WO2016139122A1

WO2016139122A1 - Hair treatment product containing methionyl methionine and cationic surfactants

Info

Publication number: WO2016139122A1
Application number: PCT/EP2016/053969
Authority: WO
Inventors: Erik Schulze Zur Wiesche; Volker Scheunemann
Original assignee: Henkel Ag & Co. Kgaa
Priority date: 2015-03-04
Filing date: 2016-02-25
Publication date: 2016-09-09
Also published as: DE102015203824A1

Abstract

The present invention relates to hair treatment products containing - relative to the total weight of the product - a) 0.0001 to 30% by weight of methionyl methionine, b) 0.001 to 5% by weight of a cationic surfactant, c) 0.0001 to 3.0% by weight of an organic acid, d) 0.01 to 20% by weight of a hair care polymer, and e) an aqueous or aqueous-alcoholic carrier. The hair treatment product is particularly used in the care of human hair.

Description

HAIR TREATMENT CONTAINING METHIONYLMETHIONINE AND CATIONIC TENSIDES

The present invention relates to hair treatment compositions containing a cationic surfactant, an organic acid, a hair care polymer and a dipeptide.

Environmental influences and oxidative hair treatments often lead to impaired combability of dry and wet hair. Furthermore, the gloss and suppleness are adversely affected by the attacked outer structure of the keratinic fibers. Another consequence of repeated treatments of keratinic fibers with surface-active and / or oxidative agents is a strong re-greasing of the keratinic fibers and a strong tendency to increased scaling of the scalp. conventional

Compositions, which often contain silicones, often lead to a weighting of the hair and thus in particular in persons with fine hair to problems in the

Hair styling.

There is a need to further improve hair care products and to give them further advantageous properties. In particular, a better care of the hair surface should be provided. Accordingly, it is therefore an object of the present invention, the side effects of environmental influences and of oxidative and surfactant

To reduce hair treatments.

It has now surprisingly been found that the aforementioned objects in

excellent degree by a hair treatment agent containing methionylmethionine, a cationic surfactant, an organic acid and a hair care polymer.

This hair treatment agent improves the finish, in particular the wet and dry combability, improves the gloss, improves the moisture balance, and protects the destructuring of human hair. The hair treatment agent also causes an increase in the inner hair structure.

A first subject of the present invention is therefore a hair treatment composition containing - based on the weight of the total composition - a) 0.0001 to 30 wt .-% methionylmethionine,

b) from 0.001 to 5% by weight of cationic surfactant,

c) 0.0001 to 3.0% by weight of an organic acid, d) 0.01 to 20 wt .-% of a hair care polymer and

e) an aqueous or aqueous-alcoholic carrier.

The hair treatment agent containing methionylmethionine is preferably used immediately after the oxidative or surfactant hair treatment. For the purposes of the invention, the term "oxidative or surfactant hair treatment" is understood as meaning an application which is either directly connected to the oxidative or surfactant hair treatment, wherein the

Hair treatment agent is applied after rinsing the oxidative or surfactant acting on the preferably still wet, towel-dried hair, or only after several hours or days on the preferably wet hair is applied. The

Hair treatment agent can be rinsed out after a contact time of a few seconds up to 45 minutes or completely remain on the hair. Oxidative hair treatment is defined as the action on hair of an oxidative cosmetic agent containing at least one oxidizing agent in a cosmetic carrier.

The hair treatment composition contains as component a) methionyl methionine in an amount of 0.0001 to 30 wt .-% based on the weight of the total composition.

Methionylmethionine is the dipeptide of methionine and has the following structure:

From the dipeptide methionylmethionine exist the four different stereoisomers DD, LL, DL and LD. Of the four stereoisomers, only the L-methionyl-L-methionine is natural, the three other dipeptides L-methionyl-D-methionine, D-methionyl-L-methionine, and D-methionyl-D-methionine are all unnatural. The described positive effects in hair treatment compositions can be achieved with all four stereoisomeric dipeptides. The Methionylmethionin can as

DD / LL / LD / DL mixture, used as DL / LD mixture or DD / LL mixture. In principle, the use of a stereoisomeric dipeptide alone or in combination with one or two further stereoisomers is conceivable. If only one stereoisomeric dipeptide is used, preference is given to choosing L-methionyl-L-methionine or D-methionyl-D-methionine.

The two pairs DD / LL-methionylmethionine and DL / LD-methionylmethionine are diastereomeric and have different physical data. Thus, for example, the diastereomeric pair DD / LL at room temperature has a solubility of 21.0 g / l in water. whereas the solubility of the pair of diastereomers DL / LD is 0.4 g / l. Accordingly, it may be preferable to use the methionylmethionine as a DD / LL mixture or as a DD / LL / LD / DL mixture with a high proportion of the DD / LL diastereomeric pair. These mixtures can be easily incorporated / dissolved in an aqueous phase or an aqueous-surfactant phase of a cosmetic product.

The hair treatment compositions contain the methionyl methionine preferably in an amount of 0.01 to 5.0 wt .-% and particularly preferably from 0, 1 to 3.0 wt .-%, each based on the weight of the ready hair treatment agent.

A second essential ingredient b) in the hair treatment compositions is a cationic surfactant. The effectiveness of the hair treatment agent is further increased and the stability of the composition promoted considerably.

Cationic surfactants are monomeric cationic or amphoteric ammonium compounds, monomeric amines or aminoamides. From these many possible cationic surfactants, the following groups have proven to be particularly suitable and are used in each case in an amount of 0.001 to 5.0 wt .-%. This amount is also not exceeded or exceeded when a mixture of different compounds of the cationic surfactants is used.

Cationic ammonium compounds of formula (Tkatl) form the first group of cationic surfactants.

(Tkatl)

In the formula (Tkatl), R 1, R 2, R 3 and R 4 each independently represent hydrogen, a methyl group, a phenyl group, a benzyl group, a saturated, branched or unbranched alkyl group having a chain length of 8 to 30 carbon atoms, optionally with a or multiple hydroxy groups. A is a physiologically acceptable anion, for example halides such as chloride or bromide and methosulfates.

Examples of compounds of formula (Tkatl) are lauryltrimethylammonium chloride,

Cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, cetyltrimethylammonium methosulfate, dicetyldimethylammonium chloride, tricetylmethylammonium chloride, stearyltrimethyl ammonium chloride, distearyldimethylammonium chloride, lauryldimethylbenzylammonium chloride, behenyltrimethylammonium chloride, behenyltrimethylammonium bromide, behenyltrimethylammonium methosulfate. Monoalkyl quats, ie compounds of the formula (Tkat1) having an alkyl radical with a chain length of 8 to 30 carbon atoms, are preferably used as cationic surfactants in the hair treatment compositions.

Esterquats according to the formula (Tkat2) form another preferred group of cationic surfactants.

R2

l ₊

R1 N-X-R4

I

R3

(Tkat2)

Here, the radicals R1, R2 and R3 are each independently and may be the same or different. The radicals R1, R2 and R3 mean:

a branched or unbranched alkyl radical having 1 to 4 carbon atoms, which may contain at least one hydroxyl group, or

a saturated or unsaturated, branched or unbranched or a cyclic saturated or unsaturated alkyl radical having 6 to 30 carbon atoms, which may contain at least one hydroxyl group, or

an aryl or alkaryl radical, for example phenyl or benzyl,

the radical (--X - R4), with the proviso that at most 2 of the radicals R1, R2 or R3 can stand for this radical:

The rest - (X - R4) is contained at least once to three times.

Where X stands for:

1) - (CH 2) n - with n = 1 to 20, preferably n = 1 to 10 and particularly preferably n = 1 - 5, or

2) - (CH 2 -CHR 5 -O) n - where n = 1 to 200, preferably 1 to 100, particularly preferably 1 to 50, and particularly preferably 1 to 20 with R 5 in the meaning of hydrogen, methyl or ethyl,

3) a hydroxyalkyl group of one to four carbon atoms, which may be branched or unbranched, and which contains at least one and at most 3 hydroxy groups. Examples are: -CH ₂ OH, -CH ₂ CH ₂ OH, -CHOHCHOH, -CH ₂ CHOHCH 3,

-CH (CH ₂ OH) ₂ , -COH (CH ₂ OH) ₂ , -CH ₂ CHOHCH ₂ OH, -CH ₂ CH ₂ CH ₂ OH and

Hydroxybutylreste,

and R4 stands for:

1) R6-0-CO-, wherein R6 is a saturated or unsaturated, branched or

unbranched or a cyclic saturated or unsaturated alkyl radical having 6 to 30 Carbon atoms which may contain at least one hydroxy group, and which may optionally further be ethoxylated with 1 to 100 ethylene oxide units and / or 1 to 100 propylene oxide units, or

2) R7-CO-, wherein R7 is a saturated or unsaturated, branched or unbranched or cyclic saturated or unsaturated alkyl radical having 6 to 30

Carbon atoms which may contain at least one hydroxy group, and which may optionally be further ethoxylated with 1 to 100 ethylene oxide units and / or 1 to 100 propylene oxide units,

and A represents a physiologically acceptable organic or inorganic anion and is defined here as representative of all structures also described below. The anion of all described cationic compounds is selected from the halide ions, fluoride, chloride, bromide, iodide, sulfates of the general formula RSO3 ^" , wherein R has the meaning of saturated or unsaturated alkyl radicals having 1 to 4 carbon atoms, or anionic radicals of organic acids such as maleate , Fumarate, oxalate, tartrate, citrate, lactate or acetate.

