FR2980702A1 - Composition, useful for coloring human keratin fibers, comprises substituted iridoid compounds and/or substituted furanol compounds, and nucleophilic compounds optionally comprising anion(s) to ensure electrical neutrality of composition - Google Patents

Abstract

Composition comprises substituted iridoid compounds (I) and/or substituted furanol compounds (II), or their plant extracts, and at least one nucleophilic compounds (a)-(h) optionally comprising an anion or its mixture to ensure electrical neutrality of the composition, and polyallylimidazolium oligomers or polymers. Composition comprises substituted iridoid compounds of formula (I) and/or substituted furanol compounds of formula (II) and their optical and geometrical isomers, inorganic or organic acid salts or solvates, or their plant extracts, and at least one nucleophilic compounds of formula (a)-(h) or its optical or geometrical isomer, organic or mineral acid salt or solvate, where the nucleophilic compounds optionally comprise an anion or its mixture to ensure electrical neutrality of the composition, and polyallylimidazolium oligomers or polymers. R1 : H, CH 3, hydroxymethyl, aldehyde, -CO 2R4 or -CH 2-glucose; R4 : H or 1-2C alkyl; R2 : H, hydroxy or glucose radical; R3 : H, hydroxy or 1-4C-alkyloxy, where the number of hydroxy groups is = 2; R5, R6 : H or -CO 2R6a; R6a : H, 1-2C alkyl, metal alkali cation or ammonium groups; n, n1 : 0-4; n2 : 0-2, where the unsubstituted carbon atoms bear a hydrogen atom; A : -CR-10-, -N- or -N +>R11; R11 : 1-4C alkyl; X : N or CR7a; R7a : H or R7; either R7 : 1-4C alkyl, OH, 1-4C alkoxy, amino or 1-4C alkylamino; or R7+R7 : 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms containing O and/or N; either R8, R10 : 1-4C alkyl (optionally substituted with at least one group of -COOR12 or -OCOR12), H, OH, amino, -COR13, -COOR14, -OCOR14 or -OSO 3 ->; and R9 : H, 1-4C alkyl, 1-4C alkylcarbonyl or acetyl; or R8R9 : 5- or 6-membered heterocycle optionally comprising another heteroatom containing O, N or S, where the heterocycle is optionally interrupted with CO group; R12, R13 : 1-4C alkyl; R14 : H or 1-4C alkyl (optionally substituted with at least one 1-4C alkoxy); A1 : S, -(CR18) 2- or -C(R19)=C(R19a)-; R18 : H or 1-4C alkyl; B1 : S; R19, R19a : H or 1-4C alkyl; R15 : 1-4C alkyl, halo, preferably Cl, or 1-4C alkoxy; R15a : 1-2C alkyl; either R16 : H or 1-4C alkyl; and R17 : 1-4C alkyl optionally bearing a hydroxyl group; or R16R17 : 5- or 6-membered fused heterocycle optionally containing one or more unsaturations (optionally substituted with at least one 1-4C alkyl radical); R16a : H or 1-4C alkyl; R17a : H or 1-4C alkyl, where the alkyl group is optionally bearing a hydroxyl or phenyl radical and optionally interrupted with a CO group; R20 : 1-4C alkyl, halo (preferably Cl, Br or I), -COOR21 or -OCOR21; R21 : H, 1-4C alkyl, amino or 6C aryl (optionally substituted with at least one hydroxyl radical); X : N, -CR22 or -CR22a-CO-, where CR22a is linked to Y1 or X; Y1 : N or -CR22aa; either R22, R22a, R22aa : H or linear or branched 1-4C alkyl (optionally substituted with amino, benzyl, phenyl, -COOR23 or -OCOR23); R23 : 1-4C alkyl or -SOR24; or R22, R22aa : fused 6-membered aryl ring; R24 : 1-4C alkyl; Y2 : CH, CR27 or N; Z : N; Z1 : N or NR27a; q : 0-3; r, s : 1 or 2; t : 0-4; u : 0 or 1, where the unsubstituted carbon atoms of the heterocycles contain a hydrogen atom; R27 : linear 1-4C alkyl, halo, preferably Cl, Br or F; R28 : H or linear 1-4C alkyl radical, where the radicals R27 located ortho to the radical NHR28 and R28 is together to form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms of O or N; R29 : linear 1-4C alkyl, where the two radicals R29 together optionally forming a saturated 5-membered heterocycle; either R27a : H, 1-4C alkyl or phenyl radicals; and R31 : 1-4C alkyl, 1-4C alkoxy (optionally substituted with OH) or amino (optionally substituted with -COCH 3); or R27aR31 : 5- or 6-membered (non)aromatic heterocycle (optionally substituted with 1-4C alkyl); or R31R31 : aromatic ring (optionally substituted with an amino radical); and R30 : OH, amino or pyrrolidyl group. Provided that: when A is N, n is 0, X is CH and R8 is NH 2, then R9 is not H or CH 3; if Y2 is CR27, then q is preferably other than 0; and at least one of the radicals R31 is other than hydrogen and/or at least u is 1. Independent claims are included for: (1) coloring human keratin fibers, preferably hair comprising applying the composition on the fibers; and (2) a multicompartment device comprising a first compartment containing (I) or their plant extracts, and a second compartment containing (a)-(h), nucleophilic oligomers or polymers. [Image] [Image].

Description

The subject of the present invention is a dyeing composition comprising, in a cosmetically acceptable medium, at least one compound of the family of non-glycosylated iridoids extracted from a non-glycosylated iridoid compound and a specific nucleoside. plants, and at least one particular nucleophilic compound, as well as a staining process using such a composition.

In recent years, there has been a growing interest in natural compounds that can be used as hair dyes. For example, in the application EP 440 494, there is described a hair dyeing method using a composition comprising at least one compound of the type (seco) iridoide-glycoside or (seco) iridoide non glycosylated (also called aglycon), extracted plants such as Rubiaceae, Euphorbiaceae, Valerianaceae, Cornaceae, Gentianaceae, Caprifoliaceae, Oleaceae, Ericaceae, Loganiaceae, etc. The problem with such stains is that they are low intensity or require repeated application over several days or weeks of the composition to obtain a satisfactory color.

In addition, it is difficult to achieve natural nuances, which is a desired advantage. And when such nuances are achieved, it is not uncommon to observe a significant color shift over time. The present invention therefore aims to overcome the disadvantages described above.

Indeed, it has surprisingly been found that dye uptake could be significantly improved from non-glycosylated iridoid compounds and its derivatives, and generally any natural extract containing them, associating with this compound a particular nucleophilic compound. It was also found that the structure of the treated fibers was not impaired by the coloring according to the invention. The subject of the present invention is therefore a composition for staining human keratinous fibers comprising, in a cosmetically acceptable medium: a compound of formula (I) and / or of formula (II) below, their optical or geometric isomers, their inorganic or organic acid, their solvates, or a plant extract comprising: (R 1, R 2) R 6 (I) (II) Formula (I) and / or (II) in which: R 1 represents a hydrogen atom a methyl radical, a hydroxymethyl radical, an aldehyde group, a group -OO2R4 in which R4 represents a hydrogen atom or a C1-C2 alkyl radical, a -CH2-glucose group, R2 represents a hydrogen atom; a hydroxyl radical or a glucose radical; R 3, which may be identical or different, represent a hydrogen atom, a hydroxyl radical or a (C 1 -C 4) alkyl radical, the number of hydroxyl groups being not greater than 2; n is an integer from 1 to 5; R5 represents a -OO2R'6 group wherein R'6 represents a hydrogen atom, a C1-02 alkyl radical, an alkali metal cation, an ammonium group; . R6 represents a hydrogen, a group -OO2R'6 in which R'6 represents a hydrogen atom, a C1-02 alkyl radical, an alkali metal cation, an ammonium group; at least one compound chosen from the compounds of the following formulas, their optical or geometrical isomers, their organic or inorganic acid salts, their solvates: (R7) n R8 X ----- N R9 (a) In which : * n is an integer from 0 to 4; unsubstituted carbon atoms bearing a hydrogen atom * A represents -CRio-, -N-, -N + Ri- with R11 representing a C1-C4 alkyl radical X represents N, CR ', and R'7 represents a hydrogen atom or R7 * R7 identical or different represent: - a C1-C4 alkyl radical - a hydroxyl radical, - a C1-C4 alkoxy radical, - an amino radical - a C1-C4 alkylamino radical two R7 radicals located ortho to each other can form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatom (s) selected from oxygen, nitrogen or their combination, * R8, R10, identical or no, represent - a hydrogen atom, - a hydroxyl radical, - an amino radical - a C 1 -C 4 alkyl radical optionally substituted with at least one -000R 12 or -000 R 12 group with R 12 representing a C 1 -C 4 alkyl radical, a -COR13 group with R13 representing a C1-C4 alkyl radical; a -000R14 or -000R14 group with R14 representing an atom of hyd a C 1 -C 4 alkyl radical optionally substituted by at least one C 1 -C 4 alkoxy group; a group -OSO3 * R9 represents a hydrogen atom, a C1-C4 alkyl radical or a (C1-C4) alkylcarbonyl group; an acetyl radical R8 and R9 radicals may form a 5- or 6-membered heterocycle optionally comprising another heteroatom selected from oxygen, nitrogen or sulfur, said heterocycle may be further interrupted by a CO group, when A represents N, that n is 0, X represents CH, and R8 represents NH2, then R9 is neither a hydrogen atom nor a methyl group; (R1 (R15) n) An R16 N R17 An (b) (b ') In which: n is an integer from 0 to 4, the unsubstituted carbon atoms carry a hydrogen atom * n is an integer from 0 to 2, the unsubstituted carbon atoms bear a hydrogen atom * A 'represents S, - (CR18) 2-, -CR19 = CR'19-, with R18, representing an atom of hydrogen, alkyl radical C1-C4, R19, R'19, identical or not, represent a hydrogen atom, a C1-C4 alkyl radical; B 'represents S * R15, which may be identical or different, represent an alkyl radical; C1-C4, a halogen atom, preferably chlorine, a C1-C4 alkoxy radical; R15 ', which may be identical or different, represent a C1-C2 alkyl radical; R16 represents a hydrogen atom or a radical; C1-C4 alkyl; R16 'represents a hydrogen atom, a C1-C4 alkyl radical; R17 represents a C1-C4 alkyl radical, optionally bearing a hydroxyl group. R17' represents: a hydrogen atom, - a C1-C4 alkyl radical, optionally bearing a hydroxyl group, optionally interrupted by a CO group, optionally bearing a phenyl radical; R16 and R17 radicals may together form a 5- or 6-membered fused heterocycle, possibly with one or more unsaturations, optionally substituted by at least one C1-C4 alkyl radical; In which * n 'is an integer ranging from 0 to 2, the unsubstituted carbon atoms carry a hydrogen atom * R20, identical or different, represent a C1-C4 alkyl radical, a halogen atom (preferably chlorine, bromine, iodine), a radical -COOR21 or -000R21 with R21 representing a hydrogen atom, a C1-C4 alkyl radical, an amino radical, a C6 aryl (phenyl) group optionally substituted with at least one hydroxyl radical * X represents N, CR22, -CR'22-00-, CR'22 being connected to Y or X. * Y represents N, CR "22 * R22, R'22, R" 22, identical or different, represent a hydrogen atom, a linear or branched C1-C4 alkyl radical optionally substituted by an amino radical, a benzyl radical, a phenyl radical, -COOR23 or -000R23 R23 representing a C1-C4 alkyl radical; , -SOR24 where R24 represents a C1-C4 alkyl radical R22 and R22 may together form an aromatic 6-membered aromatic ring (d ") -..... Y. NHR2, (d) (d ') wherein (Ro) Y represents CH, CR 27, N * z represents N; z 'is N, NR "27 * q is an integer between 0 and 3 * r is 1 or 2 * s is 1 or 2 * t is an integer between 0 and 4 * u is 0 or 1 * the atoms of unsubstituted carbon heterocycles carry a hydrogen atom * R represents a hydrogen atom or a C1-4 alkyl radical, at least one of the radicals R representing at least one hydrogen atom * R27 independently represent one of the others: a linear C1-C4 alkyl radical; a halogen selected from chlorine, bromine and fluorine; R27 represents a hydrogen atom, a linear C1-C4 alkyl radical or a phenyl radical; R 28 represents a hydrogen atom, a linear C 1 -C 4 alkyl radical; the R 27 radicals located in ortho of the NHR 28 and R 28 radical may together form a 5- or 6-membered heterocycle comprising 1 to 2 heteroatoms selected from oxygen and nitrogen. * if Y represents CR27, then q is preferably different from 0 * R29 identical or not, represent a linear C1-C4 alkyl radical, the two radicals R29 may together form a saturated 5-membered heterocycle, * R30 independently represent others a hydroxyl radical, an amino radical, a pyrrolidinyl radical * R31 represent independently of each other: - a C1-C4 alkyl radical - a C1-C4 alkoxy radical optionally substituted by a hydroxyl group - an optionally substituted amino radical by an acetyl group (-COCH3) * R "27 and R31 may form a 5- or 6-membered heterocycle having aromatic or non-aromatic optionally substituted by a C1-C4 alkyl radical. in formula (d '), at least one one of the radicals R 31 is different from hydrogen and / or at least one is equal to 1; two radicals R 31 may together form an aromatic ring optionally substituted with an amino radical; formulas of formulas (a) to (d "') comprising, where appropriate, an anion An or a cosmetically acceptable mixture of anions, guaranteeing the electroneutrality of said formulas; as well as among oligomers or polymers of the polyallylimidazolium type.

