ZA200108983B

ZA200108983B - Oxidation dyeing composition for keratinous fibres and dyeing method using the same.

Info

Publication number: ZA200108983B
Application number: ZA200108983A
Authority: ZA
Inventors: Gerard Lang
Original assignee: Oreal
Priority date: 2000-03-06
Filing date: 2001-10-31
Publication date: 2002-09-11
Also published as: CZ20014324A3; EP1181004A1; JP2003525889A; CA2373099A1; PL352292A1; HUP0202007A2; BR0105561A; AU3934101A; FR2805738A1; KR20010113913A; WO2001066072A1; FR2805738B1; AU752948B2; CN1372457A

Description

RR ba

OXIDATION DYEING COMPOSITION FOR KERATINOUS FIBERS AND

DYEING METHOD USING SAME

The subject of the invention is a composition for the oxidation dyeing of keratinous fibers, and in particular human keratinous fibers such as hair, comprising, in an appropriate dyeing medium, at least a first oxidation base chosen from certain substituted derivatives of para-phenylenediamine and their addition salts with an acid and at least a second selected oxidation base, and the dyeing method using this composition.

It is known to dye keratinous fibers, and in particular human hair, with dyeing compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para- aminophenols, heterocyclic bases, generally called oxidation bases. Oxidation dye precursors, or oxidation bases, are colorless or faintly colored compounds which, when combined with oxidizing products, can give rise, by a process of oxidative condensation, to colored and coloring compounds.

It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with couplers or color modifiers, the latter being chosen in particular from aromatic meta-

ot,

L diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.

The variety of molecules used in oxidation : bases and couplers allows a rich pallet of colors to be obtained.

The so-called “permanent” color obtained using these oxidation dyes must moreover satisfy a number of requirements. Thus, it should make it possible to obtain shades of the desired intensity and exhibit good resistance toward external agents (light, adverse weather conditions, washing, permanent waving, perspiration, rubbing).

The dyes should also make it possible to cover gray hair and should finally be the least selective possible, that is to say should make it possible to obtain the smallest possible differences in color right along the same keratinous fiber, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.

Compositions for the oxidation dyeing of keratinous fibers containing, as oxidation dye precursors, certain substituted derivatives of para- phenylenediamine, have already been proposed, in particular in Patent Applications JP-11158046,

JP-11158047 and JP-11158048. However, the colors obtained using these compositions are not always sufficiently intense, chromatic or resistant to the various attacks to which the hair may be subjected.

ol

However, the applicant has now just discovered that it is possible to obtain novel dyes capable of leading to colors with a variety of shades, which are chromatic, intense, esthetic, not very selective and which exhibit good resistance to the various attacks to which the fibers may be subjected, by combining at least a first oxidation base chosen from certain para-phenylenediamine derivatives of formula (I) defined below and their addition salts with an acid and at least a second, suitably selected, oxidation base.

This discovery forms the basis of the present invention.

The first subject of the invention is : 15 therefore a composition for the oxidation dyeing of keratinous fibers, and in particular human keratinous' fibers such as hair, characterized in that it comprises, in an appropriate dyeing medium: - at least a first oxidation base chosen from the substituted derivatives of para-phenylenediamine of the following formula (I), and their addition salts with an acid:

Reso -™

NH,

[iad 2 4 in which: - R; and R, can have one of the following meanings i) to

Vv): i) R; and R; simultaneously represent a radical - (CH) ,CHOHCH,0H; or ii) R; represents a radical -CH;{(CHOH),CH;0H and R; represents a hydrogen atom, an alkyl or aryl radical or a heterocycle; or iii) R; represents an alkyl or aryl radical or a heterocycle and R; represents an alkylene radical -(CH3)p- in which m is an integer equal to 2 or 3, said alkylene radical forming a ring together with the nitrogen atom, the carbon atom of the benzene : ring carrying the nitrogen atom and one of the two carbon atoms of the benzene ring which are adjacent thereto, it being understood that when R; is an alkyl or aryl radical, then either R;, or said alkylene radical is substituted with a radical containing at least one nitrogen, oxygen or sulfur atom; iv) R; represents a radical -(CH,CHz0)pRs in which p is an integer between 2 and 8 inclusive, Rs; and Ro, which are identical or different, represent a hydrogen atom, an alkyl or aryl radical or a heterocycle;

Vv) R; and R; form, together with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered saturated heterocycle, said heterocycle being

> substituted with at least one radical containing at least one carbon, nitrogen, oxygen or sulfur atom; - Ri represents a halogen atom, an alkyl or aryl radical, a heterocycle, a heterocycle linked to the benzene ring of the formula (I) by an ether or thio bond, a cyano, nitro, hydroxyl, carboxyl, sulfo, alkoxy, aryloxy, cyanoamino, amino, anilino, ureido, sulfamylamino, mono- or dialkylsulfamylamino, alkylthio, arylthio, alkoxycarbonylamino, sulfonamido, carbamyl, mono- or dialkylcarbamylsulfamyl, sulfonyl, alkoxycarbonyl, azo, acyloxy, carbamyloxy, mono- or dialkylcarbamyloxy, silyl, silyloxy, aryloxy-

carbonylamino, imido, sulfinyl, phosphonyl, aryloxycarbonyl, acyl or mercapto radical; said alkyl radicals comprising from 1 to 25 carbon atoms and being capable of being linear, branched or cyclic and of being substituted with one or more radicals and of then representing a mono- or polyhydroxyalkyl, alkoxyalkyl, aminoalkyl optionally substituted on the nitrogen atom, carboxyalkyl, alkylcarboxyalkyl, thioalkyl, alkylthioalkyl, cyanoalkyl, trifluoroalkyl,

sulfoalkyl, phosphoalkyl or haloalkyl radical; said alkoxy radicals comprising from 1 to 25 carbon atoms and being capable of being linear, branched or cyclic;

p]

said aryl radicals comprising from 6 to 26 carbon atoms and being capable of being substituted with one or more radicals chosen from alkyl, substituted alkyl or alkoxy radicals;

the heterocycles being mono- or polycyclic, each ring comprising 3, 4, 5 or 6 members and being capable of containing one or more heteroatoms, it being understood that in the case of polycyclic heterocycles, at least one of the rings contains at least one heteroatom such as N, O or S;

- n is an integer between 0 and 4; it being understood that when n is greater than 1, then the radicals R; may be identical or different and may form with each other a 3-, 4-, 5- or 6-membered saturated or unsaturated ring;

with the proviso that:

1) when R; and R; have the meanings defined in point v), then the compounds of formula (I) do not contain more than 3 hydroxyl radicals;

2) when R; and R; have the meanings defined in point : v) and R; and R; form a pyrrolidine ring substituted with a carbamoyl radical on the carbon

- at the alpha-position with respect to the nitrogen atom to which they are attached, then n is different from 0; or altermatively the pyrrolidine ring carries at least two substituents;

3) when R; and R; have the meanings defined in point v) and R; and R; form a pyrrolidine ring substituted with a hydroxymethyl radical on the carbon situated at the alpha-position with respect to the nitrogen atom to which they are attached, and n = 0 or 1, then either said ring carries at least two additional substituents, or said ring comprises only a second substituent different from a hydroxyl radical on the carbon situated at the

B-position with respect to the nitrogen atom and with respect to the carbon carrying said hydroxymethyl substituent; or alternatively when R; and R, have the meanings defined in point v) and R; and R, form a pyrrolidine ring substituted with a hydroxymethyl radical on the carbon situated at the alpha-position with respect to the nitrogen atom to which they are attached, and n = 1, then Rs is different from an alkyl, mono- or polvhydroxyalkyl radical; 4) when R; and R; have the meanings defined in point iii), the compounds of formula (I) must fulfill at least one of the following four conditions: a) regardless of the value of n, the alkylene ring formed by the radical R; comprises a substituent in addition to the radical R;; or b) n is greater than 1; or c¢) when n is equal to 1, then Rj represents an aryl radical or a heterocycle; or d) when n is equal to zero or to 1, then R represents an aryl radical, a heterocycle or a substituted alkyl radical different from a monohydroxyalkyl radical; 5) when R; and R; have the meanings defined in point v), the groups Rl and R2 form a heterocycle different from piperazines and diazacycloheptanes. - and at least a second oxidation base chosen from heterocyclic oxidation bases, double bases, substituted para-aminophenols, ortho-aminophenols, para- phenylenediamine derivatives of the following formula (II), and their addition salts with an acid:

NR.R, . R,

Ry (ih

NH, in which: - Rs represents a hydrogen atom, a radical C;-C4 alkyl, C;-C4 monohydroxyalkyl, C,-C4 polyhydroxyalkyl, (Ci-Cs)alkoxy(Ci-Cs)alkyl, Ci1-C4 alkyl substituted with a nitrogen-containing group, a phenyl group or a 4’-aminophenyl group; - R¢ represents a hydrogen atom, a radical C;-Cs alkyl, C;-C; monohydroxyalkyl, C.-C, polyhydroxyalkyl, (C;-Cs)alkoxy(Ci-Csq)alkyl, Ci1-C4 alkyl substituted with a nitrogen-containing group; - R; represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a

) | 9

C;-C4 alkyl, C;-C4 monohydroxyalkyl, Ci-Cq hydroxyalkoxy, C;-Cs acetylaminoalkoxy, C;-Ca mesylaminoalkoxy or C;-C4 carbamoylaminoalkoxy radical, - Rg represents a hydrogen or halogen atom or a C1-Cs alkyl radical; it being understood that when Rs, Rs and Rg simultaneously represent a hydrogen atom, then R; does not designate a hydrogen atom, a chlorine atom or a methyl radical.

