Use of cationic dibenzenic nitro compounds for dyeing...

Details Use of cationic dibenzenic nitro compounds for dyeing... Use of cationic dibenzenic nitro compounds for dyeing...

2000-01-07

2002-10-22

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S411000, C008S415000

Reexamination Certificate

active

06468316

ABSTRACT:

The present invention relates to dyeing compositions containing dibenzenic nitro 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 such compositions.
In the field of hair dyeing, direct dyes are sought, i.e., dyes which, without supplying any oxidizing agent other than ambient air, are capable by themselves of temporarily modifying the natural shade of the hair. In this application, the dyes must satisfy a certain number of criteria, and in particular they must generate reproducible dyeing results with rich and varied shades, thus making it possible to obtain a wide range of colors capable of satisfying the formulator, it also being necessary for these dyeing results to be intense and fast with respect to washing, rubbing, light and perspiration.
The inventors have now just discovered, entirely surprisingly and unexpectedly, that dibenzenic nitro 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 the keratin fibers may be subjected. Finally, these compounds have 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 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 dibenzenic nitro compounds of formula (I) below, and the acid-addition salts thereof:
in which:
B is a linker arm which represents a linear or branched alkyl chain preferably comprising from 1 to 14 carbon atoms, which can be interrupted with one or more groups Z and/or with one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or C
1
-C
6
alkoxy radicals, and which can bear one or more ketone functions;
R
1
, R
2
, R
3
, R′
1
, R′
2
and R′
3
, which may be identical or different, represent one of the two valencies of a linker arm B; a hydrogen atom; a halogen atom; a group Z; 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; 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 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; an unsubstituted or substituted amino radical, in which the substituents on the amine, which may be identical or different, have the same meanings as the variables R
4
, R
5
, R′
4
and R′
5
described below; an amino(C
1
-C
6
)alkyl 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 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; or a group OR
6
or —SR
6
; R
6
denotes one of the two valencies of a linker arm B; 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-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 (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; a C
1
-C
6
aminoalkyl radical 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, 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 and C
1
-C
6
alkylsulphonyl radicals, or with a group Z;
R
4
, R
5
, R′
4
and R′
5
, which may be identical or different, represent one of the two valencies of a linker arm B; a hydrogen atom; a group Z; 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 thiocarbamyl(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
)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; a C
1
-C
6
aminoalkyl radical; 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 chosen from alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, carbamyl, N—(C
1
-C
6
)alkyl-carbamyl 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;
Z is chosen from the unsaturated cationic groups of formulae (II) and (III) b

Affiliated with

Also associated with

Rating

Use of cationic dibenzenic nitro compounds for dyeing... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Use of cationic dibenzenic nitro compounds for dyeing..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Use of cationic dibenzenic nitro compounds for dyeing... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3000271