# US 7,410,507 B2 · Use of cationic azacyanine dyes for coloring keratin fibers

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- Number: US 7,410,507 B2
- Document ID: US7410507B2
- Status: Granted
- Kind: B2
- Application number: 11/339,351
- Filed: 2006-01-25
- Published: 2007-02-01
- Granted: 2008-08-12
- Earliest claimed: 2005-01-25
- Assignees: The Procter & Gamble Company
- Inventors: Manuela Javet; Catherine Müller; Anita Roulin; Cécile Pasquier
- Web page: https://patentgrep.com/patent/US7410507B2

## CPC

- A61K 8/4926: {having six membered rings}
- A61K 8/4913: {having five membered rings, e.g. pyrrolidone carboxylic acid}
- A61K 8/494: {with more than one nitrogen as the only hetero atom}
- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61Q 5/10: Preparations for permanently dyeing the hair
- C09B 55/009: {Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)}
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

The present invention relates to the use of cationic azacyanine dyes of the formula (Ia) or (Ib) for coloring keratin fibers, and to a method of coloring hair with various degrees of damage.

## Claims

### Claim 1

An agent for coloring keratin fibers comprising cationic azacyanine dyes of the general formula (Ia) or (Ib),
where A, B and Z is the group required to form an aromatic carbocyclic or heterocyclic 5- or 6-membered ring to which, with or without structural incorporation of R1 or R2, further carbocyclic or heterocyclic 5- or 6-membered rings can be fused, and the tertiary or quaternary nitrogen can be located either in the ring directly following the aza bridge, or else in a fused ring; furthermore, the tertiary or quaternary nitrogen in the molecular moiety Z corresponding to the general formula (Ib) may also be extracyclic;
R1 and R2, independently of one another, may be identical or different and are a substituted or unsubstituted, saturated or unsaturated (C1-C10)-alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted benzyl group, or act as a member of a fused carbocyclic or heterocyclic 5- or 6-membered ring; and An− is an anion; wherein the azacyanine dye of the formula (Ia) or (Ib) is chosen from 3-{[5-benzylamino)-1-isopropyl-1H-pyrazol-4-yl]imino}-1-methyl-2-phenyl-3H-indolium hydrogensulfate, 1-methyl-3-[(1-methyl-2-phenyl-1H-indol-3-yl)imino]-2-phenyl-3H-indolium perchlorate, 1-methyl-3-[(1-methyl-2-phenyl-3-indolizinyl)imino]-2-phenyl-3H-indolizinium chloride, 3-{[5-(benzylamino)-1-isopropyl-1H-pyrazol-4-yl]imino}-1-methyl-2-phenyl-3H-indolium hydrogensulfate, 1-methyl-3-[(1-methyl-2-phenyl-3-indolizinyl)imino]-2-phenyl-3H-indolizinium perchlorate, 1-methyl-3-[(3-methyl-2-phenyl-1-indolizinyl)imino]-2-phenyl-3H-indolizinium perchlorate, 2-{[3-(4-methoxy-phenyl)-1-indolizinyl]imino}-1,3-dimethyl-2H-indolizinium acetate,
2-[(1,3-dimethyl-2-indolizinyl)imino]-1,3-dimethyl-2H-indolizinium chloride, 1,2-dimethyl-3-[(2-phenyl-3-indolizinyl)imino]-3H-indolium bromide,
2-[(1,3-dimethyl-1H-indol-2-yl)imino]-1,3-dimethyl-2H-indolizinium chloride, 1,2-dimethyl-3-[(1-methyl-1H-indazol-3-yl)imino]-3H-indolium bromide,
