Agents for dyeing keratin fibers, containing at least one dimeric, dicationic azo dye and at least one anionic and/or cationic surfactant

Patent metadata

Field	Value
Publication number	US-10413498-B2
Application number	US-201515528530-A
Country	US
Kind code	B2
Filing date	Oct 14, 2015
Priority date	Nov 25, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

The present 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 Y1, Y2 independently represent a nitrogen atom or a group C—R9, and Q represents a special linker group of formula (II), (III), (IV) or (V), (b) at least one anionic surfactant and/or at least one cationic surfactant.

First claim

The invention claimed is:

1. An agent for dyeing keratinous fibers, the agent comprising, in a cosmetic carrier,
(a) at least one direct dye of formula (I),

wherein
R1, R2, R3, R4 represent, independently of one another, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a hydroxy C 2 -C 6 alkyl group;
R5, R6 represent, independently of one another, a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a hydroxy C 2 -C 6 alkyl group, or a cyano C 1 -C 6 alkyl group;
R7, R8 represent, independently of one another, a hydrogen atom, a C 1 -C 6 alkyl group, a halogen atom from the group consisting of chlorine, bromine, fluorine, and/or iodine, or a C 1 -C 6 alkoxy group; wherein at least one of R5, R6, R7, and R8 does not represent a hydrogen atom;
X1, X2 represent, independently of one another, a physiologically acceptable anion, chloride, bromide, iodide, methyl sulfate, methyl sulfonate, p-toluenesulfonate, acetate, hydrogen sulfate, ½ sulfate, or ½ tetrachlorozincate;
Q represents a group of formula (II);
*—(CH 2 ) n -*  (II)

n represents an integer from 3 to 6; and
(b) at least one anionic surfactant and/or at least one cationic surfactant.

2. The agent according to claim 1 , wherein the agent comprises (a) at least one direct dye of general formula (I), in which
R1, R2, R3, R4 represent, independently of one another, a methyl group or an ethyl group, and
R5, R6 represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group.

3. The agent according to claim 1 , wherein the agent comprises (a) at least one direct dye of general formula (I), in which
R7, R8 each represent a hydrogen atom.

4. The agent according to claim 1 , wherein the agent comprises (a) at least one direct dye of general formula (I) which is selected from:
salts of 5-[2-(4-{[3-({4[2-(1,4-dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}amino)propyl]amino}phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}amino)butyl)amino)phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[5-({4-[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}amino)pentyl]amino}phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[3-({4[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(methyl)amino)propyl](methyl)amino}phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(methyl)amino)butyl)(methyl)amino]phenyl}diazen-1-yl)-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[5-({4[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(methyl)amino)pentyl](methyl)amino}phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(ethyl)amino)propyl](ethyl)amino}phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(ethyl)amino)butyl](ethyl)amino}phenyl)diazen-1-yl]-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[5-({4[2-(1,4-Dimethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(ethyl)amino)pentyl](ethyl)amino}phenyl}diazen-1-yl)-1,4-dimethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[3-({442-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl}phenyl)-amino]propyl}amino}(phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl]-amino)butyl]amino}phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[5-({4[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}amino)pentyl]amino}phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[3-({4[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(methyl)amino)propyl](methyl)amino}phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(methyl)amino)butyl)(methyl)amino]phenyl}diazen-1-yl)-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[5-({4-[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(methyl)amino)pentyl](methyl)amino}phenyl)diazen-1-yl)-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[3-({4[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(ethyl)amino)propyl](ethyl)amino}phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[4-({4-}2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl)phenyl}-(ethyl)amino]butyl}(ethyl]amino]phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium,
salts of 5-[2-(4-{[5-({4-[2-(1,4-Diethyl-1H-1,2,4-triazol-4-ium-5-yl)diazen-1-yl]phenyl}-(ethyl)amino)pentyl](ethyl)amino}phenyl)diazen-1-yl]-1,4-diethyl-1H-1,2,4-triazol-4-ium.

5. The agent according to claim 1 , wherein the agent comprises, relative to the total weight of the agent, one or more direct dyes (a) of formula (I) in a total amount of about 0.01 to about 4.5% by weight.

6. The agent according to claim 1 , wherein the agent comprises (b) at least one anionic surfactant selected from:
linear and branched fatty acids having 8 to 30 C atoms;
ether carboxylic acids of formula R—O—(CH 2 —CH 2 O) x —CH 2 —COOM, in which
R represents a linear alkyl group having 8 to 30 C atoms,
x represents an integer from 0 to 16,
M represents hydrogen, a metal, an alkali metal, sodium, potassium, lithium, an alkaline-earth metal, ½ magnesium, ½ calcium, ½ zinc, or an ammonium ion (NH 4 + );
acyl sarcosides having 8 to 24 C atoms in the acyl group; acyl taurides having 8 to 24 C atoms in the acyl group;
acyl isethionates having 8 to 24 C atoms in the acyl group that can be obtained by esterification of C 8 -C 24 fatty acids with the sodium salt of 2-hydroxyethane sulfonic acid (isethionic acid),
amide ether carboxylic acids, R 1 CO—NR 2 —CH 2 CH 2 —O—(CH 2 CH 2 O) y CH 2 COOM, wherein

R 1 represents a C 2 -C 30 alkyl group,
y represents an integer from 1 to 20,
R 2 represents hydrogen or a methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, or isobutyl residue; and
M represents hydrogen, a metal, an alkali metal, sodium, potassium, lithium, an alkaline-earth metal, ½ magnesium, ½ calcium, ½ zinc, or an ammonium ion (NH 4 + ).

7. The agent according to claim 1 , wherein the agent comprises, as the anionic surfactant, (b) at least one ether carboxylic acid of formula (B1),
R—O—(CH 2 —CH 2 O) x —OH 2 —COOM  (B1),

wherein
R represents a linear alkyl group having 8 to 30 C atoms,
x represents an integer from 5 to 11;
M represents hydrogen, a metal, an alkali metal, sodium, potassium, lithium, an alkaline-earth metal, ½ magnesium, ½ calcium, ½ zinc, or an ammonium ion (NH 4 + ).

8. The agent according to claim 1 , wherein the agent comprises, relative to the total weight of the agent, one or more anionic surfactants (b) in a total amount of about 0.05 to about 4.5% by weight.

9. The agent according to claim 1 , wherein the agent comprises, as the cationic surfactant, (b) one or more compounds of formula (B2),

wherein
Ra, Rb represent, independently of one another, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 2 -C 6 hydroxyalkyl group;
Rc represents a C 1 -C 7 alkyl group, a C 8 -C 28 alkyl group,

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Gebert-Schwarzwaelder Antje
• Giesa Helmut
• Kroos Astrid

Classifications

• A61K8/4946

  Imidazoles or their condensed derivatives, e.g. benzimidazoles · CPC title

• C09B33/16

  from other coupling components · CPC title

• A61K8/416

  Quaternary ammonium compounds (A61K8/35 takes precedence) · CPC title

• A61K8/39

  Derivatives containing from 2 to 10 oxyalkylene groups · CPC title

• C09B31/14

  Heterocyclic components · CPC title