Granted Patent B2

US 7,393,366 · App. 11/341,050 · Granted Jul 1, 2008

Assignee: The Procter & Gamble Company

Abstract

Claims (29)

1. An agent for the nonoxidative coloring of keratin fibers, comprising at least one zwitterionic azo dye of the general formula (I);

wherein

R1 is an alkyl sulfonate radical of the formula (II);

R2 is hydrogen or a hydroxyl group;

m is 0 to (n−1);

p is 0 to (n−1) where m+p=(n−1);

n is an integer from 1 to 6;

X is oxygen, sulfur, N—R3 or C—R4;

Y is C—R5, nitrogen, N—R6, sulfur or oxygen;

Z is C—R7 or nitrogen; and

wherein the heterocycle of the formula (I) comprises at least two and at most three heteroatoms, where the heterocycle has at most one sulfur atom or oxygen atom; R3 and R6 may be identical or different and, independently of one another, are a saturated or unsaturated (C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkyl group substituted by a halogen atom, a hydroxy-(C 2 -C 12 )-alkyl group, an amino-(C 1 -C 12 )-alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group;

R4, R5 and R7 may be identical or different and, independently of one another, are hydrogen, a halogen atom, a saturated or unsaturated (C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkyl group substituted by a halogen atom (F, Cl, Br, I), a hydroxyl group, a hydroxy-(C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkoxy group, a cyano group, a nitro group, an amino group, a (C 1 -C 12 )-alkylamino group, a (C 1 -C 12 )-dialkylamino group, a carboxylic acid group, a C(O)O—(C 1 -C 12 )-alkyl group, a substituted or unsubstituted C(O)O-phenyl group, a substituted or unsubstituted phenyl group or a naphthyl group, or a substituted or unsubstituted heteroaryl group; or if Y and Z are C—R5 and C—R7, the radical groups R5 and R7, together with the remaining molecule, can form a heterocyclic or carbocyclic, saturated or unsaturated, substituted or unsubstituted ring system;

or if X and Y are C—R4 and C—R5, the radical groups R4 and R5, together with the remaining molecule, can form a heterocyclic or carbocyclic, saturated or unsaturated, substituted or unsubstituted ring system;

K is a radical group of the aniline or phenol series or a monocyclic or polycyclic heterocyclic radical group.

2. An agent for the simultaneous lightening and coloring of keratin fibers, comprising at least one oxidizing agent, and at least one oxidizing-agent-stable zwitterionic azo dye of the general formula (I) according to claim 1 .

3. An oxidative colorant for coloring fibers based on at least one oxidation dye precursor, comprising at least one oxidizing-agent-stable zwitterionic azo dye of the general formula (I) according to claim 1 .

4. An agent according to claim 1 , comprising at least one natural polymer customary for cosmetic agents, synthetic polymer or modified polymer of natural origin, and being in the form of a tinting setting composition or color setting composition.

5. An agent according to claim 2 , wherein said oxidizing agent is selected from the group consisting of hydrogen peroxide or its addition compounds onto urea, melamine, sodium borate and sodium carbonate.

6. An agent according to claim 3 , wherein said oxidizing agent is chosen from hydrogen peroxide or its addition compounds onto urea, melamine, sodium borate, sodium carbonate, and persulfates.

7. An agent according to claim 1 , wherein, in said formula (I), R2 is hydrogen and n is 2 or 3.

8. An agent according to claim 7 , wherein, in said formula (I), K is a radical group of the formula K1,

in which R8 and R9 may be identical or different and, independently of one another, are a saturated or unsaturated (C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkyl group substituted by a halogen atom, a hydroxy-(C 2 -C 12 )-alkyl group, an amino-(C 1 -C 12 )-alkyl group, a substituted or unsubstituted phenyl group or a benzyl group, or R8 and R9, together with the nitrogen atom, form a 5-membered to 6-membered ring system, which may comprise a further heteroatom; or R8 and/or R9 form with a carbon atom of the benzene ring an optionnally oxygen-containing or nitrogen containing five or six-membered heterocycle which may be substituted with one or several (C 1 -C 12 )-alkyl groups;

R10 and R11 may be identical or different and, independently of one another, are hydrogen, a halogen atom, a saturated or unsaturated (C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkyl group substituted by a halogen atom, a hydroxyl group, a hydroxy-(C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkoxy group, a cyano group, a nitro group, an amino group, a (C 1 -C 12 )-alkylamino group, a (C 1 -C 12 )-dialkylamino group, a carboxylic acid group, a C(O)O—(C 1 -C 12 )-alkyl group, a substituted or unsubstituted C(O)O-phenyl group.

