EP1056434A1

EP1056434A1 - Dyeing method using a specific cationic derivative and a compound selected among a specific aldehyde, a specific ketone, a quinone and a di-imino-isoindoline or 3-amino-isoindolone derivative

Info

Publication number: EP1056434A1
Application number: EP99961140A
Authority: EP
Inventors: Hervé Andrean; Alain Lagrange
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1998-12-23
Filing date: 1999-12-22
Publication date: 2000-12-06
Also published as: JP2002533371A; WO2000038639A1; FR2787707B1; CA2320925A1; US6635090B1; FR2787707A1

Abstract

The invention concerns the use for dyeing keratinous fibres of at least a specific cationic derivative and at least a compound selected among a specific aldehyde, a specific ketone, a quinone and a di-imino-isoindoline or 3-amino-isoindolone derivative for dyeing, by reaction without oxidising agent, said keratinous fibres. The invention also concerns compositions comprising said compounds and dyeing agents using them.

Description

"Dyeing process using a specific cationic derivative and a compound chosen from a specific aldehyde, a specific ketone, a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone"

The present invention relates to the use for dyeing keratin fibers of at least one specific cationic derivative and of at least one compound chosen from a specific aldehyde of formula (lu) defined below, a specific ketone of formulas (IN) or (N) defined below, a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone, to dye compositions comprising the combination of these compounds, to dyeing processes using uses said compounds and a device with several compartments containing these compounds. For the dyeing of keratin fibers, and in particular human keratin fibers such as the hair, it is known to use direct dyes or colored substances which give the fibers a temporary or semi-permanent coloring, of low dyeing power and which generally eliminates with washing or perspiration. The ranges of shades obtained by these direct processes are generally reduced. It is also known to use oxidation dyes (oxidation bases and couplers) which are initially colorless or weakly colored compounds, generating, under the action of an oxidant, compounds colored by a process of oxidative condensation. Oxidation stains are, compared to direct, permanent, powerful, and resistant to external agents (light, bad weather, washing, perspiration and friction). However, the use of the oxidizing agent can alter the keratin fibers and makes the processes for implementing oxidative dyes relatively complex. The Applicant has just discovered a new dyeing process, not implementing a process for the development of dyes by oxidative means, making it possible to obtain a wide range of shades. The compounds used by the applicant are small molecules which can easily penetrate into keratin. The Applicant has found, surprisingly, that these compounds can then condense into chromophores or dyes, larger molecules which remain trapped within keratin. The Applicant has thus found that the colors obtained are resistant to shampoos and to perspiration, stable to light, weathering and chemical agents. In a way, the Applicant has discovered a new dyeing process having the advantages of the so-called oxidation dye without having the disadvantages, no oxidizing agent being used.

The subject of the present invention is therefore the use for dyeing keratin fibers of a specific cationic derivative and of a compound chosen from Lin aldehyde of formula (III), a ketone of formulas (IN) or (N), a quinone and a derivative of diiminσ-isoindoline or 3-amino-isoindolone.

Another subject of the invention relates to dye compositions comprising these compounds.

The present invention also relates to a process for dyeing keratin fibers consisting in applying to the fibers a specific cationic derivative and a compound chosen from an aldehyde of formula (III), a ketone of formulas (IN) or (N), a quinone and a derivative of di-iminoisoindoline or 3-amino-isoindolone, either simultaneously, in the form of an extemporaneous mixture, or successively. Another object of the invention also consists of a dyeing agent for carrying out the process of the invention.

Other objects of the invention will appear in the light of the description.

The main object of the present invention is therefore the use for dyeing keratin fibers, in particular human keratin fibers such as human hair, of at least one specific cationic derivative and of at least one compound chosen from an aldehyde of formula (III), a ketone of formulas (IV) or (V), a quinone, and a derivative of diimino-isoindoline or 3-amino-isoindolone making it possible to obtain, by reaction without an oxidizing agent, a coloration of said keratin fibers.

In the context of the present invention, the canonical derivatives are chosen from:

• the compounds of formula (I) below:

in which: n denotes an integer from 1 to 4;

R ₁ denotes an alkyl, hydroxyalkyl, polyhydroxyalkyl, alkylhydroxyalkyl, alkylsulfonyl, carboxyalkyl, aminoalkyl, (di-hydroxy) alkylaminoalkyl, alkyl-NR'R "radical (in which R 'and R" are alkyl or can form together with the atom nitrogen to which they are attached a 5 or 6-membered aliphatic or heterocyclic ring), or an aryl, the alkyl radicals of the groups defined above comprising from 1 to

4 carbon atoms and can be linear or branched;

A and nitrogen together form a 5 or 6-membered, unsaturated, aromatic or heterocyclic hydrocarbon ring which can be interrupted by one or more nitrogen, oxygen or sulfur atoms, and which can be substituted by one or more radicals such that -N0 ₂ ,

-NH ₂ , acetylamino, -OH, -SO ₃ H, a halogen atom, -CH ₃ S0 ₂ , -CF ₃ , C _r C ₄ alkyl, (C _r C ₄ ) alkoxy, alkyl (C _r C ₄ ) thio, alkoxy (C _j -C ^ carbonyl, A denotes a substituted or unsubstituted carbon, a substituted or unsubstituted nitrogen, an oxygen, a sulfur; the 5 or 6-membered hydrocarbon ring formed by A and the nitrogen can also be fused with a substituted or unsubstituted aromatic ring such as, in particular aryl or naphthyl substituted by one or more halogen, allyl, alkoxy radicals;

• or the compounds of formula (II) below:

in which :

R _j is defined as above,

R ₂ , R ₃ , R ₄ or R ₅ , identical or different, denote the substituents designated by R _j .

B denotes -CH- or nitrogen; the groups R ₂ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R _} , the group R ₅ or R 4 and B, can form, jointly with the atoms to which they are attached, a hydrocarbon ring at 5 or 6-membered, unsaturated, aromatic or heterocyclic which can be interrupted by one or more nitrogen or sulfur atoms and which can be substituted by one or more radicals such as -N0 ₂ , -NH ₂ acetylamino, -OH, -S0 ₃ H , a halogen atom, -CH ₃ S0 ₂ , -CF ₃ , -OCF ₃ , C _r C ₄ alkyl, (C ₁ -C ₄ ) alkoxy, (C _r C ₄ ) alkyl thio, alkoxy (C _r C ₄ ) carbonyl, and the cosmetically acceptable salts of these compounds.

