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Public Functional Chemicals Division Personal Care 29.10.2008 Genamin ® Quats Quaternary Ammonium Compounds

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Public

Functional Chemicals Division

Personal Care

29.10.2008

Genamin® QuatsQuaternary Ammonium Compounds

Public

Functional Chemicals DivisionPersonal Care

Slide 229.10.2008

Quaternary Ammonium Compounds

Genamin® KDMP/BTLF

Behentrimonium Chloride

Genamin® STAC

Steartrimonium Chloride

Genamin® CTAC

Cetrimonium Chloride

Genamin® DSAP

Distearyldimonium Chloride

Genamin® PQ 43

Polyquaternium-43

Public

Functional Chemicals DivisionPersonal Care

Slide 329.10.2008

Hair Care Products: Conditioners

Reduced tangling, easier combing

Smooth wet feel, silky dry feel

Healthy appearance, gloss

Will not weigh hair down or build-up

Attractive appearance (rich cream,

or other)

Hair “repair” and protection from

treatment

Color protection

Natural look

Balances, rejuvenates, volumizes

What Consumers Expect: Market Trends:

Public

Functional Chemicals DivisionPersonal Care

Slide 429.10.2008

Causes of Hair Damage:

Shampooing, Grooming/ Styling,

Chemical Treatment, Environment

Sources of Hair Stress:

Hair styling, combing, rubbing,

brushing

Perms, bleaching, relaxing

Heat (curling, blow drying)

UV, chlorine

Teasing, stretching or extending

Chemical and Morphological

Effects on Hair:

Cuticle chipping

Scale abrasion/weakening

Loss of tensile strength

Textural changes, roughening

Dryness, brittleness

Lowering of isoelectric point

Public

Functional Chemicals DivisionPersonal Care

Slide 529.10.2008

Deposition of Cationic Conditioners on

Hair

The isoelectric point of virgin hair is approximately 3.67.

At pH > 3.67, hair bears a net negative charge (cationic conditioners

bind strongly).

Chemically treated hair tends to have a lower isoelectric point: more

sites for binding of quats.

Cationics bind to the hair surface, reducing friction, allowing for

easier combing.

Public

Functional Chemicals DivisionPersonal Care

Slide 629.10.2008

Water

Quat 1 - 3 %

Thickening agents,

Emulsifiers 3 - 6 %

Quat

Emulsifier

Thickening Agent

Oils

Active Ingredients

Fragrance

Acids

Dyestuff solution

Water

Problem:

more than 1000 conditioning agents,

more than 110 quats

listed @ CTFA

Composition of Hair Rinses

Public

Functional Chemicals DivisionPersonal Care

Slide 729.10.2008

0

5

10

15

20

25

30

Gar

nier

Fru

ctis S

leek

& S

hine

Sua

ve N

atur

als

Tres

emm

e

Mat

rix B

iola

ge

Alber

to V

O5

Gar

nier

Fru

ctis

Dov

e

Pan

tene

Pro

V R

esto

rativ

es

Pan

tene

Pro

V

Nex

xus Hum

ectres

s

Leading US Conditioners ranked by dollar sales (in millions)

for the year ending Oct. 7, 2007

Source: Information Resources Inc., HAPPI 12/2007 (Excludes Wal-Mart sales)

Public

Functional Chemicals DivisionPersonal Care

Slide 829.10.2008

Ingredients

Water (Aqua), Cetearyl Alcohol, Behentrimonium Chloride,

Amodimethicone, Pyrus Malus (Apple) Fruit Extract, Fragrance (Parfum),

Cetyl Esters, Lauryl PEG/PPG-18/18 Methicone, Methylparaben, Persea

Gratissima (Avocado Oil), Niacinamide, Pyridoxine HCl, Trideceth 12, Citric

Acid, Prunus Armeniaca (Apricot Kernel Oil), Saccharum Officinarum

(Sugar Cane Extract), Chlorhexidine Dihydrochloride, Cetrimonium

Chloride, Linalool, Butylphenyl Methylpropional, Citrus Limonum (Lemon

Peel Extract), Camellia Sinensis (Camellia Sinensis Leaf Extract)

Claim

Frizzy, Dry or Unmanageable Hair

For Long-Lasting, Sleek Hair*

It improves texture for all hair types, moisturizes and adds softness, without

weighing hair down.