Such products are sold, for example, under the names Rewoquat ^®, Stepantex® ^®, Dehyquart® ^®, ^® and Armocare® Quartamin ^®. The products Armocare ^® VGH-70, Dehyquart ^® F-75, Dehyquart ^® C-4046, Dehyquart ^® L80, Dehyquart ^® F-30, Dehyquart ^® AU-35, Rewoquat ^® WE18, Rewoquat ^® WE38 DPG, Stepantex ^® VS 90 and Quart amine ^® BTC 131 are examples of these esterquats.

Further preferred quaternary compounds are cationic betaine esters of the formula (Tkat3).

R8 corresponds in its meaning R7.

Further suitable quaternary compounds have the general formula (I).

X

with the proviso that n + m>38; particularly preferred is n = m; most preferably n = m = 20. a and b are independently integers between 1 and 10; particularly independently of one another are 1, 2, 3, 4 or 5, preferably the equation a + 2>b> a -2 applies here and most preferably a = b = 3.

R and R ^'are independently selected from -H and -Chta;

preferably R = R ^' , so that preferably either PEG or PPG diester quats are used; very particularly preferably, R = R ^' = -CH ₃

X is a physiologically acceptable anion, a halide such as chloride,

Bromide or iodide, toluenesulfonate, methosulfate, etc., and most preferably is methosulfate.

In particular, in the use of one of the compounds of the formula (I) as described above, it has been found that the care effects of the hair treatment compositions can be further increased and, in particular, the stability of the compositions can be further improved, if the agents are used in addition to the compound (s). en) of the formula (I) contain certain acylated diamines.

Preferred hair treatment agents are therefore characterized by containing a compound of formula (II)

where x stands for 18, 19, 20, 21, 22, 23 or 24.

Compounds of the formula (II) where n = 20 are particularly preferred. Highly preferred agents are characterized in that they always contain a compound of the formula (I) together with a compound of the general formula (II).

Another group are quaternary imidazoline compounds. The formula (Tkat4) shown below shows the structure of these compounds.

(Tkat4) The radicals R independently of one another each represent a saturated or unsaturated, linear or branched hydrocarbon radical having a chain length of 8 to 30

Carbon atoms. The preferred compounds of formula (Tkat4) contain for R each the same hydrocarbon radical. The chain length of the radicals R is preferably 12 to 21

Carbon atoms. A is an anion as previously described. Examples according to the invention are obtainable, for example, under the INCI names Quaternium-27, Quaternium-72, Quaternium-83 and Quaternium-91. Most preferred is quaternium-91.

In a particularly preferred embodiment of the invention, the agents furthermore comprise at least one amine and / or cationized amine, in particular an amidoamine and / or a cationized amidoamine having the following structural formulas:

R1 - NH - (CH ₂₎ n - N ⁺ R ² R ³ R ⁴ A (Tkat5)

wherein R 1 is an acyl or alkyl radical having 6 to 30 C atoms, which may be branched or unbranched, saturated or unsaturated, and wherein the acyl radical and / or the alkyl radical may contain at least one OH group, and

R2, R3 and R4 are each independently

1) hydrogen or

2) an alkyl radical having 1 to 4 carbon atoms, which may be identical or different, saturated or

can be unsaturated, and

3) a branched or unbranched hydroxyalkyl group having one to 4 carbon atoms having at least one and at most three hydroxy groups, for example -CH 2 OH,

-CH ₂ CH ₂ OH, -CHOHCHOH, -CH ₂ CHOHCH 3, -CH (CH ₂ OH) ₂ , -COH (CH ₂ OH) ₂ ,

-CH 2 CHOHCH 2 OH, -CH 2 CH 2 CH 2 OH and hydroxybutyl radicals, and

A is an anion as previously described and

n is an integer between 1 and 10.

Preference is given to a composition in which the amine and / or the quaternized amine according to general formulas (Tkat5) is an amidoamine and / or a quaternized amidoamine, in which R1 is a branched or unbranched, saturated or unsaturated acyl radical having 6 to 30 C atoms, which may contain at least one OH group means. Preference is given here to a fatty acid radical of oils and waxes, in particular of natural oils and waxes. Examples of these are lanolin, bees or candellila waxes.

Also preferred are those amidoamines and / or quaternized amidoamines in which R2, R3 and / or R4 in the formula (Tkat5) is a radical according to the general formula CH2CH2OR5, where R5 is the meaning of alkyl radicals having 1 to 4 carbon atoms, hydroxyethyl or hydrogen may have. The preferred size of n in the general formula (Tkat5) is an integer between 2 and 5. The alkylamidoamines are converted by protonation in a correspondingly acidic solution into a quaternary compound. Preference is given to the cationic alkylamidoamines.

Examples of such commercial products are Witcamine ^® 100, Incromine ^® BB, Mackine ^® 401 and other Mackine ^® grades, Adogen ^® S18V, and as a permanent cationic aminoamines: Rewoquat 'RTM 50, Empigen ^® CSC, Swanol ^® Lanoquat DES-50, Rewoquat ^® UTM 50, Schercoquat® ^® BAS ^® Lexquat AMG-BEO, or Incroquat ^® behenyl HE. A particularly preferred amidoamine of the formula (Tkat5) is a compound having the INCI name stearamidopropyl dimethylamine. This amidoamine is available, for example, under the name TEGO® Amide S 18 (ex Evonik).

Another suitable fatty acid amide corresponds to the general formula (III).

Formula (III)

in which R1, R2 and R3 independently of one another represent a linear branched or unbranched C6 to C30, preferably C8 to C24, more preferably C12 to C22 and most preferably C12 to C18 alkyl or alkenyl group. R1 to R3 are preferably capryl, caprylyl, octyl, nonyl, decanyl, lauryl, myristyl, cetyl, stearyl, isostearyl, oleyl, behenyl or arachidyl. Furthermore, R 2 is more preferably equal to R 3 and most preferably R 1 is R 2 equal to R 3. The

Letters n and m independently represent integers of 1 to 10, preferably 2 to 6 and most preferably 2, 3 and / or 4, most preferably n = m. Most preferably R1 is R2 equal to R3 and is selected from capryl, caprylyl, octyl, nonyl, decanyl, lauryl, myristyl, cetyl, stearyl, isostearyl, oleyl, behenyl or arachidyl and n = m = 2. Most preferably R1 = R2 = R3 and selected from lauryl, myristyl, cetyl, stearyl, isostearyl, oleyl, behenyl or arachidyl, among which cetyl, stearyl, isostearyl, oleyl or behenyl are particularly preferred and n = m = 2. The most preferred compound of formula (I) is that bearing the INCI name Bis-Ethyl (isostearylimidazoline) isostearamide. The latter compound is commercially available under the tradename Keradyn® HH from Croda.

In a particularly preferred embodiment of the invention that contains

Hair treatment agent a monoalkyl quat as a cationic surfactant. The monoalkyl quat may be the sole cationic surfactant or may be in admixture with other cationic surfactants. The amount of monoalkyl quat in the hair treatment agent is preferably from 0.05 to 4.0% by weight, based on the weight of the total composition. Especially preferred monoalkyl quats are cetyltrimethylammonium chloride and

Behenyltrimethylammonium.

In a further particularly preferred embodiment of the invention contains the

Hair treatment agent an amidoamine of the formula (Tkat5) as a cationic surfactant. The

Amidoamine may be the sole cationic surfactant or in admixture with other cationic surfactants. The amount of amidoamine in the hair treatment agent is preferably from 0.1 to 3.0% by weight, based on the weight of the total composition. A particularly preferred amidoamine is a compound with the INCI name stearamidopropyl dimethylamine.

