino-8-naphthol-3: 6-disulfonic acid.

The most scientific nomenclature is that used by Chemical Abstractsof the American Chemical Society. This is fully explained in theIntroduction to Decennial Index of Chemical Abstracts, as well as inthe Journal of the American Chemical Society.1

It, however, offers the disadvantage of requiring considerable studyto master its principles, which often vary from the practice of the dyeindustry, and furthermore there is comparatively little literature per-taining to dyes and intermediates in the years covered by ChemicalAbstracts.

On the other hand, organic chemistry is now so complex that moreattention must be paid to scientific naming of organic compounds,and also the amount of dye literature contained in Chemical Abstractsis increasing yearly, so that it is to the advantage of the dye chemistto familiarize himself with the procedure of Chemical Abstracts, and itcannot be too strongly recommended that every one make a studyof the principles of Chemical Abstracts nomenclature as disclosed inthe references given above.

This book aims to give the Chemical Abstracts name for each inter-mediate; and in the many cases where this name differs from the onein common use, this Chemical Abstracts name is so designated bybeing marked C. A. nomen., as an abbreviation for Chemical AbstractsNomenclature. If only one name is listed, it is to be understood thatthis is the one sanctioned by Chemical Abstracts.

Beginning with the 1920 volumes of Chemical Abstracts, a FormulaIndex is included, which offers the easiest way to find reference to achemical compound or its nomenclature.

In case of many benzene derivatives, the writer has adopted theChemical Abstracts nomenclature, as there is considerable confusionin the literature regarding these names, and as the Chemical Abstractsprocedure does not vary greatly as a rule from well-recognized practice.However, in case of many of the naphthalene derivatives the ChemicalAbstracts practice is so far from what is commonly used that the Chem-ical Abstracts names are only given as synonyms. The men responsiblefor Chemical Abstracts are showing a great willingness to bring their

1 Patterson and Curran, J. Amer. Chem. Soc. 39, 1623-38 (1917).

INTRODUCTION 13

system as near to that used in practice as possible, and in all probabilitythe near future will show closer accord.

The very common use of more than one of the terms ortho, mela, andpara, to indicate position of substitucnts, is very confusing and shouldbe dropped in preference either to the procedure of Chemical Abstractswhere one such term is used in connection with numbers, or to theuse of numbers alone. For example, m-nilro-p-toluidine (CH3=1) ando-amino-phenol-p-sulfonic acid should be replaced by 2-nitro-p-toluidine(NH2=1) and 2-amino-l-phenol-4-sulfonic add, the present ChemicalAbstracts usage. In the former case the writer much prefers the namel-amino-2-nitron-toluene.

Chemical Abstracts uses p-tolwidine (NH2=1) and p-phenylene-dia-mine and the like as "index compounds" with the various substituentsas modifiers, arranged in an inverted order in their indices. In thisbook the practice of Chemical Abstracts in this regard is followed,except for the inversion for the principal name of the intermediate.The other names arc given as synonyms and cross-indexed. However,in the body of the tables, such terms as o-amino-phenol-p-sulfonic acidarc used in a few cases because of their very common usage, and conse-quent quick recognition.

Treating the matter broadly, the gist of the Chemical Abstractsnomenclature practice is that the "chief function" of a compound isexpressed in the main part of the name, which with "its functionalending, if any, is placed first in the index, the names of the substituentsfollowing." The numbering starts from the "chief function" and isnot varied by the addition of substituents, for instance,—2: 7-naphtha-lene-sulfonic acid is an "index compound," as is likewise 1 naphthalene-sulfonic acid; and thoir amino, halogon, and nitro derivatives areindexed thereunder. For instance, Laurent's Acid or what is ordinarilycalled l~naphthylamine-5-sulfonic acid is indexed by Chemical Abstractsunder 1-naphthalene-sulfonic acid, and called 5-amino-l-naphthalene-sulfonic add. In the decennial index, hydroxy was also considered asa substituent.

However, naphthol-sulfonic acids and phenol-sulfonic acids are nowrecognized by Chemical Abstracts as exceptions to their rule of assigningthe chief function to acids, and of allowing only one functional endingin the index name. So that while in the decennial index these -ol-sulfonic acids had their numbering start with the sulfonic group, nowthe numbering begins with the hydroxyl. For example, l-naphthol-4-sulfonic acid and 1-naphthol-S: 6-disulfonic acid. In case of amino- nitro-

14 INTRODUCTION

chloro- derivatives and the like, the positions are referred to the setnumbering of the index compound. Take H Acid,—this is viewed as aderivative of index compound l-naphthol-3:6-disulfonic acid by ChemicalAbstracts, and is named in their index as 8-amino-l-naphthol~3:6-disulfonic add, or in their inverted form as l-naphthol-3: 6-disulfonicacid, 8-amino-.

This numbering is quite different from the ordinary numbering ofl-amino-8-naphthol-3: 6-disulfonic acid for H Acid. The giving in thisbook of both nomenclatures will help in the using of Chemical Ab-stracts, and as a further aid in this direction the first letter of theindex compound as employed in Chemical Abstracts is italicized.

The rule of Chemical Abstracts regarding arrangement of substituents,reads as follows:—"The names of substituent radicals in the name of acompound are arranged in alphabetical order." This is an excellentpractice and should be universally adopted. In conformance with this,benzyl-ethyl-aniline is recommended, and not ethyl-benzyl-aniline.

In the naming of toluene derivatives, the usual custom has been tostart numbering from the CH3 group irrespective of other substituents.In Chemical Abstracts, the numbering starts from the chief function,and the order of the chief function is: "onium compounds, acid (car-boxylic first), acid halide, amide, imide, aldehyde, nitrile, ketone, alcohol,phenol, mercaptan, amine, imine, ether, sulfide (and sulfoxide and sul-fone)" So whenever sulfonic acid is present, the start of the numberingis with this group, except that the carboxylic group, being an acid radical,is of same order as sulfonic, and has been given precedence over thesulfonic radical. Instead of toluidine-sulfonic acid with the numberingbased on the CH3, Chemical Abstracts uses amino-o- (or m- or p-)toluene-sulfonic acid and starts the numbering with the sulfonic acidgroup. Toluidines start their numbering from the NH2 group, as it hasprecedence over CH3. Another divergence of the Chemical Abstractspractice from the ordinary numbering is the place of the numbersor letters in such terms as the following:

Ordinary Practice Chemical Abstracts PracticeNaphthalene-2:7-disulfonic Acid 2: 7-Naphthalenedisulfonic AcidToluene-p-sulfonic Acid p-Toluenesulfonic Acid

The custom of using hyphens to set off radicals and substituents fromeach other and from the parent compound is extensively used in thisbook for the sake of clearness, and as an aid to the eye and the mind.No one thinks of a complex organic chemical as a whole, but as a com-

INTRODUCTION 15

plex of various substituents around a central body; therefore thewriting of a long name like tetramethyldiaminodiphenymethane as oneword is very reprehensible and should be early abandoned. Otherwisethe careless practice of writing as two or more separate words thename of one chemical individual is bound to increase; already thislatter practice is gaining too much headway, as can be seen by aninspection of our trade or semi-technical journals.

The rule about hyphens as used here is to insert them betweenall radicals, and between the radicals and the parent body, exceptin the case of compound radicals, such as mcihylamino- (CH3NH~),tetraethyl-, disulfo?iic- and the like. Melhylamino should not be writtenmethyl-amino. While Chemical Abstracts does not employ hyphensin this broad way, yet the use of hyphens has been extended to thenames otherwise following Chemical Abstracts procedure.

It is clearly recognized that the nomenclature here used is not alwaysconsistent as between the scientific and common usage. For examplewhile 2-amino-l-phenol-4-sulfonic acid is listed as the principal nameof this intermediate, yet in the body of the tables the ordinarily usedsynonym o-amino~phenol-p-suljonic acid is given because of its quickrecognition. However, the movement to a more scientific nomen-clature such as used by Chemical Abstracts should be encouraged asmuch as possible, and such terms as o-cwiino-phcnol-p-sulfcmic acidshould be dropped gradually.

P A R T 1

I N T E R M E D I A T E S

KEY TO PART I INTERMEDIATES AND DYE TABLES

The arrangement is alphabetical not only by chemical but by trivialor common names. Many trivial names are listed for intermediateswhich are not further considered. Dye tables and other data ac-company those intermediates which enter directly into the formationof the commonly used dyes.

Synonyms and trivial names are given for the intermediates, andthese synonyms and trivial names are listed not only under the ap-propriate intermediate but also separately in the alphabetical arrange-ment.

That chemical name called for by the Chemical Abstracts nomen-clature is to be found either as the principal name of each intermediateor among: its synonyms. This is distinguished by being followed bythe abbreviation C. A. nomen., except whon only one name is used foran intermediate, in which case this name is the one in common usageand is also that one sanctioned by Chemical Abstracts. In the indicesof Chemical Abstracts the names are alphabetically arranged under anumber of "parent compounds" which in ordinary usage are precededby the modifying radicals. As this book follows the ordinary usage,it was thought that it would be helpful to designate the Chemical Ab-stracts "parent compound," which is done by italicizing the firstletter of these "parent compounds" in those names following ChemicalAbstracts nomenclature.

The prefixes m-, o-, p-, a-, $- and the like are not considered in themain alphabetical arrangement. Hence /3-naphthol (beta-naphthol) isto be found under N.

The import statistics are not for each strictly individual dye mark,but represent a group identical to or closely resembling a given Schultzdye. These figures are arrived at by adding the total poundage of thesedyes arranged by Norton under each Schultz number in his book,Artificial Dyestuffs Used in U. S.

Unless otherwise marked, it is to be understood that only one mole-cule of each intermediate is a part of a dye. Furthermore, when morethan one molecule is employed of the intermediate heading a dye table,the name of this intermediate is entered under the Other Intermediatescolumn followed by the number of molecules involved.

A fuller consideration of these principles is to be found in the Intro-duction. See also abbreviations on page 5.

18

INTERMEDIATES

The intermediates are arranged alphabetically by their chemicalnames and by their trivial or common names, and they are accompaniedby the dye tables and other data. See Introduction, or page 18, forexplanation of this arrangement.

A Acidl:7-Dihydroxy-naphthalcnc-3:6-disulfonic Acid (not considered

herein)

Acenaphthenequinone (C. A. nomen.)

7: 8-Diketo-accnaphtheneCO-CO

FORMATION.—From acenaphthenc by oxidation

LITERATURE.—Cain, Intermediate Products (2d Ed.), 242

Dyes Derived from Acenaphthenequinone

Schultz

for Dye

907

90S

911

Ordinary Name andClans of Dye,

INDKJO GROUP DVIJSCibii Seiuld, CJ

Ciba Keel R

Ciba Onui&o (\

Statistics ofImport andManufacture

I '11.-22,2051 '20.-25,578I '14:— 1,001

V 14:-— 222

Other I ntcr m edict lasUwd and Notes

2-IIy(lroxy-iluo-naphthene

2-1 Iy< Iroxy-tl lioiuipl I-thono [Bromiuatioii]

5-A mino-2-1 iydroxy-tlnoiuiplithcnc

DyeAppli-cationClass

V

Y

Y

3-Acenaphthenol (C. A. nomcn.)

Sec, 3-IIydroxy-aconapl 11hone

20 DYES CLASSIFIED BY INTERMEDIATES

1-Acetamido-anthraquinone

oooNH.CO.CH3FORMATION.—From 1-amino-anthraquinone by action of acetic aihydride on solution in oleumLITERATURE.—Lange, Zwischenprodukte, #3124Dyes Derived from 1-Acetamido-anthraquinoneSchultzNumberfor Dye

813

Ordinary Name andClass of Dye

ANTHRAQUINONE ANDALLIED DYES

IndanthreneCopper R

Statistics ofImport and

Manufacture

I'14:—1,268

Other IntermediatesUsed and Notes

1:6- (or 1:7-) Diacet-amido-anthraqumone

DyeApplicatiorClass

V

2 - A c e t a m i d o - a n t h r a q u i n o n e

C C •c o •

FORMATION.—From 2-amino-anthraquinone by action of acetic arhydride on oleum solution

LITERATURE.—Lange, Zwischenprodukte, #3121:

Dyes Derived from 2-Acetamido-anthraquinone

S c h u l t z

N u m b e r

f o r D y e

8 1 2

O r d i n a r y N a m e a n d

C l a s s o f D y e

A N T H R A Q U I N O N E A N D

A L L I E D D Y E S

I n d a n t h r e n e

O r a n g e R T

S t a t i s t i c s o f

I m p o r t a n d

M a n u f a c t u r e

1 1 4 : — 2 , 1 0 3

I ' 2 0 : - - 3 8 1

O t h e r I n t e r m e d i a t e s

U s e d a n d N o t e s

1 : 6 - ( o r 1 : 7 - ) D i a c e t -

a m i d o - a n t h r a q u i n o n e

D y e

A p p l i

c a t i o n

C l a s s

V

8 - A c e t a m i d o - l - n a p h t h o l » 3 : 6 - d i s u l f o n i c A c i d

S e e , A c e t y l - H A c i d

DYES CLASSIFIED BY INTERMEDIATES

Acetanilide

NH.COCH3

21

STATISTICS.—Manufactured 1917:—1,897,703 lbs.Manufactured 1918:—2,085,088 lbs.Manufactured 1919:—1,934,125 lbs.Manufactured 1920:—2,667,252 lbs.

FORMATION.—By heating aniline with glacial acetic acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 52Lange, Zwischenprodukte, #117

USES.—For preparation of p-nitro-acetanilide, and for p-nitro-aniline

Aceto-acetic Ethyl Ester

CH3 . CO. CH2. CO. OC2 5 = C6Hio03 = 130

FORMATION.—By the reaction of dry sodium ethylate and dry ethylacetate

Schult»Numberfor Dye

19

22

2527

773

Dyes Derived


PYRAZOLONE DYESFlavazine LFast Tight Yellow

Xylcne Yellow 3 G

Dianil Yellow 3 GDianil Yellow 2 II


Anthracene Yollow

from Aceto-acetic Ethyl Ester


I > 14 .—38,908I'20:—• 9,327

I ' 14:—23,074I '20:—77,782

I '14:— 4,04a

Other Intn mediatesUsed and Notes

AnilinePlienyl-hydrazinc-p-

sulfonic Acid2: 5-Dicliloro-phcnyl-

liydra-zinc-4-sulfonicAcid

Primulinc-sulfonic AcidPrimulinc-Rulfonic AcidPhcuyl-hydrazinc-p-sul-

fonic Acid

Pyrogallol


A

A

DD

M

yV-Acetyl-l-amino-8-naphthol-3: 6-disulfonic Acid

See, Acetyl-H Acid


Acetyl-H Acid

iV-Acetyl-l-amino-8-naphthol-3:6-disulfonic Acid

8-Acetamido-l-naphthol-3: 6-disulfonic Acid (C. A. nomen.)

HO NH.CO.CH3

= C12HnNO8S2 =HO3S SO3H

STATISTICS.—Manufactured '20:—?

FORMATION.—From H acid by acetylation

Dyes Derived from Acetyl-H Acid

SchultzNumberfor Dye

42

66


MONOAZO DYESAmido Naphthol

RcdG

Amido NaphtholRed 6 B


Manufacture

I '14:— 3,500M '17:— ?M 'IS:— ?M'19:— ?M'20.-132,637I '20:— 2,028

I '14:— 45,697M'lS:— ?M'19:— ?M'20:—142,567I '20:— 1,299


Aniline

2)-Amino-acetanilide

DytApplcatioClas

A

A

Acetyl-1: 4-naphthylene-diamine-6-sulfonic Acid

8-Acetamido-5-amino-2-naphthalenc-sulf onic Acid (C A. nomer

NH2

HO3S= C12H12N2O4S:

N H . C O . C H a

:280

FORMATION.—From mixture of l~naphthylamine-6-and-7-sulfonic aci(Cleve's Acids) by acetylation with glacial acetic acid, nitrati<with mixed acid, and reduction with iron.

LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 152

DYES CLASSIFIED BY INTERMEDIATES 23

Dyes Derived from Acetyl-1: 4-naphthylene-diamine-6-sulfonic


273

274


DISAZO DYESDiaminogcn Blue BB

Diaminogcn B


Manufacture

I '14:— 8,308M'17:— ?I '20:— 5,936I '14:—313,029I '20:— 18,120


a-NaphthylamineSchaeffcr's Acid[Saponification]a-NaphthylamineGanima Acid[Saponificaiion]

Acid


D

D

Acetyl-p-phenylenediamine

See, p-Amino-acctanilide (C. A. no?nen.)

o-Acid (of Claus and Voltz)

See, Croceine Acid

1:2:4 Acid

See, l~Amino-2-naphthol-4-sulfonic Acid

/3 Acid or Beta Acid

See, Anthraquinone-2-sulfonic Acid

8 Acid or Delta Acid

See, l-Naphthylamine-4: 8-disulfonic Acid and 2-Naphthyl-amine-7-sulf onic Acid

€ Acid or Epsilon. Acid

See, l-Naphthol-3: 8-disulfonic Acid

See, l-Naphlhylamine-3: 8-disulfonic Acid

and 1: 8-Dihydroxy-naphthalcne-3-sulfonic Acid (not con-

sidered herein)

f Acid or Zeta Acid

Naphthasultone-3-sulfonic Acid (not considered herein)


X Acid or Lambda Acid

See, l-Naphthylamine-2-sulfonic Acid

/x Acid or Mu Acid

See, l-Naphthylam.ine-6-sulfonic Acid

P Acid or Rho Acid

See, Anthraquinone-1: 5-disulf onic Acid

X Acid or Chi Acid

See, Anthraquinone-1: 8-disulfonic Acid

Alen's a or Alen's Alpha Acid. {This is generally followed by the classof the compound, e.g., AUn's a Naphthylamine-disulfonic Acid)

See, Freund's Acid (l-Naphthylamine-3: 6-disulfonic Acid)

l-Nitro-naphthalene-3:6-disulfonic Acid (not consideredherein)

Alen's p or Alen's Beta Acid. (Generally followed by the class of thecompound, e.g., Alerts fi Naphthylamine-disulf onic Acid)

l-Naphthylamine-3:7-disulfonic Acid (not considered herein)

l~Nitro~naphthalene-3: 7-disulfonic Acid (not considered herein)

Alizarin

1:2-Dihydroxy-anthraquinone

a : /3-Dihydroxy-anthraquinone

CO 0 H

STATISTICS.—See #778 in following table

FOKMATION.—From sodium 2-anthraquinone-sulfonate by fusion withcaustic oda for 2-3 days at 200° C , in autoclave, and in presence ofpotassium chlorate

LITERATURE.—Schultz, Farbstofftabellen (1914 Ed.), #778



778

779

780

781

783787788

797

798

799

854

862

Dyes


ANTHEAQUINONE ANDALLIED DYES

Alizarin

Alizarin Orange

Alizarin Red

Erweco Alizarin AcidRedBS

PurpurinAlizarin Bordeaux BAlizarin Cyanine R

Alizarin Garnet R

Alizarin Maroon W

Alizarin Cyanine G

Alizarin Viridinc DG

Alizarin BlueBlack B

Derived from Alizarin


Manufacture

I '14:—202,392M'17:— ?M'18:— ?M'19:— ?M'20 — ?I '20.— 8,575I '14:— 14,239M'19:— ?M'20:— ?I '20:— 500I '14:— 81,919M'17:— ?I '20:— 12,628

I '20.— 20I '20— 16,781

I '14— 720

I '20— 2,014

I '20:— 339

I '20— 11,397

I '14— 54,706I '20.— 28,802


[Nitration]

[Sulfonation]

[Sulfonation]

[Oxidation][Oxidation][Alizarin Bordeaux B,

Oxidation][1-Nitro-alizarin, Re-

duction][Crude Nitro-alizarin,

Reduction][Alizarin Cyanine R,

Arhidation][Alizarin Bordeaux B]p-Toluidine (2 mols)[Sulfonation][Purpurin]Aniline[Sulfonation]


M

M

M

M

MMM

M

M

M

M

M

Alpha = aNote.—This is not considered in the alphabetical arrangement,

e.g. alpha-N'aphthol is indexed as a-Naphthol under "N."However P-Naphthol is placed after a-Naphthol

Alpha-NaphtholSee, a-Naphthol under N,


p-Amino-acetanilide (C. A. nomen.)

Acetyl-p-phenylene-diamine

N H . C O . C H 3

=C8Hi0N2O=150

NH2

STATISTICS.—Imported '14:—6,261 lbs.Manufactured'17:— ?Manufactured '18:—177,990 lbs.Manufactured ;19:— 62,567 lbs.Manufactured '20:— 97,275 lbs.

FORMATION.—From p-nitro-acetanilide by reduction with iron andacetic acid at not higher than 60° C.


Dyes Derived from p-Amino-acetanilide




ManufactureOther Intermediates

Used and Notes


61M O N O A Z O D Y E S

Victoria Violet I '14:— 52,365M'17M ' l SM'19I '20

M'20

-105,086- 2,082

64

65

Azo Acid Red BLanafuchsine

Azo Coralline L

I '14:— 78,305M'17M ' l SM'19I '20:—

M'20:—

M'17:—

15,272674

Chromotropic Acid[Saponification]

l-Naphthol-3: 6-disul-fonic Acid

R Acid

I J20:— 249M'20:— ?


Dyes Derived from p-Amino-acetanilide (continued)

27


66

67

239

243

244

290

296

714

715


MONOAZO DYES(continued)

Amino NaphtholRed 6B

Cliromoiropo 6B

DISAZO DYESAzotol C

Coomassie WoolBlack R

Coomassie WoolBlack S

Violet Black

Cotton Yellow G

SULFUH DYESThiophor Yellow

Bronze G

Thiocatechinc


Manufacture

I '14:— 45,697M'lS:— ?

I '20:— 1,299M'20:—142,567I '14:— 2,818M'17:— ?M'lS:— ?M'19:— 77,4S1M'20:— ?

M'lS:— ?M'19:— ?

I '14:— 31,472I '20:— 4,651


Acetyl-H Acid

Chromotropic Acid

?ft-Phcnylonc-diammc[Amino-chrysoidinc]

/3-Naphthola-NaphthylamincSchacffer's Salta-NaphthylamincB SaltNcvilc-Winthcr Acida-NaphthylamineSalicylic Acid (2 mols)p-Amino-acctanilide (2

mols)Phosgene

p-Phcnylcnc-diammeBcnzidine[Sulfur][Sulfur]

DyeA ppli-cationClass

A

A

MF

A

A

D

D

S

S

3-Amino-alizarin (C. A. nomen.)

/3-Amino-alizarin

OHCO.

CO

OHNH2

FORMATION.—From 3-nitro-alizarin by reduction.


Dyes Derived from 3-Amino-alizarin


S03

S04

SOS

S09



Alizarin Blue WX

Alizarin Blue S

Alizarin Green X

Alizarin IndigoBlueS


Manufacture

I '14:—319,394M'19:— ?I '20:— 5,585I ;14:—117,850I '20:— 43,679I '14:—135,191I '20:— 4,254


3-Nitro-alizarin[Glycerol]

3-Nitro-alizarin[Glycerol]3-Nitro-alizarin[Glycerol; Oxidation]3-Nitro-alizarin[Glycerol; Oxidation]


M

M

M

M

4-Amino-#lizarin (C. A. nomen.)

a-Amino-alizarin


FORMATION.—From 4~nitro-alizarin by reduction with alkaline sulfides

LITERATURE.—Schultz, Farbstofftabellen (1914 Ed.), #797

Dyes Derived from 4-Amino-alizarin

fichultzNumbcifor Dye

797

805



Alizarin Garnet B

Alizarin Green S


Manufacture

I 14:— 720

I'14:— 15,885


[This is 4-Amino-ali-zarin]

[Glycerol]


M

M

a-Amino-alizarin

See, 4-Amino-alizarin ( C A. nomen.)


/3-Amino-alizarinSee, 3-Amino-alizarin (C A. nomen.)

2-Amino-5-(P-amino-phenyl)-^enzene-sulfonic Acid (C. A. nome?i.SO*H=1)

See, Benzidine-sulfonic Acid

P-(p-Amino-anilino)-phenol (C. A. nomen.)

See, 4-Amino-4/-hydroxy-diphcnylamiac

1-Amino-anthraquinone (C. A. nomen.)

a-Amino-anthraquinoneN H 'CO

FORMATION.—(1) From 1-nitro-anthraquinone by reduction with sodiumsulfide

(2) From anthraquinone-1-sulfonic acid (potassium salt) byheating with 10 per cent ammonia in an autoclave to 180-190°

LITERATURE.—Ullmann, Enzy. tech. Chemie. 1, 474Lange, Zwischcnproduktc, #3066, 3109, 3158

Dyes Derived from 1-Amino-anthraquinone


814

824

826

830

834

870



Algol Yellow W G

Algol Orange R

Indanthrene Red G

Indanthrcne Red R

Algol Gray B

Algol Corinth R


Manufacture

I '14:—5,185T *OO* A.I '14:— 51I'20:— 400

I '14:—2,099I '20:—6,595

I '14:—4,192I'20:— 840I'20:— 134


Bcnzoyl chloride

2-Ghloro-anthraquinonc

2: 6-Dichloro-anthraqui-nonc

1-Amino-anthraquinone(2 mols)

2:7-Dichloro-anthra-quinono

1-Amino-anthraqui-none (2 mols)

1-Chloro-anthraquinone[Nitration, Reduction]

2-Chloro-anthraquinone[Nitration, Reduction]Benzoyl chloride

Dye,A p pli-cationClass

V

V

V

V

V


2-Amino-anthraquinone (C. A. nomen.)

/3~Amino-anthraquinone

= C1 4H9NO2=223

STATISTICS.—Manufactured '19:—?Manufactured '20:—?

FOKMATION.—From sodium anthraquinone-2-sulfonate by heating withammonia water in an autoclave at 200° C , preferably in the presenceof an oxidizing substance

LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 476Lange, Zwischenprodukte, #3107Cain, Intermediate Products (2d Ed.), 254

Dyes Derived from 2-Amino-anthraquinone


810

811

825

837

838

846


ANTHRAQXJINONE ANDALLIED DYES

HelidoneYellow 3 G N

Algol Yellow 3G

Algol Red B

Indanthrene Blue R

Indanthrene BlueRS

Indanthrene DarkBlue BT

II

II

III

IMI

M


Manufacture

'14:—'20:—

'14:—'20:—

'14:—'20:—'14:—

20,7442,515

1,604570

2,3994,151

500

'14:—187,379'17:—'20:—'20:—

?16,385

?


2-Aniino-anthraquinone(2 mols)

Phosgene2-Amino-anthraquinone

(2 mols)[Succinic acid]4-Bromo-N-methyl-

anthrapyridone2-Amino-anthraquinone

(2 mols)2-Amino-anthraquinone

(2 mols)[Alkaline Reduction][or Indanthrene Blue

R reduced]2-Amino-anthraqui-

none (2 mols)[Glycerol (4 mols)][or Benzanthrone-quin-

oline (2 mols)]


V

V

V

V

V

V



849

867

Dyes Derived from



(continued)Indanthrcnc Yellow

G

Indanthrcnc BrownB

2-Amino-anthraquinone (continued)


Manufacture

I '14:— 75,192M'19:— ?I '20:— 75,665

M'20:— ?I '14:— 6,175I '20.— 3,511


2-Amirio-antliraqumonc(2 mols)

2-Amiiio-antliraquinone(2 mols)


V

V

1:5- and 1:8-Amino-anthraquinone-sulfonic Acids

5-and 8-Amino-l-anthraquinone-sulfonic Acids (C. A. nomeri)

(HO3S) m NH2c o3 ) c

HO3S C 0

= 303

FORMATION.—Anthraquinonc is sulfonatcd to a mixture of 1: 5-and1:8-disulfonic acids, which are then partly amidated by treatmeniwith ammonia

LITERATURE.—Cain, Intermediate Products (2d Ed.), 252Ullmann, Enzy. tech. Chcmic, 1, 475Langc, Zwischcnproduktc, #3265

Dye Derived from 1: 5- and 1:8-Amino-anthraquinone-sulfonic Acids


851



Alizarin DirectBlueB


Manufacture

I '14:—10,201I '20:— 2,982


[Dibromination]Aniline[Sulfonation]


A


Amino-azo-benzene

Phenyl-azo-aniline (C A. nomen.)

C TT "\T -I A7

S T A T I S T I C S . — I m p o r t e d ' 1 4 : — v e r y s m a l l

M a n u f a c t u r e d ' 1 7 : — 1 4 1 , 8 8 8 l b s .


M a n u f a c t u r e d ' 1 9 : — 8 2 , 7 5 5 l b s .


F O R M A T I O N . — T h e a m i n o - a z o - b e n z e n e i s p r e p a r e d f r o m a n i l i n e , b y

m o l e c u l a r r e a r r a n g e m e n t o f d i a z o - a m i n o - b e n z e n e , w h i c h i n t u r n i s

m a d e f r o m a n i l i n e a n d d i a z o - b e n z e n e c h l o r i d e ( d i a z o t i z e d a n i l i n e )

L I T E R A T U R E . — C a i n , I n t e r m e d i a t e P r o d u c t s ( 2 d E d . ) , 8 1

D y e s D e r i v e d f r o m A m i n o - a z o - b e n z e n e


31

137

223

224

225

226


MONOAZO DYESAmino-azo-benzeneSpirit Yellow

Fast YellowAcid Yellow

DISAZO DYESSudan III

Cloth Red G

Croceine AZ

Croceine B


Manufacture

M'17:— ?M'18:— 52,283M'19:— ?M'20:— ?I '14:— 37,378M'17:— ?M'18:— ?I '20:— 7,848M'20:— ?

I '14:— 2,409M '17:— ?M'18:— ?M'19:— ?M'20:— ?I '14:— 401

M'19:— ?M'20:— ?I '14:— 500

'20:— 100


[Oleum]

jS-Naphthol

Nevile-Winther Acid

l-Naphthol-3:6-disul-f onic Acid

l-Naphthol-4: 8-disul-f onic Acid


ss

A

ssMF

A

A

A


Dyes Derived from Amino-azo-benzene (continued)


227

228

229

279

606697

699

701


DISAZO DYES(continued)

BrilliantCroccine M

Ponceau 5RErythrine P

Azo Acid Violet

Bcnzo Fast Scarlet

AZINE DYESIndamine BlueInduline (Spirit

Soluble)

Indulme (WaterSoluble)

ParaphenylcncBlue R


Manufacture

I '14:—125,137M'17:— ?M'18:— 84,643M'19:—157,509I '20:— 49M'20:—129,124I '14:— 2;SS0M'17:— ?•jv/rnq. ?iVJL JL!/ . II '14:— 150I '20:— 11M'20:— ?I '14:— 36,674M'19:— ?I '20:— 24,153

I '14:— 25,342M'17:— ?M'18:— 8,589M'19:—436,201M'20:—140,400I '14:— 29,177M'17:—1S3,739M'18:— 91,724M'19:—130,704I '20:— 500M'20:—168,048


G Acid

2-Naphthol-3:6:8-trisulfonic Acid

1: 8-Dihydroxy-naph-thalcnc-4-sulfonicAcid

J AcidPhosgene

Aniline (excess)Aniline (excess)

Aniline (excess)[Sulfonation]

7)-Phcnylene-diaminc


A

A

A

D

Bss

A

B

Amino-azo-benzene-disulfonic Acid

6-Amino-3:4'-azo-bis6enzene-sulfonic Acid (C. A. nomen.)

SO3H

= 357

ORMATION.—From amino-azo-benzene by sulfonation with oleum


SckultzNumberfor Dye

247

251

Dyes Derived from


DISAZO DYESDouble ScarletScarlet EC

Croccine Scarlet 0



Manufacture

I '14:— 39,522M'17:— ?M'18:— 74,203

M'20:— ?I '20:— 100


0-Naphthol

Croccine Acid


A

A

Amino-azo-benzene-sulfonic Acid

p-(p-Amino-phenyl-a2:o)-5enzene-sulfonic Acid ((7. A. nomen.)

= C12H11N3O3S = 277

FORMATION.—From amino-azo-benzene by sulfonation at low tempera-ture by means of oleum


246

248249250

Dyes Derived from


DISAZO DYESCloth Scarlet G

Fast Scarlet BCroceine Scarlet 3BMilling Orange

Ammo-azo-benzene-sulfonic Acid


Manufacture

I '14:— 9I '17:— ?I '18:— ?I '19:— ?I '20:— ?I '14:— 1,755I '14:— 9,613I '14:— 4,370


jS-Naphthol

Schacffer's AcidCroceine AcidSalicylic Acid


A

AAM

6-Amino-3: 4;-azo-bis6enzene-sulfonic Acid (C. A. nomen.)

See, Amino-azo-benzene-disulfonic Acid


a-Amino-azo-naphthalene

4-(Naphthyl-azo)-l-naphthylamine (C. A. nomen.)

=C2oH15N3 =

35

H2N

FORMATION.—From a-naphthylaminc, this compound is prepared bymixing equal molecules of a-diazo-naphthalene chloride (froma-naphthylamine) and a-naphthylamine hydrochloride in coldaqueous solution.


694

695

Dyes Derived


AZINE DYESRose MagdalaFast Pink for SilkParaphcnylcne Violet

from a-Amino-azo-naphthalene


Manufacture

I '14:— 597

I '20:— 337


a-Naphtli5damine

7;-Phcnylenc-diamine


A

B

o-Amino-azo-toluene

p-(o-Tolyl-azo)-o-foluidine (C. A. nomen.)

CH3 CH3

=CuH1 5N3 — 225

STATISTICS.—Manufactured 1917:—14,355 lbs.Manufactured 1918*— ?

FORMATION.—From o-toluidine, by molecular rearrangement of diazo-amino-toluene, which in turn is made by the reaction of equalmolecules of o-toluidine and diazo-toluene chloride (diazotizedo-toluidine)

LITERATURE.—Cain, Intermediate Products (2d Ed.), 82.


Dyes Derived from o-Amino-azo-toluene


68

149

230231

232

233

234235

236


MONOAZO DYESSpirit Yellow RYellow Fat ColorFast Yellow R

DISAZO DYESCloth Red 3 GACloth Red 3B Extra

Sudan IV

Cloth Red B

Cloth Red GCroceine 3B

Cloth Red BWool Red B


Manufacture

I 14:— 251I 14:— 15I ' 2 0 : - 84I 14:— 51

M17:— 13,334M18:— 14,904M19:— ?M'20:— ?I 14:— 1,962M18:— ? *M19:— ?M '20:— ?I 14:— 554M19:— ?M;20:— ?I 14:— 14,293

M17:— ?M18:— ?M19:— ?MJ20:— ?


[This is amino-azo-toluene]

[Oleum]

Bronner's AcidEthyl-2-naphthyl-

amine-7-sulfonic Acid0-Naphthol

Nevile-Winther Acid

SchaefTer's Acidl-Naphthol-4: 8-disul-

fonic AcidRAcid


ss

A

MM

ssMF

M

MA

A

o-Amino-azo-toluene-sulfonic Acid

4-(4-Amino-m-tolyl-azo)-m-toluene-sulfonic Acid (C.A. nomen.)

CH-3 CH3

= C14H15N3O3S = 305

FOEMATION.—o-Amino-azo-toluene is sulfonated with oleum


Dyes Derived from o-Amino-azo-toluene-sulfonic Acid

37


252253254

255


DISAZO DYESCloth Scarlet JROrseilline BBBordeaux G

Croceinc Scarlet SBPonceau 6RB


Manufacture

I'14:—2,379I720:-- 154


0-NaphtliolNcvilc-Winther's AcidSchaeffer's Acid

Croceinc Acid


MAA

A

Amino-azo-xylene

4-(2: 4-Xylyl-azo)-2: 5-zylidine (C. A. nomen.)

H3C

H 3 C < ^ ^ > N 2 < ^ ) N H 2 = C16H19N3 = 253

CH3 CH3

FORMATION.—From xylidine, and by action of diazo-m-xylidine (2:4-xylidine) on p-xylidine (2: 5-xylidine)

LITERATURE.—Nolting and Forel, Ber. 18, 2668 (1885)Nictzki, Ber. 13, 471 (1880)Schultz, Chemie Steinkohlentcers 1, 137

Dyes Derived from Amino-azo-xylene

SchultzNurnberfor Dye

23723S

Ordinary Name a?idClass of Dye

DlbAZO I)YE«Bordeaux BXUnion Fast Claret



Used and Notes

AcidH Acid

ymAppli-cationClass

AA

m -Amino~i&enzaldehyde

HCO

JNH2


FORMATION.—Benzaldehyde is nitrated, resulting in a mixture of o- andra-nitro-benzaldehyde (20 and 80 per cent). The reduction iseffected and the o-derivative is removed by treating the crudenitration mixture with sodium hydrosulfite and hydrochloric acid,whereupon the o-derivative crystallizes out as the anhydro-derivative of o-amino-benzaldehyde. The solution contains them-amino-benzaldehyde, and it is used directly

LITERATURE.—Cain, Intermediate Products (2d Ed.), 144, 145Lange, Zwischenprodukte, #316-318

USES.—For preparation of m-Hydroxy-benzaldehyde

P-Amino-Aenz aldehyde

HCO

= C7H7NO =

KH2

FORMATION.—p-Nitro-toluene, in alcoholic solution, is run into a solu-tion of sulfu in caustic soda; and the mixture is heated under areflux condenser for l j hours, and then separated

LITERATURE.—Lange, Zwischenprodukte, #319-327Ullmann, Enzy. tech. Chemie, 2, 307


129130

Dyes Derived


MONOAZO DYES

Chromazone Red AChromazone Blue R

from p-Amino-benzaldehyde


Manufacture

114:—243


Chromotropic AcidChromotropic AcidEthyl-phenyl-hydrazine


MM

p-Amino-5enzaldehyde Ethyl-phenyl-hydrazone (C. A. nomen.)

See, p-Amino-benzylidine-ethyl-phenyl-hydrazone

l-Amino-4-benzamido-anthraquinone (C. A. nomen.)

See, l-Amino-4-benzoylamino-anthraquinone


2-Amino-p-&enzene-disulfonic Acid (C. A. nomen.)

Aniline-2: 5-disulf onic Acid

SO3H

39

VSO3H

FORMATION.—The sodium salt of 4-chloro-3-nitro-benzene-sulfonate isboiled with sodium sulfite, resulting in formation of sodium 2-nitro-benzcne-disulfonate, which is reduced with iron and acetic acid toanilinc-2: 5-disulf onic acid


USES.—For preparation of ethyl-m-amino-phenol

4-Amino-/zr-5enzene-disulfonic Acid (C. A. nomen.)Aniline-2: 4-disulfonic Acid

SO3H

= C6H7NO6S2 =

NH2

FORMATION.—-By heating sulfanilic acid (p-aniline-sulfonic acid) witholeum at 170-180° C.

LITERATURE.—Ann. 198, 17

Beilstein, Organische Chcmie (3 auf.) II, 571

Dye Derived from 4-Amino-m-^enzene-disulfonic Acid


263


DISAZO DYEJet Black R



Used and Notes

a-NaphthylaminePhcnyl-a-naphthyl-

amine


A

/n-Amino-benzene-sulfonic Acid

See, Metanilic Acid


p-Amino-benzene-sulfonic AcidSee, Sulfanilic Acid

Amino-benzenyl-o-amino-thio-cresol

See, Dehydro-thio-p-toluidine

m-Amino-^enzoic Acid

COOH

FORMATION.—m-Nitro-benzoic acid is reduced with iron and acetic acid

LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 333

Dyes Derived from m-Amino-benzoic Acid


203204

486


MONOAZO DYESYellow Fast-to-soapDiamond Yellow G

TETRAKISAZO DYEDirect Brown J


Manufacture

I '14:—3,640


DiphenylamineSalicylic Acid

m-Phenylcnc-diamine(3 mols)

m-Amino-benzoic Acid(2 mols)


MM

D

o-Axoino-benzoic Acid

See, Anthranilic Acid

l-Amino-4-benzoylamino-anthraquinone

l-Amino-4-benzamido-anthraquinone ( C A. nomen.)

no NH2

oC.Uw NH. COC6HB


FORMATION.—By heating 1:4-Diamino-anthraquinone in a toluene ornitro-benzene solution with benzoyl chloride

LITERATURE.—Cf. Ullmann, Enzy. tech. Chemie, 1, 164

Bye Derived from l-Amino-4-benzoylamino-anthraquinone


833



Algol Olive R


Manufacture

I ?14:—13,334I '20:— 461


l-Bcnzoylamino-4-chloro-anthraq uinonc

[Chloro-sulfonic Acid]


V

p-Amino-benzyl-diethylamine

p-Amino-iVr:iVr-diethyl-6enzylaminc (C. A. nomen.)

CH2 .N.(C2H5)2

NH2

FORMATION.—p-Nitro-bcnzyl chloride is treated with 2 mols of dicthyl-amine in alcoholic solution at 100° C ; and the resulting p-nitro-benzyl-diethylaminc is reduced with SnCl2 and HCl to the p-amino-benzyl-dicthylaminc

LITERATURE.—Ber. 28, 1141

Cf. Lange, Zwischenprodukte, #255

Dye Derived from p-Amino-benzyl-diethylamine


435


TRISAZO DYEJanus Brown B

Statistics ofImport arid


Used and Notes

a-Naphthylaminellesorcinol or ra-phcnyl-

ene-diaminc[or Chrysoidine]


B


o-Amino-benzyl-dimethylamine

o-Amino-JV:iV-dimethyl-6enzylamine (C. A. nomen.)

CH2 .N(CH3)2

Q N H 2

FOKMATION.—o-Nitro-bcnzyl chloride is treated with 2 mols of dimethyl-amine in alcoholic solution at 100° C , and the resulting o-nitro-benzyl-dimethylamine is reduced with SnCl2 and HC1 to theo-amino-benzyl-dimethylamine

LITERATURE.—Cf. Ber. 28, 1141(7/. Lange, Zwischenprodukte, #250, 255

Dyes Derived from o-Amino-benzyl-dimethylamine


74

75


MONOAZO DYESTannin Orange

New Phosphinc G


Manufacture

I '14.-2,202I '20:— 349

I '14:— 500


p-Aminob enzyl-di-methylaminc

/3-Naphthol (2 mols)

p- Amino-b enzyl-di-methylamine

Resorcinol (2 mols)


B

B

p-Amino-benzyl-dimethylamine

p-Amino-AT:iV-dimethyl-&enzylarDine (C. A. nomen.)

CH2.NCCH3)2

NH2

FORMATION.—p-Nitro-benzyl chloride is treated with 2 mols of dimethyl-amine in alcoholic solution at 100° C ; and the resulting p-nitro-benzyl-dimethylamine is reduced with SnCl2 and HC1 to the p-amino-benzyl-dimethylamine


Lange, Zwischenprodukte, ^255


Dyes Derived from p-Amino-benzyl-dimethylamine


74

75


MONOAZO DYESTannin Orange R

New Pliospliinc G


Manufacture

I '14:—2,202I ;20:— 249

I'14:— 500


o-Amino-benzyl-di-methylamine

0-Naphthol (2 mols)

o-Amino-bcnzyl-di-methylamine

Ilcsorcinol (2 mols)


B

B

p-Amino-benzyl-ethyl-aniline-sulfonic Acid

See, Ethyl-sulfobenzyl-p-phenylene-diamine

p-Amino-benzylidene-ethyl-phenyl-hydrazone

Ethyl-phenyl-hydrazone of p-Amino-benzaldehyde

p-Amino-&enzaldehyde Ethyl-phenyl-hydrazone (C. A. nomen.)

HC:N.N<

NH2

FOKMATION.—^By condensation of ethyl-phenyl-hydrazine and p-amino-benzaldehyde

Dye Derived from p-Amino-benzylidene-ethyl-phenyl-hydrazone


130


MONOAZO DYEChromazone Blue It



Used and Notes

Chromotropic Acid


M


l-Amino-2-bromo-4-hydroxy-anthraquinone

4-Amino-3-bromo-l-hydroxy-anthraquinone (C A nomen.)

n0 NH2

FORMATION.—From l-amino-2:4-dibromo-anthraquinone by heatingwith monohydrate at 100-110°

LITERATURE.—Lange, Zwischenprodukte, #3314

Dye Derived from l-Amino-2-bromo-4-hydroxy-anthraquinone


844



Algol Blue 3G


Manufacture

I '14:—9,191I '20:—3,S96


l-Amino-2-bromo-4-hydroxy-anthraqui-none (2 mols)


V

4-Amino-3-bromo-l-hydroxy-anthxaquinone (C. A. nomen.)

See, l-Amino-2-bromo-4-hydroxy-anthraquinone

l-Amino-4-bromo-2-methyl-anthraquinone

aCO NH2

=C1 6H1 0BrNO2 =

FORMATION.—2-methyl-anthraquinone (which is obtained by the con-densation of toluene with phthalic anhydride) is nitrated andreduced. The resulting l-amino-2-methyl-anthraquinone is bromi-nated in a glacial acetic acid solution and the l-amino-4-bromo-2-methyl-anthraquinone is formed

LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 486Barnett, Anthracene and Anthraquinone, 80, 192, 229Cain, Intermediate Products (2d Ed.), 260


Dyes Derived from l-Amino-4-bromo-2-methyl-anthraquinone


859

SGO



Cyananthrol 11

Cyananllirol G


Manufacture

I '14:—1S,7O2I '20:— 2,416

I '20:— 5,127

Other IntermediatesVied and Notes

/j-Toluidine[Sulfonation]

/;-Toluidine[Sulfonation]


A

A

Cl

l-Amino-6-chloro-anthraquinone

r o NH2


827

Dye Derived from



IndanthrencBordeaux B extra

1 - Amino -6 - chloro - anthraquinone


Manufacture

I '14:—2S,72SI '20:— 4,050

Other Interim diatesUsed and Notes

1-Amino-G-ohloro-an-thraquinonc (2 mols)

2: 7-Dichloro-anthra-quinonc


V

2-Amino-6-chloro-6enzene-sulfonic Acid (C. A. nomen.)

3-Chloro-anilinc-2~sulfonic Acid

m-Chloro-anilinc-o-suKonic Acid

SOJI

5 — 207.5

FOEMATION.—By the reduction of m-chloro-nitro-benzcnc-o-sulfonicacid in the usual way.


LITERATURE.—Beil. II, 571

Dye Derived from 2-Amino-6-chloro-benzene-sulfonic Acid

SchultzNumberjor Dye

131


MONOAZO DYEPermanent Orange R



Used and Notes

j8-Naphthol


CL

l-Amino-4-chloro-3-metbyl-benzene-6-sulfonic Acid

See, 2-Amino-5-chloro~p-foluene-sulfonic Acid (C A. nomen.

2-Amino-5-chloro-p-foluene-sulfonic Acid (C. A. nomen.SOzH—1)

2-Chloro-5-toluidine-4-sulfonic Acid (CHz=l)

l-Amino-4-chloro-3-methyl-benzene-6-sulfonic Acid

SO3H

NH2 _ C7H8C1NO3S = 221.5

CH3

STATISTICS.—Manufactured '20:—22,753 lbs

FORMATION.—From o-chloro-toluene-p-sulfonic acid (CHz=l) by nitra-tion and subsequent reduction


Dye Derived from 2-Amino-5-chloro-p-toluene-sulfonic Acid (S0sH=l)


153


MONOAZO DYELake Red C


Manufacture

I '14:—306,607M'19:— ?I '20:— 4,105


jS-Naphthol


CL


4-Amino-chrysoidine (C.A. nomen.)

2:4:4'-Triamino-azo-benzene

H2N

~ 2 = C l 2 H l 3 N 5 = 2 2 7

47

FORMATION.—(1) p-Amino-acetanilide (acetyl-p-phenylene-diamine) isdiazotized and combined with m-phenylene-diamine, and then theacetyl group removed

(2) p-Nitro-aniline is diazotized and combined with m-phenylene-diamine, and the product reduced with sodium sulfide


Dye Derived from 4-Amino-chrysoidine


239


DISAZO DYEAzotol C



Used and Notes

0-Naphthol


MF

2-Amino-p-cresol (011=1, C. A.nomen.)

m-Amino-p-cresol (CH$=1)

3-Amino-p-cresol (Eng. and Germ, nomen.

OH

/ ]NH2 _

CH3

_ 1 2 3

FORMATION.—(1) p-Cresol is nitrated and then reduced with SnC^ andHC1. (2) p-Toluidinc is treated with nitric and nitrous acids so asto form 2-nitro-p-cresol (OH = i ) , which is then reduced to theamino compound

LITERATURE.—Ber. 22, 348; 24,1960

Beil. II , 752


Dye Derived from 2-Amino-p-cresol


260


DISAZO DYEErio-Chrome

Verdon


Manufacture

I '14:—8S2


Sulfanilic acid/3-Naphthol


ACr

3-Amino-p-cresol (Eng. andGer. nomen. CHz=l)

See, 2-Amino-p-cresol (OH =1, C. A. nomen.)

3-Amino-p-cresol (OH^l, C. A. nomen.)

6-Amino-p-cresol (CHZ = 1)

o-Amino-p-cresol (CHz—l: Ger. and English nomen.)

OH

FORMATION.—p-Toluidine is nitrated, and the 3-nitro-p-toluidinesulfate (NHz^l) therefrom is treated with NaNO2 in the coldand then boiled with dilute sulfuric acid, thus forming 3-nitro-p-cresol, which latter on reduction with SnCk and HCl gives 3-amino-p-cresol

LITERATURE.—Beil. II, 751, 753

Dye Derived from 3-Amino-p-cresol


576


XANTHONE DYERhodamine 3G


Manufacture

I '14:—19,568I ' 2 0 : - 855


Dimcthylamino - hy~droxy - benzoyl- ben-zoic acid

[Ethyl estcrification]


B

6-Amino-p-cresol (C Hz=1)See 3-Amino-p-cresol (OH ••--1, C. A. nomen.)


m-Amino-Jp-cresol (CH3=1)

See, 2-Amino-p-cresol (OH =17 C. A. nomen)

o-Amino-p-cresol (CH3-1)

See, 3-Amino-p-cresol (OH =./, C. A. nomen)

2-Amino-p-cresol Methyl Ether (OCIIZ=1)

6-Methoxy-m-toluidine (C. A. nomen. NH2=1)

m-Amino-p-cresol Methyl Ether

3-Amino-4-cresol Methyl Ether

OCH3

49

CH3

FORMATION.—2-Nitro-p-cresol (OH = 1), obtained by action of nitrousand excess nitric acids upon p-toluidine, is methylated and reduced

LITERATURE.—Ber. 22, 348; 24, 960

Dyes Derived from 2-Amino-/>-cresol Methyl Ether (OCH3=1)


9G

100

101

439

440


MONOAZO DYESChrome Fast

Yellow GG

Eosamine B

Cocchnue B

TRISAZO DYESDirect Indigo Blue.

Direct IndigoBlue BK


Manvfacture

I '14:— 150I'20:— 500

I '14:—1,914I '20:—1,600

AM'18:— ?


Salicylic Acid


R Acid

BcnzidineH Acid (2 mols)

BenzidinoGamma Acid (2 mols)


M

A

A

D

D


m-Amino-£-cresol Methyl EtherSee, 2-Amino-p-cresol Methyl Ether (OCHZ = 1)

l-Amino-2:4-dibromo-anthraquinone

CO N H 2

f | Y J B r = Ci4H7Br2NO2 = 381

C 0 Br

FORMATION.—1-Amino-anthraquinone is treated in nitro-benzene solu-tion and at about 120-130° with an excess of bromine

LITERATURE.—Ullmann, Enzy. tech Chcmie, 1, 475Ger. Pat., 160,169

Dye Derived from l-Amino-2:4-dibromo-anthraquinone


855



Alizarin Pure Blue B



Used and Notes

p-Toluidine[Sulfonation]


ACr

2-Amino-4: 6-dichloro-phenol

OH

_ 1 7 8

Cl

FORMATION.—4:6-Dichloro-2-nitro-phenol is reduced with tin andhydrochloric acid

LITERATURE.—Beil. I I , 727

Dye Derived from 2-Amino-4: 6-dichloro-phenol


86


MONOAZO DYEAzarine S



Used and Notes

0-Naphthol


M


4-Amino-l-diethylamino-benzene-3-thiosulfonic AcidSee, Diethyl-p-phenylene-diaminc'thiosulfonic Acid

^-Amino-diethyl-aniline

See, N: iVVDiethyl-p-phenylene-diamine (C A. nomen.)

^-Amino-diethyl-aniline-thiosulfonic Acid

See, Diethyl-p-phenylene-diamine-thiosulfonic Acid

^-Amino-iV: JV-diethyl-fcenzylamine ((7. A. nomen.)

See, p-Amino-benzyl-diethylamine

2-Amino-5-dimethylamino-i6enzene-thiosulfonic Acid (C. A,nomen.)

See, Dimethyl-p-phenylene-diam"ne-thiosulfonic Acid

m-Amino-dimethyl-anilineSee N: N Dimethyl-m-phenylene-diamine C. A. nomen.)

j!>-Amino-dimethyl-anilineSee, iV.'iV-Dimethyl-p-phenylene-diainme (C A. nomen.)

/>-Amino-diniethyl-aniline-thiosulfonic Acid

See, D'mcthyl-p-phenylcnc-diamine-thiosulfonic Acid

o-Amino-iV: N-dimethyl-6enzylainine (C. A. nomen.)

See, o-Amino-benzyl-dimethylamine

^-Amino-iV': iV-dimethyl-&enzylamine (C. A. nomen.)

See, p~Amino-benzyl-dimethylamine

4/-Amino-2:4-dinitro-diphenylamineN- 2:4-Pinitro~phenyl)-p-phcnylene-diamine (C A. nomen.)

NO2

^ =1C12H10N4O4=274


FORMATION.—l-Ch'oro-2:4-dinitro-benzene is condensed with p-phenyl-ene-diamine


Dye Derived from 4/~Amino-2: 4-dinitro-diphenylamine


727


SULFUR DYEAuronal Black B



Used and Notes

[Glycerol; S+Na,S]


S

o- Amino -diphenylamine

iV-Phenyl-o-phenylene-diamine (C. A, nomen.)

NH2

/ ~ " > = Ci2H12N2 r=r 184

FORMATION.—By reducing o-nitro-diphenylamine (from o-bromo-nitro-benzene and aniline) by heating with ammonium sulfide

LTTERATURE.—Lange, Zwischenprodukte, #1611Chem. Zeitung, 18, 1095Ber. 23, 1843

Dye Derived from o-Amino- diphenylamine


668


AZINE DYEFlavinduline 0


Many fact arc

J '14:—6G0

Other IntermediatesUt>ed and Notes

PI icnanthrenc-quinonc


B

£-Amino-diphenylamine

-ph nylene-diamine (C. A. nomen.)

= C12H12N2 = 184


FORMATION.—This intermediate can be prepared by reducing OrangeIV, by means of sodium sulfide and sulfur. The Orange IVresults from the coupling of diazotized sulfanilic acid with di-phenylamine

LITERATURE.—Langc, Zwischenprodukte, #1611Cain, Intermediate Products (2d Ed.), 74

Dyes Derived from £-Amino-diphenyIamine


687

922


AZINE DYERosolan 0

ANILINE BLACKGROUP

Diphenyl Black


Manufacture

I '20:—1,083

I '14:—1,470M'19:— ?M'20:— ?


Anilineo-Toluidinc[Oxidation]

?;-A min o-diphcnyl-iUiiiiK* (x mols)

[Oxidation]


B

Special

^-Amino-diphenylamine-2-sulfonic Acid

2-Anilino-5-amino-I)cnzcnc-sulfonic Acid (C. A. nomen.)

SO3H

C C i 2 H i 2 N - ° 3 S = 2 G *

FORMATION.—p-Chloro-nitro-bcnzene is sulfonatcd to 2-chloro-5-nitro-benzene-sulfonate, which latter in presence of glycerol and sodiumcarbonate is condensed with aniline to form p-nitro-diphenylamine-2-sulfonic acid. This is reduced by iron and hydrochloric acid,resulting in p-amino-diphcnylaminc-2-sulfonic acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 75Cf. Lange, Zwischenprodukte, #1646, 1647

USES.—For preparation of the Nerol Dyes


a-(^-Amino-JVP-ethyl-anilino)-^~toluene-sulfonic Acid (C. A.nomen.)

, Ethyl-sulfobenzyl-p-phenylene-diamine

a-(4-Amino-i\T-ethyl-3-sulfomercapto-anilino)-J!>-^oluene-sulfonicAcid (C A. nomen.)

Ste, Ethyl-sulf obenzyl -p-phenylene-diamine-thiosulf onic Acid

^-Amino-ethyl-o-toluidine (C#3 = 1)

See, iV3-Ethyl-4-m-tolyene-diamine (C. A. nomen.

^-Amino-ethyl-o-foluidine

See, JN^-Ethyl-p-tolylene-diamine

Amino-G Acid1

2-Naphthylamine-6:8-disulfonic Acid

7-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)

j8-Naphthylamine-Y-disulfonic Acid

/3-Naphthylamine-disulfonic Acid G

HO3S

H ° 3 S \ / \ / = C l ° H 9 N ° 6 S 2 = 3 ° 3

STATISTICS.—^Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:—894,624 lbs.

FORMATION.—From G acid, by heating the sodium salt with ammoniaand sodium bisulfite solution, in an autoclave under pressure

LITERATURE.—Lange, Zwischenprodukte, #2599Cain, Intermediate Products (2d Ed.), 209

1 Occasionally in the older literature, this 2-naphthylamine-6: 8-disulf onic Acidhas been called G Acid.


Dyes Derived from Amino-G Acid

55


178

270

271

272

Ordinary Name andClabh of Dye

MONOAZO DYECrumpsall Yellow

DISAZO DYESBiilhcint Cioteme 9B

Diaminc Blue 6G

Naphthol Black BBrilliant Black B


Manufacture

I '14 -—103,598M'19— ?I '20 — 50


Salicylic Acid

ArnlmeG and R Acids

1 -Ammo-2-naphtholethyl ether

0-Naphthol

a-NaphthylammeR Acid


A

A

D

A

l-Amino-4-hydroxy-anthraquinone

4-Ammo-l-hydroxy-anthraquinone (C. A. nomen.)

NH2

FORMATION.—(1) From quinazarin by heating with ammonia. (2) From1-amino-anthraquinone by heating with sulturic acid (66° Be.) andboric acid to 180-200° C.

LITERATURE.—Lange, Zwischenprodukte, #3253-3255

Dye Derived from l-Amino-4-hydroxy-anthraquinone


818



Algol Pink It


Manufacture

I '14— 126I '20 —1,368


Bcnzoyl chloride


V


4-Amino-l-hydroxy-anthraquinone (C. A. nomen.)

See, l~Amino-4-hydroxy~anthraquinone

4-Amino-4'-hydroxy-dIphenylamine

p-(p-Amino-anilino)-phenol ( C A. nomen.)

= C l 2 H l 2 N 2 ° — 2 0 0

FORMATION.—From phenol and p-phenylene-diamine by oxidation atlow temperature


Dye Derived from. 4-Amino-4'-hydroxy-diphenylamine


732

Ordinary Name andClass oj Dye

SULFUR DYEAutogene Black


Manufacture

I '14:—7,495


Phenol[S2C12; S+Na^S]


s

2-Amino-7-hydroxy-diphenylenazine

See, 2-Amino-8-hydroxy-phenazine

2-Amino-4r-hydroxy-4-nitro-diphenylamine

4-Nitro-2-arnino-4/-hydroxy-diphenylamine

p-(2-Amino-4-nitro-anilino)-phenol (C A. nomen.)

NH2

O o N < f ~ V - N H — ( ^ " " N O H = C u H u N a O s = 245

FORMATION.—Chloro-dinitro-benzene is condensed with p-amino-phenol in presence of an acetate to 2: 4-dinitro-4'-hydroxy-di-phenylamine, which by partial reduction furnishes the above de-rivative.

LITERATURE.—Beil II, spL, 399; IV, spl, 397Lange, Zwischenprodukte, #1670Thorpe, Die. Chemistry, 2, 245


Dyes Derived from 2-Amino-4'-hydroxy-4-nitro-diphenylamine


726

730

736


SULFUR DYES

Pyrogcne Direct BluePyrogene Blue

Pyrogene Black G

Thion Blue B


Manufacture

I '14:—10,934I '20:— 2,49S

I '14:— 8,725

I '14:— 7,353I '20:—11,855


[Alcohol; S+Na*S]

[S+Na^S; It is not cer-tain that the amino-hy-droxy - nitro - diphenyl-amine referred to isthe one with the posi-tions given above]

[CS2; S+Na2S]


S

s

s

2-Amino-8-hydroxy-phenazine

2-Amino-7-hydroxy-diphcnylenazine

8-Amino-2-phenazinol (C. A. nomen.)

H 0 ( X l X ) N H ! =

FORMATION.—l-Chloro-2:4-dinitro-benzenc condensed with p-amino-phenol, the product reduced, and the resulting diamino-hydroxy-diphenylamine oxidized in alkaline solution with manganese dioxide

LITERATURE.—Lange, Zwischcnprodukte, #1969Cain, Intermediate Products (2d Ed.), 83

Dye Derived from 2-Amino-8-hydroxy-phenazine


739


SULFUR DYEImmedial

Bordeaux GImmedial Maroon B

Statistics ofI'm port and

Manufacture

I '14:—15,496


[S+Na^S]


s


5-Amino-2-hydroxy-fhionaphthene (C. A. numbering)

6-Amino-3-hydroxy-thionaphthene (German numbering)

orOH

= C 8 H T N O S = 1 6 5

FORMATION.—4-Acetarnido-2-amino-benzoic acid is diazotized, reactedfirst with potassium xanthate (C2H5O . CS . SK) and then withchloro-acetic acid, forming 4-acetamido-2-thioglycolic-benzoic acid,which by melting forms the desired 5-amino-2-hydroxy-thio-naphthene

LITERATURE.—Lange, Zwischenprodukte, #2166Ullmann, Enz. tech. Chemie, 3, 568

Dyes Derived from 5-Amino-2-hydroxy-thionaphthene





Used and Notes


902

903

904

911

914

INDIGO GROUP DYESHelindone Brown 2R

Helindone Brown 5R

Helindone Brown G

Ciba Orange G

Helindone Orange D

I ;14:-~ 876I '20:— 1,778

I '14:—13,086I '20:— 2,200

I '14:— 222

I '20: 17

2-Isatin-anilide[Bromination; ? classi-

fication]

2-Isatm-anilide[Bromination]

Isatin[Bromination]

Acenaphthenequinone[Bromination]

5-Amino-2-hydroxy-thionaphthene (2 mols)[Bromination]

V

V

V

V

6-Amino-3-hydroxy-thionaphthene (German numbering)

See, 5~Amino-2~hydroxy-thionaphthene (C. A. numbering)


l-Amino-4-methoxy-anthraquinone

•C(X

59

OCH3

FORMATION.—Probably by the nitration and subsequent reduction of1-methoxy-anthraquinone. The 1-methoxy-anthraquinone is ob-tained from 1-nitro-anthraquinone by heating with an alcoholicsolution of potassium methylate with exclusion of water

LITERATURE.—Cf. Barnett, Anthracene and Anthraquinonc, 169, 279,280, 287


815

829

Dyes Derived from



Algol Scarlet G

Algol Bordeaux 3B



Manufacture

I '20:—959

I '20:-— 61


Bcnzoyl chloride

l-Amino-4-mcllioxy-an-thraquinone (2 mols)

2: 6-Dichloro-anthra-quinone


V

V

l-Amino-2-methyl-anthraquinone

•CCXCH3 _ ,

FORMATION.—2-Methyl-anthraquinone is dissolved in sulfuric acidsolution and nitrated with sodium nitrate. The nitro compoundis then separated and reduced with sodium sulfi.de

LITERATURE.—Cain, Intermediate Products (2d Ed.) , 260Lange, Zwischenprodukte, #3209


Dye Derived from l-Amino-2-methyl-anthraquinone


868



Cibanone Brown B


Manufacture

I '14:—399


[Sulfur]


V

3~Amino-4-methyl-diphenylamineSee, iV^Phenyl^-Tft-tolylene-diamine

IV-Amino-5-methyl-2-phenyl-thiazol-sulfonic Acid

See, Dehydro-thio-p-toluidine~sulfonic Acid

N- (3-Amino-4-methyl-phenyl) -^-toluene-sulf amide

3'-Ajnino~(p^oluene~sulfo)-p-toluide (C. A. nomen.)

(Example of m-amino-arylsulfamide)

N H . = C M H M N A S = 2 7 6

FORMATION.—3-Nitro-p-toluidine (NH2 = 1) is suspended in water,p-toluene-sulfochloride and soda added. The reaction productis purified by solution in dilute caustic soda and precipitation withhydrochloric acid. This nitro body is now reduced with zinc dustand hydrochloric acid to the amino-sulfamide

LITERATURE.—Lange, Zwischenprodukte, #1801Schultz-Heumann, Anilinfarben, 4, 2103Ger. Pat. 135,016

Dyes Derived from iNT-(3-Amino-4-inethyl-phenyl)-^-toluene-sulfamide


92


MONOAZO DYEMetachrome

Bordeaux R



Used and Notes

Picramic Acid


M


a-Amino-naphthalene

See, a-Naphthylamine

/3-Amino-naphthalene

See, /3-Naphthylamine

3-Amino-2:7-naphthalene-disulfonic Acid (C. A. nomen.)

See, Amino-R Acid

4-Amino-l: 5-7iaphthalene-disulfonic Acid (C. A. nomen.)

See, l-Naphthylamine-4: 8-disulfonic Acid


See, l-Naphthylamine-4: 6-andA: 7-disulfonic Acids


See, l-Naphthylamine-4: 6-andA: 7-disulfonic Acids

4-Amino-2:-7-naphthalene-disulfonic Acid (C. A. nomen.)

See, Freund^s Acid


See, l-Naphthylaminc-5: 7-disulfonic Acid


See, 2-Naphthylaminc-5: 7-disulfonic Acid

7-Amino-l: 3-naphthalene-disulfonic Acid (C A. nomen.)

See, Amino-G Acid

8-Amino-l: 6-napthalene-disulfonic Acid (C. A, nomen.)

See, l-Naphthylaminc-3:8-disulfonic Acid

l-Amino-naphthalene-4-sulfonic Acid

See, Naphthionic Acid

l-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)



2-Anuno-l-naphthalene-sulfonic Acid (C. A. nomen.)

See, 2-Naphthylamine-l-sulfonic Acid

4-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)



See, Laurent's Acid

6-Anuno-2-naphthalene-sulfonic Acid (C. A. nomen)


5-and-8-Amino-2-naphthalene-sulfonic Acids (C A. nomen.)

See, l-Naphthylamine-6-and~7-sulfonic Acids

6-Amino-2-naphthalene-sulfonic Acid (C A. nomen.)

See, Broenner's Acid

6-and-7-Amino-l-naphthalene-sulfonic Acids (C. A. nomen.)

See, 2-Naphthylamine~5~and-8~sulfonic Acids

7~Ainino-2-naphthalene-sulfonic Acid (C. A. nomen.)

See, 2-Naphthylamine-7~sulfonic Acid



8-Amino-l: 3: 6-naphthalene-trisulfonic Acid (C. A. nomen.)

See, l-Naphthylamine-4: 6: 8-trisulfonic Acid

8-Amino-l: 3:6-naphthalene-trisulfonic Acid (C. A. nomen.)

See, l-Naphthylamine-3: 6: 8-trisulfonic Acid

6-Amino-l-naphthol

OH


FORMATION.—From l-amino-naphthalene-5-sulfonic acid by fusion withcaustic soda at 250°


Dye Derived from 5-Amino-l-naphthol


187


MONOAZO DYELanacyl Blue BB


Manufacture

I '14:—1,200


H Acid


A

Amino-naphthol 8

l-Amino-7-naphthol (not considered herein)

l-Aminc-8-naphthol-2:4-disulfonic Acid

8~Amino-l-7iaphthol-5: 7-disulfonic Acid (C. A. nomen.)

SS Acid or 2S Acid

Chicago Acid

Amino-naphthol-disulfonic Acid SS

HO NH2

—319

SO3H

STATISTICS.—Manufactured '19:— ?Manufactured ;20:— ?

FORMATION.—By caustic fusion at 180-190° of sodium l:8-naphtha-sultam-2:4-disulfonate (anhydride of l-amino-naphthalene-2:4: 8-trisulfonic acid), which in turn is made from 1-naphthylamine-4:8-disulfonic acid



Lange, Zwischenprodukte, #2719

Thorpe, Die. Chemistry, 3, 641

Dyes Derived from l-Amino-8-naphthoI-2:4-disulfonic Acid


419

422

424


DISAZO DYESChicago Blue RW

Chicago Blue 4B

Chicago Blue 6B


Manufacture

I 14:— 15,176M'19:— ?I '20:— 150

I '14:— 8,269

I '14:—118,542M'19:— ?I '20:— 7,480

M'20:— ?


Dianisicline/3-Naphthol

Dianisidine1- Amino-8-naphthol-

4-sulfonic Acid

Dianisidine1 -Amino-S-naph thol-

2:4-disulfonic Acid(2 mols)


D

D

D

l-Amino-8-naphthol-3: 5-disulfonic Acid

8-Amino-l-naphthol-4: 6-disulfonic Acid (C. A. nomen.)

Amino-naphthol-disulfonic Acid B

B Acid

HO NH2

:C10H9NO7S2=:319

HO3S

FORMATION.—By sulfonation of l-amino-S-naphthol-S-suKonic acid

LITERATURE.—Amer. Pat. 606,437

Ger. Pat. A. F . 8626


Dyes Derived from l-Amino-8-naphthol-3:5-disulfonic Acid


216

389

466


DISAZO DYESDomingo Blue

Black B

Eboli Blue B

TRISAZO DYEEboli Green CW



Used and Notes

Anilinep-Nitro-anilmc

Tolidine1- Amino- 8- naphthol-

3: 5-disulfonic Acid(2 mols)

BcnzidineSalicylic AcidSulfanilic Acid


A

D

D

l-Amino-8-naphthol-3:6-disulfonic Acid

See, H Acid


See, K Acid

2-Amino-8-naphthol-3: 6-disulfonic Acid

See, 2R Acid

7-Amino-l-naphthol-3:6-disulfonic Acid (C. A. nomen.)

See, 2R Acid

8-Amino-l-naphthol-3:5-disulf onic Acid (C A. nomen.)

See, K Acid


See, H Acid


See, l-Amino-8-naphthol-3: 5-disulf onic Acid



See, l-Amino-8-naphthol-2: 4-disulfonic Acid

Amino-naphthol-disulfonic Acid B

See, l~Amino-8-Naphthol-3: 5-disulfonic Acid

Amino-naphthol-disulfonic Acid H

See, H Acid

Amino-naphthol-disulfonic Acid K

See, K Acid

Amino-naphthol-disulfonic Acid RR

See, 2R Acid

Amino-naphthol-disulfonic Acid SS

See, l-Amino~8-naphthol-2: 4-disulfonic Acid

l-Amino-2-naphthol Ethyl Ether

Naphthylamine Ether

2~Ethoxy-l-naphthylamine ( C A. nomen.)

NH2

O. C2H5 — nxi

FOKMATION.—l-Nitro-2-naphthol ethyl ether is reduced in an alcoho]solution with iron turnings and hydrochloric acid

LITERATURE.—Lange, Zwischenprodukte, #2345, 2333


Dyes Derived from l-Amino-2-naphthol Ethyl Ether

67


268

271


DISAZO DYENaphthyl Blue

Black N

Diamine Blue 6 G


ManvfactureOther Intermediates

Used and Notes

l-Naphthylamme-4: 6-and 4: 7- disulfonicacids

a- Naphthylamine

Amino-G acid/3-Naphthol


A

D

l-Amino-2-naphthol-4-sulfonic Acid (C. A. nomen.)

1:2:4 Acid

NH2

C 0 O H -SO3H

239

STATISTICS.—Manufactured '18:—169,999 lbs.Manufactured '19:—837,384 lbs.Manufactured ;20:—971,370 lbs.

FORMATION.—/3-Naphthol is changed to the l-nitroso-£-naphthol,which is treated with sodium bisulfite. Upon acidification thefree sulfurous acid effects simultaneous reduction and sulfonation

LITERATURE.—Cain, Intermediate Products (2d Ed.), 233Langc, Zwischcnprodukte, #2507

Dyes Derived from l-Amino-2-naphthol-4-sulfonic Acid


29


MONOAZO DYESErio chrome Red B


Manufacture

I '14:— 5,491


3-Mcthyl-l-phcnyl-5-pyrazolone


ACr


DyesSchultz

Numberfor Dye

ISO

181

Derived from l-Amino-2-naphthol-4-sulfonic Acid (continued)



Erichrome BlueBlack B

Palatine ChromeBlack 6B

Salicine Black


Manufacture

I '14:— 57,000M'17:— 9,326M'18:— ?M'19:— ?I '20:— 20,317M'20:— 29,255

I '14:—248,721M'17:— ?M'18:—469,159M'19:—739,372I '20:— 2,001M'20:—

1,074,248


a-Naphthol

/3-Naphthol


ACr

ACr

l-Amino-2-naphthol-6-sulfonic Acid (C. A. nomen.)

NH2

HO3SOH

FORMATION.—Schaeffer's acid is treated with nitrous acid resulting inl-nitroso-2-naphthol-6-sulfonic acid. This latter is reduced withzinc and hydrochloric acid

LITERATURE.—Meldola, Chem. Soc. Trans. 39, 47 (1881)Thorpe, Die. Chemistry, 3, 637


656

Dye Derived from l-Amino-2-naphthol-6-sulfonic Acid


OXAZINE DYEAlizarin Green G


Manufacture

M'19:— ?


1: 2-Naphthoquinone-4-sulfonic acid


M


l-Amino-5-naphthol-7-sulfonic Acid

5-Amino~l-?2aphthol~3-sulfonic Acid (C A. nomen.)

M Acid

NH2

HO3Sf A _ c10H9NO4S = 239

69

HO

FORMATION.—By fusing l-naphthylaminc-5:7-disulfonic acid withcaustic soda at 160-220°

LITERATURE.—Cain, Intermediate Products (2d Ed.) 234Thorpe, Die. Chemistry, 3, 638


345

421

Dyes Derived from


DISAZO DYESOxamine Maroon

Oxamine Blue B



Manufacture

I J14:—35,891I ;20:— 13


BenzidincSalicylic Acid

DianisidincNcvile-Winthcr's Acid


D

D


8-Amino-l-naphthol-5H3iilfonic Acid (C A. nomen.)

Amino-naphthol-sulfonic Acid H

S Acid

HO NH2

SO3H

STATISTICS.—Manufactured '20:— ?

FORMATION.—By caustic aocki fusion of l-naphthylamine-4: 8-disulfonicacid at 200-230°




Lange, Zwischenprodukte, #2524 et seq.

Dyes Derived from l-Amino-8-naphthol-4-sulfonic Acid




Manufacture



220

324

325

336

384

387

388

390

420

422

DISAZO DYES

Palatine Black

Chicago Blue 4R

Columbia Blue R

Benzo Cyanine R

Chicago Blue 2RDiamineBlueC2R

Columbia Blue G

Chicago Blue R

Benzo Cyanine B

Azidine Wool Blue B

Chicago Blue 4B

I '14:-I '20:-

I '14:-

I '14:-

I '14:-

I '14:-

I '14:-

-299,274200

- 1,199

- 3,071

201

- 23,877

- 7,094

I '14:- 201

I '14:— 8,269

a-NaphthylamineSulfanilic Acid

BenzidineCroceine Acid

Benzidinel-Naphthol-3: 8-disul-

fonic Acid

BenzidineHAcid

TolidineCroceine Acid

Tolidinel-Naphthol-3: 8-disul-

fonic Acid

Tolidinel-Amino-8-naphthol-

4-sulfonic Acid (2mols)

TolidineHAcid

DianisidineCroceine Acid

Dianisidinel-Amino-8-naphthol-

2: 4-disulfonic Acid

A

D

D

D

D

D

D

D

D

D


Dyes Derived from l-Amino-8-naphthol-4:-sulfonic Acid (continued)


423

425

465

478



Chicago Blue B

Benzo Cyanine 3B

TRISAZO DYEColumbia Black

Green D

Columbia Green


Manufacture

M'lS:— ?

I '14:— 1,001

I '14:— 45,162

I '20:— 7*555


Dianisidinel-Amino-8-naphthol-4-

sulfonic Acid (2 mols)

DianisidinePI Acid

BenzidineSalicylic AcidAniline

BenzidineSalicylic AcidSulfanilic Acid


D

D

D


8-Amino-l-naphthol-4-sulfonic Acid (C. A. nomen)

O H N H 2

FORMATION.—By heating l -naphthylamine-5: 8-disulfonic acid with

75 per cent caustic potash a t about 150°

L I T E R A T U R E . — G e r . Pa t . 75,055


Langc, Zwischenprodukte, #2450

Dye Derived from l-Amino-8-naphthol-5-sulfonic Acid


218


DISAZO D Y ENigrophor BASF



Used and Notes

p-Nitro-anilino2:5-Dichloro-aniline


MF


2-Amino-l-naphthol-4-sulfonic Acid

OH

= Ci0H9NO4S = 239

FORMATION.—By heating 2~nitroso~l~naphthol with 35 per cent sodiumbisulfite solution

LITERATURE.—Schmidt, J. pr. Chem [II], 44, 531 (1891)Thorpe, Die. Chemistry, 3, 639

Dye Derived from 2-Amino-l-naphthol-4-sulfonic Acid


657


OXAZINE DYEAlizarine Green B


Manufacture

I ' 14:—551


1: 2- Naphthoquinone-4-sulfonic Acid


M

2-Amino-3-naphthol-6-sulfonic Acid

Amino-naphthol-sulfonic Acid R

3-Amino-2-naphthol-7-sulfonic Acid ( C A. nomen.)

HO3S

FORMATION.—From Amino-R acid (2-naphthylamine-3: 6-disulfonicacid) by caustic soda fusion at 240°

LITERATURE.—Lange, Zwischenprodukte, #2534Thorpe, Die. Chemistry, 3, 639

Dye Derived from 2-Amino-3-naphthol-6-sulfonic Acid


185


MONOAZO DYEAnthracene Chrome

Black


Manufacture

I '14:—51,577I '20:— 2,339


/3-Naphthol


M



See, J Acid


See, Gamma Acid

3-Amino-2-naphthol-7-sulfonic Acid (C A. nomen.)

See, 2-Amino~3-naphthol-6-sulfonic Acid

5-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)

See, l-Amino-5-naphthol-7-sulfonic Acid


See, J Acid


See, Gamma Acid


See, l-Amino-8~naphthol-5-sulfonic Acid

8-Amino-l-naphthol-5-sulfonic Acid (C. A. nomen.


Amino-naphthol-sulfonic Acid G

See, Gamma Acid

Amino-naphthol-sulfonic Acid J

See, J Acid

Amino-naphthol-sulfonic Acid R

See, 2-Amino-3-naphthol-6-sulfonic Acid

Amino-naphthol-sulfonic Acid S


Amino-naphthol-sulfonic Acid 7

See, Gamraa AcicJ


/>-(2-Amino-4-nitro-anilino)-phenol (C A. nomen.)

See, 2-Amino-4'-hydroxy-4-nitro-diphenylamine

2-Amino-5-nitro-frenzene-sulfonic Acid (C. A. nomen. SO3H = 1)

p-Nitro-aniline-o-sulfonic Acid (NH2 = 1)

4-Nitro-aniline-2-sulfonic Acid (NH2 = 1)

SO3H

O2N

STATISTICS.—Manufactured 1918; amount not disclosed

FORMATION.—2-Chloro-5-nitro~benzene-sulfonic acid (by oleum sulfona-tion of p-chloro-nitro-bcnzene) is heated in an autoclave at 120-140°with alcoholic ammonia


Dyes Derived from 2-Amino-5-nitro-benzene-sulfonic Acid





Used and Notes


132MONOAZO DYES

Lake Red P

133

458

EriochromcPhosphinc R

TRISAZO DYESCarbon Black

? 14:—60,345M ' 1 7 : — ?M ' 1 8 . — ?M ' 1 9 : — ?I '20:— 1,750

I '14:— 1,433

jS-Naphthol

Salicylic Acid

l-Naphthylamine-6-or-7-sulfonicAcid

m-Phenylene-diamineor m-Tolylene-dia-mine or 1: 3-Naph-thylene-diamine-6-sulfonic Acid

CL

ACr

D


4-Amino-3-nitro-benzene-sulfonic Acid (C. A. nomen.)

o-Nitro-anilinc-p-sulfonic Acid

2-Nitro-aniline-4-sulfonic Acid

SO3H

75


FORMATION.—From chloro-benzene-p-sulfonic acid by nitration, fol-lowed by amidation with ammonia


Dye Dsrived from 4-Amino-3-nitro-benzene-sulfonic Acid


148


MONOAZO DYEFast Orange 0


Manufacture

I '14:—1,250M'17:— ?


/3-Naphthol


CL

2-Amino-6-nitro-£-cresol (C. A. nomen. 011=1)

o-Nitro-o-amino-p-cresol

OH

O 2 N / \ N H 2

FORMATION.—The above cresol derivative is obtained by partiallyreducing the 2: 6-dinitro-p-cresol. This latter results either fromthe direct dinitration of p-cresol; or by the dinitration of p-tolui-dine, and subsequent hydrolysis with alkali

LITERATURE.—Ber. 15,1859


Dye Derived from 2-Amino-6-nitro-£-cresol (OH=1)


85


MONOAZO DYEOmega Chrome

Black PV



Used and Notes

Plieny 1-1 -naph thy 1-amine-S-sulfonic Acid


ACr

l-Amino-8-nitro-2-naphthol-4-sulfonic AcidNitro-1:2:4 Acid

O2N NH2

C 0 O H =SO3H

C10H8N2O6S —284

FORMATION.—From l-amino-2-naphthol-4-sulfonic Acid by nitration


Dyes Derived from l-Amino-8-nitro-2-naphthol-4-sulfonic Acid


183

184


MONAZO DYESEriochrome Black T

Eriochrome Black A


Manufacture

I '14:—129,550M'18:— ?M'19:— ?I '20:—2,624M'20:— ?

I '14:— 96,570M'17:— ?M'18:— ?M'19:—686,710I '20:— 14,262M'20:— ?


a-Naphthol

0-Naphthol


ACr

ACr

2-Amino-6-nitro-l-jphenol-4-sulfonic Acid (C. A. nomen. OH--

6-Nitro-2-amino-phenol-4-sulfonic Acid2-Nitro-6-amino-phenol-4-sulfonic Acid

-1)


OH

O 2 N / \ N H 2

SO3H

FORMATION.—From phenol by sulfonation, dinitration and partialreduction with sodium sulfi.de


Lango, Zwischcnproduktc, #1130

Dye Derived from 2-Amino-6-nitro-phenol-4-sulfonic Acid


159

Ordinary Name a?idClass of Dye

MONOAZO DYEAcid Alizarin

Black R


Manufacture

I '14:—16,800M'19:— ?I J20:— 439M'20:— ?


jS-Naphthol


M

6-Amino-5-nitroso-2-7iaphthalene-sulfonic Acid (C. A. nomen.)

See, l-Nitroso-2-naphthylamine-6-sulfonic Acid

m-Amino-phenol

OH

=CeH7NO =

FORMATION.—By the fusion of Metanilic Acid (3-amino-benzene-sulfonic acid) with caustic soda at about 280-290°

LITERATURE.—Ber. 32,2112-2124

Lange, Zwischenprodukte, #582-584


Dyes Derived from m-Amino-phenol


90

923


MONOAZO DYEChrome Brown P

ANILINE BLACKGROUP

Fuscamine


Manufacture

I '14:— 54,005M '19:— ?

I '20:— 1,600(M'20:—168,459)


Picramic Acid

?n-Ammo-phenol(x mols)

[Oxidation on hair]


M

Fur

jp-Amino-phenol

OH

NH2

STATISTICS.—Imported '14:— 10,631 lbs.Manufactured '17:— ?Manufactured '18:—113,428 lbs.Manufactured '19:—128,627 lbs.Manufactured '20:— 41,474 lbs.

FORMATION.—Phenol is treated with sodium nitrite in the cold and theresulting p-nitroso-phenol is reduced with sodium sulfide

LITERATURE.—Cain, Intermediate Products (2d Ed.), 117Lange, Zwischenprodukte, #585-589

Dyes Derived from ^-Amino-phenol


14

84


STILBENE DYEDiphenyl Chrysoine

MONOAZO DYEAzo Chromine


Manufacture

I '14:— 9,898


p-Nitro-toluene-o-sul-f onic Acid (2 mols)

Pyrogallol


D

M


Dyes Derived from j&-Amino-phenol (continued)

79





Used and Notes


709

717

724

725

726

733

734

923

SULFUR DYESItalian Green

Vidal Black I

Immedial Black

Immedial DarkBrown A

Immedial Brown B

Pyrogene Direct BluePyrogcne Blue

Immedial Indonc

Pyrogene Yellow

ANILINE BLACK

GROUP

Ursol P

'14:— 298M'18:— ?I '20:— 2,603

I 14:— 7,495

I '14:— 54,696M'18:— ?

I '14:— 23,887M'18:— ?

I '14:— 10,934I '20:— 2,498

I '14:— 4,236

I '14:— 18,515I '20:— 2,701

I '14:— 54,005M'19:— ?I '20:— 1,600M'20:—168,459

[Sulfur, etc.]

[Na2S+S]

l-Chloro-2: 4-dinitro-benzene

[S+Na2S]


[NaOH; S+Na2S]


[Alcohol; S+Na2S]

o-Toluidine[S+Na2S]

p-Nitro-benzyl chloride

p-Amino-phenol(x mols)

[Oxidation]

S

S

Fur

4-Amino-l-i>henol-2:6-disulfonic Acid (011=1) (C. A. nomen.)

p-Amino-phcnol-a-disulfonic AcidOH

H O 3 S | / \ S O 3 H _ C J

N H 2

Note.—Position of the sulfonic groups not fully established.


FORMATION.—Nitroso-dimethyl-aniline hydrochloride or nitroso-phenolis introduced into a solution of sodium bisulfite, and warmed toeffect solution. Then concentrated hydrochloric is added and theliquor boiled for two hours, using direct steam

LITERATURE.—Gcr. Pat . 65,236Boil. spl. I I , 492Lange, Zwischenprodukte, #1154

Dye Derived from 4-Amino-l-phenol-2: 6-disulfonic Acid


15S


MONOAZO DYEChrome Brown

RR


Manufacture

I '14:—7,241M'17:— ?I '20:—2,183


Pyrogallol


M

/j-Amino-phenol Ethyl Ether

See, p-Phenetidine

2-Amino-l-phenol-4-sulfonic Acid (C. A. nomen. OH=1)

o-Amino-phenol-p-sulfonic Acid

o n

SO3H

STATISTICS.—

= C 6 H 7 NO 4 S=189

Manufactured '18:— ?Manufactured 19:— ?Manufactured '20:— ?

FORMATION.—Chloro-benzene is sulfonated and nitrated. The chloro-body is then hydrolyzed to the phenol by boiling with caustic soda,and finally reduced to 2-amino-phenol-4-sulfonic acid by means ofsodium sulfide



Dyes Derived from 2-Amino-l-phenol-4-sulfonic Acid

Schultz

XV VtlWjZrTfor Dye

154

155

156

157


MONOAZO DYESAcid Alizarin

Brown BPalatine Chrome

Brown W

Acid AlizarinGarnet R

Acid AlizarinViolet N

Palatine ChromeViolet

Diamond Black PV

Statistics of

1 TripOTl aTl/ClManufacture

I '14:— 18,264M'17:— ?M'18:— ?M'19:— ?I '20:— 845M'20:— ?

I '20:— 201M'20:— ?

I '14:— 1,199M'19:— ?M'20:— ?

I '14:—285,074M'20:— ?


m-Phcnylene-diamine

Hcsorcinol

jS-Naphthol

1:5-Dihydroxy-naph-thalene


M

M

ACr

M

3-Amino-l-jf>henol-4-sulfonic Acid (C. A. nomen. OH=1.)

Amino-phenol-sulfonic Acid III

FORMATION.—^By fusion with caustic soda of the aniline-disulfonic acidprepared by sulfonation of mctanilic acid.

Note.—^Amino-phenol-sulfonic acid I I I is not 5-amino-phenol-2-sulfonic acid




Dyes Derived from 3-Amino-l-phenol-4-sulfonic Acid


339

481


DISAZO DYEBrilliant Orange G

TEISAZO DYEAzo Corinth


Manufacture

I '14:—6,321M'17:— ?


BenzidineSalicylic Acid

TolidineNaphthionic AcidResorcinol


D

D

o-Amino-phenol-^-sulfonic AcidSee, 2~Amino-l-phenol-4-sulfonic Acid

Amino-phenol-sulfonic Acid IIISee, 3~Amino-l-phenol~4-sulfonic Acid (OH = 1)

Amino-phenol-sulfonic Acid IV3-Amino-l-phenol-6-sulfonic Acid (not considered herein)

Amino-phenol-sulfonic Acid V3-Amino-l-phenol-5-sulfonic Acid (not considered herein)

/>-(/>-Amino-phenyl-azo)-&enzene-sulfonic AcidSee, Amino-azo-benzene-sulfonic Acid

l-(/>-Amino-phenyl)-5-methyl-benzothiazole (C ^L nomen.)

See, Dehydro-thio-p-toluidine

IV-Amino-2-phenyl-5-methyl-thiazolSee, Dehydro-thio-p-toluidine

^-Amino-phenyl-toluthiazoleSee, Dehydro-thio-p4oluidine

(m-Amino-phenyl) -trimethyl-ammonium Chloride

Trimethyl-m-amino-phenyl-ammonium chloride

C1N(CH3)3

JNH2 ~ = 186.5


FORMATION.—m-Nitro-aniline by heating in methanol (methyl alcohol)solution, with hydrochloric acid is transformed into m-nitro-phenyl-trimethyl-ammonium chloride (and m-nitro-dimethyl-aniline). The7?2-nitro-phenyl-trimethyl-ammonium chloride is dissolved in waterand reduced with zinc dust and hydrochloric acid

LITERATURE.—Lange, Zwischenprodukte, #549,564Green, Organic Coloring Matters (1908), 12

Dyes Derived from (m-Amino-phenyl)-trimethyl-ammonium Chloride


60

222

240

435


MONOAZO DYEAzo Phosphine GO

DISAZO DYESJanus Yellow G

Janus Red B



Manufacture

I '14:— 50

I '14:—23250I '20:— 75S

I ' 1 4 : - 250I'20:— 176


Rcsorcinol

Resorcinolm-Nitro-anilinc

m-Toluidinc0-Naphthol

a-Naphthylamineor m-Toluidine

Anilinem-Phcnylcne-diamine


B

B

B

B

Amino-R Acid

2-Naphthylaminc-3: 6-disulfonic Acid

/3-Naphthylamine-disulfonic Acid R

j8-Naphthylamino-a-disulfonic Acid

3-Amino-2: 7-^aphthalcne-disulfonic Acid (C. A nomen.)

HO3SNH,SO3H

FORMATION.—By heating R salt with ammonia in an autoclave, inpresence of ammonium bisulfite

LITERATURE.—Cain, Intermediate Products (2d Ed.), 207Lange, Zwischenprodukte, #2594Thorpe, Die. Chemistry, 3, 604


Dyes Derived from Amino-R Acid


120

314

315

316

332

358

359

369

370

373


MONOAZO DYESalmon Red

DISAZO DYESPyramine Orange 2R

Congo Orange R

Brilliant Congo G

Dianil Garnet BBenzo Fast Red

Brilliant DianolRedR

Diphenyl Red

Trypan Red

Brilliant Purpurin R

Brilliant Congo R

Congo Orange R


Manufacture

M'20:— ?

I '14:— 2,7S9

I '14:— 1,623I '20:— 75

I '14:— 5,985I '20:— 3,799

I '14:—14,305I '20:— 3,704

I '14:— 8,051

I '14.-19,133I '20:—11,129

I '14:— 7,027I '20:— 254


Dchydro-thio-m-xyli-dine

BenzidineNitro-m-phcnylene-

diamine

BenzidinePhenol[Etliylation]

BenzidineBroenner's Acid

BenzidineGamma Acid

Dichloro-benzidineAmino-R Acid (2 mols)

Benzidine-sulfonic AcidAmino-R Acid (2 mols)

TolidineNaphthionic Acid

TolidineBroenner's Acid

TolidinePhenol[Etliylation]


D

D

D

D

D

D

Medi-cinal

D

D

D

6-Amino-salicylic AcidCOOH


STATISTICS.—Imported 14:— 9,188 lbs.

Manufactured 17:— ?Manufactured '18:— ?Manufactured 19:—37,769 lbs.Manufactured '20:— ?

FORMATION.—(1) From the corresponding nitro-salicylic acid by re-duction. (2) By reducing the azo-dye, benzene-azo-salicylic acid



275

276

277

492

550

Dyes Derived


DISAZO DYESDiamond Black F

Diamond Green B

Anthracene AcidBlack DSF

TJBTRAKJSAZO DYEAnthracene Acid

Brown B

TRIPHENYL-METHANEDYE

Chrome Bordeaux

from 5-Amino-saIicylic Acid


Manufacture

I 14:—462,306M17:— ?M18:— ?M 19:—222,938I '20:— 2,226M'20:— ?

I 14:— S;622M18:— ?I '20:— 4,016

I 14:— 17,793

Other Intermediates"Used and Notes

a-NaphthylamineNevile-Winther Acid or

1 - n aph thol-5-sulf onicAcid

a-Naphthylamine1:8-Dihydroxy-naph-

thalene- 4- sulfonicAcid

l-Naphthykmine-6-and 7-sulfonic Acids,etc.

l-Naphthylamine-6-sul-fonic Acid (2 mols)

ra-Phenylene-diamineAmino- salicylic Acid

(2 mols)

Hydrol[Oxidation]


ACr

ACr

M

MACr

M

Amino-Schaefler's Acid

See, Brocnncr's Acid


l-(4-Amino-?-sulfo-phenyl)-5-methyl-6enzothiazole (C. A. nomen.)

See, Dehydro-thio-p-toluidine-sulfonic Acid

4-Amino-4:5-sultam-l:3: 6-naphthalene-trisulfonic Acid (C. A.nomen.)

See, 1: 8-Naphthasultam-2: 4-disulfonic Acid

m-Amino-tetramethyl-/>': ^"-diamino-triphenyl-methaneN': N': N": iV"-Tetramethyl-m: p': p'^methenyl-trisaniline (C.

A. nomen.)

= C2aH27N3 = 345

N H 2

FORMATION.—m-Nitro-benzaldehyde and dimethyl-aniline are con-densed in the presence of acids or zinc chloride to m-nitro-tetra-methyl~p: p-diamino-triphenyl-methane, which by reduction givesthe m-amino-derivative

LITERATURE.—Schultz, Chcmie Steinkohlenteers (3 aufl.), 1, 115, 116.

Dye Derived from m-Amino-tetramethyl-^': ^''-diamino-triphenyl-methane

SchultzNumberfor D'ye

510



Azo Green



Used and Notes

Salicylic Acid


M

4-Amino-m-foluene-sulfonic Acid (C. A. nomen. SOzH=l)

o-Toluidine-m-sulfonic Acid (CH3 = 1)

SO,H

JCH3


FORMATION.—From o-toluidine acid sulfate by heating in an oven


Dyes Derived from 4-Amino-m-toluene-sulfonic Acid (SO3H=1)


24

151


PYRAZOLONE DYEPigment Fast

Yellow R

MONOAZO DYEOrange RO, T


Manufacture

I '14:—90,747M'17:— ?M'19:— ?I '20:— 20M'20:— ?


3-Methyl-l-phenyl-5-pyrazolone


CL

A

6-Amino-o-foluene-sulfonic Acid (C A. nomen. SOnH=l)p-Toluidinc-o-sulfonic Acid (CH3 = 1)

SO3H

H2N = C7H9NO3S:=187

STATISTICS.—Manufactured ;20:— ?

FORMATION.—From p-toluidine sulfate by heating in oven (bakingprocess)

LITERATURE.—Green, Organic Coloring Matters (1908), 22Langc, Zwischenproduktc, //839,237

Dyes Derived from 5-Amino-o-toluene-sulfonic Acid (SOzH

SchtdtzNumberfor Dye

150

152


MONOAZO DYESFast Yellow N

Lithol Rubiue BPermanent Red 413


Manufacture

I '14:—101,395

I '20:— 2,983M'20:— ?


Diphcnylamine

3~Hydroxy-2-naphthoicAcid

= 1)Dye

Appli-cationClass

A

CL

'< DYES CLASSIFIED BY INTERMEDIATES

Dyes Derived from 5-Amino-o-toluene-sulfonic Acid (continued)


S52

SG5



Alizarin DirectViolet R

Alizarin DirectGreen G


Manufacture

I '20:— 251

I '14:— 2,000I '20:— 31,851M'20:— ?


Quinizarin

Quinizarinp-Toluidine-3-sulfonic

Acid (2 mols)


A

ACr

3'-Amino-(/)-foluene-sulfo)-/)-toluide (C. A. nomen.)

See, iV-(3~Amino-4-mcthyl~phenyl)-p-toluene-sulfamide

4-(4-Amino-7n-tolyl-azo)-m-^oluene-sulfonic Acid (C. A. nomen.)

See, o-Amino-azo-toluene-sulfonic Acid

l-(4-Amino-m-tolyl)-3: 5-dimethyl-&enzothiazole (C A. nomen.)

See, Dchydro-thio-m-xylidine

l-(6-Amino-m-tolyl)-3: 5-dimethyl-&enzothiazole (C. A. nomen.)

See, iso-Dehydro-thiO'-m-xylidine

l-Amino-4: 5: 8-trihydroxy-anthraquinone8-Amino-l: 4: 5-trihydroxy-anthraquinone (C A. nomen.)

HO CO

FOUMATION.—4: 8-Dinitro-anthrarufm (p-dinitro-anthrarufin) is heatedwith sulfuric and boric acids at temperature of water bath, formingl-nitro-4: 5: 8-trihydroxy-anthraquinone. (At higher tempera-tures the 1: 4: 5: 8-tetrahydroxy-anthraquinone is formed.) Byreduction of the 1-nitro-dcrivative, the desired ammo-derivativeresults.


LITERATURE.—Ger. Pat. 125,579; FrdL 6, 335; Chem. Zen. 1901, I I ,1189

Dye Derived from l-Amino-4: 5: 8-trihydroxy-anthraquinone

tichullzNumberfor Dye

823

Ordinary Name andClans of Dye

ANTHRAQUINONE ANDALUND DYJUS

Algol Violet B


Manufacture

I '20:—G9


Benzoyl chloride


V

Andresen's Acid

See, l-Naphthol-3: 8-disulfonic AcidThin trivial 7iame also applied to:—

2-Naphthylaminc-4: 7-disulfonic Acid

Anhydro-formaldehyde-aniline1:3: 5-Triphenyl-hcxahydro-$-friazme (C. A. nomen.)Formaniline

=C2 iH2 iN3 —315II2C CII2

II6Ce. N N . CIIs

Note.—Some of the older books give the formula as CeH^N

STATISTICS.- -Manufactured 1920, but in an undisclosed amount.

FORMATION. By condensation of aniline and formaldehyde

LITERATURE. -Beilstein, Organisehe Ohomio (3d auf.), 2, spl. 233

Cain and Thorpe, Synthetic Dyestuffs, 90

Dye Derived from Anhydro-formaldehyde-aniline

SchulizNumberfor Dye

511

, Ordinary N(Jtnr andClaxx of Dye

DYEPanifurliMncPunimngeuta

titatifitics ofImport and

Manufacture

M7U:--()5,O2GM'ltS:- ?M;M):— ?M72()-- ?


AnilineAniline hydro-chloride[Nitro-benzeue and

ferric chloride)


B


Anhydro-formaldehyde-o-toluidine

N:CH2

FORMATION.—By condensation of o-toluidine and formaldehyde


513

Dyes Derived from



New Fuchsine 0

Anhydro-formaldehyde-o-toluidine


Manufacture

I '14:—300M'18:— ?M'19:— ?M720:— ?


o-Toluidine0-Toluidine

hydrochloride[o-Nitro-toluene and

ferrous chloridel

DyAppcaticCla

B

STATISTICS.—Imported '14:— 4,553,028 lbs.Manufactured '17:—30,149,397 lbs.Manufactured '18:—25,867,488 lbs.Manufactured '19:—25,792,095 lbs.Manufactured '20:—41,259,142 lbs.

FORMATION.—Benzene is nitrated to nitro-benzene with mixed nitand sulfuric acid. The nitro-benzene is reduced to aniline wiiron turnings and hydrochloric acid





12

19

20

31

32

33

Dyes


STILBENE DYEDiphcnyl

Citronine G

PYRAZOLONE DYESFlavazine LFast Light Yellow

Flavazine S

MONOAZO DYESAmino-azo-bcnzcneSpirit Yellow

Butter YellowOil Yellow

Chrysoidine

Derived from -


Manufacture

I '14:— 3S,908I '20:— 9,327

I '14:— 81,375I '20:— 1,500

M'17:— ?M'18:— 52,283M'19:— ?M '20:— ?

I '14:— 4,062M'17:— 33,180M'18:— 27,669M'19:— 31,156M'20:— 74,182

I '14:— 63,303M'17:—195,756M'18:—376,495M'19:—314,581M'20:—585,648

Aniline


Aniline (2 mols)Dinitro-dibenzyl-

disulfonic Acidor

Dinitro-distilbene-disulfonic Acid

orp-Nitro-toluene-o-sul-

fonic Acid (2 mols)

3-Methyl-l-p-sulfo-phenyl-5-pyrazolone

orPhenyl-hydrazine-p-

sulfonic AcidAceto-acetic Ethyl

Ester

l-p-Sulfophenyl-5-pyrazolone-3-car-boxylic Acid


sulf onic AcidOxal-acetic Ester

Aniline (2 mols)

Dimethyl-aniline

w-Phenylene-diamine


D

A

A

ss

ss

B

Dyes Derived from Aniline {continued)





Used and Notes



Chrysoidine R

Sudan G

Sudan IOil Orange

Ponceau 4 GBCroceine Orange

Orange G

Ponceau G

Chromotrope 2R

Fast AcidFuchsine B

I '14:—111,006M'17:— 58,115M'lS:—137,035M'19:--220,542M'20:—186,793I J20:— 1,102

m-Tolylene-diamine B

I '14:-M'17:-M'18:-M'19:-M'20:-

t:— 798

- 4,554- 32,45,- 29,670- 75,868-116,624

I '14:— 13,046M'17M ' l SM'19M'20

30,82417,27496,573

I '14:— 48,456M'17M'18M'19M'2OI '20

M'17:—M'19:—

-120,874- 100

I '14:M'17:M'18:M'19:M'20:

5,000???

?

R e s o r c i n o l

0 - N a p h t h o l

s s

ss

Scliaeffer's Acid

GAcid

RAcid

Chromotropic Acid

M'18:— ?M'19:— 26,699M'20:— 30,678

HAcid


Dyes Derived from Aniline (continued)





Used and Notes


42

45

5<S

124

125

126

127

MONOAZO DYES

(continued)Amiclo Naphtliol

lied G

Tolanc Red B, G

Azo Archil R

Brilliant Lake Red R

Alizarin Yellow R

I '14:—M'17:—M'18:—M'19:—I '20:—

3,500

2,028

Acctyl-II Acid A

Diazine Green S

Diazinc Black

Indoinc Blue RUnion Blue R

Methyl Indonc B

M '20:—132,637

I '14:— 31,674I '20:— 1,071

I '14:— 97,057M'17:—215,468M'IS:—385,910M'19:—130,424I '20:— 860M'20:— 83,334

I '14:— 1,340

K Acid

2 R Acid

3~Hydroxy-2-naphthoicAcid

Salicylic Acid[Nitration]

A

A

CL

M

I '14:—I '20:—

2,630701

I '14:— 15,353M'17:— ?M'18:— ?

M'17:— ?

0-Toluidinep-Tolylcnc-diaminc[or Safraninc]Dimethyl-aniline

o-Toluidincp-Tolylcnc-diamine[or Safraninc]Phenol

o-Toluidinep-Tolylcne-diaminc[or Safraninc]0-Naphthol

o-Toluidinep-Tolylene-diamine[or Safraninc][" Amino-naphtliols "]

B

B

B

B







Used and Notes

128

182

215

216

217

219

241

242

270


Janus Gray B

Fast Sulf onViolet 5BS

Brilliant SulfonRedB

DISAZO DYESBlue Black N

Domingo BlueBlack B

Naphthol Blue Black

I '14:-I '20:-

4,8714,740

I '14:-- 2,653

Chrome PatentGreen N

Neutral Gray G

Sulfone Black G

Brilliant Croceine 9B

I '14:—431,027M'17:—620,218M'18:—

1,158,309M'19:—

1,877,860I '20:— 340M'20:—

2,608,864

o-Toluidinep-Tolylene-diamine[or Safranine], etc.

HAcidBenzene- (or Toluene-)

sulfonyl Chloride

K Acidp-Nitro-aniline


p-Nitro-aniline

HAcidp-Nitro-aniline

I '14:-M'19:-I '20:-

M'20:-

2,546

3,472

KAcidPicramic Acid

a-NaphthylamineGamma Acid

l-Naphthylamine-6-cm<27-sulfonic Acid

1:8-Dihydroxy-naphth-alene-4-sulfonic Acid

Amino-G AcidR and G Acids




279

435

444

445

462

463

464

465



Benzo Fast Scarlet

TRISAZO DYESJanus Brown B

Crumpsall DirectFast Brown B

Crumpsall DirectFast Brown 0

Erie DirectBlack GX

Direct DeepBlack E, EW

Erie DirectBlack KX

Cotton Black E

Erie DirectGreen ET

Columbia BlackGreen D


Manufacture

I '14:— 36,674M'19:— ?I '20:— 24,153

I '14:—1,246,536

M'17:— ?M'18:— ?M'19:—

7,250,007M'20:—

7,736,994

I '14:—248,567M'19:— ?M'20:—

2,050,741

M'17:— ?M'18:— ?M'19:— 69,700M'20:— ?


J AcidPhosgene

Trimethyl-m-amino-phcnyl-ammoniumchloride or p-Amino-benzyl-dicthylamine

ct-Naphthylamine or?w-Toluidine

m-Phenylenc-diamine

BenzidineSalicylic AcidGamma Acid

BenzidineSalicylic AcidPhcnyl-gamma Acid

BenzidineH Acidm-Phcnylenc-diamine

BenzidineH Acidm-Tolylene-diamino

BenzidineH AcidPhenol

BenzidineSalicylic Acidl-Amino-8-Naphthol-

4-sulf onic Acid


D

B

D

D

D

D

D

D



SchultNumbeforDy

482

511

512

514


TRISAZO DYES(continued)

Alizarin Yellow FS

TRIPHENYL-METHANEDYES

ParafuchsineParamagenta

FuchsineMagenta

Red Violet 5R


Manufacture

I '14:— 65,026M'18:— ?M'19:— ?M'20:— ?