The compounds of formula (I) are especially chosen from the following compounds: - 1,2,3-Trimethyl-3H-imidazol-1-ium; iodine - 2,3,4-Trimethyl-thiazol-3-ium; iodine

- 3-ethyl-methylbenzothiazolium iodide -3-methyl-methylbenzothiazolium methosulfate -l, 2,3,3-tetramethyl-3H-indolium iodide - 3-ethyl-methylbenzooxazolium iodide

- 1,2,3-Trimethyl-3H-imidazol-l-ium methosulfate

- 3- (2-Carboxy-ethyl) -2,5-dimethyl-benzooxazol-3-ium; bromide

- 3-ethyl-methylbenzothiazolium toluene-4-sulfonate

- 5-Chloro-3-ethyl-2-methyl-benzothiazol-3-ium; toluene-4-sulfonate - 1-Ethyl-2-methyl-naphtho [1,2-d] thiazol-1-ium; toluene-4-sulfonate

- 1,2,3-Trimethyl-3H-benzoimidazol-l-ium tetrafluoroborate

- 2-Ethyl-3-methyl-benzo [d] isothiazol-2-ium; tetrafluoro borate

- 2-Methyl-3- (3-sulfonate-propyl) -benzothiazol-3-ium

- 3-tert-Butyl-2-methyl-benzothiazol-3-ium; bromide - 3- (2-Carboxy-ethyl) -2,5-dimethyl-benzooxazol-3-ium; bromide

- 5-Methoxy-2-methyl-3- (3-sulfonate-propyl) -benzothiazol-3-ium

- 2-Methyl-l- (3-sulfonate-propyl) -naphtho [1,2-d] oxazol-l-ium

- 2-Methyl-3- (3-sulfonate-propyl) -naphtho [2,3-d] oxazol-3-ium

- 2,5,6-Trimethyl-3- (3-sulfonate-propyl) -thieno [2,3-d] thiazol-3-ium - l-Ethyl-2-methyl-naphtho [1,2-d] oxazol -l-ium; perchlorate

- 1,2-Dimethyl-naphtho [1,2-d] thiazol-l-ium, Methosulfate

- 3-Ethyl-2,5,6-trimethyl-benzooxazol-3-ium; iodine

- 2-Methyl-l- (3-sulfonate-propyl) -naphtho [1,2-d] thiazol-l-ium

- 1-Ethyl-2-methyl-naphtho [1,2-d] thiazol-1-ium; perchlorate - 2-Methyl-5-phenyl-3- (3-sulfonate-propyl) -benzooxazol-3-ium

- 3-Ethyl-6-methoxy-2-methyl-benzothiazol-3-ium; iodine

- 5-Methoxy-1,2-dimethyl-naphtho [1,2-d] thiazol-l-ium; iodine

- 5-Chloro-3-ethyl-2-methyl-benzothiazol-3-ium; toluene-4-sulfonate

- 5,6-Dimethoxy-2,3-dimethyl-benzothiazol-3-ium; toluene-4-sulfonate - 3-Ethyl-2-methyl-benzo [4,5] thieno [2,3-d] thiazol-3-ium; toluene-4-sulfonate

- 1-Ethyl-2-methyl-naphtho [1,2-d] thiazol-1-ium; toluene-4-sulfonate

- 5,6-dichloro-3-ethyl-2-methyl-l- (3-sulfonate-butyl) -3H- benzoimidazol- 1 -ium - 2,3-Dimethyl-5-phenyl-benzooxazol-3-ium methosulfate - 5-Methoxy-1,2-Dimethyl-benzo [cd] indolium; perchlorate

- 1-Butyl-2,3,3-trimethyl-3H-indolium; iodine

- 1,1,2,3-Tetramethyl-1H-benzo [e] indolium; iodine

The compounds of formula (II) can be chosen from:

- 1,2-Dimethyl-quinolinium; iodine

- 1,2-Dimethyl-quinolinium; chloride

- 1,4-Dimethyl-quinolinium; iodide - 1-Ethyl-2-methyl-quinolinium; tetrafluoro borate

- 2-Methyl- 1- (3-sulfonate-propyl) -quinolinium

- 2,3-Dimethyl-isoquinolinium; iodine

- 4-Chloro-1,2-dimethyl-quinolinium methosulfate

- 7-Chloro-1,4-dimethyl-quinolinium - 1-Ethyl-2,6-dimethyl-quinolinium; iodine

- 4-Methoxy-1,2-dimethyl-quinolinium; iodine

- 1-Ethyl-4-methyl-quinolinium; iodine

- 1,2,3,4-Tetrahydro-pyrido [1,2-a] quinolinylium; toluene-4-sulfonate

- l, r-trimethylenebis (2,4-dimethylpyridinium), bromide - 1, -tetramethy lenebis (2,5-dimethylpyridinium) perchlorate

- 1, l - (oxydiethylene) bis (2-methylquinolinium) perchlorate

- 1,2-Dimethyl-pyridinium methosulfate

- 1,2,4-Trimethyl-pyridinium; chloride

- 1,2,4,6-Tetramethyl-pyridinium; chloride - 4-Methoxy-1,2,6-trimethyl-pyridinium; perchlorate

- 1- (2-Hydroxy-ethyl) -2-methyl-pyridinium; chloride

The aldehyde corresponds to the following formula (lu):

HR _ô - C≈O (ni) in which :

R ₆ denotes a group of formula (lu A) below:

in which :

R ₇ and Rg, identical or different, denote a hydrogen atom, an alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl, alkoxy, -CF ₃ or -OCF _{3 group} ,

R ₇ and R ₈ can also form, together with the atoms to which they are attached, an aryl or heterocyclic ring with 5 or

6 links, said rings being able to be substituted or not; m denotes an integer from 0 to 3,

R _g denotes the substituents designated by R ₇ , a substituted or unsubstituted aryl or alkylaryl group, a substituted or unsubstituted 5 or 6-membered heterocyclic group, or with the cosmetically acceptable salts of these compounds.

The ketone is chosen from the ketones of formulas (IV) or (V) below:

in which :

R ₁₀ denotes the substituents designated by R ₆

R _u denotes an alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl group, an aryl, alkylaryl group, a substituted or unsubstituted 5 or 6-membered heterocyclic,

R ₁₀ and R _n can also form, together with the atoms to which they are attached, a 5 or 6-membered aryl ring, or a heterocyclic comprising heteroatoms such as N or S, the said ring being able itself to be attached to a 5 or 6-membered aryl ring or to a heterocycle comprising heteroatoms such as N or S, the said rings being able to be substituted or not, or to the cosmetically acceptable salts of these compounds.

Quinone can meet the following formulas (VI) and (VII):

in which :

R ₁₂ denotes a hydrogen or halogen atom, a sulfonic or alkoxy group.

R ₁₃ , R ₁₄ and R ₁₅ , which are identical or different, denote a hydrogen atom, a halogen atom, a hydroxy, alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl, alkylsulfonyl, carboxyalkyl, aminoalkyl, alkylaminoalkyl, (di-hydroxy) alkylaminoalkyl, or alkyl-NR'R "(with R 'and R" denoting alkyl or which can form, together with the nitrogen atom to which they are attached, an aryl ring or a 5 or 6-membered heterocycle), an aryl group, a group amino which may be substituted by an alkyl or a hydroxyalkyl,

R ₁₂ and R ₁₃ , R ₁₃ and R ₁₄ or R ₁₄ and R ₁₅ may form, together with the atoms to which they are attached, an aryl ring or a 5 or 6-membered heterocycle, substituted or not; or to the cosmetically acceptable salts of these compounds.