Nutritive Fruit Micro-Oils

The new Garnier Fructis Sleek & Shine System, containing nourishing fruit

micro-oils, specifically responds to the needs of frizzy, dry, difficult-to-smooth hair.

It nourishes the hair, smoothes the hair from root to tip, tames frizz & flyaways so

hair stays sleek all-day.

*In brushing/combing tests, compared to an ordinary shampoo.

Garnier Fructis Sleek and Shine

Get 4x smoother hair with all of the shine, none of the weight.*

Public

Functional Chemicals DivisionPersonal Care

Slide 929.10.2008

Dove Moisturizing Conditioner

Ingredients

Water (Aqua), Cetearyl Alcohol, Cetrimonium Chloride, Cyclopentasiloxane,

Dimethiconol, Glycerin, Quaternium-18, Fragrance (Parfum), Propylene Glycol,

Hydroxyethylcellulose, Potassium Chloride, Disodium EDTA, DMDM Hydantoin,

TEA-Dodecylbenzenesulfonate, Lysine Hydrochloride, Silk Amino Acids

[Alanine, Glycine, Serine, Arginine, Isoleucine, Cystine, Histidine, Glutamic

Acid], Borage (Borago Officinalis) Extract [Palmitic Acid, Stearic Acid, Linoleic

Acid, Oleic Acid, Eicosenoic Acid], Methylchloroisothiazolinone,

Methylisothiazolinone.

Claim

Dove® Moisturizing formula delivers deep replenishment for

dry or damaged hair. It intensely hydrates and restores dry

hair, leaving hair noticeably softer, smoother and more

naturally vibrant. The Dove Difference is our Weightless

Moisture™

Public

Functional Chemicals DivisionPersonal Care

Slide 1029.10.2008

Infusium 23Conditioner, Moisturizing for Normal to Dry Hair

Ingredients

Water, Cetearyl Alcohol, Behentrimonium Chloride, Cetyl Esters,

Ammodimethicone, Panthenol, Dimethicone Copolyol, Glycerin, Betaine,

Sorbitol, Serine, Glutamic Acid, PEG-8/SMDI Copolymer,

Hydroxyethylcellulose, Glycine, Lysine, Threonine, Arginine, Alanine, Palmitoyl

Myristyl Serinate, Behenic Acid, Oleic Acid, Palmitic Acid, Linoleic Acid, Stearic

Acid, Proline, Arachidic Acid, PEG-8, Cetrimonium Chloride, Fragrance,

Trideceth-12, Polyquaternium-11, Sodium PCA, Phenoxyethanol, DMDM

Hydantoin, Propylparaben

Claim

Corrects, Restores, Structurizes

• Infuses hair with 23 essential pro-vitamin & treatment ingredients

• Releases tangles and leaves hair feeling silky and clean

• Clean rinsing formula

Infusium 23 is specially formulated to fortify the hair cuticle, giving it healthy

texture, improved manageability and liveliness. It rinses easily, releases

tangles and leaves hair feeling clean, silky and greaseless without oily buildup.

Public

Functional Chemicals DivisionPersonal Care

Slide 1129.10.2008

Monoalkyl-

trimethyl

Lauryl Cocoyl Cetyl Stearyl Behenyl

C12 C8-18 C16 C18 C22

CTAC STAC KDMP/BTLF

R - N+ - CH3 X-

CH3

CH3

water solubility

conditioning effect

Influence of Chemical Structure on

Performance

Public

Functional Chemicals DivisionPersonal Care

Slide 1229.10.2008

Genamin CTAC

Cetrimonium chloride

Genamin KDMP/BTLF

Behentrimonium chloride

+++

++

+

++

+

+

Wet

combingSoftening

effectAntistatic

action

0

+++

+Genamin STAC

Steartrimonium chloride

Genamin DSAP

Distearyldimonium chloride++ +++

Usage

concentration

[% AI]

1.0 - 3.0

0.5 - 2.0

0.5 - 2.0

0.5 - 2.0

Properties of Clariant Quaternary

Ammonium Compounds

Product

Public

Functional Chemicals DivisionPersonal Care

Slide 1329.10.2008

C R E A M R I N S E B II/1118 with Genamin

® BTLF for excellent dry combability and volume, with

Genamin®

CTAC for perfect wet combability and anti-static effect

A Genamin® BTLF (Clariant) 2.50 %

Behentrimonium Chloride

Genamin® CTAC (Clariant) 3.00 %

Cetrimonium Chloride

Hostacerin® T-3 (Clariant) 1.50 %

Ceteareth-3

Cetyl Alcohol 3.00 %

B Water ad 100.00 %

C Fragrance 0.30 %

Dyestuff solution q.s.