I '14:— 87,102M '17:— 17,739M'18:—71,675M '19.-155,830I '20:— 189M'20.-284,285

I '14— 331I '20— 750


o-Toluidine andp-Toluidine

[or Fuchsine]Salicylic Acid (3 mols)

p-ToluidincAniline (2 mols)[Iron and nitro-benzcne

or arsenic Acid]or

p-Nitro-benzaldehydeAniline sulfate (2 mols)[Zinc chloride; ferrous

chloride]or

p: p'Diamino-diphenyl-methane or anhydro-formaldehyde-aniline

[Nitro-benzene and fer-ric chloride]

p-Toluidineo-Toluidine[Nitro-benzene, iron

and zinc chloride orarsenic acid]

[Magenta methylatedor ethylated]

oro-Toluidinep-Toluidine[Nitro-benzene, iron

and zinc chloride orarsenic acid]

[Methylation or ethyl-ation]


M

B

B

B







Used and Notes


520

521

TKIPHENYL-METHANE^DYES (continued)

Light Blue SuperfineSpirit Soluble

Diphenylamine Blue

Spirit BlueBlue

I '14:— 2,149

524

525

Fuchsine SAcid Magenta

Red Violet 5RS

526 Acid Violet 4RS

M'17:M'lS:M'19:I '20:M'20:

50,5639

9

:— 723

I '14:-I '20:-M720:-

19,098• 524

535 Methyl Alkali Blue I '14M'18M'19I '20

:— 273

:— 29

[Para-rosanilinc tri-phcnylatcd]

orAniline (5 mols)p-Toluidine[Bcnzoic Acid]

[Magenta phenylated]or

Aniline (2-4 mols)o-Toluidinep-Toluidine[Bcnzoic Acid]

[Magenta sulfonated]or

o-Toluidincp-Toluidine[sulfonation]

[Magenta cthylatcd andsulfonated]

oro-Toluidinc??-Toluidine[Ethylation and

sulfonation]

[Magenta dimethylatcd,trisulfonated]

oro-Toluidinep-Toluidine[Dimcthylation, Tri-

sulfonation]

[Triphenyl-p-rosanilinesulfonated]

orp-ToluidineAniline (5 mols)[Sulfonation]

ss

A




536

537

538

539


TKIPHENYL-METHANEDYES

(continued)Alkali Blue

Methyl Blue for SilkMarine Blue B

Methyl BlueCotton Blue

Water BlueSoluble Blue


Manufacture

I '14:—286,751M'17:— ?M'18:— 43,184M'19:— 77,796I '20:— 6,778M'20:— 74,253

I '14:— 34,867M '18:— ?M'19:— ?I '20:— 2,395M'20:— ?

I '14:— 50,255

I '14:— 91,152M '18:— ?M'19:— 16,315I '20:— 1,387M'20:— 98,770


[Spirit BlueorTriphenyl-p-rosaniline+di-phenyl-rosanilinesulfonated]

oro-Toluidinep-ToluidineAniline (3-5 mols)[Sulfonation]

[Triphenyl-p-rosanilinemono- and di-sulfo-nated]

oro-Toluidinep-ToluidineAniline (4 mols)[Sulfonation]

[Triphenyl-p-rosanilinedi- and tri-sulfonatcd]

oro-Toluidinc2)-ToluidineAniline (4 mols)[Di-and Tri-sulfonation]

[Spirit Blue or Tri-ph enyl-p-rosanilinc+diphenyl-rosanilincdi- and tri-sulf onatcd]

oro-Toluidinep-ToluidineAniline (3-5 mols)[Di- and tri-sulfonation]


A

A

B

A


Dyes Derived from Aniline {continued)





Used and Notes


540

TRIPHENYL-ME THANEDYES {continued)

Pacific Blue

541 Brilliant DianilBlue 6G

572XANTHONE DYES

Rhodaminc G

580 Fast Acid Violet B

606ACMDINE DYE

Phosphine

'14:-'20:-

2,648517

I '14:-M '19:-I '20:-

20,688

2,907

I '14:—168,175M'17M'18M'19I '20M'20

14,64819,259

[p-Rosanilinc+diamino-diphcnyl-methaneand sulfonation]

oro-Toluidinep-ToluidineDiamino-diphenyl-

methane[Sulfonation]

[/3-Naphthyl-rosanilinesulfonatcd]

or/3-Naphthylamine

(3 mols)o-Toluidinep-Toluidine[Disulfonation]

[Rhodamine B heatedwith aniline to re-move one C2H5 group]

orPhthalic anhydrideDiethyl-m-amino-

phenol (2 mols)

[Dichloro-fluoresceineand aniline or p-tol-

uidine; sulfonation]or

Aniline (2 mols)Phthalic AnhydrideResorcinol[PC1B; Sulfonation]

[Magenta by-product]or

p-Toluidinco-Toluidine

D

B

B







Used and Notes


622OXAZINE DYES

Delphine Blue B M'17:— ?M'18:— ?M'19:— 43,827I '20:— 29,643M'20:— 76,719

630

640

646

Cyanazurine

Modern Azurine DH

Coreine AR

672AZINE DYES

Azo Carmine G I '14:— 17,500M'17:-M'18:-M'19:-I '20:-

M'20:• :— 196

673 Azo Carmine B I '20:— 549

Nitroso-dimethyl-aniline

Gallic Acid[Sulfonation]

or[Gallocyanine treated

with aniline; Sulfo-nation]


Gallamide[Reduction]

Gallic Acid MethylEster


GallamideNitroso-diethyl-aniline

or Diethyl-amino-azo- benzene

[Sulfonation]or

[Coreine RR; Sulfona-tion]

Aniline (3 mols)a-Naphthylamine[Disulfonation]

Aniline (3 mols)a-Naphthylamine[Trisulfonation]

M

M

M

M



101



AZINE DYES(continued)

Rosinduline 2G

Rosinduline G

Safranine

MethyleneViolet BN

Nigramino

Safranine MN

Brilliant RhodulineRed

Amethyst Violet

I '14:— 59,921M'17:— ?M ' 1 8 :M'19:-I '20:-

M'20:-


Manufacture

I J20:— 201

I '20:— 40

-106,591-131,042- 386-149,629

I '14:-M'17:-I '20:-

1,521?

33

I '14:-M'lS:-M'19:-M '20:

198???


Aniline (3 mols)a-Naphthylamine[Trisulfonation; heated

to 160°]

Aniline (2 mols)l-Mtroso-2-naphthyl-

amine-6-sulfonic Acid

p-Tolylcne-diamineo-Toluidine

Aniline (2 mols)Dimethyl-p-phenylene-

diamine[Oxidation]


Dimethyl-p-phcnylene-diamine

o- or p-Toluidine[Oxidation]

N3-Ethyl-4-m-tolylcne-diamine

Methyl-o-toluidine

D icthyl-p-ph cny lcnc-diamine

Diethyl-aniline[Oxidation]



Schultz-Numberfor Dye




Used and Notes


687

693


Eosolane O

RosolaneMauve

Milling Bluo

696

697

698

Indamine Blue

Induline, SpiritSoluble

Nigrosine, SpiritSoluble

699 Induline, WaterSoluble

I '20:— 1,083

I '14:-I '20:

7963

I '14:— 3,082

'14:— 25,342M'17:— ?M'18:— 8,589M'19:—436,201M'20:—140,400

I '14:—186,595M'17:—302,706M'18:—314,151M'19:—346,167M'20:—919,242

I '14:— 29,177M'17:—183,739M ;18:— 91,724M '19:—130,704I '20:— 500

M'20.-168,048

p-Amino-diphcnyl- Bamine

o-Toluidine[Oxidation]

Toluidines (3 mols) B[Oxidation]

Aniline (3 mols) Ma-Naphthylamino

(2 mols)[Sulfonation]

orAniline (2 mols)Phenyl-a-naphthyl-

amine (2 mols)Phenol[Sulfonation]

Aniline (excess) BAmino-azo-benzcne

Aniline (excess) ssAmino-azo-benzcne

Aniline (excess)Nitro-benzene[Iron]

orAniline (excess)Nitro-phcnol

Aniline (excess)Amino-azo-benzcne[Sulfonation]


Dyes Derived from. Aniline (continued)

103


700

702

719

729

851

857


AZINE DYES

(continued)Nigrosine, Water

Soluble

Para Blue

SULFUR DYESThional Black

Kryogcnc PureBlueE


Alizarin DirectBlueB

Erweco AlizarinAcid Blue R


Manufacture

I '14:—398,112M'17:—

1,968,458M'18:—

1,191,343M'19:—

1,660,149I '20:— 501M'20:—

2,743,021

I '14:—• 16,865

I '14:-- 10,201I '20:— 2,982


Aniline (excess)Nitrobenzene[Iron; Sulfonation]

orAniline (excess)Nitro-phenol[Sulfonation]

Aniline (3-4 mols)o-Toluidinep-Toluidincp-Phenylcne-diaminc

or[Spirit Blue and p-

Phcnylcno-diamino]

p- (o- or m-)Nitro-ani-

linco-Nitro-phcnol (2 mols)[Na,S+S]

Aniline (2 mols)Dimcthyl-p-phenylenc-

diamine[Na«S+S]

or[Mctliylcnc Violet;

S, Na2S]

1:5- (and 1:8-) Amino-anthraquinonc-sul-fonic Acid

[Dibromination, Sulfo-nation]

Dinitro-anthraflavin-disulfonic Acid

Aniline (2 mols)[Sulfonation]


A

B

S

s

A

ACr







Used and Notes


861

862

864

874

876


(continued)Anthraquinone

Blue SR


AnthraquinoneGreen GX

INDIGO GROUP

DYESIndigo

Indigo MLBIndigo White

:— 917

I '14:— 54,706I '20:— 28,802

I '14:I '20:

1,7092,531

I '14:—8,507,359

M '17:—274,771M ' l S : —

3,083,888M>19:—

8,863,824I '20:—520,347

M'20:—18,178,231

Aniline (2 mols)Tetrabromo-1: 5-di-

amino-anthraquinone[Sulfonation]

Purpurin [or throughAlizarin, or 2-Anthra-quinone-sulfonic acid]

[Sulfonation]

1-Nitro-anthraquinone-6-sulfonic Acid

[Halogenation]p-Toluidine

Aniline (2 mols)[Chloro-acetic, Soda-

mide][or CS2, KCN, etc.]

Aniline (2 mols)[Chloro-acetic, Soda-

mide, Reduction][or CSs, KCN, etc.,

Reduction][or Indigo, Reduction]

ACr

M

ACr

V



105


877

878

879

880

881

882

883

884

885


INDIGO GROUP DYES(continued)

Indigotine

Indigotine P

Brom IndigoRathjen

Indigo MLB/RR

Helindone Blue BBIndigo RB

Dianthrene Blue 2BBromo IndigoCiba Blue 2B

Indigo MLB/5BCiba Blue G

Indigo MLB/6B'Indigo KG

Brilliant IndigoBASF/2B

Brilliant IndigoBASF/B

IM

M

M

IM

IM

IMM

IMI

II

II

M

I

II


'14'17

'18

'19

:— 19,329:—1,876,787

:—1,434,703

:—1,699,670

'20:— 5,512'20

'14'20

'14'17'20

'14'19'20

'14'20

'14'20'20

'14

'14'20

:—1,395,000

:— 53,610. ?

:— 6,856:— 14,100:— ?

:— 16,880:— ?:— 35,857

:— 1,356:— 1,008

:— 3,191:— 4,130:— ?

:•— 4,518

:— 8,175:— 3,503


Aniline (2 mo Is) etc.[or Indigo, Sulfonation]

Aniline (2 mols), etc.[or Indigo, Sulfonation]

Aniline (2 mols), etc.[or Iodigo, Bromination]

Aniline (2 mols), etc.[or Indigo, Bromination

Aniline (2 mols), etc.[or Indigo, Bromination'



Aniline (2 mols), etc.[or Indigo, Chlorination,

Bromination]

Aniline (2 mols), etc.ror Indigo, Chlorination]


A

A

V

V

V

V

V

V

V




SS6

889

890

922


INDIGO GKOUP DYES(continued)

Brilliant IndigoBASF/G

Indigo Yellow 3G

Ciba Yellow G

ANILINE BLACKGROUP

Aniline Black


Manufacture

I '14:-- 12,057

I '14:—- 48

I '14:— 1,470M'19:— ?M'20:— ?


Aniline (2 mols), etc.[or Indigo, Chlorination,

Bromination]

Aniline (2 mols), etc.Benzoyl chloride[or Indigo, Benzoyl

chloride]

Aniline (2 mols), etc.Benzoyl Chloride[Bromination][or Indigo Yellow 3G,

Bromination]

Aniline (x mols)[Oxidation on fiber]


V

V

V

MF

Aniline-2: 4-disulfonic AcidSee} 4-Amino-m-benzene-disulfonic Acid

Aniline-2: 5-disulfonic AcidSee, 2-Amino-p-benzene-disulfonic Acid

Aniline-^-sulfonic AcidSee, Sulfanilic Acid

2-Anilino-5-amino-&enzene-sulfonic Acid (C A. nomen.)

See, p-Amino-diphenylamine-2-sulfonic Acid

4-(^-Anilino-anilino)-o-cresol ((7. A. nomen.)See, 4-Phenylamino-4/-hydroxy-(plieiiyl-3/-tolylamme)

)-phenol (C. A. nomen.)/See, 4-Phenylamino-4/-hydroxy-diphenylamine


Anilino-benzene-sulfonic Acid (C. A. nomen.)

See, Diphenylamine-sulfonic Acid

8-Anilino-5-(j5>-hydroxy-anilino)-l-naphthalene-sulfonic Acid(C. A. nomen.)

See, 4-(p-Hydroxy~phenyl~amino)-l-phenylamino~naphtha-lene-8-sulfonic Acid

8-Anilino-l-naphthalene-sulfonic Acid (C. A. nomen.)

See, Phenyl-l-naphthylamine-8-sulfonic Acid

7-Anilino-l-7iaphthol-3-sulfonic Acid (C A. nomen.)

See, Phenyl-gamma Acid

m-Anilino-j&henol (C. A. nomen.)

See, m-Hydroxy-diphenylamine

2-Anilino-3-^seudoindolone (C. A. nomen.)

See, 2-Isatin Anilide

Aniline Salt

Note.—This is Aniline Hydrochloride.

See, Aniline

o-Anisidine

NH2

f jOCH 3 _ C 7 H f l N 0 = 123

STATISTICS.—Imported '14:—1,411 lbs.Manufactured '18:— ?Manufactured ;19:— ?Manufactured '20:— ?

FORMATION.—o-Nitro-anisole is reduced at 100-110° by means of iroand hydrochloric acid



Dyes Derived from o-Anisidine


93

94

95

96

259


MONOAZO DYESPigment Purple ASudan R

Azo Eosine

Azo CochinealCochineal Scarlet B

Chrome FastYellow GG

DISAZO DYEPonceau 10 RB


Manufacture

I '14:— 99

I '14:—1,001M'18:— ?M'19:— ?

I '14:— 952

I '14:— 150I '20:— 500

I '14:— 201


/^Naphthol

Nevile Winther Acid

l-Naphthol-4:8-disulfonic Acid

Salicylic Acid

Sulfanilic AcidCroceine Acid


CL

A

A

M

A

Anthracene

178

STATISTICS.—Imported '14:—$37,240 in valueManufactured '17:— ?Manufactured '18:— 225,552 lbs.

Manufactured '19:—1,381,944 lbs.Imported '19:— 51,895 lbs.

Manufactured '20:— 711,258 lbs.Imported '20:— 648,095 lbs.

FORIMATION.—From coal-tar by extraction and purification


USES.—For manufacture of anthraquinone and anthraquinone deriva-tives


Dye Derived from Anthracene

109


791



IndanthrcneOlive G


Manufacture

I J20:—11M'18:— ?


[Sulfur]


V

Anthrachrysone

1:3:5:7-Tetrahydroxy-anthraquinone

HO

CO 0 H

^0 — CuHsOe = 272

FORMATION.—From 3: 5-Dihydroxy-benzoic acid by heating with con-centrated sulfuric acid

LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 483Beil. I l l , 436; I I I spl. 312

Dyes Derived from Anthrachrysone

SchultzNumberfor Dyes

790

796



Acid AlizarinBlue BB

Acid AlizarinGreen G


Manufacture

I '14:—26,642I '20:— 3,539

I '20:— 1,334


[Sulfonation, Nitration,Reduction, etc.]

[Sulfonation, Nitration,Sodium sulJide reduc-tion]


ACr

ACr

1:9-Anthradiol (C. A. nomen.)

See, 1-Hydroxy-anthranol


Anthraflavic Acid2:6-Dihydroxy-anthraquinone (not considered herein)

Anthranilic Acid ((7. A. nomen. COOH^l)

o-Amino-benzoic Acid

COOH

STATISTICS.—Imported '14:— 106 lbs.Manufactured '17:— ?Manufactured '18:—11,826 lbs.Manufactured '19:—22,976 lbs.Manufactured '20:— ?

FORMATION.—Phthalic anhydride is melted and heated to 240°, where-upon ammonia gas is introduced, forming phthalimide. Thislatter is treated with sodium hypochlorite, forming anthranilicacid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 147Lange, Zwischenprodukte, #357-367, 1619

Dyes Derived from Anthranilic Acid

SchulteNumberfor Dye

200

201

202

Ordi ary Name andClass of Dye

MONOAZO DYESLake Red D

Pigment Scarlet G

Acid Alizarin Red BPalatine Chrome

RedB


Manufacture

I '14:— 2,428M'17:— ?M'18:— ?M'19:— ?M'20:— ?

M'17:— ?M'18:— ?M'19:— ?

I '14:— 7,374M'18:— ?M'19:—28,081I '20:— 1,342M'20:—67,817


0-Naphthol

Schaeffer's Acid

R-Acid


CL

CL

ACrCL


Dyes Derived from Anthranilic Acid (continued)


832



IndanthreneViolet RN


Manufacture

I '141—11,667I '20:— 49


Anthranilic Acid(2 mols)

1:5-Dichloro-anthraqui-none


V

Anthrano

See, 9-Anthrol

Anthraquinone

.CO.

STATISTICS.—Imported '14:— 29,850 lbs.

Manufactured '18:— ?

Manufactured '19:—294,260 lbs.


FOKMATION.—(1) From anthracene by appropriate oxidation means;for example, chromic acid. (2) From o-benzoyl-benzoic acid byaction of sulfuric acid. The o-benzoyl-benzoic acid is preparedby reacting together phthalic anhydride, benzene and aluminumchloride

LITERATUKE.—Cain, Intermediate Products (2d Ed.), 244Lange, Zwischenprodukte, #23, 648, 3065-3080


Dye Derived from Anthraquinone

SchultzNumberCOT Dye

863



AnthraquinoneBlue Green BXO

Statistics ofImport an i

Manufacture

I'14:—6,552I'20:— 849

Other IntermediatesUsed and Note^

m


A

Note.—Most of the dyes listed in the class ''Anthraquinone and AlliedDyes" (Schultz, #758-878) are derived indirectly from anthraquinone.These dyes are, however, not tabulated under anthraquinone, but under thatintermediate from which directly derived.

Anthraquinone-1: 5-and-l: 8-disulfonic Acids

Rho Acid is trivial name for the 1:5-disulfonic Add

Chi Acid is trivial name for the 1:8-disulfonic Acid

SO3H HO3S n n SO3H

= C14H8O8S2 = 368

STATISTICS.—^The anthraquinone-1: 5-disulfonate was manufactured in1918, 1919, 1920 by one company. Amount was not disclosed

FORMATION.—Anthraquinone is sulfonated with strong oleum in thepresence of mercury or mercuric oxide to a mixture of the 1: 5- and1:8-disulfonic acids, which are separated by crystallization


USES.—The 1:5-acid is employed for making anthrarufin, 1:5-dichloro-anthraquinone, etc.

Anthraquinone-2:6-disulfonic Acid

a-Anthraquinone-disulfonic Acid

H ° 3 S C \ C O X ) S O 3 H= C14H8O8S2== 368


FOKMATION.—From anthraquinone by heating with 45 per cent oleumto 160-170° C , dilution with water, neutralization with causticsoda and evaporation until the 2: 6 acid crystallizes out (2: 7 acidin mother liquor)


Dyes Derived from Anthraquinone-2:6-disulfonic Acid

£ • § 1 " " S E X - "

785

786


Alizarin GIFlavopurpurin

Alizarine Red 3WS


Manufacture

I '14:—49,021


[Alkaline Fusion]

[Alkaline fusion,sulfonation]


M

M


/3-Anthraquinone-disulfonic Acid

STATISTICS.—Manufactured ; 19:— ?


FORMATION.—From anthraquinone by heating with 45 per cent Oleum,dilution with water, neutralization with caustic soda, and evapora-tion until the 2: 6 disulfonic acid crystallizes out. The 2: 7 disul-fonic acid is then obtained (as sodium salt) by evaporating thismother liquor to dryness





784

Dye Derived from



Alizarin SXIsopurpurin



Manufacture

I '14:—14,273M'19:— ?I '20:— 49M'20:— ?


[Alkaline fusion]


M

a-Anthraquinone-disulfonic Acid


/3-Anthraquinone-disulfonic Acid


Anthraquinone-2-sulfonic Acid

Anthraquinone-jS-sulfonic Acid

j8 Acid or Beta Acid

Silver salt (Sodium derivative)

0-Sulfonic Acid

SO3H

STATISTICS.—^Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:— ?

FORMATION.—From anthraquinone by sulfonating with an equalweight of 45-50 per cent oleum and heating up to 160° C , diluting,neutralizing with caustic soda, and evaporating to crystallizationof the sodium salt ("Silver salt")



778

779

780

781

783

787

788

797

798

799

854

862



Alizarin

Alizarin Orange

Alizarin Red

Erweco AlizarinAcid Red BS

Purpurin

Alizarin Bordeaux B

Alizarin Cyaninc R

Alizarin Garnet R

Alizarin Maroon W

Alizarin Cyanine G

Alizarin Viridine DG



Manufacture

I 14:—202,392M17:— ?M18:— ?M19:— ?I '20:— 8,575M'20:— ?

I 14:— 14,239M19:— ?I '20:— 500M'20:— ?

I 14:— 81,919M17:— ?I '20:— 12,628

I '20:— 20

I '20:— 16,781

I 14:— 720

I '20:— 2,014

I '20:— 339

I '20:— 11,397

I 14:— 54,706I '20:— 28,802


[Oxidation]

[Alizarin, Nitration]

[Alizarin, Sulfonation]

[Alizarin, Sulfonation]

[Alizarin, Oxidation]

[Alizarin, Oxidation]

[Alizarin Bordeaux B,Oxidation]

[4-Nitro-alizarin, Re-duction]

[Crude Nitro-alizarin,Reduction]

[Alizarin Cyanine R,Amidation]

[Alizarin Bordeaux B]p-Toluidine (2 mols)[Sulfonation]

[Purpurin]Aniline[Sulfonation]


M

M

M

M

M

M

M

M

M

M

M

M


Anthraquinone-/3-sulfonic Acid


2-Anthraquinone-urea Chloride

See, 2-Anthraquinonyl-urea Chloride

2-Anthraquinonyl-urea Chloride

2-Anthraquinone-urea Chloride

. CO. Cl

FORMATION.—From 2-Amino-anthraquinone in nitro-benzene solutionby action of phosgene at 50°


Dyes Derived from 2-Anthraquinonyl-urea Chloride


835

836



HelindoneOrange GRN

HelindoneBrown 2GN


Manufacture

I '20:— 74

I '20:—15,238


2-Anthraquinonyl-ureachloride (2 mols)

2-Anthraquinonyl-urcachloride (2 mols)

Diamino-anthraqui-noncs, [various]


V

V

Anthrarufin


CO. 0 H

HO


STATISTICS.—Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:— ?

FORMATION.—This compound is obtained by the action of milk of limeon either anthraquinone-1: 5-disulfonic acid or on 1: 5-dinitro-anthraquinone

LITERATURE.—Cain, Intermediate Products (2d Ed.), 257Ullmann, Enzy. tech. Chemie, 1, 481Lange, Zwischenprodukte, #3269, 3272, 3287

Dye Derived from Anthrarufin


858



Alizarin Saphirol B


Manufacture

M'18:— ?M;19:— ?I '20:— 28,210M'20:— ?


[Sulfonation, Nitration,Reduction]


ACr

1-Anthrol (C. A. nomen.)a-Anthrol

1-Hydroxy-anthracene

OH

FORMATION.—Prom 1-anthracene-sulfonic acid by fusion with 5 partsof caustic soda at about 250°

LITERATURE.—Schmidt, Ber. 37, 66 (1904)Thorpe, Die. Chemistry, 1, 274; (1921 Ed.), 1, 352

Dye Derived from 1-Anthrol


893


INDIGO GROUP DYEAlizarin Indigo G


Manufacture

I'20:—1,596


Dibromo-isatin chloride


V


9-Anthrol (C. A. nomen.)


Anthranol

OH

FORMATION.—Anthraquinone is reduced with tin in boiling glacialacetic acid solution, or with iron and ferrous chloride solution

LITERATUKE.—Cain, Intermediate Products (2d Ed.), 262Thorpe, Die. Chemistry, 1, 272; (1921 Ed.), 1, 349Lange, Zwischenprodukte, #3038-3040

Dyes Derived from 9-Anthrol


763

764

765

872



IndanthreneDark Blue BO

IndanthreneViolet RT

IndanthreneGreen B

Leucol Brown B


Manufacture

I '14:—11,096I '20:—13,917

M'20:— ?

I '14:—72,251M'19:— ?I '20:— 6,765M'20:— ?

I '20:— 22


9-Anthrol (2 mols)[Glycerol (2 mols)]

9-Anthrol (2 mols)[Glycerol (2 mols),Halogcnation]

or[Indanthrene Dark BlueBO and Halogenation]

9-Anthrol (2 mols)[Glycerol (2 mols),

Nitration]or

[Indanthrene Dark BlueBO and Nitration]


V

V

V

V

Armstrong's Acid

See, Naphthalene-1: 5-disulfonic Acids


Armstrong's 8 Acid

See, Naphthalene-1: 5-disulfonic Acid

Armstrong and Wynne's Acid

l-Naphthol-3-sulfonic Acid (not considered herein)

Armstrong and Wynne's Acid II

See, 2-Naphthylamine-5: 7-disulfonic Acid

5: 6'-A oxy-bis-o-foluidine (C. A. nomen.)

See, Diamino-azoxy-toluene

^-Azoxy-o-toluidine

See, Diamino-azoxy-toluene

B Acid

See, l-Amino-8-naphthol-3: 5-disuIfonic Acid

This trivial name also applied to


2: 3-Dihydroxy~naphthalene-6: 8-disulfonic Acid

Badische Acid

See, 2-Naphthylamine-8-sulfonic Acid

Baum's Acid


Bayer's Acid

See, Croceine Acid


Benzal-bisxylidine (C. A. nomen.)

Seey Diamino-dixylyl-phenyl-methane


Benzaldehyde

HCO

STATISTICS.—Imported '14:— 20,475 lbs.Manufactured ' 17:—132,336 lbs.Manufactured '18:—360,591 lbs.Manufactured '19:—518,634 lbs.Manufactured '20:—702,543 lbs.

FOEMATION.—(1) From toluene by chlorination to benzylidine chloride,C6H5CHCI2, and by heating this with milk of lime under pressure.(2) From toluene by oxidation with manganese dioxide andsulfuric acid


Dyes Derived from Benzaldehyde





Used and Notes


495

TRIPHENYL-METHANE DYES

Malachite Green

499 Brilliant Green

I '14:—183,852M '17:—130,229M'18.-290,416M'19—560,301I '20— 100M'20:—654,237

I '14— 73,904M'18M'19I '20M'20

>— 25

502 Guinea Green BAcid Green 3BG

I '14— 49,971M'17— ?M'18 — ?M'19 — ?I '20M>20

Dimethyl-aniline(2 mols)

[Oxidation]

Diethyl-aniline (2 mols)[Oxidation]

Ethyl-sulfobenzyl-aniline (2 mols)

[Oxidation]

B

B

i— 278


Dyes Derived from Benzaldehyde (continued)


504

505

604

605


TRTPHENYL-METHANEDYES (continued)

Light Green SFBluish

Light Green SFYellowish

ACRIDINE DYESAcridine Orange R

Benzoflavine


Manufacture

I J14:M'17:M'18:-

6,693??

I '14:— 71,462M ' 1 9 : - - ?I '20:— 7,490

M'20:— ?

I '14:— 600


Benzyl-methyl-aniline (2 mols)

[Sulfonation andOxidation]

Benzyl-ethyl-aniline (2 mols)

[Sulfonation andOxidation]

Dimethyl-m-phenylene-diamine (2 mols)

[Ammonia removal;Oxidation]

m-Tolylene-diamine(2 mols)

[Ammonia removal,Oxidation]


B

B

Benzaldehyde-disulfonic Acid

4-Formyl~m-6enzene-disulfonic Acid (C. A. nomen.)

H C O

SO3H

FORMATION.—Toluene is sulfonated wi th oleum to t he 2 : 4-disulfonicacid, which is then oxidized wi th manganese dioxide

L I T E R A T U R E . — L a n g e , Zwischenprodukte, #899


Dye Derived from Benzaldehyde-disulfonic Acid

SchultzNumberfar Dye

579


XANTHONE DYESSulfo Rhodamine BXylene Red B


Manufacture

I '14:—1,698


Diethyl-m-amino-phenol (2 mols)

{Oxidation]


A

Benzaldehyde-o-sulfonic Acid

o-Formyl-frenzene-sulfonic Acid (C A. nomen.)

HCO

FORMATION.—By heating o-chloro-benzaldehyde with Na2SO3 at around170-180° under pressure


Dyes Derived from Benzaldehyde-o-sulfonic Acid


506

553



Erioglaucine

EriochromeCyanine R


Manufacture

I '14:—66,526M'19:~ ?I '20:— 6,160M'20:— ?

I '14:— 2,249I '20:— 2,205


Ethyl-sulfobcnzyl-aniline

orBenzyl-ethyl-aniline

(2 mols) [and sulfona-tion]

[Oxidation]

o-Cresotic Acid (2 mols)[Oxidation]


A

ACr


Benzamido- (C. A. nomen. for ft H&CO. N H)

See, Benzoylamino-

Note.—The C. A. name for this radical is the scientific one, and it is listedas an alternate, but in view of the widespread use of benzoylamino-, thelatter is given precedence at the present time.

l-Benzamido-4-chloro-anthraquinone (C. A. nomen.)

See, 1-Benzoylamino^-chloro-anthraquinone

7-meso-Benzanthren-7-one (C. A. nomen.)

See, Benzanthrone

Benzanthrone

7~meso-Benzanthren-7-one (C. A. nomen.)

STATISTICS.—Manufactured J19:— ?


FORMATION.—(1) From anthranol and glycerol by condensation bymeans of sulfuric acid. (Anthranol is made from anthraquinone.)(2) From anthracene in sulfuric acid solution, by addition of glyceroland heating to 100-110° C. until the anthracene disappears. Thereaction mass is then diluted with water, salted out and purified



Dyes Derived from Benzanthrone

SchvltzNumberfor Dye




Ustd and Notes


763

764

765


IndanthreneDark Blue BO

IndanthreneViolet RT

IndanthreneGreen B

I '14:— 11,096I ;20:— 13,917

I '14:—72,251M'19:— ?I '20:— 6,765M'20:— ?

Benzanthrone (2 mols)

Benzanthrone (2 mols)[Halogenation][or Indanthrene Dark

Blue BO and halo-genation]

Benzanthrone (2 mols)[Nitration][or Indanthrene Dark

Blue BO and Nitra-tion]

Benzanthrone-quinolinePhenanthroquinolinone (C A. nomen.)

O

FORMATION.—From 2-amino-anthraquinone and glycerol by warmingwith condensing agents, for example, sulfuric acid

LITERATURE.—Lange, Zwischenprodukte, #3596Ullmann, Enzy. tech. Chemie, 3, 314

Dye Derived from Benzanthrone-quinoline


846



Indanthrene DarkBlue BT



Used and Notes

Benzanthrone-quino-line (2 mols)


V


Benzene-azo-diethylaniline

See, p-Diethylamino-azo-benzene

Benzene-sulfonyl Chloride

SO2C1

= 176.5

125

FORMATION.—From benzene-sulfonic acid by treatment with phos-phorus pentachloride

LITERATURE.—Bucherer, Farbenchemie, 78, 150

Dye Derived from Benzene-sulfonyl Chloride


182


MONOAZO DYEFast SuLfon VioletBrilliant Sulfon

RedB


Manufacture

I '14:—4,871I '20:—4,740


H AcidAniline


A

Benzidine

H2N«

STATISTICS.—Imported '14:— 55,245 lbs.Manufactured '17:—1,766,582 lbs.Manufactured 718:—2,501,887 lbs.Manufactured '19:—1,319,629 lbs.Manufactured '20:—2,183,583 lbs.

FORMATION.—Nitro-benzene is reduced to hydrazo-benzene with zincor iron in presence of caustic soda; the hydrazo-benzene is re-arranged to benzidine by treatment with acid



Dyes Derived from Benzidine





Used and Notes


MONOAZO DYESChicago Orange G

Diamond Flavine G

Dutch Yellow

DISAZO DYESPyramine Orange 3G

Congo Red

Diazo Black B

Glycine Red

Glycine Corinth

Orange TA

Congo Corinth G

I '14:— 23,089M'17:— ?M'18:— ?M'19:— ?M'20:— ?

:— 7,8630:— 396

I '14:— 20,629M'17:— ?M'18:—587,153M'19:—873,734M'20:—

1,502,630

I '14:— 62,854

p-Nitro-toluene-o-sulfonic Acid

Salicylic Acid

Salicylic Acid[Sodium sulfite]

Nitro-m-phenylene-diamine

m-Phenylene-diamine-disulfonic Acid

Naphthionic Acid(2 mols)

I '14:—M'17:—M'18:—M'19:—M'20:—

602??

??

'14:— 44,157M'17:— ?M'18.— ?M'19:—137,704M'20.-242,503

Laurent's Acid (2 mols)

a-Naphthyl-glycineNaphthionic Acid

a-Naphthyl-glycine(2 mols)

Naphthionic AcidCresol

Nevile Winther's AcidNaphthionic Acid

M

M

D

D

D

D

D

D

D


Dyes Derived from Benzidine (continued)

127


313

314

315

316

317

318

319

320

321

322



Congo Bubine

PyramineOrange Ml

Congo Orange G

Brilliant Congo G

PyramidolBrown BG

Benzidine Puce

Diamine Scarlet

^Bordeaux

Heliotrope 2B

TrisulfonViolet B


Manufacture

I '14:— 46,213M'17:— ?M'18:— ?I '20:— 2,601

I '14:— 2,789

I '14:— 1,623I '20:— 75

I '14:— 41,175I '20:— 11,340

I '14:— 1,335M'18:— ?M'19:— ?M'20:— ?

I '14:— 1,473I '20:— 60

I '14:— 1,124M'17:— ?M'18:— ?M'19:— ?I '20:— 7,927

M'20:— ?


Croceine AcidNaphthionic Acid


Amino-R Acid

PhenolAmino-R Acid[Ethylation]

Amino-R AcidBroenner's Acid

Resorcinol (2 mols)

0-Naphthol

PhenolG Acid[Ethylation]

Croccine Acid (2 mols)

Croccine Acidl-Naphthol-4: 8-

disulfonic Acid

0-Naphtholl-Naphthol-3:6:8-tri-

sulfonic Acid


D

D

D

D

D

MF

D

D

D

D




323

324

325

326

327

328

329

330

331

332

333



Dianil Blue R

Chicago Blue 4R

Columbia Blue R

Oxamine VioletOxydiamine Violet BF

Diamine Violet N

Diamine Black RODianol Black RW

Diamine Brown V

Zambesi Brown G

Alkali DarkBrown GV


Diamine Black BHOxamine Black BHN


Manufacture

M'20:— ?

I 14:— 1,199

I 14:— 3,071

I 14:— 23,981I '20:— 732

I 14:— 18,263M19:— ?M'20:— 92,503

I 14:— 8,253

M19:— ?

I 14:— 4,028I '20:— 1,104

I 14:— 5,985I '20:— 3,799

I 14:—619,430M17:— ?M'18:— ?M19 :--485,046I '20:— 5,512M '20.-803,501


Chromotropic Acid(2 mols)

Croceine Acid1 -Amino-8-naphthol-4-

sulfonic Acid

l-Naphthol-3: S-disul-fonic Acid

l-Amino-8-naphthol-4-sulf onic Acid

J Acid (2 mols)

Gamma Acid (2 mols)

Gamma Acid (2 mols)

m-Phenylene-diamineGamma Acid

Gamma Acid2: 7-Naphthylene-diamine-sulfonic Acid

Nitroso-/3-naphtholGamma Acid

Gamma AcidAmino-R Acid

Gamma AcidHAcid


D

D

D

D

D

D

D

D

D

D

D




334

335

336

337

338

339

340

340 (1)

341


DISAZO DYES

{continued)Diphenyl Blue

Black

NaphthamineBlack RE

Benzo Cyanine R

Diamine Blue BBBenzo Blue BB

Naphthamine Blue2B

Brilliant Orange G

Benzo Orange R

ChlorazolOrange 2R

Crumpsall DirectFast Red R


Manufacture

I '14:— 26,240

I '14:— 49,016

I '14:— 201

I '14:— 19,035M'17:—

1,445,059M'18:—

1,523,985M'19:—

1,380,335M'20:—

1,789,774

I '14:— 11,707I '20:— 400

I '14:— 6,321M717:— ?

I '14:— 1,073M'17:— ?M'lS:— 50,422M'19:— 42,807I '20:— 220M'20:— 86,210

M'17:— ?M'18:— ?M'19:— ?M'20:— ?


Ethyl-gamma AcidH Acid

Gamma AcidKAcid

H Acidl-Amino~8-naphthol-4-

sulfonic Acid

H Acid (2 mols)

K Acid (2 mols)

Salicylic Acid3-Amino-phenol-4-

sulfonic Acid

Salicylic AcidNaphthionic Acid

Salicylic Acid2~Naphthylamine-7-

sulfonic Acid

Salicylic AcidRSalt


D

D

D

D

D

D

D

D

D




342

343

344

345

346

347

348

349

350

351



Chrysamine G

Diamine FastRedF

Diamine Brown M

Oxamine Maroon

Oxamine Red

Diphenyl Brown RN

Diphenyl Brown BIS

Diamine Brown B

Alkali Yellow R

Cresotine Yellow G


Manufacture

I '14:— 608M'17:— 26,061M'18:— 28,846M'19:— 54,279I '20:— 9,810M'20:— 49,342

I '14:— 50,479M'19:— 56,864I '20:— 4,040M'20:—115,865

I '14:— 65,396M'18:— ?M'19:— 15,957M'20:—257,872

I '14:— 11,636I '20:— 848

I '14:— 13,471

I '20:— 24

I '14:— 1,74M'17:— ?M'18:— ?M'19:— ?M'20:— ?


Salicylic Acid(2 mols)

Gamma AcidSalicylic Acid

Salicylic AcidGamma Acid

Salicylic Acidl-Amino-5-naphthol-7-

sulf onic Acid

J AcidSalicylic Acid

Salicylic AcidMethyl-gamma Acid

Salicylic AcidDimethyl-gamma Acid

Salicylic AcidPhenyl-gamma Acid

Salicylic AcidDehydrothio-p-tolui-

dine-suHonic Acid

o-Cresotic Acid(2 mols)


D

D

D

D

D

D

D

D

D

D


Dyes Derived from Benzidine {continued)

131


352

353

354

438

439

440

441

442

443

444

445


DISAZO DYES

{continued)Direct Violet R

Direct IndigoBlue BN

Direct Gray R

TRISAZO DYESMelogene Blue BH

Direct IndigoBlue A


Diazo BlueBlack RS

Direct Black V

Direct IndoneBlueR

Crumpsall DirectFast Brown B



Manufacture

I '14:— 661M'19:— ?

I '14:— 6,000

I '20:— 4,927

M'17:— ?M'18:— ?

M'18:— ?

M'19:— ?M'20:-~ ?

I '14.-145,738


m-Tolylene-diamineI: 7-Dihydroxy-6~naph-

thoie-3-sulfonic Acid

1: 7-Dihydroxy-6-naph-thoic-3-sulfonic Acid

H Acid

1: 7-Dihydroxy-6-naph-lhoic-3-sulfonic Acid(2 mols)

H Acid (2 mols)p-Xylidine

H Acid (2 mols)m-Amino-p-cresol

Methyl Ether

Gamma Acid (2 mols)m-Amino-p-cresol

Methyl Ether

H Acid (2 mols)a-Naphthylamine

Gamma Acida-Naphthylamine2 R Acid

a-NaphthylamineII Acid2 R Acid

Salicylic AcidAnilineGamma Acid

Salicylic AcidAnilinePhenyl-gamma Acid


D

D

D

D

D

D

D

D

D

D

D


Dyes Derived from Benzidine {continued)


446

447

448

449

462

463

464

465



Benzo Olive

Benzo Gray S Extra

Diamine Bronze G

TrisulfonBrown B

Erie DirectBlack GX

Direct DeepBlack EW

Erie DirectBlack RX

Cotton Black E

Erie DirectGreen E T



Manufacture

I '14:— 1,149

I '14:— 802

I '14:— 4,495

I '14:— 16,781I '20:— 38,616

I '14:—1,246,536

M'17:— ?M'18:— ?M'19:—

7,250,007M'20:—

7,736,994

I '14:—248,567M'19:— ?M'20:—

2,050,741

M'17:— ?M'18:— ?M'19:— 69,700M'20:— ?


Salicylic Acida-NaphthylamineHAcid

Salicylic Acida-NaphthylamineNevile Winther's Acid

Salicylic AcidHAcidm-Phenylene-diamine

2 R AcidSalicylic Acidm-Phenylene-diamine

AnilineHAcidm-Phenylene-diamine

AnilineHAcidm-Tolylene-diamine

AnilineHAcidPhenol

Salicylic AcidAniline1: 8-Amino-naphthol-4-

sulfonic Acid


D

D

D

D

D

D

D

D



133


466

467

468

469

470

471

472

473

474



Eboli Green

Diphenyl Green G

Diphenyl Green 3G

Chloramine Black N

ChloramineGreen B

Chloramine Blue 3G

ChloramineBlue HW

Diamine Black HW

Diamine Green BOxamine Green B


Manufacture

I '20:— 2,205

I '14:— 39,600M'19:— ?I '20:— 1,763M'20:— ?

I '14:— 1,675M'19:— ?

I '14:— 286M'19:— ?I '20:— 882

I '20:— 342

I '14:— 77,100M'17:— ?M'18:—295,147M'19:—305,854I '20:— 2,460M'20:—420,138


l-Amino-8-naphthol-3: 5-disulf onie Acid

Salicylic AcidSulfanilic Acid

PhenolH Acido-Chloro-p-nitro-

aniline

Salicylic AcidII Acid0-Chloro-p-nilro-

aniline

m-Phenylene-diamineH Acid2: 5-Dichloro-aniline

PhenolH Acid2: 5-Dichloro-aniline

H Acid (2 mols)2:5-Dichloro-aniline

Gamma AcidH Acid2: 5-Dichloro-aniline

Gamma AcidII Acidp-Nilro-aniline

PhenolH Acid7;-Nitro-aniline


D

D

D

D

D

D

1)

D

D


Dyes Derived from Beuzidine (continued)


475

476

477

478

479

480

489

490


TKISAZO DYES(continued)

Diamine Green GOxamine Green G

BenzamineBrown 3GO

Congo Brown GNaphthamin*

4G

Columbia Green

Dianil Black

Congo Brown

TETEAKISAZO DYESHessian Brown BBN

Cotton Brown A


Manufacture

I '14:—- 7,329M'17:— ?M ;18:— 29,118M'19:—136,638I '20:— 1,332

M'20:— 53,292

I '14:— 16,988M'17:— ?M'18:— ?M'19:— ?M '20.-623,757

I '14:— 52,141e Brown M '17:— ?

M'18:— ?M'19:— ?I '20:— 443

M'20:—229,489

I '14:— 45,162M'18:— ?I '20:— 7,555

I '14:— 3,045

I '14:— 29,074


Salicylic AcidH Acidp-Nitro-aniline

Sulf anilic Acidm-Phenylene-diamineSalicylic Acid

Sulfanilic AcidResorcinolSalicylic Acid

Salicylic AcidSulfanilic Acidl-Amino-8-naphthol-4-

sulfonic Acid

Chromotropic AcidNaphthionic Acidm-Phenylene-diamine

ResorcinolSalicylic AcidLaurent's Acid

Sulfanilic Acid (2 mols)Hesorcinol (2 mols)


m-Phenylene-diamine(2 mols)




712

714


SULFUR DYESKyrogene Yellow G

Thiophor YellowBronze G


Manufacture

I '14:— 1,126I '20:— 1,543


m-Tolylene-dithio-urea[Sulfur]

p-Phenylene-diaminep-Amino-acetanilide[Sulfur]


S

S

Benzidine-disulfonic Acid

6: e'-Diamino-mrm'-bi^enzene-sulfonic) Acid (C. A. nomen.)

4:4'-Diamino-diphenyl-3: 3'-disulfonic Acid

= C12H12N2O6S2 = 344

HO3S SO3H

FORMATION.—From benzidine sulfate by heating with 2 parts of sulfuricacid at about 210° for forty-eight hours

LITERATURE.—Cain, Intermediate Products (2d Ed.), 94Griess and Duisberg, Ber7 22, 2464 (1889)Cf. Griess, Ber., 14, 300 (1881)Cf. Farbenfabriken, Ger. Pat. 27954

Dyes Derived from Benzidine-disulfonic Acid


360

459

460


DISAZO DYEPyramine Orange R

TRISAZO DYESBenzo Black Blue G

Benzo Black Blue 5G


I '14:— 21,329I '20:— 7,821

I '14:— 602


Nitro~m-phenylcne-diamine

Ncvile-Winther's Acid(2 mols)

a-Naphthylamine

1:8-Dihydroxy-naph-thalene-4-sulfonic

Acid (2 mols)a-Naphthylamine


D

D

D


Benzidine-sulfon-disulfonic Acid

4:4'-Diamino-diphenyl-2: 2'-sulfon-disulfonic Acid

2:7-Diamino-9-dioxide-? :?-dibenzothiophene-disulfonic Acid (C

A. nomen.)

2(SO3H)

= C12H10N2O8S3 = 406

FORMATION.—Benzidine sulfate is heated with 40 per cent oleum for

1 hour at 100° in an autoclave, and then at 150° until a sample

dissolves in hot water and does not give a yellow precipitate with

alkali

LITEBATUEE.—Lange, Zwischenprodukte, #1275

Dyes Derived from Benzidine-sulfon-disulfonic Acid


361


DISAZO DYESulfonazurine


Manufacture

I '14:—300


Plienyl-a-naphthyl-amine (2 mols)


D

Benzidine-sulfonic Acid

2-Amino-5-(p-amino-phenyl)-6enzene-sulfonic Acid (C. A. nomen

SO>H=1)

>NH2=Ci2Hi2N2O3S = 264

HO3S


FORMATION.—From benzidine sulfate by evaporating to drynoss withdilute sulfuric acid (1J^ mols), and then heating in air bath atabout 170° for 24 hours


Dyes Derived from Benzidine-sulfonic Acid


359

491


DISAZO DYETrypan ^ e ^

TETRAKISAZO DYEDianil Black PR



Used and Notes

Amino-R Acid (2 mols)

Gamma Acid (2 mols)ra-Phcnylene-diaminc

(2 mols)


Medi-cinal

D

Benzoic Acid

COOH

= C7H6O2=:122

STATISTICS.—Imported '14:—352,201 lbs.


Manufactured ;18:—282,212 lbs.



FORMATION.—(1) From toluene by chlorination to benzo-trichloride,and hydrolysis with milk of lime. (2) From toluene by directoxidation with nitric acid


e, Zwischenprodukte, #24, 59


Dyes Derived from Benzoic Acid





Used and Notes


509

520

521

770

782


Chrome Green


Diphenylamine Blue

Spirit BlueAniline Blue

I '14:— 2,149

I '14M'17M'18M'19I '20

M'20

50,563

:— 723


Alizarin Yellow A

Anthracene BrownAlizarin Brown

I '14:—115,586M'17M'18M'19I '20

M'20

40,4262,728

42,840

Hydrol[Oxidation]

Aniline (5 mols)p-Toluidine

or[p-Rosaniline tripheny-

lated]

Aniline (2-4 mols)o-Toluidinep-Toluidine

or[Fuchsine or Rosaniline

base phcnylated]

Pyrogallol

Gallic Acid

M

ss

ss

M

M

Benzo-trichloride

a-Trichloro-toluene (C. A. nomen.)

CC13

=C7H5C13 = 195.5

STATISTICS.—Imported ' 14:—very smallManufactured '18:— ?Manufactured '20;— ?


FORMATION.—From toluene by treatment with chlorine, preferably inpresence of catalyst


Dyes Derived from Benzo-trichloride


610

770


QUINOLINE DYEQuinoline Red

ANTHBAQUINONE ANDALLIED DYES

Alizarin Yellow A



Used and Notes

QuinaldincIsoquinoline

Pyrogallol


B

M

l-Benzoylamino-4-chloro-anthraquinone

l-Benzamido-4-chloro-anthraquinone (C A. nomen.)

CO NH.COC 6HS

o ^:C2iH12ClNO3 = 361.5

FORMATION.—By heating l-Amino-4-chloro-anthraquinonc with ben-zoyl chloride

LITERATURE.—Ullmann, Enzy. tech. Chcmie, 1, 164

Dye Derived from l-Benzoylamino-4-chloro-anthraquInone


833



Algol Olive R


Manufacture

I '14:— 13,334I '20:— 461


l-Bcnzoylamino-4-amino-anthraquinono

[Chloro-sulfonic acid]

DyeAppli-cationClam

V


o-Benzoyl-6enzoic Acid

COOH

STATISTICS.—Manufactured 1920:— ?

FORMATION.—By condensation of phthalic anhydride and benzene inpresence of aluminum chloride

LITERATURE.—Heller, Zeit. angew. Chem., 19, 669 (1906)Heller, Ber., 41, 3631 (1908)Cain, Intermediate Products (2d Ed.), 249

USES.—For synthesis of anthraquinone

Benzoyl Chloride

COC1

STATISTICS.—Manufactured J17:—20,621 lbs.Manufactured '18:— 6,585 lbs.Manufactured '19:— ?Manufactured '20:—14,277 lbs.

FORMATION.—From benzoic acid by action of sulfuryl chloride

LITERATURE.—TJllmarjii, Enzy. tech. Chemie, 2, 329Lange, Zwischenprodukte, #42

Dyes Derived from Benzoyl Chloride


814

815



Algol Yellow WG

Algol Scarlet G


Manufacture

I '14:— 5,185I '20:— 4

I '20:— 959


1-Amino-anthraqui-none



V

V


Dyes Derived from Benzoyl Chloride (continued)

chultzumber•r Dye




Used and Notes



(continued)Algol Red 5G

Algol Yellow R

Algol Pink R

Algol Red R

Algol BrilliantViolet 2B

Algol BrilliantOrange FR

Algol Violet B

Algol Corinth R

I '14:-I '20:-

I '14:—I '20:—M'20:—

I '14:—I '20:—

I '14:—I '20:—

1,33851

4,SS72,299

1261,368

2,3227,335

I '14:— 3,893I '20:— 827

I '14:-I '20:-

I '20:—

6,195482

69

I '20:— 134

1:4-Diamino-anthra-quinone

BonzoyJ chloride(2 mols)


Benzoyl chloride(2 mols)

l-Amino-4~hydroxy-anthraquinone

1: 5-Diamino-anthra-quinone


[Oxidation]

Diamino-anthrarufinBenzoyl cliloride

(2 mols)

1:2: 4-Triamino-an-thraquinone (?)

l-Amino-4: 5:8-tri-hydroxy-anthraqui-none

1-Amino-anthraquinone2-Chloro-anthraquinone[Nitration, Reduction]

V

V

V

V


Dyes Derived from Benzoyl Chloride (continued)




Manufacture



889

INDIGO GBOUPDYES

Indigo Yellow 3G

890 Ciba Yellow G I '14:— 48

Indigo or Phenyl-gly-cine or Phenyl-gly-cine-o-carboxylic acidor Thiocarbanilide orAniline or PhthalicAnhydride

Indigo or Phenyl-gly-cine or Phenyl-gly-cine-o-carboxylic acidor Thiocarbanilide orAniline or PhthalicAnhydride

[Bromination]

JV-Benzoyl-o-folidine

H3C CH3

== 316


FORMATION.—Tolidine is heated in toluene solution with benzoylchloride under a reflux condenser


Dyes Derived from AT-Benzoyl-o-folidine


104


MONOAZO DYEBenzoyl Pink


Manufacture


Nevile-Winther's Acid


D


[(N-Benzyl-anilino) -methylj-fcenzene-sulfonic Acid (C. A. nomen.)

See Dibenzyl-anjiine-sulfonic Acid

Benzyl Chloride

a-Chloro-foluene (C. A. nomen,)

CH2C1

= C7H7C1= 126.5

STATISTICS.—Imported '14:— 4,589 lbs.Manufactured '17:— 136,179 lbs.Manufactured'18:— 690,930 lbs.Manufactured '19:— 720,953 lbs.Manufactured '20:—1,246,412 lbs.

FORMATION.—From boiling toluene by passing in chlorine until thetheoretical amount (37.5%) has been absorbed


Dyes Derived from Benzyl Chloride


517

523

586


TRTPHENYL-METHANE DYES

Methyl Violet 5BBenzyl Violet

Fast Green

XANTHONE DYEChrysoline


Manufacture

I '14:— 22,387M'17:— ?I '20:— 3,313

I '14:— 14,347I '20:— 3,612

I '20:— 1,402


[Benzylation of MethylViolet]

orDimethyl-aniline

(3 mols)Phenol

m-Nitro-henzaldehydeDimethyl-aniline

(2 mols)Benzyl chloride (2 mols)[Sulf onation, Oxidation]

Phthalic AnhydrideKesorcinol (2 mols)

DyeApplir-cationClass

B

A

A


Benzyl-ethyl-aniline

Ethyl-benzyl-aniline

A7-Ethyl-Ar-phenyl-&enzylamine (C A. nomen.)

STATISTICS.—Imports 1914:—small amountManufactured 1917:— ?Manufactured 1918:— ?Manufactured 1919:— ?Manufactured 1920:—159,636 lbs.

FORMATION.—From one part of ethyl-aniline and two parts of benzylchloride, by boiling under a reflux condenser for four hours


Dyes Derived from Benzyl-ethyl-aniline





Used and Notes


505

506

508

TRIPHENTL-^IETHANEDYES

Light Green SFYellowish

Erioglaucine

Xylene Blue AS

I 14:— 71,462M'19: - - ?I '20:— 7,490M ;20:— ?

I 314:-M'19:-I '20:-MJ20:-

I '14:-I '20:

66,526

6,160

8,2385,573

Benzyl-ethyl-aniline(2 mols)

Benzaldehyde[Sulfonation; Oxidation]


Benzaldehyde-o-sul-fonic acid

[Sulfonation; Oxidation]


3-Methyl-benzalde-hyde-4:6-disulfonicAcid

[Oxidation]


Dyes Derived from Benzyl-ethyl-aniline (continued)


545



(continued)Patent Blue A


Manufacture

I '14:— 03,744M'18:— ?I '20:— 44,801


B enzyl-ethyl-aniline(2 mols)

m-Nitro-benzaldehydeor m-Hydroxy-benzal-dehyde

[Sulfonation; Oxidation


A

Benzyl-ethyl-aniline-disulfonic Acid

iV-Ethyl-iV-(29-sulfo-beDzyl)-metanilic Acid (C A. nomen.)

Note.—Position of sulfonic group in the benzyl radical is not fully de-

termined

STATISTICS.—Manufactured in 1919 and 1920 in undisclosed amounts

FORMATION.—B enzyl-ethyl-aniline is dissolved with cooling in two parts

of 20 per cent oleum, and is then treated with two and a half parts

of 80 per cent oleum, and the mixture warmed at 60° until the

sulfonation is complete




Dye Derived from Benzyl-ethyl-aniline-disulfonic Acid

SchidtzNumberfor Dye

528


TEEPHENYL-MEIHANE DYES

Fast AcidViolet 10B


Manufacture

I '14:— 12,919M'17:— ?M'18:~- ?M'19:— ?I '20:— 10,086M '20:— ?


Hydrol[Oxidation]


A

Benzyl-ethyl-aniline-sulfonic Acid*

See, Ethyl-sulfobenzyl-aniline

Benzyl-ethyl-^-phenylene-diainine-siilfoiiic Acid

See, Ethyl-sulfobenzyl-p-phenylene-diamine

3-Benzyliinino-4-inetliyl-diphenylamiiie

See, iV^Benzyl-iV^pheiiyl-^-m-tolyleiie-dianiine

Benzyl-methyl-aniline

Methyl-benzyl-aniline

iV-Methyl-iV-phenyl-6enzylamine (C A. nomen.)

FORMATION.—^From methyl-aniline and benzyl chloride by heatingtogether on a water bath for a few hours


1 The data and the dye table should have been placed here rather than under ethyl-sulf obenzyl-aniline- — The Author.



504

527

Dyes Derived



Light Green SFBluish

Acid Violet 4BN

from Benzyl-methyl-aniline


Manufacture

I 14:— 6,693M'17:— ?M'18:— ?

I 14:— 29,184I '20:— 23,335M'20:— ?


Benzyl-methyl-aniline(2 mols)

Benzaldehyde[Sulfonation; Oxidation]

Ketone[Sulfonation]


A

A

Benzyl-a-naphthylamine

N-Benzyl-l-naphthylamine (C. A. nomen.)

— Ci7Hi5N=233

FORMATION.—-a-Naphthylamine is heated in an autoclave with benzyl

chloride in the presence of a catalyst


Dye Derived from Benzyl-a-naphthylamine


654


OXAZINE DYENile Blue 2B



Used and Notes

5-Diethylamino-2-nitroso-phenol


B


iV3-Benzyl-iVi-phenyl-4-m-^olylene-diamine (C. A. nomen NH2—D

Phenyl-p-amino-benzyl-o-toluidine (CH3=1)

3-Benzylimino-4-metliyl-dipheiiylamiiie

NH.CH2-

CH3

FORMATION.—i-/tt-TolyIene-diamine hydrochloride is melted with ani-line at 220-270°, forming iV^phenyl-^wz-tolylene-diamine. Thislatter body upon being warmed with benzyl chloride with or with-out a diluent such as alcohol forms the benzyl-derivative desired

LITERATURE.—Lange, Zwischenprodukte, #1621, 1622, 1734

Dyes Derived from iNP-Benzyl-^-phenyM-m-tolylene-diamiiie

SchvZtzNumberfor Dye

684

684

684


AZINE DYESRhoduline Violet

RLoduline Red B

Ehoduline Red G


Manufacture

I '14:— 2,751I '20:— 35


Xitroso-dimethyl-aniline

Xitroso-ethyl-aniline

Nitroso-ethyl-o-toluidine


B

B

B

Beta=0

Note.—This is not considered in the alphabetical arrangement, e.g.beta-Naphthol is indexed as p-Naphihol under "N". However £-Naphihol is placed after a-Naphtkol

Beta Acid


Beta-Naphthol

See, j8-Naphthol under N


Bi-compoundsSee, Di-compounds, e.g.,iox binitro-benzol (or -benzene), see

dinitr o-b enz ene

£:^'-Bis(diethylamino)-&enzohydrol (C. A. nomen.)See, ^rp'-Tetraethyl-diamino-benzohydrol

^:^'-Bis(diethylamino)-&enzophencne (C. A. nomen.)

See, p: p'-Tetraethyl-diamino-benzophenone

^:j>'-Bis(dimethylamino)-benzohydrol (C. A. nomen.)

See, Hydrol

^:^/-Bis(dimethylamino)-6enzophenone (C. A. nomen.)See, Ketone

3:5-Bis[jS-(5-hydroxy-7-sulfo-2-naphthyl)-carbamido]-/>-^oluene-sulfonic Acid (C. A. nomen.)See, Sulfo-m-tolylene-diamine-bis (carbonyl-amino-naphthol-

sulfonic Acid)

Broenner's AcidSee, page 152

1-Bromo-anthraquInoneBr

Y J =Ci4H7BrO2 = 287c o A ^

FORMATION.—From potassium salt of anthraquinone-1-sulfonic acid,by treatment with bromine and acid

LITERATURE.—Lange, Zwischenprodukte, #3083Dye Derived from 1-Bromo-anthraciuinone


873



HelindoneBrown AN


Manufacture

I '14:— 2,831I '20-— 16,290


1-Br omo- anthraquinone(2 mols)



V


5-Bromo-2-hydroxyl-3-methy*-^hionaphthene (C. A. and Englishnumbering)

6-Bromo-3-hydroxyl-4-methyl-(l)-thionaphthene (German num-bering)

FORMATION.—4-Bromo-6-nitro-2-methyl~benzoic acid is reduced withN a & ; the amino-compound diazotized, and then treated withpotassium xanthogenate (potassium ethyl xanthate). The xantho-genate compound upon being treated with chloro-acetic acid formsbromo-methyl-phenyl-thioglycol-o-carboxylic acid

B r / N s . C H s . C O O H

KycooRCH3

This compound upon being fused with caustic alkali, forms thecarboxylic acid of 5-bromo-2-hydroxy-3-methyl-thionaphthene.The carboxylic acid decomposes, evolving CO2, when its solutionis acidified and warmed

LITERATURE.—Lange, Zwischenprodukte, #2169Georgievics and Grandmougin, Dye Chemistry, 433,437Ct Cain, Intermediate Products (2d Ed.), 158, 159

Dye

SckidteNumberfor Dye

910

Derived from 5-Bromo-2-hydroxyl-3-methyl-tluoiiaphthene


INDIGO GROUP DYEHelindone Pink BN


Manufacture

I '14:— 41,699I '20:-— 17,162


5-Bromo-2-hydroxyl-3-methyl-thionaphthene(2 mols)

[Oxidation]


V


I-Bromo-4-methylamino-anthraquinone

151

N H . CH3

FORMATION.—From l-methylamino-anthraquinone by treating itspyridine solution with bromine and warming on the water bath


Dye Derived from l-Bromo-4-methylamino-anthraquinone


856



Alizarin Astrol B


Manufacture

I '14:— 10,907I '20:— 15,518


p-Toluidine[Sulfonation][? Classification]


ACr

2-Bromo-l-methylamino-anthraquinone

CO

c c

NH.CH 3

iBr

FORMATION.—^From l-amino-2-bromo-anthraquinone by methylationwith dimethyl-sulfate


Dye Derived from 2-Bromo-l-methylamino-anthraquinone





Used and Notes


839


Algol Blue K I '14:—150I '20:—218

2-Bromo-l-methyl-amino-anthraqui-none (2 mols)


4-Bromo-iV-methyl-anthrapyridone

6-Bromo-3-methyl-3:7-pm'-7iaphthoquinoline-2(3): 7-dione (C.A.nomen.)

N.CHs

—340

FORMATION.—(1) From 1-methylamino-anthraquinone, by acetylationof amino group, and condensation to the JV-methyl-anthra-pyridone. Bromination of this latter compound in the 4 positionresults in 4-bromo-A^-methyl-anthrapyridone. (2) From 4-bromo-1-methylamino-anthraquinone by acetylation and closing the ring

LITERATURE.—Lange, Zwischenprodukte, #3609Georgievics and Grandmougin, Dye Chemistry, 464-465Ullmann, Enzy. tech. Chemie, 1, 192

SchultzNumberJor Lye

825

Dye Derived from


ANTHRAQUINOXE AXDALLIED DYES

Algol Red B

4-Bromo-i^-methyl-anthrapyridone


Manufacture

I '14:— 2,399I '20:— 4,151


2-Amino-aiitliraqui-none


V

6-Bromo-3-methyl-3:7-^eri-naphthoquinoline-2(3): 7-dione (C. Anomen.)

See, 4-Bromo-AT-methyl-anthrapyridone

Broenner's Acid2-Naphthylamine-6-sulfonic Acid6-Amino-2-naphthalene-sulfonic Acid (C A. nomen.)

Naphthylamine-sulfonic Acid Br.)3-Naphthylamine-iS-sulfonic AcidAmino-Schaeffer's Acid


1NH2 _ <

153

STATISTICS.—Imported '14:—2,316 lbs.Manufactured 18:— ?Manufactured ' 19:— ?Manufactured '20:— ?

FORMATION.—By heating the sodium salt of Sehaeffer's Acid with con-centrated ammonia in an autoclave at 180°

LITERATURE.—Cain, Intermediate Products (2d Ed.), 206Lange, Zwischenprodukte, #2371-2376Thorpe, Die. Chemistry, 3, 601

Dyes Derived from Broenner's Acid


172

174

176

177

230

302


MONOAZO DYESFast Brown 3B

Double BrilliantScarlet G

Double ScarletExtraS

Scarlet 2R

Chrome Yellow DMordant Yellow 0

DISAZO DYESCloth Bed 3G, 3GA

Hessian BrilliantPurple


Manufacture

I '14:— 1,477

I '14:—210,429M '17:— ?M'20:— ?

I '14:— 10,182M'17:— ?I '20:— 1,653

I '14:—129,651M'17:— ?M'18:— 32,011M'19:— ?I '20:— 1,389M '20:— ?

I '14:— 251


a-Naphthol

/3-Naphthol


Salicylic Acidor

o-Cresotic Acid

o-Ainino-azo-toluene

Diamino-stilbene-disulf onic Acid

Broenner's Acid(2 mols)


A

A

A

M

M

D


Dyes Derived from Broenner's Acid {continued)

SchuUzNumberfor Dye




Used and Notes


316

357

365

366

368

370


Brilliant Congo G

Dianol Red B

Benzo Purpurin B

Diamine Red BDelta Purpurin 5B

Brilliant Purpurin4B

Brilliant Congo R

I '14:— 21,090M'17:— ?M'18:— ?M'19:~- ?

I '14:— 21,058M '17:— ?M '18:— ?I '20:— 1,896

I '14:— 6,634

I '14:— 19,133I '20:— 11,129

BenzidineAnoino-R Acid

Dichloro-benzidine DBroenner's Acid

(2 mols)

TolidineBroenner's Acid

(2 mols)

Tolidine D2-Naphthylamine-7-

sulf onic Acid

Tolidine DNaphthionic Acid

Tolidine DAmino-R Acid

CAcid

1: 5-Dihydroxy-naphthalene-2-sulfonic Acid

2-Naphthol-4: 8-disulfonic Acid


(These intermediates not considered herein)

Carbazole

Dibenzo-pyrrole

Diphenylene-imide

H


STATISTICS.—Imported ' 14:—very smallManufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?

FORMATION.—By extraction from coal-tar or crude anthracene

LITERATURE.—Ullmann, Enzy. tech. Chemie, 3, 274Lange, Zwischenprodukte, page 308

Dyes Derived from Carbazole

155


748


SULFUR DYEHydron Blue


Manufacture

I ;14:—296,723I '20:— 19,210M'20:— ?


p-Nitroso-phenol[S+Na*S]


V

Carbolic Acid

See, Phenol

Carbonyl Chloride

See, Phosgene

2-Carboxy-5-chloro-phenyl-thioglycolic Acid

See, 5-Chloro-phenyl-thioglycol-a-carboxylic Acid

iV-(Caxboxy-methyl)-anthranilic Acid (C. A. nomen.)

See, Phenyl-glycine-o-carboxylic Acid

2-(Carboxy-methyl-mercapto)-4-chloro-benzoic Acid (C A. nomm.)

See, 5-Chloro-phcnyl-thioglyco!-o-carboxylic Acid

Cassella's Acid

See, 2-Naphthol-7-sulfonic Acid

Cassella's Acid F



Chi AcidSee, Anthraquinone-1: 8-disulfonic Acid

Chicago AcidSee, l-Amino-8~naphthol-2:4-disulf onic Acid

3-Chloro-aniline-2-sulfonic AcidSee, 2-Amino-6-chloro-benzene-sulfonic Acid

5-Chloro-o-anisidine (N

NH2

| | 0 C H 3 = C7H8C1XO = 157.5Cl

FORMATION.—1: 4~Dichloro-3-nitro-benzene is boiled with caustic potashand methyl alcohol and the resulting chloro-nitro-anisol is reducedwith iron and acetic acid

LITERATURE —J. Soc. Chem. Ind. 21, 610 (1902)U. S. Pat. 695,812Laaige, Zwischenprodukte, #1034

Dye Derived from 5-Chloro-o-anisidine


97


MONOAZO DYEChloranisidine

Scarlet



Used and Notes

jS-Naphthol

DyeAwl'cationClass

MF

I-Chloro-anthraquinone (C. A. nomen.)a-Chloro-anthraquinone

nr\ Cl

>2 = 242.5

FORMATION.—From potassium anthraquinone-l^sulfonate by treatmentat 100° with chlorine and dilute hydrochloric acid

LITERATURE.—Lange, Zwischenprodukte, #3081, 3083, 3086


Dye Derived from 1-Chloro-anthraquinone

157


834



Algol Gray B


I '14:— 4,192I '20:— 890


1-Amino-anthraquinone[Nitration, Reduction]


V

2-Chloro-anthraquinone (<7. A. nomen.)

/3-Chloro-anthraquinone

= 242.5

FORMATION.—(1) From sodium anthraquinone-2-sulfonate in aqueoussolution, by adding hydrochloric acid, and by passing in chlorineuntil all the 2-chloro-anthraquinone is precipitated out. (2) Fromphthalic anhydride and chloro-benzene by first condensing in pres-ence of A1C13 to chloro-benzoyl-benzoic acid, and then by warmingwith sulfuric acid to 2-chloro-anthraquinone

LITERATURE.—Lange, Zwischenprodukte, 3082, 3083Ullmann, Enzy. tech, Chemie, 1, 472

Dyes Derived from 2-Chloro-anthraquinone


824

828

870


ANTHRAQTJINONE ANDALLIED DYES

Algol Orange R

IndanthreneBordeaux B

Algol Corinth R


Manufacture

I '14:— 51I '20:— 406

I '20:—2,741

I'29:— 134


1-Amino-anthraquinone

2-Chloro-anthraquinone(2 mols)


1-Amino-anthraquinone[Nitration, Reduction]Benzoyl chloride


V

V

V


l-Chloro-anthraquinone-2-carboxylic Acid

.CO. Cl

c o c r^ 286.5

FORMATION.—2-Methyl-l-nitro-anthjaquinone is treated with chlorine

in nitro-benzene solution, whereby the nitro group is substituted

by chlorine and the methyl group oxidized, thus forming 1-chloro-

anthraquinone-2-carboxylic acid


Ullmann, Enzy tech. Chemie, 1, 484

Dye Derived from l-Chloro-anthraquinone-2-carboxylic Acid


831


ANTHRAQUTNONE ANDALLIED DYES

IndanthreneRedBN


Manufacture

I '14:—6,056I ;20:—4,766


/3-Naphthylamine


V

o-Chloro-fcenzaldehyde

HCO

> = 140.5


FORMATION.—From o-chloro-benzyl alcohol by oxidation with nitric

acid in a sulphuric acid solution at about 40° C.

LITERATURE.—J. Soc. Chem. Ind. 18, 576 (1899)




496

500

503

551

Dyes Derived


TRIPHENYL-METHANE-DYES

Setoglaucine

Setocyanine 0

Night Green ANeptune GreenBrilliant Milling

Green B

EriochromeAzurol B

from o-Chloro-benzaldehyde


Manufacture

I J20:— 1,102

I 14:— 923I '20:— 1,102

I 14:— 40,868M19:— ?I '20:— 10,940M'20:— ?

I 14:— 21,060I '20:— 7,275



[Oxidation]

Ethyl-o-toluidine(2 mols)

[Oxidation]

Ethyl-sulfobenzyl-ani-line (2 mols)

[Oxidation]

o-Cresotic acid (2 mols)[Oxidation]


B

B

A

ACr

2-Chloro-benzaldehyde-6-sulfonic Acid

3-Chloro-2-formyl-6enzene-sulfonic Acid (C. A. nomen.)

HCO

C1 _ c7H5C104S = 220.5

FOBMATION.—(1) 1: 3-Dichloro-2-benzaldehyde is treated with one molof sodium sulfite under pressure. (2) 3-Chloro-2-toluene-l-suKonicacid is oxidized with manganese dioxide and sulfuric acid

LITERATURE.—Lange, Zwlschenprodukte, #710

Dye Derived from 2-Chloro-benzaldehyde-6-sulfonic Acid


554


TRIPHENTL-METHANE DTE

Chrome Azurol S


Manufacture

I 14:— 2,469I '20:— 551




ACr


?-Chloro-7-me5o-benzanthren-7-one (C. A. nomen.)

See, Chloro-benzanthrone

Chloro-benzanthrone

?-Chloro-7-m€so-6enzanthren-7-one (C. A. nomen.)

Cl= C17H9C1O =264.5

STATISTICS.—Manufactured J19:— ?

FORMATION.—From benzanthrone in acetic acid solution by treatmentwith chlorine

LITERATURE.—Addition #6719 to French Patent 349,531 of Oct. 1,1906

Dyes Derived from Chloro-benzanthrone

SchulizNumberjar Dye




Used and Notes


766

767

768

ANTHEAQTHNONE AXDALLIED DYES

IndanthreneViolet R

IndanthreneViolet 2R

IndanthreneViolet B

I '14:-M'19:-I J20:

1,590?941

I '14:— 68,419I J20:— 40,782

T20:—S4,165(?)

Chloro-benzanthrone(2 mols)


[Dichlorination][or Indanthrene Violet

R, chlorinated]


PDibromination][or Indanthrene Violet

R, brominated]

V


Chloro-fcenzene (C. A, nomen.)

Monochlor-benzene

Cl

1 = 112.5

STATISTICS.—Manufactured 1917.-24,624,099 lbs.Manufactured 1918:—20,530,639 lbs.Manufactured 1919:— 4,116,666 lbs.Manufactured 1920:— 4,829,142 lbs.

FORMATION.—By passing chlorine through benzene in the presence ofa catalyst (iron) and at a relatively low temperature

LITERATURE.—Cain, Intermediate Products (2d Ed.), 6-11Lange, Zwischenprodukte, #2

Uses.—For technical preparation of o- and p-chloro-nitro-benzene,chloro-dinitro-benzcne, o-amino-phenol-p-sulfonic acid and manyother intermediates

l-Chloro-2:4-dinitro-fcenzene (C. A. nomen.)

2:4-Dinitro-chloro-benzene

Cl/ \ N O 2f J =C6H3C1N2O4 = 202.5

NO2

STATISTICS.—Manufactured 1917:—6,078,637 lbs.Manufactured 1918:— ?Manufactured 1919:—4,428,730 lbs.Manufactured 1920:—5,947,791 lbs.

FORMATION.—From chloro-benzene by dinitration with mixed nitricand sulphuric acids



Dyes Derived from l-Chloro-2:4-dinitro-benzene


724

Tlo

726

727

73S


SULFUK DYESImmedial Black


Immedial Brown B

Pyrogene DirectBlue

Pyrogene Blue

Auronal Black B

Cotton Black


Manufacture

14:— 54,696M I S : — ?

I 14:— 23,887M I S : — ?

I 14:— 10,934I '20:— 2,49S


p-Amino-phenol[S+Na«S]

p-Amino-phenol[NaOH; S+Na^S]

p-Amino-phenol[Alcohol;

p-Phen yl ene-diamine[Glycerol; S+Na^S]

Sulfanilic or Metanilicacid

[S+NaaS]


S

S

l-Chloro-2:6-dinitro-benzene-4-sulfonic Acid

See, 4-Chloro-3: 5-dinitro-benzene-sulfonic Acid

4-Chloro-3:5-dinitro-6enzene-sulfonic Acid (C. A. nomen.)

I-Chloro-2: 6-dinitro-ben^ene-4-sulfonic Acid

SO3H

O 2Nl J N O 22 O 7 S = 282.5

FORMATION.—34 Par t s of chloro-benzene are dissolved in a mixture of72 parts of monohydrate and 30 par ts of 2 5 % oleum, by aid of heat.When cold, there is added 26 parts of 8 7 % nitric acid which causesthe temperature t o rise to 40° where it is held for 2 hours. Thena further addition of oleum is made,—100 par ts of 60% followed b y40 parts of potassium nitrate, and the mixture heated for severalhours at 120-130°.



Dye Derived from 4-Chloro-3:5-dinitro-benzene-sulfonie Acid


542



Agalma Green B


Manufacture

I J14:— 2,294


HydrolMetanilic acid[Oxidation]

Appli-cationClass

A

3-Chloro-2-formyl-&enzene-sulfonic Acid (C. A. nomen.)

See, 2-Chloro-benzaldeliyde-6-sulfonic Acid

Chloro-H AcidSee, l~Chloro-8-naphthol-3: 6-disulf onic Acid

(4-Chloro-6-methoxy-3-methyl-phenyl-mercapto)-acetic Acid (C.A. nomen.)

See, 4-Chloro-6-methoxy-3-methyl-phenyl-thioglycolic Acid

^Chloro-e-methoxy-S-methyl-phenyl-tliioglycolic Acid

(4-Chloro-6-metlioxy-3-metliyl-phenyl-mercapto)-acetic Acid(C. A. nomen.)

S.CH2 .COOH

CH3O =Ci0HnClO3S=246.5

FOEMATION.—4-Chloro-6-methoxy-m-toluidine (NH2 = 1) is dissolvedin hydrochloric acid and diazotized. The diazo solution, warmedto 70°, is introduced into an alkaline solution of potassium xan-thate (C2H5O.CS.SK), the condensation product extracted andsaponified to the mercaptan. The mercaptan is reacted withchloro-acetic acid, forming the above thioglycolic acid

LITERATURE.—Ger. Pat. 245,544; 241,910Frdl. 10, 507, 502Lange, Zwischenprodukte, #1043, 688Cf. Georgievics and Grandmougin, Dye Chemistry, 436-7


Dye Derived from 4-Chloro-6-metho^-3-methyl-phenyl-ttaoglycolicAcid

Schultzdumberfor Dye

920

Ordinary A a?ne andClass of Dye

LSDIGO GROUPDYE

HelindoneViolet BB


I '14 — 28,607I '20 — 16,882


4r-Chloro-6-methoxy-3-methyl-phenyl-thio-glycolic acid (2 mols)

[Chloro-sulfonic acid]


V

l-CMoro-8-naphthol-3:6-disulfonic Acid

8-Chloro-l-rcaphthol-3: 6-disulfonic Acid (C A. nomen.)

Chloro-H Acid

HO Cl

SO3H S2= 338.5

STATISTICS.—Manufactured ' 18:— ?

Manufactured ' 19:— ?Manufactured J20:— ?

FORMATION.—H acid is diazotized; and the yellow diazo body isfiltered off, mixed with 10 per cent hydrochloric acid, cooled to10°, and a solution of cuprous chloride added. This product isnow heated to complete the reaction, purified, and the chloro-bodyisolated. (Sandmeyer Reaction)

LITERATUKE.—Cain, Intermediate Products (2d Ed.), 238Lange, Zwischenprodukte, #2451, 2671Thorpe, Die. Chemistry, 3, 628


Dyes Derived from l-Chloro-8-naphthol-3:6-disulfonic Acid]


119

418


MONOAZO DYEDiamine Rose

DISAZO DYEDiamine Brilliant

BlueG


Manufacture

I 14:— 5,269M18:— ?M19:— ?M;20:— ?

I 14:— 11,592I ;20:— 51


D eliydr o-thio-p-toluidine

Dianisidine1-Chloro-S-naphthol-

3: 6-disulfonic Acid(2 mols)


D

D

8-Chloro-l-naphthol-3: 6-disulfonic Acid (C. A. nomen.)

See, l-Chloro-8-naphthol-3: 6-disulfonic Acid

l-Chloro-8-naphthol-4-sulfonic Acid

8-Chloro-l-naphthol-5-sulfonic Acid (C. A. nomen.)

HO Cl

= C10H7ClO4S = 258.5

SO3H

FORMATION.—l-Chloro-naphthalene-4-sulfonic acid is nitrated and

reduced, forming l-chloro-8-naphthylamine-4-sulfonic acid; which

is diazotized and added slowly to a boiling hot solution of 10 per

cent sulfuric acid and the boiling continued until the nitrogen

evolution ceases

LITERATURE.—Eng. Pat., 12085 of 1898



Dye Derived from l-Chloro-8-napIithol-4-sulfonic acid


417


DISAZO DYEChlorazol Blue R


I '14:— 10,151


Dianisidinel-Chloro-8-naphthol-5-



D

l-Chloro-8-naphthol-5-sulfonic Acid

8-Chloro-l-naphthol-4-suKonic Acid (C A. nomen.)

HO

5 = 258.5

H O 3 S

FORMATION.—l-Chloro-naphthalene-5~sulfonic acid is nitrated andreduced, forming l-chloro-8-naphthylarnine-5-sulfonic acid; whichis diazotized and added slowly to a boiling hot solution of 10 percent sulfuric acid, and the boiling continued until the evolution ofnitrogen ceases.

LITERATURE.—Eng. Pat., 12085 of 1898Cf. Lange, Zwischenprodukte, #2451


417

Dye Derived from "


DISAZO DYEChlorazol Blue 3G

L-Chloro-8-naphthol-5-sulfonic acid


I '14:— 10,151


Dianisidinel-Chloro-8-naphthol-5-



D

8-Chloro-l-naphthol-4-sulfonic Acid (C. i . nomen.)

See, l-Chloro-8-naphthol-5-sulfonic Acid


8-Chloro-l-7iaphtliol-5-sulfonic Acid (C. A. nomen.)

See, l-Chloro-8-naphthol-4-sulfonic Acid

l-Chloro-3-nitro-6-aniline

See, 2-Chloro-4-nitro-aniline (C. A. nomen.)

2-Chloro-4-nitro-aniline (C. A. nomen.)

o-Chloro-p-rritro-aniline

l-Chloro-3-nitro-6-aniline

167

NH2

2 = 172.5

FORMATION.—p-Nitro-aniline is dissolved in concentrated hydrochloricacid or in sulfuric acid, ice added to cool under 0°, and chlorine isconducted into the solution under 0°, until the proper increase inweight has taken place


o-Chloro-£-nitro-aniline

See, 2-Chloro-4-nitro-aniline ((7. A. nomen.)

SchultzNumberfor Bye

467

468

Dyes Derived


FRISAZO DYESDiphenyl Green G

Diphenyl Green 3G

from 2-Chloro-4-nitro-aniline


Manufacture

I '20:— 2,205


BeruzidinePhenolHAcid

BenzidineSalicylic AcidHAcid


D

D


2-Chloro-5-nitro-&enzaldehyde

HCO

: l = C7H4CINO3 = 185.5

FORMATION.—o-Chloro-benzaldehyde is dissolved in sulfuric acid, andnitrated cold with mixed acid

LITERATURE.—Beil., I l l , 16

Dye Derived from 2-Chloro-5-nitro-benzaldeliyde


552


TREPHENYL-METHANE "DYE

Chromal Blue G


Manufacture

I 14:— 1,335




M

2-Chloro-6-nitro-6enzaldehyde (C. A. nomen.)

o-Chloro-onitro-beiizaldeliyde

HCO

O 2 N / p i _ C7H4C1NO3 = 185.5

FORMATION.—This can be prepared from 2-chloro-6-nitro-benzyl bromideby action of strong nitric acid, or from 2-chloro-6-nitro-benzylalcohol by oxidation

LITERATURE.—Lange, Zwischenprodukte, #699Beil. I l l , , spl. 11

Bye Derived from 2-Chloro-6-nitro-benzaldehyde

SchuUzNumberfor Dye

887


INDIGO GROUPDYES

Brilliant IndigoBASF/4G


Manufacture

I '20:— 1,207


2-CHoro-6-nitro-ben-zaldehyde (2 mols)

[Acetone; Bromination]


V


o-CMoro-o-uitro-benzaldehyde

See, 2-Chloro-6-nitro-&enzaldehyde (C. A. nomen.)

o- and -Chloro-nitro-benzenes (C. A. nomen.)

o- a?id p-Nitro-chloro-benzenes

N0 2 N0 2

C 1 and I J = C6H4C1NO2 = 157.5

STATISTICS.— Mixed orth. paraManufactured 1917:— 602,192 lbs.Manufactured 1918:— ?Manufactured 1919:—2,520,991 lbs.Manufactured 1920:— 349,386 lbs. 959,405 lbs.

FORMATION.—Chloro-benzene, upon being nitrated, gives a mixture oabout 30 per cent of o-chloro-nitro-benzene and about 70 per centof p-chloro-nitro-benzene. The separation is carried out byalternate crystallization (of the p-compound) and fractionaldistillation

LITERATURE.—Cain, Intermediate Products (2d Ed.), 11-13Lange, Zwischenprodukte, #193, 194

USES.—o-Chloro-nitro-benzene is employed for preparation of o-nitro-anisole, which in turn leads to o-anisidine and dianisidine. I t isalso used for 4-chloro-3-rjitro-benzene-sulfonic acid

p-Chloro-nitro-benzene is employed for preparation of sub-stituted diphenylamines (Sulfur Dyes), and for 2-chloro-5-nitro-benzene-sulfonic acid

2-Chloro-5-nitro-5enzene-sulfonic Acid

SO3H

= C6H4C1NO5S = 237.5


FORMATION.—By sulfonation of p-chloro-nitro-benzene with 10-12 percent oleum


LITERATURE.—Cain, Intermediate Products (2d Ed.), 14USES.—For preparation of -i-nitro-aniline-2-sulfonic acid (p-nitro-

aniline-o-sulfonic acid)

4-Chloro-3-nitro-&enzene-sulfonic Acid

SO3H

= 237.5

FORMATION.—By sulfonation of o-chloro-nitro-benzene with 5 parts of30 per cent oleum

LITERATURE.—Cain, Intermediate Products (2d Ed.), 13USES.—For preparation of aniline-2: 5-disulfonic acid

(4-Chloro-2-nitro-phenyl-mercapto)-acetic Acid (C. A. nomen.)

See 4-Chloro-2-nitro-phenyl-thioglycolic Acid

4-CWoro-2-mtro-phenyl-ttaoglycolic Acid

(4-Chloro-2-nitro-phenyl-mercapto)-acetic Acid (C A. nomen.)

S.CH 2 .CO0H

INO2 _ C8H6C1NO4S = 247.5

FORI^ATION.—(1) 4-Chloro-2-nitro-phenyl-mercaptan is reacted withchloro-acetic acid in an alkaline solution. (2) Probably also by re-acting the nitro-derivative of p-dichloro-benzene (l:4-dichloro-3-nitro-benzene) with thioglycolic acid

LITERATURE.—Cf. Lange, Zwischenprodukte, #2171, 611, 1041, 674

Dye Derived from 4-Chloro-2-nitro-phenyl-thioglycolic Acid


921


INDIGO GROUP DYESHelindone Grav BR,

2B


Manufacture

I '14:—470I '20:—508


4-Chloro-2-nitro~plienyl-thioglycolic acid (2mols)

[Chloro-sulfonic acid:Reduction]


V


a-Chloro-^-nitro-foluene (C. A. nomen.)

See, p-Nitro-benzyl Chloride

(m-Ohloro-phenyl-mercapto)-acetic Acid (C A. nomen.)

See, m-Chloro-phenyl-thioglycolic Acid

m-Chloro-phenyl-thioglycolic Acid(m-Chloro-phenyl-mercapto)-acetic Acid (C. A. nomen.)

S.CH2 .COOH

= C8H7C1O2S = 202.5

FORMATION.—m-Chloro-aniline is diazotized, coupled with potassiumxanthate (C2H5O . CS. SK), hydrolyzed to the mercapto-derivative,and condensed with chloro-acetic acid

LITERATURE.—Cf. Lange, Zwischenprodukte, #688

Dye Derived from m-Chloro-phenyl-thioglycolic Acid


917


INDIGO GROUP DYESHelindone Red B


Manufacture

I 14:—100I '20:—200


m-Chloro-phenyl-thio-glycolic Acid (2 mols)

[Oleum Condensation]


V

5-Chloro-phenyl-thioglycol-o-carboxylic Acid2-Carboxy-5-chloro-phenyl-thioglycolic Acid2-(Carboxy-methyl-mercapto)-4-chloro-&enzoic Acid (C. A.

nomen.)

FOEMATION.—4-Chloro-anthranilic acid is diazotized, and reacted withpotassium ethyl xanthate, and then with chloro-acetic acid,resulting in the formation of the chloro-phenyl-thioglycol-o-carboxyacid

LITERATURE.—Lange, Zwischenprodukte, #2170; cf. #518


Dye Derived from 5-Chloro-phenyl-thioglycol-o-caxboxylic Acid


909


INDIGO GROUP DYECiba Red B



Used and Notes

5-Chloro-phenyl-tliio-glycol-o-carboxylicacid (2 mols)


V

a-Chloro-toIuene (C. A. nomen.)

See, Benzyl Chloride

2-Chloro-5-toluidine-4-sulfonic Acid (CH3=1)

See, 2-Amino-5-chloro-p-toluene-sulfonic Acid (C, A. nomen

SOzH-1)

(4-Chloro-o-tolyI-mercapto)-acetic Acid (C. A. nomen,)

See, 4-Chloro-2-tolyl-thioglycolic Acid

4-Chloro-2-tolyl-thioglycolic Acid

(4"Chloro-o-tolyl-mercapto)-acetic Acid (C. A. nomen.)

S.CH2COOH

Q C H , =

Cl

=216.5

FORMATION.—4^Chloro-o-toluidine (NH^^l) is diazotized, coupled

with potassium xanthate (C2H5O. C S . SK), hydrolyzed to the

mercapto-derivative, and condensed with chloro-acetic acid

LITEBATURE.—Lange, Zwischenprodukte, #688

Cf. Geogievics and Grandmougin, Dye Chemistry, 437


Dye Derived from 4-Chloro-2-tolyl-thioglycolic Acid





Used and Notes


918INDIGO GROUP DYEHelindone Red 3B I '14:— 27,874

I '20:— 4,3854-Chloro-2-tolyl-thio-

glycolic Acid (2 mols)[Oleum Condensation][There is some question

as to the Cl- andCH3- positions of thatchloro-tolyl-thiogly-colic acid used]

V

Chromogen ISee, Chromotropic Acid

Chromotrope AcidSee, Chromotropic Acid

Chromotropic Acid1: 8-Dihydroxy-naphthalene-3: 6-disulfonic Acid4: 5-Dihydroxy-2: 7-naphthalene-disulfonic Acid (C. A. nomen.)Chromotrope AcidChromogen I

HO OH

HO3S SO3H

STATISTICS.—Manufactured ' 18:— ?Manufactured '19:—164,654 lbs.Manufactured '20:—152,352 lbs.

FORMATION.—(1) From l-Naphthol-3: 6:8-trisulfonic acid by fusionof the sodium salt of this acid with caustic soda at 170-220°.(2) From H acid by heating with a dilute caustic soda solutionin an autoclave at about 265°

LITEEATURE.—Cain, Intermediate Products (2d Ed.), 232Lange, Zwischenprodukte, #2775, 2670


Dyes Derived from Chromotropic Acid





Used and Notes


40

57

61

67

114

129

130

171

MONOAZO DYESChromotrope 2R

Chromotrope 2B

Victoria Violet

Chromotrope 6B

Chromotrope 10B

Chromazone Red A

Chromazone Blue R

Chromotrope 8B

I '14:—JVT17:—M '18:—M'19:—M '20:—

5,00????

Aniline

I '14M'18M'19M'20

. «>

I '14:— 52,36£M'17M'18M'19:I '20;1 '20

105,0862,182

I '14:— 2,818M'17:— ?VI'18:— ?M'19:—77,481

M'20:— ?

19:— ?

I '14:— 24;

p-Nitro-aniline

p-Phenylene-diamineactually from

p-Nitro-aniline andReduction

orp-Ammo-acetanilide

and Saponification

p-A m m o-acetanilide

£'18:-

a-Napiithylamine

p-Amino-benzaldehyde

p-A mino-benzaldebydeIthyl-phenyl-liydra-zine

or2>-Amino-benzylidine-

ethyl-phenyl-hydra-zone

Naphthionic Acid

A

ACr

A

M

M


Dyes Derived from Chromotropic Acid (continued)

175


292

323

379

380

415

479

777


DISAZO DYESAcid Alizarine

Black I

Dianil Blue R

Dianil Blue 2EBenzo New Blue 2B

Dianil Blue B

Dianil Blue G

TRISAZO DYEDianil Black E

ANTHBAQUINONE ANDALLIED DYES

Chromogen I


Manufacture

M'20:— ?

I ;14:— 14,434

M'19:— ?M'20:— ?


p-Pheny lene-diam m eSalicylic Acid

BenzidineChromotropic Acid

(2 mols)

TolidineNevtte-Winther's Acid

TolidineChromotropic Acid

(2 mols)

DianisidineChromotropic Acid

(2 mols)

BenzidineNaphthionic Acidwz-Phenylene-diainine

[Oxidation on fiber]


M

D

D

D

D

D

ACr

Chrysazin1: 8-Dihydroxy-anthraqTiinone (not considered herein)

Chryseic Acid4-Nitro-l-naphthol (not considered herein)

Cincholepidine

See, Lepidine

Cleve's AcidSee, l-Naphthol-5-sulfonic AcidSee, l-Naphthylanune-6-sulfonic AcidSee, l-Naphthylamine-7-sulfonic Acid


Cleves a Acid

See, Laurent's Acid (l-Naphthylamine-5-sulfonic Acid)

Cieve's p Acid


Also applied to l-Nitro-naphthalene-6-sulfonic acid

Cieve's T Acid

l-Naphthylamine-3-sulfonic Acid (not considered herein)

Cieve's 5 Acid



l-Nitro-naphthalene-7-sulfonic Acid (not considered herein)

Cieve's 6 Acid

See, l-NaphthyIamine-7-sulfonic Acid



l-Nitro-naphthalene-7-suKonic Acid (not considered herein)

Cieve's Acids

See, l-Naphthylamine-6-and-7-sulfonic Acids

Cieve's a-Nitro-naphthalene-sulfonic Acid

l-Nitronapthalene-5-sulf onic Acid (not considered herein)

Cieve's 7-Nitro-naphthalene-sulfonic Acid


Cieve's 5-Nitro-naphthalene-sulfonic Acid


Cieve's 0-Nitro-naphthaIene-sulfonic Acid




Cresol

177

Note.—C. A. practice is to start the numbering of cresols from the OHgroup unless there is present a substituent of uhigher order" as SOzH.European practice is generally to start numbering with CHZ

STATISTICS.—Imported '14:—245,835 lbs.Manufactured '19:— ?Manufactured '20:— ?

FORMATION.—Extracted from coal tar

LITERATTJKE.—Lange, Zwischenprodukte, #438-452

Dye Derived from Oresol


311


DISAZO DYEOrange TA


Manufacture

I '14:—602M'17:— ?M'18:— ?M'19:— ?M'20:— ?


BenzidineNaphthionic Acid


D

2:3-Cresotic Acid (C. A. nomen.)

See, o-Cresotic Acid

o-Cresotic Acid

o-Cresotinic Acid

2: 3-Cresotic Acid (C. A. nomen.)

o-Homo-salicylic Acid

COOH


STATISTICS.—Imported 314:—very small


FORMATION.—By dissolving o-cresol in caustic soda, evaporating to a

dry powder; then by treating this powder with carbon dioxide

under pressure



Dyes Derived from o-Cresotic Acid






177

351

392

395

551

552

MOXOAZO DYEChrome Yellow D

DISAZO DYESCresotine Yellow G

ToluyleneOrange G

Cresotine Yellow R

TRJPHESTYL-

METHANE DYESEriochrome

Azurol B

Chromal Blue G

I '14M'17M'18M'19:M '20;

I '14:-M'18:-M '19:-I '20:-M'20:-

1,748

; 9

67,022??

273?

I '20:—21,060

7,275

I '14:— 1,335

Broenner's Acid

Benzidineo-Cresotic Acid (2 mols

Tolidine4: 6-Diamino-m-

toluene-sulf onic Acid

Tolidineo-Cresotic acid (2 mols)

o- Chloro-benzaldehyde[or other halogen]


2-Chloro-5-nitro-ben-zaldehyde


M

D

D

D

ACr

M


Dyes Derived from o-Cresotic Acid (continued)

179

SchultzNumberor Dye

553

554


TRIPHENYL-METHANEDYES {continued)

EriochromeCyanine R

Chrome Azurol S


Manufacture

I '14:— 2,249I '20:— 2,205

I '14:— 2,469I '20:— 551


Benzaldehyde-o-sulforricAcid


2-Chloro-benzaldehyde-6-sulfonic Acid



ACr

ACr

o-Cresotinic AcidSee, o-Cresotic Acid

Croceine Acid2-Naphthol-8-sulfonic Acid (C. A. nomen.)

Bayer's Acid

iS-Naphthol-sulfonic Acid B (of Schultz)

j3-Naphthol-a-sulfonic Acid (0/ Bayer & Co.'s Patents)

Croceine Sulfonic Acido-Acid (0/ Claus and Voltz)1

Rumpff AcidHO3S

C 0 O H - «STATISTICS.—Manufactured 1919:— ?

Manufactured 1920:— ?FORMATION.—/3-Naphthol is sulfonated at a low temperature, forming

mostly croceine acid, but accompanied by some Schaeffer's acid.They are generally separated by crystallization of their salts


1 Claus and Voltz incorrectly assigned to this acid the constitution, 2-naphthol-3-sulfonic acid,


Dyes Derived from Croceine Acid


167

249

251

255

259

313

320

321

324


MOXOAZO DYESCroceine Scarlet

3BX

DISAZO DYESCroceine Scarlet 3B

Croceine Scarlet 0

Croceine Scarlet SBPonceau 6 RB

Ponceau 10 RB

Congo Rubine

Bordeaux

Heliotrope 2B

Chicago Blue 4R

IMMMIM

I

I

II

I

IMMI


Manufacture

'14:—'17:—'IS:—'19:—'20:—'20:—

'14:—

'20:—

'14:—'20:—

'14:—

'14:—'17:—'IS:—'20:—

I '14:—M '18:—M'19:—M '20:—

II :

14:—20:—

14:—

3,10???650?

9,613

100

2,3791D4

201

46,213??

2,601

1,335???

1,47360

1,199


Naphthionic Acid

Amino-azo-benzene-sulfonic Acid


Aroino-azo-toluene-sulfonic Acid

Sulfanilic Acid6-Anisidine


BenzidineCroceine Acid (2 mols)

Benzidinel-Naphthol-4:8-

disulfonic Acid

Benzidine1 - Amino-8-naphthol-4-

sulfonic Acid


A

A

A

A

A

D

D

D

D


Dyes Derived from Croceine Acid (continued)

181


384

420



Chicago Blue 2RDiamine Blue C2R

Azidine WoolBlueB


Manufacture

I '14:— 23,877


Tolidinel-Anrino-8-naphthol-4-

sulfooic Acid

Dianisidinel-Amino-S-naphthol-4-

sulfonic Acid


D

D

Croceine-sulfonic AcidSee, Croceine Acid

4> CumidineSee, Pseudocumidine (C A. nomen.)

Dahl's AcidSee, 2-Naphthylamine-5-sulfoDic Acid

Dahl's Acid IISee, l-Naphtliylamine-4:6-disulfonic Acid

DahTs Acid IIISee, l-Naphthylamine-4:7-disulfonic Acid

Dahl's Acidsl-Naphthol-4:6-and-4:7-disulfonic Acids (not considered herein)

Dehydro-thio-j)-toluidineIV-Amino-5-methyl-2-phenyl-thiazolAjDaino-benzenyl-a-amino-tliio-cresolp-Amino-phenyl-tolutMazolel-(2?-A.Tnino-pheiiyl)-5-inethyl-5enzotliiazole (C A. nomen.)

\


FORMATION.—By heating together 3}4 parts of p-toluidine with 1 partof sulfur, gradually raising the temperature to the boiling point, andfinally fractionally distilling off the dehydro-thio-p-toluidine in avacuum

LITERATURE.—Cain, Intermediates (2d Ed.), 77Lange, Zmsehenprodukte, #2219-2223

Dyes Derived from Dehydro-thio-^-toluidine

SckuUzNumberfor Dye




Used an$ Notes


117

118

119

614

618

MONOAZO DYESErica 2GN

GeranineBrilliant Geranine

I '14:M'19:I '20:-

1,171?337

I '14:— 18,917M'19:-- ?I '20:— 527

Diamine Rose

THIOBENZENYL DYESChromine G

Thioflavine T

I '14:—M'18:—M'19:—M'20:—

5,269??

I ' 1 4 : — 1,001

I ' 1 4 : — 3 5 , 2 2 4

I ' 2 0 : — 5,807

l - N a p h t h o l - 3 : 8 -

d i s u l f o r d c A c i d

l - N a p h t h o l - 4 : 8 - d i s u l -

f o n i c A c i d or 1 - N a p h -

t h o l - 3 - s u l f o n i c A c i d

or 1 : 8 - D i h y d r o x y -

n a p h t h a l e n e - 4 - s u l -

f o n i c A c i d

l - C h l o r o - 8 - n a p h t h o l -

3 : 6 - d i s u K o t d c A c i d

[Sul fur , M e t h y l a t i o n ,

S u l f o n a t i o n ]

[ M e t h y l a t i o n ]

D

D

D

D

B

Dehydro-thio-^-toluidine-sulfonic Acid

IV-Amino~5-methyl--2--phenyl4hiazol-sulfonic Acid

D T S {abbreviation for above in compounds, less NH2)

l-(4-Amino-?-sulfo-phenyl)-5-methyl-fcenzothiazole (C. A. nomen.)

C H s | \ C. . N H 2 = C 1 4 H i 2 N 2 O 3 S 2 = 3 2 0


STATISTICS.—Manufactured ' 19:— ?Manufactured '20:—51,961 lbs.

FORMATION.—By sulfonation of the "primuline melt" (from p-toluidineand sulfur), and purification from the primuline-sulfonic acid alsoformed

LITERATURE.—Cain, Intermediate Products (2d Ed.), 78Lange, Zwischenprodukte, #2237Ullmaim, Enzy. tech. Cherrde, 3, 677

Dyes Derived from Dehydro-thio-^-toluidine-sulfonic Acid






16

17

18

51

190

193

STILBENE DYESCurcuphenine

Chlorophenine

Diphenyl FastYellow

I '14:— 10,2291,102

MONOAZO DYESNitrophenineThiazol Yelow R

Alkali BrownBenzo Brown 5R

Clayton Cloth RedStanley Red

I '14M'20

M'19:-M'20:-

I '14M'18M'19M'20

:— 423:— ?

?2,*987

:— 100

'.— ?. ?

Dehydro-tMo-p-tolui-dine-sulfonic Acid(2 mols)

p-Nitro-toluene-o-sul-fonic Acid (4 mols)

Dehydro~thio-p-tolui-dine-sulfonic Acid(2 mols)

p-Nitro-toluene-o-suL-f onic Acid (4 mols)

[Reduction]

D ehydro-thio-p-tolui-dine-sulfordc Acid(2 mols)

Dinitro-dibenzyl-disul-f onic Acid orDirdtro-stilbeiie-

disulf onic Acid

p-Nitro-aniline

7n-Phenylene-diamine

/3-Naphthol

D

D

D

D

A


Dyes Derived from Dehydro-tMo-£-toluidine~sulfonic Acid (continued)


194

196

198

199

209

350

617


MOXOAZO DYES

(continued)Rosophenine 10BThiazine Red R

Titan Red

Clayton YellowThiazol YellowMimosa C

Oriol YellowCotton Yellow R

DISAZO DYETerracotta FC

Alkali Yellow R

THIOBENZENYL DYEChloramine YellowDiamine Fast YellowColumbia Yellow


Manufacture

I '14:— 3,077M'19:— ?M'20:— ?

I '14:— 886M'19:— ?M'20:— ?

I '14:— 29,879M'lS:— ?M'19:— ?I '20:— 11,182M'20:— ?

I '14:— 13,416I '20:— 125M'20:— ?

I '14:— 551

I '14:—180,497M'17:— ?M'18:—123,816M'19:— 54,077I '20:— 4,810M'20:—100,248



Schaeffer's Acid

Dehydro-thio-p-tolui-dine-sulfonic Acid(2 mols)

Salicylic Acid

NaphtMonic Acidm-Phenylene-diamine


[Oxidation]


D

D

D

D

D

D

D

Dehydro-thio-m-xylidine

IV-Amiao-2-phenyl-5:7: III-trimetiyl-thiazol

l-(4-Amino-m-tolyl-)-3:5-dimethyl-&erLzothiazole (C. A. nomen.)

CH3




185

FORMATION.—From m-xylidine and sulfur by heating to the boilingpoint until there is no further evolution of hydrogen sulfide; and byseparating by distillation from the excess m-xylidine, and by solutionin 30% hydrochloric acid from the {so-dehydro-thio-m-xylidine

LITERATURE.—Lange, Zwischenprodukte, #2232Cain, Intermediate Products (2d Ed.), 80Anschutz and Schultz, Ber., 22, 582 (1889)Paul, Zeitsch. angew. Chem., 9, 679 (1896)

Dyes Derived from Dehydro-thio-m-xylidine


120

121

122


MONOAZO DYESSalmon Red

Erica B

Erica G


Manufacture

M'20:— ?

I '14:— 5,349I '20:-- 2,393M'19:— ?

I 14:— 2,370I '20:— 1,142M'18:— ?


Amino-R Acid

l-Naphthol-3:8-disulf onic Acid

GAcid


D

D

D

fso-Dehydro-thio-m-xylidine

l-(6-Amino-w-tolyl)-3: 5-dimethyl-6enzothiazole (C. A. nomen.)

= 268

FORMATION.—As a by-product in the manufacture of dehydro-thio -mxylidine (see dehydro-thio-m-xylidine)

LITERATURE.—See dehydro-thio-m-xylidine

Heumann, Aailinefarben, 4, 752


Dyes Derived from fso-Dehydro-thio-m-xylidine


123


MONOAZO DYEEmine Red



Used and Notes

Schaeffer's Acid


A

Delta Acid


and 2-Naphthylamine-7-sulf onic Acid

1:6-(or 1:7-)Diacetamido-anthraquinone

H 3 C.OC.NH

r. NH.CO.CH3o\y\

I j =Ci8H1

FORMATION.—The above intermediate is obtained by reduction andacetylation of the easily soluble dinitro-anthraquinone, preparedfrom the crude dinitration product of anthraquinone.

LITERATURE.—Ger. Pat. 72,685, 198,048Lange, Zwischenprodukte, #3218

Dyes Derived from 1:SchuitzNumberfor Dye

812

813



IndanthreneOrange RT

IndanthreneCopper R

6-(or 1:7-)Diacetamido-anthraquinoneStatistics ofImport andManufacture

I '14:— 2,103I J20:— 382

I '14:— 1,268





V

V


Diacetyl-o: o'-dinitro-benzidine

Diacetyl-3: 3'niinitro-benzidine (numbering from point of attach-ment)

2:2/-Dinitro-p:p/-biacetanilide (C. A. nombn. with numbering fromu chief function" or the acetamido groups)

O2N

H,COC.HN<

N02

>NH.COCH3 = <

FORMATION.—Benzidine is acetylated by boiling with acetic acid undera reflux, and the resulting diacetyl-compound is nitrated by dissolv-ing in 10 parts of nitric acid (sp. gr. 1.48) with cooling

LITERATURE.—Beil, IV, 964Brunner and Witt, Ber. 20, 1024 (1887)

Dye Derived from Diacetyl-o: o'-dinitro-benzidine


715


SULFUR DYEThiocatechine



Used and Notes

[Sulfur and NasS]


S

£-(2:4-Diamino-anilino)-phenol (C. A. nomen.)

See, 2:4-Diamino-4/-hydroxy-diphenyla,mine

1:4-Diamino-anthraquinoue

CO,

co

NH2

NH2

FORMATION.—From l-nitro-4-amino-anthraquinone (derived from 1-amino-anthraquinone) by reduction with alkaline sodium sulfide

LITERATURE.—Lange, Zwischenprodukte, #3221, 3232, 3233Ullmann, Enzy. tech. Chemie, 1, 477


Dyes Derived from l:4-Diamino-anthraquinone


816

873

Ordinary Xame andClass of Dye


Algol Red 5G

HelindoneBiwn AN


I '14 — 1,338I '20:— 51

I '14:— 2,831I '20:— 16,290



1-Bromo-anthraquinone(2 mols)


V

V

1:5-Diamino-anthraquinone

I | =Ci4H10N2O2 = 238AnnA/

H2X

FORMATION.—(1) From 1:5-dinitro-anthraquinone by reduction.(2) From 1:5-anthraquinone-disulfonic acid by treatment withammonia

LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 477Lange, Zwischenprodukte, #3109, 3115, 3222, 3265

Dyes Derived from 1: 5-Diamino-anthjaquinone

SchvUzNumberfor Dye

817

819

828


ANTHRAQUTSONE ANDALLIED DYES

Algol Yellow R

Algol Red R

IndantkreneBordeaux B


Manufacture

I '14:— 4,887I '20:— 2,299

M'20:— ?

I '14:— 2,322I '20:— 7,335

I '20:— 2,741




[Oxidation]

2-Chloro-anthraquinone(2 mols)


V

V

V


Dyes Derived from l:5-Diamino-anthraquinone (continued)


845

848



(continued)Indanthrene

Maroon B,

IndanthreneGray B


Manufacture

I '20:— 46

I '14:— 401I '20:— 2,639


1:5-Diamino-anthra-quinone (2 mols)

1:5-Diamino-anthra-quinone (2 mols ?)


