IP Library Granted Patent US 7,473,281
Granted Patent B2
US 7,473,281 · App. 11/728,855 · Granted Jan 6, 2009

Colorants containing cationic indazoline thiazolazo dye

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Quick Facts
Patent No.
US 7,473,281
App. No.
11/728,855
Granted
Jan 6, 2009
Kind
B2
Abstract

Colorant for keratin fibers containing cationic indazoline thiazolazo dyes of the general formula (I).

Claims (45)

1. An agent for non-oxidative coloring of keratin fibers, comprising at least one cationic indazoline thiazolazo dye of the general formula (I),

wherein

R1 stands for a hydrogen atom, a C 1 -C 6 -alkyl amino group, a tert-butyl group, an iso-propyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl sulfonic acid group, and a C 1 -C 6 -alkyl sulfonic acid ester group;

R2 represents a group of the general formulas (II), (III), or (IV);

R3 represents a C 1 -C 6 -alkyl group, a C 2 -C 4 -hydroxy alkyl group or a C 4 -C 6 -polyhydroxy alkyl group;

R4 and R5, independently from one another, are either hydrogen, a C 1 -C 6 -alkyl amino group, a C 1 -C 6 -N-N-dialkyl amino group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxy alkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, a benzyl group, or a phenyl group;

R6 and R7, independently from one another, are either hydrogen, an amino group, a C 1 -C 6 -alkylamino group, a C 1 -C 6 -N,N-dialkylamino group, a C 1 -C 6 -N,N-(dihydroxyalkyl)amino group, a halogen atom, a cyano group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -hydroxy alkyloxy group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, a phenyl group, or a sulfonic acid group;

R8 is either hydrogen, a C 1 -C 6 -alkylamino group, a C 1 -C 6 —N,N-dialkyl amino group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, or a phenyl group;

R9 is either a hydrogen atom, an amino group, a C 1 -C 6 -alkyl amino group, a C 1 -C 6 —N,N-dialkyl amino group, a C 1 -C 6 -alkyl cyano group, a hydroxyl group, a nitro group, a methoxymethyl group, a tert-butyl group, an iso-propyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, or a carboxylic acid group (—COOH);

wherein the alkyl groups can either be branched or linear, and

X − represents an anion;

wherein said agent comprises at least one natural polymer, synthetic polymer, or modified polymer of natural origin customary for cosmetic agents, wherein said natural polymer, synthetic polymer, or modified polymer is present in the form of a tinting strengthener or a color strengthener.

2. An agent according to claim 1 , wherein the cationic indazoline thiazolazo dye of the general formula (I) is selected from the group consisting of 6-{(E)-[4-(dimethylamino)phenyl]diazenyl}-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 7-methyl-6-{(E)-[4-(methylamino)phenyl]diazenyl}-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-{(E)-[4-(ethylamino)phenyl]diazenyl}-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-{(E)-[4-(diethylamino)-phenyl]diazenyl}-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-((E)-{4-[(2-hydroxyethyl)amino]phenyl}diazenyl)-7-methyl-1H-[1,3]thiazolo-[5,4-f]indazole-7-ium-methylsulfate, 6-((E)-{4-[bis(2-hydroxyethyl)amino]phenyl}-diazenyl)-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 2-hydroxyethyl {4-[(E)-(7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-6-yl)diazenyl]phenyl}cyanamid methylsulfate, 6-((E)-{4-[(2-hydroxyethyl)(methyl)-amino]phenyl}diazenyl)-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-((E)-{4-[ethyl(2-hydroxyethyl)amino]phenyl}diazenyl)-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-{(E)-[4-(dimethylamino)-phenyl]diazenyl}-1,7-dimethyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-{(E)-[4-(dimethylamino)phenyl]diazenyl}-1-(2-hydroxyethyl)-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-{(E)-[4-(diethylamino)-phenyl]diazenyl}-1-(2-hydroxyethyl)-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-((E)-{4-[bis(2-hydroxyethyl)amino]phenyl}diazenyl)-1-(2-hydroxyethyl)-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-((E)-{4-[bis(2-hydroxyethyl)amino]phenyl}diazenyl)-1,7-dimethyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-[(E)-(4-hydroxyphenyl)-diazenyl]-1,7-dimethyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-[(E)-(4-hydroxyphenyl)diazenyl]-7-methyl-1H-[1,3]thiazolo[5,4-f] indazole-7-ium-methylsulfate, 6-[(E)-(4-methoxyphenyl)diazenyl]-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-[(E)-(4-methoxyphenyl)-diazenyl]-1,7-dimethyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, 6-[(E)-(3,4-dimethoxyphenyl)diazenyl]-1,7-dimethyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate, and 6-[(E)-(3,4-dimethoxyphenyl)diazenyl]-7-methyl-1H-[1,3]thiazolo[5,4-f]indazole-7-ium-methylsulfate.

3. An agent according to claim 1 , wherein the cationic indazoline thiazolazo dye of the general formula (I) is present in a total quantity of 0.01% to 10% by weight of said agent.

