Use of p-ureidoalkylamino-nitrobenzene derivatives in hair dyein

Details Use of p-ureidoalkylamino-nitrobenzene derivatives in hair dyein Use of p-ureidoalkylamino-nitrobenzene derivatives in hair dyein

1985-08-14

1986-12-16

Clingman, A. Lionel

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

8405, 8407, 564 47, A61K 713, C07C12719, D06P 119, D06P 314

Patent

active

046294678

DESCRIPTION:

BRIEF SUMMARY
It is an object of the invention to use nitro dyes for hair dyeing, whereby p-ureidoalkylamino-nitrobenzene derivatives in hair dyeing compositions are used as well as new p-ureidoalkylamino-nitrobenzene derivatives.
Nitro dyes are nowadays widely used in hair dyeing compositions. They are used in oxidation hair dyeing compositions as additions for generating natural or modern dye nuances. By combining of a plurality of differently dyed nitro dye compounds it is also possible to produce hair dyes which are able to dye the hair in natural to modern nuances without the use of oxidation agents.
For example, by combining an orange dye with a blue coloring nitro dye a natural appearing brown coloring may be obtained. However, it is also possible to achieve a similar result with a yellow coloring nitro dye substance.
Therefore, special nitro dye substances are required which are able to color the hair in an intensive pure lemon yellow which must be free from red constituents. Moreover, many other requirements are necessary. The nitro dye substances must be unobjectionable with respect to toxicological and dermatological requirements. Their use in oxidation hair dyes presumes that they are stable in the presence of hydrogen peroxide in an alkaline solution. Furthermore, they should be stable with respect to reduction agents which very often are constituents of oxidation hair dyes. Furthermore, a good light, acid and friction genuiness is required for the generated hair coloring. Furthermore, the nitro compounds should be able to be made very simply and cost effective.
The substituted amino-nitrophenoles which are heretofore described in the literature for a yellow coloring of the hair fulfill the aforementioned requirements only insufficiently. The 4-nitro-3-(2'-hydroxyethyl amino)-phenol described in the International Journal of Cosmetic Science 1982, pages 25-35 results in a lemon yellow coloring, but it is rather weak in its color. Two further isomers, namely the 4-nitro and the 5-nitro-2-(2'-hydroxyethyl amino)-phenol are not yellow coloring but orange coloring nitro dyes with interfering red constituents (see DE-PS 928,909 and DE-OS 3 231 455). The latter mentioned nitro dye is very pH-sensitive and shows undesirable color changes in acid or alkaline effects.
Further known yellow nitro color substances are the o- and p-nitroaniline derivatives mentioned in the DE-AS 1,619,393. These compounds substantially fulfill the requirements when applied, but are unsatisfactory with respect to the physiological characteristics.
Surprisingly it had been found that the aforementioned disadvantage can be overcome by using a 1-ureidoalkyl amino-4- nitrobenzene compound of the general formula I ##STR3## wherein R represents hydrogen or a hydroxy alkyl residue with 2 to 4 carbon atoms and n a whole number of 2 to 4 as a dye in hair dye compositions.
The discovery that compounds of the general formula I do fulfill all requirements necessary for yellow coloring nitro dyes used in hair dyeing compositions is very surprising because a compound of the general formula I with R=H and n=2 is already known from DE-OS 1,945,451 as a preliminary stage for the synthesis of the recommended compound N-(.beta.-ureidoethyl)-paraphenylene diamine as a color base for oxidation hair dyes.
The dyes of the formula I which are described for the inventive application, the ones wherein R denotes a hydroxy alkyl residue with 2 to 4 carbon atoms are new.
Therefore, a subject matter of the present invention are also new 1-[N-hydroxy alkyl), N-(ureidoalkyl)-amino]-4-nitrobenzenes of the general formula II ##STR4## whereby R' constitutes a hydroxy alkyl residue with 2 to 4 carbon atoms and n a whole number of 2 to 4.
These compounds are characterized by an improved water solubility in contrast to the ones of formula I with R=H.
The p-ureidoalkyl amino-nitrobenzenes of the formula I (which include the new compounds of the formula II) may be made from inexpensive preliminary steps as follows:
Based on p-chloro-or p-fluoro nitrobenzene III a nucleophilic e

REFERENCES:
patent: 3629330 (1971-12-01), Brody et al.
patent: 3642423 (1972-02-01), Bil et al.
patent: 3697215 (1972-10-01), Kalopissis et al.
patent: 4008272 (1977-02-01), Kalopissis et al.
International Journal of Cosmetic Science 1982, vol. 4, 1982, pp. 25-35.
Colour Index, Third Edition, vol. 4, published by The Society of Dyers and Colourists.
Hair Dyes, J. C. Johnson, Noyes Data Corporation, 1973, pp. 3-91 and 113-139.
Cosmetics, Science and Technology (1957), Interscience Publishers Inc., N.Y. pp. 503-511.

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