V

V

Diamino-anthraquinones

(Probably a mixture of the 1:4, 1' 5 and 1:8)

cCSchultzNumberfor Dye836

Dyes DerivedOrdinary Name andClass of DyeANTHRAQUINONE ANDALLIED DYESHelindoneBrown 3GN

from. Diamino-anthraqumonesStatistics ofI?ri port andManvfactureI '20:— 15,238

Other IntermediatesUsed and Notes2-Anthraquinonyl-ureachloride (2 mols)

DyeAppli-cationClassV

4:8-Diamino-anthrarufinH2N co OHllw A.> XJ.2FORMATION.—1: 5-Dinitro-anthraquinone is partly reduced, giving 1: 5-dihydroxyamino-anthraquinone, which is then transformed intodiamino-anthrarunnLITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 275


Dyes Derived from 4:8-Diamino-anthrarufin

SckulizNumberfor Dye

820

821


ANTKRAQTTINONE ANBALLIED DYES

Algol BrilliantViolet R

Algol BrilliantViolet 2B


Manufacture

I '14:— 12,784I '20:— 7,856

I '14:— 3,893I '20:— 827


Diamino-anthraruiSn(2 mols)

[Succinic Acid]

Benzoyl cMoride(2 mols)


V

V

Diamino-azoxy-toluene

p-Azoxy-o-toluidine

5: S'-Azoxy-bis-o-foluidine (C. A. nomen.)

= C14H16X4O = 256

NH2

FORMATION.—From 5-rdtro-o-toluidine (NH2 = 1) by reduction, usingzinc dust and caustic soda


SchvMzNumberfor Dye

483

484

Dyes Derived


TEISAZO DYESSt. Denis RedRosophenine 4B

Milling Scarlet B,S

from Diamino-azoxy-toluene


I '14:— 1,496I '20:— 550


Nevile-Winther's Acid(2 mols)

Nevile-Winther's AcidRAcid


D

A


4:6-Diamino-m-benzene-disulfonic Acid (C. A. nomen.)

See, m-Phenylene-4iamine-disulfonic Acid

2:5-Diamino-benzene-sulfonic Acid (C. A. nomen.)

See, p-Phenylene-diamine-sulfonic Acid

6: 6'-Diamino-m: m'-bi(benzene-sulfonic) Acid (C. A. nomen.)

See, Benzidine-disulfonic Acid

2:2/-Diamino-5: S'-bi-m-toluene-sulfonic Acid (C. A. nomen.)

See, o-Tolidine-disulfonic Acid

1:4-Diamino-2:3-dibromo-anthraquinone

191

c C

NH2

g =(

FORMATION.—By brominating 1:4-diamino-anthraquinone, probably innitro-benzene solution. (The corresponding chloro-compound ismade by action of sulfuryl chloride)

LITERATURE.—Cf. Lange, Zwischenprodukte, #3334Barnett, Anthracene and Anthraqirinone, 170-175, 190-

231

Dyes Derived from l:4-Diamino-2:3-dibromo-anthraquinone

ScktdtzNumberfor Dye

847


ANTHRAQUINONE ANDALLIED DYE

Algol Green B


Manufacture

I '14:— 2,796I '20:— 527


l:4-Diairdno-2:3-di-bromo-anthraqui-none (2 mols)


V


2:7-Diamino-9-dioxide-?: ?-<f ibenzothiophene-disulfonic(C. A. nomen.)

See, Benzidine-sulfon-disulfonic Acid

p: /-Diamino-diphenylamine

prp'-Imino-bisaniline (C A. nomen.)

>NH2 =Ci2H 1 3 N 3 =199

Acid

STATISTICS.—Imported '14:—very small amount

FORMATION.—Equal molecules of aniline and p-phenylene-diamine areoxidized at 0° by means of potassium permanganate to a blue in-damine, which is then reduced with zinc dust and hydrochloric acid

LITERATURE.—Nietzke, Ber., 16, 474Lange, Zwischenprodukte, #1636, 1753

Dye Derived from j&:j&'-Diamino-diplienylamine

SchuttzNumberfor Dye




Used and Notes


923

ANILINE BLACKGROUP

Furreine DB I '14:— 54,005 p.M'19:— ?I '20:— 1,600

M'20:—168,459

•: p'-DiaTTiin o-diphenyl-amine (x mols) (?)

[Oxidation on hair]

Fur

4:4'-Diamino-diphenyl-3: S'-disulf onic Acid

See, Benzidine-disulfonie Acid

jp:^'-Diainiiio-diphenylethylene-o: o'-disulfonic Acid

See, Diamino-stilbene-disulfonic Acid

p: ^'-Diamino-diphenyl-met&ane

p:p'-Methylene-bisaniline (C A. nomen.)



FORMATION.—50 parts of anhydro-formaldehyde-aniline (from equalparts of aniline and 40 per cent formaldehyde), 100 parts of anilineand 70 parts of aniline salt are heated together on a water bath,condensing to the p: p'-diamino-diphenyl-methane

LITERATURE.—Schultz, Farbstofftabellen (1914), #511Lange, Zwischenprodukte, #1297

Dyes Derived from ^://-Diamino-diphenyl-raethane


298

511

540


DlSAZO DTEMilling Red R

TRIPHENTL-METHANEDYES


Pacific Blue


I 14 — 65,026M'18:— ?M'19:—• ?M'20:— ?


R Acid (2 mols)

AnilineNitro-benzene

Anilineo-Toluidinep-Toluidine[Sulfonation]

or[p-Rosaniline+Benzoicacid and sulfonation]


A

B

D

p: ^'-Diamino-diphenyl-sulfide

See, Thioaniline

4:4/-Diamino-diphenyl-2:2'-sulfon-disul£onic Acid

See, Benzidine-sulfon-disulfonic Acid

Diamino-diphenyl-urea-disulfonic Acid

5.5/-Ureido-bis(2-amino~?)enzene-sulfonic Acid) ( C A. nomen.)

H O 3 S v ^

-NH—CO—NH


FORMATION.—24 Parts of 4-nitro-amino-benzene-3-sulfonic acid is dis-solved in water containing 5.5 parts of soda ash, and phosgeneconducted in until the reaction is completed, as indicated by testnot diazotizing. The dinitro-body is now reduced with iron

LITERATURE.—Lange, Zwischenprodukte, #1823.

Dye Derived from Diamino-diphenyl-urea-disulfonic acid

SchultzNumberfor Bye

297


DISAZO DYEBenzo Fast

Pink2BL


I '14:— 3,252I '14:—- 1,226


Gamma acid (2 mols)


D

p: ^'-Diamino-ditolyl-amine

4:4/-Imino-bis-o-^oluidine (C A. nomen. NH2=il)

H3C CH3

) ^ ) = C14H17N2 = 227

FORMATION.—By semidine rearrangement of amino-azo-0-toluenewhereby the hydrochloride of amino-azo-0-toluene is dissolved insulfurous acid solution and reduced with zinc dust, the productpoured into 50 per cent sulfuric acid, boiled and crystallized

LITERATURE.—Barber and Sisley, Sur un noveau mode de formation dela p-diamino-diphenylamine

Bull. Soc. Chim. [3] 33, 1232-34 (1905)Chem. Centr. 1906 [1], 232

Dye Derived from ^i^'-Diamino-ditolyl-amine


295


DISAZO DYEDiphenyl Fast Black


I J14:— 882


Gamma Acidw-Tolylene-diamine


D


p: /-Diamino-ditolyl-methane

4:4'-Methylene-bis-o-2oluidine (C. A. nomen.)

H3C CH3

^ I 2 ^ ^ V - N H 2 =

195

FORMATION.—100 parts of anhydro-formaldehyde-aniline + 250 parts ofo-toluidine hydrochloride + 500 parts of o-toluidine are warmedtogether on a water bath; and after 12 hours the mass is made al-kaline and the aniline is distilled off with the aid of steam. (Theanhydro-formaldehyde-aniline is only used as a carrier for the for-maldehyde)


Dye Derived from j&:£'-Diamino-ditolyl-methane

Schultz

for Dye

513


TRIPKENYL-METHANEDYE

New Fuchsine O


Manufacture

I '14:— 300M'18:— ?M'19:— ?'MJ20:— ?


o-Toluidineo-Nitro-toluene


B

Diamino-dixylyl-methane

Methylene-biszylidine (<7. A. nomen)

NH2CH3CH3

NH2CH3CH3

FORMATION.—From formaldehyde and xylidine in the presence of acondensing agent


Dye Derived from Diamino-dixylyl-methane


299


DISAZO DYECinnabax Scarlet BF



Used and Notes

R Acid (2 mols)


CL

Diamino-dixylyl-phenyl-methane

Benzal-biszylidine (JO. A. nomen.)

NH2CHsCH3

NH2CH3CH3

FORMATION.—From benzaldehyde and xylidine in. the presence of acondensing agent


Dye Derived from Diamino-dixylyl-phenyl-methane

SchuUzNumberfor Dye

300


DISAZO DYECotton PonceauCinnabar Scarlet G



Used and Notes

R Acid (2 mols)


CL

Di-^-aroino-ethoxy-diphenyl

See, Ethoxy-benzidine

l:3-Diamino-2-hydroxy-benzene-5-sulfonic Acid

See, 2: 6-Diamino-l-phenol-4-suKonie Acid


2:4-Diamino-4'-hydroxy-diphenylaminep-(2:4-Diamino-anilino)-phenol (C. A. nomen.)

= 2 1 5

197

NH2

FORMATION.—Molecular proportions of 4-chloro-l: 3-dinitro-benzeneand p-amino-phenol are heated to boiling in aqueous suspension withsomewhat more than theoretical amount of limestone. The heat-ing is done by direct steam in a vessel provided with a reflux con-denser. After all the chloro-nitro-benzene has disappeared, theliquid is cooled and the crystalline 2: 4-dinitro-4'-hydroxy-diphenyl-amine is separated and washed. This is then reduced to the de-sired 2:4-diamino-4/-hydroxy-diphenylamine


Dye Derived from 2:


732


SULFUR DYEAutogene Black

4-Diamino-4/-hydroxy-diphenylamine


Manufacture

I 14:— 7,495


Phenol[S.O, S+NasS]


S

a-Diamino-naphthalene1: 5-Diamino-naphthalene (not considered herein)

jS-Diamino-naphthalene1: 8-Diamino-naphthalene (not considered herein)

4:5-Diamino-2:7-naphthalene-disulfonic Acid (C. A. nomen.)

See, 1:8-Naphthylene-diamine-3: 6-disulfonic Acid

4:8-Diamino-2:6-naphthalene-disulfonic Acid (C. A. nomen.)See, 1: 5-Naphthylene-diamine-3: 7-disulfonic Acid

1:4-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)See, 1:4~Naphthylene-diamine-2-sulfonic Acid


2:7-Diajnino-naphthalene-sulfonic Acid (C. A. nomen.)

See, 2: 7-Naphthylene-diamine-sulfonic Acid

5:7-Diamino-2-naphthaIene-suUonic Acid (C. A. nomen.)

See, 1:3-Naphthylene-diamine-6-sulfonic Acid

6:8-Diamino-2-naphthalene~sulfonic Acid (C. A. nomen.)

See, 1: 4-N*aphthylene-diamine-6-sulfonic Acid

2:6-Diamino-l-phenol-4-sulfonic Acid (C. A. nomen. OH—1)

1: 3-Diamino-2-hydroxy-benzene-5-sulfonic Acid

OH

™ ! = 204

SO3]

FORMATION.—Phenol is sulfonated by dissolving in hot sulfurie acid,cooled, diluted, and then dinitrated, using nitric acid and heatingto boiling. The dinitro-phenol-sulfonate is then isolated, dissolvedin water, and reduced with ammonium sulfide, and the diamineprecipitated by acidification

LITERATURE.—Lange, Zwischenprodukte, #1137Cain, Intermediate Products (2d Ed.), 129, 130

Dyes Derived from 2


288

289


DISAZO DYESAcid Alizarin

Black SEPalatine Chrome

Black F

Acid AlizarinBlack SN

Palatine ChromeBlackS

: 6-Diamino-l-phenol-4-sulfonic Acid


Manufacture

I '14:— 19,185I '20:— 34,302

M '17:— ?M'18:— ?M 19:— ?


0-Naphthol (2 mols)

/3-NaphtholSchaeffer's Acid


ACr

ACr


Diamino-stilbene-disulfonic Acidp: p'-Diamino-diphenylethylene-a: o'-disulfonic Acid

DS (abbreviation for above in com/pounds, less 2-NH2)

4:4'-Diamino-2:2'-stilbene-disulfonic Acid (<7. A. nomen.)

SO3H HO3S

\ = CuHuNiOflS* = 370

STATISTICS.—Manufactured '17:— ?Manufactured ' 18:— ?Manufactured '19:—5,021 lbs.Manufactured '20.-142,227 lbs.

FORMATION.—From sodium salt of p-nitro-toluene-0-sulfonate by dis-solving in water and boiling with caustic soda until the color be-comes deep red. Then reduction is effected by adding zinc dustuntil the liquid is decolorized



301

302

303

304

305

Dyes Derived from


DISAZO DYESHessian Purple N

Brilliant HessianPurple

Brilliant YellowPaper Yellow

Chrysophenine G

Hessian Yellow

L Diamino-stilbene-disulfonic Acid


I '14:— 465

I '14:—278,000M'17:— ?M'18:— 1,664M'19:— 48,723I '20:— 126M'20:— 91,218

I '14:—157,799M'17.— ?M'18:—41,663M'19:— 86,795I '20:— 3,661M'20:—247,202


jft-Naphthylamine(2 mols)


Phenol (2 mols)

Phenol (2 mols)[Ethylation]

Salicylic Acid (2 mols)


D

D

DA

D

D


3:5-Diamino-^-foluene-sulfonic Acid (C. A. nomen.

l-Tolylene-2: 6-diamine-4-sulfonic Acid

Toluylene-diamine-sulfonie Acid

l-Methyl-2: 6-diainino-benzene-4-sulfoiiic Acid

SO3H

CH3

FORMATION.—From o-nitro-toluene by sulfonation, nitration and re-duction

LITERATURE.—Lange, Zwisehenprodukte, #1096

Dyes Derived from 3:5-Diamino-p-toluene-sulfonic Acid


285

286

287

488


DISAZO DYESTohiylene Brown G

Toluylene Yellow

ToluyleneOrange RR

TETHAKTSAZO DYEToluylene Brown R


Manufacture

I '14:— 5,485

I '14:— 500

I '14:— 201


m-Phenylene-diamine

Nitro-m-phenylene-diamine (2 mols)

j3-Naphthylamine(2 mols)




D

D

D

D

4:6-Diamino-m-^oluene-sulfonic Acid (C. A. nomen.

w-Tolylene-diamine-sulfonic Acid

7n-Toluyleneniiannne-suKonic Acid

l-Methyl-2:4-diamino-benzene-5-sulfonic Acid

SO3H

= 2 0 2


STATISTICS.—Manufactured in 1918, 1919, 1920, but in undisclosedquantities

FORMATION.—By addition of m-tolylene-diamine sulfate to oleum, andheating the mixture for three hours on a water bath.


Dyes Derived from 4: 6-Diamino-m-toluene-sulfonic Acid (SOZH = 1)


362

392


DISAZO DYESToluylene Orange ROxydiamine

Orange R

Toluylene Orange G


Manufacture

I '14:— 25,908M'19:— ?I '20:— 1,653

I '14:— 67,022M'18:— ?M'19:— ?M'20:— ?I '20:-- 273


Tolidine4: 6-Diamino-m-

toluene-sulfonicAcid (2 mols)

Tolidineo-Cresotic Acid


D

D

Dianisidineo-Dianisidine

D (abbreviation for Dianisidine in compounds, without the 2-NH2

groups)

O O.CH 3

/ ~ ^ = Ci4Hi6N2O2 = 244

STATISTICS.—Imported '14:—10,656 lbs.Manufactured '17:—11,702 lbs.Manufactured ' 18:— ?Manufactured '19:—107,441 lbs.Manufactured ;20:— ?

FORMATION.—o-Nitro-anisole is reduced by zinc dust in presence ofcaustic soda and alcohol to hydrazo-anisole, which is rearranged todianisidine by being warmed with dilute sulfuric acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 96I^ange, Zwischenprodukte, ^1204


Dyes Derived from Dianisidine



DISAZO DYESBenzopurpurin 10B

Diazurine B

Azo Violet

Dianisidine Blue

Azophor Blue D

Azophor Black S

Trisulfon Blue B

Benzoazurine G

Benzoazurine 3G

Congo Blue 2B

Direct Violet BB

I '14:M'18:M'19:M'20:I '20:


Manufacture

47,768??

41,2652,205

I '14:-

I '14:—

140

813

I '14:— 7S,699M'18M'19I '20M'20

-150,589- 287-237,328

I '20:— 201

I '14:— 4,396



l-Naphthylamine-6-sulf onic Acid (2 mols)

0-Naphthol (2 mols)

Naphthionic AcidNevile-Winther's Acid

/3-Naphthol (2 mols)

[Stable tetrazo-dianisoleused with p-nitro-aniline]

[Stable tetrazo-dianisolemixed with diazo m-nitro-aniHne, etc.]

l-Naphthol-3:6:8-trisulfonic Acid

i8-Naphthol


l-Naphthol-5-sulfonic(2 mols)

It AcidNevile-Winther's Acid

1:7-Dihydroxy-naph-thalene-4-sulfonicAcid

w-Tolylene-diamine


D

D

D

ME

MF

D

D

D


Dyes Derived from Dianisidine {continued)

SchulizNumberfor Lye




Used and Notes


414

415

416

417

418

419

420

421

422

DISAZO DYES{continued)

Indazurine B

Dianil Blue G

Brilliant Azurine 5G

Chlorazol Blue3G or R

Diamine BrilliantBlueG

Chicago Blue RW

Azidine Wool Blue B

Oxamine Blue B

Chicago Blue 4B

M'19:-

M'20:-

I '14:-I '20:-

22,3241,563

I '14:— 10,151

I '14:-I '20:-

I '14:-M'19:-I '20:-

M'20:-

11,59251

15,176?351

I '14:-I '20:-

I '14:-

35,89113

8,269

1:7-Dihydroxy-naph-thalene-4-sulfonic Acid

RAcid

Chromotropie Acid(2 mols)

1:8-Dihydroxy-naph-thalene-4-sulfonic Acid(2 mols)

l-Chloro-8-naphthol-5-sulf onic Acid (2 mols)

orl-Chloro-8-naphthol-4-

sulf onic Acid (2 mols)

l-Chloro-8-naphthol-3:6-disulf onic Acid(2 mols)


iS-Naphthol

Croceine Acidl-Amino-8-naphthol-

4-sulfonic Acid

l-Amino-5-naphthol-7-suKonic Acid

Nevile-"Wlnther's Acid




Dyes Derived from Dianisidine (continued)


423

424

425

426

427

428

429

430

455



Chicago Blue B

Chicago Blue 6B

Benzo Cyanine 3B

Diamine Pure BlueBenzaminePure

Blue

Indazurine GM

Direct Blue B

Indazurine BB

Indazurine 5GM

TRISAZO DYESColumbia Black B

M'18:— ?

I '20:M '20:


Manufacture

k—118,5423:— ?

7,480?

I '14:— 1,001

I '14:M '17:M'18 :M'19:

'20:M J20:

I '14:M'17:M'18:I '20:

12,881??

192,350652

223,100

21,42114,823

?7,055

I '14:—165,727


l-Amino-8-naphthol-4-sulf onic Acid (2 mols)

l-Amino-8-naphthol-2:4-disulfonic Acid(2 mols)

H Acidl-Ainino-8-naphthol-4-

sulf onic Acid

H Acid (2 mols)

1:7-DIhydroxy-2-napli-thoic-4-sulfonic Acid


1:7-DIhydroxy-6-naph-thoic-3-sulf onic Acid


1:7-Dmydroxy-2-naph-thoic-4-sulf onic Acid

RAcid

1:7-Dihydroxy-2-naph-thoic-4-sulf onic Acid

H Acid

2 R Acidm-Tolylene-diamine

(2 mols)

DyeAppli-cation


Dyes Derived from Dianisidine (continued)

205


456

457



Congo Fast Blue BBenzo Fast Blue B

TrisulfonBrown GG


Manufacture

I '14:—100,495I '20:— 1,821

I '14:— 7,562I '20:— 38,411


a-Naphthylaminel-Naphthol-3: 8-disul-

fonic Acid



D

D

Dibenzo-pyrroleSee, Carbazole

Dibenzyl-aniline-sulfonic (disulfonic) Acid[(iVr-Benzyl-anilino)-methyl]-6enzene-sulfonic Acid (C A. nomen.)

C6H5. CH2—N—CH2. C6H4. SO3H

FORMATION.—Aniline, benzyl chloride and sodamide are mixed togetherand then heated up on water bath until ammonia is all off, resultingin the formation of dibenzyl-aniline. This latter is then sulfonated


Dye Derived from Dibenzyl-aniline-sulfonic (disulfonic) Acid


531



Eriocyanine A


Manufacture

I '14:— 25,091I '20:— 8,223


Tetramethyl-p: p'-dia-roino-benzohydrol-sulfonic Acid

[Oxidation]


A


5:7-Dibromo-2-chloro-3-pseudoindolone (C. A. nomen.)

See, 5:7-Dibromo-isatin Chloride

5:7-Dibromo-isatin Chloride

5: 7-Dibromo-2-chloro-3-23Seudoindolone (C A. nomen.)

Br N

( Y CB r

C . Cl = C8H2Br2ClNO = 323.5

FORMATION.—Isatin is gently wanned with bromine in concentratedsulfuric acid, giving 5:7-dibromo-isatin, which is then wannedwith phosphorus pentachloride and benzene

LITERATURE.—Ullmann, Enzy. tech. Chemie, 6, 526Lange, Zwischenprodukte, #2122

Dyes Derived from 5:7-Dibromo-isatin Chloride


893

895


INDIGO GROUP DYESAlizarin Indigo G

Alizarin Indigo ZR


Manufacture

I '20:— 1,596

I '20:— 3,514


1-Anthrol

a-Naphthol


V

V

2:6-DicMoro-aniline

NH2

FORMATION.—From 2:5-dichloro-nitro-benzene by reduction with ironand hydrochloric acid

LITERATURE.—Cain, Intermediate Products (2d Ed.)> 50


Dyes Derived from 2:5-Dichloro-aniline

207


218

469

470

471

472


DISAZO DYENigrophor BASF

TEISAZO DYESChloramine

Black N

ChloramineGreen B

ChloramineBlue 3G

ChloramineBlueHW


I '14:— 39,600M'19:— ?I '20:— 1,763M '20:— ?

I '14:— 1,675M'19:— ?M'20:— ?

I '14:— 286M'19:— ?I '20:— 882



p-Nitro-aniline

Benzidinem-Phenylene-diamineHAcid

BenzidinePhenolHAcid

BenzidineH Acid (2 mols)

BenzidineGamma AcidHAcid


MF

D

D

D

D

1:5-Dichloro-anthraquinone

Cl

Y J =C1 4H6Cl2O2=277

FORMATION.—Sodium 1: 5-anthraquinone-disulfonate in dilute hydro-

chloric acid is heated to boiling and treated with a solution of

sodium chlorate

LITERATOBE.—Cain, Intermediate Products (2d Ed.), 250Lange, Zwischenprodukte, #3083, 3086Ullmann, Enzy. tech. Chemie, 1, 472


Dye Derived from l:5-Dichloro-anthraquinone


832



IndanthreneViolet RN


Manufacture

I '14:— 11,667I '20:— 49


Anthranilic Acid(2 mols)


V

2:6-Dichloro-anthraquinone

X ? -0

FORMATION.—2:6-Anthraquinon.e-disulforue acid is treated withchlorine

LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 472Cf. Ber., 37, 4706Lange, Zwischenprodukte, #3164, 3165

Dyes Derived from 2:6-Dichloro-anthraquinone


826

829


ANTHH A QUINONE ANDALLIED DYES

Indanthiene Red G

Algol Bordeaux 3B


I '20:— 61


1-A miTi o-anthraquiaone(2 mols)

l-Amino-4-metlioxy-anthjaquinoiie (2 mols)


V

V

2:7-Dichloro-anthraqvdnone

= C l 4 H 6 C l 2 ° 2 = 2 7 7


FORMATION.—From anthraquinone-2:7-disulfonic acid by treatmentwith hydrochloric acid and sodium chlorate; or better from 9:10-dichloro-anthracene-2: 7-disulfonic acid by treatment with the samereagents

LITERATURE.—Ullmann, Enzy. tech. Chemie, 1, 472Lange, Zwischenprodukte, #3165

Dyes Derived from 2:7-Dichloro-anthraquinone


827

830



IndanthreneBordeaux B extra

Indanthrene Red R


I '14:— 28,728I '20:— 4,056

I '14:— 2,099I '20:— 6,595


l-Amino-6-chloro-an-thraquinone (2 mols)

1-Amino-anthraquinone(2 mols)


V

V

2:5-Dichloro-benzaldehyde

HCO

FORMATION.—From 2-chlor-5-mtro-benzaldehyde by the substitutionof the nitro group by chlorine

LITERATURE.—Lange, Zwischenprodukte, #669Beil, III , 13

Dyes Derived from 2:5-Dichloro-benzaJdehyde


497

501



New Fast Green 2BVictoria Green 3B

Glacier BlueBrilliant Glacier

Blue


Manufacture

I '14:— 44,595

I '14:— 2,495



[Oxidation]

Methyl-o-toluidine(2 mols)

[Oxidation]


B

B


o: o'-Dichloro-benzidine

2: 2'-Dichloro-benzidine (C. A. nomen. NH2=1)

3: 3'-Dichloro-benzidine (Usualnumbering, 'point of attachment = 1)

Cl Cl

= CiaHioCljNa = 253

FORMATION.—(1) By chlorinating of diacetyl-benzidine, and hydrolyz-ing product. (2) By reducing o-chloro-nitro-benzene in alkalinesolution with zinc, and rearranging with acid the o: o'-dichloro-hydrazo-benzene formed (similar to benzidine formation from nitro-

benzene)

LITERATURE.—Cain, Intermediates (2d Ed.), 94Lange, Zwischenprodukte, #1229, 1230

Dyes Derived from o: o' Dichloro-benzidine

SchuLtzNumberfor Dye

356

357

358


DISAZO DYESDianol Red 2B

Dianol Red B

Brilliant Dianol RedR extra

Diphenyl Red


Manufacture

I '14:— 4,422I '20:— 17,632

I '14:— 14,305I '20:— 3,704




Amino-R Acid(2 mols)


D

D

D

2:5-Dichloro-4~(4: 5-dihydro-5-keto-3-methyl-l-pyrazolyl)-6en-zene-sulfonic Acid (C. A. nomen,)

See, l-(2 /: S^Dic

2:5-Dichloro-nitro-benzene

NO2


FOKMATION.—By nitration of p-dichloro-benzene with mixed acidLITERATURE.—Cain, Intermediate Products (2d Ed.), 14


USES.—For preparing 2: 5-dichloro-aniline

3:6-Dichloro-£hthalic Acid

COOH

C I / N C O O H

V C 1= C8H4CI2O4 — 235

STATISTICS.—Imported '14:—very smallManufactured '18:— ?

FORMATION.—(1) From dichloro-naphthalene tetrachloride, by oxida-tion with nitric acid. (2) From phthalic anhydride dissolved inoleum by chlorination in presence of iodine, and by separation fromthe isomers formed at the same time

LITERATURE.—Lange, Zwischenprodukte, #992Cain, Intermediate Products (2d Ed.), 165

Dyes Derived from 3:6-Dichloro-phthalic Acid

tSchuiteNumberfor Dye

584

593


XANTHONE DYESFast Acid

BlueR

Phloxine P


Manufacture

I '14:— 3,022I '20:— 130

I '14:— 2,244M'17:— ?M'18:— ?M '19:— ?M'20:— ?


Resorcinol (2 mols)p-Phenetidine (2 mols)[PC15; Sulfonation]

or[Tetrachloro-fluores-ceine and p-phene-tidine; Sulfonation]

Resorcinol (2 mols)[Bromination]

or[Dichloro-fluoresceine

brominated]


A

A


Dyes Derived from 3


594

595


XANTHONE DYES(continued)

Cyanosine, SpiritSoluble

Rose Bengal

: 6-Dichloro-phthalic Acid (continued)


Manufacture

I '14:— 2,277M'20:— ?


Resorcinol (2 mols)[Bromination, methyla-

tion]or

[Phloxine P methylester]

Resorcinol (2 mols)[Iodation]

or[Dichloro-fiuoresceine

iodated]


A

A

l-(2:5-Dichloro-4-snlfo-phenyl)-3-methyl-5-pyrazolone

2: 5-Dichloro-4-(4 roniihydr o-5-ket o-3-methyl-l-py r azoly 1) -&en-

zene-sulfonic Acid (C. A. nwnen.)

Cl

N

C 1

2C—C • CH3

FORMATION.—^2:5-Dichloroaniline-4-sulfonic acid is diazotized and re-

duced to 2:5-dichloro-phenyl-hydrazirie-4-sulfonic acid, which latter

body by condensation with ethyl acetoacetate forms the above

pyrazolone derivative




Dye Derived from l-(2:5-Dichloro-4-sulfo-phenyl)-3-methyl-5-pyrazolone


22


PYRAZOLONE DYEXylene YeUow 3G


Manufacture

I 14:— 23,074I '20:— 77,782


Sulfanilic Acid


A

jp-Diethylamino-azo-benzeneBenzene-azo-diethylanilineiV":iV-Diethyl-p-plienylazo-aniline (C. A. nomen.)

)N 2 <Q)N(C2H 5 ) 2 = Ci6Hi9N3=253

FORMATION.—By coupling diazo-benzene chloride (diazotized aniline)with diethyl-aniline


Dyes Derived from ^-Diethylamino-azo-benzene


641

646


OXAZINE DYESCoreine ERCoelestine Blue B

Coreine Alt


Manufacture

I 14:— 1,320I J20:— 44


Gallamide

GaJlamideAniline[Sulfonation]

or[Coreine E.R, Aniline,

Sulfonation]


M

M

^-Diethylamino-benzoyl Chloride

COC1

= 211.5


FORMATION.—(1) p-Amino-benzoic acid is ethylated, and then treatedwith phosphorus pentachloride to form the desired acid chloride.(2) Diethyl-aniline is subjected to the action of phosgene first atordinary temperatures until no more gas is absorbed, and then aftermelting the crystalline mass first obtained. The product is mixedwith water and the excess of diethyl-aniline removed by acetic acid.The acid chloride is formed by treatment with phosphorus penta-chloride


Dye Derived from ^-Diethylamino-benzoyl Chloride


534


TRIPHENYL-METHA2STEDYE

Acid Violet 7B


Manufacture

I '14:— 21,665I '20:— 51


iV-Methyl-diphenyl-amine (2 mols)


A

3-Diethylamino-^-cresol (C. A.nomen.0H=l)

Diethyl-wz-amino-p-cresol (OH=1)

OH

Q N ( C 2 H 5 ) 2 = C n H

CH3

FORMATION.—From diethyl-o-toluidine by sulfonation in the cold with

oleum and caustic soda fusion of the sulfonic acidLITERATURE.—Mohlau, Klimmer and Kahl, Zeit. Farb. Chem., 1902

316Lange, Zwischenprodukte, #815

Dye Derived from 3-Diethylamino-^-cresol (OH=1)


620


OXAZINE DYECapri Blue GON


T 14:— 128


Nitroso-dimethyl-ani-line


B


Diethyl-m-amino-jfr-cresol (OH=1)

See, 3-Diethylamino-p-cresol (C A, nomen. OH=1)

5-Diethylaznino-2-nitroso-£henol (C. A. nomen.)

Nitroso-diethyl-m-amino-phenol

OH

215

FORMATION.—Diethyl-m-amino-phenol (which can be prepared by sul-fonating diethyl-aniline and then fusing the sulfonic acid to pro-duce the diethyi-m-amino-phenol) is dissolved in hydrochloric acid,cooled with ice to 0° C , and sodium nitrite solution introduced


Dyes Derived from 5-Diethylamino-2-nitroso-phenol


653

654


OXAZINE DYES

Nile Blue A

Nile Blue 2B


Manufacture

I '14:— 1,518I '20:— 1,241


a-Naphthylamine

Benzyl-a-naphthyl-amine


B

B

m-Diethylamino-^henol (C. A. nomen.)

Diethyl-m-amino-phenol

OH

J N ( C 2 H 5 ) 2

STATISTICS.—Manufactured ' 18:— ?Manufactured '19:— ?Manufactured '20:— ?

FORMATION.—Diethyl-aniline is sulfonated with oleum, and the re-sulting diethyl-aniline-m-sulfonic acid fused with caustic soda

LITERATURE.—Cain, Intermediate Products (2d Ed.), 122Lange, Zwischenprodukte, #603-606, 2263


SchuUzNumberfor Dye

570

572

573

574

579

581

Dyes Derived


XANTHONE DYESRhodamine S

Rhodamine G

Rhodamine B

Rhodamine 3B

Sulfo Rhodamine BXylene Red B

Fast Acid Eosine GFast Acid

Phloxine A

from m-Diethylamino-phenol

II

II

IMMMMI

I

II


'14:-'20:-

'14:-'20:-

'14:-'17:-'18:-'19:-'20:-'20:-

'14:-

'14:-'20:-

- 600- 273

- 2,648- 517

- 59,354- ?- ?- ?- ?- 24,709

- 1,698

- 650- 5,234


Diethyl-m-amin o-phenol (2 mols)

[Succinic Anhydride]

Phthalic AnhydrideDiethyl-m-amino-

phenol (2 mols)Aniline [Removes one

C2H5 group]or

[Rhodamine B heatedwith Aniline Salt]


phenol (2 mols)


phenol (2 mols)[Ethyl esterification]

or[Rhodamine B

ethylated]

Benzaldehyde-di-sulfonic Acid


[Oxidation]

Phthalic AnhydrideDiethyl-m-ainino-

phenol (2 mols)or

[Rhodamine B, sulfo-nated]


A

B

B

B

A

A


Diethyl-anilineN: N-Diethyl-aniline (C. A. nomen.)

N(C2H5)2

STATISTICS.—Imported 14:—very small quantityManufactured 17:— 3,955 lbs.Manufactured 18:—48,048 lbs.Manufactured 19:—30,000 lbs.Manufactured '20:—180,542 lbs.

FORMATION.—Aniline is heated in an autoclave with ethyl alcohol inthe presence of a catalyst, for example, hydrochloric acid, hydro-bromic acid, or iodine


Dyes Derived from Diethyl-aniline

SchvlizNumberfar Dye




Used and Notes


499


Brilliant Green

507

518

Xylene Blue VS

Ethyl VioletEthyl Purple

I 14:— 73,904M 1 8 : — ?M19:— ?I '20:— 25

M'20:— ?

I 14:— 2,130I '20:— 27,254

I 14:— 51,933

Diethyl-aniline (2 mols)Benzaldehyde[Oxidation]

Diethyl-aniline (2 mols)3-Methyl-benzalde-

hyde-4:6-disulfonicAcid

[Oxidation]

Tetraethyl-diamino-benzophenone

orDiethyl-aniline (3 mols)Phosgene

orTetraethyl-diamino-

diphenyl-methane

B


Dyes Derived from Diethyl-aniline {continued)





Used and Notes

DyeAppli-cation

530

543

544

686

TBIPHENYL-METHANEDYES (continued)

Acid Violet 6BFonnyl VioletGuinea Violet

Patent Blue V

Cyanine B

AZINE DYEAmethyst Violet

I '14:—161,624M'17M'18M'19I '20

M'20- 3,925-144,207

-196,228- ?

I '14M'17M'18I '20:— 36,420

'14:-'20:-

8,39824


[Formaldehyde, Oxida-tion}

Diethyl-aniline (2 mols)w^Nitro-benzaldehyde

or m-Hydroxy-benzaldehyde

[Sulfonation, Oxidation]

Diethyl-aniline (2 mols)m-Nitro-benzaldehyde

or m-Hydroxy-benzaldehyde

[Sulfonation, Oxidation]or

[Patent Blue Oxidized]

Diethyl-p-phenylene-diamine

AniHne or p-Toluidine[Oxidation]

Diethyl-aniline-m-sulfonic Acid

N: iV-Diethyl-metanilic Acid (C. A. nomen.)

= C10H15NO3S =

FORMATION.—From diethyl-aniline by sulfonation with oleum

LITERATURE.—Cain , Intermediate Products (2d Ed. ) , 122Lange, Zwischenprodukte, #631


Dyes Derived from Diethyl-aniline-m-sulfonic Acid

219


59


MONOAZO DYEWool Violet S


Manufacture

I '14:— 308M'18:— ?M'19:— ?


2:4-Dinitro-ardline


A

N: N-Diethyl-metanilic Acid (C. A. nomen.)

See, Diethyl-aniline-m-sulfonic Acid

N: iV-Diethyl-^-nitroso-aniline (C. A. nomen.)

See, p-Nitroso-diethyl-aniline

N: iV-Diethyl-^-phenylazo-aniline (C. A. nomen.)

See, p-Diethylamino-azo-benzene

N: iV'-Diethyl-m-plienylene-diamine (C. A. nomen.)

s-Diethyl-m-phen^ lene-diamine

HNC2H5

JNH. C2H5 = C l o H i e N 2 ~ 1 6 4

FORMATION.—Probably by heating resorcinol with ethylamine in thepresence of a dehydrating agent

LITERATURE.—Cf. Green, Organic Coloring Matters (1908), 37.Cf. Calm, Ber., 16, 2792 (1883)

Dye Derived from JV: iNT-Diethyl-m-phenylene-diamine


678


AZENE DYEFast Neutral

Violet B


Manufacture

MJ17:— ?




B


N: JV-Diethyl-p-jphenylene-diamine (C. A. nomen.)

p-Amino-diethy 1-an iline

N(C2H5)2

NH2

FORMATION.—Diethyl-aniline is converted into p-nitroso-diethyl-anilineby nitrous acid, which by reduction with zinc dust and hydrochloricacid yields the p-amino-diethyl-aniline

LITERATURE.—Cf. Lange, Zwischenprodukte, #561-563

Dye Derived from N: iV-Diethyl-/>-phenylene-diamine


686


AZINE DYEAmethyst Violet



Used and Notes

Diethyl-anilineAniline or p-Toluidine[Oxidation]


A

s-Diethyl-m-phenylene-diamine

See, N: iV'-Diethyl-m-phenylene-diamine

Dietlayl-^-phenylene-diannne-thiosiilfonic Acidp-Amino-diethyl-aniline-thiosulfonic Acid

4-Anainc)-lHiiethylamino-benzene-3-thiosuifonic Acid

2-Amino-5-diethylamino-6enzene-thiosulfonic Acid (C. A. nomen.)

N(C2H5)2

FORMATION.—12 parts of the zinc chloride double salt of diethyl-p-phenylene-diamine are dissolved in 90 parts of water, treated witha solution of 25 parts of aluminum sulfate and 20 parts of sodiumthiosulfate in 70 parts of water, and finally oxidized with 3 parts ofpotassium bichromate dissolved in 30 parts of water



Dye Derived from Diethyl-^-phenylene-diamine-thiosulfonic Acid


666


TKLAZINE DYEIndochromogen S



1:2-Naphthoquinone-4: 6-disulfonic Acid


M

3:4-Dihydro-3:4-diketo-l:7-naphthalene-disulfonic Acid (C A.nomm.)

See, 1: 2~Naphthoquinone-4:6-disulfonic Acid

3:4-Dihydro-3:4-diketo-l-naphthalene-sulf onic Acid (C. A.nomen.)

See, 1: 2-Naphthoquinone-4-sulfonic Acid

£-(4 '• 5-Dihydro-5-keto-3-methyl-l-pyrozolyl)-6enzene-snlf onicAcid (C. A. nom&n.)

See, 3-Methyl-l-(p-sulfo-phenyl)-5-pyrazolone


See, Alizarin


See, Anthranifin

2:4-Dihydroxy-benzoic Acid

See, j8-Resorcylic Acid (C A. nomen.)


See, a-Resorcylic Acid (C A. nomen)

m-Dihydroxy-benzoic Acid

See, a-Resorcylic Acid (C. A. nomen.)

1:7-Dihydroxy-2-carboxy-naphthalene-4-sulfonic Acid

See, 1: 7-Dihydroxy-2-naphthoic-4r-sulfonic Acid


1: 7-Dihydroxy-6-carboxy-naphthalene-3-sulfonic Acid

See, 1: 7-Dihydroxy-6-naphthoic-3-sulfonic Acid

Diliydroxy-£-methyl-coumariii

See, 7:8-Dihydroxy-4-methyl-coumarin (C. A. nomen.)

7:8-Dihydroxy-4-methyl-couinarin (C. A. nomen.)

Dihydroxy-0-methyl-coumarin

HO

FORMATION.—From pyrogallol and acetoacetic ethyl ester

LITEKATUEE.—J. pr. Ch. (2) 26, 68Ber., 16, 2127 (1883)

SchvtizNumberfor Dye

773

Dye Derived from



Anthracene Yellow

7:8-Dihydroxy-4-methyl-coumarin


Manufacture

I J14:— 4,046


[Bromination]


M

1: S-Dihydrosy-naphthalene

1:5-NaphthaJenediol (C A. nomen.)

OH

HO

STATISTICS.—Manufactured '19:—Manufactured '20:—


FOBMATION.—By caustic soda fusion of sodium naphthalene-1: 5-disul-fonate or of sodium l-naphthol-5-sulfonate


Dye Derived from l:5-Dihydroxy-naphthalene


157


MONOAZO DYEDiamond Black PV


Manufacture

I '14:—285,074


o-Amino-phenol-p-sulf onic Acid


M

2:7-Dihydroxy-naphthalene

2: 7-Naphthalenediol (C. A. nomen.)

H ° C O ° H =

FORMATION.—By caustic soda fusion of F acid (2-naphthol-7-sulfonicacid)

LITERATURE.—Lange, Zwischenprodukte, #2401Green, Organic Coloring Matters (1908), 54Thorpe, Die. Chemistry, 3, 647

Dyes Derived from 2:7-Dihydroxy-naphthalene


3

655


NITROSO DYEDioxine

OXAZINB DYEMuscarine


Manufacture


[Nitrous Acid]

Nitroso-dimethyl-aiuline


M

B


1:7-Dihydroxy-naphthalene-2-carboxylic-4-sulfonic Acid

See, 1:7-Dihydrox>'-2-naphthoic-4-sulfonic Acid

1: T-Dihydroxy-naphthalene-e-caxboxylic-S-sulfonic Acid

See, 1: 7-Dihydroxy-6-naphthoic-3-siilfonic Acid

1:8-Dihydroxy-naphthalene-3:6-disulfonic Acid

See, Chromotropic Acid

4:5-Dihydroxy-2:7-naphthalene-disulfonic Acid (C. A. norntn.)

See7 Chromotropic Acid

1:7-Dihydroxy-naphtlialene-4-siilfonic Acid

4:6-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)

HO

OH

s o j a

FORMATION.—From 1 hydroxy-naphthaIene-2-carboxylic-4: 7-disulfonicacid by fusion -with alkalis, whereby first a sulfonic group is replacedby hydroxyl and then at a higher temperature carbon dioxide issplit out

LITERATURE.—Lange, Zwischenprodukte, #2617, 2618Thorpe, Die. Chemistry, 3, 650

Dyes Derived from l:7-Dihydroxy-naphthalene-4-sulfonic Acid

SchuUzNumberfor Dye

413

414

Ordinary Same andClass of Dye

DISAZO DYESDirect Violet BB

Indazurine B


Manufacture

I '14:— 4,396


Dianisidin.6m-Tolylene-diamine

DiardsidineRAcid


D

D


1:8-Dihydroxy-naphthalene-4-sulfonic Acid

Dihydroxy-naphthalene-sulfonic Acid S

S Acid

4: 5-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)

HO OH

= Ci0H8O5S =

STATISTICS.—Imports '14:—2,178 lbs.

FORMATION.—(1) From l-naphthol-4: 8-disulfonic acid by fusion withcaustic soda, preferably in an autoclave. (2) From 1-naphthyl-amine-4:8-disulfonic acid by fusion with caustic soda, in an auto-clave. (3) From l-amino-8-naphthol-4-sulfonic acid by heatingwith sodium sulfite

LITERATURE.—Cain, Intermediate Products (2d Ed.), 230Lange, Zwischenprodukte, #2621, 2622

Dyes Derived from l:8-Dihydroxy-naphthalene-4-sulfonic Acid



Statistics ofImpo?t andManufacture



63

71

118

146

147

MONOAZO DYESAzo Acid Blue

Azo Fuchsine B

Brilliant Geranine

Azo Fuchsine G

Azo Fuchsine 6B

I '14:-I ;20:-

45,0989,222

I '14:-M19:-I '20:-

I 14:-I' 20:-

18,917

527

17,8193,694

I 1 4 : — 13,206M17:— ?M18:— ?

Dimethyl-p-phenylene-diamine

orp-Nitro-aniline [Reduc-

tion and alkylation]

Toluidine

Dehydro-thio-p-toluidine

Sulfanilic Acid

Sulfanilic Acid (?)

A

D


Dyes Derived from l:8-Dihydroxy-naphthalene-4:-siilfonic(continued)

Acid


229

242

262

276

416

452

460

Ordinary Nanne andClass oj Dye

DISAZO DYESAzo Acid Violet

Sulfon Black G

Victoria Black B

Diamond Green B

BrilliantAzurine 5G

TEISAZO DYESBenzo Indigo Blue

Benzo BlackBlue5G

II

M

I

IMI

II

I

Statistics ofImpoit andManufacture

'14:—'20:—'20:—

'14:—

'14:—'18:—'20:—

'14:—'20:—

'14:—

150119

557

8,622

4,061

22,3241,563

602


Amino-azo-benzene

Anilinel-Naphthylamine-6-

and 7-sulfonic Acids[Cleve's Acids]

Sulfanilic Acida-Naphthylamine

Ammo-salicylica-Naphthylamine

Dianisidine1:8-Dihydroxy-naph-

thalene-4-suJfonicAcid (2 mols)

Tolidinea-Naphthylamine1:8-Dihydrox3r-naph-

thalene-4-s ulf onicAcid (2 mols)

Benzidine-disulfonic-Acid

a-Naphthylamine1: 8-Dihydroxy-naph-

thalene-4-sulfonicAcid (2 mols)


A

A

A

ACr

D

D

D


See, 1:8-Dihydrox3"-rLaphthalene-4-sulfonic Acid


See, 1:7-Dihydrox}r-rLaphthalene-4-sulfonic Acid


Dihydroxy-naphthalene-sulfonic Acid SSee, 1: 8-Dihydroxy-naphthalene-4-sulfonic Acid

Dihydroxy-naphthoic Acid L2: 6-Dihydroxy-3-naphthoic Acid (not considered herein)

Dihydroxy-naphthoic Acid S1: 7-Dihydroxy-6-naphthoic Acid (not considered herein)

1: 7-Dihydroxy-2-naphthoic-4-sulfonic Acid1: 7-Dihydroxy-naphthalene-2-carboxylic-4-sulfonic Acid

1: 7-Dihydroxy-2-carboxy-naphthalene-4-sulfonic Acid

1: 7-Dmydroxy-4-sulfo-2-7iaphthoic Acid (C. A. nomen.)

OH

= C l l H 8 O 7 S =

FORMATION.—l-Hydroxy-2-naphthoic acid is disulfonated with 4 partsof 20 per cent oleum, the product isolated and fused with causticsoda at 190-200°

LITERATURE.—Cain, Intermediate Products (2d Ed.), 242Lange, Zwischenprodukte, 2677

Dyes Derived from l:7-Dihydroxy-2-naphthoic-4-sulfonic Acid


396

399

427

429

430


DISAZO DYES

Indazurine RM

Indazurine TS

Indazurine GM

Indazurine BB

Indazurine 5GM



TolidineNevile-Winther's Acid

TolidineGamma Acid

DianisidineNevile-Winther's Acid

DianisidineR Acid

DianisidineHAcid


D

D

D

D

D


1: 7-Diliydroxy-6-naphthoic-3-sulfonic Acid

1: 7-Dibydroxy-naphthalene-6-carboxylic-3-sulfonic Acid

1: 7-Dihydroxy~6-carboxy-naphthalene-3-sulforjic Acid

Xigrotic Acid

Nigrotinic Acid

3: 5-Dihydroxy-7-sulfo-2-waphthoic Acid {C. A. nomen.)

OH

HOHOOC SO3H

= CnH8O7S =

FORMATION.—2-Hydroxy-3-naphthoic acid is disulfonated with 4 parts

of 24 per cent oleum at 125-150° for from two to three hours, the

product isolated, and fused with 2 parts of caustic soda at about

210-220° and then at 230-240°


Lange, ZTvischenprodukte, #2678

Dyes Derived from l:7-Diliydroxy-6-naphthoic-3-sulfoiiic Acid

SchvJUzNumberfor Dye

352

353

354

397


DISAZO DYES

Direct Violet R


Direct Gray R

Direct Blue R


Manufacture

I '14:— 661M'19:— ?

I '14:— 6,000

I J20:— 4,927

MJ17:— ?


Benzidinem-Tolylene-diamine

BenzidineH Acid

Benzidine1:7-Dihydroxy-6-napli-

thoic-3-sulf onic Acid(2 mols)



D

D

D

D


Dyes Derived from l:7-Dihydroxy-6-naphthoic-3-sulfonic Acid(continued)


398

428



Direct Gray B

Direct Blue B

Statistics ojImport andManufacture

I '14:— 21,421MJ17:— 14,823MJ18:— ?I '20:— 7,055


Tolidine1:7-Dihydroxy-6-napL.-

thoic-3-sulfonic Acid(2 mols)

DianisidineNevile-Wintlier's Acid


D

D

1:2-Dihydroxy-naphthoquinone

See, Naphthazarin

5:6-Dihydroxy-l: 4-naphthoquinone

See, Naphthazarin

5:6-Dihydroxy-a-naphthoquinone

See, Naphthazarin

1:7-Dihydroxy-4-sulfo-2-naphthoic Acid (C. A. nomen.)

See, 1: 7~Dihydrox^-2-naphthoic^-sulfonic Acid

3:5-Dihydroxy-7-sulfo-2-/iaphthoic Acid (C. A. nomen.)


Dihydroxy-tartaric Acid

Dioxy-tartaric Acid

C:(OH)2.COOH

C:(OH)2.COOH


FORMATION.—By oxidation of tartaric acid with strong nitric acid inpresence of oleum


Dyes Derived from Dihydroxy-tartaric Acid

Sckultz

for Dye

23


PYRAZOLOXE DYETartrazine


Manufacture

I '14:—272,477M'17:— ?M '18:— ?M'19:— ?I '20:— 47,877M '20:—701,722


Phenyl-hydrazine-p-sulfonic Acid (2 mols)


A

3:6-Dihydroxy-9-jcanthene-proprionic Acid, 7-Lactone (C. A.nomen.)

See, Resorcinol-suecinein

p-(ft-DimethylaTnfno-anilino)-jhenol (C. A. nomen.)

See, 4-Dimethylamino-4'-bydrox\r-diphenylamine

Diniethylarnino-azo-benzene-disulf onic Acids

5-DimethyIamino-o: p/-azo-bis(l!>enzene-sulfonic Acid) (C. A.nomen. for I)

6-Dimethylamino-m: p'-azo-bisCbenzene-sulfonic Acid) (C A.nomen. for II)

HO3S

= 385


FORMATION.—The compound represented by "Formula I " is preparedby coupling diazotized sulfanilic acid with dimethyl-aniline-m-sulfonic acid (prepared by sulfonating dimethyl-aniline). The iso-meric compound represented in all probabiKty by "Formula I I , "is made by direct sulfonation of dimethylamino-azo-benzene bymeans of oleum

LITERATURE.—Ger. Pat. 80434, Methods (b) and (a). Frdl. 4, 490

Cf. Ullmann, Enzy. tech. Chemie, 2, 81

Dye

SchvlizNumberfor Dye

628

Derived from Dunethylamino-azo-benzene-disulfonic Acids


OXAZINE DYEGallocyanine MS


I '20:— 22


Gallic Acid


M

/>-Dimethylamino-benzaldehyde

HCO

0-N(CH3)2FORMATION.—Dimethyl-aniline is changed into dimethylamino-benzylalcohol by treatment with hydrochloric acid and formaldehyde.This is then oxidized by adding nitroso-dimethyl-aniline directlyto the crude alcohol, resulting in the formation of dimethylamino-benzylidene-amino-dimethyl-aniline, (CH3)2N.C6H4.CH: N.CeH-N(CH3)2. This latter by treatment with nitrous acid or formalde-hyde forms pure p-dimethylamino-benzaldehydeLITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 307Lange, Zwischenprodukte, #333-335


Dyes Derived from />-Dimethylamino-benzaldehyde


529

564


TEIPHENYL-METHAXEDYE

Acid Violet 6B

Naphthalene GreenV


Manufacture

I '14:— 22,144I '20:— 9,291


Ethyl-sulfobenzyl-aniline (2 mob)

[Oxidation]

Dimethyl-anilinewi-Xylene


A

A

^-Dimethylamino-benzoyl Chloride

OCC1

= C9Hi0ClXO = 183.5

X(CH3)2

FORMATION.—From dimethyl-aniline by action of phosgene

LITERATURE.—Beil., 2, 1271

Dye Derived from ^-Dimethylamino-benzoyl Chloride

SchuttzNumberfor Dye

533


TRIPHENTL-METHANEDYE

Acid Violet 7BX



Used and Notes

Methyl-diphenylamine-sulfonic Acid (2 mols)


A

Diinetliylainino-benzoyl-inethyl-aaiiline

DimethylarnincHbenzcHmethyl-aniliiie (Schultz nomen.)

2>-Dimethylajiiino-xVrmethyl-benzanilide (<7. A. nomen.)

(CH3)2N

CH3

CO.X —254


FORMATION.—Dimethyl-aniline reacting with phosgene forms p-di-methylamino-benzoyl chloride, which latter unites with methyl-aniline to form the p-dimethylamino-benzoyl-methyl-aniline

LITERATURE,—Cf. Ger. Pat. 41751, 44077Cf. Georgievics and Grandmougin, Dye Chemistry, 174

Dye Derived from Dimethylamino-benzoyl-methyl-aniline

SchultzJSwtnoerfor Dye

493


DlPHENYL-METHANEDYE

Auramine


I '14:-449,276M'17:— ?M'18:— 45,634M'19:—127,567M'20:— ?I '20:— 74,414


Dimethyl-aniline


B

-^: JV-cHmethyl-metanilic Acid (C. A.nomen.)

See, p: pr - Tetramethyl - diamino - diphenylmethane - sulfonicAcid

5- Dimethylamino- a- (p- dimethylamino- phenyl)- a- hydroxy- o-^oluene-sulfonic Acid (C. A. nomen.)

See, pip'-Tetramethyl-diamino-benzohydrol-sulfonic Acid

(Dimethylamino-hydroxy-benzoyl) -benzoic Acid

o-(4-Dunethylamino-2~hydroxy-benzoyl)-&enzoic Acid (C A. no-men.)

OH

" C O Y S - C J I N O - 2 8 5CUOil <. >±X (Cxi3J2

FORMATION.—By condensing phthalic anhydride and ?n-dimethylainino-phenol


LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 232

Lange, Zwischenprodukte, #1394, 1395 (Note Lange9 s

formula is at variance with structure given above, which,

however, corresponds to the generally accepted for?nula)

Dyes


575

576

577

578

Derived from (Dimethylamino-hydroxy-benzoyl)benzoic


XANTHONE DYESRhodine 12GM

Rhodamine 3G

Rhodine 2G

Rhodamine 12GF


Manufacture

I '14:— 19,568I '20:— 855


Resorcinol MethylEther

[Ethyl esterification]

3-Amino-p-cresol[Ethyl esterificationj

Ethyl-m-amino-phenol[Ethyl esterification]

Resorcinol[Formaldehyde;

esterification]

Acid


B

B

B

B

4-Dimethylamino-4/-hydroxy-diplienylaraine

p-(p-Dimcthylamino-anilino)-phenol (C A. nomen.)

-No.-(CH3)2N

FORMATION.—(1) Dimethyl-p-phenylene-diamine is heated with thehydrochloride of p-nmino-ph pn ol. (2) Dimethyl-p-phenylene-diamine and phenol are simultaneously oxidized and the productcarefully reduced


e, Swefelfarbstoffe, 145, 157


Dye Derived from 4-Dimethylamino-4;-hydroxy-diplienylamiiie


728


SULFUE DYEImmedial Sky Blue


Manufacture

M'17:— ?


[S+Na*S]


S

l-Dimetliylamino-S'-methoxy-benzophenone {C. A, nomen.)

Methoxy-dimethylamino-benzophenone

FORMATION.—10 parts of m-methoxy-benzanilide, 14 parts of dimethyl-aniline and 7 parts of phosphorus oxychloride are heated togethercarefully on the water bath at 90°. The melt is treated with 50parts of water and 5 parts of hydrochloric acid, and the yellow brownsolution warmed to 70-80° until the color has disappeared, whichindicates the completion of the splitting off of the aniline. Morewater is now added, the precipitate filtered, washed, dried, andcrystallized from two parts of alcohol. From the filtrate anilineand dimethyl-aniline can be recovered


Dye Derived from 4-Dimethylamino-3'-methoxy-benzoplienone


547

Ordinary Nome andClass oj Dye

TlUPHENYL-METHANEDYE

Ketone Blue 4BN



Methyl-diphenylamine[Sulfonation]

DyeAppli-cadonClass

A

^-Dimethylaanino-i\T-methyl-6enzanilide (C. A. nomen.)

See, Dimethylamino-benzoyl-methyl-aniline

23G DYES CLASSIFIED BY INTERMEDIATES

2-Diinethylainiiio-8-naphthol-6-siilfonic Acid

See, Dimethyl-gamma Acid

7-Dimethylairrino-l-naphthol-3-sulfoiiic Acid (C. A. nomen.)

See, Dimethyl-gamma Acid

5-Dimetfoylamino-2-iiitffoso-£-cresol (OH=1,C. A. nomen.)

Nitroso-dimethyl-m-amino-p-cresol (OH =1)

OH

( C H ^ x i ^ / =

CH3

FORMATION.—3-DimethyIamino-p-cresol (OH = 1) [which can be ob-tained by decomposing diazo-dimethyl-o-toluidine in an acid solu-tion] is dissolved in hydrochloric acid, cooled to 0° C , and nitrosifiedwith aqueous solution of sodium nitrite


Dye Derived from S-Dinietliylanuno-2-nitroso-^-cresol

" S ^ Ordinary Xa^earul I g g ^ gfor Dye | Class oj Dye | Ma^ujacture

621OXAZINE DYE |

Cresyl Blue 2BS 1!

Other IntermediatesUesd and Notes

p-Phenylene-diamine


B

m-Dimethylamino-^henol (C A. nomen.)

t7Z-Hydrox3r-dimeth}rl-aniline

Dunethyl-wz-amino-phenol

OH

) N C C H O .

FORMATIOX.—By caustic soda fusion of dimethyl-aniline-m-sulfonicacid, prepared by sulfonating dimethyl-aniline with oleum

LITERATURE.—Lange, Zwischenprodukte, #603-606, 2263


Dyes Derived from m-Dimethylamino-phenol

237

%& **%£$%."*



Used and Notes


568

569

570

XANTHONE DYESPyronine G

Acridine Red B

Rhodamine S I '14:—I '20:—

600273

m-Dimethylainino-phenol (2 mols)

[Oxidation]

m-Dimethylamino-phenol (2 mols)

[Oxidation]or

[Oxidation of PyronineGwithKMnO4]

m-Dimethylairdno-phenol (2 mols)

[Succinic Anhydride]

B

B

Dimethyl-aniline

iV:iV-Dimethyl-aniline ( C A. nomen.)

N(CH3)2

STATISTICS.—Imported J14:— 48,642 lbs.

Manufactured ' 17:—2,847,093 lbs.

Manufactured '18:—4,263,458 lbs.


Manufactured J20:—5,447,107 lbs.

FOR]&ATTON.—By heating aniline and methanol (methyl alcohol) in an

autoclave in the presence of sulfuric acid

LITERATURE.—Cain, Intermediate Products (2d Ed. ) , 62



Dyes Derived from Dimethyl-aniline

Schult?Numberfor Dye

32

124

138

493

495

496

497


MOXOAZO DYESButter YellowOil Yellow

Diazine Green S

HelianthineMethyl Orange

AUEAMINESAuramine

TRIPHEXYL-METH4JSEDYES

Malachite Green

Setoglaucine 0

New Fast Green 2BVictoria Green 3B

Statistics ojImport aridManufacture

I '14:— 4,062M'17:—33,180M'18:—27,669M'19:— 31,156M'20:— 74,182

I '14:— 1,340

I '14:— 500M'18:— ?M'19:— ?M'20:— ?

I '14:—449,276M'17:— ?M'18:— 45,634M'19:—127,567I '20:— 74,414

M'20:— ?

I '14:—183,852M'17:—130,229M '18:—290,416M'19:—560,301I '20:— 100

M'20:—654,237

I '20:— 1,102

I '14:— 44,595


Aniline

p-Tolylene-diamineo-ToluidineAniline or a-Toluidine

orSafranine

Sulf anilic Acid

Dimethylamino-benzo-methylaniline


Benzaldehyde[Oxidation]


o-Chloro-benzaldehyde[Oxidation]


2:5-Dichloro-benzalde-hyde

[Oxidation]


ss

B

A

B

B

B

B


Dyes Derived from Dimethyl-aniline (continued)


Oi dinary Name andClass of Dye



Used and Notes


510

TRIPHENYL-METHANEDYES (continued)

Azo Green

515 Methyl Violet

516 Crystal Violet

517 Methyl Violet 5BBenzyl Violet

519 Methyl Green

I '14:—255,063M17:—375,107M'18:—632,196M'19:—574,436

:— 3,312M'20:—600,873

I '14:— 51,872M'17:—M'18:—M'19:—I '20:—M'20:—

???

2,919?

I '14:— 22,387I '20:— 3,313M'17:— ?


m-Nitro-benzaldehydeSalicylic Acid[Oxidation]


[Phenol][Oxidation]

Ketoneor


Phosgeneor

Hydrol[Oxidation]


orBenzyl-chlorideDimethyl-aniline

(3 mols)[Phenol]

[Methyl Chloride ofMethyl Violet]

orDimethyl-aniline

(3 mols)[Phenol and Methyl

Chloride]

M

B

B

B

B


Dyes Derived from Dimethyl-aniline (continued)

SchvJtzX umberjor Dye

523

5G4

659

660

661

Ordinary Xame andClahs of Dye

TRIPHEXYL-METHANEDYES {continued)

Fast Green

NaphthaleneGreen V

THIAZIXE DYESMethylene Blue

Methylene Green 0

Thionine Blue G 0


Many fact we

I '14:— 14,347I '20:— 10,461

I J14:— 22,144I '20:— 9,291

I ' 14:—185,958M '17:—268,435M'IS:—312,572M319:—465,992I '20:— 2,053M'20:—577,264

I' 14:— 30,812M'lS:— ?M'19:— 2,435I '20:— 1,049

I '14:— 18,618I '20:— 330

Other IntermediatesUsed and Xotes

7?z-Xitro-benzaldeh3TdeDimethyl-aniline

(2 mols)Benzyl-chloride

(2 mols)[Sulfonation, Oxidation]

p-Dimethylarxiino-benzaldehyde

m-Xylene


[Naa&Os, etc.]or


pNTa2S2O3, etc.]or

Dimethyl-p-phenylenediamine

Psa2S2O3, etc.]


[Naa&Os, Nitration]or

Nitroso-d i methyl-aniline

[Naf&Os, etc.; Nitra-tion]

orDimethyl-p-phenylene-

diamine[Na^Os, etc.; Nitra-

tion]or

[Methylene Bluenitrated]

Ethyl-methyl-aniline[Nas&Os, etc.]


A

A

B

B

B


N: N-Dimethyl-p: /-azo-bisaniline (<7. A. nomen.)

See, Dimethyl-p: p'-diamino-azo-benzene

2:2/-Dimethyl-l: r-Manthraquinone (C. A. nomen.)

2: 2/-Dimethyl-l: l'-dianthraquinonyl

FORMATION.—l-Amino-2-methyl-anthraquinone is dissolved in sulfuricacid and sodium nitrite added. The isolated and dried diazoniumsulfate is stirred into acetic anJiydride, and copper powder added.Nitrogen is evolved and the combination takes place, forming thebianthraquinone derivative

LITERATURE.—Lange, Zwischenprodukte, #3491-3493Cain, Intermediate Products (2d Ed.), 261

Dyes Derived from 2:2'-Dimethyl-l: l'-bianthraquinone





Used and Notes


760

761

762


IndanthreneGold Orange G

Pyranthrone

IndanthreneGold Orange R

IndanthreneScarlet G

I '14:— 20,092I '20:— 7,617

I '14:— 50,496I '20:— 35,338

I '14:—I '20:—

99399

[2 mols H2O removed]

[2 mols H2O removed,Chlorinationl

[or Pyranthrone 760,chlorinated]

[2 mols H2O removed,Bromination]

[or Pyranthrone 760,brominated]


Dimethyl-^: ^'-diamino-azo-benzene.V: JV-Dimethyl-p: p'-azo-bisaniline (C. A. nomen.)

X X XH2 =Ci4Hi6X4 =(CH3)2X

FORMATION.—(1) By coupling of diazotized p-nitro-aniline with dimethyl-aniline and subsequent reduction with sodium sulfide.(2) By coupling of diazotized p-amino-acetanilide with dimethyl-aniline and splitting off of acetyl group

LITERATURE.—Heumann, Anilinfarben, 3, 1467; 4, 1026Cf. Lange, Zwischenprodukte, #1760

Dye Derived from Dimethyl-^: y-diamino-azo-benzene

SchulizNumber1 or Dye

239


DISAZO DYEAzotol C



jS-Naphthol


MF

4:4/-Dimethyl-diamino-3:3'-ditolyI-methaneDimethyl-diamino-di-o-tolyl-methane4:4/-Methylene-bis(AT-meth3i-o-toluidine) (C. A, nomen,)

CHs.HX, j j XH . CH3

FORMATION.—By condensing formaldehyde and two molecules ofmethyl-o-toluidine


Dye Derived from 4:4'-Diinethyl-(iiainiiio-3:3'-ditolyl-inethane

SckultsNumberfor Dye

494


AUTUMTNTISAuramine G


Manufacture

I 14:— 1,902


[Sulfur, Ammoniumchloride, etc.}


B


Dimethyl-diamino-di-o-tolyl-methane

See, 4:4/-Dimeth3'l-diamino-3: 3'-ditolyl-methane

2:2-Dimethyl-l: r-dianthraquinonyl

See, 2: 2'-Dimethyl-l: l'-&ianthraquinone (C. A. nomen.)

Dimethyl-gamma Acid

2~Dimethylamino-8-naphthol-6-sulfonic Acid

7~Dimethylamino-l-naphthol-3-sulfonic Acid (C A. nomen.)

HO

N(CH3)2 _ Cl2H13NO4S = 267HO3S

FOKMATION.—G acid is heated with dimethylamine in an autoclavearound 200°, the dimethylamino-G acid thus obtained is fused withcaustic soda at 210-220°, and the dimethyl-gamma acid isolated


Dyes Derived from Dimethyl-gamma Acid


206

348

393


MONOAZO DYEDiphenyl

CatecMne G

DISAZO DYESDiphenyl

Brown BN

DiphenylBrown 3GN


Manufacture

I 14:— 8,642

I '14:— 13,471

M'20:— ?


p-Nitro-toluene-o-sulf onic Acid

p-Phenylene-diamine[Diphenyl Orange RR1

Salicylic AcidBenzidine

Salicylic AcidTolidine


D

D

D

N: iV-Dimethyl-£-mtroso-ajiiline (C. A. nomen.)

See, p-Nitroso-dimethyl-aniliAe


N: JV-Dimethyl-m-£henylene-diamine (C. A. nomen.)

w-Amino-dimethvl-aniline

FORMATION.—Dimethyl-aniline is nitrated "with mixed acid, and them-nitro-dimethyl-aiiiline separated from the para isomer. Them-derivative is novr reduced to dimethyl-??2~phen3'lene-diamine

LITERATURE.—Green, Organic Coloring Matter (1908), 32

Dyes Derived from N: iV-Dimethyl-m-phenylene-diamine

Ordinary Xame and \ *£$»$ | Otker InterrnediatesCl f D u | i d d A

i S S . y £ $ $ |forDye1, Class of Dye Manufacture | isedandAotes


603

604

ACRIDINE DYES ' 'Acridine Orange NO I J14:— 2,336i Dimethyl-m-phenylene-

, I J20:— l,92n| diamine (2 mols)i [Formaldehyde, Oxida-| i tion, etc.]! I

i Dimethyl-wi-phenylene-I diamine (2 mols)I Benzaldehyde' [Ammonia removal;

Oxidation]

Acridine Orange R

B

B

N: iV-Dimethyl-^-phenylene-diamine (C. A. nomen.)

y)~Amino

N(CH 3 ) 2

STATISTICS.—Imported ' 14:—very smallManufactured 717:— ?Manufactured ' 18:— ?Manufactured ?20:—314,931


FORMATION.—Dimethyl-aniline by action of nitrous acid forms nitroso-dimethyl-aniline, which by reduction with zinc dust and hydro-chloric acid furnishes dimethyl-p-phenylene-diamine

LITERATURE.—Lange, Zwischcnprodukte, #561-563

Dyes Derived from N: iV-Dimethyl-^-phenylene-diamine


62

63

619

627

659

660

661

Ordinary Name andCalss of Dye

MONOAZO DYESAzogalleine

Azo Acid Blue

INDOPHENOLIndophenol

OXAZINE ANDTHIAZINE DYES

Modem Cyanine

Methylene Blue

Methylene Green 0

Thionine Blue G 0


Manufacture

I '14:— 45,09SI '20:— 4,485

M '18*:— ?M '19.-126,611

I '14:—185,958M'17:—268,435M'18:—312,572M'19:-HJ:65,992I '20:— 2,053M'20:—577,264

I '14:— 30,812M'18:— ?M'19:— 2,435I '20:— 1,047

I '14:— 18,618I '20:— 2,030


Pyrogallol

1:8-Dihydroxy-naph-thalene-4-sulf onic Acid

a-Naphthol[Oxidation]


Gallamide

Dimethyl-aniline[Na2S2O3, etc.]

Dimethyl-aniline[Na^^Os, etc.][Nitration]

or[Methylene Blue

nitrated]

Ethyl-m ethyl-aniline[Na^Os, etc.]


M

M

V

M

B

B

B


Dyes Derived from N: N-Dimethyl-^-phenylene-diaroine (.continued)


669

670

680

681

683

690

729

731


AZINE DYESNeutral Violet

Neutral Red

MethyleneViolet BN

Methylene Gray 0New Fast Gray

Safranine MN

Diphene Blue RMetaphenylene

BlueR

SULFUR DTESKrvogene Pure

BlueR

Thiophor Indigo C J


Manufacture

M'18:— ?

I '14:— 1,521M'17:— ?I '20:— 33

I '14:— 29,507M'17:— ?M'lS:— 16,746M'19:— 2S,458I '20:— 509M'20:— 31,620I '14:— 198M'18:— ?M'19:— ?M'20:— ?

I 720:— 3,124


Dimethyl-p-phenylene-diamine (2 mols)

m-Phenylene-diamine

m-Tolylene-diamine

Aniline (2 mols)[Oxidation]

Dimethyl-p-phenylene-diamine (2-|-mols)

[Oxidation]

Anilineo- or p-Toluidine[Oxidation]

st/m-Di-p-tolyl-m-phenylene-diamine

[Oxidation]

Aniline (2 mols)[S+NaaS]

or[Methylene Violet;

a-Naphthol[S+Na*S]


B

B

B

B

B

B

S

S

N: AT»IHinethyl .phftny1ftnft.-di>rninft-thingii7fnrii>. Acidp-Amino-dimethyl-aniliiie-thiosulfonic Acid

!~Aii3ino-4^imetbyIamino-bei]Lzene-2~thiosuIfoiiic Acid2-Amino-OKiimethylaniino-6€rizene-thiosulfoiiic Acid (C.

rumen.)


N(CH,)a

247

HOsS.Sl

NH2

FORMATION.—10 parts of dimethyl-p-phenylene-diamine sulfate are dis-solved in 100 parts of water and cooled to 0°, and a cold solution of5.5 parts of potassium bichromate in 60 parts of water and 18 partsby volume of 50 per cent acetic acid, is introduced quickly duringagitation. To the crystal mass is now added at once a solution of22 parts of sodium thiosulfate and 27 parts of aluminum sulfatein 70 parts of water, and the mixture agitated at 10-20°. Uponcooling to 0° the desired product separates out


Dyes Derived from i^iiST-Dimethyl-^-phenylene-cnainine-thiosulfoiiicAcid


661

664

665

667


THIAZINE DYESThionine Blue G O

Lenco-galloThionine DH

Urania Blue

Brilliant AlizarinBlueG

Indochromine T


I '14:— 18,618I '20:— 2,030

I '14:— 132

I '14:— 19,481M'19:— ?I '20:— 3,214M'20:— ?


Ethyl-methyl-aniline

Gallic Acid

N: #'-Di-2-naphthyl-7n-phenylene-diamine

1:2-Naphthoquinone-4: 6-disulfonic Acid


B

M

A

M

N: iV'-Di^-naphthyl-m-phenylene-diamine

24S DYES CLASSIFIED BY INTERMEDIATES

FORMATION.—108 parts of m-phenylene^liamine, 432 parts of £-naphtholand 2-3 parts of iodine are heated together at 200° and finallyat 260°. The melt is powdered, and washed successively withdilute caustic soda, hydrochloric acid, water, alcohol, and ether.The residue is crj'stallized from aniline. Yield good

LITERATURE.—Lange, Zwischenprodukte, £2875, 2876

Dyes Derived from Ar:iV/-Di-2-naphthyl-m-phenyleiie-diamine

SchultzNumberJor Dye

665



Manufacture

THIAZINE DYE JUrania Blue . I '14 :— 132

1 AZIXE DYE *692 Xaphtbazine Blue I '14:— 6,261

I '20:— 2/249

Other Intermediatessed and Notes

Dimethyl-p-phenylene-diamine- thiosulfonicAcid



2:4-Dirritro-aniline (C. A. nomen.)7w-Dinitro-anilineXH2

< <xo2 _4 — 1 8 3

XO2

FORMATION.—Aniline is condensed with phthalic acid, and the phthal-anil dinitrated. Upon heating the latter product with anilineunder pressure the 2:4-dinitro-aniline is split off

LITERATURE.—Lange, Zwischenprodukte, #539Dyes Derived from 2:4-Dinitro-aniline


59


MONOAZO DYEWool Violet S

Statistics ofImport ond

Manufacture

I '14:— 308MJ18:— ?M '19:— ?


Diethyl-aniline-?n-sulf onic Acid


A


m-Dinitro-aniline

See, 2:4-Dinitro-aniline (C. A. nornen.)

p-(2:4-Dinitro-anilino)-phenol (C. A. nomen.)

See, 2:4-Dinitro-4/-hydroxy-diphenylamine

4:8-Dinitro-anthrachrysone-2:6-disulfonic Acid

OH

>W3-»-»- . fi. TT "VT /~\ rj COO\fX v_yi4JJL6lN 2 ^ 1 6 ^ 2 O i i

H O " " " ' N O 2

F O R M A T I O N . — A n t h r a e h r y s o n e i s s u l f o n a t e d a n d n i t r a t e d

L I T E R A T U R E . — G r e e n , O r g a n i c C o l o r i n g M a t t e r s ( 1 9 0 8 ) , # 5 5 4 a n d # 5 5 7

D y e D e r i v e d f r o m 4 : 8 - D i n i t r o - a n t h r a c h r y s o n e - 2 : 6 - d i s u l f o n i c A c i d


796



Acid AlizarinGreen G


I '20:— 1,334


[Sodium sulfidereduction]


ACr

1:5-Dinitro-anthraflavic-3:7-disulfonic Acid

. C O N ° 2

c o ) 0 ^ H

NO2

FORMATION.—By the sulfonation and nitration of anthraflavic acid(which is prepared by heating m-hydroxy-benzoic acid with sul-furic acid at 190° C.)

LITERATURE.—Thorpe, Die. Chemistry, 1, 84

Cf. Bucherer, Lehrbuch des Farbenchemie, 339 (1914)


Dye Derived from l:5-Dinitro-anthraflavic-3:7-disulfonic Acid

SchxdtzNumbe,for Dye

857


ANTHEAQUTN'ONE ANDALLIED DYES

Erweco AlizarinAcid Blue R



Aniline (2 mols)[Sulfonation}


ACr

Dinitro-anthraquinone(1: o-and 1: S-Dinitro-anthraquinones)

0 2 N


FORMATION".—The mixed compounds are obtained from anthraquinone,by nitration in sulfurie acid solution, and by pouring the nitrationproduct into ^vater


Dyes Derived from Dinitro-anthxaquinone

SchuUz1

Numberfor Dye


SiaiistiGs ofImport and


Used and Notes


749

790

801

802

SULFTB DYEAnthraquinone Black

AynraA QOK ONE ANDALLIED DYES

AnthraceneBlue

AnthraceneBlue WGG

AnthraceneBlue WG new

I 'U:— 26,642I '20:— 3,539

I '20:— 1,500

[S+Na*SJ


[Oxidation]

[Oxidation]

S

ACr

M

M


1:5-Dinitro-anthraquinone

CO N ° 2

•—O14X1IV S c W02N


FORMATION.—From anthraquinone in sulfuric acid solution by nitra-tion with HNO3 or NaNO3. The mixed 1: 5 and 1:8 dinitro-anthraquinones are recovered by pouring the nitration mixture intowater. By extraction of the mixed dinitro-compounds with ace-tone or alcohol, the 1: 5-dinitro-anthraquicone is left behind

LITERATUBE.—Cain, Intermediate Products (2d Ed.), 253Lange, Zwischenprodukte, #3218

Dyes Derived from l:5-Dinitro-anthraquinone

SchuiizNumberfor Dye

749

800

853


SULFUR DYEAnthraquinone Black


AnthraceneBlue WG

AnthraquinoneViolet


I '14:— 54,812I '20:— 2,049

I '14:— 1,202I '20:— 1,649


[S+Na^S]

[Oxidation]

p-Toluidine (2 mols)[Sulfonation]


s

M

ACr

m-Dinitro-benzene

NO2

STATISTICS.—Imported '14:— 164,650 lbs.Manufactured '17:—2,333,192 lbs.Manufactured '18:—4,115,269 lbs.Manufactured '19:—2,280,282 lbs.Manufactured '20:—3,380,il2 lbs.


FORMATION.—By nitration of nitro-benzene or of benzene, using mixedacid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 32Cf. Lange, Zwi^ehenprodukte, #543

USES.—For the manufacture of m-nitro-aniline and ?n-phenylene-diamine

2:2'-Dinitro-j>: £'-biacetanilide

See, Diacetyl-o: o'-dinitro-benzidine

2:4-Dinitro-chloro-benzene

See, l-Chloro-2: 4-dinitro-benzene (C. A. nwnenS)

Dinitro-^-cresol

OH 1

• i = C7H6X0O5 — 198

CH».

FORMATION.—Probably by the dinitration of p-cresol

LITERATURE.— Cf. Thorpe, 2, 165Cf. Lange, Schwefelfarbstoffe, 132, 381

Dye Derived from Dinitro-^-cresol

for Dye ManufactureOther Intermediates

Used and Notes


t SULFUR DTE725 Immedial Dark

Brown AImmedial Brown B

I '14:— 23,SS7 [S+Na*S]M'18:— ?

Dinitro-dibenzyl-disulfonic Acid

2:2r-Ethylene-bis(o-nitro-?>enzene-sulfonic Acid) (C. A. nomenS)

SO3H HO3S

= 4 3 2


FORMATION.—12 parts of sodium p-nitro-toluene-sulfonate are dissolved

in 50 parts of hot water, and treated with 100 parts of sodium

hypochlorite solution (2 per cent HOC1) and 50 parts of caustic

soda solution (40°) at 70°. At end of reaction, cooled with ice to

40° and after crystallizing several hours, the product is filtered off.


Dyes Derived from Dinitro-dibenzyl-disulfonic Acid


10

12

18


STILBENE DYESMikado YellowStilbene Yellow

DiphenylCitronine G

Diphenyl FastYellow


Manufacture

I '14:— 85,795M'18:— ?M'20:— ?

I '14:— 10,229

I '20:— 1,102


Dinitro-dibenzyl-disul-fonic Acid (2 mols)

Aniline

Dehydrothio-toluidine-sulf onic Acid (2 mols)

or Primulin e-sulf onicAcid (2 mols)


D

D

D

2: S-Dinitro-diphenylamine-S': 4-disulfonic Acid

3: 5-Dinitro-3': 4-imino-bis(&enzene-sulfonic Acid) (C. A. nomen.)

NO2 SO3H

NH = Ci2H9N3OioS2=419

NO2

FORMATION.—By reaction of l-chloro-2:6-dinitro-benzene-4-sulfonic

acid and metanilic acid in presence of sodium acetate


Cf. Schultz, Farbstofftabellen, #542

5i DYES CLASSIFIED BY INTERMEDIATES

Dye Derived from 2:5-Dinitro-diphenylamine-3':4-disulfonic Acid


AgaJma Green B 11 '14.— 2,294


2:4-DMtaro-diphenylamine-3'-sxilfonic Acid

*Y-(2:4-Dinitro-phenyi)-w2etanilic Acid (C. A. nornen.)

_X0 2 SO3H

02X<^ V - X H - = C12H9N3O7S = 339

FORMATION.—From chloro-dinitro-benzene and metanilic acid

LITERATURE.—Lange, Z^ischenprodukte, #1673Cf. Schultz, FarbstofftabeUen (1914), #738

Dye Deriyed from 2:4-Dinitro-diphenylamine-3'-sulfonic Acid

SchulUNumberfor Dye

738

Ordinary Name andCkssofDye

SULFUR DYECotton Black

Statistics ofImpoi t andManufacture


[S+NasS]


S

2:4-Dinitro-diphenyIaznine-4/-sxilfonic Acid

^"-(2:4-Dinitro-phenyl)-5iilfanilic Acid ((7. A. nomen.)

NO,

N H ^ ~ ^ S O C = 339

FORMATION.—From chloro-dinitro-benzene and sulfanilic Acid

LITERATURE.—Lange, Zwischenprodukte, #1673Cf. Schultz, FarbstofftabeUen, #738


Dye Derived from 2:4-Dinitro-diphenylamine-4/-sulfonic Acid


738



Statistics ofImpott endManufacture

Other IntermediatesUsed and Noies

[S+Na*S]

DyeAppli-cotionClass

S

2:4-Dinitro-4'-hydroxy-(Hphenylamine

p-(2:4-Dinitro-anilino)-phenol (C. A. nomen.)

NO2

O2N< •NH 5 —275

STATISTICS.—Manufactured 1919 but amount not disclosed

FORMATION.—From chloro-dinitro-benzene and p-amino-phenol byboiling molecular proportions in an aqueous suspension withslightly more than the theoretical amount of limestone


Dyes Derived from 2:4-Dinitro-4'-hydroxy-diphenylamine





Used and Notes


724

725

726

SULFUR DYESImmedial Black


Immedial Brown B

Pyrogene Direct BluePyrogene Blue

14:— 54,696M18:— ?

14:— 23,887M'18:— ?

[NaOH;

I 14:— 10,934 [Alcohol; S+Na*S]I '20:— 2,498

3:5-Dinitro-3': 4-imino-bis(6enzene-sulfonic Acid) (C. A. nomen.)

See, 2: 5-Dimtro-diphenylamine-3': 4-disulfonic Acid

25G DYES CLASSIFIED BY INTERMEDIATES

1:5-and 1:8-Dinitro-naphthaJenes

02N X0 2

and I | 1 =C10H6X2O4 = 218

STATISTICS.—Imported '14:—very small amount

Manufactured 'IS:— ?


FORMATION.—From a-nitro-naphthalene by nitration

LITERATURE.—Cain, Intennediate Products (2d Ed.), 170

Dyes Derived from 1:5- and 1:8-Dinitro-naphthalenes

for Dye

774

775

776

ANTHRAQUDTONE ANDALLIED DYES

Alizarin Black

Alizarin DarkGreen W

Printing Black forWool

Manufacture

I '14:—205,439I '20:— 17,421


[Oxidation]

Phenol[Oxidation]

[Reduction]


M

M

A

1:5-Dinitro-naphthalene

a-Dinitro-naphthalene

NO2

FORMATION.—a-Nitro-naphthalene is nitrated, resulting in formationof 1:5 and 1:8-<iinitro-naphthalenes ia the proportion of about


1:2. This crude product is washed with water and dried, and

then extracted first with carbon disulfide to remove nitro-naph-

thalene, and second with acetone to remove the 1:8 isomer,—

leaving behind the 1: 5 isomer. (See 1: 8-dinitro-naphthalene)




745

789

Dyes Derived


SULFUR DYEMelanogene Blue


AnthraceneBlue WR

from 1:5-Dinitro-naphthalene

Statistics ojImport and

Manufacture

I 14:—107,778I '20:-103,913M'20:— ?


[S+Na*S]

[Oxidation]


S

M

1:8-Dinitro-naphthalene

/3-Dinitro-naphthalene

02N N02

FORMATION.—a-Nitro-naphthalene is nitrated, resulting in the formation

1: 5 and 1:8-dinitro-naphthalenes in the proportion of about 1: 2.

The nitration mass upon cooling deposits most of the 1: 5-isomcr,

and upon pouring this filtrate into water the 1:8-isomer is pre-

cipitated, which can be purified by crystallization from benzene.

(See 1:5-dinitro-benzene)




Dyes Derived from l:8-Dinitro-naphthalene

for Dye j

1740 I

741 i!

742

743 l

!750

SULFUR DYESFast Black B

Fast Black BS

Printing Blue forWool

Kryogene Brown A

Kryogene Brown A, G

Stotisttcs ofImport and

Manufacture

I '14:— 10,313

Other Inter medic iesUsed and Notes

[Na/>S; Alkalies]or

[Fast Black B; Alkalies]

[NaaS,NaHSO*,NaOH]

[NaaS,NaHSO»,NaOH;S+NaaS]

[NaHSO3; S+NasS]

DyeAppli-cationClcss

S

S

S

S

S

a-Dinitro-naphthalene

See, 1:5-Dinitro-naphthalene

jS-Dinitro-naphthalene

See, 1:8-Dinitro-naphthalene

7-Dinitro-naphthalene

1:3-Dinitro-naphthalene (not considered herein)

5-Dimtxo-naphthalene

1: 6-Dinitro-naphthalene (not considered herein)

2:4-Dinitro-phenol

OH

= C«H4N"2O5 = 184

STATISTICS.—Manufactured '20:


FORMATION.—From chloro-dinitro-benzene by boiling with sodium

carbonate solution


Dyes Derived from 2:4-Dinitro-phenol


720

721

722

723


SULFUR DYESSulfur Black

Sulfur BlackThio Cotton Black

Auronal Black

Autogene Black EEB


Manufacture

I '14:—4,923,981 (?)

M'17:—9,298,631

M'18:—12,385,130

M'19:—14,504,770

I '20:— 662M'20:—

16,305,037

I '14:— 50,879


[S+NaaS]

[p-Amino-phenol-sulfonic Acid]

[S+Na,S]

[S+NaaS]


S

S

S

S

N-(2:4-Dinitro-phenyl)-metanilic Acid (C. A. nomen.)

See} 2:4-Dinitro-diphenylamine-3/-sulfonic Acid

^-(2:4-Dinitro-phenyl)-^-^henylene-diamine (C. A. nomen,)

See 4'-Amino-2:4-dinitro-diphenylamine

iV-(2:4-Dinitro-phenyl)-sulfanilic Acid (C. A. nomen.)

See 2:4-Dinitro-diphenylamine-4'~sulfonic Acid


Dinitro-stilbene-disulfonic Acid

4: 4'-Dinitro-$tilbene-2: 2'-disulfonic Acid (C. A. nomen.)

SO3H HO3S

0 aX =430


FORMATION'.—p-Xitro-toluene-sulfonic acid is dissolved in weak caustic

soda solution and oxidized with sodium hypochlorite solution. If

the product contains dinitro-dibenz^l-disulfonic acid, it is again

oxidized with sodium hypochlorite in caustic Soda solution.


Dyes Derived from Dinitro-stttbene-disulfonic Acid

Ordinary Xame and 'Class of Dye


\Othei Intermediates

Used and Notes


10

11

12

13

18

1 STILBENE DTESMikado YellowStilbene Yellow

]IMikado Orange

1 Chloraminej Orange G

DiphenylCitronine G

I '14:— 85,795M'18:— ?M'20:— ?

I '14:— 26,010M'17:— ?M'18:— ?M'19:— ?M'20:— 38,287

Polychromine B I '14:— 16,113Diphenyl Orange KR;M' 18:— ?

Diphenyl FastYellow

I '14:— 10,229I '20:— 1,102

Dinitro-stilbene-disul-fonie Acid (2 mols)

Dinitro-stilbene-disul-fonic Acid (2 mols)

[Reduction]

Aniline (2 mols)

p-Phenylene-diamine(2 mols)

Dehydrothio-toluidine-sulfonic Acid (2 mols)

or Primuline-sulfonicAcid (2 mols)

D

D

D

DYES CLASSIFIED BY INTERMEDIATES 2(

2:4-Dinitro-tfoluene (C. A. nomen.)

mJDinitro-toluene

CH3

/\$O2 _ C7H6N2O4 = 182

NO2

STATISTICS.—Imported '14:—547,701Manufactured '18:— ?Manufactured ' 19:—746,266Manufactured '20:—1,847,191

FORMATION.—From toluene by nitration with mixed acid

LITERATUEE.—Cain, Intermediate Products (2d Ed.), 34


USES.—For manufacture of m-tolylene-diamine

Diphenylamine

\ = Ci2HuN = 169

STATISTICS.—Imported ' 14:—81,137





FORMATION.—By heating aniline and aniline hydrochloride togclhiin an autoclave, provided with a replaceable acid-proof enamolUlining



2G2 DYES CLASSIFIED BY INTERMEDIATES

Dyes Derived from Diphenylamine

Sckuliz

134

135

136

139

140

141

142

150

203


MONOAZO DYESMetanil Yellow

Metanil Yellow,Brominated

Acid YellowMGS, GG

Orange IV

Azoflavine RSCurcumeine

Azo Yellow 3G

Brilliant Yellow SCurcumine

Fast Yellow X

Yellow Fast To Soap


Manufacture

I '14.-284,606M'17:— ?M'18:— ?M'19:—477,143I '20:— 8,456

M '20:—629,437

I '14:— 19,020

I '20:— 608

I '14:— 39,869I '20:— 5,225

I '14:—114,689M'17:— ?M '18:— ?M '19:— ?I '20:— 4,818M'20:— ?

I '14:— 9,934

Other IntermediatedUsed and Notes

Metanilic Acid

Metanilic Acid[Bromination]

Metanilic Acid[Sulfonation]

Sulfanilic Acid

Sulfanilic Acid[Nitration]

Sulfanilic Acid[Nitration]

Sulfanilic Acid[Sulfonation]

p-Toluidine-o-sulfonicAcid

TO-Arnino-benzoic Acid

Appli-cationClass

A

A

A

A

A

A

A

A

M

Diphenylamine-sulfonic AcidAnilino-&en2ene-suKonic Acid (C. A, nornen.)

-XH-


FORMATION.—By sulfonation of diphenylamine, and purification from

the disulfonate formed simultaneously

LITERATURE.—Schultz, Die Chemie des Steinkohlentheers (3 aufl.), 1 ,181


SchuhzNumberfor Dye

538

Dyes Derived from Diphenylamine-sulfonic Acid



Methyl BlueCotton. Blue


Manufacture

I '14:— 50,255


Diphenylamine-sulfonicAcid (3 mols)


B

Diphenylene-imide

See, Carbazole

Diphenyl-methyl-amine

See} iV-Methyl-rfiphenylamine (C, A. nomen.)

Diphenyl-naphthyl-methane

1-Naphthyl-diphenyl-methane (C. A. nomen.)

— C23H18 '==: 294

FORMATION.—From benzo-hydrol by heating with naphthalene andP2O5 at 140°-145° for some hours

LITERATURE.—A. Lehne, Ueber die Condensation von Benahydrol undNaphthalin, Ber, 13, 358 (1880)

Richter, Lex. d. Kohlenstoff Verbindungen, 4193


Dye Derived from Diphenyl-naphthyl-methane

SchidtzNumb*jorDye

Statistics ojDve Import andDye j ^anufacture

DlPHENYlr-NAPHTHYL- iMETHANE DYE |

565 Acid Blue B, Wool Blue G

I '14:—1SO,423! I '20:— 1,852!M'2O:— ?


[Sulfonation]


N: A^-Diphenyl-m-^henylene-diajnine (C A. nomen.)

s-Diphenyl-77z-phenylene-diamine

•HN—/N—NH-

FORMATION.—From resorcinol and aniline by heating together in presence

of calcium chloride and a little zinc chloride at 210°

LITERATURE.—Green, Organic Coloring Matters (1908), 3 7

Cf. Schultz, Farbstofftabellen, #689

Dyes Derived from N: AT-Diphenyl-m-phenylene-diamine


Used and Notes


267

267

689

DISAZO DYESPhenylene Black

Anthracite Black

A23NB DTEIndaziiieM

I '14M '17I '20

:— 99— ?— 220

l-Naphthylamine-4: 7-disulfonic Acid

a-NaphthylandiiB

Freund's Acida-Naphthylamine

NitroscKJim ethylaniline(1 and 2 mols)

B


Diphenyl-thiourea

See, Thio-carbanilide (C. A. nomen.)

Disulfo Acid C

2-Naphthylamine-4: 8-disulfonic Acid (not considered herein)

Disulfo Acid E

See, l-Naphthol-3:8-disulfonic Acid

Disulfo Acid F

2-Naphthylamine-3: 7-disulfonic Acid (not considered herein)

Disulfo Acid S


N: N'-(p:p'-T)itolyl)-2: 7-naphthylene-diamine

265

H3C •NH-, —NH

FORMATION.—By heating 2: 7-dihydroxy-naphthalene with p-toluidine

and p-toluidine hydrochloride

LITERATURE.—Green, Organic Coloring Matters (1908), 38


Dye Derived from N: AT-C£:£'-Ditolyl)-2:7-naphthylene-diamine


677


AZINB DYEBasle Blue R



Used and Notes



B


iVi^-Coco'-DitolylJ-m-phenylene-diainiiie (C. A. nomen.)

Di-o-tolyl-m-phen3iene-diamine

CH3 H.3C

2 = 288

FORMATION.—Presumably by heating resorcinol with o-toluidine inpresence of con Jensing agent. Cf. Di-p-tolyl-?rc-phenylene-diamine

LITERATURE.—Uilmann, Enity. tech. Chemie, 9, 63

Dye Derived from iVr^-Coio'-Ditolyy-m-phenylene-diainine


691


AZINE DYEMetaphenylene

BlueB


Manufacture

I '14:— 50




B

(C. A. nomen.)

Di-p-tolyl-m-phenylene-diamine

= 288

FORMATION.—From resorcinol, p-toluidine, and p-toluidine hydro-chloride by heating together in presence of calcium chloride and alittle zinc chloride

LITERATURE.—Uilmann, Enzy. tech. Chemie, 9, 63

Green, Organic Coloring Matters (1908) 7 37


Dye Derived from N: AT-(£:/-Ditolyl)-m-phenylene-diamine


690


AZINE DYEDiphene Blue RMetaphenylene

Blue It



Used ahd Notes

I '20:— 3,124 Dimethyl-p-phenylene-diamine

DyeAppli-cc tionClass

B

D SSee, Diamino-stilbene-disulfonic Acid

D TSee} Dehydro-thio-p-toluidine-sulfonic Acid

Ebert and Merz a Acid

See, Naphthalene-2: 7-disulfonic Acid

Ebert and Merz /3 Acid

Naphthalene-2: 6-disulfonic Acid (not considered here)

Epsilon Acid

See, l-Naphthol-3: 8-disulfonxc Acid


and 1:8-Dihydroxy-naphthalene-3-sulfonic Acid (not con-sidered herein)

Erdxnann's /i Acid


Ethoxy-benzidine

Di-p-amino-ethoxy-diphenyl

2-Ethoxy-6en2iidiiie (C. A. nomen. NH^^l)

H5C2O

^ T = 228

2G8 DYES CLASSIFIED BY INTERMEDIATES

FORMATION.—Aniline is diazotized and coupled with phenol-p-sulfonicacid and the product ethylated with ethyl bromide, thus forming,—benzene-azo-phenetole-sulfonic acid. This is t h e n reduced in anaqueous solution with zinc dust and caustic soda followed byacidification with hydrochloric acid, resulting i n preparation ofethoxy-benzidine-sulfonic acid which is heated in a n autoclave withwater (at 170°) to split out the sulfonic acid group

LITERATURE.—Weinberg, Ber. 20, 3171Lange, Zwischenprodukte, #1224, 1249Heumann, Anilinfarben 4, 380

Dyes Derived from Etkoxy-benzidine

SchultiNumberfor Dye

401

402

403

404

Ordinary A ome endClass of Dye

DISAZO DYESDiamine Blue 3R

Diamine Blue BlackE

Diamine Black BO

Diamine Yellow N


Manufacture

M'17:— ?I '20:— 313



2-Naphthol-3:7-disul-fonic Acid

Gamma Acid

Gamma Acid (2 mols)

Salicylic AcidPhenol[Ethylation]


D

D

D

D

5-Ethoxy-2-hydroxy-^hionaphthene-l-carboxylic Acid (C. A.nomen.)

6-Ethoxy-3-hydroxyr-l-thionaphthene-2-carboxylic Acid (Germannumbering)

COOH


FOKMATION.—5-Hydroxy-o-toluidine (amino-p-cresol) is acetylated toprotect the amino group, and then ethylated with diethyl-sulfatefor example. The resulting 2-acetamido-4-ethoxy-toluene isoxidized with potassium permanganate to 2-acetamido-4-ethoxy-benzoic acid. The acetyl group is split off by boiling with causticsoda, acid added, and the amino group diazotized with sodiumnitrite, and reacted with potassium xanthate. This xanthatecompound, upon being" treated with sodium chloro-acetate andcaustic soda, yields 5-ethoxy-phenyl-thioglycol-o-carboxylic acid.This latter heated with caustic soda condenses to 5-ethoxy-2-hydroxy-thionaphthenc-1-carboxylic acid. The successive reactionsteps are as follows:—

. COCH3. COCH3I J C H 3

. CS . OC2H5 ^ C 2 H 5 o / \ s . CH2 . COOH

C2H5O CH.COOH

LITERATURE.—Lange, Zwischenprodukte, #2167, 2168Georgievics and Grandmougin, Dye Chemistry, 437

Dyes Derived from 5-Ethoxy-2-hydroxy-thionaphthene-l-carboxylicAcid

SchulUNumberfor Bye

913

915


INDIGO GROUP DYESHelindone Orange R

Helindone FastScarlet R


I '14:— 14,511I '20:— 3,155

I '14:— 4,302I '20:— 3,748

Other IntermediatesUsed dnd Notes

5-Ethoxy-2-h y d r 0 x y-thionaphthene-1-car-boxylic Acid (2 mols)

5-Ethoxy-2-h y d r 0 x y-thionaphthene-1-car-boxylic Acid (2 mols)

[Bromination]


V

V


3-Etfcoxy~4'-methyl-diphenylamine (C A. nomen.)

3-Ethoxy-phenyl-4M;olyl-ainine

C2H5O

FORMATION.—100 parts of w-hydroxy-phenyl-p-tolyl-amine, 20.5 partsof caustic soda solution. (40° ?), 200 parts of alcohol, and 75 parts ofethyl chloride are heated together in an autoclave at 110-120° for7-8 hours


Dye Derived from S-Ethoxy-d'-methyl-diphenylamine


548



Acid Violet 6BN

Statistics ofImpoi t and

Manufacture

I '14:— 6,861I '20:— 5,582


Ketone[Sulfonation]


A

2-Ethoxy-l-naphtliylamiiie (C. A. nomen.)

See, l-Anxino-2-naphthol Ethyl Ether

3-Et±iylainino-4-methyl-diplienylaniine

See, ^-Ethyl-iV^phenyl^m-tolylene-diamine

7-Ethylamino-2-naphthaIene-sulfonic Acid (C. A. nomen.)

See, Ethyl-2-naphthylamine-7-sulfonic Acid

2-Et3aylamino-8-naphtliol-6-stilf onic Acid

See, Ethyl-gamma Acid

7-Ethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)



Ethyl-amino-naphthol-sulfonic Acid 7


m-Ethylamino-/>henol (C. A. nomen.)

Ethyl-m-amino-phenol

OH

/NH. C2H5

FORMATION.—Ethyl-aniline is sulfonated with 23 per cent oleum, the

sodium ethyl-aniline-m-sulfonate isolated and fused with caustic

potash for ten hours at 200-220°




571

577

Dyes Derived


XANTHONE DYESRhodamine 6G

Rhodine 2G

from m-Ethylamino-phenol

Statistics ojImport a'nd

Manufacture

I '14:— 37,515I >20:— 8,574


m-Ethylamino-phenol(2 mols)

Phthalic anhydride[Ethyl esterification]

Dimethylamino - hy-droxy - benzoyl - ben-zoic Acid



B

B

iV-Ethyl-«niline (C. A. nomen.)

Ethyl-aniline

NH.C2H5


STATISTICS.—Manufactured '17:— ?Manufactured 18:— ?Manufactured '19:—195,161Manufactured '20:— ?

FORMATION.—By heating aniline hydrochloride and ethyl alcoholtogether in an autoclave


USES.—For preparation of ethyl-methyl-aniline and benz^l-ethyl-aniline

a-(iV-ethyl-anilino)-^-toluene-sulfonic Acid (C A. nomen.)

See, Ethyl-sulfobenjzyl-aniline

Ethyl-benzyl-aniline

See, Benzyl-ethyl-aniline

Ethyl-benzyl-aniline-sulf onic Acid

See, Ethyl-sulfobenzyl-aniline

2:2'-Ethylene-bis (5-nitro-benzene-sulfonic Acid) (C. A. nomen.)

See, Dinitro-dibenz3i-disulfonic Acid

Ethyl-F Acid

See, Ethyl-2-naphthylamine-7-sulfonic Acid

Ethyl-gamma Acid

2-Ethylamino-8-naphthol-6-sulfonic Acid

Ethylamino-naphthol-sulfonic Acid y

7-Ethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)

[HO

HO A 1 J K H *C 2 H 5 = Ci2H13NO4S = 267


FORMATION.—G acid (2-naphthol-6: 8-disulfonic acid) is heated with

ethylamine in an autoclave at about 200°. The ethylamino-G acid

thus obtained is fused with caustic soda at 210-220°, and the ethyl-

gamma acid isolated


Dye Derived from Ethyl-gamma Acid


334


DISAZO DYEDiphenyl Blue Black


Manufacture

I 14:— 26,240

Othtzr IntermediatesUsed and Notes

HAcidBenzidine


D

6-Ethylmercapto-2-hydroxy-^hionaphthene-l-carboxylic Acid (C

A. nomen.)

5-Ethylthio-2~hydroxy-thionaphthene-l-carboxylic Acid

6-Ethylthio-3-hydroxy-l-thionaphthene-2-carboxylic Acid (Ger-man numbering)

C C O O H or C2RS CH.COOH

— 254

FORMATION.—4-Acetamido-anthranilic acid is diazotized and treated

with potassium xanthate. This xanthatc compound is reacted

with chloro-acetic acid and then hydrolyzed to split the acetyl

group from the 4-amino radical. This amino group is now diazo-

tized and reacted with potassium xanthate. This second xanthate

compound is treated with ethyl-sulfate, resulting in the formation of

5-ethylmercapto-phenyl-thioglycol-o-carboxylic acid. This latter,

upon being heated with caustic soda, condenses to 5-ethylmercapto-


2-hydroxy-thionaphthene-l-carboxylic acid. The successive re-action steps are as follows:—

CH3CO. CH3CO.

CH3CO. H N / \ s . CH2. COOHI J C O O H

. CS. OC2H5

. CH2 . COOH

CsHsO.SC.Sf' X,S.CH2.COOHI J C O O H

S.CH2.COOHCOOH

: . C O O H

(Y

LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 436-437Lange, Z^ischenprodukte, #2175

Dye Derived from 5-Et]iylmercapto-2-hydroxy-thioiiaphthene-l-carboxylic Acid

° Z Ordinary Name andClass of Dye



sed and Notes


J INDIGO GROUP DYES916 I Helindone Scarlet S I '14:— 5,515

I '20:— 565-Ethylmercapto-2-hy-

droxy-thionaphthene1-carboxylic Acid (2mols)

(C. A. nomen.)

Ethyl-methyl-aniline

Methyl-ethyl-aniline

FORMATION.—From ethyl-aniline by methylation, or from methyl-aniline by ethylation



Dye Derived from Ethyl-methyl-aniline


661

Ordinary Name andClass 0} Dye

THIAZINE DYEThionine Blue GO


I '14:— 18,618I '20:— 2,030


Dimethyl-p-phenylene-diamine - thiosulfonicAcid

[Oxidation, etc.]or


[Reduction, Oxidation,Na^Os, etc.]

orDimethyl-p-phenylene-

diamine[Na2S2O3, Oxidation,

etc.]or

Dimethyl-aniline[Naa^Os, etc.]

DyeAppli-cationCloss

B

Ethyl-a-naphthylamine

iV-Ethyl-1-naphthylamine (C. A. nomen.)


FOKMATION.—By treating a-naphthylamine with ethyl bromide

LITERATURE.—Limpricht, Ann. 99, 117 (1856)

Friedlaender and Welmans, Ber. 21, 3124 (1888)

Bamberger and Helwig, Ber. 22, 1315 (1889)



Dyes Derived from Ethyl-a-naphthyl-amine

Schidtz'Number

1S6

55S


MONOAZO DYELanacyl Violet B

DlPHENYL-XAPHTHYL-METHAXE-DYE

Victoria Blue R


I '14:— 3,628M'17:— ?M'lS:— ?

I '14:— 4171I '20:— 97

Other Intermediatessed and Notes

HAcid

Hydrol or Ketone


A

B

Ethyl-2~naphthyla-mine-7-sulfonic AcidEthyl-F AcidEthyl-j3-naphthylamine-5-sulfonic Acid7-Ethylamino-2-7iaphthalene-suIfonic Acid (C. A. nomen.)

HO3S; ;NH.C2H5 _ ,

FORMATION.—By eth\rlation of 2-naphtbyIamine-7-sulfonic acid bymeans of an ethyl halide or sodium ethyl sulfate, in an autoclaveat 100-110° C. for several hours

LITERATURE.—Lange, Zwischenprodukte, #2385Dyes Derived from Ethyl-2-naphthylamiiie-7-sulfoiiic Acid


231

371

372


DISAZO DYESCloth Red 3B

Extra

Roseazurine G

RosazurineB

Statistics ofImport andManujactwe

I '14:— 15I ;20:— 84


fl-Aroino-azo-toluene

Tolidine2-Naphthylamine-7-

sulfonic Acid

TolidineEthyl-2-naphthyl-

amine-7-sulf onic Acid(2 mols)


M

D

D


Ethyl-jS-naphthylamine-5-sulfonic AcidSee, Ethyl-2-naphthylamine-7-sulfonic Acid

iV-Ethyl-^-nitroso-aniline (C. A. nomen.)

See, p-Nitroso-ethyl-aniline

i\T~Ethyl-4-nitroso-o-£oluidine (C. A. nomen. NHR =1)

See, Nitroso-ethyl-o-toluidine

N-Ethyl-iV-phenyl-&enzylamine {C. A. nomen.)

See, Benzyl-ethyl-aniline

Ethyl-phenyl-hydrazine

a-Ethyl-a-phenyl-Aydrazine (C A. nomen.)

