IP Library Granted Patent US 7,553,337
Granted Patent B2
US 7,553,337 · App. 10/587,763 · Granted Jun 30, 2009

Hair colorants for simultaneous dyeing and brightening of keratin fibers

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Quick Facts
Patent No.
US 7,553,337
App. No.
10/587,763
Granted
Jun 30, 2009
Kind
B2
Abstract

The present invention has for an object agents for the simultaneous brightening and coloring of keratin fibers—particularly hair—which are characterized in that (a) they contain an oxidant and (b) at least one thiazolium dye of formula (I) and that (c) they have a basic pH

Claims (19)

1. An agent for the simultaneous brightening and coloring of keratin fibers, wherein the agent contains an oxidant and at least one thiazolium dye of formula (I) and has a basic pH

wherein

R1 stands for a saturated or unsaturated (C1-C12)-alkyl group, a halogen atom-substituted (C1-C12)-alkyl group, a hydroxy-(C1-C12)-alkyl group, a (C1-C6)-alkoxy-(C1-C12)-alkyl group, an amino-(C1-C12)-alkyl group, a (C1-C6)-alkylamino-(C1-C12)-alkyl group, a di(C1-C6)-alkylamino-(C1-C12)-alkyl group, a cyano-(C1-C12)-alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group;

R2 and R3 can be equal or different and independently of each other stand for hydrogen, a halogen atom, a saturated or unsaturated (C1-C12)-alkyl group, a (C1-C12)-alkoxy group, a nitro group, an amino group, a (C1-C12)-alkylamino group, a di(C1-C12)-alkylamino group, a (C1-C12)-hydroxyalkylamino group, a di(C1-C12)-hydroxyalkylamino group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted heteroaryl group;

R4 stands for hydrogen, a saturated or unsaturated (C1-C12)-alkyl group, a halogen atom-substituted (C1-C12)-alkyl group, a hydroxy-(C1-C12)-alkyl group, an amino-(C1-C12)-alkyl group or a benzyl group;

R5 and R6 can be equal or different and independently of each other stand for hydrogen, a halogen atom, a saturated or unsaturated (C1-C12)-alkyl group, a hydroxyl group, a (C1-C12)-alkoxy group, a cyano group, a nitro group, an amino group, a (C1-C12)-alkylamino group or a di(C1-C12)-alkylamino group and

A − stands for an anion of an organic or inorganic acid.

2. The agent as defined in claim 1 , wherein R1 stands for a saturated or unsaturated (C1-C12)-alkyl group.

3. The agent as defined in claim 2 , wherein R4 stands for a saturated or unsaturated (C1-C12)-alkyl group.

4. The agent as defined in claim 1 , wherein A − stands for a chloride, bromide, iodide, hydrogen sulfate, sulfate, toluenesulfonate, benzenesulfonate, monomethylsulfate, hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate, tetraphenylborate, formate, acetate or propionate anion.

5. The agent as defined in claim 1 , wherein the compound of formula (I) is selected from the group consisting of:

3-methyl-2-[[4-[4-methyl(phenylmethyl)amino]-phenyl]-azo]thiazolium chloride; 3-methyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium bromide; 3-methyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium monomethyl-sulfate; 3-methyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium acetate; 3,4-di-methyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium chloride; 3,4-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium bromide; 3,4-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium monomethylsulfate; 3,4-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium acetate; 3,5-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium chloride; 3,5-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium bromide; 3,5-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium monomethylsulfate; 3,5-dimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium acetate; 3,4,5-trimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium chloride; 3,4,5-trimethyl-2-[[-4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium bromide; 3,4,5-trimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium monomethylsulfate; 3,4,5-trimethyl-2-[[4-[methyl(phenylmethyl)amino]phenyl]thiazolium acetate; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3-methylthiazolium chloride; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3-methylthiazolium bromide; 2-[[4-[methyl(phenylmethyl)amino]-2-methylphenyl]azo]-3-methylthiazolium monomethylsulfate; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3-methylthiazolium acetate; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4-dimethylthiazolium chloride; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4-dimethylthiazolium bromide; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4-dimethylthiazolium monomethylsulfate; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4-dimethylthiazolium acetate; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,5-dimethylthiazolium chloride; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,5-dimethylthiazolium bromide; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,5-dimethylthiazolium monomethylsulfate; 2-[[-4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,5-dimethylthiazolium acetate; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4,5-trimethylthiazolium chloride; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4,5-trimethylthiazolium bromide; 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4,5-trimethylthiazolium monomethylsulfate; and 2-[[4-[ethyl(phenylmethyl)amino]-2-methylphenyl]azo]-3,4,5-trimethylthiazolium acetate.

6. The agent as defined in claim 1 , wherein the agent contains the compound of formula (I) in an amount from 0.01 to 10 weight percent.

7. The agent as defined in claim 1 , wherein the agent additionally contains at least one other oxidation-resistant direct dye and/or oxidation dye precursor.

8. The agent as defined in claim 1 , wherein the agent is a ready-to-use colorant and has a pH of 8 to 11.

9. The agent as defined in claim 1 , wherein the oxidant is selected from among hydrogen peroxide and the compounds of addition thereof to urea, melamine, sodium borate or sodium carbonate.

10. The agent as defined in claim 1 , wherein the agent additionally contains a persulfate.

11. The agent as defined in claim 1 , wherein the agent is in the form of a 2-component agent consisting of a dye carrier composition (A) containing at least one thiazolium dye of formula (I) and a component (B) containing an oxidant.

12. The agent as defined in claim 1 , wherein the agent is a hair colorant.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE EXECUTION DATE PREVIOUSLY RECORDED AT REEL: 055344 FRAME: 0422. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 29, 2021
From: HFC PRESTIGE INTERNATIONAL HOLDING SWITZERLAND SÀRL
To: HFC PRESTIGE INTERNATIONAL OPERATIONS SWITZERLAND SÀRL
Reel/Frame 056712/0333 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2021
From: HFC PRESTIGE INTERNATIONAL OPERATIONS SWITZERLAND SARL
To: WELLA INTERNATIONAL OPERATIONS SWITZERLAND SARL
Reel/Frame 055428/0174 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2021
From: HFC PRESTIGE INTERNATIONAL HOLDING SWITZERLAND SÀRL
To: HFC PRESTIGE INTERNATIONAL OPERATIONS SWITZERLAND SÀRL
Reel/Frame 055344/0422 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2016
From: WELLA GMBH
To: HFC PRESTIGE INTERNATIONAL HOLDING SWITZERLAND S.A.R.L
Reel/Frame 040420/0478 →