Indolizine derivatives, compositions comprising at least one...

Details Indolizine derivatives, compositions comprising at least one... Indolizine derivatives, compositions comprising at least one...

2001-02-26

2003-06-03

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S405000, C008S409000, C008S410000, C008S423000, C424S062000, C424S489000, C546S112000

Reexamination Certificate

active

06572664

ABSTRACT:

The present invention relates to compositions for oxidation dyeing of keratin fibers comprising at least one oxidation base and at least one coupler chosen from specific indolizine derivatives.
Dye compositions comprising oxidation dye precursors are known in the art for dyeing keratinous fibers, such as human hair. The oxidation dye precursors include ortho-phenylenediamines, para-phenylenediamines, ortho-aminophenols, para-aminophenols, and heterocyclic compounds. 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 coupling.
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, meta-aminophenols, meta-diphenols, and certain heterocyclic compounds, such as indole compounds. The variety of oxidation bases and couplers may allow a rich palette 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 fibers may be subjected, such as light, bad weather, washing, permanent-waving, perspiration, and rubbing. The dyes should allow coverage of white hairs, and should be as unselective as possible, that is, they should allow only the the smallest possible differences in coloration along the same keratin fiber, which may be differently sensitized (i.e. damaged) between its end tip and its root.
Indazole-type compounds have been used in the field of hair dyeing. For example, in DE-A-1 492 166, the disclosure of which is incorporated herein by reference, the polycondensation of such compounds via oxidation has been proposed, in DE-A-2 623 564, the disclosure of which is incorporated herein by reference, it has been proposed to combine hydroxy-indazoles with tetraaminopyrimidines, and in U.S. Pat. No. 4 013 404, the disclosure of which is incorporated herein by reference, certain aminoindazoles and their use as oxidation dye precursors have been proposed.
The inventors have discovered that it may be possible, by using specific indolizine derivatives, to obtain novel dyes which are at least one of the following: powerful, unselective, resistant, and capable of generating intense colorations in varied shades.
Specifically, one subject of the present invention is a composition for oxidation dyeing of keratin fibers comprising, in a medium suitable for oxidation dyeing:
(i) at least one oxidation base; and
(ii) at least one coupler chosen from indolizine derivatives of formula (I) and the acid addition salts thereof:
wherein:
n is an integer ranging from 0 to 4;
R
1
and R
3
, which may be identical or different, are each chosen from a hydrogen atom; halogen atoms; C
1
-C
4
alkyl radicals; C
1
-C
4
alkoxy radicals; C
1
-C
4
monohydroxyalkyl radicals; C
2
-C
4
polyhydroxyalkyl radicals; C
1
-C
4
aminoalkyl radicals; acetylamino radicals; acetylamino(C
1
-C
4
)alkyl radicals; (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radicals; mono(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals; di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals; aminocarboxy(C
1
-C
4
)alkyl radicals; acetyl(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals; and aromatic rings, optionally substituted with at least one radical chosen from halogen atoms, C
1
-C
4
alkyl radicals, trifluoromethyl radicals, C
1
-C
4
alkoxy radicals, amino radicals and mono- and disubstituted amino radicals wherein the substituent is chosen from C
1
-C
4
alkyl radicals, (C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals, di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals, carboxyl radicals and sulphoxy radicals;
wherein R
3
may optionally further be chosen from 5- and 6-membered unsaturated heterocycles; and
with the proviso that at least one of R