The dyeing composition in accordance with the invention leads to colors in a variety of shades, which are chromatic, intense, esthetic, which exhibit low selectivity and excellent properties of resistance to « atmospheric agents such as light and adverse weather conditions and to perspiration and various treatments to which the hair may be subjected.

According to a particular embodiment, the oxidation base is chosen from the substituted derivatives of para-phenylenediamine of the following formula (I), and their addition salts with an acid:

Ro _R,

Cre (1)

A, in which:

- R; and Ry; can have one of the following meanings i) to

Vv): i) R; and R; simultaneously represent a radical -(CH;) ,CHOHCH,0OH; or ii) R; represents a radical -CH;(CHOH),CH,O0H and R; represents a hydrogen atom, an alkyl radical; or iv) R; represents a radical -(CHCH;0)pRs in which p is an integer between 2 and 8 inclusive, Ry; and R, which are identical or different, represent a hydrogen atom, an alkyl radical; v) R; and R; form, together with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered saturated heterocycle, said heterocycle being substituted with at least one radical containing at least one carbon, nitrogen or oxygen atom, not situated at the meta-position with respect to the nitrogen atom of the heterocycle; - R3; represents a halogen atom, an alkyl or aryl radical, or a heterocycle, - n is an integer equal to 0, 1 or 2;

According to one embodiment of the invention, the groups R1 and R2 form a heterocycle comprising a single heteroatom, nitrogen, for example a pyrrolidine heterocycle.

Among the substituted derivatives of para- phenylenediamine of formula (I) above, there may be mentioned most particularly 1-N,N-bis(3’,4’'-dihydroxy- butyl) -para-phenylenediamine, 1-N,N-bis(3’,4’'-di-

hydroxybutyl)-3-methyl-para-phenylenediamine, 1-N,N-bis (3',4’-dihydroxybutyl)-3-ethyl-para-phenylenediamine, 1-N,N-bis(3',4'-dihydroxybutyl)-3-propyl-para- phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-

methoxy-para-phenylenediamine, 1-N,N-bis(3’,4’'- dihydroxybutyl) -3-ethoxy-para-phenylenediamine, 1-N,N- bis(3’,4’-dihydroxybutyl)-3-propyloxy-para- phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3- hexyloxy-para-phenylenediamine, 1-N,N-bis(3’,4'-di-

hydroxybutyl)-3-(1“-N-3”,5”-dimethylpyrazolyl-para- phenylenediamine, 1-N,N-bis(3’,4’-dihydroxybutyl)- 3-ureido-para-phenylenediamine, 1-N,N-bis(3’,4’'-di- | ] hydroxybutyl)-3-trimethyl-1~,3",3”-ureido-para- phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-di-

methylamino-para-phenylenedaimine, 1-N,N-bis(3’,4’'-di- hydroxybutyl)-3-methylthio-para-phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-ethylthio-para- phenylenediamine, 1-N,N-bis(3’,4'-dihydroxybutyl)- 3-mercapto-para-phenylenediamine, 1-N,N-bis(3’,4’'-di-

hydroxybutyl)-3-n-butylthic-para-phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-n-octylthio-para- phenylenediamine, 1-N,N-bis(3’,4’-dihydroxybutyl)- 3-mercaptoethyl-para-phenylenediamine, 1-N,N-bis(3’,4’- dihydroxybutyl)-3-mercaptoethylthio-para-

phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)- 3-hydroxyethylthio-para-phenylenediamine, 1-N- (2',3’,4',5’,6'-pentahydroxyhexyl)-para-phenylene- diamine, 1-N-(2’,3’,4’,5’,6’-pentahydroxyhexyl)-

i 12 3-methyl-para-phenylenediamine, 1-N-(2',3’,4',5',6'~ pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine, 1-N-(2",3",4',5',6'-pentahydroxyhexyl) -3-methoxy-para- phenylenediamine, 1-N-(2’,3’,4’,5',6’~pentahydroxy- hexyl)-1-N-(4”,-N"-methylpiperidyl)-3-ethoxy-para- phenylenediamine, 1-N-(2‘,3’,4’',5',6'- pentahydroxyhexyl) -3-isopropyloxy-para-phenylene- diamine, 1-N-(2’,3’,4'’,5'’,6'-pentahydroxyhexyl)-3-di- methylamino-para-phenylenediamine, 1-N-(2’',3’,4',5',6'- pentahydroxyhexyl)-3-methylthio-para-phenylenediamine, 1-N-(2’,3’,4',5’,6'-pentahydroxyhexyl)-3-mercapto-para- prhenylenediamine, 1-N-(hexyl)-1-N-(2',3’',4’,5',6'- pentahydroxyhexyl) -3-isopropyl-para-phenylenediamine, 1-N- (methyl)-1-N-(2’',3’,4',5’,6'-pentahydroxyhexyl)-3- isooctyloxy-para-phenylenediamine, 1-N-{(methyl)-1-N- (27,3",4',5",6'-pentahydroxyhexyl) -3-isopropyloxy-para- phenylenediamine, 1-N- (methyl)-1-N-(2’',3’,4’,5’,6'- pentahydroxyhexyl) -3-methyl-para-phenylenediamine, 1-N- (methyl)-1-N-{(2’,3’,4',5’,6’-pentahydroxyhexyl) -3- ethyl-para-phenylenediamine, 1-N-(methyl)-1-N- (2',37,4',5’,6' -pentahydroxyhexyl) -3-hydroxyethyloxy- para-phenylenediamine, 1-N-{(methyl)-1-N- (2',3’,4',5',6'-pentahydroxyhexyl)-3-mercaptoethyloxy- para-phenylenediamine, 1-N-{(methyl)-1-N- (2',3',4r,5',6'-pentahydroxyhexyl)-para-- phenylenediamine, 1-N-(phenyl)-1-N-(2',3’,4’',5',6'~ pentahydroxyhexyl)-3-ethyloxy-para-phenylenediamine, 1-

N- (4”-N-methylpiperidyl)-1-N-(2’,3',4’,5',6"-

pentahydroxyhexyl) -3-ethyloxy-para-phenylenediamine, 4-

N- (methyl)-4-N-(2’,3’,4',5’,6'-pentahydroxyhexyl)amino- 7-amino-l-methylindole, 1-N- (hydroxyethyloxyethyl)-1-N- - (2',3',4',5',6'-pentahydroxyhexyl)-3-ethyl-para- phenylenediamine, and their addition salts with an acid.

Preferably, the oxidation base is chosen from 1-N,N-bis(3’,4'-dihydroxybutyl) -para-phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-methyl-para- phenylenediamine, 1-N,N-bis(3’,4’-dihydroxybutyl)-3- ethyl-para-phenylenediamine, 1-N,N-bis(3’,4’- dihydroxybutyl) -3-propyl-para-phenylenediamine, 1-N- (2',37,4',5’,6'-pentahydroxyhexyl)-para-phenylene- diamine, 1-N-(2’',3’,4',5',6'-pentahydroxyhexyl)-3- methyl-para-phenylenediamine, 1-N-(2’',3’,4’',5',6'- pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine, 1-N- (hexyl) -1-N-(2’,3',4',5',6'-pentahydroxyhexyl)-3- isopropyl-para-phenylenediamine, 1-N-(methyl)-1-N- (2’,3',4',5’,6' -pentahydroxyvhexyl) -3-methyl-para- phenylenediamine, 1-N- (methyl)-1-N-(2',3’',4’',5',6'- pentahydroxyhexyl)-3-ethyl-para-phenylenediamine, 1-N- (methyl)-1-N-(2’,3’,4',5',6'-pentahydroxyhexyl) -para- phenylenediamine, 1-N- (hydroxyethyloxyethyl)-1-N- (2,3',4',5',6'-pentahydroxyhexyl)-3-ethyl-para- phenylenediamine, and their addition salts with an acid.

