WO2010029267A1

WO2010029267A1 - Cosmetic composition containing quaternary ammonium esters and thickening polymers, and use for hair conditioning

Info

Publication number: WO2010029267A1
Application number: PCT/FR2009/051715
Authority: WO
Inventors: Estelle Mathonneau; Virginie Le Chaux
Original assignee: L'oreal
Priority date: 2008-09-12
Filing date: 2009-09-11
Publication date: 2010-03-18

Abstract

The present invention relates to cosmetic compositions containing quaternary ammonium ester-type cationic compounds, particularly 2-[2-(diethylamino)ethoxy]ethanol derivatives combined with thickening polymers, to the use thereof, particularly for hair conditioning, and to a cosmetic treatment method, particularly for hair, using said compounds. The hair treated with said compositions has good conditioning properties, particularly softness and lack of tangling.

Description

"COSMETIC COMPOSITION COMPRISING AMMONIUM ESTERS

QUATERNARIES AND THICKENING POLYMERS, USE

FOR CONDITIONING HAIR »

The present invention relates to novel cosmetic compositions comprising particular quaternary ammonium esters and one or more particular thickening polymers, as well as their use in particular for hair conditioning. It is well known that hair which has been sensitized, in particular damaged and / or weakened, to varying degrees under the action of atmospheric agents or under the action of mechanical and / or chemical treatments, such as colorings, stains, discolorations and perms, are often difficult to disentangle and comb, and also lack sweetness. It has already been proposed for the treatment of keratin materials and in particular hair, cosmetic compositions containing conditioning cationic surfactants, such as those described in US2006 / 0078529. However, such compositions do not yet have the desired cosmetic qualities, in particular in terms of sensory properties, in particular to touch the hair after treatment.

Now, the Applicant has now discovered, unexpectedly and surprisingly, that certain specific cationic compounds can bring interesting conditioning properties to the hair, in particular concerning the improvement of the flexibility of the hair when the composition is applied to wet hair. , then obtaining, after rinsing, hair still having improved flexibility. This relaxation of the hair is particularly remarkable with the compositions according to the invention. Moreover, in addition to flexibility, these compositions also make it possible to improve the disentangling and the smoothing of the hair; the shaping of the hair is easier, and the touch of the hair is very pleasant and fluid.

Thus, an object of the present invention is a cosmetic composition comprising in a physiologically acceptable medium one or more quaternary ammonium esters of formula (I) as defined below and one or more thickening polymers chosen from: a) polymers thickeners not comprising sugar units and b) the thickening polymers different from inulin and pectin and comprising one or more sugar units.

The quaternary ammonium esters according to the invention therefore correspond to formula (I):

in which :

n is an integer between 1 and 10;

- R1, R2 and R3 denote, independently of each other, a saturated or unsaturated, linear or cyclic or branched, hydrocarbon-based hydrocarbon group comprising 1 to 22 carbon atoms (in particular alkyl or alkenyl), optionally substituted by a or more hydroxyl (-OH) and / or amino radicals (-NRR 'with R and R' selected from, independently of one another, H and C1-C6 alkyl); or

- R1 denotes a saturated or unsaturated, linear or cyclic or branched, hydrocarbon-based hydrocarbon group comprising 1 to 22 carbon atoms (in particular alkyl or alkenyl), optionally substituted by one or more hydroxyl (-OH) and / or amino radicals; (-NRR 'with R and R' selected from, independently of one another, H and C1-C6 alkyl); and

R2 and R3 form, with the nitrogen atom to which they are bonded, a saturated or unsaturated carbon-containing heterocyclic ring comprising 5 or 6 ring members, one or two non-adjacent carbon atoms possibly being replaced by an oxygen atom or sulfur atom; or nitrogen (-NR "with R" = H or C1 -C22); said heterocycle possibly being substituted by one or more radicals, which may be identical or different, chosen from aryl, C 1 -C 22 alkyl, hydroxyl (OH), amino (-NRR 'radicals with R and R' chosen from, independently of one another; on the other, H and C 1 -C 6 alkyl),

- R4 designates:

a linear C 1 -C 30 or branched C 3 -C 30 alkyl radical, optionally interrupted by a 3-, 4- or 5-membered carbon ring, and / or optionally substituted with (i) an aryl itself optionally substituted with one or a plurality of radicals, which may be identical or different, chosen from C1-C6 alkyl, hydroxyl (OH) and amino radicals (-NRR 'with R and R' chosen from, independently of each other, H and C1-alkyl) C6) and / or (ii) one or more radicals, which may be identical or different, chosen from the hydroxyl (OH) and amino (-NRR 'radicals with R and R' chosen from, independently of one another, H and C1-C6 alkyl), a C2-C30 or branched C3-C30 alkenyl linear radical comprising one or more double bonds, especially 1 to 6 C = C double bonds, or even 1 to 3 C = C double bonds; optionally substituted by one or more radicals, which may be identical or different, chosen from the hydroxyl (OH) and amino (-NRR 'radicals with R and R' chosen from, independently of one another, H and C 1 -C 6 alkyl; )

an aryl group, optionally substituted with one or more radicals, which may be identical or different, chosen from C 1 -C 22 alkyl, C 1 -C 22 alkylcarbonyl, hydroxyl (OH), amino (-NRR 'radicals with R and R' chosen from , independently of each other, H and C 1 -C 6 alkyl);

- X- denotes an anion, or an organic or inorganic mixture of anions, to ensure the electroneutrality of the compounds of formula (I).

The carbon group representing R 1, R 2 and / or R 3 can in particular be a C 1 -C 22 linear alkyl group, a C 3 -C 22 branched alkyl group, a C 2 -C 22 linear alkenyl group or a C 3 -C 22 branched alkenyl group.

Preferably, n is an integer between 1 and 4, especially 1, 2 or 3.

Preferably, R 1 denotes a linear C 1 -C 4 alkyl, branched C 3 -C 4 alkyl, linear C 2 -C 4 alkenyl or branched C 3 -C 4 alkenyl group. Preferably, R 1 represents methyl or ethyl.

Preferably, R2 denotes a C1-C4 linear alkyl, C3-C4 branched alkyl, C2-C4 linear alkenyl or C3-C4 branched alkenyl group. Preferably, R2 represents methyl or ethyl.

Preferably, R 3 denotes a linear C 1 -C 22 alkyl, branched C 3 -C 22 alkyl, linear C 2 -C 22 alkenyl or branched C 3 -C 22 alkenyl group. Preferably, R3 represents a C1-C22, in particular C1-C18, linear alkyl group.

Preferably, R4 denotes: - a linear or branched C6-C30, especially C8-C24, alkyl radical, said alkyl radical possibly being interrupted by a 3-, 4- or 5-membered carbon ring, and / or optionally substituted by aryl itself optionally substituted with one or more radicals, which may be identical or different, chosen from C1-C6 alkyl, hydroxyl and amino radicals; a linear or branched C 6 -C 24, especially C 8 -C 22, alkenyl radical; an aryl group, optionally substituted by one or more radicals, which may be identical or different, chosen from alkylcarbonyl (-C (O) -R) and C4-C18 and / or hydroxyl radicals.

Even more preferably, n is equal to 1, R4 denotes a linear or branched C10-C24 alkyl radical and R1, R2, R3 denote, independently of one another, a linear or branched C1-C6 alkyl radical, and more particularly methyl. and ethyl.

Preferably X ^"is an anion, or a mixture of anions, such as acetate, lactate, tartrate, citrate, halogen, SO ₄ ^2-", MeSO ₄ ^", andSO _^4"; preferably Cl ^" , Br ^" , MeSO ₄ ^" , EtSO ₄ ^" .

The compounds of formula (I) may be used as they are or in the form of solvates, in particular hydrates.

Among the preferred compounds, mention may be made of the following compounds, as well as their solvates:

N, N, N -trimethyl-13-oxo-3,6,9,12-tetraoxahexacosan-1-aminium, An- (1) 18

H ₄₃ - {2- [2- (docosanoyloxy) ethoxy] ethoxy} -N, N, N-trinneethylethananniniunn, An- (1) 19

(20E, 23E) -N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxatriaconta-20,23-dien-1-aminium, An- (1)

N, N, N-trimethyl-20- (2-octylcyclopropyl) -13-oxo-3,6,9,12-tetraoxaicosan-1-aminium, An- (1) 21

N, N, N-Triethyl-2- (2- {2 - [(2-hydroxy-5-octanoylbenzoyl) oxy] ethoxy} ethoxy) ethanaminium, An- (1) 22

N, N, N-Triethyl-2- [2- (2 - {[5- (4-hydroxyphenyl) pentanoyl] oxy} ethoxy) ethoxy] ethanaminium, An- (1) 32

In these compounds, preferably An- (= X-) represents Cl ^" , Br ^" , MeSO ₄ ^" or

EtSO ₄ ^" .

The compounds of formula (I) 2 are very particularly preferred.

The compounds according to the invention may be prepared by those skilled in the art on the basis of their general knowledge.

In particular, they can be prepared according to the following synthesis scheme:

The synthesis of amines A can in particular be carried out according to the process described in patent FR2869902.

The quaternized ester B may be obtained by reacting an alkylating agent, such as methyl iodide, dimethyl sulphate, ethyl iodide, diethyl sulphate or a haloalkane, such as bromohexadécyle. Tertiary amine A and the alkylating agent may be mixed and heated at 15 ° C. to 140 ^° C. for 2 to 80 hours. After cooling, the excess of alkylating agent can be removed by washing with diisopropyl ether.

The solid obtained can be filtered, preferably under an inert atmosphere, washed and dried under reduced pressure, optionally in the presence of P ₂ O ₅ . An ion exchange can be carried out at the end of the reaction, by contact with an ion exchange resin chosen according to the desired exchanges. These resins are, for example, IRA 402 (alkyl sulphate exchange in chlorides) or IRA 400 (iodide exchange in chloride). Thus, the anion can be exchanged by treating an aqueous or (hydro) alcohol solution of the compound with the ion exchange resin. The solvent can be removed, the product washed for example with diisopropyl ether, then filtered and dried under reduced pressure, optionally in the presence of P ₂ O ₅ .

