5-alkoxy-2,4-diamino-alkyl-benzenes and hairdye compositions bas

Details 5-alkoxy-2,4-diamino-alkyl-benzenes and hairdye compositions bas 5-alkoxy-2,4-diamino-alkyl-benzenes and hairdye compositions bas

1988-02-26

1989-08-08

Willis, Prince E.

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

8411, 8416, 8421, 564443, 564305, A61K 713, C07C 9140, C07C 8752

Patent

active

048549355

DESCRIPTION:

BRIEF SUMMARY
The subject of the invention is new 5-alkoxy-2,4-diaminoalkylbenzenes and compositions for oxidative hair coloring based on known developer substances and 5-alkoxy-2,4-diaminoalkylbenzenes as coupler substances.
For hair coloring, oxidation dyes have attained substantial significance. Here the coloring is produced by the reaction of particular developer substances with particular coupler substances, in the presence of a suitable oxidation agent.
The coupler substances preferably used are m-phenylenediamine and its derivatives, such as 2,4-diaminoanisole, 2,4-diaminophenetole, 2,4-diaminophenoxyethanol, 3,5-diamino-2,6-dimethoxypyridine, 2-amino-4-(2'-hydroxyethyl)aminoanisole, as blue couplers; 1-naphthol, m-aminophenol, 3-amino-5-hydroxy-2,6-dimethoxypyridine, and 5-amino-o-cresol, as red couplers; and resorcin, 2-methylresorcin and 4-chlororesorcin, as couplers for the brown-blonde range.
Preferred developer substances are 2,5-diaminotoluol, 4-aminophenol and 1,4-diaminobenzene, but 2,5-diaminoanisole, 2,5-diaminobenzylalcohol and 2-(2'-hydroxyethyl)-1,4-diaminobenzene have also attained a certain importance. In particular cases, tetraaminopyrimidine can also be used as a developer substance.
Numerous special requirements are made for oxidation dyes used for coloring human hair. For instance, they must be toxicologically and dermatologically unobjectionable, and must enable the attainment of colorings having the desired intensity. It is also necessary to be able to produce a broad palette of different shades, by combining suitable developer and coupler substances. Furthermore, the attainable hair dyes must have good light fastness, permanent wave fastness, and acid resistance and must not rub off. In each case, however, such hair dyes must remain stable, without being affected by light, chemicals and rubbing, over a period of at least 4 to 6 weeks.
Although the combinations of the above-mentioned developer and coupler substances used at the present time in hair dye compositions do largely meet these requirements in terms of their technical application properties, they cannot satisfactorily meet the requirements in terms of toxicological properties. In particular, it is now being required that compounds used in hair dye compositions be non-mutagenic, or only slightly mutagenic, in test systems such as those of B. N. Ames.
For instance, 2,4-diaminotoluol, which has good coloring properties, is prohibited in many countries as a hair dye because of its mutagenic action.
A reddish tinge such as is obtained with the known coupler substance 2-amino-4-(2'-hydroxyethyl)aminoanisole, makes it difficult to attain a range of shades, because the proportion of red that is obtained in addition to the desired blue has to be compensated for by the addition of further color components. The shift of the depth of tone that then occurs must also be taken into consideration.
A green tinge, resulting for example from dyeing with 3,5-diamino-2,6-dimethoxypyridine, is also problematic. This kind of green tinge makes it difficult to produce ash-blonde tones, in which a bluish highlight is desirable. Compensating for the greenish coloring again necessitates the addition of further color components, which once again makes it more difficult to attach gradations of light tones.
2,4-Diamino-5-tetrafluoroethoxytoluol, known from the applicant's own German Patent Disclosure Document DE-OS No. 3 430 513, although it exhibits no mutagenic action in the Ames test, nevertheless is not completely satisfactory in terms of color depths and light fastness of the colors attainable with this compound. Furthermore, pure 2,4-diamino-5-tetrafluoroethoxytoluol can be produced only with expensive chromatographical separations on the gram scale, so that hair dye compositions containing 2,4-diamino-5-tetrafluoroethoxytoluol are much more expensive.
It is therefore the object of the invention to furnish a hair dye composition based on novel coupler substances which can be produced and inexpensively, and which in combination with suitable developer substa

REFERENCES:
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patent: 4125367 (1978-11-01), Bugaut et al.
patent: 4171203 (1979-10-01), Rose et al.
patent: 4323360 (1982-04-01), Bugaut et al.
patent: 4324553 (1982-04-01), Bugaut et al.
patent: 4566876 (1986-01-01), Brown et al.
John F. Corbett, Benzoquinone Imines etc., J. Chem. Soc., Perkin Trans., 2, 1972, pp. 999-1005.

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