EP2249779A2 - Cosmetic composition comprising a cationic surfactant compound, novel compounds, use as conditioner and cosmetic treatment method - Google Patents

Abstract

The present application relates to cosmetic compositions comprising cationic compounds of the type of quaternary ammonium esters derived from 2-[2-(diethylamino)ethoxy]ethanol, to the use of these cationic compounds, especially as conditioning agent, to a cosmetic, in particular hair, treatment method employing these compounds, and to the novel cationic compounds.

Description

 Cosmetic composition comprising a surfactant cationic compound, novel compounds, use as a conditioner and cosmetic treatment method

The present invention relates to novel surface-active cationic compounds, of the quaternary ammonium ester type of 2- [2- (diethylamino) ethoxy] ethanol derivatives, to the cosmetic compositions comprising them, and to their use, in particular for cosmetically treating the hair.

It is well known that hair which has been sensitized, in particular damaged and / or embrittled, to varying degrees under the action of atmospheric agents or under the action of mechanical and / or chemical treatments, such as stains, stains and 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 of touching the hair after treatment.

Now, the Applicant has now discovered, unexpectedly and surprisingly, that certain very specific cationic compounds can bring about advantageous conditioning properties to the hair, in particular concerning the improvement of the flexibility of the hair when the composition is applied to the hair. wet hair, then obtaining, after rinsing, hair still having improved flexibility, the hair is therefore less stiff. 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 disentangling, smoothing, combing and maneuverability of the hair; the shaping of the hair is easier, and the touch of the hair is very pleasant and fluid.

It has also been found that, in the presence of fatty alcohols, the cationic surfactants according to the invention do not destabilize the composition, in particular the emulsion, comprising them, contrary to what may be observed with certain cationic amine surfactants. non-quaternary compounds of the prior art, in particular cationic surfactants comprising tertiary amines. Thus, a particularly surprising advantage of the present invention lies in the possibility of formulating fatty alcohols, especially C16-C18, in the presence of cationic amine surfactants. In addition, the compounds according to the invention are easily transportable in aqueous cosmetic media, which facilitates their implementation.

Thus, an object of the present invention is a process for the cosmetic treatment of keratinous materials comprising the application on said materials of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) as hereinafter after defined. Another subject of the invention is the use of at least one compound of formula (I) as defined below, as a conditioning agent, in particular in a hair cosmetic composition.

Another subject of the invention is a cosmetic composition comprising at least one compound of formula (I) as defined below, and a cosmetically acceptable medium comprising at least one usual cosmetic ingredient, chosen in particular from propellants ; water, carbonaceous oils; C8-C40 esters, C8-C40 acids; C 1 -C 40 alcohols, 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; silicones; polymeric thickeners or not; emulsifiers; polymers in particular conditioning or styling. Another subject of the invention is a compound of formula (Ia) as defined below and the cosmetic compositions comprising it.

The compounds according to the invention thus 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, especially hydrocarbon-based, linear, cyclic or branched, carbon 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' chosen from, independently of one another, H and C 1 -C 6 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 radicals (-OH) and / or or amino (-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 alkyl); said heterocycle possibly being substituted by one or more radicals, identical or otherwise, chosen from aryl, C1-C22 alkyl, hydroxyl (OH), amino (-NRR 'radicals with R and R' chosen from, independently one of 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 one another, H and alkyl; C1-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 by one or more radicals, which are identical or different, chosen from C1-C22 alkyl, C1-C22 alkylcarbonyl, hydroxyl (OH), amino radicals (-NRR 'with R and R'); selected 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 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 branched C 3 -C 3 alkenyl group. C22.

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. Preferentially, 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. Preferentially, 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. Preferentially, R3 represents a C1-C22, in particular C1-C18, linear alkyl group.

Preferably, R4 designates:

an alkyl radical, linear or branched, C 6 -C 24, in particular C 8 -C 22, said alkyl radical possibly being interrupted by a 3-, 4- or 5-membered carbon ring, and / or optionally substituted with 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 with one or more radicals, which may be identical or different, chosen from C 4 -C 18 alkylcarbonyl (-C (O) -R) and / or hydroxyl radicals.

Preferably X ^" denotes an anion, or a mixture of anions, such as acetate, lactate, tartrate, citrate, halogen, SO ₄ ^2" , HSO ₄ ^" , MeSO ₄ ^" , EtSO ₄ ^" , mesylate, tosylate; preferably Cl ^" , Br ^" , MeSO ₄ ^" , EtSO ₄ ^" , mesylate, tosylate.