The derivatives of di-imino-isoindoline or of 3-amino-isoindolone can be those corresponding to the following formula (VIII):

in which :

R ₁₆ and R ₁₇ , identical or different, denote a hydrogen atom, an alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl, aminoalkyl, alkylaminoalkyl, (di-hydroxy) alkylaminoalkyl group, or an alkyl group NR'R ", with R ' and R "denoting alkyl or possibly forming, together with the nitrogen atom to which they are attached, an aryl ring or a 5 or 6-membered heterocycle, A denotes an oxygen or NH atom,

X and Z together form an aryl ring or a 5 or 6-membered heterocycle, substituted or not; or to the cosmetically acceptable salts of these compounds.

Among the preferred compounds of formula (III), mention may in particular be made of benzaldehyde, 2,3,4, monohydroxy-benzaldehydes, 2,3,4, monomethoxy-benzaldehydes,

2,3,4, monomethyl-benzaldehydes, the (2,3), (2,4), (2,5), (2,6), (3,5) - dihydroxy benzaldchydcs, the (2,3) , (2,4), (2,5), (2,6), (3,5) -dimethoxy benzaldehydes, vaniline, isovaniline, syringaldehyde, (2,3), (2,4) , (2,5), (2,6), (3,5) -dimethyl-benzaldehydes, 4-isopropyl-benzaldehyde, 4-dimethylamino-benzaldehyde, 4-diethylaminol-bnnaldehyde, piperonal, the (2,6 ), (3,5) -dimethyl-4-hydroxybenzaldehyde, 2,3,4-mononitro-benzaldehydes. 2-hydroxy-3-methoxy-benzaldehyde, 2-hydroxy-4-methoxy-benzaldehyde, 2-hydroxy-5-methoxy-benzaldehyde. 2-hydroxy-6-melhoxybenzaldehyde, 4-methylthio-benzaldehyde, (2,3,4), (2,4,6), (3,4,5), (2,4,5) -tπhydroxy -benzaldehydes, methyls 2, 3 and 4-formylbenzoates, 2,3,4-mono (2-hydroxyethoxy) -benzaldehydes, 4-nitro-3-hydroxy-benzaldehyde, 3-nitro-4-hydroxy-benzaldehyde , 2-nitro-4-hydroxy-benzaldehyde, 3-nitro-2- hydroxy-benzaldehyde, 2,3,4-monotrifluoro-benzaldehydes, 2,3-dihydroxy-4-methoxy-benzaldehyde, 3,4-dihydroxy-5-methoxy-benzaldehyde, 3,5-dihydroxy-4- methoxy-benzaldehyde, 3-methoxy-2-nitrobenzaldehyde, 4-methoxy-2-nitrobenzaldehyde, 2-methoxy-3-nitrobenzaldehyde, 4-methoxy-3-nitrobenzaldehyde, (2,3,4), ( 2,4,6), (3,4,5), (2,4,5) -trimethoxy-benzaldehydes, 5-niUOvaniline, the (2,4), (2,6) -dinitrobenzaldehydes, pentamethyl- benzaldehyde, 4-methylsulfonyl-benzaldehyde, 2,3,4-monoformylphenoxyacetic acids, 4-diethylamino-salicylaldehyde, 4 (3-dimethylaminopropoxy) -benzaldehyde, 2,3-dihydrobenzo

(b) furan-5-carboxaldehyde, 1 and 2 naphthhaldehyde, 6 and 5 carboxaldehyde-1,4-benzodioxane, 2,4-monl ydroxy-l-naphthaldehydes, l-monhydroxy-2-naphthaldehyde, 1 (4-formylphenyl) -imidazole, 4-pyrrolidinol-benzaldehyde, 2,4 monomethoxy-1-naphthhaldehydes, 2,3-dimethyl-chroman-6-carboxaldehyde, 2,3,6,7-tetrahydro- 1H, 5H-pyrido (3.2, 1-IJ)

Quinoline-9-carbaldehyde, 4 dimethylamino-1-naphthhaldehyde, 9-anthraldehyde, 3-nitro-4-pyrrolidino-benzaldehyde, 3-nitro-4-piperidino-benzaldehyde, 3-nitro-4-morpholino- benzaldehyde, pyridines 2,3,4-monocarboxaldehydes, 5-formyl-6-methyluracil, pyridoxale, quinolines - 2,3,4-monocarboxaldehydes, 8-hydroxy-quinoline-2-carboxaldehyde- 2 and 3 -furaldehydes, 2 and 3-thienylcarboxaldehydes, 2 and 3-imidazo-carboxaldehydes, 2-pyrrolcarboxaldehyde, 5-nitro-2-furaldehyde, 5- (dimethylamino) - 2-furaldehyde, pyrazol-3-carbaldehyde , 5-nitro-2-thiophene-carboxaldehyde, 5-nitro-3-thiophenecarboxaldehyde, indole-3-carboxaldehyde, N-methyl-indole-3-carboxaldehyde, 2-methyl-indole-3-carboxaldehyde , 4,5,6,7-monomethyl-indole-carboxaldehyde and 5-formyl-2-furansulfonic acid. The ketones of formulas (IV) and (V) can be chosen from 2,3 indolinedione, 2,3-butanedione, 2,3-pentanedione, (2,3), (3,4) -hexanedione, l-phenyl-1,2-propanedione, benzyl, furil, 2,2'-pyridil, nitro-benzyl, anisil, 3,3'-dimethoxybcnzyl, 4,4'-bis ( dimethylamino) benzyl, camphoroquinone, cyclohexane-1,2-dione, isatin, N-methyl-isatin, 4,5,6,7- monomethyl-isatin, (4,5), (4,7), (5,7), (6,7) -dimethyl-isatinc, N-ethyl-isatin, N-hydroxymethyl-isatin, 5, 6.7 monomethoxyisatin, 4,5,6,7 monochloroisatin, 4,5,6,7 monobromoisatin, N-isopropyl-isatin, N-butyl-isatin, N-propyl- isatin, 5-nitro-isatin, 5-sulfonic-isatin, 2,4,5-trihydroxypyrimidine, alloxane, 1,3-dimethyl-hexahydro-2,4,5,6-pyrimidinetettaone, ninhydrin, chinisatin, 1,3-indenedione, squaric acid, croconic acid. 3,4-dimethoxy-3-cyclobutene-1,2-dione, 3,4-ethoxy-3-cyclobutene-1,2-dione, 3,4-isopropoxy-3-cyclobutene-1,2-dione , 3,4-di-N-butoxy-3-cyclobutene-1,2-dione, rhodizonic acid, oxindole, N-methyl-2-indolinone, N-methyl-nitro-2-indolinone , 6-methoxyoxindole, 5,6-dimethoxyoxindolc and 5 and 6-monochlorooxindole.