In a most preferred embodiment of the invention, the hair treatment composition contains a monoalkyl quat and an amidoamine as cationic surfactants.

As component c), the hair treatment composition contains - based on its weight - 0.0001 to 3.0 wt .-% of an organic acid.

Typical representatives of organic acids are aliphatic mono- and dicarboxylic acids such as acetic acid, propionic acid, oxalic acid and 1, 3-propanedioic acid and aromatic carboxylic acids such as benzoic acid. Other suitable organic acids are hydroxycarboxylic acids such as glycolic acid, citric acid, tartaric acid, malic acid and lactic acid.

Also unsaturated mono- or dicarboxylic acids such as fumaric acid or o

Ketocarboxylic acids such as pyruvic acid (2-oxopropionic acid) are suitable.

Citric acid, tartaric acid, malic acid or lactic acid is particularly preferably used as organic acid, with citric acid and lactic acid being particularly preferred.

The hair treatment compositions further contain a hair care polymer. Hair care polymers are polymers that improve at least one of the following properties: lighter ones

Combability, softness, shine and smoothness of the hair. The hair care polymer is preferably selected from the group consisting of cationic polymers, amphoteric polymers, nonionic polymers, polyorganosiloxanes, and mixtures thereof.

The cationic hair care polymers can be homopolymers or copolymers or polymers based on natural polymers, wherein the quaternary nitrogen groups are contained either in the polymer chain or preferably as a substituent on one or more of the monomers.

Suitable cationic monomers are unsaturated, free-radically polymerizable compounds which carry at least one cationic group, in particular ammonium-substituted Vinyl monomers such as trialkylmethacryloxy-alkylammonium,

Trialkylacryloxyalkylammonium, dialkyldiallylammonium and quaternary

Vinyl ammonium monomers with cyclic, cationic nitrogen-containing groups such as pyridinium, imidazolium or quaternary pyrrolidones, e.g. alkylvinylimidizolium,

Alkylvinylpyridinium, or Alyklvinylpyrrolidon salts. The alkyl groups of these monomers are preferably lower alkyl groups such as C1 to C7 alkyl groups, more preferably C1 to C3 alkyl groups.

The ammonium group-containing monomers may be copolymerized with non-cationic monomers. Suitable comonomers are, for example, acrylamide, methacrylamide; Alkyl and dialkyl acrylamide, alkyl and dialkyl methacrylamide, alkyl acrylate, alkyl methacrylate,

Vinylcaprolactone, vinylcaprolactam, vinylpyrrolidone, vinylester, e.g. Vinyl acetate, vinyl alcohol, propylene glycol or ethylene glycol, wherein the alkyl groups of these monomers are preferably C1 to C7 alkyl groups, more preferably C1 to C3 alkyl groups.

From the large number of these polymers have proven to be particularly:

Homopolymers of the general formula - {CH ² - [CRCOO- (CH 2) m N ⁺ R ² R ³ R ⁴ ]} _n X-,

in which R = -H or -Chta, R ² , R ³ and R ^{4 are} independently selected from C1-4-

Alkyl, alkenyl or hydroxyalkyl groups, m = 1, 2, 3 or 4, n is a natural number and

X ^"is a physiologically acceptable organic or inorganic anion

Polymers are preferred those for which at least one of the following conditions applies: R represents a methyl group, R ² , R ³ and R ⁴ stand for methyl groups, m has the value 2.

As a physiologically acceptable counterion X ^" come, for example, halide ions,

Sulfate ions, phosphate ions, Methosulfationen and organic ions such as lactate, citrate, tartrate and acetate ions into consideration. Preference is given to methosulfates and halide ions, in particular chloride.

Suitable cationic polymers are, for example, copolymers of the formula (Copo).

Formula (Copo)

in which:

x + y + z = Q Q is from 3 to 55,000, preferably from 10 to 25,000,

particularly preferably from 50 to 15,000, more preferably from 100 to 10,000, even more preferably from 500 to 8000 and in particular from 1000 to 5000,

x stands for (0 to 0.5) Q, preferably for (0 to 0.3) Q and in particular for the values 0, 1, 2, 3, 4, 5, wherein the value 0 is preferred,

y is (0, 1 to 0.95) Q, preferably (0.5 to 0.7) Q and

in particular for values of 1 to 24,000, preferably of 5 to 15,000, more preferably of 10 to 10,000 and in particular of 100 to 4800,

z is (0.001 to 0.5) Q, preferably (0, 1 to 0.5) Q and

in particular for values of from 1 to 12,500, preferably from 2 to 8,000, particularly preferably from 3 to 4,000 and in particular from 5 to 2,000.

Regardless of which of the preferred copolymers of the formula (Copo) are used, preference is given to hair treatment compositions according to the invention which are characterized in that the ratio of (y: z) is 4: 1 to 1: 2, preferably 4: 1 to 1: 1 is.

Regardless of which copolymers are used in the compositions are

Hair treatment compositions in which the copolymer has a molecular weight of 10,000 to 20 million gmor, preferably from 100,000 to 10 million gmol ^{~ 1} , more preferably from 500,000 to 5 million gmol ^~ and in particular from 1, 1 million to 2.2 million gmol ^-1 having.

A most preferred copolymer, constructed as previously shown, is commercially available under the name Polyquaternium-74.

A particularly suitable homopolymer is, if desired, crosslinked,

Poly (methacryloyloxyethyltrimethylammonium chloride) with the INCI name Polyquaternium 37. Such products are, for example, under the names Cosmedia® ^® CTH or Cosmedia® ^® Ultragel® 300 (BASF SE) or Synthalen® ^® CR (3V Group) are commercially available.

The homopolymer is preferably used in the form of a nonaqueous polymer dispersion. Such polymer dispersions are available under the names Salcare ^® SC 95 and Salcare ^® SC 96 in the trade. Also suitable is a polymer dispersion sold under the name Cosmedia® Triple C (ex BASF SE).

Suitable cationic polymers derived from natural polymers are cationic derivatives of polysaccharides, for example, cationic derivatives of cellulose, starch or guar. Also suitable are chitosan and chitosan derivatives. Cationic polysaccharides have the general formula G-O-B-N + R _a RbRc A ^~

G is an anhydroglucose residue, for example starch or cellulose anhydroglucose;

B is a divalent linking group, for example alkylene, oxyalkylene, polyoxyalkylene or

hydroxyalkylene;

R _a , Rb and R _c are independently alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl or alkoxyaryl each having up to 18 carbon atoms, wherein the total number of carbon atoms in R _a , Rb and R _{c is} preferably at most 20;

A ^" is a common counteranion and is preferably chloride.

Cationic, ie quaternized celluloses are available on the market with varying degrees of substitution, cationic charge density, nitrogen content and molecular weights. For example, Polyquaternium-67 is commercially available under the names SoftCat® Polymer SL or SoftCat® Polymer SK (Dow). Under the trade designation Mirustyle CP ^® of the company. Croda another most preferred cellulose is available. This is a trimonium and cocodimonium hydroxyethyl cellulose derivatized cellulose with the INCI name

Polyquaternium-72. Polyquaternium-72 can be used pre-dissolved both in solid form and already in aqueous solution.

Other cationic celluloses are Ucare® Polymer JR 400 (Dow, INCI name

Polyquaternium-10) and polymer Quatrisoft ^® LM-200 (Dow, INCI name Polyquaternium-24). Other commercial products are the compounds Celquat ^® H 100 and Celquat ^® L 200th

Particularly preferred cationic celluloses are Polyquaternium-24, Polyquaternium-67 and Polyquaternium-72.

Suitable cationic guar derivatives are marketed under the trade name Jaguar ^® and have the INCI name guar hydroxypropyltrimonium chloride. Also particularly suitable cationic guar derivatives also by the company. Hercules under the name N-Hance ^® commercially. Other cationic guar derivatives are marketed by the company. BASF SE under the name Cosmedia® ^®. A preferred cationic guar derivative is the commercial product AquaCat® ^® from. Hercules. This raw material is an already pre-dissolved cationic guar derivative. The cationic guar derivatives are preferred.

A suitable chitosan is sold, for example, by Kyowa Oil & Fat, Japan under the trade name Flonac ^®. A preferred chitosan salt is

Chitosoniumpyrrolidoncarboxylat, which is sold for example under the name Kytamer ^® PC by Amerchol, USA. Other chitosan derivatives are among the

Trade names Hydagen® ^® CMF, Hydagen® ^® HCMF and Chitolam ^® NB / 101 freely available commercially. Another group of excellent polymers to use are polymers based on glucose. The following figure shows such a cationic alkyl oligoglucoside.