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:

2- [2- (dodecanoyloxy) ethoxy] -N N -trimethylethanaminium, An-

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

N, N, N-triethyl-2- {2 - [(9Z) -octadec-9-enoyloxyethoxy} ethanaminium, An-

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

N, N, N-triethyl-2- {2 - [(16-methylheptadecanoyl) oxy] ethoxy} ethanediamine,

N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxatetracosan-1-aminium, 2- [2- (Decanoyloxy) ethoxy] -N, N, N-triethylethanaminium, An-

N, N-diethyl-N- {2- [2- (palmitoyloxy) ethoxy] ethyl} hexadecan-1-aminium, An-

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

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

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

N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxahexacosan-1-aminium,

2- {2- [2- (docosanoyloxy) ethoxy] ethoxy} -N, N, N-trimethylethanaminium, An-

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

N, N, N-triethyl-2- (2- {2 - [(2-hydroxy-5-octanoylbenzoyl) oxy] ethoxy} ethoxy) ethanaminium,

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

Year-

N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxatetratriacontan-1-aminium, An-

N- {2- [2- (dodecanoyloxy) ethoxy] ethyl} -N, N-diethyldodecan-1-aminium, An-

N, N, N-triethyl-2- [2- (2 - {[5- (4-hydroxyphenyl) pentanoyl] oxy} ethoxy) ethoxy] ethanamine,

In these compounds, preferably An- (= X) is Cl ^{", Br",} MeSO ₄ ^", Et- SO ^_4", SO ₄ ^{2- ",} HSO ^_4", mesylate, or tosylate and mixtures thereof.

Among these compounds, some are novel as such, and form an object of the present invention. These are the compounds of formula (Ia) below, as well as their solvates:

in which :

n is an integer between 1 and 10;

- Ri = R2 = ethyl

R3 denotes a linear or branched alkyl radical comprising 1 to 22 carbon atoms, optionally substituted with one or more hydroxyl (-OH) and / or amino radicals (-NRR 'with R and R' chosen from, independently of one another; on the other, H and C1-C6 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 one or more radicals, which may be identical or different, chosen from the radicals hydroxyl (OH) and amino waters (-NRR 'with R and R' chosen from, independently of each other, H and C 1 -C 6 alkyl),

a linear or branched C 6 -C 30 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; )

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 one another, H and C 1 -C 6 alkyl); and

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

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

Preferably, R 3 represents a linear C 1 -C 22 alkyl group, especially a C 1 -C 18 alkyl group.

Preferably, R4 designates:

an alkyl radical, linear or branched, C 6 -C 24, in particular C 8 -C 22, said alkyl radical possibly being interrupted by a carbon ring with 3, 4 or 5 members;

a linear or branched C 6 -C 24, especially C 8 -C 22, alkenyl radical; an aryl group, optionally substituted with one or more radicals, which may be identical or different, chosen from C 4 -C 18 alkylcarbonyl (-C (O) -R) and / or hydroxyl radicals.

Preferably X ^" denotes an anion, or a mixture of anions, such as acetate, lactate, tartrate, citrate, halogen, SO ₄ ^2" , HSO ₄ ^" , MeSO ₄ ^" , EtSO ₄ ^" , mesylate, tosylate; preferably CI ^" , Br ^" , MeSO ₄ ^" , EtSO ₄ ^" , and mixtures thereof.

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: ^R

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 compounds according to the invention, (I) or (Ia), find a very particular application in the cosmetics or pharmaceutical field, particularly in the hair field, and in particular as a conditioning agent.

The amount of compound (I) or (Ia), 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 0.01 and 50% by weight, preferably between 0.1 and 30% by weight, in particular 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) or (Ia).

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; a gel aqueous or anhydrous, 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) or (Ia) in dispersion in an aqueous phase or in solution in a fatty phase.

The compositions according to the invention comprise a physiologically acceptable medium, that is to say a medium which 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 nails. Said physiologically acceptable medium is preferably a cosmetically acceptable medium, the composition then being a cosmetic composition intended in particular for topical application.

Said physiologically acceptable medium preferably comprises at least one usual cosmetic ingredient, especially chosen from propellants; water, carbonaceous oils; C8-C40 esters, C8-C40 acids; C1-C40 alcohols, 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; hydroxyacids; pigments; the charges; silicones; polymeric thickeners or not; emulsifiers; polymers in particular conditioning or styling. Said medium can of course include several cosmetic ingredients listed above.

Depending on their nature and the purpose 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 included, for each ingredient, between 0.01 to 80% by weight .

The composition may especially comprise water and / or one or more C 1 -C 40 alcohols; mention may especially be made of C 1 -C 7 aliphatic or aromatic monoalcohols, polyols and polyol ethers, which may therefore be used alone or mixed with water; advantageously, the composition comprises a water / ethanol, water / isopropanol or water / benzyl alcohol mixture. The oils, in particular carbonaceous or even hydrocarbon-based oils, can be present in a proportion of from 0.01 to 20% by weight, in particular from 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; silicone oils, volatile or not, organomodified or otherwise, water-soluble or not; fluorinated or perfluorinated oils; their mixtures.