There may also be mentioned most particularly 1-N-(3’,4’'~-dihydroxybutyl)-5-aminoindoline,

1-(2’'-hydroxyethyl)-2-methyl-5-aminoindoline, l-methyl- 2-hydroxymethyl-5-aminoindoline, 6-methyl-2-hydroxy- ethyl-5-aminoindoline, 2-hydroxyethyloxyethyl-5-amino- indoline, 2-hydroxyethyloxyethyloxyethyloxyethyl-5-

aminoindoline, 2-hydroxyethyloxyethyloxyethyloxyethyl- oxyethyloxyethyl-6-isopropyl-5-aminocindoline, 2-hydroxyethyl-3-methyl-5-aminocindoline, 2-hydroxy- ethyloxyethyloxyethyl-5-aminoindoline, l-carboxymethyl- 2,3,3-trimethyl-5-aminoindoline, l-methyl-

sulfonamidoethyl-3-methyl-5-aminoindoline, l-ureido- ethyl-6-methoxy-5-aminoindoline, 1-(2’,3’,4',5’,6'- prentahydroxyhexyl)-5-aminoindoline, 1-N-(2’'-mercapto- ethyl) -5-aminoindoline, dimethyl ester 6-amino- l-methyl-1,2,3,4-tetrahydrofuro-[(2,3,hlquinoline

4-methyl ester of phosphoric acid, 6-amino-1,2,2-tri- methyl-4-trimethylsilanyloxy-1,2,3,4-tetrahydro- quinoline, 6-amino-l-hexyl-2,2,7-trimethyl-4-mercapto- methyl-1,2,3,4-tetrahydrogquinoline, 6-amino- 1-(3',4’'-dihydroxybutyl)-2,2,3-trimethyl-1,2,3,4-tetra-

hydroquinoline, 6-amino-1- (ethoxyethoxyethoxyethoxy- 3’,4'-dihydroxybutyl)-2,2,3,7-tetramethyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxy- ethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl- 1,2,3,4-tetrahydroquinoline, 6-amino-

1-(hydroxyethyloxyethyl)-2,2,3-trimethyl-1,2,3,4-tetra- hydroquinoline, 6-amino-1-(ethylbis(hydroxyethyloxy- ethyloxyethyloxyethyl))-2,2,3,7-tetramethyl- 1,2,3,4-tetrahydroquinoline, 1l- (carboxymethyl) -

2,2,3,7-tetramethyl-1,2,3,4-tetrahydroquinoline, 1- (hydroxypropyl)-2,2,3-trimethyl-7-methoxy- 1,2,3,4-tetrahydrogquinoline, 6-amino-1-(hydroxyethyl- oxyethyloxyethyl)-2,2,3-trimethyl-7-isopropyl-

1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyl- oxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxy- ethyl)-2,2,3-trimethyl-7-isopropyl-1,2,3,4-tetrahydro- quinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyloxy- ethyloxyethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl-

1,2,3,4-tetrahydroquinoline, 6-amino-1-(mercaptoethyl)- 1,2,3,4-tetrahydroquinoline, 6-amino- 1-(3’,4'-dihydroxybutyl)-2,2,3-trimethyl-7-isopropyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1-(3’,4’'-di- hydroxybutyl)-2,2,7-trimethyl-4-hydroxymethyl-

1,2,3,4-tetrahydroquinoline, 6-amino-1-(3’,4’-di- hydroxybutyl)-2, 2-dimethyl-4-hydroxymethyl-7-isopropyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1-(3-hydroxy- propyl) -2,2-dimethyl-4-hydroxymethyl-7-isopropyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyl-

oxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxy- ethyl) -2,2-dimethyl-4-hydroxymethyl-7-isopropyl- 1,2,3,4-tetrahydrogquineoline, 6-amino-1- (hydroxyethyl- oxyethyloxyethyloxyethyl)-2,2-dimethyl-4-hydroxymethyl- 7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-

1- (hydroxyethyloxyethyloxyethyloxyethyloxyethyl) - 2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyloxyethyloxy- ethyloxyethyl)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetra-

hydroquinoline, 6-amino-1- (hydroxyethyloxyethyl) - 2,2-dimethyl-1,2,3,4-tetrahydroquinoline, 6-amino- 1,2,2,4,7-pentamethyl-3-hydroxy-1,2,3,4-tetrahydro- quinoline, 6-amino-1-(3’'-hydroxypropyl)-4- (hydroxy-

ethyloxyethyloxyethyloxyethyl)-2,2-dimethyl-7-iso- propyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxy- ethyloxyethyloxyethyloxyethyl)-4,4-dimethyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1-(3’,4’'-di- hydroxybutyl)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetra-

hydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxy- ethyloxyethyl) -4- (hydroxyethyloxyethyloxyethyloxy- ethyl)-2,2,7-trimethyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyloxyethyl) - 2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline,

6-amino-1-(2',3’',4',5',6’'-pentahydroxyhexyl)-2,2,4-tri- : methyl-7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (mercaptoethyl)-2,2,4-trimethyl-7-(2’,3’'-di- hydroxypropyloxy)-1,2,3,4-tetrahydroquinoline, 6-amino- 1-(3’,4'-dihydroxybutyl)-2,2,7-trimethyl-

3-mercaptomethyl-1,2,3,4-tetrahydroquinoline, 6-amino- 1- (ureidoethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydro- quinoline, 6-amino-2,2-dimethyl-7-chloro-1,2,3,4-tetra-~ hydroquinoline-l-propylsulfonic acid, 6-amino- 1-(4’'-pyridinyl)-2,2,7-trimethyl-1,2,3,4-tetrahydro-

quinoline, 6-amino-1-(3’,4’-dihydroxybutyl)- 2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline, 6-amino-1, 7-diisopropyl-2,2-dimethyl-4-trimethyl- silanyloxy-1,2,3,4-tetrahydroquinoline, 6-amino-

1,2,2,4-tetramethyl-3-hydroxy-1,2,3,4-tetrahydro- : quinoline, 6-amino-l-bromo-2,2-dimethyl-4-mercapto- 7-isopropyloxy-1,2,3,4-tetrahydroquinoline, and their addition salts with an acid.

There may also be mentioned most particularly 1-(4’'-amino-3'-isopropyloxyphenyl)-2,6-dimethyl- pyrrolidine, 1-(4’'-amino-3’-methylphenyl)-3-hydroxy- ethyloxypyrrolidine, 1-(4'-amino-3’'-methylphenyl)- 4-hydroxy-2-methylpyrrolidone, 1-(4’'-amino- 3’-methylphenyl)-3-methylsulfonamidopyrrolidine, 1-(4’-amino-3‘'~phenoxyphenyl) -3-methylsulfonamido- pyrrolidine, 3-n-butylpyrrolidine-1-(4’'-amino- 3’-phenylsulfonic) acid, 1-(4’'-amino-3’'-acetylamino- phenyl) -3-hydroxymethylpyrrolidine, 7-amino- 4-(2’'-methyl)-pyrrolydinylbenzofuran, 1-(4’'-amino- phenyl) -2- (4“-aminophenoxymethyl) piperidine, 1-(4’'-amino-3’'-acetylphenyl)-4-hydroxypiperidine, 1-(4’'-aminophenyl)-2- (hydroxyethyl) piperidine, 1-(4’-amino-3'-methoxyphenyl) -2, 6-dihydroxymethyl- piperidine, 1-(4’'-amino-3’'-isopropyloxyphenyl) - 2, 6-dimethylpiperidine, 1-{(4’'-amino-3’'-isopropyl- phenyl) -2-hydroxymethylpiperidine, 1-(4'-amino- 3’ -isopropyloxyphenyl) -2-hydroxymethylpiperidine, 1-(4'-amino-3'-aminophenyl) -2-hydroxymethylpiperidine, 1-(4’-amino-3’'-dimethylaminophenyl)-2-mercaptoethyl- oxyethylpiperidine, 1-(4'-amino-3’-(2",4"-di- chloro)anilinophenyl)-4-methylpiperidine, 1-(4’-amino- phenyl) -4-methylpiperidine, 1-(4’-aminophenyl)-