4. An agent according to claim 1 , wherein it is a hair colorant.

5. An agent for simultaneous lightening and coloring of keratin fibers, comprising,

(i) on oxidizing agent; and

(ii) at least one cationic indazoline thiazolazo dye of the general formula (I);

wherein

R1 is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl amino group, a tert-butyl group, a isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl sulfonic acid group, and a C 1 -C 6 -alkyl sulfonic acid ester group;

R2 is selected from the group consisting of the general formulas (II), (III), and (IV);

R3 is selected from the group consisting of a C 1 -C 6 -alkyl group, a C 2 -C 4 -hydroxy alkyl group and a C 4 -C 6 -polyhydroxy alkyl group;

R4 and R5, independently from one another, are selected from the group consisting of a

C 1 -C 6 -alkylamino group, a C 1 -C 6 —N,N-dialkylamino group, a

C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxy alkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, a benzyl group, and a phenyl group;

R6 and R7, independently from one another, are selected from the group consisting of hydrogen, an amino group, a C 1 -C 6 -alkylamino group, a C 1 -C 6 —N,N-dialkylamino group, a C 1 -C 6 —N,N-(dihydroxyalkyl)amino group, a halogen atom, a cyano group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl acid group, a C 1 -C 6 -hydroxy alkyloxy group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, a phenyl group, and a sulfonic acid group;

R8 is selected from the group consisting of hydrogen, a C 1 -C 6 -alkyl amino group, a C 1 -C 6 —N,N-dialkylamino group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, and a phenyl group;

R9 is selected from the group consisting of a hydrogen atom, an amino group, a C 1 -C 6 -alkyl amino group, a C 1 -C 6 —N,N-dialkyl amino group, a C 1 -C 6 -alkyl cyano group, a hydroxyl group, a nitro group, a methoxymethyl group, a tert-butyl group, an iso-propyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, and a carboxylic acid group (—COOH);

wherein the alkyl groups can either be branched or linear, and

X − represents an anion.

6. An agent according to claim 5 , wherein the oxidizing agent is selected from the group consisting of hydrogen peroxide, persulfates, perborates, and mixtures of these compounds.

7. An agent for oxidative coloring of keratin fibers based on oxidative dye precursors, comprising at least one cationic indazoline thiazolazo dye of the general formula (I),

wherein

R1 is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl amino group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl sulfonic acid group, and a C 1 -C 6 -alkyl sulfonic acid ester group;

R2 is selected from the group consisting of a the general formulas (II), (III), and (IV);

R3 is selected from the group consisting of a C 1 -C 6 -alkyl group, a C 2 -C 4 -hydroxy alkyl group and a C 4 -C 6 -polyhydroxy alkyl group;

R4 and R5, independently from one another, are selected from the group consisting of hydrogen, a C 1 -C 6 -alkyl amino group, a C 1 -C 6 —N,N-dialkyl amino group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxy alkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a

C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, a benzyl group, and a phenyl group;

R6 and R7, independently from one another, are selected from the group consisting of hydrogen, an amino group, a C 1 -C 6 -alkylamino group, a C 1 -C 6 —N,N-dialkylamino group, a C 1 -C 6 —N,N-(dihydroxyalkyl)amino group, a halogen atom, a cyano group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -hydroxy alkyloxy group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, a phenyl group, and a sulfonic acid group;

R8 is selected from the group consisting of hydrogen, a C 1 -C 6 -alkylamino group, a C 1 -C 6 —N,N-dialkylamino group, a C 1 -C 6 -alkyl cyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl carboxylic acid amide group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, a C 1 -C 6 -alkyl sulfonic acid amide group, and a phenyl group;

R9 is selected from the group consisting of a hydrogen atom, an amino group, a C 1 -C 6 -alkylamino group, a C 1 -C 6 —N,N-dialkylamino group, a C 1 -C 6 -alkyl cyano group, a hydroxyl group, a nitro group, a methoxymethyl group, a tert-butyl group, an iso-propyl group, a C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyloxy group, a C 1 -C 6 -hydroxyalkyl group, a C 1 -C 6 -alkyl carboxylic acid group, a C 1 -C 6 -alkyl carboxylic acid ester group, a C 1 -C 6 -alkyl sulfonic acid group, a C 1 -C 6 -alkyl sulfonic acid ester group, and a carboxylic acid group (—COOH);

wherein the alkyl groups can either be branched or linear, and

X − represents an anion.

8. An agent according to claim 7 , comprising 0.01% to 12% by weight of at least one oxidative dye precursor.

9. An agent according to claim 7 , wherein said agent is mixed with an oxidizing agent before use.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2021
From: NOXELL CORPORATION
To: WELLA OPERATIONS US, LLC
Reel/Frame 056339/0928 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE NAME OF ASSIGNOR PREVIOUSLY RECORDED ON REEL 040437 FRAME 0133. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Dec 15, 2016
From: THE PROCTER AND GAMBLE COMPANY
To: GALLERIA CO.
Reel/Frame 040941/0637 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2016
From: GALLERIA CO.
To: NOXELL CORPORATION
Reel/Frame 040436/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2016
From: PROCTER AND GAMBLE COMPANY
To: GALLERIA CO.
Reel/Frame 040437/0133 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 17, 2007
From: SPECKBACHER, MARKUS; BRAUN, HANS-JURGEN
To: PROCTER & GAMBLE COMPANY, THE
Reel/Frame 019718/0164 →