The quantity of the quaternary ammonium ester, alone or as a mixture, present in the compositions depends, of course, on the type of composition and the desired properties, and can vary within a very wide range, generally between 0.degree. , 01 and 50% by weight, preferably between 0.1 and

30% by weight, especially between 0.5 and 25% by weight, or even between 1 and 20% by weight, more preferably between 1, 5 and 10% by weight, relative to the total weight of the composition. The compositions according to the invention may of course comprise a mixture of compounds of formula (I).

For the purposes of the present invention, the term "thickening polymer" is understood to mean a polymer which introduces at 1% by weight into an aqueous or aqueous-alcoholic solution containing 30% of ethanol, and at pH = 7, makes it possible to attain a viscosity of at least 100 cps, preferably at least 500 cps, at 25 ° C and at a shear rate of 1 s ^-1 This viscosity can be measured using a cone / planar viscometer (Haake R600 Rheometer or the like).

Per sugar unit used in the context of the present invention a unit derived from a carbohydrate of the formula C _n (H 2 O) _n _i or (CH ^ O) _n may be optionally modified by sustitution, and / or by oxidation and / or dehydration.

The thickening polymers of the invention may be ionic polymers or not, associative or not.

As regards the non-associative thickening polymers, it is first of all pointed out that for the purposes of the present invention, the non-associative thickening polymers are thickening polymers not containing a C 10 -C 30 fatty chain.

Among the non-associative thickening polymers which do not comprise sugar units, mention may be made of crosslinked acrylic or methacrylic acid homopolymers or copolymers, crosslinked homopolymers of 2-acrylamido-2-methylpropanesulphonic acid and their crosslinked acrylamide copolymers. homopolymers of ammonium acrylate or copolymers of ammonium acrylate and acrylamide alone or in mixtures.

A first family of suitable nonassociative thickening polymers is represented by crosslinked acrylic acid homopolymers.

Among the homopolymers of this type, mention may be made of those crosslinked with an allylic alcohol ether of the sugar series, for example the products sold under the names CARBOPOLS 980, 981, 954, 2984 and 5984 by the company

NOVEON or the products sold under the names SYNTHALEN M and SYNTHALEN K by the company 3 VSA.

The non-associative thickening polymers may also be crosslinked (meth) acrylic acid copolymers such as the polymer sold under the name AQUA SF1 by the company NOVEON. The non-associative thickening polymers may be chosen from cross-linked homopolymers of 2-acrylamido-2-methylpropanesulphonic acid and their crosslinked acrylamide copolymers.

With regard to these homopolymers and copolymers, which may be partially or completely neutralized, mention may be made of polymers comprising from 90 to 99.9% by weight, relative to the total weight of the polymer, of units of formula (j) below:

wherein X + denotes a cation or mixture of cations, or a proton.

More particularly, the cations are chosen from alkali metals (such as sodium, potassium), ammonium ions substituted or not by one to three identical or different alkyl radicals, comprising 1 to 6 carbon atoms, optionally carrying at least a hydroxyl radical, the cations derived from N-methylglucamine, basic amino acids such as arginine and lysine. Preferably, the cation is an ammonium or sodium ion.

In addition, the polymer comprises from 0.01 to 10% by weight, relative to the total weight of the polymer, of crosslinking units originating from at least one monomer having at least two ethylenic unsaturation (carbon-carbon double bond).

The crosslinking monomers having at least two ethylenic unsaturations are chosen for example from diallyl ether, triallyl cyanurate, diallyl maleate, allyl (meth) acrylate, dipropylene glycol diallyl ether, polyglycol diallyl ethers, triethylene glycol divinyl ether, hydroquinone-diallyl ether, tetralyl-oxethanoyl, tetra- or di-ethylene glycol di (meth) acrylate, thallylamine, tetraallylethylenediamine, trimethylolpropane diallyl ether, trimethylolpropane triacrylate, methylenebis (meth) acrylamide or divinylbenzene, allyl ethers of alcohols of the series of sugars, or other allyl- or vinyl-ethers of polyfunctional alcohols, as well as the allyl esters of phosphoric and / or vinylphosphonic acid derivatives, or mixtures thereof. of these compounds.

For more details about these polymers, reference can be made to EP 815828.

Among the crosslinked copolymers of 2-acrylamido-2-methyl-propanesulfonic acid and of acrylamide partially or totally neutralized, mention may be made in particular of the product described in Example 1 of EP 503 853 and it will be possible to refer to this document for these polymers. The composition may also comprise, as non-associative thickening polymers, homopolymers of ammonium acrylate or copolymers of ammonium acrylate and acrylamide.

As examples of homopolymers of ammonium acrylate, mention may be made of the product sold under the name MICROSAP PAS 5193 by the company HOECHST. Among the copolymers of ammonium acrylate and acrylamide, mention may be made of the product sold under the name BOZEPOL C NEW or the PAS 5193 product sold by HOECHST. In particular, documents FR 2 416 723, US 2798053 and US 2923692 may be referred to for the description and preparation of such compounds.

The composition may also comprise homopolymers of dimethylaminoethyl methacrylate quaternized with methyl chloride or copolymers of dimethylaminoethyl methacrylate quaternized with methyl chloride and acrylamide. Among the homopolymers of this type, mention may be made of the products sold under the names SALCARE SC95 and SALCARE SC96 by the company CIBA. Among the copolymers of this family, mention may be made of the product SALCARE SC92 sold by CIBA or the product PAS 5194 sold by HOECHST. These polymers are in particular described and prepared in EP 395282 to which reference may be made.

Among the thickening agents, it is also possible to use thickening systems based on associative polymers well known to those skilled in the art and in particular of nonionic, anionic, cationic or amphoteric nature. It is recalled that the associative polymers are hydrophilic polymers capable, in an aqueous medium, to associate reversibly with each other or with other molecules.

Their chemical structure more particularly comprises at least one hydrophilic zone and at least one hydrophobic zone. Hydrophobic group is understood to mean a radical or polymer with a saturated or unsaturated, linear or branched hydrocarbon-based chain, comprising at least 10 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms, and more preferably from 18 to 30 carbon atoms. Preferably, the hydrocarbon group comes from a monofunctional compound. By way of example, the hydrophobic group may be derived from a fatty alcohol such as stearyl alcohol, dodecyl alcohol or decyl alcohol. It can also denote a hydrocarbon polymer such as for example polybutadiene. Among the associative polymers which do not comprise sugar units of anionic type, mention may be made of:

(I) those comprising at least one hydrophilic unit, and at least one fatty-chain allyl ether unit, more particularly those whose hydrophilic unit is constituted by an ethylenic unsaturated anionic monomer, more particularly by a vinyl carboxylic acid and especially with an acrylic acid or a methacrylic acid or mixtures thereof, and whose fatty-chain allyl ether unit corresponds to the following monomer of formula (II): CH ₂ = CR ¹ CH ₂ OB _n R

in which R 'denotes H or CH ₃ , B denotes the ethyleneoxy radical, n is nil or denotes an integer ranging from 1 to 100, R denotes a hydrocarbon radical chosen from alkyl, arylalkyl, aryl, alkylaryl and cycloalkyl radicals, comprising 8 to 30 carbon atoms, preferably 10 to 24, and more particularly 12 to 18 carbon atoms. A more particularly preferred unit of formula (II) is a unit in which R 'denotes H, n is equal to 10, and R denotes a stearyl (Ci ₈ ) radical.

Anionic associative polymers of this type are described and prepared according to an emulsion polymerization process in EP-0,216,479.

Among these anionic associative polymers, polymers formed from 20 to 60% by weight of acrylic acid and / or methacrylic acid, from 5 to 60% by weight of (meth) acrylates, are particularly preferred according to the invention. from lower alkyls, from 2 to 50% by weight of fatty-chain allyl ether of formula (II), and from 0 to 1% by weight of a crosslinking agent which is a well-known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate, and methylenebisacrylamide. Among these, the crosslinked terpolymers of methacrylic acid, ethyl acrylate, polyethylene glycol (10 EO) stearyl alcohol ether (Steareth 10), especially those sold by the company CIBA under the trade names SALCARE, are particularly preferred. SC80® and SALCARE SC90® which are 30% aqueous emulsions of a crosslinked terpolymer of methacrylic acid, ethyl acrylate and steareth-10-allyl ether (40/50/10).

(M) those comprising at least one hydrophilic unit of unsaturated olefinic carboxylic acid type, and at least one hydrophobic unit of the (C 10 -C 30) alkyl ester of unsaturated carboxylic acid type. Preferably, these polymers are chosen from those whose hydrophilic unit of unsaturated olefinic carboxylic acid type corresponds to the following monomer of formula (III):

in which, R 1 denotes H or CH ₃ or C ₂ H ₅ , that is to say units of acrylic acid, methacrylic acid or ethacrylic acid, and whose hydrophobic unit of alkyl ester type (CiO-C ₃₀ ) unsaturated carboxylic acid corresponds to the following monomer of formula (IV):

in which, R ₂ denotes H or CH ₃ or C ₂ H ₅ (iv), ie acrylate, methacrylate or ethacrylate units and preferably acrylate dentifants) or CH ₃ (methacrylate units), R ₃ denoting an alkyl radical, C ₁ -C ₃₀ , and preferably C ₂ -C ₂₂ .

Alkyl (C ₁₀ -C ₃₀ ) esters of unsaturated carboxylic acids according to the invention include, for example, lauryl acrylate, stearyl acrylate, decyl acrylate, isodecyl acrylate and the like. , dodecyl acrylate, and corresponding methacrylates, lauryl methacrylate, stearyl methacrylate, decyl methacrylate, isodecyl methacrylate, and dodecyl methacrylate.