The preferred quinones of formulas (VI) and (VII) are, inter alia, 1,4 naphthoquinone, spinulosin, aromentine, aurentioglyocladine, 2,5-dihydroxy-6-methylbenzoquinone, 2-hydroxy- 3-methyl-6-methoxylbenzoquinone, 2,5-dihydroxy-3,6-diphenylbenzoquinone, 2,3-dimethyl-5-hydroxy 6-methoxy-benzoquinone, 2,5-dihydroxy 6-isopropyl-benzoquinone, lawsone, juglone, fafioline, naphtazarin, naphtopurpurin, lapachol, plumbaginc, chloroplumbagine, droserone, shikonin, 2-hydroxy-3-methyl-1,4-naphthoquinone. 3,5-dihydroxy-1,4-naphthoquinone, 2,5-dihydroxy-1,4-naphtoquinone, 2-methoxy-5-hydroxy- 1,4-naphtoquinone, 3-methoxy-5-hydroxy- 1, 4-naphthoquinone, (1,4), (1,2) naphthoquinone, 4,5-dimethoxy-1,2-benzoquinone, phenanthrenequinone and 4-sulfonic acid (1, 2) naphthoquinone.

The derivatives of formula (Vffl) are in particular represented by 3-imino-3H-isoindol-ylamine, 3-imino-4-methyl-3H-isoindol-1-ylamine, 3-imino-4-terbutyl-3H- isoindol-1-ylamine, 3-imino-7-nitiO-3H-isoindol-1 -ylamine, 3-amino-1-imino-1H-isoindol-4-ol, 3-imino-7-isopropoxy-3H -isoindol-1-ylamine, 3-imino-7- (2,2,2-trifluoroethoxy) -3H-isoindol-1-ylamine, 3-imino-7-ethoxy-3H- isoindol-1 -ylamine, 3-imino-7-butoxy-3H-isoindol-1 -ylamine, 3-amino-1-imino-1H-isoindole-4-sulfonic, 3-imino-7- chloro-3H-isoindol-1 -ylamine, 3-imino-5-methyl-3H-isoindol-1-yiamine, 3-imino-5-ethyl-3H-isoindol-1-ylamine, 3-imino-5 - terbutyl-3H-isoindol-1-ylamine, 3-imino-5-amino-3H-isoindol-1-ylamine, N- (1-amino-3-imino-3H-isoindol-5-yl) -acetamide , 3- imino-5-nitro-3H-isoindol-l -ylamine, 3-imino-5-fluoro-3H- isoindol-1 -ylamine, 3-imino-5-chloro-3H-isoindol-l- ylamine- 3- imino-5-methylsulfanyl-3H-isoindol-l -ylamine, 3-imino-5-methoxy- 3H-isoindol-l-ylamine, 3-imino-5-ethoxy-3H-isoindol-l -ylamine, 3-imino-5-propoxy-3H-isoindol-1-ylaminc, 3-imino-5-isopropoxy- 3H-isoindol-1-ylamine, 3-imino-5-butoxy-3H-isoindol- l-ylamine, la

3-imino-5-isobutoxy-3H-isoindol-l -ylamine, 3-imino-5-terbutoxy- 3H-isoindol-l-ylamine, 3-imino-5- (2,2,2-trifluoromethyl) - 3H- isυindol-1 -y lamine, 3-imino-5- (2,2,2-trifluoroethoxy) -3H-isυindol- 1-ylamine, 3-imino-5-methanesulfonyl-3H-isoindol-l-ylamine . 3- imino-5,6-dimethyl-3H-isoindol-1-ylamine, 3-imino-5,6-diethyl-3H-isoindol-1-ylamine, 3-imino-5,6-dimethoxy-3H -isoindol-ly lamine, 3-imino-5,6-diethoxy-3H-isoindol-l-ylaminc, 3-iminυ-5,6- dibutoxy-3H-isoindol- 1 -ylamine, 3-imino-5 , 6-bis-trifluoromethyl- 3H-isoindol-1-ylamine, 3-imino-5,6-dichloro-3H-isoindol-1-ylamine, 5,6-bis-ethoxymedιyl-3-imino-3H-isoindol -l-ylamine, the

3-amino-1-imino-1H-isoindol-4,7-diol, 4,7-dichloro-3-imino-3H- isoindol-1-ylamine, 4,5,7-trichloiO-3-imino-N6, N6-dimethyl-3H- isoindol-1, 6-diamine, 4,5,6,7-tetrachloro-3-imino-3H-isoindol-1 - ylamine, 4,5,6,7-tetrafluoro-3- imino-3H-isoindol-1-ylamine, 3-butylimino-3H-isoindol-1 -ylamine, 2- (3-amino-isoindol-1-ylideneamino) -ethanol, 3- (3-amino-isoindol- l-ylideneamino) -3- methyl-pentane-1,5-diol, N- (3-amino-isoindol-l-ylidene) -guanidine, 7-imino-7H-pyrrolo [3,4-b] pyridin -5-ylamine, 7-imino-7H- pyrrolo [3,4-b] pyrazin-5-ylaminc, 7-imino-2,3-dimethyl-7H- pyrrolo [3,4-b] pyrazin-5 -ylamine. 7-imino-7H- [1,4] dithiino [2,3-c] pyrrol-5-ylamine, 7-imino-2,3-dimethyl-7H- | l, 4] dithiino | 2,3-c] pyrrol-5-ylamine, 7-imιno-2,3-dihydro-7H- [1,4] dithiino [2,3- c] pyrrol-5-ylamine, 7-imino-2 -methyl-2,3-dihydro-7H- [1,4] dithiino [2,3-c] pyrrol-5-ylamine, 3-amino-isoindol-l-one, 3-amino-7-methyl- isoindol-1-one, 3-amino-7-hydroxymethyl-isoindol-1-one, 3-amino-7-chloro-isoindol-1-one, 3-amino-4-chloro-isoindol- 1-one, 3-amino-1-oxo-1H-isoindole-4-sulfonic, 3 -amino-4-nitro-isoindol-1-one, 3-amino-6-nitro-isoindol-l -one, 3-amino-6- methyl-isoindol-1-one, 3-amino-6- chloro-isoindol-1-one, 3-amino-6-bromo-isoindol-1-one, 3-amino-6-methylsulfanyl-isoindol-

1-one, 3-amino-6-methoxy-isoindol-1-one, 3-amino-5-chloro-isoindol-1-one, 3-amino-5-fluoro-isoindol-1-one, 3-amino-5-methoxy-isoindol-1-one, 3-amino-5-nitro-isoindol-1-one, the ethyl ester of 3-amino-1-oxo-1H-isoindole-5 acid -carboxylic, 3-amino-5,6-dichloro-isoindol-l-one, 3-amino-5,6-dibromo-isoindol-