2,7-dimethylazacycloheptane, 1-(4’-amino-3'-methyl- phenyl) -2-methylazacycloheptane, 1-(4’-amino-3'-ureido- phenyl) -3-hydroxyazacycloheptane, 1-(4'-amino- 3’-sulfamoylaminophenyl)-2, 7-dimethylazacycloheptane, 1-(4’-amino-3'-methylthiophenyl)-2,7-dimethylazacyclo- heptane, 1-N-4'-hydroxybutyl-1-N- (hydroxyethyloxy- ethyloxyethyl)-3-isopropyl-para-phenylenediamine, 1-N- methyl-1-N- (hydroxyethyloxyethyloxyethyl) -para- phenylenediamine, 1-N-phenyl-1-N- (hydroxyethyloxy- ethyl)-para-phenylenediamine, 1l-N-benzyl-1-N- (hydroxy- ethyloxyethyloxyethyloxyethyloxyethyl)-3-trimethyl- silyl-para-phenylenediamine, 1-N-methyl-1-N- (hydroxy- ethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl- oxyethyl)-3-trimethylsilyloxy-para-phenylenediamine, 1-N-ethyl-1-N- (methoxyethyloxyethyloxyethyloxyethyl- oxyethyl) -3-phenoxycarbonylamino-para-phenylenediamine, 1-N-methyl-1-N- (methoxyethyloxyethyloxyethyl) - 3-(2',5’~-dioxopyrrolidinyl) -para-phenylenediamine, 1-N- ethyl-1-N- (hydroxyethyloxyethyloxyethyl) - 3,4'-pyridinylthio-para-phenylenediamine, 1-N-propyl- 1-N- (hydroxyethyloxyethyloxyethyl)-3-sulfinyl-para- phenylenediamine, 1-N-methyl-1-N- (hydroxyethyloxyethyl) -3-phenoxycarbonyl-para- phenylenediamine, 1-N,N-

Dbis(hydroxyethyloxyethyloxyethyloxyethyl)-para- phenylenediamine, 1-N,N-bis (methoxyethyloxyethyloxy- ethyloxyethyl) -3-isopropyloxy-para-phenylenediamine, 1-N,N-bis (hydroxyethyloxyethyloxyethyl)-3-isopropyloxy=-

para-phenylenediamine, 1-N,N-bis (hydroxyethyloxy- ethyloxyethyloxyethyl) -3-isopropyl-para-phenylene- diamine, 1-N,N-bis(hydroxyethyloxyethyloxyethyloxy- ethyl) -3-isopropyl-para-phenylenediamine, 1-N,N-bis- (methoxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl- oxyethyl)-3-methoxy-para-phenylenediamine, 1-N,N-bis- (hydroxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl- oxyethyloxyethyl)-3-methyl-para-phenylenediamine, 1-N,N-bis (hydroxyethyloxyethyloxyethyloxyethyl)-3-iso- propyloxy-para-phenylenediamine, 1-N,N-bis (hydroxy- ethyloxyethyl)-3-mercaptoethyl-para-phenylenediamine, 1-N,N-bis(benzyloxyethyloxyethyloxyethyl)-3-isopropyl- para-phenylenediamine, and their addition salts with an acid.

Preferably, the oxidation base is chosen from 1- (4’-amino-3'-methylphenyl) -3-hydroxyethyloxy- : pyrrolidine, 1-(4’-amino-3’-methylphenyl)-4-hydroxy- 2-methylpyrrolidine, 1-(4’-amino-3’-methylphenyl)- 3-methylsulfonamidopyrrolidine, 1-(4’-amino- 3’-phenoxyphenyl)-3-methylsulfonamidopyrrolidine, 1- (4’-aminophenyl) -2- (4”-aminophenoxymethyl)piperidine, 1- (4’-aminophenyl) -2- (hydroxyethyl) piperidine, 1-(4’-amino-3’-isopropylphenyl)-2-hydroxymethyl- piperidine, 1-(4’-aminophenyl)-4-methylpiperidine, 1-(4’-aminophenyl)-2,7-dimethylazacycloheptane, 1- (4’-amino-3'-methylphenyl) -2-methylazacycloheptane, 1- (4’-amino-3’'-ureidophenyl) -3-hydroxyazacycloheptane, 1-N-4’-hydroxybutyl-1-N- (hydroxyethyloxyethyloxyethyl) -

3-isopropyl-para-phenylenediamine, 1-N-methyl- 1-N- (hydroxyethyloxyethyloxyethyl) -para- phenylenediamine, 1-N,N- bis (hydroxyethyloxyethyloxyethyloxyethyl) -para- phenylenediamine, 1-N,N-bis(hydroxyethyloxyethyloxy- ethyloxyethyl)-3-isopropyl-para-phenylenediamine, 1-N,N-bis (hydroxyethyloxyethyloxyethyloxyethyl)-3-iso- propyl-para-phenylenediamine, 1-N,N- bis (hydroxyethyloxyethyloxyethyloxyethyloxyethyloxy- ethyloxyethyloxyethyl)-3-methyl-para-phenylenediamine, 1-N,N-bis (benzyloxyethyloxyethyloxyethyl)-3-isopropyl- para-phenylenediamine, and their addition salts with an acid.

The para-phenylenediamine derivative(s) of formula (I) used as oxidation base in the dyeing composition in accordance with the invention preferably represent from 0.0001 to 20% by weight approximately, more preferably from 0.001 to 15% by weight and more preferably still from 0.01 to 10% by weight relative to the total weight of the composition.

Among the para-phenylenediamines of formula (IT) which can be used as second oxidation base in the dyeing composition in accordance with the invention, there may be mentioned more particularly 2,3-dimethyl- para-phenylenediamine, 2, 6-dimethyl-para-phenylene- diamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para- phenylenediamine, N,N-diethyl-para-phenylenediamine,

N,N-dipropyl-para-phenylenediamine, 4-amino-N,N- diethyl-3-methylaniline, N,N-bis(B-hydroxyethyl)-para- phenylenediamine, 4-N,N-bis (B-hydroxyethyl)amino- 2-methylaniline, 4-N,N-bis(f-hydroxyethyl)amino- 2-chloroaniline, 2-B-hydroxyethyl-para-phenylene- diamine, 2-fluoro-para-phenylenediamine, 2-isopropyl- para-phenylenediamine, N- (B-hydroxypropyl)-para- phenylenediamine, 2-hydroxymethyl-para-phenylene- diamine, N,N-dimethyl-3-methyl-para-phenylenediamine,

N,N- (ethyl, B-hydroxyethyl)-para-phenylenediamine,

N- (B,y-dihydroxypropyl) -para-phenylenediamine,

N- (4’-aminophenyl) -para-phenylenediamine, N-phenyl-para- phenylenediamine, 2-B-hydroxyethyloxy-para-phenylene- diamine, 2-P-acetylaminoethyloxy-para-phenylenediamine,

N- (B-methoxyethyl)-para-phenylenediamine, and their addition salts with an acid. among the para-phenylenediamines cof formula (II) above, there are most particularly preferred 2-isopropyl-para-phenylenediamine, 2-B-hydroxyethyl- para-phenylenediamine, 2-f-hydroxyethyloxy-para- phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para- phenylenediamine, N,N-bis(pf-hydroxyethyl)-para- phenylenediamine, 2-f-acetylaminoethyloxy-para- phenylenediamine, and their addition salts with an acid.

More preferably still, there are preferred among the para-phenylenediamines of formula (II) above,

Claims

1. A composition for the oxidation dyeing of keratinous fibers, and in particular human keratinous fibers such as hair, characterized in that it comprises, in an appropriate dyeing medium: - at least a first oxidation base chosen from the substituted derivatives of para-phenylenediamine of the following formula (I), and their addition salts with an acid: Re © NH, in which: - R; and R; can have one of the following meanings i) to Vv): i) R; and R; simultaneously represent a radical - (CH) ,CHOHCH,0H; or ii) R; represents a radical -CH;(CHOH).CH,0H and R, represents a hydrogen atom, an alkyl or aryl radical or a heterocycle; or iii) R; represents an alkyl or aryl radical or a heterocycle and R; represents an alkylene radical -(CH2)n- in which m is an integer equal to 2 or 3, said alkylene radical forming a ring together with the nitrogen atom, the carbon atom of the benzene ring carrying the nitrogen atom and one of the two carbon atoms of the benzene ring which are adjacent thereto, it being understood that when R; is an alkyl or aryl radical, then either R;, or said alkylene radical is substituted with a radical containing at least one nitrogen, oxygen or sulfur atom;

iv) R; represents a radical -(CH;CHz0)pRs in which p is an integer between 2 and 8 inclusive, R; and Ry, which are identical or different, represent a hydrogen atom, an alkyl or aryl radical or a heterocycle; Vv) R; and R; form, together with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered saturated heterocycle, said heterocycle being substituted with at least one radical containing at least one carbon, nitrogen, oxygen or sulfur atom;