Anionic polymers of this type are, for example, described and prepared according to US Pat. Nos. 3,915,921 and 4,509,949. Among this type of anionic associative polymers, polymers formed from a monomer mixture comprising : essentially acrylic acid, an ester of formula (IV) described above and in which R ₂ denotes H or CH ₃ , R ₃ denoting an alkyl radical having from 12 to 22 carbon atoms, and

(iii) a crosslinking agent, which is a well-known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate, and methylenebisacrylamide . Among this type of anionic associative polymers, use will more particularly be those consisting of 95 to 60% by weight of acrylic acid (hydrophilic unit), 4 to 40% by weight of C ₁₀ -C ₃₀ alkyl acrylate (unit hydrophobic) and 0 to 6% by weight of crosslinkable polymerizable monomer, or those consisting of 98 to 96% by weight of acrylic acid (hydrophilic unit), 1 to 4% by weight of C ₁₀ -C ₃₀ alkyl acrylate (Hydrophobic unit), and 0.1 to 0.6% by weight of crosslinking polymerizable monomer such as those described above. Among said polymers above, the products sold by the company Goodrich under the trade names Pemulen TR1®, Pemulen TR2® and Carbopol 1382®, and even more preferentially Pemulen TR1®, are particularly preferred according to the present invention. product sold by the company SEPPIC under the name COATEX SX®. Mention may also be made of polymers which, in addition to the monomers of formula

(III) and formula (IV) contain one or more other monomers. This additional monomer can be in particular a vinyllactam and in particular vinylpyrrolidone.

As an example of a polymer, mention may be made of the acrylic acid / lauryl methacrylate / vinylpyrrolidone terpolymer sold under the name Acrylidone LM by the company ISP.

(III) the terpolymers of maleic anhydride / α-olefin C ₃₀ -C ₃₈ / alkyl maleate such as the product (maleic anhydride copolymer / α-olefin C ₃₀ -C ₃₈ / isopropyl maleate) sold under the name PERFORMA V 1608® by the company NEWPHASE TECHNOLOGIES.

- (IV) acrylic terpolymers comprising:

(a) about 20% to 70% by weight of an α, β-monoethylenically unsaturated carboxylic acid,

(b) about 20 to 80% by weight of a non-surfactant α, β-monoethylenic unsaturation monomer other than (a),

(c) about 0.5 to 60% by weight of a nonionic mono-urethane which is the reaction product of a monohydric surfactant with a monoethylenically unsaturated monoisocyanate, such as those described in the patent application EP-A-0173109 and more particularly that described in Example 3, namely, a methacrylic acid / methyl acrylate / dimethyl metaisopropenyl benzyl isocyanate terpolymer of ethoxylated behenyl alcohol (40OE) in a 25% aqueous dispersion.

(V) copolymers comprising among their monomers an α, β-monoethylenically unsaturated carboxylic acid and an α, β-monoethylenically unsaturated carboxylic acid ester and an oxyalkylenated fatty alcohol. Preferably, these compounds also comprise, as monomer, an ester of carboxylic acid with α, β-monoethylenic unsaturation and of alcohol in dC ₄ . By way of example of this type of compound, mention may be made of Aculyn 22® sold by the company Rohm and Haas, which is a methacrylic acid / ethyl acrylate / stearyl methacrylate oxyalkylenated terpolymer.

Among the associative polymers which do not comprise sugar units of cationic type, mention may be made of:

- (I) the cationic associative polyurethanes whose family has been described by the Applicant in the French patent application No. 0009609; it can be represented by the following general formula (V):

RX- (P) n- [L- (Y) m] r-L '- (P') pX ¹ -R ¹ (V)

in which :

R and R ', which may be identical or different, represent a hydrophobic group or a hydrogen atom;

X and X ', which are identical or different, represent a group comprising an amino function bearing or not a hydrophobic group, or else the group L ";

L, L 'and L ", identical or different, represent a group derived from a diisocyanate;

P and P ', which may be identical or different, represent a group comprising an amino function bearing or not a hydrophobic group; Y represents a hydrophilic group; r is an integer from 1 to 100, preferably from 1 to 50 and in particular from 1 to 25, n, m, and p are each independently from 0 to 1000; the molecule containing at least one protonated or quaternized amino function and at least one hydrophobic group.

In a preferred embodiment of these polyurethanes, the only hydrophobic groups are the R and R 'groups at the chain ends.

A preferred family of cationic associative polyurethanes is that corresponding to the formula (V) described above and wherein:

R and R 'both independently represent a hydrophobic group, X, X' each represent a group L ", n and p are between 1 and 1000 and

L, L ', L ", P, P', Y and m have the meaning indicated above Another preferred family of cationic associative polyurethanes is that corresponding to formula (V) above in which: R and R 'are each independently a hydrophobic group, X, X' are each L ", n and p are 0, and L, L ', L", Y and m are as defined above.

The fact that n and p are 0 means that these polymers do not comprise units derived from an amine-functional monomer incorporated in the polymer during the polycondensation. The protonated amine functions of these polyurethanes result from the hydrolysis of isocyanate functional groups, in excess, at the end of the chain, followed by the alkylation of the primary amine functions formed by hydrophobic group alkylation agents, i.e. to say compounds of the type RQ or R ¹ Q, in which R and R 'are as defined above and Q denotes a leaving group such as a halide, a sulphate, etc.

Yet another preferred family of cationic associative polyurethanes is that corresponding to formula (V) above wherein:

R and R 'both independently represent a hydrophobic group,

X and X 'each independently represent a group having a quaternary amine, n and p are zero, and

L, L ', Y and m have the meaning indicated above. The number-average molecular weight of the cationic associative polyurethanes is preferably between 400 and 500,000, in particular between 1,000 and 400,000 and ideally between 1,000 and 300,000.

Hydrophobic group is understood to mean a radical or polymer with a hydrocarbon chain, saturated or unsaturated, linear or branched, which may contain one or more heteroatoms such as P, O, N, S, or a perfluorinated or silicone chain radical. When it refers to a hydrocarbon radical, the hydrophobic group comprises at least 10 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms and more preferably from 18 to 30 carbon atoms. Preferably, the hydrocarbon group comes from a monofunctional compound.

By way of example, the hydrophobic group may be derived from a fatty alcohol such as stearyl alcohol, dodecyl alcohol or decyl alcohol. It can also denote a hydrocarbon polymer such as for example polybutadiene.

When X and / or X 'denote a group comprising a tertiary or quaternary amine, X and / or X' may represent one of the following formulas: for X

_ _R2 _ _γ _ -R _{2 for χ (}

in which :

R ₂ represents an alkylene radical having 1 to 20 carbon atoms, linear or branched, with or without a saturated or unsaturated ring, or an arylene radical, one or more of the carbon atoms may be replaced by a heteroatom chosen from N, S, O, P;

R 1 and R ₃ , which may be identical or different, denote a linear or branched C 1 -C ₃₀ alkyl or alkenyl radical, an aryl radical, at least one of the carbon atoms may be replaced by a heteroatom chosen from N, S, O, P; A ^" is a physiologically acceptable counterion.

The groups L, L 'and L "represent a group of formula:

- ZC-NH-R ₄ -NH-CZ-II ⁴ II

Wherein Z is -O-, -S-, or -NH-; and

R ₄ represents an alkylene radical having 1 to 20 carbon atoms, linear or branched, with or without a saturated or unsaturated ring, an arylene radical, one or more of the carbon atoms may be replaced by a heteroatom selected from N, S , O and P. The groups P and P 'comprising an amino function may represent at least one of the following formulas:

I ⁸

-R ₅ -NR ₇ - or - R ₅ -NR ₇ -

⁵ I ^{7 3} I + '

R ₆ R ₆ A

^R 6s, ^R 8

N or - R ₅ -CH-R ₇ - or - R ₅ -CH-R ₇ -

R ₆ -NR ₉ A

R ₈

in which :

R ₅ and R ₇ have the same meanings as R ₂ defined above; R ₆ , Rs and R ₉ have the same meanings as R 1 and R ₃ defined above;

Rio represents an alkylene group, linear or branched, optionally unsaturated and may contain one or more heteroatoms selected from N, O, S and P, and A ^" is a physiologically acceptable counterion.

As regards the meaning of Y, the term "hydrophilic group" means a water-soluble polymeric group or not.

By way of example, non-polymers include ethylene glycol, diethylene glycol and propylene glycol. When it comes, according to a preferred embodiment, a hydrophilic polymer, there may be mentioned by way of example polyethers, sulfonated polyesters, sulfonated polyamides, or a mixture of these polymers. Preferably, the hydrophilic compound is a polyether and especially a poly (ethylene oxide) or poly (propylene oxide). The cationic associative polyurethanes of formula (V) that can be used according to the invention are formed from diisocyanates and from various compounds having functions with a labile hydrogen. The functions with a labile hydrogen may be alcohol, primary or secondary amine or thiol functions giving, after reaction with the diisocyanate functions, respectively polyurethanes, polyureas and polythioureas. The term "polyurethanes" usable according to the present invention encompasses these three types of polymers with namely polyurethanes themselves, polyureas and polythioureas as well as copolymers thereof.

A first type of compound used in the preparation of the polyurethane of formula (V) is a compound comprising at least one amino-functional unit. This compound can be multifunctional, but preferentially the compound is difunctional, that is to say that according to a preferred embodiment, this compound comprises two labile hydrogen atoms carried for example by a hydroxyl function, primary amine, secondary amine or thiol.

It is also possible to use a mixture of multifunctional and difunctional compounds in which the percentage of multifunctional compounds is low.

As indicated above, this compound may comprise more than one amino function unit. It is then a polymer carrying a repetition of the amino-functional unit. This type of compound can be represented by one of the following formulas:

Wherein Z, P, P ', n and p are as defined above.

As an example of an amino-functional compound, mention may be made of N-methyldiethanolamine, N-tert-butyl diethanolamine and N-sulfoethyldiethanolamine.

The second compound used in the preparation of the polyurethane of formula (V) is a diisocyanate corresponding to the formula:

O = C = NR ₄ -N = C = O in which R ₄ is defined above.

