Diaminopyrazole derivatives and oxidation hair dyes...

Details Diaminopyrazole derivatives and oxidation hair dyes... Diaminopyrazole derivatives and oxidation hair dyes...

2002-10-08

2004-09-21

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S408000, C008S409000, C008S570000, C008S573000, C008S576000, C008S649000, C008S668000, C008S669000, C008S670000

Reexamination Certificate

active

06793687

ABSTRACT:

BACKGROUND OF THE INVENTION
The object of the present Invention are agents for oxidatively dyeing hair, which contain certain diaminopyrazole derivatives as developer substance and certain pyazolone derivatives as coupler substance.
Hair dyeing agents are divided mainly into oxidation dyeing agents and non-oxidative tinting, depending on the starting color of the hair, which is to be dyed, and on the desired end result. At the present time, oxidative hair dyes have attained a significant importance. The dyeing is brought about here by the reaction of certain developer substances with certain coupler substances in the presence of suitable oxidizing agents.
As developer substances, particularly 2,5-diaminotoluene, 2.5-diaminophenylethyl alcohol, p-aminophenol and 1,4-diaminobenzene are used. Frequently used coupler compounds are resorcinol, 1-naphthol, 3-aminophenol, 5-amino-2-methylphenol, 4-chlororesorcinol and derivatives of m-phenylenediamine.
Oxidation dyes, which are used to dye human hair, must fulfill numerous requirements. They must be physiologically compatible and provide dyeings in the desired intensity. In addition, the hair dyeings should be highly resistant to the effects of light, permanent waving agents and acids, as well as friction, and remain stable for at least 4 to 6 weeks under normal conditions.
In addition, an oxidative dyeing system must make possible a wide range of different color nuances in the range of natural shades as well as of fashion shades. This means that, on the one hand, yellow, red and blue dyes must be available for the fashion shade range and, on the other, blond, brown and black dyes for the natural shade range. The natural shades can also be obtained by mixing different dyes, which produce yellow, red and blue.
As developer substances in the fashion shade range, 4,5-diaminopyrazole derivatives, which are tolerated well physiologically, have gained acceptance recently. They produce very intensive red, violet and blue color shades with different coupler compounds. Such oxidation dyeing agents, which contain pyrazoles, are described, for example, in the DE-OS 42 34 885, DE-OS 42 34 887, DE-PS 197 30 412, EP-OS 0 375 977 and the EP-OS 0 740 931.
Color nuances in the yellow and orange range have not previously been described with the pyrazole derivatives named above.
SUMMARY OF THE INVENTION
it is therefore an object of the present invention to make available a system of developer and coupler substances, which is suitable for the yellow and orange color ranges and contains certain diaminopyrazole derivatives as developer substance.
It has now been discovered that this objective can be accomplished by using certain pyrazolone derivatives as coupler substance.
The object of the present invention therefore is an agent for the oxidative dyeing of keratin fibers, especially of hair, wherein the agent contains (a) at least one 4,5-diaminopyrazole derivative of Formula (I), (II) or (III) or its salt with organic or inorganic acids,
wherein R1 and R2 independently of one another represent hydrogen, a linear or branched C
1
-C
6
alkyl group, an optionally substituted phenyl group or a linear or branched C
2
-C
4
-hydroxyalkyl group;
R3 represents a halogen atom (F, Cl, Br, I), a linear or branched C
1
-C
4
alkyl group or a linear or branched C
1
-C
4
alkoxy group and R4 represents hydrogen, a linear or branched C
1
-C
4
alkyl group or a linear or branched C
2
-C
4
hydroxyalkyl group;
R5 represents hydrogen, a linear or branched C
1
-C
6
alkyl group, a C
1
-C
4
hydroxy alkyl group, a C
1
-C
4
aminoalkyl group, a C
1
-C
8
alkylamino group, a di(C
1
-C
8
) alkylamino group, a C
1
-C
4
alkylamino-(C
1
-C
4
)alkyl group or a di(C
1
-C
4
) alkylamino-(C
1
-C
4
)alkyl group, an aryl group or a heteroaryl group;