Alcohols, esters and acids, having 8 to 40 carbon atoms, can be present in a proportion of 0.01 to 50% by weight, especially 0.1 to 20% by weight relative to the total weight of the composition. Mention may in particular 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 C8-C40 fatty alcohols, in particular C16-C20, which are oxyalkylenated, in particular oxyethylenated, preferably comprising from 10 to 50 moles of ethylene oxide and / or propylene oxide, such as olethoxide. -12, ce-teareth-12 and ceteareth-20, oxypropylene stearyl alcohol in particular comprising 15 moles of propylene oxide, oxyethylenated lauryl alcohol, including more than 7 oxyethylene groups, and mixtures thereof. 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 fatty esters containing in total between 8 and 40 carbon atoms, such as esters of monoalcohols or polyols of fatty acids containing from 8 to 30 carbon atoms, and their oxyalkylenated derivatives. and in particular oxyethylenated, the polyols being preferentially chosen from sugars, C2-C6-alkylene glycols, glycerol, polyglycerols, sorbitol, sorbitan, polyethylene glycols, polypropylene glycols and mixtures thereof. Mention may be made, as monoalcohol esters, of myristate or isopropyl palmitate, as well as myristates, palmitates and stearates of myristyl, cetyl and stearyl, alone or as a mixture.

The composition may also include as carbonaceous oils, vegetable oils such as avocado oil, olive oil, apricot oil, argan oil, jojoba oil, butter shea, which may be present in a proportion of 0.1 to 10% by weight in the composition, in particular 0.2 to 5% by weight. In a preferred embodiment, the composition according to the invention comprises C 8 -C 40 fatty alcohols, which may be present especially in an amount of 1 to 15% by weight, in particular 2.5 to 10% by weight, or even 3 to 8% by weight, in the cosmetic composition.

These fatty alcohols can be saturated or unsaturated, linear or branched; mention may be made in particular of cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleic alcohol, ricinoleic alcohol, linoleic alcohol, alone or as a mixture; saturated fatty alcohols, alone or as a mixture, are preferred.

The surfactants, nonionic, cationic, anionic, amphoteric or zwitterionic, other than those of formula (I), and mixtures thereof, may be present in a proportion of from 0.01% to 50% by weight, in particular 0.1% to 40% by weight, or even 0.5 to 30% by weight, more preferably 1 to 15% by weight, relative to the total weight of the composition.

In particular, the weight ratio between the amount of fatty alcohols and the amount of surfactants in the composition is preferably greater than or equal to 1, 5, in particular between 1, 5 and 10, or even between 1, 6 and 8, even better between 1, 7 and 6.

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 from 0.1 to 30% by weight, in particular 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 may be present in an amount of from 0.001 to 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, in particular 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; polyorganosiloxanes, which may or may not be modified, 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, may especially be mentioned. 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 thickeners, polymeric or not, 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, in particular conditioners or styling agents, in particular water-soluble or soluble in carbonaceous and / or silicone oils, can be present in a proportion of from 0.01 to 20% by weight, in particular 0.1 to 10% by weight with respect to port 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 hair , a sunscreen or self-tanning product, a personal hygiene product, a hair product, especially care, cleaning, styling, shaping, hair dyeing. It finds particularly a particularly interesting application in the hair field, including the maintenance of the hairstyle or the shaping of the hair, or the care, the cosmetic treatment or the cleaning of the hair. The hair compositions are preferably shampoos, conditioners, styling or care gels, lotions or care 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-borrheic 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.

It may also be in the form of a hair coloring product, in particular oxidation dyeing or direct dyeing, optionally in the form of a coloring shampoo; in the form of a composition of permanent, de-waxing or discoloration, or in the form of a composition to be rinsed, to be applied before or after a coloring, 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, in particular a moisturizer, for the skin of the body or of the face, the lips and / or the integuments, in particular of a care product intended to treat cosmetically the skin and in particular to moisturize it, smooth it, depigment it, nourish it, protect it from the sun's rays, or give it a specific cosmetic treatment. Thus 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 vi - wise; 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; In particular, the compounds according to the invention can 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 make-up, care, cleaning, coloring, shaping, keratin materials, in particular of the skin of the body or of the face, of the lips, nails, hair and / or eyelashes, comprising the application to said materials of a cosmetic composition comprising at least one compound according to the invention.

