Use of cationic phenyl-azo-benzene compounds for dyeing...

Details Use of cationic phenyl-azo-benzene compounds for dyeing... Use of cationic phenyl-azo-benzene compounds for dyeing...

2000-01-18

2002-10-01

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S407000, C008S411000, C008S429000, C008S662000, C534S630000, C534S676000, C534S857000

Reexamination Certificate

active

06458167

ABSTRACT:

The present invention relates to dyeing compositions containing phenyl-azo-benzene compounds comprising at least one cationic group Z 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 the use of such compositions as direct dyes in dyeing applications for keratin substances, in particular human keratin fibers and especially the hair, and to the direct dyeing processes employing these compositions.
In the field of hair dyeing, direct dyes are sought, i.e., dyes which, without an oxidizing agent being supplied, are capable by themselves of temporarily modifying the natural shade of the hair, while satisfying a certain number of criteria. In particular, it is desired that these direct dyes generate reproducible dyeing effects with rich and varied shades, making it possible to obtain a wide range of colors capable of satisfying formulators, and that these dyeing effects are intense and fast with respect to washing, rubbing, light and perspiration.
The inventors have just discovered, entirely surprisingly and unexpectedly, that phenyl-azo-benzene compounds of formula (I) defined below, comprising at least one cationic group Z 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 suitable for use as direct dyes for direct dyeing, and also that they make it possible to obtain dye compositions which lead to intense and varied colorations which have excellent properties of fastness with respect to the various treatments to which keratin fibers properties of fastness with respect to the various treatments to which keratin fibers may be subjected. Finally, these compounds display better solubility in the media conventionally used for dyeing keratin fibers and are found to be easy to synthesize.
These discoveries form the basis of the present invention.
A first subject of the invention is thus the use, as direct dyes, in, or for the manufacture of, dye compositions for keratin substances, and in particular for human keratin fibers such as the hair, of phenyl-azo-benzene compounds of formula (I) below, and the acid addition salts thereof:
in which:
R
1
, R
2
, R
3
, R′
1
, R′
2
and R′
3
, which may be identical or different, represent a hydrogen atom; a halogen atom; a group Z defined below; a (C
1
-C
6
)alkylcarbonyl radical; an amino(C
1
-C
6
)alkylcarbonyl radical; an N-Z-amino(C
1
-C
6
)alkylcarbonyl radical; an N-(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl radical; an N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl radical; an amino(C
1
-C
6
)alkylcarbonyl-(C
1
-C
6
)alkyl radical; an N-Z-amino(C
1
-C
6
)-alkylcarbonyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
)-alkylamino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl-(C
1
-C
6
)alkyl radical; a carboxyl radical; a (C
1
-C
6
)alkylcarboxyl radical; a C
1
-C
6
alkylsulphonyl radical; an aminosulphonyl radical; an N-Z-aminosulphonyl radical; a C
1
-C
6
N-alkylaminosulphonyl radical; a C
1
-C
6
N,N-dialkylaminosulphonyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N-Z-aminosulphonylalkyl radical; an N-(C
1
-C
6
)-alkylaminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; a carbamyl radical; an N-(C
1
-C
6
)alkylcarbamyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl radical; a carbamyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a cyano radical; a nitro radical; an amino group NR
4
R
5
in which R
4
and R
5
are defined below; a group OR
6
or SR
6
in which R
6
is defined below; or a C
1
-C
6
aminoalkyl radical in which the alkyl may be unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two identical or different radicals chosen from C
1
-C
6
alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, carbamyl, N-(C
1
-C
6
)alkylcarbamyl or N,N-di(C
1
-C
6
)alkylcarbamyl, C
1
-C
6
alkylsulphonyl, formyl, trifluoro(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl and thiocarbamyl radicals, or with a group Z defined below;
A represents a group NR
4
R
5
in which R
4
and R
5
are defined below or a group OR
6
in which R
6
is defined below;
R
4
and R
5
, which may be identical or different, represent a hydrogen atom; a group Z defined below; a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; an aryl radical; a benzyl radical; a cyano(C
1
-C
6
)alkyl radical; a carbamyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; a thio-carbamyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
sulphoalkyl radical; a (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylsulphinyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N-Z-aminosulphonylalkyl radical; an N-(C
1
-C
6
)alkyl-aminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
aminoalkyl radical; a C
1
-C
6
aminoalkyl radical in which the alkyl can be unsubstituted or substituted with one or more hydroxyl radicals radicals which are chosen from C
1
-C
6
alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, carbamyl, N-(C
1
-C
6
)alkylcarbamyl or N,N-di(C
1
-C
6
)-alkylcarbamyl, C
1
-C
6
alkylsulphonyl, formyl, trifluoro-(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl, thiocarbamyl radicals, and a group Z defined below, or which may together form, with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more identical or different hetero atoms;
R
6
denotes a hydrogen atom; a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a group Z; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; an aryl radical; a benzyl radical; a carboxy(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyl radical; a cyano(C
1
-C
6
)alkyl radical; a carbamyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N-Z-amino-sulphonylalkyl radical; an N-(C
1
-C
6
)alkyl-aminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylsulphinyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)-alkylsulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)-alkylcarbonyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; a C
1
-C
6
aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two identical or different radicals which are chosen from C
1
-C
6
alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, formyl, trifluoro(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl, carbamyl, N-(C
1
-C
6
)alkylcarbamyl, N,N-di(C
1
-C
6
)alkylcarbamyl, thiocarbamyl, C
1
-c
6
alkylsulphonyl radicals, and a group Z defined below, or which may together form, with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or

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