9. An agent according to claim 1 , wherein the zwitterionic azo dye of said formula (I) is selected from the group consisting of 4-(2-{[4-(dimethylamino)phenyl]diazenyl)}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl)}-4-methyl-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethyl-amino)phenyl]diazenyl}-4-methyl-1,3-thiazol-3-ium-3-yl)-1-propane-sulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-5-methyl-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-5-methyl-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(dimethyl-amino)phenyl]diazenyl}-4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-butane-sulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-(5-bromo-2-{[4-(dimethylamino)-phenyl]-diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(5-bromo-2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propane-sulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-5-methoxy-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]-diazenyl}-5-methoxy-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-5-nitro-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-5-nitro-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-[(2-{4-[benzyl(methyl)amino]-phenyl}diazenyl)-1 ,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[(2-{4-[benzyl(methyl)amino]phenyl}diazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-(2-{[4-(1-pyrrolidinyl)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(1-pyrrolidinyl)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(4-morpholinyl)phenyl]-diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{4-(4-morpholinyl)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(4-methyl-1-piperazinyl)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(4-methyl-1-piperazinyl)-phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate, 4-[2-(2,3,6,7-tetrahydro-1H,5H-pyrido [3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 4-[2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[5-methyl-2-(2,3,6,7-tetrahydro-1H,5H-pyrido [3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 4-[5-methyl-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[4-methyl-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 4-[4-methyl-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[4,5-dimethyl-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 4-[4,5-dimethyl-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yldiazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-benzothiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-benzothiazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(dimethylamino)-phenyl]diazenyl }-6-methoxy-1,3-benzothiazol-3-ium-3-yl)-1-butane-sulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-6-methoxy-1,3-benzothiazol-3-ium-3-yl)-1-propanesulfonate, 4-[2-({4-[benzyl(ethyl)-amino]phenyl}diazenyl)-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]-phenyl}diazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl(ethyl)amino]phenyl}diazenyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]-phenyl}diazenyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl(ethyl)amino]-phenyl}diazenyl)-5-methyl-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]phenyl}diazenyl)-5-methyl-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl(ethyl)-amino]phenyl}diazenyl)-4,5-dimethyl-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]phenyl}diazenyl)-4,5-dimethyl-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl-(ethyl)amino]-2-methylphenyl }diazenyl)-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]-2-methylphenyl}diazenyl)-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl(ethyl)amino]-2-methylphenyl}diazenyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-butane-sulfonate, 3-[2-({4-[benzyl(ethyl)amino]-2-methylphenyl}diazenyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl(ethyl)-amino]-2-methylphenyl}diazenyl)-5-methyl-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]-2-methylphenyl}diazenyl)-5-methyl-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-[2-({4-[benzyl-(ethyl)amino]-2-methylphenyl}diazenyl)-4,5-dimethyl-1,3-thiazol-3-ium-3-yl]-1-butanesulfonate, 3-[2-({4-[benzyl(ethyl)amino]-2-methylphenyl}-diazenyl)-4,5-dimethyl-1,3-thiazol-3-ium-3-yl]-1-propanesulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1-methyl-1H-imidazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1-methyl-1H-imidazol-3-ium-3-yl)-1-propanesulfonate, 4-{2-[(4-aminophenyl)-diazenyl]-1-methyl-1H-imidazol-3-ium-3-yl}-1-butanesulfonate, 3-{2-[(4-aminophenyl)diazenyl]-1-methyl-1H-imidazol-3-ium-3-yl}-1-propanesulfonate, 4-(1-methyl-2-{[4-(methylamino)phenyl]diazenyl}-1H-imidazol-3-ium-3-yl)-1-butanesulfonate, 3-(1-methyl-2-{[4-(methylamino)-phenyl]diazenyl}-1H-imidazol-3-ium-3-yl)-1-propanesulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,4,5-trimethyl-1H-imidazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,4,5-trimethyl-1H-imidazol-3-ium-3-yl)-1-propanesulfonate, 4-(5-{[4-(dimethylamino)phenyl]diazenyl}-4-methyl-4H-1,2,4-triazol-1-ium-1-yl)-1-butanesulfonate, 3-(5-{[4-(dimethylamino)phenyl]diazenyl}-4-methyl-4H-1,2,4-triazol-1-ium-1-yl)-1-propanesulfonate, 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3,4-thiadiazol-3-ium-3-yl)-1-butanesulfonate, 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3,4-thiadiazol-3-ium-3-yl)-1-propanesulfonate, 4-(5-{[4-(dimethylamino)-phenyl]diazenyl}-1,2,4-thiadiazol-4-ium-4-yl)-1-butanesulfonate, 3-(5-{[4-(dimethylamino)phenyl]diazenyl}-1,2,4-thiadiazol-4-ium-4-yl)-1-propanesulfonate, 3-(3-{[4-(dimethylamino)phenyl]diazenyl}-1-methyl-1H-pyrazol-2-ium-2-yl)-1-propanesulfonate, 4-(3-{[4-(dimethylamino)phenyl]-diazenyl}-1-methyl-1H-pyrazol-2-ium-2-yl)-1-butanesulfonate, 3-(3-{[4-(dimethylamino)phenyl]diazenyl}isoxazol-2-ium-2-yl)-1-propanesulfonate, 4-(3-{[4-(dimethylamino)phenyl]diazenyl}isoxazol-2-ium-2-yl)-1-butanesulfonate, 4-{2-[(1-methyl-2-phenyl-1H-indol-3-yl)diazenyl]-1,3-thiazol-3-ium-3-yl}-1-butanesulfonate, 3-{2-[(1-methyl-2-phenyl-1H-indol-3-yl)diazenyl]-1,3-thiazol-3-ium-3-yl}-1-propanesulfonate, 4-{2-(1,2-dimethyl-1H-indol-3-yl)diazenyl]-1,3-thiazol-3-ium-3-yl}-1-butanesulfonate and 3-{2-(1,2-dimethyl-1H-indol-3-yl)diazenyl]-1,3-thiazol-3-ium-3-yl}-1-propanesulfonate.

10. An agent according to claim 1 , wherein the zwitterionic azo dye of said formula (I) is present in an amount of from 0.01 to 10% by weight.

11. An agent according to claim 1 , wherein the agent additionally comprises at least one further direct dye selected from the group consisting of nitro dyes, azo dyes, anthraquinone dyes, triphenylmethane dyes and basic or acidic dyes.

12. An agent according to claim 11 , wherein said additional direct dye is present in a total amount of from 0.01 to 15% by weight.

13. An agent according to claim 1 , wherein the agent has a pH of from 2 to 11.

14. An agent according to claim 1 , wherein the agent is a hair colorant.

Assignments (9)

Priority Claims (1)

Continuity (1)