In the formula shown above, the radicals R independently of one another are a linear or branched C 6 to C 30 alkyl radical, a linear or branched C 6 -C 30 alkenyl radical, preferably the radical R is a radical R selected from: lauryl, myristyl, cetyl, stearyl, Oleyl, behenyl or arachidyl.

The radicals R 1 independently of one another are a linear or branched C 6 to C 30 alkyl radical, a linear or branched C 6 to C 30 alkenyl radical, preferably the radical R is a radical selected from: butyl, capryl, caprylyl, octyl, nonyl, decanyl, lauryl, Myristyl, cetyl, stearyl, oleyl, behenyl or arachidyl. More preferably, the radicals R1 are the same. More preferably, the radicals R1 are selected from technical mixtures of the fatty alcohol cuts of C6 / C8 fatty alcohols, C8 / C10 fatty alcohols, C10 / C12 fatty alcohols, C12 / C14 fatty alcohols, C12 / C18 fatty alcohols, and most preferred are those technical Fatty alcohol cuts of plant origin. The counterion to the cationic charge is a physiologically acceptable anion, for example, halide,

Methosulfate, phosphate, citrate, tartrate, etc. Preferably, the counterion is a halide such as fluoride, chloride, bromide or methosulfate. Most preferably, the anion is chloride.

Particularly preferred examples of the cationic alkyl oligoglucosides are the compounds with the INCI names Polyquaternium-77, Polyquaternium-78, Polyquaternium-79,

Polyquaternium-80, Polyquaternium-81 and Polyquaternium-82. Most preferred are the cationic alkyl oligoglucosides designated Polyquaternium-77, Polyquaternium-81 and Polyquaternium-82. Such compounds can be obtained, for example, under the name Poly Suga® Quat from the company Colonial Chemical Inc.

Of course, it is also understood that more mixtures of cationic alkyl oligoglucosides can be used. In this case, preference is given to using one long-chain and one short-chain cationic alkyl oligoglucoside at the same time.

Another preferred cationic polymer may be obtained based on ethanolamine. The polymer is commercially available under the name Polyquaternium-71.

Cl Cl Cl ci

This polymer can, for example, under the name Cola® Moist 300 P from the Fa.

Colonial Chemical Inc.

Furthermore, it is particularly preferable to use a cationic alkyl oligoglucoside as shown in the following figure.

In the above formula, the radical R 2 is a linear or branched C 6 to C 30 alkyl radical, a linear or branched C 6 -C 30 alkenyl radical, preferably the radical R is a radical R selected from: lauryl, myristyl, cetyl, stearyl, oleyl, Behenyl or arachidyl.

The radical R 1 is a linear or branched C 6 to C 30 alkyl radical, a linear or branched C 6 to C 30 alkenyl radical, preferably the radical R 1 is a radical selected from: butyl, capryl, caprylyl, octyl, nonyl, decanyl, lauryl, myristyl, Cetyl, stearyl, oleyl, behenyl or arachidyl. More preferably R1 is selected from technical mixtures of the fatty alcohol cuts of C6 / C8 fatty alcohols, C8 / C10 fatty alcohols, C10 / C12 fatty alcohols, C12 / C14 fatty alcohols, C12 / C18 fatty alcohols, and most preferred are those technical fatty alcohol cuts of plant origin. The subscript n represents a number between 1 and 20, preferably between 1 and 10, more preferably between 1 and 5, and most preferably between 1 and 3. The counterion to the cationic charge, A ^~ , is a

physiologically acceptable anion, for example halide, methosulfate, phosphate, citrate, tartrate, etc. Preferably, the counterion is a halide, such as fluoride, chloride, bromide or methosulfate. Most preferably, the anion is chloride.

Particularly preferred examples of the cationic alkyl oligoglucosides are the compounds having the INCI names Laurdimonium hydroxypropyl decyl glucosides chlorides,

Laurdimonium hydroxypropyl lauryl glucosides chlorides, stearyl dimonium hydroxypropyl

Decylglucosides chlorides, stearyldimonium hydroxypropyl lauryl glucosides chlorides,

Stearyldimonium hydroxypropyl lauryl glucosides chlorides or cocoglucosides

Hydroxypropyltrimonium chlorides.

Such compounds can be obtained, for example, under the name Suga® Quat from the company Colonial Chemical Inc.

Another preferred cationic polymer comprises at least one structural unit of the formula (IV), at least one structural unit of the formula (V), at least one structural unit of the formula (VI) and at least one structural unit of the formula (VII)

wherein

R and R ⁴ independently of one another represent a hydrogen atom or a methyl group, X ¹ and X ² independently of one another represent an oxygen atom or a group NH, A and A ² independently of one another represent a group ethane-1,2-diyl, propane 1, 3-diyl or butane-1, 4-diyl,

R ² , R ³ , R ⁵ and R ⁶ independently of one another represent a (C 1 to C 4) -alkyl group, R ⁷ is a (Cs to C30) alkyl group.

According to the above formulas and all following formulas, a chemical bond marked with the symbol ^{* stands} for a free valency of the corresponding structural fragment.

To compensate for the positive polymer charge in the agent are all possible physiologically acceptable anions, such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.

Examples of (C 1 to C 4) -alkyl groups according to the invention are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl.

Examples of (Cs to C30) alkyl groups according to the invention are octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl), docosyl (behenyl) ,

Subsequent cationic polymers can be used in the compositions if the cationic polymers of the abovementioned formulas (IV) to (VII) fulfill one or more of the following characteristics:

R and R ⁴ each represent a methyl group,

X ¹ stands for a group NH,

X ² stands for a group NH,

A and A ² independently of one another are ethane-1, 2-diyl or propane-1,3-diyl, R ² , R ³ , R ⁵ and R ⁶ independently of one another are methyl or ethyl, (particularly preferably methyl),

R ⁷ is a (C 10 to C 24) alkyl group, in particular decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl).

It is preferable to select the structural unit of the formula (VI) from at least one structural unit of the formula (VI-1) to (VI-8)

In addition, it is found to be particularly preferred to choose the structural unit of the formula (VI-7) and / or of the formula (VI-8) as the structural unit of the formula (VI). The structural unit of formula (VI-8) is a most preferred structural unit.

Furthermore, in view of achieving the object, it has proved to be preferable, when the structural unit of the formula (VII) is selected, to consist of at least one structural unit of the formulas (VI 1-1) to (VII-8)

(VII-4)

(VII-8), wherein each R ⁷ is a (Ce to C3o) alkyl group.

In turn, particularly preferred structural unit of the formula (VII) are the structural units of the formula (VII-7) and / or the formula (VII-8) wherein each R ⁷ is octyl (capryl), decyl (caprinyl), dodecyl (lauryl ), Tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl). The structural unit of the formula (VII-8) represents a very particularly preferred structural unit of the formula (VII).

A very particularly preferably cationic polymer present in the composition comprises at least one structural unit of the formula (IV), at least one structural unit of the formula (V), at least one structural unit of the formula (VI-8) and at least one structural unit of the formula (VII-8) .

wherein R ⁷ is octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl).

A very particularly preferred cationic polymer is the copolymer of N-vinylpyrrolidone, N-vinylcaprolactam, N- (3-dimethylaminopropyl) methacrylamide and 3- (methacryloylamino) propyl lauryl-dimethylammonium chloride (INCI name: Polyquaternium-69), which is described, for example, in US Pat the trade name Aqua style ^® 300 marketed (28-32 wt .-% of active substance in ethanol-water mixture, molecular weight 350,000) by the company ISP.

Further preferred cationic polymers are, for example cationized honey, for example the commercial product Honeyquat ^® 50,

polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid. The under the names Merquat ^® 100

(Poly (dimethyldiallylammonium chloride)) and Merquat ^® 550 (dimethyldiallylammonium chloride-acrylamide copolymer) are examples of such cationic polymers having the INCI - designation Polyquaternium-7,

Vinylpyrrolidone vinylimidazoliummethochloride copolymers, such as those offered under the names Luviquat.RTM ^® FC 370, FC 550 and the INCI name Polyquaternium-16 and FC 905 and HM 552,

quaternized vinyl pyrrolidone / dimethylaminoethyl methacrylate, for example

Vinylpyrrolidone / dimethylaminoethyl methacrylate methosulfate copolymer, which is among the

Trade names Gafquat ^® 755 N and Gafquat ^® 734, United States is marketed by Gaf Co. and the INCI - name Polyquaternium-1 1,

quaternized polyvinyl alcohol,

and the polymers known under the names Polyquaternium-2, Polyquaternium-17, Polyquatenium-18 and Polyquaternium-27 with quaternary nitrogen atoms in the

Polymer backbone,

Vinylpyrrolidone-Vinylcaprolactam-acrylate terpolymers, such as those with acrylic acid esters and acrylamides as a third monomer building commercially, for example, under the

Designation Aquaflex ^® SF 40 are offered.

