FR2937551A1 - Use of compounds derived from chlorotriazine for protection of color during the washing of artificially dyed keratin fibers especially human keratin fibers, preferably hair - Google Patents

Abstract

Use of one or more compounds (I) derived from chlorotriazine as an agent for protection of color during the washing of artificially dyed keratin fibers especially human keratin fibers, preferably hair, is claimed. Independent claims are included for: (1) protecting the color during washing of artificially dyed keratin fibers such as human keratin fibers, preferably hair, comprising applying (I) or a composition comprising (I) in a medium, to the fibers; (2) dyeing keratin fibers, especially human keratin fibers, preferably hair, comprising: applying a direct dye composition (A) or an oxidation composition (A) optionally in the presence of one or more oxidizing agents, to the fibers for a time sufficient to develop the color, and preceded or followed by the application of a composition (B) containing (I) in a medium; or applying a direct dye composition (A) or an oxidation composition (A) to the fibers, where the composition (A) contains (I) in a medium; and (3) a kit comprising at least one first component comprising a composition (B) comprising (I) in an aqueous medium, and at least one second component comprising a coloring composition (A) comprising at least one oxidation dye and/or or at least one direct dye, where the two components are optionally associated with a third component comprising one or more oxidizing agents.

Description

USE OF A CHLOROTRIAZINE DERIVATIVE COMPOUND FOR PROTECTING COLOR FROM THE WASHING OF ARTIFICIALLY ARTIFICIENT KERATIN FIBERS; The invention relates to the use of one or more compounds derived from chlorotriazine as an agent for protecting the color vis-à-vis the washing of dyed keratin fibers by direct dyeing or by oxidation dyeing, in particular human keratin fibers and more particularly hair.

It is known to dye particularly human keratinous fibers and in particular the hair with dyeing compositions containing oxidation dye precursors, generally called oxidation bases.

These oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, give rise to colored compounds by a process of oxidative condensation. It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or color modifiers. The variety of molecules involved in the oxidation bases and couplers allows a rich palette of colors to be obtained.

It is also known to dye keratinous fibers by direct dyeing. The method conventionally used in direct dyeing consists in applying to the keratin fibers direct dyes which are colored and dyestuff molecules having an affinity for the fibers, allowing the fibers to be laid and then rinsed. This direct coloration may be optionally carried out in the presence of an oxidizing agent, it is then called direct lightening coloring.

The resulting colorings are particularly chromatic colorations that are however temporary or semi-permanent because the nature of the interactions that bind the direct dyes to the keratinous fiber and their desorption from the surface and / or the core of the fiber are responsible for their low dye power and their poor resistance to washes.

The artificial color of the hair provided by a direct coloring or oxidation treatment gradually fades due to repeated washing and leads in time to a fading of the hair coloring. The use of rinsed and rinsed care products marketed does not improve sufficiently the holding of the artificial color of the hair.

It is therefore necessary to develop means to protect the artificial color of the effect of repeated washing.

The Applicant has now surprisingly discovered that the use of one or more compounds derived from chlorotriazine made it possible to protect the artificial color of the keratin fibers dyed by direct dyeing or by oxidation dyeing in the presence, possibly with respect to the washing. an oxidizing agent.

This discovery is the basis of the present invention. For the purposes of the invention, the term "oxidizing agent" means any compound having oxidizing properties and being different from oxygen in the air.

By human keratin fibers is meant hair, hair including a beard or mustache, eyelashes, eyebrows.

The term "keratin fibers" artificially dyed keratin fibers dyed by a direct dyeing process or by an oxidation dyeing process.

By washing is meant one or more applications on the keratinous fibers of an aqueous composition that is eliminated, most often a detergent such as a shampoo. This expression also includes swimming, especially at sea or in swimming pools.

By compound derived from chlorotriazine is meant a compound comprising one or more triazine groups of which at least one of the carbon atoms is carrying a chlorine atom.

The subject of the invention is therefore the cosmetic use of one or more compounds derived from chlorotriazine, as an agent making it possible to protect the color of artificially dyed keratin fibers with respect to washing, in particular human keratin fibers and more particularly hair. Preferably, the keratinous fibers are dyed by oxidation dye, especially in the presence of one or more oxidizing agents.

The invention also relates to a method for protecting the color vis-à-vis 40 washing artificially dyed keratinous fibers, characterized in that it consists in applying to said fibers, one or more compounds derived from chlorotriazine or composition comprising in a cosmetically acceptable medium one or more compounds derived from chlorotriazine. Preferably, the keratinous fibers are dyed by oxidation dyeing in the presence of one or more oxidizing agents.

The compound (s) derived from chlorotriazine may be introduced into the dye composition applied to the keratinous fibers. They can be introduced preferably into a composition applied before or after dyeing keratinous fibers. More preferably, the compounds derived from chlorotriazine are introduced into an applied composition after dyeing the keratinous fibers.

In addition, the protection afforded by the treatment according to the invention is durable, that is to say not requiring frequent reapplications of the product.

Another subject of the invention relates to a dyeing process consisting in applying to the keratinous fibers, in particular human keratinous fibers and more particularly the hair, a direct dye composition (A) or an oxidation dye composition (A) during a sufficient time to develop the color, and to follow or precede this application by the application of a composition (B) containing in a cosmetically acceptable medium one or more compounds derived from chlorotriazine. Preferably, the composition (A) is an oxidation dye composition in the presence of one or more oxidizing agents.

Another subject of the invention relates to a dyeing process consisting in applying to the keratinous fibers, in particular human keratinous fibers and more particularly the hair, a direct dye composition (A) or an oxidation dye composition (A) during a sufficient time to develop the color, said composition (A) comprising in a cosmetically acceptable medium one or more compounds derived from chlorotriazine.

Preferably, the composition (A) is an oxidation dye composition in the presence of one or more oxidizing agents.

The different objects of the invention will now be detailed. All the meanings and definitions of the compounds used in the present invention given below are valid for all the objects of the invention.

The cosmetically acceptable medium of the color-protecting compositions according to the invention may for example consist of water or a mixture of water and at least one cosmetically acceptable organic solvent. Examples of organic solvents that may be mentioned are lower C 1 -C 4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and mixtures thereof.

By triazine within the meaning of the invention is meant 1,3,5 triazines, 1,2,5 triazines, 1,2,4 triazines and 1,2,3 triazines. Preferably, the triazines of the invention are 1,3,5 triazines.

The compounds derived from chlorotriazine are preferably soluble in water at a concentration greater than or equal to 0.1% by weight in water at 25 ° C., that is to say that they form, under these conditions, a isotropic solution transparent to the eye. They preferably have a molecular weight of less than 5000 g / mol and even more preferentially less than 2500 g / mol and even more preferentially less than 1000 g / mol.

The compounds derived from chlorotriazine are chosen in particular from the compounds of formula (I): ## STR1 ## ## STR2 ## in which R 1 and R 2, which may be identical or different, denote a hydrogen atom, a halogen atom or a C 1 alkyl radical; -C10, a C1-C10 alkoxy radical, a sulfo radical, a carboxy radical, a hydroxy radical, an amino radical, a C1-C10 aminoalkyl radical, a heterocyclic radical containing from 5 to 10 members and from 1 to 5 identical heteroatoms or different, a group comprising a 1,3,5-triazine ring bearing at least one chlorine atom.

Preferably, R1 and / or R2 denotes a halogen, in particular chlorine, an amino radical, a C1-C10 alkoxy radical, preferably C1-C4, and more particularly methoxy radical.

By heteroatom is meant according to the present invention, oxygen, nitrogen, silicon, phosphorus. Particularly preferred chlorotriazine compounds are chosen from the following compounds: Active Molecular structure 1 2,4-dichloro-6-methoxy-1,3, 5- N / A triazine, CAS = 3638-04-8, C1 marketed by Aldrich under the reference 21353-5 CH3 O 2 PEG (Polyethylene glycol) (Mw CI 600) terminated bis NN (dichlorotriazine) N / where (CH2cH2O) ## STR2 ## 4,6-dichloro-1,3,5-triazine-2-ol HO Cl N CAS =, 168677-46-1, marketed by Pfaltz & Bauer 4 2-amino-4,6-dichlorotriazine , CI ~ 1 NN NH2 CAS = 933-20-0, commercially available from ABCR N 2- (N, N-diethylamino) -4,6-Cl / N-NNCH3 dichlorotriazine marketed by CHC J by ABCR 6 2 Commercially available 4-dichloro-6-morpholino-Cl-1 NN N 1,3,5-triazine and MAYBRIDGE -INT N The compounds derived from chlorotriazine according to the invention may be present in the protective compositions of the neck in concentrations ranging preferably from 0.005 to 30% by weight and more preferably from 0.01 to 15% by weight and even more preferably from 0.3 to 10% by weight relative to the total weight of the composition containing them.

The solvents are preferably present in proportions preferably ranging from about 40% by weight relative to the total weight of the composition, and still more preferably from 3 to 20% by weight approximately.

The composition according to the invention containing the agent or agents for protecting the color of keratin fibers may also contain various adjuvants conventionally used in hair treatment compositions, such as anionic, cationic, nonionic or amphoteric surfactants. , zwitterionic or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, penetration agents , sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.

The compositions according to the invention may in particular contain one or more conditioning agents.

In the context of the present invention, the term "conditioning agent" is understood to mean any agent whose function is to improve the cosmetic properties of the hair, in particular the softness, the disentangling, the touch, the smoothing, the static electricity.

Conditioning agents may be in liquid, semi-solid or solid form such as, for example, oils, waxes or gums. 2,4,6-trichloro-1,3,5-triazine CAS = 108-77-0, sold by Pfaltz & Bauer Cl ClCl 7 According to the invention, the conditioning agents may be chosen from synthetic oils such as polyolefins, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers, ceramide-type compounds, cationic surfactants, fatty amines, saturated fatty acids or sodium esters. fatty acids as well as mixtures of these different compounds.

The synthetic oils are in particular polyolefins, in particular poly-α-olefins and more particularly: polybutene type, hydrogenated or not, and preferably polyisobutene, hydrogenated or otherwise.

Isobutylene oligomers with a molecular weight of less than 1000 and their mixtures with polyisobutylenes with a molecular weight greater than 1000 and preferably between 1000 and 15000 are preferably used.

As examples of poly-α-olefins that may be used in the context of the present invention, mention may be made more particularly of the polyisobutenes sold under the name Perrmyl 99 A, 101 A, 102 A, 104 A (n = 16) and 106A (n = 38) by the company PRESPERSE Inc, or even the products sold under the name ARLAMOL HD (n = 3) by the company ICI (n denoting the degree of polymerization), - of the polydecene, hydrogenated or no.

Such products are sold, for example, under the names ETHYLFLO by the company ETHYL CORP., And ARLAMOL PAO by the company ICI.