Another subject of the present invention is represented by a process for staining human keratin fibers, in which such a composition is used. A final subject of the invention is constituted by a multi-compartment device comprising a first compartment containing at least one compound of formula (I) and / or (I1) or the plant extract comprising it, and a second compartment containing at least a compound of formula (a) to (d "), oligomers or nucleophilic polymers The composition according to the invention makes it possible to obtain various colorations that are not hair-degrading and stubborn to shampoos.

Other characteristics and advantages of the invention will emerge more clearly on reading the description and examples which follow. It should be noted, unless otherwise indicated, that the limits of the value domains given in the description are included in the fields.

The human keratinous fibers treated by the process according to the invention are preferably the hair In the following, the terms "at least one", "one or more" are considered synonymous. The mineral acid salts are more particularly hydrochlorides, hydrobromides, sulphates, phosphates; the organic acid salts are more particularly citrates, succincts, tartrates, lactates, tosylates, benzenesulfonates, and acetates. The solvates are more particularly hydrates. Compounds of formulas (I) and (II) or plant extract comprising as indicated above, the composition comprises, in a cosmetically acceptable medium, at least one compound of formula (I) and / or of formula (II) above, or a plant extract comprising It should be noted that the compounds used in the process according to the invention, and in particular those of formula (I) and / or of formula (II), are said to be unglycosylated insofar as they do not carry any Sugar units on the oxygen atom in the pseudo-anomeric position (on the alpha carbon atom of the intracyclic oxygen atom). Preferably, R 1 represents a hydrogen atom, a methyl radical, a hydroxymethyl radical, an aldehyde group; a hydroxycarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group. Preferably, R2 represents a hydrogen atom or a hydroxyl radical. Preferably, R 3, which may or may not be identical, represent a hydrogen atom, a hydroxyl group, a methoxy group, an ethoxy group or an n-butyloxy group. Preferably R5 is a hydroxycarbonyl radical, a methoxycarbonyl radical, an ethoxycarbonyl radical.

Preferably, R6 represents a hydrogen, a hydroxycarbonyl radical, a methoxycarbonyl radical or an ethoxycarbonyl radical. According to a particularly advantageous embodiment of the invention, the compound of formula (I) and / or of formula (II) is genipin (R1 represents a methoxycarbonyl group) and / or genipotic acid or one of its salts (R1 represents a carboxylic group in acid or salified form) and / or genipic acid (R5 represents a hydroxycarbonyl radical and R6, a hydrogen atom) and / or genipinic acid (R5 represents a hydroxycarbonyl radical and R6, a methoxycarbonyl radical). The compounds of formula (I) and / or of formula (II) are generally found in plant extracts from the following plants: Veronica persica; Genipa americana; Apodytes dimidiata; Randia canthioides; Tarenna attenuata and preferably Genipa americana. It should be noted that by extract, juices, or powders obtained by one or more operations of separation of plant parts of the plant, of enrichment, concentration and, optionally, of drying, from natural plant substances are designated. These compounds of formula (I) and / or of formula (II) are in particular extracted from plants in a manner known per se. It will be possible in particular to refer to the procedure described in the international application WO 2005/105020.

Thus, in the case of the aerial parts, they are washed if necessary, or crushed, optionally in a frozen form, or cut at room temperature, and then macerated in a suitable solvent, in particular ethanol or water then filtered, concentrated and optionally dried. In the particular case of fruits, they are optionally frozen, washed with water to remove impurities present. It may optionally be sterilized, especially with a solution comprising ethanol and chlorine. For the actual extraction, the fruits are defrosted if necessary and pressed for example by means of a specially adapted hydraulic press. The juice thus recovered is filtered, degassed in the presence of nitrogen, this operation avoiding the oxidation of genipin or its derivatives, increasing the amount of dissolved gas. The juice is then stored in an airtight container protected from the air. The recovered juice can then, if necessary, be the subject of a concentration and drying step. According to a preferred embodiment of the invention, the extract used is derived from Genipa americana. In this case, the extract is obtained from the immature fruit of Genipa americana. The first step of preparation of the extract consists of freezing the fruit beforehand and carrying out a cryomilling step, for example at a temperature of between -20 ° C. and -200 ° C. on the frozen fruit. A fine and homogeneous powder is thus collected. Once this operation is performed, the active ingredient (s) of formula (I) and / or (II) are extracted for example with water. The extract is then concentrated and then optionally dried.

The content of compound of formula (I) and / or of formula (II) in the solids content varies from 0.01 to 30% by weight. The content of compound of formula (I) and / or of formula (II) of the composition is between 0.001 and 20% by weight relative to the weight of the composition.

Additional dyes The dye composition may further comprise additional dyes, different from the compounds of formula (I) and / or formula (II) above. Among these additional dyes, mention may be made of natural or synthetic direct dyes, oxidation dyes with bases possibly associated with couplers, as well as their combinations. These direct dyes may be, for example, chosen from neutral, acidic or cationic nitro-benzene direct dyes, neutral azo, acid or cationic direct dyes, tetraazapentamethine dyes, neutral or acidic or cationic quinone dyes, in particular neutral anthraquinones, direct dyes azines, triarylmethane direct dyes, direct indoamine dyes and natural direct dyes. Among the natural direct dyes that may be mentioned are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, anthragallol, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, chlorophylls, chlorophyllins, orceins, haematein, hematoxylin, brazilin, braziline, safflower dyes (eg, carthamine), flavonoids (with examples are morine, apigenidine, sandalwood), anthocyans (of the apigeninidine type), carotenoids, tannins, sorghum and cochineal carmine, or mixtures thereof. It is also possible to use the extracts or decoctions containing these natural dyes, and in particular poultices or extracts made from henna. Among the oxidation bases that may be mentioned are para-phenylenediamines, bisphenylalkylenediamines, para-aminophenols, bis-para-aminophenols, ortho-aminophenols, heterocyclic bases and their addition salts.