Suitable amphoteric polymers are those polymers in which a cationic group is derived from at least one of the following monomers:

(i) monomers having quaternary ammonium groups of the general formula (monol),

R is -CH = CR ² -CO-Z- (C n H ₂ n) -N ^<+) R ² R ³ R ⁴ A <> (monol)

in which R and R ² independently of one another represent hydrogen or a methyl group and R ³ , R ⁴ and R ⁵ independently of one another represent alkyl groups having 1 to 4 carbon atoms, Z denotes an NH group or an oxygen atom, n denotes an integer of 2 to 5 and A ^{() is} the anion of an organic or inorganic acid,

Monomers having quaternary ammonium groups of the general formula (Mono 2),

wherein R ⁶ and R ⁷ independently of one another represent a (C 1 to C 4) -alkyl group, in particular a methyl group and

A ^"is the anion of an organic or inorganic acid,

monomeric carboxylic acids of the general formula (mono 3),

R ⁸ -CH = CR ⁹ -COOH (mono 3) in which R ⁸ and R ^{9 are} independently hydrogen or methyl groups.

Particularly preferred are those polymers in which monomers of type (i) are used in which R ³ , R ⁴ and R ^{5 are} methyl groups, Z is an NH group and A ^{() is} a halide,

Methoxy sulfate or ethoxy sulfate ion; Acrylamidopropyltrimethylammonium chloride is a particularly preferred monomer (i). As the monomer (ii) for the polymers mentioned, acrylic acid is preferably used.

Particularly preferred amphoteric polymers are copolymers of at least one monomer (monol) or (mono 2) with the monomer (mono 3), in particular copolymers of the

Monomers (Mono2) and (Mono3). Very particularly preferably used amphoteric polymers are copolymers of diallyl dimethyl ammonium chloride and acrylic acid. These copolymers are sold under the INCI designation Polyquaternium-22, inter alia, with the trade name Merquat ^® 280 (Nalco).

In addition, the amphoteric polymers in addition to a monomer (Monol) or (Mono2) and a monomer (Mono3) additionally a monomer (Mono4)

(iv) monomeric carboxylic acid amides of the general formula (mono 4),

in which R ⁰ and R independently of one another are hydrogen or methyl groups and R ^{2 is} a hydrogen atom or a (C 1 to C 8) -alkyl group.

Very particularly preferred amphoteric polymers based on a comonomer (Mono4) are terpolymers of diallyldimethylammonium chloride, acrylamide and acrylic acid. These copolymers are marketed ^® under the INCI name Polyquaternium-39, among others, with the trade name Merquat Plus 3330 (Nalco).

The amphoteric polymers can generally be used both directly and in salt form

Neutralization of the polymers, for example, with an alkali metal hydroxide, are used.

The polymers described so far represent only a part of the polymers which can be used. In order not to have to describe all suitable cationic and / or amphoteric polymers together with their composition, the INCI declarations of the preferred polymers are given in summary. The preferred polymers bear the INCI name:

Polyquaternium-2, Polyquaternium-4, Polyquaternium-6, Polyquaternium-7, Polyquaternium-10, Polyquaternium-1 1, Polyquaternium-15, Polyquaternium-16, Polyquaternium-17, Polyquaternium- 18, Polyquaternium-22, Polyquaternium-24, Polyquaternium-28, Polyquaternium-32, Polyquaternium-33, Polyquaternium-34, Polyquaternium-35, Polyquaternium-37, Polyquaternium-39, Polyquaternium-41, Polyquaternium-42, Polyquaternium-44, Polyquaternium-47,

Polyquaternium-55, Polyquaternium-67, Polyquaternium-68, Polyquaternium-69, Polyquaternium-72, Polyquaternium-74, Polyquaternium-76, Polyquaternium-86, Polyquaternium-89,

Polyquaternium-95 and Polyquaternium-101 and mixtures thereof.

Suitable nonionic hair care polymers preferably include alcohol and / or water-soluble vinylpyrrolidone polymers such as a vinylpyrrolidone homopolymer or copolymer, in particular with vinyl acetate.

Suitable vinylpyrrolidone polymers are, for example, the products known by the trade name "Luviskoi®", for example the homopolymers "Luviskoi® K 30, K 60 and K 90" and the water- or alcohol-soluble copolymers of vinylpyrrolidone and vinyl acetate, which are sold under the trade name "Luviskoi® VA 55 or VA 64" are sold by BASF SE.

Other suitable nonionic hair care polymers are

Vinyl pyrrolidone / vinyl acetate Vinyl propionate copolymers such as "Luviskoi® VAP 343".

Vinylpyrrolidone / (meth) acrylic acid ester copolymers and chitosan derivatives.

However, it is very particularly preferred that the hair treatment agent a

Polyorganosiloxane as hair care polymer included.

Particularly preferred hair treatment agents contain as polyorganosiloxane

Polyalkylsiloxane, polyarylsiloxane, polyalkylarylsiloxane, silicone rubber, silicone resin, with

organofunctional groups modified polyorganosiloxane or mixtures thereof.

Very particularly preferred hair treatment compositions are characterized in that

(a) the polyalkylsiloxanes are selected from:

- trimethylsilyl endblocked polydimethylsiloxanes;

- Dimethylsilanol-terminated polydimethylsiloxanes;

- polyalkyl (Ci-2o) siloxanes;

(b) the polyaryl siloxanes are selected from:

The be linear and / or branched and have a viscosity in the range of 1 ^■ 10 ⁵ to 5 10 ^-2 m ² / s at 25 ° C polydimethylmethylphenylsiloxanes, polydimethyldiphenylsiloxanes;

(c) said silicone gums are selected from polydiorganosiloxanes having number average molecular weights in the range 200,000 to 1,000,000 and used as such or in admixture with a solvent; (d) the resins are selected from the group consisting of R3S1O1 / 2, R2S1O2 / 2, RS1O3 / 2 and S1O4 / 2 units, wherein the group R is a hydrocarbon group of 1 to 16 carbon atoms or a phenyl group;

(E) the organomodified polyorganosiloxanes are selected from polyorganosiloxanes having in their structure one or more organofunctional groups bonded through a hydrocarbon group.

Particularly preferred agents contain the or the polyorganosiloxane (s) preferably in amounts of 0.1 to 10 wt .-%, preferably from 0.25 to 7 wt .-% and in particular from 0.5 to 5 wt .-%, in each case based on the total mean.

Particularly preferred agents are characterized in that they contain at least one

Polyorganosiloxane of the formula Si-I

(CH ₃ ) 3 Si - [0-Si (CH ₃ ) 2] x -O-Si (CH ₃ ) 3 (Si-I),

in which x is a number from 0 to 100, preferably from 0 to 50, more preferably from 0 to 20 and in particular 0 to 10.

These polyorganosiloxanes are referred to according to the INCI nomenclature as DIMETHICONE.

Of course, mixtures of polyorganosiloxanes in the

Be included hair treatment products.

Preferred polyorganosiloxanes which can be used have viscosities of from 0.2 to 2 mm ² s at 20 ° C., with polyorganosiloxanes having viscosities of from 0.5 to 1 mmV being particularly preferred.

Preferred hair treatment agents are characterized in that the polyorganosiloxanes used singly or in admixture are selected from the following structures

polydimethylsiloxane

Polydimethylsiloxane / methylvinylsiloxanes,

Polydimethylsiloxane / diphenylsiloxane,

Polydimethylsiloxane / phenylmethylsiloxane,

Polydimethylsiloxane / diphenylsiloxane / methylvinylsiloxane and the following mixtures: mixtures formed from a chain-end hydroxylated polydimethylsiloxane and a cyclic polydimethylsiloxane,

Mixtures formed from a polydimethylsiloxane gum and a cyclic silicone, and

Mixtures of polydimethylsiloxanes of different viscosities. Particularly preferred agents contain one or more organomodified polyorganosiloxanes, since the performance properties of the polyorganosiloxanes can be adapted by the modification of the application even more detailed. preferred

Hair treatment agents are characterized in that the organomodified silicones are selected from the polyorganosiloxanes containing

a) polyethyleneoxy and / or polypropyleneoxy groups,

b) substituted or unsubstituted aminated groups,

c) thiol groups,

d) alkoxylated groups,

e) hydroxyalkyl groups,

f) acyloxyalkyl groups,

g) carboxyalkyl groups,

h) 2-hydroxyalkylsulfonate groups,

i) 2-hydroxyalkyl thiosulfonate groups,

j) hydroxyacylamino groups.