The animal or vegetable oils are preferably chosen from the group consisting of sunflower, corn, soybean, avocado, jojoba, squash, grape seed, sesame, hazelnut, fish oil, tricaprocaprylate glycerol, or vegetable or animal oils of formula R90O0R10 wherein R9 represents the residue of a saturated higher fatty acid having 7 to 29 carbon atoms and R10 represents a linear or branched hydrocarbon chain containing from 3 to 30 atoms carbon, especially alkyl or alkenyl, for example, Purcellin oil.

It is also possible to use natural or synthetic essential oils such as, for example, eucalyptus, lavandin, lavender, vetiver, litsea cubeba, lemon, sandalwood, rosemary, chamomile, savory oils, nutmeg, cinnamon, hyssop, caraway, orange, geraniol, cade and bergamot; Waxes are natural substances (animal or plant) or synthetic solid at room temperature (20 ° -25 ° C). They are insoluble in water, soluble in oils and are capable of forming a water-repellent film.

On the definition of waxes, for example, D.D. Dorgan, Drug and Cosmetic Industry, December 1983, pp. 30-33.

The wax or the waxes are chosen in particular from Carnauba wax, Candelila wax, and Alfa wax, paraffin wax, ozokerite, vegetable waxes such as olive wax, rice wax , hydrogenated jojoba wax or absolute waxes of flowers such as the essential wax of blackcurrant sold by the company BERTIN (France), animal waxes such as beeswax, or modified beeswax (cerabellina) ; other waxes or waxy raw materials that can be used according to the invention are, in particular, marine waxes, such as the one sold by SOPHIM under the reference M82, and polyethylene or polyolefin waxes in general.

The cationic polymers that may be used in accordance with the present invention may be chosen from all those already known per se as improving the cosmetic properties of the hair treated with detergent compositions, namely in particular those described in the patent application EP-A-0 337 354 and in French patent applications FR-A-2 270 846, 2 383 660, 2 598 611, 2 470 596 and 2 519 863.

Even more generally, within the meaning of the present invention, the expression "cationic polymer" denotes any polymer containing cationic groups and / or ionizable groups in cationic groups.

The preferred cationic polymers are chosen from those containing units containing primary, secondary, tertiary and / or quaternary amine groups that may either be part of the main polymer chain or may be carried by a lateral substituent directly connected thereto.

The cationic polymers used generally have a number-average molecular weight of between about 500 and 5 × 10 6, and preferably between about 103 and 3 × 10 6.

Among the cationic polymers, mention may be made more particularly of polyamine, polyaminoamide and quaternary polyammonium polymers, cationic polymers derived from polysaccharides. These are known products.

The polymers of the polyamine, polyamidoamide or quaternary polyammonium type which can be used in accordance with the present invention, which may be mentioned in particular, are those described in French Pat. Nos. 2,505,348 or 2,542,997. Among these polymers, mention may be made of: ) homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the following units of formula: ## STR5 ## wherein R 5 R 5 C 5 -C 10 H 2 H 2 H 2 O p 1 X-AAN R 6 1 N + 1 R 8 / R 3 R 4 (II) In which: R3 and R4, which may be identical or different, represent hydrogen or an alkyl group having from 1 to 6 carbon atoms and preferably methyl or ethyl; R5, which may be identical or different, denote a hydrogen atom or a CH3 radical; A, which may be identical or different, represent a linear or branched alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms or a hydroxyalkyl group of 1 to 4 carbon atoms; R6, R7, R8, which may be identical or different, represent an alkyl group having 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group having 1 to 6 carbon atoms; X denotes an anion derived from a mineral or organic acid such as a methosulphate anion or a halide such as chloride or bromide.

The copolymers of family (1) may further contain one or more comonomer-derived units which may be selected from the family of acrylamides, R 5 C C-

H2O H2 ~~

NH NH X

AAN R6 N + ù R8 R3 R4 (IV) R7 (V) methacrylamides, acrylamide diacetones, acrylamides and methacrylamides substituted on the nitrogen by (C1-C4) lower alkyls, acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.

Thus, among these copolymers of the family (1), mention may be made of: the copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate or with a dimethyl hologenide, such as that sold under the name HERCOFLOC by the company Hercules, the copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium chloride described, for example, in the patent application EP-A-080976 and sold under the name BINA QUAT P 100 by the company CIBA GEIGY, the copolymer of acrylamide and methacryloyloxyethyltrimethylammonium methosulphate sold under the name RETEN by the company HERCULES, - vinylpyrrolidone / dialkylaminoalkyl acrylate or methacrylate copolymers quaternized or otherwise, such as the products sold under the name "GAFQUAT" by the company ISP such as "GAFQUAT 734" or "GAFQUAT 755 "or the products referred to as" COPOLYMER 845, 958 and 937 ". These polymers are described in detail in French patents 2,077,143 and 2,393,573, dimethylaminoethyl methacrylate / vinylcaprolactam / vinylpyrrolidone terpolymers, such as the product sold under the name GAFFIX VC 713 by the company ISP, vinylpyrrolidone copolymers. / methacrylamidopropyl dimethylamine marketed in particular under the name STYLEZE CC 10 by ISP. and the quaternized vinylpyrrolidone / dimethylaminopropyl methacrylamide copolymers, such as the product sold under the name "GAFQUAT HS 100" by the company ISP, and the crosslinked polymers of methacryloyloxyalkyl (C1-C4) trialkyl (C1-C3) ammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo or copolymerization being followed by crosslinking with an unsaturated compound olefinic acid, especially methylenebisacrylamide. It is more particularly possible to use a crosslinked acrylamide / methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of said copolymer in mineral oil. This dispersion is marketed under the name SALCARE SC 92 by the company CIBA. It is also possible to use a crosslinked homopolymer of methacryloyloxyethyltrimethylammonium chloride, for example in dispersion in mineral oil or in a liquid ester. These dispersions are sold under the names SALCARE SC 95 and SALCARE SC 96 by CIBA. (2) polymers consisting of piperazinyl units and straight or branched chain alkylene or hydroxyalkylene divalent radicals, optionally interrupted by oxygen, sulfur, nitrogen or aromatic or heterocyclic rings, as well as oxidation and / or quaternization of these polymers. Such polymers are in particular described in French Patents 2,162,025 and 2,280,361; (3) water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides may be crosslinked by an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis-unsaturated derivative, a bishalohydrin, a bis-azetidinium, a bis-haloacyldiamine, an alkyl bis-halide or a oligomer resulting from the reaction of a bifunctional compound reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, an alkyl bis-halide, a epilhalohydrin, a diepoxide or bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 moles per amine group of the polymaoamide; these polyaminoamides can be alkylated or if they contain one or more tertiary amine functional groups, quaternized. Such polymers are described in particular in French Patents 2,252,840 and 2,368,508;

(4) polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents. Mention may be made, for example, of adipic acid-diacoylaminohydroxyalkyldialoylene triamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl. Such polymers are described in particular in French Patent 1,583,363.

Among these derivatives, mention may be made more particularly of the adipic acid / dimethylaminohydroxypropyl / diethylene triamine polymers sold under the name "Cartaretine F, F4 or F8" by the company Sandoz. (5) polymers obtained by reacting a polyalkylene polyamine comprising two primary amine groups and at least one secondary amine group with a dicarboxylic acid chosen from diglycolic acid and saturated aliphatic dicarboxylic acids having from 3 to 8 carbon atoms. The molar ratio between the polyalkylene polylamine and the dicarboxylic acid being between 0.8: 1 and 1.4: 1; the polyaminoamide resulting therefrom being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1.8: 1. Such polymers are described in particular in the patents US 3,227,615 and 2,961,347.

Polymers of this type are in particular sold under the name "Hercosett 57" by the company Hercules Inc. or under the name "PD 170" or "Delsette 101" by the company Hercules in the case of the adipic acid copolymer / epoxypropyl / diethylenetriamine.

(6) cyclopolymers of alkyl diallyl amine or of dialkyl diallyl ammonium, such as homopolymers or copolymers having, as the main constituent of the chain, units of formula (VI) or (VII): / (CH 2) k - (CH 2 wherein k and t are 0 or 1, the sum k + t being 1; R12 denotes a hydrogen atom or a methyl radical; R 10 and R 11, independently of each other, denote an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, a lower amidoalkyl group ( C1-C4) or R10 and R11 may designate, together with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl; Y- is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate, phosphate. These polymers are in particular described in French Patent 2,080,759 and in its addition certificate 2.190.406.

R10 and R11, independently of one another, preferably denote an alkyl group having 1 to 4 carbon atoms.

Among the polymers defined above, mention may be made more particularly of the homopolymer of dimethyldiallylammonium chloride sold under the name "Merquat 100" by the company Nalco (and its counterparts of low molecular weight average) and the chloride copolymers. diallyldimethylammonium and acrylamide sold under the name "MERQUAT 550". (CH2) k - (CH2) t-CR12C (R12) -CH2CH2CH2CH2CH2CH2N + Y- (VII) NR10R11R10 (7) The quaternary diammonium polymer containing recurring units corresponding to the formula:

13 i 15

Wherein R13, R14, R15 and R16, which may be identical or different, represent aliphatic, alicyclic, or arylaliphatic radicals containing from 1 to 20 carbon atoms; carbon or lower hydroxyalkylaliphatic radicals, or else R13, R14, R15 and R16, together or separately, together with the nitrogen atoms to which they are attached, constitute heterocycles optionally containing a second heteroatom other than nitrogen or R13, R14, R15 and R16 represent a linear or branched C1-C6 alkyl radical substituted with a nitrile, ester, acyl, amide or -CO-O-R17-D group or -CO-NH-R17-D where R17 is an alkylene and D a quaternary ammonium group; Al and B1 represent polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated, and may contain, bound to or intercalated in the main chain, one or more aromatic rings, or one or more atoms of oxygen, sulfur or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and X- denotes an anion derived from a mineral or organic acid; A1, R13 and R15 can form with the two nitrogen atoms to which they are attached a piperazine ring; furthermore, if Al denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, B1 may also denote a (CH2) n-CO-D-OC- (CH2) p-n group and p are integer numbers ranging from From 2 to about 20 wherein D denotes: a) a glycol residue of formula: -OZO-, where Z denotes a linear or branched hydrocarbon radical or a group corresponding to one of the following formulas: - (CH2-CH2- 0) x-CH 2 -CH 2 - - [CH 2 -CH (CH 3) -O] y -CH 2 -CH (CH 3) - where x and y denote an integer of 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization; b) a bis-secondary diamine residue such as a piperazine derivative; c) a bis-primary diamine residue of formula: -NH-Y-NH-, where Y denotes a linear or branched hydrocarbon radical, or alternatively the divalent radical - CH 2 -CH 2 -S-S-CH 2 -CH 2 -; d) a ureylene group of formula: -NH-CO-NH-; Preferably, X- is an anion such as chloride or bromide.