C2H5

*.NH2 =C8H1 2N2 = 136

FORMATION.—Phenyl-hydrazine is treated with metallic sodium toform the sodium compound, from which by means of ethyl iodidethe ethyl-phenyl-hydrazine is prepared


Dye Derived from Ethyl-phenyl-hydrazine


130


MONOAZO DYEChromazone Blue R


ManufactureOihei Intermediates

Used and Notes

p-Amino-benzaldehydeChromotropic Acid


M

. nomen.)

Phenyl-p-amino-ethyl-o-toluidine

3-Ethylamino-4-methyl-diphenylamine

NH-

JNH.C2H5

CH3


FORMATION.—JV^Phenyl-^m-tolylene-diamine (q.v.) is heated for ten

hours with ethyl bromide at 150-175°

LITERATURE.—Ger. Pat. 87,667, Frdl. IV, 85

Beilstein, Organische Chemie (3 auf.), IV spl. 400

Lange, Zwischenprodukte, #1750, 1755, referring to the

same patent, gives a different formula

Dye Derived from i^-Ethyl-iSTi-phenyl^-m-toIylene-diainine

SchvlteNumberfor Dye

684


AZINE DYEBrilliant Rhoduline

Red



sed and Notes

Nitroso-ethyl-o-toluidine


B

Ethyl-sulfobenzyl-aniline

Benz^^l-ethyl-aniline-sulfonic Acid

Ethyl-benzyl-aniline-sulfonic Acid

a-(i\T-Ethyl-anilino)-p-toluene-suhconic Acid (C. A. nomen.)

. N . = 291

STATISTICS.—Manufactured 1919 and 1920, but in undisclosed quantities

FORMATION.—By sulfonation of benz^l-ethyl-aniline with 20 per centoleum at 40-50°




Dyes Derived from Ethyl-sulfobenzyl-aniline






50

502

503

506

529

530

662

MONOAZO DYEAzo Cardinal G

TRIPHENYL-METHANE

DYESGuinea GreenAcid Green 2BG

M'14:— ?

Night Qreen ANeptune GreenBrilliant Milling

Green B

Erioglaucine

Acid Violet 6B

Acid Violet 6BFormyl VioletGuinea Violet

THIAZINE DYE

Thiocarmine R

I '14:— 49,971M'17:— ?M'18:—M'19:—I '20:—

M'20:—

??278

I '14:-M'19:-I '20:-M320:-

I '14:-M'19:-I '20:-

M'20:

40,868

10,940

66,526

6,160

I '14.-161,624M'17M'18M'19I '20

M'20- 3,925-144,207

I '14:— 1,399

p-Nitro-aniline


Benzaldehyde[Oxidation]




Benzaldehyde-0-sulf onic Acid

[Oxidation]

Ethyl-sulf ob enzyl-aniline (2 mols)

Dimethyl-p-amino-benzaldehyde

[Oxidation]

Diethyl-anilineEthyl-sulfobenzyl-

aniline (2 mols)[Oxidation]

Ethyl-sulf ob enzyl-p-phenylene-diamine

etc.]


iV-Ethyl-i^-(^-sulfo-benzyl)-metanilic Acid (C. A. nomen.)

See, Benzyl-ethyl-anftine-disulfonic Acid

Ethyl-sulfobenzyl-^-phenylene-diamine

Benjzyl-ethyl-p-phen}iene-diamine-sulfonic Acid

p-Amino-benzyl-ethyl-aniline-sulfonic Acid

a-(p-Amino-A'-ethyl-anilino)-p-toluene-sulfonic Acid (C A.nomen.)

y~K = 3 0 6

FORMATION.—Ben^yl-ethyl-ardline-sulfonic acid is changed into therdtroso-derivative with nitrous acid, and this latter is reduced withsulfite

LITERATURE.—Lange, Zwischenprodukte, #1499, 929Cf. Cain, Intermediate Products (2d Ed.), 69

Dye Derived from Ethyl-sulfobemiyl-^-phenylene-diainine

SchuLttNumberj or Dye

662

Ordinaly Name andClass of Dye

THIAZIXB DYEThocannine R


Manufacture

I '14:— 1,399



[Na^Oa, etc.]


A

Et^Lyl-sulfobenzyl-^-phenylene-diamine-tidostilfonic Acid

a-(4-Amino-Ar-ethyl-3-sulfomercapto-ardlino)-p^oluene-sulfonicAcid (C. A. nomen.)

CJEL-—X—CH

NHs

S.SO3H


FORMATION.—Ethyl-sulfobenzyl-p-phenylene-diamine is dissolved indilute hydrochloric acid, zinc chloride solution and sodium thio-sulfate solution added; and then oxidized quickly with solution ofsodium bichromate


Dye Derived from Ethyl-sulfobenzyl-^-phenylene-diamine-thiosulfonicAcid


667


THIAZINE DYEBrilliant Alizarin

BlueIndochromine T


Manufacture

I '14:— 19,481M'19:— ?I '20:— 3,214M'20:— ?


1:2-Naphthoquinone


M

6-Ethylthio-2-hydroxy-thionaphthene-l-carboxylic Acid

See, 5-Ethylmercapto-2-hydroxy-thionaphthene-l-carboxylicAcid (C A. nomen.)

6-Ethylthio-3-hydroxy-l-thionaphthene-2-carboxylic Acid (Ger-man numbering)

See, S-Ethylmercapto^-hydroxy-thionaphthene-l-carboxylicAcid (C A. nomen.)

JV-Ethyl-o-*oluidine (C. A. nomen.)

Ethyl-o-toluidine

HNC2H5

FORMATION.—From o-toluidine hydrochloride and ethyl alcohol ^byheating together in an autoclave at about 200°. The crude productcontains considerable o-toluidine, which can be removed as sulfateby adding just sufficient sulfuric acid to combine with it; allowingto cool, and centrifugating



Dyes Derived from 2V-Ethyl-o-toluidine


500

546

663



Setocyanine 0

Cyanol

THIAZINE DTENew Methylene Blue

N


Manufacture

I >14:— 923I '20:— 1,102

I ' 14 : - 40,015I '20:— 7,954

I '14:— 30,392I 320:— 513





m-Hydroxy-benzalde-hyde



[Nitroso-derivative,Nas&Oa, etc.]

orp-Amino-etliyl-o-

toluidine[Na2S2O3, etc.]


B

A

B

iV-Ethyi-p-*oluidine (C. A. nomen.)

Ethyl-p-toluidine

HNC2H5

FORMATION.—From p-toluidine hydrochloride and ethyl alcohol byheating together in an autoclave and purification of resultingproduct

LITERATURE.—C/. Cain, Intermediate Products (2d Ed.), 71Lange, Zwischenprodukte, #128Ger. Pat. 21,241, Frdl. 1, 21


Dye Derived from N-Ethyl-^-toluidine

283




Manufactw eOther Intermediates

Used and Notes


671AZINE DYE

Induline Scarlet I '14:— 198I '20:— 154

a-Naphthylamine

iV*~Ethyl-4-m-folylene-diamine (C. A. nomen. NH2=1)

p-Amino-ethyl-o-toluidine

NH2

W . C 2 H 5 — CoHuNTi —150

FOKMATION.—From 5-nitro-ethyl-o-toluidine (NH2 = 1) [4-nitro-ethyl-o-toluidine (CH3==1)] by reduction with zinc dust and hydro-chloric acid

LITERATURE.—Beilstein, Organische Chemie (3 auf.), IV, 601J. Chem. Soc, 67, 247

Dye Derived from iV3-Ethyl-4-m-tolylene-diamine

SchultzNumbeifor Dye

684


AZINE DYEBrilliant Rhodulinc

Red

Statistics ofImpoi * and

Manujactu. eOther Intermediates

Used and Notes

Methyl-o-toluidineAniline


B

JN^-Ethyl-^-^olylene-diamine (C. A. nomen.)

p-Amino-ethyl-o-toluidine

NH.C 2 H 5

Q O H , _

NHS

= C 9 H u N 2 =150


FORMATION.—From 4-nitroso-ethyl-o-toluidine (NHR= 1) by reductionwith SnCl2+HCl


Dye Derived from JV^-Ethyl-^-tolylene-diamine

SchvltzNumberJor Dye

663


THIAZINE DYENew Methylene Blue

N


I '14:— 30,392I '20:— 513


Ethyl-o-toluidine[Na SsOs]


B

Ewer and Pick's Acid

See, Naphthalene-1:6-disulfonic Acid

FAcid

See, 2-Naphthol-7-sulfonic Acid


2-Naphthylamine-3: 7-disulfonie Acid (not considered herein)

2-Amino-7-naphthol-3-sulfonic Acid (not considered herein)

2: 7-Dihydrox5r-naphthalene-3-sulfonic Acid (not considered herein)

Formaniline

See, Anhydro-formaldehyde-aniline

4-Formyl-m-&enzene-disulfonic Acid (C. A. nomen.)

See, Benzaldehyde-disulfonic Acid

o-Formyl-frenzene-sulfonic Acid (C. A. nomen.)

See, Benzaldehyde-o-sulfonic Acid

4-Formyl-6-methyl-m-benzene-disulfonic Acid

See, 3-methyl-benzaldehyde-4: 6-disulfonic Acid

Jorsling's Acid I



Forsling's Acid II


Freund's Acid

l-Naphthylamine-3: 6-disulfonic Acid

4-Amino-2: 7-naphthalene-disulfonic Acid (C A. nomen.)

a-Naphthylamine-a-disulfonic Acid

A16n's a Acid

NH2

285

HO3S SO3H

STATISTICS.—Imported '14:—5,246 lbs.Manufactured ' 18:— ?Manufactured ' 19:— ?

FORMATION.—Naphthalene is heated with five parts of concentratedsulfuric acid for about 8 hours at 160-200°, the mixture is cooledand two parts of 50 per cent nitric acid are added. After reactingfor some time the nitration mass is diluted and reduced with iron

LITERATURE.—Cain, Intermediate Products (2d Ed.), 195Thorpe, Die: Chemistry, 3, 592Lange, Zwischenprodukte, #2591

Dyes Derived from Freund's Acid

SchultzNumbet

Bye

266

267


DISAZO DYESNaphthylamine

Black D

Anthracite Black


Manufacture

I '14:—152,141M'17:— ?M'18:— 29,724M'19:— ?I '20:— 1,687M'20:— ?

I '14:-- 99M'17:— ?I '20:— 220

Oihei Intermedic tesUsed and Notes

a-Naphthylamine(2 mols)

a-NaphthylamineDiphenyl-m-phenylene-diamine


A

A


G Acidl

2-Naphthol-6: 8-disulfonic Acid (C A. nomen.)

j3-Naphthol-]5-disulfonic Acid

/3-Naphthol-Y-disulfonic Acid

/3-Naphthol-disulfonic Acid G

/3-Naphthol-disulfonic Acid 7

YAcid

HO3S

HO3S0 H =

STATISTICS.—Imported 14':—11,624 lbs.Manufactured'18:— ?Manufactured '19:—732,192 lbs.Manufactured '20:—1,446,605 lbs.

FORMATION.—Sulfonation of /S-naphthol and separation from the Racid simultaneously formed

LITERATURE.—Cain, Intermediate Products (2d Ed.), 227Thorpe, Die. Chemistry, 3, 627Lange, Zwischenprodukte, #2659-2661

Dyes Derived from G- Acid


38


MONOAZO DYESOrange G


Manufacture

I '14:— 48,456M'17:— ?M'18:— ?M'19:— ?I '20:— 100

M'20:—120,874


Aniline


A

1 Occasionally in the old literature G acid is used to mean Gamma acid (or2-Amino-8-naphthol-6-sulfonic acid), or 2-Naphthylamine-6:8-disulfonic acid, or1:7-Dihydroxy-naphthalene-3-sulfonic acid.


Dyes Derived from G Acid (continued)

287


113

122

169

227

270

319

566



Crystal Ponceau

Erica G

Cochineal Red A

DISAZO DYESBrilliant Croceine M


Diamine Scarlet B

DlPHENYL-NAPHTHYL-METHANE DYE

Wool Green S


I 14:— 628

I 14:— 2,370M18:— ?I '20:— 1,142

I 14:— 32,645M17:— ?M18:— ?M19:—231,519M'20:—288,945

I 14:—125,137M17:— ?M18:— 84,643M19:—157,509I '20:— 49M'20:—129,124

I 14:— 41,175I '20:— 10,565

I 14:— 60,073M17:— ?M19:— ?I '20:—127,764M '20:—212,362


a-Naphthylamine

Dehydro-thio-ra-xyli-dine

Naphthionic Acid

Amino-azo-beiizene

Amino-G AcidAnilineRAcid

BenzidinePhenol[Ethylation]

Hydrol


A

D

A

A

A

D

A

Gallamic AcidSee, Gallamide (C. A. nomen.)

Gallamide (C. A. nomen.)Gallamic AcidGallic Acid Amide


CO.NH*

FORMATION.—From tannin by boiling with strong solution of am-monium sulfite and aqueous ammonia until the excess of ammoniahas been driven off. The amide crystallizes out upon cooling

LITERATURE.—Green, Organic Coloring Matters (1908), 46Lange, Zwischenprodukte, #1546

Dyes Derived from Gallamide





Used and Notes


627

630

637

638

641

646

OXAZINE DYESModern Cyanine

Cyanaznrine

Gallamine Blue

Amido GallainliieBlue

Coreine RRCoelestine Blue B

Coreine AR

I '14:I '20:

Nitroso-dimethyl-anilineDimethyl-p-phenylene-

diamineReduction]

Nitroso-dimethyl-anilineAniline[Reduction]

2,756 Nitroso-dimethyl-aniline16,446

Nitroso-dimethyl-aniline[Ammonia, Reduction]

1,320 Nitroso-diethyl-anilineI '20:— 44 or Diethylamino-azo-

benzene

Nitroso-diethyl-ardlineor Diethylamino-azo-

benzeneAniline[Sulfonation]

or[Coreine RR; Aniline;

Sulfonation]

M

M

M

M

M

M


Gallanilic Acid

See, Gallanilide (C. A. nomen.)

Gallanilide (C. A. nomen.)

Gallanilic Acid

Gallic Acid Anilide

CO—NH

289

H

STATISTICS.—Manufactured '19:—Manufactured '20:—

FORMATION.—From tannin by heating with aniline

LITERATURE.—Green, Organic Coloring Matters (1908), 46Cf. Lange, Zwischenprodukte, #1546

Dye Derived from Gallanilide


639


OXAZINE DYEGallanilic Violet R, B



Used and Notes

Nitroso-dimethyl-(ordiethyl-) aniline


M

Gallic Acid

3:4: 5-Trihydroxy-benzoic Acid

COOH

STATISTICS.—Imported '14:—61,644 lbs.Manufactured regularly, but in amounts that are not

yearly disclosed


FORIMATION.—From nut galls (Chinese or Aleppo) by action of ferments

or acids, and subsequent extraction and crystallization



Dyes Derived from Gallic Acid





Used and Notes


599

601

622

624

625

626

XANTHONE DYESGalleine

Coeruleine S

OXAZINE DYESDelphine Blue B

Modern Violet N

Chrome Heliotrope

Gallocyanine

I '14:— 15,404M'19:— ?

'20:— 5,075M'20:— ?

I '14:—M'19:—I '20:—

3,404

9,392

M'17:— ?M'18:— ?M'19:— 43,827I '20:— 29,643M '20:— 76,719

I '20:— 5,688

I '14:— 78,253M'17:— ?M '18:—435,460M'19:—365,243I '20:— 12,414M'20:— 70,169

Phthalic AnhydrideGallic Acid (2 mols)

Phthalic AnhydrideGallic Acid (2 mols)[Dehydration]

or[Galleine dehydrated]

Nitroso-dimethylanilineAniline[Sulfonation]

or[Gallocyanine, Aniline,

Sulfonation]

Nitroso-dimethylaniline[CO2 split off]

or[Gallocyanine heated]

Nitroso-methyl-aniline[Reduction]

Nitroso-dimethylaniline

M

M

M

M

M

M


Dyes Derived from Gallic Acid (continued)





Used and Notes


628

629

631

632

633

634

635

OXAZINE DYES(continued)

Gallocyanine MS

Gallogreen DHModern Blue

Chromocyanine V

Ultra Violet LGP

Indalizarine R

Indalizarine Green

Blue 1900 TCModern Violet

I '20:— 22 Dimethylamino-azo-benzene-disulfonicAcid

orNitroso-dimethyl-

aniline[Sulfonation; Oxidation]


[Formaldehyde, Reduc-tion]

or[Gallocyanine, Formal-

dehyde, Reduction]

M'18:-MJ19:-I '20:-M'20:-

I '14:

??

1,287?

4,368

I '20:— 551

I '20:— 1,933


[Sulfonation]or

[Gallocyanine, Sulfites]

Nitroso-dimethyl-aniline (2 mols)

Gallic Acid (2 mols)


[Sulfonation]


[Sulfonation; Nitration]or

[Indalizarine nitrated]


[Reduction]




642

643

644

645

664


OXAZINB DYES(continued)

Phenocyanine TC

Phenocyanine TV

Ultracyanine B

Gallazine A

THIAZINE DYELeuco-gallo

Thionine DH

Statistics ofImpart and

Manufacture

I '20:— 4,740

MJ17:— ?I '20:— 1,543



Resorcinolor

[Gallocyanine, Resorci-nol]


Resorcinol[Sulfonation]

or[Phenocyanine sulfo-

nated]


Resorcinol [AlkalineCondensation]

or[Gallocyanine; Resorci-

nol; Alkaline Con-densation]


Schaeffer's Acid[Oxidation]

or[ G a l l o c y a n i n e ,

Schaeffer's AcidOxidation]

Dimethyl-p-phenylene-diamine-thiosulfonicAcid


M

M

M

M

M




772

782



Galloflavine W



Manufacture

I '14:— [838I '20:— 24

I '14:—115,586M/17:— ?M'18:— ?M'19:— 40,426I '20:— 2,728M'20:— 42,840


Gallic Acid (2 mols)

Benzoic Acidor Phthalic Anhydride


M

M

Gallic Acid Amide

See, Gallamide (C. A. nomen.)

Gallic Acid Anilide

See, Gallanilide (C. A. nomen.)

Gallic Acid Methyl Ester

CO.OCHs

OH

FOKMATION.—From gallic acid by heating with methanol (methylalcohol) and hydrochloric acid



Dyes Derived from Gallic Acid Methyl Ester




Manufacture



636

640

OXAZINE DYES

Prune

Modern Azurine DH

I '14:— 3,197 Nitroso-dimethyl-anilineI '20

3,4,418

Nitroso-dimethyl-anilineAniline

M

M

Gamma Acid


Amino-naphthol-sulfonic Acid 7

Amino-naphthol-sulfonic Acid G

G Acid (occasionally in old literature)


H O

=:Ci0H9NO4S = 239HO3S

STATISTICS.—Manufac tured J 18:— ?

Manufac tured ;19:—155,025 lbs.

Manufac tured '20:—418,456 lbs.

FORMATION.—£-Naph tho l is sulfonated to R and G acids, and these

two /3-naphthol-disulfonic acids are separated. The sodium salt

of G acid is hea ted in an autoclave with ammonia and sodium

bisulfite solution to form amino-G acid (2-naphthylamine-6:8-

disulfonic acid). This la t ter is fused in an autoclave with caustic

soda, t h u s forming gamma acid.

L I T E R A T U R E . — C a i n , In te rmedia te Products (2d Ed. ) , 236



Dyes Derived from Gamma Acid

295


241

245

274

295

297

327

328

329

330

331

332


DISAZO DYESNeutral Gray G

Nyanza Black B

Diaminogene BB

Diphenyl Fast Black

Benzo FastPink 2BL

Diamine Violet N

Diamine Black HODianol Black RW

Diamine Brown V

Zambesi Brown G

Alkali DarkBrown GV


IMIM

II

I

II

IMM

I

M

II

II

Statistics ofImport aridManufacture

14:—19:—'20:—'20:—

2,546?

3,472?

14:—313,629'20:— 18,120

14:—

14:—'20:—

14:—19:—'20:—

14:—

19:—

14:—'20:—

14:—'20:—

882

3,2521,226

18,263?

92,503

8,253

?

4,0281,104

5,9853,799


Anilinea-Naphthylarnin

p-Nitro-anilineq-Naphthylamin e[p-Nitro-aniline reduced

after coupling]

Acetyl-1:4-naphthy-lene-diamine-6-sul-f onic Acid

a-Naphthylamin

p: p'-Diamino-ditolyl-amine

m-Tolylene-diamine

Diamino-diphenyl-urea-disuKonic Acid

Gamma Acid (2 mols)

BenzidineGamma Acid (2 mols)

BenzidineGamma Acid (2 mols)

Benzidine7n-Phenylene-dianrine

Benzidine2:7-Naphthylene-dia-

mine-sulf onic Acid

BenzidineNitroso-jS-naphthol

BenzidineAmino-R Acid


D

D

D

D

D

D

D

D

D

D

D



333

335

343

344

399

402

403

436

437

Dyes Derived



Diamine Black BHOxamine Black BHN

i

NaphthamineBlack RE

Diamine Fast Red F

Diamine Brown M

Indazurine TS

Diamine BlueBlack E

Diamine Black BO

TKISAZO DYESColumbia Black FF

Iso-DiphenylBlack R

from Gamma


Manufacture

I '14:—619,430M'17:— ?M'18:— ?M'19 :—485,046I '20:— 5,512M'20:—803,501

I '14:— 49,016

I '14:— 50,479M'19:— 56,864I '20:— 4,040M'20:—115,865

I J14:— 65,396M'lS:— ?M'19:— 15,959M'20:—257,872

I '14:—102,997M'18:— ?M'19:— ?I '20:— 23,350M'20:— ?

Acid (continued)


BenzidineHAcid

BenzidineKAcid



Tolidin1:7-Dihydroxy-2-naph-

thoic-4-sulfonic Acid

Ethoxy-benzidine2-Naphthol-3:7-disul-

f onic Acid

Ethoxy-benzidineGamma Acid (2 mols)

l-Naphthylamine-6-and 7-sulf onic Acids

m-Phenylene-diaminep-Phenylene-diamine

Resorcinolp-Phenylene-diaminem-Phenylene-diamine


D

D

D

D

D

D

D

D

D


Dyes Derived from Gamma Acid (continued)






440

442

444

461

472

473

491



Direct Black V

Cr umpsall DirectFast Brown B

Coomassie UnionBlacks

Chloramine Blue HW

Diamine Black HW

TETRAKISAZO DYEDianil Black PR

I 14:—145,738

I '20:-- 342

Benzidinera-Amino-p-cresol

Methyl EtherGamma Acid (2 mols)

Benzidine2R Acida-Naphthylamine


1:4-Naphthylene-dia-mine-2-suLfonic Acid

m-Phenylene-(or Toly-lene-) diamine orResorcinol (2 mols)

Benzidine2: 5-Dichloro-anilineHAcid

Benzidinep-Nitro-anilineHAcid

Benzidine sulf onic AcidGamma Acid (2 mols)m-Phenylene-diamine

(2 mols)

G R Acid

See, l -Naphthol-3: 6-disulfonic Acid


H Acid


Amino-naphthol-disulfonic Acid H

8-Amino-l~naphthol-3: 6-disulfonic Acid (C. A. nomen.)

HO NH2

HO3S SO3H

STATISTICS.—Imported '14:— 96,296 lbs.Manufactured '17:—3,089,273 lbs.Manufactured '18:—3,837,534 lbs.Manufactured '19:—2,883,228 lbs.Manufactured '20:—5,180,993 lbs.

FORMATION.—Naphthalene is trisulf onated with oleum, and then nitratedand reduced with iron, resulting in the formation of Koch acid orl-naphthylamine-3:6: 8-trisulfonic acid. This latter is now fused inan autoclave with caustic soda, forming H acid



41

182

186

Dyes


MONOAZO DYESFast Acid

Fuchsine B

Fast Sulf onViolet 5BS

Brilliant Sulf onRedB

Lanacyl Violet B

Derived from 1


M'18:— ?M'19:— 26,699M'20:— 30,678

I '14:— 4,871I '20:— 4,740

I '14:— 3,628M'17:— ?M'18:— ?

H Acid


Aniline

AnilineBenzene-(or Toluene-)

sulf 0 chloride



A

A

A


Dyes Derived from H Acid (continued)






187

188

189

217

261

264

333


Lanaeyl Blue BB

Tolyl Blue SRSulfon Acid Blue R

Sulf on Acid Blue B

'14:— 4,200

14:— 45,038M'17:— ?M'18:— ?M'19:— ?M'20:—454,185

'14:— 35,560M'17:— ?M'19:— ?M'20:— ?

DISAZO DYESNaphthol Blue BlackAgalma Black 10B

I '14:—431,027M'17:—620,218M'18:—

1,158,309M'19:—

1,877,860I '20:— 840M'20:—

2,608,864

5-Amino-l-naphthol

Phenyl-1-naphthyl-amine-8-sulf onic Acid

Tolyl-1-naphthylamine-8-sulfonic Acid

p-Nitro-anilineAniline

Buffalo Black 10B

Fast Sulf onBlack F

M '17:-M'18:-M'19:-M'20:-

M'19:— ?I '20:— 2,204M'20:— ?

Diamine Black BHOxamine Black BHN M

I '14:—619,430'17:— ?

M'18:— ?M'19:—485,046I '20:— 5,512M'20:—803,501

Sulf anilic Acida-Naphthylamine

Naphthionic AcidjS-Naphthol

BenzidineGamma Acid

D


Dyes Derived from H Acid {continued)





Used and Notes


334

336

337

353

381

382

383

386

390


Diphenyl Blue Black

Benzo Cyanine E

I '14:— 26,240

:— 201

Diamine Blue 2BBenzo Blue 2B


Azo Black Blue B, R

Azo Mauve B

Naphthazurine B

Diamine Blue BXBenzo Blue BX

I '14:— 19,035M'17:—

1,445,059M'18:—

1,523,985

1,380,335M'20:—

1,789,774

I '14:— 6,000

BenzidineEthyl-gamma Acid

Benzidinel-Amino-8-naphthol-4-

sulf onic Acid


Benzo Cyanine B

M'17:— ?M'20:— ?

I '14:— 4,782

I '14:— 1,740M'17:— ?M'18:— ?M'19:— 92,214I '20:— 4,520

M'20:— 90,147

I '14:— 201

Benzidine1:7-Dihydroxy-6-naph-


Tolidinem-Hydroxy-diphenyl-

amine

a-NaphthylamineTolidine

Tolidine/3-Naphthylamine


Tolidinel-Amino-8-naphthol-4-

sulf onic Acid



301

SchuUzNumberfor Dye

391

425

426

430

438

439

441

443

446




Benzo Cyanine 3B

Diamine Pure BlueBenzamine Pure

Blue

Indazurine 5 GM

TBISAZO DYESMelogene Blue BH

Direct Indigo Blue A

Diazo Blue Black RS

Direct IndoncBlue R

Benzo Olive


Manufacture

I '14:— 1,365M'17:— 14,533M'18:— 99,645M'19:—182,940I '20:— 1,124M'20:—136,S91

I '14:— 1,001

I '14:— 12,881M'17:— ?M'18:— ?M'19:—192,350I '20:— 662M'20:—223,100

M'17:— ?M'18:— ?

M'18:— ?

M'19:— ?M'20:— ?

I '14:— 1,149


TolidineH Acid (2 mols)

Dianisidinel-Amino-8-naphthol-4-

sulfonic Acid

DianisidineH Acid (2 mols)

Dianisidine1:7-Dihydroxy-2-naph-

thoic-4-sulf onic Acid

Benzidinep-XylidineH Acid (2 mols)

H Acid (2 mols)Benzidinem-Amino-p-cresol

Methyl Ether

Benzidinea-NaphthylamineH Acid (2 mols)

Benzidinea-Naphthylamine2 R Acid

BenzidineSalicylic Acida-Naphthylamine


D

D

D

D

D

D

D

D

D



SchultsNumberfar Dye





448

462

463

464

467

468

469

470

TEISAZO DYES(continued)

Diamine Bronze G

Erie DirectBlack GX

Direct. DeepBlack EW

I '14:— 4,495

I '14:—1,246,536

M'17:— ?

M'19:—

M'20:

Erie DirectBlack RX

Cotton Black E

Erie DirectGreen ET

Diphenyl Green G

Diphenyl Green 3G

Chloramine Black N

Chloramine Green B

BenzidineSalicylic Acidm-Phenylene-diamine

BenzidineAnilinem-Phenylene-diainine

7,250,007

'7,736,994

I '14:—248,567M'19:— ?M '20:—

2,050,741

M'17:— ?M'18:— ?M'19:— 69,700M'20:— ?

I '20:— 2,205

I '14:— 39,600M'19:— ?I '20:— 1,76;

I '14:— 1,675M'19:— ?M'20:— ?

BenzidineAnilinew-Tolylene-diamine

BenzidineAnilinePhenol

Benzidineo-Chloro-p-nitro-anilinePhenol

Benzidineo-Chloro-p-nitro-aniHneSalicylic Acid

Benzidine2:5-DicUoro-anilinem-Phenylene-diamine

Benzidine2:5-Dichloro-anilinePhenol



303



Statistics ojImpoii and


Used and Notes


471

472

473

474

475


Chloramine Blue 3G

ChloramineBlue HW

Diamine Black HW



I '14:-M'19:-I '20:-

286

882

I '20:- 342

I '14:— 77,100M'17:— ?M'18:—295,147M '19:—305,854I '20:— 2,460M'20:-420,138

I '14:— 7,329M'17:— ?M'18:— 29,118M'19:—136,638I '20:— 1,332

M '20:— 53,292

Benzidine D2: 5-Dichloro-anilineH Acid (2 mols)

Benzidine D2: 5-Dichloro-anilineGamma Acid

Benzidine Dp-Nitro-anilineGamma Acid

Benzidine Dp-Nitro-anilinePhenol

Benzidine Dp-Nitro-anilineSalicylic Acid

Histazarin

2: 3-Dihydroxy-anthraquinono (not considered herein)

o-Homo-salicylic Acid

See, o-Cresotic Acid

ji-Hydrazine-6enzene-sulfonic Acid (C. A. nomen.)

See, Phenyl-hydrazine-p-sulfonic Acid

a-Hydro-juglone

1:4: 5-Trihydroxy-naphthalene (not considered herein)


HydrolTetramethyl-diamino-benzohydrol

p: p'-Bis(dimethylamino)-&enzohydrol (C. A. nomen.)

Michler's Hydrol

H

/ ~ \ N (CH3)2 = C17BWS"2O = 270

OH

STATISTICS.—Manufactured '20:

FORMATION.—Dimethyl-aniline

-88,583 lbs.

is condensed with formaldehyde inpresence of hydrochloric acid, and the resulting product is oxidizedwith lead peroxide; or the corresponding ketone (tetramethyl-diamino-benzophenone) is reduced with zinc

LITERATTJEE.—Cain, Intermediate Products (2d Ed.), 102-3Lange, Zwischenprodukte, #1358

Dyes Derived from Hydrol

SchultzNumberfar Bye





498

509

516

TRIPHENYL-METHANE

D Y E S

Turquoise Blue

Chrome Green

Crystal Violet

I '14:-I '20:

1,5411,407

'14:— 51,872M ' 1 7 : — ?M ' 1 8 : — ?M ' 1 9 : —I '20:—

M ' 2 0 : —

p-Nitro-toluene[Oxidation]

Benzoic Acid[Oxidation]

Dimethyl-aniline[Oxidation]

B

M

B

?2,919

?

528 Fast Acid Violet 10B I '14:— 12,919M ' 1 7 : — ?M ' 1 8 : — ?M ' 1 9 : — ?I '20:— 10,086

M ' 2 0 : — ?

Benzyl-ethyl (me thyl) -aniliri e-disulf onic Acid

[Oxidation]

A


Dyes Derived from Hydrol (continued)

305





Used and Notes


542

549

550

558

559

562

563

564


Agalma Green B I '14:— 2,294

Chrome Violet

Chrome Bordeaux

DlPHENYL-NAPHTHYL-METHANE DYES

Victoria Blue R,

Victoria Blue B

I '14:— 51

I '14:-I '20:-

4,17197

I '14:—127,769M'17M'18M'19I '20

M'20>:— 4,171

Fast Acid Blue B

New Patent Blue B

I '14:— 33,251I '20:— 6,478

I '14:-I '20:-

59.1,814

Naphthalene Green V I '14:— 22,144I '20:— 9,291

4-Chloro-3: 5-dinitro-benzene-sulfonic Acid

Metanilic Acidor

Dinitro-diphenylamine-disulf onic Acid

Salicylic Acid[Oxidation]

Amino-salicylic Acid[Oxidation]

Ethyl-a-naphthylamine[Oxidation]

Phenyl-a-naphthyl-aminc

[Oxidation]

l-Naphththylamine-2-sulf onic Acid

[Oxidation]

Naphthionic Acidor

Laurent's Acid[Substitution of -NH2by -SOsNa and Oxida-

tion]

Naphthaleneor

Naphthalene-2:7-disulf onic Acid


Dyes Derived from Hydrol (continued)

SchullzNumberfor Dye



Other IntermediatesUsed ,and Notes


566

567

652

DlPHENYL-NAPHTHYL"METHANE DYES

(continued)Wool Green S

Chrome Blue

OXAZINE DYENew Fast Blue F

I '14:— 60,073M'17:— ?M'19:— ?I >20:—127,764M'20:—212,362

I '14:— 2,502

GAcid

l-Hydroxy-2-naphthoicAcid

[Oxidation]


/3-Naphtholor

[Meldola's Blue]

M

B

3-Hydroxy-acenaphthene

4-Hydroxy-acenaphthene (German numbering)

3-Acenaphthenol (C. A. nomen.)

CH2-CH2

FORMATION.—From 3-amino-acenaphthene by diazotizing and thenboiling to hydrolyze the diazo group

LITERATURE.—Lange, Zwischenprodukte, #2957Frdl. 10, 544

Dye Derived from 3-Hydroxy-acenaphthene


894


INDIGO GROUP DYESAlizarin Indigo B


Manufacture

I 14:— 402I '20:— 291


2-Isatin Anilide


V


4-Hydroxy-acenaphthene (German numbering)

See, 3-Hydroxy-acenaphthene


See, 1-Anthrol (C A. nomen.)


See, 9-Anthrol (C A. nomen.)

1-Hydroxy-anthranol

l-Hydroxy-9-anthrol

a-Hydroxy-anthranol

1: 9-Anthradiol (C A. nomen.)

OH

OH

307

H

FORMATION.—1-Hydroxy-anthraquinone is reduced with hydrosulfiteand alkali or with stannous chloride and hydrochloric acid

LITERATURE— Ger. Pat. 242,053; Frdl. 10, 532Barnett, Anthracene and Anthraquinone

Dye Derived from 1-Hydroxy-anthranol

SchuUzNumberfor Dye

896


INDIGO GROUP DYESHclindone Blue 3GN


Manufacture

I '14:— 622I '20:-— 2,527


2-Isatin Anilide


V

a-Hydroxy-anthranol


l-Hydroxy-9-anthrol



m-Hydroxy-benzaldehyde

FORMATION.—From m-amino-benzaldehyde by diazotizing the amino-group and then boiling until the nitrogen evolution ceases


Dyes Derived from m-Hydroxy-benzaldehyde





Used and Notes


543

544

545

546

TEIPHENYL-METHANE

DYES

Patent Blue V

Cyanine B

Patent Blue A

Cyanol

I 314:—196,228M317:— ?M' lS :— ?I '20:— 36,420

I '14:-I '20:-

8,39824

I '14:-M'18:-I '20:— 44,801

63,744?

I ' 1 4 : -

I ' 2 0 : -

4 0 , 0 1 5

7 , 9 5 4

D i e t h y l - a n i l i n e (2 m o l s )[Sulf o n a t i o n , O x i d a t i o n ]

D i e t h y l - a n i l i n e (2 m o l s )[ S u l f o n a t i o n , O x i d a t i o n ]

or

[ O x i d a t i o n of P a t e n tB l u e ]

B e n z y l - e t h y l - a n i l i n e(2 m o l s )

[ S u l f o n a t i o n , O x i d a t i o n ]

E t h y l - o - t o l u i d i n e(2 m o l s )

[ S u l f o n a t i o n , O x i d a t i o n 1

A

m - H y d r o x y - d i m e t h y l - a n i l i n e

See, 7 n - D i m e t h y l a m i n o - p h e n o l ( C . A. nomen.)


m-Hydroxy-diphenylamine

Phenyl-ra-amino-phenol

m-Anilino-phenol (C. A. nomen.)

HO

^ -NH

309

FORMATION.—(1) From resorcinol by heating with aniline and zincchloride at 280-290°. (2) From m-amino-phenol by heating withaniline hydrochloride in an autoclave at 210-215°


Dyes Derived from m-Hydroxy-diphenylamine


381

658


DISAZO DYEAzo Black Blue B, R

OXAZINE DYEFast Black

Statistics ofImport andManvfacturc

I '14:— 1,960I '20:— 2,S83


TolidineH Acid

Nitroso-dimeiliyl-aniline


D

B

iV-(3-Hydroxy-4-keto-l(4)-naphthylidene)-sulfanilic Acid (C. A.nomen,)

See, j3-Hydroxy-naphthoquinonyl-aniline-p-bulfonic Acid

l-Hydroxy-naphthalene-2-carboxylic Acid

See, l-Hydroxy-2-naphthoic Acid (C. A. nomen.)

2-Hydroxy-naphthalene-3-carboxylic Acid

See, 3-Hyclroxy-2-naphthoic Acid (C. A. nomen.)

Hydroxy-naphthalene-sulfonic Acids

See, Naphthol-sulfonic Acids


l-Hydroxy-2-naphthoic Acid (C. A. nomen.)

l-Hydroxy-naphthalene-2-carboxylic Acid

a-Oxy-naphthoic Acid

a-Naphthol-carboxylic Acid

OH

S

FORMATION.—a-Naphthol is converted into sodium a-naphtholate, andtreated with the theoretical amount of carbon dioxide under pressureand at 120-145°


Dye Derived from l-Hydroxy-2-naphthoic Acid

SchvltzNumber*or Dye

567


DlPHENTL-NAPHTHYL-METHANE DYES

Chrome Blue



Used and Notes

Hydrol[Oxidation]


M

2-Hydroxy-3-naphthoic Acid

See, 3-Hydroxy-2-naphthoic Acid (C. A. nomen.)

3-Hydroxy-2-naphthoic Acid (C. A. nomen.)

2-Hydroxy-3-naphthoic Acid

2-Hydroxy-naphthalene-3-carboxylic Acid

/3-Oxy-naphthoic Acid

/?-Naphthol-carboxylic Acid

OH


STATISTICS.—Imports '14:—2,359 lbs.Manufactured '19:— ?Manufactured '20:— ?

FORMATION.—/3-Naphthol is converted into the sodium /3-naphtholate,and treated with the theoretical amount of carbon dioxide underpressure and at 200-250°

LITEKATUEE.—Cain, Intermediate Products (2d Ed.), 241

Lange, Zwischenprodukte, #775, 2308

Dyes Derived from 3-Hydroxy-2-naphthoic Acid


45

152

179


MONOAZO DYESBrilliant Lake

RedR

Lithol Rubine BPermanent Red 4B

Lake Bordeaux B


Manufacture

I '14:— 31,674I '20:— 1,071

I '14:—101,395M'19:— ?I '20:— 2,983M'20:— ?


Aniline

p-Toluidine-o-sulfonicAcid

2-Naphthylamine-l-sul-fonic Acid


CL

CL

CL

]3-Hydroxy-naphthoquinone

1:2-Dihydroxy-naphthalene (not considered herein)

/3-Hydroxy-naphthoquinonyl-aniline-^-sulfonic Acid

A7'-(3-Hydroxy-4-keto-l(4)-naphthylidene)-sulfanilic Acid (C. A.

-o O3H


FORMATION.—The potassium salt of 1: 2-naphthoquinone-4-sulfonic

acid is condensed with the sodium salt of sulfanilic acid, splitting

off a sulfonic group and furnishing the /3-hydroxy-naphthoquinonyl-

aniline-p-sulfonic acid

LITERATURE.—Lange, Schwefelfarbstoffe, 393,139

Lange, Zwischenprodukte, #2870, 2871Schultz, Farbstofftabellen, #747

Dye Derived from /5-Hydroxy-naphthoquinonyl-aniline-^-sulfonicAcid


747


SULFUR DYEThional Brown G


Manufacture

I '14:— 110I '20:— 43,219


[S+Na*S]


s

4-(^-Hydroxy-phenyl-amino)-l-phenylamino-naphthalene-8-sulfonic Acid

8-Anilino-5-(p-hydroxy-anilino)-l-?zaphthalcne-sulfonic Acid (C.

A. nomen.)

HO3S NH-

NH OH

FORIMATION.—By condensation of phenyl-l-naphthylamine-8-sulfonic

acid and p-amino-phenol

LITERATURE.—Lange, Schwefelfarbstoffe, 425


Dye Derived from 4-(^-Hydroxy-phenyl-amino)-l-phenylamino-naph-thalene-8-sulfonic Acid


746


SULFUR DYEThional Green BKatigene Green


Manufacture

I '14:— 63,929I '20:-- 14,370


[NasS+S]


S

2-Hydroxy-tfhionaphthene (C. A. and English nomen.)

3-Hydroxy-l-thionaphthene (German numbering)

Thioindoxyl

CH2 or I | CH =

FORMATION.—Thiosalicylic acid with chloro-acetic acid gives phenyl

thioglycolic-o-carboxylic acid:

[S .CH 2 .COOH

ICOOH

This body, by heating with a little water and caustic soda, closes

up the second ring and forms 2-hydroxy-thionaphthene-l-carboxylic

acid, which in warm acid solution decomposes, losing CO2 and form-

ing 2-hydroxy-thionaphthene


Georgievics and Grandmougin, Dye Chemistry, 432-434

Schultz, Farbstofftabellen (5 auf.), #912

Cain, Intermediate Products (2d Ed.), 159


Dyes Derived from 2-Hydroxy-thionaphthene


899

900

900

901

905

906

907

908

912

919


INDIGO GROUP DYESCiba Gray G

Ciba Violet 3B

Thio Indigo Violet K

Ciba Violet B

Thio IndigoScarlet R

Thio IndigoScarlet G

Ciba Scarlet G

Ciba Red R

Thio Indigo Red B

Ciba Bordeaux B

I

I

II

I

I

II

I

II

II


Manufacture

'14:—

'14:—

'14:—'20:—

'20:—

'20:—

'14:—'20:—

'14:—

'14:—'20:—

'14:—'20:—

675

2,667

20,83618,287

270

1,291

22,26525,578

1,001

1,102275

8991,786


2-Isatin anilide[Bromination]




Isatin

Isatin[Bromination]

Acenaphthenequinone

Acenaphthenequinone[Bromination]

2-Hydroxy-thionaph-thene (2 mols)

2-Hydroxy-thionaph-thene (2 mols)

[Bromination]or

[Bromination of ThioIndigo Red R]


V

V

V

V

V

V

V

V

V

V

3-Hydroxy-thionaphthene

See, 2-Hydroxy-thionaphthene


2-Hydroxy-Aionaphthene-l-carboxylic Acid (C. A, nomm.)

3-Hydroxy-(l)-thionaphthene-2-carboxylic Acid (German num-bering)

Thioindoxyl-carboxylic Acid

C. COOH = C9H6O3S = 194

FORMATION.—From phenyl-thioglycol-o-carboxylic acid through closingof the side chain upon fusion with caustic soda. (The carboxylicgroup is very easily split off with the formation of 2-hydroxy-thionaphthene.) Cf. 2-hydroxy-thionaphthene


USES.—See 2-hydroxy-thionaphthene

I Acid

See, J Acid

p: ^'-Imino-bisaniline (C A. nomen.)

See, p: p'-Diamino-diphenylamine

4:4/-Imino-bis-o-foluidine (C. A. nomen. NHz=l)

See, p: p'-Diamino-ditolyl-amine

Indanthrene

See, Indanthrone

Indanthrene-sulfonic Acid

See, Indanthrone-sulfonic Acid


Indanthrone

Dianthraquinone-dihydroazine

Indanthrene (C. A. nomen.)

)—NHxO C X .

FORMATION.—Anthraquinone is sulfonated with oleum to 2-anthraqui-none-sulfonic acid, which upon being heated in an autoclave withammonia forms 2-amino-anthraquinone. This latter by the actionof alkali at 200-300° is converted to indanthrone

LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 449-450Barnett, Anthracene and Anthraquinone, 342Schultz, Farbstofftabellen (1914 Ed.), #837

Dyes Derived from Indanthrone





Used and Notes


837

838

840

841

842

ANTHKAQUINONE ANDALLIED DYES

IndanthreneBlueR

IndanthreneBlue RS

IndanthreneBlue

IndanthreneBlue 2GS

IndanthreneBlue GCD

I '14:— 500

'14:—187,379M'17:— ?I '20:— 16,385M'20:— ?

I '14:— 6,120I '20:— 551

I '14:— 10,163I '20:— 500

I '14:—478,980M'19:— ?I '20:—147,620

[This is indanthrone]

[Reduction]

[Oxidation]

m

[Dichlorination]

V

V

V

V

V


Dyes Derived from Indanthrone (continued)

317


843

850



(continued)Indanthrene

Blue GC

IndanthrencBlue WB


I '14:— 1,499I >20:— 4,700

I '14:— 32,957I '20:— 2,998


[Dibrominationl

[?]


V

V

Indanthrone-sulfonic Acid

Indanthrene-sulfonic Acid (C. A. nomen.)

/ \ / C 0

FORMATION.—(1) From 2-amino-anthraquinonc-sulfonic acid by fusionwith caustic alkali at 200-300° C. (2) By sulfonating indan-throne (obtained by alkaline fusion of 2-amino-anthraquinone)

LITERATURE.—Barnett, Anthracene and Anthraquinone, 352Thorpe, Die. Chemistry, 3, 101 et seq.

Dye Derived from Indanthrone-sulfonic Acid


840



IndanthreneBlue


I '14:— 6,120I '20:— 1,702



V


IndigoNote.—Indigo is of course a dye and not an intermediate. However

because of their close mutual connection, it was considered worth while tolist together the dyes derived directly from indigo. All of these dyes arealso classified by the various intermediates that are used for the manufactureof indigo, namely:—

L Phenyl-glytine (2 mols)

2. Phenyl~glycine-o-carboxylic Acid (2 mols)

S. Thiocarbanilide (2 mols)

4- Aniline {2 mols)

5. Phthalic anhydride (2 mols)


874

876

877

878

Dyes


INDIGO GEOUP DYESIndigo


Indigotine

Indigotine P

Derived from


I '14:—8,507,359

M'17:—274,771M'18:—

3,083,888M'19:—

8,863,824I '20:—520,347M'20:—

18,178,231

I '14:— 19,329

' 1,876,787M'18:—

1,434,703M'19:—

1,699,670I '20:— 5,512M'20:—

1,395,000

Indigo


[Reduction]

[Sulfonation]

[Sulfonation]


V

V

A

A


Dyes Derived from Indigo (continued)

SchultaNumberfor Dye




Used and Notes


879

880

881

882

883

884

885

886

889

890


Brom IndigoRathjen

Indigo MLB/RR


DianthreneBlue 2B

Bromo Indigo FBCiba Blue 2B


Indigo MLB/6BIndigo KG




Indigo Yellow 3G

Ciba Yellow G

I 14:— 53,610M'20:— ?

14:— 6,856M17:— 14,100I '20:— 3,691M'20:— ?

I 14:— 16,880M19:— ?I '20:— 35,857

I 14:-I '20:-

I 14:-I '20:-M'20:-

1,3561,008

3,1914,130

I 14:— 4,518

I 14:-I '20:-

8,1753,503

I 14:— 12,057

I 14.— 48

[Bromination]

[Bromination]

[Bromination]

[Bromination]

[Bromination]

[Chlorination, Bromina-tion]

[Chlorination]


Benzoyl Chloride

Benzoyl ChloridePromination]

Indigo Red

See, Indirubin


Indirubin (C A. nomen.)

Oxindole-[A3'2']-pseudoindoxylIndigo Red

H

<x> ~\/\co/FORMATION.—By reaction of indoxyl on isatin in the " indoxyl melt"LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 410Ger. Pat. 192,682; Frdl. 9, 533Dye Derived from IndirubinSchultzNumberfor Dye

897


INDIGO GROUP DYESCiba Heliotrope B

Statistics ofImpart and


Used and Notes

[Bromination]


V

Indoxyl (C. A. nomen.)

3-Hydroxy-indole

(XNHNCH2 or CH =

FORMATION.—From phenyl-glycme by fusion with sodamide


Dye Derived from Indoxyl


897





Used and Notes

Isatin[Bromination]


V


Isatin (C. A. nomen.)

2-Hydroxy-3-pseudoindolone

( X .

NH \CO or C.OH = (

STATISTICS.—Imported '14:—very smallManufactured '20:— ?

FORMATION.—From indoxyl by oxidation

LITERATURE.—Lange, Zwischenprodukte, #1815, 2023, 2110-2116

Dyes Derived from Isatin


897

898

904

905

906



Helindonc Violet D

Helindone Brown G

Thio IndigoScarlet R

Thio IndigoScarlet G

2-Isatin Anilide

a-Isatin Anilide

Isatin-2-phenylimide


Manufacture

I '14.— 13,080I '20.— 2,200

I '20.— 370

I '20:— 1,291


Indoxyl[Bromination]

7-Methyl-indoxyl[Bromination]

5-Amino-2-hydroxy-thionaphthene

[Bromination]

2-Hydroxy-thionaph-thene


[Bromination]

2-Anilino-3-pseudoindolone (C A. nomen.)

( i4HioNtO = 222


V

V

V

V

V


FORMATION.—Aniline is condensed with carbon disulfide to thiocarbani-

lide (CeEU. NH)2 CS, which is treated in solution with potassium

cyanide and lead carbonate, resulting in the formation of the

corresponding cyanide. This cyanide is reacted with yellow am-

monium sulfide (containing NH4.S.S.NH4), and a thioamide is

formed:

. N . / N H

> o - c = s

This compound upon being heated with sulfuric acid gives a good

yield of 2-isatin anilide

LITERATURE.—Lange, Zwischenprodukte, #2132-2134Georgievics and Grandmougin, Dye Chemistry, 413

Dyes Derived from 2-Isatin Anilide





Used and Notes


894

896

899

900

900

901

INDIGO GROUP DYESAlizarin Indigo B

Helindone Blue 3GN

Ciba Gray G

Ciba Violet 3B

Thioindigo Violet K

Ciba Violet B

I '14:-I '20:-

I '14:-I '20:-

402291

6222,527

=:— 675

I '14:— 2,667

I '14:-I '20:-

20,83618,287

3-Hydroxy-acenaph-thene

1-Hydroxy-anthranol


[Brom iiiation]


[Bromination]


[Bromination]


[Bromination]

V

V

V


Dyes Derived from 2-Isatin Anilide (continued)

323


902

903



Helindone Brown 2R

Helindone Brown 5R


Manufacture

I '14:— 876I '20:— 1,778


5-Amino-l-hydroxy-thionaphthene

[Bromination]

5-Amino-l-hydroxy-thionaphthene

[Bromination]


V

V

a-Isatin Anilide


Isatin-2-phenylimide


Isoanthraflavic Acid

2: 7-Dihydroxy-anthraquinone (not considered herein)

Iso-7 Acid

See, J Acid

Iso-naphthazarin

2: 3~Dihydroxy-l: 4-naphthoquinone (not considered herein)

Isoquinoline

N

STATISTICS.—Imported '14:—very small


FORMATION.—Isoquinoline is extracted from coal-tar or prepared bysynthetical means


Dye Derived from Isoquinoline


610


QUINOLINE DYEQuinoline Red



Benzo-trichlorideQuinaldine


B

J Acid


Amino-naphthol-sulfonic Acid J

6-Armno-l-naphthol-3-sulfonic Acid (C. A. nomen.)

I Acid

Iso-7 Acid

STATISTICS.—Imports J14:—1,153 lbs.


FORMATION.—j3-Naphthylamine is disulfonated to a mixture of 2-naphthylamine-5:7-disulfonic acid and 2-naphthylamine-6:8-disulfonic acid. The latter is amino-G acid and is a step in thepreparation of gamma acid. The former is fused with caustic sodain an autoclave to form J acid





Dyes Derived from J Acid

SchultzNumberjot Dye




Used and Notes

279

326

346

385

DISAZO DYESBenzo Fast Scarlet '14:— 36,674

M'19:— ?I '20:— 24,153

Oxamine VioletOxy Diamine Violet

BF

Oxamine Red

Oxamine Blue 4R

I '14:— 23,981I '20:— 732

I '14:— 11,636I '20.— 848

I '14:— 573M'20:— ?

J Acid (2 mols)PhosgeneAniline or

Toluidine orXylidine orjS-Naphthylamine orAmino-azo-benzene

(2 mols)

BenzidineJ Acid (2 mols)



D

D

Juglone

5-Hydroxy-l: 4-naphthoquinone (not considered herein)

K Acid*

l-Amino-8-naphthol~4: 6-disulfonic Acid

Amino-naphthol-disulfonic Acid K

8-Amino-l-naphthol~3: 5-disulfonic Acid (C. A. nomen.)

HO N H 2

HO3S= C10H9NO7S2 =

1 K acid is also occasionally used as trivial name for 1:-- Dihydroxy-naphthalene-3: 5-disulfonic acid.


FOKMATION.—Naphthalene is disulfonated to the 1: 5 acid, and thenfurther sulfonated to the 1:3: 5-trisulfonic acid. This trisulfonicacid while still in the sulfonation mixture is diluted with a little ice,and cooled, and it is then nitrated cold with the theoretical amountof mixed acid. I t is reduced with iron, forming 1-naphthylamine-4:6 : 8-trisulfonic acid, which upon being fused with caustic sodain an autoclave yields the K acid


Dyes Derived from K Acid





Used and Notes


43

215

219

335

338

MONOAZO DYETolane Red B, G


Chrome PatentGreen N

JSTaphthamine BlackRE

Naphthamine Blue2B or 3B

I '14:— 2,653

I '14:— 49,016

I '14:— 11,707I '20:— 400

Aniline

Anilinep-Nitro-aniline

AnilinePicramic Acid

BenzidineGamma Acid

Benzidine orToHdine

K Acid (2 mols)

A

ACr

D

Kalle's Acid

l-Naphthylamine-2:7-disulfonic Acid (not considered herein)


Ketone

Tetramethyl-diamino-benzophenone

p: p'-Bis(dimethylamino)-6enzophenone (C A. nomen.)

Michler's Ketone

Ketone Base

(CH 3 ) 2 N<^>—CO—/~^>N(CH 3 )2 = CITHMNJO = 268

STATISTICS.—Imported ' 14:—small amountManufactured ' 17:— ?Manufactured '18:— 73,208 lbs.Manufactured '19:—281,057 lbs.Manufactured '20:— 90,664 lbs.

FORMATION.—From dimethyl-aniline by reaction with phosgene


327


493

516

522

Dyes


ATJBAMINESAuramine


Crystal Violet

Victoria Blue 4R

Derived fron\ "


Manufacture

I 14:—449,276MT7:— ?M'18:— 45,634M19:—127,567I '20:— 74,414M'20:— ?

I 14:— 51,872M17:— ?M18:— ?M19:— ?I '20:— 2,919M'20:— ?

I 14:— 9,599I '20:— 152

Ketone


[Ammonium chlorideand Zinc chloride]

Dimethyl-aniline

Methyl-phenyl-a-naphthylamine


B

B

B


Dyes Derived from Ketone (continued)


527

548

558

559

561

566

607


TmPHENYL-METHANEDYES

{continued)Acid Violet 4BN

Acid Violet 6BN

DlPHENYT/-NAPTHYL-METHANE DYES

Victoria Blue R

Victoria Blue B

Acid Violet 5BNS

Wool Green S

ACEIDINE DYERheonine


I '14:— 60,073M'17:— ?M'19:— ?I '20:—127,764M'20:—212,362

I '14:— 19,704


I '14:— 29,184I '20:— 23,335

I '14:— 6,861I '20:— 5,582

I '14:— 4,171I '20:— 97

I '14:—127,769M'17:— ?M'18:— ?M'19:— ?I J20:— 11,782M'20:— ?

I '14:— 1,896 MethyHEthyl-) phenyl-/?-naphthylamine

Benzyl-methyl-aniline

3-Ethoxy~4'-methyl-diphenylamine

[Sulfonation]


Phenyl-a-napthyl-amine

/3-Naphthol[Sulfonation]

m-Phenylene-diaTnin e


6-Keto-l-(^-sulfo-phenyl)-3-A2-y^razoline-carboxylic Acid (C. A.nomen.)See, l-(p-S\ilfo-pheiiyl)-5-pyrazoloiie-3-carboxylic Acid

Koch's AcidSee, l-Naphthylamine-3:6:8-trisulfonic Acid


L Acid

See, l-Naphthol-5-sulfonic Acid (C. A. nomen.)See Laurent's Acid2:6-Dihydroxy-naphthalene-3-carboxylic Acid (not con-

sidered herein)

Lambda Acid or X Acid

See, l-Naphthylaminc-2-sulfonic Acid

Landschoft and Meyer's Acidl-Naphthylamine-2: 5-disulfonic Acid (not considered here)

Laurent's a Acidl-Nitro-naphthalene-5-sulfonic Acid (not considered herein)

Laurent's Acid

l-Naphthylamine-5-sulfonic Acida-Naphthylamine-sulf onic Acid L5-Axnino-l-naphthalene-sulfonic Acid (C A. nomen.)Naphthalidine-sulfonic AcidNaphthalidinic AcidCleve's a AcidL AcidLaurent's Naphthalidinic Acid

NH2

C10H9NO3S =

HO3S

riSTics.—Imported '14:— 2,832Manufactured '18:— ?Manufactured ' 19:— ?Manufactured 720:—294,352

.MATioN.—(1) From a-naphthylamine by sulfonation with oleum.(2) From a-naphthalene-sulfonic acid by nitration reduction andseparation from the l-naphthylamine-8-sulfonic acid also formed

ERATURE.—Cain, Intermediate Products (2d Ed.), 190Lange, Zwischenprodukte, #2360-2Thorpe, Dict Chemistry, 3 ; 590


Dyes Derived from. Laurent's Acid



Siatisiics ofImport and


Used and Notes


53

162

265

308

364

480

563

MONOAZO DYEArchil Substitute

3VN

Brilliant FastRedG

DISAZO DYESSulfoncyanine

Black B

Diazo Black B

Benzopurpurin 6B

TRISAZO DYECongo Brown R

DlPHENYL NAPHTHYL-METHANE DYE

New Patent Blue B

I '14:-M'17:-M '18:-M'19:-M'20:-

69,590????

:— 62,854

I '14:—I '20:—

9,1714,743

I '14:— 3,041

I '14:I '20:-

59,1,814

p-Nitro-aniline

^-Naphthol

a-Naphthylamine or1-Naphthylamine-6- and 7-sulfonicAcids

Phenyl-1-naphthyl-amine-8-sulfonic Acid

Laurent's Acid (2 mols)Benzidine

Laurent's Acid (2 mols)Tolidine

BenzidineResorcinolSalidylic Acid

Hydrol[Substitution of NH2 by

SO3H; Oxidation]

Laurent's Naphthalidinic Acid

See, Laurent ' s Acid (l-Naphthylamine-5-sulfonic Acid)


Lepidine (C. A. nomen.)

4-Methyl-quinoline (N = l)

7-Methyl-quinoline

Cincholepidine

331

CH3

FORMATION.—(1) From cinchonine by distillation with caustic potash,(2) By saturating a mixture of methylal [CH2(OCH3)2] and acetonewith gaseous hydrochloric acid, and then, heating this with anilineand concentrated hydrochloric acid


Dye Derived from Lepidine


611


QUINOLINE DYEQuinoline Blue



Quinoline[Amyl-iodide]


Photo-graphy

^-Leucaniline

See, Triamino-triphenyl-methane

Leuco-iso-naphthazarin

1:2:3:4-Tetrahydroxy-naphthalene (not considered herein)

Leuco-naphthazarin

1:2: 5: 8-Tetrahydroxy-naphthalene (not considered herein)

Leucotrope

Benzyl-dimethyl-phenyl-ammonium Chloride (not consideredherein)


Liebman and Studer's Acid


MAcid

See, l-Aniino~5-naphthol-7-sulfonic Acid

l-(or 2-)Mercapto-anthraquinone

SH

= C14H8O2S = 240

FORMATION.—By forming mercapto-benzoyl-benzoic acid and thenclosing the ring

LITERATURE.—Barnett, Anthracene and Anthraquinone, 183, 184Lange, Zwischenproduckte, #3143-3147, 3527

Dye Derived from l-(or 2-)Mercapto-anthraquinone


869



Algol Brown B


Manufacture

I '14:— 1,596I '20:— 4,727



V

o-Mercapto-benzoic Acid (<7. A. nomen.)

See, Thio-salicylic Acid

Mesidine (C A. nomen.)

2:4:6-Trimethyl-aniline

NH2

H3


FORMATION.—By the nuclear methylation of aniline, whereby anilinehydrochloride is heated with methanol (methyl alcohol) underpressure at 300-350°. There is formed, in addition to mesidine,p- and o-toluidine, m-xylidine, etc.


Dye Derived from Mesidine


583


XANTHONE DYEAcid Rosamine A


Manufacture

I '14:— 50I '20:— 141


Mesidine (2 mols)Resorcinol (2 mols)Phthalic Anhydride[PC15; Sulfonation]

or[Dichloro-fluoresceine;

Mesidine (2 mols);Sulfonation]


A

Meta=mNote.—This is not considered in the alphabetical arrangement, e.g.

meta-Phenylene-diamine is indexed as m-Phenylene-diamine under "P."However m-Phenylene-diamine precedes p-Phenylene-diamine

Metanilic Acid (C. A. nomen.)

m-Amino-benzene-sulfonic Acid

m-Sulfanilic Acid

SO3H

STATISTICS.—Manufactured '17:— ?Manufactured '18:—249,922 lbs.Manufactured 19:—453,137 lbs.Manufactured '20:—499,304 lbs.

FORMATION.—By sulfonating nitro-benzene with oleum, and reductionwith iron



Dyes Derived from Metanilic Acid






134

135

136

210

256

257

258

542

MONOAZO DYESMetanil Yellow

Metauil YellowBrominated

Acid YellowMGS, GG

DISAZO DYESCotton Orange R

Sulf on Black 3B

Sulfoncyauine

Naphthalene AcidBlack 4B

I '14:—284,606M'17:— ?M'18:— ?M'19 :—477,143I '20:— 8,456M '20:—629,437

Diphenylamine

I '14:— 16,459I '20:— 51

I '14:—145,694M'17: ?M'18:— ?M'19:— ?I '20:— 18,327M'20:— ?

I '14:— 7,994

TRIPHENYL-METEANEDYE

Agalma Green B I '14:— 2,294

Diphenylamine[Bromination]

Diphenylamine[Sulfonationj

PrimiiliD e-sulf omc Acidm-Phenylene-diamine-disulfonic Acid

a-NaphthylaminePhenyl-1-naphthyl-

amine-8-sulf onic Acid

a-Naphthylamine orl-Naphthylamine-6-and 7-sulf onic Acids

Phenyl- or Tolyl-1-naphthylamine-8-sulf onic Acid

1 -Naphthylamine-6-and 7-sulf onic Acids

a-Naphthylamine

4-Chloro-3:5-dinitro-benzene-sulf onic Acid

Hydrol


Dyes Derived from Metanilic Acid (continued)

335


738





Used and Notes


[S+Na*S]


S

Methoxy-dimethylamino-benzophenone

See, 4-Dimethylamino~3-methoxy-benzophenonenomen.)

6-Methoxy-m-toluidine (C. A. nomen. NH2=1)

See, 2-Amino-p-cresol Methyl Ether

1-Methylamino-anthraquinone

(C A.

FORMATION.—1-Chloro-anthraquinone is reacted with p-toluene-sulfon-methyl-amide (CH3 . C6H4. SO2 . NH . CH8), splitting off HC1 andforming l-(p-toluene-sulfon-methyl-amino)-anthraquinone. Thislatter readily decomposes in presence of sulfuric acid, forming1-methylamino-anthraquinone

LITERATURE.—Lange, Zwischenprodukte, #3113, 3115, 3117, 3118,3476Barnett, Anthracene and Anthraquinone, 197, etc.

Dye Derived from 1-Methylamino-anthraquinone


866



Leucol DarkGreen B


Manufacture

I '20:— 120



V


2-Methylamino-8-naphthol-6-sulfonic Acid

See, Methyl-gamma Acid

7-Methylamino-l-waphthol-3-sulfonic Acid (C. A. nomen.)

See, Methyl-gamma Acid

JV-Methyl-aniline

Methyl-aniline

HNCH3

z=rC7H9N=107

FORMATION.—By heating aniline and methanol (methyl alcohol) in thepresence of sulfuric acid in an autoclave; or by heating anilinehydrochloride and methanol in an autoclave


USES.—For preparation of ethyl-methyl-aniline and for benzyl-methyl-aniline

2-Methyl-anthraquinone (C. A. nomen.)

£-Methyl-anthraquinone

oco- =C15H10O2 =

FORMATION.—Phthalic anhydride is dissolved in toluene, and heatedwith AICI3 whereby p-toluyl-o-benzoic acid is formed, which latter,upon being dissolved in oleum and heated, forms the 2-methyl-anthraquinone

LITERATURE.—Cain, Intermediate Products (2d Ed.), 259Heller and Sehiilke, Ber. 41, 3632 (1908)Cf. Elbs, J. pr. Chem. [II] 33, 318 (1886)Cf. Limpricht and Wiegand, Ann. 311, 178 (1900)


Dyes Derived from 2-Methyl-anthraquinone

337


759

792

795



Anthraflavone G

Cibanone Orange R

Cibanone Yellow R


Manufacture

I '14:— 7,143I '20:— 2,354

I '20:— 6,125

I '14:— 298I '20:— 14,032


2-Methyl-anthraqui-none (2 mols)

[Sulfur]

[Sulfur]


V

V

V

0-Methyl-anthraquinoneSee, 2-Methyl-anthraquinone3-Methyl-benzaldehyde-4:6-disulfonic Acid4-Formyl-6-methyl-m-6enzene-disulfonic Acid (C A. nomen.)CHOHO3sUSO3HFORMATION.—Probably by oleum sulfonation of m-tolualdehyde(m-tolualdehyde can be made by oxidation of m-xylene)LITERATURE.—Thorpe, Die Chemistry, 5, 516Cf. Lange, Zwischenprodukte, #784Dyes Derived from 3-Methyl-benzaldehyde-4:6-disulfonic Acid

SchultzNumberfor Dye507508

Ordinary Name andClass of DyeTRIPHENYL-METHANJDDYESXylene Blue VSXylene Blue AS

Statistics ofImport andManufactureI '14:— 2,130I '20:— 27,254I '14:— 8,238I '20:— 5,573


Diethyl-aniline (2 mols)[Oxidation]Benzyl-ethyl-aniline(2 mols)[Oxidation]

DyeAppli-cationClassAA


Methyl-benzanthrone

9-Methyl-7-meso-benzanthrenone (C A. nomen.)

H3C

FORMATION.—By condensation of 2-methyl-anthrone with glycerol andsulfuric acid at about 120° C.

LITERATURE.—Barnett, Anthracene and Anthraquinone, 324Fr. Pat. 407,593Cf. Ger. Pat. 209,351. Frdl. 9, 836

Dyes Derived fronx Methyl-benzanthrone


793

794



Cibanone Blue 3G

Cibanone Black B


I '14:— 2,802


[Sulfur]

[Sulfur]


V

V

l-Methyl-2:4-diamino-benzene-5-sulfonic AcidSee, 4:6-Diamino-m-foluene-sulfonic Acid (C. A. nomen.

l-Methyl-2:6-diamino-benzene-4-sulfonic AcidSee, 3:5-Diamino-p-foluene-sulfonic Acid (C. A. nomen.

JV-Methyl-diphenylamine (C. A. nomen.)Diphenyl-methyl-amine


FORMATION.—From diphenylamine by heating with hydrochloric acidand methanol (methyl alcohol) in an autoclave at 250°

LITERATURE.—-Cain, Intermediate Products (2d Ed.), 73

Dyes Derived from iV-Methyl-diphenylamine






532

534

547


Alkali Violet 6B

Acid Violet 7B

Ketonc Blue 4BN

:— 3,020

I '14:— 21,665I '20:— 51


[Sulfonation]

Diethyl-p-amino-benzoyl Chloride

iV-Methyl-diphenyl-amine (2 mols)

Methoxy-dimethyl-amino-benzophenone

[Sulfonation]

A

A

N-Methyl-diphenylamine-sulfonic Acid

• N — < ( ~ y \ SO3H = Ci3H13NO3S = 263

C H 3

FORMATION.—By sulfonation of methyl-diphcnylamine

LITERATURE.—Beils te in , Organische Chemie (3 auf.), II spl., 324

Dye Derived from N-Methyl-diphenylamine-sulfonic Acid


533



Acid Violet 7BN



Used and Notes

p-Dimethylamino-benzoyl chloride

iV-Methyl-d i p h e n y 1-amine-sulfonic Acid(2 mols)


A


^:£'-Methylene-bisaniline (C. A. nomen.)

See, p.'p'-Diamino-diphenyl-methane

^:/>'-Methylene-bis(iV:iSr-diet3iyl-aniliiie) (C. A. nomen.)

See, p: p'-Tetraethyl-diaimno-diphenyl-methane

^:£'-Methylene-bis(iV: iV-dimethyl-aniline) (C. A. nomen.)

See, p: p'-Tetramethyl-diamino-diphenyl-methane

4:4/-Metbylene-bis(iV-niethyl-o-/olui(iine) (C. A. nomen.)

See, 4:4/-Dimethyl-diamino-3: S'-ditolyl-methane

4: ^-Methylene-bis-o-Zoluidine (C. A. nomen.)

See, p: p'-Diamino-ditolyl-methaae

Methylene-bisjcylidine (C. A. nomen.)

See, Diamino-dixylyl-methane

Methyl-ethyl-aniline

See, Ethyl-methyl-aniline

Methyl-gamma Acid

2-Methylamino-8-naplithol-6-sulfonic Acid

7-Methylamino-l-naphtliol~3-sulfoiuc Acid (C. A. nomen.)

HO

H O 3 s ( Y ) N H * C H 3 = CnH.NO.S = 253

FORMATION.—G salt (Sodium salt of 2-naphthol-6:8-disulfonic acid)is heated in aja autoclave with methylamine; and the resulting2-methylamino-naphthalene-6: 8-disulfonic acid is fused with causticsoda in an autoclave, forming methyl-gamma acid. (See Gammaacid)

,—Lange, Zwischenprodukte, #2550


Dye Derived from Methyl-gamma Acid

341


347


DISAZO DYEDiphenyl Brown RN



Used and Notes



D

7-Methyl-indoxyl

C H a N HCH2 =

FORMATION.—o-Toluidine is reacted with chloro-acetic acid, formingo-tolyl-glycine. This body upon fusion with sodamide will in allprobability form 7-methyl-indoxy. (There is no direct referencein the literature to 7-methyl-indoxyl)

LITERATURE.—Lange, Zwischenproduktc, #241

Dye Derived from 7-Methyl-indoxyl


898


INDIGO GROUP DYEHelindone Violet D



Used and Notes

Isatin[Bromination]


V

9-Methyl-7-meso-&enzanthrenone (C. A. nomen.)

See, Methyl-benzanthrone

N-Methyl-^-nitroso-aniline (C. A. nomen.)

See, p-Nitroso-methyl-aniline



iV-Methyl-iV-phenyl-1-naphthylamine (C A. nomen.)

FORMATION.—Phenyl-a-naphthylamine is methylated by heating with

methanol (methyl alcohol) and hydrochloric acid under pressure

LITERATURE.—Schultz, Chemie des Steinkohlentheers (3 aufl. 1900)

1,117


522

Dye Derived from


TRIPHBNYL-METHANEDYE

Victoria Blue 4R



Manufacture

I '14:— 9,599I '20:— 152


Ketone


B

Methyl-(Ethyl-)phenyl-j3-naphthylamine

iV-Methyl-(Ethyl-)iVr-phenyl-2-naphthylamine (C. A. nomen.)

CH3

FORMATION.—Phenyl-^-naphthylamine is methylated by heating in

an autoclave with methanol (methyl alcohol) and hydrochloric

acid

LITERATURE,—Lange, Zwischenprodukte, #2897


Dye Derived from Methyl-(Ethyl-) phenyl-0-naphthylamine


561



Acid Violet 5BNS


Manufacture

I '14:— 1,896


Ketone[Sulfonation]


A

3-Methyl-l-phenyl-5-£yrazolone (C. A. nomen.)

l-Phenyl-3-methyl-5-pyrazolone

N-

OC NN

H 2 C — C . C H 3

STATISTICS.—Imported '14:—449 lbs.

FORMATION,—By heating the reaction product of phenyl-hydrazineand aceto-acetic ethyl ester

LITERATURE.—Lange , Zwischenprodukte. #138

Dyes Derived from 3-Methyl-l-phenyl-5-pyrazolone






21

24

26

28

29

PYRAZOLONE DYESPigment Chrome

Yellow L

Pigment FastYellow R

Dianil Yellow R

Pigment FastYellow G

Eriochrome Red B

M'19:— ?I '20:— 170

I '14:— 5,491

Toluidine

o-Toluidine-m-sulfonicAcid

Prim uline-sulf onicAcid

p-Sulfo-anthranilicAcid


CL

CL

D

CL

CL


2-Methyl-quinoline

See, Quinaldine (C. A. nomen.)

4-Methyl-quinoline (N=l)

See, Lepidine (C. A. nomen.)

a-Methyl-quinoline

See, Quinaldine (C A. nomen.)

7-Methyl-quinoline

See, Lepidine (C. A. nomen.)

Methyl Resorcinol

See, Resorcinol Methyl Ether

3-Methyl-l-(^-sulfo-phenyl)-5-pyrazolone

l-(p-Sulfophenyl)-3-methyl-5-pyra2!olone

p-(4:5-Dihydro-5-keto-3-methyl-l-py razolyl)-&enzene-sulf onic

Acid (C. A. nomen.)

OC N 1 0 1 0 2 4

H2C—C. CH3

FORMATION.—(1) By sulfonating 3-methyl-l-phenyl-5-pyrazolone by

heafcing with 4 parts of 30 per cent oleum. (2) By heating phenyl-

hydrazine-p-sulfonic acid with aceto-acetic ethyl ester in 50 per

cent acelic acid solution for few hours



Dyes Derived from 3-Methyl-l-(^-sulfo-phenyl)-5-pyrazolone


19

27


PYKAZOLONE DYESFlavazine LFast Light Yellow

Dianil Yellow 2R


I '14:— 38,908I '20:— 9,327


Aniline

Primuline-sulfonic Acid


A

D

N-Methyl-o-foluidine (C. A. nomen. NHRMethyl-o-toluidine

HN—CH3

STATISTICS.—Manufactured ' 19:— ?

FORMATION.—(1) By heating o-toluidine, methanol (methyl alcohol)and hydrochloric acid in an autoclave. (2) By condensing o-toluidine and formaldehyde, and reducing to methyl-o-toluidine

LITERATURE.—Cain, Intermediate Products (2d Ed.), 60, 70C/. Lange, Zwischenprodukte, #128

Dyes Derived from AT-Methyl-o-toluidine


•494

501

684


AURAMINE DYEAuramine G


Glacier BlueBrilliant Glacier

Blue

AZINE DYEBrilliant Rhoduline

Eed


Manufacture

I '14:— 1,902

I '14:— 2,495


Methyl-o-toluidine (2mols)

[Formaldehyde, sulfur,ammonium chloride,etc.]

Methyl-o-toluidine (2mols)

2:5-Dichloro-benzalde-hyde

[Oxidation]

iV^-Ethyl-4-m-tolylene-diamine

Aniline


B

B

B


Michler's HydrolSee, Hydrol

Michler's Ketone or BaseSee, Ketone

Monochloro-benzene1

See, Chloro-benzene

Monoethyl-aniline1

See, Ethyl-aniline

Monomethyl-aniline1

See, Methyl-aniline

Mononitro-chloro-benzene1

See, Chloro-nitro-benzene

Monosulfonic Acid PSee, 2-Naphthol-7-sulfonic Acid

Monosulfo Acid Hl-Amino-8-naphthol-3-sulfonic Acid (not considered herein)

Mu AcidSee, l-Naphthylamine-6-sulfonic Acid

Myrbane OilSee, Nitro-benzene

Naphtha-See also, Naphtho-

a-Naphthahydroquinone1:4-Dihydroxy-naphthalene (not considered herein)

i^-Naphthahydroquinone1:2-Dihydroxy-naphthalene (not considered herein)

1 " Mono " is superfluous and is consequently not recommended.


Naphthalene (C. A. nomen.)

Naphthalin

Note.—Naphthalene is a crude and not an intermediate as a rule

— CioHs —128

STATISTICS.— Refined NaphthaleneManufactured Imported

Calendar Year 1917:—35,342,911 lbs. 267,057 lbs." 1918:—33,701,779 lbs. 2,795 lbs." 1919:—17,625,235 lbs. 7,650 lbs.

" 1920:—30,230,734 lbs. 3,697,562 lbs.

FORMATION.—From coal tar by extraction and purification


Dyes Derived from Naphthalene


564

758



NaphthaleneGreen V


Sirius Yellow G


Manufacture

I 714:— 22,144I '20:— 9,291


Hydrol

Phthalic anhydride


A

CL

1: 5-Naphthalenediol (C. A. nomen.)

See, 1:5-Dihydroxy-naphthalene

2:7-Naphthalenediol (C. A, nomen.)

See, 2: 7-Dihydroxy-naphthalene


Naphthalene-1:5- and 1:6-disulfonic Acids

'he 1:5 acid is also called:

Armstrong's AcidArmstrong's 8 Acid

Naphthalene-7-disulfonic Acid of Armstrong and Wynne

Naphthalene-5-disulfonic Acid of Beilstein and Schultz

'he 1: 6-acid is also called:Ewer and Pick's Acid

Naphthalene-? : /3-disulfonic Acid of Armstrong and Wynne


SO3H SO3H

omd ^n^l I I =Ci0H8O6S2 = 288

HO3S

ORMATION.—The above acids are prepared by sulfonation of naphtha-lene with five parts of 23 per cent oleum at 60°; or with five partsof ordinary sulfuric acid (66°) using first one part at 180° to form the/3-sulfonic acid and then four parts at 95-100° for 20-24 hours

If the 1: 5-acid alone is wanted the conditions of sulfonation arevaried slightly, generally starting with the a-sulfonic acid. Theseparation is effected by crystallizing out the 1: 5 acid or its sodiumsalt from the diluted sulfonation product

ITERATUKE.—Cain, Intermediate Products (2d Ed.), 176, 177Thorpe, Die. Chemistry, 3, 575

SES.—The mixed acids are used for the preparation of 1-naphthyl-amine-3: 8- and 4: 8-disulfonic acids, and the separation then made

The 1: 5-acid is used for making naphthalene-1: 3: 5-trisulfonicacid

Naphthalene-2:7-disulfonic Acid

a-Naphthalene-disulfonic Acid (of Ebert and Merz)

Ebert and Merz a Acid


STATISTICS.—Manufactured 1918, 1919, 1920 in undisclosed quantitiesFORMATION.—Sodium 2-naphthalene-sulfonate is further sulfonated by

dissolving in about two parts of monohydrate or a larger amountof 66° sulfuric acid, and heating to 180° for 6-8 hours. There isformed principally naphthalene-2: 6- and 2: 7-sulfonic acids, andthe separation is effected through the calcium salts, the 2:6 saltbeing less soluble

LITERATURE.—Lange, Zwischenprodukte, #2442Ger. Pat. 61,730Thorpe, Die. Chemistry, 3, 577

Dyes Derived from Naphthalene-2:7-disulfonic Acid


564



NaphthaleneGreen V


Manufacture

I '14:— 22,144I '20:— 9,291


Hydrol[Oxidation]


A

Naphthalene-? : /3-disulfonic Acid of Armstrong and WynneSee, Naphthalene-1: 6-disulfonic Acid

Naphthalene-7-disulfonic Acid of Armstrong and WynneSee, Naphthalene-1: 5-disulf onic Acid

Naphthalene-5-disulfonic Acid of Beilstein and SchultzSee, Naphthalene-1:5-disulf onic Acid


See, Naphthalene-1:6-disulfonic Acid

a-Naphthalene-disulfonic Acid of Ebert and MerzSee, Naphthalene-2: 7-disulfonic Acid

Naphthalene-1:3:5-trisulfonic Acid

SO8H

OA TT :==: C10H.8O9S3 '==:-368


FORMATION.—By sulfonation of naphthalene-1: 5-disulfonic acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 179Thorpe, Die. Chemistry, 3, 578

USES.—For preparation of l-naphthylamine-4: 6: 8-trisulfonic acid

Naphthalene-1:3:6-trisulfonic Acid

Trisulfonic Acid

SO3H

= C l o H 8 ° 9 S 3 = 3 6 8

FORMATION.—By sulfonating naphthalene for some hours at 180° with24 per cent oleum, or preferably by sulfonating sodium naphtha-Iene-j3-sulfonate at a low temperature with forty per cent oleum


USES.—For preparation of l-naphthol-3:6-disulfonic acid and 1-naph-thylamine-3:6: 8-trisulfonic acid. The latter acid is the last stepprior to the manufacture of H acid (l-amino-8-naphthol-3: 6-di-sulfonic Acid)

Naphthalic Acid

Naphthalene-1:8-dicarboxylic Acid (not considered herein)

Naphthalidam


Naphthalidine


Naphthalidine-sulfonic Acid

SeeT Laurent's Acid


Naphthalidinic Acid

See, Laurent's Acid

Naphthalin

See, Naphthalene

Naphthapyrogallol

1:2: 3-Trihydroxy-naphthalene (not considered herein)

a-Naphthaquinol


0-Naphthaquinol


1:2-Naphthaquinone

See, 1: 2-Naphthoquinone (C. A. nomen.)

a-Naphthaquinone

1:4-Naphthoquinone (not considered herein)

jS-Naphthaquinone

See, 1:2-Naphthoquinone

1:8-Naphthasultam-2:4-disulfonic Acid

4-Amino-4: 5-sultam-l: 3: 5-naphthalene-trisulfonic Acid (C. A,nomen.)

SO2-NH

SO3H — c10H7NO8S3=365

SO3H

FORMATION.—The acid sodium l-naphthylamine-4:8-disulfonate is sul-fonated with two parts of 40 per cent oleum, and wanned to 80-90°.This warming is continued until a sample no longer diazotkes anddoes not form a dye with diazotized sulf anilic acid



USES.—For preparation of l-amino-8-naphthol-2:4-disulfonic Acid

Naphthazarin (C. A. nomen.)

5: 6-Dihydroxy-l: 4-naphthoquinone

5: 6-Dihydroxy-a-naphthoquinone

1: 2-Dihydroxy-naphthoquinone

Oxy-juglone

FORMATION.—Crude dinitro-naphthalene (a mixture of 1:5- and 1: 8-dinitro-naphthalene) is treated with oleum and sulfur

LITERATURE.—Georgievics and Grandmougin, Dye Chemistry, 333Cf. Lange, Zwischenprodukte, #2759Schultz, Farbstofftabellen (1914), #774Thorpe, Die. Chemistry, 3, 656, 569

Dyes Derived from Naphthazarin

SchvXizNumberfor Dye

774

775



Alizarin Black



Manufacture

I '14:—205,439I '20:— 17,421


[NaHSO3]

Phenol


M

M

1:2-jS-Naphthazoledione (C. A. nomen.)

See, jS-Naphthisatin


o-Naphthionic Acid


Naphthionic Acid

Naphtholic Acid

Piria's Acid

l-Naphthylamine-4-sulfonic Acid

l-Amino-naphthalene-4-sulfonic Acid

4-Amino-l-naphthalene-sulfonic Acid ( C A. numbering)

Note.—C. A. nomenclature is Naphthionic Acidy but C. A. numbers-om the -SOzH group, instead of from -NHz group, as is the usual procedure

NH2

= Ci0H9NO3S =

TATISTICS.—Manufactured ' 17:— ?Manufactured '18:—1,462,216 lbs.Manufactured '19:—2,008,189 lbs.Manufactured '20:—3,773,191 lbs.

OKMATION.—By "baking" a-naphthylaminc and sulfuric acid plus alittle oxalic acid in pans in an oven

ITERATUBE.—Cain, Intermediate Products (2d Ed.), 189Lange, Zwischenproduktc, #2359Thorpe, Die. Chemistry, 3, 590

Dyes Derived from Naphthionic Acid

chultzumber•r Dye

52

91


MONOAZO DYES

Archil Substitute V

Anthracyl ChromeGreen AD


Manufacture

I '14:— 4,596M'18:— ?I '20:— 3,316


p-Nitro-aniline

Picramic Acid


A

ACr


Dyes Derived from Naphthionic Acid (continued)


160

161

163

164

165

166

167



NaphthylamineBrown

Fast Brown N

Fast Red A

Azo Rubine

Fast Red VR

Azo Red A

Fast Red E

Croceine Scarlet 3BX


Manufacture

I J14:— 68,281M'17:— ?M'18:-— ?M'19:— ?M320:— ?

I '14:— 46,359M'17:—191,424M'18:—242,215M'19:—267,582I '20:— 948M'20:-433,989

I '14:—230,763M'17:—197,621M'18:— 79,779M'19:—187,264I '20:— 1,102M'20:-470,949

I '14:— 20,714M'17:— ?M'18:— ?M'19:— ?I '20:— 6,290M'20:— ?

I '14:— 2,473M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I '14:— 13,101M'17:— ?M'18:— ?M'19:— ?I '20:— 651M'20:— ?


a-Naphthol

/3-Naphthol


l-Naphthol-5-sulfonicAcid


Schaeffer's Acid

Croceine Acid


ACr

A

A

ACr

A

A

A







168

169

170

171

209

213

264

307

MONOAZO DYES(continued')

Amaranth

CochinealRed A

Ponceau 6R

Chromotrope 8B

DISAZO DYESTerra Cotta FC

Fast Brown

Fast SulfonBlack F

Congo Red

I '14:— 86,067M'17:— 66,069M'18:— 73,539M'19:— 294,416I '20:— 110M'20:—204,958

I '14:— 32,645M'17:— ?M'18:— ?M'19:—231,519M'20:—288,945

M'18:— ?

I '14:— 551

I '14:-M'17:-M'18:-M'19:-M'20:-

3,206????

I '20.— 2,204M'20:— ?

I '14:— 20,629M'17:— ?M'18:—587,153M'19:—873,734M'20:—

1,502,630

R Acid

G Acid

2-Naphthol-3: 6:8-trisulfonic Acid

Chromotropic Acid

Primuline orDehydro-thio-toluidine-sulfonicAcid

m-Phenylene-diamine

ResorcinolNaphthionic Acid

(2 mols)

HAcid/3-Naphthol

BcnzidineNaphthionic Acid

(2 mols)






Used and Notes



Glycine Red

Orange TA

Congo Corinth G

Congo Rubine

Benzo Orange R

Dianol Red 2B

Benzo Purpurin 4B

BrilliantPurpurin 4B

I '14:—M'17:—M'18:—M'19:—M'20:—

602????

I '14:— 44,157M'17:—- ?M'18:— ?M'19:—137,704M'20:—242,50:

I '14:— 46,213M'17.— ?M'18:— ?I '20:— 2,601

I '14:— 1,073M'17:— ?M'18:— 50,422M'19:— 42,807I '20:— 220M '20:— 86,210

I '14:— 4,422I '20:— 17,632

I '14:—351,712M'17:— ?M'18:—356,522M'19:—288,021I '20:— 3,492M'20:—617,629

I '14:— 6,634

Benzidine Da-Naphthyl-glycine

Benzidine DCresol

Benzidine DNevile-Winther's Acid



Dichloro-benzidineNaphthionic Acid

(2 mols)


(2 mols)

Tolidine DBroenner's Acid







Used and Notes


Brilliant Purpurin R

Congo 4RCongo Red 4R

Congo Corinth B

Benzopurpurin 10B

Azo Violet

TRISAZO DYESDianil Black R

Azo Corinth

TETRAKISAZO DYESBenzo Brown B

Toluylene Brown R

I ' 1 4 : — 8 , 0 5 1

M ' 1 8 : — ?

2 , 1 9 6

4 7 , 7 6 8

I '14*M'19:-

I ' 1 4 : —

M'18 :«

M ' 1 9 : -

I ' 2 0 :

M ' 2 0 :

2,20541,265

I '14:M'20:-

4389

I ' 1 4 : — 2 0 1

T o l i d i n e

A m i n o - R A c i d

T o l i d i n e

R e s o r c i n o l

T o l i d i n e

N e v i l e - W i n t h e r ' s A c i d

D i a n i s i d i n e

N a p h t h i o n i c A c i d

( 2 m o l s )

D i a n i s i d i n e


B e n z i d i n e

C h r o m o t r o p i c A c i d

m - P h e n y l e n e - d i a m i n e

T o l i d i n e

R e s o r c i n o l

3 - A m i n o - l - p h c n o l - 4 -

s u K o n i c A c i d

m - P h c n y l e n c - d i a m i n e

(3 m o l s )


(2 m o l s )

3 : 5 - D i a m i n o - p - t o l u e n e -

s u l f o n i c A c i d


(2 m o l s )


(2 m o l s )




490

563


TETRAKISAZO DYES{continued)

Cotton Brown A

DlPHENYL-NAPHTHYL--METHANE DYE

New Patent Blue B


I '14:— 29,074

I '14:— 595I '20:— 1,814


Benzidinem-Phenylenc-diamine

(2 mols)Naphthionic Acid

(2 mols)

Hydrol[Substitution of NH2 by

SO3H; Oxidation]


D

A

/3-Naphthisatin

2-Naphthisatin

1: 2-/3-Naphthazoledione (C A. nomen. for ketoform)

1:2-Diketo-l: 2-dihydro-/3-naphthindole

CO—CO CO—C.OH

- N H —N= C12H7NO2 =

FORMATION.—/3-Naphthylamine is reacted with glyoxal sodium bisul-fite compound forming /3-naphthindol-sulfonate

<CH

NH

. SO3Na

By adding acetic acid and sodium nitrite to a solution of this latterbody in warm water, there results isonitroso-naphthoxindole

. C : N . O HC10HX >CO , which upon being boiled with sulfuric acid

\forms the jS-naphthisatin

LITERATURE.—Beilstein, Organische Chemie (2 auf.) II, 624; I I spl.342Cf. Lange, Zwischenprodukte, #2965


Dyes Derived from /3-Naphthisatin

359


891

892


INDIGO GROUP DYESCiba Green G

Helindone Green G


Manufacture

I '14:— 119

I '20:— 1,248


/3-Naphisatin (2 mols)[Bromination]

/3-Naphthisatin (2 mols)[Bromination]


V

V

2-Naphthisatin

See, jS-Naphthisatin

1-Naphthol/See, a-Naphthol

2-NaphtholSee, /3-Naphthol

a-Naphthol1-Naphthol (C A. nomen.)

OH

STATISTICS.—Imported '14:—405,578 lbs.Manufactured '17:— 72,329 lbs.Manufactured '18:—136,723 lbs.Manufactured '19:—135,025 lbs.Manufactured '20:— ?

FORMATION.—(l)Naphthalene is sulfonated cold to a-naphthalene-sulfonic acid, which is then fused with caustic soda to form thea-naphthol. (2) a-Naphthylamine hydrochloride or sulfate ishydrolyzed to a-Naphthol by heating with water in an autoclave



Dyes Derived from a-Naphthol

SchidtsNumberfor Dye

105

144

160

172

ISO

183


NITRO DYESMartius Yellow

Naphthol Yellow S

MONOAZO DYESSudan Brown

Orange I

XaphthylamineBrown

Fast Brown N

Fast Brown 3B

Erio Chrome BlueBlack B

Erio Chrome Black T

Statistics ofImport andManujacture

I '14:— 3,295I '20:— 26

I '14:—251,222M'17:— ?M'18:— ?M'19:— ?M'20:— ?

M'17:— ?M '18:— ?M'19:— ?

I '14:— 8,30;M'17:— ?M'18:— ?M'19:— ?I '20M'20

1,32314,684

I '14:— 68,281M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I '14:— 1,477

I '14:-M'17:-M'18:-M'19:-I '20:-M'20:-

I '14:-M'18:-M'19:-I '20:-M'20:-

57,0009,326

- 20,371- 29,255

-129,550

- 2,624


[Dirutration]

[Dinitration, Sulf ona-tion]

a-Naphthylamine

Sulfanilic Acid

Naphthionic Acid

Broenner's Acid


Nitro-l-amino-2-napli-thol-4-sulfonic Acid


Dyes Derived from a-Naphthol (continued)

301


212

214

619

731

895


DISAZO DYESFast Brown GAcid Brown G

Fast Brown 0

INDOPHENOL DYEIndophenol

SULFUR DYEThiophor Indigo CJ

INDIGO GROUP DYEAlizarin Indigo 3H


Manufacture

I '14:— 17,407I '20:— 485

I '14:— 2,000

M'17:— ?M'18;— ?M19:—126,611M'20:— ?

I '20:— 3,514


Sulfanilic Acid (2 mols)

Xylidinc-sulfonic Acid(2 mols)

Nitroso-dimethyl-anilinc orDimethyl-p-phenylenc-diamine

Dimcthyl-p-phenylcnc-diaminc

[S+Na*S]

Dibromo-isatinChlorido

DyeA ppli-cntlonClass

A

A

V

S

V

0-Naphthol

2-Naphthol (C A. nomen.)

(^ J J 0 H = CioH80 = 144

STATISTICS.—Imported '14:— 1,264,525 lbs.Manufactured '17:— 5,952,772 lbs.Manufactured '18:— 5,254,637 lbs.Manufactured ;19:— 4,916,416 lbs.Manufactured '20:—11,920,714 lbs.

FORMATION.—Naphthalene is sulfonated to /^naphthalene-sulfonie acid;this is fused with caustic soda, and the resulting /5-naphlhol isisolated and purified

LITERATURE.—Cain, Intermediate Products (2d Ed.), 212Thorpe, DicT Chemisiry, 3, G14; 623


Dyes Derived from /3-Naphthol

SchidtzNumberj or Dye

2

36

46

56

72

73

74

76

86

93


NITROSO DYEGambine YFast Printing Green

MOXOAZO DYESSudan IOil Orange

7n-NitranilineOrange

Paranitraniline Red

Pigment Orange R

Pigment FastRedHL

Lithol FastScarlet R

Helio Fast Red RL

Tannin Orange R

Sudan II

AzarineS

Pigment Purple ASudan R

Statistics ojImport arid

Manufacture

I '14:— 4,554M'17:— 32,455M'18:—29,670M'19:— 75,868M'20:—116,624

I »14:—4:9,847M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I '14:— 49,708M'17:— ?M'18:— ?M'19:— ?I '20:— 1,001M'20:— ?

I '14:— 2,202I '20:— 347

I '14:— 501M'17:— 27,595M'18:— 23,692M'19:— ?M'20:—170,658

I '14:— 99


[Nitroso-derivative]

Aniline

m-Nitro-aniline

p-Nitroaniline

p-Nitro-o-toluidine

m-Nitro-p-toluidine

o- and p-Amino-benzyl-dimetKyl-amine

Xylidine

2-Amino-4: 6-dichloro-pbenol

o-Anisidine


M

ss

MF

MF

CLMF

CL

B

ss

M

CL


Dyes Derived from /?-Naphthol {continued)

363


97

98

99

106

115

126

131

132

145


MONOAZO DYES{continued)

ChloranisidineScarlet

Naphthol PinkNitrosamine

PinkBX

Tuscaline Orange G

Carmine NaphthGarnet

Autol Red RL

Azo Turkish Red

Indoin Blue RUnion Blue R

Permanent Orange R

Lake Red P

Orange II


Manufacture

I '14:— 99

I '14:— 6,505M'17:— ?M'18:— ?M'19:— ?M '20:— ?

I '14:— 15,353

I '14:— C0,345M'17:— ?M'18:— ?M'19:— ?I '20:— 1,750

I '14:—128,877M'17:—712,586M'18:—916,890M'19:—

1,133,925I '20:— 2,265M'20:—

1,850,341


Chloro-anisidinc

p-Nitro-o-anisidine

m-Nitro-o-anisidine

ct-Napl ithylamine

jft-Naphthylamino

Safr&nineor

m-Toly lenc-diamin eo-ToluidiixeAniline

2-Amino-C-chloro-bcn-zene-sulfonic Acid

p-*Nitro-anilino-o-sul-f onic Acid

Sulfanilic Acid

DyeA ppli-catlonClass

MF

MF

CLMF

CL

MF

B

CL

CL

A


Dyes Derived from 0-Naphthol (continued)



ManufactureOthei Intermediates

Used and Notes



Fast Orange 0

Orange T and RO

Lake Red C

Acid AlizarinViolet N

Palatine ChromeViolet

Acid AlizarinBlack R

Fast Red A

Brilliant Fast Red G

Lithol Red R

I 14:-— 1,250M'17:— ?

I 14:— 90,747M'17:— ?M19:— ?I '20:— 20M'20:— ?

I '14:—306,607M'19:— ?I '20:— 4,105M'20:-- ?

I '14:— 1,199M'19:— ?M'20:— ?

14:— 16,800M'19:— ?I '20:— 439M'20:— ?

I '14:— 46,359M17:—191,424M18:—242,215M19:—267,582I '20:— 948M'20:—433,989

I 14:—281,963M 17:— ?M18:—353,104M19:—269,169M'20:— ?

o-Nitro-aniline-p-sulfonic Acid

o-Toluidine-m-sulfonicAcid

2~Chloro-5-toluidine-4-sulfonic Acid

o-Amino-phenol-p-sul-fonic Acid

2-Amino-6-nitro-l-phenol-4-sulfonicAcid

Naphthionic Ac'd

Laurent's Acid

2-Naphthylamine-l-sulfonic Acid

CL

CL

ACr

M

A

CL


Dyes Derived from /?-Naphthol {continued)

365

SchulizNumberjor Dye

174

175

181

184

185

193

200

223

Ordinary Na?ne andClass oj Dye


Double BrilliantScarlet

Ponceau for Silk

Palatine ChromeBlack 6B

Salicine Black U

Erio ChromeBlack A

Anthracene ChromeBlack

Clayton Cloth RedStanley Red

Lake Red D

DISAZO DYESSudan III


Manufacture

I '14:—210,429M'17:— ?M'20:— ?

I '14:— 727

I '14:—248,721M'17:— ?M'18:—469,159M'19:—739,372M'20:— 2,001M'20:—

1,074,248

I '14:— 96,570M'17:— ?M'18:— ?M'19:—686,700I '20:— 14,262M'20:— ?

I '14:— 51,577I '20:— 2,339

I '14:— 100M'18:— ?M'19:— ?M'20:— ?

I '14:— 2,428M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I '14:— 2,409M'17:— ?M'18:— ?M'19:— ?M'20:— ?


Broenner's Acid

2-Naphthylamine-8-and 5-sulfonic Acids


Nitro-l-amino-2-naph-thol-4-sulfonic Acid

2-Amino-3Jnaphthol-6-gulfonic Acid

Dchydro-thio-p-toluidine-sulfonicAcid

Anthranilic Acid

Amino-azo-benzene


A

A

ACr

ACr

M

A

CL

S3MF


Dyes Derived from jS-Naphthol (continued)

SchidtsNumberfor Dye

232

239

240

246

247

252

260

264



Sudan IV

Azotol C

Janus Red B

Cloth Scarlet G

Double ScarletScarlet EC

Cloth Scarlet R

Erio ChromeVerdon A

Fast Sulf on Black F


Manufacture

I '14:M'17:-M'18:-M'19:-M'20:-

5113,33414,904

?

I '14I '20

:— 250:— 176

I '14M'17:3VT18:M'19;M'20:-

I '14:-M'17:-M'18:-M'19:-M'20:-

:— 9:— ?:— ?:— ?

:— ?

39,522

74,203

I '14:— 882

M'19:I '20:M'20:-

?2,204



o-Amino-azo-toluene

Amino-chrysoidineor

p-Amino-acetanilide andm-phenylene-diamine

ori\T-Dimethyl-p: p'-dia-

mino-azo-benzene

m-Amino-phenyl-tri-methyl-ammoniuinChloride

??2-Toluidine

A m in o-azo-benzene-sulf onic Acid


o-Ainino-azo-toluene-sulf onic Acid

Sulfanilic Acidm-Amino-p-cresol

Naphthionic AcidHAcid


Dyes Derived from /3-Naphthol (continued)




Diamine Blue 6G

Acid AlizarineBlack SE

Palatine ChromeBlack F

Acid AlizarineBlack SN

Palatine ChromeBlack S

Benzidine Puce

Trisulf on Violet B

Trisulfon Blue R

Milling Scarlet 4RAcid Anthracene

Red3B

Diazurine B


Manufacture

I '14:— 19,185I '20:— 34,302

M'17:M'18:-M'19:-

I '14:— 1,124M'17:— ?M'18:— ?M'19:— ?I '20:— 7,927M'20:— ?

911I '14:—M'19:— ?M'20:— ?

I '14:— 18,330I '20:— 2,336


Amino-G Acidl-Amino-2-naphthol

Ethyl Ether

2:6-Diamino-phenol-4-sulfonic Acid

0-Naphthol (2 mols)

2: 6-Diamino-phenol-4-sulfonic Acid

SchaelTer's Acid

Benzidinej3-Naphthol (2 mols)

Benzidinel-Naphthol-3: G

sulf onic Acid

l-Naphthol-3: 6: 8-tri-sulf onic Acid

Tolidine

o-Tolidine-disulfonicAcid

i8-Naphthol (2 mols)

Dianisidinel-Naphthylamine-6-

sulf onic Acid (2 mols)/3-Naphthol (2 mols on

fiber)


Dyes Derived from /3-Naphthol (continued?)


408

409

419

434

566

649

650



Dianisidine Blue

Trisulf on Blue C

Chicago Blue RW

Coomassie NavyBlue


Wool Green S

OXAZINE DYESNew Blue RMeldola's BlueCotton Blue

New Blue B


Manufacture

:— 240

I '14:— 813

I '14:— 15,176M'19:— ?I '20:— 351M'20:— ?

I '20:— 42,357

I '14:— 60,073M'17:— ?M'19:— ?I '20:—127,764M'20:—212,362

I '14:— 32,509M'17:— ?M'18:— 22,613M'19:— ?I '20:— 5,240M'20:— ?


Dianisidine0-Naphthol (2 mols)

Dianisidinel-Naphthol-3: 6:8-

trisulfonic Acid

Dianisidinel-Amino-8-naphthol-

2:4-disulfonic Acid

1:4-Naphthylene-dia-mine-2-sulfonic Acid

RAcid

Ketone[Sulfonation]


Nitro so-dimetliyl-aniline (2 mols)



651

652

Dyes Denvec


OXAZINE DYES{continued)

New MethyleneBlue GG

New Fast Blue F

; from /3-Naphthol {continued)


Manufacture

I '14:— 2,502



[Dimethyl-amine,Oxidation]

or[Meldola's Blue, Di-

methyl-amine, Oxi-dation]


Hydrolor

[Meldola's Blue;Hydrol]


B

B

a-Naphthol-carboxylic Acid

See, l-Hydroxy-2-naphthoic Acid

/3-Naphthol-carboxylic Acid

See, 3-Hydroxy-2-naphthoic Acid

l-Naphthol-3:6-disulfonic Acid (C. A. nomen.)

R G Acid

G R Acid

a-Naphthol-disulfonic Acid R G

OH

HO3S SO3H = CioH807S2 =

STATISTICS.—Manufactured '19:— ?Manufactured '20:— ?


FORMATION.—(1) By fusing sodium naphthalene-l:3:6-trisulfonatewith half its weight of caustic soda and half its weight of water inan autoclave. (2) By diaaotizing l-naphthylamine-3: 6-disulfonicacid and adding to boiling dilute sulfuric acid


Dyes Derived from l-Naphthol-3:6-disulfonic Acid

SchiltzNumberJor Dye

64

81

109

165

225


MONOAZO DYESAzo Acid Red BLanafuchsine

Palatine Scarlet ABrilliant Cochineal

2R

Palatine Red A

Azo Red A

DISAZO DYESCroceine AZ

IMMMIM

I

IMJLVxM

II


'14:—'17:—'18:—'19:—'20:—'20:—

'14:—

'14:—MQ.'19t—

'14:—'20:—

78,305??

15,272674?

7,510

3009i

500100


p-Amino-acetanilide

m-Xylidine

a-Naphthylamine

Naphthionic Acid

A min o-azo-benzene


A

A

A

A

A


Andresen's Acid€-Acid or Epsilon Acida-Naphthol-e-disulfonic AcidDisulfo Acid E

HO3S OH

SO H — C10H8O7S2=304



FOKMATION.—Heat a solution of the acid sodium salt of 1-naphthyl-

amine-3: 8-disulfonic acid in an autoclave for 5 hours at 180°

LITERATURE.—Cain, Intermediate Products (2d Ed.), 219Lange, Zwischenprodukte, #2638, 2639Thorpe, Die. Chemistry, 3, 619



100

117

121

325

387

451

456

Ordinary Name andClass o/ Dye

MONOAZO DYESEosamine B

Erica 2 GN

Erica B

DISAZO DYESColumbia Blue R

Columbia Blue G

TRISAZO DYESCongo Fast Blue E


II

IMI

IMI

I

I

IMI

II


1 4 : -'20:—

1 4 : -1 9 : -'20:-

1 4 : -1 9 : -'20:-

1 4 : -

1 4 : -

1 4 : -1 8 : -'20:-

1,914• 1,600

1,171

• 337

• 5,349• ?- 2,393

• 3,071

- 7,094

- 4,449- ?- 723

14:—100,495'20:- - 1,821


m-Amino-p-cresol-methyl ether

Dehydro-thio-p-tolui-dine

D ehydr o-thio-m-xylidine

Benzidinel-Amino-S-naphthol-4-

sulfonic Acid

Tolidinel-Ammo-8-naphthol-4-

sulfonic Acid

Tolidinca-Naphthylaminel-Naphthol-3:8-disul-

fonic Acid (2 mols)

Dianisidinea-Naphthylaminel-Naphthol-3: 8-disul-

fonic Acid (2 mols


A

D

D

D

D

D

D



Schoellkopf s Acid

a-Naphthol-disulfonic Acid Sch

a-Naphthol-5-disulfonic Acid

a-Naphthol-disulfonic Acid S

SAcid

HO3S OH

SO3H


FORMATION.—From l-naphthylamine-4: 8-disulfonic acid by diazotizingand running this diazo solution into dilute sulfuric acid. Thislatter is now boiled to complete the decomposition




80

95

110

118

226

235

321


MONOAZO DYESWool Scarlet R

Azo CochinealCochineal Scarlet B

Buffalo Rubine

Geranine

DISAZO DYESCroceine B

Croceine 3B

Heliotrope 2B


Manufacture

I '14:— 39,888

I '14:— 952

I '14:— 18,917M'19:— ?I '20:— 527

M'19:— ?M'20:— ?

I '14:— 1,473I '20:— 60


Xylidine

0-Anisidiiie

a-Naphthykmine

Dchydro-tlrio-p-toluidine

Amino-azo-benzene

Amino-azo-toluene



A

A

A

D

A

A

D


2-Naphthol-3: 6-disulfonic Acid

See, R Acid

2-Naphthol-3:7-disulfonic Acid (C. A. nomen.)