Particularly preferred agents contain one or more amino-functional polyorganosiloxanes. Such polyorganosiloxanes may be exemplified by the formula

M (RaQbSiO (4-a-b) / 2) x (RcSiO (4-c) / 2) y M

be described, wherein in the above formula R is a hydrocarbon or a

Is a hydrocarbon radical of 1 to about 6 carbon atoms, Q is a polar radical of the general formula -R HZ, where R is a divalent linking group bonded to hydrogen and the radical Z, composed of carbon and hydrogen atoms, carbon, Hydrogen and oxygen atoms or carbon, hydrogen and nitrogen atoms, and Z is an organic, amino-functional group containing at least one amino-functional group; "a" assumes values in the range of about 0 to about 2, "b" assumes values in the range of about 1 to about 3, "a" + "b" is less than or equal to 3, and "c" is a number in the range from about 1 to about 3, and x is a number ranging from 1 to about 2,000, preferably from about 3 to about 50, and most preferably from about 3 to about 25, and y is a number ranging from about 20 to about 10,000 , preferably from about 125 to about 10,000, and most preferably from about 150 to about 1,000, and M is a suitable silicone end group as known in the art, preferably trimethylsiloxy. Non-limiting examples of the groups represented by R include alkyl groups such as methyl, ethyl, propyl, isopropyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl, 4-bromobutyl, 3,3,3-trifluoropropyl, chlorocyclohexyl, bromophenyl, chlorophenyl and the like, and sulfur-containing radicals such as mercaptoethyl, mercaptopropyl, mercaptohexyl, mercaptophenyl and the like; Preferably R is an alkyl radical containing from 1 to about 6 carbon atoms, and am most preferably R is methyl. Examples of R include methylene, ethylene, propylene,

Hexamethylene, decamethylene, -CH ₂ CH (CH ₃ ) CH ₂ -, phenylene, naphthylene, -CH ₂ CH ₂ SCH ₂ CH ₂ -, - CH ₂ CH ₂ OCH ₂ -, -OCH ₂ CH ₂ -, -OCH ₂ CH ₂ CH ₂ -, -CH ₂ CH (CH ₃ ) C (O) OCH ₂ - (CH ₂ ) 3CC (O) ₂ CH ₂ -, - C 6 H 4 C 6 H 4 -, -C 6 H 4 CH ₂ C 6 H 4 -; and - (CH 2) ₃ C (O) SCH ₂ CH 2 -.

Z is an organic, amino-functional radical containing at least one functional

Amino group. A possible formula for Z is NH (CH 2) z NH 2, wherein z is 1 or more. Another possible formula for Z is -NH (CH 2) z (CH 2) zzNH wherein both z and zz are independently 1 or more, this structure including diamino ring structures such as piperazinyl. Z is most preferably a -NHCH 2 CH 2 NH 2 radical. Another possible formula for Z is -N (CH 2) z (CH 2) zzNX 2 or -NX 2 wherein each X of X 2 is independently selected from the group consisting of hydrogen and alkyl groups of 1 to 12 carbon atoms, and zz is 0.

Q is most preferably a polar amine-functional radical of the formula -CH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2. In the formulas, "a" assumes values in the range of about 0 to about 2, "b" assumes values in the range of about 2 to about 3, "a "+" b "is less than or equal to 3, and" c "is a number in the range of about 1 to about 3. the molar ratio of R _a Q b SiO _(4-a-b) / 2 units to RcSiO (4 c) / 2 units range from about 1: 2 to 1:65, preferably from about 1: 5 to about 1:65, and most preferably from about 1:15 to about 1:20

Polyorganosiloxanes of the above formula, then the various variable substituents in the above formula may be different for the various polyorganosiloxane components present in the polyorganosiloxane mixture.

Preferred agents are characterized in that they contain an amino-functional silicone of the formula (Si-II)

R'aG ₃ - _a -Si (OSiG ₂ ) n - (OSiG _b R ' ₂ - b) m -O-SiG ₃ -a-R'a (Si-II),

contain, in which means:

G is -H, a phenyl group, -OH, -O-CH ₃ , -CH ₃ , -O-CH ₂ CH ₃ , -CH ₂ CH ₃ , -O-

CH2CH3 CH _2, -CH 2 CH ₂ CH 3, -0-CH (CH ₃₎ _2, -CH (CH ₃₎ _2, -O-CH2CH2CH2CH3, - CH2CH2CH2CH3, -0-CH ₂ CH (CH ₃₎ 2, -CH ₂ CH _(CH3) 2, -0-CH (CH ₃₎ CH ₂ CH _3, - CH (CH ₃₎ CH ₂ CH _3, -0-C (CH ₃₎ 3, -C (CH ₃₎ _3;

a is a number between 0 and 3, in particular 0;

b is a number between 0 and 1, in particular 1,

m and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n is preferably values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000, in particular from 1 to 10,

- R ^' is a monovalent radical selected from

o -QN (R ") - CH ₂ -CH ₂ -N (R") 2 o -QN (R ") ₂

o -QN ⁺ (R ") ₃ A- o -QN ⁺ H (R") ₂ A- o -QN ⁺ H ₂ (R ") A- o -QN (R") - CH 2 -CH 2 -N ⁺ R "H ₂ A,

where each Q is a chemical bond, -CH ₂ -, -CH ₂ -CH ₂ -, -CH ₂ CH ₂ CH ₂ -, -C (CH ₃ ) ₂ -, -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH ₂ C (CH ₃ ) 2, -CH (CH ₃ ) 2 ₃ ) CH ₂ CH ₂ -, R "is identical or different radicals from the group -H, -phenyl, -benzyl, -CH 2 -CH (CH ₃ ) Ph, the Ci-20-alkyl radicals, preferably -CH ₃ , -CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₃ , - CH (CH ₃ ) ₂ , -CH ₂ CH ₂ CH ₂ H ₃ , -CH ₂ CH (CH ₃ ) ₂ , -CH (CH ₃ ) CH ₂ CH ₃ , C (CH ₃ ) ₃ , and A represents an anion, which is preferably selected from chloride, bromide, iodide or methosulfate.

amino-functional silicone of the formula (Si-Ila)

(CH ₃ ) ₃ Si [0-Si (CH ₃ ) ₂ ] _n [OSi (CH ₃ )] m -OSi (CH ₃ ) ₃ (Si-Ila),

I

CH ₂ CH (CH ₃ ) CH ₂ NH (CH ₂ ) ₂ NH ₂

in which m and n are numbers whose sum (m + n) is between 1 and 2000, preferably between 50 and 150, where n preferably values of 0 to 1999 and in particular of 49 to 149 and m preferably values of 1 to 2000 , in particular from 1 to 10 assumes.

These polyorganosiloxanes are named after the INCI declaration

Called TRIMETHYLSILYLAMODIMETHICONE.

Also particularly preferred are agents which are an amino-functional polyorganosiloxane of the formula (Si-IIb)

R- [Si (CH ₃ ) ₂ -O] ni [Si (R) -O] m- [Si (CH ₃ ) ₂ ] n 2 -R (Si-Ilb),

I

in which R is -OH, -O-CH ₃ or a -CH ₃ group and m, n1 and n2 are numbers whose sum (m + n1 + n2) is between 1 and 2,000, preferably between 50 and 150 , where the sum (n1 + n2) preferably assumes values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000, in particular from 1 to 10.

These silicones are referred to as AMODIMETHICONE according to the INCI declaration. Regardless of which amino-functional silicones are employed, preferred are agents containing an amino-functional silicone whose amine number is above 0.25 meq / g, preferably above 0.3 meq / g and especially above 0.4 meq / g. The amine number stands for the milliequivalents of amine per gram of the amino-functional silicone. It can be determined by titration and also expressed in mg KOH / g.

Preferred agents contain - based on their weight - 0.01 to 10 wt.%, Preferably 0.1 to 8 wt.%, Particularly preferably 0.25 to 7.5 wt.% And in particular 0.5 to 5 wt.%

amino-functional silicone (s).