- R3 represents a halogen atom, an alkyl or aryl radical, a heterocycle, a heterocycle linked to the benzene ring of the formula (I) by an ether or thio bond, a cyano, nitro, hydroxyl, carboxyl, sulfo, alkoxy, aryloxy, cyanoamino, amino,

anilino, ureido, sulfamylamino, mono- or dialkylsulfamylamino, alkylthio, arylthio, alkoxycarbonylamino, sulfonamido, carbamyl, mono- or dialkylcarbamylsulfamyl, sulfonyl,

alkoxycarbonyl, azo, acyloxy, carbamyloxy, mono- or dialkylcarbamyloxy, silyl, silyloxy, aryloxy- carbonylamino, imido, sulfinyl, phosphonyl, aryloxycarbonyl, acyl or mercapto radical;

said alkyl radicals comprising from 1 to 25 carbon atoms and being capable of being linear, branched or cyclic and of being substituted with one or more radicals and of then representing a mono- or polyhydroxyalkyl, alkoxyalkyl, aminoalkyl optionally substituted on the nitrogen atom, carboxyalkyl, alkylcarboxyalkyl, thioalkyl, alkylthicalkyl, cyanoalkyl, trifluoroalkyl, sulfoalkyl, phosphoalkyl or haloalkyl radical; said alkoxy radicals comprising from 1 to 25 ’

carbon atoms and being capable of being linear, branched or cyclic; said aryl radicals comprising from 6 to 26 carbon atoms and being capable of being substituted with one or more radicals chosen from alkyl,

substituted alkyl or alkoxy radicals; the heterocycles being mono- or polycyclic, each ring comprising 3, 4, 5 or 6 members and being capable of containing one or more heteroatoms, it being understood that in the case of polycyclic heterocycles, at least one of the rings contains at least one heteroatom such as N, 0 or S;

- n is an integer between 0 and 4; it being understood that when n is greater than 1, then the radicals R; may be identical or different and may form with each other a 3-, 4-, 5- or 6-membered saturated or unsaturated ring; : with the proviso that:

2) when R; and R; have the meanings defined in point v) and R; and R; form a pyrrolidine ring substituted with a carbamoyl radical on the carbon at the alpha-position with respect to the nitrogen atom to which they are attached, then n is different from 0; or alternatively the pyrrolidine ring carries at least two substituents;

3) when R; and R; have the meanings defined in point v) and R; and R; form a pyrrolidine ring substituted with a hydroxymethyl radical on the carbon situated at the alpha-position with respect to the nitrogen atom to which they are attached,

and n = 0 or 1, then either said ring carries at least two additional substituents, or said ring comprises only a second substituent different from a hydroxyl radical on the carbon situated at the B-position with respect to the nitrogen atom and with respect to the carbon carrying said hydroxymethyl substituent; or alternatively when R; and R; have the meanings defined in point v) and R; and R; form a pyrrolidine ring substituted with a hydroxymethyl radical on the carbon situated at the alpha-position with respect to the nitrogen atom to which they are attached, and n = 1, then R; is different from an alkyl, mono- or polyhydroxyalkyl radical;

4) when R; and R; have the meanings defined in point iii), the compounds of formula (I) must fulfill at least one of the following four conditions:

a) regardless of the value of n, the alkylene ring formed by the radical R;, comprises a substituent in addition to the radical R;; or b) n is greater than 1; or c) when n is equal to 1, then R; represents an aryl radical or a heterocycle; or d) when n is equal to zero or to 1, then R; represents an aryl radical, a heterocycle or a substituted alkyl radical different from a . monohydroxyalkyl radical; 5) when R; and R; have the meanings defined in point v), the groups Rl and R2 form a heterocycle different from piperazines and diazacycloheptanes;

- and at least a second oxidation base chosen from heterocyclic oxidation bases, double bases, substituted para-aminophenols, ortho-aminophenols, para-phenylene- diamine derivatives of the following formula (II), and their addition salts with an acid:

NR:R, R; Rg (i) NH, in which: - Rs represents a hydrogen atom, a radical C;-Cy alkyl, C;-C4 monohydroxyalkyl, C;-C4 polyhydroxyalkyl, (C;-Cy)alkoxy(Ci-Cs)alkyl, Ci1-C4 alkyl substituted with a nitrogen-containing group, a phenyl group or a 4‘'-aminophenyl group; - Re represents a hydrogen atom, a radical Ci;-C4 alkyl, C1-Cy monohydroxyalkyl, C;-Cs; polyhydroxy- alkyl, (C;-Cy)alkoxy(C;-Cs)alkyl, C1-C4 alkyl substituted with a nitrogen-containing group; - R; represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C1-C4 alkyl, C;-C; monohydroxyalkyl, C;-C; hydroxy- alkoxy, C;-C; acetylaminoalkoxy, C;-Cs mesylamino- alkoxy or C;-C, carbamoylaminoalkoxy radical, - Rg represents a hydrogen or halogen atom or a C;-C4 alkyl radical; it being understood that when Rs, Rg and Rg simultaneously represent a hydrogen atom, then R; does not designate a hydrogen atom, a chlorine atom or a methyl radical. :

2. The composition as claimed in claim 1, in which the oxidation base is chosen from the substituted derivatives of para-phenylenediamine of the following formula (I), and their addition salts with an acid: Res NH, in which: - R; and R; can have one of the following meanings i) to Vv): 1) R; and R; simultaneously represent a radical - (CH;) ,CHOHCH,0H; or ii) R; represents a radical -CH,;(CHOH),CH,O0H and R, represents a hydrogen atom, an alkyl radical; or iv) R; represents a radical -(CHyCHz0)pRs in which p is an integer between 2 and 8 inclusive, Rs; and R,, which are identical or different, represent a hydrogen atom, an alkyl radical; Vv) R; and R; form, together with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered saturated heterocycle, said heterocycle being substituted with at least one radical containing at least one carbon, nitrogen or oxygen atom, not situated at the meta-position with respect to the nitrogen atom of the heterocycle; - R; represents a halogen atom, an alkyl or aryl radical, or a heterocycle, - n is an integer equal to 0, 1 or 2.

3. The composition as claimed in claim 1 or 2, characterized in that the substituted derivatives of para-phenylenediamine of formula (I) are chosen from 1-N,N-bis(3’,4’-dihydroxybutyl) -para-phenylenediamine, 1-N,N-bis(3’,4’-dihydroxybutyl)-3-methyl-para- phenylenediamine, 1-N,N-bis(3’,4'-dihydroxybutyl)-3- ethyl-para-phenylenediamine, 1-N,N-bis{(3’,4'-di- hydroxybutyl) -3-propyl-para-phenylenediamine, 1-N,N- bis(3’,4’-dihydroxybutyl)-3-methoxy-para-phenylene- diamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-ethoxy-para- phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3- propyloxy-para-phenylenediamine, 1-N,N-bis(3’,4’'-di- hydroxybutyl) -3-hexyloxy-para-phenylenediamine, 1-N,N- bis(3’,4’'-dihydroxybutyl)-3-(1"-N-3”,5”-dimethyl- pyrazolyl-para-phenylenediamine, 1-N,N-bis(3’,4’'-di- hydroxybutyl) -3-ureido-para-phenylenediamine, 1-N,N- bis(3’',4’-dihydroxybutyl)-3-trimethyl-1“,3”,3”-ureido- para-phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)- 3-dimethylamino-para-phenylenediamine, 1-N,N-bis(3’,4"'- dihydroxybutyl)-3-methylthio-para-phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-ethylthio-para- phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)- 3-mercapto-para-phenylenediamine, 1-N,N-bis(3’,4’'-di-

) a7 hydroxybutyl) -3-n-butylthio-para-phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3-n-octylthio-para- phenylenediamine, 1-N,N-big(3’,4’'-dihydroxybutyl)- 3-mercaptoethyl-para-phenylenediamine, 1-N,N-bis(3’',4’'-

dihydroxybutyl)-3-mercaptoethylthio-para-

phenylenediamine, 1-N,N-bis(3’,4‘'-dihydroxybutyl)- 3-hydroxyethylthio-para-phenylenediamine, 1-N- (2',3',4',5’,6' -pentahydroxyhexyl)-para-phenylene- diamine, 1-N-(2',3’,4',5',6'-pentahydroxyhexyl)-