Among these couplers, there may be mentioned meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts. The oxidation base (s) present in the dyeing composition are in general each present in an amount of between 0.001% and 10% by weight relative to the total weight of the dyeing composition, preferably between 0.005% and 6% by weight. The coupler or couplers are each generally present in an amount of between 0.001 and 10% by weight of the total weight of the dye composition, preferably between 0.005 and 6%. In general, the addition salts of the oxidation bases and couplers that can be used in the context of the invention are chosen especially from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates. Nucleophilic Compounds As indicated above, the composition according to the invention comprises at least one nucleophilic compound of formulas (a) to (d "') or at least one particular nucleophilic polymer. The combination of the compounds of formulas (I) and / or (II) with these particular nucleophilic compounds makes it possible to improve the efficiency of the coloration reaction According to a first variant, the nucleophilic compound is of formula (a) above, its isomers, or its salts, this compound being alone or in a mixture As examples of compounds of this type (formula (a)), mention may be made of the following compounds, their isomers, their salts, their solvates, these compounds being alone or in admixture: Structure Chemical Name OH 1-butyl-2-methyl-1H-benzimidazol-7-ol * N, N, CH, NL CH 3 HO 1H-benzimidazol-5-ol * N-OH Y 1H-benzimidazol-4-01. N OH N 1H-benzimidazol-4-ol hydrobromide * BrH S [1,3] thiazolo [3, 2-a] benzimidazol-3 (2H) -one g> Ni N HO N 1H-benzimidazole-5,6-diol hydrobromide HO NH am 013 2- (2-methoxy-2-oxoethyl) methosulphate 3-dimethyl-1H-3,1-benzimidazol-3-ium-1-methyl-1H-CH3 Structure Chemical name NH, CIH2 2-methyl-1H-1-benzimidazole dihydrochloride ## STR2 ## o / *. 1H-benzimidazol-4-amine dihydrochloride dihydrochloride M. H2N 1 H-benzimidazol-5-amine N H2N go N 2 -methyl-1H-benzimidazol-5-amine CH, NH Structure Chemical name H2N - HN NH2 1H-benzimidazole-2,5-2-dihydrochloride CIH / 1H-benzimidazole-2,5,6-H21- [1H] -NH-dihydrochloride 1H-benzimidazole-1H-dihydrochloride 1H-benzamidazole dihydrochloride 4-amino-1H-benzimidazol-7-ol-2-dihydrochloride Chemical Name HO of 1H-indole-5,6-diol HO 0 0 \ H 5H- [, dioxolo [4,5-flindole OH] / 5,6-dihydroxy-11-1- ethyl indole-2-carboxylate HO H 0. Ethyl 6-hydroxy-1F-1-indole-2-carboxylate HO 1 H-1-indol-5-ol OH 2-methyl-1H-indol-4 -ol PI. 0 (:) - K + the salt of 1 H-indol-3-yl potassium sulfate 0 0 H 0. 1H-Indol-6-ol-NH-OH-1H-OH-1H-NH-OH-4H-4,6-dimethoxy-1H-indole-2-carboxylic acid ## STR1 ## wherein N is a 1-ethyl-1-ethyl-1-ol-indole-2-carboxylate. 1H-indol-4-amine N 2 H-indol-3-yl 3-methoxypropanoate 1H-indol-3-yl H / H 2 N II 1H-indol-6-amine eH NMR 11-1- Indo-7-amine NH 2 NH. 2N is 11-1-indol-5-amine H leila N-ethyl-1H-indol-6-amine HH 5-hydroxy-1H-indole-2-carboxylate of ethyl HO go HN HO 2-nnethy1-11-1-indole-5,6-diol hydrobromide HBr HO el \ 0 6-h drox acid -1H-indole-2-carboxy YY YI q NH OH o. 1- (3-Hydroxy-1H-indol-1-yl) ethanone N-OH-O-1H-pyrrolo [2,3-b] pyridin-3-ylacetate The compounds of formula (a) are selected from those wherein * n is an integer of 0 to 4; the unsubstituted carbon atoms carry a hydrogen atom, A represents -CR10-, -N-, X represents CR ', and R' 7 represents a hydrogen atom or R7 * R7, which may be identical or different, represent: a C 1 -C 4 alkyl radical - a hydroxyl radical, - a C 1 -C 4 alkoxy radical, - an amino radical - a C 1 -C 4 alkylamino radical - two R 7 radicals located ortho to one another can form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatom (s) selected from oxygen, nitrogen or a combination thereof, preferably oxygen, with R14 representing an atom * R8, R10, identical or not, represent a hydrogen atom, a C1-C4 alkyl radical, a hydrogen -COOR14 or -000R14 group or a C1-C4 alkyl radical optionally substituted with at least one C1-C4 alkoxy group; R 9 represents a hydrogen atom, a C 1 -C 4 alkyl radical, when A represents N, n is 0, X represents CH, and R 8 represents NH 2, then R 9 is neither a hydrogen atom nor a methyl group. As examples of compounds (a) which are more particular, the following compounds may be mentioned, their isomers, their salts, their solvates, these compounds being alone or as a mixture: Structure Chemical name OH 1-butyl-2-methyl- 11 1 -Benzimidazol-7-ol®N yrCH 3 NCH 3 HO 1H-benzinnidazol-5-ol 1H-benzimidazol-1-ol (.1NH 2 OH 1H BrH 1H hydrobromide 1H-benzimidazole-5,6-diol HO HBH 1H-1-benzimidazol-4-ol NH 1H -benzimidazole hydrobromide Structure Structure Chemical Name N 0111 CH3 CIH 2-Methyl-1H-1-benzimidazol-4H dihydrochloride, 2 amine N 1,...,... N-NH 2 Ni 1,5,6-trimethyl-1H-benzimidazol-4-amine H 3 C 2 CH 2 H, C 1 O 1H 1H dihydrochloride 4-Amino-benzimidazol-4-amine dihydrochloride 1H-benzimidazol-5-amine H 2 H -NH 2 -methyl-1-benzimidazol-5-amine 1H-benzimidazole dihydrochloride -2.5- 2 CIH / diamine N H2N 1H-NH2H-benzimidazole-2,5,6-HCl 2H-dihydrochloride 1HCl / triamine NH 2 N 2 ClH 4-amine dihydrochloride No. 1H-benzimidazol-7-el OH Structure HO Chemical Name of 1H-indole-5,6-diol HO 0 0H 5H- [, dioxolo [4,5-flindole 0 HO el Ethyl 5,6-dihydroxy-11-1-indole-2-carboxylate HO H 0. Ethyl 6-hydroxy-1F-1-indole-2-carboxylate HO 1 H-1-indol-5-ol OH 2-methyl-1H-indol-4 1H-Indol-7-OH OH. 1H-Indol-6-ol HO N. 1H-ethyl-4-ol-1-ethyl-5-ethoxy-1H-indole-2-carboxylic acid, and 5-hydroxy-1H. Ethyl-indole-2-carboxylate 2-methyl-1H-indole-5,6-diol hydrochloride HO NH HBr. hydroxy-1H-indole-2-carboxylic acid H Structure Chemical name 1H-indol-4-amine NH 2 I e 0 1H-indol-3-yl 3-methoxypropanoate I / OH / H2N I 1H-Indol-6-amine NH 11-1-indol-7-amine NH 2 NH 2 N, 11-1-indol-5-amine N, N-ethyl-1H-indole Examples of suitable nucleophilic compounds corresponding to formulas (b) or (b ') include the following compounds, their isomers, their salts, their solvates, these compounds being alone or as a mixture: Chemical name CH, 1,4-dimethylquinolinium methylsulfate salt, N, N, CH, ICH, 1,2 N methylsulfate salt dimethylquinolinium I , cil o, ', s /' o, "_ oo C H3 CH the methylsulfate salt of 6 1-methoxy-1,2- (1, 3 100 -., dimethylquinolinium) -S-O-CH 2 CH 2 CH 2 CH 2 CH 2 -methyl-pyrrolo chloride [1.2- Cl a] quinolinium el ... - 1-ethyl-2-methylquinoline CH3 H3C I-CH iodide, 6,8-dimethoxy-1,4-H, C-0 1101 N 0 dimethylquinolinium methylsulphate salt ## STR2 ## Structure Chemical Name H3C CI-13 10,10-dimethy-7,8,9,10-tetrahydro-6H-pyrido [1,2-dimethy] -a] indolium / N Cl Structure Chemical name S 0 the salt of 2,3-dimethyl-1,3---H 3 S thiazol-3-ium methyl sulfate 113C 0 \ C) N 0 \ CH 3 "\. ... B.1.-,, / H, 4,5-olimethy1-3- (2-oxo-2-scH, phenylethyl) -1,3-thiazol-3-ium bromide 11 1 1 ---- + Gi '° -s ri = D 4-methylbenzenesulfonate salt of 5-chloro-3. Ethyl-2-methyl-1,3-benzothiazol-3-ium. , _,. oa, 3- (2-oxo-2-phenylethyl) -1,3-thiazol-3-bromide bromide, N, -IF. 2-Amino-4-methoxy-3-methyl-1,3-benzothiazol-3-lmol methyl sulfate salt binds 3- (3-bromide) bromide; 2-hydroxyethyl) -2-methyl-1,3-benzothiazol-3-ium-OH Preferably, the compound (s) are of formulas (b) and (b ') such that: n and n are 0; the unsubstituted carbon atoms carry a hydrogen atom; * A 'represents G. - (CR18) 2-, with R18, representing a hydrogen atom, a C1-C4 alkyl radical; * B' represents S * R16 represents a hydrogen atom, a C1-C4 alkyl radical; R16 'represents a hydrogen atom or a C1-C4 alkyl radical; R17 represents a C1-C4 alkyl radical, optionally substituted by a C1-C4 alkyl radical; a hydroxyl group. R. 17 'represents: a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical, optionally carrying a hydroxyl group, the radicals R.sub.16 and R.sub.17 may together form a hydrogen atom; 5- or 6-membered condensed heterocycle optionally having one or more unsaturations, optionally substituted by at least one C1-C4 alkyl radical. As examples of compounds (b) or (b ') that are more particular, mention may be made of the following compounds, their isomers, their solvates, or their salts, these compounds being alone or as a mixture: Structure Chemical name S 0 salt 2,3-dimethyl-1,3-thiazol-3-methyl-3-methyl-3-methyl-3- (2-hydroxyethyl) -2-methyl bromide; -1,3-) - CH, B benzothiazol-3-ium OH H3C C1-1 ^ 10,10-dimethy1-7,8,9,10-tetrahydro-6H-pyrido [1,2- a] indolium till. N CI CH, the methylsulfate salt of A-dimethylquinolinium. ## STR1 ## and 1,2-CH3 methyl dimethylquinolinium salt, , o ex, - s. According to a particular variant, the compound (s) are of formulas (c) such that in which n is an integer ranging from 0 to 2, the unsubstituted carbon atoms carry a hydrogen atom. R20, which may be identical or different, represent a C1-C4 alkyl radical, a chlorine atom, a -COOR21 or -000R21 radical with R21 representing a hydrogen atom, a C1-C4 alkyl radical, an amino radical or a group phenyl * X represents N, CR22, CR'22 being connected to Y or X. * Y represents N, CR "22 * R22, R'22, R" 22, which may be identical or different, represent a hydrogen atom, a C1-C4 linear or branched alkyl radical optionally substituted by an amino radical, a benzyl radical, a phenyl radical, - * R22 and R "22 may together form an aromatic 6-membered fused ring. The compounds of formula (c) which may be mentioned by way of example are the following compounds, their isomers, their solvents, these compounds being alone or in mixtures: Structure Chemical name 1 H-imidazo [1,2-b] pyrazole II N N NH N 3,6-dimethyl-1H-pyrazolo [5,1-c] [1,2,4] triazole NI N 2 -methyl-4H-pyrazolo [1,5-a] benzirnidazole) NN-1-G 7-chloro-2,6-olimethyl-1H-pyrazolo [1,5-] b] [1,2,4] triazole N, N, N, 7-chloro-3,6-dimethyl-1H-pyrazolo [5,1-c] [1,2,4] triazole NH) 4 N-6-ethyl- 3-methyl-1H-pyrazolo [5,1-c] [1,2,4] triazole N 1 NH) = N, Ni-3,6-d and-1H-pyrazolo [5,1-cl] [1,2,4] triazole NH 3 -3-ethyl-6-nnethyl-1H-pyrazolo [5,1-c] [1,2,41-triazole NH] has 3-phenyl-1H-pyrazolop, 1 [N-CH] -3-phenyl-1H-pyrazolo [5,1-c] [1,2,41triazol-6] -c] [1,2,4] triazole-6- sodium carboxylate N / Arnethanol NH / -N 41-6-ethyl-3- (propan-2-yl) -1H-pyrazolo [5,1-cl [1,2,4] triazole NiNNN NH y = 4 NI-11 Hydrate and hydrochloride of 3,6-dimethyl-1H-H 2 O pyrazolo [5,1-c] [1,2,4] triazol-7-amine NH) 2H 1H hydrochloride 1H -imidazo [1,2-1D] pyrazol-7-NH amine // N + H + NH NH 2 2- (7-Chloro-6-methyl-1H-pyrazolo [1,5-N to] [1,2,4] triazol-2-ylpropan-1-amine] NH 2 2 -ClI 2-methyl dihydrochloride 4H-pyrazolo [1,5-NHa] benzimidazol-3-amine N - With respect to the nucleophilic compound (s) of formula (d), (d '), (d "), (d"'), the following compounds may be mentioned by way of example, their isomers, their salts, their solvates, these compounds being alone or in mixtures: Structure Chemical name H2 OH 3-amino-1H-pyrazol-5-ol / H. N- (5-Hydroxy-1-phenyl-1H-pyrazol-3-ypacetam ide] HNN 3-meth} 4H-pyrazol-5-o] N 1-12 sulphate 5- (1-pyrrolidin-1-yl) imidazo [1,2-a] pyridin-8-amine HO-S-OH NH 2 NH, 2-Methyl-2H-H2O-1N-indazole-3,5-diamine dihydrochloride and hydrate The 2,3-diamino-6,7-dihydro-NH 2 H-dihydrochloride dihydrochloride 5H-pyrazolo [1,2-a] pyraopyl-1-one / N-amino-2-chloro-3-amino-6,7-dihydro-11-1,5H-pyrazolo [1, hydrochloride] 2-a] pyrazol-1-one 4-amino-1,2-diethy-5-N (pyrrolidin-1-yl) -1,2-dihydro-3H hydrochloride pyrazol-3-one 1N-1 Ecl 4-amino-1,2-diethyl-5-hydroxy-1,2-dihydro-3H-pyrazol-3-one hydrochloride VNIN ç o N-12 J-13 4,5-diamino-1,2-diethy1,1,2-dihydro-3H-pyrazol-3-one dihydrochloride NF1 / NX ç Cl OH HCI hydrochloride 3-amino-2-chloro-6H-2-methylphenol HO 3,4-dihydro-2H-1,4-benznoxazin-6-ol H 2 NH 2 FCl 2 [(3-aminopyrazolo [1.5] hydrochloride - ° - \ -OH a] pyr idin-2-yl) oxy] ethanol NNH2 2-aminopyridin-3-ol OH As regards the nucleophilic oligomers or polymers, these are chosen from polymers of the polyallylimidazolium type, in particular those made from 1-allyl. -3-butylimidazolium. Preferably, the carbonyl compound (s) are chosen from compounds of formulas (a), (c), (d), (d '), (d "), (d"') or mixtures thereof.

More particularly, the content of compound (s) of formula (s) (a) to (d-) or oligomers or nucleophilic polymers is between 0.001% and 30% by weight relative to the weight of the composition. Amine According to one embodiment of the invention, the composition may comprise at least one primary amine, secondary amine or its addition salts, ammonia, hydroxylamine, or mixtures thereof. In general, the addition salts of these amine compounds that may be used in the context of the invention are chosen especially from acid addition salts such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, dodecylbenzenesulfonates, phosphates and acetates, preferably hydrochlorides, citrates, succinates, tartrates, phosphates, lactates.

In particular, the primary or secondary amine or amines which can be used in the context of the invention are chosen from the amines of formula (III) which will be detailed below, the amine polymers, the purine bases and their salts. addition, and their combinations. In particular, the formula (III) is the following: R'7R'8NH (III) Formula (III) in which R'7, R'8, represent independently of one another - a hydrogen atom - a linear, branched and / or cyclic, saturated and / or unsaturated, aromatic or non-aromatic, C1-C20 hydrocarbon radical which may contain from 1 to 5 carbon-carbon and / or optionally substituted double bonds, optionally interrupted by one or more heteroatoms; and / or with one or more groups comprising at least one heteroatom or group comprising at least one heteroatom (preferably chosen from oxygen, nitrogen, sulfur, C = O, C = S, SO, SO 2 or their combinations ); said R'7 and R'8 hydrocarbon radicals possibly being able to form, with the nitrogen atom to which each is attached, a 5- or 7-membered, optionally substituted, optionally aromatic, saturated or unsaturated heterocycle, optionally fused to an aromatic ring or heteroaromatic 6-membered ring, optionally comprising another heteroatom identical to or different from nitrogen; the hydrocarbon radical having no nitro, nitroso, peroxo or diazo function. The compounds of formula (III) are advantageously not oxidation bases or oxidation couplers used in the dyeing of keratinous fibers. Among the groups present as substituents for hydrocarbon groups, heterocyclic groups, mention may be made of the following groups: carboxylic, sulphonic, phosphonic, in acid or salified form, hydroxyl, C 1 -C 4 alkoxy, (C 1 -C 8) alkoxycarbonyl, alkyl (C 1 -C 8), C4) sulfonate, (C1-C8) alkyl phosphonate, tri (C1-C4) alkylsilyl, tri (C1-C4) alkoxy silanyl, amino, (di) (C1-C4) alkylamino, tri (C1-C4) alkylammonium, thiol , (C1-C4) alkylthio, aminosulfonyl, (di-) (C1-C4) alkylaminosulfonyl, aminocarbonyl, (di-) (C1-C4) alkylaminocarbonyl, (C1-C4) alkylcarbonylamino, guanidine, ureido (N (R) 2-CO-NR'-) in which the radicals R and R ', independently of one another, represent a hydrogen atom, a C1-C4 alkyl radical or a (C1-C4) alkylsulphonylamino; phenyl, indolyl, pyrolynyl, imidazolyl optionally substituted by one or more C1-C2 alkyl, hydroxyl. Preferably, the groups present as substituents are chosen from carboxylic groups, in acid or salified form; hydroxyl; C1-C4 alkoxy,; C1-C8 alkoxycarbonyl; thiol; (C1-C4) alkylthio; amino; mono- and di-C 1 -C 4 alkylamino; aminocarbonyl; mono- and di-(C1-C2) alkylaminocarbonyl; (C1-C4) alkylcarbonylamino; phenyl, indolyl, pyrrolinyl, imidazolyl optionally substituted with one or more C1-C12 alkyl, hydroxyl. In particular, the amine (s) of formula (III), which may be identical or different, comprise from one to five primary and / or secondary amine functions; the amine or amines having no N-N bond. Also, the amine (s) of formula (III) do not comprise more than two heteroatoms bonded together. Preferably, the amine or amines are compounds of formula (III), more particularly chosen from compounds of formulas (IIIa) to (IIIi), (IIIr) below, and also their addition salts: amino and / or derivatives of general formula (IIIa): O, H (IIIa) Formula (IIIa) in which: - R9 represents a hydrogen atom or a linear or branched C1-C8 alkyl radical, preferably substituted with one or several hydroxyl, hydroxycarbonyl, thiol, (C 1 -C 4) alkylthio, amido, amino, guanidine groups, a phenyl radical, optionally substituted with one or more hydroxyls, an indolyl radical optionally substituted by one or more hydroxyls, an imidazolyl radical, a pyrrolinyl radical optionally substituted with a C1-C2 alkyl group; or an unsubstituted phenyl radical - R "9 represents hydrogen, a C1-C4 alkyl radical, or an unsubstituted phenyl radical - R10 represents a hydrogen or a C1-C4 alkyl radical - R" 9 and R9 may form together with the nitrogen atom to which they are attached, a 5- or 6-membered saturated heterocycle.