These polymers have a number-average molecular weight generally of between 1000 and 100,000. Polymers of this type are described, for example, in French patents 2,320,330, 2,270,846, 2,316,271, 2,336,434 and 2,413,907 and patents. US 2,273,780, 2,375,853, 2,388,614, 2,454,547, 3,206,462, 2,261,002, 2,271,378, 3,874,870, 4,001,432, 3,929,990, 3,966,904, 4,005,193, 4,025. .617, 4,025,627, 4,025,653, 4,026,945 and 4,027,020. Polymers which consist of recurring units having the formula: ## STR2 ## in which R18, R19, R20 and R21 may be used more particularly. , identical or different, denote an alkyl or hydroxyalkyl radical having from 1 to 4 carbon atoms, r and s are integers ranging from 2 to about 20 and X- is an anion derived from a mineral or organic acid. A particularly preferred compound of formula (IX) is that for which R18, R19, R20 and R21, represent a methyl radical and r = 3, s = 6 and X = CI, called Hexadimethrine chloride according to the INCI nomenclature (CTFA). (8) quaternary polyammonium polymers consisting of units of formula (X): ## STR5 ## where ## STR2 ## Wherein R22, R23, R24 and R25, which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, 3-hydroxyethyl, 13-hydroxypropyl or -CH2CH2 (OCH2CH2) pOH radical; where p is 0 or an integer from 1 to 6, with the proviso that R22, R23, R24 and R25 do not simultaneously represent a hydrogen atom, 25 t and u, the same or different, are integers between 1 and 6, v is 0 or an integer between 1 and 34, X- is an anion such as a halide, A is a radical of a dihalide or is preferably -CH2- CH2-O-CH2-CH2-. Such compounds are described in particular in patent application EP-A-122,324. The products "Mirapol A 15", "Mirapol AD1", "Mirapol AZ1" and "Mirapol 175" may for example be mentioned among them. sold by Miranol.

(9) The quaternary vinylpyrrolidone and vinylimidazole polymers such as, for example, the products sold under the names Luviquat FC 905, FC 550 and FC 370 by the company B.A.S.F. (10) Cationic polysaccharides, in particular cationic celluloses and cationic galactomannan gums.

Among the cationic polysaccharides, mention may be made more particularly of cellulose ether derivatives containing quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer and cationic galactomannan gums.

The cellulose ether derivatives containing quaternary ammonium groups described in French Patent 1,492,597. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose having reacted with an epoxide substituted with a trimethylammonium group. The cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, are described in particular in US Pat. No. 4 131 576, such as hydroxyalkyl celluloses, such as hydroxymethyl-, hydroxyethyl- or hydroxypropyl-grafted celluloses in particular. with a salt of methacryloylethyl trimethylammonium, methacrylmidopropyl trimethylammonium, dimethyl diallylammonium.

The cationic galactomannan gums are described more particularly in US Pat. Nos. 3,589,578 and 4,031,307, in particular guar gums containing cationic trialkylammonium groups. For example, guar gums modified with a salt (eg chloride) of 2,3-epoxypropyltrimethylammonium are used. Other cationic polymers which can be used in the context of the invention are cationic proteins or protein hydrolysates. cationic polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and epichlorohydrin, quaternary polyureylenes and chitin derivatives.

The proteins or hydrolysates of cationic proteins are in particular chemically modified polypeptides carrying at the end of the chain, or grafted onto it, quaternary ammonium groups. Their molecular weight may vary for example from 1500 to 10000, and in particular from 2000 to 5000 approximately. Among these compounds, mention may in particular be made of:

collagen hydrolysates bearing triethylammonium groups, such as the products sold under the name "Quat-Pro E" by the company MAYBROOK and referred to in the CTFA dictionary "Triethonium Hydrolyzed Collagen Ethosulfate"; collagen hydrolysates bearing trimethylammonium chloride and trimethylstearylammonium groups, sold under the name "Quat-Pro S" by the company MAYBROOOK and referred to in the CTFA dictionary "Steartrimonium Hydrolyzed Collagen"; animal protein hydrolysates bearing trimethylbenzylammonium groups, such as the products sold under the name Crotein BTA by the company CRODA and referred to in the CTFA dictionary as "Benzyltrimonium hydrolyzed animal protein"; the protein hydrolysates carrying on the polypeptide chain quaternary ammonium groups comprising at least one alkyl radical having from 1 to 18 carbon atoms.

Among these protein hydrolysates, mention may be made inter alia of: - "Croquat L" whose quaternary ammonium groups comprise a C12 alkyl group; "Croquat M" whose quaternary ammonium groups contain Cao-C18 alkyl groups; "Croquat S" whose quaternary ammonium groups contain a C18 alkyl group; "Crotein Q" whose quaternary ammonium groups contain at least one alkyl group having from 1 to 18 carbon atoms. These different products are sold by Croda.

Other quaternized proteins or hydrolysates are, for example, those corresponding to the formula (XI): ## STR5 ## in which X- is an anion of an organic or mineral acid, A denotes a residue of protein derived from hydrolysates of collagen protein, R29 denotes a lipophilic group having up to 30 carbon atoms, R30 represents an alkylene group having 1 to 6 carbon atoms. Mention may be made, for example, of the products sold by the company Inolex under the name "Lexein QX 3000", referred to in the CTFA dictionary as "Cocotrimonium Collagent Hydrolysate".

Mention may also be made of quaternized vegetable proteins such as wheat, corn or soya proteins: as quaternized wheat proteins, mention may be made of those marketed by the company Croda under the names "Hydrotriticum WQ or QM", referred to in the dictionary CTFA "Cocodimonium Hydrolysed wheat protein", "Hydrotriticum QL" called in the CTFA dictionary "Laurdimonium hydrolysed wheat protein", or "Hydrotriticum QS", called in the CTFA dictionary "Steardimonium hydrolysed wheat protein".

Among all the cationic polymers that may be used in the context of the present invention, it is preferred to use cationic cyclopolymers, in particular homopolymers or copolymers of dimethyldiallylammonium chloride, sold under the names MERQUAT 100, MERQUAT 550 and MERQUAT S by NALCO, quaternary vinylpyrrolidone and vinylimidazole polymers, cationic polysaccharides and mixtures thereof.

The silicones that can be used in accordance with the invention are in particular polyorganosiloxanes that are insoluble in the composition and can be in the form of oils, waxes, resins or gums.

Organopolysiloxanes are further defined in Walter Noll's "Chemistry and Technology of Silicones" (1968) Academie Press. They can be volatile or nonvolatile.

When volatile, the silicones are more particularly chosen from those having a boiling point of between 60 ° C. and 260 ° C., and more particularly from:

(i) cyclic silicones containing from 3 to 7 silicon atoms and preferably from 4 to 5. It is, for example, octamethylcyclotetrasiloxane marketed in particular under the name "VOLATILE SILICONE 7207" by UNION CARBIDE or "SILBIONE" 70045 V 2 "by RHODIA CHIMIE, decamethylcyclopentasiloxane marketed under the name" VOLATILE SILICONE 7158 "by UNION CARBIDE," SILBIONE 70045 V 5 "by RHODIA CHIMIE, as well as their mixtures.

Mention may also be made of cyclocopolymers of the dimethylsiloxane / methylakylsiloxane type, such as the "VOLATILE SILICONE FZ 3109" marketed by UNION CARBIDE, of chemical structure: ## STR5 ## with CH 3 CH 2 CH 2 O 3 mention may also be made of mixtures of cyclic silicones with organic compounds derived from silicon, such as the mixture of octamethylcyclotetrasiloxane and tetramethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1 '(hexa-2) 2,2 ', 2', 3,3'-trimethylsilyloxy) bis-neopentane;

(ii) linear volatile silicones having 2 to 9 silicon atoms and having a viscosity less than or equal to 5 × 10 -6 m 2 / s at 25 ° C. It is, for example, decamethyltetrasiloxane marketed in particular under the name "SH 200 "by the company TORAY SILICONE. Silicones included in this class are also described in the article published in Cosmetics and toiletries, Vol. 91, Jan. 76, p. 27-32 - TODD & BYERS "Volatile Silicone fluids for cosmetics".

Non-volatile silicones and more particularly polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, polyorganosiloxanes modified with organofunctional groups and their mixtures are preferably used.

These silicones are more particularly chosen from polyalkylsiloxanes, among which, for example, polydimethylsiloxanes containing trimethylsilyl end groups having a viscosity of 5 × 10 -6 to 2.5 m 2 / s at 25 ° C. and preferably 1 × 10 -5 to 1 m 2 / s may be mentioned. . The viscosity of the silicones is for example measured at 25 ° C. according to ASTM standard 445 Appendix C.

Among these polyalkylsiloxanes, mention may be made, without limitation, of the following commercial products: SILBIONE oils of the 47 and 70 047 series or MIRASIL oils marketed by RHODIA CHIMIE, such as, for example, the 70 047 V 500 000 oil; oils of the MIRASIL series marketed by RHODIA CHIMIE

the oils of the 200 series of Dow Corning, such as, more particularly, the DC200 with a viscosity of 60,000 Cst; - VISCASIL oils from GENERAL ELECTRIC and some oils from SF series (SF 96, SF 18) from GENERAL ELECTRIC.

Mention may also be made of polydimethylsiloxanes containing dimethylsilanol end groups (Dimethiconol according to the CTFA name), such as the oils of the 48 series of the company Rhodia Chimie.

In this class of polyalkylsiloxanes, mention may also be made of the products sold under the names "ABIL WAX 9800 and 9801" by GOLDSCHMIDT, which are poly (C1-C20) alkylsiloxanes. The polyalkylarylsiloxanes are particularly chosen from polydimethyl methylphenylsiloxanes and linear and / or branched polydimethyl diphenylsiloxanes with a viscosity of from 1 × 10 -5 to 5 × 10 -2 m 2 / s at 25 ° C.

Among these polyalkylarylsiloxanes, mention may be made, by way of example, of the products sold under the following names: SILBIONE oils of the 70 641 series from RHODIA CHIMIE; . RHODORSIL 70 633 and 763 series oils from RHODIA CHIMIE; . DOW CORNING 556 COSMETIC GRAD FLUID oil from DOW CORNING; 25. silicones of the PK series from BAYER, such as the product PK20; . silicones of the PN and PH series of BAYER, such as the PN1000 and PH1000 products; . certain oils of the series SF of GENERAL ELECTRIC such as SF 1023, SF 1154, SF 1250, SF 1265. The silicone gums that can be used in accordance with the invention are, in particular, polydiorganosiloxanes having high average molecular masses of between 200 000 and 1,000,000 used alone or as a mixture in a solvent. This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecanes or their mixtures.