By way of example, mention may be made of methylenediphenyl diisocyanate, methylenecyclohexane diisocyanate, isophorone diisocyanate, toluene diisocyanate, naphthalene diisocyanate, butane diisocyanate and hexane diisocyanate. A third compound used in the preparation of the polyurethane of formula (V) is a hydrophobic compound intended to form the terminal hydrophobic groups of the polymer of formula (V).

This compound consists of a hydrophobic group and a function with a labile hydrogen, for example a hydroxyl, primary or secondary amine, or thiol function. By way of example, this compound may be a fatty alcohol, such as in particular stearyl alcohol, dodecyl alcohol or decyl alcohol. When this compound comprises a polymeric chain, it may be, for example, hydrogenated polybutadiene alpha-hydroxyl. The hydrophobic group of the polyurethane of formula (V) can also result from the quaternization reaction of the tertiary amine of the compound having at least one tertiary amine unit. Thus, the hydrophobic group is introduced by the quaternizing agent. This quaternizing agent is a compound of the type RQ or R ¹ Q, in which R and R 'are as defined above and Q denotes a leaving group such as a halide, a sulphate, etc.

The cationic associative polyurethane may further comprise a hydrophilic block. This sequence is provided by a fourth type of compound used in the preparation of the polymer. This compound can be multifunctional. It is preferably difunctional. One can also have a mixture where the percentage of multifunctional compound is low.

The functions with a labile hydrogen are alcohol, primary or secondary amine or thiol functions. This compound may be a polymer terminated at the chain ends by one of these functions with labile hydrogen.

By way of example, non-polymers include ethylene glycol, diethylene glycol and propylene glycol.

When it is a hydrophilic polymer, mention may be made by way of example of polyethers, sulphonated polyesters, sulphonated polyamides, or a mixture of these polymers. Preferably, the hydrophilic compound is a polyether and especially a poly (ethylene oxide) or poly (propylene oxide). The hydrophilic group Y in formula (V) is optional. Indeed, the quaternary or protonated amine functional units may be sufficient to provide the solubility or hydrodispersibility necessary for this type of polymer in an aqueous solution.

Although the presence of a hydrophilic Y group is optional, cationic associative polyurethanes having such a group are preferred.

(III) the cationic polymer (s) obtained by polymerization of a monomer mixture comprising one or more vinyl monomers substituted with one or more amino groups, one or more hydrophobic nonionic vinyl monomers, and one or more associative vinyl monomers.

In particular, among these cationic polymers, mention may be made in particular of the compound marketed by NOVEON under the name AQUA CC and which corresponds to the name INCI POLYACRYLATE-1 CROSSPOLYMER. POLYACRYLATE-1 CROSSPOLYMER is the product of the polymerization of a monomer mixture comprising:

a di (C ₁ -C ₄ alkyl) amino methacrylate (C ₁ -C ₆ alkyl),

- one or more alkyl esters of C1-C30 and (meth) acrylic acid, - an alkyl methacrylate -C ₀ -C ₃₀ polyethoxylate (20-25 moles ethylene oxide unit),

an allyl ether of polyethylene glycol / polypropylene glycol 30/5,

- a hydroxy methacrylate (C ₂ -C _6), and

an ethylene glycol dimethacrylate.

The amphoteric associative polymers not comprising sugar units are preferably chosen from those comprising at least one non-cyclic cationic unit. Even more particularly, those prepared from or comprising 1 to 20 mole% of monomer having a fatty chain, and preferably 1.5 to 15 mole% and more particularly 1.5 to 6 mole%, based on the number, are preferred. total moles of monomers.

The preferred amphoteric associative polymers according to the invention comprise, or are prepared by copolymerizing at least one monomer of formula (VI) or (VII):

^A R

R -CH = C- -c- -Z- (C _n H _2n ) -N-R ₅ (VI)

R ₂ O

F

\

in which, R 1 and R ₂ , which may be identical or different, represent a hydrogen atom or a methyl radical, R ₃ , R ₄ and R ₅ , which may be identical or different, represents a linear or branched alkyl radical having from 1 to 30 carbon atoms, carbon,

Z represents an NH group or an oxygen atom, n is an integer of 2 to 5,

A ^" is an anion derived from an organic or inorganic acid, such as a methosulphate anion or a halide such as chloride or bromide;

2) at least one monomer of formula (VIII) R ₆ - CH = C-COOXR ₈ (IX)

R ₇ in which, R ₆ and R ₇ , identical or different, represent a hydrogen atom or a methyl radical; and

3) at least one monomer of formula (IX):

(IX)

R ₆ -CH = C _o (IX)

R ₇

in which R ₆ and R ₇ , which are identical or different, represent a hydrogen atom or a methyl radical, X denotes an oxygen or nitrogen atom and R ₈ denotes a linear or branched alkyl radical having from 1 to 30 atoms of carbon ; at least one of the monomers of formula (VI), (VII) or (VIII) comprising at least one fatty chain.

The monomers of formula (VI) and (VII) of the present invention are preferably chosen from the group consisting of:

dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl methacrylate, diethylaminoethyl acrylate,

dimethylaminopropyl methacrylate, dimethylaminopropyl acrylate,

dimethylaminopropyl methacrylamide, dimethylaminopropyl acrylamide, these monomers being optionally quaternized, for example by a dC ₄ alkyl halide or a dC ₄ dialkyl sulphate.

More particularly, the monomer of formula (VI) is chosen from acrylamidopropyltrimethylammonium chloride and methacrylamidopropyltrimethylammonium chloride.

The monomers of formula (VIII) of the present invention are preferably selected from the group consisting of acrylic acid, methacrylic acid, crotonic acid and 2-methylcrotonic acid. More particularly, the monomer of formula (VIII) is acrylic acid.

The monomers of formula (IX) of the present invention are selected preferably from the group consisting of alkyl acrylates or methacrylates C12-C22 and more particularly -C ₆ -C _8.

The monomers constituting the amphoteric fatty-chain polymers of the invention are preferably already neutralized and / or quaternized. The ratio of the number of cationic charges / anionic charges is preferably equal to about 1.

The amphoteric associative polymers according to the invention preferably comprise from 1 to 10 mol% of the monomer comprising a fatty chain (monomer of formula (VI), (VII) or (IX), and preferably from 1.5 to 6 mol% .

The weight average molecular weight of the amphoteric associative polymers according to the invention can vary from 500 to 50,000,000 and are preferably between 10,000 and 5,000,000.

The amphoteric associative polymers according to the invention may also contain other monomers such as nonionic monomers and in particular such as alkyl acrylates or methacrylates in dC ₄ .

Amphoteric associative polymers according to the invention are for example described and prepared in the patent application WO9844012.

Among the amphoteric associative polymers according to the invention, acrylic acid / (meth) acrylamidopropyltrimethylammonium chloride / stearyl methacrylate terpolymers are preferred.

The associative polymers which do not comprise sugar units of nonionic type which can be used according to the invention are preferably chosen from: (a) copolymers of vinylpyrrolidone and of hydrophobic fatty-chain monomers, which may be exemplified by:

products ANTARON V216® or GANEX V216® (vinylpyrrolidone / hexadecene copolymer) sold by I. S. P.

products ANTARON V220® or GANEX V220® (vinylpyrrolidone / eicosene copolymer) sold by I. S. P.

(b) copolymers of methacrylates or of alkyl acrylates in dC ₆ and of amphiphilic monomers comprising at least one fatty chain such as for example the methyl acrylate / stearyl acrylate oxyethylenated copolymer sold by GOLDSCHMIDT under the name ANTIL 208®. (c) copolymers of hydrophilic methacrylates or acrylates and of hydrophobic monomers comprising at least one fatty chain, such as, for example, polyethylene glycol methacrylate / lauryl methacrylate copolymer.

(d) polyether polyurethanes comprising in their chain, both hydrophilic sequences of mostly polyoxyethylenated nature and hydrophobic sequences which may be aliphatic sequences alone and / or cycloaliphatic and / or aromatic sequences.

(e) polymers having an aminoplast ether skeleton having at least one fatty chain, such as the compounds PURE TH IX® proposed by the company SUD-CHEMIE. Preferably, the polyether polyurethanes comprise at least two hydrocarbon-based lipophilic chains having from 6 to 30 carbon atoms, separated by a hydrophilic sequence, the hydrocarbon chains possibly being pendant chains or chains at the end of the hydrophilic sequence. In particular, it is possible that one or more pendant chains are provided. In addition, the polymer may comprise a hydrocarbon chain at one end or at both ends of a hydrophilic block.

The polyether polyurethanes may be multiblocked, in particular in the form of a triblock. The hydrophobic sequences may be at each end of the chain (for example: hydrophilic central block triblock copolymer) or distributed at both the ends and in the chain (multiblock copolymer for example). These same polymers may also be graft or star.

The nonionic polyurethane polyethers with a fatty chain may be triblock copolymers whose hydrophilic sequence is a polyoxyethylenated chain containing from 50 to 1000 oxyethylenated groups. Nonionic polyurethane polyethers have a urethane bond between the hydrophilic blocks, hence the origin of the name.

By extension are also included among the nonionic polyurethane fatty chain polyethers those whose hydrophilic sequences are linked to the lipophilic blocks by other chemical bonds.

As examples of fatty-chain nonionic polyurethane polyethers that may be used in the invention, it is also possible to use also the urea-functional Rheolate 205® sold by Rheox or the Rheolates® 208, 204 or 212, as well as Acrysol RM 184®.

One can also cite the product Elfacos T210® C12-14 alkyl chain and the product Elfacos T212® containing alkyl chain ₈ from Akzo.

The product DW 1206B® from ROHM & HAAS with a C ₂₀ alkyl chain and a urethane linkage, proposed at 20% solids content in water, can also be used.

It is also possible to use solutions or dispersions of these polymers, especially in water or in an aqueous-alcoholic medium. By way of example, such polymers include RHEOLATE® 255, RHEOLATE® 278 and

RHEOLATE® 244 sold by RHEOX. It is also possible to use the product DW 1206F and the DW 1206J proposed by the company Rohm & Haas.

