Use of cationic fused polycyclic compounds for dyeing...

Details Use of cationic fused polycyclic compounds for dyeing... Use of cationic fused polycyclic compounds for dyeing...

2000-02-09

2002-05-21

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S407000, C008S453000, C008S461000

Reexamination Certificate

active

06391062

ABSTRACT:

This application claims priority to French patent application Nos. 99-01504, filed Feb. 9, 1999, and 99-04185, filed Apr. 2, 1999, the disclosures of both of which are incorporated by reference herein. The invention relates to compositions containing fused polycyclic compounds 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. In particular, the invention relates to the use of such compounds as direct dyes in compositions for dyeing keratin substances and, preferably, compositions for dyeing human keratin fibers, especially the hair. The invention is also drawn to the use of such compounds in cosmetic compositions for making up the skin, the nails and the lips. Finally, the invention is drawn to dye compositions or make-up compositions containing the fused polycyclic compounds and to the corresponding direct dyeing process.
In the field of hair dyeing, direct dyes are sought, ie., dyes which, without supplying an oxidizing agent, 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 give rise to reproducible dyeing results with rich and varied shades allowing a wide range of colors to be obtained to be able to satisfy formulators, these dyeing results also needing to be intense and able to withstand washing, rubbing, permanent-waving, light and perspiration.
The inventors have now discovered, entirely surprisingly and unexpectedly, that fused polycyclic compounds 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 suitable for use as direct dyes for direct dyeing, and that they also make it possible to obtain dye compositions leading to intense and varied colorations that have excellent properties of resistance with respect to the various treatments to which keratin fibers may be subjected, and, in particular, with respect to light, washing, permanent-waving and perspiration. 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.
Additional features and advantages of the invention are set forth in the description that follows, and, in part, will be apparent from the description or may be learned from practice of the invention. The advantages of the invention will be realized and attained by the compositions and processes particularly pointed out in the written description and claims. Both the foregoing general description and the following detailed description of the invention are exemplary and explanatory only and are not restrictive of the claimed 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 fused polycyclic compounds of formula (I) below, and the acid addition salts thereof:
in which:
R
1
represents a hydrogen atom; a group Z defined below; 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; an amino-sulphonyl(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(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;
R
2
and R
3
, which may be identical or different, represent 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
)alkylcarboxy 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 hydroxyl radical; a nitro 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 amino radical; an N—(C
1
-C
6
)alkylamino radical; an N,N-di(C
1
-C
6
)alkylamino radical (the two alkyl substituents possibly forming a 5- or 6-membered ring); an N-hydroxy (C
1
-C
6
)alkylamino radical; an N,N-bis(hydroxy (C
1
-C
6
)alkyl)amino radical; an N-polyhydroxy(C
2
-C
6
)alkylamino radical; an N,N-bis(polyhydroxy(C
2
-C
6
)alkyl)amino radical; an amino (C
1
-C
6
)alkylamino radical in which the terminal amino group is unsubstituted or substituted with one or two C
1
-C
6
alkyl radicals, the alkyl radicals possibly forming a saturated or unsaturated 5- or 6-membered ring; an amino group protected with a (C
1
-C
6
)alkylcarbonyl, trifluoro(C
1
-C
6
)alkylcarbonyl, amino(C
1
-C
6
)alkylcarbonyl, N—Z-amino(C
1
-C
6
)alkylcarbonyl, N—(C
1
-C
6
)alkylamino (C
1
-C
6
)alkylcarbonyl, N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl or formyl radical; a group OR
4
or SR
4
;
R
4
denotes 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 and C
1
-C
6
alkylsulphonyl radicals.
The substituents R
2
and R
3
can together form an unsaturated ring of structure (II) below:
Z is chosen from the unsa

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