Use of cationic monobenzene nitroanilines in the dyeing of...

Details Use of cationic monobenzene nitroanilines in the dyeing of... Use of cationic monobenzene nitroanilines in the dyeing of...

2000-01-07

2002-11-12

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, C008S411000, C008S414000, C008S415000, C008S416000

Reexamination Certificate

active

06478827

ABSTRACT:

The present invention relates to dyeing compositions containing monobenzene nitroanilines having at least one cationic charge delocalized over an unsaturated 5-membered polynitrogenous heterocycle, and comprising at least one cationic group chosen from certain types of aliphatic chains, and to the use of such compositions as direct dyes in dyeing applications for keratinous substances, in particular for human keratinous fibers and especially the hair.
It is known to dye keratinous fibers, and in particular the hair, with dyeing compositions comprising direct dyes, i.e., coloring molecules having an affinity for the fibers. The dyeing process which employs them is a so-called direct coloring process, wherein the direct dyes are allowed to stand on the fibers and are then rinsed.
The colorings which result therefrom are temporary or semi-permanent colorings, because the nature of the interactions which bind the direct dyes to the keratinous fiber and their desorption from the surface and/or from the core of the fiber are responsible for their weak dyeing power and their poor ability to withstand washing operations or perspiration.
Cationic nitroanilines have certainly already been described among known direct dyes but their cationic charge is localized on the nitrogen atom of an aliphatic chain. Such nitroanilines are disclosed, for example, in U.S. Pat. Nos. 5,135,543 and 5,256,823, the disclosures of which are incorporated by
However, in hair dyeing, there is a constant search for direct dyes which exhibit improved characteristics.
It is therefore after a great deal of research directed at this question that the inventors have now just discovered, entirely unexpectedly and surprisingly, that cationic monobenzene nitroanilines with at least one cationic charge delocalized over an unsaturated 5-membered polynitrogenous heterocycle and therefore comprising at least one Z cationic group, 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 suitable for use as direct dyes in direct dyeing and, in addition, that they make it possible to obtain dyeing compositions resulting in powerful and varied colorings exhibiting excellent properties of resistance to various attacks which hair may be subject to (light, rubbing, bad weather, shampoos or perspiration) which are significantly improved with respect to those of the colors achieved with known cationic nitroanilines of the prior art, the cationic charge of which is localized on the nitrogen atom of an aliphatic chain.
Finally, these nitroanilines exhibit a better solubility in the media conventionally used for the dyeing of keratinous fibers and prove to be easy to synthesize.
These discoveries form the basis of the present invention.
A subject of the present invention is thus the use, in direct dye compositions or for the manufacture of dyeing compositions for keratinous substances and in particular for human keratinous fibers, such as the hair, of cationic monobenzene nitroanilines of following formula (I) and their acid addition salts:
in which formula,
R
1
and R
2
, which can be identical or different, represent a hydrogen atom; a Z group defined below; a (C
1
-C
6
)alkyl radical; a monohydroxy(C
1
-C
6
)alkyl radical; a polyhydroxy(C
2
-C
6
)alkyl 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 thiocarbamyl(C
1
-C
6
)alkyl radical; a trifluoro(C
1
-C
6
)alkyl radical; a sulpho(C
1
-C
6
)alkyl 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; an aminosulphonyl(C
1
-C
6
)alkyl radical; an N—Z-aminosulphonyl(C
1
-C
6
)alkyl 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 (C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an amino(C
1
-C
6
)alkyl radical, the alkyl of which is unsubstituted or substituted by one or more hydroxyl radicals; or an amino(C
1
-C
6
)alkyl radical, the alkyl of which is unsubstituted or substituted by one or more hydroxyl radicals and the amine of which is substituted by one or two identical or different radicals 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 heteroatoms, or which are chosen from alkyl, monohydroxy(C
1
-C
6
)alkyl, polyhydroxy(C
2
-C
6
)alkyl, (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 or thiocarbamyl radicals, or from a Z group defined below;
R
3
and R
4
, which can be identical or different, represent a hydrogen atom; a halogen atom; a Z group 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; an N-(C
1
-C
6
)alkylaminosulphonyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl radical; an aminosulphonyl(C
1
-C
6
)alkyl radical; an N—Z-aminosulphonyl(C
1
-C
6
)alkyl 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 monohydroxy(C
1
-C
6
)alkyl radical; a polyhydroxy(C
2
-C
6
)alkyl radical; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; a trifluoro(C
1
-C
6
)alkyl radical; a cyano radical; an OR
5
or —SR
5
group defined below; or an amino(C
1
-C
6
)alkyl radical, the alkyl of which is unsubstituted or substituted by one or more hydroxyl radicals and the amine of which is unsubstituted or substituted by one or two identical or different radicals 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 heteroatoms, or which are chosen from (C
1
-C
6
)alkyl, monohydroxy(C
1
-C
6
)alkyl, polyhydroxy(C
2
-C
6
)alkyl, (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 or thiocarbamyl radicals, or from a Z group defined below;
R
5
denotes a hydrogen atom; a (C
1
-C
6
)alkyl radical; a monohydroxy(C
1
-C
6
)alkyl radical; a polyhydroxy(C
2
-C
6
)alkyl radical; a Z group; 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 trifluoro(C
1
-C
6
)alkyl radical; an aminosulphonyl(C
1
-C
6
)alkyl radical; an N—Z-aminosulphonyl(C
1
-C
6
)alkyl 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 (C
1
-C
6
)alkylsulphinyl(C
1

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