Bridged diaminopyrazole compounds and dye compositions...

Details Bridged diaminopyrazole compounds and dye compositions... Bridged diaminopyrazole compounds and dye compositions...

2001-12-14

2004-04-06

Huang, Evelyn Mei (Department: 1625)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S429000, C548S365100, C548S365400, C548S364400, C546S256000

Reexamination Certificate

active

06716257

ABSTRACT:

BACKGROUND OF THE INVENTION
The subject matter of the present invention includes new 4,5-diaminopyrazole compounds and their physiologically compatible salts with organic or inorganic acids. The subject matter of the present invention also includes dye compositions containing these new compounds as dyestuff pre-cursor compounds.
Oxidation dyestuffs have been important in the field of traditional hair dyeing for a long time. The effective dyeing agent is produced by reaction of certain developer and coupler substances in the presence of an oxidizing agent. Hair dye compositions for dyeing hair natural color shades are of special significance. Besides those dye compositions combinations of suitable oxidation dye precursor compounds are used to produce currently fashionable color nuances and accents. Currently brown shades with outstanding aubergine or copper tones, especially glowing red tones that deviate from natural colors, can be produced.
Oxidation dyestuffs, which are used for treatment of human hair, have very stringent requirements besides the requirements for producing certain predetermined color effects. The dyestuff must be both toxicologically and dermatologically unobjectionable and also not sensitizing. A broad palette of different color shades and nuances are required, which must be obtained by suitable combination of appropriate developer and coupler components. The hair dyeing compositions obtained should have good wash-fastness, light-fastness, sweat-fastness, permanent wave-fastness, acid-fastness, base-fastness and friction-fastness. In each case these hair dye compositions must remain stable under the common current daily conditions for at least four to six weeks.
In the past 4-aminophenol was the predominant developer used to cover the increasingly important red range. Pyridine derivatives and pyrimidine derivatives, which generally are not satisfactory for dyeing, have also been employed because of considerations regarding the physiological compatibility of 4-aminophenol. A significant improvement in the color stability, especially in the red range, was obtained by the exchange of p-aminophenol by the 4,5-diaminopyrazole compounds described in German Patent Applications DE-OS 42 34 885, DE-OS 42 34 887 and EP-OS 0 375 977. The manufacture of these latter dye compounds by the methods described in those applications is however, in part, very expensive and requires, in part, starting materials, which are expensive and not widely available. 4,5-diaminopyrazoles substituted in the 3 position are known from EP-OS 0 740 931. These compounds however must be made, in part, according to an expensive method, since components, especially C3 components, are not readily available. The pyrazoles described in EP-OS 0 740 931 are also not entirely satisfactory in regard to the attainable color palette and color saturation.
While most oxidation dyestuffs are characterized by hardly any weakening or impairment on undamaged hair, serious differences result when they are used on damaged hair. The hairstylist knows from his daily practice that dyestuffs are not absorbed uniformly on the hair to be dyed. While the hair roots are usually intact, the hair tips are generally damaged because of the effects of weather, frequent washing and combing as time goes on. The damage increases from the roots to the tips. A non-uniform color is thus produced from the roots to the tips when the hair is dyed because of the non-uniform condition of the hair from the roots to the tips. An additional problem is that the absorbed dyestuffs are more easily washed from the damaged part of the hair than from the undamaged part of the hair. As a result after a few washings of the dyed hair the differences in the color of the dyed damaged part of the hair and the dyed undamaged part of the hair are more clearly visible.
SUMMARY OF THE INVENTION
Thus there is a great long-standing need for new dye precursor compounds suitable for oxidative dye systems for coverage of the red range, which provide a considerably improved color stability against shampooing on hair of different quality, especially on hair that has been damaged by permanent shaping and bleaching, besides good absorption properties. It is an object of the present invention to provide these new dye precursor compounds.
Certain special new bridged pyrazole compounds attain this object in an outstanding manner.
The subject matter of the present invention thus includes the bridged 4,5-diaminopyrazole compounds of formula (I) or their salts with organic or inorganic acids:
wherein
R1 represents hydrogen, a straight-chain or branched C
1
- to C
6
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group, a C
1
- to C
4
-aminoalkyl group, a C
1
- to C
8
-alkylamino group, a di(C
1
- to C
8
-alkyl)amino group, a C
1
- to C
4
-alkylamino-(C
1
- to C
4
-alkyl) group or a di(C
1
- to C
4
-alkylamino)- C
1
- to C
4
-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 C
1
- to C
6
-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 C
1
- to C
4
-hydroxyalkyl group, or R2 and R3 together represent an unsubstituted or substituted C
1
- to C
6
-alkylene group;
Z represents a C
1
- to C
10
-alkyl diradical, which is optionally interrupted by a heteroatom, for example by a nitrogen atom, an oxygen atom or a sulfur atom, an aromatic or heteroaromatic diradical, which may be substituted optionally with a hydroxy group or a C
1
- to C
6
-alkyl group and/or may be subjected to a benzo-condensation once or twice; or a diradical of formula —Ar(Alk)
n
—Ar—, wherein Ar represents an arylene group or a heteroarylene group (especially a phenylene group or a pyridylene group), which may optionally be substituted, Alk represents a —CH
2
— group and n represents a number from 0 to 6; and x and y independently of each other represent 0 or 1.
The following bridged pyrazole compounds of formula (I) are, for example, suitable:
Compounds of the general formula (I), in which R1 is a hydrogen atom, a methyl group, a phenyl group, a thienyl group or a furyl group; R2 and R3, independently of each other, each represent a hydrogen atom, a phenyl group, a carboxylic acid amide group or a hydroxymethyl group; Z represents an unsubstituted alkylene diradical, phenylene diradical or heteroaryl diradical, and x and y each represent, independently of each other, 0 or 1, are especially preferred as dye compounds of the invention and in the dye compositions of the invention.
Compounds of formula (I), in which R1 to R3 each represent a hydrogen atom; Z represents an unsubstituted alkylene diradical, phenylene diradical or heteroaryl diradical, and x and y each represent, independently of each other, 0 or 1, are especially preferred as dye compounds of the invention and in the dye compositions of the invention.
The compounds of formula (I) can be made with different methods.
One possible synthesis schema 1 is described hereinbelow. First two equivalents of 3,5-dibromo-4-nitropyrazole are bridged with a dihalogenide. After conversion to the corresponding 5-benzylamino compound and subsequent catalytic hydrogenation one obtains the corresponding 4,5-diaminopyrazole of the general formula (I).
However in the case of certain embodiments the preparative schema 2 is advantageous. In the method of schema 2 first cyanoethyl hydrazine is reacted with dialdehydes or diketones to form the corresponding dihydrazones. Subsequently the dihydrazones so obtained are cyclized to form the bridged 5-aminopyrazoles. The intermediate steps in the method are performed, for example, according to the procedure set forth in FR-A 1 403 372. The subsequent introduction of the second pyrazole amino group into position 4, which for example is possible by azo coupling or nitrosation, similarly makes 4,5-diaminopyrazoles of the general formula (I) available. This synthesis sche

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