Preferably, it is a cosmetic treatment method for conditioning the hair, in particular to provide or improve the flexibility, disentangling, smoothing and / or combability of the 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) ethoxy-N, N, N-triethylethanamino 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 IRA 400 ion exchange resin. After removing the solvent, washing the compound with diisopropyl ether, filtering and drying under reduced pressure. 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- [2- (Decanoyloxy) ethoxy] -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 treating an aqueous solution of the compound with 300 g of IRA 402 ion exchange resin. After removal of the solvent, washing the compound with diisopropyl ether, filtering 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) ethoxyethanammonium 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, filtering 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 / z): M ₊ = 428 Example 4 Synthesis of 2- [2- (docosanoyloxy) ethoxy] -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 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 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 and acetone ( 80/20).

After removing the solvent, washing the compound with diisopropyl ether, filtering 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- (2- (palmitoyloxy) ethoxy] ethyl) 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 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: - Chicory root inulin (Inutec N25 from Orafti) 15% MA

- Lemon pectin (CU 201 from Herbstreith and Fox) 2% MA

- Composed of example 2 1%

- Water qs 100%

1 g of the composition is applied to a strand of bleached hair (SA20) of 2.5 g, previously wetted. The wick is then rinsed and combed. It is observed that the wet wick has a smooth feel, it is flexible and easy to disentangle. The wick is dried under a helmet for 15 minutes. To the touch, the dry wick is soft and smooth to the ends. She disentangles well.

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

Example 8

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

- Cetearyl Alcohol 7% MA

- Cetyl esters 1, 5% MA

- Compound of Example 3 3% - Water qs 100% A comparative composition is prepared by replacing the compound according to the invention with 2- (2- (diethylamino) ethoxy) ethyl palmitate (3% by weight). After storage of the compositions obtained for 8 hours at 25 ^° C., they are visually observed and it is found that the composition according to the invention is stable (homogeneous) while the comparative composition is not stable: a suspension is observed.

Example 9

Synthesis of a compound of formula (I) in which n = 1, R 4 = C ₂ H ₄₃ and R 1 = R 2 = R 3 = ethyl and X - is an ethosulphate, hydrogen sulfate mixture.

Step 1: Synthesis of 2- [2- (diethylamino) ethoxy] ethyl docosanoate of formula:

To a solution of 25 g of 2- [2- (diethylamino) ethoxy] ethanol (0.155 mol) dissolved in 500 ml of dichloromethane was added 45 ml of triethylamine (0.32 mol). After stirring for 30 minutes at room temperature, a solution of 55 g of behenic acid chloride was added dropwise. There is a slight exotherm of 8 ° C. After the addition was complete, the reaction mixture was stirred for 8 hours. After filtration on sintered glass, the reaction medium was poured into 500 ml of water and then the organic phase was washed with water until pH 9. After drying over sodium sulphate and filtration, the mixture was evaporated under reduced pressure. organic phase to obtain 70 g of the expected compound as a white paste, with a yield of 93%. Melting point: 88.7 ° C NMR spectrum ¹ H 400 MHz and ¹³ C 100 MHz: compliant Conforming mass spectrum: M (m / z): [M + H] + = 484

Step 2: Synthesis of 2- [2- (docosanoyloxy) ethoxy] -N, N, N-triethylethanaminium Ethosulfate / Hydroxenosulfate Mixture

II

To 65 g of 2- [2- (diethylamino) ethoxy] ethyl docosanoate (0.134 mol) introduced into a reactor, 41 ml of diethylsulphate (0.312 mol) were added all at once. The reaction medium was then stirred at 40 ^° C. for 48 hours. 50 ml of acetone were then added and stirred until solubilization of the reaction medium. This medium was then poured into 2 liters of isopropyl ether kept under stirring and under argon. The precipitate formed was then filtered on a sintered glass and then dried under vacuum to obtain 71 g of 2- [2- (docosanoyloxy) ethoxy] -N, N, N-triethylethanaminium in the form of an ethosulfate / hydrogen sulphate mixture whose percentage is determined by NMR: 0.52 / 0.48. The percentage of hydrogen sulphate may vary depending on the water content present in the precipitation medium. The product is in the form of a white powder; the yield is 83%. Melting point: 76.3 ° C

¹ H NMR spectrum and ¹³ C 400Mhz 100Mhz: comply

Conformal mass spectrum: M (m / z): [M] + = 512 [M] - = 97 and 125

Example 10 Synthesis of a compound of formula (I) wherein n = 1, R 4 = C ₂ H ₄₃ and R 1 = R 2 = R 3 = ethyl and X - is hydrogen sulfate.

