Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-11-29
2003-04-29
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000
Reexamination Certificate
active
06554872
ABSTRACT:
The present invention relates to cationic aminodianthraquinones containing at least one cationic group Z, with Z being chosen from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring, and aliphatic chains containing at least one quaternized unsaturated ring, their use as direct dyes in applications for dyeing keratinous materials, such as human keratinous fibers, for example hair, the dyeing compositions containing them, as well as the dyeing methods using them.
It is known to dye keratinous fibers, and in particular hair, with dyeing compositions containing direct dyes. Direct dyes are dye molecules having affinity for keratinous fibers. The dyeing method which uses them is a so-called direct dyeing method which comprises allowing the direct dyes to act on the fibers, and subsequently rinsing the fibers.
The colors resulting therefrom are temporary or semipermanent colors, because the nature of the interactions which links the direct dyes to the keratinous fiber, and their desorption from the surface and/or the core of the fiber are responsible for their weak dyeing power, and their poor resistance to washings and perspiration.
Cationic aminoanthraquinones have already been described among the known direct dyes. Such aminoanthraquinones are described in, for example, French Patent Nos. 1,422,016 (and its addition 87,902), 1,391,675, 1,401,163, 1,379,649, 1,430,089, 1,584,965, 2,050,397, 2,548,895, U.S. Pat. Nos. 5,169,403, 5,314,505, 5,486,629, 5,520,707, and European Patent Nos. 818,193 and 852,136, and contain only one anthraquinone nucleus.
However, in hair dyeing, direct dyes are being continually sought which exhibit increasingly better characteristics.
It is thus after major research studies carried out on this subject that the inventors have discovered a new class of cationic aminoanthraquinones, the cationic aminodianthraquinones containing at least one cationic group Z, with Z being chosen from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring, and aliphatic chains containing at least one quaternized unsaturated ring.
This new family of dyes can exhibit the very advantageous characteristic feature of greater solubility in the dyeing media. These new dyes can also generate colors, by direct dyeing, having an intensity and a resistance to various attacks to which the hair may be subjected: light, adverse weather conditions, shampoos, and perspiration, which is substantially improved compared with that of the colors produced with known prior art cationic aminoanthraquinones.
This discovery forms the basis of the present invention.
A subject of the present invention is thus the aminodianthraquinones of formula (I)
in which formula,
B is a linking chosen from a linear or branched alkyl chain preferably containing 1 to 14 carbon atoms, which may be interrupted by one or more groups Z, defined below, one or more heteroatoms such as oxygen, sulphur or nitrogen atoms, or a mixture of one or more groups Z and one or more heteroatoms; and which may be unsubstituted or substituted with one or more hydroxyl or C
1
-C
6
alkoxy radicals, and which may carry one or more ketone functions;
R
1
, R
2
, R
3
, R
4
, R′
1
, R′
2
, R′
3
and R′
4
, which may be identical or different, are chosen from one of the two valencies of a linking arm B; a hydrogen atom; a halogen atom; a group Z, 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 cyano radical; a nitro radical; a carboxyl radical; a carbamyl radical; a sulpho radical; a substituted or unsubstituted amino radical, having the same meanings as NHR
5
or NHR′
5
defined below, and which may be identical or different; a group OR
6
or SR
6
or OR′
6
or SR′
6
defined below; R
5
and R′
5
, which may be identical or different, are chosen from one of the two valencies of a linking arm B; a hydrogen atom; a group Z, 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, wherein the alkyl is unsubstituted or substituted with at least one hydroxyl radical; an amino(C
1
-C
6
alkyl) radical, wherein the alkyl is unsubstituted or substituted with at least one hydroxyl radical, and wherein the amine is substituted with at one or two radicals, identical or different, chosen from the 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, and thiocarbamyl radicals, or from the group Z, defined below, or which may form, together with the nitrogen atom to which they are attached, a 5- or 6-membered ring containing carbon or containing at least one heteroatom;
R
6
and R′
6
, which may be identical or different, are chosen from one of the two valencies of a linking arm B; 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 group Z, defined below; 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
-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 amino(C
1
-C
6
alkyl) radical, wherein the alkyl is unsubstituted or substituted with at least one hydroxyl radical; an amino(C
1
-C
6
alkyl) radical, wherein the alkyl is unsubstituted or substituted with at least one hydroxyl radical, and wherein the amine is substituted with one or two radicals, identical or different, chosen from the C
1
-C
6
alkyl, monohydroxy(C
1
-C
6
alkyl), polyhydroxy(C
2
-C
6
alkyl), (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, the groups Z, defined below, or which may form, together with the nitrogen atom to which they are attached, a 5- or 6-membered ring containing carbon or containing at least one heteroatom;
Z is chosen from the unsaturated cationic groups of the formulae (11) and (111), and the saturated cationic groups of the formula (IV):
in which:
D is a linking arm chosen from linear and branched alkyl chains, preferably containing from 1 to 14 carbon atoms, which may be interrupted by one or more heteroatoms such as oxygen, sulphur or nitrogen, and which may be substituted with at least one radical chosen from hydroxyl and C
1
-C
6
alkoxy, and which may carry at least one
Genet Alain
Lagrange Alain
Einsmann Margaret
Finnegan Henderson Farabow Garrett and Dunner, LLP
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