US 2002/0170125 A1 · Bridged diaminopyrazole compounds and dye compositions containing same

Abstract

The new diaminopyrazole compounds are bridged 4,5-diaminopyrazole compounds or salts thereof. These diaminopyrazole compounds have the formula (I): 1 wherein R1 represents hydrogen, a C1- to C6-alkyl, a C1- to C4-hydroxyalkyl, a C1- to C4-aminoalkyl, a C1- to C8-alkylamino, a di(C1- to C8-alkyl)amino, a C1- to C4-alkylamino-(C1- to C4-alkyl), a di(C1- to C4-alkylamino)-C1- to C4-alkyl, an aryl or a heteroaryl; R2 and R3 each represent hydrogen, a straight-chain or branched C1- to C6-alkyl, an aryl, a heteroaryl, a carboxylic acid, a carboxylic acid ester, an unsubstituted or substituted carboxylic acid amide, a hydroxy or a C1- to C4-hydroxyalkyl group, or R2 and R3 together represent a C1- to C6-alkylene group; Z represents a C1- to C10-alkyl diradical, optionally interrupted by a heteroatom, an aromatic or heteroaromatic diradical, optionally substituted with a hydroxy group, a C1- to C6-alkyl group and/or is subjected to a benzocondensation once or twice; or Z is —Ar(Alk)n—Ar—, wherein Ar represents an arylene group or a heteroarylene group, Alk represents a —CH2— group and n is 0 to 6; and x and y are 0 or 1.

Claims16

Dependent claims

A 4,5-diaminopyrazole compound of formula (I), or a salt thereof with an organic or an inorganic acid:

8
wherein
R1 represents hydrogen, a straight-chain or branched C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a C1- to C4-aminoalkyl group, a C1- to C8-alkylamino group, a di(C1- to C8-alkyl)amino group, a C1- to C4-alkylamino-(C1- to C4-alkyl) group or a di(C1- to C4-alkylamino)-C1- to C4-alkyl group, an aryl group or a heteroaryl group;
R2 and R3, independently of each other, are the same or different and each represent hydrogen, a straight-chain or branched C1- to C6-alkyl group, an aryl group, a heteroaryl group, a carboxylic acid group, a carboxylic acid ester group, an unsubstituted or substituted carboxylic acid amide group, a hydroxy group or a C1- to C4-hydroxyalkyl group, or R2 and R3 together represent an unsubstituted or substituted C1- to C6-alkylene group;
Z represents a C1- to C10-alkyl diradical, which is optionally interrupted by a heteroatom, an aromatic or heteroaromatic diradical, which is optionally substituted with a hydroxy group, a C1- to C6-alkyl group or subjected to a benzo-condensation once or twice;
or Z is a diradical of formula —Ar(Alk)n—Ar—, wherein Ar represents an arylene or heteroarylene group, which is optionally substituted, Alk represents a —CH2— group and n represents a number from 0 to 6;
and x and y independently of each other represent 0 or 1.

4 more elements

A dye composition for oxidative dyeing of keratin fibers, wherein said dye composition comprises at least one 4,5-diaminopyrazole compound of formula (I), or a salt thereof:

9
wherein
R1 represents hydrogen, a straight-chain or branched C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a C1- to C4-aminoalkyl group, a C1- to C8-alkylamino group, a di(C1- to C8-alkyl)amino group, a C1- to C4-alkylamino-(C1- to C4-alkyl) group or a di(C1- to C4-alkylamino)-C1- to C4-alkyl group, an aryl group or a heteroaryl group;
R2 and R3, independently of each other, are the same or different and each represent hydrogen, a straight-chain or branched C1- to C6-alkyl group, an aryl group, a heteroaryl group, a carboxylic acid group, a carboxylic acid ester group, an unsubstituted or substituted carboxylic acid amide group, a hydroxy group or a C1- to C4-hydroxyalkyl group, or R2 and R3 together represent an unsubstituted or substituted C1- to C6-alkylene group;
Z represents a C1- to C10-alkyl diradical, which is optionally interrupted by a heteroatom, an aromatic or heteroaromatic diradical, which is optionally substituted with a hydroxy group, a C1- to C6-alkyl group or subjected to a benzo-condensation once or twice;
or Z is a diradical of formula —Ar(Alk)n—Ar—, wherein Ar represents an arylene or heteroarylene group, which is optionally substituted, Alk represents a —CH2— group and n represents a number from 0 to 6;
and x and y independently of each other represent 0 or 1.

