Cationic aminoanthraquinones, their use for dyeing...

Details Cationic aminoanthraquinones, their use for dyeing... Cationic aminoanthraquinones, their use for dyeing...

2002-07-09

2003-11-11

Shah, Mukund J. (Department: 1624)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S426000, C008S428000, C008S643000, C008S654000, C008S655000, C552S255000, C548S335100, C546S269700, C546S271700, C544S106000, C544S111000, C544S180000, C544S359000

Reexamination Certificate

active

06645259

ABSTRACT:

The present invention relates to aminoanthraquinones containing at least one cationic group chosen from aliphatic chains containing at least one cationic charge delocalized on a 5-membered unsaturated polynitrogen-containing ring, their use as a direct dye in applications for dyeing keratinous materials, such as human keratinous fibers, for example hair, and dyeing compositions containing them.
It is known to dye keratinous fibers, and in particular hair, with dyeing compositions containing direct dyes. Direct dyes are dye molecules having an affinity for keratinous fibers. The dyeing method that 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 link 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 whose charge is localized on the nitrogen atom have already been described among the known direct dyes. Such aminoanthraquinones are described, for example, in French Patent No. 1,422,016 and its addition No. 87,902, No. 1,391,675, No. 1,401,163, No. 1,379,649, No. 1,430,089, No. 1,584,965, No. 2,050,397, and No. 2,548,895, U.S. Pat. Nos. 5,169,403, 5,314,505, 5,486,629, and 5,520,707, and European Patent Nos. 818,193 and 852,136.
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 new cationic aminoanthraquinones in which at least one cationic charge is delocalized on a five-membered unsaturated polynitrogen-containing heterocycle and contain at least one cationic group Z, 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 aminoanthraquinones of the formula (I):
in which formula:
R
1
, R
2
, R
3
and R
4
, which may be identical or different, are chosen from 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; an unsubstituted amino radical; a substituted amino radical of formula NHR′
5
, wherein R′
5
has the same meaning as R
5
defined below, and wherein R′
5
may be identical to or different from R
5
; and an OR
6
and an SR
6
group, wherein R
6
is defined below;
R
5
is chosen from 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 portion is unsubstituted or substituted with at least one hydroxyl radical; an amino(C
1
-C
6
alkyl) radical, wherein the alkyl is substituted with at least one hydroxyl radical and wherein the amine is substituted with one or two radicals, wherein each amine radical is identical or different, and is 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, 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, thiocarbamyl, and the group Z defined below, or 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
is chosen from 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 substituted with at least one hydroxyl radical and wherein the amine is substituted with one or two radicals, which radicals are identical or different, and 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, 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, and 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;
Z is chosen from the unsaturated cationic groups of formulae (II) and (III), and the saturated cationic groups of formula (IV):
in which:
D is a linking arm chosen from linear and branched alkyl chains, which may be interrupted by at least one heteroatom 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 ketone function; in one embodiment of the invention, the alkyl chains contain from 1 to 14 carbon atoms;
the members E, G, J, L and M, which are identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms;
n is an integer ranging from 0 to 4;
m is an integer ranging from 0 to 5;
the radicals R, which are identical or different, are chosen from a group Z′, which has the same definition as the group Z, and which definition is identical to or different from the group Z; a halogen atom; a hydroxyl 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 nitro radical; a cyano radical; a cyano(C
1
-C
6
alkyl) radical; a C
1
-C
6
alkoxy radical; a tri(C
1
-C
6
)al

Affiliated with

Also associated with

Rating

Cationic aminoanthraquinones, their use 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 Cationic aminoanthraquinones, their use for dyeing..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cationic aminoanthraquinones, their use for dyeing... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3155768