The polyether polyurethanes that can be used according to the invention are in particular those described in the article by G. Fonnum, J. Bakke and Fk. Hansen - Colloid Polym. Sci 271, 380, 389 (1993).

More particularly still it is preferred to use a polyether polyurethane obtainable by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to

180 moles of ethylene oxide, (ii) stearyl alcohol or decyl alcohol and (iii) at least one diisocyanate.

Such polyether polyurethanes are sold in particular by the company ROHM & HAAS under the names ACULYN 46® and ACULYN 44® [ACULYN

46® is a polyethylene glycol polycondensate containing 150 or 180 moles of ethylene oxide, stearyl alcohol and methylene bis (4-cyclohexyl isocyanate)

(SMDI), 15% by weight in a matrix of maltodextrin (4%) and water (81%); ACULYN 44® is a polycondensate of polyethylene glycol with 150 or 180 moles of ethylene oxide, decyl alcohol and methylenebis (4-cyclohexylisocyanate) (SMDI), at 35% by weight in a propylene glycol mixture ( 39%) and water (26%)].

Preferably, the thickening polymers not comprising sugar units according to the invention are chosen from associative polymers. Among the associative polymers, the compounds of family (II) are preferred and particularly the terpolymers acrylic acid / lauryl methacrylate / vinylpyrrolidone.

The thickening polymers comprising one or more sugar units may be ionic or non-ionic polymers, associative or otherwise.

The sugar units that can be used in the composition of the thickening polymers of the invention are preferably derived from the following sugars:

.glucose

.galactose .arabinose

.rhamnose

.mannose

.xylose

.fucose .anhydrogalactose

galacturonic acid

glucuronic acid

mannuronic acid

.galactose sulfate .anhydrogalactose sulfate In particular, thickening polymers of the invention may be mentioned:

-natural gums such as: a) exudates from trees or shrubs including: .gum arabic ((branched polymer of galactose, arabinose, rhamnose and glucuronic acid)

ghatti gum (polymer derived from arabinose, galactose, mannose, xylose and glucuronic acid)

karaya gum (polymer derived from galacturonic acid, galactose, rhamnose and glucuronic acid)

tragacanth gum (or tragacanth) (galacturonic acid, galactose, fucose, xylose and arabinose polymer) b) gums derived from algae including:

agar (polymer derived from galactose and anhydrogalactose). alginates (polymers of mannuronic acid and glucuronic acid)

carrageenans and furcellerans (polymers of galactose sulphate and anhydrogalactose sulphate); c) gums derived from seeds or tubers of which:

Guar gum (mannose and galactose polymer) Locust bean gum (mannose and galactose polymer)

Fenugreek gum (polymer of mannose and galactose)

-tamarin gum (galactose, xylose and glucose polymer)

konjac gum (glucose polymer and mannose) d) microbial gums including: xanthan gum (glucose polymer, mannose acetate, mannose / pyruvic acid and glucuronic acid)

gellan gum (partially acylated glucose polymer, rhamnose and glucuronic acid)

scleroglucan gum (glucose polymer) e) plant extracts including:

. cellulose (glucose polymer)

starch (glucose polymer)

These polymers can be modified physically or chemically. As a physical treatment, mention may in particular be made of temperature.

By way of chemical treatments, mention may be made of esterification, etherification, amidation and oxidation reactions. These treatments lead to polymers that can be nonionic, anionic, cationic or amphoteric. Preferably, these chemical or physical treatments are applied to the guar gums, locust bean gum, starch and celluloses.

The nonionic guar gums which may be used according to the invention may be modified with hydroxylalkyl groups of C ₁ -C ₆ .

Among the hydroxyalkyl groups, there may be mentioned by way of example, the hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.

These guar gums are well known in the state of the art and may for example be prepared by reacting corresponding alkene oxides such as, for example, propylene oxides with guar gum so as to obtain a guar gum. modified by hydroxypropyl groups.

The level of hydroxyalkylation preferably ranges from 0.4 to 1.2 and corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functions present on the guar gum.

Such nonionic guar gums optionally modified with hydroxyalkyl groups are for example sold under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120 by Rhodia Chimie.

The guar gums modified with cationic groups that are more particularly usable according to the invention are guar gums comprising cationic thalkylammonium groups. Preferably, 2 to 30% by number of the hydroxyl functions of these guar gums carry thalkyammonium cationic groups. Even more preferably, 5 to 20% of the number of hydroxyl functions of these guar gums is connected by cationic thalkyammonium groups.

Among these thalkylammonium groups, trimethylammonium and methylammonium groups may be mentioned in particular.

Even more preferentially, these groups represent from 5 to 20% by weight relative to the total weight of the modified guar gum.

According to the invention, it is possible to use guar gums modified with 2,3-epoxypropyltrimethylammonium chloride. These guar gums modified with cationic groups are products already known in themselves and are described, for example, in US Pat. Nos. 3,589,578 and 4,013,307. Such products are also sold in particular under the trade names of Jaguar. C13 S, JAGUAR C 15, JAGUAR C 17 by RHODIA CHEMISTRY.

As modified carob gum can be used cationic locust bean gum containing hydroxypropylthmmonium groups such as Catinal CLB 200 proposed by the company TOHO.

The starch molecules used in the present invention may have as botanical origin cereals or tubers. Thus, the starches are, for example, chosen from starches of maize, rice, cassava, barley, potato, wheat, sorghum and peas.

The starches can be modified chemically or physically: in particular by one or more of the following reactions: pregelatinization, oxidation, crosslinking, esterification, etherification, amidification, heat treatments.

More particularly, these reactions can be carried out as follows:

- pregelatinization by bursting the starch granules (for example drying and cooking in a drying drum);

oxidation by strong oxidants leading to the introduction of carboxyl groups into the starch molecule and to the depolymerization of the starch molecule (for example by treating an aqueous starch solution with sodium hypochlorite);

crosslinking with functional agents capable of reacting with the hydroxyl groups of the starch molecules which will thus be bonded together (for example with glyceryl and / or phosphate groups);

alkaline esterification for the grafting of functional groups, in particular C 1 -C 6 acyl (acetyl), C 1 -C 6 hydroxyalkyl (hydroxyethyl, hydroxypropyl), carboxymethyl and octenyl succinic groups.

In particular, it is possible to obtain, by means of crosslinking with phophorated compounds, mono-starch phosphates (of the Am-O-PO- (OX) 2 type), diamidon phosphates (of the Am-O-PO- (OX) -O-Am type). or even triamidon (of the type Am-O- PO- (O-Am) 2) or their mixtures (Am signifying starch). X denotes in particular alkali metals (for example sodium or potassium), alkaline earth metals (for example calcium, magnesium), ammonium salts, amine salts such as those of monoethanolamine, diethanolamine, triethanolamine, amino-3-propanediol-1,2, ammonium salts derived from basic amino acids such as lysine, arginine, sarcosine, ornithine, citrulline.

The phosphorus compounds may be, for example, sodium tripolyphosphate, sodium orthophosphate, phosphorus oxychloride or sodium trimetaphosphate.

Diamidon phosphates or diamidon phosphate-rich compounds such as the product proposed under the references PREJEL VA-70-T AGGL (hydroxypropylated gelatinized hydroxypropyl diamidon phosphate) or PREJEL TK1 (gelatinized manioc diamidon phosphate) are preferably used. PREJEL 200 (gelatinized acetylated manioc diamidon phosphate) by the company AVEBE or STRUCTURE ZEA by NATIONAL STARCH (gelatinized cornstarch).

A preferred starch is a starch which has undergone at least one chemical modification such as at least one esterification.

According to the invention, it is also possible to use amphoteric starches, these amphoteric starches comprise one or more anionic groups and one or more cationic groups. The anionic and cationic groups may be bonded to the same reactive site of the starch molecule or to different reactive sites; preferably they are linked to the same reactive site. The anionic groups may be of carboxylic, phosphate or sulfate type and preferably carboxylic. The cationic groups may be of primary, secondary, tertiary or quaternary amine type.

The amphoteric starches are in particular chosen from compounds of the following formulas:

R 'R

CH-CH-COOM

St-O - (CH ₂ ) -N

CH-CH-COOM

R 'R _(M) COOM R

CH CH -COOM

St-O - (CH ₂ ) -N _,

R 's / R "

N St-O-CH ₂ CH-COOM, | _V)

R 's / R "

N St-O-CH - CH ₂ -COOM, y, formulas in which:

St-O represents a starch molecule,

R, identical or different, represents a hydrogen atom or a methyl radical, R ', which is identical or different, represents a hydrogen atom, a methyl radical or a -COOH group, n is an integer equal to 2 or 3,

M, identical or different, denotes a hydrogen atom, an alkali or alkaline earth metal such as Na, K, Li, NH _4, a quaternary ammonium or an organic amine,

R "represents a hydrogen atom or an alkyl radical having 1 to 18 carbon atoms.

These compounds are described in particular in US Pat. Nos. 5,455,340 and 4,017,460, which are incorporated by reference.

The starch molecules can be derived from all plant sources of starch, such as in particular corn, potato, oats, rice, tapioca, sorghum, barley or wheat. It is also possible to use the hydrolysates of the starches mentioned above. The starch is preferably from the potato.

Starches of formula (II) or (III) are especially used. 2-chloroethylaminodipropionic acid-modified starches, that is to say the starches of formula (II) or (III) in which R, R ', R "and M represent a hydrogen atom, are more particularly used. and n is 2. The preferred amphoteric starch is a starch chloroethylamidodipropionate. As indicated above, the cellulose derivatives may be anionic, cationic, amphoteric or nonionic.