3-methyl-para-phenylenediamine, 1-N-(2’,3’,4',5',6'- pentahydroxyhexyl) -3-isopropyl-para-phenylenediamine, 1-N-(2',3',4',5',6'-pentahydroxyhexyl)-3-methoxy-para- phenylenediamine, 1-N-(2',3',4’,5’,6'-pentahydroxy- hexyl)-1-N-(4”",-N"-methylpiperidyl)-3-ethoxy-para-

phenylenediamine, 1-N-(2’,3’,4',5',6’'-pentahydroxy- hexyl) -3-isopropyloxy-para-phenylenediamine, 1-N- (2,3",4',5',6’-pentahydroxyhexyl)-3-dimethylamino- para-phenylenediamine, 1-N-(2',3’,4',5'’,6'-penta-

hydroxyhexyl)-3-methylthio-para-phenylenediamine, 1-N-

(2',3',4',5',6’-pentahydroxyhexyl)-3-mercapto-para- phenylenediamine, 1-N- (hexyl)-1-N-(2’,3’,4’,5',6'- pentahydroxyhexyl) -3-isopropyl-para-phenylenediamine, 1-N- (methyl)-1-N-(2',3’,4’,5',6'-pentahydroxyhexyl)-3- isooctyloxy-para-phenylenediamine, 1-N- (methyl)-1-N-

(2',3',4',5’,6'-pentahydroxyhexyl)-3-isopropyloxy-para- phenylenediamine, 1-N-(methyl)-1-N-(2‘,3’,4',5’,6'- pentahydroxyhexyl)-3-methyl-para-phenylenediamine, 1-N- (methyl)-1-N-(2',3’,4',5',6'-pentahydroxyhexyl)-3-

ethyl-para-phenylenediamine, 1-N- (methyl)-1-N- (2',3,4',5",6’-pentahydroxyhexyl) -3-hydroxyethyloxy- para-phenylenediamine, 1-N-(methyl)-1-N- (2',3',4’,5',6'-pentahydroxyhexyl) -3-mercaptoethyloxy-

para-phenylenediamine, 1-N- (methyl)-1-N- (2,37,4',5',6’ -pentahydroxyhexyl) -para- phenylenediamine, 1-N-(phenyl)-1-N-(2’,3’',4',5',6'- pentahydroxyhexyl)-3-ethyloxy-para-phenylenediamine, 1- N- (4”-N-methylpiperidyl)-1-N-(2',3’,4',5',6'-

pentahydroxyhexyl)-3-ethyloxy-para-phenylenediamine, 4- N- (methyl)-4-N-(2’,3’',4’,5',6'-pentahydroxyhexyl) amino- 7-amino-l-methylindole, 1-N-(hydroxyethyloxyethyl)-1-N- (2',37,4’,5’,6’'-pentahydroxyhexyl)-3-ethyl-para- phenylenediamine, 1-N-(3',4'-dihydroxybutyl)-5-

aminoindoline, 1-(2’'-hydroxyethyl)-2-methyl-5- aminoindoline, l-methyl-2-hydroxymethyl-5- aminoindoline, 6-methyl-2-hydroxyethyl-5-aminoindoline, 2-hydroxyethyloxyethyl-5-aminocindoline, 2-hydroxyethyloxyethyloxyethyloxyethyl-5-aminoindoline,

2-hydroxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl-

6-isopropyl-5-aminoindoline, 2-hydroxyethyl-3-methyl-5- aminoindoline, 2-hydroxyethyloxyethyloxyethyl-5- aminoindoline, l-carboxymethyl-2,3,3-trimethyl-5- aminoindoline, l-methylsulfonamidoethyl-3-methyl-5-

aminoindoline, l-ureidoethyl-6-methoxy-5-aminoindoline,

: 1-(2',3',4’',5',6'-pentahydroxyhexyl)-5-aminoindoline, 1-N-(2'-mercaptoethyl)-5-aminoindoline, dimethyl ester 6-amino-1-methyl-1,2,3,4-tetrahydrofuro-

[2,3,h]lquinoline 4-methyl ester of phosphoric acid, 6-amino-1,2,2-trimethyl-4-trimethylsilanyloxy-1,2,3,4- tetrahydroquinoline, 6-amino-1l-hexyl-2,2,7-trimethyl- 4-mercaptomethyl-1,2,3,4-tetrahydroquinoline, 6-amino-

1-(3’,4’'-dihydroxybutyl)-2,2,3-trimethyl-1,2,3,4-tetra- hydroquinoline, 6-amino-1- (ethoxyethoxyethoxyethoxy- 3’,4'-dihydroxybutyl)-2,2,3,7-tetramethyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxy- ethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl-

1,2,3,4-tetrahydroguinoline, 6-amino-1- (hydroxyethyl- oxyethyl)-2,2,3-trimethyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (ethylbis (hydroxyethyloxyethyloxyethyloxy- ethyl))-2,2,3,7-tetramethyl-1,2,3,4-tetrahydro- quinoline, 1-(carboxymethyl)-2,2,3,7-tetramethyl-

1,2,3,4~tetrahydrogquinoline, 1- (hydroxypropyl) - 2,2,3-trimethyl-7-methoxy-1, 2,3, 4-tetrahydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyl)-2,2,3-tri- methyl-7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyloxyethyloxy-

ethyloxyethyloxyethyloxyethyl)-2,2,3-trimethyl-7-iso- propyl-1,2,3,4-tetrahydrogquinoline, 6-amino-

1- (hydroxyethyloxyethyloxyethyloxyethyloxyethyloxy- ethyloxyethyloxyethyl)-2,2,3-trimethyl-1,2,3,4-tetra- hydroguinoline, 6-amino-1-(mercaptoethyl)-

1,2,3,4-tetrahydroquinoline, 6-amino-1-(3’',4’-di- hydroxybutyl)-2,2,3-trimethyl-7-isopropyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1-(3',4'-di- hydroxybutyl)-2,2,7-trimethyl-4-hydroxymethyl-

N

1,2,3,4-tetrahydroquinoline, 6-amino-1-(3',4’'-di- hydroxybutyl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1- (3-hydroxy- propyl) -2,2-dimethyl-4-hydroxymethyl-7-isopropyl-

1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyl- oxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxy- ethyl)-2,2-dimethyl-4-hydroxymethyl-7-isopropyl- 1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyl- oxyethyloxyethyloxyethyl)-2,2-dimethyl-4-hydroxymethyl-

7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-

1- (hydroxyethyloxyethyloxyethyloxyethyloxyethyl)- 2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyloxyethyloxy- ethyloxyethyl)-2,2-dimethyl-7-isopropyl-1,2,3,4-tetra-

hydroquinoline, 6-amino-1-(hydroxyethyloxyethyl)- 2,2-dimethyl-1,2,3,4-tetrahydroquinoline, 6-amino- 1,2,2,4,7-pentamethyl-3-hydroxy-1,2,3,4-tetrahydro- quinoline, 6-amino-1-(3’'-hydroxypropyl)-4- {hydroxy- ethyloxyethyloxyethyloxyethyl)-2,2-dimethyl-7-iso-

propyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxy- ethyloxyethyloxyethyloxyethyl)-4, 4-dimethyl- 1,2,3,4-tetrahydrogquinoline, 6-amino-1-(3’,4'-di- hydroxybutyl)-2, 2-dimethyl-7-isopropyi-1,2,3,4-tetra- hydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxy-

ethyloxyethyl)-4- (hydroxyethyloxyethyloxyethyloxy- ethyl)-2,2,7-trimethyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (hydroxyethyloxyethyloxyethyloxyethyl)- 2,2-dimethyl-7-isopropyl-1,2,3,4-tetrahydrogquinoline,

\

6-amino-1-(2',3’,4',5’,6’'-pentahydroxyhexyl)-2,2,4~-tri- methyl-7-isopropyl-1,2,3,4-tetrahydroquinoline, 6-amino-1- (mercaptoethyl)-2,2,4-trimethyl-7-(2’,3'-di- hydroxypropyloxy)-1,2,3,4-tetrahydroquinoline, 6-amino-

1-(3',4’-dihydroxybutyl)-2,2,7-trimethyl- 3-mercaptomethyl-1,2,3,4-tetrahydroquinoline, 6-amino- 1-(ureidoethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydro- quinoline, 6-amino-2,2-dimethyl-7-chloro-1,2,3,4-tetra- hydrogquinoline-l-propylsulfonic acid, 6-amino-

1-(4’'-pyridinyl)-2,2,7-trimethyl-1,2,3,4-tetrahydro- quinoline, 6-amino-1-(3’,4’'-dihydroxybutyl)-

