Cationic monobenzene nitrophenylenediamines, their use in...

Details Cationic monobenzene nitrophenylenediamines, their use in... Cationic monobenzene nitrophenylenediamines, their use in...

2000-01-07

2002-10-15

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S409000, C008S410000, C546S184000, C548S400000

Reexamination Certificate

active

06464731

ABSTRACT:

The present invention relates to monobenzene nitrophenylenediamines having at least one cationic charge delocalized on an unsaturated 5-membered polynitrogenous heterocycle, and comprising at least one cationic group which is chosen from certain aliphatic chains, to their use as direct dyes in dyeing applications for keratinous substances, in particular for human keratinous fibers and especially the hair, to the dyeing compositions comprising them, and to the dyeing processes employing such compositions.
It is known to dye keratinous fibers, and in particular the hair, with dyeing compositions comprising direct dyes, that is to say coloring molecules having an affinity for the fibers. The dyeing process which employs them is a so-called direct dyeing 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 nitrophenylenediamines have certainly already been described among known direct dyes but their cationic charge is localized on the nitrogen atom of an aliphatic chain or of a mononitrogenous heterocycle. Such nitrophenylenediamines are disclosed, for example, in British Patent No. 1,164,824 and U.S. Pat. No. 4,018,556, the disclosures of which are incorporated by reference herein.
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, novel cationic monobenzene nitrophenylenediamines 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.
This novel family of dyes exhibits the highly advantageous distinguishing feature of a greater solubility in dyeing media, and these novel dyes produce colors, by direct coloring, which possess a power and a resistance (to the 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 produced with known cationic nitrophenylenediamines of the prior art, the cationic charge of which is localized on the nitrogen atom of an aliphatic chain or of a mononitrogenous heterocycle.
This discovery forms the basis of the present invention.
The subject of the present invention is thus the cationic monobenzene nitrophenylenediamines of following formula (I):
in which formula,
R
1
, R
2
, R
3
and R
4
, 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
5
and R
6
, 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
8
)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
7
or —SR
7
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
7
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-da(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; an a

Affiliated with

Also associated with

Rating

Cationic monobenzene nitrophenylenediamines, their use in... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cationic monobenzene nitrophenylenediamines, their use in..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cationic monobenzene nitrophenylenediamines, their use in... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2995076