Drug – bio-affecting and body treating compositions – Inorganic active ingredient containing – Carbon disulfide – monoxide – or dioxide
Patent
1994-06-07
1996-07-09
Venkat, Jyothsna
Drug, bio-affecting and body treating compositions
Inorganic active ingredient containing
Carbon disulfide, monoxide, or dioxide
5483714, 8409, A61K 713, C07D23138
Patent
active
055342671
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/02641 filed Sep. 29, 1993.
BACKGROUND OF THE INVENTION
The subject matter of the invention concerns compositions for the oxidative dyeing of hair based on 4,5-diaminopyrazole derivatives as developers and new 4,5-diaminopyrazole derivatives.
In the area of hair coloring, oxidative dyes have achieved considerable importance. The dyeing is effected by the reaction of certain developers with certain couplers in the presence of a suitable oxidizing agent.
Such developers are, in particular, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol and 1,4-diaminobenzene. Resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol, 5-amino-2-methylphenol and derivatives of m-phenylenediamine are preferably used as couplers.
Oxidative dye compositions for dyeing human hair have numerous special requirements. For example, they must be unobjectionable in toxicological and dermatological respects and must enable the desired intensity of coloring. In addition, a favorable fastness to light, permanent waving, acids and rubbing is required of the achieved hair dyes. But, in every instance, such hair dyes must remain stable over a period of at least 4 to 6 weeks without being affected by light, rubbing or chemical agents. Moreover, it is necessary that a wide assortment of various color shades can be produced by means of combining suitable developers and couplers. 4-Aminophenol above all is used to achieve natural shades and especially fashionable shades in the red range either by itself or in a mixture with other developers in combination with suitable couplers.
The developer 4-aminophenol, whose chief use was formerly for the red range of the color scale, has been criticized in the past with respect to its physiological compatibility, while developers such as pyrimidine derivatives which have been recommended more recently are not completely satisfactory with respect to coloring. The pyrazole derivatives described in DE-OS21 60 317 such as 3-amino-1-phenyl-2-pyrazolone-5 have insufficient depth of color when used to dye hair and are not usable in hair dyeing practice.
Pyrazole derivatives which achieve intense coloring with various couplers are described in DE-OS 38 43 892. The compounds described therein can only be obtained by very expensive synthesizing processes and have low yields.
Various methods have been described in technical literature for producing 1-methyl-4,5-diaminopyrazole. According to H. Dorn, et al., Chem. Ber. 98, p. 3368 (1965), 5-amino-1-methylpyrazole-4-carboxylic acid is obtained in a yield of 53 percent from ethoxymethylene cyanoacetic acid ethyl ester and methylhydrazine and is decarboxylated to obtain 5-amino-1-methylpyrazole with a yield of 75 percent (total yield : 40 percent). DE-OS 2 141 700 describes a single-step process for obtaining 5-amino-1-methylpyrazole from N,N-dimethylaminoacrylonitrile and methylhydrazine in a yield of 71 percent. For further conversion, this compound can be convened to 5-amino-1-methyl-4-nitropyrazole with a yield of 23 percent according to M. A. Khan, et al., Can. J. Chem. 49, p. 3566 (1971).
According to V. P. Perevalov, et al., Khim. Geterotsicl. Soedin. 8, p. 1090 (1985), catalytic reduction of this product produces 1-methyl-4,5-diaminopyrazole dihydrochloride with a yield of approximately 79 percent. According to this reaction sequence, the total yield of 1-methyl-4,5-diaminopyrazole amounts to 13 percent throughout all steps.
Better yields are obtained when 5-amino-1-methylpyrazole is converted with isoamyl nitrite, according to H. Dorn, et al., Liebigs Ann. Chem. 717, p. 118 (1968), to produce 5-amino-1-methyl-4-nitrosopyrazole (gross yield approximately 97 percent) and then reduced with tin(II)chloride to give the end product (yield: 67 percent) so that the total yield according to this process is 46 percent throughout all steps.
A corresponding synthesis for 1-benzyl-4,5-diaminopyrazole is described in DE-OS 34 32 983. 5-Amino-1-benzylpyrazole-4-carboxylic acid ethyl ester is obtained from ethoxymethylen
REFERENCES:
patent: 5061289 (1991-10-01), Clausen et al.
M. A. Khan, et al, Canadian Journal of Chemistry, vol. 49, 1971, p. 3566.
K. J. Klebe, et al, Synthesis, 1973, p. 294.
J. P. H. Juffermanns, et al, Journal of Organic Chemistry 51, 1986, p. 4656.
Balzer Wolfgang R.
Clausen Thomas
Gerstung Stefan
Neunhoeffer Hans
Striker Michael J.
Venkat Jyothsna
Wella Aktiengesellschaft
LandOfFree
Composition for the oxidative dyeing of hair containing 4,5-diam does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Composition for the oxidative dyeing of hair containing 4,5-diam, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Composition for the oxidative dyeing of hair containing 4,5-diam will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1865548