The following products may be mentioned more particularly: - polydimethylsiloxane gums - polydimethylsiloxane / methylvinylsiloxane gums, - polydimethylsiloxane / diphenylsiloxane gums, - polydimethylsiloxane / phenylmethylsiloxane gums, - polydimethylsiloxane / diphenylsiloxane / methylvinylsiloxane gums.

More particularly useful products according to the invention are mixtures such as: mixtures formed from a hydroxylated polydimethylsiloxane at the end of the chain (called dimethiconol according to the CTFA code nomenclature) and a cyclic poly-dimethylsiloxane (called cyclomethicone according to the CTFA dictionary nomenclature), such as the product Q2 1401 sold by the company Dow Corning; . mixtures formed from a polydimethylsiloxane gum with a cyclic silicone such as the product SF 1214 Silicone Fluid from the company General Electric, this product is an SF 30 gum corresponding to a dimethicone, having a number average molecular weight of 500,000 solubilized in oil SF 1202 Silicone Fluid corresponding to decamethylcyclopentasiloxane; . mixtures of two PDMS of different viscosities, and more particularly of a PDMS gum and a PDMS oil, such as the product SF 1236 from the company General Electric. The product SF 1236 is the mixture of an SE 30 gum defined above having a viscosity of 20 m 2 / s and an SF 96 oil with a viscosity of 5 × 10 -6 m 2 / s. This product preferably comprises 15% of SE 30 gum and 85% of an SF 96 oil.

The organopolysiloxane resins that can be used in accordance with the invention are crosslinked siloxane systems containing the units: R2SiO212, R3SiO112, RSiO312 and SiO412 in which R represents a hydrocarbon group having 1 to 16 carbon atoms or a phenyl group. Among these products, those particularly preferred are those in which R denotes a lower alkyl radical C1-C4, more particularly methyl, or a phenyl radical.

Among these resins may be mentioned the product sold under the name "Dow Corning 593" or those sold under the names "Silicone Fluid SS 4230 and SS 4267" by the company General Electric and which are silicones of dimethyl / trimethyl siloxane structure.

Mention may also be made of the trimethylsiloxysilicate type resins sold in particular under the names X22-4914, X21-5034 and X21-5037 by the company Shin-Etsu.

The organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon radical.

Among the organomodified silicones, mention may be made of polyorganosiloxanes comprising: polyethyleneoxy and / or polypropyleneoxy groups optionally comprising C 6 -C 24 alkyl groups such as the products called dimethicone copolyol marketed by the company Dow Corning under the name DC 1248 or the oils SILWET L 722, L 7500, L 77, L 711 of the company UNION CARBIDE and the alkyl (C12) methicone copolyol marketed by the company Dow Corning under the name Q2 5200; substituted or unsubstituted amine groups such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning. The substituted amino groups are, in particular, C1-C4 aminoalkyl groups; thiol groups such as the products sold under the names "GP 72 A" and "GP 71" from GENESEE; alkoxylated groups, such as the product marketed under the name "Silicone Copolymer F-755" by SWS Silicones and Abil Wax 2428, 2434 and 2440 by the company GOLDSCHMIDT; hydroxyl groups such as the hydroxyalkyl-functional polyorganosiloxanes described in the French patent application FR-A-85 16334 corresponding to the formula (XII): ## STR5 ## in which the identical R 26 radicals or different are selected from methyl and phenyl radicals; at least 60 mol% of the radicals R 26 denoting methyl; the radical R '26 is a C2-C18 hydrocarbon divalent alkylene chain; p 'is from 1 to 30 inclusive; q 'is from 1 to 150 inclusive; acyloxyalkyl groups such as, for example, the polyorganosiloxanes described in US Pat. No. 4,957,732 and corresponding to formula (X111): ## STR1 ## in which: R27 denotes a methyl, phenyl, -OCOR28, hydroxyl group, only one of the R27 radicals per silicon atom that may be OH; R'27 denotes methyl, phenyl, at least 60 molar percent of all the R4 and R'4 radicals; denotes methyl; R28 denotes C8-C20 alkyl or alkenyl; R "denotes a divalent, linear or branched C2-C18 hydrocarbon alkylene radical; r 'is from 1 to 120 inclusive; p 'is from 1 to 30; q 'is 0 or less than 0.5 p', p '+ q' being from 1 to 30; the polyorganosiloxanes of formula (XII) may contain groups: 1 CH 3 Si-OH O in proportions not exceeding 15% of the sum p + q + r.

anionic groups of the carboxylic type, for example in the products described in the patent EP 186 507 of the company Chisso Corporation, or of the alkylcarboxylic type, such as those present in the product X-22-3701E from the company Shin-Etsu; 2-hydroxyalkylsulfonate; 2-hydroxyalkylthiosulphate such as the products marketed by GOLDSCHMIDT under the names "ABIL S201" and "ABIL S255".

hydroxyacylamino groups, such as the polyorganosiloxanes described in patent application EP 342 834. Mention may be made, for example, of the product Q2-8413 from the company Dow Corning.

According to the invention, it is also possible to use silicones comprising a polysiloxane portion and a portion consisting of a non-silicone organic chain, one of the two portions constituting the main chain of the polymer and the other being grafted onto said chain. main. These polymers are for example described in patent applications EP-A-412 704, EP-A-412 707, EP-A-640 105 and WO 95/00578, EP-A-582 152 and WO 93/23009 and the US Patents 4,693,935, US 4,728,571 and US 4,972,037. These polymers are preferably anionic or nonionic.

Such polymers are, for example, copolymers which can be obtained by radical polymerization from the monomer mixture consisting of: a) 50 to 90% by weight of tert-butyl acrylate; b) 0 to 40% by weight of acrylic acid; c) 5 to 40% by weight of silicone macromer of formula: ## STR3 ##

Where (CH 2) 3 SiO 2 CH 3 CH 3 (XIV) with v being a number from 5 to 700; the percentages by weight being calculated with respect to the total weight of the monomers.

Other examples of grafted silicone polymers are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene type connecting link, mixed polymeric units of the poly (meth) acrylic acid type and of the type alkyl poly (meth) acrylate and polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene type connecting member, polymer units of the poly (meth) acrylate isobutyl type. According to the invention, all the silicones can also be used in the form of emulsions, nanoemulsions or microemulsions.

The polyorganosiloxanes which are particularly preferred according to the invention are the non-volatile silicones chosen from the family of polyalkylsiloxanes with trimethylsilyl end groups, such as oils having a viscosity of between 0.2 and 2.5 m 2 / s at 25 ° C. that the oils of the DC200 series of DOW CORNING, in particular that of viscosity 60 000 Cst, series SILBIONE 70047 and 47 and more particularly the oil 70 047 V 500 000 marketed by RHODIA CHIMIE, the polyalkylsiloxanes end groups dimethylsilanol such as dimethiconol or polyalkylarylsiloxanes such as the SILBIONE 70641 V 200 oil marketed by RHODIA CHIMIE; The organopolysiloxane resin sold under the name Dow Corning 593; polysiloxanes containing amino groups, such as amodimethicones or trimethylsilylamodimethicone; ## STR1 ## According to the present invention, the ceramide-type compounds are in particular ceramides and / or glycoceramides and / or pseudoceramides and / or neoceramides, natural or synthetic.

Ceramide-type compounds are for example described in patent applications DE4424530, DE4424533, DE4402929, DE4420736, WO95 / 23807, WO94 / 07844, EP-A-0646572, WO95 / 16665, FR-2,673,179, EP-A- 0227994 and WO 94/07844, WO94 / 24097, WO94 / 10131, the teachings of which are hereby incorporated by reference.

Particularly preferred ceramide compounds according to the invention are for example: 2-N-linoleoylamino-octadecane-1,3-diol, 2-N-oleoylamino-octadecane-1,3-diol, N-palmitoylamino-octadecane-1,3-diol, 2-N-stearoylamino-octadecane-1,3-diol, 2-N-behenoylamino-octadecane-1,3-diol, 2-N [2-hydroxy-palmitoyl] -aminooctadecane-1,3-diol, 2-N-stearoylaminooctadecane-1,3,4-triol and in particular N-stearoyl phytosphingosine, 2-N -methyl-hexadecane-1,3-diol (bis- (N-hydroxyethyl-N-cetyl) malonamide), - N- (2-hydroxyethyl) -N- (3-cetyloxy-2-hydroxypropyl) amide cetyl acid. N-docosanoyl N-methyl-D-glucamine or mixtures of these compounds.

It is also possible to use cationic surfactants among which may be mentioned in particular: salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated; quaternary ammonium salts; imidazoline derivatives; or oxides of amines with a cationic character.

The quaternary ammonium salts are, for example: those which have the following general formula (XV): + (XV) in which the radicals R 31 to R 34, which may be identical or different, represent a linear or branched aliphatic radical, having 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl. The aliphatic radicals can comprise heteroatoms such as, in particular, oxygen, nitrogen, sulfur, halogens. The aliphatic radicals are, for example, chosen from alkyl, alkoxy, polyoxyalkylene (C 2 -C 6), alkylamide, (C 12 -C 22) alkylamido (C 2 -C 6) alkyl, (C 12 -C 22) alkyl acetate, hydroxyalkyl, with about 1 to 30 carbon atoms; X is an anion chosen from the group of halides, phosphates, acetates, lactates, (C 2 -C 6) alkyl sulphates, alkyl-or-alkylarylsulphonates,

the quaternary ammonium salts of imidazolinium, such as for example that of formula (XVI) below: ## STR2 ## in which R36 represents an alkenyl or alkyl radical containing from 8 to 30 carbon atoms, for example derived from tallow fatty acids, R37 represents a hydrogen atom, a C1-C4 alkyl radical or an alkenyl or alkyl radical containing from 8 to 30 carbon atoms; carbon atoms, R38 represents a C1-C4 alkyl radical, R39 represents a hydrogen atom or a C1-C4 alkyl radical, X is an anion chosen from the group of halides, phosphates, acetates, lactates, alkyl sulphates and alkyls. -or-alkylarylsulfonates. Preferably, R 36 and R 37 denote a mixture of alkenyl or alkyl radicals containing from 12 to 21 carbon atoms, for example fatty acid derivatives of tallow, R 38 denotes methyl and R 39 denotes hydrogen. Such a product is for example marketed under the name REWOQUAT W 75 by the company Degussa,

the quaternary diammonium salts of formula (XVII): ## STR5 ## wherein R 40 denotes an aliphatic radical containing from about 16 to 30 carbon atoms, R 41, R 42 , R43, R44 and R45, which are identical or different, are chosen from hydrogen or an alkyl radical containing from 1 to 4 carbon atoms, and X is an anion chosen from the group of halides, acetates, phosphates, nitrates and methylsulphates. Such diammonium quaternary salts include in particular propane dichloride diammonium.

the quaternary ammonium salts containing at least one ester function + R37 The quaternary ammonium salts containing at least one ester function which can be used according to the invention are, for example, those of formula (XVIII) below: (CrH2rO) z R49 OII ( Wherein R 46 is selected from C 1 -C 6 alkyl radicals and C 1 -C 6 hydroxyalkyl or dihydroxyalkyl radicals; - R47 is chosen from: O - the radical R50 ùC - the radicals R51 hydrocarbon C1-C22 linear or branched, saturated or unsaturated, - the hydrogen atom, - R49 is chosen from: O - the radical R52ùC- - the linear or branched, saturated or unsaturated, C1-C6 hydrocarbon radicals R53, R48, R50 and R52, which are identical or different, are chosen from linear or branched C7-C21 hydrocarbon radicals, saturated or unsaturated; n, p and r, which may be identical or different, are integers ranging from 2 to 6; y is an integer from 1 to 10; x and z, identical or different, are integers ranging from 0 to 10; - X- is a simple or complex anion, organic or inorganic;

with the proviso that the sum x + y + z is 1 to 15, that when x is 0 then R47 is R51 and that when z is 0 then R49 is R53.