£-Naphthol-5-disulfonic Acid

/3-Naphthol-disulfonic Acid F

373

HO3SSO H

FORMATION.—2-Naphthol-7-sulfonic acid is heated with 66° sulfuricacid for a considerable time at 120°

LITERATURE.—Lange, Zwischenprodukte, #2653, 2654Thorpe, Die. Chemistry, 3, 627

Dye Derived from 2-Naphthol-3:7-disulfonic Acid


402


DISAZO DYEDiamine Blue

Black E



Used and Notes

Ethoxy-b enzidineGamma Acid


D

2-Naphthol-6:8-disulfonic Acid

Seef G Acid

a-Naphthol-5-disulfonic Acid


a-Naphthol-€-disulfonic Acid


a-Naphthol-disulfonic Acid GR


a-Naphthol-disulfonic Acid RG



a-Naphthol-disulf onic Acid S


a-Naphthol-disulfonic Acid Sch


j3-Naphthol-a-disulf onic Acid

See, R Acid

£-Naphthol-j3-disulfonic Acid

See, G Acid

0-Naphthol-7-disulfonic Acid

See, G Acid

/S-Naphthol-5-disulfonic Acid

See, 2-Naphthol-3:7-disulfonic Acid

0-Naphthol-disulfonic Acid C

2-NTaphthol-4: 8-disulfonic Acid (not considered herein)

£-Naphthol-disulf onic Acid P

See, 2-Naphthol-3: 7-disulfonic Acid

jS-Naphthol-disulf onic Acid G

See, G Acid

j3-Naphthol-disulf onic Acid R

See, R Acid

Naphtholic Acid


l-Naphthol-4-sulf onic Acid

See, Nevile-Winther's Acid


l-Naphthol-5-sulfonic Acid (C. A. nomen.)

L Acid

Cleve's Acid

a-Naphthol-sulfonic Acid C

a-Naphthol-sulfonic Acid L

OH

375

HO3S

STATISTICS.—Imported '14:—25,126 lbs.Manufactured 18:— ?Manufactured ' 19:— ?Manufactured '20:— ?

FOKMATION.—(1) From naphthalene-1: 5-disulfonic acid by fusion withcaustic soda. (2) From l-naphthylamine-5-sulfonic acid by diazo-tizing, and boiling the diazo solution with dilute sulfuric acid

LITERATXJEE.—Cain, Intermediate Products (2d Ed.), 218Lange, Zwischenprodukte, #2422-2424Thorpe, Die. Chemistry, 3, 617

Dyes Derived from l-Naphthol-5-sulfonic Acid


78

108

164


MONOAZO DYESCochineal Scarlet 4R

Double Ponceau R

Fast Red VR


I >14:— 20,714M'17:— ?M'18:— ?M'19:-~ ?I ' 2 0 : - 6,290M'20:— ?


Xylidine

a-Naphthylamine

Naphthionic Acid


A

A

ACr


Dyes Derived from l-Naphthol-5-sulfonic Acid (continued)


275

411


DISAZO DYESDiamond Black F

Benzoazurine 3G


Manufacture

I '14:—462,306M'17:— ?M'18:— ?M'19:—222,938I '20:— 2,226M'20:— ?

I '20:— 201


Ammo-salicylic Acida-Naphthylamine

Dianisidinel-Naphthol-5-sulfonic

Acid (2 mols)


ACr

D

2-Naphthol-l-sulfonic Acid

Tobias Acid

(Falsely called 0-naphthyl-sulfuric Acid)

SO3H

C 0 O H

STATISTICS.—Manufactured in 1918, 1919, 1920 in indeterminate

amounts

FOBMATION.—By sulfonating /3-naphthol with

per cent sulfuric acid at about 40°

parts of 90-92




USES.—For preparation of 2-naphthylamine-l-sulfonic acid

2-Naphthol-6-sulfonic Acid

See, Schaeffer's Acid


2-Naphthol-7-sulfonic Acid (C. A. nomen.)


/3-Naphthol-sulfonic Acid F

FAcid

Monosulfonic Acid F

Cassella's Acid

H 0 3 S | 0 0 ° H = c i ° H 8 a s = 2 2 4

STATISTICS.—Imported '14:—1,996 lbs.Manufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?

FOKMATION.—By fusing sodium naphthalene-2:7-disulfonate withcaustic soda solution in an autoclave


Dyes Derived from 2-Naphthol-7-sulfonic Acid


56


MONOAZO DYEParanitraniline Red


Manufacture

I '14:— 49,847M'17:— ?M'18:— ?M'19:— ?


p-Nitro-aniline[0-Naphthol]


MF


See, Croceine Acid

a-Naphthol-sulfonic Acid d



a-Naphthol-sulfonic Acid C

See, l-Naphthol-5-sulfonic Acid

a-Naphthol-sulfonic Acid L

See, l-Naphthol-5-sulfonic Acid

a-Naphthol-sulfonic Acid NW


a-Naphthol-sulfonic Acid S


/9-Naphthol-a-sulfonic Acid of Armstrong and Schultz


/S-Naphthol-a-sulfonic Acid (of Bayer & Co.'s patents)

See, Croceine Acid

j5-Naphthol-j8-sulfonic Acid


iS-Naphthol-7-suIf onic Acid

2-Naphthoi-5-sulfonic Acid (not considered herein)

0-Naphthol~S-sulf onic Acid

See, 2-Naplitliol-7-siilfoiiic Acid

/5-Naphthol-sulf onic Acid B

See, Croceine Acid

0-Naphthol-sulfonic Acid F

See, 2-Naphtiiol-7-fiulfonic Acid

0-Naphthol-sulf onic Acid S



/3-Naphthol-sulfonic Acid Schaeffer


379

l-Naphthol-3: 6:8-trisulfonic Acid (C. A. nomen.)

HO3S OH

SO3H = 384

STATISTICS.—Imported '14:—6,443 lbs.Manufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?

FORMATION.—From l-naphthylamine-3: 6: 8-trisulfonic acid by diazo-tizing in the presence of a large excess of sulfuric acid and thenboiling and purifying



322

378

409

Dyes Derived from


DISAZO DYESTrisulfon Violet B

Trisulfon Blue R

Trisulf on Blue B

l-Naphthol-3


Manufacture

I '14:— 1,124M'17:— ?M'18:— ?M'19:— ?I '20:— 7,927M'20:— ?

I '14:— 911M'19:— ?M'20:— ?

I '14:— 813

6:8-trisulfonic Acid


Bcnzidine/J-Naphthol.

Tolidine0-Naphthol

Dianisidine/J-Naphthol


D

D

D


2-Naphthol-3:6:8-trisulfonic Acid (C. A. nomen.)

/S-Naphthol-trisulfonic Acid

HO3S

HO3SOHSO3H

— 384


FORMATION.—From /3-naphthol by sulfonation with 2 parts of con-centrated sulfuric acid at 70-80°, then with 2 more parts of concen-trated sulfuric acid at 120°, and finally with 2 parts of 40 per centoleum at 150°

LITERATURE.—Cain, Intermediate Products (2d Ed.), 229Lange, Zwischenprodukte, #2792Thorpe, Die. Chemistry, 3, 628Ullmann, Enzy. tech. Chemie, 8, 351


170

228

Dyes Derived from


MONOAZO DYEPonceau 6R

DISAZO DYEPonceau 5B,Erythrine P

2-Naphthol-3


Manufacture

I '14:— 2,880M'17:— ?M'18:— ?

• 6:8-trisulfonic Acid


Naphthiordc Acid

Amino-az o-benzene


A

A

/3-Naphthol-trisulfonic Acid

See, 2-Naphthol-3:6:8-trisulfonic Acid

a-Naphthol-trisulfonic Acid S

l-Naphthol-2:4: 8-trisulfonic Acid (not considered herein)

Naphtho-picric Acid

2:4: 5-Trinitro-l-naphthol (not considered herein)


1: 2-Naphthoquinone (C. A. nomen.)

0-Naphthaquinone

1:2-Naphthaquinone

= 0

FORMATION.—From Orange II as follows: Sulfanilic acid is diazotizedand coupled with /3-naphthol to form Orange II. This azo dye isreduced with stannous chloride to l-amino-2-naphthol, which isoxidized with sodium bichromate and sulfuric acid to /?-naphtho-quinone

LITERATURE.—Thorpe, Die. Chemistry, 3, 654Lange, Zwischenprodukte, #23, 648, 2408

Dye Derived from 1:2-Naphthoquinone


667


THIAZINE DYEBrilliant Alizaiin

BlueGIndochromine T


Manufacture

I '14 — 19,481M'19— ?I '20.— 3,214M '20 — ?


Ethyl-sulfobcnzyl-p-phenylene-diamine-tlriosulfonic Acid


M

1:2-Naphthoquinone-4:6-disulfonic Acid

/3-Naphthoquinone-4:6-disulfonic Acid

3:4-Dihydro-3:4-diketo-l: 7-naphthalene-disulfonic Acid (<7. A.nomen.)

0

HO3S—i=0 _ — 318

SO3H


FORMATION.—l-Nitroso~2-naphthol-6-sulfonic acid is treated with bi-

sulfite forming l-amino-2-naphthol-4: 6-disulfonic acid. This latter

body is now oxidized with nitric acid under 15°, resulting in 1:2-

naphthoquinone-4: 6-disulfonic acid

LITERATURE.—Ullmann, Enzy, tech. Chemie, 8, 358



Dyes Derived from 1:


666

667


THIAZINE DYESIndochromogen S

Brilliant AlizarinBlueG

Indochromine T

2-Naphthoquinone-4:6-disulfonic Acid


Manufacture

I '14:— 19,481M'19:— ?I '19:— 3,214M'20:— ?


Diethyl - p - phenylene-diamine-thiosulfonic-Acid

Dimethyl-p-phenylene-diamine-thiosulfonicAcid


M

M

/S-Naphtlioquinone-4:6-disulfonic Acid

See, 1:2-Naphthoquinone-4:6-disulfonic Acid

1:2-Naphthoquinone-4-sulfonic Acid

/3-Naphthoquinone-4-sulfonic Acid

3:4-Dihydro-3:4-diketo-l-naphthalene-sulfonic Acid (C. A.nomen.)

O

Q M = 0 = C W S A S =

SO;


FORMATION.—2-Amino-l-naphthol-4-sulfonic acid or l-amino-2-napthol-4-sulfonic acid is oxidized with nitric acid

LITERATURE.—Ullmann, Enzy. tech. Chemie, 8, 358Thorpe, Die. Chemistry, 3, 657Cf. Lange, Zwischenprodukte, #2631


656

657

Dyes Derived from


OXAZINE DYES

Alizarin Green G

Alizarin Green B

1: 2-Naphthoquinone~4-sulf onic Acid


Manufacture

M'19:— ?

I '14:— 551



2-Amino-l-naphtliol-4-sulfonic Acid

DyeApphcatioiClas*

M

M

/3-Naphthoquinone-4~sulfonic Acid

See, 1: 2-Naphthoquinone-4-sulf onic Acid

Naphtho-resorcin

1: 3-Dihydroxy-naphthalcne (not considered herein)

Naphthoyl-benzoic Acid

o-l-Naphthoyl-fcenzoic Acid ( C A. nomen.)

—CO.OH _ p TT n _

FORMATION.—From phthalic anhydride and naphthalene by heatingtogether in the presence of benzene and aluminium chloride

LITERATURE.—Lange, Zwischenprodukte, #2812Schultz, Farbstofftabellen (1914), #758


Dye Derived from Naphthoyl-benzoic Acid

SchuUzNumberfor Dye

758


ANTHEAQUINONB ANDALLIED DYES

Sirius Yellow G




CL

Naphthsultam-disulfonic Acid Sl~Naphthylamine-2:4:8-trisulfonic Acid (not considered herein)

1-NaphthylamineSee, a-Naphthylamine

2-NaphthylamineSee} /3-Naphthylamine

a-Naphthylamine1-Naphthylamine (<7. A. nomen.)a-Amino-naphthaJeneNaphthalidamNaphthalidine

NH2

STATISTICS.—Imported '14:— 112,226 lbs.Manufactured '17:—3,516,686 lbs.Manufactured '18:—2,671,601 lbs.Manufactured '19:—1,552,828 lbs.Manufactured '20:—5,177,547 lbs.

FORMATION.—Naphthalene is mononitrated, using mixed acid, and theresulting a-nitro-naphthalene is reduced with iron and hydrochloricacid to a-naphthylamine



Dyes Derived from a-Naphthylamine


105

106

107

108

109

110

111

112

113

114


MONOAZO DYESSudan Brown

Carmine NaphthGarnet

Autol Red RL

Sulfamine Brown A

Double Ponceau R

Palatine Red A

Buffalo Rubino

Fast Red BT

Fast Red BBordeaux B

Crystal Ponceau

Chromotrope 10B


Manufacture

M' 17:— ?MIS:— ?M'19:— ?

I 14:— 6,565M17:— ?M18:— ?M19:— ?M'20:— ?

I 14:— 132M18:— ?M19:— ?I '20:— 2,630M'20:— ?

I 14:— 300M18:— ?M10:— ?

M'17:— ?M18:— ?M'19:— ?

I 14:— 25,821M17:—120,595M18:—200,415M19:—161,862I '20:— 7,882M'20:—217,406

I 14:— 628

M19:— ?


a-Naphthol

/3-Naphthol

Nitroso-jft-naphthol

l-Naplitliol-5-sulfonicAcid

l-Naphtlu>l-3:6-disul-fonic Acid

l-Naphthol-4: 6-disuJ-fonic Acid

Schacffor's Acid

RAcid

GAcid

Chromotropic Acid

DyeApplicationClass

S3

CL

M

A

A

A

A

A

A

A


Dyes Derived from a-Naphthylamine (continued)




ManufactureOther Intermediaies

Used and Notes


218

220

241

243

244

245

256

257

258

261

DISAZO DYESNigrophorBASF

Palatine Black A

Neutral Gray G


Coomassie WoolBlack S

Nyanza Black B

Sulf on Black 3B

Sulfoncyanine


Buffalo Black 10B

I '14:-I '20:

I '14:-M'19:-I '20:-M'20:-

M'lS:-M'19:-

-299,274- 200

2,546

3,*472

I '14:—145,694M'17:— ?M'18:— ?M'19:— ?I '20:— 18,327M'20:— ?

I '14:— 7,994

M'19:M'20:


2: 5-Dichloro-aniline


Sulfanilic Acid

AnilineGamma Acid

Aeetyl-p-phcnylene-diamine

Schaeffer's Acid

Acetyl-p-phenylcne-diamine

RAcid

p-Nitro-aniline[Reduced]

Gamma Acid

Metanilic AcidPhenyl-1 -naphthyl-

aminc-8-sulfonic Acid

Metanilic AcidPhcnyl- or Tolyl-

1 -naphthylaminc-8-sulfonic Acid

Metanilic Acid1-Naphthyl amine-6-

and 7-sulfonic Acids

Sulfanilic AcidHAcid




262

263

265

266

267

267

268

269



Victoria Black B

Jet Black

SulfoncyanineBlack B

Naphthyl amineBlack D

Anthracite Black

Phenylene Black

Naphthyl BlueBlack N

Naphthol Black 6B


Manufacture

I '14:— 557

I '14:— 09,590MT7:— ?M'18:— ?M'19:— ?M'20:— ?

I '14:—152,141M'17:— ?M'18:— 29,724M'19:—I '20:—M 720:—

?1,687?

I '14:—M '17:—I '20.—

99?220

I '14:—120,512I '20:— 1,500M'20:— ?


Sulfanilic Acid1:8-Dihydroxy-naph-

thalcne-4-sulfonicAcid

Aniline-2:4-disulfonicAcid

Phcnyl-a-naphthyl-amine

Laurent's AcidPhenyl-1-naphthyl-

aininc-8-sulfonic Acid

Frcund's Acida-Naplitliylainine

(2 inols)

Fround's AcidDiphcnyl-m-phcnylone-

diamine

l-Naphthylamino-4: 7-disulfonic Acid

Diphenyl-m-phcnylcne-diamino

l-Naphthylamine-4: 6-ancZ4: 7-disulfonicAcids

l-Amino-2-naphtholEthyl Ether

l-Naphthyiaminc-4:6-and 4:7-disulfonicAcids

RAcid



SchidtsNumberjor Dye




Used and Notes

272

273

274

275

276

278

290

382



Diaminogen Blue BB

Diaminogen B

Diamond Black F

I '14:—103,598M'19:— ?

'20:— 50

Diamond Green B

Biebrich PatentBlack

Violet Black

Azo Mauve B

I '14:-M '17:-I '20:-

8 ,308

5,936

I '14:—-313,629I '20:— 18,120

I '14:—462,306M'17:— ?M'18 :— ?M'19:—222,938I '20:— 2,226

M'20:— ?

I '14:M ' 1 8 :I '20:— 4,061

8,622?

M ' 1 7 : -

M ' 2 0 : -

A m i n o - G A c i d

R A c i d

A c e t y l - 1 : 4 - d i a m i n o -

n a p h t h a l e n e - 6 - s u l -

f o n i c A c i d

S c h a e f f e r ' s A c i d

A c e t y l - 1 : 4 - d i a m i n o -n a p h t h a l e n e - 6 - s u l -f o n i c A c i d

G a m m a A c i d

A m i n o - s a l i c y l i c A c i dJNTevi le-Winther ' s A c i d

or l - N a p h t h o l - 5 -s u l f o n i c A c i d

A m i n o - s a l i c y l i c A c i d1 : 8 - D i h y d r o x y - n a p h -

t h a l e n e - 4 - s u 1 f o n i cA c i d

l ~ N a p l i t h y l a m i n e - 6 -and 7 - su l fon i c A c i d se t c .


p - P h e n y l e n e - d i a m i n e or

A m i n o - a c e t a n i l i d e

T o l i d i n eH A e i d




432

435

441

442

443

446

447

450



Diamine CutchNaphthylene Violet


Diazo BlueBlack RS

Direct Black V

Direct IndoneBlue R

Benzo Olive

Benzo Gray S

Benzo Black Blue R


Manufacture

M'19:— ?M'20:— ?

I 14:—145,738

I '14:— 1,149

I 14:— 802


1:5-Naphtliylcno-dia-minc-3:7-disulfonicAcid


Trimethyl-m-amino-phcnyl-ammoniumChloride

Anilinem-Phcnylcnc-diamino

orp-Amino-benzyl-

diethyl-amineResorcinolm-Phenylenc-diamine

BenzidinoH Acid (2 mols)

Benzidino2R AcidGamma Acid

Benzidino2R AcidH Acid

BenzidineSalicylic AcidII Acid

BenzidinoSalicylic AcidNovilc-Winthcr'a Acid

TolidineNcvilc-Winthcr's Acid

(2 mob)

DyiApplccdioClos

D

B

D

D

D

D

D

D



SchtdisNumberfor Dye

451

452

456

459

460

653

671

672

673



Congo Fast Blue R

Benzo Indigo Blue


Benzo Black Blue G

Benzo Black Blue 5G

OXAZINE DYENile Blue A

AZINE DYESInduline Scarlet

Azo Carmine G

Azo Carmine B


Manufacture

I '14:M'19:I '20:

4,449

723

'14:'20:

-100,495- 1821

I '14:— 602

I '14:-I '20:

1,5181,241

I '14I '20

I '14:M'17;M'18:M'19:I '20M'20

:— 198:-- 154

:— 17,500. 9

:— 196

I '20:— 549


Tolidinel-Naphthol-3: 8-disul-

fonic Acid (2 mols)

Tolidine1:8-DIhydroxy-naph-


Dianisidinel-Naphthol-3: 8-disul-

f onic Acid

Benzidine-disulfonicAcid



1:8-Dihydroxy-naph-thalene-4-s u If o n i cAcid (2 mols)

5-Diethylamino-2-nitroso-phenol

Ethyl-p-toluidine

Aniline (3 mols)CDisulfonation]

Aniline (3 mols)[Trisulfonation]



391


674

693

694



Rosinduline 2G

Milling Blue

Rose MagdalaFast Pink for Silk


Manufacture

I '20:— 201

I '14:— 3,082

I '14:— 597


Aniline (3 inols)[Trisulfonation, heated

to 160°]or

[Azo Carmine B heatedto 160°]

Aniline (3 mols)a-Naphthylamine

(2 mols)[Sulfonation]

a-Amino-azo-naph-thalcne


M

j3-Naphthylamine

2-Naphthylamine (C. A. nomen)

/3-Amino-naphthalene

C C r

STATISTICS.—Impor ted '14:—11,204 lbs.Manufactured ' 17:— ?Manufactured 18:—31,317 lbs.Manufactured 19:—99,597 lbs.Manufactured '20:— ?

F O R M A T I O N . — F r o m /3-naphthol by heating in an autoclave with am-monium sulfite and ammonia.

L I T E R A T U R E . — C a i n , Intermediate Products (2d Ed. ) , 187Lange, Zwischenprodukte, #2262Thorpe , Die. Chemistry, 3, 598


Dyes Derived from /3-Naphthylamine

SchvltsNumberfor Dye

115

116

281

282

287

301

383

433


MONOAZO DYESAzo Turkish Red

Sul famine Brown B

DISAZO DYESAzidine Fast

Scarlet 4BS

Azidine FastScarlet 7BS

Toluylene OrangeRR

Hessian Purple N

Naphthazurine B

Coomassie Black B


Manufacture

I '14:— 500

I '14:— 465

I '14:— 4,782


0-Naphthol

Nitroso-jS-naphthol[Sodium bisulfite]

o-ToluidineSulfo-m-tolylene-dia-

mine-bis(carbonyl-amino-n apht h o 1-sulfonic Acid)

/3-Naphthylainine(2 mols)

Sulfo-m-tolylene-dia-mine-bis (carb onyl-amino-naphth. ol-sulf onic Acid)

j8-Naphthylamine(2 mols)

3: ^Diamino-p-toluene-sulfonic Acid

i8-Naplithylamine(2 mols)

Diamino-stilbene-disul-f onic Acid

TolidineHAcid


R Acid


MF

M

D

D

D

D

D

A


Dyes Derived from |S-Naphthylamine {continued)


541

831



Brilliant DianilBlue 6G

ANTHRAQUINONE DYEIndanthrene Red BN


Manufacture

I '14:— 6,056I '20:— 4,7G6

Other InfermedialasUsed and Notes

/?-Naphthylaminc(3 mols)

Aniline0-Toluidin.cp-Toluidino[Disulfonaiion]

or/3-Napliiliylaminc

(3 mols)[Rosaniiinc; DLsulfoiui-

nation]

1-Chloro-anthraqiu-nonc-2-carboxylicAcid

3!

DyeApplcatioi

B

l-Naphthylamine-3:6-disulfonic Acid

See, Freund's Acid


a-Naphthylamine-e-disulfonic Acid

€ Acid or Epsilon Acid

8-Amino-l: 6-naphthalenc-disulfonic Acid (C. A. no men.)

HO3S NH2

STATISTICS.—Manufactured in 1919 and 1920 but in undisclosed quantties

FOBMATION.—Naphthalene-1:5- and 1:6-disulfonic acids are nitrateand reduced, resulting in l-naphthylaminc-3: 8- and 4: 8-disulfoniacids. The separation is effected by crystallizing out the aci(sodium salt of l-naphthylamine-3: 8-disulfonic acid


LITERATUKE —Cain, Intennediate Products (2d Ed.), 196Lange, Zwischenprodukte, #2575, 2576Thorpe, Die. Chemistry, 3, 592

l-Naphthylamine-4: 6- and 4:7-disulfonic Acidsa-Naphthylamine-disulfonic Acids D

Dahl's Acids II and I I I (respectively)

4-Amino-l: 6-naphthalene-disulfonic Acid (C. A, nomen.)

4-Amino-l: 7-naphthalene-disulfonic Acid (C. A. nomen)

NH2 NH2

andrrr\ci\ I 1 ana \ \ I = C i o H 9 N 0 6 S 2 — 303

3O3H

(Acid I I ) (Acid I I I )


FORMATION.—From naphthionic acid by sulfonation w i t h 25 per cent

oleum

LITERATURE.—Cain , Intermediate Products (2d Ed. ) , 198Thorpe, Die. Chemistry, 3, 593, 594Lange, Zwischenprodukte, #2577-2582

Dyes Derived from l -Naphthylamine-4 :6- and 4 :7-disul fonic Acids

SchidtsNumberfar Dye



ManufactureOther Intermediates- Used and Notes


267

268

269

MONOAZO DYES

Apollo Red B

DISAZO DYESPhenylene Black

Naphthyl BlueBlack N

Naphthol Black 6B

I '14:— 904

I '14:-M'17:-I '20:-

99

220

I 14:—120,512I '20:— 1,500M'20:— ?

p-Nitro-aniline

a-NaphthylamineDipheny-w-phenylene-

diamine[4:7 Acid only]

a-Naphthylaminel-Amino-2-naphthol

Ethyl Ether

a-NaphthylamineR Acid



d Acid or Delta Acid

Schoellkopf s Acid

Disulfo-acid S

4-Amino-l: 5-naphthalene-disulfonic Acid ( C A. nomen.)

a-Naphthylamine~£-disulfonic Acid

a-Naphthylamine-disulfonic Acid S

S Acid

HO3S NH2


FORMATION.—When naphthalene-1: 5- and 1: 6-disulfonic acids arenitrated and reduced, there is formed a mixture of 1-naphthylamine-3:8- and 4: 8-disulfonic acids. See under l-naphthylamine-3:8-disulfonic acid. The 4:8-acid is also made by sulfonating 1-naphthylamine-8-sulfonic acid with three parts of 10 per centoleum.

LITERATURE.—Cain, Intermediate Products (2d Ed.), 200Lange, Zwischenprodukte, #2575, 2583-2585Thorpe, Die. Chemistry, 3, 594

USES.—For making l-amino-8-naphthol-4-sulf onic acid, l:8-dihydroxy-naphthalene-4-sulfonic acid, and 1:8-naphthasultam-2:4-disulfonicacid


5-Amino-l: 3-naphthalene-disulfonic Acid ( C A. nomen.)

HO3S


FORMATION.—By sulfonation of the acetyl derivative of 1-naphthyl-amine-5-sulfonic acid or of a-naphthylamine

LITERATURE —Cain, Intermediate Products (2d E d ) , 200Lange, Zwischenprodukte, #2586Thorpe, Die. Chemistry, 3, 594

USES.—For preparation of l-amino-5-naphthol-7-suIfonic acid


See, Amino-R Acid


6-Amino-l: 3-?iaphthalene-disulfonic Acid (C. A. nomen.)

i8-Naphthylamine-disidfordc Acid II of Armstrong and Wynne

Armstrong and Wynne's Acid I I

H ° 3 S i i ] N H 2 =i ] C10H9NO6S2 = 303

HOsS


FORMATION.—By sulfonation of either 2-naphthylamine-5-S"ulfonic acid,or jS-naphthylamine, or 2-naphthylamine-7-sulfonic acid


USES.—For preparation of J acid (2-amino-5-naphthol-7-sulfonic acid)

2-Naplithylamine-6:8-disulfonic Acid

See, Amino-G Acid

a-Naphthylamine-a-disulf onic Acid

See, FreunxTs Acid


a-Naphthylamine-j3-disulfonic Acid

l-Naphthylaminc-3: 7-disulf onic Acid {not considered herein)

a-Naphthylamine-5-disulfonic Acid

See, l-Naphthylaminc-4: 8-disulfonic Acid

a-Naphthylamine-e-disulfonic Acid

See, l-Naphtliylaminc-3: 8-disulfonic Acid

a-Naphthylamine-disulfonic Acids D

See, l-Naphthylaminc-4: 6- and 4: 7-disulfonio Acids

a-Naphthylamine-disulfonic Acid S


/3-Naphthylamine-a-disulfonic Acid

See, Amino-R Acid

iS-Naphthylamine-7-disulfonic Acid

See, Amino-G Acid

/3 -Naphthylamine-5-disulfonic Acid

2-Naphthylamino-2: 7-disulf onic Acid {not considered herein)

/3-Naphthylamine-disulfonic Acid II of Armstrong and Wynne

See, 2-Naphthylaminc-5: 7-disulf onic Acid

/3-Naphthylamine-disulfonic Acid C

2-Naphthylaminc-4: 8-disulfonic Acid {not considered herein)

0-Naphthylamine-disulfonic Acid F

2-Naphthylamine-3: 7-disulf onic Acid {not considered herein)

/3-Naphthylamine-disulfonic Acid G

See, Amino-G Acid


0-Naphthylamine-disulf onic Acid R

See, Amino-R Acid

Naphthylamine Ether

See, l-Amino-2-naphthol Ethyl Ether

l-Naphthylamine-2-sulf onic Acid

X Acid

0-Naphthionic Acid

l-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)

NH2

= CioH9N03S=223

STATISTICS.—Manufactured '18:— ?Manufactured ' 19:— ?

FORMATION.—By heating naphthionic acid and naphthalene in a panfitted with a stirrer and reflux condenser, at the boiling point ofnaphthalene (217°) for few hours

LITERATURE.—Cain, Intermediate Products (2d Ed.), 189Thorpe, Die. Chemistry, 3, 589Lange, Zwischenprodukte, #2352-2355

SchuttsNumberfor Dye

562

Dye Derived from


DlPHENYL-NAPHTHTIr-METHANE

DYEFast Acid Blue B



Manufacture

I >U:— 33,251I '20:— 6,478


Hydrol[Oxidation]


A

l-Naphthylamine-4-sulf onic Acid



l-Naphthylamine-5-sulfonic AcidSee, Laurent's Acid

l-Naphthylamine-6-sulfonic Acid1

a-Naphthylamine-jft-sulfonic Acida-Naphthylamine-/3-sulfonic Acid ClCleve's jS AcidCleve's AcidErdmann's /x Acid or ix Acid

5-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)

NH2

HO3S1 = Ci0H9NO3S=223

STATISTICS.—Imported '14:—5,493 lbs.Manufactured ' 18:— ?Manufactured ' 19:— ?Manufactured '20:— ?

FOBMATION.—From napththionic acid by heating with sulfuric acid at120-130°

LITERATURE.—Lange, Zwischenprodukte, 2363Thorpe, Die. Chemistry, 3, 591Cf. Cain, Intermediate Products (2d Ed.), 192

Dyes Derived from l-Naphthylamine-6-sulfonic Acid


406

492


DJSAZO DYEDiazurine B

TETRAKISAZO DYEAnthracene Acid

Brown B



Used and Notes

l-Naphthylamine-6-sulf onic Acid (2 mols)

DianisidinejS-Naphthol (2 mols on

fiber)

l-Naphthylamiae-6-sulf onic Acid (2 mols)

Ammo-salicylic Acid(2 mols)

m-Phenylene-diamine


DJ

M|ACr

• See l-Naphthylamine-6- and 7-sulfonic Acids, page 400


l-Naphthylamine-6- and 7-sulfonic Acids

Cleve's Acids

Naphthylamine-sulfonic Acids Cleve

a-Naphthylamine-sulf onic Acids Cl

5-and 8-Amino-2-naphthalene-sulfonic Acids ( C . 4 . nomen.)

NH2

HO3Sand

H M C 0 -

FORMATION.—Naphthalene is sulfonated hot to /3-naphthalene-sul-fonic acid, this latter in sulfuric acid solution is nitrated cold withmixed acid. The excess acidity is removed with ground limestone(CaCO3), and the nitro-compounds reduced with iron borings anda little acetic acid to a mixture of l-naphthylamine-6-and-7-sulf onicacids


Dyes Derived from l-Naphthylamine-6- and 7-sulfonic Acids

SchutisNumberfor Dye

242

257


DISAZO DYESSulfon Black G

Sulfoncyanine


Manufacture

I '14:—145,694M'17:— ?MJ18:— ?M'19:— ?I J20:— 18,325M'20:— ?


Aniline1:8-Dihydroxy-naph-

thalene-4-sulfonicAcid

Metanilic AcidPheQyl-orTolyl-

1-naphthylamine-8-sulf onic Acid


A

A


Dyes Derived from l-Naphthylamine-6- and 7-sulf onic Acid (continued)






AnthraceneAcid Black

Biebrich PatentBlack

TEISAZO DYESColumbia Black

FF

Carbon Black

:— 7,704.

I '14:— 09,590M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I J14:— 17,793


Manufacture

I '14:—402,997M'18:— ?M'19:— ?

'20:— 23,350M'20:— ?


Mctanilic Acida-Naplithylamino

Laurent's AcidPlionyl-1-naphthyl-

ammc-8-sulfonic Acid

Amino-salicylic Acid,etc.

ct-Naplithylaininc, etc.

p-Phcnylcnc-diaminoGamma Acidm-Phcnylcnc-diamino

??-Phcnylonc-diamiiio-Hulfonic Acid fromp-nitro-an iliuo-o-sul-fonic Acid

m-Phcnylcnc-(or Toly-lenc-)-diamino or1:3-naphthyleno-dia-mine-C-sulfonic Acid(2 mob)

DyeA ppU-cationClass

l-Naphthylamine-7-sulfonic Acida-Naphthylamine-0-sulfonic Acid

Cleve's 6 AcidCleve's 8 AcidCleve's Acid

See, l-Naphthylamine-6- and 7-sulf onic Acids



8-Amino4-naphthalene-sulfonic Acid (C A. nomen.)

a-Naphthylamine-sulfonic Acid S

S Acid

Peri Acid

Schoellkopf s Acid

HO3S

STATISTICS.—Manufactured J19:— ?Manufactured '20:—562,939 lbs.

FORMATION.—Naphthalene is sulfonated at 60° to a-naphthalene-sulfonic acid and then nitrated below 40° to l-nitro-naphthalene-8-sulfonic acid, which latter upon reduction with iron furnishes t h el-naphthylamine-8-sulfonic acid


USES.—For manufacture of l-naphthylamine-4: 8-disulfonic acid

2-Naphthylamine-l-sulfonic Acid

Tobias Acid

2-Amino-l-naphthalene-sulfonic Acid (C A. nomen.)

SO3H

' = 2 2 3

STATISTICS.—^Manufactured '18:— ?Manufactured '19:— 84,260 lbs.Manufactured '20:—325,036 lbs.


FORMATION.—Sodium 2-naphthol-l-sulfonate (from 0-naphthol andsulfuric acid at 40°) is heated with ammonium hydrogen sulfiteand ammonia in an autoclave at from 100° to 150°


Dyes Derived from 2-NaphthyIamine-l-sulfonic Acid

SchultzNumbenJor Dye

173

179


MONOAZO DYESLithol Red E,

Lake Bordeaux B


Manujactvn e

I '14:—2S1,963M'17:— ?M'18:—353,104M '19:—-269,169M'20:~- ?

Other IntermediatesUsed and N"otes

/3-Naphthol

3-Hydroxy-2-naph-thoic Acid

DyeAppli-cotionClass

CL

CL

2~Naphthylamine-5-sulfonic Acid

i3-Naphthylamine-7-sulfonic Acid

iS-Naphthylamine-sulfonic Acid D

Dahl's Acid

Forsling's Acid II

See, 2-Naphthylamine-5- and 8-sulfonic Acids

2-Naphthylamine-5- and 8-sulfonic Acids i

6~ and 7-Amino-l-?iaphthalenc-sulfonic Acids (C. A. nomen.)

HO3S

CO- —STATISTICS.—Imported '14:—23,265 lbs. for the 2-naphthylamine-8-sulfonic Acid1 Sec 2-Naphthylamine-5-sulfonic Acid and 2-Naphtfiylamino-S-sulfonic Acid,


FORMATION.—By sulfonation of /3-naphthylamine

LITERATURE.—Cain, Intermediate Products (2d Ed.), 205Lange, Zwischenprodukte, #2368-2370, 2380-2383Thorpe, Die. Chemistry, 3, 601, 603

Dye Derived from 2-Naphthylamine-5- and 8-sulfonic Acids

Schult2Numberjor Dye

175

Ordinal y Name andClass of Dye

MONOAZO DYEPonceau for Silk


Manufacture

I '14:— 727


0-Naphthol


A

2~Naphthylamine-6-sulf onic Acid


2-Naphthylamine-7-sulfonic Acid

/?-Naphthylamine-5-sulfonic Acid

jS-Naphthylamine-sulfonic Acid F

FAcid

Delta Acid

BayerJs Acid

Cassella's Acid F

7-Amino-2-naphthalene-sulfonic Acid (C. A, nomen.)

FORMATION.—Sodium 2-naphthol-7-sulfonic acid (from caustic sodafusion of naphtlialene-2:7-disulfonic acid) is heated with am-monium acid sulfite solution and ammonia water in an autoclaveat 100° to 150°

LITERATURE.—Cain, Intermediate Products (2d Ed.), 207Lange, Zwischenprodukte, #2377-2379Thorpe, Die, Chemistry, 3, 602


Dyes Derived from 2-Naphthylamine-7-sulfonic Acid




Manvfacture



340

366

367

371

DISAZO DYESChlorazol Orange 2R

Diamine Red BDeltapurpurin 5B

Diamine Red 3BDeltapurpurin 7B

Rosazurine G

'14:— 21,058M'17:— ?M'18:— ?I '20:— 1,896

BcnzidineSalicylic Acid

TolidincBrocimcr's Acid

Tolidine2 -Naphthylarninc-7-sul-

sulfoiric Acid (2 mols)

TolidincEthyl-2-naphthyl-

aminc-7-sulf onic Acid

D

D

D

D

2-Naphthylamin.e-8-sulfonic Acid

i3-Naphthylamine-a-sulfonic Acid

Badische Acid

Forsling's Acid I

See, 2-Naphthylamine-5 and -8-sulfonic Acids

a-Naphthylamine-/3-sulfonic Acid


a-Naphthylamine-5-sulfonic Acid


Naphthylamine-sulfonic Acid Br


a-Naphthylamine-/3-sulfonic Acid Cl



a-Naphthylamine-sulf onic Acids Cl

See, l-Naphthylamine-6-and! 7-sulfonic Acids

Naphthylamine-sulfonic Acids Cleve

See, l-Naphthylamine-6-and 7-sulfonic Acids

a-Naphthylamine-sulfonic Acid L

See, Laurent's Acid

a-Naphthylamine-sulfonic Acid S

See, l-Naptohylamine-8-sulfonic Acid

/3-Naphthylamine-a-sulfonic Acid

See, 2-JSTaphthylamine-8-sulfonic Acid

/3-Naphthylamine-i3-sulfonic Acid


jS-Naphthylamine-r-sulf onic Acid


j3-Naphthylamine-5-sulf onic Acid


j8-Naphthylamine-sulfonic Acid D


/3-Naphthylamine-sulfonic Acid F

See, 2-Naphthylamine-7-suKonic Acid

l-Naphthylaroine-3:6:8-trisulfonic Acid

Koch's Acid

8-Amino-l: 3: 6-naphthalene-trisulfonic Acid (C A. nomen.)

HO3S NH2

/ V=C10H9NO9S3 =


STATISTICS.—Manufactured '17:— ?Manufactured '18:— ?Manufactured '19:—1,418,560 lbs.Manufactured '20:—3,921,950 lbs.

FORMATION.—Naphthalene is sulfonated to naphthalene-1: 3:6-trisul-fonic acid, using oleum; and this trisulfonic acid is nitrated cold,and then reduced with iron

LITERATURE.—Cain, Intermediate Products (2d Ed.), 202Lange, Zwischenprodukte., #2747, 2748Thorpe, Die. Chemistry, 3, 595

USES.—For preparation of H acid (l-Amino-8-naphthol-3: 6-disulfonicacid)

l-Naphthylamine-4:6: 8-trisulfonic Acid

8-Amino-l: 3: 5-naphthalene-trisulfonic Acid (C. A. nomen.)

HO3S NH

HO3S' X ) = C l o H 9 N O j S 3 = 3 8 3

FORMATION.—Sodium naphthalenc-1: 5-disulfonate is sulfonated tonaphthalene-1:3:5-trisulfonic acid, and this is nitrated cold, andthen reduced with iron


USES.—For preparation of K acid (l-amino-8-naphthol-4: 6-disulfonicacid)

2-Naphthylamine-3:6:8-trisulfonic Acid

7-Amino-l: 3: 6-naphthalenc-trisulfonic Acid (C A. nomen.)

HO3S

HO 3s l I J sO 3 H = C i o


FORMATION.—By sulfonation of amino-G acid (as potassium or sodiumsalt of 2-naphthylamine-6:8-disulfonic acid) with 40 per centoleum at 80-90° and finally at 120-130°. The amino-G acid ismade by amidation of G salt or by sulfonating /5-naphthylamine


USES.—For making 2R acid (2-Amino-8-naphthol-3: 6-disulfonic Acid)

4-(Naphthyl-azo)-l-naphthylamme (C. A. nomen.)See, o-Amino-azo-naphthalene

1-Naphthyl-diphenyl-methane (C. A. nomen.)See, Diphenyl-naphthyl-methane

1:5-Naphthylene-diamine-3:7-disulfonic Acid4:8-Diamino-2: 6-naphthalene-disulfonic Acid (C A. nomen)

NH2

FORMATION.—Naphthalene-2:6-disulfonic acid (from sulfonation ofnaphthalene) is dissolved in sulfuric acid and nitrated at 20-30°.The resulting 1: 5-dinitro~naphthalene-3: 7-disulfonic acid is saltedout and reduced


Dyes Derived from 1:5-Naphthylene-diamine-3:7-disulfonic Acid

SchtdtzNumberjor Dye

431

432


DISAZO DYESDiamine Golden

YeUow

Diamine CutchNaphthylene Yiolet


I 14:— 300I '20:— 49




DyeAppli-cadonClass

D

D


1:8-Naphthylene-diamine-3:6-disulfonic Acid

4: 5-Diamino-2: 7-naphthalene-disulfonic Acid (C. A. nomen.)

400

H2N NH2

H0 3 s — 318

FORMATION.—Naphthalene-2:7-disulfonic acid (from sulfonation ofnaphthalene) is dissolved in strong sulfuric acid and is then di~nitrated warm with strong nitric acid and sodium nitrate. Thedinitro-acid is reduced

LITERATURE.—Lange, Zwischenprodukte, #2704Cf. Cain, Intermediate Products (2d Ed.), 178Thorpe, Die. Chemistry, 3, 613

Dyes


55

Derived from 1: 8-Naphthylene-diarnine-3:6-disulfonic Acid


MONOAZO DYEBrilliant Archil C


Manufacture

I '14:— 401

Other 1rUenncdialesUsed and Notes

p-Nitro-aniline


A

1:3-Naphthylene-diamine-6-sulfonic Acid

5: 7-Diamino-2-waphthalenC'-sulfonic Acid (C. A. nomen.)

HO3S

NH2

NH2 = <

FORMATION.—l-Naphthylamine-3: 6-disulfonic acid (by nitration andreduction of naphthalenc-2:7-disulfonic acid) is heated withammonia in an autoclave at 160-180°

LITERATURE.—Lange, Zwischenprodukte, #2483Thorpe, Die. Chemistry, 3, 612Cf. Cain, Intermediate Products (2d Ed.), 195


Dye Derived from 1:3-Naphthylene-diamine-6-sulfonic Acid


458

Oidinary Name andClass of Dye

TRISAZO DYECarbon Black



Used and Notes

1:3-Naphthylene-dia-mine-6-sulf onic Acid(2 mols)

p-Nitro-aniline-0-sul-fonic Acid

l-Naphthylamine-6- or7-sulfonic Acid


D

1:4-Naphthylene-diamine-2-sulfonic Acid

1:4-Diamino-2-naphthaIene-sulfonic Acid (C. A. nomen.)

NH2

FORMATION.—^By reduction of the azo derivatives of l-naphthylamine-2-sulf onic acid

LITERATXJKE.—Cf. Thorpe, Die. Chemistry, 3, 611, 612

Dyes Derived from 1:4-Naphthylene-diamine-2-sulfonic Acid


433

434

461


DISAZO DYESCoomassie Black B

Coomassie NavyBlue

TRTSAZO DYECoomassie Union

Black


Manufacture

I '20:— 42,357


RAcid£-Naphthylamine

RAcidjS-Naphthol

Gamma Acidm~Phenylene- (or Toly-

lene-)diamine orResorcinol (2 mols)


A

A

D


1:4-Naphthylene-diamine-6-sulf onic Acid

5: 8-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)(Acetyl-compound used)

411

HO3S= Ci0H10N2O3S =

NH2

FORMATION.—A mixture of l-naphthylamine-6-(ancJ 7-)sulfonic acids(Cleve's Acids) is acetylated with glacial acetic acid, the excess ofacetic acid distilled off, and the acetylated acids dissolved in 5 partsof sulfuric acid. These acids are nitrated with mixed acid contain-ing 43 per cent nitric acid, cooled, diluted with ice and water, andsalted out with about 2 parts of salt. The sodium l-acetamido-4-nitro-6-(and 7-)sulfonates are now reduced hot with iron and someacetic acid. The acetyl-compound is isolated and used as such,the acetyl-group being split off after coupling


Dyes Derived from 1:4-Naphthylene-diamine-6-sulfonic Acid

SchultsNumberfor Dye

273

274


DISAZO DYEDiaminogen Blue BB

Diandnogen B


Manufacture

I '14:— 8,308M'17:— ?I '20:— 5,936

I '14:—313,629I '20:— 18,120


a-NaphthylamineSchaeffer's Acid

a-NaphthylamineGamma Acid


D

D

2:7-Naphthylene-diamine-sulfonic Acid

2: 7-Diamino-naphthalene-sulfonic Acid (C. A. nomen.)

=C10H10N2O3S =


FORMATION.—Probably by first sulfonating the 2: 7-dihydroxy-naphtha-lene and then by action of ammonia on the 2: 7-dihydroxy-naphtha-lene-sulfonic acid

LITERATURE.—Ger. Pat. 79780, 80070; Frdl. 4, 948, 949Cf. Thorpe, Die. Chemistry, 3, 610, 611, 650

Dye Derived from 2


330


DISAZO DYEZambesi Brown G

: 7-Naphthylene-diamine-sulfonic Acid


Manufacture

I '14:— 4,028I '20:— 1,104


BenzidineGamma acid


D

o-Naplithylene-diamine-£-sulfonic Acid

1:2-Naphthylene-diamine-6-sulf onic Acid (not consideredherein)

o-Napthylene-diamine-7-sulf onic Acid

1:2-Naphthylene-diamine-5~sulfonic Acid (not consideredherein)

o-NaphthyIene-diamine-5-sulfonic Acid

l:2-Naphthylene-diamine-7-sulfonic Acid (not consideredherein)

a-Naphthyl-glycine

iV-(l-Naphthyl)-fiflycine (C. A. nomen.)

NH.CHoCOOH

FORMATION.—From a-naphthylamine by reaction with chloro-aceticacid

LITERATURE.—Lange, Zwischenprodukte, #2264Ger. Pat. 79861 of 1893


Dyes Derived from a-Naphthyl-glycine

413

SchultzNumbefor Dye

309

310


DISAZO DYESGlycine Red

Glycine Corinth



Used and Notes


Benzidenea-Naphthyl-glycine

(2 mols)


D

D

/3-Naphthyl-sulfuric Acid

See, 2-Naphthol-l-sulfonic Acid


l-Naphthol-4-sulfonic Acid (C A. nomen.)

NWAcid

a-Naphthol~sulfonic Acid NW

OH

STATISTICS.—Manufactured '18:—340,074 lbs.Manufactured '19:—344,449 lbs.Manufactured '20:—561,929 lbs.

FORMATION.—From the sodium salt of naphthionic acid by hydrolyzingthe amino group

LITERATUEB.—Cain, Intermediate Products (2d Ed.), 217Thorpe, Die. Chemistry, 3, 617Lange, Zwischenprodukte, #2415-2421


Dyes Derived from Nevile-Winther's Acid


77

94

104

163

176

194

195

224

233

253


MONOAZO DYESAzo Coccine 2R

Azo Eosine

Benzoyl Pink

Azo Rubine

Double Scarlet SScarlet 2R

Rosophenine 10BTMazine Red R

Rosophenine SG

DISAZO DYESCloth Red G

Cloth Red B

OrseUline BB


Manufacture

I 14:— 1,001M'18:— ?M19:— ?

I '14:—230,763M17:—197,621M18:—79,779M19:—187,264I '20:— 1,102M '20:^470,949

I 14:— 10,182M17:— ?I '20:— 1,653

r 14:— 3,077M19:— ?M'20:— ?

M18:— ?M19:— ?M'20:— 19,639

I 14:— 401M19:— ?M'20:— ?

I 14:— 1,962M18:— ?M19:— ?M'20:— ?


Xylidine

o-Anisidine

Benzoyl-o-tolidine

Naphthionic Acid

Broenner's Acid

Dehydrothio-p-tolui-dine-sulfonic Acid

Primuline

Amino-azo-benzene

Amino-azo-toluene

Amino-azo-toluene-siil-fonic Acid


A

A

D

A

A

D

D

A

M

A


Dyes Derived from Nevile Winther's Acid (continued)

415




Diamond Black F

Violet Black

Azo AlizarinBordeaux W

Congo Corinth

Anthracene Red

Congo Corinth B

Azo Blue

Dianil Blue 2RBenzo New Blue 2B

Oxamine Blue 4R


Manufacture

I '14:—462,306M'17:— ?M'18:— ?M'19:—222,938I '20:— 2,226M 320:— ?

I '14:— 44,157M'17:-M'18:-M'19:-M'20:-

-137,704-242,503

I '14:-M'19:-I '20:-M'20:-

3,873

104

I '14:— 2,196M'19:— ?

I '14:—M'19:—M'20:—

498

I '14:— 14,434

I '14:— 573M'20:— ?


a-NaphthylamineAmino-saHcylic Acid

a-Naphthylaminep-Phenylene-diamine

or Amino-acet-anilide

Salicylic Acidp-Phenylene-diamine


o-Nitro-benzidineSalicylic Acid



(2 mols)

TolidineChromotropic Acid

TolidineJ Acid


Dyes Derived from Nevile-Winther's Acid (continued)


386

396

397

401

407

410

412

421

427

428

Ordinary Name, andClass of Dye



Indazurine RM

Direct Blue R

Diamine Blue 3R

Azo Violet

Benzoazurine G

Congo Blue 2B

Oxamine Blue B

Indazurine GM

Direct Blue B


Manufacture

I '14:— 1,740M '17:— ?M '18:— ?M '19:— 92,214I '20:— 4,520M '20:— 90,147

M'17:— ?

I '14:— 78,699M'18:— ?M '19:—150,589I '20:— 287M'20:—237,328

I '14:— 35,891I '20:— 13

I '14:— 21,421M'17:— 14,823M'18:— ?I '20:— 7,055


TolidineH Acid

Tolidine1:7-Dihydroxy-2-naph-


Tolidine1:7-Dihydroxy-6-naph-


Ethoxy-benzidineNevile-Winther's Acid

(2 mols)

DianisidineNaphthionic Acid


(2 mob)

DianisidineR Acid

Dianisidinel-Ainino-5-naphthol-7-

sulf onic Acid






D

D

D

D

D

D

D

D

D

D


Dyes Derived from Nevile-Winther's Acid (continued)

417





Used and Notes


447

450

459

483

484

TRISAZO DYESBenzo Gray S

Benzo Black Blue R

Benzo Black Blue G

I '14:— 802

St. Denis RedRosophenine 4B

Milling Scarlet B

I '14:-I '20:-

1,496550

BenzidineSalicylic Acida-Naphthylamino

Tolidinea-NaphthylamineNevile-Winther's Acid

(2 mols)

B enzidine-disulf onicAcid

a-NaphthylamineNevile-Winther's Acid

(2 mols)

Diamino-azoxy-tolucneNevile-Winthcr's Acid

(2 mols)

Diamino-azoxy-tolucncR Acid

D

D

D

D

Nigrotic Acid


Nigrotinic Acid


N i t r o - l : 2 : 4 A c i d

See, l-Amino-8-nitro-2-naphthol-4-sulfonic Acid

j^-Nitro-acetanilide

N H . C O C H 3

N O ,


STATISTICS.—Manufactured '17:— ?Manufactured '18:—541,552 lbs.Manufactured '19:—669,658 lbs.Manufactured '20:—569,728 lbs.

FORMATION.—Aniline is acetylated to acetanilide, which is dissolved i nsulfuric acid and then nitrated with mixed acid in the cold


USES.—For the manufacture of p-nitro-aniline and acetyl-p-phenylene-diamine (p-amino-acetanilide)

Nitro-alizarin, crude

Ci4H7NO6=285

FORMATION.—Alizarin is dissolved in sulfuric acid and nitrated

Dye Derived from Nitro-alizarin, crude


798



Alizarin Maroon W


Manufacture

I '20:— 2,014


[Reduction]


M

3-Nitro-alizarin (C. A. nornen.)

j3-Nitro-alizarin

1:2-Dihydroxy-3-nitro-anthraquinone

STATISTICS.—liefer to the dye, Alizarin Orange, which is 3-nitro-alizarin

FORMATION.—From alizarin by nitration of its boric ester

LITERATURE.—Schultz, Farbstofftabellen (1914), #779Lange, Zwischenprodukte, #3341Georgievics and Grandmougin, Dye Chemistry, 268


Dyes Derived from 3-Nitro-alizarin





Used and Notes


779

803

804

808

809

ANTHRAQUINONB ANDALLIED DYES

Alizarin Orange

Alizarin Blue WX

Alizarin Blue S

Alizarin Green X

Alizarin IndigoBlueS

— 14,239— ?— 500

M'20:— ?

I '14:M'19:

I '14M'19I '20

I '14I '20

I '14I '20

—319,394— ?— 5,585

—117,850— 43,679

—135,191—- 4,254

[This is 3-nilro-alizarin]

3-Ami no-alizarin[Glyccrol]

3-Amino-alizarin[Glyccrol]

3-Ami no-alizarin[Glyccrol; Oxidation]

3-Amino-alizarin[Glyccrol; Oxidation]

M

M

M

M

M

4-Nitro-alizarin (C. A. nomen.)

a-Nitro-alizarin

•OCX O H

0 H =

NO 2

F O R M A T I O N . — T h i s compound is made by ni t ra t ion of alizarin in weak

oleum solution, or by nitrat ion of t he methyl , benzoyl, or arsenic

ester of alizarin

LITERATURE.—Georgiev ics and Grandmougin, D y e Chemistry , 2G8

Schultz, Farbstofftabellen (1914), #779


Dyes Derived from 4-Nitro-alizarin


797

805



Alizarin Garnet R

Alizarin Green S


Manufacture

I '14:— 720

I '14:-- 15,885


[Reduction]

Nitro-benzene[Reduction; Glycerol]


M

M

a-Nitro-alizarinSee, 4-Nitro-alizarin

0-Nitro-alizarinSee, 3-Nitro-alizarin

6-Nitro-m-amino-benzene-sulfonic AcidSee, 6-Nitrometanilic Acid (C A. nomen.)

o-Nitro-o-amino-^-cresolSee, 2-Amino-6-nitro-p-cresol (C A. nomen. OH = 1)

2-Nitro-6-amino-l-phenol-4:-sulfonic AcidSee, 2-Amino-6-nitro-l-phenol-4-sulfonic Acid

6-Nitro-2-amino-l-phenol-4:-sulfonic AcidSee, 2-Amino-6-nitro-l-phenol-4-sulfonic Acid

m-Nitro-aniline

NH2

STATISTICS.—^Imported j14:— 3,527 lbs.Manufactured 17:—228,279 lbs.Manufactured 18:—630,802 lbs.Manufactured 19:— 68,600 lbs.Manufactured ;20:— ?


FORMATION.—Benzene is nitrated with mixed acid to dinitro-benzene,

and this body is reduced with sodium sulfide


Lange, Zwischenprodukte, #537, 542

Dyes Derived from m-Nitro-aniline


46

47

48

49

222

408


MONOAZO DYESra-Nitraniline Orange

Orange III

Alizarin Yellow GG

Prague AlizarinYellow G

DISAZO DYESJanus Yellow G

Azophor Black S

Statistics ofImpoi t and

Manufacture

M'18:— ?

I ' 14:—144,761MJ17:—

1,452,622M'18:—

2,233,208M'19:—163,170M'20:—211,580

I '14:— 2,250I '20:— 758


0-Naphthol

R Acid

Salicylic Acid

0-Resorcylic Acid

Resorcinolm-Amino-phenyl-tri-

methyl-ammoniumChloride

m-Nitro-aniline (? mols)Dianisidine


MF

A

M

M

B

D

^-Nitro-aniline

NO2







FORMATION.—(1) Aniline is acetylated to acetanilide, which is t h e n

nitrated with mixed acid to p-nitro-acetanilide. T h e la t ter c o m -

pound is hydrolyzed by boiling with caustic soda to p-ni tro-ani l ine.

(2) p-Chloro-nitro-benzene is heated with ammonia under p r e s s u r e

LITERATURE.—Cain , Intermediate Products (2d Ed . ) , 51

Lange, Zwischenprodukte, #533, 538-541

Dyes Derived from ^-Nitro-aniline





Used and Notes


50

51

52

53

54

55

56

MONOAZO DYESAzo Cardinal G

NitrophenineThiazol Yellow R

Archil Substitute V

Archil Substitute3VN

Apollo Red B

Brilliant Archil C

Paranitraniline Red

M'18:— ?

I '14M'20

:— 423:— ?

:— 904

I '14:-I '20:

401100


Dehydrothio-toluidine-sulf onic Acid

Naphthionic Acid

Laurent's Acid

l-Naphthylainiiie-4: 6-and -4: 7-disulfordcAcids

1:8-Naplithyleiie-dia-mine-3:6-disulfonicAcid

D

A

A

A

I '14M'17M'18M J19JVT20

:— 49,847: ?

:— ?

:— ?

M F


Dyes Derived from jfr-Nitro-aniline (continued)





Used and Notes

57

58

61

63

215

216

217


Chromotrope 2B

Alizarin Yellow R

Victoria Violet

I '14:M'18:-M'19:-M'20:-

7,970???

Azo Acid Blue B


Domingo BlueBlack B

Naphthol Blue BlackAgalma Black 10B

I '14:— 97,059M' 17:—215,468M'18:—385,910M '19:—130,424I '20:— 860M'20:— 83,334

I '14:— 52,365M'17:— ?M;18:— ?M'19:—105,086I '20:— 2,182M'20:— ?

I '14:— 45,09SI '20:— 4,4S5

Chromotropio Acid

Salicylic Acid

Chromotropic Acid[RcducUon]

I '14:- 2,653

I '14:—431,027M'17:—620,218M'18:—

1,158,309M'19:—

1,877,860I '20:— 840M'20:—

2,608,864

1:8-Dihydroxy-uaph-thalcnc-4-sulfonicAcid

[Methylation]

Anilinel-Amino-8-napliil iol-

4: 6-disulfonic Acid

Anilinel-Amino-8-naphtl lol-

3:5-disulfonic Acid

AnilineH Acid


Dyes Derived from j>-Nitro-aniline (continued)


218

221

245

408

473

474

475

719


DISAZO DYES

{continued)NigrophorBASF

Anthracene AcidBrown G

Nyanza Black B

Azophor Blue DAzophor Black S

TRISAZO DYESDiamine Black HW



SULFUR DYEThional Black


Manufacture

MJ17:— ?M'18:— ?I '20:— 225

I '20:— 342

I '14:— 77,100M'17:— ?M '18:—295,147M'19:—305,854I '20:— 2,460M'20:-^20,138

I '14:— 7,329M'17:— ?M'18:— 29,118M'19:—136,638I '20:— 1,332M'20:— 53,292

I '14:— 16,865


2: 5»Dichloro-anilinel-Amino-8-naphthol-5-

sulf onic Acid

Sulfanilic AcidSalicylic Acid

a-NaphthylamineGamma Acid[p-Nitro-aniline reduced

after coupling]

Dianisidine

BenzidineGamma AcidHAcid

BenzidinePhenolHAcid

BenzidineSalicylic AcidHAcid

o-Nitro-phenol[Na*S plus S]

oro-Nitro-phenol (2 mols)Aniline[Na^S plus S]


M F

ACr

D

D

D

D

D

S


2-Nitro-aniline-4-sulfonic Acid (NH2=1)

See, 4~Amino-3-nitro-benzene-sulfonic Acid (C. A. nomen.)

4-Nitro-aniline-2-sulfonic Acid (NH2=1)

See, 2-Amino-5-nitro-benzene-sulfonic Acid ( C A. nomen.SOiH-1)

4-Nitro-aniline-3-sulfonic Acid

See, 6-Nitro-metanilic Acid (C. A. nomen.)

o-Nitro-aniline-j&-sulfonic Acid (NH2=1)

See, 4-Amino-3-nitro-benzene-sulfonic Acid (C A, nomen.)

^-Nitro-aniline-o-sulfonic Acid (NH2=1)

See, 2-Amino-5-nitro-benzene-sulfonic Acid ( C A. nomenSOzH-1)

4-Nitro-o-anisidine (C. A. nomen. NIh=l)

p-Nitro-o-anisidine

NH 2

/ N 0 C H 3

NO2

_ C 7 H 8 N 2 O 3 = 168

FORMATION.—o-Anisidine is acetylated, then nitrated, and saponifiedby heating with 70 per cent sulfuric acid. The resulting mixtureof 4- and 5-nitro-o-anisidines, is separated by crystallization from40 per cent sulfuric acid


Dye Derived from 4-Nitro-o-anisidine


98


MONOAZO DYESNaphthol PinkNitrosamine

PinkBX


Manufacture

I '14:— 99


0-Naphtkol

DyeAppli-cationChaw

MF


5-Nitro-o-anisidine (C. A. nomen. NH2=1)

m-Nitro-0-anisidine

2

OOCH3O s N l ^ :C7H8N2O3 =

FORMATION.—o-Anisidine is acetylated, then nitrated, and saponifiedby heating with 70 per cent sulfuric acid. The resulting mixtureof 4- and 5-nitro-o-anisidines is separated by crystallization from40 per cent sulfuric acid


Dye Derived from 5-Nitro-o-anisidine


99


MONOAZO DYETuscaline Orange G



Used and Notes

0-Naphthol


CLMF

m-Nitro-o-anisidine (NH%=1)

See, 5-Nitro-o-anisidine (C. A. nomen.

/>-Nitro-o-anisidine

See, 4-Nitro-o-anisidine (C. A. nomen. NH2-I)

o-Nitro-anisole

OCH3

STATISTICS.—Manufactured 718:— ?Manufactured '19:— ?Manufactured '20:—273,327 lbs.

FORMATION.—(1) From o-nitro-phenol by methylation. (2) Fromo-chloro-nitro-benzene by action of methanol (methyl alcohol) andcaustic


LITERATURE.—Cain, Intermediate Products (2d Ed.), 96Cf. Lange, Zwischenprodukte, #578

USES.—For preparation of dianisidine

l-Nitro-anthraquinone-6-sulfonic Acid

5-Nitro-2-anthraquinone~sulfonic Acid (C. A. nomen.)

, . . N0 2<xFORMATION.—When anthraquinone-2-sulfonate of sodium is nitratedwith a mixture of equal parts of "fuming" nitric acid and sulfuricacid (66°) there arises a mixture of the a-nitro and /3-nitro-an-thraquinone-sulfonic acid which can be separated by dilution,whereupon the a-acid is precipitated. The a-acid is undoubtedlyl-nitro-anthraquinone-6-sulfonic acidLITERATURE.—Claus, Ber. 15, 1515 (1882)Cf. Lange, Zwischenprodukte, #3160, 3263Dye Derived from l-Nitro-anthraquinone-6-sulfonic AcidSchultzNumberfor Dye864

Ordinary Name andClass of DyeANTHKAQUINONE ANDALLIED DYESAnthraquinoneGreen GXStatistics ofImport andManufactureI '14:—- 1,709I '20:— 2,531

Other IntermediatesUsed and NotesAniline[Halogonation]p-Toluidine

DyeAppli-cationClassACr

5-Nitro-2-anthraquinone-sulfonic Acid (C. A. nomen.)

See, l-Nitro-anthraquinone-6-sulfonic Acid

m-Nitro-&enzaldehyde

CHO

= C 7 H 6 N O 3 = 1 5 1


STATISTICS.—Imported ' 14:—very smallManufactured ; 17:— ?Manufactured '18:— ?Manufactured '20:— ?

FOKMATION.—From benzaldehyde by nitration at not above 30-35'(Twenty per cent o-nitro-derivative also formed)

LITEKATURE.—Cain, Intermediate Products (2d Ed.), 144Lange, Zwischenprodukte, #296

Dyes Derived from m-Nitro-benzaldehyde





Used and Notes

DyeApplicatioiClasi

510

523

543

544

545


Azo Green

Fast Green

Patent Blue V

Cyanine B

Patent Blue A

I 14:— 14,347I '20:— 10,461

I 14:—196,228M17:— ?M18:— ?I '20:— 36,420

I 14:— 8,398I '20:— 24

I 14:—- 63,744M18:— ?I '20:— 44,801


Salicylic Acid[Oxidation]


Benzyl Chloride (2 mols)[Sulfonation, Oxidation]

Diethyl-aniline (2 mols)[Sulfonation, Oxidation]

Diethyl-aniline (2 mols)[Sulfonation, Oxidation]



M

A

A

o-Nitro-fcenzaldehyde

HCO

Q H O , =



FOKMATION.—When benzaldehyde is nitrated, there results about 20per cent of the o-nitro- and about 80 per cent of the m-nitro-derivative. The nitration product is poured into water, and theoily o-derivative is separated from the solid w-compound bypressing

LITERATURE.—Cain, Intermediate Products (2d Ed.), 143Lange, Zwischenprodukte, 22, 37, 38, 40, 181, 254, 275,

278, 289-302


875

Dye Derived


INDIGO GROUP DYEIndigo Salt T

from o-Nitro-benzaldehyde



Used and Notes

[Acetone; NaOH]


Print-ing

^-Nitro-benzaldehyde

CHO

= C7H5NO3 =


FORMATION.—From p-nitro-toluene by oxidation

LITERATURE.—Lange, Zwischenprodukte, #275, 303-312

Dye Derived from ^-Nitro-benzaldehyde


511





Manufacture

I '14:— 65,026M'18:— ?M'19:— ?M'20:— ?


Aniline (Sulfate)(2 mols)

[Zinc chloride; ferrouschloride]


B


Nitro-benzene

Myrbane Oil

NO2

STATISTICS.—Imported '14:— 1,502,205 lbs.

Manufactured 17:—42,975,655 lbs.Manufactured 18:—38,250,332 lbs.Manufactured 19:-^2,544,017 lbs.Manufactured '20:—53,244,008 lbs.

FOEMATION.—From benzene by nitration with mixed acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 20Lange, Zwischenprodukte, #264r-268

Dyes Derived from Nitro-benzene


511

512



ParafuchsineParana agenta

MagentaFuchsine


Manufacture

I '14:— 65,026M'18:— ?M19:— ?M'20:— ?

I '14:— 87,102M'17:— 17,739M'18:— 71,675M'19:—155,830I '20:— 189M'20 :—284,285


Aniline (2 mols)p-Toluidine

orp :p/-Diamino-dipheiiyl-

methane orAnhydro-formalde-hyde-aniline

Aniline and anilinB hy-drochloride

[Ferric chloride]

Anilineo-Toluidinep-Toluidine[Iron and zinc chloride]


B

B


Dyes Derived from Nitro-benzene (continued)

431


698

700

718

805


AZINE DYESNigrosine, Spirit

Soluble

Nigrosine, WaterSoluble

SULFUR DYESt. Denis Black


Alizarin Green S


Manufacture

I '14:—186,595M ' 17:—-302,706M'18:—-314,151M'19:—346,167M'20:—919,242

I '14:—398,112M'17:—

1,968,458M'18:—

1,191,343M'19:—

1,660,149I '20:— 501

M'20:—2,743,021

I '14:— 15,885


Aniline (excess)[Iron]

Aniline (excess)[Iron, Sulfonation]

p-Phenyleno-diaminePhenol[fcCl,, S, N*S]

4-Amino-alizarin.[Reduction; glycorol]

DyeAppli-cationCla83

ss

A

S

M

3-Nitro-benzidine (C. A. nomen.

See, o-Nitro-fcenzidine

o-Nitro-benzidine

3-Nitro-&enjzidine (C. A. nomen.

N0 2

= C l * H n N 8 ° 2 — 2 2 9

STATISTICS.—^Manufactured ' 19:— ?

FORMATION.—By nitration of benzidine in sulfuric acid solution


LITERATURE.—Green, Organic Coloring Matters (1908), 41Eng. Pat. 13475 of 1892Lange, Zwischenprodukte, #1220

Dye Derived from o-Nitro-benzidine




ManufactureOther Intermediate*

Used and Notes

355DISAZO DYE

Anthracene Red I '14:—M'19:—I '20:—M'20:—

3,873

104

Salicylic AcidNevile-Winther's Avul

^-Nitro-benzyl Chloride

a-Chloro-p-nitro-toluene (C. A. nomen.)

CH2C1

= C7H6C1NO2 = 171.5

NO2

FORMATION.—(1) By passing chlorine into p-nitro-toluene185-190°. (2) By dropping benzyl chloride intoacid cooled to -15° C.

LITERATURE.—Ann. 185, 271

Ber. 6, 1056Cf. Lange, Zwischenprodukte, #250

Dye Derived from ^-Nitro-benzyl Chloride


734


SULFUR DYEPyrogene Yellow


Manufacture

I '14:— 18,515I '20:— 2,701


p-Ammo-phenol[S+Na^S]


o- and ^-Nitro-chloro-benzenes

See, o- and p-Chloro-nitro-benzenes (C A. nomen.)

Nitro-diphenylamine-sulfonic Acid

433

FORMATION.—Diphenylamine in sulfuric acid solution is heated with

20 per cent oleum at 80-100°, and is then nitrated with nitric

acid at 50-80°, resulting in formation of " nitrated diphenylamine-

sulfonic acid"

LITERATURE.—Lange, Die Schwefel-farbstoffe, 145

Dye Derived from Nitro-diphenylamine-sulfonic Acid


737


SULFUR DYECotton BrownSulfine Brown


Manufacture

I '14:— 2,206


[S+Na*S]


S

3-Nitro-flavopurpurin (C. A. nomen.)

0-Nitro-flavopurpurin

3-Nitro-l: 2: 6-trihydroxy-anthraquinone

0 HCO

FORMATION.—By nitration of flavopurpurin

LITERATURE.—Ger. Pat. 54,624, Frdl. 2, 122


Dyes Derived from 3-Nitro-flavopurpurin


806

807



Alizarin Black P

Alizarin Black S


Manufacture

I '14:—229,500

I '14:—259,991


[Glycerol]

[Glycerol]


M

M

jS-Nitro-flavopurpurin

See, 3-Nitro-flavopurpurin

6-Nitro-metanilic Acid (C. A. nomen.)

4-Nitro-aniline-3-sulf onic Acid

6-Nitro-77i-amino-benzene-sulfonic Acid

SO3H

= C6H6N2O5S = $

FORMATION.—Sodium metanilate is acetylated, dissolved in sulfuric acidand nitrated with mixed acid


USES.—For preparation of mtro-?ra-phenylene-diamine

Nitro-phenol crude

OH OH

and =C6H5NO3 =

N0 2

STATISTICS.—Manufactured '17:— ?Manufactured'18:— ?Manufactured '19:— ?

FORMATION.—From phenol by nitration with nitric acid

ain, Intermediate Products (2d Ed.), I l l


Dyes Derived from Nitro-phenol crude

435


698

700


AZINE DYESNigrosine, Spirit

Soluble

Nigrosine, WaterSoluble


Manufacture

I 14:—186,595M'17:—362,706M18:—314,151M' 19:—346,167M'20:—919,242

I '14:—398,112M'17:—

1,968,458M'18:—

1,191,343M19:—

1,660,149I '20:— 501M'20:—

2,743,021


Aniline (excess)

Aniline (excess)[Sulfonation]


ss

A

o-Nitro-^henol

OH

STATISTICS.—Imported '14:—very smallManufactured '17:— 58,128 lbs.Manufactured '18:—143,277 lbs.Manufactured '19:— 18,373 lbs.Manufactured '20:— ?

FORMATION.—(1) Phenol is nitrated with nitric acid, resulting in anoily mixture of o- and p-nitro-phenol. The o-derivative is separatedby distillation and purified by steam distillation. (2) o-Chloro-nitro-benzene is hydrolyzed to the o-nitro-phenol by boiling withcaustic soda

LITERATURE.—Cain, Intermediate Products (2d Ed.), I l lLange, Zwischenprodukte, #574-577


Dye Derived from o-Nitro-phenol


719


SULFUR DYEThional Black


Manufacture

I >14:— 16,865


p-(o- or m-)Nitro-aniline

[N^S+S]or

p-(o- or ??i-)Nitro-aniline

Anilineo-Nitro-phenol (2 mols)[Na^S+S]


S

STATISTICS.—Imported '14:— 4,780 lbs.Manufactured '17:—413,216 lbs.Manufactured 18:—192,259 lbs.Manufactured '19*— 76,191 lbs.Manufactured '20*—125,693 lbs.

FORMATION.—(1) Phenol is nitrated with nitric acid to an oily mixtureof o- and p-nitro phenol, from which the o-isomer is removed bydistillation. The residue upon being extracted with hot wateryields the p-isomer, which crystallizes out from the aqueous extractupon cooling. (2) p-Chloro-nitro-benzene is hydrolyzed to thep-nitro-phenol by boiling with caustic soda

LITEBATDBE.—Cain, Intermediate Products (2d Ed.;, I l l



Dye Derived from />-Nitro-phenol

437


709


SULFUR DYEItalian Green



Used and Notes

[Sulfur, etc.]


S

4-Nitro-m-phenylene-diamine

NH2

NH2 =C6H7N3O2 =

FORMATION.—5-Amino-2-nitro-benzene-sulfonic Acid (4-nitro-aniline-3-sulfonic acid) is heated in an autoclave with 25 per cent ammoniawater for three hours at 170-180°

LITERATURE.—Cain, Intermediate Products (2d Ed.), 86Dyes Derived from 4-Nitro-m-phenylene-diamine




Manufacture0 fh er hi tcrmediates

Used avd Notes


191

286

306

314

360

MONOAZO DYEPyramine Yellow R

DISAZO DYESToluylcne Yellow

Pyramine Orange 3G

Pyramine Orange 2R

Pyramine Orange R

I '14:-I '20:

I '14:-

I '14:I '20:-

5,727100

5,485

7,863396

I '14:— 2,789

I '14:-I '20:-

21,3297,821

Primulinc-sulfonic Acid

3:5-Diamino-p-toluene-sulfonic Acid

Nitro-m-plienylene-diamine (2 mols)

Bcnziclincm-Phcnylcnc-diamine-

disulfonic Acid

BenzidincAmino-R Acid


Nitro-m-phenylene-diamine (2 mols)

D

D

D

D


(o-Nitro-phenyl-mercapto)-acetic Acid (C. A. nomen.)

See, o-Nitro-phenyl-thioglycolic Acid

o-Nitro-phenyl-thioglycolic Acid

(o-Nitro-phenyl-mercapto)-acetic Acid (C A. nomen.)

S.CH2.COOH

FOKMATION.—o-Chloro-nitro-benzene in hot alcoholic solution is treatedwith thioglycolic acid and caustic soda solution, and then boiledfor two hours under a reflux condenser


Dye Derived from o-Nitro-phenyl-thioglycolic Acid

SchultsNumberfor Dye

921


INDIGO GROUP DYESHelindone Gray 2B



Used and Notes

0-Nitro-pb.enyl-thio-glycolic Acid (2 mols)

[Chloro-sulfonic Acid;Reduction]


V

Nitroso-diethyl-m-amino-phenol

See, 5-Diethylamino-2-nitroso-phenol (C. A. nomen.)

^-Nitroso-diethyl-aniline

iV:iV-Diethyl-p-rdtroso-aniline (C. A. nomen.)

=C10H14N2O = 178



FORMATION.—From diethyl-aniline by action of nitrous acid


Dyes Derived from ^-Nitroso-diethyl-aniline

430


639

641

646


OXAZINE DYESGallanilic Violet R, B

Coreine RRCoelestine Blue B

Coreine AR


I '20:— 100

I '14:— 1,320I '20:- 44


Gallanilide

Gallamide

GallamideAniline[Sulfonation]

or[Coreine RR, Aniline,

Sulfonation]


M

M

M

Nitroso-dimethyl-m-amino-^-cresol

See, 5-Dimethylamino-2-nitroso-p~crcsol (C. A. nomen.)

j)-Nitroso-dimethyl~aniline

i\T:iV-Dimethyl-p-nitroso-aniline (C. A. nomen.)

N(CH3)2

STATISTICS.—Manufactured '17:— 96,166 lbs.Manufactured '18:—851,821 lbs.Manufactured J19:—592,663 lbs.Manufactured '20:—155,986 lbs.

FORMATION.—From dimethyl-aniline by action of nitrous acid upon acold solution of the hydrochloride



Dyes Derived from jfr-Nitroso-dimethyl-aniline


Ordinary "Same andClass of Dye

619

620

622

623

624

626

627

INDOPHENOL

Indophenol

OXAZINE ANDTHIAZIXE DYES

Capri Blue G O N

Delphine Blue B

Pyrogallol-Cyanine-Sulfonic Acids

Modern Violet X

Galloeyanine

Modern Cyanine


Manufacture

M'17:— ?M'18:— ?M'19:—126,61M '20:— ?

:— 128

M'17:— ?M'lS:— ?M719.— 43,827MJ20:— 76,719I '20:— 29,643

I '20:— 5,688

I '14:— 78,25iM'17:— ?M'18:~435,460M'19:—365,243I '20:— 12,414M'20:— 70,169


a-Naplitliol

3-Diethylamino-p-cresol (OH=*1)

Gallic AcidAniline[Sulfonation]

or[Aniline on Galloeya-

nine, Sulfonation]

PyrogaUol-5-sulfonicAcid

Gallic Acid[CO2 removed by heat]

or[Galloeyanine heated]

Gallic Acid

GallamideDimethyl-p-phenylene-

diamine[Reduction]

or"Galloeyanine; Di-

methyl-p-phenylene-diamine; Reduction]


Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)

441




ManufactureOther Intermediate

Used and Notes


628

629

630

631

632

633

634

635

636

OXAZINB ANDTHIAZINB DYES

(continued)Gallocyanine MS

Gallogreen DHModern Blue

Cyanazurine

Chromocyanine Y

Ultraviolet LGP

Indalizarino R

Indalizarine Green.

Blue 1900 TCModern Violet

Prune

M'18:-M'19:-I '20:-

M '20:-

??

1,289?

I '14:—• 4,308

I '20:— 551

I '20:— 1,933

I '14:I '20:

3,1974,418


or[Leuco-gallocyardne sul-

fonated; oxidized]

Gallic Acid[Formaldehyde]

or[Formaldehyde on

Gallocyanine]

GallamideAniline[Reduction]


or[Sulfite on Gallo-

cyanine]

Gallic Acid (2 mols)Nitroso-dimethyl-ani-

line (2 mols)


Gallic Acid[Sulfonation; Nitration

or[Nitration of Indaliza-

rine]

Gallic Acid[Reduction]








Used and Notes

637

638

639

640

642

643

644

645

647

OXAZINE -ANDTHIAZINB DYES

(continued)Gallamine Blue

Amido GallamineBlue

Gallanilic Violet R , B

Modern Azurine DH

Phenocyanine TC

Phenocyanine TV

I '14:— 2,756I '20:— 16,446

I '2 :— 100

I '20:— 4,740

M'17:— ?I '20:— 1,543

Ultracyanine B

Gallazine A

Nitroso Blue MRResorcine Blue

Gallamide

Gallamide[Ammonia; Reduction]

Gallanilide


Aniline

Gallic AcidResorcinol

Gallic AcidResorcinol[Sulfonation]

or[Phenocyanine sulfo-

nated]

Gallic AcidResorcinol

or[Gallocyanine;

Resorcinol]

Gallic AcidSchaeffer's Acid[Oxidation]

or[Gallocyanine,

Schaeffer's, Oxidation]

Resorcinol



443


649

650

651

652

655

658

659

660


OXAZINB ANDTHIAZINB DYES

(continued)New Blue RMeldola's BlueCotton Blue

New Blue B

New MethyleneBlue GG

New Fast Blue F

Muscarine

Fast Black

Methylene Blue

Methylene Green 0


Manufacture

I '14:— 32,509M'17:— ?MIS:— 22,613M'19:— ?I '20:— 5,240M'20:— ?

I '14:— 2,502

I '14:— 1,960I '20:— 2,883

I '14:—185,958M '17:—268,435M'18:—312,572M'19:—465,992I '20:— 2,053

M'20:—577,264

I '14:— 30,812M'18:— ?M'19:— 2,435I '20:— 1,047


/3-Naphthol

/3-NaphtholNitroso-dimethyl-

aniline (2 mols)

/3-Naphthol[Dimethyl-amine,

Oxidation]or

[Meldola's Blue, Di-methyl-amine, Oxida-tion]

0-NaphtholHydrol

or[Meldola's Blue, Hydrol]

2: 7-Dihydroxy-naph-thalene

m-Hydroxy-diphenyl-amine

Dimethyl-aniline[Naa&Os, etc.]

Dimethyl-aniline[Na2S2O3 etc.; Nitration]

or[Methylene Blue

nitrated]

DyoAppli-cationClass

B

B

B

B

B

B

B

B




661

670

676

677

678

681

682

684

685

689


OXAZINE ANDTHIAZINE DYES

(continued)Thionine Blue GO

AZINE DYESNeutral Red

Neutral Blue

Basle Blue B,

Fast NeutralViolet B

Methylene Gray 0New Fast Gray

Nigramine

Rhoduline Violet

Tannin Heliotrope

Indazine M

II

M

I

M

IMMMI

M

II

II


'14:-'20:-

'18:-

'14:-

'17:-

'14:-'17:-'18:-'19:-'20:-'20:-

'14:-'20:-

'14:-'20:-

- 18,618- 2,030

- ?

- 615

- ?

- 29,507?

- 16,746- 28,458

9- 31,620

- 2,75135

- 1,398249


Ethyl-methyl-aniline[Nas&Oa, etc.]

m-Tolylene-diamine[Oxidation]

i\^Phenyl-/5-naphthyl-amine

N: i\r-Ditolyl-2: 7-napht hyl ene-diamine

N: iV;-Diethyl-m-phenylene-diamine

[Boiling with alcohol]

Aniline

JV^PhenyW-m-toly-lene-diamine

oriV^Benzyl-JV^phenyW-

m-tolylene-diamine

Xylidine

Nitroso-dimethyl-ani-line (1 and 2 mols)

Diphenyl-m-phenylene-diancdne


B

B

B

B

B

B

B

B

B

B




691

692

703

704

705



MetaphenyleneBlueB

Naphthazine Blue

Rubramine

Indamine 3R

Indamine 6R


I '14:—

I '14:—I '20:—

50

6,2612,249

I '14:— 66,170I '20:— 9,681


N: N'-Di-o-tolyl-m-phcnylene-diamine

N:2V'-Di-2-naphthyl-?n-phenylene-diaminc

[Sulfonation]

o-Toluidinep-Toluidine

o-Toluidine

o-Toluidinep-Toluidine


B

A

B

B

B

^-Nitroso-ethyl-anilineiV-Ethyl-p-nitroso-aniline (C. A. nomen.)

NH.C2H5

FORMATION.—From ethyl-aniline by action of nitrous acid on the solu-tion in strong alcoholic hydrochloric acid

LITERATURE.—Cf. Lange, Zwischenprodukte, #529Dye Derived from ^-Nitroso-ethyl-aniline

ScttuitzNumberfor Dye

684


AZINE DYERhoduline Red B



Used and Notes

iV1-Phenyl-4-m-tolylene-diamine

oriV^Benzyl-iV^phenyl-

4-m-tolylene-diamine


B


^-Nitroso-ethyl-o-toluidine

JV-Ethyl-4-nitroso-o-foluidine (C. A. nomen. NHR=1)

NH.C2H5

/\CHZ =C9Hi2N2O =

NO

FORMATION.—From ethyl-o-toluidine in an alcoholic solution of hydro-chloric acid, by action of NaNO2 solution in the cold

LITERATURE.—Beilstein, Organische Chemie (3d aufl.), II, spl., 248Cf. Lange, Zwischenprodukte, #529

Dyes Derived from Nitroso-ethyl-o-toluidine


684

684


AZINE DYESRhoduline Red G

Brilliant RhodulineRed



Used and Notes

W-Phenyl-i-m-tolylene-diamine

ori^-Benzyl-iV^-phenyl-

4-m-tolylene-diamine

JV^-Ethyl-^^phenyl-^-m-tolylene-diamine


B

B

^-Nitroso-methyl-aniline

iV-Methyl-p-nitroso-aniline (C. A. nomen.)

NH.CHs

FORMATION.—^From methyl-aniline by action of nitrous acid on thesolution in strong alcoholic hydrochloric acid



Dye Derived from ^-Nitroso-methyl-aniline

447


625


OXAZINE DYEChrome Heliotrope



Used and Notes

Gallic Acid[Reduction]


M

l-Nitroso-2-naphthol (C. A. nomen.)

a-Nitroso-j3-naphthol

N . O HNO ||

STATISTICS.—Manufactured in 1918 and 1919, but in undisclosedquantities

FOBMATION.—From /3-naphthol by action of nitrous acidLITERATURE.—Cain , Intermediate Products (2d Ed.)j 216


Dyes Derived from l-Nitroso-2-naphthol


2

107

116

331


NITROSO DYEGambinc Y

MONOAZO DYESSulfamine Brown A

Sulfamine Brown B

DISAZO DYESAlkali Dark

Brown GV


Manufacture

I '14:— 132M 'IS:— ?M'19:— ?I '20:— 2,630M'20:— ?


[This is l-Nitroso-2-naphthol]

a-Naphthylamine

/?-Naplithylamine

BenzidineGamma Acid


M

M

M

D

U8 DYES CLASSIFIED BY INTERMEDIATES

l-Nitroso-2-naphthylamine-6-sulfonic Acid

6-Ammo-5-nitroso-2-naphthalene-sulfonic Acid (C A. nomen.)

NO

FORMATION.—One part of l-nitroso-2-naphthol-6-sulfonic acid (nitroso-Schaeffer's Acid) is heated with one part of 25 per cent ammoniafor three hours at 60°


Dye Derived from l-Nitroso-2-naphthylamine-6-sulfonic Acid


675


AZINE DYERosinduline G



Used and Notes

Aniline (2 mols)


A

^-Nitroso-^henol

OH

= C6H5NO2=123

NO

STATISTICS.—Imported J14:—very small amountManufactured '17:— ?Manufactured '18:— ?Manufactured '19:—155,273Manufactured '20:—167,855

FOBMATION.—From phenol by action of nitrous acid in the cold

LITERATURE.—Cain, Intermediate Products (2d Ed.), I l lLange, Zwischenprodukte, 573


Dye Derived from ^-Nitroso-phenol


748


SULFUR DYE

Hydron Blue


Manufacture

I '14 —296,723I '20.— 19,210

M'20:— ?

Oth< r hiU rmvthaU &Used and Nol(,s

Carbiizolo

449

DyeA impli-cationClfHH

4-Nitroso-resorcinol

O H

H = C 6 H 5 N O 3 = 1 3 9

N O

FORMATION.—Resorc inol is dissolved in alcohol, one molecule of caust icsoda added, and then gradually one molecule of isoamyl ni t r i te isintroduced with cooling

LITERATURE.—Bei l s te in , Organische Chemie (3d Ed . ) , II, 923

Dye Derived from 4-Nitroso-resorcinol


648


OXAZINE D Y EIris Blue

Statistic* ofImport and

ManufactureOther Int<tnudiali« ' A ppli-

Lhcd and Notts I (ationCUlHH

Rosoroinol[Bromination)

2-Nitro-m-folualdehyde (C. A. nomen.)

o-Nitro-tolylaldehyde

HCO

O o H . = '


FORMATION.—m-Tolylaldehyde is nitrated, and then the two isomeric

nitro-compounds separated by distillation under reduced pressure


Ger. Pat. 113,604 Frdl. 6, 128

Dye Derived from 2-Nitro-m-tolualdehyde

Schvltz Ordinary xame and Statistics ofImport and


Used and Notes


INDIGO GROUP DYESSS Indigo MLB/T I '14:— 10,730

I '20:— 8272-Nitro-m-tolualdehyde

(2 mols)[Acetone, NaOH]

o-Nitro-foIuene (C. A. nomen.)

0-Xitro-toluol

CH3

] i X 0 * =CrH 7 NO 2 =137



Manufactured J18:—1,240,499 lbs.



FORMATION.—Toluene is nitrated with mixed nitric and sulfuric acidsto a mixture of o- and p-nitro-toluenes. The separation is effectedby means of fractional distillation and freezing—the o-isomer beingdistilled off and the p-body separated as a solid by cooling thestill residue




Dyes Derived from o-Nitro-toluene


513



New Fuchsine 0


Manufacture

I '14:— 300M 'IS:— ?M'19:— ?M'20:— ?


Anhydro-formaldehyde-o-toluidine orDiamino-o-di-tolyl-methane

o-Toluidine


B

^-Nitro-foluene (C. A. nomen.)

p-Nitro-toluol

= C7H7NO2=137

NO2






FORMATION.—Toluene is nitrated with mixed nitric and sulfuric acids

to a mixture of 0- and p-nitro-toluene. The separation is effected

by means of fractional distillation and freezing,—the o-isomer

being distilled off and the p-body separated as a solid by cooling

the still residue




Dye Derived from ^-Nitro-toluene

Schultz 'Numbe,for DyeS

andvClas*


Manufacture


498

TRIPHENYL-METHANE

DYETurquoise Blue I '14:-

I J20:-1,5411 Hydrol or1,407' 4:4 /-Tetraethyl-

diamino-benzoliydrol


B

5-Nitro-o-fo luene-sul fonic Acid (C. A. nomen. >

p-Xi t ro - to luene-o-su l fon ic Ac id

S O 3 H

O2^

STATISTICS.—Manufactured ;20:— ?

FORMATION.—From p-nitro-toluene by sulfonation with oleum



Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid

10

Ordinary Same andClJsofDye

STILBEXE D Y E S

Sun YellowDirect Yellow R


Manufacture

Mikado YellowStilbene Yellow

, I '14:—232,6SSM'17:—420,685M J18:—307,702M719:—4iO,924

1 I '20:— 1,404M J20:—348,S49

, I 'U:— 85,795M 1 8 : — ?M J 1 9 : — ?


p-Nitro-t oluene-o-sul-fonic Acid (4 mols)

[Alkalies]


[Alkalies; Oxidation]


D

D


Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid (continued)



STILBENE DYES(continued)

Mikado OrangeChloramine

Orange G

Diphenyl Citronine G

I J14:— 26,010M'17:— ?M'18:— ?M'19:— ?M'20:— 38,2S7

Polychromine BDiphenyl Orange RR M

Diphenyl Chrysoine

Chicago Orange G

Curcuphenine

Chlorophenine


Manufacture

I '14:— 16,11318:— ?

I '14:— 9,898


p-Mtro-toluene-o-sul-ionic Acid (4 mols)

[Alkalies; Oxidation]


Aniline (2 mols)




p-Amino-phenol(2 mols)

[Ethylation]

Benzidine

p-Ni tro-toluene-o-sul-fonic Acid (4 mols)

Dehydro-thio-p-tolui-dine-sulf onic Acid(2 mols)


Dehydro-thio-p-tolui-dine-sulfonic Acid(2 mols)

[Reduction]


Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid (continued)





Used and Notes


205

206

207

MONOAZO DYESDiphenyl Chrysoine

RR

Diphenyl CatechineG

Diphenyl FastBrown G

I '14:— S,642

I '14:— 992

p-Xitro-toluene-o-sul-fonic Acid (2 mols)


Phenol[Ethylation]

p-Xitro-toluen e-o-sul-fonic Acid (2 mols)


Dimethyl-gamma Acid

p-Nitro-toluene-0-sul-fonic Acid (2 mols)


Phenyl-gamma Acid

D

D

^-Nitro-toluene-o-sulfonic Acid (CHZ=1)

See, 5-Xitro-o-toluene-sulfonic Acid (C. A. nomen. SOJEI

2-Nitro-^-foluidine (C. A. nomen.

m-Nitro-p-toluidine (CH3 = 1)

N H 2

CH 3

STATISTICS.—^Imported '14:—10,513 lbs.Manufactured '17:— ?Manufactured ' 18:—24,415 lbs.Manufactured 19:—58,454 lbs.Manufactured '20:—71,197 lbs.


FORMATION.—From acetyl-p-toluidine by nitration


Dye Derived from 2-Nitro-^-toluidine (iV#2=-0

455

SchulteNumberjor Dye

73


MONOAZO DYEPigment Fast

RedHLLithol Fast Red RLLithol Fast Scarlet


Manufacture

I 14:— 49,708M'17:— ?M'18:— ?M'19:— ?I '20:— 1,001M'20:— ?


/3-Naphthol


CL

3-Nitro-£-foluidine (C.A.nomen.

o-Nitro-p-toluidine (CHz—1)

STATISTICS.—20,737 lbs. imported in fiscal year 1914

FORMATION.—From dinitro-toluene by partial reduction, using iron andsulfur dioxide

LITERATURE.—Lange, Zwischenprodukte, #536, 539, 790, 791

5-Nitro-o-tfoluidine (C. A. nomen. NH2 =1)

p-Nitro-o-toluidine (CH3 = 1)

NH2

STATISTICS.—Imported '14:—30,642 lbs.Manufactured '20:— ?


FOR?V£ATION.—From o-toluidine by nitration

LITERATURE.—Cain, Intermediate Products (2d Ed.), 5&Lange, Zwischenprodukte, y790

Dyes Derived from 5-Nitro-o-toluidine (NH2 =1)

SckvltzNumberfor Dye

8

72


NITRO DYEPigment Chlorine

MONOAZO DYEPigment Orange R


Manufacture

M'19:— ?M720:— ?


5-Xitro o-toluidine(2 mols)

/9-Xaphthol


CL

CLMF

m-Nitro-^-toluidine (CHZ=1)

See, 2-Nitro-p-toluidine (C. A. nomen. NH2~1)

o-Nitro-^-tolnidine (CiJ3=i)

See, 3-Nitro-p-toluidine (C. A. nomen.

^-Nitro-o-toluidine (CHZ=1)

See, 5-Nitro-o-toluidine (C. A. nomen.

o-Nitro-toluol

See, o-Nitro-toluene (C. A. nomen.)

£-Nitro-toluol

See, p-Nitro-toluene (C. ^i. nomen.)

o-Nitaro-toIylaldehyde

See, 2-Nitro-m-tolualdehyde (C A. nomen.)

3-Nitro-l: 2: S-taihydroxy-anthraquinone

See, 3-Nitro-flavopurpurin (C. A. nomen.)


NWAcid


Ortho=o

Note.—This is not considered in the alphabetical arrangement, e.g.,orlho-Toluidine is indexed as o-Toluidine under "T." However, o-Toluidine precedes p-Toluidine

Oxy-compounds

See, Hydroxy-compounds

Oxy-juglone

See, Naphthazarin

a-Oxy-naphthoic Acid

See, l-Hydroxy-2-naphthoic Acid

/3-Oxy-naphthoic Acid

See, 3-Hydroxy-2-naphthoic Acid

a-Oxy-naphthoic-sulf onic Acid

l-Hydroxy-2-napMhoic-4-sulfonic Acid {not considered herein)

/3-Oxy-naphthoic-sulf onic Acid L

2-Hydroxy-3-naphthoic-6-sulfonic Acid {not considered herein)

/3-Oxy-naphthoic-sulf onic Acid S

2-Hydroxy-3-naphthoic-8-sulfordc Acid {not considered herein)

Note,—This is not considered in the alphabetical arrangement, e.g., para-Nitro-aniline is indexed as p-Nitro-aniline under "N." However, p-Nitro-aniline follows m-Nitro-aniline


Peri AcidSee, l-Naphthylamine-8-sulfonic Acid

Peri-naphthylene-diamine1: 8-Naphthylene-diamine (iiot considered herein)

PhenanthraquinoneSee, Phenanthrene-quinone

Phenanthrene-quinone (C. .4. nomen.)

9:10-Dihydro-9:10-diketo-phenanthrene

Phenanthraquinone

0 0

= 208

FORMATION.—From phenanthrene by oxidation with sodium bichromateand sulfuric acid

LITERATURE.—Lange, Zwischenprodukte, ^648Green, Organic Coloring Matters (1908), 65

SchuiizNumberfor Dye

668

Dye Derived


AZINB DYEFlavinduline 0

from Phenanthrene-quinone


Manufacture

I 14:— 660


o-Amm o-diphenyl-amine


B

Phenanthroquinolinone (C. A. noynen.)

See, Benzanthrone-quinoline

^-Phenetidine (C A. nomen.)

p-Amino-phenol Ethyl Ether

NH2


STATISTICS.—Imported '14:—125,524 lbs.Manufactured ' 17:— ?Manufactured '18:— ?Manufactured '19:— ?

FOKMATION.—From p-amino-phenol by ethylation of the hydroxyl.Before ethylation the amino group is protected; for example, byforming the benzylidine compound by treatment of the p-amino-phenol with benzaldehyde


Dye Derived from ^-Phenetidine


584


XANTHONE DYEFast Acid Blue R


Manufacture

I '14:— 4,022I '20:— 130


p-Phenetidine (2 mols)3:6-Dichloro-plithalic

AnhydrideResorcinol (2 mols)[PC15; Sulfonationl


A

Phenol ((7. A. nomen.)

Carbolic Acid

= C6H6O=94

STATISTICS.—Imported '14:— 10,108,781 lbs.Manufactured '17:— 64,146 499 lbs.Manufactured '18:—106,794,277 lbs.Manufactured '19:— 1,543,659 lbs.Manufactured '20:— ?

FORMATION.—(1) By distillation from coal tar. (2) By synthesis frombenzene, in which case the benzene is suKonated to benzene-sulfonicacid, which is then fused with caustic soda

LITERATURE.—Cain, Intermediate Products, 104Lange, Zwischenprodukte, #142-145


Dyes Derived from Phenol


5

125

205

303

304

315

319

373


NITRO DYEPicric Acid

MONOAZO DYESDiazine Black

DiphenylChrysoine RR

DISAZO DYESBrilliant YellowPaper Yellow

Chrysophenine G

Congo Orange G

Diamine Scarlet B

Congo Orange R


Manufacture

M'19:— ?M '20:— ?

I '14:— 2,630I '20:— 701

I '14:-27S,000M'17:— ?M'lS:— 1,664M'19:— 4S,723I '20:— 126M'20:— 91,218

I '14:—157,799M'17:— ?M'18:— 41,663M'19:— 86,795I '20:— 3,661

M'20:—247,202

I '14:— 1,623I '20:— 75

I '14:— 41,175I '20:— 10,565

I '14:— 7,027I '20:— 254


p-Tolylene-diamineo-ToluidineAniline or

o-Toluidineor

[Safranine]

p-Nitro-toluene-o-sul-fonic Acid

p-Phenylene-diairrine

Diarmn o-stilbene-disuKonic Acid

Phenol (2 mols)

Diamino-stilbene-disuL-fonic Acid


BenzidineAmino-R Acid[Ethylationl

BenzidineGAcid

TolidineAmino-R Acid[Ethylation]


B

B

D

DA

D

D

D

D


Dyes Derived from Phenol {continued)

461


404

431

464

467

470

474

515



Diamine Yellow N

Diamine GoldenYellow

TBISAZO DYESErie Direct

Green ET

Diphenyl Green G

Chloramine Green B



Methyl Violet


Manufacture

M'17:— ?I '20:— 313

M'17:— ?M'18:— ?M'19:—• 69,700M'20:— ?

I '20:— 2,205

I '14:— 1,675M19:— ?M'20:— ?

I 14:— 77,100M'17:— ?M'18:—295,147M'19 :—305,854I '20:— 2,460M'20:-420,138

I 14:—255,063M17:—375,107M18:—632,196M19:—574,436I '20:— 3,312

M'20:—600,873


Ethoxy-benzidineSalicylic Acid[Ethylation]

1:5-Naphthylene-dia-rnine-3:7-disulfonicAcid


BenzidineHAcidAniline

BenzidineHAcido-Chloro-p-nitro-

aniline

BenzidineHAcid2: 5-Dichloro-aniline

BenzidineHAcidp-Nitro-aniline



D

D

D

D

D

D

B


Dyes Derived from Phenol {continued)

SchidtzNumberjor Dye



Manufacture

517


(continued)Methyl Violet 5BBenzyl Violet

519

555

556

693

718

Methyl Green

Aurine

Red Coralline

AZINE DYEMilling Blue

SULFUB DYESSt. Denis Black B

I '14:— 22,3S7M'17:— ?

'20:— 3,313

I '14:-M'18:-I '20:-

7S4

336

I '14:— 3,082



orDimethyl-aniline

(3 mols)Benzyl Chloride

[Methyl Chloride ofMethyl Violet]

orDimethyl-aniline

(3 mols)[Methyl Chloride]

Phenol (3 mols)[Heated with oxalic and

sulfuric acids]

[Aurine treated withammonia]

orPhenol (3 mols)[Heated with oxalic and

sulfurie acid; treatedwith ammonia]

Aniline (2 mols)Phenyl-a-iiaphthyl-

amine (2 mols)[Sulfonation]

p-Phenylene-diamineNitro-benzene


B

B

CL

CL

M


Dyes Derived from Phenol (continued)

iSchultzNumberfor Dye

732

775


SULPUE DYES(continued)

Autogene Black

ANTHEAQUINONE ANDALLIED DYES



Manufacture

I 14:— 7,495


4-Amino-4/-hydroxy-diphenylamine

or2: 4-Diamino-4'-hy-

droxy-diphenylamine[S2CI2; S+Na^S]

Naphthazarinor

Dirdtro-naphthalene


S

M

Phenyl-^-amino-benzyl-o-toluidine (CH3=1)

See, ^-Benzyl-JV^phenyl^-m-tolylene-diamine

Phenyl-/>-amino-ethyl-o-toluidine (CH3 =1)

See, N^Ethyl-N^phenyM-m-tolylene-diamine

4-Phenylamino-4/-hydroxy-diphenylamine

p-(p-Anilino-anilino)-phenol (C. A. nomen.)

= 276

FOEMATION.—(1) From p-amino-diphenylamine and phenol by oxida-tion in acid solution and then reduction of the indophenol.(2) From diphenylamine and p-amino-phenol (p-nitroso-phenol)by oxidation and then reduction of the indophenol

LITEEATUEE.—Cain, Intermediate Products (2d Ed.), 76Lange, Zwischenprodukte, #1721Lange, Schwefelfarbstoffe, 161


Dye Derived from l-Phenylamino^'-hydroxy-diphenylainine


735


SULFUR DYEPyrogene Indigo


Manufacture

I '14:— 22,661


[S+NaaS]


S

l-Phenylairdno^'-liydroxy-Cphenyl-S'-tolylainiiie)

4-(p-Anilino-anilino)-o-cresol (C. A. nomen. OH = 1

CH3

•XH

N.—From p-amino-diphenylamine and o-cresol by oxidationand subsequent reduction of the indophenol formed


Dye Derived from 4-Phenylaj3ciino-4'-hydroxy-(phenyl-3A-tolylaniine)

Numt Ordinary Name andfor Dye Cla^sofDye

SULFUR DYE735 Pyrogene Indigo


Manufacture

I 314:— 22,661


[S+NaaS]


s

2-Phenylamino-8-iiaphthol-6-sulf onic Acid

See, Phenyl-gamma Acid

Phenyl-m-amino-phenol

See, m-Hydroxy-diphenylamine

Phenyl-^-amino-o--toluidine

See, iY^Phenyl-^r-m-tolylene-diamine


Phenyl-azo-aniline (C. A. nomen.)

See, Amino-azo-benzene

m-Phenylene-diamine

N H 2

J N H 3

STATISTICS.—Manufactured '17:-—220,956 lbs.Manufactured '18:—641,299 lbs.Manufactured '19:—609,789 lbs.Manufactured '20:—658,313 lbs.

FORMATION.—From m-dinitro-benzene by reduction with iron andhydrochloric acid


Dyes Derived from m-Phenylene-diamine





Used and Notes


33MONOAZO DYES

Chrysoidine Y

88

89

Acid AnthraceneBrown R

MetachromeBrown B

I '14:— 63,303M'17:—195,756W18:—376,495M'19:—314,581M'20:—585,648

I '14:— 33,053M'17:— ?M'19:~- ?I ' 20:— 1,400M'20:— ?

I '14:— 1,001M'17:— ?M'18:—349,961MJ19:— ?M'20:—192,914

Aniline B

Picramic Acid[Substituted phenylene-diamine-suHonic Acids]

Picramic Acid

ACr

M


Dyes Derived from 7n-Phenylene-diamine (continued)


154

190

208

209

239

283

285

329



Acid AlizarineBrown B

Palatine ChromeBrown W

Alkali BrownBenzo Brown 5B,

DISAZO DYESLeather BTown

Terracotta FC

AzotolC

Bismarck Brown

Toluylene Brown G

Diamine Brown V

I '14:— 18,264M'17:— ?M'lS:— ?M'19:— ?I '20:—M'20:—

M'19:—M '20:—


Manufacture

845

?2,987

I '14:— 500M'19:— ?MJ20:— ?

I '14:— 551


o-A m in o-phenol-p-sulfonic Acid

Dehydro-thio-p-tolui-dine-sulfonic Acid

or

I '14:— 35,020M'17:—309,857M 'IS:—378,208M'19:^12,574M'20:—514,218

M'19:— ?

Primuline

?>-Phenylene-diamme(2 mols)

Primuline or Dehydro-thio-p-toluidine-sulf onic Acid

Naphthionic Acid

p-Amino-acetanilidej3-Naphthol

ifl-Phenylene-diaTnin e(3 mols)

3:5-Diamino-2>-toluene-sulfonic Acid

BenzidineGamma Acid


M

D

B

MF

B

D

D


Dyes Derived from m-Phenylene-diamine (continued)

467





Used and Notes



Columbia Black FF

Isodiphenyl Black R

Diaminc Bronze G

Trisulfon Brown B

Trisulf on Brown G

Trisulfon. Brown GG

I 14:—402,997M18:— ?M19:— ?I '20:— 23,350MJ20:— ?

:— 4,449

I 14:— 16,781I '20:— 38,616

I 14:— 1,323

I 14 — 7,562I '20:— 38,411

Trimethyl-m-amino-phenyl-arnmoniumChloride orp •Amino-benzyl-di-ethylamine

a-Naphthylamine orm-Toluidine

Aniline

l-Naphthylamine-6-cmd7-sulfonic Acids

p-Phenylene-diamineGamma Acid

p-Phenylene-diamineGamma AcidRcsorcinol

BcnzidineSalicylic AcidH Acid

BenzidincSalicylic Acid2R Acid

TolidineSalicylic Acid2R Acid

DianisidineSalicylic Acid2R Acid


Dyes Derived from m-Phenylene-diamine {continued)


458

461

462

469

476

479


TRISAZO DYES{continued)

Carbon Black

Coomassie UnionBlack

Erie Direct Black GXDirect Deep

Black EW

Chloramine Black N

Benzamine Brown3GO

Dianil Black R


Manufacture

I '14:—1,246,53C

M'17:— ?M'lS:— ?M'19:—

7,250,007M'20:—

7,736,994

I '14:— 39,600M'19:— ?I '20:— 1,763M'20:— ?

I '14:— 16,9SSM'17:— ?M'18:— ?

M'20:—623,757


p-Phenylene-diamine-sulfonic Acid (from p-nitro-aniline-o-sul-fonic Acid)

l-Xaphthykmine-6 (7)-sulf orric Acid

??2-Phenylene-diamine(2 mols)

1:4-Xaphthylene-dia-mine-2-sulf onic Acid

Gamma AcidTn-Phenylene-diaTnine

(2 mols)

BenzidineAnilineHAcid

BenzidineH Acid2:5-Dichloro-aniline

BenzidineSulfanilic AcidSalicylic Acid

BenzidineNaphthionic AcidChromotropic Acid


D

D

D

D

D

D


Dyes Derived from m-Phenylene-diamine (continued)





Used and Notes


485

486

487

488

490

491

492

TETRAKISAZO DYES

Benzo Brown G

Direct Brown J

Benzo Brown B

Toluylene Brown ~R

I '14:— 41,905M'17:— ?M'18:— ?M 1 9 : — 83,506I '20:— 2,286M'20:—109,648

I '14:— 3,640

I '14M'20

:— 438• ?

