Hair dyeing compositions

Details Hair dyeing compositions Hair dyeing compositions

1991-02-20

1992-04-14

Clingman, A. Lionel

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

8406, 8407, 8408, 8409, 8410, 8412, 8414, 8416, 8425, 8435, A61K 713

Patent

active

051044129

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to hair dyeing compositions based on oxidation dyes. Hair dyeing compositions of the type in question contain oxidation dye intermediates in a cosmetic carrier. The oxidation dye intermediates used are primary intermediates and coupler substances which form dyes under the effect of oxidizing agents or atmospheric oxygen. The cosmetic carriers used for the oxidation dye intermediates are creams, emulsions, gels, shampoos, foam aerosols or other compositions suitable for application to the hair.
2. Statement of Related Art
By virtue of their intense colors and good fastness properties, so-called oxidation dyes, which are formed by the oxidative coupling of one or more primary intermediate components with one another or with one or more coupler components, play a prominent part in the dyeing of hair. The primary intermediates used are normally primary aromatic amines containing another free or substituted hydroxy or amino group in the para position or ortho position, diamino-pyridine derivatives, heterocyclic hydrazone derivatives, 4-aminopyrazolone derivatives, and tetraaminopyrimidines, while the so-called coupler substances are m-phenylene-diamine derivatives, naphthols, resorcinol derivatives and pyrazolones.
Good oxidation dye intermediates have to satisfy above all the following requirements: they must form the required shades with sufficient intensity during the oxidative coupling reaction. In addition, they must be readily absorbed by human hair without excessively staining the scalp. Dye absorption should also be uniform, i.e. the more heavily stressed ends should not be dyed to a greater extent than the less damaged hair roots. The hair colors produced with them should be highly stable to heat, light, and the chemicals used in the permanent waving of hair. Finally, the oxidation hair dye intermediates should be safe to use from the toxicological and dermatological viewpoint.
3-Aminophenols are already known as oxidation dye intermediates, for example from DE-AS 11 43 605, DE-AS 11 51 900, DE 24 47 017 C2 and DE 30 16 882 Al. However, the hair dyeing compositions produced with these products and known primary intermediate components are unsatisfactory with regard to the fastness properties of the hair colors obtained with them. In particular, it is not possible with the known 3-aminophenols to obtain browns of satisfactory naturalness, brilliance, and depth of color.


DESCRIPTION OF THE INVENTION

It has been found that these requirements are satisfied to a high degree by hair dyeing compositions containing oxidation dye intermediates in a carrier which contain as oxidation dye intermediates N-cycloalkyl-3-aminophenols corresponding to formula (I): ##STR2## which n is an integer of 4 to 8 and R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, methyl groups or chlorine, or salts thereof as coupler components and the primary intermediate components typically used in oxidation hair dyes.
N-Cycloalkyl-3-aminophenols corresponding to formula I in which R.sup.1, R.sup.2 and R.sup.3 represent hydrogen and the group ##STR3## is a cyclopentyl or cyclohexyl group optionally substituted by 1 or 2 methyl groups, are preferred, particularly by virtue of their ready accessibility. The compounds mentioned as examples (coupler components C1, C2 and C3) are particularly preferred.
The N-cycloalkyl-3-aminophenols corresponding to formula I, in which R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, are compounds known from the literature. Their production is known, for example, from EP 181 505 Al. The other N-cycloalkyl-3-aminophenols corresponding to formula I, in which R.sup.1, R.sup.2 and R.sup.3 represent methyl groups or chlorine, may be similarly obtained by the process described therein from the corresponding aminophenol and a cycloalkanone in the presence of a reducing agent in accordance with the following formula scheme: ##STR4##
In addition to 3 aminophenol, suitable aminophenols are, for example, 5-chlo

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