The alkyl radicals R46 can be linear or branched and more particularly linear.

Preferably R46 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl radical and more particularly a methyl or ethyl radical.

Advantageously, the sum x + y + z is from 1 to 10. R48 ù C ù (O CnH2n) y N ù (Cp H2p O) X. When R 47 is a hydrocarbon radical R 51, it may be long and have from 12 to 22 carbon atoms or may be short and have from 1 to 3 carbon atoms.

When R49 is a hydrocarbon radical R53, it preferably has 1 to 3 carbon atoms.

Advantageously, R48, R50 and R52, which are identical or different, are chosen from linear or branched, saturated or unsaturated C11-C21 hydrocarbon radicals, and more particularly from linear or branched C11-C21 alkyl and alkenyl radicals, saturated or unsaturated.

Preferably, x and z, identical or different, are 0 or 1. Advantageously, y is equal to 1. Preferably, n, p and r, which are identical or different, are equal to 2 or 3 and even more particularly are equal to 2 .

The anion is preferably a halide (chloride, bromide or iodide) or an alkyl sulphate more particularly methyl sulphate. However, methanesulfonate, phosphate, nitrate, tosylate, an organic acid derivative anion such as acetate or lactate or any other anion compatible ammonium anion can be used.

The X- anion is even more particularly chloride or methylsulfate.

Ammonium salts of formula (XVIII) are more particularly used in which: R 46 denotes a methyl or ethyl radical, x and y are equal to 1; z is 0 or 1; N, p and r are 2; - R47 is selected from: O - the radical R50ùC- - methyl, ethyl or hydrocarbon radicals C14-C22 - the hydrogen atom; - R49 is selected from: O - the radical R52ùC- - the hydrogen atom; R48, R50 and R52, which are identical or different, are chosen from linear or branched, saturated or unsaturated C13-C17 hydrocarbon radicals and preferably from linear or branched, saturated or unsaturated C13-C17 alkyl and alkenyl radicals.

Advantageously, the hydrocarbon radicals are linear.

There may be mentioned, for example, the compounds of formula (XVI) such as the salts (in particular chloride or methyl sulphate) of diacyloxyethyl dimethyl ammonium, of diacyloxyethyl hydroxyethyl methyl ammonium, of monoacyloxyethyl dihydroxyethyl methyl ammonium, of triacyloxyethyl methyl ammonium, of monoacyloxyethyl hydroxyethyl dimethyl ammonium and their mixtures. The acyl radicals preferably have from 14 to 18 carbon atoms and come more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains more than one acyl radical, the latter may be identical or different.

These products are obtained for example by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine optionally oxyalkylenated on fatty acids or mixtures of fatty acids of plant or animal origin or by transesterification of their esters methyl. This esterification is followed by a quaternization using an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (methyl or preferably ethyl), methyl methanesulphonate, methyl paratoluenesulfonate, glycol or glycerol chlorohydrin.

Such compounds are, for example, sold under the names DEHYQUART by the company COGNIS, STEPANQUAT by the company STEPAN, NOXAMIUM by the company CECA, REWOQUAT WE 18 by the company DEGUSSA. It is also possible to use the ammonium salts containing at least one ester function described in US-A-4874554 and US-A-4137180.

Among the quaternary ammonium salts of formula (XV), tetraalkylammonium chlorides, for example dialkyldimethylammonium or alkyltrimethylammonium chlorides, in which the alkyl radical contains from about 12 to 22 carbon atoms, are preferred. carbon, in particular behenyltrimethylammonium, distearyl dimethylammonium, cetyltrimethylammonium, benzyl dimethylstearylammonium chlorides or, on the other hand, stearamidopropyldimethyl (myristylacetate) ammonium chloride sold under the name CERAPHYL 70 by VAN DYK. The saturated fatty acids are more particularly selected from myristic acid, palmitic acid, stearic acid, behenic acid, and isostearic acid.

The fatty acid esters are in particular the carboxylic acid esters, in particular the mono, di, tri or tetracarboxylic esters.

The esters of monocarboxylic acids are different from those of the invention and are in particular the monoesters of saturated or unsaturated aliphatic acids, linear or branched C1-C26 and saturated or unsaturated aliphatic alcohols, linear or branched C1-C26 , the total carbon number of the esters being greater than or equal to 10.

Among the monoesters, mention may be made of dihydroabiethyl behenate; octyldodecyl behenate; isoketyl behenate; cetyl lactate; C12-C15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate oleyl lactate; (iso) stearyl octanoate; isocetyl octanoate octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methyl ricinoleate acetyl; myristyl stearate; octyl isononanoate; 2-ethylhexyl isononate; octyl palmitate; octyl pelargonate; octyl stearate; octyldodecyl erucate; oleyl erucate; ethyl palmitates and isopropyl palmitate, ethyl-2-hexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl, 2-octyldodecyl myristate; hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isostearyl neopentanoate, isodecyl neopentanoate.

It is also possible to use esters of C 4 -C 22 di or tricarboxylic acids and of C 1 -C 22 alcohols and esters of mono di or tricarboxylic acids and of C 2 -C 26 di, tri, tetra or pentahydroxy alcohols.

These include: diethyl sebacate; diisopropyl sebacate diisopropyl adipate; di-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; dicaprylate propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisotearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate.

Among the esters mentioned above, it is preferred to use ethyl and isopropyl palmitates, ethyl-2-hexyl palmitate, 2-octyldecyl palmitate and alkyl myristates such as isopropyl myristate. butyl, cetyl, 2-octyldodecyl, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate and isononyl isononanate, cetyl octanoate, isostearyl neopentanoate, isodecyl neopentanoate.

The fluorinated oils are for example perfluoropolyethers described in particular in the patent application EP-A-486135 and the fluorohydrocarbon compounds described in particular in the patent application WO 93/11103. The teaching of these two applications is fully included in this application for reference.

The term fluorohydrocarbon compounds refers to compounds whose chemical structure includes a carbon skeleton some of whose hydrogen atoms have been substituted by fluorine atoms.

The fluorinated oils may also be fluorocarbons such as fluoroamines, for example perfluorotributylamine, fluorinated hydrocarbons, for example perfluorodecahydronaphthalene, fluoroesters and fluoroethers;

Perfluoropolyethers are for example sold under the trade names FOMBLIN by the company MONTEFLUOS and KRYTOX by the company DU PONT.

Among the fluorohydrocarbon compounds, mention may also be made of fluorinated fatty acid esters such as the products sold under the name NOFABLE FO by the company Nippon Oil. It is of course possible to use mixtures of conditioning agents.

The preferred conditioning agents according to the invention are cationic polymers and silicones.

According to the invention, the conditioning agent (s) may represent from 0.001% to 20% by weight, preferably from 0.01% to 10% by weight and more particularly from 0.1% to 3% by weight relative to total weight of the final composition 40.

The compositions protecting the color of the keratinous fibers according to the invention may be in the form of aqueous or aqueous-alcoholic lotions. The cosmetic compositions according to the invention may also be in the form of an oil, a gel, a milk, a cream, an emulsion or a mousse.

The compositions for protecting the color of the keratin fibers may be packaged in various forms, in particular in vaporizers, pump bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in the form of a foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for the treatment of the hair. The pH of the protective composition of the keratinous fibers generally varies from 1 to 11. It is preferably from 2 to 6, and may be adjusted to the desired value by means of acidifying or basifying agents well known from the state of the art. compositions applied to keratinous fibers. Among the alkalinizing agents that may be mentioned, for example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, hydroxyalkylamines and ethylenediamines oxyethylenated and / or oxypropylenated, sodium or potassium hydroxides and compounds of the following formula: R54 R56 RN - R58N -

Wherein R58 is a propylene moiety optionally substituted with a hydroxyl group or a C1-C4 alkyl radical; R54, R55, R56 and R57, which may be identical or different, represent a hydrogen atom, a C1-C4 alkyl radical or a C1-C4 hydroxyalkyl radical. The acidifying agents are conventionally, for example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, or acids. sulfonic. The subject of the invention is also a method for protecting the color of artificially dyed keratin fibers from washing, characterized in that it consists in applying to said fibers, preferably before or after dyeing, one or more compounds derived from chlorotriazine or at least one composition comprising in a cosmetically acceptable medium one or more compounds derived from chlorotriazine.

Preferably, the composition comprising the compound (s) derived from chlorotriazine will be applied to said fibers after the dyeing step.

It is also possible to provide a rinse step and / or a shampoo washing step before or after the application of the composition containing the chlorotriazine derivative compound (s). The process according to the invention may comprise an additional step of total or partial drying of the keratinous fibers with a dryer.

According to one particular form of the invention, the method for protecting the color of the keratinous fibers may comprise a step of heating the composition comprising the chlorotriazine derivative compound (s) which will then be applied directly to the keratinous fibers. The temperature will preferably be less than or equal to 120 ° C.

According to one particular form of the invention, the method for protecting the color of the keratinous fibers may comprise a step of heating the keratinous fibers during or after application of the composition comprising the compound (s) derived from chlorotriazine.

The heating of the keratinous fibers may for example be carried out by means of an iron, a liquid water / steam mixture or by means of a heating helmet.

The heating iron useful in the context of the invention is a heating iron 25 conventionally used in the hair field. Such an iron, for example a curling iron or a straightening iron, is well known in the field of hair treatment. For example, irons useful for practicing the present invention are flat or round irons described in US Pat. Nos. 4,103,145, 4,308,878, 5,983,903, 5,957,140 and 5,494,058. Application of the iron can be made by successive separate keys of a few seconds, or by progressive displacement or sliding along the wicks. It is possible between the application of the composition protecting the color and the application of the heating iron on the keratinous fibers to provide a pause time. Said pause time preferably will vary from 30 seconds to 60 minutes and more preferably from 1 to 30 minutes. The temperature is preferably from 60 ° C to 120 ° C.