2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline, 6-amino-1,7-diisopropyl-2,2-dimethyl-4-trimethyl-

silanyloxy-1,2,3,4-tetrahydroquinoline, 6-amino-

1,2,2,4-tetramethyl-3-hydroxy-1,2,3,4-tetrahydro- quinoline, 6-amino-l-bromo-2,2-dimethyl-4-mercapto- 7-isopropyloxy-1,2,3,4-tetrahydroquinoline, 1-(4’-amino-3’'-isopropyloxyphenyl)-2,6-dimethyl- pyrrolidine, 1-(4’'-amino-3’'-methylphenyl)-3-hydroxy-

ethyloxypyrrolidine, 1-(4’-amino-3’'-methylphenyl)- 4-hydroxy-2-methylpyrrolidone, 1-(4‘'-amino-3'-methyl-

: phenyl) -3-methylsulfonamidopyrrolidine, 1-{(4'-amino- 3’ -phenoxyphenyl) -3-methylsulfonamidopyrrolidine, 3-n- butylpyrrolidine-1-(4’'-amino-3’'-phenylsulfonic) acid,

1-(4’'-amino-3’-acetylaminophenyl) -3-hydroxymethyl- pyrrolidine, 7-amino-4-(2'-methyl)-pyrrolydinyl- benzofuran, 1-(4’'-aminophenyl)-2-(4”-aminophenoxy- methyl)piperidine, 1-(4‘'-amino-3’-acetylphenyl)-

4-hydroxypiperidine, 1-(4'-aminophenyl)-2- (hydroxy- ethyl)piperidine, 1-(4’'-amino-3'-methoxyphenyl)-2,6-di- hydroxymethylpiperidine, 1-(4'-amino-3’'-isopropyloxy- phenyl) -2, 6-dimethylpiperidine, 1-(4’'-amino-3’-iso-

propyloxyphenyl)-2-hydroxymethylpiperidine, 1-(4’'-amino-3’'-isopropyloxyphenyl) - 2-hydroxymethylpiperidine, 1-(4’'-amino-3’-aminophenyl)- 2-hydroxymethylpiperidine, 1-(4'-amino- 3’-dimethylaminophenyl) -2-mercaptoethyl-

oxyethylpiperidine, 1-(4’-amino-3’-(2",4"”-dichloro)- anilinophenyl)-4-methylpiperidine, 1-(4’-aminophenyl)- 4-methylpiperidine, 1-(4’-aminophenyl)-2,7-dimethylaza-

cycloheptane, 1-(4’-amino-3’-methylphenyl)-2-methyl- azacycloheptane, 1-(4’-amino-3'-ureidophenyl) -

3-hydroxyazacycloheptane, 1-(4’-amino-3’'-sulfamoyl- aminophenyl) -2, 7-dimethylazacycloheptane, 1-(4’-amino- 3’-methylthiophenyl) -2, 7-dimethylazacycloheptane, 1-N- 4’-hydroxybutyl-1-N- (hydroxyethyloxyethyloxyethyl) - 3-isopropyl-para-phenylenediamine, 1-N-methyl-1-N-

(hydroxyethyloxyethyloxyethyl)-para-phenylenediamine, 1-N-phenyl-1-N- (hydroxyethyloxyethyl) -para-phenylene- diamine, 1-N-benzyl-1-N- (hydroxyethyloxyethyloxy- ethyloxyethyloxyethyl)-3-trimethylsilyl-para- phenylenediamine, 1-N-methyl-1-N-(hydroxyethyloxy-

ethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl)- 3-trimethylsilyloxy-para-phenylenediamine, 1-N-ethyl- 1-N- (methoxyethyloxyethyloxyethyloxyethyloxyethyl) - 3-phenoxycarbonylamino-para-phenylenediamine, 1-N-

" methyl-1-N- (methoxyethyloxyethyloxyethyl) - 3-(2’,5’-dioxopyrrolidinyl) -para-phenylenediamine, 1-N- ethyl-1-N- (hydroxyethyloxyethyloxyethyl) - 3,4’ -pyridinylthio-para-phenylenediamine, 1-N-propyl- 1-N- (hydroxyethyloxyethyloxyethyl)-3-sulfinyl-para- phenylenediamine, 1-N-methyl-1-N- (hydroxyethyloxyethyl) -3-phenoxycarbonyl-para- phenylenediamine, 1-N,N-bis- (hydroxyethyloxyethyloxyethyloxyethyl) -para-phenylene- diamine, 1-N,N-bis(methoxyethyloxyethyloxyethyloxy~- ethyl) -3-isopropyloxy-para-phenylenediamine, 1-N,N-bis- (hydroxyethyloxyethyloxyethyl) -3-isopropyloxy-para- phenylenediamine, 1-N,N-bis(hydroxyethyloxyethyl- oxyethyloxyethyl) -3-isopropyl-para-phenylenediamine, 1-N,N-bis(hydroxyethyloxyethyloxyethyloxyethyl) - 3-isopropyl-para-phenylenediamine, 1-N,N-bis(methoxy- ethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl) - 3-methoxy-para-phenylenediamine, 1-N,N-bis- (hydroxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl- oxyethyloxyethyl)-3-methyl-para-phenylenediamine, 1-N,N-bis (hydroxyethyloxyethyloxyethyloxyethyl)-3-iso- propyloxy-para-phenylenediamine, 1-N,N-bis (hydroxy- ethyloxyethyl) -3-mercaptoethyl-para-phenylenediamine, 1-N,N-bis (benzyloxyethyloxyethyloxyethyl)-3-isopropyl- para-phenylenediamine, and their addition salts with an acid.

4. The composition as claimed in any one of the preceding claims, in which the oxidation base is oo 54 chosen from 1-N,N-bis(3’,4’'-dihydroxybutyl)-para- phenylenediamine, 1-N,N-bis(3’,4’'-dihydroxybutyl)-3- methyl-para-phenylenediamine, 1-N,N-bis(3’,4'-di- hydroxybutyl)-3-ethyl-para-phenylenediamine, 1-N,N- bis(3’,4’'-dihydroxybutyl)-3-propyl-para-phenylene- diamine, 1-N-(2',3’,4’,5’,6’' -pentahydroxyhexyl)-para- phenylenediamine, 1-N-(2’,3’,4',5’,6'-penta- hydroxyhexyl) -3-methyl-para-phenylenediamine, 1-N- (2',37,4',5',6’-pentahydroxyhexyl)-3-isopropyl-para- phenylenediamine, 1-N-(hexyl)-1-N-(2’,3’,4',5',6'- pentahydroxyhexyl)-3-isopropyl-para-phenylenediamine, 1-N- (methyl)-1-N-(2',3’,4’,5',6'-pentahydroxyhexyl)-3- methyl-para-phenylenediamine, 1-N- (methyl)-1-N- (2’,3',4’,5',6'-pentahydroxyhexyl)-3-ethyl-para- phenylenediamine, 1-N-(methyl)-1-N-(2’,3’,4’,5',6'~ pentahydroxyhexyl) -para-phenylenediamine, 1-N- (hydroxy- ethyloxyethyl)-1-N-(2',3’,4’,5',6'-pentahydroxyhexyl) - 3-ethyl-para-phenylenediamine, and their addition salts with an acid.

5. The composition as claimed in any one of claims 1 to 3, in which the oxidation base is chosen from 1-(4’-amino-3’-methylphenyl)-3-hydroxyethyloxy- pyrrolidine, 1-(4’-amino-3’-methylphenyl)-4-hydroxy- 2-methylpyrrolidine, 1-(4’-amino-3’-methylphenyl)- 3-methylsulfonamidopyrrolidine, 1-(4’-amino-3’-phenoxy- phenyl) -3-methylsulfonamidopyrrolidine, 1-(4’-amino- phenyl) -2- (4”-aminophenoxymethyl) piperidine, 1-(4’-aminophenyl) -2- (hydroxyethyl) piperidine,

A 1- (4’-amino-3’'-isopropylphenyl) -2-hydroxymethyl- piperidine, 1-(4’-aminophenyl)-4-methylpiperidine, 1- (4’-aminophenyl) -2,7-dimethylazacycloheptane, 1- (4’-amino-3’-methylphenyl) -2-methylazacycloheptane, 1-(4’-amino-3’-ureidophenyl)-3-hydroxyazacycloheptane, 1-N-4’-hydroxybutyl-1-N- (hydroxyethyloxyethyloxyethyl) - 3-isopropyl-para-phenylenediamine, 1-N-methyl- 1-N- (hydroxyethyloxyethyloxyethyl) -para- phenylenediamine, 1-N,N- bis (hydroxyethyloxyethyloxyethyloxyethyl)-para- rhenylenediamine, 1-N,N-bis(hydroxyethyloxyethyloxy- ethyloxyethyl)-3-isopropyl-para-phenylenediamine, 1-N,N-bis (hydroxyethyloxyethyloxyethyloxyethyl)-3-iso- propyl-para-phenylenediamine, 1-N,N-bis(hydroxyethyl- oxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxy- ethyl) -3-methyl-para-phenylenediamine, 1-N,N-bis- (benzyloxyethyloxyethyloxyethyl)-3-isopropyl-para- phenylenediamine, and their addition salts with an acid.

