Diaminopyrazole derivatives and dyes containing said compounds

Details Diaminopyrazole derivatives and dyes containing said compounds Diaminopyrazole derivatives and dyes containing said compounds

2002-09-09

2003-07-29

Ramsuer, Robert W. (Department: 1751)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S371700, C008S409000

Reexamination Certificate

active

06600050

ABSTRACT:

The invention relates to new diaminopyrazole derivatives, as well as to agents containing these compounds for dyeing keratin fibers.
In the field of dyeing keratin fibers, especially of dyeing hair, oxidation dyes have achieved appreciable importance. The dyeing takes place here by the reaction of certain developer substances with certain coupler substances in the presence of suitable oxidizing agents. As developer substances, especially 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol and 4,5-diaminopyrazole derivatives are used and, as coupler substances, resorcinol, 4-chlororesorcinol, 1-napthol, 3-aminophenol and derivates of m-phenylenediamine may be mentioned.
Oxidation dyes, which are used to dye human hair, must satisfy numerous requirements in addition to dyeing the hair in the desired intensity. For example, the dyes must be safe from a toxicological and dermatological point of view and the hair dyeings achieved must have good light fastness, acid fastness and crocking fastness and not interfere with permanent wave stability. In any case, however, such dyeings, in the absence of the effects of light, rubbing, and chemical agents, must remain stable for a period of at least 4 to 6 weeks. In addition, it is necessary that a broad palette of different color nuances can be produced by combinations of suitable developer substances and coupler substances. Until now, to cover the increasingly important red region, primarily 4-aminophenol was widely used as a developer. The use of certain diaminopyrazole derivatives in oxidation hair dyeing agents is known from the EP-OS 740 931, DE-OS-42 34 886 and EP-OS 0 786 244. However, the requirements, which must be met by oxidation dyes, are not fulfilled in every respect by these compounds. For example, the dyeings obtained in some cases do not have a satisfactory color intensity and/or pure red shades are not obtained. There is therefore a continued need for new developer substances which fulfill the aforementioned requirements particularly well.
For this purpose, it has now surprisingly been found that new diaminopyrazole derivates of the general Formula (I) fulfill the requirements imposed on developer substances particularly well. For example, color nuances, which are exceedingly intensive, light fast and wash fast, are obtained using these developer substances with most of the known coupler substances.
The object of the present invention therefore are diaminopyrazole derivatives of the general formula (I) or their physiologically tolerated, water soluble salts with inorganic or organic acids
wherein
R1 represents a C
1
-C
6
alkyl group, a C
2
-C
4
hydroxyalkyl group, a C
3
-C
4
dihydroxyalkyl group or a C
2
-C
6
alkoxy (C
1
-C
2
) alkyl group, a phenyl group, a benzyl group or a substituted benzyl group;
R2 and R3 independently of one another are hydrogen, a C
1
-C
6
alkyl group, a hydroxy (C
2
-C
4
) alkyl group, a dihydroxy (C
3
-C
4
) alkyl group or a C
2
-C
4
alkoxy (C
1
-C
2
) alkyl group or R2 and R3, together with the nitrogen, form a 4-member to 8-member heteroaliphatic ring;
R4 represents hydrogen or a C
1
-C
6
alkyl group;
R5 is hydrogen, a C
1
-C
6
alkyl group, an unsaturated C
2
-C
6
alkyl group, a hydroxy (C
2
-C
4
) alkyl group, a dihydroxy (C
3
-C
4
) alkyl group, an amino (C
2
-C
4
) alkyl group, a dimethylamino (C
2
-C
4
) alkyl group, an acetylamino (C
2
-C
4
) alkyl group, a methoxy (C
2
-C
4
) alkyl group, an ethoxy (C
2
-C
4
) alkyl group, a C
1
-C
4
cyanoalkyl group, a carboxy (C
1
-C
4
) alkyl group or an aminocarbonyl (C
1
-C
4
) alkyl group;
R6, R7, R8, R9, R10 independently of one another represent hydrogen, a halogen atom (F, Cl, Br, I), a cyano group, a hydroxy group, a C