1-one, 3-amino-4,7-dichloro-isoindol-1-one, 3-amino-4,5,7- trichloro-isoindol-1-one, 3-amino-4,5,6 , 7-tetrachloro-isoindol-l-one, 3-amino-4,5,7-trichloro-6-methylsulfanyl-isoindol-l-one, 3-amino-4,5,6,7-tetrabromo-isoindol -l-one, 3-amino-4,5,6,7- tetrafluoro-isoindol-1-one, 3-methylamino-isoindol-1-one, 3-ethylamino-isoindol-1-one, 3 -propylamino-isoindol-1-one, 3-dimethylamino-isoindol-1-one, 7-ethylamino-pyrrolo [3,4-b] pyridin-5-one, 7-amino-pyιτolo [3,4- b] pyridin-5-one, 3-amino-pyrrolo [3,4-c] pyridin-5-one, 3-amino-6-methyl-pyrrolo [3,4- c] pyridin-1-one, 5-amino-pyrrolo [3,4-b] pyridin-7-one, 7-amino-pyrrolo [3,4-b] pyrazin-5-one, 7-amino-2-methyl-pyrrolo [3 , 4- b] pyrazin-5-one, 7-amino-2,3-dimethyl-pyriOlo [3,4-b] pyrazin-5 one, 7-amino-2,3-dihydro- [1, 4] dithiino [2,3-c] pyrrol-5-one, 3-imino-2-methyl-2,3-dihydro-isoindol-l-one, 3-imino-2-ethyl-2,3- dihydro-isoindol-1-one, 3-imino-2-propyl-2,3-dihydro-isoindo ll-one, 2-hydroxymethyl-3-imino-2,3-dihydro-isoindol-1-one, 2- (2-hydroxyethyl) -3-imino-2,3-dihydro-isoindol-1 -one, 2- (1 -imino- 3-oxo-1,3-dihydro-isoindol-2-yl) -ethane sulfonic acid, 3- (l-imino-3-oxo-1,3, di-hydro-) acid isoindol-2-yl) -propionic, 2- (3-hydroxypropyl) -3-imino-2,3-dihydiO-isoindol-l-one and 5-imino-6-methyl-5,6-dihydro-pyrrolo [3,4-b] pyridin-7-one. In the context of the present invention:

The halogen atoms preferentially denote a fluorine, chlorine, bromide or iodine atom; The alkyl and monohydroxyalkyl radicals polyhydroxyalkyles, alkylhydroxyalkyle, alkylesulfonyle, carboxyalkyle, aminoalkyle, alkylaminoalkyle, dihydroxyaminoalkyle can be linear or branched;

The alkyl groups denote in particular the groups of 1 to 20 carbon atoms, such as for example, the methyl, ethyl, propyl, isopropyl, n-propyl, butyl, n-butyl, tert-butyl, pentyl, n-pentyl, isopentyl groups. , n-hexyl, isohexyl, heptyle, octyl, nonyle, decyle, undecyle, dodecyle and pentadecyle. Preferably, the alkyl groups denote a group of 1 to 6 carbon atoms; these alkyl groups can be substituted; for example, by a halogen atom, a cyano or hydroxy radical, and can thus represent the trifluoromethyl, δ-chloropropyl, β-cyanoethyl or β-hydroxyethyl radicals.

Among the monohydroxyalkyl groups, mention may in particular be made of hydroxymethyl, hydroxy ethyl, hydroxypropyl and hydroxybutyl groups.

Among the polyhydroxyalkyl radicals, mention may, for example, be made of the dihydroxyethyl, dihydroxypropyl, trihydroxypropyl and dihydroxybutyl radicals. The alkoxy groups denote a group -O-R, R representing an alkyl group as defined above.

Alkenyl groups denote a monovalent radical corresponding to ethylenic carbons, such as, for example, alkyl or 3,3dimethylallyl. Acetyloxy groups denote an -O-CO- group

R, R representing an alkyl group as defined above.

Among the cycloalkyl radicals, mention may in particular be made of cyclohexyl and cyclopentyl.

Among the aryl radicals, which may be mono or polycyclic, mention may in particular be made of phenyl or naphthyl groups.

Among the heterocycles, which may be mono or polycyclic and containing one or more heteroatoms, mention may be made of the thiophene, pyrrole, imidazole, pyrazole, triazole, thiazole, furan, benzofuran, benzimidazole, benzothiazole, pyridyl rings benzoxazole, quinolyl, quinazoyl, quinoxalyl or naphthyl.

Among the alkylaryl radicals, mention may in particular be made of the benzyl, phenethyl or naphthylmethyl group.

Aminoaryl groups denote the -NHR groups, R representing an aryl radical.

In the context of the present invention, the cycloakyles, aryl and heterocycles may be substituted or polysubstituted, for example by halogen, a C _j -C alkoxy, C _j -C nitro, hydroxy, a carboxylic group, an acetyloxy group, C - ^ - C ^, carboxamide, sulfonamide, sulfonic group, nitrile, -CF _3, -OCF _3, or with a cycloalkyl or aryl radical which may be substituted by alkyl C _j - C ₄ .

In the context of the present invention, the formulas (I) to (VIII) are not limited to those specifically described but also include their tautomeric forms when they exist.

Within the meaning of the present invention, the cosmetically acceptable salts of the abovementioned compounds can be hydrochlorides, sulphates, hydrobromides or tartrates. The compositions for dyeing keratin fibers, in particular human keratin fibers such as the hair, in accordance with the present invention are essentially characterized in that they comprise at least one cationic derivative as defined above and at least one compound chosen from an aldehyde as defined above, a ketone as defined above, a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone as defined above, in a medium suitable for dyeing.

Preferably, the cationic derivative of these compositions is chosen from 3-ethyl-methylbenzothiazolium iodide, 1,2,3,3-tetramethyl-3H-indolium iodide, 3-ethyl-methylbenzooxazolium iodide, 1,2-dimethylquinolinium iodide , 5-chloro-3-ethyl-2-methylbenzothiazolium iodide, 2-methyl-l- (3-sulfo-propyl) - naphthof 1, 2-d] thiazolium betaine. In a preferred embodiment of the invention, the compound chosen from an aldehyde of formula (III), a ketone of formulas (IV) or (V), a quinone and a derivative of di-iminoisoindoline or 3-amino-isoindolone is chosen from 1,4-naphthoquinone , isatin, N-methylisatin, 3-imino-3H-isoindol-1-ylamine, 4-dimethylaminobenzaldehyde and 4-dimethylaminonaphthaldehyde.

The cationic derivative can be present in a concentration ranging from 0.01 to 10%, and preferably from 0.05 to 5% by weight relative to the total weight of the composition. The compound chosen from an aldehyde of formula (III), a ketone of formulas (IV) or (V), a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone can be present in a concentration ranging from 0.01 to 10% and preferably from 0.05 to 5% by weight relative to the total weight of the composition. The medium suitable for dyeing is preferably an aqueous medium consisting of water and / or cosmetically acceptable organic solvents, and more particularly, alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, ethylene glycol and its monomethyl, monoethyl and monobutyl ethers, propylene glycol or its ethers such as, for example, propylene glycol monomethyl ether, butylene glycol, dipropylene glycol as well as the diethylene glycol alkyl ethers such as, for example, the monoethyl ether or the monobutyl ether of diethylene glycol, in concentrations of between approximately 0.5 and 20% and, preferably, between approximately 2 and 10% by weight relative to the total weight of the composition.

It is also possible to add to the composition according to the invention fatty amides such as mono- and di-ethanolamides of acids derived from coconut, lauric acid or oleic acid, at concentrations of between approximately 0.05 and 10% by weight.

It is also possible to add to the composition according to the invention surfactants well known from the prior art and of anionic, cationic, nonionic, amphoteric, zwitterionic type or their mixtures, preferably in a proportion of between about 0, 1 and 50% by weight and advantageously between about 1 and 20% by weight relative to the total weight of the composition.