By way of example of compounds of formula (IIIa) and most particularly asparagine, cysteine, glutamine, histidine, lysine, methionine, phenylalanine, proline, pyrrolysine, serine, threonine, tryptophan, tyrosine, and their addition salts. According to another variant, the compounds of formula (IIIa) are advantageously chosen from 2-amino-2-methylpropanoic acid; alpha-methyl-DL-phenylalanine; D, L-alpha- (hydroxymethyl) alanine; D, L-alpha-methyl-meta-tyrosine; alpha-methyl-D, L-tryptophan; D, L-alpha-methylhistidine dihydrochloride; L-2-methylserine; (S) - 2-methylcysteine dihydrochloride; (S) -2-methyl-2-pyrrolidine carboxylic acid. o esters derived from amino acids and / or derivatives of general formula (IIIb): R9 R10 0, R '_, - NH Ri 9 (111b) Formula (IIIb) in which: - R9 represents a hydrogen atom a linear or branched C1-C6 alkyl radical, preferably substituted with one or more hydroxyl, hydroxycarbonyl, (C1-C4) alkoxycarbonyl, thiol, (C1-C4) alkylthio, amido, amino, guanidine, a phenyl radical, optionally substituted by one or more hydroxyls, an indolyl radical optionally substituted by one or more hydroxyls, an imidazolyl radical or a pyrrolinyl radical optionally substituted with a C1-C2 alkyl group; or an unsubstituted phenyl radical - R "9 represents hydrogen, a C1-C4 alkyl radical, or an unsubstituted phenyl radical - R10 represents a hydrogen or a C1-C4 alkyl radical - R" 9 and R9 may form together with the nitrogen atom to which they are attached, a 5- or 6-membered saturated heterocycle. - R11 represents: - a linear or branched, saturated or unsaturated C1-C18 hydrocarbon radical and optionally comprising one to five conjugated or non-conjugated carbon-carbon double bonds, optionally substituted as indicated above, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen, sulfur, C = O, C = S, SO, SO 2 or combinations thereof; the alkyl radical having no nitro, nitroso, peroxo or diazo function; an unsubstituted benzyl radical.

According to a particular variant, R 9 and R 11 may optionally form a saturated carbon ring with 5 members. Preferably, R 11 represents a linear or branched, optionally substituted C 1 -C 10 alkyl radical; a benzyl radical; and even more preferably, a linear or branched C1-C4 alkyl radical optionally substituted with at least one hydroxyl group, preferably from 1 to 2 hydroxyl groups; a benzyl radical. As examples of formula (IIIb) there may be mentioned methoxytyrosine, ethylpiperidine-2 carboxylate; the methyl ester of D, L phenylalanine; Lystine dimethyl ester dihydrochloride; the methyl ester of L-leucine; methyl ester of 2-amino-3-methyl-butyric acid; L-phenylalanine ethyl ester hydrochloride; L-glutamic acid diethyl ester hydrochloride; (S) ethyl-2-amino-3-methylbutanoate hydrochloride; D, L, serine methyl ester hydrochloride; tyrosine methyl ester hydrochloride; L-cysteine ethyl ester hydrochloride; L-histidine methyl ester hydrochloride; (S) pyrrolidine-2-carboxylic acid methyl ester hydrochloride; methyl 2-aminoacetate hydrobromide; ethylglycine; H-DL-alanine ethyl ester hydrochloride; DL tyrosine ethyl ester hydrochloride; methyl-2- (phenylamino) acetate; ethylglutamate; aspartic acid diester alpha, beta, tert-butyl dichloride hydrochloride; L-alpha-aminoisocaproic acid ethyl ester hydrochloride; paratoluene benzyl glycinate sulphonate; DL alanine methyl ester hydrochloride; 5-hydroxy-DL-tryptophan methyl ester hydrochloride; DL-threonine methyl ester hydrochloride; tert-butyl ester of DL proline; DL phenylalanine methyl ester hydrochloride. amides and thioesters derived from amino acids and / or derivatives of general formula (IIIc): X, R12 o (IIIc) Formula (IIIc) in which: R9 represents a hydrogen atom, a C1-alkyl radical -C6, linear or branched, preferably substituted by one or more hydroxyl, alkoxy (C1-C4) carbonyl, hydroxycarbonyl, thiol, (C1-C4) alkylthio, amido, amino, guanidine, a phenyl radical, optionally substituted by one or more hydroxyls, an indolyl radical optionally substituted with one or more hydroxyls, an imidazolyl radical or a pyrrolinyl radical optionally substituted by a C1-C2 alkyl group; R 9 represents a hydrogen or a C 1 -C 4 alkyl radical optionally substituted with a hydroxysulfonyl radical; R 10 represents a hydrogen or a C 1 -C 4 alkyl radical; R 9 and R 9 may form together with the atom to which they are attached, a saturated 5-membered heterocycle; - R12 represents: * a hydrogen atom * a C1-C6 alkyl radical, preferably substituted by one or more hydroxyl, thiol, (C1-C4) alkylthio, amido, amino groups, a phenyl radical, optionally substituted with one or several hydroxyls, an indolyl radical optionally substituted by one or more hydroxyls, an imidazolyl radical or a pyrrolinyl radical optionally substituted by a C1-C2 alkyl group; X represents a sulfur or nitrogen atom. According to a particular variant, R 9 and R 12 may optionally form a saturated carbon ring with 5, 6, 7 members.