To a suspension of 2 g of the 2- [2- (docosanoyloxy) ethoxy] -N, N, N-triethylethanaminium hydrogenosulfate / ethosulfate mixture prepared in Example 9, in 100 ml of acetone, was added 0.1 ml of 36% concentrated sulfuric acid. The reaction mixture was then refluxed for 5 hours and after cooling to 5 ° C a precipitate formed. After filtration and drying under vacuum, there was thus obtained 1.2 g of the expected product in total form of hydrogen sulfate. 400MHz ¹ H NMR spectrum and ¹³ C 100 Mhz: comply

Conformal mass spectrum: M (m / z): [M] + = 512; [M] - = 97

Example 1 1 Synthesis of a compound of formula (I) wherein n = 1, R 4 = C ₂ H ₄₃ and R 1 = R 2 = R 3 = ethyl and X - is methanesulfonate (mesylate).

General synthetic route for Examples 1 1 and 12:

,. . . form mesylate form toesylate

Step 1: synthesis of 2- (2-hydroxyethoxy) ethyl docosanoate

To a solution of 250 ml of dichloromethane was added 250 ml of diethylene glycol (26 moles) and then the reaction medium was cooled to 50 ^° C by an ice bath. 45 g of N, N-diisopropylethylamine (0.348 mol) were then added and stirred for 30 minutes. A solution of 84 g (0.233 moles) of behenic acid chloride pre-dissolved in 250 ml of dichloromethane was then added dropwise, so as to maintain a temperature of between 5 ° C. and 10 ° C. When the addition was complete, the reaction medium was stirred for 6 hours at room temperature. The reaction medium was then poured into 2 liters of water and then the organic phase was washed three times with 300 ml of water, and finally with 200 ml of a saturated solution of ammonium chloride. After drying over sodium sulphate and filtration, the organic phase was evaporated under reduced pressure; 92 g of the expected compound were obtained in the form of a white powder with a yield of 91%. ¹ H NMR spectrum 400 MHz, ¹³ C 100 MHz. Conforms Mass spectrum: M (m / z): [M + H] + = 429

Step 2: Synthesis of 2- (2-r (methylsulfonyloxyethoxy) ethyl docosanoate To a solution of 5 g of 2- (2-hydroxyethoxy) ethyl docosanoate (0.01 16 mol) dissolved in 100 ml of dichloromethane cooled to 5 ° C was added 1.7 g of N, N-diisopropylethylamine (0.013 mol). . A solution of 1.33 g of methanesulphonic acid chloride (0.0166 mol) dissolved in 50 ml of dichloromethane was then added dropwise so as to maintain a temperature of less than 10 ^° C. The addition was complete. The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was then poured into 300 ml of water, the organic phase washed twice with 150 ml of water and then once with 100 ml of saturated ammonium chloride solution. After drying over sodium sulfate, filtration and evaporation under reduced pressure, the crude product obtained was purified on a silica column in a dichloromethane / methanol mixture.

3.5 g of the expected compound was obtained in the form of a white powder with a yield of 60%. ¹ H NMR spectrum 400 MHz, ¹³ C 100Mhz: consistent Mass spectrum: M (m / z): [M + Na] + = 529

Step 3: Synthesis of 2-r 2 - (docosanoyloxy) ethoxy-N, N, N-triethylethanaminium methanesulfonate

To a suspension of 3.4 g of 2- {2 - [(methylsulfonyl) oxy] ethoxy} ethyl docosanoate (0.00691 mol) in 100 ml of acetonitrile was added 25 ml of triethylamine (0.179 mol). The reaction medium was then refluxed for 72 hours. After evaporation under reduced pressure, the residue was taken up in 100 ml of acetone and the precipitate formed filtered off.

After drying under reduced pressure, 3 g of the expected compound was obtained in the form of a white powder with a yield of 71%. NMR spectrum 1H 400Mhz, 13C 100Mhz: conform. Mass spectrum: M (m / z): [M] + = 512 - [M] - = 95

Example 12

Synthesis of a compound of formula (I) in which n = 1, R4 = C ₂ i H ₄₃ and

R1 = R2 = R3 = ethyl and X- is paratoluene sulfonate (tosylate).