I ' 1 4 : — 2 0 1

Cotton Brown A I ' 1 4 : — 2 9 , 0 7 4

Dianil Black PR

Anthracene AcidBrown B

S u l f a n i U c A c i d (2 m o l s )

m - P h e n y l e n e - d i a m j n e

(3 m o l s )

m - A m i n o - b e n z o i c A c i d(2 m o l s )

m - P h e n y l e n e - d i a i n i n e

(3 m o l s )

N a p h t h i o n i c A c i d(2 m o l s )


(3 m o l s )

N a p h t h i o n i c A c i d(2 m o l s )

3 : 5 - D i a m i n o - p - t o l u e n e -

s u l f o n i c A c i dm - P h e n y l e n c - d i a m i n e

(2 m o l s )

B e n z i d i n eN a p h t h i o n i c A c i d

(2 m o l s )m - P h e n y l e n e - d i a m i n e

(2 m o l s )

B e n z i d i n e - s u l f o n i c A c i dG a m m a A c i d (2 m o l s )m - P h e n y l e n e - d i a m i n e

(2 m o l s )

A m i n o - s a l i c y l i c A c i d

(2 m o l s )

l - N a p h t h y l a m i n e - 6 - s u l -

f o n i c A c i d (2 m o l s )


Dyes Derived from m-Phenylene-diamine {continued)


607

669


ACRIDINE DYERheonine

AZINE DYENeutral Violet


Manufacture

I '14:— 19,704


Ketone

Dimethyl-p-phenylene-diamine (2 mols)

[Oxidation]


B

^-Phenylene-diamine

Note.—In a number of cases where p-phe?iylene-diamine was apparentlyused, actually its acetyl-derivative p-amino-acetanilide, or even p-nitro-aniline, was employed; and after the first coupling, the second amino groupwas then freed and diazoiized. Here both compounds are generallyindexed.

NH2

NH2

— C6H8N2 =


Manufactured '17:—272,056 lbs.Manufactured '18:—215,148 lbs.Manufactured '19:—234,332 lbs.Manufactured '20:— ?

FORMATION.—(1) From amino-azo-benzene by reduction. (2) From p-nitro-aniline by reduction




Dyes Derived from ^-Phenylene-diamine

471





Used and Notes

13

61

205

206

207

208

290

291

STILBENE DYEPolychromine BDiphenyl Orange RR M

I '14:— 16,113:— ?

MONOAZO DYESVictoria Violet I '14:— 52,365

M'17:— ?M'18:~~ ?M'19:—105,086I '20:— 2,182M'20:— ?

Diphenyl ChrysoineRR

Diphenyl CatechineG

Diphenyl FastBrown G

DISAZO DYESLeather Brown

Violet Black


I '14:- 8,642

I '14: 992

I '14M'19M'20

:— 500:— ?:— ?


p-Nitro-toluene-o-sul-foDic Acid (2 mols)

Chromotropic Acid[The p-Phenylene-dia-

mme from p-Nitro-aniline or p-Amino-acetanilide]


p-Nitro-toluene-0-sul-fonic Acid (2 mols)

Phenol[Ethylation]



Dimethyl-gamma Acid

p-Phenylenc-diamine(2 mols)


Phenyl-gamma Acid


w-Phcnylene-diamine

Nevile-Winther^s Acida-Naphthylamine

Salicylic AcidNevile-Winther's Acid


Dyes Derived from ^-Phenylene-diamine (continued)

SchvltzNumberor Dye

292

436

437

621

695

701

702

713

714

718



Azo AlizarinBlack I

TRISAZO DYESColumbia Black FF

Isodiphenyl Bkck R

OXAZIXE DYECresyl Blue 2BS

Azrs"E DYESParaphenylene

Violet

Paraph enyleneBlue R~

Para Blue

SULFUR DYESThiophor Bronze 5G

Thiophor YellowBronze C

St. Denis Black B


Manufacture

I J14:—402,997M'lS:— ?M'19:— ?I '20:— 23,350^l '20:— ?

I J20:— 337

M'19:— ?


Salicylic AcidChromotropic Acid

l-Naphthylamine-6-anrf-7-sulfonic Acids

Gamma Acid?w-Phenylene-diamine

Gamma AcidResorcinolw-Phenylene-diamine

5-Dimethylamino-2-nitroso-p-cresol

a-Amino-azo-napli-thalene

Amino-azo-benzene

Aniline (3-4 mols)o-Toluidinep~Toluidine

or[Spirit Blue]

[p-Amino-acet-black][Sulfur]

p-A m in o-acetanilideBenzidine[Sulfur]

PhenolNitro-benzene[S2CI2, S, Na^S]


M

D

D

B

B

B

B

S

S

s


Dyes Derived from ^-Phenylene-diamine (continued)

473


727

923


Auronal Black B

ANILINE BLACKGROUP

Ursol D, DB



Ut>ed and Notes

l-Chloro-2:4-dinitro-benzene

[Glycerol; S+Na^S]

[Oxidation on hair]


S

Fur


4: 6-Diamin.o-m-benzene-disulfonic Acid (C A. nomen.

NH2

= C6H8N2O6S2=268

SO3H

FOEMATION.—From ra-phenylene-diamine hydrochloride by treating itwith five parts of 40 per cent oleum, heating at 100° for severalhours, then at 120° for 6-10 hours

LITERATURE.—Lange, Zwischenprodukte, #1146, 1147Green, Organic Coloring Matters (1908), 36

Dyes Derived from m-Phenylene-diamine-disulfonic Acid


192

210

306

Ordinary Name andClass 0] Dye

MONOAZO DYESCotton Orange G

DISAZO DYESCotton Orange R

Pyramine Orange 3G


Manufacture

I 14:— 1,877

I '14:— 16,459I '20:— 51

I ' 1 4 : - 7,863I '20— 396


Primuline

Primuline-sulfonic AcidMetanilic Acid

BenzidineNitro-m-phenylene-

diamine


D

D

D


^-Phenylene-diamine-sulfonic Acid

2: 5-Dtamino~&enzene-sulfonic Acid (C A. nomen.)

Note.—As a rule this compound is not used as such, being formed as the

azo derivative in the dye molecule from the reduction of the azo derivative of

p-nitro-aniline-o-sulfonic add

NH2

{ 1SO3H = :

NIL

FORMATION.—From p-nitro-aniline-o-sulfonic acid by reduction



458

Dye Derived from


TRISAZO DYECarbon Black

^-Phenylene-diamine-sulfonic Acid



Used and Notes

l-Naphthylaminc-6(7)-sulf onic Acid

w-Phenylene-(Toly-lene-)diamine or1:3-Naphthylcne-diamine-6-sulfonicAcid (2 mols)


D

Phenyl-gamma Acid

2-Phenylamino-8-naphthol-6-sulfonic Acid

7-Anilino-l-naphthol-3-sulfonic Acid (C A. nomen.)

HO

HO3s = 315

DYES CLASSIFIED BY INTERMEDIATES 4 75

FORMATION.—From gamma acid (2-amino-8-naphthol-6-sulfonic acid)

by heating with aniline and aniline hydrochloride at 160°


Dyes Derived from Phenyl-gamma Acid




ManvfactureOther Intermediates

Used and Notes


207

349

445

MONOAZO DYEDiphenyl Fast

Brown G

DISAZO DYESDiamine Brown B

TRISAZO D Y ECrumpsall Direct

Fast Brown 0

I '14:— 992

I '20:— 24

p-Nitro-toluene-o-sul-fonic Acid

p-Phenylene-diamine

BcnzidineSalicylic Acid


D

D

D

Phenyl-glycine

iV-Phenyl-tflycine ( C A. nomen.)

N H . C H 2 . C O O H




FORMATION.—By action of chloro-acetic acid on aniline

L I T E R A T U R E . — C a i n , Intermediate Products (2d Ed . ) , 153

Langc, Zwischenprodukte, #96-109, 111


Dyes Derived from Phenyl-glycine

SchultcX umberfor Dye

874

876

877

878

879

SSO

Ordinary Xnnie andCla<*> of Dye

INDIGO GROUP DYESIndigo


Indigotine

Indigotine P

Brom IndigoRathjen

Indigo MLB, RR


I

MM

MiIM

i

IM

M

M

IM

1

ii

iM

i

IM' I

/Statistics ofImpoit andManufacture

'14

'17'IS

'19

:—S,507,359

:—274,771:—3,0S3,SSS

:—S,S63,824

'20—520,347'20

'14'17

'IS

'19

"20'20

'14'20

'14717'20

MT20

;18,178,231

:— 19,329:—1,S76,7S7

:—1,434,703

:—1,699,670

:— 5,512•1,395,000

:— 53,640:— ?

:— 6,S56:— 14,100:— 3,691:— ?


Phenyl-glycine (2 mols)[Sodamide]

Phenyl-glycine (2 mols)[Sodamide, Reduction]

or[Indigo, Reduction]

Phenyl-glycine (2 mols),etc.

or[Indigo, Sulfonation]

Phenyl-glycine(2 mols), etc.



or[Indigo, Bromination]




V

V

A

A

V

V


Dyes Derived from Phenyl-glycine {continued)




Dianthrene Blue 2BBromo Indigo FBCiba Blue 2B






Indigo Yellow 3G

I '14:M'19:I '20:

I '14:I '20:

I '14:-I '20:-M'20:


Manufacture

16,880

35,857

1,3561,008

3,1914,130

I '14:— 4,518

I '14:I '20:

8,1173,503

I 14:— 12,057









or[Indigo, Chlorination,

Bromination]


or[Indigo, Chlorination]



Bromination]


Benzoyl chlorideor

[Indigo, Benzoylchloride]

47S DYES CLASSIFIED BY INTERMEDIATES

Dyes Derived from Phenyl-glycine (continued)

Fchult: si, - \- J Statistics of

for Dye ^ yc Manufacture

INDIGO GEOCP DYE{continued)

890 ' Ciba Yellow G I '14:— 4S! i

>i1 j

!


Phenyl-glycine(2 inols), etc.

Benzoyl chlorideor

[Indigo, Benzoylchloride, Bromina-tion]


V

Phenyl-glycine-o-carboxylic Acid

A'-(Carbox\*-methyl)-anthranilic Acid (C. A. nomen.)

COOH

V

FORSCATION.—Phthalic anhydride is coaverted through phthalimideinto anthranilic acid. This latter by reaction with chloro-aceticacid form? the phony 1-glycine-o-earboxy acid

.—Lange, Zwischenprodukte, ?379, 383-393

Dyes Derived from Phenyl-glycine-o-carboxylic Acid

for Dy* Cla** <* D^c Manufacture

INDIGO GROUP DYESS74 Indigo I '14:—

, ; 8,507,359! M17:—274,771

M '18:—i 3,083,888jM '19:—! 8,863,824

i 11 '20:—520,347!M*20:—

J , 18,178,23!


Phenyl-glycme-a-ca«r-boxylic Add (2 mols)

[Sodarnide]


V


Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)


876

877

878

879

880

881


INDIGO GROUP DYES{continued)


Indigotine

Indigotine P

Bromo IndigoRathjen

Indigo MLB/RR


Manthrene Blue 2BBromo Indigo FBCiba Blue 2B

IM

M

M

IM

I


Manufacture

1417:

18:

19:

'20:'20:

14:-M'20:-

IMIM

IMI

14:-17:-'20:-'20:-

14:19:'20:

— 19,329—1,876,787

—1,434,703

—1,699,670— 5,512—1,395,000

- 53,610- ?

- 6,856- 14,100- 3,691- ?

- 16,880- ?— 35,857


Phenyl-glycine-o-car-boxylic Acid (2 mols)

[Sodamide, Reduction]or

[Indigo, Reduction]

Phenyl-glycine-o-car-boxylic Acid (2 mols),etc.


Phenyl-glycine-o-car-boxylic Acid (2 mols),etc.


Phenyl - gly cine - o - car-boxylic Acid (2 mols)etc.


Phenyl - gly cine - o - car-boxylic Acid (2 mols)",etc.


Phenyl - glycine - o - car-boxylic Acid (2 mols),etc.


Dy,Appli-cationClass

V

A

A

V

V

V











Indigo Yellow 3G

I '14:-I '20 >

I '14:-I '20:-M'20:-

I '14 >


Manufacture

4,3561,002

3,1914,130

4,518

I '14:-I '20:-

8,17,3,503

I '14:— 12,057








Bromination]


or[Indigo, Chlorination]

Phenyl - glycine - o - car-boxylic Acid (2 mols)etc.

or[Indigo, Bromination,

Chlorination]


Benzoyl chlorideor

[Indigo, Benzoylchloride^





890



Ciba Yellow G


Manufacture

V 14:— 48


Phenvl - glycine - o - car-boxylic Acid (2 mols),etc.

Bcnzoyl chloride[Bromination]

or[Indigo Yellow 3G,

Brominationl


V

Phenyl-hydrazine-^-sulfonic Acid

p-Hydrazino-frenzene-sulfonic Acid (C. A. nomen.)

N H . N H 2

SO3H

STATISTICS.—Manufactured '20:—441,117 lbs.

FOKMATTON.—(1) Sulfanilic acid is diazotized and then reduced withsodium bisulfite. (2) Aniline is diazotized and reduced withsodium bisulfite, forming phenyl-hydrazinc, which is then sulfonatedwith 66° sulfuric acid at 100°

LITEEATURE.—Cain, Intermediate Products (2d Ed.), 49Lange, Zwischenprodukte, #629


19

20

Dyes Derived from Phenyl-hydrazine-£-sulfonic Acid


PYRAZOLONE DYESFlavazine LFast Light Yellow

Flavazine S


Manufacture

I '14:— 38,908I '20:— 9,327

I '14:— 81,375I '20:— 1,500


Aniline[Ethyl Aceto-acetatc]

Aniline[Ethyl Oxal-acetate]


A

A


Dyes Derived from Phenyl-hydrazine-^-sulfonic Acid {continued)


23

27


PYRAZOLONE DYES(continued)

Tartrazine

Dianil Yellow 2R


Manufacture

I '14:—272,477M'17:— ?M'18:— ?MJ19:— ?I '20:— 47,877M;20:—701,722


Phenyl-hydrazine-p-sulfonic Acid (2 mols)

Dihydroxy-taTtaricAcid

orSulfanilic Acid[Ethyl Oxal-acetate]

Primuline-sulfonic Acid[Ethyl Aceto-acetate]


A

D

l-Phenyl-3-methyl-5-pyrazolone

See, 3-Methyl-l-phenyl-5-pyraz"olone

Phenyl-a-naphthylamine

iV-Phenyl-1-mphthylamine (C A, nomen.)

NH-

STATISTICS.—^Manufactured '17:—Manufactured '18:—Manufactured'19:—Manufactured '20:—

FOKMATION.—From a-naphthylamine hydrochloride and aniline byheating together

LITERATURE.—Cain, Intermediate Products (2d Ed.), 187Cf. Lange, Zwischenprodukte, #2827Thorpe, Die. Chemistry, 3, 587


SchultzNumber}or Dye

263

361

559

693

Dyes Derived


DISAZO DYESJet Black R

Sulfonazurine


Victoria Blue B

AZINE DYEMilling Blue

Prom Phenyl-a-naphthylamine


I '14:— 300

I '14:—127,769M'17:— ?M'18:— ?M'19:— ?I }20:-~ 11,782

M'20:— ?

I 14:— 3,082


Aniline-2:4-disuIfonicAcid

a-Naphthylamine

B enzidine-sulf on-disul~fonic Acid

Phenyl-a-naphthyl-amine (2 mols)

Ketoneor

Hydrol

Aniline (2 mols)Phenyl-a-naphthyl-

amine (2 mols)Phenol[Sulfonation]


A

D

B

M

Phenyl-0-naphthylamine

iV-Phenyl-2-naphthylamine (C A. nomen.)

—NH—-

FORMATION.—From i3-naphthol and aniline (or hydrochloride) byheating together in an open vessel to around 200°

LITERATURE.—Lange, Zwischenprodukte, #2827Thorpe, Die. Chemistry, 3, 599


Dye Derived from Phenyl-i3-naphthylamine


676


AZINE DYENeutral Blue


Manufacture

I '14:— 615




B

Phenyl-l-naphthylamine-8-sulfonic Acid

8-AniMno-l-naphthalene-sulfonic Acid (C. A. nomen.)

Phenyl-peri Acid

HO3S NH

STATISTICS.—Imported '14:—9,139 lbs.Manufactured '18:— ?Manufactured 19:— ?Manufactured '20:— ?

FORMATION.—l-Naphthylamine-8-sulfonic acid, aniline, and anilinehydrochloride are heated together in an autoclave


Dyes Derived from Phenyl-l-naph.tliylamine-8-sulfonic Acid


85

188


MONOAZO DYEOmega Chrome

Black PY

Tolyl Blue SRSulfon Acid Blue R


Manufacture

I '14:— 45,038M '17:— ?M318:— ?MJ19:— ?M '20:-454,185


2-A TTiirt 0-6-nitro-p-cresol

HAcid


ACr

A


Dyes Derived from Phenyl-l-naphthylamine-8-sulfonic Acid (continued)


256

257

265


DISAZO DTESSulf on Black 3B

Sulfoncyanine



Manufacture

I ' 14:—145,649M'17:— ?M'18:— ?M'19:— ?I '20:— 18,327

M'20:— ?

I '14:— 69,590M'17:— ?M'18:— ?M'19:— ?M'20:— ?


Metanilic Acida-Naphthylamine


Laurent's Acida-Naphthylamine or

l-Naphthylamine-6-and 7~su]f onic Acids

Di/eAppli-cationClass

A

A

A

iV-Phenyl-o-phenylene-diamine ((7. A. nomen.)

See, o-Amino-diphenylamine

AT-Phenyl-^-phenylene-diamine (C. A. nomen.)

See, p-Ammo-diphenylannne

JVi-Phenyl-4-m-folylene-diarnine (C. A. nomen. NH2=1)

Phenyl-p-amino-o-toluidiae (CH3=1)

3-Amiao-4-metliyl-diphenylamine

NH

= 013^4^2=198

FORMATION.—^From m-tolylene-diamine hydrochloride by melting withaniline at 220-270°

LITERATUEE.—Lange, Zwischenprodukte, #1621, 1622


Dyes Derived from iV1-Phenyl-4-m-tolylene-diaDaine


684

684

684


AZESTE DYESHhoduline Violet

Rhoduline Red B

Rhoduline Red G


I '14:— 2,751I '20:— 35


Mtroso-dimethyl-aniline

Kitroso-ethyl-aniline

Mtrosoethyl-o-toluidine

Appli-cationClass

B

B

B

Phosgene (C. A, nomen.)

Carbonyl Chloride

\ c i

= CC12O=99

STATISTICS.—Imported J14:—very smallManufactured in recent years in undisclosed quantities

FORMATION.—From cMorine and carbon monoxide, in presence of acatalyst, for example, a suitable charcoal

LITERATURE.—LTlmanu, Enzy. tech. Chemie, 3, 498

Dyes Derived from Phosgene


279

296


DISAZO DYESBenzo Fast Scarlet

Cotton Yellow G

Statistics ofImport end

Manufacture

I '14:— 36,674M'19:— ?I '20:— 24,153

I '14.— 31,472I '20:— 4,651


J Acid (2 mols)AnilineAmino-azo-benaene

Acetyl-p-phenylene-diamine (2 mols)



D

D


Dyes Derived from Phosgene (continued)





Used and Notes


516

518

810


Crystal Violet



Helidone Yellow3GN

'14:— 51,872M'17:— ?M'18:— ?M'19:— ?I '20:— 2,919M'20:— ?

I '14:— 51,933

I '14:— 20,744I '20:— 2,515


B

Diethyl-aniline (3 mols)

2-Amino-anthraqui-none (2 mols)

B

Phthalic Anhydride

O = C 8 H 4 O 3 = 148

STATISTICS.—Imported 14:— 63,574 lbs.

Manufactured 17:—138,857 lbs.Manufactured 18:—227,414 lbs.Manufactured 19:—290,677 lbs.Manufactured '20:—796,210 lbs.

FORMATION.—(1) Naphthalene is oxidized with air in presence of acatalyst. (2) Naphthalene is oxidized by means of sulfur trioxidein presence of mercury.



Dyes Derived from Phthalio Anhydride

Sekultz Qr(iinari/ Name and

571XANTHONE DYES

Rhodamine 6G

572 Rhodamine G

573 I Rhodamine B

574

580

Rhodamine SB

Past Acid Yiolet B


Manufacture

I '14:— 37,515I '20:— 8,574

I '14:-I '20:-

2,648217

I J14:— 59,354M317:-M '18:-MJ19:-I '20:-M J20:-

24,709?

I '14:— 20,6S8I '20:— 2,907

M'19:— ?


Ethyl-Tft-amino-phenol(2 mols)

[Ethylation]

Diethyl-772-amino-phenol (2 mols)

Aniline [removes oneC2H5 group]

or[Heating of Rhodamine

B with aniline salt]


orResorcinol (2 mols)[PC15; diethyl-amine]

Diethyl-wz-amino-phenol (2 mols)

[Ethyl esterification]or

[Ethyl ester of Rhoda-mine B]

Resorcinol (2 mols)Aniline or

p-Toluidine (2 mols)[PC15; sulfonation]

or[Dichloro-fluoresceine

and Aniline orp-Toluidine; sul-fonation]


B

B

B

B


Dyes Derived from Phthalic Anhydride (continued)

489




Fast Acid Eosine GFast Acid Phloxine A

Fast AcidViolet A2R

Acid Rosamine A

UranineFluoresceine

Chrysoline

Eosine

I '14:I '20:-M'20:-


Manufacture

I '14:-I '20:-

I '14:-I '20:

6505,234

8752,679

• ?

5 0

1 4 1

I ; 1 4 : — 2 , 2 7 3

M ' 1 7 : — ?

M ' 1 9 : — ?

I ' 2 0 : — 1 0

I ' 2 0 : — 1 , 4 0 2

I ' 1 4 : — 9 4 , 5 2 8

M ' 1 7 : — 6 8 , 4 9 6

M ' 1 8 : — 1 6 1 , 1 5 3

M ' 1 9 : — 1 2 1 , 3 0 3

I ' 2 0 : — 2 9 6

M ' 2 0 : — 8 5 , 4 8 9

Other Intermediates

Used and Notes

D i e t h y l - m - a m i n o ~

p h e n o l ( 2 m o l s )

[ S u l f o n a t i o n ]

or

[ R h o d a m i n e B , s u l f o -

n a t e d ]

R e s o r c i n o l ( 2 m o l s )

o - T o l u i d i n e ( 2 m o l s )

[ P C l s , S u l f o n a t i o n ]

or

[ D i c h l o r o - f l u o r e s c e i n e

and o - t o l u i d i n e ,

S u l f o n a t i o n ]


M e s i d i n e ( 2 m o l s )

[ P C 1 5 , S u l f o n a t i o n ]

or

[ D i c h l o r o - f l u o r e s c e i n e

and m e s i d i n e , s u l f o -

n a t i o n ]



B e n z y l C h l o r i d e


[ B r o m i n e ]

or

[ T e t r a b r o m o - f l u o r e -

s c e i n e ]

Dye

Appli-

cation

Class


Dyes Derived from Phthalic Anhydride {continued)





Used and Notes


588

589

590

591

592

599


Eosine Spirit Solubl.Methyl Eosine

Eosine S

Eosine BNAcid Eosine

Erythrosine G

Erythrosine B

Galleine

I '14:-M'20:-M'20:-

'14:-'20:-

M'20:-

2,315??

20,1431,132

I '14:—

I '14:-M'17:-M'18:-M'19:-I r20:-M720:-

I '14:-M'19:-I '20:-M'20,

Resorcinol (2 mols)[Bromine; Methyl

esterincation]or

99

4,35050,

1,636

6,874

15,404

7,469

Eosine methyl ester]

Resorcinol (2 mols)[Bromine; Ethyl

esterification]or

[Eosine ethyl ester]

Resorcinol (2 mols)Promination, Nitra-

tion]or

[Dibromo-flTioresceinenitrated]


or[Diiodo-fluoresceine]


or[Tetraiodo-fluoresceine]

Gallic Acid (2 mols)or

Pyrogallol (2 mols)



491


600

601

612

613

758

782

874



Coeraleine B

Coeruleine S

QUINOLINE DYESQuinoline Yellow

Spirit Soluble

Quinoline YellowWater Soluble


Sirius Yellow G




Manufacture

MM

IMI

II

II

IMMMIM

I

MM

M

M

I

'19:'20:

'14:'19:'20:

'14:'20:

'14:'20:

— ?— ?

— 3,404— ?— 9,392

— 79,553— 205

— 15,354— 34,440

'14:—115,586'17:'18:'19:'20:'20:

'14:

'17'18.

'19'

'20

— ?— ?— 40,426— 2,728— 42,840

—8,507,359—274,771——3,083,888

8,863,824—18,178,231

'20:—520,347


Resorcinol (2 mols)[Dehydration]

or[Fluoresceine

dehydrated]

Gallic Acid (2 mols)or

Pyrogallol (2 mols)[Dehydration]


Quinaldine

Quinaldine[Sulfonation]

Naphthalene

Gallic Acid

Phthalic Anhydride(2 mols)


M

M

ss

A

CL

M

V



SchultzNumberJOT Dye

S76

877

878

879

880

881

882

883


INDIGO GROUP DYES{continued)


Indigotine I '14M'17

M ' l S

M'19

M'20

I '20;

Indigotine P

Brom IndigoRath j en






Manufacture

:— 19,329

1,876,787

1,434,703

' 1,699,670

1,395,000:— 5,512

I '14M'20

:— 53,610:— ?

I '14M'17I '20M720

I 14:-MJ19:-I '20:-

I '14:-I '20-

I '14:-I '20:-

M'20:-

:— 6,856:— 14,100:— 3,691

16,880

35,857

1,3561,008

3,1914,130



[Reduction]


[Sulfonation]


[Sulfonation]


[Bromination]


[Bromination]


PBromination]


promination]

Phthalic Aiihydride(2 mols)

[Bromination]



493





Used and Notes


884

885

886

890





Indigo Yellow 3G

Giba Yellow G

I '14:— 4,518

I '14:I '20:

8,1753,503

I '14:— 12,057

I '14: 48




[Chlorination]




Benzoyl Chloride


Benzoyl Chloride[Bromination]

Phthalimide

f T N H =

STATISTICS.—Manufactured in 1920 in undisclosed amountFORMATION.—By treatment of molten phthalic anhydride with gaseous

ammoniaLITERATURE.—Cain, Intermediate Products (2d Ed.), 147USES.—For preparation of anthranilic acid

Piria's AcidSee, Naphthionic Acid

494 DYES CLASSIFIED BY INTERMEDI TES

Picramic Acid

OH

NO2

STATISTICS.—Manufactured '17:— ?Manufactured '18:—235,652 lbs.Manufactured '19:—150,458 lbs.Manufactured '20:—138,350 lbs.

FORMATION.—From picric acid by reduction, using sodium hydrogensulfide or sodium sulfide


Dyes Derived from Picramic Acid

SchtdtzNumberfor Dye

88

89

90

91

92

219


MONOAZO DYESAcid Anthracene

Brown B,

MetachromeBrown B

Chrome Brown P

Anthracyl ChromeGreen D

MetachromeBordeaux R

DIRAZO DYEChrome Patent

Green N


Manufacture

I '14:— 33,053M'17:— ?M'19:— ?I '20:— 1,400M'20:— ?

I '14:— 1,001M'17:— ?M'18:—349,961M'19:— ?M '20:—192,914

I '14:— 4,596M'18:— ?I '20:— 3,316


m-Phenylene-diamine-[sulf onic Acids]

m-Phenylene-diamineor

m^Tolylene-diamineor

Chloro-m-phenylene-diamine

m-A mino-phenol

Naphthionic Acid

3-Amino-4-methyl-phenyl-p-tolyl-sul-famide

AnilineKAcid

DyeApplication"Class

ACr

M

M

ACr

M

ACr


Picric Acid

OH

STATISTICS.—Manufactured in 1919 and 1920 in an indeterminateamount for dyeing purposes. Prior to 1919 it was made in verylarge quantities for explosive uses

FORMATION.—Phenol is sulfonated and then trinitrated

LITERATURE.—Cain, Intermediate Products (2d Ed.), 114Lange, Zwischenprodukte, #1116-1121Schultz, Farbstofftabellen (1914), #5

USES.—For the manufacture of picramic acid. I t is also a dye, Schultz #5

Primuline-sulfonic Acid (Sodium Salt)

(This is the "Primuline" of commerce)

(Primuline "base" is the unsulfonated product)


FORMATION.—p-Toluidine and sulfur are heated together, resulting in amixture of primuline base and p-dehydro-thio-p-toluidine, knownas primuline "melt." This can be separated by vacuum distilla-tion. However it is generally sulfonated, using 23 per cent oleum,and then separated by the greater solubility of the ammonium saltof the primuline-sulfonic acid

LITERATURE.—Schultz, Farbstofftabellen, #616Wahl, Organic Dyestuffs, 299Thorpe, Die. Chemistry, 4, 386


Dyes Derived from Primuline-sulfonic Acid


18

25

26

27

190

191

192

195

197


STILBENE DYEDiphenyl Fast

Yellow

PYRAZOLONE DYESDianil Yellow 3G

Dianil Yellow R

Dianil Yellow 2R

MONOAZO DYESAlkali BrownBenzo Brown 5R

Pyramine Yellow R

Cotton Orange G

Rosophenine SG

Tniazine Red G


Manufacture

I '14:— 10,229I '20:— 1,102

M'19:— ?M'20:— 2,9S7

I '14:— 5,727I '20:— 100

I '14:— 1,877

M'18:— ?M'19:— ?M'20:— 19,639

I '14:— 4,861M '18:— ?M'19:— 11,886M '20:— 13,988


Primuline-sulfonicAcid (2 mols)

Dinitro-dibenzyl-disul-fonic Acid orDinitro-stilbene-di-sulfonic Acid

[Ethyl aceto-acetate]


3-Methyl-l-p-sulfo-phenyl-5-pyrazolone


sulf onic Acid[Ethyl aceto-acetate]

m-Phenylene-diamine


771-Phenylene-diamine-disulfonic Acid


Schaeffer's Acid


D

D

D

D

D

D

D

D

D


Dyes Derived from Primuline-sulfonic Acid (continued)


198

199

209

210

615

616



Clayton YellowThiazol Yellow


DISAZO DYESTerra Cotta FC

Cotton Orange R

THIOBENZENYL DYESThioflavinc S

Primuline

IMMMI

IMI

I

II

IMMI

IMMMMI


'14:—'18:—'19:—'20:—'20:—

'14:—'20:—'20:—

'14:—

'14:—'20:—

'14:—'19:—'20:—'20:—

'14:—'17:—'IS:—

29,879???

11,182

13,416?125

551

16,45951

4,948??675

67,97672,46172,788

;19:—271,33S'20:—183,179'20:— 441


Deliydrotliio-p-tolui-dine-sulfonic Acid(2 mols)

orPrimuline (2 mols)

Salicylic Acid

m-Phenylene-diamineNaphthionic Acid


Mctanilic Acid

[Methylation]


D

D

D

D

D

D

Pseudocumidine (C. A. nomen.)

i/'-Cumidine

2 :4 : 5-Trimethyl-anilme

1:2:4-Trimethyl-5-amino-bcn25cne

NH2

CH3


STATISTICS.—Imported '14:— 6,617 lbs.Manufactured '17:— ?Manufactured ' 18:— ?Manufactured '19:— ?Manufactured '20:—28,405 lbs.

FORMATION.—Xylidine hydrochloride is digested with methanol(CH3OH) in an autoclave at 280-300° and the product convertedto nitrates and crystallized. The sparingly soluble nitrates areseparated and washed, and treated with alkali to convert to bases,which are a mixture of xylidines and cumidines. The bases arethen fractionally distilled, and that fraction coming over at 225-245° is allowed to crystallize and is pressed to remove oily products.It consists largely of pseudocumidine

LITERATUBE.—Thorpe, Die. Chemistry, 2, 177 (1912 Ed.); or 2, 434(1921 Ed.)


Dye Derived from Pseudocumidine


83


MONOAZO DYEPonceau 4E


Manufacture

I '14.— 3,557M'17:— ?M'18:— ?M'19:— 24,152M'20:— ?


RAcid


A

Purpurin (C. A. nomen.)

1:2:4-Trihydroxy-aoithraquiaoiie

OH


FORMATION.—From alizarin by oxidation with manganese dioxide and

sulfuric acid

LITERATURE.—Lange, Zwischenprodukte, #3129, 3271Barnett, Anthracene and Anthraquinone

Dyes Derived from Purpurin


783

862



Purpurin



Manufacture

I '14:— 54,706I '20:— 28,802


Aniline[Sulfonation]


M

M

Pyrogallic Acid

See, Pyrogallol

Pyrogallol (C. A. nomen.)

1:2:3-Trihydroxy-benzene

Pyrogallic Acid

OH

) S 5 - <


Manufactured regularly, but amounts not disclosed

FORMATION.—From gallic acid by heating in an autoclave in presence ofwater


Green, Organic Coloring Matters (1908), 45


Dyes Derived from Pyrogallol

Schvltz!Number;•for Dye

62

84

158

599

601

769

770

773


MONOAZO DYEAzo Galleine

Azo Chromine

Chrome Brown RR

XANTHONE DYESGalleine

Coeruleine S

AXTHRAQUINOXE ANDALLIED DYES

Alizarin Yellow C

Alizarin Yellow A

Anthracene Yellow

IMI

IMIM

IMI

I

Statistics ofImport and\fanujaeiure

'14:—'17:—720:—

514:—J19:—J20:—J20:—

'14:—'19:—'20:—

'14:—

7,2419

2,183

15,404?

5,075?

3,404

9,392

4,046



p-Amino-phenol

4-Aniino-l-phenol-2: 6-disulfonic Acid

Phthalic AnhydridePyrogallol (2 mols)

Phthalic AnhydridePyrogallol (2 mols)[Dehydration]


[Acetic Acid]

Benzoic Acidor

Benzo trichloride

[Aceto-acetic EthylEster; Bromination]


M

M

M

M

M

M

M

M

PyrogaUol-5-sulfonic Acid

3:4:5-Trihydroxy-&enzene-sulfonic Acid (C. A. nomen.)

OH

OH


FORMATION.—1: 3-Dichloro-2-hydroxy-benzene-5-sulfonic acid (as po-tassium salt) is fused with concentrated caustic potash solution at150-160°


Ger. Pat., 203,145; Frdl. 9, 247

Dyes Derived from Pyrogallol-5-sulfonic Acid


623


OXAZINE DYEPyrogallol-cyanine-

sulf onic Acid


ManujactureOther Intermediates

Used and Notes

Nitroso-dimcthyl-aniline


M

Quinaldine (C. A. nomcn.)

2-Methyl-quinoline

a-Methyl-quinolinc

= CIOHBN =



FORMATION.—By condensing aniline and piaracetaldehydc cither cold,or hot,—in the latter case using hydrochloric acid and aluminum orzinc chloride to catalyze the reaction


Lange, Zwischenproduktc, #2000-2002


Dyes Derived from Quinaldine


610

612

613


QUINOLINE DYESQuinoline Red

Quinoline YellowSpirit Soluble

Quinoline YellowWater Soluble


Manufacture

I '14:— 79,553I '20:— 205

I '14:— 15,354I '20:— 34,440


Benzo-trichlorideIsoquinoline

Phthalic Anhydride

Phthalic Anhydride[Sulfonation]


B

ss

A

Quinizarin (C. A. nomen.)


FORMATION.—From anthraquinone by oxidation with sulfuric acid inpresence of boric acid

LITERATURE.—Lange, Zwischenprodukte, #3233, 3260, 3268, 3270,3274,3276,3314,3351


Dyes Derived from Quinizarin


852

852



Alizarin Irisol D

Alizarin DirectViolet R



Used and Notes

y-Toluidine[SuHonation]

4-Toluidine-3-sulfonicAcid


A

A



865

865

Dyes Derived


ANTHRAQUINOSTE ANDALLIED DYES

(continued)Alizarin Cyanine

Green E

Alizarin DirectGreen G

from. Quinizarin {continued)


Manufacture

I 14:— 2,000I '20:— 31,851

M'20:— ?


p-Toluidine (2 mols)[Sulfonation]

4-Toluidine-3-sulfonieAcid (2 mols)


ACr

ACr

Quinoline


Manufactured ' 19:— ?

FORMATION.—(1) By extraction from coal-tar. (2) By synthesisthrough the heating together of aniline, nitrobenzene, glycerol andsulfuric acid for some time, first at 125° and then at 180°

LITERATURE.—Lange, Zwischenprodujtte, #1995Thorpe, Die. Chemistry, 4, 468

Dye Derived from Quinoline


611


QUINOLINE DYEQuinoline Blue



Used and Notes

Lepidine[Amyl iodide]


Photo-graphy


RAcid

2-Xaphthol-3: 6-disulfonic Acid (C A. nomen.)

j^Xaphthol-disulfonic Acid R

£-Xaphthol-a-disulfonie Acid

Note.—R Acid is occasionally applied to other naphthalene derivatives,e.g., 2-amino-3-naphthol-6-$ulfonic acid, 2-naphthylamine-S: 6-disulfonicacid} 2:3-dihydroxy-nai)hthale7w-6-mlfonic Acid

HO3SOHSO3H

STATISTICS.—Imported '14:— 46,267 lbs.Manufactured '18:— 712,033 lbs.Manufactured ' 19.—1,008,007 lbs.Manufactured '20:—1,250,674 lbs.

FORMATION.—From /3-naphthol by disulfonation, and separation, fromthe G acid simultaneously formed

LITERATURE.—Cain, Intermediate Products (2d Ed.) , 226Lange, Zwisehenprodukte, #2651, 2652Thorpe, Die. Chemistry, 3, 626


39

47

65

Dyes


MOXOAZO DYESPonceau G

Orange III

Azo Coralline L

Derived from


Manufacture

M '17:— ?

M'17:— ?M'18:— ?

I '20:— 249:U'2O:— ?

R Acid


Aniline

jS-Xaphthol

p-Amino-acetanilide


A

A

A


Dyes Derived from R Acid (continued)

505


82

83

101

112

168

202

236



Ponceau R, 2RScarlet R, 2R

Ponceau 4R

Coccinine B

Fast Red BBordeaux B

Amaranth

Acid Alizarin Red BPalatine Chrome

RcdB

DISAZO DYESCloth Red BWool Red B


Manufacture

I '14:— 35,259M'17:—633,429M'18:—

1,189,054M '19:—552,680M'20:—

1,286,002

I '14:— 3,557M'17:— ?M'18:— ?M'19:— 24,152M'20:— ?

I '14:— 25,821M'17:—120,595M'18:—200,415M'19:—161,862I '20:— 7,882M'20:—217,406

I '14:— 86,067M'17:— 66,069M'18:— 73,539M'19:—294,416I '20:— 110M'20:—204,958

I '14:— 7,374M'18:— ?M'19:— 28,081I '20:— 1,342M'20:— 67,817

I '14:— 14,293M'17:— ?M'18:— ?M'19:— ?M'20:— ?


Xylidine

Pseudocumidine

m-Amino-p-cresolMethyl Ether

a-Naphthylamine

Naphthionic Acid

Anthranilic Acid

o-Amino-azo-toluene


A

A

A

A

A

ACrCL

A




238

244

2G9

270

272

298

299

300

341

412



Union Fast Claret

Coomassie WoolBlackS

Naphthol Black GB



Milling Red R

Cinnabar Scarlet BF

Cinnabar Scarlet GCotton Ponceau

Crumpsall DirectFast Red R

Congo Blue 2B


Manufacture

M18:— ?M'19:— ?

I '14:—120,512I '20:— 1,500M'20:— ?

I '14:—103,598M'19:— ?I '20:— 50

M '17:— ?M'18:~- ?M'19:— ?M'20:— ?

Other IntermediatesUstd and Notes

Amino-azo-xylene


a-Naphthylamine

l-Naphthylamine-4: 6-and -4: 7-disulfonicAcids

a-Naphthylamine

Amino-G AcidAnilineG Acid or R Acid

Amino-G Acida-Naphthylamine

Diaroino-diphenyl-methane

R Acid (2 mols)

Diamino-dixylyl-methane

R Acid (2 mols)

Diamino-dixylyl-phenyl-methane

R Acid (2 mols)




A

A

A

A

A

A

CL

CL

D

D



507


414

429

433

434

484



Indazurine B

Indazurine BB

Coomassie Blade B

Coomassie NavyBlue

TRISAZO DYEMilling Scarlet B


Manufacture

I '20:-— 42,357



thalene-4-s u 1 f o n i cAcid


thoic-4 sulfonic Acid


jS-Naphthylamine

1:4-Naphthylene-dia-mine-2-suKonic Acid

0-Naphthol

Diamino-azoxy-tolueneNevile-Winther's Acid


2R Acid

2-Amino-8-naphthol-3:6-disulfonic Acid

Amino-naphthol-disulfonic Acid RR or 2R


HO

H O 3 S I I J S O 3 H

FORMATION.—From sodium 2-naphthylamine-3: 6: 8-trisulfonate byfusion with caustic soda at 220-260°


)8 DYES CLASSIFIED BY INTERMEDIATES

Dyes Derived from 2R Acid

'chvltz

44

442

443

449

453

454

455

457


MOXOAZO DYEAzo Archil R

TRISAZO DYESDirect Black V

Direct IndoneBlueR

Trisulfon Brown B

Columbia Black R

Trisulfon Brown G

Columbia Black B

TrisulfonBrown GG


Manufacture

I '14:—145,73S

I '14:— 16,781I '20:— 38,616

I '14:— 1,307

I '14:— 1,323

I '14:—165,727

I '14:— 7,562I '20:— 38,411


Aniline

Benzidinea-NaphthylamineGamma Acid

Benzidinea-NaphthylamineHAcid

BenzidineSalicylic Acidm-Phenylene-diamine

Tolidinem-Tolylene-diamine

(2 mols)

TolidineSalicylic Acidm-Phenylene-diamine

Dianisidinem-Tolylene-diamine

(2 mols)

DianisidineSalicylic Acid7n-Phenylene-diamine


A

D

D

D

D

D

D

D

Red Acid

l:5-Dihydrox>^naphthalene-3:7-disulfoiiic Acid (not consideredherein)

Resorcine

See, Resorcinol (C. A. nomen.)


Resorcinol (C. A. nomen.)

Resorcine

509

STATISTICS.—Imported '14:— 61,624 lbs.Manufactured ' 17:— ?Manufactured ' 18:— 2,087 lbs.Manufactured '19:— 96,397 lbs.Manufactured '20:—139,315 lbs.

FORMATION.—Benzene is disulfonated with oleum, and the resultingbenzene-m-disulfonic acid is fused with a large excess of causticsoda


Dyes Derived from Resorcinol





Used and Notes


11

35

60

75

NITROSO DYESolid Green O

STILBENE DYEMikado OrangeChloramine

Orange G

MONOAZO DYESSudan G

Azo Phosphine GO

New Phosplrine G

I '14:— 26,010M'17:— ?M'18:— ?IVT19:— ?MJ20:— 38,287

I '14:-

I '14:-

798

50

I '14:— 500

[Dinitroso Derivative]

2>-Nitro-tolucnc-o-sul-fonic Acid (4 mols)

[Resorcinol as reducingagent]

Aniline

m-Amino-phcnyl-tri-methyl-ammoniumChloride

Amino-benzyl-^dimethyl-ainme

M

D

ss

B

B


Dyes Derived from Besorcinol (continued)


143

155

211

213

222

317

374

376

435



ChrysoineTropaeoline

Acid AlizarinGarnet R

DISAJZO DYESResorcine Brown

Fast Brown

Janus Yellow G

PyramidolBrown BG


Pyramidol Brown T

^HISAZO DYESJanus Brown B


Manufacture

I '14:— 6,252M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I '20:— 201M'20:— ?

I '14:— 13,189M'17:— ?M'18:— ?M'19:— ?I '20:— 2,484M'20:— ?

I 714:— 3,206M'17:— ?

MJ19:— ?M '20:— ?

I 14:— 2,250I '20:— 758

M'18:— ?


Sulfanilic Acid

a-A m\ T) o-plienol-p-sulf onic Acid

w-XylidineSulfanilic Acid

NaplithAoiiic Acid(2 mols)

m-Nitro-anilinem-Amino-phenyl-tri-

methyl-amnioniiLniChloride

BenzidineResorcinol (2 mols)


TolidineResoTcinol (2 mols)

p-Amino-benzyl-diethyl-arnine

a-Naphtkylarniae


A

M

A

A

B

D

D

D

B


Dyes Derived from Resorcinol (continued)

511




Used and Notes



Isodiphenyl Black R

Coomassie UnionBlacks

Congo Brown GNaphthamine

Brown 4G

Congo Brown R

Azo Corinth

TETRAKISAZO DYEHessian Brown BBN

XANTHONE DYESRhodamino B

I 14:— 52,141M17M18M19I '20M'20

- 443-229,489

I 14:— 3,045

Rhodamine 12 GF

I '14:— 59,354M17:— ?M18:— ?M'19:~ ?I '20:— 24,709M'20:-~ ?


Gamma Acid

1: 4-lSTaphthylene-dia-mine-2-sulf onic Acid

Gamma AcidResorcinol (2 mols)

BenzidineSulf anilic AcidSalicylic Acid

BenzidineLaurent's AcidSalicylic Acid

TolidineNaphthionic Acid3-Amino-phenol-4-sul-

f onic Acid

BenzidineSulf anilic Acid (2 mols)Resorcinol (2 mols)

Phthalic AnhydrideResorcinol (2 mols)[Phosphorus penta-

chloridc; diethyl-anaine]

Dimethylamino-hy-droxy-benzoyl-benzoic Acid

[Formaldehyde;esterincation]

D

D

D

D

D

B

B



for Dye,

Statistics of 'Import and ,

Manufacture iOther Intermediates

Used and Notes

XANTHONE DYES S |(continued) t \

Fast Acid Violet B «I '14:— 2O,6SS Phthalic AnhydrideM '19:— ? ! Resorcmol (2 mols)I '20:— 2,907 Aniline or p-tol-

uidine (2 mols)[PC15; sulfonation]

Fast Acid VioletA2R I '14:— 875 Phthalic AnhydrideI '20:— 2,679 Resorcinol (2 mols)

o-Toluidine (2 mols)[PC15; sulfonation]

Phthalic AnhydrideResorcmol (2 mols)Mesidine (2 mols)[PC15; Sulfonation]

3:6-Dichloro-phthalicAcid

Resorcinol (2 mols)p-Phenetidine (2 mols)[PC15; Sulfonation]

Phthalic AnhydrideResorcinol (2 mols)

Acid Rosamine A

Fast Acid Blue R

I '14:' I '20:

I '14:-I '20:-

50141

4,022130

franineFluoresceine

Chrysoline

Eosine

I '14:— 2,273

'20:— 10

I '20:— 1,402

I '14:M'17:M'18:-M'19:I '20:-M'20:-

- 94,52S- 68,496-161,153-121,303- 296- 85,489

Phthalic AnhydrideResorcinol (2 mols)Benzyl Chloride

Phthalic AnhydrideResorcinol (2 mols)[Bromination]

or[Fluoresceine

brominated]




513




Used and Notes



Eosine Spirit SolubleMethyl Eosine

Eosine SP

Eosine BNAcid Eosine

Erythrosine G

Erythrosine B

Phloxine P

I J14:-M;20:-

2,315?

I '14:-I '20:-M'20:

20,1431,132

I '14:— 99

I '14:-M'17:-M'18:-M'19:-I '20:-

4,350505

1,636

96,874

I '14:-- 2,244M'17:— ?

M'20:—

Phthalic anhydrideResorcinol (2 mols)[Bromination, methyla-

tion]or

[Eosine methyl ester]

Phthalic AnhydrideResorcinol (2 mols)[Bremination, ethyla-

tion]or

[Eosine ethyl ester]

Phthalic AnhydrideResorcinol (2 mols)[Bromination, nitration]

or[Dibromo-fluoresceine

dinitratcd]

Phthalic AnhydrideResorcinol (2 mols)[Iodation]

or[Fluoresccine iodated]

Phthalic AnhydrideResorcinol (2 mols)[Iodation]

or[Fluoresceine iodated]

3: 6-Dichloro-phthalicAcid

Resorcinol (2 mols)[Bromination]

ss

A







Used and Notes


XAOTHONE DYES(continued)

Cyanosine SpiritSoluble

Rose Bengal

Phloxine

Rose Bengal B

Cyanosine B

Coemleine B

OXAZINE DYESPhenocyanine TC

I '14M'20

:— 2,277

I '14:

I '14:M'17:-M'lS:-M'19:-

1,020

1,354

?

M'19:-M '20:-

I '20:— 4,740


Eesorcinol (2 mols)[Bronaination, methyla-

tion]or

[Phloxine methyl ester]



Tetrachloro-phthalicAcid

Resorcinol (2 mols)[Bronaination]




Resorcinol (2 mols)[Ethylation]

or[Phloxine ethylated]

Phthalic AnhydrideResorcinol (2 mols)[Dehydration][Fluoresceine

dehydrated]

Mtroso-dimethyl-aniline

Gallic Acidor

[GaUocyanine]

ss

M

M






ManufactureOthar Intermediates

Used and Notes


643

644

647

648

OXAZINE DYES(continued)

Phcnocyanine T V

Ultracyanine B

Nitroso Blue MRResorcine Blue

Iris Blue

M'17I '20:- 1,543



or[Gallocyanine;

Sulfonation]


Gallic Acid[Allcaline Condensation]

or[Gallocyanine alkaline

condensation withresorcinol]


Nitroso-resorcinol[Bromination]

M

M

MF

Resorcinol Methyl Ether

Methyl-resorcinol

m-Methoxy-phenol ( C A. nomen.)

JOCHs

FORMATION.—From resorcinol by methyla t ion

LITERATURE.—Ul lmann , Enzy. tech. Chemie, 9, 490


Dye Derived from Resoreinol Methyl Ether


575

Ordinary Kane aM j fJ^aSClass of Dye Manufacture

!XANTHOXE DYE

Rhodine 12 GM 1

!


Dimethylamino-liy-droxy-b e n z o y l -benzoic Acid



B

Resorcinol-succinein3:6-Dihydrox3'-9-xanthene-propionic Acid; y-Lactone (C. A

nomen.)

HO—( \-O-f X , - O H _

CH. O

CH2. CO

FORMATION-.—^From resoreinol and succinic acid (or its anhydride) byheating together at about 200° C.

LITERATURE.—Cohen, Theoretical Organic Chemistry (1918 Ed.), 461

Dye Derived from Resorcinol-succinein

" t a w I S 2 £

XANTHONE DYE570 Rhodamine S I JU:— 600

I '20:— 273


[Dimethyl-amine2mols]


a-Resorcylic Acid (C. A. nomen.)

3:5-Dihydroxy-benzoic Acid7n-Dihydrox^r-ben2oic Acid

COOH


FORMATION.—From 3: 5-disulfo-benzoic acid by caustic soda fusion


Ullmann, Enzy. tech. Chemie, 2, 345

Dye Derived from a-Resorcylic Acid


771



Resoflavine W



Used and Notes

a-Resorcylic Acid(2 mols)

[Oxidation]


M

j3-Resorcylic Acid (C. A. nomen.)


=C 7 H 6 O 4 =154

FORMATION.—By heating resorcinol with a solution of potassium bi-carbonate under reflux

LITERATURE.—Ullmann, Enzy. tech. Chemie, 2, 345Bistrzycki and Kostanecki, Ber. 18, 1984 (1885)

Dye Derived from /3-Resorcylic Acid


49


MONOAZO DYEPrague Alizarin

Yellow G



Used and Notes

m-Nitro-aniline


M

RG Acid



Rho AcidSee, Anthraquinone-1: 5-disulfonic Acid

Eumpff AcidSee, Croeeine Acid

S AcidSee, l-Amino-S-naplithol-4-sulfonic Acid

See, 1: S-Diliydruxy-napLtLalene-4-?ulfonic Acid

Sit, l-Naplithylarnint-S-sulfunic Acid

tfte, l-Xaphthylamine-4: S-di<ulfunic Acid

1-XapLtbol-S-tulfonie Acid (not considered herein)

1: S-DiLydruxy-napLtLalene-2:4-disulfonic Acid (notconsidered herein)

1: 7-DiLydrox\"-naphthalene-6-carbosylic Acid (not con-

Note.—The use of S as a trivial name is very confusing and should beai aided

2S Acid

See, l-Amino-S-naplithol-2:4-disulfonic Acid

Salicylic Acid0-Hydroxy-beiizGic Acid

COOH

OH =C:H £O 3=13S

Technical U. S. P.11s. lbs.

STATISTICS.—Manufactured '17:-— 960,339 2,495,285Manufactured 'IS:—1,395,630 3,270,462Manufactured ' 19:—3,467,055 2,619,726Manufactured '20:—3^914,163 2,663,494

FORMATION.—PLenol is treated -with caustic soda, dried and powdered;and tLt-n >ul)jtct(-d to aetiun of carbon dioxide under pressure andat lU>-l-i:r


LITERATURE.—Cain, Intermediate Products (2d Ed.), 149Lange, Zwischenprodukte, £145, 471—£75, 479

Dyes Derived from Salicylic Acid

for Dye

48

58

96

102

103

133

177

MONOAZO DYESAlizarin Yellow GG

Alizarin Yellow R

Chrome FastYellow GG

Diamond Flavine G

Dutch Yellow

EriochromePhospMne R

Chrome Yellow DMordant Yellow 0

Manufacture

I '14:—144,761M'17:—

1,452,622M'18:—

2,233,208M'19:—163,170M'20:—211,5S0

I '14:— 97,059M'17:—215,46SM '18:—385,910M'19:—130,424I '20:— 860M'20:— S3,334

I '14:— 150I '20:— 500

I '14:— 23,0S9M '17:— ?

M'19:— ?M'20:— ?

I '14:— 1,433

I '14:—129,651M'17:— ?M'18:— 32,011M'19:— ?I '20:— 1,389M'20:— ?

Other IntermediatesUsed and Xotes ]

mOsitro-aniline

p-Nitro-anilineor

Aniline [with nitrationafter coupling]

o-Anisidineor

m-Amino-p-cresolMethyl Ether

Benzidine

Benzidine[Sodium sulfite]

p-Nitro-aniline-o-sulf onic Acid

Broenner's Acid

DyeAppli-cation

M

M

M

M

M

ACr

M


Dyes Derived from Salicylic Acid (continued)


178

199

204

221

250

291

292

294

296

305

339



Crumpsall Yellow


Diamond Yellow G

DISAZO DYESAnthracene Acid

Brown G

Milling Orange

M'17M'18I '20


Azo AlizarinBlack I

Anthracene Yellow CFast Mordant

Yellow

Cotton Yellow G

Hessian Yellow

Brilliant Orange G


Manufacture

I '14:-I '20:-M'20:

13,416125

:— ?:— ?:— 225

I 'U:— 4,370

I '14:I '20:

I '14:-I '20:-

3,678

31,4724,651

I '14:—M'17:—

6,321?


Amino-G Acid

Dehydrothio-p-tolui-dine-sulfonic Acid

orPrimuline

m- or p-Amino-benzoicAcid

Sulfanilic Acidp-Nitro-aniline

Ammo-azo-benzene-sulfonic Acid

p-Phenylene-diamineNevile-Winther's Acid

p-Phenylene-diamineChromotropic Acid

Thio-anilineSalicylic Acid (2 mols)

p-Amino-acetanilide(2 mols)

Salicylic Acid (2 mols)Phosgene

Diamino-stilbene-disul-f onic Acid


Benzidine3 -Amino-phenol-4-

sulfonic Acid



340

340

341

342

343

344

345

346

Dyes Derived


DI-SAZO DYES(continued)

Benzo Orange R

Chlorazol Orange 2R

Cnunpsall DirectFast Red R

Chrysamine G

Diamine FastRedF

Diamine Brown. M

Oxamine Maroon

Oxamine Red

from Salicylic


Manufacture

I '14:— 1,073M'17:— ?M'18:— 50,422M'19:— 42,807I '20:— 220M'20:— 86,210

M'17:— ?M'18:— ?M'19:— ?M'20:— ?

I '14:— 608M'17:— 26,061M'18:— 28,846M'19:— 54,279I '20:— 9,810M'20:— 49,342

I '14:— 50,479M'19:— 56,864I '20:— 4,040M'20:—115,865

I '14:— 65,396M'18:— ?M'19:— 15,959M'20:—257,872

I '14:— 11,636I '20:— 848

Acid (continued)



Benzidine2-Naphthylamine-7-

sulfonic Acid

BenzidineRSalt


(2 mols)

BenzidineGamma Acid[Acid coupling]

BenzidineGamma Acid[Alkaline coupling]


sulf onic Acid

BenzidineJ Acid


D

D

D

D

D

D

D

D




347

348

349

350

355

393

394

404

444

445

446



Diphenyl Brown RN

Diphenyl Brown BN

Diamine Brown B

Alkali Yellow R

Anthracene Red

Diphenyl Brown3GN

Ckrysamine R

Diamine Yellow N

TRISAZO DYESCrumpsall Direct

Fast Brown B


Benzo Olive


Manufacture

I '14:— 13,471

I '20:— 24

I '14:— 3,873M'19:— ?I '20:— 104M'20:— ?

M'20:— ?

I '14:— 6,261M'20:— ?

M'17:— ?I '20:— 313

I '14:— 1,14


BenzidineMethyl-gamma Acid

BenzidineDimethyl-gamma Acid

BenzidinePhenyl-gamma Acid

BenzidineDehydrothio-p-tolui-

dine-sulf onic Acid

o-Nitr o-b enzidineNevile-Winther's Acid

TolidineDimethyl-gamma Acid

TolidineSalicylic Acid (2 mols)

Ethoxy-b enzidinePhenol[Ethylation]

BenzidineAnilineGamma Acid

BenzidineAnilinePhenyl-gamma Acid

Benzidineq-NaphthylammeH Acid


D

D

D

D

ACr

D

D

D

D

D

D







Used and Notes


447

448

449

454

457

465

466

468

475


Benzo Gray S

Diamine Bronze G

TrisulfonBrown B

TrisulfonBrown G

TrisulfonBrown GG


Eboli Green

Diphenyl Green 3G


:— 802

:— 4,495

I '14:— 16,781I '20:— 38,616

I '14:— 1,323

I '14:— 7,562I '20:— 38,411

I '14:— 7,329M'17:— ?M'18:— 29,118M'19:—136,638I '20:— 1,332M'20:— 52,292

Benzidinea-NaphthylamineNevile-Winther's Acid

Benzidinem-Phenylene-diamineHAcid

BenzidinewvPhenylene-diamine2R Acid

TolidineTtt-Phenylene-rH a/mine2R Acid

Dianisidinem-Phenylene-diamine2R Acid


sulf onic AcidAniline

BenzidineSulfanilic Acidl-Amino-8-naphthol-

3:5-disulfonic Acid

BenzidineHAcido-Chloro-2>-nitro-

aniline

BenzidineH Acid2>-Nitro-aniline







Used and Notes


476

477

478

480

482

510


Benzamine Brown3GO

Congo Brown GNaphthamine

Brown 4G

Columbia Green

Congo Brown R

Alizarin Yellow FS

I '14:— 16,988M'17:— ?M'18:— ?M'19:— ?M'20:—623,757

I '14:— 52,141M'17:-M'18:-MJ19:-I '20:-M'20:

- 443-229,489

I '14:-M'18: -I '20:-

45,162

7,555

I '14:— 3,045


Azo Green

BenzidineSulf anilic Acidm-Phenylene-diamine

BenzidineSulfanilic AcidResorcinol

BenjzidineSulfanilic Acidl-Amino-8-naphthol-4-

sulfonic Acid

BenzidineLaurent's AcidResorcinol

Aniline ando-Toluidinep-ToluidineSalicylic Acid (3 mols)

or[FucLsine and

Salicylic Acid]

m-Amino-tetramethyl-p ^ ' - d i a m i n o - t r i -phenyl-methane

or fromm-Nitro-benzaldehyde

and dimethyl-aniline(2 mols)

[Oxidation]

D

D

D

D

M

M



525


549

557



(continued)Chrome Violet

Chrome Violet


Manufacture

I '14:— 51

I '14:— 220M 'IS:— ?


Hydrol[Oxidation]

Salicylic Acid (3 mols)[Formaldehyde and

sulfuric Acid]


M

M

Schaeffer's a Acid


Schaeffer's Acid*

Schaeffer's /3 Acid

2-Naphthol~6-sulfonic Acid (C. A. nomen.)

/3-Naphthol-sulfonic Acid S

/3-Naphthol-sulfonic Acid Schaeffer

/3-Naphthol-a-sulfonic Acid of Armstrong and Schultz

/3-Naphthol-/3-sulfonic Acid

HO3S0 H =

STATISTICS.—Manufactured '17:—13108,049 lbs.2

Manufactured '18:— 169,383 lbs.Manufactured '19:— 146,111 lbs.Manufactured '20:— 475,243 lbs.

FORMATION.—By sulfonation of jS-naphthol, and separation from theCroceine acid formed simultaneously

1 Schaeffer's Acid is very occasionally used when referring to l-Naphthol-2-sulfonicacid, but this is more properly known as Schaeffer's a acid.

2 Includes Croceine Acid.


LITERATTJBB.—Cain, Intermediate Products (2d Ed.), 223Lange, Zwischenprodukte, #2430-2432Thorpe, Die. Chemistry, 3, 624


4

37

70

79

111

123

166

Dyes Derivec


MONOAZO DYESNaphthol Green

Ponceau 4GBCroceine Orange

Brilliant Orange 0

Brilliant Orange RXylidine Orange RR

Fast Red BT

EmineRed

Fast Red E

I fromL Schaeffer's Acid


Manufacture

IMMMIM

IMMMM

IMMMM

IMMMM

MMM

IMi.VJLMMM

'14:—'17:—'18:—'19:—'20:—'20:—

'14:—'17:—'18:—'19:—'20:—

'14:—'17:—'18:—'19:—'20:—

'14:—'17:—'18:—'19:—'20:—

'17:—'18:—'19:-

'14:—J17.'18:—'19:—'20:—

19,14675,85022,46534,646

100?

13,046?

30,82417,27496,573

21,480????

4,204?

18,9097

??

2,473????


[Nitroso-Derivative]

Aniline

Toluidine

Xylidine

a-Naphthylamine

Isodehydrothio-m-xylidine

Naphthionic Acid


A

A

A

A

A

A

A


Dyes Derived from Schaeffer's Acid (continued)

527


196

197

201

234

237

243

248

254

273

289

293



Titian Red

Thiazine Red G

Pigment Scarlet G

DISAZO DYESCloth Red G

Bordeaux BX


Fast Scarlet B

Bordeaux G

DiaminogeneBlue BB

Acid AlizarinBlack SN

Palatine ChromeBlack S

Milling Red G


Manufacture

I '14:— 886M'19:— ?M'20:— ?

I 14:— 4,861M18:— ?M19:— 11,886M'20:— 13,988

M17:— ?M18:— ?M19:— ?

I 14:— 554

I 14:— 1,755

I 14:— 8,308M17:— ?I '20:— 5,936

M17:— ?M18:— ?M19:— ?

I 14:— 69I '20:— 20C


D ehy dro-thio-p-tolui-dine-sulfonic Acid

Primuline

Anthranilic Acid

o-Amino-azo-toluene

Amino-azo-xylene


a-Naphthylamine

Amino-azo-benzene-sulf onic Acid

Amino-azo-toluene-sulf onic Acid

Acetyl-1:4-naphthyl-ene-diamine-6-sul-f onic Acid

a-Naphthylamine

2: 6-Diamino-l-phenol-4-sulfonic Acid

/3-Naphthol

ThioanilineSchaeffer's Acid

(2 mols)


D

D

CL

M

A

A

A

A

D

ACr

A


Dyes Derived from Schaeffer's Acid (continued)


645


OXAZINE DYEGallazine A



Used and Notes


Gallic Acid[Oxidation]


M

Schoellkopf's Acid




Also used for l-Naphthol-8-sulfonic Acid, which is nothere indexed, but the intermediate generally referred tois (fiat one listed first above

Semi-naphthalidam

1:5-Diamino-naphthaleDe (not considered herein)

Siver Salt (Sodium derivative)


SS Acid or 2S Acid

See: l-Amino-8-naphthol-2:4-disxdfonic Acid

m-Sulf anilic Acid

See, Metanilic Acid

Sulfanilic Acid (C. A. nomen. SOzH=l)

p-Amino-benzene-sulfonic acid

Aniline-jp-sulfonie acid

SOsH

NH2


STATISTICS.—Imported '14:— 4,477 lbs.Manufactured '17:—1,184,412 lbs.Manufactured '18:—1,247,478 lbs.Manufactured '19:—1,023,861 lbs.Manufactured J20:—1,796,838 lbs.

FORMATION.—From aniline by heating with sulfuric acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 47Lange, Zwisehenprodukte, #615-620

Dyes Derived from Sulfanilic Acid

529


22

23

138

139

140

141


PYRAZOLONE DYESXylene Yellow 3G

Tartrazine

MONOAZO DYESHelianthineMethyl Orange

Orange IV

Azoflavine RSCurcumeine

Azo Yellow 3G


Manufacture

I '14:— 23,074I '20:— 77,782

I '14:—272,477M'17:— ?M'18:— ?M'19:— ?I '20:— 47,877M '20:—701,722

I '14:— 500M'18:— ?M'19:— ?M'20:— ?

I '14:— 19,020M'19:— ?I '20:— 608

I 14:— 39,869I '20:— 5,225

I '14:—114,689M'17:— ?M'18:— ?M'19:— ?I '20:— 4,818M'20:— ?


l-(2:5-Dichloro-4-sulfo-phenyl) -3-methyl-5-pyrazolone

p-Phenyl-hydrazine-sulf onic Acid

Dimethyl-aniline

Diphenylamine

Diphenylamine[Nitration]

Diphenylamine[Strong nitration]


A

A

A

A

A

A


Dyes Derived from Sulfanilic Acid (continued)


142

143

144

145

146

147

211



Brilliant Yellow SCurcumine

ChrysoineTropoeoline

Orange I

Orange II

Azo Fuchsine G

Azo Fuchsine 6B

DISAZO DYESResorcine Brown

I 14:—

I 14:—M17:—M18:—M19:—M'20:—

I 14:—M17:—M18:—M'19:—I '20:—


Manufacture

9,934

6,252

8,305?

1,323M'20:— 14,684

r 14:—128,877M17:—712,586M18:—916,890M19:—

1,133,925I '20:— 2,265M'20:—

1,850,341

I 14:— 17,819I '20:— 3,694

I 14:— 13,206M17:— ?M18:— ?

I 14:— 13,189M17:— ?M18:— ?M19:— ?I '20:— 2,484M'20:— ?


Diphenylamine[Sulfonation]

Resorcinol

a-Naphthol

jS-Napnthol

1:8-Dihydroxy-naph-thalene-4-sulfonicAcid

1:8-Dihydroxy-naph-thalene-4-sulfonic

Acid[? Classification]

m-XylidineResorciaol



531


212

220

221

259

2C0

261

2G2

4GG

476


MONOAZO DYES{continued)

Fast Brown GAcid Brown G

Palatine Black ABuffalo Black PY

Anthracene AcidBrown G

Ponceau 10 RB

EriochromeVerdone A

Buffalo Black 10B

Victoria Black B

TRTSAZO DYESEboli Green

Benzamino Brown3 GO


Manufacture

I 14:— 17,407I '20:— 485

I 14:—299,274I '20:— 200

M17:— ?M18:— ?I '20:— 225

I 14.— 201

I 14:— 882

M17:— ?M18:— ?M 1 9 : ~ ?M'20:— ?

I 14:— 557

I 14:— 16,988M17:— ?M18:— ?M19:— ?M'20:—623,757


a-NaphtholSulfanilic Acid (2 mols)


a-Naphthylamine

p-Nitro-anilineSalicylic Acid

o-AnisidineCroceine Acid

ra-Amino-p-cresoliS-Naphthol

a-NaphthylamineHAcid

a-Nai >hthylamine1:8-Dihydroxy-naph-thalcnc-4-sulf onic Acic

BcnzidincSalicylic Acidl-Amino-8-naphthol-

3: 5-disulf onic Acid

Benzidinem-Phcnylcne-diamineSalicylic Acid


A

A

ACr

A

ACr

A

A

D

D






ManufactureOther Intennediates

Used and Notes


477

478

485

489

738


Congo Brown GNaphthamine Brown M

4G

I '14:— 52,14117:— ?

M'18:— ?M'19:— ?I '20:— 443

M'20:—229,4S9

Columbia Green

TETBAKISAZO DYESBenzo Brown G

I '14:— 45,162VI'18:— ?I '20:— 7,555

I '14:— 41,905M'17:— ?M'18:— ?M'19:— 83,506I '20:— 2,286M '20:—109564S

Hessian Brown BBN


BenzidineResorcinolSalicylic Acid

BenzidineSalicylic Acidl-Amino-8-naphthol-4-

sulf onic Acid


Sulfanilic Acid (2 mols)

BenzidineResorcinol (2 mols)Sulfanilic Acid (2 mols)

l-Chloro-2: 4-dinitrobenzene

[S plus

D

D

^-Sulfo-anthranilic Acid (C. A. nomen.)

2-Amino-4-sulfo-benzoic AcidP-ATD i no-p-sulfobenzoic Acid

COOH

_ 217


FORMATION.—o-Nitro-toluene is sulphonated with oleum. The resulting

o-nitro-toluene-p-sulfonic acid is converted into the sodium salt

and heated with a 40 per cent caustic soda solution at 90-95°


Dye Derived from ^-Sulfo-ajrthranilic Acid


28


PYRAZOLONE DYEPigment Fast

Yellow G


Manufacture

MJ19:— ?I J20:— 170




CL

Sulfo-naphthalic Acid

Naphthalene-1-sulfonic Acid (not considered herein)

/3-Sulfonic Acid

See} Anthraquinone-2-sulfonic Acid

l-(/>-Sulfo-phenyl)-3-methyl-5-pyrazolone

See, 3-Methyl-l-(p-sulfo-phenyl)-5-pyrazolone

l-(^-Sulfo-phenyl)-5-p3n:azolone-3-caxboxylic Acid

Tartrazinogen-sulfonic Acid

5-Keto-l-(p-sulfo-phenyl)-3-A2-pyrazoline-carboxylic Acid (C. A.

nomen.)

O3H

OC

H2C

N

-C.COOH


FORMATION.—By condensation of phenyl-hydrazine-p-sulfonic acid andethyl oxalacetate

LITERATURE.—Cain, Intermediate Products (2d Ed.), 168LaDge, Zwischenprodukte, #138

Dye Derived from l-(^-Sulfo-phenyl)-5-pyrazolone-3-carboxylic Acid


20


PYEAZOLONE DYEFlavazine S


Manufacture

I '14:— 81,375I '20:— 1,500


Aniline


A

Sulfo-m-tolylene-diamine-bis-(carbonyl-ainino-naphthol-sul--fonic Acid)

SuKcKm-tolylene^iajniaeHiicarbonyl-dihydroxy-dinaphthylamine-

disulfonic Acid

3:5-Bis[i3-(5-hydroxy-7-sulfo-2-napbtriyl)-carbamido]-p4olTiene-

sulfonic Acid (C. A. nomen.)

CH3

. C O . H N / N N H . C O .

SOaH

FORMATION.—^By condensation of tolylene-diamine-suKonic acid

(CH3:NH2:NH2:SO3H=1:2:6:4) with two molecules of J acid

(2-amino-5-naplithol-7-STilfonic acid), by means of phosgene

(COCI2)

LITERATURE.—Ger. Pat. 236,594, Frdl. 10, 904Lange, Zwischenprodukte, #2912


Dyes


280

281

282

Derived from Sulfo-m-tolylene-diamine-bis-(carbonyl-amino-naphthol-sulfonic Acid)



Scarlet GGS





Used and Notes

o-Toluidine (2 mols)

o-Toluidine/3-Naphthylamine

/3-Naphthylamine(2 mols)


D

D

D

Tartrazinogen-sulf onic Acid

See, l-(p-Sulfo-phenyl)-5-pyrazolone~3-carboxylie Acid

2:4:6:8-Tetrabromo-l: 5-diamino-anthraquinone

Br r;o N H 2

V J B r =CMHJJrJN'j0j=554

H2N t V ^

FORMATION.—By bromination of 1: 5-diamino-anthraquinone

LITERATURE.—Scholl and Berblinger, Ber. 37, 4180 (1904)Barnett, Anthracene and Anthraquinone, 229Cf. Lange, Zwischenprodukte, #3231, 3404, 3405

Dye Derived from 2:4:6:8-Tetrabromo-l:5-diamino-anthraquinone


861



AnthraquinoneBlue SR


Manufacture

I '20:— 917




ACr


Tetrachloro-phthalic Acid

Cl

Cll yCOOH ~C8H2C14O4=302


FORMATION.—Phthalic anhydride is warmed for some hours at 200° with6 parts of antimony pentachloride, and chlorine is conductedthrough the molten mass for from 8 to 12 hours


Dyes Derived from Tetrachloro-phthalic Acid


596

597

598


XANTHONE DYESPhloxine

Rose Bengal B

Cyanosine B


Manufacture

I '14:— 1,020

I '14:— 1,354M'17:— ?M'18:— ?M'19:— ?


Hesorcinol (2 mols)[Bromination]

Hesorcinol (2 mols)[Iodation]

Resorcinol (2 mols)[Bromination;

Ethylation]or

[Phloxine ethylated]


A

A

ss

pi ^'-Tetraethyl-diamino-benzohydrol

p: p'-Tetraethyl-diamino-diphenyl-carbinol

p:p'-Bis(diethylamino)-benzohydrol (C A. nomen.)

H

i N < ^ ^ C - < ^ ) > N ( C 2 H 5 ) 2 =C21:


FORMATION.—Diethyl-ardline is condensed with formaldehyde in thepresence of hydrochloric acid to tetraethyl-diamino-diphenyl-methane. This body is now oxidized to the hydrol with leadperoxide



498

Dye Derived from p



Turquoise Blue

^'-Tetraethyl-diamino-benzohydrol


Manufacture

I '14:— 1,541I '20:— 1,407


p-Nitro-toluene[Oxidation]


B

p: ^'-Tetraethyl-diamino-benzophenone

p: p'-Bis(diethylamino)-&enzophenone (C. A. nomen.)

—CO = C2iHo8N2O = 324

FORMATION.—By condensation of diethyl-aniline (2 mols) and phosgene(carbonyl chloride)


Dyes Derived from ^:^'-Tetraethyl-diamino-benzoplienoiie


518

532

560

Ordinary Naine andClass oj Dye



Alkali Violet 6B


Night Blue


Manufacture

I '14:— 51,933

I '14:— 3,020

I '14:— 361M'19:— ?I '20:— 11


Diethyl-aniline

Methyl-diphenyl-amine

[Sulfonation]

y-Tolyl-a-naphthyl-andne


B

A

B


p: j>'-Tetraethyl-diamino-diphenyl-carbinol

See, p: p'-Tetraethyl-diamino-benzohydrol

p: /-Tetraethyl-diamino-diphenyl-methane

p: p'-Methylene-bis-[iV:iV-diethyl-aniline] (C. A. nomen.)

= C2iH30N2 = 310

FORMATION.—By condensation of diethyl-aniline with formaldehydein the presence of hydrochloric acid

LITERATURE.—C/. Cain, Intermediate Products (2d Ed.), 102Cf. Lange, Zwischenprodukte, #1301

Dye Derived from p: ^'-Tetraethyl-dianiino-diphenyl-methane


518





Manufacture

I '14:— 51,933


Diethyl-aniline


B

1:3:5:7-Tetrahydroxy-anthraquinone

See, Anthrachrysone

Tetramethyl-diamino-benzohydrol

See, Hydrol

p: ^'-Tetramethyl-diamino-benzohydrol-sulf onic Acid

5-Dimethylamino-a-(p-dimethylamino-phenyl)-a-hydroxy-o-folu-ene-sulfordc Acid (C. A. nomen.)

(CH3)2N<

H0

SO3H

HN(CH3)2 — Ci7H22N2O4S = 350


FORMATION.—Tetramethyl-diamino-diphenyl-methane (from condensa-

tion of dimethyl-aniline and formaldehyde) is dissolved in mono-

hydrate and sulfonated with 25 per cent oleum at 110°. This

methane-sulfonic acid is now oxidized with lead peroxide to the

hydrol derivative

LITERATURE.—Ger. Pat. 88085; Frdl. 4, 219



Georgievics and Grandmougin, Dye Chemistry, 208

Dye Derived from Tetramethyl-diamino-benzohydrol-sulfonic


531



Eriocyanine A


Manufacture

I '14:— 25,091I '20:— 8,223

M'20:-~ ?


Dibenzyl-aniline-sul-fonic [or disulfonic}Acid

[Oxidation]

Acid


A

Tetramethyl-diamino-benzophenone

See, Ketone

p: //-Tetramethyl-diamino-diphenyl-methane

p: p'-Methylene-bis-[iV: i\r-dimethyl-aniline] (C. A. nomen.)

) = 254


FORMATION.—From dimethyl-aniline (2 mols) by condensing with

formaldehyde in the presence of hydrochloric acid




Dyes


493

603

Derived from p: ^-Tetramethyl-diamino-diphenyl-methane


ATJRAMINESAuramine

ACRIDINE DYEAeridine Orange NO


Manufacture

I '14:—449,276M'17:— ?M'18:— 45,634M'19:—127,567I '20:— 74,414

M'20:— ?

I '14:— 2,336I '20:— 1,925


[Sulfur and ammonia]

[Dinitration, Reduc-tion]

[Ammonia Removal,Oxidation]


B

B

p: j)'-Tetramethyl-diamino-diphenylmethane-sulf onic Acid

6-(p-Dimethylamino-benzyl)-iV: iV-dimethyl-metanilic Acid (C.A.nomen.)

HO3S

/ " " N N (CH3)2 = C17H22N2O3S = 334

FORMATION.—By sulfonation of tetramethyl-diamino-diphenylmethane;or by condensation of dimethyl-metanilic acid and dimethyl-anilinewith formaldehyde


Cain, Intermediate Products (2d Ed.), 102Georgicvics and Grandmougin, Dye Chemistry, 208

USES.—For preparation of prp'-tetramethyl-diamino-benzohydrol-sul--fonic acid

N':N': N": JV'-Tetramethyl-m: pr: '-methenyl-trisaniline {C.A.nomen.)

See, m-Amino-tetramethyl-p': p^-diamino-triphenyl-methane


a-Tetranitro-naphthalene

From 1:5-Dinitro-naphthalene

/3-Tetranitro-naphthalene

1:3:6: 8-Tetranitro-naphthalene (not considered herein)

Y-Tetranitro-naphthalene

1:3:5: 8-Tetranitro-naphthalene (not considered herein)

5-Tetranitro-naphthalene

1: 2: 5: 8-Tetranitro-naphthalene (not considered herein)

Thioaniline

p: p'-Thio-bisaniline (C A. nomen,)

p: p'-Diamino-diphenyl-sulfide

"VTTT ____ f^\ TT "XT C< ___ C\ -\ £»>I\ JC12 L/12-tt i2iN 2U A1D

FORMATION.—^From aniline by heating with sulfur in presence of leadoxide

LITERATURE.—Meyer-Jacobson, Organische Chemie (1902), II, 1, 476

Dyes Derived from Thioaniline


293

294


DISAZO DYES

Milling Red G

Anthracene Yellow CFast Mordant

Yellow


Manufacture

I '14:— 699I '20:— 200

I '14:— 3,678I '20:— 887


Schaeffer's Acid(2 mols)



A

AACr

p: /-Thio-bisaniline (C. A. nomen.)

See, Thioaniline


Thio-carbanilide (C. A. nomen.)

Diphenyl-thiourea

N H . CS . NH = Ci3Hi2N2S = 228

STATISTICS.—Manufactured ' 17:— ?Manufactured '18:—1,326,236 lbs.Manufactured '19:—2,268,375 lbs.Manufactured '20:—2,226,807 lbs.

FORMATION.—From aniline by action of carbon disulfide


Dyes Derived from Thio-carbanilide


874

876

877




Indigotine


Manufacture

I '14:—8,507,359

M'17:—274,771M'18:—

3,083,888M'19:—

8,863,824I '20:—520,347M'20:—

18,178,231

I '14:— 19,329M'17:—

1,876,787M'18:—

1,434,703M'19:—

1,699,670I '20:— 5,512M'20:—

1,395,000


Thio-carbanilide(2 mols)

[KCN, etc.]

Thio-carbanilide(2 mols)

[KCN, etc.; Reduction]or

[Indigo Reduced]

Thio-carbanilide(2 mols), etc.

or[Indigo Sulf onated]


V

V

A


Dyes Derived from Thio-carbanilide (continued)





Used and Notes


878

879

880

881

882

883

884

885


Indigotine P

Brom IndigoRath j en







I '14:— 53,610M'20:— ?

I '14:— 6,856M'17:— 14,100I '20:— 3,691M'20:— ?

I '14:— 16,880M'19:— ?I '20:— 35,857

I '14:-I '20:-

I '14:-I '20:-M'20:-

1,3561,008


or[Indigo Sulf onated]


or[Indigo Brominated]


or[Indigo, Brominated]





3,1914,130

I '14:— 4,518

I '14:-I '20:-

8,1753,503



Thio-carbanilide(2 mols), etc,

or[Indigo, Chlorinated

Brominated]


or[Indigo Chlorinated]


Dyes Derived from Thio-carbanilide (continued)


886

889

890


INDIGO GKOUP DYES(continued)


Indigo Yellow 3G

Ciba Yellow G


Manufacture

I '14:— 12,057

I '14:— 48



or[Indigo Chlorinated,

Brominated]


Benzoyl Chlorideor

[Indigo, BenzoylChloride]

Thio- carbanilide(2 mols), etc.

Benzoyl Chloride[Bromination]

or[Indigo Yellow 3G,

Brominated]


V

V

V

Thio-indoxylSee, 2-Hydroxy-thionaphthene

Thio-indoxyl-carboxylic AcidSee, 2-Hydroxy-thionaphthene-l-carboxylic Acid

o-Thiol-benzoic AcidSee, Thio-salicylic Acid

Thio-salicylic Acido-Mercapto-&enzoic Acid (C. A. nomen.)

o-Thiol-benzoic Acid

Thiophenol-o-carboxylic Acid

COOH

M S H =C7H6O2S = 154


FORMATION.—(1) From o-chloro-benzoic acid by reaction with potas-sium hydrogen sulfide. (2) From anthranilic acid by diazotizingand then running into a solution of sodium polysulfide and sodiumhydroxide



912

919

Dyes Derived


INDIGO GROUP DYESThio Indigo Red B

Ciba Bordeaux B

from Thio-salicylic Acid


Manufacture

I 'U:— 1,102I '20:— 275

I '14:— 899I '20:— 1,786


Thio-salicylic Acid(2 mols)

[Chloro-acetic Acid2 mols; etc.]

Thio-salicylic Acid(2 mols)

[Chloro-acetic Acid2 mols; etc.jBromi-nation]

or[Thio Indigo Red,

brominated]


V

V

Tobias Acid

See, 2-Naphthylamine-l-sulfonic Acid

Also applied to, 2-Naphthol-l-sulfonic Acid

Tolidine

See, o-Tolidine

o-Tolidine (C. A. nomen.)

Tolidine

E3C


STATISTICS.—Imported '14:— 5,874 lbs.Manufactured ' 17:— ?Manufactured ' 18:— ?Manufactured '19:—143,012 lbs.Manufactured '20:—375,905 lbs.

FORMATION.—From o-nitro-toluene by reduction with zinc dust andhydrochloric acid, and conversion of the hydrazo-toluene intotolidine by boiling with hydrochloric acid

LITERATURE.—Cain, Intermediate Products (2d Ed.), 95Lange, Zwisehenprodukte, #1204, 1216

Dyes Derived from o-Tolidine





Used and Notes


338

362

363

DISAZO DYESNaphthamine

Blue 3BI '14:— 11,707I '20:— 400

Toluylene Orange ROxy Diamine Orange M

I '14:— 25,908- ?

I '20:— 1,653

Benzopurpurin 4B

364

365

366

Benzo Purpurin 6B

Benzopurpurin B

Diamine Red BDeltapurpurin 5B

I '14:—351,712M'17:— ?M'18:—356,522M'19.-288,021I '20— 3,492

M'20—617,629

I '14— 9,171I J20:— 4,743

I '14— 21,090M'17:— ?M'18:— ?M'19:— ?

I ' 14— 21,058M ' 1 7 — ?M'18:— ?I ' 20— 1,896

K Acid (2 mols)

4: 6-Diamino-m-tolu-ene-sulf onic Acid(2 mols)


D

D

Laurent's Acid (2 mols)


2-Naphthylarmn e-7-snJfonic Acid

Broenner's Acid

D

D

D


Dyes Derived from o-Tolidine (continued)

547


367

368

369

370

371

372

373

374

375

376

377

378



Diamine Eed 3BDeltapurpurin 7B

Brilliant Purpurin4B

^Brilliant Purpurin R

Brilliant Congo R

Rosazurine G

Rosazurine B

Congo Orange R


Congo Corinth B

Pyramidol Brown T

Azo Blue

TrisulfonBlueR

r

I

II

II

M

IM

IMM

IMM


14:—

'14:—

'14:—'20:—

'14:—'20:—

'18:—

'14:—'19:—

'14:—'19:—'20:—

'14:—'19:—'20:—

6,634

8,051

19,13311,129

7,027254

?

2,196?

198??

911??


2-Naphthykmine-7-sulfonic Acid (2 mols)

Naphthionic AcidBroenner's Acid

Amino-R AcidNaphthionic Acid

Amino-R AcidBroenner's Acid

Ethyl-2-naphthyl-amine-7-sulf onic Acid

2-Naphthylarnine-7-sulfonic Acid

Ethyl-2-naphthylamine-7-suKonic Acid(2 mols)

Amino-R AcidPhenol[Ethylation]

Naphthionic AcidResorcinol

Naphthionic AcidNevile-Winther's Acid

Resorcinol (2 mols)


l-Naphthol-3:6:8-trisulf onic Acid

0-Naphthol


D

D

D

D

D

D

D

D

D

D

D

D




379

380

381

382

383

384

385

386

387

388



Dianil Blue 2RBenzo New Blue 2B

Dianil Blue B

Azo Black Blue B,H

Azo Mauve B

Naphthazurine B

Chicago Blue 2B,Diamine Blue C2R

Oxamine Blue 4R


Columbia Blue G

Chicago Blue R


Manufacture

I '14:— 14,434

M'17:— ?M'20:— ?

I '14:— 4,782

I '14:— 23,877

I '14.— 573M'20:— ?

I '14:— 1,740M'17:— ?M'18:— ?M'19:— 92,214I '20:— 4,520M'20:— 90,147

I '14:— 7,094


Chromotropic AcidNevile-Winther's Acid

Chromotropic Acid(2 mols)

HAcidm-Hydroxy-diphenyl-

amine

HAcida-Naphthylamine

HAcid/3-Naphthylamine

Croceine Acidl-Amino-8-naphthol-4-

sulfonic Acid

J AcidNevile-Winther's Acid

Nevile-Winther's AcidHAcid

l-Naphthol-3:8-disulfonic Acid


l-Amino-8-naphthol-4-sulfonic Acid (2 mols'


D

D

D

D

D

D

D

D

D

D



549

SohultzNumberfor Dye

389

390

391

392

393

394

395

396

397

398



Eboli Blue B

Benzo Cyanine B


Toluylene Orange G

Diphenyl Brown3GN

Chrysamine R

Cresotine Yellow E

Indazurine RM

Direct Blue R

Direct Gray B

Statistics cjImport and

Manufacture

I '14:— 201

14:— 1,365M17:— 14,533M18:— 99,645M19:—182,946I '20:— 1,120

M'20 :—136,891

I 14:— 67,022M18:— ?M19:— ?I J20:— 273

M'20:— ?

M'20:— ?

I 14:-M32O:-

6,261?

M17:— ?


l-Anuno-8-naplitliol-3:5-disulfonic Acid(2 mols)

HAcidl-Amino-8-naplitliol-4-

sulf onie Acid

H Acid (2 mols)

4: 6-Diamino-m-tolu-ene-sulf onic Acid

o-Cresotic Acid

Salicylic AcidDimethyl-gamma Acid


o-Cresotic Acid(2 mols)

1: 7-Dihydroxy-2-naplithoic-4-sulf onic Acid

Nevile-Wintlier's Acid

1:7-DLhydroxy-6-iiaplithoic-3-sulfonic Acid


1:7-Dihydroxy-6-naph-thoic-3-sulfonic Acid(2 mols)








Used and Notes


399

450

451

452

453

454

481


Indazurine GS

TRISAZO D Y E SBenzo Black Blue R

Congo Fast Blue R

Benzo Indigo Blue

Columbia Black R

Trisulf on Brown G

Azo Corinth

I ?14:-M'19:-I '20:-

4,449

723

I '14:— 1,307

I '14:- 1,323

1:7-Dihydroxy-2-naph-thoic-4-sulfonic Acid

Gamma Acid

a-NaphthylamineNevile-Winther's Acid

(2 mols)

a-Naphthylaminel-Naphthol-3: 8-disul-

fonic Acid (2 mols)

a-Naphthylamine1:8-Dihydroxy-naph-


2 R Acidm-Tolylene-diamine

(2 mols)


Naphthionic AcidResorcinol3-Amin o-l-phenol-4-

sulf onic Acid

o-Tolidine-disulfonic Acid

2:2 / -Diamino-5: 5'-bi-m-Zoluene-sulfonic Acid (C. A. nomen.)

H3C CH 3

^ ^ - < ^ ) > N H 2 = C u H 1 6 N 2 O c S 2 = 3 7 2

HO3S SO3H


FORMATION.—From tolidine sulfate by heating with 2 parts of sulfuricacid at 210° from 36 to 48 hours

LITERATUEE.—Cain, Intermediate Products (2d Ed.), 96Lange, Zwischenprodukte, #1269-1271

Dye Derived from o-Tolidine-disulfonic Acid


400


DISAZO DYEMilling Scarlet 4RAcid Anthracene

Red3B


Manufacture

I '14:— 18,330I '20:— 2,336

DjeOther Intermediates Appli-

Used and Xotes cationClass

£-Naphthol (2 mols) } A

^-Toluene-sulfochloride

See, p-Toluene-sulfonyl Chloride (C. A. nomen.)

^-Toluene-sulfonyl Chloride (C. A. nomen.)

p-Toluene-sulfochloride

SO2C1

=: 190.5

STATISTICS.—Imports '14:—small amountManufactured ' 17:— ?Manufactured '18:— ?Manufactured '19:—58,932 lbs.Manufactured '20:— ?

FORMATION.—Toluene is sulfonated with oleum giving a mixture ofo- and p-toluene-sulfonic acids, which are converted to sodiumsalts and dried, and then treated with PCl^+Cl, resulting in o- andp-toluene-sulfonyl chlorides. The POOs formed is first distilledoff and then the mass cooled, whereupon the p-toluene-sulfonylchloride crystallizes out


BieL, II, 132


Dye Derived from j5-Toluene-sulfonyl Chloride

Schvltz Quinary Xame and/ < £ & Class of Dye

1S2MONOAZO DYE

Fast Sulfon VioletBrilliant Sulfon

RedB

Statistics ofI?nport andManufacture

I '14:— 4,871I '20:— 4,740


HAcidAniline

Appli-cationClass

A

Toluidines, mixed

Mixed Toluidines

CH3


Manufactured '171—1,366,321 lbs.Manufactured '18:— 308,667 lbs.Manufactured '19:— 806,210 lbs.Manufactured '20:—1,145,361 lbs.

FORMATION.—Toluene is nitrated using mixed acid, and the mixture ofo- and p-nitro-toluenes is reduced with iron and hydrochloric acid


Dyes Derived from Toluidines, mixed


21


PYBAZOLOXE DTEPigment Chrome

Yellow L



Used and Notes



CL



70

71

688

Dyes Derived from Toluidines,


MONOAZO DYES

Brilliant Orange 0

Azo Fuchsine B

AZINE DYERosolaneMauve


Manufacture

I '14:— 21,480M'17:— ?M'lS:— ?M'19:— ?M'20:— ?

I '14:— 796I '20:— 3

mixed (continued)


Schaeffer's Acid

1:8-Dihydroxy-naph-thalene-4-sulf onic Acid

AnilineToluidines (3 mols)


A

A

B

m-ToluidineNote.—C. A. numbering begins with iV£f2, while German and English

numbering generally start from CHz

NH2

STATISTICS.—Imported '14:—945 lbs.Manufactured '20:— ?

FORMATION.—m-Nitro-benzaldehyde is chlorinated to m-nitro-benzyli-dine chloride (C6H4 . NO2 • CHC12), which by reduction with zincat low temperatures, forms m-toluidine

LITERATURE.—Ber. 13, 677; 15, 2011; 18, 3398Dyes Derived from m-Toluidine


240


DISAZO DYEJanus Red B


Manufacture

I '14:— 250I '20:— 176

Other IntertncdiatesXJsed and Notes

m-Amino-phenyl-tri-methyl-ammoniumChloride

0-Naphthol


B



435

Dyes Derived



from m-Toluidine {continued)



Used and Notes

m-Amino-phenyl-tri-methyl-ammoniuinChloride

Anilinem-Phenylene-diamine


B

o-Toluidine

Note.—C. A. numbenng begins with NH%, while German and Englishnumbering generally starts from CHz

C7H9N =

STATISTICS.—Imported 14:— 656,320 lbs.Manufactured '17:— 336,985 lbs.Manufactured 18:— 638,874 lbs.Manufactured 19:—1,002,982 lbs.Manufactured ;20:—1,302,097 lbs.

FORMATION.—Toluene is nitrated to a mixture of o- and p-nitro-toluenes,which are separated. The o-nitro-toluene is reduced with ironand hydrochloric acid


Dyes Derived from o-Toluidine


68

69


MONOAZO DYESSpirit Yellow R

Chrysoidine R


Manufacture

M19:— ?M'20:— ?


o-Toluidine (2 mols)

m-Tolylene-diamine


ss

B


Dyes Derived from o-Toluidine (continued)

555


124

125

126

127

128



Diazine Green S

Diazine Black

Indoine Blue RUnion Blue R

Methyl Indoine B

Janus Gray B


Manufacture

I '14:— 1,340

I '14:— 2,630I '20:— 701

I '14:— 15,353M'17:— ?M'lS:— ?

MJ17:— ?


p-Tolylene-diamineAniline or2d mol o-Toluidine[Preceding used as

Safranine]with

Dimethyl-aniline

p-Tolylcne-diamineAniline or2d mol o-Toluidine[Preceding used as

Safranine]with

Phenol


Safranine]with

0-Naphthol


Safranine]with

t' Amino-naphthols''


Safranine][Other intermediate

unknown]


B

B

B

B

B




280

2S1

482

512

513

514



Scarlet GGS


TBISAZO DYEAlizarin Yellow

FS


MagentaFuchsine

New Fuchsine 0

Red Violet 5R


Manufacture

I '14:-M '17:-M'18:-M' 19:-I '20:-

M'20:-

I '14M'18MJ19M'20

I '14:-I '20:-

- 87,102- 17,739- 71,675-155,830- 189-284,285

:— 300

331750


o-Toluidine (2 mols)Sulfo-m-tolylene-dia-

mine-bis (carbonyl-amino-naphtliol-sul-fonic Acid)

ft-Naphthylamin eSulfo-TTz-tolylene-dia-

mine-bis(carbonyl-amino-naplithol-sul-fonic acid)

Aniline andp-Toluidine [as

Fuchsine]Salicylic Acid (3 mols)

Anilinep-Toluidine[Arsenic Acid or

Nitro-benzene]

Anhydro-formalde-hyde-o-toluidine orDiamino-o-ditolyl-methane

[o-Nitro-toluene, etc.]

Anilinep-Toluidine[Mtro-benzene, etc., or

Arsenic Acid][Methylation or ethyl-

ation]or









Used and Notes

521


{continued)Spirit BlueAniline Blue

524 Fuchsine SAcid Magenta

525 Red Violet 5RS

526 Acid Violet 4RS

536 Alkali Blue

I '14:— 50,563M'17:—M'18:—MJ19:—I '20:—M'20:—

?

?

?723

I '14:— 19,098I '20:— 524

M'20:— ?

I '14:—286,751M'17:— ?M'18:— 43,184M'19:— 77,796I '20:— 6,778

M'20:— 74,253

Aniline (3-4 mols)p-Toluidine[Benzoic Acid]

or[Magenta phenylated]

Anilinep-Toluidine[SuKonation]

or[Magenta sulf onated]

Anilinep-Toluidine, etc.[Ethylation Sulf ona-

tion]or

[Red Violet 5R,sulfonated]

Anilinep-Toluidine[Dimcthylation,

TrisuKonation]or

[Magenta dimetliylated,trisulfonated]

p-ToluidineAniline (3-4 mols)[Sulfonation]

or[Spirit Blue sulfonated]




537

538

539

540

541

582

606


TRIPHENTL-METHANEDYES (continued)

Methyl Blue for SilkMarine Blue



Pacific Blue

Brilliant DianilBlue 6G

XANTHONE DYEFast Acid Violet

A2R

ACRTDIKE DYEPhosphine

IMMI


Manufacture

14:—18:—19:—'20:—

M'20:—

I

IMMI

14:—

14:—18:—19:—'20:—

M '20:—

II

14:—'20:—

M'20:—

IMMMI

34,867??

2,395?

50,255

91,152?

16,3151,387

98,770

8752,679?

14.-168,17517:—18:—19:—'20:—

M'20:—

??

14,64819,259

?


Aniline (4 mols)2>-Toluidine[Sulfonation]

Aniline (4 mols)p-Toluidine[Di- and trisulf onation]

p-ToluidineAniline (3-4 mols)[Di- and tri-sulf onation]

or[Spirit Blue di- and tri-

sulfonated]

Anilinep-ToluidineDiamino-diphenyl-


ft-Naphthylamine(3 mols)

Aniline2>-Toluidine[Disulfonation]

Phthalic AnhydrideResorcinol (2 mols)o-Toluidine (2 mols)[PC15, Sulfonation]

p-ToluidineAniline[Magenta by-product]


A

B

A

D

B

A

B



559


679

683

687

702

703

704

705

733

888


AZINE DYESSafranine

Salfranine MN

Rosolane 0

Para Blue

Rubramine

Indamine 3R

Indamine 6R

STJLFTJE DYEImmedial Indone

INDIGO GEOTJP DYEIndigo MLB/T


Manufacture

I '14:— 59,921M'17:— ?M'18:—106,591M'19:—131,042I '20:— 386M'20:—149,629

I '14:— 198M'18:— ?M'19:— ?M'20:— ?

I '20:— 1,083

I '14:— 66,170I '20:— 9,681

I '14:— 4,236

I '14:— 10,730I '20:— 827


p-Tolylene-diamineAniline oro-Toluidine (extra

mol)

Dimethyl-p-phenylene-rlmiminft

Aniline[Oxidation]

o-Amino-diphenylamineAniline[Oxidation]

Aniline (3-4 mols)p-Toluidinep-Phenylene-diamine

or[Spirit Blue, p-Pheny-

lene-diamine]


p-Toluidine



p-Toluidine

p-Amino-phenol[S+Na*S]

o-Toluidine (2 mols)[Chloro-acetic, soda-

mide, etc.]


B

B

B

B

B

B

B

S

V

.-,60 DYES CLASSIFIED BY INTERMEDIATES

p-Tolwdine

Xote.—C. A. numbering begins with XH2, while German and Englishhnmbaing generally starts from

/ \

: H 3

STATISTICS.—Imported 14:— 24,686 lbs.Manufactured 17:—223,778 lbs.Manufactured 18:—205,852 lbs.Manufactured 19:—575,841 lbs.Manufactured '20:—894,169 lbs.

FORMATION.—Toluene is nitrated to a mixture of o- and p-nitro-toluenes,which are separated. The p-nitro-toluene is reduced with ironand hydrochloric acid

LITERATURE.—Cain, Intermediate Products (2d Ed . ) , 58Lange, Zwischenprodukte, #234-240, 261

Dyes Derived from ^-Toluidine


4S2

511

512


TRISAZO DYESAlizarin Yellow FS

TRIPHENYI/-METHANEDYES

ParafuehsineParamagenta

MagentaFuchsine


Manufacture

I 14:— 65,026M18:—• ?M19:— ?M'20:— ?

I 14:— 87,102M17:— 17,739M IS:— 71,675M19:—155,830I '20:— 189M'20:—284,285


Aniline ando-Toluidine [or

Magenta]Salicylic Acid (3 mols)

Aniline (2 mols)[Nitro-benzene and iron

or Arsenic Acid]

Anilineo-Toluidine[Nitro-benzene, etc.; or

Arsenic Acid]


M

B

B


Dyes Derived from ^-Toluidine (continued)





Used and Notes

DyeAppli-cation

514

520

521

524

525

526

TRIPHENYL-METHANEDYES (continued)

Red Violet 5R I '14:—I '20:—

331750


Diphenylamine Blue

Spirit BlueAniline Blue

I '14:— 2,149

I '14:— 50,563M'17:— ?M'18:—M'19:—I '20:—M'20:—

??723

Fuchsine SAcid Magenta

Red Violet 5RS

I '14:— 19,098I '20:— 524M'20:— ?

Acid Violet 4RS

Anilineo-Toluidine[Nitro-benzcne, etc.;

or Arsenic Acid][Methylation or ethyla-

tion]or


Aniline (5 mols)[Benzoic Acid]

Aniline (3-4 mols)o-Toluidine[Benzoic Acid]

or[Magenta phenylatcd]

Anilineo-Toluidine[Sulfonation]

or[Magenta sulfonated]

Anilineo-Toluidine[Ethylation, Sulfona-

tion]or

[Red Violet 5Rsulfonated]

Anilineo-Toluidine[Dimethylation, Tri-

sulfonation]or

[Magenta methylated,sulfonated]


Dyes Derived from ^-Toluidine {continued)

Schultz Ordinary xame andSumher Class of Dyefor Dye J *


Manufacture

535

536

537

53S

539

540

541

TRIPHEXYL-METHANDYES

{continued)Methyl Alkali Blue

Alkali Blue

Methyl Blue for SilkMarine Blue



Pacific Blue

Brilliant DianilBlue6G

I '14M'18M'19I '20

:— 27;

:— 2\

I '14:—286,75M '17:— ?M '18:— 43,184M'19:—77,796I '20:— 6,771

M'20.— 74,253

I '14.— 34,867M'18:— ?M'19:— ?I '20:— 2,395

M'20:— ?

I '14:— 50,255

I '14:— 91,152M'18:— ?M '19:— 16,31I '20:— 1,387

M '20:— 98,770



o-ToluidineAniline (3 -4 mols)[Sulfonation]

0-ToluidineAniline (4 mols)[Sulfonation]

o-ToluidineAniline (4 mols)[Di- and tri-sulf onation

o-ToluidineAniline (3-5 mols)[Di- and tri-sulf onation]

or[Spirit Blue Sulf onated]

Anilineo-ToluidineDiamino-dipnenyl-


iS-Naphthylamine(3 mols)

Anilineo-Toluidine[Disulfonation]


B

D



580

606

616

683

686

702

703

Dyes Derived


XANTHONE DYEFast Acid Violet B

ACRIDINE DYEPhosphine

THIOBENZENYL DYEPrimuline

AZINE DYESSafranine MN

Amethyst Violet

Para Blue

Hubramine

from />-Toluidine (continued)


Manufacture

I '14:— 20,688M'19:— ?I '20:— 2,907

I '14:—168,175M '17:— ?M'18:— ?M'19:— 14,648I '20:— 19,259

M'20:— ?

I '14:— 67,976M'17:— 72,461M '18:— 72,778M'19:—271,338I '20:— 441

M '20:—183,179

I '14:— 198M'18:— ?M'19:— ?M'20:— ?


Phthalic anhydrideResorcinol (2 mols)p-Toluidine (2 mols) or

Aniline (2 mols)[PCI5, Sulfonation]

Anilineo-Toluidine or

2d mol Aniline[Magenta by-product]

p-Toluidine (4 mols)[Sulfur, Sulfonation]


Aniline[Oxidation]

Diethyl-p-phcnylene-diamine

Diethyl-aniline[Oxidation]

Aniline (3-4 mols)o-Toluidinep-Phenylene-diamine

or[Spirit Blue and p-

Phenylenc-diamine]


o-Toluidine


A

B

D

B

D

B

B

5&4 DYES CLASSIFIED BY INTERMEDIATES

Dyes Derived from j5>-Toluidine (continued)

Schultz'

for Dye' of Dye

AZIXE DYE(continued)

705 I Indamine 6R


S52 Alizarin Irisol D, R

S53

S54

855

856

859

860

864

AnthraquinoneViolet

Alizarin ViridineDG,FF

Alizarin PureBlueB

Alizarin Astrol B

Gyananthrol R

Cyananthrol G

AnthraquinoneGreen GX


Manufacture

I '14:— 66,170I '20:— 9,681

I '20:— 401

I '14:-I '20:-

1,2021,649

I J20:— 11,397

I '14:I '20:

I '14:-I '20:-

10,90715,518

1S,7922,416

I '14:-I '20:-

1,7092,531



o-Toluidine

Quinizarin[Sulfonation]

1:5-Dinitro-anthraqui-none

[Sulfonation]

Anthraquinone-2-sul-fonic Acid

[Sulfonation][Or through Alizarin

Bordeaux from Aliz-arin]

l-Amino-2:4-dibromo-antliraquinone

[Sulfonation]

l-Bromo-4-methyl-amino-antliraquinone

[Sulfonation]

l-Amino-4-bromo-2-methyl-anthraquinone

[Sulfonation]

l-Amino-4-bromc-(chloro)-2-methyl-an-thraquinone, etc.

[Sulfonation]

1-Nitro-anthraquinone-6-sulf onic Acid

Aniline

DyeAppli-cation

ACr


Dyes Derived from ^-Toluidine (continued)

565


865



(continued)Alizarin Cyanine

Green E



Used and Notes

Quinizarinp-Toluidinc (2 mols)[Sulfonation]


ACr

o-Toluidine-m-sulfonic Acid

See, 4-Amino-m-toluene-sulfonic Acid (C. A. nomen.)

/>-Toluidine-o~sulfonic Acid

See, 5-Amino-o-toluene-sulfonic Acid (C. A. nomen.)

8-^-Toluino-l-naphthalene-sulfonic Acid (C. A. nomen.)

See, p-Tolyl-l-naphthylamme-8-sulfonic Acid

m-Toluylene-diamine

See, m-Tolylene-diamine

o: ^-Toluylene-diamine

See, m-Tolylcne-diamine

Toluylene-diamine-sulfonic Acid

See, 3: 5-Diamino-p-toluene-sulfonic Acid (C. A. nomen.)

m-Toluylene-diamine-sulfonic Acid

See, 4: 6-Diamiixo-m-tolucne-sulfonic Acid (C. A. nomen.)

/>-(o-Tolyl-azo-)-o-toluidine (C. A. nomen.)

See, o-Amino-azo-toluene


4-m-Tolylene-bis(thiourea) (C. A. nomen.)

See, m-Tolylene-dithiourea

4-m-Tolylene-diamine (C. A. nomen.)

See7 m-Tolylene-diamine

m-Tolylene-diamine

4-7n-Tolylene-diamine (C. A. nomen.

m-Toluylene-diamine

o: p-Toluylene-diainine

Note.—English and Germans often start numbering from

NH:

= C7HioN2=122

STATISTICS.—Imported J14:—135,383 lbs.Manufactured '17:—302,596 lbs.Manufactured '18:—612,163 lbs.Manufactured '19:—139,544 lbs.Manufactured '20:—689,036 lbs.

FORMATION.—From ;?i-dinitro-toluene by reduction with iron and hydro-chloric acid


Dyes Derived from m-Tolylene-diamine

SchuhNumberfor Dye

34


MONOAZO DYESChrysoidine R


Manufacture

I '14:—111,006M'17:— 58,115M '18:—137,035M '19:—220,542I '20:— 1,102M'20:—186,793


Aniline


B


Dyes Derived from m-Tolylene-diamine (continued)

567





Used and Notes


69

284

295

352

413

453

455

458


Chrysoidine R

DISAZO DYESVesuvine BBismarck Brown II

Diphenyl FastBlack

Direct Violet R

Direct Violet BB

TRISAZO DYESColumbia Black R

Columbia Black B

Carbon Black

I '14:—171,133M' 17 :—262,600M' 18 :—295,080M'19:—631,308M'20:—484,929

I '14:— 882

I '14:— 661M'19:— ?