Thickening agents can also be used in an amount ranging from about 0.2 to 20%. Said dye composition may also contain various usual adjuvants such as antioxidants, perfumes, sequestering agents, dispersing agents, hair conditioning agents, preserving agents, opacifying agents, as well as any other adjuvant used usually in tincture of keratin materials.

Of course, those skilled in the art will take care to choose the optional compound (s) mentioned above, in such a way that the advantageous properties intrinsically attached to the dye composition according to the invention are not, or not substantially, altered. by the addition (s) envisaged.

The dye composition according to the invention can be formulated at acidic, neutral or alkaline pH, the pH being able to vary for example from 2 to 11 and preferably from 5 to 10, and being able to be adjusted by means of alkalinizing agents or d previously known acidifying or buffering agents.

As alkalizing agents, there may be mentioned ammonia, alkali carbonates, alkanolamines, for example mono- and triethanolamines and their derivatives, sodium or potassium hydroxides, and the compounds of formula:

in which, R is a propylene residue optionally substituted by a hydroxyl group or a C _r C ₄ alkyl radical; Ra, Rb, Rc and Rd, simultaneously or independently of one another represent a hydrogen atom, an alkyl radical in C _r C ₄ hydroxyalkyl c _r c _4. Acidifying agents are typically mineral acids or organic, such as hydrochloric, tartaric, citric and phosphoric acids.

Among the buffers, there may be mentioned, for example, potassium diacid phosphate / sodium hydroxide. The composition applied to the hair can be in various forms, such as in the form of a liquid, cream, gel or in any other form suitable for dyeing keratin fibers. In particular, it can be packaged under pressure in an aerosol can in the presence of a propellant and form a foam.

According to the present invention, the process for dyeing keratin fibers, in particular human keratin fibers such as the hair, is essentially characterized in that a component (A) consisting of a composition containing is applied to said fibers. in a medium suitable for dyeing, at least one cationic derivative such as those defined above, and a component (B) consisting of a composition containing in a medium suitable for dyeing, at least one compound chosen from an aldehyde of formula (III), a ketone of formulas (IV) or (V), a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone such as, for example, one of those defined above , so as to allow the development of a dye on said keratin fibers.

In a preferred embodiment of the process of the invention, the components (A) and (B) are mixed just before use, then the resulting composition is immediately applied to the keratin fibers, and left to act for 1 to 60 minutes and preferably from 1 to 30 minutes; the keratin fibers then being rinsed, washed with shampoo, rinsed again, then dried.

Another process of the present invention consists essentially in applying the component (A) to the keratin fibers, followed or preceded by the application to the said fibers of the component (B), in leaving each component to act for 1 to 60 minutes and preferably 1 to 30 minutes, if necessary rinse with water between each application; the keratin fibers then being rinsed, washed with shampoo, rinsed again, then dried.

An object of the invention also consists of a dyeing agent for keratin fibers, in particular human hair, characterized in that it consists of the components (A) and (B) stored in separate form, such as defined above.

The components (A) and (B) are intended either to be mixed all just before use, or to be applied successively to the fibers to be treated.

According to one embodiment, the different components (A) and (B) can be packaged in a device with several compartments also called a "dye kit" comprising all the components intended to be applied for the same dye on keratin fibers, in especially human keratin fibers such as the hair, in successive applications with or without premix.

Such devices may comprise a first compartment containing the component (A) containing the cationic derivative and a second compartment comprising the component (B) containing the compound chosen from an aldehyde, a ketone, a quinone and a derivative of di-imino- isoindoline or 3-amino-isoindolone.

Another variant may also consist in storing the component (A) or the component (B) in an anhydrous solvent medium and in providing a third compartment containing an aqueous medium suitable for dyeing and cosmetically acceptable. In this case, the contents of the third compartment are mixed just before use in one or the other or the two compartments containing the anhydrous components (A) and (B) or else the three compartments are mixed before use.

Concrete examples illustrating the invention will now be given. Example 1

The following dye composition was prepared just before use: 3 -imino-3H-isoindol-1 -ylamine 0.435 g

3-ethyl-methylbenzothiazolium iodide 0.915 g ethyl alcohol 30.0 g water q.s.p. 100, g

The above composition was applied to locks of natural gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a golden yellow shade.

Example 2

The following dye composition was prepared just before use:

4-dimethylaminobenzaldehyde 0.447 g 3-ethyl-methylbenzothiazolium iodide 0.915 g ethyl alcohol 30.0 g water q.s. 100, g

The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for

30 minutes. After rinsing with running water and drying, the hair was dyed in a bright neon pink shade.

Example 3

The following dye composition was prepared just before use: 1,4-naphthoquinone 0.474 g

3-ethyl-methylbenzothiazolium iodide 0.915 g ethyl alcohol 30.0 g water qs 100, g The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a blue violet shade.

Example 4

The following dye composition was prepared just before use: 1,4-naphthoquinone 0.474 g l, 2,3.3-tetramethyl-3H-indolium iodide 0.903 g ethyl alcohol 30.0 g water q.s.p. 100, g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a purple shade.

Example 5

The following dye composition was prepared just before use: isatin 0.441 g l, 2,3.3-tetramethyl-3H-mdolium iodide 0.915 g ethyl alcohol 30.0 g water q.s.p. 100, g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a light orange shade. Example 6

The following dye composition was prepared just before use: 4-dimethylaminobenzaldehyde 0.447 g l, 2,3,3-tetramethyl-3H-indolium iodide 0.915 g ethyl alcohol 30.0 g water q.s.p. 100, g

The above composition was applied to locks of permanent gray hair and allowed to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a raspberry red shade.

Example 7

The following dye composition was prepared just before use: 3 -imino-3H-isoindol-l -ylamine 0.435 g l, 2,3,3-tetramethyl-3H-indolium iodide 0.903 g ethyl alcohol 30.0 g water q.s. 100, g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a pale apricot shade. Example 8

3-ethyl-methylbenzooxazolium iodide 0.867 g ethyl alcohol 30.0 g water q.s. 100, g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a light coppery shade.

Example 9

The following dye composition was prepared just before use:

1, 4-naphthoquinone 0.474 g 3-ethyl-methylbenzooxazolium iodide 0.867 g ethyl alcohol 30.0 g water q.s. 100, g

Example 10

The following dye composition was prepared just before use: isatin 0.441 g

3-ethyl-methylbenzooxazolium iodide 0.867 g ethyl alcohol 30.0 g water qs 100, g The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a sandy shade.

Example 11

The following dye composition was prepared just before use: 4-dimethylaminobenzaldehyde 0.447 g

The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a light straw shade.

Example 12

The following dye composition was prepared just before use:

3-imino-3H-isoindol-l -ylamine 0.435 g 3-ethyl-methylbenzooxazolium iodide 0.867 g ethyl alcohol 30.0 g water q.s. 100, g

The above composition was applied to locks of bleached gray hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a light straw shade. Example 13

The following dye composition was prepared just before use: 3-imino-3H-isoindol-1-ylamine 0.435 g

1, 2-dimethylquinolinium iodide 0.805 g ethyl alcohol 30.0 g water q.s.p. 100.0 g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a straw yellow shade.