1
-C
4
alkoxy group, a hydroxy (C
2
-C
4
) alkoxy group, a C
1
-C
6
alkyl group, a C
1
-C
4
alkylthioether group, a mercapto group, a nitro group, an amino group, a (C
1
-C
4
) alkylamino group, a hydroxy (C
2
-C
4
) alkylamino group, a di(C
1
-C
4
) alkylamino group, a di(hydroxy(C
2
-C
4
)alkyl) amino group, a (dihydroxy(C
3
-C
4
)alkyl) amino group, a (hydroxy(C
2
-C
4
)alkyl)-(C
1
-C
4
)alkylamino group, a trifluoromethyl group, a —C(O)H group, a —C(O)CH
3
group, a —C(O)CF
3
group, an —Si(CH
3
)
3
group, a hydroxy(C
2
-C
4
) alkyl group or a dihydroxy(C
3
-C
4
) alkyl group or two adjacent R6 to R10 groups form an —O—CH2—O— bond.
As compounds of Formula (I), the following may be mentioned by way of example:
2-isopropyl-5-phenylaminomethyl-2H-pyrazole-3,4-diamine, 4-[(4,5-diamino-1-isopropyl-1H-pyrazole-3-ylmethyl)-amino]-phenol, 3-[(4,5-diamino-1-isopropyl-1H-pyrazole-3-ylmethyl)-amino]-phenol, 5-[(4,5-diamino-1-isopropyl-1H-pyrazole-3-ylmethyl)-amino]-2-methyl-phenol, 5[(3,4-dimethoxy-phenylamino)-methyl]-2-isopropyl -2H-pyrazole-3,4-diamine, 2-[(4,5-diamino-1-isopropyl-1H-pyrazole-3-ylmethyl)-amino]-4-nitro-phenol, 5-[(3-amino-phenylamino)-methyl]-2-isopropyl-2H-pyrazole-3,4-diamine, 5-[(4-amino-phenylamino)-methyl]-2-isopropyl-2H-pyrazole-3,4-diamine, 5[(4-amino-2 or 3-methyl-phenylamino)-methyl]-2-isopropyl-2H-pyrazole-3,4-diamine, 2-{5 or 6-amino-2 or 3-[(4,5-diamino-1-isopropyl-1H-pyrazole-3-ylmethyl)-amino]-phenyl}-ethanol, 2-{4-amino-2-[(4,5-diamino-1-isopropyl-1H-pyrazole-3-ylmethyl)-amino]-phenoxy}-ethanol, 5-[(4-dimethylamino-phenylamino)-methyl]-2-isopropyl-2H-pyrazole-3,4-diamine, 2-{4,5-diamino-3-[(3-amino-phenylamino)-methyl]-pyrazole-1-yl}-ethanol, 2-{4,5-diamino-3-[(4-amino-phenylamino)-methyl]-pyrazole-1-yl}-ethanol, 2-{4,5-diamino-3-[(4-amino-2-methyl-phenylamino)-methyl]-pyrazole-1-yl}-ethanol, 2-(4,5-diamino-3-{[4-amino-2-(2-hydroxy-ethyl)-phenylamino]-methyl}-pyrazole-1-yl)-ethanol, 2-{4,5-diamino-3-[(4-dimethylamino-phenylamino)-methyl]-pyrazole-1-yl}-ethanol, 2-[4,5-diamino-3-(benzo[1,3]dioxol-5-yl-aminomethyl)-pyrazole-1-yl]ethanol, 4-chloro-2-{[4,5-diamino-1-(2-hydroxy-ethyl)-1H-pyrazole-3-ylmethyl]-amino}-phenol, 2-(4,5-diamino-3-phenylaminomethyl-pyrazole-1-yl)-ethanol, 4-{[4,5-diamino-1-(2-hydroxy-ethyl)-1H-pyrazole-3-ylmethyl]-amino} phenol, 3-{[4,5-diamino-1-(2-hydroxyethyl)-1H-pyrazole-3-ylmethyl]-amino}-phenol, 5-{[4,5-diamino-1-(2-hydroxy-ethyl)-1H-pyrazole-3-ylmethyl]-amino}-2-methyl-phenol, 2-{[4,5-diamino-3-[(3,4-dimethoxy-phenylamino)-methyl]-pyrazole-1-yl}-ethanol, 2-{[4,5-diamino-1-(2-hydroxy-ethyl)-1H-pyrazole-3-ylmethyl]-amino}-4-nitro-phenol, 2-(4-methyl-benzyl)-5-phenylaminomethyl-2H-pyrazole-3,4-diamine, 2-benzyl-5-phenylaminomethyl-2H-pyrazole-3,4-diamine, 2-methyl-5-phenylaminomethyl-2H-pyrazole-3,4-diamine, 2-phenyl-5-phenylaminomethyl-2H-pyrazole-3,4-diamine, 2-t-butyl-5-phenyl-aminomethyl-2H-pyrazole-3,4-diamine, 5-[(4-amino-phenylamino)-methyl]-2-(4-methyl-benzyl)-2H-pyrazole-3,4-diamine, 5-[(4-amino-phenylamino)-methyl]-2-benzyl-2H-pyrazole-3,4-diamine, 4-[(4,5-diamino-1-(4-methyl-benzyl)-1H-pyrazole-3-ylmethyl)-amino]phenol, 4-[(4,5-diamino-1-benzyl-1H-pyrazole-3-ylmethyl)-amino]-phenol.
Preferred are compounds of Formula (I), in which (i) R2 and R3 represent hydrogen and R1 represents a C
1
-C
4
alkyl group, a C
2
-C
4
hydroxyalkyl group, a benzyl group or a methylbenzyl group and/or (ii) R2, R3, R4 and R5 represent hydrogen and R1 represents a C
1
-C
4
alkyl group, a C
2
-C
4
hydroxyalkyl group, a benzyl group or a methylbenzyl group, and/or (iii) R2, R3, R4 and R5 represent hydrogen and R1 represents a C
1
-C
4
alkyl group, a C
2
-C
4
hydroxyalkyl group, a benzyl group or a methylbenzyl group, and at least one of the R6 to R10 groups is a hydroxy group or an amino group, while the remaining R6 to R10 groups are hydrogen.
In particular, the following compounds or their salts with inorganic or organic acids may be mentioned:
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