Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-10-20
2003-03-11
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S406000, C008S407000, C008S408000, C008S409000, C008S410000, C008S411000
Reexamination Certificate
active
06530960
ABSTRACT:
The present invention is directed to compositions for oxidation dyeing of keratin fibres comprising (a) at least one oxidation base, (b) at least one coupler chosen from 2-substituted 5-aminoalkylphenol derivatives and the acid addition salts thereof, and (c) at least one additional coupler chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, heterocyclic couplers and the acid addition salts thereof, in a medium suitable for dyeing. The inventive compositions can be used for oxidation dyeing of human keratin fibres such as hair. The present invention is also directed to dyeing processes using these compositions.
Dye compositions comprising oxidation dye precursors are known in the art for dyeing keratinous fibres, in particular human hair. These oxidation dye precursors include ortho-phenylenediamines, para-phenylenediamines, ortho-aminophenols, para-aminophenols and heterocyclic bases. These are generally known as oxidation bases. The oxidation dye precursors, or oxidation bases, are generally colorless or weakly colored compounds which may give rise to colored compounds and dyes when combined with oxidizing products via oxidative condensation.
The shades obtained with these oxidation bases may be varied by combining them with couplers or coloration modifiers. Such coloration modifiers may, for example, be chosen from aromatic meta-diamines, aromatic meta-aminophenols, aromatic meta-diphenols and certain heterocyclic compounds. The variety of oxidation bases and couplers may allow a wide range of colors to be obtained.
The so-called “permanent” coloration obtained from using these oxidation dyes should have at least one of the following desirable characteristics. The coloration should have no toxicological drawbacks, the shades obtained should have the desired intensity, and the coloration should have good resistance to external agents to which the fibres may be subjected such as light, bad weather, washing, permanent-waving, perspiration and rubbing. The dyes should allow coverage of grey hair and should be as unselective as possible, that is, they should allow only the smallest possible differences in coloration along the same keratinous fibre which may be differently sensitized (i.e. damaged) between its tip and its root.
Also known in the art are dye compositions containing 2-substituted 5-aminoalkylphenol derivatives for use as couplers. These may be in combination with one or more oxidation bases chosen from, for example, certain para-phenylenediamines, para-aminophenol, para-methylaminophenol, ortho-aminophenol and certain heterocyclic oxidation bases such as 2,5-diaminopyridine and tetraaminopyrimidine. Such dye compositions have been proposed, for example, in patent application JP-2 521 636, the disclosure of which is incorporated herein by reference. However, the colorations obtained using these compositions may not always be sufficiently strong, chromatic and/or resistant to various external agents to which the fibres may be subjected.
The inventors have now discovered that by combining (i) at least one oxidation base, (ii) at least one coupler chosen from 2-substituted 5-aminoalkylphenol derivatives of formula (I) as defined below and the acid addition salts thereof and (iii) at least one additional coupler chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, heterocyclic couplers and the acid addition salts thereof, it may be possible to obtain novel dyes which may result in chromatic, strong, aesthetic colorations in a variety of shades, which may be mainly unselective and which may show satisfactory resistance to one or more external agents to which the fibres may be subjected.
Specifically, one subject of the present invention is compositions for oxidation dyeing of keratin fibres comprising:
(a) at least one oxidation base;
(b) at least one coupler chosen from 2-substituted 5-aminoalkylphenol derivatives of formula (I) and the acid addition salts thereof:
wherein:
R
1
is chosen from hydrogen atoms and C
2
-C
5
acyl groups, optionally substituted;
R
2
is chosen from hydrogen atoms, C
1
-C
4
alkyl groups, optionally substituted, C
1
-C
4
alkoxy groups, optionally substituted, and amino groups, optionally substituted;
R
3
is chosen from hydrogen atoms, halogen atoms, C
1
-C
4
alkoxy groups and C
1
-C
4
monohydroxyalkoxy groups; and
R
4
is chosen from C
1
-C
4
alkyl groups; and
(c) at least one additional coupler chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, heterocyclic couplers and the acid addition salts thereof, in a medium suitable for dyeing. For example, the keratin fibres may be human keratin fibres, such as hair.
By virtue of the present invention, it may be possible to obtain chromatic, strong, aesthetic colorations in a variety of shades which may show low selectivity and may show excellent properties of withstanding not only at least one atmospheric agent (such as light and bad weather) but may also withstand perspiration and/or various treatments to which the hair may be subjected.
Another subject of the present invention is processes for oxidation dyeing of keratin fibres using the inventive compositions.
The nature of the at least one oxidation base that may be used in the present invention is not a critical factor. For example, the at least one oxidation base can be chosen from para-phenylenediamines, double bases, para-aminophenols, ortho-aminophenols, heterocyclic oxidation bases and the acid addition salts of any of the foregoing at least one oxidation bases.
For example, the para-phenylenediamines suitable for use in the present invention can be chosen from compounds of formula (II) and the acid addition salts thereof:
wherein:
R
5
is chosen from hydrogen atoms, C
1
-C
4
alkyl groups, C
1
-C
4
monohydroxyalkyl groups, C
2
-C
4
polyhydroxyalkyl groups, (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl groups, C
1
-C
4
alkyl groups substituted with at least one nitrogen-containing group, phenyl groups and 4′-aminophenyl groups;
R
6
is chosen from hydrogen atoms, C
1
-C
4
alkyl groups, C
1
-C
4
monohydroxyalkyl groups, C
2
-C
4
polyhydroxyalkyl groups, (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl groups and C
1
-C
4
alkyl groups substituted with at least one nitrogen-containing group;
R
7
is chosen from hydrogen atoms, halogen atoms such as a chlorine, bromine, iodine or fluorine atom, C
1
-C
4
alkyl groups, C
1
-C
4
monohydroxyalkyl groups, C
1
-C
4
hydroxyalkoxy groups, acetylamino(C
1
-C
4
)alkoxy groups, C
1
-C
4
mesylaminoalkoxy groups and carbamoylamino(C
1
-C
4
)alkoxy groups; and
R
8
is chosen from hydrogen atoms, halogen atoms and C
1
-C
4
alkyl groups.
Non-limiting examples of nitrogen-containing groups comprised in groups of formula (II) include amino groups, mono(C
1
-C
4
)alkylamino groups, di(C
1
-C
4
)alkylamino groups, tri(C
1
-C
4
)alkylamino groups, monohydroxy(C
1
-C
4
)alkylamino groups, imidazolinium groups and ammonium groups.
In one embodiment, compounds of formula (II) are chosen from para-phenylenediamine, para-tolylenediamine, 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)-2-methylaniline, 4-amino-2-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,N-(ethyl-&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-phenylenediamine, N-(&bgr;-methoxyethyl)-para-phenylenedia
Lagrange Alain
Pastore Florent
Elhilo Eisa
Finnegan, Henderson Farabow, Garrett and Dunner L.L.P.
Gupta Yogendra N.
L'Oreal (S.A.)
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