Preservative q.s.

D Citric Acid (10 % in water) to pH 4,0 q.s.

I Melt A at 75 °C.

II Heat B to 75 °C.

III Stir II into I.

IV Stir until cool.

V At 35 °C add the components of C to IV.

VI Finally adjust the pH with D.

Public

Functional Chemicals DivisionPersonal Care

Slide 1429.10.2008

Genamin® KDMP

INCI: Behentrimonium chloride

Outstanding conditioner quat, long behenyl (C20/22) alkyl chain gives

highest substantivity to hair

Excellent silkening/smoothing effect provides "natural" feeling

– volume and body to hair, excellent dry combability

Excellent antistatic properties, especially when formulated together with

Hostaphat® KL 340D or Hostaphat® KW 340D

Synergystic effects in combination with Genamin CTAC

Especially good for “deep conditioners” or for damaged hair

Easy-to-handle pellet form

Typical use level: 0.5 - 2.0%

R N CH3

CH3

CH3

+Cl

_

R = predominantly C20/22

Public

Functional Chemicals DivisionPersonal Care

Slide 1529.10.2008

Genamin® BTLF

INCI: Behentrimonium Chloride

Same advantages as Genamin KDMP

Free of flammable solvents – no IPA, 30% dipropylene glycol

Still high activity ~70%, pellets

Typical use level: 0.5 - 3.0%

R N CH3

CH3

CH3

+Cl

_

R = predominantly C20/22

Public

Functional Chemicals DivisionPersonal Care

Slide 1629.10.2008

Genamin® BTLF in DoveIntensive Pflege, Regenerierende Aufbau-Spülung

(“Intensive care, regenerating structure flushing”)

Public

Functional Chemicals DivisionPersonal Care

Slide 1729.10.2008

Genamin® CTAC

INCI: Cetrimonium Chloride

Shorter (C16) alkyl chain gives better water solubility: no build-up

Clear conditioner formulations are possible

Excellent antistatic properties, especially when formulated together

with Hostaphat® KL 340D

– excellent wet combability

Synergystic effects in combination with Genamin KDMP

Available in two concentration levels (~30% and ~50%)

Typical use level (100% basis): 1 - 3% (for leave-in products limit is

0.25% active)

R N CH3

CH3

CH3

+Cl

_

R = predominantly C16

Public

Functional Chemicals DivisionPersonal Care

Slide 1829.10.2008

Genamin® STAC

INCI: Steartrimonium Chloride

Provides softening and antistatic properties to hair

Soluble in aqueous systems

Compatible with cationic and amphoteric surfactants

Compatible with film-forming polymers

Excellent stability over wide pH range

Typical use level: 0.5 - 2% (active)

R N CH3

CH3

CH3

+Cl

_

R = predominantly C18

Public

Functional Chemicals DivisionPersonal Care

Slide 1929.10.2008

Genamin® DSAP

INCI: Distearyldimonium Chloride

Product is ~95% Active

Superb softening and antistatic properties

High substantivity

Typical use level: 0.5 - 2% (active)

Excellent cationic emulsifier

Available as pellets

R N CH3Cl

R

CH3

+

R = C18

-

Public

Functional Chemicals DivisionPersonal Care

Slide 2029.10.2008

Genamin® PQ 43

INCI: Polyquaternium-43

High performance cationic tetrapolymer

Liquid additive (15% active) for rinse-off surfactant based

formulations: hair care and skin cleansing products

Properties :