Eatope 1: Synthesis of 2- (2- {| ^{"(4-methylphenyl)} sulfonyl] oxylethoxy) ethyl docosanoate

To a solution of 70 g of 2- (2-hydroxyethoxy) ethyl docosanoate (0.1633 mol) dissolved in 500 ml of dichloromethane cooled to 5 ° C was added 17 g of triethylamine (0.168 mol). A solution of 32 g of para-toluenesulphonic acid chloride (0.1678 mol) dissolved in 250 ml of dichloromethane was then added dropwise so as to maintain a temperature below 10 ° C. After the addition was complete, the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was then poured into 2 liters of water, the organic phase washed with 3 times 300 ml of water, then 3 times 200 ml of a saturated solution of sodium hydrogencarbonate and 1 x 200 ml of a solution. saturated solution of ammonium chloride. After drying over sodium sulphate, filtration and evaporation under reduced pressure, the crude compound obtained was purified on a silica column in a dichloromethane / methanol mixture. There was thus obtained 70 g of the expected compound in the form of a white powder with a yield of 74%. NMR Spectrum 1 H 400 Mhz, 13 C 100 Mhz: consistent Mass Spectrum: M (m / z): [M + Na] + = 605

Step 2: Synthesis of 2- [2- (docosanoyloxy) ethoxy] -N, N, N-triethylethanaminium

4-methylbenzenesulfonate

To a suspension of 10.66 g of 2- (2 - {[(4-methylphenyl) sulfonyl] oxy} ethoxy) ethyl docosanoate (0.0182 mol) in 100 ml of acetonitrile was added 25 ml of triethylamine ( 0.179 moles). The reaction medium was then refluxed during

36 hours. After evaporation under reduced pressure, the residue was taken up in 100 ml of acetone and the precipitate formed filtered off. After drying under reduced pressure, 11 g of the expected compound were obtained in the form of a white powder with a yield of 88%.

NMR spectrum 1H 400Mhz, 13C 100Mhz: conform.

Mass Spectrum: M (m / z): [M] + = 512 - [M] - = 171

Example 13

Various cosmetic compositions are prepared comprising the compounds prepared in Examples 9 to 12 (% by weight).

Some of these compositions are applied to the hair in the following manner: 1 g of cosmetic composition is applied to a strand of 2.5 g of discolored hair (SA20).

Composition 1:

- Composed of Example 9 or Example 12 1, 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

- citric acid qs pH 2.5 - water qs 100% These compositions provide a smooth feel on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10 or 11 may be prepared.

Composition 2:

- Compound of Example 9 1, 5% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

- myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 0.5%

- citric acid qs pH 2.5 - water qs 100%

This composition provides a smooth feel on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 3:

- Compound of Example 9 1, 5% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

- myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 0.5%

- PDMS with aminoethyl iminopropyl groups in emulsion (DC 939 Dow Corning emulsion) 2%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 4:

- Composed of example 9 1, 5%

- cetylstearyl alcohol (C16 / C18 50/50) (Lanette O or flakes of Cognis) 3%

- myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 0.5% - avocado oil 2%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10 to 12 can be prepared.

Composition 5:

- Compound of Example 9 1, 5% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

- myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 0.5%

- PDMS with aminoethyl iminopropyl groups in emulsion (DC 939 Dow Corning emulsion) 2%

- avocado oil 1%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 6:

- Compound of Example 9 3.25% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5.5%

- citric acid qs pH 2.5

- water qs 100% This composition provides a smooth touch on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 7:

- Composed of Example 9 3.25%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5.5% - myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1%

- citric acid qs pH 2.5 - water qs 100% This composition provides a smooth touch on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 8: - Compound of Example 9 3.25%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5.5%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1% - PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 4%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 9:

- Compound of Example 9 3.25% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5.5%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 1%

- olive oil 2% - citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 10:

- Composed of Example 9 3.25%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5.5% - myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1%

- PDMS with aminoethyl iminopropyl groups in emulsion (DC 939 emulsion from Dow Corning) 4%

- 1% olive oil

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 1 1: - Compound of Example 9 or compound of Example 12 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 8%

- citric acid qs pH 2.5

- water qs 100% These compositions provide a smooth touch on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10 or 11 may be prepared.

Composition 12:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50) (Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5%

- citric acid qs pH 2.5

- water qs 100% This composition provides a smooth touch on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 13:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50) (Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5% - PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 4%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 14: - Compound of Example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5% - apricot oil 2%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 15:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50) (Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5%

- PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 Dow Corning emulsion) 4% - apricot oil 1%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 16:

- Composed of example 9 1, 5%

- cetylstearyl alcohol (C16 / C18 50/50) (Lanette O or flakes of Cognis) 8%

- citric acid qs pH 2.5

- water qs 100% This composition provides a smooth feel on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 17:

- Compound of Example 9 1, 5% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5%

- citric acid qs pH 2.5 - water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 18:

- Composed of example 9 1, 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5%

- PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 4%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 19: - Compound of Example 9 1, 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5% - argan oil 3%

- citric acid qs pH 2.5

- water qs 100% Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 20:

- Composed of example 9 1, 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 8%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1, 5%

- PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 4%

- 0.5% argan oil

- citric acid qs pH 2.5 - water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 21:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5%

- citric acid qs pH 2.5 - water qs 100%

This composition provides a smooth feel on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 22:

- Compound of Example 9 5% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 1%

- citric acid qs pH 2.5 - water qs 100% Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 23: - Compound of Example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 1% - PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 3%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 24:

- Compound of Example 9 5% - cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 1%

- jojoba oil 2% - citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 25:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 5% - myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 1%

- PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 3%

- jojoba oil 1, 5% - citric acid qs pH 2.5

- water qs 100% Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 26: - Composed of Example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

- citric acid qs pH 2.5

- water qs 100% This composition provides a smooth touch on wet hair, the wick is relaxed and disentangles easily. On dry hair, the wick is easily disentangled, the touch is smooth.