The cyclic dimethicones designated INCY as CYCLOMETHICONE are also preferred. Here are preferred agents which at least one polyorganosiloxane of the formula Si III

in which x is a number from 3 to 200, preferably from 3 to 10, more preferably from 30 to 7 and in particular 3, 4, 5 or 6.

Cyclic silicones having 3 to 7, preferably 4 to 5, Si atoms are, for example

Octamethylcyclotetrasiloxane, available as "Volatile Silicone 7207" (Union Carbide) or "Silbione 70045 V 2" (Rhodia Chemie), decamethylcyclopentasiloxane, available as "Volatile Silicone 7158" (Union Carbide) and "Silbione 70045 V 5" (Rhodia Chimie) and Mixtures thereof.

Cyclocopolymers of the dimethylsiloxane / methylalkylsiloxane type are e.g. "Volatile Silicone FZ 3109" (Union Carbide having the structure:

It is also possible to use mixtures of cyclic silicones with

Organosilicone compounds such as the mixture of octamethylcyclotetrasiloxane and Tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1'-bis (2,2,2 ', 2', 3,3'-hexatrimethylsilyloxy) neopentane.

The silicones described above have a backbone composed of -Si-O-Si units. Of course, these Si-O-Si units may also be interrupted by carbon chains. Appropriate molecules are accessible by chain extension reactions and are preferably used in the form of silicone-in-water emulsions.

Also preferred agents include a silicone of formula Si-IV

R _{3 is} -Si- [O-SiR 2] x- (CH 2) n - [O-SiR 2] _y -O-SiR 3 (Si-IV),

in the R for identical or different radicals from the group -H, -phenyl, -benzyl, -CH 2 -CH (CH ₃ ) Ph, the Ci-20-alkyl radicals, preferably -CH ₃ , -CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₃ , - CH (CH ₃ ) 2, -CH ₂ CH ₂ CH 2 H 3, -CH ₂ CH (CH ₃ ) 2, -CH (CH ₃ ) CH ₂ CH ₃ , -C (CH ₃ ) ₃ , x and y is a number from 0 to 200 , preferably from 0 to 10, more preferably from 0 to 7 and especially 0, 1, 2, 3, 4, 5 or 6, and n is a number from 0 to 10, preferably from 1 to 8 and especially for 2 , 3, 4, 5, 6 stands.

A likewise particularly preferably usable polyanilosiloxane has the general formula (A):

has,

wherein

Xi and X2 independently of one another denote OH, OR, R ² , O-PDMS or O-f siloxane,

X _{3 is} hydrogen or a monovalent hydrocarbon radical having 1 to 8 carbon atoms each

Rest, PDMS or siloxane means

X4 is a radical of the formula

-CH ₂ NO

-CH ₇ NHR ⁴ -CH ₂ NR 2 or

is and

a is a number from 1 to 100.

in which

R is an alkyl radical having 1 to 8 carbon atoms,

R ^{2 is} a monovalent, optionally substituted with the elements N, P, S, O, Si and halogen, saturated or unsaturated hydrocarbon radical having 1 to 200 carbon atoms per radical, PDMS for

stands,

siloxane for

stands,

R ³ are each independently a monovalent, optionally with the elements N, P, S,

O, Si and halogen substituted, saturated or unsaturated hydrocarbon radical with 1 to

200 carbon atoms per radical means

A is a radical of the formula R ⁶ - [NR ⁷ -R ⁸ -] fNR ⁷ 2,

in which

R ^{6 is} a divalent linear or branched hydrocarbon radical having 3 to 18

Carbon atoms means

R ^{7 represents} a hydrogen atom, an alkyl radical having 1 to 8 carbon atoms or an acyl radical,

R ^{8 is} a divalent hydrocarbon radical having 1 to 6 carbon atoms,

b is a number from 1 to 2000,

c is 0 or a number from 1 to 2000

d is a number from 1 to 1000,

e is 0 or a number from 1 to 5,

f is 0, 1, 2, 3 or 4,

Z is hydrogen, an alkyl radical having 1 to 8 carbon atoms or

means

R ⁴ denotes a monovalent hydrocarbon radical having 1 to 18 carbon atoms and optionally containing N and / or O atoms, and R ^{5 is} a divalent optionally N and / or O atoms containing hydrocarbon radical having 3 to 12 carbon atoms.

A particularly preferred polyorganosiloxane of the formula (A) is known, for example, under the INCI name amodimethicone / morpholinomethyl silsesquioxane copolymer and / or under the CAS number 1293390-78-9. Commercially available this polyorganosiloxane under the name Belsil® ADM 8301 E (ex Wacker). The raw material is a microemulsion and has the following constituents: amodimethicone / morpholinomethyl silsesquioxane

Copolymer, trideceth-5, glycerin, phenoxyethanol and water.

Very particularly preferred hair treatment agents contain trimethylsilyl-terminated polyalkylsiloxanes, dimethylsilanol-terminated polyalkylsiloxanes,

Polyalkylarylsiloxanes, mixtures of two polydimethylsiloxanes (PDMS) formed from a gum and an oil of different viscosities, mixtures of organosiloxanes and cyclic silicones or organopolysiloxane resins.

Trade names preferred as conditioning agents used silicones are, for example

Decamethyltetrasiloxane "SH 200" (Toray Silicone)

Silbione® oils of the 47 and 70 047 series

Mirasil® oils (Rhodia Chimie) like 70 047 V 500 000

200 series oils (Dow Corning), such as DC200 with a viscosity of 60,000 cSt (mm ² / s) Viscasil® Oils (Momentive Performance Materials Inc.)

SF Series (SF 96, SF 18, SF 1023, SF 1 154, SF 1250 and SF 1265) oils from Momentive Performance Materials Inc.

Dimethiconols such as oils of the 48 series (Rhodia Chimie)

Abil® Wax 9800 and 9801 (Evonik)

Silbione Oils of the 70 641 Series (Rhodia Chimie)

Oils of Rhodorsil 70 633 and 763 series (Rhodia Chimie)

Dow Corning 556 Cosmetic Grade Fluid (Dow Corning)

PK series (Momentive Performance Materials) silicones, such as Baysilone® PK20

Silicones of the PN and PH series (Momentive Performance Materials), e.g. Oil PN1000 and

Oil PH 1000

Q2 1401 (Dow Corning)

SF 1214 Silicone Fluid (Momentive Performance Materials)

SF 1236 (Momentive Performance Materials)

"Dow Corning 593" or "Silicone Fluid SS 4230 and SS 4267" (Momentive Performance Materials)

X22-4914, X21-5034 and X21-5037 (Shin-Etsu) DC 1248 and Q2 5200 (Dow Corning)

GP 4 Silicone Fluid and GP 7100 (Genesee Polymers Corporation)

Q2 8220 and Dow Corning 929 or 939 (Dow Corning)

GP 72 A and GP 71 (Genesee Polymers Corporation)

Silicone Copolymer F-755 (SWS Silicones) and Abil Wax 2428, 2434 and 2440 (Evonik)

X-22-3701E (Shin-Etsu)

Abil S201 and Abil S255 (Evonik)

Q2-8413 (Dow Corning).

The hair treatment composition further contains an aqueous or an aqueous-alcoholic carrier. An aqueous cosmetic carrier contains at least 50% by weight of water. For the purposes of the present invention, aqueous-alcoholic cosmetic carriers include aqueous solutions containing from 3 to 70% by weight of a C 2 -C 6 -alcohol, in particular ethanol or propanol,

Isopropanol, butanol, isobutanol, tert-butanol, n-pentanol, iso-pentanols, n-hexanol, isohexanols, glycol, glycerol, 1, 2-pentanediol, 1, 5-pentanediol, 1, 2-hexanediol or 1 To understand 6-hexanediol. The agents may additionally contain other organic solvents, such as, for example, methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. Preference is given to all water-soluble organic solvents.

The pH of the hair treatment agent is preferably from 3 to 5.

Preferred hair treatment agents are characterized as follows:

From 0.01% to 5.0% by weight of methionylmethionine,

0.001 to 5.0% by weight of a cationic surfactant,

0.0001 to 3.0% by weight of an organic acid,

0.01 to 20 wt .-% of a hair care polymer as well

an aqueous or aqueous-alcoholic carrier.

More preferred hair treatment agents are further characterized as follows:

0.1 to 3.0% by weight of methionylmethionine,

0.001 to 5.0% by weight of a cationic surfactant,

0.0001 to 3.0% by weight of an organic acid,

0.1 to 10% by weight of a hair care polymer as well

an aqueous or aqueous-alcoholic carrier.