– leaves a pleasant and smooth/soft feel

– compatible with all types of surfactants (anionic, cationic,

amphoteric) for clear or pearlized formulations

– enhances shine

– antistatic benefits

– formulations are less slippery than PQ 10 based systems

Applications: shower gels, soaps, shampoos

hairstyling mousses, conditioners, hair gels, sprays

Very effective: Typical usage concentration : 0.1 - 2 %

Public

Functional Chemicals DivisionPersonal Care

Slide 2129.10.2008

Genamin® PQ 43 co-polymer is built up

of 4 different functionalized subunits:

AMPS anionic water solubility

(2-Acrylamido-2-methylpropane sulfonic acid)

MAPTAC cationic conditioning

(3-[Methacrylamidopropyl] trimethylammoniumchloride)

DMAPMA amphoteric softness, foaming

(N-[3-dimethylamino]propyl- methacrylamide)

Acrylamide neutral backbone

Public

Functional Chemicals DivisionPersonal Care

Slide 2229.10.2008

AMPS MAPTAC DMAPMA Acrylamide

CH

CH

2 CO

NH

C(CH3)2

CH2

S

** a

OO

O

* CH

2

CH

CO

NH2

*d

CH

2 CO

NH

CH2

CH3

** c

CH2

CH2

N+

CH3

CH3

H

CH2

CH2

CH2

N+

CH3

CH3CH

3

CH

2 CO

NH

CH3

** b

Cl

Genamin® PQ 43 Structure

Public

Functional Chemicals DivisionPersonal Care

Slide 2329.10.2008

Benefits of Genamin® PQ 43

Genamin PQ 43 combines different functional sub-units within one

polymer structure:

– solubility

– conditioning

– softness

– film forming ability

acts as a skin moisturizer since it absorbs the humidity of the air

and thus prevents the skin from drying out.

considerably makes the skin smooth and soft

can act as a carrier substance for other active ingredients to prevent

them from penetration or rinse off.