In the case where X represents a nitrogen atom and R12 represents an alkyl radical defined as above and very particularly an amino acid residue and / or their corresponding methyl or ethyl ester chosen from alanine, arginine, asparagine, aspartate, cysteine, glutamate, glutamine, glycine, histidine, lysine, methionine, phenylalanine, proline, pyrrolysine, serine, threonine, tryptophan, tyrosine, valine, leucine, isoleucine, the compound of formula (IIIc) represents a dipeptide, an oligopeptide. By way of examples of compounds of formula (IIIc) mention may be made of 3-amino-dihydrothiophene-2-one hydrochloride; DL homocysteine thiolactone; DL-leucyl-DL-alanine, aspartame; (S) -pyrrolidine 2 carboxamide; [N - (- acetamido)] 2-aminoethanesulfonic acid, DL-Alanyl-DL-phenylalanine; 2- (2-aminoacetamido) -3- (4-hydroxyphenyl) propanoic acid; 2- (2-aminoacetylamino) acetic acid; (R) -3-aminoazepan-2-one; glycinamide hydrochloride; L-Leucine amide hydrochloride; 2-aminopropane diamide; 2- (2-amino-3-methylbutanamido) propanoic acid; L-tyrosyl-L-alanine; L-valyl-L-phenylalanine; sarcosyl-L-phenylalanine; L-tyroylbeta-alanine; glycyl-L-proline; glycyl-DL-valine; 2-aminomalonamide; L-methionamide hydrochloride; 2-amino-3-methylbutanamide; Dalaninamide hydrochloride; L-tyrosinamide hydrobromide; the amide of aspartic acid; L-tyrosine amide hydrochloride; L-arginine amide dihydrochloride; lysine amide dihydrochloride; threonine amide hydrochloride; isoleucine amide hydrochloride; histidine amide dihydrochloride; DL amide hydrochloride, alanine; 2-amino-3- (4-hydroxy-phenyl) -propionamide; DL-triptophanamide hydrochloride; N-hydroxy-L-arginine acetate (H-ARG-NH 2 2 AcOH); asparagine amide hydrochloride; alpha-diamide hydrochloride, L-glutamic acid gamma; D-phanylalanine amide; D-leucinamide hydrochloride; L-glutamic acid alpha-amide; L-methionineamide; L-cystine bisamide dihydrochloride; glycinamide acetate; D-lysine amide dihydrochloride; glycinamide; L-isoglutamine gamma-methyl ester hydrochloride; D-arginine amide dihydrochloride; (S) pyrrolidine carboxamide; prolyl histamine hydrochloride. Amino compounds of general formula (IIId): ## STR2 ## in which: R 13, R 14, R 15 and R 16 represent independently of each other: a hydrogen atom a linear, branched and / or cyclic, saturated and / or unsaturated, C1-C20 hydrocarbon radical which may contain from 1 to 5 carbon-carbon double bonds, optionally aromatic, optionally substituted as indicated above, optionally interrupted by one or more heteroatoms; and / or with one or more groups comprising at least one heteroatom, preferably chosen from oxygen, nitrogen, sulfur, CO, C = S, SO, SO 2 or combinations thereof, optionally carrying at least one group hydroxyl or C1-C2 alkoxy, said alkyl radicals R13 and R14 or R14 and R15 or R15 and R16 may optionally form with the carbon atom to which each is attached, a 5- or 7-membered saturated or unsaturated heterocycle, optionally t substituted as indicated above, optionally aromatic, optionally comprising another heteroatom identical to or different from nitrogen; the alkyl radical having no nitro, nitroso, peroxo or diazo function; more particularly an optionally substituted C1-C10 alkyl radical; and preferably, a linear or branched C1-C8 alkyl radical optionally substituted by at least one hydroxyl group, preferably from 1 to 2 hydroxyl groups, a hydroxycarbonyl radical, an ureido radical or a (C1-C4) alkoxycarbonyl radical; an unsubstituted phenyl radical; X represents a nitrogen, oxygen or sulfur atom. - R17 represents: * a hydrogen atom * a linear or branched, saturated or unsaturated C1-C18 hydrocarbon radical and optionally comprising one to five carbon-carbon conjugated or non-conjugated double bonds, optionally substituted as indicated above, optionally interrupted by one or a plurality of heteroatoms and / or one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen, sulfur, CO, C = S, SO, SO 2 or combinations thereof; the alkyl radical having no nitro, nitroso, peroxo or diazo function; more particularly R 17 represents a hydrogen, a linear or branched, optionally substituted C 1 -C 10 alkyl radical; and preferably, hydrogen, a linear or branched C1-C4 alkyl radical optionally substituted with at least one hydroxyl group, preferably from 1 to 2 hydroxyl groups; - R18 represents: * a hydrogen atom * a linear or branched C1-C8 alkyl radical optionally substituted as indicated above, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen, sulfur, CO, C = S, SO, SO2 or combinations thereof, optionally carrying at least one hydroxyl group or C1-C2 alkoxy; the alkyl radical having no nitro, nitroso, peroxo or diazo function, o is an integer between 0 and 5. According to another variant of the invention, the radicals R16 and R17 may optionally form with the carbon atom for R16 and the X atom for the radical R17 to which each is attached, a 5- or 6-membered, saturated or unsaturated heterocycle, optionally substituted as indicated above, optionally aromatic, optionally comprising another heteroatom identical to or different from nitrogen. According to another variant of the invention, the radicals R18 and R15 may optionally form, with the nitrogen atom for R18 and the carbon atom for the radical R15 to which each is attached, a 5- or 6-membered heterocycle, saturated or unsaturated, optionally substituted as indicated above, optionally aromatic, optionally comprising another heteroatom identical to or different from nitrogen. As examples of compounds of formula (111d), mention may be made of L-2-aminohexanoic acid amide hydrochloride; L-phenylalanine amide; (S) (+) aminosuccinic acid; (R) -2- (methylamino) succinic acid; ethyl nipecotate; the carboxylic acid 3-piperidine; 3-phenyl-beta-alanine; ethyl-3-aminobutyrate; 2-carboyethylamine; DL beta-amino adipic acid; beta-alanine ethyl ester hydrochloride; 3-amino-3-ureido-N-butyric acid ethyl ester; dimethyl (S) -aminosuccinate hydrochloride; beta-L-alanine methyl ester hydrochloride; 4-carboxyyethoxypiperidine; 4-aminobutyric acid; DL-beta-amino adipic acid; 4- (methylamino) butyric hydrochloride; ethyl-gamma-aminobutyrate hydrochloride; hexahydronicotinamide; 4-carboxamide piperidine; 3-carbamoyl-2,2,5,5-tetramethylpyrrolidine. Amino compounds of general formula (III): ## STR2 ## in which: R 13, R 14, R 15, R 16 and R 18 have the same meaning as above . - R19 represents: * a hydrogen atom * a linear or branched C1-C8 alkyl radical optionally substituted as indicated above, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen, sulfur, CO, C = S, SO, SO2 or combinations thereof, optionally carrying at least one hydroxyl group or C1-C2 alkoxy; the alkyl radical having no nitro, nitroso, peroxo or diazo function, - p is an integer between 0 and 7. - u is an integer equal to 1 or 2. When u is 2 then the radical R 18 represents a hydrogen. According to another variant of the invention, the radicals R13 and R14 may optionally form, with the carbon atom for R13 and R14 to which these substituents are attached, a saturated 5- or 6-membered heterocycle. By way of examples of compounds (III), mention may be made of the following acids, their enantiomers if they exist, and their salts, their hydrates: (1-aminoethyl) phosphonic acid, (aminomethyl) phosphonic acid, (1-aminoethyl) -1 cyclohexyl) phosphonic acid, (1-aminopropyl) phosphonic acid, (1-aminobutyl) phosphonic acid imino-bis (methylphosphonic), (1-amino-2-methylpropyl) phosphonic acid, (1-amino-2-phenylethyl) phosphonic acid, -amino-1-methylethyl) phosphonic acid (1-amino-3-methylbutyl) phosphonic acid, 1-amino-benzyl phosphonic acid, 1-amino hexyl phosphonic acid, diethyl (aminoethyl) phosphonic acid (especially oxalate salt), tetraethyl (aminomethylene) bisphosphonic acid (in particular its salts), (1-amino-2,2-dimethylpropyl) phosphonic acid, N-methylaminomethylphosphonic acid, (1-aminopentyl) phosphonic acid, (1-amino-2-methylbutyl) phosphonic acid, (1-aminooctyl) phosphonic acid (1-amino-1-methylpropyl) phosphonic acid, (1-amino-1,2-dimethylpropyl) phosphonic acid, (1-amino-1,3-dimethylbutyl) phosphoni (1-amino-1-methylbutyl) phosphonic acid, (1-amino-1-cyclopentyl) phosphonic acid, (1-amino-hydroxycarbonyl) propyl phosphonic acid, (1-amino-1-methylethyl) phosphonic acid, 1-amino-2 methyl-butyl phosphonic acid, 1-phosphono-2-phenylethylamine, (aminomethyl) phosphonic acid, 3-aminopropyl phosphonic acid, 2-amino-2-methyl-4-phosphonobutanoic acid and their ethyl esters, (diethyl (3-aminopropyl) phosphonic acid (in particular salt oxalate), 3- (N-hydroxyamino) propylphosphonic acid, 2-amino-2-methyl-4-phosphonobutyric acid, (3-aminopropyl) phosphonic acid diethyl ester, 2-amino-4-phosphonobutyric acid, 2-aminoethylphosphonic acid, 2- amino-3-phosphonopropionic acid, (2-aminoethyl) phosphonic diethyl ester, diethyl (2-aminoethyl) phosphonic acid, (2 - ((2-pyrrolidinylcarbonyl) amino) ethyl) phosphonic acid, diethyl (2-amino) 1-methyl-2-phenyl) ethyl phosphonic acid, (2-amino-2-phenyl) ethyl phosphonic acid diethyl ester, or mixtures thereof. Amino compounds of general formula (IIIf): ## STR2 ## wherein Furthermore, the radicals R13, R14, R15 and R16 independently of each other may also represent a hydroxy radical, a (C1-C4) alkoxycarbonyl radical, a carboxaldehyde radical, an (C1-C3) alkoxy-q is a integer between 1 and 18 - X represents an oxygen atom, an SH or OH group, a methylene group optionally substituted by a hydroxyl radical. When X represents an oxygen atom, then R 18 forms a 5- or 6-membered ring optionally substituted by one or more hydroxy (methyl), preferably from 1 to 4, hydroxy (methyl) groups. According to another variant of the invention, the radicals R16 and R18 or R13 and R18 may optionally form with the carbon atom for R16 (or for R13) and the nitrogen atom for the radical R18 to which each is attached. a saturated or unsaturated 5- or 6-membered heterocycle, optionally substituted as indicated above, optionally with an aromatic X, optionally comprising another heteroatom which is identical or different from nitrogen. According to another variant of the invention, the amine of formula (IIIf) may contain a p-aminoalcohol resulting from the reduction of the acid or ester function to alcohol of one of the twenty esterified or non-esterified amino acids. By way of examples of compounds (IIIf), mention may be made of the following compounds, their enantiomers if they exist, as well as their salts, their hydrates: isopropanolamine, isopropylamine, methylethanolamine, methylglucamine, stearamine, tromethamine, promethazine, 1, 3- Dimethylpentylamine, octodrine, spermidine, theanine, octamylamine-2-amino-1-phenyl-propane-1,3-diol, 1,3-dihydroxy-2-amino-2-methylpropane, 2-amino-2- (hydroxymethyl) propane-1,3-diol tris, 2-amino-1,3-dihydroxy-2-ethylpropane, 2-amino-3-methylbutan-1-ol, 2-amino-2-methylpropan-1-ol, phenylglycinol, alcohol 2-aminopropyl, 2-hydroxyethylamine, 2-aminohexan-1-ol, 1-amino-1-cyclopentanemethanol, histidinol, 2-amino-3- (3-indolyl) propanol, 3- (4-hydroxyphenyl) -2- amino-1-propanol, beta-aminoisobutanol, 2-amino-1-propanol, 2-amino-1,3-propanediol, 2-amino-4-methyl-1-pentanol, 1-butano-2-amino-3 methyl, beta-amino benzenepropanol, 2-aminopropan-1-ol, 2-amino-1-butanol, 2-amino-4-methyl lpetan-1-ol, 3-aminopropanethiol, ethyl 2-amino-4-mercaptobutanoate, 6-hydroxyhexylamine, beta-D-galactopyranosylamine, BD-glucopyranosylamine, 1-amino-2,5-anhydro-D-mannitol, 1-amino 1-deosy-D-fructose, D-glucosamine, 2-pyrrolidinemethanol, 1-amino-2,3-dihydroxypropane, 3-propanolamine, 3 - [(2-hydroxyethyl) amino] propan-1-ol, dibethane hydroethylamine, bis (3-hydroxypropyl) amine, N-2'-aminoethyl-N-propanolamine, 4-amino-N-butyl alcohol, methyl 3-amino-3-deoxy-AD-mannopyranoside, N-butyl-4-hydroxybutylamine , 4-amino-4- (3-hydroxypropyl) -1,7-heptanediol, 1-hexylamine, 1-octylamine, 1 -nonylamine, 1-decylamine, laurylamine, 1-tetradecylamine, 1-hexadecylamine, 3-acid amino-2-hydroxypropionic acid, 3-amino-2-hydroxy-4-phenylbutanoic acid, 4-amino-3-hydroxybutyric acid, ethyl 4-hydroxy-2-pyrrolidinecarboxylate and mixtures thereof. Amino compounds of general formula (IIIg): ## STR2 ## wherein R13, R14, R15, R16 and R18 have the same meaning as above; R15 R16 R20 R18NH / oSi R13 R14 O SiR20 R20 (IIIg) . R 20 represents a linear C 1 -C 4 alkyl radical; a C 1 -C 4 linear alkoxy radical is an integer between 0 and 5. Y is an integer of 1 or 2. When y is 2, then R 18 represents a hydrogen.

As examples of compounds (IIIg) mention may be made of aminopropyl triethoxysilane, (aminomethyl) trimethylsilane, 2- (trimethylsilyl) ethanamine, 3- (trimethylsilyl) propan-1-amine, 4- (triethoxysilyl) butan-1-amine. N- [3- (trimethoxysilyl) propyl] ethylene diamine, 3- (tri methoxysilyl) propylamine, 3-triethoxysilyl-1-propanamine, (3-methylaminopropyl) trimethoxysilane, and mixtures thereof. Amino compounds of general formula (IIIh): ## STR2 ## in which: R13, R14, R15, R16 and R18 have the same meaning as above. the radicals R13, R14, R15 and R16 independently of each other may also represent a hydroxyl radical, a (C1-C4) alkoxycarbonyl radical, a carboxaldehyde radical or a C1-C3 alkoxy radical; R21 and R22 represent independently of each other: * a hydrogen atom * a linear, branched and / or cyclic, saturated and / or unsaturated C 1 -C 20 hydrocarbon radical which may contain from 1 to 5 carbon-carbon double bonds optionally substituted as indicated above, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least one heteroatom, preferably chosen from oxygen, nitrogen, sulfur, CO, C = S, SO , SO2 or combinations thereof, possibly carrying at least one gro hydroxyl or C 1 -C 2 alkoxy addition, more particularly an optionally substituted C 1 -C 10 alkyl radical; and preferably, a linear or branched C1-C4 alkyl radical optionally substituted by at least one hydroxyl group, preferably from 1 to 2 hydroxyl groups; - R21 and R22 may optionally form with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, saturated or unsaturated, optionally substituted as indicated above, optionally aromatic, optionally comprising another heteroatom identical to or different from the 'nitrogen; the alkyl radical having no nitro, nitroso, peroxo or diazo function, - w is an integer between 1 and 10. According to another variant of the invention, the alkyl radicals R16 and R21 may optionally form with the atom of carbon for R16 and the nitrogen atom for the radical R21 to which each is attached, a 5- or 6-membered, saturated or unsaturated heterocycle, optionally substituted as indicated above, optionally aromatic, optionally comprising another heteroatom identical to or different from the 'nitrogen. According to another variant of the invention, the alkyl radicals R18 and R21 may optionally form with the first nitrogen atom for R18 and the last nitrogen atom for the radical R21 to which each is attached, a heterocycle comprising from 5 to 14-membered, saturated or unsaturated, optionally substituted as indicated above, optionally aromatic, optionally comprising another heteroatom identical to or different from nitrogen.