Among these derivatives, there are cellulose ethers, cellulose esters and cellulose ether esters. Among the cellulose esters, there are inorganic esters of cellulose (cellulose nitrates, sulphates or phosphates, etc.), cellulose organic esters (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates or acetatetrimellitates, etc.). and mixed organic / inorganic cellulose esters such as cellulose acetate and acetate sulphates and cellulose acetate propionates. Among the cellulose ether esters, mention may be made of hydroxypropyl methylcellulose phthalates and ethylcellulose sulphates.

Among the nonionic cellulose ethers, mention may be made of alkylcelluloses such as methylcelluloses and ethylcelluloses (for example Ethocel Standard 100 Premium from DOW CHEMICAL); hydroxyalkylcelluloses such as hydroxymethylcelluloses, hydroxyethylcelluloses (for example Natrosol 250 HHR proposed by AQUALON) and hydroxypropylcelluloses (for example Klucel EF from AQUALON); mixed hydroxyalkyl-alkylcellulose celluloses such as hydroxypropyl-methylcelluloses (for example Methocel E4M from Dow Chemical), hydroxyethyl-methylcelluloses, hydroxyethylethylcelluloses (for example Bermocoll E 481 FQ from Akzo Nobel) and hydroxybutyl-methylcelluloses.

Among the anionic cellulose ethers, mention may be made of carboxyalkylcelluloses and their salts. By way of example, mention may be made of carboxymethylcelluloses, carboxymethylmethylcelluloses (for example Blanose 7M from AQUALON) and carboxymethylhydroxyethylcelluloses and their sodium salts.

Among the cationic cellulose ethers, mention may be made of quaternized hydroxyethylcelluloses which may or may not be crosslinked. The quaternizing agent may especially be diallyldimethylammonium chloride (for example Celquat L200 from National Starch). As other cationic cellulose ether include hydroxyethylcellulose hydroxypropyltrimethylammonium (e.g., Ucare polymer JR 40O d ¹ Amerchol).

Among the associative thickening polymers of the invention, mention may be made of celluloses or their derivatives, modified with groups comprising at least one fatty chain, such as alkyls, arylalkyls, alkylaryls or mixtures thereof, where the alkyl groups are C ₈ - C ₂₂ ; nonionic alkylhydroxyethylcelluloses such as the products NATROSOL PLUS GRADE 330 CS and POLYSURF 67 (C _1-6 alkyl) sold by AQUALON;

quaternized (cationic) alkylhydroxyethylcelluloses such as the products QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-

18-B (alkyl ₂₎ and Quatrisoft LM-X 529-8 ₍₈ alkyl) sold by the company Amerchol, the products Crodacel QM, Crodacel QL (C12 alkyl) and Crodacel QS (alkyl ₈₎ sold by the company CRODA and the product SOFTCAT SL 100 sold by the company AMERCHOL. nonionic nonoxynylhydroxyethylcelluloses such as the AMERCELL product

HM-1500 sold by the company Amerchol;

nonionic alkylcelluloses such as the product BERMOCOLL EHM 100 sold by the company BEROL NOBEL;

As associative guar derivatives, it is possible to use hydroxypropyl guars modified with a fatty chain, such as the product ESAFLOR HM 22 (modified with a C22 alkyl chain) sold by the company LAMBERTI; the product MIRACARE XC 95-3 (modified with a C1 ₄ alkyl chain) and the product RE 205-146 (modified with a C ₂ 0 alkyl chain) sold by RHODIA CHIMIE;

The thickening polymer or polymers comprising one or more sugar units of the invention are preferably chosen from guar gums, starches and modified or unmodified celluloses.

The thickening polymer (s) is (are) present in the composition according to the invention in a content ranging from 0.01% to 10% by weight and preferably from 0.1% to 5% by weight relative to the total weight of the composition.

Preferably the weight ratio between the compound (s) of formula (I) and the thickening polymer (s) according to the invention is between 0.1 and 10 and even more preferably between 1 and 8.

The compositions according to the invention can be in any of the galenical forms conventionally used, and especially in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension or oily; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the O / W, W / O or multiple type; a suspension or emulsion of soft consistency of cream (O / W) or (W / O) type; an aqueous or anhydrous gel, or any other cosmetic form. These compositions may be packaged in pump bottles or in aerosol containers, in order to ensure application of the composition in vaporized form (lacquer) or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a mousse, for the treatment of hair. In these cases, the composition preferably comprises at least one propellant.

Preferably, the composition is in the form of an emulsion comprising the compound of formula (I) in dispersion in an aqueous phase or in solution in a fatty phase.

The compositions according to the invention comprise a cosmetically acceptable medium, that is to say a medium that is compatible with keratin materials, in particular the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and the nails. . The composition is preferably a cosmetic composition, in particular intended for application to keratin materials and in particular the hair.

The compositions according to the invention may also comprise at least one usual cosmetic ingredient, especially chosen from propellants; water, carbonaceous oils; silicone oils; ; esters fatty acids; C 1 -C 4 lower alcohols, fatty alcohols, ketones, other organic solvents, nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants, zwitterionic surfactants; solar filters; moisturizing agents; antidandruff agents; antioxidants; reducing agents; oxidation bases, couplers, oxidizing agents, direct dyes; hair straightening agents, pearlescent and opacifying agents; plasticizing or coalescing agents; hydroxy acids; pigments; the charges; silicone gums and resins; thickeners other than those of the invention, non-thickening polymers. The compositions may of course include several cosmetic ingredients listed above.

Depending on their nature and the destination of the composition, the usual cosmetic ingredients may be present in customary amounts, easily determinable by those skilled in the art, and which may be understood, for each ingredient, between 0.01 to 80% by weight .

By cosmetically acceptable medium is meant within the meaning of the present invention, a medium compatible with the hair. The cosmetically acceptable medium consists of water or a mixture of water and one or more cosmetically acceptable solvents schoisi from alcohols -C _4, such as in particular ethanol, isopropanol, tert-butanol or n-butanol; polyols such as glycerol, propylene glycol and polyethylene glycols, polyol ethers; and their mixtures.

The carbonaceous oils, in particular hydrocarbon oils, and / or the silicone oils may be present in a proportion of 0.01 to 20% by weight, especially 0.02 to 10% by weight relative to the total weight of the composition. Mention may be made of vegetable, animal or mineral oils, hydrogenated or not, linear or branched, saturated or unsaturated hydrocarbon, cyclic or aliphatic synthetic oils, such as, for example, polyalpha-olefins, in particular polydecenes and polyisobutenes; fluorinated or perfluorinated oils; their mixtures. Fatty alcohols, fatty esters and fatty acids may be present in a proportion of from 0.01 to 50% by weight, especially 0.1 to 20% by weight relative to the total weight of the composition.

Mention may especially be made of C12-C32 linear or branched chain fatty alcohols, in particular C12-C26, and in particular cetyl alcohol, stearyl alcohol, cetylstearyl alcohol, isostearyl alcohol, octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol.

Mention may also be made of C16-C40 linear or branched chain fatty acids, and in particular 18-methyl eicosanoic acid, coconut oil acids or hydrogenated coconut oil acids; stearic acid, lauric acid, palmitic acid and oleic acid, behenic acid, and mixtures thereof; Mention may also be made of linear or branched chain C 16 -C 40 fatty esters, such as esters of polyols derived from fatty acids containing from 8 to 30 carbon atoms, and their oxyalkylenated and especially oxyethylenated derivatives, the polyols being preferentially chosen. among the sugars, C2-C6-alkylene glycols, glycerol, polyglycerols, sorbitol, sorbitan, polyethylene glycols, polypropylene glycols and mixtures thereof.

The surfactants, nonionic, cationic, anionic, amphoteric or zwitterionic, other than those of formula (I), and mixtures thereof, may be present in a proportion of 0.01 to 50% by weight, in particular 0.05 to 40% by weight. by weight, or even 0.1 to 30% by weight, relative to the total weight of the composition. The propellants may be present in a proportion of 5 to 90% by weight relative to the total weight of the composition, and more particularly in a proportion of 10 to 60% by weight. The sunscreens may be present in a proportion of 0.01 to 20% by weight, especially 0.5 to 10% by weight relative to the total weight of the composition.

The moisturizing agents may be present in a proportion of 0.01 to 20% by weight, especially 0.1 to 7% by weight relative to the total weight of the composition. The anti-dandruff agents may be present in a proportion of 0.001 to 20% by weight, especially 0.01 to 10% by weight relative to the total weight of the composition, preferably 0.1 to 5% by weight.

The antioxidants may be present in a proportion of 0.05 to 1.5% by weight, relative to the total weight of the composition. The reducing agents may be present in a proportion of 0.1 to 30% by weight, especially 0.5 to 20% by weight relative to the total weight of the composition.

The oxidation bases may be present in an amount between

0.001 to 10% by weight, preferably from 0.005 to 6% by weight, of the total weight of the composition. The couplers can be present in an amount of between 0.001 and

10% by weight, preferably from 0.005 to 6% by weight, of the total weight of the composition.

The oxidizing agents may be present in an amount of between 1 and

40% by weight, preferably between 1 and 20% by weight, relative to the weight of the composition.

The direct dyes may be present in an amount of from 0.001 to 20% by weight, preferably from 0.01 to 10% by weight, relative to the total weight of the composition.

The relaxing agents may be present in a proportion of 0.01 to 3.5% by weight, especially 0.05 to 1.5% by weight relative to the total weight of the composition.

The pearlescent and opacifying agents may be present in a proportion of 0.01 to 3% by weight, especially 0.05 to 2.5% by weight relative to the total weight of the composition.

The plasticizing or coalescing agents may be present in a proportion of 0.1 to 25% by weight, especially 1 to 10% by weight relative to the total weight of the composition.

The hydroxy acids may be present in a proportion of 1 to 10% by weight, especially 2 to 5% by weight relative to the total weight of the composition.

The pigments and fillers may be present in a proportion of 0.01 to 50% by weight, especially 0.02 to 30% by weight relative to the total weight of the composition.