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6. The composition as claimed in any one of the preceding claims, characterized in that the para- phenylenediamine derivative (s) of formula (I) represent from 0.0001 to 20% by weight of the total weight of the composition.

7. The composition as claimed in claim 1 or 2, characterized in that the groups Rl and R2 form a pyrrolidine heterocycle.

™

8. The composition as claimed in any one of the preceding claims, characterized in that the para- phenylenediamines of formula (II) are chosen from 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para- phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N- diethyl-3-methylaniline, N,N-bis(P-hydroxyethyl)-para- phenylenediamine, 4-N,N-bis (B-hydroxyethyl)amino- 2-methylaniline, 4-N,N-bis (f-hydroxyethyl)amino- 2-chloroaniline, 2-B-hydroxyethyl-para-phenylene- diamine, 2-fluoro-para-phenylenediamine, 2-isopropyl- para-phenylenediamine, N- (B-hydroxypropyl)-para- phenylenediamine, 2-hydroxymethyl-para-phenylene- diamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N- (ethyl, P-hydroxyethyl)-para-phenylenediamine, N- (PB, y-dihydroxypropyl) -para-phenylenediamine, N- (4’-aminophenyl) -para-phenylenediamine, N-phenyl-para- phenylenediamine, 2-P-hydroxyethyloxy-para-phenylene- diamine, 2-P-acetylaminoethyloxy-para-phenylenediamine, N- (B-methoxyethyl) -para-phenylenediamine, and their addition salts with an acid.

9. The composition as claimed in claim 8, characterized in that the para-phenylenediamines of formula (II) are chosen from 2-isopropyl-para- phenylenediamine, 2-PB-hydroxyethyl-para-phenylene- diamine, 2-PB-hydroxyethyloxy-para-phenylenediamine,

a 2,6-dimethyl-para-phenylenediamine, 2, 6-diethyl-para- phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis (B-hydroxyethyl)-para-phenylenediamine, 2-§- acetylaminoethyloxy-para-phenylenediamine, and their addition salts with an acid.

10. The composition as claimed in claim 9, characterized in that the para-phenylenediamines of formula (II) are chosen from 2-B-hydroxyethyl-para- phenylenediamine, N,N-bis (f-hydroxyethyl)-para- phenylenediamine, and their addition salts with an acid.

11. The composition as claimed in any one of claims 1 to 7, characterized in that the double bases are chosen from the compounds of the following formula (III), and their addition salts with an acid: 2, | z, Rat | R,2 EY Lt Ea (1 NR,,R,, i NR sR6 in which: - Z; and Z,, which are identical or different, represent a hydroxyl or -NH; radical which may be substituted with a C;-Cs alkyl radical or with a linking arm Y; - the linking arm Y represents a linear or branched alkylene chain comprising from 1 to 14 carbon atoms,

which may be interrupted by or which may end with one or more nitrogen-containing groups and/or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms, and optionally substituted with one or more hydroxyl or C,-Cg¢ alkoxy radicals; - Rg and Rig represent a hydrogen or halogen atom, a C:-Cs alkyl radical, a monohydroxy (Ci1-Cs alkyl) radical, a polyhydroxy (C;-C; alkyl) radical, an amino (C;-C4 alkyl) radical or a linking arm Y; - Rji, Riz, Riz, Ris, Ris and Rj, which are identical or different, represent a hydrogen atom, a linking arm Y or a C;-C4 alkyl radical; it being understood that the compounds of formula (III) contain only one linking arm Y per molecule.

12. The composition as claimed in claim 11, characterized in that the double bases of formula (III) are chosen from N,N’'-bis (Bf-hydroxyethyl)-N,N’-bis(4’~ aminophenyl)-1, 3-diaminopropanol, N,N’-bis (B-hydroxy- ethyl)-N,N’-bis(4’'-aminophenyl) ethylenediamine, N,N’- bis (4-aminophenyl) tetramethylenediamine, N,N’ ~bis (B- hydroxyethyl) -N,N’'-bis (4-aminophenyl) tetramethylene- diamine, N,N’-bis(4-methylaminophenyl)tetramethylene- diamine, N,N’-bis(ethyl)-N,N’'-bis(4’'-amino-3’'-methyl- phenyl) ethylenediamine, 1,8-bis(2,5-diaminophenoxy)- 3,5-dioxaoctane, and their addition salts with an acid.

13. The composition as claimed in any one of claims 1 to 7, characterized in that the substituted para-aminophenols are chosen from the compounds of the

Ea following formula (IV), and their addition salts with an acid: OH Riz Sa Rig NH, in which: - Rj; represents a hydrogen or halogen atom, a C;-Ca alkyl, monohydroxy(Ci:-Cs alkyl), (Ci-Cs)alkoxy(Ci-C4)- alkyl, amino(C;-C4 alkyl) or hydroxy (C:i-Cs)alkylamino- (C1-C4 alkyl) radical, - Rig represents a hydrogen or halogen atom, a C;-C4 alkyl, monohydroxy(C;-Cs alkyl), polyhydroxy (C,-Cs alkyl), amino (C;-Cs alkyl), cyano(C;-C; alkyl) or (C1-Cy)alkoxy (Ci1-C4)alkyl radical, it being understood that at least one of the radicals R17 or Rig is different from a hydrogen atom.

14. The composition as claimed in claim 13, characterized in that the para-aminophenols of formula (IV) are chosen from para-aminophenol, 4-amino-3- methylphenol, 4-amino-3-fluorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2- hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (f-hydroxy- ethylaminomethyl)phenol, 4-amino-2-fluorophenol, and their addition salts with an acid.

15. The composition as claimed in any one of claims 1 to 7, characterized in that the ortho-amino- phenols are chosen from 2-aminophenol, 2-amino-5- methylphenol, 2-amino-6-methylphenol, 5-acetamido-2- aminophenol, and their addition salts with an acid.

16. The composition as claimed in any one of claims 1 to 7, characterized in that the heterocyclic bases are chosen from pyridine derivatives, pyrimidine derivatives, pyrazole derivatives, and their addition salts with an acid.

17. The composition as claimed in any one of the preceding claims, characterized in that the . oxidation base(s) used as second oxidation base represent from 0.0005 to 12% by weight of the total - weight of the dyeing composition.

18. The composition as claimed in claim 17, characterized in that the oxidation base (s) used as second oxidation base represent from 0.005 to 6% by weight of the total weight of the dyeing composition.

19. The composition as claimed in any one of the preceding claims, characterized in that it contains at least one coupler chosen from meta-phenylene- diamines, meta-aminophenols, meta-diphenols and heterocyclic couplers, and their addition salts with an acid.

20. The composition as claimed in claim 19, characterized in that the couplers are chosen from 2-methyl-5-aminophenol, 5-N- (B-hydroxyethyl)amino-2-

hY methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxy- benzene, 2,4-diamino-1- (B-hydroxyethyloxy)benzene, 2-amino-4- (f-hydroxyethylamino) -1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, l-amino-2-methoxy-4,5-methylenedioxybenzene, o-naphthol, 2-methyl-l-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxy-

. indoline, 2,6-dihydroxy-4-methylpyridine, 1-H-3-methyl- pyrazol-5-one, l-phenyl-3-methylpyrazol-5-one, and their addition salts with an acid.

21. The composition as claimed in claim 19 or 20, characterized in that the coupler(s) represent from 0.0001 to 15% by weight relative to the total weight of the composition.

22. The compesition as claimed in any one of the preceding claims, characterized in that it contains one or more additional oxidation bases chosen from para-phenylenediamine, para-tolylenediamine, 2-chloro- para-phenylenediamine, 4-aminophenol, and their addition salts with an acid.

23. The composition as claimed in any one of the preceding claims, characterized in that the addition salts with an acid are chosen from hydrochlorides, hydrobromides, sulfates, tartrates, lactates and acetates.

24. A method for the oxidation dyeing of keratinous fibers, and in particular human keratinous fibers such as hair, characterized in that at least one dyeing composition as defined in any one of claims 1 to 23 is applied to said fibers, the color being developed at acidic, neutral or alkaline pH with the aid of an oxidizing agent which is added just at the time of use to the dyeing composition or which is present in an oxidizing composition applied simultaneously or sequentially, separately.

25. The method as claimed in claim 24, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts and oxidative enzymes.

26. A multicompartment device, or multi- compartment dyeing “kit”, in which a first compartment contains a dyeing composition as defined in any one of claims 1 to 23 and a second compartment contains an oxidizing composition.