Among the compounds of formula (IIIh), mention may be made of the amines below, their enantiomers if they exist, as well as their salts, their hydrates: gerontine, N43-aminopropyl] -1,4-butane-diamine, 1, 4-butanediamine, 4- (ethylamino) -N-butylamine, 24342-hydroxy-1,1-bis-hydroxymethyl-ethylamino-propylamino] -2-hydroxymethyl-propane-1,3-diol, 1,4 8,11-tetraazacyclotetradecane, 1,4-diazacycloheptane, 1,3-diamino-2-hydroxypropane, N, N'-bis (2-aminoethyl) propane-1,3-diamine, 3-methylamino propylamine, 1, 3-bisamino propane, N, N'-dimethyltrimethylenediamine, 2,2-dimethyltrimethylenediamine, 2,2-dimethyl-1,3-diaminopropane, N- (2-hydroxyethyl) -1,3-diaminopropane, N- (2- hydroxyethyl) -1,3-diaminopropane, cystamine, 1,5-diaminopentane, 1,6-diaminohexane, lauraminopropylamine, 2-methylheptylamine (2- (N-methyl) heptylamine), ethylenediamine, N, N-bis (2-hydroxyethyl) ethylenediamine, 3-aminoalanine, piperazine-2-carboxylic acid, beta-N-methylamino-alanine, the methyl ester of piperazine-2-carboxylic acid, ethyl 3 amino-prolinate, 2,4-diamino-N-butyric acid, N- [3- (trimethoxysilyl) propyl] ethylene diamine or mixtures thereof. The amino compounds of general formula (IIIi) and / or (IIIi '): H2N (R23) x NH2 z' Y (R24)) e -Z (IIIi) 0110 Formulas (IIIi) and / or (IIIi ') in which: R23 and R24 represent, independently of one another, an optionally substituted C1-C6 alkyl radical, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least one heteroatom, of preferably selected from oxygen, nitrogen, sulfur, CO, SO, SO2 or combinations thereof; the alkyl radical having no nitro, nitroso, peroxo or diazo function; an alkylcarbonyl radical (R-00-) in which R represents a C 1 -C 4 alkyl radical. an alkylsulphonyl radical (RSO 2 -) in which R represents a C 1 -C 4 alkyl radical. a (di-) (alkyl) aminosulphonyl radical ((R) 2 N -SO 2 -) in which the radicals R independently represent a hydrogen or a C 1 -C 4 alkyl radical. a radical (di-) (alkyl) aminocarbonyl (R) 2N-O-) in which the radicals R independently represent a hydrogen or a C 1 -C 4 alkyl radical. a halogen atom preferably chosen from bromine, chlorine or fluorine. a C1-C4 alkoxy group; a C2-04 (poly) hydroxyalkoxy group; a hydroxycarbonyl group (H0-00-) * an alkoxycarbonyl group (RO-CO-) in which R represents a C1-C4 alkyl radical, * an alkylcarbonylamino group (RCO-NR'-) in which the radical R represents a C1-C4 alkyl radical and the radical R 'represents a hydrogen atom or a C1-C4 alkyl radical; an alkylsulphonyl radical (RSO 2 -) in which the radical R represents a C 1 -C 4 alkyl radical; - Y represents a carbon or nitrogen atom - z, z ', z "represents independently of each other a carbon atom, a nitrogen atom or a nitrogen atom substituted by a hydrogen - x is an integer between 0 and 2, when x is less than 2, the unsubstituted carbon atom (s) bear (s) a hydrogen atom - x 'is an integer equal to 0 or 1, when x' is less than 1, the unsubstituted carbon atom (s) bears (s) a hydrogen atom, Among the compounds of formula (IIIi) and / or (IIIi '), mention may be made in particular of the compounds listed below, their enantiomers they exist, as well as their salts, their hydrates alpha-pyridylamine, 2-amino-3-hydroxypyridine, 2-amino-nicotinic acid, 2-amino-3-methylpyridine, 6-methoxy-3-pyridylamine, 3-aminopyridine, 3- amino-4-pyridinylamine, 2,5-aminopyridine, gamma-pyridylamine, 2,3-dimethylpyridine-4-amine, amino (4-) salicylic acid, methylpara-amino benzoate, benzocaine, friendly acid N-benzoic acid, 4-amino-M-anisic acid, 4-amino-3-hydroxy-benzoic acid, 3,4-diaminobenzoic acid methyl ester, methyl 4-amino-3-methoxybenzene carboxylic acid, 2-aminoanisole acid 4-carboxylic acid, 3-amino-4-hydroxy benzoic acid, 3-aminobenzoic acid ethyl ester, 1-amino-3-carboxybenzene, 2-aminobenzoic acid methyl ester, anthranylate ethyl, 1H-pyrazol-3-ylamine, 3-amino-4-carbethoxy-1Hpyrazole, 5-amino-1-ethyl-pyrazole, 1H-benzoimidazol-2-amine, 2-imidazolamine, 1-methylbenzoimidazol-2-amine and their mixtures. It is also possible to use the following amines, in the form of salts or not, lauroyl Ethylenediamine, octopamine, oleamine, palmitamine, 2- (2-aminoethoxy) ethanol, 2-amino-4,5-dimethylthiazole, hexetidine, mecamylamine, tranylcypromine, triamterene methyl [2- (3-trimethoxysilylpropylamino) ethylamino], bis (triethoxysilylpropyl) amine, N1- (3- (trimethoxysilyl) propyl) hexane-1,6-diamine, diethylene triaminopropyl trimethoxy silane, N- (3-triethoxysilylpropyl) ethylene diamine, N- (3-trimethoxysilylethyl) ethylenediamine.

According to another variant of the invention, the amine or amines are chosen from amino polymers, as well as their addition salts. Amino polymer is understood to mean macromolecules of higher or lower molecular weight having one or more primary or secondary amine functions. By "polymer" is meant a compound having at least 5 repeating units chained by covalent bonds. The aminated polymer can be synthesized by radical reactions (polyacrylates, polymethacrylates, polyvinyls, etc.), by condensation reactions (polyesters, polyethers, polyamides, polyurethanes, polydimethylsiloxanes, polypeptides, etc.) by reaction reactions. ring opening (polyesters ...).

It can be of natural origin, chemically modified or not, such as for example polysaccharides (cellulose, dextran, chitosan, guar and their amino or thiolated derivatives, The polymers can be in any type of topology: linear chain, branched, in star or hyperbranched (like dendrimers for example), sequenced, statistical or alternating chains.

The chemical groups can be naturally present on the polymer chain, at the end of the chain, grafted along the main chain or secondary chains, on the branches of star or hyperbranched polymers. Particularly preferred are: 1 / polyamides containing OH groups, or free NH 2 or SH or COOH, for example polylysine 2 / natural or modified polysaccharides having functions NH2 or SH 3 / amino silicones 4 / synthetic polymers with NH 2 or SH functional groups, in particular amine-substituted vinyl polyvinyls and polymers made from the following commercial monomers: ## STR2 ## in which NH 2 and NH 2 NH 2 NH 2 especially among polylysine; chitosan; polyethoxylated amines, such as carboxyPEG8 amine, carboxyPEG12 amine, carboxyPEG24 amine; or their combinations. According to another variant of the invention, the amine or amines are chosen from purine bases, in particular chosen from adenine, adenosine, guanine, guanosine G, thymine, thymidine T, uracil, uridine U, cytosine, cytidine C, their addition salts, and combinations thereof. It would not be outside the scope of the invention by combining several of these variants.

Preferably, if the composition comprises one or more amines, the latter are chosen from ammonia, the compounds of formulas (IIIa), (IIIb), (IIIc), (IIle), (IIIg), in particular when R20 represents a grouping. C1-C4 linear alkoxy, (IIIi ').

If the composition comprises one or more primary or secondary amines, ammonia, hydroxylamine, their content represent in the composition between 0.001 and 65% by weight; and preferably between 0.001 and 30% by weight, based on the weight of the composition.

Enzyme The composition according to the invention may optionally comprise at least one enzyme chosen for example from isolase, β-glucosidase resulting for example from sweet almond (EC 3.2.1.21), alcohol oxidase (EC 1.1.3.13 ), alcohol dehydrogenases EC 1.1.1.1, alcohol dehydrogenases EC 1.1.1.2, alcohol dehydrogenases EC 1.1.1.71, aromatic alcohol dehydrogenases EC 1.1.1.90 still called aryl alcohol dehydrogenases, aromatic alcohol dehydrogenases EC 1.1.1.97, 3-hydroxybenzyl alcohol dehydrogenases EC 1.1.1.97, alcohol coniferylic dehydrogenases EC 1.1.1.194, cinnamyl alcohol dehydrogenases EC 1.1.1.195, methanol dehydrogenases EC 1.1.1.244, aromatic alcohol oxidases EC 1.1.3.7 also called aryl alcohol oxidases, the alcohol oxidases EC 1.1.3.13, the 4-hydroxymandelate oxidases EC 1.1.3.19, the long chain alcohol hydrocarbon oxidases EC 1.1.3.20, the methanol oxidases EC 1.1.3.31, the alcohols shydrogenases EC 1.1.99.20, methylglutamate dehydrogenases EC 1.5.99.5, 2-oxo-acids decarboxylases EC 4.1.1.1, benzoylformate decarboxylases EC 4.1.1.7, phenylpyruvate decarboxylases EC 4.1.1.43, threonine aldolase EC 4.1.2.5. If it is present, the concentration of the enzyme used in the dyeing composition is between 0.005% and 40% by weight relative to the total weight of said composition and preferably between 0.05% and 10% by weight per relative to the weight of this composition. Salts The composition comprising the compound (s) of formulas (I) and / or (11) may optionally comprise one or more salts.

When present, they are generally chosen from organic salts and / or inorganic salts, as well as combinations thereof. In particular, the anions composing these salts can be as well inorganic (chloride, carbonate, hydrogencarbonate, sulphate, hydrogen sulphate, silicate, phosphate, hydrogen phosphate, hydroxide, etc.), as organic (aspartate, formate, acetate, lactate, citrate, gluconate, succinate, malate, fumarate, orotate ...) The cations composing these salts, associated with the anions above, can come from both alkali metals (preferably lithium, sodium, potassium) and alkaline earth metals (preferably magnesium, calcium), only transition metals (scandium, titanium, vanadium, manganese, molybdenum, iron, cobalt, nickel, copper, zinc, silver, gold). Other cations may also form salts such as ammoniums. Preferably, the cations will be chosen from alkali metals (lithium, sodium, potassium), alkaline earth metals (magnesium, calcium), ammoniums, as well as the following transition metals: manganese, molybdenum, iron, copper, zinc , silver and gold. When present, their content represents 0.001 and 40% by weight relative to the weight of the composition, and even more preferably between 0.001 and 20% by weight, relative to the weight of the composition. Other ingredients The cosmetically acceptable medium generally comprises at least water or a mixture of water and at least one organic solvent. Examples of organic solvents that may be mentioned are lower C1-C4 alkanols, such as ethanol and isopropanol; polyols such as 1,3-propanediol or else 1,6-hexanediol and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof. The solvents when they are present are preferably present in proportions preferably of between 1 and 99% by weight relative to the weight of the composition, and still more preferably between 5 and 95% by weight, relative to the weight of the composition. the composition.

The composition used in the process according to the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic polymers. cationic, nonionic, amphoteric, zwitterionic or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or not, such as amino silicones, film-forming agents, ceramides, preserving agents, opacifying agents, polymers conductors. The adjuvants above are generally present in an amount for each of them between 0.01 and 20% by weight relative to the weight of the composition. Of course, one skilled in the art will take care to choose this or these optional additional compounds in such a way that the advantageous properties intrinsically attached to the dyeing composition according to the invention are not, or not substantially, impaired by the or the additions envisaged.

The pH of the composition is generally between 3 and 14 approximately, and preferably between 4 and 11 approximately, more preferably between 6 and 11. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used in dyeing keratinous fibers or even using conventional buffer systems.

Among the acidifying agents, mention may be made, for example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids. Among the alkalinizing agents that may be mentioned, for example, ammonia, alkaline carbonates, the amines mentioned above. The composition may be in various forms, such as in the form of liquid, cream, gel, powders to be mixed before use to obtain poultices, infusions, or in any other form suitable for dyeing keratinous fibers, and in particular hair.

The ingredients of the aforementioned composition are advantageously stored separately. In particular, the compound (s) of formula (I) and / or (11) or the plant extract comprising and the nucleophile or nucleophiles of formulas (a) to (d-) or the oligomer or oligomers or nucleophilic polymers are stored separately. It should also be noted that if one or more amino compounds are present, the latter are also stored separately from the compound or compounds (I) and (11) or the plant extract comprising it. It may also be advantageous to store at least the compound (s) of formulas (I) / (11) or the plant extract comprising, in a container protected from air. The composition used in the process according to the invention may also comprise one or more oxidizing agents. In this case, we speak of ready-to-use compositions.

Oxidizing agent In particular, when an oxidizing agent is present, the ready-to-use composition is advantageously obtained by extemporaneous mixing before the application of a previously described composition, with at least one composition comprising one or more oxidizing agents. The oxidizing agent is preferably chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for example alkali or alkaline earth metal persulfates, perborates and percarbonates. like sodium, potassium, magnesium. Also suitable are enzymatic oxidizing agents such as 4-electron oxidoreductases (such as laccases), 2-electron oxidoreductases (such as uricase), where appropriate in the presence of their donor or co-factors. respective peroxidases. The use of hydrogen peroxide is particularly preferred. This oxidizing agent is advantageously constituted by hydrogen peroxide in aqueous solution (hydrogen peroxide), the titre of which may vary, more particularly, from 1 to 40 volumes, and even more preferably from 5 to 40 volumes. It should thus be noted that the composition used in the invention may result from the extemporaneous mixing of several compositions. The composition which has just been described is therefore applied to human keratin fibers, in particular the hair. Coloring method According to a first embodiment, the composition applied does not comprise an oxidizing agent. This embodiment is appropriate especially in the case where the composition does not comprise oxidation dye (bases / couplers). According to a second embodiment, the ready-to-use composition which has been described above and which is obtained by extemporaneous mixing before application of the composition previously described without any oxidizing agent, with a coating, is applied to the fibers. oxidizing composition. This embodiment is particularly suitable in the case where the composition comprises one or more oxidation dyes (bases / couplers) or that it is desired to obtain a lightening effect.

According to a second variant of this embodiment, the composition without oxidizing agent is applied, and an oxidizing composition, successively and without intermediate rinsing. The oxidizing composition used comprises one or more oxidizing agents as defined above.

Regarding the organic solvents possibly present in the oxidizing composition, reference may be made to the list indicated previously in the context of the description of the composition according to the invention. Usually, the pH of the oxidizing composition is less than 7. The oxidizing composition may be in the form of a solution, an emulsion or a gel. It may optionally comprise one or more additives conventionally used in the field of human keratin fiber staining, depending on the desired dosage form. We can again refer to the list of additives given above. Whatever the embodiment chosen (with or without oxidizing agent, extemporaneous mixing or successive applications of the composition and the oxidizing agent), the mixture applied to the fibers is left in place for a period, in general, of the 1 minute to 5 hours, preferably 10 minutes to 3 hours. As for the temperature at which the composition or compositions are applied, this is generally between 20 and 200 ° C, advantageously between 20 ° C and 55 ° C. This operation can thus be carried out using, for example, a heating helmet, an infra-red lamp, a hair iron or curling iron. The method according to the invention can advantageously be implemented in the presence of a light stimulus.