The liquid water / steam mixture useful in the context of the invention generally has a temperature of at least 35 ° C. The liquid water / steam mixture constitutes a mist. Said mixture may additionally contain at least one other gas such as oxygen or nitrogen, mixtures of gases such as air or else other vaporizable compounds. The temperature of the liquid water / steam mixture is preferably greater than or equal to 40 ° C, and more preferably between 40 ° C and 75 ° C.

Preferably, the liquid water / steam mixture is brought into contact with the fiber for a period ranging from 1 second to 1 hour, and even more preferably from 5 minutes to 15 minutes. Of course, the application of said mixture can be repeated several times on the same fiber, each operation being carried out according to a duration as indicated above. More preferably, the composition containing zinc-based compounds is first applied to the hair, then the wicks thus impregnated are subjected to the action of the liquid-water / steam mixture according to the conditions mentioned above, and then the wicks thus treated for example by sending on or through them a stream of cold air or air at room temperature.

The production of the liquid water / steam mixture used according to the invention can be carried out using any apparatus known per se and provided for this purpose. However, according to the present invention, use is preferably made of an apparatus comprising at least one steam generator directly connected to a helmet diffusing on the keratinous fibers, in particular human hair, the mixture of liquid water and water vapor. As a type of apparatus, use will be made more particularly that sold under the name MICROMIST by TAKARA BELMONT.

Another subject of the invention relates to a dyeing method consisting in applying to the human keratinous fibers and more particularly to the hair, a direct dye composition (A) or an oxidation dye composition (A) in the presence, if appropriate, of one or more oxidizing agents, for a time sufficient to develop the color, and to precede or follow this application by the application of a composition (B) containing in a cosmetically acceptable medium one or more compounds derived from chlorotriazine such as previously defined.

The application of the composition (A) may be followed by rinsing and / or drying the keratinous fibers.

The application of the composition (B) may be followed by rinsing and / or drying the keratinous fibers. The composition (B) may be previously heated under the same conditions defined above. The application of the composition (B) may be followed by heating the keratinous fibers under the same conditions defined above.

Preferably, the composition (B) will be applied after the application of the composition (A) direct dye or oxidation. The composition (B) comprising the chlorotriazine derivative compound (s) may be applied immediately after staining or in a delayed manner. By deferred, we mean an application being a few hours, a day or several days (from 1 to 15 days) after coloring. Preferably, the composition (B) will be applied immediately after staining the keratinous fibers. ; the applications of said composition being able to be repeated between two colorings.

In the case of direct lightening dyeing, the dyeing compositions (A) result from the mixing at the time of use of a dye composition containing one or more direct dyes and a composition containing one or more oxidizing agents. .

In the case of oxidation dyeings, the dyeing compositions (A) result from the mixing at the time of use of a dye composition (A3) containing one or more oxidation bases and optionally one or more couplers and / or a or more direct dyes and a composition (A4) containing one or more oxidizing agents.

Another subject of the invention relates to a dyeing process consisting in applying to the keratinous fibers, in particular human keratinous fibers and more particularly the hair, a direct dye composition (A) or an oxidation dye composition (A) during a sufficient time to develop the color, said composition (A) comprising in a cosmetically acceptable medium one or more compounds derived from chlorotriazine.

The direct dyes are more particularly compounds that absorb light radiation in the visible range (400-750 nm). They may be of a nonionic, anionic or cationic nature.

Generally, the direct dyes are chosen from nitrobenzene dyes, azo, anthraquinone, naphthoquinone, benzoquinone, phenotiazine, indigo, xanthene, phenanthridine dyes, phthalocyanine dyes, and triarylmethane dyes, alone or as mixtures.

Among the nitrated benzene dyes, mention may be made of the following red or orange compounds: 1-hydroxy-3-nitro-4-N- (γ-hydroxypropyl) amino benzene, N-03-hydroxyethyl) amino-3-nitro 4-amino benzene, 1-amino-3-methyl-4-N-O-hydroxyethyl) amino-6-nitro benzene, 1-hydroxy-3-nitro-4-N-O-hydroxyethyl-amino benzene 1,4-diamino-2-nitrobenzene, 1-amino-2-nitro-4-methylamino benzene, N-O-hydroxyethyl) -2-nitro-para-phenylenediamine, 1-amino-2-nitro-4 - ([3-hydroxyethyl) amino-5-chlorobenzene, 2-nitro-4-amino-diphenylamine, 1-amino-3-nitro-6-hydroxybenzene, 1 - ((3-aminoethyl) amino -2-nitro-4-03-hydroxyethyloxy) benzene, 1 - ([3, y-dihydroxypropyl) oxy-3-nitro-4 - ([3-hydroxyethyl) amino benzene, 1-hydroxy-3-nitro 4-aminobenzene, 1-hydroxy-2-amino-4,6-dinitrobenzene, 1-methoxy-3-nitro-4-yl-hydroxyethyl) amino benzene, 2-nitro-4'-hydroxydiphenylamine, -amino-2-nitro-4-hydroxy-5-methylbenzene, alone or in mixtures.

With regard to the nitrobenzene direct dyes, it is possible to use dyes of this type, yellow and green-yellow, such as for example 1-13-hydroxyethyloxy-3-methylamino-4-nitrobenzene, 1-methylamino-2 -Nitro-5-03, 'dihydroxypropyl) oxybenzene, 1- [(3-hydroxyethyl) amino-2-methoxy-4-nitrobenzene, 1 - ((3-aminoethyl) amino-2-nitro-5- methoxybenzene, 1,3-di ((3-hydroxyethyl) amino-4-nitro-6-chlorobenzene, 1-amino-2-nitro-6-methylbenzene, 1- (3-hydroxyethyl) ) amino-2-hydroxy-4-nitrobenzene, N - ([3-hydroxyethyl) -2-nitro-4-trifluoromethylaniline, 4 - ([3-hydroxyethyl) amino-3-nitro-benzenesulfonic acid, l 4-ethylamino-3-nitro-benzoic acid, 4- ([3-hydroxyethyl) amino-3-nitro-chlorobenzene, 4- (3-hydroxyethyl) amino-3-n-butromethylbenzene, 4- ( [3, γ-dihydroxypropyl) amino-3-nitro-trifluoromethylbenzene, 1 - ([3-ureidoethyl) amino-4-nitrobenzene, 1,3-diamino-4-nitrobenzene, 1-hydroxy-2-amino -5-nit robenzene, 1-amino-2- [tris (hydroxymethyl) methyl] amino-5-nitro-benzene, 1- [(3-hydroxyethyl) amino-2-nitrobenzene, 4- (3-hydroxyethyl) amino) 3-nitrobenzam ide.

It is likewise possible to use blue or violet nitrobenzene dyes, such as, for example, 1- (R-hydroxyethyl) amino-4-N, N-bis- (R-hydroxyethyl) amino 2-nitrobenzene, the (4-hydroxypropyl) amino 4-N, N-bis - ([3-hydroxyethyl) amino-2-nitrobenzene, 1- (3-hydroxyethyl) amino-4- (N-methyl, N- [3-hydroxyethyl) amino 2-Nitrobenzene, 1- (N-ethyl, N- [3-hydroxyethyl) amino] -Nitrobenzene, 1- (N- [3-yl-dihydroxypropyl) amino) -4- (3-hydroxyethyl) amino- ethyl, N-13-hydroxyethyl) amino 2-nitrobenzene, 2-nitroparaphenylenediamines of the following formula: NR 6 R 7 in which: R 6 represents a C 1 -C 4 alkyl radical, a [3-hydroxyethyl or [3-hydroxypropyl or hydroxypropyl; R5 and R7, which may be identical or different, represent a [3-hydroxyethyl, 13-hydroxypropyl, γ-hydroxypropyl or β, γ-dihydroxypropyl radical, at least one of R6, R7 or R5 being radical radicals. hydroxypropyl and R6 and R7 can not simultaneously denote a 33-hydroxyethyl radical when R6 is a γ-hydroxypropyl radical, such as those described in French Patent FR 2,692,572.

It is recalled that azo dyes are compounds comprising in their structure at least one sequence N = N- not included in a ring; the methine dyes are compounds comprising in their structure at least one sequence - C = C- not included in a ring; the azomethine dyes are compounds comprising in their structure at least one sequence C = N- not included in a ring.

The dyes derived from triarylmethane comprise in their structure at least one following sequence: A designating an oxygen or nitrogen atom

The xanthene dyes comprise in their structure at least one sequence of formula: The phenanthridine dyes comprise in their structure at least one sequence of formula The phthalocyanine dyes comprise in their structure at least one sequence of formula:

The phenol azine dyes comprise in their structure at least one following sequence: The direct dyes may also be chosen from basic dyes such as those listed in the Color Index, 3rd edition, in particular under the names "Basic Brown 16", "Basic Brown 17 "," Basic Yellow 57 "," Basic 10 Red 76 "," Basic Violet 10 "," Basic Blue 26 "and" Basic Blue 99 "; or among the acid direct dyes, listed in the Color Index, 3rd edition, under the names "Acid Orange 7", "Orange Acid 24", "Acid Yellow 36", Acid Red 33 "," Acid Red 184 "," Acid Black 2 "," Acid Violet 43 ", and" Acid Blue 62 ", or cationic direct dyes such as those described in patent applications WO 95/01772, WO 95/15144 and EP 714954 and in particular Basic Red 51 Basic Orange 31, Basic Yellow 87, the contents of which form an integral part of the present invention.

When present, the direct dye (s) preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dyeing composition, and still more preferably from 0.005 to 6% by weight approximately of this weight.

The oxidation bases may be chosen from the oxidation bases conventionally used in oxidation dyeing, among which may be mentioned paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.

Among the para-phenylenediamines, para-phenylenediamine, paratoluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine and 2,6-diethyl-para-phenylenediamine may be mentioned by way of example; , 2,5-dimethyl-para-phenylenediamine, N, N-dimethyl-para-phenylenediamine, N, N-diethyl-para-phenylenediamine, N, N-dipropyl-para-phenylenediamine, 4-amino-N, N-diethyl-3-methylaniline, N, N-bis- (33-hydroxyethyl) paraphenylenediamine, 4-N, N-bis- (33-hydroxyethyl) amino-2-methylaniline, 4-N, N-bis (33-hydroxyethyl) amino-2-chloroaniline , 2-33-hydroxyethyl paraphenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-O-hydroxy-propyl) paraphenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N, N-dimethyl-3-methyl-para-phenylenediamine, N, N- (ethyl, 33-hydroxyethyl) paraphenylenediamine, N- ( 3, γ-dihydroxypropyl) para-phenylenediamine, N- (4'-aminophenyl) paraphenylenediamine, N-phenyl-para-phenylenediamine, 2-33-hydroxyethyloxy-para-phenylenediamine, 2-33-acetylaminoethyloxy-para-phenylenediamine, N-03-methoxyethyl-para-phenylenediamine, and their addition salts with an acid.