Public

Functional Chemicals DivisionPersonal Care

Slide 2429.10.2008

Market Products with Genamin® PQ 43

Garnier 2-in-1 Shower & Care

Aqua, sodium laureth sulfate, glycerin, coco

betaine, laureth-11, carboxylic acid, sodium

chloride, parfum, hexylene glycol, disodium

laureth sulfosuccinate, citric acid, sodium

methylparaben, PEG-150 distearate,

polyquaternium-43, DMDM hydantoin,

polyquaternium-10, tocopheryl acetate

Public

Functional Chemicals DivisionPersonal Care

Slide 2529.10.2008

Market Products with Genamin® PQ 43

Tetesept: HydroCreme Dusche Milk & Flower

Aqua, sodium laureth sulfate, glycerin,

cocomidopropyl betaine, ammonium lauryl

sulfate, parfum, cocamide DEA,

polyquaternium-43, PEG-7 glyceryl cocoate,

styrene/acrylates copolymer, sodium

caseinate, propylene glycol, bletilla striata,

citric acid, hydroxypropyl guar

hydroxypropyltrimonium chloride,

phenoxyethanol, methylparaben,

ethylparaben, propylparabem, butylparaben,

isobutylparaben, dehydroacetic acid,

disodium EDTA

Public

Functional Chemicals DivisionPersonal Care

Slide 2629.10.2008

Genamin® Quats: Summary

BTAC (Genamin KDMP/BTLF) in combination with CTAC (Genamin

CTAC) is the established market standard for superior cream rinse

formulations

Clariant market leader in BTAC production

Depending on the final product segment, Clariant provides various

grades of Genamin Quats

Genamin PQ 43 (Polyquaternium-43) is a unique aqueous solution

for body wash formulation: Compatible with SLES and other anionic

surfactants, easy to handle, effective

Clariant formulation expertise: Broad variety of guide recipes and

manufacturing advises available on request

– Cream rinse formulation for all type of hair

– Two phase leave on

– Foam / mousse

Public

Functional Chemicals DivisionPersonal Care

Slide 2729.10.2008

CREAMRINSE FOR COLORED HAIR BII / 1128

A Genamin® KDMP (Clariant) 2.50 %Behentrimonium Chloride

Genamin® CTAC (Clariant) 3.00 %

Cetyltrimonium Chloride

Cetearyl Alcohol 4.00 %

Hostacerin® DGSB (Clariant) 1.50 %

PEG-4 Polyglyceryl-2-Stearate

Isopropylpalmitate 1.50 %

Olive Oil 1.00 %

SilCare® Silicone 41M15 (Clariant) 0.50 %

Caprylyl Methicone

Uvinul MS 40 0.50 %

Benzophenone-4

B Water ad 100 %

Sorbitol 2.00 %

Glycerin 2.00 %

D- Panthenol 1.00 %

C Tocopherylacetate 0.50 %

Extrapone Eibisch Spezial 2.00 %

Aqua, Ethoxydiglycol, Propylene Glycol, Althea Officinalis Extract, Butylene Glycol

Cosi Silk soluble 1.00 %

Hydrolyzed Silk

Chitin Liquid 1.00 %

Carboxymethylchitin

Hydrotriticum WQ 1.00 %

Hydroxypropyltrimonium Hydrolyzed Wheat Protein

Fragrance 0.30 %

Dyestuff solution q.s.

Preservative q.s.

D Sodium Hydroxid > pH 4.0 q.s

Procedure

I Melt A at 80 °C

II Dissolve B and

heat it to 80 °C

III Stir II into I and

stir until cool

V At 35 °C add

the components of

C to IV

VI Finally adjust

the pH with D.

Public

Functional Chemicals DivisionPersonal Care

Slide 2829.10.2008

R&D Personal Care Clariant GmbH

Division Functional Chemicals

D-65926 Frankfurt am Main

2 P H A S E - C O N D I T I O N E R , leave on BII 3018clear, with SilCare 31M50

A Genamin

CTAC (Clariant) 0.80 %

Cetrimonium Chloride

Genamin

PDAC (Clariant) 2.00 %

Polyquaternium-6

Bozequat

4000 (Clariant) 2.00 %

Polyquaternium-43

Genamin

KSL (Clariant) 2.00 %

PEG-5 Stearyl Ammonium Lactate

D-Panthenol 0.50 %

Glycerin 2.00%

Fragrance 0.40 %

Uvinul MS40 0.10%

Benzophenone-4

Dyestuff solution q.s.

Preservative q.s.

Alcohol denat. 10.00 %

B Water ad 100 %

C SilCare® Silicone 31M50 (Clariant) 15.00 %

Caprylyl Trimethicone

Procedure:

I Stir the components of A into B; stir until clear

II Add C to I

III If necessary adjust the pH

Genamin PQ 43

Public

Functional Chemicals DivisionPersonal Care

Slide 2929.10.2008

Quats – Regulatory Issues (SCCP)

Clariant defends the following

– Cetrimonium and Steartrimonium Chloride

– Rinse-off hair care up to 2.5%

– Leave-on hair care up to 1.0%

– Leave-on facial cream up to 0.5%

– Behentrimonium Chloride

– Rinse-off hair care up to 5.0%

– Leave-on hair care up to 3.0%

SCCP Opinion of March 2007 for rinse-off cosmetics

– The sum of CTAC and STAC should not exceed 0.5%

– Total sum of BTAC, CTAC and STAC should not exceed 3.0%

Public

Functional Chemicals DivisionPersonal Care

Slide 3029.10.2008

SCCP Opinion on Use of Alkyl

Trimethylammonium Chlorides

steartirimonium chloride and cetrimonium chloride have concentration limits

– The limits are based on skin irritation potential

Considering the fact that quaternary ammonium compounds are known to be

irritating, combination effects should also be taken into account. Therefore the

following concentration limits should apply for rinse-off cosmetic products:

– the sum of the cetrimonium and steartrimonium chloride

concentrations should not exceed 0.5%, and

– the total sum of behentrimonium, cetrimonium and/or steartrimonium

chloride should not exceed a maximum level of 3%.

The submission requests evaluation of the use of these quaternary ammonium

derivatives in leave-on (face)-cream products. This dossier only allows the

safety evaluation of quaternary ammonium compounds in leave-on cosmetic

products when present in a maximum level of 0.1% (preservative or

nonpreservative). The safety evaluation of the leave-on (face)-cream products

containing these substances needs to be assessed on a case by case basis.

Public

Functional Chemicals Division

Personal Care

29.10.2008

Questions?