It consists more particularly in applying to the keratinous fibers thus treated, a UVA radiation, (in particular with an irradiance of between 0.01 and 0.40 milliwatt / cm 2, preferably between 0.1 and 0.2 milliwatt / cm 2, delivered by continuous spectrum lamps or by line-spectrum lamps) and / or UVB radiation (in particular with an irradiance of between 0.01 and 0.20 milliwatt / cm 2, preferably between 0.01 and 0, 1 milliwatt / cm2 delivered by continuous spectrum lamps or line-of-sight lamps). Preferably, these compounds are alkali metal, alkaline earth metal or ammonium salts, carbonate, hydrogencarbonate, chloride, sulfate, silicate, monobasic phosphate, acetate. According to a preferred variant of the invention, this stimulus is carried out by using a composition, comprising in a cosmetically acceptable medium, at least one salt selected from lithium carbonate, sodium, potassium, calcium, ammonium; sodium hydrogencarbonates, potassium; calcium chloride, lithium, sodium; ammonium, sodium, magnesium sulphate; sodium silicate; sodium phosphate monobasic, potassium; sodium acetate.

The composition advantageously has a salt content ranging from 0.001 to 40% by weight relative to the weight of the composition, and even more preferably from 0.001 to 20% by weight, relative to the weight of the composition. It is not beyond the scope of the present invention by performing several successive steps combining stimuli different from each other.

At the end of the pause time, the keratinous fibers may be rinsed with water, optionally washed with shampoo, rinsed with water and dried or allowed to dry. A final subject of the invention consists of a multi-compartment device comprising a first compartment containing at least one compound of formula (I) and / or (II) or the plant extract comprising it, and a second compartment containing at least one a nucleophilic compound of formula (a) to (d "), oligomer or nucleophilic polymer Preferably, the compound (s) of formulas (I) / (11) or the plant extract comprising them are (are) kept away from the air, advantageously under an inert atmosphere.

The device may optionally comprise a third compartment comprising one or more amines.

The examples below illustrate the invention without limiting its scope.

EXAMPLES The staining compositions are obtained by dissolving the extract of Genipa americana (5.10-3mo1.%), 9.4% enriched in genipin and a nucleophilic compound (10-2 mol%) in solution in a sonicator for 20 minutes. comprising a mixture of benzoic acid, benzyl alcohol, ethanol and water). Each composition is applied to natural gray hair with 90% white hair (1 g of lock to 12 g of solution) and said locks are put 30 minutes at 50 ° C (hotplate). Each wick is then rinsed, washed with shampoo and dried in a hair dryer. The Genipa americana extract is obtained using the following method: Immature Genipa americana fruits (100 g) are cut into pieces, frozen, freeze-dried and ground before being extracted with milliQ water.

The bath ratio is 1/20 (= 1 g of lyophilizate per 20 ml of solvent). The suspension is stirred for one hour at room temperature. The raw material is then separated from the solvent by centrifugation at 7500 rpm for 15 minutes, the supernatant is then filtered through Whatman GF / C filter. This filtered extract is then frozen and freeze-dried.

HPLC analysis indicates that the extract is enriched to 9.4% genipin. The summary table below indicates the colorations obtained as a function of the added nucleophilic compounds.

30 Color structure observed on wick test 1 HO NH black H - test 2 / '' '\\ N dark gray HH test 3 NH N gray black 2H the 2HCI OH test 4 NH2 0-1C1 black purple N NH - test 5 r \ I-12 HO black ° ---- \ - OH test 6 - N 'black Cl- test 7 OH \ NH golden brown el test 8 HO el HI \ golden brown 9 HO 0 N elessai H golden test 10 HO IO \ NH golden brown test 11 the NH golden brown OH test 12 CI OH HG 'H2N golden

Claims (6)