Of the para-phenylenediamines mentioned above, paraphenylenediamine, paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2-3-hydroxyethyl paraphenylenediamine, 2-3-hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, , 6-diethyl paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, N, N-bis- (33-hydroxyethyl) paraphenylenediamine, 2-chloro-para-phenylenediamine, 2-3-acetylaminoethyloxy-para-phenylenediamine, and their addition salts with a acid.

Among the bis-phenylalkylenediamines, N, N'-bis- (3-hydroxyethyl) N, N'-bis- (4'-aminophenyl) -1,3-diamino propanol may be mentioned by way of example, N, N'-bis-03-hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- 03-hydroxyethyl) N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methylaminophenyl) tetramethylenediamine, N, N'-bis (ethyl) N, N ' -bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis- (2,5-diamino phenoxy) -3,5-dioxaoctane, and their addition salts with an acid.

Among the para-aminophenols, para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro phenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-hydroxyethylaminomethyl) phenol, 4 amino-2-fluoro phenol, and their addition salts with an acid.

Among the ortho-aminophenols, 2-amino phenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-amino phenol may be mentioned by way of example, and their addition salts with an acid. Among the heterocyclic bases, there may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.

Among the pyridine derivatives, mention may be made more particularly of the compounds described for example in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino-3-amino pyridine, 2,3-diamino-6-methoxy pyridine, 2-03-methoxyethyl) amino-3-amino-6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid. Among the pyrimidine derivatives, there may be mentioned more particularly the compounds described for example in DE 2,359,399; JP 88-169,571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765 such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine , 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of pyrazolo [1,5-a] pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine; pyrazolo [1,5-a] pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo [1,5-a] pyrimidine-3,5-diamine; 3-amino pyrazolo [1,5-a] pyrimidin-7-ol; 3-amino pyrazolo [1,5-a] pyrimidin-5-ol; 2- (3-amino pyrazolo [1,5-a] pyrimidin-7-ylamino) ethanol, 2- (7-amino pyrazolo [1,5-a] pyrimidin-3-ylamino) - ethanol, 2 - [(3-amino-pyrazolo [1,5-a] pyrimidin-7-yl) - (2-hydroxyethyl) amino] ethanol, 2 - [(7-amino-pyrazolo) [1,5-a] pyrimidin-3-yl) - (2-hydroxyethyl) amino] ethanol, 5,6-dimethyl pyrazolo [1,5-a] pyrimidine-3,7 -diamine, 2,6-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine, 2,5-N-7-N-7-tetramethyl-pyrazolo [1,5-a] -pyrimidine -3,7-diamine, 3-amino-5-methyl-7-imidazolylpropylamino pyrazolo [1,5-a] pyrimidine and their addition salts with an acid and their tautomeric forms, when there is an equilibrium 35 tautomeric. Among the pyrazole derivatives, mention may be made more particularly of the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43. 988 such as 4,5-diamino-1-methyl pyrazole, 4,5-diamino-1-yl-hydroxyethyl) pyrazole, 3,4-diamino pyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4,5-diamino-1,3-dimethyl pyrazole, 4,5-diamino-3-methyl-1-phenyl pyrazole, 4,5-diamino-1-methyl-3-phenyl pyrazole, 4-amino-1,3 dimethyl 5-hydrazino pyrazole, 1-benzyl 4,5-diamino-3-methyl pyrazole, 4,5-diamino-3-tert-butyl-1-methyl pyrazole, 4,5-diamino-1-tert-butyl-3- methyl pyrazole, 4,5-diamino-1-yl-hydroxyethyl) 3-methyl pyrazole, 4,5-diamino-1-ethyl-3-methyl-pyrazole, 4,5-diamino-1-ethyl-3- (4'-methoxyphenyl) pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethyl pyrazole, 4,5-diamino-3-hydroxymethyl-1-methyl-pyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropyl pyr azole, 4,5-diamino-3-methyl-1-isopropyl pyrazole, 4-amino-5- (2'-aminoethyl) amino-1,3-dimethyl pyrazole, 3,4,5-triamino pyrazole, 1-methyl 3,4,5-triamino pyrazole, 3,5-diamino-1-methyl-4-methylamino pyrazole, 3,5-diamino-4-yl-hydroxyethyl) amino-1-methyl pyrazole, and their addition salts with an acid .

As pyrazole derivatives, mention may also be made of diamino-N, N-dihydropyrazolopyrazolones and especially those described in application FR 2 886 136 such as the following compounds and their addition salts. Among these compounds, the preferred ones are: 2,3-Diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one, 2-amino-3-ethylamino-6, 7-Dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one, 2-amino-3-isopropylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one, 2-amino-3- (pyrrolidin-1-yl) -6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one, 4,5-diamino 1,2-dimethyl-1,2-dihydro-pyrazol-3-one, 4,5-diamino-1,2-diethyl-1,2-dihydro-pyrazol-3-one, 4,5-diamino-1 2-di- (2-hydroxyethyl) -1,2-dihydro-pyrazol-3-one, 2-amino-3- (2-hydroxyethyl) amino-6,7-dihydro-1H, 5H-pyrazolo [1 2-a] pyrazol-1-one, 2-amino-3-dimethylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one, 2,3-diamino-1-ene 5,6,7,8-tetrahydro-1H, 6H-pyridazino [1,2-a] pyrazol-1-one, 4-amino-1,2-diethyl-5- (pyrrolidin-1-yl) -1 2-Dihydro-pyrazol-3-one, 4-amino-5- (3-dimethylamino-pyrrolidin-1-yl) -1,2-diethyl-1,2-dihydro-pyrazol-3-one, 2, 3-diamino-6-hydroxy-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one,

As heterocyclic bases or other oxidation dyes other than 3-amino-2-methylamino-6-methoxypyridine or one of its addition salts with an acid, 4,5-diamino-1-one may be preferably used. hydroxyethyl) pyrazole and / or 2,3-diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one and their addition salts.

When used, these oxidation bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.

The oxidation dyeing compositions according to the invention may also contain at least one coupler and / or at least one direct dye, in particular for modifying the shades or enriching them with glints.

The couplers that can be used in the oxidation dyeing compositions according to the invention can be chosen from the couplers conventionally used in oxidation dyeing, among which mention may be made in particular of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives, indazole derivatives, pyrazolo [1,5-b] -1,2,4-triazole derivatives, pyrazolo derivatives [ 3,2-c] -1,2,4-triazole, benzimidazole derivatives, benzothiazole derivatives, benzoxazole derivatives, 1,3-benzodioxole derivatives and pyrazolones, and their addition salts with a acid.

These couplers are more particularly chosen from 2-methyl-5-aminophenol, 5-N-O-hydroxyethylamino-2-methylphenol, 3-amino phenol, 1,3-dihydroxybenzene, 1,3-dihydroxybenzene, dihydroxy-2-methyl benzene, 4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-hydroxyethyloxybenzene, 2-amino-4-hydroxyethylamino) -methoxy benzene, 1,3 diamino benzene, 1,3-bis- (2,4-diaminophenoxy) propane, sesamol, α-naphthol, 2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy N-methylindole, 6-hydroxyindoline, 6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine, 1-N- (hydroxyethyl) amino-3,4-methylenedioxybenzene, 2, 6 bis ((3-hydroxyethylamino) toluene, 2,6-dihydroxy-4-methyl pyridine, 1-H 3 -methyl pyrazole-5-one, 1-phenyl-3-methyl-pyrazole-5-one, and their addition salts with an acid.

When they are present, the coupler (s) preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately of this weight.

The dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or mixtures thereof, inorganic or organic thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example silicones, film-forming agents, preservatives, opacifying agents.

Of course, one skilled in the art will take care to choose this or these optional additional compounds such that the advantageous properties intrinsically attached to the oxidation dyeing composition according to the invention are not, or not substantially impaired by the addition or additions envisaged.

The dye composition according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratinous fibers, and especially human hair.

The oxidizing agent used in the lightening direct dyeing (direct dyeing with an oxidizing agent) or in the oxidation dyeing is preferably chosen from the group formed by hydrogen peroxide, urea peroxide and bromates. or ferricyanides of alkali metals, persalts such as perborates and persulfates. It is also possible to use one or more oxidation-reduction enzymes such as laccases, peroxidases and 2-electron oxidoreductases (such as uricase) as oxidizing agent, if appropriate in the presence of their respective donor or cofactor. Hydrogen peroxide is preferred.

According to a particular embodiment of the invention, the method of the invention may be used on hair sensitized by hair treatments other than those of the invention mentioned above.

The subject of the invention is also a multi-component (or multi-compartment) coloring agent or kit comprising at least one first component (or compartment) comprising a composition (B) containing, in a cosmetically acceptable aqueous medium, one or more compounds chlorotriazine derivatives and a second component (or compartment) comprising a dye composition (A) comprising at least one oxidation dye and / or at least one direct dye, these 2 components possibly being associated with a third component (or compartment) comprising one or more oxidizing agents.

The subject of the invention is also a multicomponent (or multi-compartment) coloring agent or kit comprising at least a first component (or compartment) comprising a composition (A) containing, in a cosmetically acceptable aqueous medium, one or more compounds chlorotriazine derivatives and at least one oxidation dye and / or at least one direct dye, optionally associated with a second component (or compartment) comprising one or more oxidizing agents.

The invention will now be more fully illustrated with the aid of the following examples which can not be considered as limiting.

EXAMPLES The compositions according to the invention that can be used for protecting the coloration may be exemplified by the following non-exhaustive list: EXAMPLE 1 Rinsed lotions The rinsed lotions are prepared from the following ingredients in the following proportions indicated in% by weight. 1 2 3 4 5 6 Ethanol 15% - 15% 5% 10% 10% Active 1 5% - - - - Active 2 - 5% - - - Active 3 - - 5% - - Active 4 - - - 5% - Active 5 - - - - 5% Active 6 5% Preservative qs qs qs qs qs qs Perfume qs qs qs qs qs qs Water qsp 100% qsp qsp qsp qsp qsp 100% 100% 100% 100% 100% Active Molecular structure15 1 2 4-dichloro-6-methoxy-CH3 ON / N-1,3,5-triazine, CAS = 3638-Cl 04-8, sold by Aldrich under the reference 21353-5 2 PEG (Polyethylene glycol) (CI Cl Mw 600 ) terminated bis NN (dichlorotriazine) N o- (CH 2 CH 2 O) ~ o / \ NNN CI CI 3 4,6-dichloro-1,3,5-triazine-2 HO Cl NN ol CAS =, 168677-46-1, marketed by Pfaltz & Bauer 4 2-amino-4,6-Cl / NN NH 2 dichlorotriazine, CAS = 933-120-0, marketed by N ABCR 2- (N, N-diethylamino) -4,6-Cl / N Dichlorotriazine ## STR1 ## marketed by ABCR 6 2,4-dichloro-6-morpholino-Cl / 1 NN N 1,3,5-triazine marketed by MAYBRIDGE -INT N Demonstration of the protective effect of color Coloring step:

A mixture of the composition of Table 1 below and hydrogen peroxide (L'Oreal Professional Peroxide 20 volumes at 6%) is applied weight for weight on strands of 90% white hair permed in an amount sufficient to be safe. well impregnate the wicks (in this case 10 g of dye mixture / g of wick). The break time is 15 minutes on each side of the wick. The locks are then rinsed with water, then washed with DOP Chamomile shampoo and dried.