Example 14

The following dye composition was prepared just before use:

4-dimethylaminobenzaldehyde 0.447 g 1.2-dimethylquinolinium iodide 0.805 g ethyl alcohol 30.0 g water q.s. 100.0 g

30 minutes. After rinsing with running water and drying, the hair was dyed in an orange-pink shade.

Example 15 The following dye composition was prepared just before use:

1,4-naphthoquinone 0.474 g

1,2-dimethylquinolinium iodide 0.805 g ethyl alcohol 30.0 g water qs 100.0 g The above composition was applied to locks of natural gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a yellow green shade.

Example 16

The following dye composition was prepared just before use: i satin 0.441 g

1,2-dimethylquinolium iodide 0. 805 g ethyl alcohol 30.0 g water q.s.p. 100.0 g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a golden yellow shade.

Example 17

The following dye composition was prepared just before use:

4-dimethylaminobenzaldehyde 0.447 g 5-chloro-3-ethyl-2-methylbenzothiazolium iodide 1J51 g ethyl alcohol 30.0 g water q.s. 100.0 g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a purplish red shade. Example 18

The following dye composition was prepared just before use:

3-imino-3H-isoindol-1-ylamine 0.435 g 5-chloro-3-ethyl-2-methylbenzothiazolium toluene-4 sulfonate 1, 151 g ethyl alcohol 30.0 g water q.s. 100.0 g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a lemon yellow shade.

Example 19

The following dye composition was prepared just before use:

1,4-naphthoquinone 0.474 g

5-chloro-3-ethyl-2-methylbenzothiazolium toluene-4 sulfonate 1.151 g ethyl alcohol 30.0 g water q.s.p. 100.0 g

The above composition was applied to locks of bleached hair and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a blue violet shade. Example 20

The following dye composition was prepared just before use: isatin 0.441 g 5-chloro-3-ethyl-2-methylbenzothiazolium toluene-4 sulfonate 1.151 g ethyl alcohol 30.0 g water q.s. 100.0 g

Example 21

The following dye composition was prepared just before use:

4-dimethylaminobenzaldehyde 0.447 g 2-methyl-l- (3-sulfo-propyl) -naphtho [1,2-d] thiazolium betaine 0.963 g benzyl alcohol 7.0 g ethyl alcohol 23.0 g water q.s. 100.0 g

The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a light rosewood shade. Example 22

The following dye composition was prepared just before use: 3-imino-3H-isoindol-l-ylamine 0.435 g 2-methyl-l- (3-sulfo-propyι) ~ naphtho [l, 2-d] thiazolium betaine 0.963 g benzyl alcohol 7.0 g ethyl alcohol 23.0 g water qs 100.0 g

The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a light orange shade.

Example 23

The following dye composition was prepared just before use:

1,4-naphthoquinone 0.474 g

2-methyl-1- (3-sulfo-propyl) -naphtho [1,2-d] thiazolium betaine 0.963 g benzyl alcohol 7.0 g ethyl alcohol 23.0 g water q.s.p. 100.0 g

The above composition was applied to locks of natural gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a green shade. Example 24

The following dye composition was prepared just before use: isatin 0.441 g 2-methyl-l- (3-sulfo-propyl) -naphtho [1,2-d] thiazolium betaine 0.963 g benzyl alcohol 7.0 g ethyl alcohol 23 0.0 g water qs 100.0 g

Example 25

The following dye composition was prepared just before use:

4-dimethylaminobenzaldehyde 0.447 g

5-methoxy-2-methyl-3- (3-sulfo-propyl) benzothiazolium betaine 0.904 g benzyl alcohol 7.0 g ethyl alcohol 23.0 g water q.s. 100.0 g

30 minutes. After rinsing with running water and drying, the hair was dyed in a rosewood shade. Example 26

The following dye composition was prepared just before use: 3-imino-3H-isoindol-1-yalmine 0.435 g 5-methoxy-2-methyl-3- (3-sulfo-propyl) - benzothiazolium betaine 0.904 g benzyl alcohol 7 0.0 g ethyl alcohol 23.0 g water qs 100.0 g

The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a golden yellow shade.

Example 27

The following dye composition was prepared just before use:

1,4-naphthoquinone 0.474 g 5-methoxy-2-methyl-3- (3-sulfo-propyl) benzothiazolium betaine 0.904 g benzyl alcohol 7.0 g ethyl alcohol 23.0 g water q.s. 100.0 g

The above composition was applied to locks of natural gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in a yellow green shade. Example 28

The following dye composition was prepared just before use: isatin 0.441 g 5-methoxy-2-methyl-3- (3-sulfo-propyl) benzothiazolium betaine 0.904 g benzyl alcohol 7.0 g ethyl alcohol 23.0 g water q.s. 100.0 g

The above composition was applied to locks of permanent gray hair containing 90% white hairs and left to stand for 30 minutes. After rinsing with running water and drying, the hair was dyed in an iridescent orange shade.

Claims

1. Use for dyeing keratin fibers, in particular human keratin fibers such as human hair, of at least one cationic derivative chosen from the compounds of formula (I) below:

in which: n denotes an integer from 1 to 4;

R _j denotes an alkyl, hydroxyalkyl, polyhydroxyalkyl, alkylhydroxyalkyl, alkylsulfonyl, carboxyalkyl, aminoalkyl, (di-hydroxy) alkylaminoalkyl, alkyl-NR'R "radical (in which R 'and R" are alkyl or can form together with the atom nitrogen to which they are attached a 5 or 6-membered aliphatic or heterocyclic ring), or an aryl, the alkyl radicals of the groups defined above comprising from 1 to

4 carbon atoms and can be linear or branched;

-NH ₂ , acetylamino, -OH, -S0 ₃ H, a halogen atom, -CH ₃ S0 ₂ , -CF ₃ , C _r C ₄ alkyl, (C ₁ -C ₄ ) alkoxy, (C _j alkyl -C ^ thio, alkoxy (C _j -

C ₄ ) carbonyl,

A denotes a substituted or unsubstituted carbon, a substituted or unsubstituted nitrogen, an oxygen, a sulfur; the 5 or 6-membered hydrocarbon ring formed by A and the nitrogen can also be fused with a substituted or unsubstituted aromatic ring; or the compounds of formula (II) below

in which :

R _j is defined as above,

B denotes -CH- or nitrogen; the groups R _j and R ₂ , R ₂ and R, R ₃ and R ₄ , R ₅ and R _j , the group R ₅ or R4 and B, can form, jointly with the atoms to which they are attached, a hydrocarbon ring containing 5 or 6-membered, unsaturated, aromatic or heterocyclic which can be interrupted by one or more nitrogen or sulfur atoms and which can be substituted by one or more radicals such as -N0 ₂ , -NH ₂ acetylamino, -OH, -S0 ₃ H, a halogen atom, CH ₃ S0 _2, -CF _3, -OCF _3, C _j -C alkoxy (C ₁ -C ₄₎ alkyl (C ₁ -C ₄ alkyl) thio, alkoxy (C ₁ - C ₄ ) carbonyl, and the cosmetically acceptable salts of these compounds;

and at least one compound chosen from:

• an aldehyde corresponding to the following formula (III):

H R - C = O (III)

in which :

Rg denotes a group of formula (111 A) below:

in which :

R ₇ and R ₈ , which are identical or different, denote a hydrogen atom, an alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl, alkoxy, -CF ₃ or -OCF _{3 group} ,

R ₇ and Rg can also form, together with the atoms to which they are attached, an aryl or heterocyclic ring with 5 or

Rc denotes the substituents designated by R ₇ , a substituted or unsubstituted aryl or alkylaryl group, a substituted or unsubstituted 5 or 6-membered heterocyclic group, or with the cosmetically acceptable salts of these compounds,

• a ketone corresponding to the following formulas (IV) or (V):

O o

(IV) \ / (V)

/ / \

R 10 \, R 10 R 1 1

in which :

R ₁₀ denotes the substituents designated by R ₆

R _1} denotes an alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl group, an aryl, alkylaryl group, a substituted or unsubstituted 5 or 6-membered heterocyclic,

R _j0 and R- _Q can also form, together with the atoms to which they are attached, a 5 or 6-membered aryl ring, or a heterocyclic ring comprising heteroatoms such as N or S, the said ring itself being able to be attached to an aryl ring with 5 or 6 links or with a heterocycle comprising heteroatoms such as N or S, the said rings possibly being substituted or not, or to the cosmetically acceptable salts of these compounds,

• a quinone, and a derivative of diiminoisoindoline or 3-amino-isoindolone making it possible to obtain, by reaction without oxidizing agent, a coloration of said keratin fibers.

2. Use according to claim 1, characterized in that the quinone corresponds to the following formulas (VI) and (VII):

in which :

R ₁₂ denotes a hydrogen or halogen atom, a sulfonic or alkoxy group.

R ₁₃ , R ₁₄ and R ₁₅ , identical or different, denote a hydrogen or halogen atom, a hydroxy, alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl, alkylsulfonyl, carboxy alkyl, aminoalkyl, alkylaminoalkyl, (di-hydroxy) alkylaminoalkyl group , or alkyl-NR'R "(with R 'and R" denoting alkyl or which can form, together with the nitrogen atom to which they are attached, an aryl ring or a 5 or 6-membered heterocycle), an aryl group, a amino group which can be substituted by an alkyl or a hydroxyalkyl,

R ₁₂ and R ₁₃ , R ₁₃ and R ₁ or R ₁ and R ₁₅ may form, together with the atoms to which they are attached, an aryl ring or a 5 or 6-membered heterocycle, substituted or not; or to the cosmetically acceptable salts of these compounds.

3. Use according to any one of claims 1 or 2, characterized in that the derivatives of di-imino-isoindoline or of 3-amino-isoindolone correspond to the following formula (VIII):

in which :

R ₁₆ and R ₁₇ , identical or different, denote a hydrogen atom, an alkyl, mono or polyhydroxyalkyl, alkylhydroxyalkyl, aminoalkyl, alkylaminoalkyl, (di-hydroxy) alkylaminoalkyl group, or an alkyl group NR'R ", with R ' and

R "denoting alkyl or possibly forming, together with the nitrogen atom to which they are attached, an aryl ring or a 5 or 6-membered heterocycle, A denotes an oxygen or NH atom,

4. Composition for dyeing keratin fibers, in particular human keratin fibers such as the hair, characterized in that it comprises at least one cationic derivative chosen from the compounds defined according to claim 1 and at least one compound chosen from one aldehyde chosen from the compounds defined according to claim 1, a ketone chosen from the compounds defined according to claim 1, a quinone, and a derivative of di-iminoisoindoline or 3-amino isoindolone in a medium suitable for dyeing, allowing to obtain, without an oxidizing agent, a dye of said keratin fibers.

5. Dye composition according to claim 4, characterized in that the quinone and the derivative of di-iminoisoindoline or of 3-amino-isoindoline is chosen from the compounds defined according to claims 2 or 3.

6. Dye composition according to any one of claims 4 or 5, characterized in that it has a pH of between 2 and 11.

7. Composition according to Claim 4, characterized in that the cationic derivative is present in a concentration ranging from OJ to 10% and preferably from 0.5 to 5% by weight relative to the total weight of the composition.

8. Composition according to any one of claims 4 or 5, characterized in that the compound chosen from an aldehyde, a ketone, a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone is present in a concentration ranging from OJ to 10% and preferably from 0.5 to 5% by weight relative to the total weight of the composition.

9. Composition according to any one of claims 4 to 8, characterized in that the medium suitable for dyeing is an aqueous medium consisting of water and / or organic solvents chosen from alcohols, glycols and glycol ethers, in proportions of between 0.5 and 20% by weight relative to the total weight of the composition.

10. A process for dyeing keratin fibers, in particular human keratin fibers such as the hair, characterized in that it consists in applying to said fibers a component (A) consisting of a composition containing in a medium suitable for the dye, at least one cationic derivative chosen from the compounds defined according to claim 1 and at least one component (B) consisting of a composition containing, in a medium suitable for dyeing, at least one compound chosen from an aldehyde chosen from the compounds defined in claim 1, a ketone selected from the compounds defined in claim 1, a quinone and a derivative of di-imino-isoindoline or 3-amino-isoindolone so as to allow the development of a dye with said keratin fibers.

11. Method according to claim 10, characterized in that the quinone and the derivative of di-imino-isoindoline or 3-amino-isoindolone is chosen from the compounds according to any one of claims 2 or 3.

12. Method according to any one of claims 10 or 11, characterized in that it consists in mixing the components (A) and (B) just before use, immediately applying the resulting composition to the keratin fibers and leaving to act for 1 to 60 minutes and preferably for 1 to 30 minutes; the keratin fibers then being rinsed, washed with shampoo, rinsed again, then dried.

13. Method according to any one of claims 10 or 11, characterized in that it consists in applying to the keratin fibers the component (A), followed or preceded by the application to said fibers of the component (B), leaving each component to act for 1 to 60 minutes and preferably for 1 to 30 minutes, optionally rinsing with water between each application; the keratin fibers then being rinsed, washed with shampoo, rinsed again, then dried.

14. Agent for dyeing keratin fibers, and in particular human keratin fibers such as the hair, characterized in that it comprises the components (A) and (B) as defined in claims 10 to 13, in the form separate; the components (A) and (B) being intended to be either mixed just before use, or applied successively to the fibers to be treated.

15. Device with several compartments or "dyeing kit", characterized in that it comprises at least two compartments, one of which contains the component (A) as defined in claim 10, and the second of which contains the component (B) as defined in claim 10 or 11.

16. Device according to claim 20, characterized in that the component (A) and / or the component (B) is (are) in the form of an anhydrous composition and that it comprises a third compartment containing a cosmetically acceptable aqueous medium suitable for dye intended to be mixed before use in one or both of the first compartments containing each component

(A) or (B).