4 more elements

A dye composition for oxidative dyeing of keratin fibers, said dye composition comprising at least one 4,5-diaminopyrazole compound selected from the group consisting of bis-(4,5-diaminopyrazol-1-yl)methane, 1,2-bis-(4,5-diamino-pyrazol-1-yl)ethane, 1,3-bis-(4,5-diaminopyrazol-1-yl)propane, 1,3-bis-(4,5-diamino-3-phenylpyrazol-1-yl)propane, 2,3-bis-(4,5-diaminopyrazol-1-yl)propan-1-ol, N-benzyl-2,3-bis-(4,5-diaminopyrazol-1-yl)propionamide, 1,3-bis(4,5-diamino-pyrazol-1-yl)cyclohexane, 1,4-bis(4,5-diaminopyrazol-1-yl-methyl)benzene, 1,4-bis(4,5-diaminopyrazol-1-yl-methyl)-2,5-dimethoxy-benzene, 1,3-bis(4,5-diaminopyrazol-1-yl-methyl)benzene, 2,6-bis(4,5-diaminopyrazol-1-yl-methyl)-4-methyphenol, 1,2-bis(4,5-diaminopyrazol-1-yl-methyl)benzene, 1,2-bis(4,5-diaminopyrazol-1-yl-methyl)-4,5-dimethoxybenzene, 2,3-bis(4,5-diamino-pyrazol-1-yl-methyl)naphthalene, 2,3-bis(4,5-diaminopyrazol-1-yl-methyl)-anthracene, 9,10-bis(4,5-diaminopyrazol-1-yl-methyl)anthracene, 4,4′-bis(4,5-diaminopyrazol-1-yl-methyl)biphenyl, 1,2-bis-[4-(4,5-diaminopyrazol-1-yl-methyl)-phenyl]ethane, 2,5-bis-(4,5-diaminopyrazol-1-yl-methyl)furan, 2,5-bis-(4,5-diaminopyrazol-1-yl-methyl)thiophene, 2,8-bis-(4,5-diaminopyrazol-1-yl-methyl)-dibenzothiophene, 4,4′-bis(4,5-diaminopyrazol-1-yl-methyl)-[2,2′]bipyridyl and 1,2′-bis[6-(4,5-diaminopyrazol-1-yl-methyl)pyridin-2-yl]ethane;

or a physiologically compatible salt thereof with an organic or inorganic acid.

A ready-to-apply dye mixture made by mixing a dye composition with an oxidizing composition in a weight ratio of said dye composition to said oxidizing composition of from 5:1 to 1:3, wherein said dye composition comprises at least one 4,5-diaminopyrazole compound of formula (I), or a salt thereof:

10
wherein
R1 represents hydrogen, a straight-chain or branched C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a C1- to C4-aminoalkyl group, a C1- to C8-alkylamino group, a di(C1- to C8-alkyl)amino group, a C1- to C4-alkylamino-(C1- to C4-alkyl) group or a di(C1- to C4-alkylamino)-C1- to C4-alkyl group, an aryl group or a heteroaryl group;
R2 and R3, independently of each other, are the same or different and each represent hydrogen, a straight-chain or branched C1- to C6-alkyl group, an aryl group, a heteroaryl group, a carboxylic acid group, a carboxylic acid ester group, an unsubstituted or substituted carboxylic acid amide group, a hydroxy group or a C1- to C4-hydroxyalkyl group, or R2 and R3 together represent an unsubstituted or substituted C1- to C6-alkylene group;
Z represents a C1- to C10-alkyl diradical, which is optionally interrupted by a heteroatom, an aromatic or heteroaromatic diradical, which is optionally substituted with a hydroxy group, a C1- to C6-alkyl group or subjected to a benzo-condensation once or twice;
or Z is a diradical of formula —Ar(Alk)n—Ar—, wherein Ar represents an arylene or heteroarylene group, which is optionally substituted, Alk represents a —CH2— group and n represents a number from 0 to 6;
and x and y independently of each other represent 0 or 1.

4 more elements

Dependencies are inferred from the claim text.

Bridged diaminopyrazole compounds and dye compositions containing same

Life of this patent

Bridged diaminopyrazole compounds and dye compositions containing same

Life of this patent

Abstract

Claims16