1
and R
3
is a hydrogen atom;
R
2
and R
4
, which may be identical or different, are each chosen from a hydrogen atom, halogen atoms, C
1
-C
4
alkyl radicals, C
1
-C
4
monohydroxyalkyl radicals, C
2
-C
4
polyhydroxyalkyl radicals, C
1
-C
4
aminoalkyl radicals, mono(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals, di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals, carboxyl radicals, cyano radicals, carboxy(C
1
-C
4
)alkyl radicals, nitro radicals, and 5- and 6-membered aromatic rings, optionally substituted with at least one radical chosen from halogen atoms, C
1
-C
4
alkyl radicals, trifluoromethyl radicals, C
1
-C
4
alkoxy radicals, amino radicals and mono- and disubstituted amino radicals wherein the substituent is chosen from C
1
-C
4
alkyl radicals, (C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals, di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals, carboxyl radicals and sulphoxy radicals.;
As used herein, “at least one” means one or more and thus includes individual components as well as mixtures/combinations. Further, as used herein, unless otherwise noted, alkyl radicals may be chosen from substituted, unsubstituted, linear, branched, and cyclic alkyl radicals. Similarly, as used herein and unless otherwise noted, the alkyl radicals of alkoxy radicals may be chosen from substituted, unsubstituted, linear, branched, and cyclic alkyl radicals.
Non-limiting examples of 6-membered aromatic rings of formula (I) include phenyl rings, nitrophenyl rings, alkylphenyl rings, alkoxyphenyl rings, polyalkyl-phenyl rings and polyalkoxyphenyl rings.
Non-limiting examples of unsaturated 5- and 6-membered heterocycles include pyrrole rings, pyridine rings, pyrimidine rings, imidazole rings, pyrazole rings, oxazole rings, thiazole rings, triazole rings, pyrazolotriazole rings, pyrazoloimidazole rings, pyrrolotriazole rings, pyrazolopyrimidine rings, pyrazolopyridine rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, indole rings, indoline rings, indolidine rings, isoindolidine rings, benzotriazoline rings, pyrazine rings, oxazine rings, triazine rings, quinoline rings, tetrahydro-quinoline rings, benzimidazolidine rings and benzopyrimidine rings.
Compounds comprised within those of formula (I) may be known, for example, in the field of photography, and methods of preparing this type of compound may be disclosed in Chichibabin, Ber. 1927, 60, 1607; Borrows et al., J. Chem. Soc., 1946, 1069; and/or T. Uchida et al.,
Synthesis,
1976, 209-236.
Colorations obtained using the inventive dye compositions may possess at least one of the following desirable characteristics: unselectivity, power, ability to enable a variety of shades, and excellent properties of resistance to at least one of atmospheric agents chosen from light and bad weather, perspiration and treatments to which the hair may be subjected (such as shampooing, permanent-waving, etc.).
In one embodiment, indolizine derivatives of formula (I) are chosen from:
indolizine;
2-methyl-1-phenylindolizine;
2,8-dimethylindolizine;
methyl 2-methylindolizine-6-carboxylate;
2,7-dimethylindolizine;
2-methyl-1-(4-nitrophenyl)indolizine;
8-methyl-2-phenylindolizine;
2-methylindolizine;
7-methyl-2-phenylindolizine;
2-phenylindolizine;
7-methyl-2-(3-nitrophenyl)indolizine;
7-methyl-2-(2,5-dimethoxyphenyl)indolizine;
2-(2-pyridyl)indolizine;
2-(4-N,N-dimethylaminophenyl)indolizine;
2-phenyl-3-[2-(4-pyridyl)ethyl]indolizine;
2-phenyl-3-[2-(2-pyridyl)ethyl]indolizine;
2-ethyl-7-methoxyindolizine;
2-ethyl-8-methoxyindolizine;
ethyl 2-butyl-7-indolizinecarboxylate;
1-ethylindolizine;
6,8-dimethylindolizine;
5-ethyl-7-methylindolizine;
N,N-diethyl-2-methyl-1-indolizinethanamine;
N,N-dimethyl-2-methyl-1-indolizinethanamine;
N-ethyl-2-methyl-1-indolizinethanamine;
N-methyl-2-methyl-1-indolizinethanamine;
2-methyl-1-indolizinethanamine;
5,7-dimethylindolizine;
8-cyano-2-methylindolizine;
1-ethyl-2-methylindolizine;
5-in

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