R6 and R7 may be identical or different and represent hydrogen, a linear or branched C
1
-C
6
alkyl group, an aryl group, a heteroaryl group, a carboxylic acid group, a carboxylic ester group, an unsubstituted or substituted carboxylic acid amide group, a hydroxy group or a C
1
-C
4
hydroxyalkyl group or R2 and R3 jointly form an optionally substituted C
1
-C
6
alkylene group;
Z is a C
1
-C
10
alkyl diradical, which is optionally interrupted by a hetero atom (such as a nitrogen, oxygen or sulfur atom), an aromatic or heteroaromatic diradical, which is optionally condensed with one or two benzene rings and/or substituted by a hydroxy group or a C
1
-C
6
alkyl group, or a diradical of formula —Ar-(Alk)
n
-Ar—, in which Ar is an optionally substituted aryl or heteroaryl group, especially a phenylene or pyridyl group, Alk is a —CH
2
group and n is a whole number from 0 to 6; and
x and y independently of one another are equal to 0 or 1;
and (b) at least one pyrazol-5-one derivative of the general Formula (IV), (V) or (VI), especially (IV) or (VI), or its salt with organic or inorganic acids,
wherein
R8 is a linear or branched C
1
-C
4
alkyl group, a linear or branched C
1
-C
4
alkoxy group, a linear or branched C
1
-C
4
alkoxy-(C
1
-C
8
)alkyl group or a linear or branched C
2
-C
4
hydroxyalkyl group; and
R9 to R13 independently of one another in each case are hydrogen, a linear or branched C
1
-C
4
alkyl group, a linear or branched C
2
-C
4
hydroxyalkyl group, a hydroxy group, an amino group, a linear or branched C
1
-C
4
alkoxy group, a linear or branched C
1
-C
4
alkoxy-(C
1
-C
4
)alkyl group or a C
1
-C
4
hydroxyalkylamino group.
In particular, the following may be mentioned as preferred 4,5-diaminopyrazole derivatives of Formulas (I), (II) and (III): 4,5-diamino-1-methyl-1H-pyrazole; 4,5-diamino-1-(4′-methylbenzyl)-pyrazole; 4,5-diamino-1-(3′-methylbenzyl)-pyrazole; 4,5-diamino-1-(2′-methylbenzyl)-pyrazole; 4,5-diamino-1-(2′-hydroxyethyl)-1H-pyrazole; 4,5-diamino-1-benzyl-1H-pyrazole; 4,5-diamino-1-ethyl-1H-pyrazole; 4,5-diamino-1-isopropyl-1H-pyrazole; 4,5-diamino-1-pentyl-1H-pyrazole; 4,5-diamino-1-(4′-methoxybenzyl)-1H-pyrazole; 4,5-diamino-1H-pyrazole; 4,5-diamino-1-(3′-methoxybenzyl)-1H-pyrazole; 4,5-diamino-1-(2′-methoxybenzyl)-1H-pyrazole; 4,5-diamino-1-(4′-chlorobenzyl)-1H-pyrazole; 4,5-diamino-1-(3′-chlorobenzyl)-1H-pyrazole; 4,5-diamino-1-(2′-chlorobenzyl)-1H-pyrazole; 4-amino-5-methylamino-1-(4′-methoxybenzyl)-1H-pyrazole; 4-amino-5-(2′-hydroxyethyl)amino-1-(4′-methoxybenzyl)-1H-pyrazole; 4-amino-5-methylamino-1-(2′-hydroxyethyl)-1H-pyrazole; bis-(4,5-diamino-pyrazole-1-yl)-methane; 1,2-bis-(4,5-diamino-pyrazole-1-yl)-ethane; 1,3-bis-(4,5-diamino-pyrazole-1-yl)-propane, 1,3-bis-(4,5-diamino-3-phenyl-pyrazole-1-yl)-propane; 2,3,-bis-(4,5-diamino-pyrazole-1-yl)-propane-1-ol; N-benzyl-2,3-bis-(4,5-diamino-pyrazole-1-yl)-propionamide; 1,3-bis-(4,5-diamino-pyrazole-1-yl)-cyclohexane; 1,4-bis-(4,5-diamino-pyrazole-1-yl-methyl)-benzene; 1,4-bis-(4,5-diamino-pyrazole-1-yl-methyl)-2,5-dimethoxy-benzene; 1,3-bis-(4,5-diamino-pyrazole-1-yl-methyl)-benzene; 2,6-bis-(4,5-diamino-pyrazole-1-yl-methyl)-4-methyl-phenol; 1,2-bis-(4,5-diamino-pyrazole-1-yl-methyl)-benzene; 1,2-bis-(4,5-diamino-pyrazole-1-yl-methyl)-4,5-dimethoxy-benzene; 2,3-bis-(4,5-diamino-pyrazole-1-yl-methyl)-naphthalene; 2,3-bis-(4,5-diamino-pyrazole-1-yl-methyl)-anthracene; 9,10-bis-(4,5-diamino-pyrazole-1-yl-methyl)-anthracene; 4,4′-bis-(4,5-diamino-pyrazole-1-yl-methyl)-biphenyl; 1,2-bis-[4-(4,5-diamino-pyrazole-1-yl-methyl)-phenyl]-ethane; 2,5-bis-(4,5-diamino-pyrazole-1-yl-methyl)-furan; 2,5-bis-(4,5-diamino-pyrazole-1-yl-methyl)-thiophene; 2,8-bis-(4,5-diamino-pyrazole-1-yl-methyl)-dibenzothiophene; 4,4′-bis-(4,5-diamino-pyrazole-1-yl-methyl)-[2,2′]bipyridyl and 1,2-bis-[6-(4,5-diamino-pyrazole-1-yl-methyl)-pyridine-2-yl]-ethane or their salts with organic and inorganic acids.
In particular, the following may be mentioned as preferred pyrazolone derivatives of Formulas (IV), (V) and (VI): 3-amino-1-phenyl-pyrazole-5-one, 3-methyl-1-phenyl-pyrazole-5-one, 1,3-dimethyl-pyrazole-5-one, 3-methyl-1-(4-sulfphenyl)-pyrazole-5-on

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