Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-04-13
2004-08-24
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S421000, C008S423000
Reexamination Certificate
active
06780203
ABSTRACT:
The present invention relates to a composition for the oxidation dyeing of keratin fibres, in particular human keratin fibres such as the hair, comprising at least one oxidation base chosen from diaminopyrazoles and triaminopyrazoles, in combination with at least one meta-aminophenol which is halogenated ortho to the phenol, as coupler, and to the dyeing process using this composition with an oxidizing agent.
It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds such as pyrazole derivatives, which are generally referred to as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds and dyes by means of a process of oxidative condensation.
It is also known that the shades obtained with oxidation bases can be varied by combining them with suitably selected couplers or coloration modifiers, the latter possibly being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained.
The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must have no toxicological drawbacks, it must allow shades to be obtained in the desired intensity and it must satisfactorily withstand external agents (light, bad weather, washing, permanent-waving, perspiration or rubbing).
The dyes must also be able to cover white hair, and, lastly, they must be as unselective as possible, i.e. they must allow only the smallest possible differences in colour along the same keratin fibre, which may in fact be differently sensitized (i.e. damaged) between its tip and its root.
Compositions for the oxidation dyeing of keratin fibres, containing pyrazole derivatives such as 4,5-diaminopyrazoles, 3,4-diaminopyrazoles or 3,4,5-triaminopyrazoles as oxidation base, in combination with couplers conventionally used for oxidation dyeing, such as, for example, meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers such as, for example, indole derivatives, have already been proposed, in particular in German patent applications DE 3 843 892, DE 4 234 887, DE 4 234 886, DE 4 234 885 and DE 195 43 988. However, such compositions are not entirely satisfactory, in particular as regards the fastness of the colorations obtained with regard to the various attacking factors to which the hair may be subjected, and in particular with regard to perspiration.
However, the Applicant has now discovered that it is possible to obtain novel powerful dyes that are particularly resistant to the various attacking factors to which the hair may be subjected, by combining, as oxidation base, at least one diaminopyrazole and/or at least one triaminopyrazole and, as coupler, a meta-aminophenol halogenated in a position ortho to the phenol.
This discovery forms the basis of the present invention.
A first subject of the invention is thus a composition for the oxidation dyeing of keratin fibres and in particular human keratin fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing:
at least one oxidation base chosen from diaminopyrazoles and triaminopyrazoles;
and at least one coupler chosen from the halogenated meta-aminophenols of formula (I) below, and the addition salts thereof with an acid:
in which:
R
1
and R
2
, which may be identical or different, represent a hydrogen atom, a halogen atom such as chlorine, bromine, iodine or fluorine, a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
2
-C
4
polyhydroxyalkyl radical, a C
1
-C
4
alkoxy radical, a C
1
-C
4
monohydroxyalkoxy radical or a C
2
-C
4
polyhydroxyalkoxy radical;
R
3
and R
4
, which may be identical or different, represent a hydrogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
2
-C
4
polyhydroxyalkyl radical or a C
1
-C
4
monoaminoalkyl radical; it being understood that at least one of the radicals R
1
and R
2
represents a halogen atom.
The oxidation dye composition in accordance with the invention makes it possible to obtain intense colorations in varied shades, which are relatively unselective and which have excellent properties of resistance both with respect to atmospheric agents such as light and bad weather, and with respect to perspiration and the various treatments to which the hair may be subjected (shampooing, permanent-waving). These properties are particularly noteworthy especially as regards the resistance of the colorations with respect to perspiration.
Among the C
1
-C
4
alkyl and C
1
-C
4
alkoxy radicals of the compounds of formula (I) above, mention may be made in particular of the methyl, ethyl, propyl, methoxy and ethoxy radicals.
Among the halogenated meta-aminophenols of formula (I), mention may be made more particularly of 3-amino-6-chlorophenol, 3-amino-6-bromophenol, 3-(&bgr;-aminoethyl)amino-6-chlorophenol, 3-(&bgr;-hydroxyethyl)-amino-6-chlorophenol and 3-amino-2-chloro-6-methylphenol, and the addition salts thereof with an acid.
Among the diaminopyrazoles which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more particularly of:
a) the diaminopyrazoles of formula (II) below, and the addition salts thereof with an acid:
in which:
R
5
represents a hydrogen atom, a C
1
-C
6
alkyl radical, a C
2
-C
4
hydroxyalkyl radical, a benzyl radical, a phenyl radical, a benzyl radical substituted with a halogen atom or with a C
1
-C
4
alkyl or C
1
-C
4
alkoxy group, or forms, with the nitrogen atom of the group NR
7
R
8
in position 5, a hexahydropyridazine or tetrahydropyrazole heterocycle which is optionally monosubstituted with a C
1
-C
4
alkyl group;
R
6
and R
7
which may be identical or different, represent a hydrogen atom, a C
1
-C
4
alkyl radical, a C
2
-C
4
hydroxyalkyl radical, a benzyliradical or a phenyl radical;
R
8
represents a hydrogen atom, or a C
1
-C
6
alkyl or C
2
-C
4
hydroxyalkyl radical; with the proviso that R
6
represents a hydrogen atom when R
5
represents a substituted benzyl radical or forms a heterocycle with the nitrogen atom of the group NR
7
R
8
in position 5;
b) the diaminopyrazoles of formula (III) below, and the addition salts thereof with an acid:
in which:
R
9
, R
10
, R
11
, R
12
and R
13
, which may be identical or different, represent a hydrogen atom; a linear or branched C
1
-C
6
alkyl radical; a C
2
-C
4
hydroxyalkyl radical; a C
2
-C
4
aminoalkyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or a C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro, trifluoromethyl, amino or C
1
-C
4
alkylamino radical; a benzyl radical; a benzyl radical substituted with a halogen atom or with a C
1
-C
4
alkyl, C
1
-C
4
alkoxy, methylenedioxy or amino radical; or a radical
in which m and n are integers, which may be identical or different, between 1 and 3 inclusive, X represents an oxygen atom or an NH group, Y represents a hydrogen atom or a methyl radical, and Z represents a methyl radical, a group OR or NRR′ in which R and R′, which may be identical or different, denote a hydrogen atom, a methyl radical or an ethyl radical, it being understood that when R
10
represents a hydrogen atom, then R
11
can also represent an amino or C
1
-C
4
alkylamino radical,
R
14
represents a linear or branched C
1
-C
6
alkyl radical; a C
1
-C
4
hydroxyalkyl radical; a C
1
-C
4
aminoalkyl radical; a (C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical; a di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical; a hydroxy(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical; a (C
1
-C
4
)alkoxymethyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or with a
Audousset Marie-Pascale
Maubru Mireille
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
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