I '14:— 4,396

I '14:— 1,307

I '14:—165,727

o-Toluidine


Gamma Acidp: p'-diamino-ditolyl-

amine

Benzidine1:7-Dihydroxy-6~naph-



thalene-4-sulfonicAcid

Tolidine2R Acidm-Tolylene-diamine

(2 mols)

Dianisidine2R Acidm-Tolylene-diamine

(2 mols)

p-Phenylene-diamine-sulf onic Acid

[from p-Nitro-aniline-o-eulf onic Acid]

l-Naphthylamine-6(7)-sulf onic Acid



Dyes Derived from m-Tolylene-diamine (continued)





Used and Notes


461

463

602

605

670

710

711


Coomassie UnionBlack

Erie DirectBlack RX

Cotton Black E

ACRIDINE DYES

Acridine Yellow

Benzoflavine

AZINE DYE

Neutral Red

I '141—248,567M'19:— ?M'20:—

2,050,741

I '14-M'19:-

1,913?

1:4-Naphthylene-dia-mine-2-sulf onic Acid

Gamma Acidm-Tolylene-diamine

(2 mols)

BenzidineAnilineHAcid


[Formaldehyde, Am-monia removal,Oxidation]

I '14:— 600

MJ18:— ?

SULFUR DYE

Immedial Yellow D

Immedial Orange N

I '14:— 13,400

I '14:— 500


Benzaldehyde[Ammonia removal,

Oxidation]

Nitroso-dimethyl-aniline or


[Oxidation]

[Sulfur]

[Sulfur]


^-Tolylene-diamine (C. A. nomen. NHt=l)

p-Toluylene-diamine

Note.—English and Germans often start numbering with CHz

569

NH2

C^| CH3 n n vrI O7XI10JN2

H2

122


FORMATION.—By reduction of amino-azo-toluene (from 0-toluidine)

with zinc dust and hydrochloric acid

LITERATURE.—Nietzki, Ber. 10, 1158

Green, Organic Coloring Matters (1908), 37

Dyes Derived from ^-Tolylene-diamine

JSchultz

for Dye

124

125

126


MONOAZO DYES

Diazine Green S

Diazine Black

Indoine Blue R

Statistics ojj. lYtporz ana

Manvfacture

I '14:— 1,340

I '14:— 2,630I '20:— 701

I '14:— 15,353M'17:— ?M'18:— ?


o-ToluidineAniline or o-Toluidine[or Safranme]Dimethyl-aniline

o-ToluidineAniline or o-Toluidine[or Safranino]Phenol

o-ToluidineAniline or o-Toluidine[or Safranme]jS-Naphthol


B

B

B


Dyes Derived from />-Tolylene-diamine {continued)


127

128

679



Methvl Indone B

Janus Gray B

AZINE DYESafranine

M '17:—


Manufacture

I '14:— 59,920M '17:M'18:-M'19:-I '20:-

M '20:-

-106,591-131,042- 386-149,629


0-ToluidineAniline or o-Toluidine[or Safranine][" Amino-naphthols "]

o-ToluidineAniline or o-Toluidine[or Safranine]etc.

o-ToluidineAniline or

2d mol o-Toluidine


B

B

B

l-ToIylene-2:6-diamine-4-sulfonic Acid

See, 3 : 5-Diamino-p-toluene-siilfoinc Acid (C. A. nomen.)

m-ToIylene-diamine-sulfonic Acid

See, 4:6-Diajnino-m-toluene-siilfonic Acid ( C A, nomen.)

m-Tolylene-dithiourea

4-m-Tolylene»bis[thiourea] (C. A. nomen.)

N H . C S . N H 2

X H . C S . NH» = C9Hi2N4S2=240


FORMATION.—By heating m-tolylene-diamine thiocyanate several hourson a water bath


Dyes Derived from m-Tolylene-dithiourea


712

716


SULFUR DYESKryogene Yellow G

Kryogene Yellow R


Manufacture

I '14:— 1,126I '20:— 1,543

I 14:— 4,804


Bcnzidine[Sulfur]

[Sulfur]


S

S

/>-Tolyl- a-naphthylamine

iV-p-Tolyl-1-naphthylamine (C. A. nomen)

FORMATION.—From a-naphthylamine hydrochloride and p-toluidine

by heating together to about 280°


Dye Derived from />-Tolyl-a-naphthylamine


560



Night Blue


Manufacture

I 14:— 361M'19:— ?I '20:— 11




B

!2 DYES CLASSIFIED BY INTERMEDIATES

^-Tolyl-l-naphthylamine-8-sulfonic Acid

S-p-Tolumo-l-rcaphthalene-sulfonic Acid (C. A. nomen.)

Tolyl-peri Acid

HO3S

CAUSTICS.—Imports '14:—1,097 lbs.Manufactured '18:— ?Manufactured '19:— ?Manufactured '20:— ?

)RMATION.—From l-naphthylamine-8-sulfonic acid and p-toluidineb}r heating together in an autoclave

TERATURE.—Cain, Intermediate Products (2d Ed.), 195Lange, Zwischenprodukte, #2859

Dyes Derived from ^-Tolyl-l-naphthylamine-8~sulfonic Acid

I*2 Ordinary Name andClass of Dye

89

157

MONOAZO DYESulf on Acid Blue B

DISAZO DYESulfoncyanine


Manufacture

I '14:— 35,560M '17:— ?M '19:— ?M '20:— ?

I '14:—145,694M '17:— ?M'18:— ?M'19:— ?I '20:— 18,327

M'20:— ?


HAcid



A

Tolyl-peri Acid

See, 2>*Tolyl-l-naphthylajnine-8-sulfonic Acid


1:2:4-Triamino-anthraquinone

CO

573

NH2

FORMATION.—1:4-Diamino-anthraquinone is diacetylated, and then

nitrated with nitric acid of sp. gr. 1.5. By reduction of the nitrated

product the 1: 2:4-triamino-anthraquinone is prepared


Dye Derived from l:2:4-Triamino-anthraquinone


822



Algol BrilliantOrange FR


Manufacture

I J14:— 6,195I >20:— 482


Benzoyl Chloride


V

Triamino-triphenyl-methane

Tris(p-amino-phenyl)-?nethane (C A. nomen.)

p-Leucaniline

H2N< >NH2

FORMATION.—(1) From para-rosaniline by reduction with zinc. (2) From

corresponding nitro-compounds by reduction

LITERATITRE.—Beilstein, Orgardsche Chemie (3d Ed.), 4,1194

•4 DYES CLASSIFIED BY INTERMEDIATES

Dye Derived from Triamino-triphenyl-methane

rJlvltZimberr Dye

511


TBIPHENTL-METHAXEDYE



I '14:— 65,026M'18:— ?M'19:— ?M'20:— ?


(Oxidation)

Appli-cationClass

B

a-Trichloro-toluene

See, Benzo-tricHoride

3:4:5-Trihydroxy-benzoic Acid

See, Gallic Acid

Trimethyl-m-aoiiino-phenyl-aminoniiini Chloride

See, (w-Amin(>phenyl)4rimethyl-aminoiiium Chloride

a-Trinitro-naphthalene

1:3:5-Trinitro-naphthalene (not considered herein)

/3-Trinitro-naphthaJene


7-Trinitxo-naphthaleiie


5-Trinitro-naphthalene

1:2:5-Trinitro-naphthaJene (not considered herein)

l:3:5-TriphenyI-hexahydro-s-triazine (C. A. nomen.)

See, Aiihydro-formaldehyde-aniline


Tris(^-amino-phenyl)-methane (C. A. nomen.)

See, Triamino-triphenyl-methane

575

Trisulfonic Acid

See, Naplithalenc-1: 3: 6-trisulfonic Acid

5: 5'-Ureido-bis(2-amino-benzene-sulfonic Acid) (C. A. nomen.)

See, Diamino-diphenyl-urea-disulfonic Acid

m-Xylene (C. A. nomen.)

m-Xylol

JCH3

FORMATION.—This occurs in commercial crude xylol as the most abun-dant constituent, and is separated from its isomers by treating thecrude xylol with a limited quantity of sulf uric acid, and by hydroly-sis of the sulfonatc formed

LITERATURE.—Green, Organic Coloring Matters (1908 Ed.), 5

Dye Derived from m-Xylene


564


TLUPIIENYL-METHANEDYE(?)

Naphthalene GreenV

Statistics ofI in'port and

Manufacture

I '14:— 22,144I '20:— 9,291


p-Dimethylamino-benzaldehyde

Dimethyl-aniline


A


XylidineThe crude mixture contains the following isomers:-

NH3

CH3

CH3

NH2

32 4-xylidine(m-4-xyhdme)

H3C

2 5-xyhdine(p-xylidme)

NH2

2 6-xylidine(m-2-xylidine)

(C A nomen(CHl)

2 3-xyhdine(o-3-xylidine)

Q

CH33 4-xyhdine(o-3 -xylidine)

(C A Tiotnen. NHz=l)(CHl)

STATISTICS.—Imported '14:— 21,836 lbs.Manufactured '17:-^25,873 lbs.Manufactured '18:—534,834 lbs.Manufactured '19:—386,635 lbs.Manufactured '20:—1,054,476 lbs.

FORMATION.—Xylene is nitrated with mixed acid, preferably cold.The mixed nitro-xylenes are then reduced with iron and hydro-chloric acid


Dyes Derived from Xylidine


76

77

78


MONOAZO DYESSudan II

Azo Coccine 2R,

Cochineal Scarlet 4R


Manufacture

I '14:— 501M'17:— 27,595M'18:— 23,692M'19:— ?M;20:—170,658


/3-Naphthol

Nevile-Wlnther's Acid

l-Naphthol-5-sulfonicAcid


S3

A

A


Dyes Derived from Xylidine (continued)

577


Ordinary Name andClas* of Dye



Used and Notes


79

80

82

685


Brilliant Orange RXylidine Orange 2R

Wool Scarlet R

Ponceau R

AZINB DYETannin Heliotrope

I '14:— 4,204M'17:— ?M'18:— 18,909M'19:— ?M'20:— ?

I '14:— 39,8

'14:— 35,259M'17:—633,429M'18:—

1,189,054M'19:—552,680M'20:—

1,286,002

I '14:— 1,398I '20:— 249

SchaefTer's Acid

l-Naphthol-4: 8-disul-f onic Acid

R Acid


A

A

B

2:4-Xylidine (C. A. nomen. NH2=1)

m-Xylidine

N H

= C 8 H u N = :0

CH 3

STATISTICS.—Manufactured '20:—but amoun t not disclosed

FORMATION.—By separation from commercial xylidine as ace ta te

LITERATUBE.—Cain , Intermediate Products (2d Ed . ) , 59


Dyes Derived from 2:4-Xylidine


81

82

211


MONOAZO DYESPalatine Scarlet ABrilliant Cochineal

Ponceau 2RScarlet 2R

DISAZO DYEResorcine Brown


Manufacture

:— 7,510

I '14:— 35,259M'17:—633,M '18:—

1,189,054M'19:—552,680M ' 2 0 : -

1,286,002

I '14:— 13,189M'17:— ?M'18:—M'19:—I '20:—

M '20:—

??

2,484?


l-Naphthol-3:6-disul-fonic Acid

R Acid429 [Only small part of total

production from m-xylidinc]

Sulfanilic AcidResorcinol


2: 6-Xylidine (C. A. nomen. NH>2=1)

p-Xylidine(CH3=JO

H3C

FORMATION.—Crude xylidine is treated with sufficient glacial acetic

acid to cause the m-xylidine acetate to crystallize out . T h e mother

liquor is mixed with hydrochloric acid, and after a few days the

p-xylidine hydrochloride is separated

LITERATURE.—Cain, Intermediate Products (2d Ed. ) , 59



Dye Derived from 2:6-Xylidine

579


438


TBISAZO DYEMelogene Blue BH


Manufacture

M '17:— ?M'18:— ?




D

m-Xylidine

See, 2: 4-Xylidine (C. A. nomen.)

m-4-Xylidine

See, 2: 4-Xylidine (C A. nomen.)

/>-Xylidine

See, 2: 5-Xylidine {C. A. nomen.)

Xylidine-sulfonic Acid

C6H2. NH 2 . (CH3)2. SO3H = = 201

FORMATION.—^Probably by sulfonation of either crude or purified

xylidine with sulf uric acid in a vacuum or in a current of an indiffer-

ent gas

LITERATURE.—Thorpe, Die. Chemistry, 5, 797, 798

Junghahn, Ber. 35, 3747-3767 (1902)

SchultzNumherfor Dye

214

Dye Derived


DISAZO DYEFast Brown 0

from Xylidine-sulfonic Acid


Manufacture

I '14:— 2,000


Xylidine-sulfonic Acid(2 mols)

a-Naphthol


A


4-(2:4-Xylyl-azo)-2:5-xylidine (C. A. nomen.)

See, Amino-azo-xylene

Y Acid

See, G Acid

Yellow Acid

l:3-Dihydroxy-naphthalene-5:7-disulfonic Acid (not consideredherein)

Zeta Acid

Naphthasultone-3-sulfonic Acid (not considered herein)

F O R M U L A I N D E X O F I N T E R M E D I A T E S

The formulas are indexed here for the 487 intermediates for whichdata and tables are listed. Only one chemical name is given, but onthe pages referred to there are enumerated the various trivial names andsynonyms.

The arrangement of the formulas follows that of the 1920 ChemicalAbstracts (C. A. 14, 4557) where "The arrangement of symbols informulas is alphabetical except that in carbon compounds C alwayscomes first, followed immediately by H." "The arrangement of theformulas is also alphabetical except that the number of atoms of anyspecific kind influences the order of compounds/7 e.g., all compoundswith C6 come before those with C7, thus CcHsCl precedes C7HcClNO2.This is likewise true for all the other atoms, and consequently we findC7H6C1NO2 before C7H9N, and C8H2Br2ClNO before C8H2C14O4.

I t is believed that a formula index affords the easiest and surest wayto find an organic compound, and it is for this reason that this indexis given. This is paiticularly true of intermediates where often manynames are used for the same chemical individual.

CClaO

CeHsClWuC«HsClN2O7S

CeHsClaNOaC6H3N3O7CeEUCINO*CaEUClNOsS

CeEUNaOs

CaHsCKhSCeHaClaNCaHtClaNOCeHsNOa

CaHsNOs

CaHsNsOiCeHsNaOsCaHaClNOjS

CeHaNaOa

PAGEPhosgene 486Dihydroxy-tartaric Acid 229l-Chloro-2 4-dmitro-bonzeno 1614-Chloro-3 5-dmitro-bcnzeno-

bulfonic Acid 1622 5-Dichloro-nitro-benzono 210Picric A( id 495o-and p-Chloro-nitro-bonzonea 1092-Chloro-5-nitro-bonzo no-sul-

f onic Acid4-Chloro-3-nitro-b( nzono-sul-

f onic Acidtn-Dinitro-benzono2 4-Dinitro-phonolChloro-benzone2-Chloro-4-nitro-amhneBonzene-sulf onyl Chloride2 5-Dichloro-amhno2-Ammo-4 6-diohloro-phenolNitro-bonzenop-Nitroso-phonolNitro-phonol, crudeo-Nitro-phonolp-Nitro-phenol4-Nitro80-rG3orcinol2 4-Dinitro-anilinePicramic Acid2-Ammo-6-chloro-bonzene-8ul-

f onic Acid»7i-Nitro-anilinep-Nitro-anilme2-Amino-5-mtro-bonzonc-sul-

fonic Acid4-Amino-3-nitro-benzonc-sul-

fonic Acid6-Nitro-motanihc Acid

109

170251258161107125200504304484J44*5436449248494

45420421

74

75434

CoHsNaOiS

CJIsNaOoSa

CeHioOsCai^ClNOs

C7EUCI2O

PAGECoHcNaOeS 2-Ammo-6-nitro-phenol-4-

sulf onic Acid 77CcHoO Phenol 459CeHoOa llosorcinol 509CeHeOs Pyrogallol 499CeHeOoS Pyrogallol-5-sulfonic Acid 500CaH7N Anxlmo 90CaH7NO m-Amino-phenol 77

p-Armno-phcnol 78CeHyNOaS Motamhc Acid 333

Jjulfanihc Acid 528CetfrNTQiS 2-Amino-phonol-4-sulfonic

Acid 803-Amino-phenol-4-sulfomc

Acid 81C«H7NOoSa 2-Amino-p-bonzono-disulfonic

Acid 394-Amino-m-bonzono-disul-

fonic Acid 39CaH7NO7Sa 4-Arnino-phcnol-2 C-disul-

fonic Acid 79CaEhNsOa 4-Nitro-m-phenylono-diamino 437CoIisNa w-Phonylono-diamino 405

7)-Phonylene-diamme 470CoIIsNaOaS p-Phonylono-diaimne-sulfonic

474AndP lieny 1-hy drazinc-p-sulf onic

A( id 4812 O-Diannno-l-phonol-4-aul-

fonic Acid 198m-Phonylone-di amino-disul-

fonio Acid 473Aooto-acetic Ethyl Ester 212-Chloro-5-mtro-benzaldehydo 1682-Chloro-6-nitro-benzaldchydo 1682 5-Dichloro-benzaldehyde 209

5 8 1

582 FORMULA INDEX OF INTERMEDIATES

C7H6C1O

C7H6C1NO2CHNOC 7 6 2 5CTHCOC7HflO2

C7HGO2SC7HCO3C H O

C7HCO4SCrHeOEC7H6O7S2C7H7CIC7H C1OSC7H7NOC7H7NO2

C7H7NO3

C7H7NO4C7H7NO6S

CrHaCINOCvHaClNOsS

CTHSNSOC7H8N2O2

C7H8N2O3

C7H8OC7HaO2C7H0N

CTHQNO

CTHQNOSS

C7HioN2

C7HioN2OsS

CsH-BrzClNO

C8H4CI2O4CH4O3C8H5NO2

C8H6C1NO4S

sflOSCSHTCIOS

C«H7NOC*H7NOS

Benzoyl Chlondeo-Chloro-benzaldehyde2-Chloro-benzaldehyde-G-sul-

f onic AcidBcnzo-trichlondew-Nitro-bcnzaldehydeo-Nitro-benzaldehydep-Nitro bcnzaldehvdcp-Nitro-benzyl Chloride2 4-Dimtro-toIucnoDimtro-p cresolBenzaldehydeBeii7oic Acidwi-Hydroxy-benzaldehj doThio-sahcyhc AcidSalicylic Acida-RehOicyhc Acid/S Resorcvhc AcidBen/caldehydc-o-sulfomc AcidGallic AcidBenzaldehydc-disulfonic AcidBenzyl Chlondep-Toluenc-sulfonyl Chloridem-Ammo-benzaldohj dep-Amino-ben7aldehydom Ammo-benzoic AcidAnthranihc Acido-Nitro-toluenep-Nitro-tohicne5-Ammo-sahcylic 4.cido-Nitio-amsoleGallamide5-Nitro-o-toluene-sulfoiuc

Acidp-Sulfo-anthramhc Acid5-Chloro-o-anisidme2-Annno-5-chloi o-p tolucne-

sulfomc Acidp-NitrofeO-methyl-anihno2-Niti o-p-toluidme3-Nitro-p-i oluidme5-Nitro-o-tokudino2-Amino-G-mtro-p-crcsol4-Nitr o-o-ani aid me5-Nitro-o-amsidmoCresolResorcmol Methyl EtherJV-Methyl-amlmeToluidincs (mixed)m-Toluidinoo-Toluuhnep-T oluidme2-Annno-p-cresol3-Amino-p-( icsolo-Anisidine4-Annno-m-toluone-sulfonic

Acid5-Amino-o-toluone-aulfonic

Acidm-Tolylenc-diammcp-Tolylene-diammo3 5-Diammo-p-toluone-sul-

fomc Acid4 6-Diirnino-m-toluene-sul-

fonic Acid5 7-Dibromo-isatm ChlorideTetrachloro-phlhahc A( id3 G-Dichloro-plithahe AcidPhthahc AnhydrideIsatmPhthahmide4-Chloro-2-mtro-phf»nyl-

thioglycohc Acid2-Hyrlroxy-thionaphthenem-Chloro plu nyl-thioslycolic

AcidIndoxyl5-Amino-2-hydroxy-thionaph-

thene

PAGE140158

15913842742S42943226125212013730S5445185lf5171222 SO12114 3551

373840

110450451

SI-42G2S7

452532150

4044045445515575

4254201775153 30552553554500

4748

107

80

r S 7

500

200

2002005,3 (>2114S7J21493

170313

171320

58

C8H7NO3C8H7NO4S

CsHaNaOsCsHsOs

CsH8O75S2

CsHoN

C8H0NOCsHoN02CsHioC8HioN20

CsHnN

CsHnNO

CaHuNOaSCaIIi2N2

C8Hi2N2O3S2

CsIIoOsS

CoII7BrOS

C8Il7C104S

C0II7N

C«HoC102S

COHDNOC»HoN04

CBIIIOCINO

C0II11NO

CBH12N2O2

CeHj2N 12CalliaN

CDITi4N2

3oErnCiivr2

C10II6N2O4

CioITe02Ciollc04C10H0O&S

CioHoOaSa

PAGE2-Nitro-m-tolualdehyde 449o-Nitro-phenyl-thioglycoho

Acid 438p-Nitro-acetanihde 417o-Cresotic Acid 177Gallic Acid Methyl Ester 2933-Methyl-benzaldehyde-4 G-

disulfonic Acid 337Anhydro-formaldehyde-o-

tolmdme 90Acetanihde 21Phcnyl-glycme 475w-Xylene 575p-Amino-acetamlide 26p-Nitroso-dnnethyl-anihno 4 307>-Nitroso-oih'sl-anihno 445Dirnethyl-amlme 237iV-Ethyl-inilmo 271JV-Methyl-o-toluidino 345X> hdine 5702 4-Xyhdine (NH2 = 1) 5772 5-Xj hdme (NH<> = 1) 5782-Arnmo-p-ci esol Methyl

Ether 40m Dimethylamino-phenol 230m-Ethvlimiiio-phcnol 271p--Phenetidmo 458Xyhdine-sulfonic Acid 579N iV-Diinethyl-m-phcnylcne-

diim me 244N 2V"-Dimethyl-p-plieny]one-

dinmme 244F t h\ 1-phenyl-liydi azine 277JZV JV-Dinicthyl-7)-phenylene-

diamine-tlnosulfonic Acid 2402-H ydroxy-thionaphthcne-1-

caiboxvhc Acid5-B r om o-2-l i y d r oxy 1-3-m 0 tl ly 1-

thionaphthcno5-Chloro-phenyl-thioglycol-

o-caibo^cyhc AcidIsoquinohnoQumolmo4-Chloi o-2-Toly 1-thioglycohc

Acid7-Methyl-mdoxylPhenyl-glycmo-o-carboxyhc

Acidp-Dimethylannno-benzoyl

Chlondep-Dimethylammo-benzalde-

hvdep-Nitroso-ethyl-o-tolindino5-Dimethy lununo-2-m troso-

75-creHolm-Tolylone-ditlnourcaAT-Ethyl-JV-niothyl-anilmoA^-Ethyl-o-toluidinoA^-13thyl-p-toluidinoMesidmcPseudocumidmoo-Amino-ben/yl-djmethylainmo 42p-Ammo-bcn/yl-diniethyl-

amineA^-Ethyl-4-m-tolyk ne-dia-

minuA^-Ethyl-p-t olylcno-diamine(m-Annr o-phenyl)-ti lmothyl-

ammonium Chlondo1 5-Dmitro-naphtlialcno

315

150

171323503

172341

478

232

231440

230570274281282332497

42

28,3

1 5-and 1 8-Dimtio-naphtlia-loncH

1 8-Dinitro-naphtlialcno1 2-NaphthoqumonoNaphtha/ann1 2-Naphthoqmnon(i-4~Hul-

fonic Acid1 2-Naphthoq\nnonc-4 C-

disulfomc Acid

82250

25G257381352

382

381


PAGEC10H7CIO4S l-Cbloro-8-naphthol-4-sulfonic

Acid 1GIl-Chloro-8-naphthol-5-suifomc

Acid 16CCioH7Ci07S2 l-Chloro-8-naphthol-3 6-

disulfonic Acid 16-iC10H7NO2 l-Nitroso-2-naphthol 44'CioH7N08S3 1 8-Naphthasultam-2 4-di-

sulfonic Acid 35!CioH8 Naphthalene 317CioHaChNaOiS l-(2 5-Dichloro-4-sulfo-phcn-

yl)-3-methyl-5-pyrazolone 212C10H8N2O4S l-Nitroso-2-naphthylannnc-

6-sulfomc Acid 418CioHsNaOeS l-Ammo-8-mtro-2-naphthol-

4-sulfonic Acid 76l-(p Sulfo-phenyl)-5-pyrazo-

lone-3-carboxyhc Acid 533CioH80 a-Naphthol 359

/9-Naphthol 3(>1C10H8O2 1 5-Dihydroxy-naphthalenc 222

2 7-Dihydroxy-naphth ilenc 223CioHgOi 7 S-Dihydroxy-4-methyl-

coumann 222CioHaOiS Croccme Acid 179

l-Naphthol-5-sulfomc Acid 372-Naph.thol-l-3ulfomc Acid 37b2-Naphthol-7-sulfomc Acid 377Nevile-Wmther s Acid 413Sch leffcr'g Acid 525

CioHsO&S 1 7-Dihydioxy-na,phihalcne-4-sulfomc Acid 221

1 8-Dihj. droxy-naphthalcne-4-sulfomc Acid 225

C10II8O0S2 Naphthalenc-1 5-disulfomcAcid 348

Naphthalcnc-1 G-disulfonicAcid 318

Naphthalenc-2 7-disulfomoAcid 348

CioIIsOS. G Acid 280l-Naphlhol-3 0-disulfomo

Acid 309l-Naphthol-3 8-diaulfonio

Acid 370l-Naphtliol-4:8-disulf 01110

Acid 3722-Naphthol-3 7-disulfomc

Acid 373R Acid 504

CioHsOsSa Chroinodopic Acid 173CioIIaOoba Naphth ilc nc-1 3 5-lnsul-

fonic Acid 349Niiphlhaleno-1 3 G-tnaul-

fonic Acid 350CioHsOioSa l-Naphthol-3 G 8-tnsulfomt

Acid 3792-Naphthol-3 G 8-LriHulforuc

Acid 380C10H9N Lopichne 331

a-Nciphthylannno 381/5-NaphthyLiti)ino 391Quinaldmc 501

C10H0NO 5-Ainmo-l-nuphthol 02C10H9NO3S Biocnnor s Aeid 152

Laurent's Acid 32<)Naphthiomo Acid 6r)$l- Japhthyla1Inlnc-2-sulfonlo

Acid 39Sl-NaphtliyIammc-6-sulfoinc

Acid 300, 400l-Naphthylanuno-7-sutfomc

Acid 400, 4011-Naphthylammc-S-sulfomc

Acid 4022-Naphthvlammc-l-sulfonic

Acid 4022-NaphthyKmine-5-8ulfonic

Acid 403

CioIIoNOfiS2

C10IIBNO7S2

C10II0NO0S3

PAGE2-NaphthyIamine-7-suIfonic

Acid 4042-Naphthylamine-8-sulfonic

Acid 403, 405l-Ammo-2-naphthol-4-sulfonic

Acid 67l-Amino-2-naphthol-6-sulfonic

Acid 68l-Ammo-5-naphthol-7-sulfomc

Acid 69l-Amino-8-n iphthol-4-sulfonic

Acid 69l-Anuno-8-naphthol-5-sulfonic

Acid 712-Ainino-l-naphthol-4-sulfonic

Acid 722-Amino-3-naphthol-6-sulfonic

Acid 72Gamma Acid 294J Acid 324Aimno-G Acid 54Ammo-R Acid 83Treund's Acid 285l-Naphthylamine-3 8-disuI-

fonic Acid 3931-N aphthy 1 imme-4 6-disul-

fomc Acid 3941-N aphthy lamine-4 7-disul-

fonic Acid 394l-Naphthylamme-4 S-dibul-

fonic Acid 395l-Naphthylamine-5 7-disul-

fonic Acid 3952-Naphthylainine-5 7-disul-

fonic Acid 396l-Anni)o-S-naphthol-2 4-di-

sulf onic Aoid 631-Anuno-S naphthol-3 5-di-

Hulfonic Acid 64II Acid 208K Acid 3252 11 Add 507l-Naphthvlamino-3 G 8-

tnsulfoDU Acid 4061-Niphthj 1 umm-4 G 8-

trisxilfonic Acid 4072-Naphthylammc~3 6 fc>-

tnaulfonic Acid 4073-Mct hyl-l-phenyl-5-pyra-

/olono 3131 3-Naphthylc nc-diammc-6-

auHonic Acid 4091 1-Napht hj 1< nc-diannnc-2-

Hulfonio Acid 4101 4-N aphthy lonc-diaminc-G-

eulfomc Acid 4112 7-Naphthylpne-diammc-

sulfonic Acid 4113-Mothyl-l-(27-aulfophenyl)-

5-pyiazolone 3441 5-N aphthy lcnc-diammc-

3 7-diauHomc Acid 4081 8-Nnphthylone-diaminc-

6 0-diaulf0111c AcidCh] 409

10343S

215217215

218

219

220L olli 0N2O 3S2 Diethy 1-p-phenylonc-dian unc-

thiuHulfomc Acid 220

/10II11CIO3S 4-CWoro-6-mcthoxY-3-mc thyl-phonyl-thioRljcolic Acid

J10II14N2O 73-NitiOBo-dicthyl-amlme5-Dicthvlammo-2-nitroao-

ph( nolDicihyl-anihncm-Dioi hylammo-phcnolDiothyl-anilinc-w-sulfomc

AcidN iV'-Diethyl-m-phenylene-

diaminoN iV'-Diethyl-j^-phenylenc-

diamine

d o I I u N^IOIIIBNO

IOIIIBNOSS

584 FORMULA INDEX OF INTERMEDIATES

CnHsOjCUHSOTS

C11H10O3S2

C11H10O4SC11H11NO4SCnHnClNOCnHnNOC H NC12H7NO2Ci-EUNCi2H9N3OCHNO

C12H10CI2N2Ci2HioN2OfiS

C12H10N4O4isio

C12H11NCiaHuNOC12H11NOOCi2HnNO3SCHNOSCi2iiNOCuHuN.Ci2HnN3O2CisHuNaOiCiaHuNiOaS

CI2H12N2O

GaHwNaOiS

Ci2H12N2O«Ci2HI2N2SCVH13NGJHWNO

Ci2Hx»NO3S

CisHxaNaCuHuNOiCiaH12N2SCiaHuNCiaH13NOsS

PAGEl-Hydroxy-2-naphthoic Acid 3103-Hydroxy-2-naphthoic Acid 3101, 7-Dmydroxy-2-naphth.oic-

4-sulfonic Acid 2271 7-Dihydroxy-6-naphthoic-

3-sulf omc Acid 2285-Ethvlmercapto-2-hydroxy-

thionaphthene-1-carboxykcAcid 273

5-Eth oxy-2-hydroxy-thionapn-thene-l-carbo\yhc Acid 268

Methyl-gamma Acid 340p-Diethylamino-benzoyl

Chloride 2133-Diethylamino-p-cresoI 214p-Amino-benzyl diethylamme 41Acenaphthenequinone 19-Napbthisatm 358

Carbazole 1542-Ammo8-hydroxy-phena7ine 572 4-Dinitro-4'-hydroxy-

diphenylamine 2552 4-Dimtro diphenylamine-

3'-sulfonic Acid 2542 4-Dimtro-diphenylamme-

4/-sulfonic Acid 2542 5 Dimtro diphenylamine-

3 4 disulfonic Acid 253o 0 -Dichloro-bpnzidine 210Nitro-diphenylarmne-sulfonic

Acid 433Benzidine sulfon-disulfonic

Acid 1364 -Amino-2 4-dinitro di-

phenylamme 513-Hydro\y-acenaphthene 306Diphenylamine 261m-Hydroxy-diphenylatnino 309a-Naphthyl-glycme 412Diphenylarmne-aulfonic Acid 262Acetyl-H Acid 22Ammo-azo-benzene 320-Nitro-benzidme 4312-Amino-4'-hydroxy-4-nitro

diphenylamine 56Amino-azc-benzene-sulfonic

Acid 34Armno-azc-benzene-disulfonic

Acid 33o-Amino-diphenylamine 52p-Amino-diphenylamino 52Benzidme 1254-Amino-4'-hy dioxy-diplieny 1-

atnme 56p-Amino-diphenylamine-2-

sulfomc Acid 53Benzidine-sulfomc Acid 136Acetyl-1 4-naphthylene dia-

mine-6-sulfonic Acid 22Benzidine-di8iilfonic Acid 135Thioanihne 541Ethyl-a-naphthylamme 275l-Amino-2-naphthol Ethyl

Ether 66Ethyl-2-naphthylannne-7-sul-

fonic Acid 276Dimethyl-gamma Acid 243Ethyl-gamma Acid 272j> p'-Diamino-diphenylamine 1922 4~Diamino-4'-hydroxy-di-

phenylarrune 1974-Anuno-chry8Oidine 47Gallanilide 289Tbiocarbarnb.de 542iV-Methyl-diphonylamino 338JV-Methyl diphenylamme-

sulfomc Acid 339p p'-Diamino-diphenyl-

methane 192

Ci4HaBr4N2O2

Ci4HoN206Ci4H«N2Oi4S2C14H6N2O16S2

Ci4H7ClO2

CX4H7NO6

C14H7NO7C14H7NO7SCnHsBrNO 3

CuHaClNOiC14H8O2CuH8O2SCulUQi

CHHSOSSCwHsOeCHOS

Ci4H»NO2

CuHsNCUCHHBNOS

CuIhNObSCuHioCuHioNsOCi4HioN802

i4HioO14H10O2

C14H10O3'14H11N3O2

C14H1SN2O882

uHiaNsSC14H14N 2O eS2

PAGEiV -Phenyl- -m-tolylene-

diamine 485Diamino-diphenyl-urea-disul-

fomc Acid 1932 4 6 8-Tetrabromo-l 5-

diamino-anthraqumone 5351 5 Dichloro-anthraquinone 2072 6-Dichloro-anthraquinone 2082 7-Dichloro-anthraquinone 208Dmitro-anthraquinones 2501 5-Dimtro-anthraq\iinone 2511 5-Dimtro-anthraflavic-3 7-

disulfonic Acid 2494 8-Dmitro-anthrachrysone-

2 6-disulfonic Acid 2491-Bromo-anthraquinone 149l-Anuno-2 4-dibromo-anthra-

quinone 501-Chloro-anthraquinone 1562-Chloro-anthraquinone 157Nitro-ahzann {crude) 4183-Nitroalizann 4184-Nitro-ahzarin 4193-Nitro-flavopurpunn 433l-Nitro-anthraquinone-6-

sulfonic Acid 427l-Amino-2-bromo-4-hydroxy-

anthraquinone 441 4-Diamino-2 3-dibromo-

anthraquinone 191l-Ammo-6-chloro-anthra-

qvanone 45Anthraquinone 111Pbenanthrene-qumone 458l-(or 2-)Mercapto-anthra-

qumone 332Alizarin 24Anthrarufin 116Quimzann 502Purpurm 498Anthraquinone-2-sulfomc Acidl 14Anthrachrysonc 109Anthraqmnone-1 5 and 1 8-

disulfonic Acids 112Anthraquinone-2 6-disulfonic

Acid 112Anthraquinone-2 7-disulfonic

Acid 1131-Amino-anthraquinone 292-Amino-antbraqiunone 30l-Ammo-4-hydroxy-anthra-

qumone 553-Amino-alizaTin 274-Amino-ahzann 28l-Amino-4 5 8-tnhydroxy-

anthraqumone 881 5-and 1 8-Amino-antlira-

quinone sulfomc Acids 31Anthracene 1082-Isatin Anihde 321Diamino-anthraquinones 1891 4-Diamino-anthraqumone 1871 5-Dianamo-anthraqumono 1884 8-Diammo-anthrarufin 189Dmitro-stilbene-disulfonio

Acid 2601-Anthrol 1179-Anthrol 1181-Hydioxy-anthranol 307o-Benzoyl-benzoic Acid 1401 2 4-Tnammo-anthra-

quinone 573Denydro-thio-p toluidme-

sulfomc Acid 182Dinitrc~dibcn7yl-di8\ilfomo

Acid 252Dehydro-thio-p-toluidme 181Diamino-stilbenc-disulf omc

Acid 199


C14H15N Benzyl-methyl-anilino 14C14H16N3 o-Ammo-a7o-toluene 3C14H15N3O3S o-Ammo-azo-toluenc sulfomc

Acid 3C14H15N3O8S2 Dimethvlamino-azo-benzene-

disulfomc Acids 23C14H16N2 o-Tohdine 54C14H16N2O 4-Dimethylamino-4'-hydroxy-

diphenylamme 234Fthoxy-bcnzidme 20'

C14H16N2O2 Dianisidine 20C14H16N2O2S JV-(3-Ammo~4-methyl-phenyl)-

p-toluenc-sulf amide 0(C14H16N2O6S2 o-Tohdme-disulfoino Acid 55(Ci4HicN4 Dimethyl-p p'-dianuno-azo-

bemene 242CMHISN<0 Diammo-17 ox>-toluene 19C14H17N3 p p-Diammo-ditolyl-amino 194C16H7CIO4 1-Chloro-anthi aquinone-2-

carboxylic Acid 158C16H8CINO3 2-Anthraquinonyl-urea

Chloride IKl-Amino-4-bromo-2-methyl-

anthraquinonel-Bromo-4-methylamino-

anthraqumone 1512-Bromo-l-methylammo-

anthraqiunone 1512-Methyl-anthraqumono 336l-Ammo-2-methy l-anthri-

quinone 59l-Methylammo-anthraquinone335l-Anuno-4-methoxy-antlira-

quinone 59Benzyl-ethyl aniline 1443-Ethoxy-4'-methyl-diplienyl-

amme 27027S145

C15H10O2C16H11NO2

C16H11NO3CisHnNCieHnNOC1CHX7NO3SCi5HnNO«S2C15H17N3

C15II18N2O3SC16H18N2O6S3

C10H10N2O2CHNOC16H11NCHSCK5H12O6CieHisN

CHH13NO4SC1BH14N4O6

C16H16N2S

Ci«Hi8N2O

Ci7H«ClOCi7HioBrN02

Ethyl-sulf obenz 1-anihneBenzyl ethvl-anihno-disul-

fonic Acidp-Amino-bcnzyhdene-ethyl-

phenyl-hydrazone 43p p'-Diammo-ditolyl-methane 195iV -Et hyl-iV1~phenyl-4-7n-

tolyleno-diammo 277rthyl-sulfobenzyl-p-phcny-

lene-diamine 280

2803202020

3115164S24S348447418723318418523523237

213100152

y o b y p p h 3 lene-diannnc-thiosulfonicAnd

Indirubin1-Aoetamido-anthraquinono2-Acctuniido-anthraqiunone/3-H\ droxy-naphthoquinonjl-

amlme-p-sulf onic A cidRosorcmol-suocmeinPhcnyl-a-naphthylammoPhenvl-jS-naphthylammcPhcnvH-naphthylaimnc-S-

sulfomc AcidPhenyl gamma AcidDiacetyl-o o'-dinitro-ben/i-

dine(Dimethylamino-hydroxy-

benzoyl)-bc nzoic AoidDphydro-tliio-ra-xylidinciso-Dehydro-thio-w-xyhdme4-Dimethylamino-3 '-mcthoxy

benzophenoneDimethylamino-bcnzoyl-

methyl-amhneAmmo-a7o-xvlene7)-DicthyIammo-azo-bcnzeneChloro-bcnzanthrone4-Bromo-JV-methyl-anlhra-

pyndopo

PAQBC17H10O Benzanthrone 123C17H16N Bcnzyl-a-naphthylaimne 147

Methyl-phcnyl-a-naphthyl-amine 312

Mcthy 1-phcny l-j9-naphthyl-anunc 342

p-Tolyl-a-naphthy]aminc 571CITHUNOSS p-Tolyl-l-naphthylannn( -S-

sulfomc Acid 572C17H20N2O Ivetono 327C17H22N3 Diamino-dixylyl-mcthane 105

4 4/-Din\cUiyl-di iinmo-3 3 -ditolyl-moth.uio 212

p p'-retramcthyl-diamino-diphcnyl-mcthaiic 539

C17H22N2O Hydrol 01C17H22N2O3S p p'-retramothyl-dnimino-

diphenyl-ixiethane-Hulf 0111cAcid 510

C17H22N2O4S p p'-Tctramcthyl-diaimno-benzoliydrol-**\ilion\c Acid 538

Ci8Hi2O Mothyl-ben7 uithronc 338C18H12O3 Naphthoyl-ben/oic Acid 3b JC18H14N2O4 1 b-(or 1 7-)Diacotanndo-

anthraqumone 18GC18H10N2 N A -Diphcnyl-w-phcnylenc-

diamine 2G44 Ph( nylamino-4'-hydroxy-

diphcnylamino 403C1BH18N2O 4-Phenylamino-4'-hvdi oxy-

(phcnyl-3'-tolylanniH) 464C10H10N3 Tnamino-tnphcnyl-mctliano 57 iC20H11NO Benzanthrono-quinohnt 124C20II15N3 a-Amino a o-naphthalcno 5C20HK1NO3S Dibenzyl-anihnc-BiiKoxiK Acid 205C20H20N2 JV Bcnzyl-iV -pbcn 1-4-m-

tolvlcne-dianuno 14.SN Nf-{o o'-Di1olvl)-rn-

phf nyknc-duumne 200N N'(p p'-Ditolyl)-?/!-

phcnyU ne-diamine 2bOC2iIIi2ClNO3 l-Bcnzoylannno-4-cliloi o-an-

thi aqmnonc 1V)C21H14N2OS l-Annno-4-bon7oylammo-

antliiaqumono 40JV-Bcn7oyl-o-tolidino 112Anhj dro-fornnaldohydo-nnihna bi)

C21H28N2O 2 V -rl otraothyl-diamino-bon-/ophcnonc 537

C21II30N2 p p'-Tc trap thy 1-diammo-di-plienyl-methano 538

p. p'-lotrac<hyl-di immo-bi n-7ohydiol 530

C22H18N3O4S 4-(p-IIydroxy-phtnyl-amiiio)-1-phonylanuiio-iJaplit halon< -8-sulfonic Acid «H2

2sHi8 Dipheiiyl-naphlhyi-inclluiiu 203Diamino-dixyiyl-phcnyl-nu -

thane 100C23H27N3 m-Animo-toirainothvl-p' P '-

diammo-triplu nj. I-nu thunc bOwI Na 2V N'-(p p'-Ditol>l)-2 7-

naphthyleno-diunnnc 2(J5i2ttH2oN3 N Jv'-Di-2-nuphlhyl-m-

phony]cn(-diammo 217C28H14N2O4 Indanthrono •ilOC28HHN2O7S Indanthrono-sulfonic A( id 317

Pnmulmo-aulfonic Acid (bo-dium Salt) 405

—-- Pnmuhno-sulfomc Acid 495C2BH24N4O1383 Sulfo-wi-tolylone-diainino-biH-

(earbonyl-ammo-naph1 hol-sulfomo Acid) 531

2 2'-Dimethyl-l l'-bumthra-quinono 211

P A R T I I

G L O S S A R Y O F D Y E N A M E S

AND

P A G E I N D E X O F S C H U L T Z N U M B E R S

G L O S S A R Y O F D Y E N A M E S

'he number of dye names in use is very large. Norton, in Artificial'stuffs Used in U. S., lists almost six thousand in his index wheren a number of individual marks are grouped together under thereviation V.M. (Various Marks).'he list of dyes in stock in the German dye factories on August 15,3, the so-called Reparation Dyes, embrace over seven thousand•ks.hroughout Germany, Switzerland, United States, France and Eng-, there are probably twelve thousand different dye marks in use,Ly of these being for the same chemical compound of the same orifferent degrees of purity.bis glossary is based largely upon the list given in the index of Dr.tnas H. Norton's Artificial Dyestuffs Used in the U. S., which isby permission. A number of corrections have been made to this

and a great number of additions. These additions comprise alllames first given in Schultz's Farbstofftabellen, and many more fromJUS sources. However, a number of the separate marks for ao. name are often here listed on the same line to save space,le new American and English names that have arisen during thefew years have not been included, due to difficulty of adequatelying them.lis glossary copies Norton in assigning Schultz numbers followed byrs to dyes closely related to a given Schultz Dye. Norton's prac-regarding dyes of unknown composition is also used, the numbersemployed being the same as given in Norton. Hence ready refer-can be made to Norton's book for statistical information con-

ng these dyes of unknown composition, which could not be classi-m these tables. Some of Norton's dyes of unknown compositionbeen identified and the proper Schultz number assigned.Lder Serial Number Column those numbers without any letterced refer to Schultz Numbers; those with a prefix of A, S, or Uto Azo, Sulfur or unclassified dyes of unknown composition.is used for Various Marks as applied to dye names, and Var.

s various manufacturers and is employed rather than list a con-ible number of manufacturers for a given dye.

589

590 GLOSSARY OF DYE NAMES

The following abbreviations are used for manufacturers.A Actien-Gesellschaft fur Anilin-Fabrikation, BerlinAW A. Wiescher & Co., Successors, Haeren, BelgiumB Badische Anilin- und Soda-Fabrik, LudwigshafenBrAlizCo. British Alizarin Co.BD British Dyes, Ltd., HuddersfieldBK Leipziger Anilinfabrik Beyer & Kegel, FurstenbergBy Farbenfabriken vorm. F. Bayer & Co., LeverkusenByCo Bayer & Co., Rensselaer, N. Y.C Leopold Cassella & Co., Frankfort on the MainCICo . . . . Clayton Aniline Co., Clayton near ManchesterCDCo. . .Central Dyestuff Co., Newark, N . J.CG Chemikalienwerk Griesheim, Griesheim on the MainCJ "Carl Jager Anilinfarbenfabrik, DiisseldorfCR Clauss & Co. (formerly Claus & R6e), Clayton near ManchesterCV Colne Vale Chemical Co., Milnsbridge near HuddersfieldDH Farbwerke vorm. L. Durand, Huguenin & Co., Germany and

FranceFA Farbwerk Ammersfoort, Ammersfoort, NetherlandsG Geigy, BaselGrE Chemische Fabrik GriesheimJElektron, Offenbach on the MainH Read Holliday & Sons, HuddersfieldH&M... .Heller & Merz Co., Newark, N. J .I Gesellschaft ftir chemische Industrie, BaselK Kalle & Co., Biebrich on the RhineKi Kinzlberger & Co., in PragueL Farbwerk Mulheim vorm. A. Leonhardt & Co., MtilheimLev Levenstein, Ltd., Crumpsall ValeM Farbwerke vorm. Meister Lucius & Bruning, HochstNF NiederlandeseheFarben-und Chemikalienfabrik Delft, Delft.P SociSte Anonyme desMatieres colorantesetproduits chimiques

St. Denis (formerly A. Poirrer), St. DenisQ Imports of Unknown SourceS Chemische Fabrik vorm. Sandoz & Co. BaselSch Schoellkopf Aniline & Chemical Works, Buffalo, now National

Aniline & Chemical Co.tM Chemische Fabriken vorm. Weiler-ter-Meer, UerdingerWB W. Beckers Aniline and Chemical Works, BrooklynWD Wtilfing Dahl & Co., Barmen

Note, Within the past few years many of these companies have consolidated orchanged names.


Name

Acetyl Red GXAcetylene Blue 3 BAcetylene Blue b BAcid Alizarin BlaclAcid Alizarin Black RAcid Alizarin Black brAcid Aluann BUck bNAcid Ahzann Black bllAcid Ahzann Biown BAcid Alizarin BlueAcid Ahzann Blue BB GRAcid Ah/ann GarnetAcid Ah/ann Gainct RAcid Ali/ann Green B GAcid Ah/ann Gieen 3 GAcid Aluann Hod BAcid Ahzann Violet NAcid Ahzann Yellow GGWAcid Anthi icene BiownAcid Ant hi accne Brown M IAcid Anthi accne Biown PGAcid Antln \ccne Biown RAnd Anthracene Biown

RH WAcid Antln accne Brown

WSGAcid Anth ac*ene Red ^ BAcid Antln uencRcdSBL GAcid BlackAcid Black AOAnd Black ASAcid Blacl 10 BAcid Black b BAAcid Black 4 BDAcid Black BRAcid Black BRAcid Black DAcid Blacl EAcid Black EWAcid Black G 1IA HASAcid Black IIAcid Black IvBAndBla<kMAcid Black MAcid Black MAcid Black SOAcid Black 32Acid Blac k 203 \Acid Black 2195Acid BlueAcid BlueAcid BlueAcid Blue greenishAcid Blue BAcid Blue 7 BAcid Blue BA C DRSAcid Blue LAcid Blue EXAcid Blue OGAcid Blue AGAcid Blue PNAcid Blue RAcid Blue RAcid Blue 5 RAcid Blue RBrAcid Blue VAcid Blue YAcid Blue 466Acid Blue 22244Acid Blue 23579Acid Blue BlackAcid Brilliant Red 2 BAcid Brown

Manufacturer

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SerialNo

UOOUbisUb49

1503 502SS2 SO2ssa15470070015515579179(a20220415(88SSaSSa8bSSaSSa

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Name-

And Brown GAnd Brown RAcid Brown RNAcid Brown SRAnd Biown VAnd Biown YAcid Chr )inc Black GAnd Cl lomeBlick I GAnd Chi ome BUck RHAnd Chrome BUck RHVcid Chrome Black RHNAnd Chi one Black WSA< id Chr >me BUck 1551Acid C hi ome BlueAcid Chi ome Blue (reddish)And Chi ome Red BAnd Chioi io Blue BAcid Chrome Blue * G\nd Chi ome Red NAcid Chroi le Blue 2 RAcid Chi ome Blue 5 R\ad C lnooc Violet RAnd ConnthAnd Comilh 240 SAcid Cresol Black 119GAcid CrimsonAnd Crimson D\ id Cyamne BPAcid Daik GreenAcid EosinoAnd Tosine CA GAnd Eosine 3 GAnd Fosinc I new LBA id Eosine L 27314 bPAnd 1 osinc 11 $2Vnd Eosine 13389And Tast Blue SBAc id rant BlucbRAnd 1 ast Giee n b BAcid 1 ast ViolotAcid FuchsmeAcid GreenA id Gree n\cid GreenAnd Green (V M )And Giecn 2 A B 2 BAAnd Grcon2 BAcid Green (B BW\ndGrcen2 BGAcid Gucn GAcid CrcenGGAcid IndigounoAcid Kraft BiownAcid MagentaAnd MJ,( enl i4cid Ma c nta 6 BAcid Magenta B PAcid M igc nta TCNSAcid Magenta GAnd Magenta 0Acid Magenta SAnd Magenta &Acid Magenta 2Acid Magenta Ciyst ils IAcid Milling Black BAnd Milling Red GAcid Milling ScarletAcid Navy Blue SIAc id Olive 27( IAcidol Azo Viole t RAcidol A7O Violot SAcidol I ast Violot A 2 RAcidol Violet BR

Manu-facturer

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GICoAWKtMtMtMtM

Soi lalNo

212212a212a212a212a212

Al47aA117A11SAblOAllSaA149A723U302A5J2U209A724U200A725U207U20SU210U522U002U501

lbba100a705b505b590500a590a590a500a590a590ft189188

A5UU551

521501502a505505a502a502504502505505877U9152452 It521524521521524r>2\52152 \52420529*484

A5.KTJ39*A512A513ASHTJ523


NameManu-fac-turer

SerialNo. Name

Manu-fac-turer Serial

No.

Acid Phosphine RAcid Pure Blue RAcid Pure Blue RCAcid PurpleAcid Red2B, 4BAcid Red 6 BFAcid Red CBAcid Red FLAcid Red GAcid Red GAcid Red3GAcid Red RAcid Red 4 RAcid Red SAcid Red 3 SAcid Red C19Acid Red 1622Acid Red 1642Acid Red 1645Acid Rhodamine BAcid Rhodamine 3 BAcid Rhodamine BGAcid Rhodamine GAcid Rhodamine RAcid Rosamine A.-Acid RubineAcid Scarlet GAcid Scarlet 2 RAcid Scarlet SGAcid Silk Black RAcid Silver Black RAcid Silver GravAcid Sky BlueAzo VioletAcid Violet (V. M.)Acid Violet BAcid Violet BBAcid Violet 2 BAcid Violet 4 BAcid Violet 4 BAcid Violet 5 BAcid Violet 5 BAcid Violet 6 BAcid Violet 6 BAcid Violet 6 BAcid Violet 7 BAcid Violet 7 BAcid Violet 7 BAcid Violet SBAcid Violet 4 BCAcid Violet 5 BFAcid Violet 4 BLAcid Violet 4 BLOAcid Violet 4 BLOOAcid Violet 4 BLOOFAcid Violet 4 BNAcid Violet 6 BNAcid Violet 6 BNAcid Violet 6 BXAcid Violet 7 BNAcid Violet 7 BNAcid Violet 6 BNBAcid Violet 6 BNGAcid Violet 3 BNOAcid Violet 6 BNOAcid Violet 6 BNOOAcid Violet 4 BNSAcid Violet 5 BNSAcid Violet 4 BSAcid Violet 6 BSAcid Violet BSCAcid Violet 4 BVAcid Violet BW

CRGGBK

IKSKKAWKKKKKBBBBBMCJAByAWBy.etc,CBKB, KHBy,KVar.AW, ByG, KA, ByG, tMHAWB.H.IKrMBBKBB,IB,MI.WDtMBBKSSKAWBy

606d•TJ603U604U774U304U47SU775U694U304U776U304U304U304A536U304U304U304U304U304U92U93U94U95U955S3524U777U77SU779A150A150U7S0A535407530a530a530a534a530530530530a52953054S527534530a527a530530a530a530a530a53052754854S530527533527530530a530a530a527561530548530a530a527a

[Acid Violet C 2 B , C l O B . . .Acid Violet C l O BAcid Violet DAcid Violet H BAcid Violet H WAcid Violet K B . . . 'Acid Violet N F D SAcid Violet N GAcid Violet P WAcid Violet RAcid Violet R ,Acid Violet RAcid Violet 4 RAcid Violet 4 RAcid Violet 4 RAcid Violet 4 R NAcid Violet 4 R SAcid Violet R XAcid Violet SAcid Violet S BAcid Violet 1704Acid Violet 2405Acid Violet 4746Acid Violet 10471Acid Violet 10475Acid Violet 18502Acid Violet 2644frAcid Violet B lueAcid Violet R e dAcid Wool B l a c kJAcid YellowAcid Yellow A CAcid Yellow DAcid Yellow F XAcid Yellow GTA c i d Y e l l o w GAcid Yellow G GAcid Yellow G FAcid Yellow L RAcid Yellow M G SAcridine Golden Y e l l o w . . .Acridine Golden Yel low

54666AAcridine Golden Ye l low, G,

G G . WAcridine OrangeAcridine Orange N O O , N O .Acridine Orange R,Acridine Red BAcridine Yellow ,Afghan Yellow G XAgalma Black 4 B XAgalma Black 10 B X , 10 B .Agalma Black 201211Agalma Black G r e e n TAgalma Green BAlgol Blue GAlgol Blue 3 GAlgol B l u e KAlgol Blue 3 I t , 3 R PAlgol Bordeaux 3 BAlgol Brilliant O r a n g e F R . .Algol Brilliant R e d 2 BAlgol Brilliant V io le t 2 B . . .Algol Brilliant V io le t R . . . .Algol Brown BAlgol Brown RAlgoi Corinth RAlgol Da rk G r e e n BAlgol GrayAlgox Gray B , B BAlgol Green BI Algol Olive R

LD HLLLLB DBBBBBB yB yB yB yB yB yB yB yB yB yB yB yB yB yB yB yB y

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U781U7S2

217h137137139137137137136137137136602a

602a

6026036036045696029

217a217217a217b542844a844839821829822819821820869869a870847a834834847833


NameManu-fac-turer Serial

No.Name

Manu-fac-turer

SerialNo.

I Orange R>lPinkRIRedBIRedBB, FF!Red2G, 3 G1 Red 5 GIRed, FF, R1 Scarlet G1 Violet B1 Yellow 3 G1 Yellow 6 GL1 Yellow R1 Yellow WF.WG....tdine Blackidine Black Midine Deep Biown 3 Rtdine Orange M:dine Yellow Yrin Orangexin pasterin powder.

rin 11 ABrin D 1M0rinD 1149rin D 1399rin DCRrin GDrinGGXrin GIrin Irin IBrin IPin ITi W SlWSinRGin RVTin Sin SDGin SXin SXGDin V 1,V 2 Ain Win 11 Xin XGPin XPin 744, 1140in Astrol B, Gin Azurine D 3 R. . .in Black (V.M.)in Black (V.M.)in Black ABin Black ACin Black B, 3 BLnBlackSBLn Black DES, EN..in Black ENTin Black IAin Black Pn Black Rn BlackSn Black S, SEu Black SET, SN...n Black SNTn Black SR.WR...n Blue (V.M.)n Blue A, ASn Blue An Blue Bn Blue BB, DBn Blue BR, BR 3 G.

ByByByByByByByByByBy

IIHH*HBr.Ali;Co.

Br.Ali;Co.

Q, etc.ByMMMMB

IMBy,MByMMB

MBBBByBvByByMByMBCAW, CVMByAWMMByMMBMMMBCByMMMBy

82481SS25819816a816819815823811811a817814

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U746U748778

778

78077S77877S778806a7S47S5a785778778778778780785784a784b78578478477878077S785a7S5a778856

U401774774b774b806a774b774b806a806a774b806806a774807807807774803a803a803803a803a I

Alizarin Blue C 2 G. . . .Alizarin Blue CWRB,

CWRRAlizarin Blue DHG GM, ~ .Alizarin Blue D 2 R, D 4 RAlizarin Blue GR, GW...Alizarin Blue GWDS, HJAlizarin Blue IIXAlizarin Blue JRAlizarin Blue NFA, NHNAlizarin Blue NSAlizarin Blue NSGAlizarin Blue SAlizarin Blue SAEAlizarin Blue SAPAlizarin Blue SAWSAAlizarin Blue SBAlizarin Blue SRMAlizarin Blue WGAlizarin Blue WXAlizarin Blue 942Alizarin Blue (violet shadeAlizarin Blue (violet shade)Alizarin Blue BlackAlizarin Blue Black B •Alizarin Blue Black BAlizarin Blue Black BAlizarin Blue Black B, 3 B.Alizarin Blue Black B, 3 B.Alizarin Blue Black GT. . .Alizarin BordeauxAlizarin Bordeaux B, BD..Alizarin BiownAlizarin Brown B, D3GO, GAlizarin Brown DR, N, RR.[Alizarin Brown 0Alizarin Claret RAlizarin Claret Red DB . . .Alizarin Claret Red DG...Alizarin Chrome Blue T...Alizarin Chrome Brown DCAlizarin Chrome Brown DBAlizarin Crimson DB.Alizarin Crimson DGAlizarin Chrome Green A. .Alizarin Cyanine G, 2 G, 3 GAlizarin Cyanine RAlizarin Cyanine WRR. . ..Alizarin Cvanine Green E

(&V.M.)Alizarin Cyanole BAlizarin Dark Blue DR, S..Alizarin Dark Gieen W . . ..Alizarin Direct Blue BAlizarin Direct Blue EBAlizarin Direct Blue ESB...Alizarin Direct Blue ESR...Alizarin Direct Cyanine FA.Alizarin Direct Green CG, GAlizarin Direct Violet EMizarin Direct Yellow DR.alizarin Direct Yellow DS..Alizarin Fast Blue DGLAlizarin Fast Brown DB. ..Alizarin Fast Brown D 3 R.Alizarin Fast Biown 3 R . . .Alizarin Fast Gray DBL. ..Alizarin Fast Orange DO...Alizarin Fast Red D 244. ..Alizarin Fast Scarlet D 6 BSAlizarin Fast Scarlet D S BSAlizarin GarnetAlizarin Garnet R

MMMByByByByBvByVar.ByByByMM

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U405U406803b

U402U403U407U408260799788788

8C5851804b775851851a851a851a

U409865852

U410U411U412U413U4HU435U416U417U418U419U420797797


NameManu-fac-turer

SerialNo. Name

Manu-fac-turer

Alizarin GrayAlizarin Gray GAlizarin Green BAlizarin Green BBAlizarin Green CE, CK.. .Alizarin Green C, CGAlizarin Gieen DGN, DMAAlizarin Green GAlizarin Green 3 G, SAlizarin Green SAlizarin Green SP 4Alizarin Green S"WAlizarin Green V, VDAlizarin V 3 WAlizarin Green WBAlizarin Green XAlizarin Indigo BAlizarin Indigo GAlizarin Indigo 3 IIAlizarin Indigo Blue S. .. .Alizarin Indigo Green B....Alizarin Indifeo Violet B....Alizarin Trisol D, RAlizarin LukeAlizarin Light Red D 8 BWAlizarin Milling Black 8 B.Alizarin Maroon WAlizarin OrangeAlizarin Orange A •Alizarin Orange DG,DN,GHAlizarin Orange RAlizarin Pure Blue B. . .Alizarin P\ire Blue DPH. . .Alizarin Pure Yellow DHS..Alizarin Red (V.M.)Alizarin Red (yellow)Alizarin Red D4B, DlOB, DGAlizarin Red GAlizarin Red IWSAlizarin Red SWB, SWBB .Alizarin Red SWR, WB ....Alizarin Red SXAlizarin Red 3 WSAlizarin Red YCAAlizarin Rose GWGAlizarin Rubinol 5 G, RAlizarin Saphirol B, SE ....Alizarin Sky Blue BAlizarin Uianol 12 BAlizarin Uranol RAlizarin Violet (V.M.)Alizarin Violet BLAlizarin Violet DHAlizarin Viridine DG, FF...Alizarin Violet NAlizarin Yellow AAlizarin Yellow CAlizarin Yellow CYAlizarin Yellow DGG, D 3 GAlizarin Yellow DOG, DOO,

DRAlizarin Yellow FFAlizarin Yellow FSAlizarin Yellow GAlizarin Yellow GGAlizarin Yellow 5 GAlizarin Yellow GGWAlizarin Yellow OAlizarin Yellow TLAlizarin Yellow 3 RNAlizarin Yellow RWAlkali Azurine GAlkali Black

CMWDMgWDMBByMByBMB

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U423U424780780a7S0a7SG7807807S0784780785

U784850a85S855

U211U2125995995998545997707694848

4848482484S484858a585858410

U538

Alkali Blue.

Alkali BlueAlkali Blues, green shades.Alkali Blues, red shades...Alkali Blue (V.M.)Alkali Blue (for printing ink'Alkali Blue IIIAlkali Blue IV AAlkali Blue 2 ASAlkali Blue AWG, A W R . .Alkali Blue AWRGAlkali Blue 2 BAlkali Blue 2 BAlkali Blue 3 BAlkali Blue 4 BAlkali Blue 5 BA•Alkali Blue BK 2Alkali Blue 5 BLAlkali Blue 7 BOOAlkali Blue DAlkali Blue H 5 BKOOO..Alkali Blue HEOOOAlkali Blue HHRROOO.. .Alkali Blue IAlkali Blue MNAlkali Blue NAlkali Blue RAlkali Blue 3 R, 5 R, C R .Alkali Blue RM, R R M . . .Alkali Blue 2Alkali Blue 1756Alkali Blue 1757Alkali Blue 11408Alkali Brilliant Blue GAlkali BrownAlkali Dark Brown GVAlkali Fast Green 3 GAlkali Fast Yellow.lkali Green. D.lkali Orange GTlkali Rubinelkali Violet

Ukali Violet ASAlkali Violet 6 BUkali Violet 6 BOUkiili Violet LRUkali Violet 421Ukali YellowUkali Yellow RUpha Black 6 BNUpha Black JC ,Upha Chrome Blue AUpha Chrome Brown 0 GAUpha Chrome Brown N . . .Upha Chrome Green 6 B . . .Upha Chrome Orange RK,Upha Chrome Red 3 B . . . .Upha Chrome Yellow C. . .Uphanol Black (V.M.)Uphanol Blue (V.M.)AmaranthiVmaranthAmaranth BAmaranth. DAmaranth DE.maranth SA.methy.st Violet.mido Acid Black B, 4 B, BS|.mido-azo-benzeno.mido Az'o Black.mido-azo-tolueno.mido Black A 2 G

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Name

Aimdo Black 10 BAmido Blat k 4024Amido Blue BAmido Blue GGRAmido Daik Bottle Green BAnndo Gall imine BlueAmido Naphthol Bl lek 4 BAmido Naphthol BHck RIvAmido Naphthol Red 2 BAmido Naphthol Red fa BAmido Naphthol Red GAmido Red BLAmido Yellow FAmmo Blac k 1 BAmine Black 10 BAmmo Black IBMAmine Black S 4 BAmine Black SIAmine Black Green BAmmo RedAniline Bl ickAniline Bl usk 1500SAniline Bluo Spirit SolubleAniline Blue BAniline Blue 2 BAniline Blue 3 B RNAniline Blue B410Aniline Red BAniline YellowAniline YellowAnthosme BAnthosme 3 BAnthosme 5 BAnthracene A< id Black

(VM)Anthracene \cidBluc (V M )Anthracene Acid BtownAnthracene Acid Biown BAnthracene Acid Brown G ItAnthracene Acid GreenAnthracene Acid Red 3 BAnthiacenc Blacl FlAnthracene BlueAnthracene Blue 3 GAnthracene Bluo SWGAnthracene Blue SWGG

SWRAnthracene Blue SW\Anthracene Blue WB WGAnthracene Blue WGGAnthraecno Blue WNAnthiacenc Blue WR W 3 RAnthraeone Blue WG newAnthracene Blue Blaek

(VM)Anthiacenc BrownAntht icene Brown G ItAnthracene Blown R1IAnthracene Brown VVAnthracene Biown SWAnthracene Chromate Brow n

(VM)Anthracene Chrornate GreenFFAnthracene Chromafc YellowAnthracene Chrome Bluo

(V Tu)Anthracene Chrome Blick

(VM)Anthracene Chrome Black

IT exAnthracene Chrome BrownAnthracene Chrome Green

Manu-fac-turer

MMMMMDHMMMMMMMAAAAAAAVarBVartMAtMCGIBQBBBC etcCM CCGCVarMBBBBBBBBCBBy11ByBCCcccccc

SerialNo

217217f

U425U42t>U427

b3SA414A415

(ibafafa12

A41bA417UblUfa5U(bUb7UfbUlOU70<)22)225-1521521521521512

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lit 50355

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A318805

A322

A3131S51S5

AmA325

Name

Anthricene Chrome lted(VM)

Anthiacone Dark Bluo WAnthiacene Direct GiecnAnthneenc ltcdAnthiacene Red WBAnthracene Red 10430Anthracene VioletAnthracene YellowAnthricene Yellow (V M )Anthracene Yellow CAntluoccno Yellow Cniht loone Y low G

Vnlhivcnc. Yellow RN 3 ltNAnthnchromc Red AAntlnaute BlaekAnthracyimno S SRAnthiacyl Blue SWRAnthiacyl Chrome1 Blue 2 BAn1 hr ic> 1 Chrome Plue I3>Anthrics 1 Chrome Biovt n D\ntl nt\ IChronieGieenA DAnthnflwone GAnthi uiol Gieen BAnthrnquinonc Blick\nthraqumone Blue bitAnthiaquinonc Blue Gicen

BXOAnthnqumone Green

GXNO GXAnthrtquinone VioletAnthraiubine 395Apollo Rod BApollo Re d GAichil Substitute VAichil Substitute 3 VNArtificial Silk Black RArtificial bilk Bla< k GAuxaeme GAurammoAurimme GVuia nnc GAuummc NAair unine OAurammc ()OAuranunc OO 3 OO 1Aut innnc OODAu umnt OOPAuratnine OEAAu umm 2 3112Aurammc baseAui moAuro r wine KitUuonal Bliuk

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Manu-fac-turer

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SonalNo

A?2<>7<)0b

U2713r>53P53r>55«)<)77 i177a2<)l2<)t77 hir>hb

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NameManu-

fac-turer Serial

No.Name

Manu-fac-turer

Azidine Blue BXAzidine Blue 24574Azidine Bordeaux GAzidine Dark BrownAzidine Fast Orange ES..Azidine Fast Scarlet 4 BS.Azidine Fast Sacrlet 7 BS.Azidine Fast Scarlet E 4 BAzidine Fast Scarlet GGS.Azidine Oiange GAzidine Sky Blue FFAzidine Yellow CPAzidine Wool Blue BAzo Acid Black B 15Azo Acid Black 3 BLAzo Acid Black RAzo Acid Black TL II... .Azo Acid BlueAzo Acid Blue BAzo Acid Blue BAzo Acid Blue 2 G....Azo Acid Brown 26049Azo Acid Magenta GAzo Acid Red BAzo Acid Red 5 BAzo Acid Red BAAzo Acid RubineAzo Acid Rubine (V.M.). .Azo Acid Rubine 2 BAzo Acid "VioletAzo Acid Violet A 2 B, ALAzo Acid YellowAzo Alizarin Black IAzo Alizarin Bordeaux W.Azo Alizarin Brown IAzo Archil RAzo Black OAzo Black Blue B, RAzo BlueAzo BordeauxAzo Brown VAzo Cardinal GAzo CarmineAzo CarmineAzo Carmine BAzo Carmine BXAzo Carmine GAzo Carmine GXAzo Cerise M, 1618Azo Chrome Blue BAzo Chrome Blue RAzo ChromineAzo Coccine 2 RAzo CochinealAzo CorallineAzo Coralline LAzo CorinthAzo Crimson LAzo Crimson SAzo EosineAzo Fast Blue (V.M.)Azo Fast VioletAzo Flavine CXAzo Flavine FF, 3 GAzo Flavine GX, 3 RAzo Flavine 3 RAzo Flavine 2 RNH, RX...Azo Flavine RSAzo Flavine SAzo Flavine SGRAzo Fuchsine BAzo Fuchsine 6 BAzo Fuchsine G, 4 Q,,.,..

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Azo Fuchsine GNAzo GalleineAzo GreenAzo Indigine 6 BAzo Indigine SAzo Indigine 419, 420A.zo Magenta 6 BXAzo Magenta GAzo Magenta RSAzo Mauve BAzo Merino BlackAzo Milling Yellow 5 G. .Azomine Black FFAzomine Fast Yellow AL.Azomine Milling Black N.Azomine Yellow GAzomine Yellow RAzo Orange RubineAzo Orscille 2 BAzo Orseille RAzo OrseillineAzophor Black SAzophor Blue DAzophor Orange MNAzo Phosphine GOAzo Red AAzoRhodine2 BAzo RubineAzo Rubine (V.M.)Azo Rubine AAzo Rubine SAzo Rubine SAzo R\ibine SGAzo Rubine WBAzotol CAzo Turkish RedAzo VioletAzo Wool Black (V.M.)...Azo Wool Blue (V.M.)Azo ^ ool Violet (V.M.)...[Azo Wool Violet 415Azo YellowAzo YellowAzo YellowAzo Yellow 3 A, 3 ANAzo Yellow A 5 WAzo Yellow 3 GAzo Yellow IAzo Yellow 3 YAzure BlueAzuie Blue A, ASIAzurinr BAzure Blue O, VSBasic Black TESBasic Blue BABasic Blue RBasic Gray ,Basic Green Z ,Basic Kraft Brown Y 2Basic VioletBenzamine Azo Blue G. . ..Benzamine Brown 3 GBcnzamino Brown 3 GO....Benzamine Pure BlueBenzamine Violet GBenzidino PureBenzine BlackBenzine BlueBenzo Azo Red BBenzoazurine (V.M.)Benzoazurine GBenzoazurine GBenzoazurine G f.,. T.

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Name

Bismarck Brown YSBismarck Brown 53Bismarck Brown 1568Black (V M )Black (V M )Black AJBlack BHBlack CBRBlack CEBlack C 2 NBlack DXBlack EBlack HBBlack MBlack NBlack NSABlack RW XBlack soluble in fatsBlack soluble in oilBlack Base BBBlack Base SBlack Black 0Blue (V M )Blue ASBlue 3 BBBlue BSBlue 5 BSBlue BS 3 BBBlue BSJBlue BSRBlue CABlue CVBlue DBBlue DRBlue DSBlue JBBlue NBlue PCNBlue PCVBlue RRBlue 3 RBlue RSBlue 25Blue 26Blue 214Blue 1900 TCBlue 16519Blue 27071Blue for silk RNBlue (greenish) spirit solubleBlue Black BBlue Black NBlue Black 0Blue Black for Half Wool GBlue Crystals 3035Blue Residue BW 6 MBoma Black BHBoma Black BHXBoma PinkBoma Yellow BBFBordeauxBordeaux extraBordeaux BBordeaux BLABordeaux BRBordeaux BXBordeaux COVBordeaux GBordeaux GBordeaux RBordeaux SBordeaux 5005Bordeaux Black

Manu-fac-turer

tMSchCVCJHPAWPHPHBAWHHPHGCBBMHSGrEPtMGiEGrEGrEIAWQ

csDHGGrEtMPSbBDHLByPMMKMByKKAWAWAWAWAWSchVartMBKByABy, MBKBK,KABIvQ

SenilNo

2832842S3

U494U749

700aU553

698U749

098U749U101U55iU749U749

700iU749U005U277U102UlOiU42SU750U695U502

539U521U503U504U505U053U700U701U7oOU27SUb96

697UbOOU500U525

5 $7bUO97Ub9SU104

035U5HU217537b521210b21 "52Mb

U218UK)0u*ioU 556U557U55SU559

16S320112}2011223732025411211210S112

U792

Name

Brilliant Acid Blue ABnlhant Acid Blue B, FF, LBnlhant Acid Blue VBnlhint Aeid Blue 25601Bnlhant Acid Canmno B

BOOBrilliant Acid Green 6 BBrilliant Acid Rod GBnlhant Ahzann BlueBrilliant Alizarin Blue D 3 GBnlhant Alizarin Blue D 6 GBnlhant Alizarin Blue DRIBrilliant Alizarin Blue R &

(VM)Bnlhant Aluarin Blue ItBnlhint Alizarin Blue 3 RBnlhant Alizarin GreenBnlhant AnthrazuroiBnlhant Arelul CBrilliant Azo Acid Blue 3 GBnlhint Azuie Blue VSBnlhant Azunno B, R, 5 RBnlhant Azunne 5 GBrilliant Benzo Blue 6 BBnlhint Benzo Gieen BBrilliant Benzo Violet BBnlh int Benzo \ lolet 2 RBnlh mt Bciuo I ast Violet

2 itLBnlhant Benzo Fast Violet

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Bnlhant Delplnno Blue BS,VS

brilliant Dianil Blue b Ginlhant Di inol Red Itinlliwit Diazino Bluo 1230

Bnlhant Double Seat lot

Manu-fac-turer

A, ByByBySGrEByKVarMMMByCRByWDBCSKByBy.A.LByByByByByByVarB etcBCVsCVQQAQBT*BsByKcA LA, LBySAAAAABycBycByGrEMMMKSMLWKBK

SerialNo

545545c543545c66b

503U312

607bO7007007607007607057a

U1055503b

U313410a41b424

A207A20SA209A20bA206a

272272272

U725UbOOU72bU79*U704

AlU79(5U106U107U10S

b2(>lS()aSI

3Lb370570370U75U74U75U7(>U7722722727022722711110$10*

U3H622541

U315170b


Name Manu-fac-turer

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SerialNo

411410385410459460450337391386419A154

A4424.155A156

487490485a485485a4S5a190485a

A157A158A159A160A161A162A163A164390425336

A165A166A167A168AflliA169456456a456a451A170

A171A172A173A174A175A176A177A17SA179A180A181

340a297332332343332

A183279279279279327327a296a296296a

Name Manu-fac-turer

GrFByByAByAByByByBvByByByBvByi kBKBKBKByByByByByByAWHIByA etcA etcBy etcA etcABKGrEQByByByByByByByByBvCRByByPIIIIIIIIKKKKByA, etcCAICV etctMSell

SerialNo

6054,196A197U71

A198U72

A199A20OA201A202

447A1844.185A186A1S7A188410410477194452379379

A189446340

A190365a365365a365a365363364405363363363363

A191A192A203A204A193A194

319A195

426517326326a104

A661U651Ub52

503A6G2

517517517541

XJ308TJ309A392

278A205

283283283283284284283

)azunne 3 G>azunne R>azunne 3 R>azunne WB> Black Blue G> Black Blue 5 G> Black Blue R> Blue 2 B> Blue 3 B> Blue BX) Blue RW) Bordeaux 6 B) Brilliant Blue 2 GDIs> Bronze E> Bronze GC> Brown B> Brown BX) Brown D 3 G> Brown G>Brown5G 2GC 3GC> Brown MC NBX> Brown 5 R> Brown RC, TR> Chrome Black Blue BChrome Biown B

> Chrome Brown BS> Chrome Brown G> Chrome Brown 5 G> Chrome Brown R> Copper Blue B> Copper Blue 2 BCyamne BCyamne 3 B

> Cyamne RDark BrownDark Green BDark Green GGDeep Black SSFast BlackFast Black LFast Blue B BNFast Blue FRL 2 GLFast Blue 4 GL 2 LFast Blue RFast Bordeaux 6 BLFast Brown 3 GLFast Brown RLFast Eosine BLFast GrayFast Gray BLFast Heliotrope BLFast Heliotrope 4 BIFast Heliotrope 5 RHTast Heliotrope 2 RLFast Orange 2 RLFast Orange SFast Orange WSFast Pink 2 BLFast RedFastRed8BL9BLDFast Red FCFast Red GL LFast Rubine BLFast ScaTlet (V M )Fast Scarlet 4BS 5BSFast Scarlet 8 BS

3NFast Scarlet GSFast Violet NCFast Violet RFast Yellow 4 GLFast Yellow 5 GLFast Yellow RL

Benzoflavine OBenzoform Blue BBenzoform Brown RBenzoform Orange GBenzoform Orange GBenzoform Red GBenzoform Red GBenzoform Red 2 GFBenzoform Scarlet BBenzoform Yellow RBenzo Gray SBenzo Green BBBenzo Green CBenzo Green FFBenzo Green TFGBenzo Green GBenzoin Blue 5 GN, RHBenzoin Brilliant Blue GDNBenzoin Brown CBenzoin Fast Red AEBenzo Indigo BlueBenzo New Blue 2 BBenzo New Blue 5 BBenzo New Red 4 BBenzo OliveBenzo Orange RBenzo Pure Yellow FFBenzopurpunnBenzopurpurmBenzopurpunnBenzopurpunn AMBenzopurpurm BBenzopurpunn 4 BBenzopurpurin 6 BBenzopurpurm 10 BBenzopurpunn 4 BMBenzopurpunn 4 BNBenzopurpunn 4 BPBenzopurpunn 4 BXBenzo Red 10 BBenzo Red 12 BBenzo Rhoduline Red BBenzo Rhoduline Red 3 BBenzo Rubine HWBenzo Rubine SCBenzo ScarletBenzo Scarlet BCBenzo Sky BlueBenzo VioletBenzo Violet OBenzo Violet Rtenzoyl Pinkienzyl Black Bienzyl Blue BBenzyl Bordeaux B 17619Benzyl Green BBenzyl RedBenzyl VioletBenzyl Violet 4 B, 6 B 10 B3enzyl Violet 5 BNBetamine Blue 8 BBiebnch Acid Blue GBiebnch Acid Blue Vhebnch Acid Violet RBiebrich Patent BlackBismarck Acid BrownBismarck Brown • •Bismarck Brown (V M )""ismarck Brown EL.ismarck Brown Ghsmarck Brown RBismarck Brown 2 R 2 RVBis.marck Brow n Y


Name

Bismarck Brown YSBismarck Brown 53Bismarck Brown 156SBlack (V M )Black (V M )Black AJBlack BHBlack CBRBlack CEBlack C 2 NBlack DXBlack EBlack HBBlack MBlack NBlack NSABlack RW, XBlack soluble in fatsBlack soluble in oilBlack Base BBBlack Base SBlack Black 0Blue (V M )Blue ASBlue 3 BBBlue BSBlue 5 BSBlue BS 3 BBBlue BSJBlue BSRBlue CABlue CVBlue DBBlue DRBlue DSBlue JBBlue NBlue PCNBlue PCVBlue RRBlue 3 RBlue R&Blue 25Blue 2t>Blue 214Blue 1900 TCBlue Ib519Blue 27071Blue for silk RNBlue (greenish) spirit solubleBlue Black BBlue Black NBlue Black 0Blue Black for Half Wool GBlue Crystals 3035Blue Residue BW 6 MBoma Black BIIBoma Black BHXBoma PinkBoma Yellow BBFBordeauxBordeaux extraBordeaux BBordeaux BLABordeaux BRBordeaux BXBordeaux COVBordeaux GBordeaux GBordeaux RBordeaux SBordeaux 5005Bordeaux Black

Manu-fac-turer

tMSchCVCJHPAWPHPHBAWHHPHGCBBMHSGrEPtMGiEGrEGrEIAWQQJ£O&DHGGrEtMPSbBDHLByPMMKMByIvIvAWAWAWAWAWSenVartMBKByABv MBKBK,KABKQ

SerialNo

2832S42S3

UlOiU749

700aU553

698U749

(>93U749U101U554U749img

700dU74<)UbO5U277U102U103U42SU750U(>05U502

5.30U521U503U501U505UG53U5"5r)U700U701U7r)0U27i>U690

007XT()()()U50bU525

5*7bU097UbOSU1U1

(>B<3U511U217r>37br)2L2(><)b2152()0b

TJ21SIH09v noU5515U557U5r)bU559

108320112?201122B7320251112112lbS112

U792

Name

Bi llliant Acid Blue ABrilliant Acid Blue B, FF, LBrilliant Acid Blue VBrilliant Acid Blue 25601Brilliant \cid Carmine B,

BOOBrilliant Acid Green b BBrilliant Acid Red GBi llliant Alizaim BlueBrilliant Ah?aim Blue D 3 GBulhant Alizarin Blue D b GBi llliant Alizarin Blue DillBrilliant Alizarin Blue R &

(VM)Bulhant Alizarin Blue RBrilliant Ah/arin Blue 3 RBulhant Aluaun GreenBrilliant AnthrazurolBrilliant Atelul CBulhant Azo Acid Blue 3 GBulhant Azuie Blue VSBulhant A-sunne B, R 5 RBulhant Azuune 5 GBulhant Bcnzo Blue b BBrilliant Bcnzo Green BBrilliant Benzo Violet BBrilliant Be nzo Violet 2 RBulhant Bcnzo Fast Violet

2 RLBulhant Benzo Fast Violet

BLBrilliant BlackBrilliant BI ick BBulhanfc Blaek 3 B, GBrilliant Blue ABrilliant Blue GBulhant Bluo GGBulhinb Bluo 217Bulhant Blue 28bBrilliant Bordeaux foDBulhant Brown 205Bulh mt Carmine GLBulh mt Can une GGBulhant Canmnc IBrilliant Chronic Blue PBulharit C hiome Violet BDBnlhint Cloth BluoBrilliant C oc lun< il 2 RBulhant Conj,o GBulhant C onto RBulh mt Congo RHulh mt Congo RBulhant Congo Blue BJtilhnnl Congo Blue 5 Uiulliunt Congo Vi >lot iiinlhant <. upper Blue BWJnlhftiit Copper Bluo GWbrilliant Cotton Bluo Nbulhant ( roctmti (V M )Brilliant Croccmo 3 B, MOObrilliant Ciot uno 0 BBulhant Croeuno 3 BA•Jrilhunt Croceino MDBrilliant Crocunt NZBulhant CrimsonBrilliant Crimson NBnlh mt Dolplimo Bluo BBulhant Delphme Blue BS

VSBrilliant Dianil Blue t> Giulhant ftianol Rod RBnlh mt Diazino Bluo 1230Julhunl Double beailoL

Manu-fac-turer

A ByByBySGrEByKVarMMMByCRByWDBCSKByBy,A,LByByByByByByVarB, etcBCVsCVQQAQBnBbByKCA LA, LBysAAAAABycBycByGrEMMMIvSMLWIvBK

SerialNo

545545c543545c66b

503U312

667(>b7(>b70b7667b(>7Cb7()57a

U1055503b

U313410a41b424

A207A208A209A200A20(>a

272272272

U725uoooU72bU79BU791

AlU705U100U107U10S

(>2(>W)alS()a81

3U>370370370U7BU71U75U7liU775iS2272272702272272271GB10*

U311622511i5S

U315170b


Name

nt Fast Blacknt Fast Bluent Fast Blue Bnt Fast Blue 3 BXnt Fast Blue 2 Gnt Fast Blue 4 Gnt Fast Red Gnt Fast Red Pnt Geranine Bnt Glacier Bluent Greennt Green Bnt Green 0 Bnt Green BNnt Green Dnt Green PNDnt Green Snt Hessian Purpleat Indigo Bat Indigo BDnt Indigo 2 B BBDat Indigo 4 Gat Indigo G GDDat I ake Red Rat Lanafuchsine1)it Milling Bluc(V M )at Milling Blue Bit Milling Green Bat Naphthol Blueat Orange Git Orange 0it Orange Rit Or&eilleit Oi seille Cit Patent Blue Ait Patent Blue Ait Phosphmeit Phosphme G 5 Git Pinkit Ponceau 5 Rit Pure L ellow 6 Git Purpunn 4 Bit Purpunn 10 Bit Pui punn Rit Red R pasteit Rhoduhn Red Bit Rhoduhn Violetit Safranme Git Safranme Rit Scarlet (V M )it Scarlet ALit Scarlet NY 47it Scarlet Rit Scarlet 2 Rit Scarlet 3 Rit Scarlet 4 R 4 RSPt Scarlet 141113it Sky Blue 5 Bit Sky Blue fa Bt Sky Blue GLt Sky Blue 5 Gt Sky Blue 8 Gt Sulfonazurme Rt Sulfon Red B 5 Bt Victoria Blue RBtWool Blue B FFR Gt Yellowt Yellowt Yellowt Yellow C

Manu-fac-turer

IAWByByByByBByByIVartMtMCGrECJLBBBBBMCCKCCA ByMM.etcCCKMIISByByA ByAA etcByByASchCMBBKtM&chtMBByByByByBySIByByVartMSch

SerialNo

UG54A 539A210A211A2124J13162

A214US5014994054994994994994993028boSS5SS48S7S8G43

TJ2S0U2S1U316

503U2S2

33970795555

U31754560Gb606571a169

U219368368a36915

6S4bGS4a679684

U2S3A424U109A443A515

109A516U110U220

424U221

5ilU223

361a182559b562a

U224303142303

Name

Brilliant Yellow SBromofluoresceic Acid A 3 GBromofluoresceic Acid BA

BLBromofluoresceic Acid Crys

talsBromo Indigo FBBromo Indigo RathjenBromo Motanil YellowBrownBrown A. 167SBrown GCBrown PCCBrown YBiown PCCBrown 43Brown 359Brown 37104Buffilo Black ADBuffalo Black 2 BBuffalo Black 4 BBuffalo Black S B 10 BBuffilo BlickEABuffalo Black NBBuffalo Black PYBuffalo Black RBuffalo Chrome Blank BWNBuff ilo Cj cinmo R 3 RBuffalo Direct Blue GBuffalo Direct Cardinal 7 BBuffalo Direct Crimson BBuffalo Direct Garnet RBuffalo Direct Orange RBuffalo Direct Orange YBuffalo Direct Red 4 BBuffalo Direct Violet 4 RBuffalo Direct Yellow CGBuffalo Direct Yellow CRRBuff ilo Fast Blue BBuffalo Fast Blue RBuffalo Fast Crimson GBuffalo Fast Crimson RBuffalo Fast Fuchfaine BBuffalo Flamme BBuffalo Flamine GBuff xlo RubmeButter YellowCachou (V M )Cachou de La\ alCalcutta Black DCalcutta BlueCalcut a Blue 2Caledon Blue IICaledon GreenCaledon PurpleCaledon VioletCandle BlueCandle VioletCanelle ALCapri Blue GONCapri Green BNCarbazole Wool GreenCarbide BlackGaibide Black E, EX SXCarbide Tast Black GrCarbide Violet VCarbmdol Blue RCarbon Black (V M )Caibon Black 4 BC irdinal 3 BCardinal Red JCarmine Blue ACarmine special

Manu-fac-turer

B etcMMMByPBKBGDHHGSLevHSchSchSchSchSch&chSchSchSchSchSchSchSchSchSchSchSchSchSchSohSch&chSchSchSchSchSchSchA etclevpHSS

KKBBy LICIIIIKMHHAWP

SerialNo

142587b5S7b5S7b8S1879135

U479UlllUfO7U596

283UbO7U700

2S3b28326627226020120S2172202612752574104053133123623923633753423941891S86466

1479495

11032

U731700

U751626

U701842765763766

U318U319

600620020a

U2S4462f462f462f462g74b458272512161

U560U592


Name

Carmine Blue VCarmine Brilliant BlueCarmine Naphth Garnet. ..CarmoisineCarmoisine BCarmoisine 3 BCarmoisine 6 B, RCarmoisine L, WSCarpet Red B, BT, RCarthamine 6 A, BCashmere Black 3 BNCashmere Black MCSCashmere Black VCashmere Blue TGCelestial BlueCelestine Blue BCerasine Brown ANCerasine Dark Red I, IICerasine Orange GCerasine Red 56 I, 56 II...Ceres Blue 4Ceres Brown 3Ceres Brown 4Ceres Orange 3Ceres Red 3Ceres Red 6Cerise DX, DIVCerise MCerise NCerofiavineCerotine Scarlet GChicago Blue BChicago Blue 4 BChicago Blue 6 BChicago Blue RChicago Blue 2 RChicago Blue 4 RChicago Blue RWChicago Blue newChicago Orange GChicago Red 111China BlueChinaldine YellowChloramine Black BHChloramine Black BHChloramine Black EXD, FFChloramine Black HWChloramine Black NChloramine Blue 2 BChloramine Blue 3 BChloramine Blue 3 GChloramine Blue BXRChloramine Blue HWChloramine Brilliant Red 8 B|Chloramine Brown GChloramine Dark Green B..Chloramine Fast Red F, FFChloramine Fast Yellow B.Chloramine Green BChloramine Green GChloramine OrangeChloramine Orange GChloramine Pure BlueChloramine Red B, 3 BChloramine Red S B, S BS.Chloramine Sky Blue AconcChloramine Sky Blue 6 B, FFChloramine VioletChloramine Violet NChloramine Violet RChloramine YellowChloramine Yellow DB, FFChloramine Yellow G

Manu-fac-turer

KAWDHA, Sl y

KtM

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CCcByUII y

tMCBCJAA

SSSSSSSssssrs

fy

ss

isrByBy.etc.ty

SerialNo.U320

U561106163163163a163a163

U321573a

A215A733A216A217U541641

U2S5223a35223

U225.U226U227U22SU229U230512512512

U112• 34b423422424388384324419422a15

A612539613469333469a473469337471a471386472358

A218470a3436174704751111

471b319358426424

A220327

A221617617617

Chloramine Y e l l o w GG,HW,M

Chloramine Yellow M.Chloramine Yellow RCChloranisidine ScarletChloranthrene Yellow GChlorantine Blue BBChlorantine Brown BBChlorantine Brown R . . . . . •Chlorantine Brown 15521...Chlorantine Brown 15895...Chlorantine Fast Blue RL. .Chlorantine Lilac BChlorantine Lilac BBChlorantine Orange T R . . . •Chlorantine Orange 11323..Chlorantine Pure BlueChlorantine RedChlorantine Violet BBChlorantine Yellow JJChlorazol Blue GBDSChlorazol Blue 3 GChlorazol Blue R • • • •Chlorazol BriUiant Blue 3 B,

Chlorazol Brilliant Blue 14 B,

Name

pihlorazol Brilliant BordeauxRH -. -A

Jhlorazol Brilliant Green GChlorazol Brown GChlorazol Brown M.Chlorazol Brown MASChlorazol Catechine BChlorazol Drab RH. . . .. . • • •Chlorazol Fast Blue RH.. . . .Chlorazol Fast Bordeaux B.

Ihlorazol Fast Red 10 B . . •Jhlorazol Fast Scarlet RH. .Chlorazol Fast Yellow A . . -Chlorazol Fast Yellow AF. .Chlorazol Fast Yellow AG..Chlorazol Fast Yellow BS. .Chlorazol Fast Yellow R . . .

ihlorazol Green BIhlorazol Green G

Jhlorazol Orange 2 KChlorazol Red AChlorazol Sky Blue F F . . . . .Chlorazol Sky Blue FFS . . . .Chlorazol Violet BChlorazol Violet 3 BChlorazol Violet R

ihlorophenineIhocolate Brown

Jhocolate Brown GChocolate Brown RChromal Blue G, G C . . . . . .Chromal Dark Blue K . . . . .Chromal Fast Brown G . . . .Chromal Fast Brown R . . . .Chromanil Black BFChromanil Black FFChromanil Blue RChromanil Brown 2 GJhromazine Blue GChromazone Blue R,Chromazone Red (new), A. .Chrome Acid BlackChrome Acid Black RSIChrome Azurol SChrome Black

Jhrome Black BA

Manu-fac-turer

SerialNo.

a r

i

i

iiHHH

HHHHHHHHHHHHHHHHHHHHHHHHHCICoAWBBGGGGAAAAMGGI

GWDQ

61761761797

849A663A664A665A666A667

451A668A669A670A671A672

358A673

617417417

417

417a

417aA734A738A735A736A737A739A740A741A742A743A744A745A746A747A748A749

474A750

340A751A752A753A754A755A756

17U568U113U114

552552a

U608U609

A2A3A4A5

XJ429130129

XJ655U656

554275a

A765


Name

- Black A- Black DFi Black DrBlack TPP G

»Black Ia Black LVi Black M ZBlack 2841

i Black 5700GsBluo> Blue ATX5 Blue B>Bluo2B IBX) Blue G> Blue RBlueRBlue RXBlue Black BBouloauxBrownBrown CSBTOWH PBrown RRBrown RVVBrown 414Brown 2813Deep Black ADeep Black ADeep Black GDeep Black GFast BlackFast Bl ick AFast Black BFast Black FFast Black F1 ast Black FWFast Black P4BPast Black PFFast Black PONFast Black PTFast Black PVFast Black PWBTPast Black PWKllFast Black 12172Fast Blue BFast Blue 4 BFast Blue RFast Blue 1336GFast Brown AFast Brown BCFast Brown GFast Brown ItFast Brown TPFast Brown TVFast Biown VFast Brown 12081Fast Brown lr>82*Fast Cyamnc GFaBt Garnet BLFast Green GI ast Green GLFast Green 1G39 IFast Orange ItFast Orange RDFast Pure Blue B\Fast Red GFast Violet BPast Yellow BNFast Yellow GPast Yellow 2 GFast Yellow GG"ast Yellow GA 0

Manu-fac-turer

CGAWMAWHKHKIIByBWBBKQAWWBBKBvAWKPGGlevKGtMGtMGCGIAIAACGAIICGBAIIIIIAByIIIIIAIIIrByiAICGAAII

SenalNo

275a275a

A425275a275a

U322275a

U322275<i507lf)3bG2Gl(3bK)3b16*599lG3b

Ui2355015ba15Sa90

158158158a158a275b275275b275275181c275cAG275275cA7AS181cA9157181181181c

XJ115U78

Uf57Ub58AG74A(>75AG7GA10

U2S1AG77AG70A078AG80AG81U79

A(82Ab8*A084A(8r)U232

551All

AC8G177d()Ga9G9Ga90a

Name

Chrome Fast Yellow R 2 RChrome Gallus Brown RRChrome GreenChrome Green (V M )Chrome Green CChrome Green GChrome HeliotropeChrome Leather Black EChrome Leather Black EChrome Leather Black LChrome Leather Black EAChrome Leather Bla k IChrome Leather Black MChrome Leather Brown RChrome Orange GitChrome Patent Green NChrome Red 2593Chrome VioletChtome VioletChrome Violet Brown 9457Chrome Violet b for print

ingChrome YellowChromo YellowChrome Yellow D DFChrome Yellow G GGChrome Yellow ItChrome Yellow RChrome Yellow SM 2501Chxomine GChromme RRChrornine BlueChromino Blue BChromine Brown ItChromme Brown VChromine Fast Blue SChrornine Violet 2 ItChromocitromne ItChi oniocyaninc B VChromo cne IChromogeno Violet BChromopurpunn IIChromotropc 2 BChromotrope G BChromotrope 8 BChromotrope 10 BChromotrope DWChromotrope I 4 BChromotrop< 2 RChromotrope SChromoxane Blue RChromoxane Violot 5 BChryaamme GChrysamme KCkryaamiiK ItChrysobauneChrysobanno ItChrysoidineChrysoidim AChryaoidin AltChrysoulme G2TChrysoidim. VChrysoidine GSChrysoidmc ^ NChrysoidmc ItChrysoidinc RChrysoidine 3 ItChrysoidinc RDChrysoidine ItLChrysoidine KGChrysoidine ItL ltl EChrysoidine T baseChrysoidine Y

Manu-fac-turer

AGByKKLDHBBy<aBWDBySByKKByGKGByIBySAWByKIvSAAWAWAWAWAWDHDHMMDHMMUMMMMMByByBy etcSBy ItMtMVarBtMPBItMVarC DHb(hCVPBBVar

SerialNo

177lr>Sa509

U324U324U515

625U11GU2S3U702U117U542V2UXJ70 5U2r>

219TJ325

540557

U32G557177177Q177177e177o177

AV)iG1461 la

U5G2Ur>0*U5(HU5()5U5(HiU507

ltt)aGU777

UliOU507

57G7

17111457a

Ib44057a

U2JGU237

H2342J0410 te30 U3ii43i3ii3340034i43t34Ha.33,


Name

Chrysoidme 2 YChrysoidme 46803Chrysoidme BaseChrysoidme crystalsChrysomeChrysolanne AChrysolineChrysophenmeChrysophenme GChrysophenme GOOChrysophenme R WChrysophenme IIIChrysophemne 190Ciba Blue BCiba Blue 2 B 2 BDCiba Blue G G 2 BCiba Bordeaux BCiba Gray B GCiba Green GCiba Heliotrope BCibanone Black B BG 2 GCibanone Blue 3 GCibanone Brown B VCibanone Green GCibanone Olive B GCibanone Orange RCibanone It ellow RCiba Orange GCiba Pink RCiba Red RCiba Red BCiba Red GCiba Scarlet GCiba Violet BCiba Violet 3 BCiba Violet RCiba Yellow GCinnabar Scarlet BFCinnabar Scarlet G, RCitronme GOOCitronme GOOO 2 ROOOOClaret NY Z 1413Claret Lake BLClaret RedClaret RedClaret Red B BOClaret Red SSClaret Red XClayton Cloth RedClayton 1 ellowCloth Blue 17C9 1770Cloth Fast Blacl BCloth Fast Blue BCloth Fast Blue GTBCloth Fast Blue RCloth Fast Red RCloth Red BCloth Red BCloth Red BBCloth Red B 2BCloth Red 3 BCloth Red BACloth Red BCCloth Red BOCloth Red GCloth Red GCloth Red GACloth Red 3 GACloth Red GFL GTCloth Red OCloth Red 17G9 25S6Cloth Scarlet C GCloth Scarlet R

Manu-fac-turer

tMAKSchVartMG S PI.SVarLByAWKIIIIIIIIIIIIIIIIIIIIIIIIBKBIvLGrEBByBHMBMCICoCICo2IIIIIByGiE IvKWDByAByGrEByBy GrEAAAMKKK

SenalNo

333*3333

143U526586304304304304a304304SSO8S188291089989189779 i793S68792a792b792795911910a90S909906907901900901890299300141140

misU23SU119A757112aU120112a

19*19STJ327UG59693UbGl25748423323G

A39423G2312362.u3a23b22423423423023423GA394246252

Name

Cloth Scarlet 2584Cloth Yellow RCocceine OiangeCoccine 2 BG 3 BGCoccinme BCochinealCochineal Red ACochineal Scarlet BCocluneal Scarlet 4 RCoerulem BCoerulem ICoerulem MS powderCoerulem SCoeiulem SL powderCoerulem SWColumbia BlackColumbia Black BColumbia Black EAColumbiaBlacklT FB T2BColumbia Black RColumbia Black WAColumbia Black Green DColumbia Blue G GMColumbia Blue RColumbia Bordeaux BColumbia Brow n MColumbia Brown RColumbia Catechme 3 BColumbia Catechme GColumbia Catechme OColumbia Catechme RColumbia Fast Black DColumbia Fast Black FFColumbia Fast Black GColumbia Fast Black VColumbia Fast Blue 2 GColumbia Fast Blue RColumbia Fast Red FColumbia Fast Scarlet 4 BColumbia GreenColumbia Green B 3 B, GColumbia Orange RColumbia Violet RColumbia \ ellowColumbo Blue 4 RCoomassie Acid Blue RCoomassie Black BCoomassie Blue BlackCoomassie Navy BlueCoomassie Is avy Blue 2 RNXCoomassie Union BlacksCoomassie Wool Black DCoomassie Wool Black SCoomassie Wool Black RConcentrated Blue BBConcentrated Cotton Blue

B, 2CongoCongo 4 RCongo Blue 2 BCongo Blue 3 BCongo BrownCongo Brown GCongo Brown RCongo CormtD BCongo Corinth GCongo Fast Blue BCongo Fast Blue R3ongo Magenta2ongo Magenta 3616Uongo Orange GDongo Orange RCongo Orange R, RG

Manu-fac-turer

KGrEPAMPBWDch

MBDHB etcBDB,ByA y

AAAAAAAAAAAAAAAAAAAAAAAAAAAABDI evLevLevBDLevLevlevLevHMAAVarA Le\A LevVarVarAAKKVarA LBy

SerialNo

U327aA458227a16710181b169957S

000G01601601601601436455455a43b4534r>5a4653S7325U80A12A13U81U82US3U84US6U87US8TJ89A1GA17343279478478A14A15617

U6631884*32174*4252461260244243

U752539307374412391477477490375312456451A395

A395315373373

GLOSSARY OF DYE NAMES


No.Name

Manu-fac-turer

Congo RedCongro Red 4 B ,Congo Red 4 R ,Congo RubineCongo Rubino GCongo Rubino ZCongo Rubine 8714Coreinc AR, ABCoioine 2 RCorioflavine G,GG,GOOO,RCoriphosphino OS, OXCorvan Black BGCorvaR "Black TCorvolino BTCotton BlackCotton BlackCotton Black (V. M.)Cotton Black 3 BCotton Black BGXCotton Black BNXCotton Black BTCotton Black CC, CTCotton Black CKCotton Black BCotton Black GBCotton Black GS, RSCotton Black PFCotton Black RWCotton Black UGCotton Black V, YCotton Black 4Cotton BlueCotton BluoCotton Bluo (V. M.)Cotton Blue BCotton Blue BCBCotton Bluo BCBCotton Blue BRCotton Blue BSJCotton Bluo CCCotton Blue GCotton Bluo NCotton Blue OOOCotton Bluo R, RNCotton Bluo 5190Cotton Blue Doublo cone...Cotton BrownCotton Brown (V. M.)Cotton Brown BCotton Brown BCotton Brown CNPCotton Brown CRCotton Brown FSCotton Brown 4 GCotton Brown MCotton Brown O, 2 RCotton Brown 3 RCotton Brown RNCotton Brown TCotton Brown VCotton Brown 100, 137, 153Cotton Corinth GCotton Cutch 21 ACotton Dark Green B, N. ..Cotton Dark Green 138....Cotton Fast Red 4 BSP, 4 BXCotton GreenCotton Green A, 88 A,

105 A, BCotton Groen DCotton Green 2 GCotton Marine BlueCotton Milling Black

VarSchByVarSBKCGDHD1IGrE

BBSWDKBBBLevKBKSBBKLevBWDLevKCGaGrEKMB§BKWDCKLevBLevKSKLevBkB

LevB.GrELovKLovBKLovSLKB

307307374313313313313UK)041GOOoUOlieA00A70U1214G2c738A39GA71A72A73402c462cA39G463A3904G2cA754G2hA39G4G20A74538049538aU32SU49053SaU32S53,SaU328539G49538a049538a539737490U329490aU122490a490aU320400aU329490aU123490aU329400a312A732U330U7323G3U331U733A714U51GU332U124

Cotton OliveCotton OrangeCotton OrangoCotton OrangeCotton Orange (V. M.)Cotton Orange FB, GIv. . . .Cotton Oiangc GCotton Orange RCotton Orange RR, R 2 O. .Cotton Orange 10737 ....Cotton Orange Brown(V.M.)Cotton Pink BCotton PonceauCotton Puro Bluo BCotton Purple 5 BNCotton RedCotton RedCotton Hod ACotton Rod 05 A, 201 ACotton Red BCotton Rod 4 BCotton Red 4 BCotton Red 8 BNCotton RubinoCotton RubyCotton ScarletCotton ScarlotCotton ScarletCotton Scarlot NP, NPX...Cotton Violet 43 ACotton Violot 2 BCotton Violet 5 BCotton Violet RCotton Violet XCotton YellowCotton Yellow CIICotton Yellow GCotton Yellow GI, GXCotton Yellow R,Crosol Black (V. M.)"Vesotino Yellow GJrcsotine Yellow GOOCrosotino Yellow RCrosyl Blue BBS, URN....Crosyl Fast Violet 2 BCrimson BBTCrimson Benino GCroccino AZCroeoino BCroccine 3 BCroccino OrangeCroocine Orange GSroceino Orange RCrocoino Orange X3roeeine Orango YCrocohio Scarlet (V. M.). . .3roecine Scarlet 3 BSioccine Scarlot 7 B, S B. . .Croccine Scarlet 10 BSroeeine Scarlet 8 BLCroeoino Scarlot 2 BXCroccino Scarlot 3 BXroccine Scarlet MOiroccino Scarlet MOOiroceino Scarlot MOOirocoino Scarlot Oirocdno Scarlot OOCross Dyo Black (V. M.)...Iross Dye Blue FRJross Dyo Brown 2 D!ross Dyo Brown 4 RIrops Dye Drab NJross Dyo Green G

LovK

LovKB, SBKILovBBKABBtMCLovSBGrECGBLovBK§LovQQItLov

?BBBGrEGrE.MGrEGrELByAWCR«USohVarVnrSchCSohK

ByBy, KWDSohWDKKHIIIIHIIII



No.Name

Manu-fac-turer

Cross Dye Yellow D... .Cross Dye Yellow RCross Dye Yellow YCrumpsall Direct Fas t

Brown BCrumpsall Direct F a 8 t

Brown OCrumpsall Direct Fast Red RCrumpsall YellowCrystal OrangeCrystal Orange 2 GCrystal PonceauCrystal Ponceau 6 RCrystal ScarletCrystal Scarlet 6 RCrystal VioletCrystal Violet 5 BOCrystal Violet 6 BCrystal Violet CVCrystal Violet 484Cumidine ScarletCupranil Brown RCupranil BrownCupranil Brown GCupranil Brown 12366Cupranil Brown 15596Cupranil Brown 15903CurcumeineCurcumeine GGCurcumeine SCurcumineCurcumine L, LCCurcumine 8000CurcuphenineCurch. BrownCurch. Brown DCutch Brown RCutch Brown 11759Cyanthracene Blue 3 B.. .Cyanthracene Blue 2 BL.. .Cyanthracene Yellow S. •..Cyanthrol BGA, G, 3 GO. .Cyananthrol R, RBCyananthrol RBA, RBX..Cyananthrol RXO, RBY...CyanazurineCyanine BCyanine BFCyanine BlueCyanine BlueCyanogen Blue 13623...Cyanol (V. M.)Cyanol Green (V. M.)Cyanol Fast Green B...Cyanosine BCyanosine spirit solubleCyprus Green BDark Navy Blue 2935...Dark Purple (printing paste)Deep Black DDeep Fat Black ColorDelphine Blue BDeltapurpurinDeltapurpurin 3 BDeltapurpurin 5 BDeltapurpurin 7 BDevelop BlackDevelop Black NZDeveloped Black BDeveloped Black BHDeveloped Black NDeveloped Black RDeveloped Black W

HHHLevLevLevLevVarB.etc.A,BKWDcVarA 'BISchIIIIIA, BKBKAtM.GGLCICoAWMSCVCVCVBBBBDHA, MACVtMCccIM.K.SALevLevtMAS,ByAWVarLevWD

AWAWAWAW

S178S179S180444

44534117S

383S

113113

U543U2S6

516516516516516

83A6S9A687A688A690A690A690

140140140142142

916

A540A426A7]<5A601U727U728U729

860859859859630544544544a

U527UC04

546566b566598594

A19537a

U736U528

U 2622366366a366367333d333d

XJ570333

U571XJ572U573

Developed Blue G GDeveloped B r o w n MDeveloped Green FDiamine Aldehyde B l u e . . .D iamine Aldehyde Scar le t .Diamine Azo BlueDiamine Azo B o r d e a u x B . .D iamine Azo Scar le t ( V . MDiamine Black (V. M. ) • • •Diamine Black B HDiamine Black B ODiamine Black H WDiamine Black R ODiamine Blue B l a c k EDiamine B lue (V. M. )Diamine B lue 2 BDiamine Blue 3 BDiamine Blue B XDiamine Blue C 2 RDiamine Blue 6 GDiamine Blue 3 RDiamine Blue R W . • • •Diamine Br i l l ian t B lue G . . .D iamineBr i l l i an tBordeauxRDiamine Bri l l iant R u b i n e . . .Diamine Bri l l iant S c a r l e t . . .D iamine Br i l l ian t V i o l e t . . .Diamine Bronze GDiamine Brown (V. M - ) . . .Diamine Brown BDiamine Brown MDiamine Brown VDiamine Ca tech ine ( V . M . ) .D iamine Ca tech ine G . . •Diamine C u t c hDiamine D a r k Blue B . . .Diamine D a r k Green NDiamine F a s t B lack (V.M.)Diamine F a s t B lue (V. M . ) .Diamine F a s t B o r d e a u x . . . .D iamine F a s t B r o w n (V.M.)Diamine F a s t G r a y . . • • • • • •D iamine F a s t Orange (V.M.)Diamine F a s t R e d F & (V.M.)Diamine F a s t Scarlet (V.M.)Diamine F a s t Violet (V.M.)Diamine F a s t Yellow (V.M.)Diamine F a s t Yellow 3 G . .D iamine GoldDiamine Golden Y e l l o w . . . .D iamine G r a y GDiamine Green (V. M . ) . . . .D iamine Green BDiamine Green GDiamine Hel io t rope (V. M.)f a m i n e J e t B lack (V. M . ) .

