Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-07-12
2001-10-23
Hardee, John (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S408000, C008S409000, C008S410000, C008S411000, C008S412000, C008S421000
Reexamination Certificate
active
06306180
ABSTRACT:
The subject-matter of the present invention is a composition for the oxidation dyeing of keratinous fibres, in particular of human keratinous fibres, such as hair, comprising 2-chloro-6-methyl-3-aminophenol as coupler, in combination with at least one suitably selected oxidation base and at least one additional coupler chosen from suitably selected meta-aminophenols and meta-phenylenediamines, and the dyeing process employing this composition with an oxidizing agent.
It is known to dye keratinous fibres and in is particular human hair with dyeing compositions comprising oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, or heterocyclic compounds, such as pyrimidine derivatives, generally known as oxidation bases. Oxidation dye precursors or oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing substances, can give rise, by an oxidative coupling process, to coloured and colouring compounds.
It is also known that it is possible to vary the shades obtained with oxidation bases by combining them with suitably chosen couplers or colouring modifiers, it being possible for the latter in particular to be chosen from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of the molecules involved as oxidation bases and couplers makes it possible to obtain a rich palette of colours.
The so-called “permanent” colouring obtained by virtue of these oxidation dyes has, however, to satisfy a certain number of requirements. Thus, it must be without disadvantage toxicologically and it must make it possible to obtain shades with the desired intensity and behave well in the face of external agents (light, bad weather, washing, permanent waving, perspiration or rubbing).
The dyes must also make it possible to cover white hair and, finally, be as non-selective as possible, that is to say make it possible to obtain the smallest possible difference in colouring along the same keratinous fibre, which can in fact be differently sensitized (i.e. damaged) between its tip and its root.
Provision has already been made, in particular in German Patent Application DE 3,016,008, for compositions for the oxidation dyeing of keratinous fibres comprising, as coupler, 2-chloro-6-methyl-3-aminophenol or 2-methyl-5-chloro-3-aminophenol in combination with oxidation bases conventionally used for oxidation dyeing, such as, for example, certain para-phenylenediamines or para-aminophenols. However, such compositions are not entirely satisfactory, in particular from the viewpoint of the behaviour of the colourings obtained with respect to various attacks which hair can be subjected to and in particular with respect to shampoos and permanent deformations.
Provision has also been made, in Patent Applications WO 96/15765 and WO 96/15766, for compositions for the oxidation dyeing of keratinous fibres comprising the specific combination of 2-chloro-6-methyl-3-aminophenol as coupler, of a specific oxidation base, such as 2-(R-hydroxyethyl)-para-phenylenediamine or 2-aminomethyl-4-aminophenol, and of a coupler, such as, for example, 2-methyl-5-aminophenol or resorcinol. However, such compositions are not entirely satisfactory either, in particular from the viewpoint of the selectivity of the colourings obtained.
The Applicant Company has now just discovered that it is possible to obtain powerful novel dyes which are particularly resistant to the various attacks which hair can be subjected to by combining 2-chloro-6-methyl-3-aminophenol, at least one suitably selected oxidation base and at least one coupler chosen from suitably selected meta-aminophenols and meta-phenylenediamines.
This discovery is at the basis of the present invention.
The first subject-matter of the invention is therefore a composition for the oxidation dyeing of keratinous fibres and in particular of human keratinous fibres, such as hair, characterized in that it comprises, in a medium appropriate for dyeing:
2-chloro-6-methyl-3-aminophenol and/or at least one of its addition salts with an acid, as first coupler;
at least one oxidation base;
and at least one additional coupler chosen from meta-aminophenols and meta-phenylenediamines; it being understood that the said composition does not simultaneously include 2-(&bgr;-hydroxyethyl)-para-phenylenediamine and 2-methyl-5-aminophenol.
The oxidation dyeing composition in accordance with the invention makes it possible to obtain powerful colourings with varied shades which are not very selective and which exhibit excellent properties of resistance both with respect to atmospheric agents, such as light and bad weather, and with respect to perspiration and various treatments which hair can be subjected to (shampoos, permanent deformations). These properties are particularly noteworthy, in particular as regards the low selectivity of the colourings obtained.
The oxidation bases which can be used in the dyeing compositions in accordance with the invention are preferably chosen from para-phenylenediamines, double bases, para-aminophenols, ortho-aminophenols and heterocyclic oxidation bases.
Mention may in particular be made, among the para-phenylenediamines which can be used as oxidation bases in the dyeing compositions in accordance with the invention, of the compounds of following formula (I) and their addition salts with an acid:
in which:
R
1
represents a hydrogen atom, 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(C
1
-C
4
)alkyl radical or a C
1
-C
4
alkyl radical substituted by a nitrogenous, phenyl or 4′-aminophenyl group;
R
2
represents a hydrogen atom, 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(C
1
-C
4
)alkyl radical or a C
1
-C
4
alkyl radical substituted by a nitrogenous group;
R
3
represents a hydrogen atom, a halogen atom, such as a chlorine, bromine, iodine or fluorine atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
1
-C
4
hydroxyalkoxy radical, a C
1
-C
4
acetylaminoalkoxy radical, a C
1
-C
4
mesylaminoalkoxy radical or a C
1
-C
4
carbamoylaminoalkoxy radical;
R
4
represents a hydrogen or halogen atom or a C
1
-C
4
alkyl radical.
Mention may in particular be made, among the nitrogenous groups of the above formula (I), of the amino, mono(C
1
-C
4
)alkylamino, di(C
1
-C
4
)alkylamino, tri(C
1
-C
4
)alkylamino, monohydroxy(C
1
-C
4
)alkylamino, imidazolinium and ammonium radicals.
Mention may more particularly be made, among the para-phenylenediamines of above formula (I), of para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 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(&bgr;-hydroxyethyl)-para-phenylenediamine, 4-amino-N,N-bis(&bgr;-hydroxyethyl)-3-methylaniline, 4-amino-3-chloro-N,N-bis(&bgr;-hydroxyethyl)aniline, 2-(&bgr;-hydroxyethyl)-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(&bgr;-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N-ethyl-N-(&bgr;-hydroxyethyl)-para-phenylenediamine, N-(&bgr;,&ggr;-dihydroxypropyl)-para-phenylenediamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-(&bgr;-hydroxyethyloxy)-para-phenylenediamine, 2-(&bgr;-acetylaminoethyloxy)-para-phenylenediamines, N-(&bgr;-methoxyethyl)amino-para-phenylenediamine and their addition salts with an acid.
Preference is very particularly given, among the para-phenylenediamines of above formula (I), to para-phenylenediamine, para-toluylenediamine, 2-isopropyl-para-phenylenediamine, 2-(&bgr;-hydroxyethyl)-para-phenylenediamine, 2-(&bgr;-hydroxyethyloxy) -para-phenylene
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Hardee John
L'Oreal (S.A.)
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