More preferred hair treatment agents are characterized as follows:

0.1 to 3.0% by weight of methionylmethionine,

0.1 to 3.0% by weight of at least one cationic surfactant selected from the group consisting of monoalkyl quats, amidoamines and mixtures thereof, 0.0001 to 3.0% by weight of an organic acid selected from the group consisting of citric acid, tartaric acid, malic acid, lactic acid and mixtures thereof,

0.1 to 10% by weight of a hair care polymer as well

an aqueous or aqueous-alcoholic carrier.

Very particularly preferred hair treatment compositions are characterized as follows:

0.1 to 3.0% by weight of methionylmethionine,

0.1 to 3.0% by weight of at least one cationic surfactant selected from the group consisting of monoalkyl quats, amidoamines and mixtures thereof,

0.0001 to 3.0% by weight of citric acid and / or lactic acid,

0.1 to 10 wt .-% of a hair care polymer selected from the group consisting of cationic polymers, polyorganosiloxanes and mixtures thereof, and

an aqueous or aqueous-alcoholic carrier.

Highly preferred hair treatment agents are characterized as follows:

0.1 to 3.0% by weight of methionylmethionine,

0.1 to 3.0% by weight of amidoamines,

0.0001 to 3.0% by weight of citric acid and / or lactic acid,

0.1 to 10 wt .-% polyorganosiloxane (s) as well as

an aqueous or aqueous-alcoholic carrier.

The hair treatment compositions have advantageous properties and also confer advantageous properties on the hair treated with them. Thus, the hair treatment agents increase the elasticity of the hair treated with them and lead to an inner-structural strengthening of the hair fibers, which, for example, in higher melting temperatures in the

Differential thermal analysis precipitates. Likewise, it comes to a hydrophobing of

Hair surface, which shows in a significant increase in the contact angle. It also shows an improvement in wet and dry combing and prevention of premature splitting in the treated hair.

In the following, further ingredients of the hair treatment compositions are described, which may be included in the compositions in addition to the above-described mandatory ingredients.

Other suitable ingredients include surfactants, nonionic polymers, anionic polymers, cationic polymers, amphoteric polymers, waxes, protein hydrolysates, amino acids,

Oligopetide, Vitamins, Provitamins, Vitamin Precursors, Betaines, Biochinones, Purines (Derivatives), Taurine (Derivatives), Nourishing Agents, Plant Extracts, Ester Oils, Ultraviolet Sunscreens,

Structuring agents, thickeners, electrolytes, pH adjusters, swelling agents, dyes, Anti-dandruff agents, chelating agents, opacifiers, pearlescers, pigments, stabilizers, propellants, antioxidants, perfume oils and / or preservatives.

The hair treatment compositions can be both single-phase and multiphase, for example in particular with two or three optically clearly separated discrete phases. When the compositions are multi-phase, the whole composition is shaken into a single-phase composition before use and applied. The hair treatment compositions can be formulated as pump spray, aerosol spray, pump foam or aerosol foam.

For this purpose, the means are assembled in a dispensing device, which is either an additionally filled with a propellant compressed gas container ("aerosol container") or a non-aerosol container.

Another object of the invention is a method for hair treatment, in which a

Hair treatment composition according to the invention is applied to the hair and is rinsed by the hair after a contact time.

The exposure time is preferably a few seconds to 100 minutes, more preferably 1 to 50 minutes and most preferably 1 to 30 minutes.

Yet another subject of the invention is a method in which a hair treatment agent according to the invention is applied to the hair and remains there. By "remaining on the hair" is meant that the agent is not rinsed out of the hair immediately after its application, but rather remains in this case for more than 100 minutes until the next hair wash on the hair.

The following examples are intended to illustrate the subject matter of the present invention without, however, limiting it.

Examples

All amounts are, unless otherwise stated, parts by weight of active substance. The following formulations were provided using known preparation methods.

Care spray, also in foam form and / or as hair cure applicable:

For application as a foam the recipe in question is either filled with a propellant in an aerosol container or discharged from a pump bottle with a corresponding pump attachment, such as Airfoamer as foam.

For use as a hair conditioner or cream will become the recipe listed above

Ethylene glycol distearate and / or glycerol monostearate added in amounts of 0.2 to 5.0 wt.%.

Hair conditioner:

Wt .-%

Cetearyl Alcohol 5.0

Stearamidopropyl dimethylamine 0.6

Glycol Distearate 1, 0

Polyquaternium-37 0.25

DL-methionyl-DL-methionine 1, 0

Lactic acid 0, 1 Behenoyl PG -trimonium chlorides 1, 5

Behentrimonium chlorides 0.5

Hydrolyzed keratin 1, 5

Glycerol 0, 1

Amodimethicone 1, 0

Water, preservation, accompanying substances and possibly perfume oils ad 100 s, the following commercial products were used:

Commercial product INCI Supplier / Manufacturer

Lanette® O Cetearyl Alcohol BASF SE

Cutina® AGS Glycol Distearate BASF SE

Cosmedia® Triple C Polyquaternium-37 / Dicaprylyl Carbonate BASF SE

/ Lauryl Glucoside

Quartamin® BTC 131 Behenoyl PG Trimonium Chloride Kao Chemicals

Genamin® KDMP Behentrimonium Chloride Clariant

ProSina Hydrolyzed Keratin Croda

TEGO® Amide S 18 Stearamidopropyldimethylamine Evonik

Xiameter® PMX 200 Silicone Fluid Dimethicone Dow Corning 60000 CS

SilCare® Silicone SEA Amodimethicone Clariant

Claims

claims:

1. hair treatment composition containing - based on the weight of the total composition - a) 0.0001 to 30 wt .-% methionylmethionine,

b) from 0.001 to 5% by weight of cationic surfactant,

c) 0.0001 to 3.0% by weight of an organic acid,

d) 0.01 to 20 wt .-% of a hair care polymer and

e) an aqueous or aqueous-alcoholic carrier.

2. Hair treatment composition according to claim 1, characterized in that the cationic surfactant is selected from the group consisting of

i) alkyl quats

ii) esterquats,

iii) quaternary imidazolines of the formula (Tkat4),

in which the radicals R are each independently a saturated or unsaturated, linear or branched hydrocarbon radical having a chain length of 8 to 30 carbon atoms and A is a physiologically acceptable anion, iv) amidoamines and / or cationized amidoamines and

v) mixtures thereof.

3. Hair treatment composition according to claim 2, characterized in that at least one cationic surfactant is an alkyl quat, in particular a monoalkyl quat.

4. Hair treatment composition according to claim 2, characterized in that at least one cationic surfactant is an amidoamine.

5. hair treatment composition according to claim 2, characterized in that the

Hair treatment agent containing a monoalkyl quat and an amidoamine as a cationic surfactant.

6. hair treatment composition according to one of claims 1 to 5, characterized in that the methionylmethionine a mixture of L-methionyl-L-methionine, L-methionyl-D-methionine, D-methionyl-L-methionine and D-methionyl-D- is methionine.

7. Hair treatment composition according to one of claims 1 to 5, characterized in that the methionyl methionine is L-methionyl-L-methionine and / or D-methionyl-D-methionine.

Hair treatment composition according to one of claims 1 to 7, characterized in that the hair care polymer is selected from the group consisting of cationic polymers, amphoteric polymers, nonionic polymers, polyorganosiloxanes and mixtures thereof.

9. hair treatment composition according to one of claims 1 to 8, characterized in that it has a pH of 3 to 5.

10. Hair treatment composition according to one of claims 1 to 9, characterized in that the organic acid is selected from the group consisting of citric acid, lactic acid and mixtures thereof.

1 1. Hair treatment composition according to one of claims 3 or 5 to 10, characterized in that the monoalkyl quat is selected from the group consisting of

Cetyltrimethylammonium chloride, behenyltrimethylammonium chloride and mixtures thereof.

12. Hair treatment composition according to one of claims 4 to 1 1, characterized in that the amidoamine comprises a compound having the INCI name stearamidopropyl dimethylamine.

13. Use of methionylmethionine in a hair treatment composition comprising

cationic surfactant, an organic acid and a hair care polymer for improving at least one of the properties

Tensile strength of keratinic fibers, especially human hair; Combability of keratinic fibers, in particular of human hair; Hydrophobing the surface of keratinic fibers, in particular human hair; or

Strengthening the internal structure of keratinic fibers, especially human hair.