Silicones can be volatile or not; mention may be made especially polyorganosiloxanes, modified or not, namely oils, gums and resins of polyorganosiloxanes, as such or in the form of solutions in organic solvents, or in the form of emulsions or microemulsions. They may be present in an amount of 0.01 to 40% by weight, especially 0.05 to 20% by weight, relative to the total weight of the composition. The different thickeners of the thickening polymers of the invention may be present in a proportion of 0.01 to 10% by weight, especially 0.1 to 5% by weight relative to the total weight of the composition.

The polymers different from the thickening polymers, in particular water-soluble or soluble in carbonaceous and / or silicone oils, may be present in a proportion of from 0.01 to 20% by weight, especially 0.1 to 10% by weight relative to the total weight of the composition.

Those skilled in the art will take care to choose the ingredients in the composition, as well as their amounts, so that they do not adversely affect the properties of the compositions of the present invention.

The cosmetic composition according to the invention may be in the form of a product for the care, cleaning and / or make-up of the skin of the body or of the face, the lips, the eyebrows, the eyelashes, the nails, and the like. a suntan or self-tanning product, a personal hygiene product, a hair product, in particular care, cleaning, styling, shaping, hair dyeing.

It finds particularly a particularly interesting application in the hair field, especially for the care, the cosmetic treatment, the cleaning of the hair or for the maintenance of the hairstyle or the shaping of the hair.

The hair compositions may be shampoos, conditioners, styling or care gels, lotions or creams, conditioners, styling lotions, blow-dry lotions, fixing compositions and the like. styling such as lacquers or spray; restructuring lotion for hair; anti-hair loss lotion or gel, anti-parasitic shampoo, anti-dandruff lotion or shampoo, anti-seborrhoeic shampoo. The lotions may be packaged in various forms, in particular in vaporizers, pump-bottles or in aerosol containers to ensure application of the composition in vaporized form or in the form of foam.

The hair compositions are preferably conditioners to be rinsed.

It may also be in the form of a hair coloring product and especially oxidation dyeing or direct dyeing; in the form of a composition of perm, straightening or discoloration, or in the form of a composition to be rinsed, to be applied before or after a coloration, a discoloration, a permanent or a straightening or between the two stages of a permanent or a straightening.

The composition according to the invention may also be in the form of a care composition, especially moisturizing, for the skin of the body or face, lips and / or integuments, especially a skincare product for cosmetically treating the skin and in particular for moisturizing, smoothing, depigmenting, feed it, protect it from the sun's rays, or give it a specific cosmetic treatment. So it can be a base of care for the lips, a fixing base for lipstick, a composition of sunscreen or artificial tanning, a composition of care (day, night, anti-aging, moisturizing) for the face ; a mattifying composition; a skin cleansing composition, for example a makeup remover or a bath or shower gel, or a cleansing bar or bar; a personal hygiene composition including a deodorant product, antiperspirant, or a depilatory composition, a gel or aftershave lotion.

It can still be in the form of a makeup product for the skin of the body or the face, lips, eyelashes, nails or hair; especially a foundation, a blush, a blush, an anti-ring product, an eyeliner, a mascara, a lipstick, a lip gloss, a lip liner; nail polish, nail care; a temporary tattoo product of the body skin.

Even more particularly, the composition according to the invention finds an interesting application for the care and the cosmetic treatment, in particular the protection, of hair, in particular weakened and / or damaged hair, for example by chemical or mechanical treatments. The compositions according to the invention can also be used after the treatment, after a step of coloring, bleaching or straightening the hair.

The subject of the invention is therefore a process for the cosmetic treatment, in particular of makeup, care, cleaning, coloring, shaping, keratin materials, in particular of the skin of the body or of the face, lips, nails , hair and / or eyelashes, comprising the application on said materials of a cosmetic composition comprising one or more quaternary esters according to the invention and one or more thickening polymers according to the invention.

Preferably, it is a cosmetic treatment method for conditioning the hair, in particular to provide or improve its flexibility, disentangling, smoothing, hair. The application of the composition may optionally be followed by a rinsing step and / or optionally a heat treatment step.

The invention is illustrated in more detail in the following examples. Example 1 Synthesis of 2-r 2 - (dodecanoyloxy) ethoxyl-N, N, N-triethylethanaminium chloride

4 g (1 eq) of 2- [2- (diethylamino) ethoxy] ethyl laurate and 10 ml (10.8 eq) of ethyl iodide are mixed; it is mixed for 72 hours at 25 ° C.

Excess alkylating agent is then removed by washing with diisopropyl ether.

The solid obtained is then filtered under nitrogen, washed and dried under reduced pressure in the presence of P ₂ O ₅ . The iodide anion is exchanged by treating an aqueous solution of the compound with 50 g of ion exchange resin IRA 400.

After removing the solvent, washing the compound with diisopropyl ether, filtering and drying under reduced pressure in the presence of P ₂ O ₅ , 2.8 g of the desired product is obtained which is in the form of a beige powder (yield:

59%).

M (m Iz): M + = 372

Example 2 Synthesis of 2-r 2 - (decanoyloxy) ethoxyl-N, N, N-triethylethanaminium chloride

8 g (1 eq) of 2- [2- (diethylamino) ethoxy] ethyl decanoate and 6.6 ml (2 eq) of diethyl sulphate are mixed; is mixed for 7 hours under heating at 60 ⁰ C. The excess of alkylating agent is subsequently removed by washing with diisopropyl ether. The solid obtained is then filtered, under nitrogen, washed and dried under reduced pressure in the presence of P ₂ O ₅ . The anion is exchanged by treatment of an aqueous solution of the compound with 300 g of ion exchange resin IRA 402. After removal of the solvent, washing the compound with diisopropyl ether, filtration and drying under reduced pressure in the presence of P ₂ O ₅ , 5.6 g of the desired product is obtained in the form of a white powder (yield: 87%). M (m Iz): M + = 344

Example 3 Synthesis of N, N, N-triethyl-2-r 2 - (palmitoyloxy) ethoxyethanaminium chloride

7.7 g (1 eq) of 2- [2- (diethylamino) ethoxy] ethyl palmitate and 5.5 ml (2 eq) of diethyl sulphate are mixed; mixed for 15 hours while heating at 65-70 ^° C.

Excess alkylating agent is then removed by washing with diisopropyl ether.

The solid obtained is then filtered, under nitrogen, washed and dried under reduced pressure in the presence of P ₂ O ₅ . The iodide anion is exchanged by treating an aqueous solution of the compound with 300 g of IRA 402 ion exchange resin.

After removing the solvent, washing the compound with diisopropyl ether, filtration and drying under reduced pressure in the presence of P ₂ O ₅ , 7.15 g of the desired product is obtained in the form of a white powder (yield:

80%).

M (m Iz): M + = 428

Example 4 Synthesis of 2-r 2 - (docosanoyloxy) ethoxyl-N, N, N-triethylethanaminium chloride

5.8 g (1 eq) of 2- [2- (diethylamino) ethoxy] ethyl docosanoate and 3.15 ml (2 eq) of diethylsulfate are mixed; mixed for 15 hours by heating at 65-

70 ^° C.

Excess alkylating agent is then removed by washing with diisopropyl ether.

The solid obtained is then filtered, under nitrogen, washed and dried under reduced pressure in the presence of P ₂ O ₅ . The iodide anion is exchanged by treatment of the compound, dissolved in a solution of pure water / acetone (80/20) over 300 g of ion exchange resin IRA 402. The compound is eluted with a mixture of pure water / acetone (80 / 20).

After removing the solvent, washing the compound with diisopropyl ether, filtration and drying under reduced pressure in the presence of P ₂ O ₅ , 5.5 g of the desired product is obtained in the form of a white powder (yield:

84%).

M (m / z): M + = 512

Example 5 Synthesis of N, N-diethyl-N- (2-r 2 - (palmitoyloxy) ethoxyethyl) hexadecan-1-aminium bromide

5 g (1 eq) of 2- [2- (diethylamino) ethoxy] ethyl palmitate and 7.63 ml (2 eq) of bromohexane are mixed; It is mixed for 48 hours while heating at 120 ^° C. The excess of alkylating agent is then removed by washing with diisopropyl ether. The solid obtained is then filtered, under nitrogen, washed with diisopropyl ether and dried under reduced pressure in the presence of P ₂ O ₅ .

4 g of the desired product is obtained which is in the form of a beige powder (yield: 76%). M (m Iz): M + = 625

Example 6 Synthesis of the following compound:

MeOSO ₃ -

30 ml of diethyl sulphate (2 eq) are poured dropwise over 38.6 g of the corresponding tertiary amine. The reaction medium is stirred under an inert atmosphere (nitrogen) at 55 ° C for 20 hours. The reaction medium is then washed 3 times with diisopropyl ether in order to remove the excess diethyl sulphate.

The product obtained is then purified on silica frit.

Eluent: CH ₂ Cl ₂ / MeOH (98/2), an eluent gradient is then produced.

38 g of the desired product are obtained in the form of a light brown paste (yield: 71%).

M (m Iz): M + = 372

Example 7

The following hair cosmetic composition (% by weight) is prepared:

SMDI / POLYETHYLENE 5% GLYCOL COPOLYMER WITH 15% ALKYL (METHYL / C18) TERMINATION IN A MALTODEXTRIN / WATER MATRIX (ACULYN 46 - ROHM & HAAS) Composed of example 4 3% ma

Citric acid qs pH 5

Preservatives 0.33%

Water qs 100%

The composition is applied at room temperature of 25 ° C. to a strand of 2.5 g of discolored hair (SA20). The wick is then rinsed and combed. It is observed that the wet wick has a smooth feel, it is relaxed and easy to unravel.

The wick is dried under headphones for 15 minutes at 60 ^° C. By the touch, the dry wick is smooth to the tips and disentangles easily.

Example 8

The following hair cosmetic composition (% by weight) is prepared:

STARCH (CARGILL GEL 03420 from CARGILL) (2% INCI Name: ZEA MAYS (CORN) STARCH)

Surfactant Example 4 3% my

CITRIC ACID pH 5

CONSERVATIVE SYSTEM 0.33%

WATER Qs 100%

The composition is applied at room temperature of 25 ° C. to a strand of 2.5 g of discolored hair (SA20). The wick is then rinsed and combed.