>iamine N e r o n ( V . M . )aJiamine N e w BlueDiamine Ni t razo l B r o w n G.Diamine Ni t razo l Green1 Diamine Ni t r azo l O r a n g e . . .Diamine Orange (V. M . ) . . .D iamine P u r e BlueDiaminera l Blue (V. M. ) . . .^ i amine ra l B r o w n GJ i a m i n e R e d (V. M. )Diamine R e d B'Diamine R e d 3 BDiamine Rose (V. M. )f a m i n e Rose F F BDiamine Scarle t (V. M. )Diamine Scarle t H SDiamine Sky B lue F F

A WA WA WCcccccccccccccccccccccccccccccs€cccccccccccccccccccccccccccccccAAccccc


NameManufac-turer

SerialNo. Namo

Manu-fac-t urcr

Diamine Sky Blue (V.M.) .Diaraine Violet NDiamine Violet Red B. . ..Diamine Yellow (V.M.)...Diamine Yellow CPDiamine Yellow NDiaminogen (V.M.)Diaminogen Blue (V.M.). .Diaminogen Blue BB, NA.Diaminogen Sky Blue N. .Diamond BlackDiamond Black AF, CY,

EA, ETDiamond Black FDiamond Black FBDiamond Black GADiamond Black GAFDiamond Black P 2 B, PV,

PVTDiamond Blue RDiamond Blue Black EB. .Diamond Bordeaux RDiamond Flavine GDiamond GreenDiamond Green BDiamond Green BDiamond Green BXDiamond Green G, GF, GNDiamond Green 3 G....Diamond Green SS.....Diamond Green special. . . .Diamond MagentaDiamond Magenta IDiamond Phosphine (V.M.)Diamond Red BHDiamond Red GDiamond Violet BBDiamond Yellow GDianil Black PRDianil Black RDianil Blue BDianil Blue GDianil Blue RDianil Blue 2 RDianil Crimson BDianil Garnet BDianil Yellow 3 GDianil Yellow RDianil Yellow 2 RDianisidine BlueDianol Black (V.M.)Dianol Black BHDianol Black EDianol Black EXDianol Black RO, RWDianol Blue 402Dianol Brilliant Blue GDianol Brown CDFBDianol Brown LFDianol Fast Red KDianol Fast Red FGDianol Green BDianol Orange 217 ADianol Orange BrownDianol Orange Brown X...Dianol Red BDianol Red 2 BDianthrene Blue 2 BDiazanil BBDiazanil Scarlet BDiazanil Scarlet 6 BDiazine BlackDiazine Black H

CCCCCCCCCCVarBy

ugyByBy

TMMMMMMMMMMMLevLevLevLevLevLevLevLevLevBDBDLevL.vLevBDLevLevMMMKSen

A36S327

A369A370

304404274273273

A373275275275275275275

157164a1S1

A22210227049527649549927(5276276

U128U129609b

A223A224U5772044914793S0415323379

A427332252627408436a436a436a436a328424a424b356a356a279343474356b356o356357356881273

A428A429125333

Diazine Black 1401Diazine Green SDiazo Black B, OB, OT...Diazo Black 11Diazo Black 10020Diazo Black B1IADDiazo Black BHNDiazo Black BHN(Diazo Blue XDiazo Blue Black RSDiazo Bordeaux 7 BDiazo Brilliant BlackDiazo Brilliant Black B. . .Diazo Brilliant Orange GRDiazo Brilliant Scarlet B. .Diazo Brilliant Scarlet 3 BDiazo Brilliant Scarlet 6 BDiazo Brilliant Scarlet 2 BLDiazo Brilliant Scarlet 5 BLDiazo Brilliant Scarlet BGDiazo Brilliant Scarlet G. .Diazo Brilliant Scarlet PR.Diazo Brilliant Scarlet PR.Diazo Brilliant Scarlet S 4 BDiazo Brown. GDiazo Brown 3 GDiazo Brown (jGDiazo Brown NilDiazo Brown 3 RBDiazo Fast BlackDiazo Flint Blaok BHX.. .Diazo Fast Black G[Diazo Fast Black MG'Diazo Fast Black SD. . .Diazo Fast Black V . . . .Diazo Fast Bordoaux BL...Diazo Fast Groen GE...Diazo Fast Rod 7 BL.. . .Diazo Fast Violet BLDiazo Fant Violet 3 RLDiazo Fast Yellow GDiazo Fast Yollow 2 GDiazogeno BlackDiazogono Black ABT)iazogono Black ADOiazogonc Black N^iazogono Bluo 11)iazogono Blue 2 R, 4585.."•iazogono Bluo RDiazogeno Garnet BB

)iazogono Had 8 B>iazo Indigo Bluo BR>iazo Indip;o Bluo 2 KL, 3 RLMazomino Hod L'iazo Olivo G•iazophenyl Black X,Hazophonyl Bluo BCHazo Pure Bluo 3 GL'iazo Rubino B'iazo Skv Bluo 3 GLiazo Sky Bluo B•iazurino B>ichroino Brownicyanino•imethyl-indigo'ioxine)ipbeno Blue Bioh^ne Bluo Itiphenylamine Blueipheny 1 Black•iphonvl Black L•iphenyl Black RC)iphenyl Blue 3 BC

KKByByBKSByW BByByBy

BvByByByByByByByByByWDByByByByByByByByByByByByByByByByByByByAWAWAWAWAWKAWAWAWBy

GByBy

M¥MAAnnMGGG


NameManu-facturer

GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGHHAW4WKQKIByCGItSKBySPByKCVKISHKK

SerialNo

A618A620Abl9A02133434834839334S347449206617ISa1414

20512

4633A622Ab23A6244625462b295207

A627343

A62SIS18

A0294b746b

A62946713a13

35S35S

A634A635U753442a

A5oOA5-1U335442a

U335A69242o9333a

1335142aL335

A2G0442aTJ3354424261

TJ335442a

U3354693442a42Sa

U336XJ336

Name Manu-fac-turer

QI1BKQKIAWSCGKIIWBICVIHByLevILKKLGLIILQKSSIAWKKKILKIKAByBy&ByIAWKByKIIIISKIKtMGrEIPI

SerialNo

428a428428a379b42 Sa

U336428a428a428a428a

U336397428a337

U336428a428a428a428a455455b42Sb

A502U337XJ337A503

457A636A504

486344

A505344a

U337A717A718A694A552U33SU340U339A695344

U341478b

U342A20462a462

U343463

A696A553U344U345A262U346

392c343343a

A698U704U347

279U348

617o617c398681354

Diphem 1 Blue BECDipbenj 1 Blue BTCDiphenjl Blue BBECDiphenjl Blue 2 RDiphenjl Blue BlackDiphenyl Brown BBNCDipbenj 1 Brown BN BVC!Diphenjl Brown 3 GN

3 GNCDiphenj 1 Brown GSDiphenyi Brown RNDiphenj 1 Brown TBDiphenyl Catechme GDipbenyl Cblonne Yellow FFDipbenj 1 Cblonne Y eilow G

229Dipbenyl Chrysome G, GCDipbenj 1 Chrjsoine 3 GNDiphem 1 Cbrysome RRDipbenyl Citronine GDipbenj 1 Dark Green BCDiphenj 1 Deep Black GCDipbenj 1 Deep Black GNDipbenj 1 Deep Black GWCDipbenj 1 Deep Black \ NDiphem 1 Deep Black VPDipbenj 1 Fast BlackDiphenjl Fast Brown G,

GNC ..Dipbenyl Fast Gray BCDipbenj 1 Fast RedDipbenj 1 Fast Violet BCDiphenj 1 Fast Yellow extnDipbenyl Fast Yellow GDipbenyl Green BCDiphenyl Green GDipbenj 1 Green 3 GDipbenj 1 Green 3 GC, 3 GFDiphem 1 Green KGWDiphenjl Orange GGDipbenj 1 Orange RRDipbenyl Red 8 B SCDiphen\ 1 Red 1S4 340Dipbenj 1 Scarlet 3 BDiphenyl \iolet B\CDisulphine Blue 47073 DSDirect Black (\ M )Direct Blac*. 4BCDirect Black CDirect Black DDirect Black DDirect Black DBDirect Black EDirect Black FBSDirect Black FBSDirect Black GDirect Black S GDnect Black 3 RDirect Black RCDirect Black RODirect Black TDirect Black VDirect Black VTDirectBlack WC 3899 3919Direct Black 7o65Direct Black 8o35Direct Black 14714Direct Black 33336Direct BiueDirect Blue (V M )Direct Biue A

Direct Blue ABDirect Blue BDnect Blue 3 BDirect Blue 5 BDirect Biue 5 BDirect Blue 7 B 12 B BK,

FFDirect Blue BXDirect Blue C GDirect Blue 3 GDirect Blue GNDirect Blue GRC N 2 B R

5RDirect Blue RDnect Blue RWDirect Blue WBBDirect Blue X 2 BDirect Blue 30Direct Blue 7079Direct Blue 13108 13503Direct Blue 51096Direct Blue Black BDirect Blue Black 313Direct Biilhant Blue 8 B[Direct BrownDirect Brown (V M )Direct Brown B, HDirect Brown GDirect Brown 2 GDirect Brown 3 GNCDirect Brown HBDirect Brown J JJB JPDirect Brown MDirect Brown NDirect Brown RWDirect Brown TBDirect Catecbine GDirect Catecbine 30Direct Chrome Black 14722Direct Chrome BrownDirect Cotton Blue GS RDBDirect Cotton GrajDirect Cotton G een 2 BDirect Cutcb GGDirect Dark Brown MDoct Dark GreenDirect Dark Green SDirect Dark \ lolet BEDirect Deep Black EDirect Deep Black EDirect Deep Black EWDirect Deep Black NTSDirect Deep Black RWDirect Fast Black BDirect Fast BlueDirect Fast Blue FFBDirect Fast Brown C GBDirect Test Brown GGDirect Fast Gray RNDirect Fast Orange 16710Direct Fast Red FDirect Fast Red 17727 25420Direct Fast Scarlet (V M )Direct Fast Scarlet 4 BSDirect Fast Scarlet 4 BS

8BSDirect Fast Scarlet SEDirect Fast \ loiet 3654Direct Fast YellowDirect Fast Yellow 00, RDirect Gray BDirect Gray B JDirect Gray R

GLOSSARY OF DYE NAMES GOT

Name

reenreen Breen Breen Creen Green Green 3 GG Yreen KGDreen Ureen 10865reen 9753, 34267ldigo Blue Aldigo Blue BKldigo Blue BNidone Blue IIavy Blueavy Blue Brange BR Grange Grange Hrange Rrange Rrange 6 Rrange 1901range 6693ore Bluenrple NededBed3BedNed 215, 1725ifranme Barlct ABarlet Barlet 3 BaTlet FBiy Bluecy Blue Bcy Blue FPiy Blue 22wy Blue 13108s.y Blue, greenishLolot BLolet BBLolet RLolet RLolet Rlolet RRiolet3C53 4561lolet 11508lolot 12932 18510ellow (V M )ellow Bellow BKellow Cellow CAellow CRellow EGOOellow Fellow G GBE GRellow Gellow 2 Gellow 6 Gellow GOOellow MCellow PCellow PIellow Rellow Rellow 2 Rrellow TOellow V

Manu-fac-turer

ICGT SCGCGICGSGfeIIgKIvS

G

KLBKICGKI SDHSK

ISBKWBSsHCGSKCGIKAKSIIIGrESoliKLKSGrEG

By GrEGrESohAW

SerialNo478aA44447SaAtlA41(>475478aA41747SaAJ1S47Ha4 404 1035 i44*tmoUJ19tf)2b302lib3b2llaAr)0l5302b*02bU101U307bJ07bAbOOUS00U705U70UU1S0A700420A719A720A70042441 *ji41 iA440H *aAWKA45041 in01)<>KUb0o

A4G000b304b9b9fA4009d9hA4610617bOo

Direct Yollow WllDirect Yollow ZBind Vllow 212Dncct \cll(w 10i0r>Donimgo Ah/aim lihu k 1'Doming > Ah/atm Hla< 1 («DoinniKo Ali/ann Bhu HDoming ) Ali/tuiti H ttl< ut(Doming) ]ihulc4(2I<Domingo Bluo llln k HDoming >Vi 1< t A•Double llulhant h(atl< IDoublo Pone can RDouble) 1'OIK oau 2 RDoublo Pont < an 1 RDoublo Sunk 1Doublo Sciulo< oxtia S[Dra/ahno Ali/aunDra/alino Blade BI1Dra7rtlmo Hlu< 10 liDia/ahno Bin 2 Bl IDiaznhno Bluo CVDia/almo Blw IDra/ahno Blu< 1 1Diazalmo Bluo 1 8Diazahno lUuo \{\ IiDia/ahno Bluo VVViDrazahno Bluo Blade llWlDraahno Iioulouirc 0 HOmzulmc HiiHmnfc YdlowDrazahno Biown ( »i 1\DLa/ahno Biown 1 LDrazahno Biovm (rDraralnio Biown * (Jdrazahno Brown 4 JDra/ahi\( Urowix 1<Oalmo Chlonno Y<J11OW (Dra7ahno Diamond ViokLBBDra/ahno TaHt liluo 4 CJ h"Jm/ahno I mi («tav3i a/ah no I aHt R< dia/ahiu I aHi Rod 1ta/almo 1 aHl dl >w Bla/ahno ( arnoi BBlaruluui ( amoi I Ita/ahno ( tiuin BXramltno Indigo Hluora/alm< Now Rodra/alinu Now Rod 10 Branihno OmrtKO I Lta/almo Oran/ufo U•ra/aliuo Orango 11•nwalmo Rod 1'raraluio Rod 1 Lra/ahno Hod 1 V)razaln)o Soarlot B•ui/almo Hky Bluo 11>ia/£ilmo Violet 1)*ra/almo Violot NI X*•razalmo Violot VBTaralmo Yollow Rrazalmo Yollow Rra7almo Yollow H'ra/anno Yollow i'uranthrono Bluo C C'uranthrono Blue R9'uranthrono Yollowurmdono Blue 4 Bunndono liluo 5 Burmdono Bluo (I Bunndono Red B»urlndone Hod N

STaxm-iao-(UK IWBO( Ko

NT ot iBvByBvAI<vAWAWAWAWAWAWKAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWAWMAWAWM>»nBOm>BD 1

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NameManu-fac-turer

BDFALLGGGGGGGGGGGGGGGAAVarVarB,ByBMBBBtMGLevBBBBBBBA, etc.SAA, LevSAASchSchSchSchSchSchSchSchSchSchSchGGGGGGGGGGGGGGGG

SerialNo.

905103389466720G

S141S142S143S144S145S146S147S148S149S150S151S152S153S1541231005875875S7a5S7a5875905S7a589588587275

U130U131U132U133U134U135U136121121121122122a122117462463463477a4773444S8464474464311

A63SA639U612U6135515541S4183180180a181

A640A641A642553

U614

NameManu-fac-turer

Durindone Scarlet RDutch YellowEboli Blue BEboli GreenEclipse Black CEclipse Brown BEclipse Brown GCEclipse Brown REclipse Fast Brown BC..Eclipse Fast Brown GC..Eclipse Fast Brown 3 GC.Eclipse Fast Brown 4 REclipse FastDarkBrownBCEclipse Fast Red Brown. .Eclipse Fast Red Brown EEclipse Phosphine GGC..Eclipse Phospliine RRC..Eclipse Yellow GEclipse Yellow 3 GEmine RedEosamine B, GEosineEosine (V. M.)Eosine AEosine AGEosine AG, A3 G, BBEosine BN, BNLEosine CA, WEosine S, SPEosine Spirit SolubleEosine (yellowish) 701....EraBlackJErgane Yellow GErgane Yellow RErgane Yellow WErganone Blue BErganone Blue GErganone Gray BErganone Violet RErica BErica BBErica BNErica GErica GErica GNErica 2 GNErie Direct Black G, GX..Erie Direct Black RErie Direct Black RXErie Direct Brown GBErie Direct Brown GRErie Direct Brown 3 RB...Erie Direct Brown RFt 2 RFErie Direct Green ETErie Direct Green MTErie Direct Green WTErie Orange 2 RErioazurine BCEriocarmine 2 BCEriochromal Brown EB....Eriochromal Gray 5 GEriocbrome Azurol B, BC..Eriochrome Aaural SEriocbrome Black AEriochrome Black TEriochrome Blue BlackB,BCEriochrome Blue Black G. .Eriochrome Blue Black R. .Eriochrome Brown RCEriochrome Brown SDEEriochrome Brown VEriochrome Cyanine R, RCEriochrome Geranol R

Eriochrome Green H.Eriochrome Green L.Eriochrome Green MEriochrome Green O....Eriochrome Olive G. ...Eriochrome Phosphine REriochrome Red AW, B.Eriochrome Verdon A, SEriochrome Violet B....Eriochrome Violet 2 BL.Eriochrome Yellow 2 G.Eriochrome Yellow 3 G.Eriochrome Yellow GR.Eriochrome Yellow S. ..Eriocyanine A, AC, R...Erio Fast Blue SWRErioflavine SXEriofloxine 6 BEriofloxine 2 GErioglaucineErioglaucine A, AP, EP, XErioglaucine 49141. . .Erio Green BErio Green NErio Green Supra.. . .Eriorubine BErio Violet BCErio Violet RLCErioviridine BErweco Alizarin Acid Blue RErweco Alizarin Acid Red BfErythrine7 BErythrine CErythrine PErythrine RRIrythrosineErythrosine A~"!rythrosine BIrythrosine G-Jthyl Acid Blue RREthyl Acid Violet S 4 BXXEthyl Blue BEthyl PurpleEthyl VioletEthyl VioletEthyl Violet 8682Euchrysine (V.M.)Euchrysine RR, GG, GNX,GRNTEuchrysine NX, RT, RRDEuchrysine 3R, 3 RXExcelsior BlackExcelsior Lake Scarlet (V.M."Excelsior Scarlet GExcelsior Scarlet 3 R ,Export Blue 1504ast Acid Blue'ast Acid Blue BFast Acid Blue 3 BFast Acid Blue RFast Acid Blue RHFast Acid Eosine GFast Acid Fuchsine BFast Acid Green RHFast Acid Magenta GFast Acid Marine BlueHBBX'ast Acid Navy Blue GRI..'ast Acid Phloxine A'ast Acid Red A'ast Acid Red EB, EGG...'ast Acid Red RH'ast Acid Violet ,

GGGGGGGGGGGGGGGGGGGGGHGGGGGGGRWCoRWCoBCBBMMM.etc.B,LBBBB, etc.B, GM, IBBBBAWCMMB

MBIMMLHAW.C


Name

.cid Violettod Violet A 2 Rtod Violet Btod Violet Btod Violet 3 Btod Violet 10 Btod Violet ERRtod Violet Rtod Violet R, RBEtod Violet RGEtod Violet RXtod Violet 416Vcid Yellow (V M )tod Yellow RBEVeid Yellow RHSlackBlackSlack BSlack BSSlack NSlue31ue AOOOOBlueBBlueBBlue BB[Slue 3 BBBlueOBlue RBlue RDBlue ZBlue 62105Bordeaux BBordeaux GBrilliant Acid CarmineBnlnant Black 12349BrownBrownBrown 3 BBrown GBrown GSBrown NBrown 0Chrome BlackChrome BlackChrome Black KChrome Blue PRCotton Blue C GOCotton YellowDiiect Yellow 22090Cosine LGrarnct 5 B3 ray BSray RGBurrcen BGrrccn CRIn en bluishenc Blue 1ene Green GGlene Violet Bene Violet Renc Yellow-Lea t her Yellow 2G855[ ight GreenLight Orange GLight Yellow G, 2 G,GGNLight Yellow 3 GLight Yellow RGMordant Black THMordant Blue BVtordant Blue BMordant Blue R

Manufac-turer

MByMKByBKMMHKCMIIGLBBBtMGrEAAWGGrEMB KAGABKBKGrEIAByAAG1*MAWHBKQIWD833AWGrLGGtMByByAWAWAWAWAV*ByBYByByISByMLevMM

SerialNo

5S25825(25S0

IH5352b

U1J9IH5J

5S0 i5S25S0i

U35 4UU()

1371U022

058740711100600t>)Ob0)7( )0

U(2*( )0b009(0)019

u m0102*(»a2 *(>a( ()C

U()00172213172212

U( 251(0211

U57S275a

IHS1HSO1115 ISUrll

301b500b

U57)0S10S1

U52052 352 i

U5S2U5S3U5S4U5S5U5S0U2 3O

52 kt3810

Ul<1010a

275U7 37A4 3OA431

Name

Past Mordant Yellow1 ast Moidani, Yellow G1 a,st Navy BlueI a,st Navy Blue APist Navy Blue BNNOO,

RZOOI nst Neutr il Violet B1 ast Orange I GI nst Ot vn^L O1 ait P ipc-i Yellow GL ast Punclast, Pink BN GN1 dht Pink f oi silk1 ast Ponceau LFast Punting GreenPast Printing Yellow Rraat Red A1 ist Hed ATast RedrxstRcdPast Red A1 ast Red ANSXPast Red AV1 ibt Rod B1 ast Red BNI ist Red BTI ist Red CJPast Red ETast Rod IBS1 ist Red NS1 ast Red OI ast Red &lastRcl VRPast Russian Green1 nst S ul( r Blue A RI ast Scarlet B1 wtSdiletBlast b(atktBX:lnstS<ailct BXGI ast Straw \ ellow V1 ast SuK< n BlackI ist Sulf nBliukTI ast buK< n Violet 5 BS1 ast Sulfon Violot 4 R1 ast Lduylcnc RedI ast \i(torm Violet S4B1 ast Vi ilot It1 ast We ol Blue I1 ast Wool bcarlct 4 RPast Yollowlast Y( How PYla«t YclbwGRI ant \ilbwN1 ftHt Y How RI ast Y( 11 w SI ant Yellow YI iwt " ellow 951 ant VioletPlava/me I 3 GL1 Iava7inc LI lava/mo S1 lava/mo T1 lavinduhno II OI lavophosphme G 4 G, It1 lavopurpunnI luoicflcemeI ( rmyl Violet (V M )1 raiHO1 i ( nch BlueI rr iuh Kod1 ucliHinc1 uchsine ASVI uohsine B

Manu-fac-turer

VarBKGiBGrl?cIMCOAWIDIIByKByVarBVarVarWBBB ByB etcBBy etcBVarBByMSehBvWDAWBKBBAW&SsGrTGiLAWAWBIvVarlevtMPKBKCBQMMMMBMVarCPQP etcVarPtM

SerialNo

29429464964964907S

5148U492

U5S0G94C04

A2652

U240lblA77Lb8lblIb6A78lbl1121121111631C6A79KS101Ml104

U515049

U1U218UH2

Ul4iA(01

2012(11S21S2T>8uOld

A(>02U5S1U1S2

1 *71*71*71501491*714913702020a192020a

608009d7S5585530

U595US02U593

512512512


Name

Fuchsme IFuchsme MBFucksine NBFuchsine Sruchsxne TRFulling Orange 1G700Fur Black DMTur Gray 279o3Furreine DBFuscamineGallamme BlueGallamhc Violet II BGallazme AGallazolBlue4GGallemeGalleme JRG pasteGalleineSR bW WGallocyanmeGallocyanme DGallocyanine DHGallocyanme FGallocyanine MSGallonavine WGallo Green DHGallop hemn PGallo Violet DGallo Violet DFGallo Sky Blue BGambine YGeramne 2B GGeranium BGentiana Violet BGentianine AGlaoier BlueGloria Black NGlvcine CorinthGlycme RedGolden BrownGolden OrangeGray NOGray Blue 0095Green AGreen BXGreen GGreen HDGreen PLXGreen VGWGreen 21Green 24.1Green 15825Green Crystals DllaGreen Crystals EGreen Crystals TGreen Crystals MGreen Crystals XGreen Crystals YDGreen Crystals HaGreen residueGreen residue DGrela Red RGuernsey Blue OGuinea Black 3 BLGuinea Bordeaux BGuinea Bordeaux 6 BGuinea Bordeaux BLGuinea Brown RGuinea Brown 2 RGuinea Carmine BGuinea Carmine DGuinea Cyanme LBGuinea Cyanme LGGuinea Cyanme LRGuinea Fast Green B

Manufacturer

GrEtMSchBfeckIByByIG ByDHDIIGB> etcGB\arBIBDHBDHByByHBjfc>AGIByIviAByfeIv11AWIvII15BSoHIvtMHtMKHIvIvKGrEMAAAAAAAAAAA

SerialNo

512512513524512250a

U241U212

923923017C 39G15

UG2G509509509G2bG2b(2GG2602S772629CpSa

IJ243U214

OU2118U46r9b501U2453103092Sb145C9ba

U35740 )a

U:>S7XJ3 >4

49 uU144U707UsO-j

40 mU35b

40540)105

Ui )b405

XJ J5(>U irr)U ir5U507

5iq115UGXJ7"UbU9

U10A22A 23Ull1312TI13503

Name

Guinea Fast Green 3 BGuinea Fast Green 2 GGuinea Fast lted BL'Guinea 1 ast Red 4 BLiGuinca last lted 2 ItGuinea I aat Violet ALGuinea Fast Violet 10 BGuinea GreenGuinea Green B GGuinea Green 2 GGuinea Red 4 RGuinea VioletGuinea Violet 4 B 6 BGuinea Violet S 4 BHalf Wool Blue 3 RHalf Wool Green b3bl6Half Wool Green 63S16 N 5Hansa Gteen GHansa Rubme GHansa Rubme OIlansa Yellow GHansa Yellow 5 GHansa Yellow RHat Black (V M )Hat Black A 4 ANHat Black BHat Black L, SHavana Brown SHehantkmeHehantlnne G GG GFF, RHelgoland Black BHHeligoland Black FFNXHeligoland Blue G BHelgoland Blue RWHclindonc Black RRGIlehndone Blue BBHelindone Blue 3 GNHelmdone Blue 3 ItHelindone BiownHelmdone Broun ANIlehndone Bro n CRIlehndone Bro"\\n GIlehndone Bro-wn 3 GNHelindone Brown 2 RHelmdone Brov. n 5 RHelindone Fast Scarlet CII hndone last Starlet R RCIlehndone Giay 2 B BRHelmdone C reen GIlchndono Printing Black

2 RGIJohndone Oian e DHe Undone Orange GRNJfchndone Orange ItHelmdone PinkHelmdone Pink AN, BNIlehndone Red BHelmdone Red 3 BHelmdone Scarlet SHelmdone VioletHelmdone Violet B BBHehndono Violet DHolmdone Violet RIlehndone Yellow CGIlehndone Yellow GG vatHelmdone Yellow 3 GNHelmdone Yellow RNHeho Bordeaux BLHeho Fast Blue BLHeho Fast RedHeho Fast Red RL TRLHeho Fast Rubenne RLHeho Fast Violet AL

Manufac-turer

AAAAAAAVarAAAVarAABvLLMMMMMMCGrEAGrECBGGGGGMMMUMMMMMMMMMMMMMMMMMMMMMMMMMMMMByByByByByBy

SctialNo

U15UlbU17UlbU19U20U21502502505A2453053Oo530U240

U519U520U437U43SU439

28U441U442A376U508U22

U50SU2S7

13814143G43b424

A453921880896896a904a873904a90483G902903907915921892921a9148-*591191001001701801b020020808020blOa810810810a

A2G68587373

A268A269


Name

Helio Tast Yellow 8 GLHelio Red RMHelio Red RMTHeliotrope 2 BHessian Brilliant PurpleHessian Brown BBNHessian Past Red FHessian Purple NHessian YellowHoffmans VioletHomophosphme GHomophosphine 00Hydranthrene Brilliant Cop

per DHydranthrene Dark BlueHydranthrene Olive RHydranthrene Yellow AG

ARHydrazme Yellow 00Hydrazme Yellow SOHydrazol BlackHydiazol Black RHydrazol Chrome Black CliHydrazol Chrome Black DBHydron Blue (V M )Hydron Blue G RHydron Brown (V M )Hydron Olive GHydron VioletHydron Yellow GHylidme Ponceau 2 RHyhdine Ponceau 2 RImmedial Black (V M )Immedial Blue (V M )Immedial Boide IUX GImmedial Brilliant Blnck BImmedml Brilliant Caibon

r, FGImmedial Brilliant Green GImmedial Brown (V M )Immedial Carbon (V M )Immedial CutchImmedial Cutch (V M )Immedial Dark Brown

(V M)Immedial Dark Gxeen BImmedial Deep Gieen GImmedial Direct Blue(V M )Immedial Green (V M )Immedial Green BluoImmedial Indo eno (V M )Immedial Indone (V M )Immedial Indono Violot BImmedial KhakiImmedial Maroon BImmedial New Blue GImmedial Olive (V M )Immedial Orange C, NImmedial Purple CImmedial Sky BluoImmedial Violet CImmedial Yellow (V M )Immedial Yellow Olive(V M)Imperial Green GIImperial Scailct 3 BImperial Yellow RIndahzann I J RIndalizann GreenIndamme i RIndamine 0 RIndamine BlueIndanthrene

Manufacturer

ByByByALByLLLBy TLPLL

GiTGrlAWAWAWAWCCCCCGtMGCCccccccccccccccGccccc0cccccByByByDIIDIICGCGM13

SerialNo

A270A271A272

321>024S031 *5013055U( 000001370*

7J1S10All 2

All *AGO*A(04AGO;AOOb

7 IS71874 SA7lbb7tSe71Sd

U027U5*2

72172 ta7*0720720SG9725720870S71725S73S74:S7r>740740S7G7337* *aS777*9S78S79711SSO728SSL710SS2

A27*247

7bCrt*0*4704705096837

Name

Indanthrene NNIndantlnene BlackIndanthrene Blaek B BBIndantluene Bluo 3 GIndantl tene Blue GCIndanlhicne Blue GCDInlmthrcne Blue GGS

GGSIEnd mthrene Blue GG SPIndmtl renoBlue 3 GPIndunthrene Blue RInd mil lene Blue RSInd xnthtenc Blue WBIndanthrene Blue WRIndantluene Bluo Green BIndmlhrene Bordeaux BIndmthrene Boiden.ux B

e\traIndantluene BiownIndanthrene Biown BIndantlnene Claret BIn lanthteno Cluet B extriIndun tin one Coppei ItIndmthrene Daik Blue BDIn 1 uUhiene Daik Blue BOIndanthienc Dark Blue BPIndanthrene last Blue RRIndanthrene Gold Oian ,e GIn lantlnene Gol 1 Or inge ItIn lantlnene Gold Orange RSInlintluene Gold Oiange

2 RT.Ind mtl lone Gray B BPIndunth one Guen BIndantlnene Mtuoon RIndanthrene Olive GIndanthrene Orange RTIndanthrene Pink BIndanthrcno Red BNInd an fch tene Red GIndanthreno Red ItIndanthrcno Rod Brown RIndanthrene Red Violet RRNIndanthreno Scarlet G, GSIndanthrene Violot BIndanthreno Violot KIndanthrene Violot ltNIndantincno Violet RRIndantlneno Violot ltlIndanlhieno Violet Yellow

G PIndantl reno Yellow G GPIndn/ino MIndnzurmo BIndazunno BBIndazuuno GMIndnmrine 5 GMIndzuurinc RMInduzunno ISIndia Ro e 17285Indian RedIndian Yellow (V M )Indian Yellow G GNIndian Yellow ItIndigene ItIndigene Blue BBIndigene Blue ItIndigoIndgio pnwloIndigo powderIndigo solutionIndifeo TBPInd go G

Manu-facturer

BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBC

IGCByAWIIVarVarVarMByB

SerialNo

873a7G8a768a840843842841841840S37838850850a705a82882780780782S8278137G37G3840S37a7G07017017G18487(584579181287 *b83182G830873o873d7027087G0832767704840a849089411429427430390390

U0G7U028

141b141140097

A701A702874874874874874888


NameManu-fac-turer Seiial

No.Name

Manu-fac-turer

Indigo 7 GIndigo KB pasteIndigo KGIndigo MLBIndigo MLB 2 BIndigo MLB 4 BIndigo MLB 5 BIndigo MLB 6 BIndigo MLBR, MLBRR. ..Indigo MLBTIndigo MLB Vat IIndigo NCIndigo RBIndigo TIndigo Acid Blue AIndigo Blue NIndigo Blue 275Indigo Carmine Blue BG...Indigo Extract A, AN 4Indigo Salt TIndigo Yellow 3 GIndigo WhiteIndigotineIndi&otine PIndigotine 500Indo CarbonIndochromineIndochromine RR, TIndochromine Black EXD..Indochromogen SIndocyanine B, 2 RFIndocyanine BIndoineIndoine BlueIndoine Blue RIndophenolIndo Violet BFIndulineIndulineInduline BInduline 2 BInduline B AInduiineDB, NInduline NN ,Induline NBLInduline RNInduline SInduline WLXInduline 1768, 1778Induline 10350Induline 38724, 38725Induline Black base 5789. .Induline Red (V. M.)Induline Scarlet (Iris Blue)Induline Spirit Soluble....Induline Water Soluble. . .Ingrain BlackIngrain Black 4 BInk Blue BJTBNOOInk Blue BJTNOInk Blue BNOOIntensive Blue BIris BlueIrisamineIrisamine GIrisamine G exIsamine Blue (V. M.)Isodiphenyl Black RIsopurpurinItalian GreenJanus Brown BJanus Gray BJanus Red B

KMMMMMMMMrCJABKBVaTBAC8SAGWDSchBDHAVarVar??tMB¥BKHKKBVatVarHHGrEGrEGrEllCCscGMMM

8748818838748808818828838798S88768748S0888545874874U2387787588987687787887774 S067667667a666705a699c126126126619U24699697699699697699699699699697699699697699700699a671697699A759A758U509U50DU5095G2648576576576U288437784709435128240

Janus YellowJanus Yellow GJapan BlackJapan Black BJapan Black MJapan Black MBGJapan Black MF"asmineasmine high coneJaune Me*tanile BromGJet Black APXi et Black RJet Black RRJute Black BJute Black IJute Black RNTJute Coal Black SKatigene Black (V. M.)....Katigene Black Brown BW.Katigene Black Brown GN.Katigene Black Brown R...Katigene Blue Black 4 BPAKatigene Brilliant Black B,FGKatigene Brilliant Green 3 GKatigene Brown 2 RKatigene Brown VKatigene Chrome Blue 5 G.Katigene Cutch BKatigene Deep Black BKatigene Direct Blue B....Katigene Direct Blue RF...Katigene GreenKatigene Green 2 B, 4 B,F2G, MICKatigene IndigoKatigene Indigo BKatigene Indigo GKatigene Indigo 3 GTKatigene Khaki GKatigene Olive GNKatigene Olive Brown R...Katigene Red Brown RKatigene Red Brown 3 R—Katigene Violet BKatigene Violet 3 RKatigene Yellow GKatigene Yellow GGKatigene Yellow GRKatigene Yellow Brown GGKatigene Yellow Brown GRKatigene Yellow Brown 9 RKatigene Yellow Brown RLKetone Blue 4 BNKetone Fast Violet 10 BKitonBlue NKitonBlue VKiton Fast Green VKiton Fast Orange GKiton Red 6 BKiton Red GKiton Fast Violet 10 BKiton Violet 12 BKiton Fast Yellow 3 GKiton Fast Yellow RKiton Yellow GKiton Yellow GGKraft Brown LKraft Brown basic YZKryogene Black BNXKryogene Black TBO, TG .Kryogene Black TGE, TGOKryogene Black TGO...,

MBBBBBGGPB

llBytMBByByByByByBy

ByByByByByByByByByBy

ByByByByByByByByByByByByByByByByByByByM

I

I

I

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IIIIBBBBBB


Name

Kryogene Blue BNOKryogene Brown AKryogene Brown A, GKryogene Brown GXKryogene Brown R B,

RBNXXKryogene Brown RXXKryogene Direct Blue BKryogene Direct Blue 3 BKryogene Direct Blue

BNAGXKryogene Direct Blue G, GOKryogene Green GXKryogene Pure Blue RKryogene Red Brown GRXXKryogene Violet 3 RXKryogene YellowIvryogene Yellow G, GGKryogene Yellow RLacquer Black RLake Black CLake Black PLake Blue ABIILake Blue ABOIILake Blue AVLake Blue AVOLake Blue ILake Blue RTLake Bordeaux BLake Purple S PLake RedLake Red CLake Red DLake Red PLake ScarletLake Scarlet Red DLake Yellow 28227Lanacyl Blue B BBLanacyl Violet B BTLanafuchame (V M)Leather Black (V M )Leather Black BOLeather Black CRLeather Black ILeather BlackLeather Black RLeather BUck TLeather Black 3553Leather BlownLeather BrownLeather Brown GGI eather Brown IXLeather Brown RLeather Flavinc 9118Leather Flavi no 9118 ..Leather Gold 5902Leather Olive 71930Leather OrangoLeather Orange BLeather Orange BYLeather Red 0Leather Yellow ALeather Yellow 1G TULeather Yellow GLeather Yellow 2 G 3 GLeather Yellow GC GS, MLeather Yellow GNLeather Yellow NLLeather Yellow 0Leather Yellow PLeather Yellow R TGLeather Yellow 1BRLeather Yellow 582Sa

Manu-fac-turer

BBBBBBBBBBBBBBBBACGMMMMBBKMBVarMMMCMByCCccBBIKtMMGrEGrDKByTcvIISBKASehLevLevMGiEQVarCOGrCAWBKMtMQtML

SerialNo

753743750750751751a753754753752754a729751b754b712712710U25

U2S9UO30U143U1UUli5UWbU150U1S*

179U157

1531532001*2

A377A4*5U217

187ISO04

U290U158U159U077U*58U5 ir)II147U511

20SU*5)U2182H*a2SiaOOOgOOOcr

UtKlTJ20211

U7*8U7S9U14S

000000000000GOO00000bGOO600000000GOO

Name

Lemon Yellow RLeueo Gallo rhionme DHLeucol Dark Green BLeucol Brown BLight BlueLight Blue GIi ht Blue Superfine Spirit

bolubleI lght Green A ex coneLight Green 2 ALight Green 2 G coner lght Green SFLi ht Green SFLight Gieen SF BluishLight Green SF YellowishLight Green SF YellowishI lght Green SLLight Green YellowishLilac PCLilac PCLiquid Oil Black NLissome GreenLithol Claiet BLithol I a-st Orange Rr ithol Fast Scarlet B G RNLithol I ast bcarlet RLithol Red 3 B GG, 3Gr ithol Red RLithol Red RG RSLithol Rubine B BN G RGMagentaMagenta AMagenta ABMagenta BMagenta 1ABSMagenta L, SMagenta IPMagenta (acetate)Magenta crystalsMagenta eiyatals 3Magenta ciystals IIMilaelute GreenMalachite G reen (V M )Malachite Groan BaseMarine Blue BMaune Blue RRMaroonMai ion C")iduMi sRid AX GX\Tiirtius \ (HowMai tiUH Yellow 7UMartma Yellow 0740Ma,uvoMelanogene BlueMchinthermo BIIMclanlheurie IIIMolanthe unc HOMdanLheunc 11818, 12700Molanthormo Blaek BllMo Idol i H BlueM( lclola s Blue 3 ItM< logouc Blue BIIMere (rme Wool Si arlot 5 BMerecrol Brown i ItMencrol Oiange 2 RMeridian Black ALMeudian Blaek ANMetachromo Blue BMctaehtoine Blue GMotaelnonxe Blue Bliok 2 BMetacliromc Blue Black 2 BXMctachrome Bordeaux RMetachromo Brown B

Manu-fac-turer

KDHByBytMtMMtMtMBBBBBQ

DIIGtMHBBBBBBBBVarBBCHBtMBVartMtMVaiVarVaiItMBy§A BIvGBKP etcMIIIIISsIIIIIIs.sAAAAAA

SerialNo

U3G0664866872521539520503518505504505504505505505505

U509U6*lU536

50bA SOAS2

73a73

17 *a173173a1525125125125125125125125125125125124954054955*751251210*

6G6

0S87i533 *c*2S***c0400404*8

U75GU754U755U708U700U27U28U20U30

9289


Name

Metachrome Brown BLMetachrome Brown BRLMetachrome Olive BMetachrome Olive Bi own GMetachrome Orange RMetachrome Orange 3 RMetachrome Red GMetachrome Violet BMetachrome Violet 2 RMetachrome Yellow RA.Metannne BrownMetanil YellowMetanil Yellow (V M )Metanil Yellow BrominatedMetanil Red 3 BMeta-Nitramline OrangeMeta-phenylene Blue B 2 BMeta-phenylene Blue RMethyl Alkah BlueMethyl Alkali Blue PureMethyl BlueMethyl BlueMethyl Blue MBSMethyl Blue for silkMethyl EosmeMethyl Gallus BlueMethyl GreenMethyl Indone BMethyl Lyons BlueMethyl OrangeMethyl Silk Blue (new)Methyl Soluble Blue 3 SMethyl VioletMethyl Violet BMethyl Violet BBMethyl Violet 3 BMethyl Violet 4 BMethyl Violet 5 BMethyl Violet 5 BMethyl Violet 6 BMethyl Violet 6 BMethyl Violet 7 BMethyl Violet base 7 BMethyl Violet B BBMMethyl Violet 3 BHNMethyl Violet BIA 2 BIAMethyl Violet 2 BP 3 BIA,

5 BIAMethyl Violet 2 BN 6 BNMethyl Violet 4 BOOATNMethyl Violet DBMethyl Violet IB IBAMethyl Violet N, NY 147Methyl Violet R 3 RMethyl Violet 5 RMethyl Violet 5 RAMethyl Violet RIAMethyl Violet 5 ROMethyl Violet 129Methyl Violet baseMethyl Violet base BBMethyl Violet base 74418Methylene BlueMethylene Blue AN, BBMethylene Blue BMethylene Blue 2 BMetb> lene Blue BAMethylene Blue BEXMethylene Blue 2 BDMethylene Blue BGMeth> lene Blue BGMothylene Blue BGNMethj lene Blue BX

Manu-fac-turer

AAAAAAAAAASVar\arPByMCCB etcItMA CGrEGrEMBGP etcCGtM etcGB etcVarVarVartMMtMBy, etctMBMBy tMBKMtMtMtMtMGrEtMByBM.tMVartMtMBKBKHVarBVarVartMBABtMBA

SerialNo

U31U32A25A20

58U33U34U35LHGA27

U710134134135

A27440

691G905355355375385375375S8

TJ63251912753713S537

U1G0515515515515515517515517515517517515515515515515515515515515515515515515515515515515515659663659659659659659659059059G59

Name

Methylene Blue DMethylene Blue DBBM,

DDBMMethylene Blue FKIIMethylene Blue GMethylene Blue HGGMethylene Blue LMethylene Blue MDMethylene Blue MDXMeth> lene Blue MEDZMethylene Blue MNXMethj lene Blue 3 RMethylene Blue &Methylene Blue VNMethylene Blue 1574GMethylene Blue 52067Methylene Gray ND 0Methylene GreenMetlii lene Green B BXMethj lene Green BXMethylene Green GMethylene Green N, 0Methylene Green PMethyJene Green 1 WMethylene Green 247Methylene Heliotrope 0Methylene SZOMethylene VioletMethylene Violet BMethylene Violet BNMethylene Violet 2 RMethylene Violet 3 RAMethylene Yellow IIMikado Brown 2 B MMikado Golden Yellow 6 G

SGMikado Orange (V M )Mikado Orange 4 RCMikado Orange 4 ROMikado YellowMilling BlueMilling Blue BCMilling Blue GRMilling Blue 2 RMilling Blue 5 RMilling Brown GMilling Brown BWMilling Green DB DSMilling OrangeMilling Orange GMilling Orange GMilling Orange JNMilling Orange ROMilling Orange 88Milling RedMilling Red GMilling Red 4 BAMilling Red 6 BAMilling Red GAMilling Red RMilling Scarlet B GMilling Scarlet BSMilling Scarlet 4 RMilling Yellow (V M)Milling Yellow 3 GMilling Yellow GAMilling Yellow 3 GOMilling Yellow H HG.H3GMimosaMimosa C R Z 2Mineral BlueModern Azurme DHModern Blue

Manu-fac-turer

I

MKIBKBBMBMCRBPtMMIs. SBKSMG IGKMDHVarDHMHKMLLL etcAA,LKKAMALLAWWDAWDLWDACAAAWDMCICoMCAACVMGGcDHDH

SerialNo

659

659659659659659659659059603059659603659659G816606606606606606606006606876596S06&06S0080680618111011111110

693693

U 37A436U38

U521503523b250TJ39

A27525058

250U40293493U41U42298400b484400

A378U43U44177177c198198

XJ291640629


Name

Modern CyanmoModern VioletModern Violet NMonochrome Black FMonochrome Black Blue GMonochrome Blue 5 RMonochrome Brown BXMonochrome Brown GMonochrome Brown VMordant Blue 13707Mordant Yellow GD, GS, RMordant Yellow GTSMordant Yellow OMordant Yellow 3 RMuscarmeNako Blue Black BNako Black DBB ONako Brown B DR, 3 GANako Brown 3 GN P, RHNako Gray B 6 BNako Yellow 0NankinNaphthalene \cid Black 4 BNaphthalene Black DNaphthalene Black 12 BNaphthalene Blue BNaphthalene Blue DLNaphthalene GreenNaphthalene Green VNaphthamme Black RENaphthamine Blue (V M )Naphthamme Blue 2 B 3 BNaphthamine Bnlhant Blue

GNaphthamineBnlli mtBlue3Naphthamme BiovsnNaphthamine Brown 4 GNaphthamine Deep Black

HWNaphthamino Direct Black

(V M)Naphthamine Direct Blue

BXRNaphthamine Direct Blue

ERNaphthamine Direct Blue

2 R 3 RNaphthamino Ducct Blue

3G92Naphthamine Direct Green

AGNaphthamine Fast Black

(V M)Naphthamine Fast Black

KSNaphthamino Fast Bor-

deaux BGNaphthamme Fast Scailet

(V M)Naphthamine Green (VM)Naphthamine Orange (V M )Naphthamine Red 3605 HNaphthamine ScarletNaphthamine Violet BENaphthamine Violet RNaphthamine Yellow (V M )Naphthamine Yellow R, XNaphthazine BluoNaphthazine Navy Blue 15GNaphthazurme B BANaphthazunne 3703Naphthochrome Violet RNapathof orm Black 3930

Manu-fac-turer

DHDHDHByBygyBy¥BBMBDIIMMMMMMtMByHIIMMMM IKKKKKKIv

K

K

K

K

K

K

K

K

K

SerialNo

G276*5621

t m oU250U251U2521125 5U254A703

17748

1775b

05 r>023 x92 5a92 5a02 U92 5a02 5a(>06g2«5S

U75S217

A157

511r)043 3533833b

370a570a477a477

335a

45b

A 599

A399

A 599

A 509

A100

U5b2

U3b3

KKKis.KKKKKWDWDGrEKIK

U5G4A401A402

UiG552(5327b

9a9a

GO 2(>02a5853b 5

U078U3G6

Name

N iphthogene Blue BNaphthogone Blue 2 RNaphthogene Blue 4 RNaphthogene Blue 6 RNaphthogenc Indigo Blue RNaphthogenc Pure Blue 4 BNaphthol Black (V M )Naphthol Black (V M )Naphthol Black ANaphthol Black BN iphthol Black 2 BNaphthol Black 3 BNaphthol Black 0 BNaphthol Black BRN iphthol Black CR, MB, N,

I RNaphthol Black greenishNaphthol BlueNaphthol Blue 2 RNaphthol Blue Black (V M )Naphthol Blue Black MN iphtlu 1 Blue Black 0 B1ST iphthol Daik Green GNaphthol GicenNaphthol Green BNaphthol Or ingeNaphthol PinkNaphthol Red (V JM )Naph th ) lRedGRNaphthol Red SNaphthol YellowNaphthol Y( How SNaphthol Yellow SLNaphthol Yellow SLC SLZNaphthylununo Black DNaphthylaimncBlackCV M )Naphthylaimne Black 4 AN,

4 BNaphthylamine Black 10 BNaphthylamino Black 4 BlvNaphthy'amino Red 5 BMNaphthylan me Black B 2 NNaphthylamino Black 0 BNNaphtha laimnc Black BOONaphthylamino Black 4 BXNaphthylanune. Black CSR

GSBNaphthylamino Black FNaphthylan inc Black NANaphlhylatnmeBlackNbBNNaphthylamino Black SXNaphthylamine Blac k2002,

200 JNaphthyl innno Bluo BlackNaphthylamino Blue 2 BNaphthylamino Bluo 3 BNaphthyl imino BrownNaphthyJanuno Grcon TNaphthyhuninebkvB] t DDNaphtliylanune YellowNaphthyl Blue Black NlNaphthylono VioletNavy BluoNavy Blue DNavy B l u e F .Navy Blue GR, 5 RNavy Bluo 17184..Navy Bluo SMNavy Bluo TNootolyl Black BNeotolyl Black BBNootolyl Black 4 BNeotolyl Black TL

Manu-fac-

turer

AAAAAACIvIvCByCVC KtM

KKCtMVarBvBlvCtMB y , CVai

CBB

VarB ByMC , KC.Iv

u

rK

B

By

KB

KCKK15BvNFKCCCI bAWCVKPAWMMMM


Name

ISeotorjl Black VLNeptune Blue B .Neptune Blue BG, BGN,KeptuneBlueBR BTE RNeptune Blue BXXNeptune Brown RXIseptune GreenIs eptune Green SAX SiiL.

SG\Iserazme (V M)Nerol Bfterol2 BNerol BLNerol 2 BLNerol \LNeutral BlueJSeutral Blue RNeutral Blue 3 RNeutral GrayNeutral Gray GNeutral RedNeutral \ioletNeutral \ lolet O _Isew \cid Chrome Black RNew Chrome Black PKNew Blue B G2s ew Blue RNew Blue RR RGNew Claret BNew Claret PNew Claret RNew CoccineISew Direct Blue SNew Ethjl Blue BSNew Ethyl Blue RSNew Fast Blue F HNew Fast Blue R RSNew Fast GrayIsew Fast Green 2 BNew Fast Pink F"New Fast Straw YellowNew Fuchsme ONew Fuchbine SNew Magenta 0New Magenta 0New Meth\ lene Blue (V M )New Meth} lene Blue FNew Methjlene Blue GGNew Methjlene Blue NN\New NigrosmeNew Patent Blue BNew Patent Blue GANew Phosphine GNew Pobchromine FBNew Toluylene Brown 00ISew Toluylene Brown ONew Toluylene Brown Ri\ew Victoria Black BNew Victonal Blue BNew Yellow for CottonNiagara Black Blue RNiagara Blue B 2BNiagara Blue 4 BNiagara Blue 6 BNiagara Blue BRNiagara Blue GW,HW RWNiagara Blue RNiagara Fast Red FDNiagara Violet 2 BNiagara \iolet 3 RNicholson Blue 4 BNight Blue

Manu-fac-turer

MBBBBBBBCAAAAACAWMACCMAWCVC etcVarBBBBAL.MMByIByIBiAWMGrEGrEMCByCB\WBjByCGGrEGrEGrEByByWDSchSchSchSchSchSchSchSchSchSchPB,I S

SerialNo

U454545543545ao45

U161503503

U293A32A33A34A35A36676676

U455221241670669

U456A607

275a650649649A83A8oA86169

U36SU457U4oS

6o26o2a681497652

A608513513513512663663651663700563545b75

616A465A464A466

262558304441337426424386336326343326327536o60

Name

Night Green ANigrammeNigrophorNigrosmeNigiosmeNigrosme (V M)Nigrosme (V M )Nigrosme spirit solubleNigrosme water solubleNigrosines from aniline (m-

dulmes)Nigrosines from nitrobenzo]Nile Blue A B, RNile Blue 2 Bm Nitraniline OrangeNitro Azomine Green FNitrophenmeNTitrosamme Pink BXFNitroso Blue MRNitrosamme RedNyan2a Black BOil Black (V M )Oil Black (V M )Oil Black 6 BOil Black 6 GOil Black HGOil BHck 11410 39694Oil BlueOil Blue Black 114Oil Brown BGOil Color BrownOil Color CanaryOil Color \ ellowOil OrangeOil Orange (V M )Oil Orange AROil Orange LGOil Orange ROil Orange 3 ROil Orange 2311Oil Red (V M)Oil Red BOil Red GOil Red 7327Oil YellowOil \ ellow (V M)Oil bellow AOil \ ellow GOil \ ellow ROil Yellow 2338Oil \ ellow 2G25Oil \ ellow 26S1Oil Yellow 7869Old GoldOleate Green OOmega Chrome Cyanme ROmega Chrome Red BOmega Chrome Black PVOpal BlueOpaline Blue ROrange 4LOrange DOrange GOrange GOrange 2 GOrange GCOrange GDOrange GRXOrange GSOrange GTOrange NOrange NAOrange PC

Manu-fac-turer

tMCGBVarVarVarVar\arVarSchSchBBMCVCICoBMBACJIvBBBHB&KHHHVarKKIBBSchBBCJVarSchBBSchSchSchQQSssMISchBVarKHKLBHByIGrEDH

SerialNo

50368221869870069870069S70069970005365446

A730519S

64756

245U495U369U163U164U165U759U166U370U371U760U761U762

36U372U372

36aU167U168

36U373U169U170U496

32U374

31U171U172

36a326832a

US04U805U711U712

85521

U679Ho37a38

139a38

139a144a37

13970

13979a

145a


Name

Orange ROrange 2 ROrange ROOrange ROOrange SOrange TOrange TAOrange XOrange IOrange IIOrange IIIOrange IVOiange 13Orange 14Orange 67 (V M )Orange 227Orange 23981Orange Cryst ilsOrange Ciystals 2 GOrange Red pureOrchil RCEPOrchil OPAGOrchil RPIIOnol YellowOnol Yellow ECOraeilhne BVOrtho Black 3 BOrtho Cyanme BOrtho Cyanine 6 GOxamme Acid Brown GOxamme Black AOxamme Black BBOxamme Black BHN BHXOxamme Black BBNXOxamme BHek BR1XOxamme Black RNOxamme BlueOxamme Blue A AXOxamme Blue BOxamine Bluo 3 B, BG

GNX, 3 11Oxamine Blue 4 IIOxamine Bnllunt Rod BXOxamine Brilliant Violet RXOxcimme Brown AOxamine Brown GOxanimo Brown 3 GOxamine Brown GROxamine Brown GXOxaramc Brown 3 GXOxamine Brown R, RGOxamine Claret BOxamine Copper Blue RROxamme Copper Blue RRXOxamme Dark Blue BGXOxamine Dark Blue BGEOxamine Dark Blue BRRXOxamme Dark Blue ROxamine Dark Brov n GOxamine Dark Brown ROxamine I aat Blur 0 VXOxamine Fast Blue RROxamme Fast Pmk BXOxamine Fast Red FOxamine Green COxamine Green B, BXOxamine Green G, GXOxamine Light Blue BOxamine Light Blue GXOxamine I lght Brown GOxamine Light Brown ROxamine I lght Green BOxamine Light Greea G

Manu-fac-turer

VarKBByBK tMA etcHVarVarPVarSSc

AWWDAAAAGGByAAABBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB

SerialNo

151139a151a

A277144151311S7J,141:11547

1305be5Sc3b3(>b58c3Sss

174UlbU47U*9ion1992>5A37A3bA39AS7ASSASJ*3 5

A00A)lA0242141042142113S5A03A04A05A90A07A08A<)9

A100344

A10]A102A103A105A101A107A10(>AlOfeA109A110A1UA112

US475474475

All iAmA115AllbA117A11S

Name

O\amine Light Green 3 GOxamine MaroonOxaminc Pure Blue 6 B,

G BO 6 BXXOxaminc RedO\ unine Red J B BNXOxumine VioletOvimme Yellow AO\ inane \ ellow 3 GOxy At id Red b BOOvy Chlor uol Blue BOxy Diammc Bl ick (V M )Oxy Diaimne Blue (V M )Oxy Dicumne Brown (V M )Oxy Diamme Caibon (VM)Oxy Diaminc Orange (V M )Oxy Diamme Red fc>Oxy Diamme Violet (V M )Ovy Diaminc YellowOxy Diuninopen (V M )Oxyehrome Blick IOxv chrome Blue Bl ick BGOOxycluotne Brown VOxichrome Biown VAOx chio nc Brown VNOxyehrome \cllow D(Jxychiomc Yellow DGOx\chiome \cllow 2 GlOxyphemnc A C, GG, RPicihc BluePalitinc IJUck A 4 BP ilatine BUck 3 GX MZ

sr brMP ilatine Chrome Bl ickP iHtine Chrome Black 0 B

6BXPalatine Chrome BHck VPalatine Chiomo Black SPalatine Chrome Blue l BP il \line Chrome Bluo W 2 BPalatine Chrome Brown "5 GPalatine Chiomo Blown

GGTXP ildtmc Chromo Brown

GGX, RP il itme Chromo Brown WP ilatine Chromo Bi own WNPalatine Chiomo Biowu

WNRPalatine Chromo Brown

WNR1XPalaiiuo CJiromo Green GPalatine Chtomc C»iccn GXPalatine Chronic Re I BPalatine Chromo Red RPal ihnt, Chronic \iolctPilitmo I lght Yellow RPalatine Orange RPalai me Red APalatine Scat let APalatine Scar lot G i 1U HPalalimtoPanama Black 3 G, RPaper Blue 0 GPapor Blue MDPaper Blue ClUiPaper Bluo 33598P iper Blues green HIHKICSPnpci Blues ted shadesPipci Biown BBPnp<r Biown BTPaper Hi own 111Paper 1 uut Boide mx B

Manu-fac-turer

BBBBBBBBGrEHCCCCCccccGrLGrEGrEGrEGrEGtEGrEGrECICoHBBBBBBBBB

BBBBBBBBBBBBBBBBbehSchMBSbchSchBBBBy


NameManu-fac-turer

SerialNo. Name

Manu-fac-turer

Paper Green DPaper Orange CRPaper Orange residue. ...Paper Red OPaper Scarlet (V.M.)Paper YellowPaper YellowPaper Yellow G, GGX?RRXPaper Yellow 3 GXPaper Yellow 3 RXXPara Black BPara BluePara Brilliant Orange GPara Brown GKPara Brown RKPara Brown SCPara Diamine Black (V.M.)Para Green 2 BLPara-FuchsinePara MagentaPara Orange GPara YellowParamineParanitraniline RedParaphenylene Blue RParaphenylene VioletParaphosphine (V. M.)Para RedParatol Chrome Yellow L. .Paratol Fast Yellow GParatol Lake Red KPParatol Lake Red LCParatol Lake Red LPParatol Scarlet 3 B, 3 BX..Parazole Brown RK.Paris VioletParis Violet 3 B, 6 B, 3 BA.Paris Violet 4 BA, 4 R, 90..Patent Alizarin Black DEB,

DFF, DFFAPatent Black (V. M.)Patent BluePatent Blue APatent Blue AEPatent Blue BPatent Blue L, LE, NOPatent Blue VPatent Blue V newPatent Blue J 3, JI, WE. ..Patent Marine BluePatent Marine Blue LER...Patent Phosphine G, GG,

M, RPatent Phosphine 19332Pegu Brown GPeii Wool Blue BPermanent Blue GRPermanent Orange RPermanent RedPermanent Red B, 2 B, R,

4RPermanent Red 4 BPersian Red RDPhenamine Blue GPhenanthrene Chrome BluePhenochrome YellowPhenocyanine TC, R, VS...Phenocyanine TVPhenylamine Black 4 B....Phenyl Crimson SPhenylene BlackPhenylene BluePhiladelphia Yellow 2 G.. .

KKKWDKVarWDBBBByCGBy§ByVarHByAWBVarWDWDCVarMMMMMMKPPPMCVarMA, MMVarMMMMIILCCGAAAABBKDHDHByCVPBKA

U375U37GU377307U37S303303a303a303303aA278702A2S2A279A280A2S1A3SSA2S3511"511A2»4U5S8U17856701695U29450U400U461U4152U4G3U404U405TJ379515515515S07aU295543545545543543543543543a543543bGOG60 GoA51187U493131152152a152U179A129U680U380642643A2S5A731267649606

PhloxinePhloxineB, GA, HMPhloxine PPhoenix Brown DPhosphine (V. M.)Phosphine APhosphine AR, GGPhosphine GPhosphine GOPhosphine LM, OPhosphine LB, PHLBPhosphine 3 RPhosphine RSPhosphine 12901Picric AcidPigment BlackPigment Black BPPigment ChlorinePigment Chrome Yellow L.Pigment Fast Red HLPigment Fast Yellow G ....Pigment Fast Yellow RPigment Orange RPigment Purple APigment Scarlet GPigment Scarlet 3 BPinachrornePinacyanolPinkPinkBPink MPink ColorPluto Black APluto Black BSPluto Black CFPluto Black FPluto Black GPluto Black SSPluto Brown GGPluto Brown NBPluto Brown RPluto Milling Black BPluto Orange GPlutoform Black 3 GLPolar Orange GSPolar Red 3 BPolar Red GPolar Red RPolar Red RSPolar Yellow GPolar Yellow 2 GPolar Yellow RPolar Orange RCPolychromine ACPolychromine BPolyphenyl Black B VCPolyphenyl Black GNCPolyphenyl Blue GCPolyphenyl Blue GFPolyphenyl Brilliant Blue3 GPolyphenyl Fast Red BC...Polyphcnyl Orange RC....Polyphenyl Yellow 3 GC...Ponceau (V. M.)Ponceau BOPonceau GPonceau 4 GBPonceau KPonceau Xt, 2RPonceau 3 RPonceau 4 RPonceau 4 RPonceau 5 R. r

DH,MMBAVarGrEtMSKMGrEAIIPBBMMMMMMMMMMMKIH

%ByByByByByBy

GGGGGGGGGGGGGGGGGGKAMA, etc.IVarVarP


Name

Ponceau 6 RPonceau 3 RBPonceau 4 RBPonceau 6 RBPonceau 10 RBPonceau RL, 2 RL, 3 RL,

2RLHPonceau 2 RLPonceau SPonceau SPJPonceau S 2 RPonceau W 3 ItPonceau XPonceau 12402Ponceau for SilkPonceau (free from arsenic)Potting Black BPrague Alizarin Yellow GPnmal BlackPrimazme Yellow GPnmulmePrimulme APnmulme (V M )Pnmulme YellowPrinting Black for WoolPrinting Blue for WoolPunting Yellow (greenish)Prune 516Prune purePure Blue AIPure Blue DS DSGPure Blue RTPuie Soluble BluePure Yellow DGPurpunn (synthetic)Pyrarmdol Brou n BGPyramidol Brown TPyramine Orange 2GXPyramine Orange 3 GPyramme Orange RPyramine Oiinge RRPyramine Orange RlPyramine Yellow GXS,

GXSCPyramme Yellow GXSPPyramme Yellow R, RXPyrarolc Orange GPyi azoic Oras p,e RPyi o allol-cy anme aulphon-

IC acidsPyrogenc Black GPyrogono BluePyrogene Blue RR, 2 RNPyrogenc Blue Green BPyrogenc Brown DPyrogenc Brown GPyrogeno Brown GXPyrogeno Brown ORPyrogene Brown ORRPyrogeno Brown 4 RPyrogono Cutch DRPyrogeno Cutch 2 GOPyrogene Cutch 2 RPyrogeno Dark Green BPyrogeno Deep Black C, D GPyrogene Direct BluePyrogene Direct Blue green

shadePyrogeno Direct Blue, red

shadePyrogene Direct Blue RLPyrogone Green GPyrogene Green 2 G

Manu-fac-turer

B, MAAAAAByAPBPBKIP.KWDIKiABVarB, MVarAW.ByBBKLevSIHBKCKBFAFABBBBBBBBSsDIIII CIIIIIIIIIIIIIIIIIII

SerialNo

17024724925525982a82

247albOb82

It ObS2b

17 117582c18449

U50AHO

(>10bib016010a770742

U3S26*60*6539"H9r>395 30

U S37S*m370302a*00toO3143G2304iOt101402

A7220237*0720720740

Slr)r>Sl%SI 57Slri88159SlbOfelOlbl62SI 0374072072072072072074b709

Name

Pyrogene Green 3 GPyrogenc IndigoPyrogenc Indigo CL 5 G GLPyroxene Indigo R RRPyio enc Olive 3 GPyrogene Oiantoe RPyrogene Yellow M O 3 RPyiol Brown GPyrol Brown 00181Pyrol Brown (yellowish)Pyronme GPyiophosphine CQueuilton Substitute VQueicitton Substitute WBLQuinolmc BluoQuinohne RedQuinolmc 'i ellowQumolmc YellowQuinohne YellowQuinohne YellowQumohnc YellowQuinohne YellowQuinohne YellowQuinohno YellowQuinohne Yellow KT NQuinohne Yellow OQumolme Yellow PQuinolmc Yellow 0272Qumohne Yellow, spirit eol-

ubloQumohne Yellow watei sol-

ubleRadial Yellow GRapid Filler Gio( n IlUpidFiltei Rod IRaven Black HSSSRed (V M)Red PCRed PCRed 2 SRed Blue BSRRed BrownRed CorallineR,cd for Leather ORed for I either RRod T ike RLRid Take RMTR( d VioletRed Violit 5RRed Violc t 5 RSReddish BrownRenol Black BUNK(nol Black Sr STR< nol Blue BRonol BordeauxRonol Bulhant YellowRenol Brown MB, RARenol Dark Grcon NOONGRenol Fast Red 4 BRenol Green BRenol Light Blue ARenol Light Blue GRonol Light Blue GR( nol Orange 3 APRenol RedRenol Yellow 3 RRenola-mme Black BHNRoHofJnvin Wltosomn BlueHcsoroin BrownResoTCin Brown GResorcin Brown QVResorcm Dark Brown

Manu-fac-turer

IIIIIIILLLI, ByWDBBGAAAWBByCIMSByMBIVarVarBMMIICJDHGPGiEbMAByBytMBBKtMtMtMtMtMtMtMtMtMtMGtMG tMtMtMG tMBMVarGGBK

SerialNo

740735735735740

S1017*1

S135S130S135508

U547U184U183

011blO012013G1261}01}013013bl2(>H01B012012C1201330

U167U108U704U497UbOOU042

483aU513

lOOo55b

U469UbO

U250U257

514514525

XJ384402b4(>2b410

A517ao*344

Ar)18A519

475A 520A 058A521

302aA522

0333771047211211211213


Name

Resorcin YellowRheonineRheonine AL, GDRhine BlueRhodamine ALRhodamine BRhodamine SBRhodamine BNRhodamine BSPRhodamine GRhodamine 3 GRhodamine 5 GRhodamine 5 GRhodamine 6 GRhodamine 12 GFRhodamine 6 GNRhodamine SRhodamine SRhodamine SPRhodamine RRhodamine 6302Rhodamine Scarlet GRhodine 2 GRhodine 12 GMRhoduline Blue 6 G .•••••Rhoduline Heliotrope 3 B.Rhoduline Orange N, NO.Rhoduline Red B, GRhoduline VioletRhoduline Yellow 6 GRoccellineRoccelline FSRoccelline MBRoccelline SRosanthrene AWLRosanthrene BRosantbrene CBRosanthrene RRosanthrene Bordeaux B..Rosanthrene Orange 16754Rosanthrene Violet SR....Rosazeine BRosazeine B 5Rosazeine 6 GRosazurine BRosazurine GRose(V.M.)Rose BengalRose BengalRose Bengal BRose Bengal BRose Bengal NRose Bengal NTORose MagdalaRoseine BRosindulineRosinduline 2 BRosinduline GRosinduline 2 GRosolaneRosolane B, ORosolane O, T, RRosophenine 4 BRosophenine 10 BRosophenine SGRubineRubine NRubine NRubramineRussian Leather Red R...Russian RedSaba Phosphine G, GGSafranine

Manu-fac-turer

SchBBQBVar

B

VarB

VarBB.ByIBQ

TkByUByC,FAHtMG,tMIIIIIMMMA, ByA, ByCJVarG,MB,LK,MCBDHSKKKKPMMCICoCICoCICoAABCGACsVar

SerialNo.

143607607631572a573574573573572576576a572a571578571570570570572a572a57Gb577575

TJ25SU259603a6S40S4618a161161161161

A704A705A706A7O7A70SA709A710

573IT471U472

372371

U498595597597597595595694512674673675674688687687483194195512512

U189703512512606679

Name

Safranine (V. M.)Safranine BSafranine 6 BSafranine F FSafranine FSafranine FBSafranine 3VINSafranine OSafranine T, TKSafranine YSafranine Ziafranine 1081

Safranine bluish .Safranine (blue shade)St. Denis Black BSt. Denis RedSalicine Black (V. M.) . .Salicine Black K, LR, SSalicine Black U , U L . . .Salicine Blue BSalicine Bordeaux R. . . .Salicine Brown (V. M.)Salicine Dark Green CSSalicine Green CPSalicine Orange 2 RSalieine Orange 2541, 2542..Salieine Red BSalicine Red GSalicine Violet RSalicine Yellow (V. M.) . . . .Salmon RedScarlet

carlet (V. M.)Scarlet ABScarlet 6 BScarlet BNScarlet CScarlet ECScarlet GAScarlet GRCL, MScarlet GXScarlet 15 NScarlet PScarlet PO, 2 PRScarlet R, 2 RScarlet R, 2 RIcarlet 2 R

Scarlet 2 RScarlet 3 R, 6 Rr 2 RCL,

3 RCLScarlet 3 RScarlet 4 RScarlet 4 RScarlet 6 R crystalsScarlet RDScarlet 4 RI, 2 RIIScarlet 4 RZScarlet S 2 RScarlet S 3 RScarlet 2 SRMScarlet X, X XScarlet 50Scarlet 231, 243Scarlet 1610Scarlet 7214Scarlet 53446Scarlet (yellow shade) 17413Scarlet (yellow shade) 24211Scarlet for silk SScarlet residueSeal Brown WSella Brilliant Yellow PSella Flavine G

Manu-fac-turer

VarVarSch

l y

BBMBSchKKhPPKKKKKKKKKKKKKKACDCoCGrEGrEBBMKBKKMVarKtMMBP,tMBKHAWMBBBKHCJKBABBPKPGG

SerialNo.679679680679679679683679679679679679680679718483181b181b181A403A404A405276A407A408A409A410A411A412177b120174247A475A476A131196a247A132174aU385A133U3S5U385174a82U385176174a8383176a223bS2d106b174aA134A135A136TJ38516976aU385A137U61A138A139247cXJ385•U594U643TJ644


Name Manu-fac-turer

IAGGGtMBBKQGrEGrEGrEQByBKKMBKQCABtMtMSAAIIIIIIICsQGrEGrEGrEQQMCQMQQByCoVarH&MVarGrECGPGrEKGrEBtMMGrEtMtMGBBBSG

SerialNo.

U(5S253950049 G500539a537559539539a539a539a539537550

U38GU473

G13US11

7007007585G

A523424A44A44a

UG84UG83UG85UG8GUG88UG87UG89U29GG99G99099099G99

US12U813U474

495499

1U814

137537539537539539539539539539539539539539539539539539 c6464U190

006U645

NameManu-fac-turer

Sepia Black FW, 1499SSerge BlueSetooyanine OSetoglaucine OSctopalineSilk BlueSilk Blue BSilk Blue BSilk Blue BSilk Blue BJBNOOSilk Blue BS3BB, BT5BOO

BTRSilk Blue BTB, BTllSilk Blue 4 RSilk Blue 4Silk Blue 5770Silk Gray CB, 281Silk Wool Black 3 BSilk Yellow NSilk Yellow NSilvor Gray N. . . .•Silver Gray PSinus Yellow GSitara Fast Red RLSitara Orange XSky Blue FFOSolaminc Blue BSolamino Roil.SolliKenc Blue Green BSoliigene Blue Green 1G444.Solligene CutchSolligene CyanineSolfigono Deep Black (V.M.)Solfigene Deep Black 14717.Solfigene Gieen GGSolid Blue (V. M.)Solid Blue 3 RSolid Blue RXSolid Blue SBAOOOOSolid Blue SBSOOOSolid Blue Base SBXBX. ..Solid BrownSolid Brown KFSolid Brown OSolid Green (V. M.)Solid Green 3 GSolid Green OSolid Red BSolid Yellow GSoluble BlueSoluble BlueSoluble BlueSoluble Blue (V. M.)Soluble Blue AOOOOSoluble Blue B, BCBIISoluble Blue BLSE, 3 BS...Soluble Blue BS 3B B, BSJ.Soluble Blue C 2, C 3, C 5,

CXSoluble BIUO'ELOOO '.!'."!Soluble Blue HA, IN, 4 R,

TB, TLSoluble Blue 5 RSoluble Blue RMSoluble Blue base SBXR. . .Soluble Blue crystalsSoluble Blue (greenest shade)Soluble Navy BlueSorbin RedSorbin Red XSpecial Blue GSpecial Phosphine GSpirit Black

Spirit Black (V.M.)Spirit BlueSpirit Blue BVESpirit Blue RSpirit Blue, green shades. ..Spirit Blue, red shadesSpirit NigrosineSpirit Nigrosine LM, VSpirit YellowSpirit Yellow RStanley RedSteam Green GStilbene YellowStilbcnc Yellow 3 GStilbene Yellow 3 GStilbono Yellow 2 GP,

3 GPX, GXStilbene Yellow RXStilbene Yellow 5912Straw Blue GSudan G, 2 G!Sudan RSudan ISudan IISudan IIISudan IVSudan BrownSudan Brown SSulfamine Brown ASulfamine Brown BSulfaniline Brown O, R. . ..Sulfine Blue BSulfine Blue RRSulfine BrownSulfine BrownSulfine Brown B, GSulfo Blacks B, 2 BSulfo Green B, CSulfo Rhodamine BSulfo Rosazeine BSulfo Rosazcinc GSulfogenc Brown G, DSulfolino GSulfolino GSulfoline RSulfon Acid Black N 2 B. ..ISulfon Acid Blue BISulfon Acid Blue RSulfon Add Green BSulfon Black 3 BSulfon Black GSulfon Blue RSulfon Orange G,5GSulfon Violet RSulfon Yellow 5 G, RSulfonazurineSulfoncyanineSulfoncyanine BB, GR,, 5 R,

SRSulfoncyanino G, GR, 5 E,

5 RTSulfoncyanine Black B, 2 BSulfoncyanino Black BB,

GR.Sulfur BlackSulfur BlackSulfur BlackSulfur Black A, AW, AWL.Sulfur Black B, 2 B, 4B. . .Sulfur Black 2 B, BR, BRH,

GFSulfur Black FAG, FTSulfur Black H, JBL

CJVarPMSchSchWDHL,tMCICoBVarCICoCllBBBByAAAAA, etc.A, etc.ASchWDWDKCGCGCGCGIINFMMMAWKAWByByByByByByByByByByByVarBByByBVarWDAAAKAA


NameManu-fac-turer

KALevKKAAAABKKAKAAAAABKKALevLevAAAAIAALevLevKKAAAAAAAALevLevAAAKKSAAAAAKSAKAAAIHHHHVarSGByByA

SerialNo.

720720720720720720SIS2S3

S123S83S4S83S6S7S8S9S10

S124S83Sll

S168S1C9S12S13S14S15

S165S16S17

S170S171S84S84SISS19S20S21S22S23S24S25S172S173S26S28S29S85SS5S167S3OS31S32S33S34

U388712S35

U388S36S37S38S166363405304d304999

U263U264A45

NameManu-

fac-turer

Sulfur Black KCB, MASulfur Black T, TFA, T G . .Sulfur Black TRSulfur Black TS, 5274, 5276Sulfur Black 5285, 52S9Sulfur Black 108583Sulfur Black Brown NSulfur Black Brown NRSulfur Blue BSulfur Blue BESulfur Blue BG, CHLSulfur Blue DSulfur BlueGSulfur Blue LSulfur Blue PRSulfur Blue RSulfur Blue 2 RSulfur Blue 4 RSulfur Blue RRSulfur Blue USulfur Brilliant Green GIC..Sulfur Bronze 136Sulfur Bronze 158Sulfur Brown CL 4 RSulfur Brown GSulfur Brown 2 GSulfur Brown 6 GSulfur Brown MSulfur Brown OSulfur Brown OBSulfur Brown 527Sulfur Brown 731Sulfur Brown (bluish)Sulfur Brown (reddish)Sulfur Catechu GSulfur Catechu RSulfur Corinth BSulfur Corinth CLBSulfur Green 2 BKSulfur Green 4 BKSulfur Green GSulfur Green 4 GKSulfur Green 309Sulfur Green 330Sulfur Indigo BASulfur Indigo CLSulfur Indigo CLGGSulfur Indigo Blue RCLSulfur Indigo Blue 827Sulfur OliveSulfur Olive BSulfur Red Brown 2 R K . . .Sulfur Red Brown 6 R K . . .Sulfur Violet RSulfur Violet YSulfur Yellow ESSulfur Yellow GSulfur Yellow GSulfur Yellow GSulfur Yellow 4 GSulfur Yellow ISulfur Yellow RSulfur Yellow RSultan 5 BSultan 10 BSultan Orange DSSultan Yellow HSun YellowSun Yellow G, GS, R RSun Yellow 3 GCSupramine Brown RSupramine Yellow RTabora Black X

Tannin HeliotropeTannin Orange RTannin Orange RTartrazineTartrazine G, X, X XTerra Cotta FCTerra Cotta 2 RN, R G N . . .Tetracyanol ATetracyanol SFVThiazine BlueThiazine Brown RThiazine Red GThiazine Red RThiazine Yellow G, 3 G, GLThiazol Yellow GThiazol Yellow GRThiazol Yellow R , R HThiocarbqne NNGThiocarmine RThio CatechineThio Cotton BlackThioflavine (V. M.)Thioflavine OIOThioflavine SThioflavine TThioflavine 654Thiogene Black BB, 5 B . . .Thiogene Black M, MA,

MMThiogene Black ML, M Z . . .Thiogene Blue RLThiogene Blue RThiogene Blue 2 RThiogene Cyanine BThiogene Cyanine GThiogene Dark Red GThiogene Deep Blue B R . . .Thiogene Deep BlueThiogene Green BLThiogene Green GThiogene Green GGThiogene Green GLThiogene Khaki NTMogene New Blue JLThiogene Olive Green GGNThiogene Orange RThiogene Violet VThiogene Yellow GGThiogene Yellow 5 GThiogene Brown GThiogene Brown GGThiogene Brown GCThiogene Brown GRThiogene Brown G 2 R . . . .Thiogene Brown RThiogene Brown SThio Indigo Brown GThio Indigo Brown 2 RThio Indigo Orange RThio Indigo Pink 247, 2475.Thio Indigo Pink Rose BW.Thio Indigo Red BThio Indigo Red 3 BThio Indigo Rose AN, BN. .Thio Indigo Scarlet GThio Indigo Scarlet RThio Indigo Scarlet S, 6086.Thio Indigo Violet 2 BThio Indigo Violet KThio Indigo Yellow 3 G N . .Thional Black GThional Brilliant Green 29..Thional Brown

CCsVarBGGCCGBBBffBDBBCPWDCKS,CCKM

MMMMMMMMMMMMMMMMMMMMMMMMMMMMKKKKKKKKKKKK


NameManu-fac-turer

SerialNo. Name

Manu-fac-turer

Thional Brown GThional Dark Green GN..Thional GreenThional Green GGThional Red BrownThion Black (V. M.)ThionBlueBThion Brown (V. M.)Thion Dark Blue BOThion Direct BlueThionine Blue GOThionine Blue 00, 3 O....Thion Green 2 GThion Green 829Thion Navy Blue (V. M.) .Thionol BlackThionol Black S, XXThionol Yellow GRThion Orange (V. M.)Thion Purple 0Thion VioletThion Violet BlackThion Yellow (V. M.)Thion Yellow 2 GThion Yellow 5 GThiophenol Black TThiophor Black WLNThiophor Blue BThiophor Bronze 5 GThiophor Dark Brown B..Thiophor Deep Green CG.Thiophor Indigo CJThiophor KhakiThiophor Orange OThiophor Yellow RThiophor Yellow Bronze GThiophor Yellow OliveThio Vesuvine BBThioxine Black ABOOOO.Thioxine Black ABBOOOOThioxine Black 3 BOOO. .Thioxine Black GB, 1151,

3705Thioxine Brown 5 GThioxine Brown 2 GRTitan Como 2 BTitan Como RTitan Fast Black BTitan OrangeTitan RedTitan Scarlet YTitan Yellow G, YTolamine VioletTolaneRedB, GToluidine BlueToluylene Black GOOToluylene Brown GToluylene Brown RToluylene Fast Brown 2 RToluylene-Fast Brown 3 GToluylene Fast Orange GLToluylene OrangeToluylene Orange GToluylene Orange GOO...Toluylene Orange RToluylene Orange RR... .Toluylene Red 00, RT ...Toluylene YellowToluylene Yellow 00Tolyl Black B, BB,BG...,Tolyl Blue 5 RTolyl Blue SBTolyl Blue SR

SSsssKKKKKA, MAKKKLevLevLevKKKKKKKICJCJCJCJCJCJCJCJCJCJCJGrEGrEGrEGrEGrEGrEHHHHHHH,BDKB,MGrEGrEGrE

VarGrE,SMGrEGrEGrEGrEMMMM

74774674674674772073(5S86S87736a601661SS8S89S90719720198S91S92S93720S96S94S95720720

S127713

S128S129731

S130S131S132714

Sl32aU815

720720720720

S133S134:A761A7G2A763A764

190196198

U69043

659 aA477

285488

XJ260U265

392d392392392287287358286286265257189188

Tolyl Blue ST, 7656Tonka Brown GSTriazol Blue B ,Triazol Blue BOOTriazol Blue BBOO ,Triazol Blue 4 BOOTriazol Blue R ,Triazol Blue 3242 ,Triazol Bordeaux BTriazol Brown GOOA....Triazol Brown GOOOTriazol Brown HROTriazol Brown SOOO.Triazol Dark Blue BHOOOTriazol Dark Blue

BHPOOOOTriazol Dark Blue BHTOOOTriazol Dark Blue BOOTriazol Dark Blue 3 GTriazol Dark Blue ROO....Triazol Fast Red LTriazol Faat Yellow 2

GOOOOTriazol Green BTriazol Green BPOOTriazol Green GPOOTriazol Pure Blue 3 BTriazol Pure Blue 11Triazol Red BTriazol Violet RTriazol Violet RRTriazol Yellow NBPOO....Trisulf on Blue BTrisulfon Blue 3 GTrisulf on Blue RTrisulf on BrownTrisulfon Brown A, B, MB.Trisulfon Brown GTrisulfon Brown GGTriaulfon Violet BTropasoline (V. M.)Tropseoline 00Trypan BlueTrypan RedTurmeric Yellow 000Turquoise BlueTurquoise Blue B, BB, G...Tuscaline Orange GTypophor Blaok FBTypophor Brown FRTypophor Black F 3 RTypophor Brown FBTypophor Rod FGTypophor Yellow FRTypophor Yellow F 3 RUltra Flavine SDUltra Orange RUltra Violet BUltra Violet FKNUltra Violet LGPUltra Violet MOUltra Violet 943Ultraoyanine BUnion Acid Black Bli, GH.Union BlackUnion Black BRNUnion Black SOJUnion Blue HUnion Blue RUnion Blue RUnion Blue (V. M.)Union Fast ClaretUnion Red B

MGrEGrEGrEGrEGrEGrEGrEGrEGrEGrEGrEGrE

GrEGrEGrEGrEGrEGrE

GrEGrEGrEGrEGrEGrEGrEGrEGrEGrESSssssssC, etc.HMM

i-BBBBBBBSSsKssKsIIcsAsMKCLevK


Name

Union Red BSUniversal Black BUrania BlueUranmeUranme AUranme NUrsolUrsol AUrsol ADFUrsol DUrsol DBUrsol DFUrsol GGUrsol PUrsol PPUrsol Gray ALVarnish BlackVarnish Black 5 RVesuvine (V M )VictonaVictoria Black BVictona Blue BVictona Blue B baseVictoria Blue BE, BS, BSSVictona Blue RVictona Blue 4 RVietona Blue BaseVictona Blue Base 61272Victona Brilliant Blue BVictona Fast Violet BVictona Fast Violet 2 RVictona GreenVictona Green BFVictona Green 4833, 4S34Victona Green BaseVictoria Navy Blue LVictona Pure Blue BVictona Scarlet RVictona Scarlet 2 R, 4 RVictona Scarlet 3 RVictona Violet (V M )Victona \ ellowVidal Black IVigoureux Brown IVigoureux Past Black TVigoureux Green BViolamine BViolamine 3 BViolamine RViolet 2 BViolet 6 BViolet DVViolet NXViolet 9 0, 300 XEViolet 5539GViolet Base 2 BViolet Base 5747Violet BlackViolet CrystalsViolet CrystalsViolet Crystals 5 BO, 6 BOViolet Crystals 0Violet Crystals 142 SViolet Direct VRViolet Modern NViolet Neutral 0Violettine 3 RVmdanthrene BVitoline Yellow 5 G, RVulcan Blue BOVulcan Blue GWater BlueWater Blue MX

Manu-fac-turer

wbA, etcBMAAAAAAAAAQGBy\ar\arBVarVarSHMByByVarBB>B tMByBMtMMVarMPMMCMMMK tMQQAWPHQBKBSKIMKGDHMAWBtMLevLevC.etcQ

SerialNo

A412bU2b7

6G55S5585585923923923923923923923923923923

U54SUS162b41692b25595o9559558522559a559a559b

TJ26SU269

497a497a497a497a

TJ270559

A439169

A44061

134717

XJ477159a

U299580584582516a517516a516a516a516a516a51ba290516516516516516

A660624516a

U591705606

U740U741

539539

Name

Water Blue S 2 KWood Red 40 FWool Black (V M )Wool Black (V M )Wool Black (V M )Wool Black b A CANWool Black B 2BWool Black BWool Black BBWool Black 3 BWool Black 4 B 6 B, 4 BCWool Black 4 BWool Black 10 BWool Black 4 BrL, G BS,

4 BXWool Black CD CLWool Black DWWool Black G GR, GRFWool Black 6 GWool Black GGWool Black HNWool Black LRWool Black MXWool Black NWool Black NNWool Black N 4 BWool Black NCWool Black NPWool Black NPWool Black NRWool Black SGWool Black VWool Black 9904Wool Black (greenish)Wool BlueWool BlueWool Blue (V M )Wool Blue (V M )Wool Blue BWool Blue 2 B 5 B, GWool Blue 2 BXWool Blue G, 2 G, G 446 NWool Blue MWool Blue NWool Blue R, RXWool Blue RWool Blue 5 RWool Blue SWool Blue SWool Blue 2 SWool Blue SBWool Blue SDOO, SLOOWool Blue SRWool Blue TBWool Blue 1092Wool Blue Black 2019Wool Brown MC, P, SVR,

UB 2S08Wool Canary ODWool Cense SRWool Claret 21 BWool Claret Red 87 B, 211,

357Wool Fast Black BFool Fast Blue BLTool Fast Blue BL

Wool Fast Blue GLWool Fast Blue LWool Fast Orange GWool Fast Yellow GWool Fast Yellow 5 GXWool Fast Yellow WG"Wool Green (V M )

Manu-fac-turer

A&chIvLevtMAKAWLevAItMAIvBKAGtMtMIvQMIBy3vByCGIvGrEBKIvcQKLevAWAAKAWByAl y

KKAWBByKAKKHKLevLevBBByByIBBBBK

SerialNo

539lbb

U390220b220b217g220b

U39O272c220b220272c2l7g220

U3902(>9220b

Ub4b217217g

U390220b

A441272c

A301U3<)0AS02

272cU390

272cU390

269U300moo

53bbU391

505a5(i55b55b5a

U3915b2b56256 5a5b2b538

um538b

U391562b530d562

U391565a

U392U393U765U394U742U743U200U201U271U272U693U202U203U204U205U395


Name

reenreen Breen BSreen Sreen SAK, 16437reenSCt Black 3 B3dd (V M)jd CdCSdG3d K 10 BXdL MC, SOCdSBd7742ailetarlet (V M ) .arlet 5 Barlet Railet RRarlet 4 Rarlet 3 RBDiet Bolet RDiet SDiet SLHowHow AT D GHow LDV, RllowSllowTHow 1501>CJB-IEosine5 BGRmEHnYDonilue AS ASL BSUue VSast Green Blght Yellowight Yellow 2 G

Manu-fac-turer

tMQByBKVarIGAKCsKBBKCGBKKLevH&chBBKBQKBKSchKKGGKIPHHHHHHSssVarK S

SerialNo

566a5b6566566566a566220cIb8b236236bIb8b

A14OA141

168bb4

168bU39b

bObbOc80

A14280a

A14359a

U39759

U39S23

U399U309

1432*

U39900bCOb590a

U770U770

284aU771U772

5085075042222

Name

Xylene Light Yellow RXylene Light Yellow RXylene Red BXylene YellowXylene Yellow 3 GXj hdine Orange RRXylidinc Scailct\ ellow (V M )\ ellow (V M )Yellow CPY ellow FYYellow NlYellow Nrbellow PCYellow 11Yellow 2 SYellow (for feathers)Yellow Black MYellow last-To boapYellow Tat ColorYellow Groen 0 BZambesi Black BZambesi Black 2 BAZambesi Black BHZambesi Black BRZambesi Black OTAZambesi Black DZambesi Black FZambesi Black OBAZambesi Black RZambesi Black VZambesi Black VMZambesi Bordeaux 7 BZambesi BrownZambesi Brown G 2 GZambesi Brown 4 RZambesi Pure Blue 4 BZambesi Red BZambesi Red 4 BZambesi Red 0 BZambesi Red 8 BZambesi Rubine BZambesi beat lot 6 BZambesi Seatlet 2 BLZambesi Seailot FRZambeHi Scarlet PR

Manu-fac-turer

KSbTvBK.lMSdiCJ1Lev11BKQDIIwpWDBKPBBKAAAAAAAAAAAAAAAAAAAAAAAA

SenalNo

2222

579111179S2

Ur>00lUd1 illl1777*

171-S7U817UbOl

Hid1*7

U5 i()U18S

20*(>S

IHSQAUiA17A1SA49Ar>*Ar>()Ar>lAr»l:Ar>2Ar)r)Ar>bAr>7**0**()* *()ll271bAr>SAWA(H)A01A(i2AOJA(nA(io

L G E I N D E X O F S C H U L T Z N U M B E R S F O R D Y E S

Ls the Glossary of Dye Names refers only to Schultz numbers, by look-in this index for the Schultz number, there can be found the pages

which any dye is tabulated.?his procedure was adopted for the reason that a given dye, eharac-zed by a Schultz number, will be known under very many names.5h names are listed in the Glossary but could not all be placed in theles without unnecessarily enlarging this book.

dtziber Page1 5092 362,4473 2234 5265 4606 3607 3608 4569 4520 253, 260, 4521 260, 453, 5092 91, 253, 260, 4533 200, 453, 471.4 78, 4535 126, 4536 183, 453,7 183, 4538 183, 253, 260, 4969 21, 91, 345, 48110 91, 481, 53411 343, 55212 21, 213, 529,3 230, 482, 52914 87, 34315 21, 49616 343, 496.7 21, 345, 482, 49018 343, 53319 67, 34310 Not classified\1 32, 9112 91, 23813 91, 46514 92, 56615 92, 50916 92, 36217 92, 52618 92, 28619 92, 50410 92, 174LI 92, 29812 22, 93L3 93, 326L4 93, 50815 93, 311L6 362, 421L7 421, 504L8 421, 519L9 421, 517>0 279, 42211 183, 42252 353, 422>3 330, 422

SchultzNumber

54555657585960616263646566676869707172737475767778798081828384858687

90919293949596979899100101102103104105106

Page394, 422409, 422362, 377, 422174, 42393, 423, 519219, 248S3, 50926, 174, 423, 471245, 500225, 245, 42326, 37026, 50422, 2727, 17436, 554554, 567526, 553225, 553362, 456362, 45542, 43, 36242, 43, 509362, 576414, 576375, 576526, 577372, 577370, 578505, 577, 578498, 50578, 50076, 48450, 362Not classified465, 494465, 49478, 494353, 49460, 494108, 362108, 414108, 37249, 108, 519156, 363363, 425363, 42649, 37149, 505126, 519126, 519142, 414360, 385363, 385

627

SchultzNumber

107108109110111112113114115116117118119120121122123124125126127128129130131132133134135136137138139140141142143144145146147148149150151152153154155156157158159

Page385, 447375, 3S5370, 385372, 385385, 526385, 505287, 385174, 385363, 392392, 447182, 371182, 225, 372165, 18284, 185185, 371185, 287186, 52693, 238, 555, 56993, 460, 655, 56993, 363, 565, 50993, 555, 57094, 555, 67038, 17438, 43, 174, 27746, 36374, 36374, 519262, 334262, 334262, 33432238, 529202, 529202, 529202, 529202, 530510, 630360, 530363, 630225, 530225, 53075, 3043687, 26287, 36487, 31146, 36481, 46681, 61081, 36481, 22380, 50077, 364

628 PAGE INDEX OF SCHULTZ NUMBERS FOR DYES

SchultzNumbei

160161162163164165166167168169170171172173174-175176177178179180181182183184185186187188189190191192193194195196197198199200201202203204205206207208209210211212213214215216217218219220221222223224225226227228229230231232233234235236237

Page354, 360354, 364330, 364354, 414354, 375354, 370354, 526180, 354355, 505287, 355355, 380174, 355153, 360364, 403153, 365365, 404153, 414153, 178, 51955, 520311, 40368, 36068, 36594, 125, 298, 55276,36076, 36572, 365276, 29863, 299299, 484299, 572183, 466, 496437, 496473, 496183, 365184, 414414, 496184, 527496, 527184, 497184, 497, 520110, 365110, 527110, 50540, 26240, 520454, 460, 471243, 454, 471454, 471, 475466, 471184, 355, 466, 497334, 473, 497510, 530, 578361, 531355, 510361, 57994, 326, 42365, 94, 42394, 299, 42371, 207, 386, 42494, 326, 49470, 386, 531424, 520, 53183, 421, 51032, 36532, 41432, 37032, 37233, 28733, 38033, 22636, 15336. 27636, 36636, 41436, 52736, 37236, 50537, 527

SchultzNumber Page238 37, 506239240241242243244245

27, 47, 242, 366, 466S3, 366, 55394,295,38694, 226, 40027, 386, 52727, 386, 506295, 386, 424

246 34, 366247 34, 366248 34, 527249 34, 180250 34, 520251 34, 180252 37, 366253 37, 414254 37, 527255 37, 180256 334, 386, 485257 334, 386, 400, 485, 572258 334, 3S6, 401259 108, 180, 531260 48, 366, 531261 299, 3S6, 531262 226, 387, 531263 39, 387, 483264 299, 355, 3(56265 330, 387, 401, 485266 2S5, 3S7267 204, 264, 285, 387, 387,

394268 67, 387, 394269 387, 394, 506270 55, 94, 2S7, 506271 55, 67, 3G7272 55, 388, 506273 23, 3S8, 411, 527274 23, 295, 388, 411275 85, 376, 388, 415276 85, 226, 388277 85,401278 38S, 401279 33, 95, 325, 4SG280 535, 550281 392, 535, 556282 392, 535283 4«6284 567285 200, 466286 200, 437287 200, 392288 198, 367289 19S, 3I>7, 527290 27, 3SS, 415, 471291 415, 471, 520292 175, 472, 520293 527, 541294 520, 541295 194, 205, 567296 27, 486, 520297 194, 295298 193, 506299 196, 506300 196, 506301 199,392302 153,199303 199,460304 199,460305 199, 520306 126, 437, 473307 126, 355308 126,330309 120, 356, 413310 126,413311 126, 177, 356312 126, 356, 415313 127, ISO, 356314 84, 127, 437

SchultzNumber Page315 84, 127, 460316 84, 127, 154317 127, 510318 127, 367319 127, 287, 460320 127, ISO321 127, 180, 372322 84, 127, 367, 379323 128, 175324 70, 128, 180325 70, 128, 371326 128, 325327 128, 295328 128, 295329 128, 295, 466330 128, 295, 412331 128, 295, 447332 84, 128, 295333 128, 296, 299334 129, 273, 300335 129, 296, 326336 70, 129, 300337 129, 300338 129, 326, 546339 82, 129, 520340 129, 129, 356, 405,

521, 521341 129, 506, 521342 130,521343 130, 296, 521344 130, 296, 521345 69, 130, 521346 130, 325, 521347 130, 341, 522348 130, 243,522349 130, 475, 522350 130, 184,522351 130, 178352 131, 228, 567353 131, 228, 300354 131, 22S355 415, 432, 522356 210, 356357 154, 210358 84, 210359 84, 137360 135,437361 136, 483362 201, 546363 356, 546364 330, 546365 154, 546366 154, 405, 546367 405, 547368 154, 356, 547369 84, 357, 547370 84, 154, 547371 276, 405, 547372 276, 547373 84, 460, 547374 357, 510, 547375 357,415,547376 510, 547377 415, 547378 367, 379, 547379 175, 415, 548380 175, 548381 300, 309, 548382 300, 388, 548383 300, 392, 548384 70, 181, 548385 325, 415, 548386 300, 410, 548387 70, 371, 548388 70, 548389 65, 549390 70, 300, 549391 301, 549

PAGE INDEX OF SCHULTZ NUMBERS FOB DYES 629

SchultzNumber Page392 178, 201, 549393 243, 522, 549394 522, 549395 178, 549396 227, 416, 549397 228, 416, 549398 229, 549399 227, 296, 550400 3b7, 551401 2b8, 416402 2b8, 206, 373403 2G8, 296404 268, 461, 522405 202, 357406 202, 3b7, 399407 202, 3r>7, 416408 202, 202, 202, 368, 421,

424409 202, 308, 379410 202, 41b411 202, 376412 202, 41b, 506413 202, 224, 567414 203, 221, 507415 17r>, 203416 203, 22b417 166, 16b, 203418 105, 203419 64, 203, 368420 70, lbl, 203421 60, 203, 416422 64, 70, 203423 71, 204424 64, 204425 71, 204, 301426 204, 301427 204, 227, 416428 204, 229, 416429 204, 227, 507430 204, 227, 301431 10b, 461432 3S0 408433 392, 410, 507434 308, 410, 507435 41, Si, 95, 389,467, 510,

554436 206, 401, 467, 472437 296, 4b7, 472, 511438 131, 301, 479439 49, 131, 301440 49, 131, 207441 131, 301, 3b9442 131, 297, 3b0, 508443 131, 301, 380 508444 95, 131, 207, 522445 95, 131, 475, 522446 132, 301, 3S0, 522447 132, 3S0, 417, 52 J448 132, 302, 4(>7, 523449 132, 467, 508, 523450 389, 417, 5r>0451 371, 390, 550452 22b, 300, 550453 508, 550, 567454 467, 508, 523, 550455 204, 508, 5b7456 205, 371, 390457 205,467,508,52 5458 74, 401, 410, 468, 474,

567459 135, 300, 417460 135, 226, 300461 297, 410, 468, 511, 568462 95, 132, 302, 468463 95, 132, 302, 5t>8464 95, 132, 302, 4bl465 71, 95, 132, 523466 65, 133, 523, 531

SchultzNumber467468469470471472473474475476477478479480481482483484485486487488489490491492493494495496497498499500501502503504505506507508509510511

512513514515516517518519520521522523524525526527528529530531532533534535536537538539540541542543

Page133, 167, 302, 461133, 167, 302, 523133, 207, 302, 4bS133, 207, 302, 461133, 207, 303133, 207, 297, 303133, 297, 303, 424133, 303, 424 4bl134, 303, 424, 523134, 468, 524, 531134, 511, 524, 53271, 134, 524 532134, 175, 357, 468134 330, 511, 52482, 357, 511 55090, 524 55b 560100 417190, 417, 507409 53240, 400357, 4b9200, 357, 469134,511 532131, 358, 469137, 297, 46985, 390 400233, 26b 327, 540242 345120, 238159 23b209 23S304 452 537120 217159, 282209 345120 270150, 270121, 147121 1U122 144, 279217, 337144 33713b, 301;SO, 239 128 52489, 06, 103, 429, 430,

5bO, 57406, 430, 556, 50000, 195, 451, 55090, 550 5012*0, 401230 30i, 327, 4b714? 239 402217, 4b7, 537, 538230, 46207, 138, 50107, 138, 557, 501327, 342143, 240, 42807, 557, 5«197, 557, 50197 557, 501147, 328140 $04232, 279218, 270205, 539339, 537232, 339214, $3907, 56298, 557, 56298, 558, 50298, 203, 558, 50208, 5r>». 56209, 193, 55b, 56299, 393, 55H, 502163, 254, 305, 33421b, 308, 42b

SchultzNumber544545546547548549550551552553554555556557558559560561562563564

565566567568569570571572573574575576577578579580581582583584585586587588589590591592593594595596597598599600601602603604605606607608609610611612613614615616617618619620

Page218, 308, 428145, 308, 428282, 308235, 339270, 328305, 52585, 305159, 178168, 178122, 179159, 179462402525270, 305, 32S305, 328, 483537, 57132b, 343305, 398305, 33C, 358232, 240, 305, 347.

349, 5752012b7, 306, 328, 368300, 310237237210, 237, 510271, 4b809, 216, 488210, 488, 511210, 488234, 5164b 234234, 2712H, 511122, 21600, 488, 512, 563210, 4b9ibO, 512, 558MS, 489, 512211, 459, 512489, r>12143, 489, 512489, 512400, 513490, 513400, 513490, 513490, 513211, 513212, 514212, 514514, 536514, 536514, 536200, 400, 500401, 514200, 491, 500568244, 540121, 244121, 56800, 558, 56332b, 470Aoi classifiedNot cla88%fied139, 324, 502331, 503191 502491, 502182497407, 503184Ib2245, 301, 440*214, 440

30 PAGE INDEX OF SCHULTZ NUMBERS FOB DYES

-huUzumber Page621 236,472622 100, 290, 440623 440, 501624 290, 440625 290, 447626 290, 440627 245, 288, 440628 231, 291, 441629 291, 441630 100, 28S, 441631 291, 441632 291, 441633 291, 441634 291, 441635 291, 441636 294, 441637 288, 442638 288, 442639 289, 439, 442640 100, 29 i, 442641 213, 288, 439842 292, 442, 514643 292, 442, 515644 292, 442, 515645 292, 442, 528646 100, 213, 288, 439647 442, 515648 449, 515649 368, 443650 368, 443651 369, 443652 306, 369, 443653 215, 390654 147, 215655 223, 443656 68, 383657 72, 383658 309, 443659 240, 245, 443660 240, 245, 443661 240, 245, 247, 275, 444662 279, 280663 282, 284664 247, 292665 247, 248666 221, 382667 247, 281, 381, 382668 52, 45S669 246, 470670 246, 444, 568671 283, 390672 100, 390673 100, 390674 101, 391675 101, 448676 444, 484677 265, 444671 219, 444679 101, 559, 570680 101, 246681 246, 444682 101, 444683 101, 246, 333, 559, 563684 101, 148, 278, 283, 34 5

444, 445, 446, 446,486, 486, 486

444, 577101, 218, 220, 56353, 102, 559102, 553264, 444246, 267266, 445248,445102, 391, 462, 48335, 39135, 47233, 102

SchultzNumber Page

697 33, 102698 102, 431, 435699 33, 102700 103, 431, 435701 33,472702 103, 472, 559, 563703 445, 559, 563704 445, 559705 445, 559, 564706 Not classified707 Not classified708 Not classified709 79, 437710 568711 568712 135, 571713 472714 27, 135, 472715 27, 187716 571717 79718 431, 462, 472719 103, 424, 436720 259721 259722 259723 259724 79, 162, 255725 79, 162, 252, 255726 57, 79, 162, 255127 52, 162, 473728 235729 103,246730 57731 246, 361732 56, 197, 463733 79, 559734 79, 432735 464, 464736 57737 433738 162, 254, 255, 335, 532739 57740 258741 258742 258743 258744 Not classified745 257746 313747 312748 155,449749 250,251750 258751 Not classified752 Not classified753 Not classified754 Not classified755 Not classified756 Not classified757 Not classified758 347, 384, 491759 337760 241761 241762 241763 118,124764 118, 124765 118, 124766 160767 160768 160769 500770 138, 139, 500771 517772 293773 21, 222, 500774 256,352

SchultzNumber

775776777778779780781782783784785786787788789790791792793794795796797798799800801802803804805806807808809810811812813814815816817818819820821822823824825826827828829830831832833834835836837838839840841842843844845846847848849850851852

Page256, 352, 46325617525, 11525, 115, 41925, 11525, 115138, 293, 49125, 115, 49911411311325, 11525, 115257109, 250109337338338337109, 24925, 28, 115, 42025, 115, 41825, 11525125025028, 41928, 41928, 420, 43143443428, 41928, 41930, 4873020, 18620, 18629, 14059, 140141, 1S8141, 18855, 141141, 188190141, 190141, 57389, 14129, 15730, 15229, 20845, 209157, 18859, 20829, 209158, 393111, 20841, 13929, 157116116, 18930, 31630, 316151316, 3173163163174418930, 1241911893131731, 10388, 502, 502, 564

GE INDEX OF SCHULTZ NUMBERS FOR DYES 631

Page51, 5645, 115, 5640, 56451, 50403, 250175, 5645, 56404, 5355, 104, 115, 4991204, 427, 5648, 503, 503, 5053510329, 141, 157Vot classified1849, 18804, 318, 476, 478, 491,542

04, 318, 476, 479, 492,542

L05, 318, 476, 479, 492,542

SchultzNumber

878879880881

882883884885886887888889890891892893894;895

Page105, 318, 476, 479, 492,

543105, 319, 476, 479, 492,

543105, 319, 476, 479, 492,105, 319, 477, 479, 492,

543105, 319, 477, 480, 492,

543105, 319, 477, 480,492,

543105, 319, 477, 480, 493,

543105, 319, 477, 480, 493,

543100, 319, 477, 480, 493,

544168450, 559106, 142, 319, 477, 480,

493, 544106, 142, 319, 478, 481,359359117, 206306, 322206, 361

SchultzNumber

896897898899900QAi9U JL902903904905906907908909910911912913914915916917918919920921922923

Page307, 322320, 320, 321321, 341314, 322314, 322, 322314, 32258, 32358, 32358, 321314,321314, 32119, 31419, 31417215019, 58314, 54526958269274171173314, 545104170, 43853, 10678, 79, 192, 473

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