Table 1 composition 1 colorant amounts 0/0 Oleyl alcohol polyglycerolated with 2 moles of glycerol 4g Oleyl alcohol polyglycerolated with 4 moles of glycerol (78% 5.69g MA) Oleic acid 3g Oleic amine 2 EO marketed under the name 7g of ETHOMEEN 012 by AKZO7 g Laurylamino diethylaminopropyl succinamate, 3g 55% sodium salt MA Oleic alcohol 5g Oleic acid diethanolamide 12g Propylene glycol 3.5g Ethyl alcohol 7g Dipropylene glycol 0.5g Propylene glycol monomethyl ether 9g Sodium metabisulphite 35% aqueous solution % MA 0.455g Ammonium acetate 0.8g Antioxidant, sequestering qs Fragrance, preservative qs p -Phenylene diamine 6.10-4mo1 4-amino-2-hydroxytoluene 6.10-4mol Ammonia at 20% NH3 10g Demineralized water qs 100g Protective treatment steps: The procedure is as follows: - application of the lotion 1 in sufficient quantity to be well impregnated on the hair (in this case 2.5 grams per gram of hair) on the colored hair - activation of the treatment 35 minutes at 60 ° C Stages of tenacity after washes with shampooinqs: The treated locks then undergo a test of tenacity washings with shampoos compared to untreated colored locks.

For this purpose, the locks undergo up to 8 successive Dop Camomile shampoos with intermediate drying.

Evaluation of the protection

The color degradation after washings of the treated and untreated locks was visually evaluated against unwashed colored locks.

Spectro-colorimetric monitoring accompanies these assessments. Measurements are made using the MINOLTA CM2022 spectrocolorimeter up to 8 washes:

The degradation caused by washes is expressed as AE AE (x shampoos - 0 shampoo) = - q (AL * 2 + Aa * 2 + Ab * 2) x represents the number of shampoos

The protection is then expressed by a difference in AE between the treated and untreated locks.

35 Results:

After exposure to the washdown tenacity test, there is a significant degradation of the color of the untreated colored locks.

Surprisingly, it is observed that after this same test, the use of the active agent 1 of the invention provides a significant protection of the color compared with the untreated locks. These results are confirmed by colorimetric measurements which indicate a significant AE gain over the untreated lock.

Results of color protection after washing wastage test Wick JE vs Gain in # of JE with locks compared to non-washed lock untreated (ref 1) Check lock untreated after 5 6.9 - shampoos Wick treated with lotion 1 after 5 4.5 2.4 shampoos Untreated control after 8 shampoos 10.2 - Wick treated with lotion 1 after 8 6.3 3.9 shampoos The smaller the AE, the less color is lost through washing. EXAMPLE 2 Rinsed Compositions Usable According to the Invention Shampoos are prepared from the following ingredients in the proportions indicated in% by weight of active ingredient. 7 8 Sodium laureth sulfate (') 30% MA 4% MA Coco-betaine (2) 4% MA 5.4% MA Cocamide MIPA (3) 2% MA - Coco glucoside [4] 5% MA Lauryl ether ( 0E) sodium carboxylate 3% MA [5] PDMS (MW 250,000) (6) 2% MA 1% MA Active 1 5% MA Active 2 5% MA Sodium cetearyl sulphate (') 0.8% MA Polyquaternium- 10 (8) 0.4% MA Polyquaternium-6 (9) 0.5% MA Carbomer (10 ~ 0.2% MA Propylene Glycol 0.1 Preservatives qs qs Perfume qs qs Water qs 100% 100% MA: active ingredient

(1) TEXAPON N 702 sold by the company COGNIS, (2) DEHYTON AB 30 OR sold by the company COGNIS, (3) EMPILAN CIS marketed by the company HUNSTMAN, (4) PLANTACARE 818 UP marketed by COGNIS (5) AKYPO RLM 45 CA marketed by KAO (6) MIRASIL DM 500 000 marketed by RHODIA, (7) LANETTE E marketed by COGNIS, (8) UCARE POLYMER JR 400 marketed by RHODIA CHIMIE, (9) MERQUAT 100 marketed by the company NALCO, (10) CARBOPOL 980 marketed by the company NOVEON. Example 3: rinse care composition usable according to the invention The composition is prepared from the following ingredients in the following proportions given in% by weight.

9 10 myristyl / cetyl / stearyl myristate / stearate blend 4% myristyl / cetyl / stearyl (1) cetylstearyl alcohol (C16 / C18 50/50) (2) 1% 1% behenyltrimethylammonium chloride (3) 4 % MA 4% MA Active 1 5% MA Active 2 5% MA Poly dimethylsiloxane with aminoethyl groups 2% MA 2% MA iminopropyl cationic emulsion4) Preservative qs qs Perfume qs qs Water qs 100% 100% MA: active ingredient (1) MIRACETI sold by the company LASERSON (2) LANETTE O OR marketed by the company COGNIS (3) GENAMIN KDMP sold by the company CLARIANT, (4) DOW CORNING 939 EMULSION sold by the company Dow Corning Example 4: non-rinse composition usable according to The invention is prepared from the following ingredients in the following proportions in% by weight.

11 Cyclopentasiloxane (') 5 Active 1 0.5% Dimethicone copolyol (2) 0.5% MA Propylene glycol 2.5 0/0 Preservative qs Perfume qs Water qs 100% MA: active ingredient (1) MIRASIL CM 5 marketed by RHODIA (2) DOW CORNING 5225C marketed by the company Dow Corning, 5

Claims (15)

REVENDICATIONS1. Use of one or more compounds derived from chlorotriazine as an agent for protecting the color of artificially-dyed keratinous fibers, especially human keratin fibers and more particularly the hair, with respect to washing. 2. Use according to claim 1, wherein the keratinous fibers are dyed by oxidation dye, especially in the presence of one or more oxidizing agents. 3. Use according to any one of claims 1 to 2, wherein the one or more compounds derived from chlorotriazine are of formula (I): ## STR1 ## in which R1 and R2, which may be identical or different, denote an atom of hydrogen, a halogen atom, a C1-C10 alkyl radical, a C1-C10 alkoxy radical, a sulfo radical, a carboxy radical, a hydroxyl radical, an amino radical, a C1-C10 aminoalkyl radical, a heterocyclic radical comprising from 5 to 10 and from 1 to 5 identical or different heteroatoms, a group comprising a 1,3,5-triazine ring bearing at least one chlorine atom. 4. Use according to any one of claims 1 to 3, wherein the one or more compounds derived from chlorotriazine are selected from the following compounds: 301 2,4-dichloro-6-methoxy-N / 1 Cl 1.3, 5-triazine, CAS = 3638-04-8, CH3O / NCI 2 PEG (Polyethylene glycol) (CI CI Mw 600) terminated bis N (dichlorotriazine) \ N where (CH2CH2o) ~ o NN CI CI 3 4,6-dichloro -1,3,5-triazine-2NClNoIoN CAS RN =, 168677-46-1, 4 2-amino-4,6-dichlorotriazine, Cl / 1 N / N NH2 CAS = 933-20- 0, 1C1 marketed by ABCR N 2- (N, N-diethylamino) -4,6-Cl / N-NNCH3 dichlorotriazine CI CH3 J6 2,4-dichloro-6-morpholino-NN 1 N 1, 3,5-triazine CI N 5. Use according to any one of claims 1 to 4, wherein the compound (s) derived from chlorotriazine are present in the compositions in concentrations ranging from 0.005 to 30% by weight and more preferably from 0.01 to 15% by weight. and more preferably from 0.3 to 10% by weight relative to the total weight of the composition. 6. Process for protecting the color vis-à-vis the washing of artificially dyed keratinous fibers including human keratinous fibers and more particularly the hair, characterized in that it consists in applying to said fibers, one or more compounds derived from chlorotriazine or a composition comprising in a cosmetically acceptable medium one or more compounds derived from chlorotriazine. 7. The method of claim 6, wherein the keratin fibers are dyed by oxidation dyeing. 8. A process for dyeing keratinous fibers, in particular human keratinous fibers and more particularly hair, consisting in applying to the fibers a direct dye composition (A) or an oxidation composition (A), optionally in the presence of one or more oxidizing agents for a time sufficient to develop the color, and to precede or follow this application by the application of a composition (B) containing in a cosmetically acceptable medium one or more compounds derived from chlorotriazine as defined in any of claims 1 to 5. 9. The method of claim 8, wherein the application of the composition (A) is followed by rinsing and / or drying keratin fibers. 10. Method according to one of claims 8 or 9, wherein the application of the composition (B) is followed by rinsing and / or drying keratin fibers and / or heating the keratin fibers. 2,4,6-trichloro-1,3,5-triazine CAS =, 108-77-0, Cl ClCl 735 The method of any one of claims 8 to 10 wherein the composition (B) is applied after the application of the direct dyeing or oxidation composition (A), either immediately or delayed, and the applications of said composition (B) can be repeated between two colorations. 12. A method according to any one of claims 8 to 11, wherein the dye composition (A) results from mixing at the time of use of a dye composition (AI) comprising one or more direct dyes and a composition ( A2) comprising one or more oxidizing agents. 10 13. A process according to any one of claims 8 to 12, wherein the coloring composition (A) results from the mixing at the time of use of a dye composition (A3) comprising one or more oxidation bases and optionally one or several couplers and / or one or more direct dyes and a composition (A4) comprising one or more oxidizing agents. 14. A process for dyeing keratinous fibers, in particular human keratinous fibers and more particularly hair, which consists in applying to the fibers a direct dye composition (A) or an oxidation dye composition (A) for a sufficient time. for developing the color, said composition (A) comprising in a cosmetically acceptable medium one or more compounds derived from chlorotriazine. A kit comprising at least a first component (or compartment) comprising a composition (B) comprising in a cosmetically acceptable aqueous medium, one or more compounds derived from chlorotriazine and at least one second component (or compartment) comprising a coloring composition ( A) comprising at least one oxidation dye and / or or at least one direct dye, these 2 components optionally being associated with a third component (or compartment) comprising one or more oxidizing agents.