It is observed that the wet wick has a smooth feel, it is relaxed and easy to unravel.

The wick is dried under a helmet for 15 minutes. To the touch, the dry wick is smooth to the tips and disentangles easily.

Similarly, hair compositions can be prepared with the compounds of Examples 1, 2, 3, 5 and 6.

Claims

Cosmetic composition comprising one or more compounds of formula

(I):

in which :

n is an integer between 1 and 10;

- R4 designates:

a linear C 1 -C 30 or branched C 3 -C 30 alkyl radical, optionally interrupted by a 3-, 4- or 5-membered carbon ring, and / or optionally substituted with (i) an aryl itself optionally substituted with one or a plurality of radicals, which may be identical or different, chosen from C1-C6 alkyl, hydroxyl (OH) and amino radicals (-NRR 'with R and R' chosen from, independently of each other, H and C1-alkyl) C6) and / or (ii) one or more radicals, identical or different, chosen from hydroxyl (OH) and amino radicals (- NRR 'with R and R' chosen from, independently of each other, H and C 1 -C 6 alkyl),

a C2-C30, or branched C3-C30 linear alkenyl radical, comprising one or more double bonds, optionally substituted with one or more radicals, which may be identical or different, chosen from hydroxyl (OH) and amino (-NRR ') radicals; with R and R 'chosen from, independently of one another, H and C 1 -C 6 alkyl),

- X- denotes an anion, or an organic or inorganic mixture of anions, to ensure the electroneutrality of the compound of formula (I);

and one or more thickening polymers chosen from: a) thickening polymers not comprising sugar units and b) thickening polymers other than inulin and pectin and comprising one or more sugar units.

2. Composition according to claim 1 wherein n is an integer between 1 and 4, in particular 1, 2 or 3.

3. Composition according to one of the preceding claims, wherein R1 and R2, independently of one another, denote a C1-C linear alkyl group.

C4, C3-C4 branched alkyl, C2-C4 linear alkenyl or C3-C4 branched alkenyl.

4. Composition according to one of the preceding claims, wherein R3 denotes a C1-C22 linear alkyl, branched C3-C22 alkyl, linear alkenyl C2-C22 or branched alkenyl C3-C22.

5. Composition according to one of the preceding claims, wherein R4 denotes: - an alkyl radical, linear or branched, C6-C24, especially C8-C22, said alkyl radical may optionally be interrupted by a carbon ring at 3, 4 or 5 members, and / or optionally substituted by an aryl itself optionally substituted by one or more radicals, which may be identical or different, chosen from C1-C6 alkyl, hydroxyl and amino radicals; a linear or branched C 6 -C 24, especially C 8 -C 22, alkenyl radical;

an aryl group, optionally substituted by one or more radicals, which may be identical or different, chosen from alkylcarbonyl (-C (O) -R) and C4-C18 and / or hydroxyl radicals.

6. Composition according to one of the preceding claims, wherein the compound of formula (I) is chosen from one of the following compounds, or their solvates:

2- [2- (dodecanoyloxy) ethoxy] -N, N, N-triethylethanaminium, An- (1) 1

2- [2- (docosanoyloxy) ethoxy] -N, N, N-triethylethanaminium, An- (1) 2

N, N, N-triethyl-2- {2 - [(9Z) -octadec-9-enoyloxy] ethoxy} ethanaminium, An- (1) 3

N, N, N-triethyl-2- {2 - [(9Z, 12Z, 15Z) -octadeca-9,12,15-trienoyloxy] ethoxyethanaminium, An- (1) 4

N, N, N-trimethyl-2- (2- {2 - [(9Z) -octadec-9-enoyloxy] ethoxy} ethoxy) ethanamine, An- (1)

N, N, N-trimethyl-2- (2- {2 - [(9Z, 12Z, 15Z) -octadeca-9,12,15-trienoyloxy] ethoxy} ethoxy) ethanaminiunn, An- (1) 16

N, N, N-trimethyl-2- (2- {2 - [(16-methylheptadecanoyl) oxy] ethoxy} ethoxy) ethanaminium, An- (1) 17

N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxahexacosan-1-aminium, An- (1) 18

- {2- [2- (docosanoyloxy) ethoxy] ethoxy} -N, N, N-trinneethylethananniniunn, An- (1) 19

N, N, N-triethyl-2- [2- (palmitoyloxy) ethoxy] ethanaminium, An- (1) 23

with An- CI representative ^" , Br ^" , MeSO ₄ ^" or EtSO ₄ ^" .

7. Composition according to one of claims 1 to 5, wherein n is 1, R4 denotes a linear or branched alkyl radical C10-C30 and R1, R2, R3. designate independently of one another a linear or branched C1-C6 alkyl radical.

8. Composition according to any one of the preceding claims, in which the compound of formula (I) is a compound of structure (I) 2.

9. Composition according to one of the preceding claims, wherein the compound of formula (I), alone or as a mixture, is present in an amount ranging from 0.1 to 20% by weight, preferably from 0.5 to 10% by weight. % by weight, especially 1 to 5% by weight, relative to the total weight of the composition.

10. Composition according to any one of the preceding claims, characterized in that the thickening polymer (s) is (are) non-associative or associative.

11. Composition according to claim 10, characterized in that the thickening polymer does not comprise sugar units is a non-associative polymer selected from homopolymers or copolymers of crosslinked acrylic or methacrylic acid, crosslinked homopolymers of 2-acrylamido-2-acid. methylpropane sulfonic acid and their crosslinked acrylamide copolymers, ammonium acrylate homopolymers or copolymers of ammonium acrylate and acrylamide, alone or in mixtures.

12. Composition according to claim 10, characterized in that the thickening polymer not comprising sugar units is chosen from anionic, nonionic, cationic and amphoteric associative thickening polymers.

13. Composition according to claim 12, characterized in that the associative anionic thickening polymer not comprising sugar units is a copolymer of an α, β-monoethylenically unsaturated carboxylic acid and an α-unsaturated carboxylic acid ester. , β-monoethylenic and oxyalkylenated fatty alcohol.

14. Composition according to Claim 13, characterized in that the copolymer of an α, β-monoethylenically unsaturated carboxylic acid and an ester of a carboxylic acid fatty alcohol with α, β-monoethylenic unsaturation and vinylpyrrolidone. .

15. Composition according to claim 12, characterized in that the associative nonionic thickening polymer comprising no sugar units is chosen from:

(a) copolymers of vinyl pyrrolidone and hydrophobic fatty-chain monomers; (b) copolymers of methacrylates or alkyl acrylates in dC ₆ and amphiphilic monomers comprising at least one fatty chain;

(c) copolymers of hydrophilic methacrylates or acrylates and of hydrophobic monomers comprising at least one fatty chain; (d) polyether polyurethanes comprising in their chain, both hydrophilic polyoxyethylenated sequences and hydrophobic sequences;

(e) polymers having an aminoplast ether backbone having at least one fatty chain.

16. Composition according to claim 15, characterized in that the polyurethane polyether is chosen from polyether polyurethanes comprising at least two hydrocarbon-based lipophilic chains having from 6 to 30 carbon atoms, separated by a hydrophilic block, the hydrocarbon chains being dangling chains or chains at the end of the hydrophilic sequence.

17. Composition according to claim 12, characterized in that the thickening polymer not comprising sugar units is a cationic associative polymer chosen from cationic associative polyurethanes.

18. Composition according to any one of the preceding claims, characterized in that the sugar unit or units that can be used in the composition of the thickening polymers comprising one or more sugar units are derived from the following sugars: .glucose

.anhydroglucose

.galactose

.arabinose

.rhamnose .mannose

.xylose

.fucose

.anhydrogalactose

galacturonic acid glucuronic acid

mannuronic acid

.galactose sulfate

anhydrogalactose sulfate

19. Composition according to any one of the preceding claims, characterized in that the thickening polymer or polymers comprising one or more sugar units are chosen from the following gums or polymers that are native or modified physically or chemically:

gum arabic, ghatti gum, karaya gum, tragacanth or tragacanth gum, alginates, carrageenans, guar gum, locust bean gum, fenugreek gum, tamarind gum, gum konjac (polymer derived from glucose and mannose), xanthan gum, gellan gum, scleroglucan gum, cellulose, starch.

20. Composition according to any one of the preceding claims, characterized in that the thickening polymer or polymers comprising one or more sugar units are chosen from guar gums, starches and modified or unmodified celluloses.

21. Composition according to any one of the preceding claims, characterized in that the thickening polymer or polymers with sugar units are celluloses or associative guars.

22. Composition according to any one of the preceding claims, characterized in that the thickeners are present in the compositions in proportions ranging, preferably, from 0.01 to 10% by weight, more preferably from 0.1 to 5%. by weight, relative to the total weight of the composition.

23. Composition according to one of the preceding claims, being in the form of a care product, cleaning and / or makeup of the skin of the body or face, lips, eyebrows, eyelashes, nails , a sunscreen or self-tanning product, a personal hygiene product, a hair product, especially care, cleaning, styling, shaping, hair dyeing.

24. Composition according to one of the preceding claims, in the form of a hair composition, in particular for maintaining the hairstyle or shaping the hair, or the care, the cosmetic treatment or the cleaning of the hair. ; or in the form of a hair coloring product and in particular oxidation dyeing; in the form of a composition of perm, straightening or discoloration, or in the form of a composition to be rinsed, to be applied before or after a coloration, a discoloration, a permanent or a straightening or between the two stages of a permanent or a straightening.

25. Cosmetic treatment process, especially for makeup, care, cleaning, coloring, shaping, keratin materials, in particular the skin of the body or face, lips, nails, hair and / or eyelashes, comprising the application on said materials of a cosmetic composition according to one of claims 1 to 20.

26. Use of a cosmetic composition according to one of claims 1 to 24 for conditioning the hair, in particular to provide or improve the flexibility, disentangling, smoothing.