Agents for dyeing keratin fibres, containing at least one dimeric, dicationic azo dye with special substitution pattern

Patent metadata

Field	Value
Publication number	US-10406089-B2
Application number	US-201515528529-A
Country	US
Kind code	B2
Filing date	Oct 14, 2015
Priority date	Nov 25, 2014
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

The disclosure relates to agents for dyeing keratin fibers, in particular human hair, containing, in a cosmetic carrier (a) at least one direct dye of formula (I), wherein Het1, Het2 represent cationic heterocycles; R1, R3 respectively represent a substitute which is not hydrogen, and Q represents a grouping of formula (VIII), (IX), or (X).

First claim

The invention claimed is:

1. An agent for changing the colour of keratinic fibers, the agent comprising, in a cosmetic support, (a) at least one direct dye with formula (I),

wherein
one of Het1 and Het2 represents one of the structures (II), (III), (IV), (V), (VI) or (VII), and
the other of Het1 and Het2 represents one of the structures (III), (V), (VI) or (VII),

R1, R3 independently of each other represent a C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group,
R2, R4 each represent a hydrogen atom,
R5, R6 independently of each other represent a hydrogen atom, a C 1 -C 6 alkyl group or a C 2 -C 6 alkenyl group,

Q represents a group with formula (VIII),
* —(CH 2 )n-*  (VIII)

n represents a whole number from 3 to 6,
R7, R10 each independently of each other represent a C 1 -C 6 alkyl group or a C 2 -C 6 alkenyl group,
R8, R9 each independently of each other represent a hydrogen atom, a C 1 -C 6 alkyl group, a halogen atom from the group chlorine, bromine, fluorine or iodine, a C 1 -C 6 alkoxy group or a nitro group, and
X represents a physiologically acceptable anion selected from the group consisting of chloride, bromide, iodide, methyl sulphate, methyl sulphonate, p-toluenesulphonate, acetate, hydrogen sulphate, ½ sulphate or ½ tetrachlorozincate.

2. The agent as claimed in claim 1 , wherein the agent comprises (a) at least one direct dye with general formula (I), in which
Het1, Het2 independently of each other respectively represent one of the structures (II), (III) or (IV):

3. The agent as claimed in claim 1 , wherein the agent comprises (a) at least one direct dye with general formula (I), in which
R5, R6 independently of each other represent hydrogen or a C 1 -C 6 alkyl group.

4. The agent as claimed in claim 1 , wherein the agent comprises (a) at least one direct dye with general formula (I), in which
R7, R10 each independently of each other represent a methyl group or an ethyl group,
R8, R9 represents a hydrogen atom.

5. The agent as claimed in claim 1 , wherein the agent comprises at least one direct dye with general formula (I) which is selected from:
3-methyl-2-[2-(3-methyl-4-{[3-({2-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)propyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-[2-(2-methyl-4-{[3-({3-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)propyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-[2-(3-methyl-4-{[4-({2-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)butyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-[2-(2-methyl-4-{[4-({3-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)butyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-[2-(3-methyl-4-{[5-({2-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)pentyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-[2-(2-methyl-4-{[5-({3-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)pentyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-(2-{3-methyl-4-[methyl({3-[methyl({2-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)propyl]amino}phenyl)diazen-1-yl]-1,3-thiazol-3-ium salts,
3-methyl-2-(2-{3-methyl-4-[ethyl({3-[ethyl({2-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl })amino]propyl })amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
3-methyl-2-(2-{2-methyl-4-[methyl({3[methyl({3-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl })amino]propyl })amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
3-methyl-2-(2-{2-methyl-4-[ethyl({3-[ethyl({3-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl })amino]propyl })amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
3-methyl-2-(2-{3-methyl-4-[methyl({4-[methyl({2-methyl-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl)}amino]butyl })amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
3-methyl-2-(2-{2-methyl-4-[methyl({4-[methyl({3-methyl-4-[2-(3-methyl-1,3 -thiazol-3-ium-2-yl)diazen-1-yl]phenyl})amino]butyl})amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
3-methyl-2-(2-{3-methyl-4-[methyl({5-[methyl({2-methyl-4-[2-(3-methyl-1,3 -thiazol-3-ium-2-yl)diazen-1-yl]phenyl})amino]pentyl})amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
3-methyl-2-(2-{2-methyl-4-[methyl({5-[methyl({3-methyl-4-[2-(3-methyl-1,3 -thiazol-3-ium-2-yl)diazen-1-yl]phenyl})amino]pentyl})amino]phenyl}diazen-1-yl)-1,3 -thiazol-3-ium salts,
2-[2-(3-methoxy-4-{[3-({2-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)propyl]amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(2-methoxy-4-{[3-({3-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)propyl]amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(3-methoxy-4-{[4-({2-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)butyl]amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(2-methoxy-4-{[4-({3-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)butyl]amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(3-methoxy-4-{[5-({2-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)pentyl]amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(2-methoxy-4-{[5-({3-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}amino)pentyl]amino }phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(3-methoxy-4-{[3-({2-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl}(methyl)amino)propyl](methyl)amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(2-methoxy-4-{[3-({3-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl }(methyl)amino)propyl](methyl)amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(3-methoxy-4-{[4-({2-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl }(methyl)amino)butyl]methyl)amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(2-methoxy-4-{[4-({3-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl }(methyl)amino)butyl]methyl)amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(3-methoxy-4-{[5-({2-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl }(methyl)amino)pentyl]methyl)amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
2-[2-(2-methoxy-4-{[5-({3-methoxy-4-[2-(3-methyl-1,3-thiazol-3-ium-2-yl)diazen-1-yl]phenyl }(methyl)amino)pentyl]methyl)amino}phenyl)diazen-1-yl]-3-methyl-1,3-thiazol-3-ium salts,
5-[2-(4-{[3-({4-[2-(1,4-dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]-2-methylphenyl }amino)propyl]amino}-3-methylphenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium salts,
5-[2-(4-{[3-({4-[2-(1,4-dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]-3-methylphenyl }amino)propyl]amino}-2-methylphenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium salts,
5-[2-(4-{[4-({4-[2-(1,4-dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]-2-methylphenyl }amino)butyl]amino}-3-methylphenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium salts,
5-[2-(4-{[4-({4-[2-(1,4-dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]-3-methylphenyl }amino)butyl]amino}-2-methylphenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium salts,
5-[2-(4-{[5-({4-[2-(1,4-dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]-2-methylphenyl }amino)pentyl]amino}-3-methylphenyl)dia

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Gebert-Schwarzwaelder Antje
• Giesa Helmut
• Kroos Astrid

Classifications

• C09B44/20

  Thiazoles or hydrogenated thiazoles · CPC title

• C09B44/18

  having three nitrogen atoms as the only ring hetero atoms · CPC title

• C09B44/16

  1,3-Diazoles or hydrogenated 1,3-diazoles {; (Benz)imidazolium} · CPC title

• C09B44/14

  1,2-Diazoles or hydrogenated 1,2-diazoles {; Pyrazolium; Indazolium} · CPC title

• A61K2800/4322

  in preparations for temporarily coloring the hair further containing an oxidizing agent · CPC title