Compositions for dyeing keratin fibers, containing cationic...

Details Compositions for dyeing keratin fibers, containing cationic... Compositions for dyeing keratin fibers, containing cationic...

2001-02-26

2003-06-17

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S407000, C008S408000, C008S409000, C008S410000, C008S412000, C546S085000

Reexamination Certificate

active

06579326

ABSTRACT:

The invention relates to compositions for the oxidation dyeing of keratin fibres, comprising at least one oxidation base and at least one coupler chosen from indolizine derivatives comprising at least one cationic group Z, wherein Z may be chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring, and aliphatic chains comprising at least one quaternized unsaturated ring, to oxidation dyeing processes using them and to novel cationic indolizine derivatives.
Dye compositions comprising oxidation dye precursors are known in the art for dyeing keratinous fibres, 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, i.e., 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 molecules used as oxidation bases and couplers may make it possible to obtain a wide range of colours.
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 white hairs, and should be as unselective as possible, that is, they should allow only 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, entirely surprisingly and unexpectedly, that the indolizine derivatives of formula (I) defined below comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring and aliphatic chains comprising at least one quaternized unsaturated ring, are not only suitable for use as couplers for oxidation dyeing, but also make it possible to obtain dye compositions which provide at least one of intense colorations in a very wide range of shades and excellent properties of resistance to the various treatments to which the keratin fibres may be subjected.
A subject of the invention is thus a composition for dyeing keratin fibres, such as, for example, human keratin fibres such as the hair, wherein the composition comprises, in a medium which is suitable for 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:
in which:
n may be an integer from 0 to 4;
R
1
and R
3
, which may be identical or different, are each chosen from hydrogen atoms; halogen atoms; Z groups; 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 which are optionally substituted with at least one radical chosen from halogen atoms, C
1
-C
4
alkyl radicals, trifluoro-methyl radicals, C
1
-C
4
alkoxy radicals, amino radicals, 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;
R
3
may optionally further be chosen from 5- and 6-membered unsaturated heterocycles;
R
2
and R
4
, which may be identical or different, are each chosen from hydrogen atoms; halogen atoms, Z groups; 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
)alkyl-amino(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 which are 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;
Z is chosen from the following unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below:
in which:
D is a linker arm which is chosen from linear and branched alkylene chains, preferably containing from 1 to 14 carbon atoms, which may be interrupted by at least one hetero atom, and which may be substituted with at least one substituent chosen from hydroxyl and C
1
-C
6
alkoxy radicals, and which may bear at least one ketone function;
the ring members E, G, J, L and M, which may be identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms;
b is an integer from 0 to 4;
m is an integer from 0 to 5;
the radicals R, which may be identical or different, are chosen from a second group Z, which may be identical to or different from the first group Z, halogen atoms, hydroxyl radicals, C
1
-C
6
alkyl radicals, C
1
-C
6
monohydroxyalkyl radicals, C
2
-C
6
polyhydroxyalkyl radicals, nitro radicals, cyano radicals, cyano(C
1
-C
6
)alkyl radicals, C
1
-C
6
alkoxy radicals, tri(C
1
-C
6
)alkylsilane(C
1
-C
6
)alkyl radicals, amido radicals, aldehydo radicals, carboxyl radicals, (C
1
-C
6
)alkylcarbonyl radicals, thio radicals, C
1
-C
6
thioalkyl radicals, C
1
-C
6
alkylthio radicals, amino radicals, amino radicals protected with at least one group chosen from (C
1
-C
6
)alkylcarbonyls, carbamyls and C
1
-C
6
alkylsulphonyl radicals; NHR″ and NR′R″ groups in which R″ and R′″, which may be identical or different, are chosen from C
1
-C
6
alkyl radicals, C
1
-C
6
monohydroxyalkyl radicals and C
2
-C
6
polyhydroxyalkyl radicals;
R
5
is chosen from C
1
-C
6
alkyl radicals, C
1
-C
6
mono-hydroxyalkyl radicals, C
2
-C
6
polyhydroxyalkyl radicals, cyano(C
1
-C
6
)alkyl radicals, tri(C
1
-C
6
)-alkylsilane(C
1
-C
6
)alkyl radicals, (C
1
-C
6
)alkoxy-(C
1
-C
6
)alkyl radicals, carbamyl(C
1
-C
6
)alkyl radicals, (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyl radicals, benzyl radicals and second Z groups which may be identical to or different from the first Z groups;
R
6
, R
7
and R
8
, which may be identical or different, are each chosen from C
1
-C
6
alkyl radicals, C
1
-C
6
monohydroxyalkyl radicals, C
2
-C
6
polyhydroxyalkyl radica

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