1,2-dimethyl-3-[(2-methyl-2H-indazol-3-yl)imino]-3H-indolium hydrogensulfate, 1-methyl-3-[(2-methyl-2H-indazol-3-yl)imino]-3H-indazol-1-ium hydrogensulfate, 1-methyl-3-[(1-methyl-1H-indazol-3-yl)imino]-3H-indazol-1-ium hydrogensulfate, 1-[(1,2-dimethyl-1H-indol-3-yl)imino]-2,3-dimethyl-1H-isoindolium hydrogensulfate, 3-{[5-(dimethylamino)-1-methyl-1H-pyrazol-4-yl]imino}-1,2-dimethyl-3H-indolium bromide, 1-methyl-2-[(1-methyl-1H-indol-2-yl)imino]-2H-indolium hydrogensulfate, 2-[(5-methoxy-1-methyl-1H-benzimidazol-2-yl)imino]-1-methyl-2H-benzimidazol-1-ium chloride, 2-[(1,3-dimethyl-1H-indol-2-yl)imino]-1-methyl-2H-benzimidazol-1-ium chloride, 2-[(1,2-dimethyl-3-indolizinyl)imino]-1-methyl-2H-benzimidazol-1-ium bromide, 2-[(1,3-dimethyl-2-indolizinyl)imino]-1-methyl-2H-benzimidazol-1-ium chloride, 2-{[3-(4-bromophenyl)-1-indolizinyl]imino}-1-methyl-2H-benzimidazol-1-ium bromide, (2Z)-2-[(2-ethyl-3-methyl-2H-isoindol-1-yl)imino]-1-(4-fluorobenzyl)-2H-benzimidazol-1-ium bromide, 2-{[5-(dimethylamino)-1-methyl-1H-pyrazol-4-yl]imino}-1-methyl-2H-benzimidazol-1-ium bromide, 5-(dimethylamino)-4-{[5-(dimethylamino)-1-methyl-1H-pyrazol-4-yl]imino}-1-methyl-4H-pyrazol-1-ium bromide, 5-anilino-4-[(5-anilino-1-isopropyl-1H-pyrazol-4-yl)imino]-1-isopropyl-4H-pyrazol-1-ium hydrogensulfate, 2,4-dimethyl-3-[(1-methyl-2-phenyl-3-indolizinyl)imino]-3H-pyrrolo[3,2-b]pyridin-4-ium chloride,
3-[(1,3-dimethyl-1H-indazol-5-yl)imino]-1-methyl-2-phenyl-3H-indolizinium chloride, 1,4-dimethyl-3-[(3-methyl-2-phenyl-1-indolizinyl)imino]-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-4-ium bromide, 2-methoxy-4-methyl-3-[(1-methyl-2-phenyl-3-indolizinyl)imino]-3H-pyrrolo[3,2-b]pyridin-4-ium hydrogensulfate, 3-{[4-(dimethylamino)phenyl]imino}-1,2-dimethyl-3H-indolium bromide, 3-[(1,6-dimethyl-2-oxo-2,6-dihydro-1H-pyrrolo[2,3-c]pyridin-3-yl)imino]-1,4-dimethyl-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-4-ium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-1-methyl-2-phenyl-3H-indolizinium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-2-phenyl-3H-indolizinium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-1,2-diphenyl-3H-indolizinium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-2-ethyl-1-phenyl-3H-indolizinium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-2-ethyl-1-methyl-3H-indolizinium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-2-(1,1-dimethylethyl)-1-phenyl-3H-indolizinium bromide, 3-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-2-(1,1-dimethylethyl)-1-methyl-3H-indolizinium bromide, 3-{[5-(benzylamino)-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-1-methyl-2-phenyl-3H-indolizinium bromide, 3-{[5-hydroxy-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-1-methyl-2-phenyl-3H-indolizinium bromide, 3-{[5-(benzyloxy)-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]imino}-1-methyl-2-phenyl-3H-indolizinium bromide, 1-methyl-3-[(1-methyl-2-phenyl-1H-indol-3-yl)imino]-2-phenyl-3H-indolizinium bromide and 1-methyl-2-phenyl-3-[(2-phenyl-3-indolizinyl)imino]-3H-indolium bromide.

### Claim 2 (depends on 1)

An agent according to claim 1, wherein the azacyanine dye of said formula (Ia) or (Ib) is contained in a total amount of from 0.01 to 15 percent by weight.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

A method of coloring hair with varying degrees of damage where the color carrier mass comprising the azacyanine dye of the formula (Ia) or (Ib) according to claim 1 without oxidizing agent—pure or mixed with an acidic, neutral or basic aqueous diluent—is applied to the predamaged sections of hair while the color carrier mass mixed with the oxidizing agent is applied to the sections of hair with little or no predamage.