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 27:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50) (Lanette O or flakes of Cognis) 3%

- myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Croda Crodamol MS-V) 0.5%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 28: - Compound of Example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 0.5% - PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 1, 5%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared. Composition 29:

- Composed of example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3% - myristate / palmitate / myristyl stearate / cetyl / stearyl blend

(Crodamol MS-V from Croda) 0.5%

- 0.5% shea butter

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Composition 30: - Compound of Example 9 5%

- cetylstearyl alcohol (C16 / C18 50/50)

(Lanette O or flakes of Cognis) 3%

myristate / palmitate / myristyl stearate / cetyl / stearyl mixture (Crodamol MS-V from Croda) 0.5% - PDMS with aminoethyl iminopropyl groups in emulsion

(DC 939 emulsion from Dow Corning) 1, 5%

- shea butter 0.1%

- citric acid qs pH 2.5

- water qs 100%

Similar cosmetic compositions comprising the compounds of Examples 10, 11 or 12 can be prepared.

Claims

1. A process for the cosmetic treatment of keratin materials comprising the application to said materials of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula

in which: - n is an integer between 1 and 10;

R 1, R 2 and R 3 denote, independently of each other, a saturated or unsaturated, linear or cyclic or branched, hydrocarbon-based hydrocarbon group comprising 1 to 22 carbon atoms, optionally substituted with one or more hydroxyl radicals; and / or amino (-NRR 'with R and R' selected from, independently of one another, H and C1-C6 alkyl); or

R 1 denotes a saturated or unsaturated, linear or cyclic or branched, hydrocarbon-based hydrocarbon group comprising 1 to 22 carbon atoms, optionally substituted by one or more hydroxyl and / or amino radicals (-NRR 'with R and R); selected from, independently of one another, H and C 1 -C 6 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 may optionally be substituted by one or more radicals, identical or otherwise, chosen from aryl, C 1 -C 22 alkyl, hydroxyl, amino (-NRR 'radicals with R and R' chosen from, independently of one of 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 and amino radicals (-NRR 'with R and R' chosen from, independently of one another, H and C1-C6 alkyl); and / or (ii) one or more radicals, which may be identical or different, chosen from hydroxyl and amino radicals (-NRR 'with R and R' chosen from, independently of one another, H and C1-alkyl) C6), 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 and amino radicals (-NRR 'with R and R 'chosen from, independently of one another, H and C 1 -C 6 alkyl),

an aryl group, optionally substituted by one or more radicals, which may be identical or different, chosen from C 1 -C 22 alkyl, C 1 -C 22 alkylcarbonyl, hydroxyl and amino radicals (-NRR 'with R and R' chosen from, independently of one another; one of the other, H and C1-C6 alkyl);

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

2. Process according to claim 1, in which the compound is of formula (I) in which:

- R1 = R2 = ethyl;

R3 denotes a linear or branched alkyl radical comprising 1 to 22 carbon atoms, optionally substituted by one or more hydroxyl and / or amino radicals (-NRR 'with R and R' chosen from, independently of one another , H and C1-C6 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 one or more radicals, which may be identical or different, chosen from the hydroxyl and amino radicals (-NRR 'with R and R' chosen from, independently of one another, H and C 1 -C 6 alkyl),

a linear or branched C 6 -C 30 alkenyl radical comprising one or more double bonds; optionally substituted with one or more radicals, which are identical or different, chosen from hydroxyl (OH) and amino (-NRR 'radicals with R and R' chosen from, independently of each other, H and C1-alkyl) - C6),

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);

3. Method according to one of the preceding claims, wherein the compound of formula (I), alone or as a mixture, is present in the composition in an amount of between 0.01 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. tion.