REVENDICATIONS1. Coloring composition of human keratinous fibers comprising, in a cosmetically acceptable medium, a compound of formula (I) and / or of formula (II) below, their optical or geometric isomers, their mineral or organic acid salts, their solvates , or a plant extract comprising: R6 (I) (II) Formulas (I) and / or (II) wherein: R1 represents a hydrogen atom, a methyl radical, a hydroxymethyl radical, an aldehyde group; a -CO2R4 group in which R4 represents a hydrogen atom or a C1-C2 alkyl radical; a -CH2-glucose group; R2 represents a hydrogen atom, a hydroxyl radical, a glucose radical; R3, which may be identical or different, represent a hydrogen atom, a hydroxyl radical or a (C1-C4) alkyl radical; the number of hydroxyl groups not being greater than 2; n is an integer from 1 to 5; R5 represents a -CO2R'6 group in which R'6 represents a hydrogen atom, a C1-C2 alkyl radical, an alkali metal cation, an ammonium group; R6 represents a hydrogen, a -CO2R'6 group in which R'6 represents a hydrogen atom, a C1-C2 alkyl radical, an alkali metal cation, an ammonium group; at least one nucleophilic compound chosen from compounds of the following formulas, their optical or geometrical isomers, their salts of organic or inorganic acid, their solvates: (R7) n R8 ^ ----- X N R9 (a). - - -. In which: n is an integer of 0 to 4, the unsubstituted carbon atoms bear a hydrogen atom, A represents -CRio-, -N-, -N + Ri- with R11 representing a radical; C1-C4alkyl * X represents N, CR ', and R'7 represents a hydrogen atom or R7 * R7, which may be identical or different, represents: a C1-C4 alkyl radical, a hydroxyl radical or a C1-C4 alkoxy radical; , an amino radical or a C1-C4 alkylamino radical; two R7 radicals located ortho to each other may form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms (s) chosen from oxygen, nitrogen or a combination thereof, R8, R10, which may be identical or different, represent a hydrogen atom, a hydroxyl radical, an amino radical or a C1-C4 alkyl radical optionally substituted by at least one -COOR12 or -000R12 group with R12 representing a C1-C4 alkyl radical, a -COR13 group with R13 representing a C1-C4 alkyl radical, a group -COOR14 or -000R14 with R14 representing a hydrogen atom or a C1-C4 alkyl radical optionally substituted with at least one C1-C4 alkoxy group; a group -OSO3 * R9 represents a hydrogen atom, a C1-C4 alkyl radical or a (C1-C4) alkylcarbonyl group; an acetyl radical R8 and R9 radicals may form a 5- or 6-membered heterocycle optionally comprising another heteroatom selected from oxygen, nitrogen or sulfur, said heterocycle may be further interrupted by a CO group, when A represents N, that n is 0, X represents CH, and R8 represents NH2, then R9 is neither a hydrogen atom nor a methyl group; (RA '(R15.) N' B '-R16 1 -R16 .N1 \ 1+ R17 \ R17, An An (b) (b') wherein: * n is an integer from 0 to 4; the unsubstituted carbon atoms carry a hydrogen atom, * n 'is an integer from 0 to 2, the unsubstituted carbon atoms carry a hydrogen atom, * A' represents S, - (CR18) 2- , -CR19 = CR'19-, with R18, representing a hydrogen atom, a C1-C4 alkyl radical, R19, R'19, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical; C4; * B 'represents S * R15 which may be identical or different and represents a C1-C4 alkyl radical, a halogen atom, preferably chlorine or a C1-C4 alkoxy radical; R15', which may be identical or different, represent an alkyl radical; C 1 -C 20 R 16 represents a hydrogen atom, a C 1 -C 4 alkyl radical; R 16 'represents a hydrogen atom or a C 1 -C 4 alkyl radical; R 17 represents a C 1 -C 4 alkyl radical; -C4, optionally carrying a hydroxyl group. * R17 'represents e: - a hydrogen atom, - a C1-C4 alkyl radical, optionally carrying a hydroxyl group, optionally interrupted by a CO group, optionally carrying a phenyl radical * the radicals R16 and R17 may together form a 5- or 6-membered fused heterocycle, optionally having one or more unsaturations, optionally substituted with at least one C1-C4 alkyl radical; Wherein * n 'is an integer from 0 to 2; the unsubstituted carbon atoms carry a hydrogen atom, R 20, which may be identical or different, represent a C 1 -C 4 alkyl radical, a halogen atom (preferably chlorine, bromine or iodine), a radical -COOR21 or -000R21 with R21 representing a hydrogen atom, a Cr4 alkyl radical, an amino radical, a C6 aryl group (phenyl) optionally substituted with at least one hydroxyl radical * X represents N, CR22, -CR -22-, CR'22 being connected to Y or X. * Y represents N, CR "22 * R22, R" 22, which may be identical or different, represent a hydrogen atom or a linear or branched alkyl radical; C1-C4 optionally substituted with an amino radical, a benzyl radical, a phenyl radical, -COOR23 or -000R23 R23 representing a C1-C4 alkyl radical, -SOR24 where R24 represents a C1-C4 alkyl radical R22 and R " 22 can together form an aromatic 6-membered aromatic ring (d) N -R29 / N0R29 (d ") (R30) tN (N) (d") HO U (R30) s, (R31), : z ( d) Formulas (d), (d '), (d "), (d"') wherein: * Y is CH, CR27, N * z is N; z 'is N, NR "27 * q is an integer between 0 and 3 * r is 1 or 2 * s is 1 or 2 * t is an integer between 0 and 4 * u is 0 or 1 * the atoms of unsubstituted carbon heterocycles carry a hydrogen atom * R represents a hydrogen atom or a C1-C4 alkyl radical, at least one of R radicals representing at least one hydrogen atom * R27 independently represent one of the others: a linear C1-C4 alkyl radical; a halogen selected from chlorine, bromine and fluorine; R27 represents a hydrogen atom, a linear C1-C4 alkyl radical or a phenyl radical; R 28 represents a hydrogen atom, a linear C 1 -C 4 alkyl radical; the R 27 radicals located in ortho of the NHR 28 and R 28 radical may together form a 5- or 6-membered heterocycle comprising 1 to 2 heteroatoms selected from oxygen and nitrogen. * if Y represents CR27, then q is preferably different from 0 * R29 identical or not, represent a linear C1-C4 alkyl radical, the two radicals R29 may together form a saturated 5-membered heterocycle, * R30 independently represent others a hydroxyl radical, an amino radical, a pyrrolidinyl radical * R31 represent independently of each other: - a C1-C4 alkyl radical - a C1-C4 alkoxy radical optionally substituted by a hydroxyl group - an optionally substituted amino radical by an acetyl group (-COCH3) * R "27 and R31 may form a 5- or 6-membered heterocycle having aromatic or non-aromatic optionally substituted by a C1-C4 alkyl radical. * in the formula (d '), at least 1 one of the radicals R 31 is different from hydrogen and / or at least one is equal to 1; two radicals R 31 may together form an aromatic ring optionally substituted with an amino radical; poses of formulas (a) to (d "') comprising, where appropriate, an anion An or a cosmetically acceptable mixture of anions, guaranteeing the electroneutrality of said formulas; as well as among oligomers or polymers of the polyallylimidazolium type. 2. Composition according to the preceding claim, wherein the plant extract is from the following plants: Veronica persica; Genipa americana; Apodytes dimidiata; Randia canthioides; Tarenna attenuata, and preferably Genipa americana. 3 Composition according to any one of the preceding claims, wherein the content of compound of formula (I) and / or of formula (II) of the composition is between 0.001 and 20% by weight relative to the weight of the composition. 4. Composition according to any one of the preceding claims, wherein the compound or compounds are of formulas (a) and are chosen from the following compounds, their isomers, their salts, their solvates, alone or as a mixture: Structure Chemical name OH CH 3 1-butyl-2-methyl-1H-benzimidazol-7-ol 1H-benzimidazol-5-01 (1H-benzimidazol-4-ol). BrH 1H-benzimidazol-4-ol hydrobromide el g> Ni S [1,3] thiazolo [3,2-appenzimidazol-3 (2H) -one HO N 1H-benzimidazole-5,6-diol hydrobromide ## STR2 ## 2- (2-methoxy-2-oxoethyl) -1,3-dimethyl-1H-3,1-benzimidazol-3-ium methosulphate CH3 Structure Chemical Name NH, CH3 CIH 2-Methyl-1H-benzimidazol-4-amino acid dihydrochloride N 1, ..., ..., n-NH 2 Nile 1,5,6-trimethy1-1H 1H-Benzimidazol-4-amin dihydrochloride, M-benzimidazol-4-amine, H 3 C-dihydrochloride, MH 2 HN-benzimidazol-5-amine dihydrochloride, N 2-methyl -1F-1-benzimidaz 5-amino-amine CH, NH Structure Chemical name H2N-HN NH2 1H-benzimidazole-2,5-2-dihydrochloride 1H-CIH / diamine H 2 N 2 H NH 2 1H-benzimidazole-2,5,6-H 2 N dihydrochloride CIH / 1riannine NH 2 N 2 CIH 4-amino-1H-benzimidazol-7-el-1-OH dihydrochloride Structure Chemical name HO of \ 11 1H-indole-5,6-diol HO 0 0 \ H 5H- 0, 31 dioxolo [4,5-triol] o HO 5H-ethyl 5,6-dihydroxy-11-1-indole-2-carboxylate. Ethyl 6-hydroxy-1H-indole-2-carboxylate HO NH 11 I-indol-5-ol OH 2-methyl-1H-indol-4-ol PI * - Os / '(:) - K + the salt of 1 H-indol-3-yl potassium sulfate 0 [^ N 0. 1H-indol-7-ol-1H-1H-indol-6-ol. Embedded image 4,6-Dimethoxy-1H-indole-2-carboxylic acid and N-methyl-1-indol-4-ol. Ethyl 1H-indole-2-carboxylate N 0 ----- HS Structure Chemical name 1H-indol-4-amine N H 2 IN \ 0 / 1H-indol-3-yl-1H-indol-6-amine N-HH-1H-indol-7-amine N-methyl-3-methoxypropanoate N H 2 N H. 2N is 1H-indol-5-amine H 1 N-ethyl-1H-indol-6-amine H5. A composition according to any one of the preceding claims, wherein the compound (s) are of formulas (a) such that: n is an integer from 0 to 4; the unsubstituted carbon atoms carry a hydrogen atom, A represents -CR10-, -N-, X represents CR ', and R' 7 represents a hydrogen atom or R7 * R7, which may be identical or different, represent: C1-C4 alkyl radical, hydroxy radical, C1-C4 alkoxy radical, amino radical, C1-C4 alkylamino radical, and 5-hydroxy-1H-inclole-2-carboxylate. Ethyl H 2 HNH 2-methyl-11-indole-5,6-diol glycol hydrobromide HO 6-hydroxy-1-1H-indole-2-carboxyl acid 6-hi YY cl N OH H 1H-pyrrolo [2,3-b] pyridin-3-yl acetate OH 1- (3-hydroxy-1H-indol-1-yl) ethanone O * two R7 radicals located ortho to each other may forming a 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms selected from oxygen, nitrogen or their combination, preferably oxygen, R8, R10, identical or different, represent a hydrogen atom , a C1-C4 alkyl radical - a -COOR14 or -000R14 group with R14 representing an atom of hy a C1-C4 alkyl radical optionally substituted with at least one C1-C4 alkoxy group; R 9 represents a hydrogen atom, a C 1 -C 4 alkyl radical, when A represents N, n is 0, X represents CH, and R 8 represents NH 2, then R 9 is neither a hydrogen atom nor a methyl group. 6. Composition according to any one of the preceding claims, in which the compound (s) are of formulas (b) and (b ') and are chosen from the following compounds, their isomers, their salts, their solvates, alone or as a mixture. Chemical name CH, methylsulfate salt del, 4-dimethylquinolinium. ## STR1 ## The 1,2-methyl dimethylquinolinium methylsulfate salt is used in the preparation of the formula. ## STR1 ## wherein the salt of 6-methoxy-1,2- (1,3,100-dimethylquinolinium) methylsulphatesulphonate is used as 2-Methyl-1H-pyrrolo [1,2-cla] quinolinium el-1-ethyl-2-methylquinolinium iodide cIl, H3CI-CH, 6,8-dimethoxy-1 methylsulphate salt 4-H, C-0 1101 N 0 dimethylquinolinium I 0,,,,,,,,,,,,, C, O-Structure Structure Chemical Name H3C CH3 10,10- dimethy1-7,8,9,10-tetrahydro6H-pyhdo [1,2-a] indolium / N Cl Structure Chemical Name S 0 the methyl sulfate salt of 2,3-dimethy1-1,3-> - CH3 is thiazol- 3-ium 113C 0 \ C) N 0 \ CH3 o \ 1 .... B ..-... 1 .7CH the bromide of 4.5-dimethyl-3- (2-oxo-2-scH, phenylethyl) -1,3-thiazol-3-ium CI. N + c ,,, Io the 4-methylbenzenesulfonate salt of 5-chloro-3. ethy1-2-methyl-1,3-benzothiazol-3-lum 0 -S = D H,. 1-1, 3- (2-oxo-2-phenylethyl) -1,3-thiazol-3-yl bromide, N, el, s / 1, methyl sulfate salt. 2-Amino-4-methoxy-3-methyl-1,3-benzothiazol-3-ium-bromide 3- (2-hydroxyethyl) -bromide A composition according to any one of the preceding claims, wherein the compound (s) are of formulas (b) and (b ') such that: ## STR5 ## n is 0, the unsubstituted carbon atoms are hydrogen, A 'is S, - (CR 18) 2-, where R 18 is hydrogen, is C 1 -C 4 alkyl; B 'represents S * R16, represents a hydrogen atom, a C1-C4 alkyl radical; * R16', represents a hydrogen atom or a C1-C4 alkyl radical; * R17 represents a C1-C4 alkyl radical; C4, optionally bearing a hydroxyl group. R17 'represents: a hydrogen atom; a C1-C4 alkyl radical, optionally carrying a hydroxyl group; the radicals R16 and R17 may together form a fused 5- or 6-membered heterocyclic ring, optionally having one or more unsaturations, optionally substituted with at least one C 1 -C 4 alkyl radical. 8. Composition according to any one of the preceding claims, in which the compound or compounds are of formulas (c) and such that: n 'is an integer ranging from 0 to 2, the unsubstituted carbon atoms carry an atom of hydrogen or R20, which may be identical or different, represent a C1-C4 alkyl radical, a chlorine atom, a -COOR21 or -000R21 radical with R21 representing a hydrogen atom, a C1-C4 alkyl radical or an amino radical; , a phenyl group * X represents N, CR22, CR'22 being connected to Y or X. * Y represents N, CR "22 * R22, R'22, R" 22, identical or different, represent an atom of hydrogen, a linear or branched C1-C4 alkyl radical optionally substituted by an amino radical, a benzyl radical or a phenyl radical, - * R22 and R "22 may together form an aromatic 6-membered condensed ring. any of the preceding claims, wherein the carbonyl compounds are of formula (c) and its t selected from the following compounds, their isomers, their salts, their solvates, these compounds being alone or as a mixture: Structure Chemical name 1 H-imidazo [1,2-b] pyrazole ii N N NH N 3,6-dinnethy1 1H-pyrazolo [5,1-c] [1,2,4] riazole NI-N 2 -methyl-4H-pyrazolo [1,5-a] benzimidazine) NN-1-G 7-chloro-2.6- methyl-1H-pyrazolo [1,5-b] [1,2,4] triazole N, N, 7-chloro-3,6-dimethyl-1H-pyrazolo [5,1-c] [1, 2,4] triazole NH) 4 N 6-Ethyl-3-methyl-1H-pyrazolo [5.1-c] [1,2,4] briazole N NH) = N-N-3,6-diethyl-1H-pyrazolo , 1 -c] [1,2,4] triazole "NH 3 -ethyl-6-methyl-1H-pyrazolo [5,1-c] [1,2,4] triazole N / NH 3" phenyl-1H-pyrazolo [5,1-cl [1,2,4] triazole-6- /%, sodium carboxylate II 'N' '' ', 1H [si.NNN NH (3-phenyl) -1H- pyrazolo [5,1-c] [1,2,4-triazol-N'-N-yl] methanol-6-ethyl-3- (propan-2-yl) -1H-pyrazolo [5,1-]; c] [1,2,4] triazole) N NIN = N-11} hydrate and hydrochloride of 3,6-dinnethyl-11-1-H20 pyrazolo [5,1-c] [1] , 2,4] triazol-7-amine NH) 1H-1H 2 H -imidazo [1,2-b] pyrazol-7-NH amine hydrochloride ## STR1 ## NH NH 2 2- (7-chloro-6-methyl-1H-pyrazolo [1.5-N b] [1,2,4] triazol-2-yl) propan-1-amine 2-Methyl-4H-pyrazolo [1,5-NHa] benzimidazol-3-amine N-10 dihydrochloride. A composition according to any one of the preceding claims, wherein the compound (s) are of formulas (d), (d '), (d "), (d-) and selected from compounds Isomers, their salts, their solvates, alone or in mixtures: Structure Chemical name H2 OH 3-amino-1H-pyrazol-5-ol / H. N-(5-hydroxy-1-phenyl-1H-pyrazol-3-yl) acetamide of N, N-3-methyl-1H-pyrazol-5-ol, N 1-12 sulphate of 5- (pyrrolidin-1-yepimidazo [1,2-a] pyridin-8-amine HO-S-OH-NH 2 NH, the dihydrochloride and hydrate of 2 Methyl-2H-H₂O-N-indazole-3,5-diamine N-HClN 2 H 2 Cl 2 2,3-diarnino-6,7-dihydro-NH 2 -5-pyrzolo dihydrochloride 12-a] pyrazol-1-one, α, N, HCl, HCl, 3-amino-67-dihydro-11-1,51-1-pyrazolo [1,2-ajpyrazol-1-one hydrochloride] 4-Annino-4,2-diethyl-5-Ni (pyrrolidin-1-yl) -1,2-dihydroxy-4-chlorohydrate dihydro-3H-pyrazol-3-one. 0 N-12 1-0 4-Amino-1,2-diethyl-5-hydroxy-1,2-dihydro-3H-pyrazol-3-one hydrochloride CH. ## STR1 ## 4,5-diamino-1,2-diethy1,1,2-dihydro-3H-pyrazol-3-one dihydrochloride NI-12 / ----. 3-amino-2-chloro-6-H-methylphenol HCl 3-amino-2-chloro-6-methylphenol hydrochloride O-3,4-dihydro-2H-1,4-benzoxazin-6-ol H 2 NH 2 FCl 2-H hydrochloride (3-Aminopyrazolo [1,5-a] pyridin-2-yl) oxylethanol NNH 2 OH 2-aminopyridin-3-ol 11. A composition according to any one of the preceding claims, wherein the or the compounds are selected from the compounds of formulas (a), (c), (d), (d '), (d "), (d-) or mixtures thereof A composition according to any one of the preceding claims, in which the content of compound (s) of formula (s) (a) to (d-) or oligomers or nucleophilic polymers is between 0.001% and 30% by weight relative to the weight of the composition. any one of the preceding claims, wherein the composition comprises at least ammonia, hydroxylamine, a primary amine or condaire, or their mixtures. Composition according to the preceding claim, wherein the amine is chosen from the amines of formula (III) detailed below, the amine polymers, the purine bases, as well as their addition salts, and combinations thereof; R'7R'8NH (III) Formula (III) in which R'7, R'8, independently of one another represent: - a hydrogen atom - a linear, branched C1-C20 hydrocarbon radical and / or cyclic, saturated and / or unsaturated, aromatic or not, which may contain from 1 to 5 carbon-carbon double bonds and / or optionally substituted, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least a heteroatom or group comprising at least one heteroatom (preferably selected from oxygen, nitrogen, sulfur, CO, = C = S, SO, SO 2 or combinations thereof); said R'7 and R'8 hydrocarbon radicals possibly being able to form, with the nitrogen atom to which each is attached, a 5- or 7-membered, optionally substituted, optionally aromatic, saturated or unsaturated heterocycle, optionally fused to an aromatic ring or heteroaromatic 6-membered ring, optionally comprising another heteroatom identical to or different from nitrogen; the hydrocarbon radical having no nitro, nitroso, peroxo or diazo function. 15. Composition according to any one of claims 13 or 14, wherein the content of amine (s) primary (s) or secondary (s) present (s) in the composition is between 0.001 and 65% by weight; and preferably between 0.001 and 30% by weight, based on the weight of the composition. 16. Composition according to any one of the preceding claims, comprising one or more inorganic organic salts chosen from: chloride, carbonate, hydrogencarbonate, sulphate, hydrogen sulphate, silicate, phosphate, hydrogen phosphate, hydroxide, or organic anions chosen from: aspartate, formate, acetate, lactate, citrate, gluconate, succinate, malate, fumarate, orotate associated with * alkaline, alkaline earth metals, transition metals such as scandium, titanium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, silver, gold, or ammoniums. 17. Composition according to the preceding claim wherein the salt content (s) is from 0.001 to 40% by weight relative to the weight of the composition, and even more preferably from 0.001 to 20% by weight, relative to the weight of the composition. composition. 18. A process for staining human keratin fibers in which a composition according to any one of the preceding claims is applied. Process according to the preceding claim, in which a temperature of between 20 and 200GC is applied. 20. Method according to one of claims 18 or 19, wherein UVA radiation is applied, in particular with an irradiance of between 0.01 and 0.40 milliwatt / cm 2, and / or UVB irradiation radiation in particular between 0.01 and 0.20 milliwatts / cm2. 21. A multi-compartment device comprising a first compartment containing at least one compound of formula (I) and / or (II) or the plant extract comprising, as described in one of claims 1 or 2, and a second compartment containing at least one compound of formula (a) to (d "'), oligomers or nucleophilic polymers, according to any one of claims 1, 4 to 11.15