4. Method according to one of the preceding claims, wherein the compound of formula (I) is selected from the following compounds, as well as their solvates:

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

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

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

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

N, N, N-triethyl-2- (2- {2 - [(5-phenylpentanoyl) oxy] ethoxy} ethoxy) ethanaminium, An-

2- [2- (Decanoyloxy) ethoxy] -N, N, N-triethylethanaminium, An-

N, N-diethyl-N- {2- [2- (palmitoyloxy) ethoxy] ethyl} hexadecan-1-aminium, An-

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

Year-

5. Method according to one of the preceding claims, characterized in that it is a cosmetic treatment method for conditioning the hair, in particular to provide or improve the flexibility, disentangling, smoothing and / or the combability of the hair.

6. Use of at least one compound of formula (I) as defined in one of claims 1, 2 and 4, as a conditioning agent, in particular in a hair cosmetic composition.

7. Cosmetic composition comprising at least one compound of formula (I) as defined in one of claims 1, 2 and 4, and a cosmetically acceptable medium comprising at least one usual cosmetic ingredient, especially chosen from propellants; water, carbonaceous oils; C8-C40 esters, C8-C40 acids; C 1 -C 40 alcohols, 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; silicones; polymeric thickeners or not; emulsifiers; polymers in particular conditioning or styling.

8. Compound of formula (la):

in which :

n is an integer between 1 and 10; - R1 = R2 = ethyl R3 denotes a linear or branched alkyl radical comprising 1 to 22 carbon atoms, optionally substituted with one or more hydroxyl (-OH) and / or amino radicals (-NRR 'with R and R' chosen from, independently of one another; on the other, H and C1-C6 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 one or more radicals, which may be identical or different, chosen from the radicals hydroxyl (OH) and amino waters (-NRR 'with R and R' chosen from, independently of each other, H and C 1 -C 6 alkyl),

a linear or branched C 6 -C 30 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; )

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 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 compounds of formula (Ia).

9. Cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (Ia) according to claim 8.

10. Composition according to claim 9, wherein the physiologically acceptable medium comprises at least one usual cosmetic ingredient selected from propellants; water, carbonaceous oils; C8-C40 esters, C8-C40 acids; C1-C40 alcohols, 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; silicones; polymeric thickeners or not; emulsifiers; polymers in particular conditioning or styling.

1 1. Composition according to one of Claims 7, 9 and 10, in which the compound of formula (I) or (Ia), alone or as a mixture, is present in a quantity between 0.01 and 50% by weight, preferably between 0.1 and 30% by weight, in particular 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.

12. Composition according to one of claims 7, 9 to 1 1, wherein the compound of formula (I) or (la) is chosen from the following compounds, and their solvates:

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

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

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

N, N, N-triethyl-2- {2 - [(9Z, 12Z, 15Z) -octadéca-9,12,15-trienoyloxy] ethoxy ethanaminium,

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

N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxatetracosan-1-aminoimin,

N, N, N-trimethyl-13-oxo-3,6,9,12-tetraoxatriacontan-1-aminium, An-

N, N, N-trimethyl-2- (2- {2 - [(8E, 11S) -octadeca-8,1 1 -dienoyloxy] ethoxy} ethoxy) ethanaminium, An-

N, N-diethyl-N- {2- [2- (palmitoyloxy) ethoxy] ethyl} dodecan-1-aminium,

N, N, N-triethyl-2- (2- {2 - [(3,4,5-trihydroxybenzoyl) oxy] ethoxy} ethoxy) ethanamide nium,

N, N, N-triethyl-2- (2- {2 - [(5-phenylpentanoyl) oxy] ethoxy} ethoxy) ethanaminium, An-

2- [2- (Decanoyloxy) ethoxy] -N, N, N-triethylethanaminium, An-

N, N-diethyl-N- {2- [2- (palmitoyloxy) ethoxy] ethyl} hexadecan-1-aminium, An-

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

N, N _! N-trimethyl-2- (2- {2 - [(9Z _: 12Z _: 15Z) -octadeca-9,12,15-trienoyloxy] ethoxy} ethoxy) ethanaminium, An-

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

H

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

2- {2- [2- (docosanoyloxy) ethoxy] ethoxy} -N, N, N-trimethylethanaminium, An-

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

Year-

13. Composition according to one of claims 7, 9 to 12, comprising C8-C40 fatty alcohols present in an amount of 1 to 15% by weight, especially 2.5 to 10% by weight, or even 3 to 8. % by weight, in the cosmetic composition.

14. Composition according to one of claims 7, 9 to 13, being in the form of a care product, cleaning and / or makeup of the skin of the body or face, lips, eyebrows, eyebrows. eyelashes, nails and hair, a suntan or self-tanning product, a personal care product, a hair product, in particular care, cleaning, styling, shaping, hair dyeing .

15. Composition according to one of claims 7, 9 to 14, in the form of a hair composition for the care and the cosmetic treatment, in particular the protection, of the hair, in particular weakened hair and / or damaged, for example by chemical or mechanical treatments.