Hair colorants based on perimidine derivatives

Details Hair colorants based on perimidine derivatives Hair colorants based on perimidine derivatives

1998-03-27

1999-07-13

Liott, Caroline D.

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

8408, 8423, 8567, A61K 713

Patent

active

059220864

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to the use of perimidine derivatives as a coupler substance for the preparation of oxidation dyestuffs, and to hair colouring compositions which comprise perimidine derivatives.
During oxidative dyeing of keratin fibres, dyestuffs or pigments are produced in the fibre by reaction of coupler substances with developer substances in the presence of oxidizing agents.
Numerous use requirements are imposed on such oxidation dyestuffs, in particular in respect of fastness to light, fastness to acid, fastness to perspiration, fastness to rubbing, fastness to permanent waving, fastness to washing, heat stability, fixation capacity, evenness and tinctorial strength. They should also be toxicologically and dermatologically acceptable. Oxidation dyestuffs have acquired particular importance because of their high tinctorial strength and good fastness properties in particular (see, for example, J. F. Corbett, in K. Venkataraman, The Chemistry of Synthetic Dyes, Vol. V, 478-505 (1971); J. F. Corbett, Rev. Progr. Coloration, Vol. V, 52-58 (1985)).
In practice, coupler and developer substances mixed with suitable auxiliaries are available as hair colouring compositions, from which the dyestuff is then formed in the keratin fibre.
To produce blue colour shades, 1,3-diaminobenzene derivatives are chiefly employed as couplers and 1,4-diaminobenzene derivatives are chiefly employed as developer substances.
To produce black and black-brown colour shades, however, it is necessary to employ mixtures of two or more coupler components, for example mixtures of 1,3-diaminobenzene derivatives with 3-aminophenol and/or 1,3-dihydroxybenzene derivatives.
Surprisingly, it has now been found that in addition to blond, red and brown colour shades, blue-black to black dyeings can be obtained by a direct route, without the need to employ mixtures, if perimidine derivatives are used as coupler substances.
The present invention accordingly relates to the use of compounds of the general formula I ##STR2## wherein R.sup.1 is hydrogen, (C.sub.1 -C.sub.6)-alkyl, hydroxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, carboxy-(C.sub.1 -C.sub.6)-alkyl, 2,3-dihydroxypropyl, 2-hydroxy-3-((C.sub.1 -C.sub.4)-alkoxy)-propyl, cyano-(C.sub.1 -C.sub.6)-alkyl, carbamoyl-(C.sub.1 -C.sub.6)-alkyl, ((C.sub.1 -C.sub.4)-alkoxy)carbonyl-(C.sub.1 -C.sub.4)-alkyl, benzyl, phenyl or substituted phenyl; -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, oxo-(C.sub.1 -C.sub.6)-alkyl, carboxy-(C.sub.1 -C.sub.6)-alkyl, ((C.sub.1 -C.sub.4)-alkoxy)carbonyl-(C.sub.1 -C.sub.6)-alkyl, carbamoyl-(C.sub.1 -C.sub.6)-alkyl, carboxyl, ((C.sub.1 -C.sub.4)-alkoxy)carbonyl, carbamoyl, phenyl, substituted phenyl or pyridyl; dyestuffs.
Alkyl groups can be straight-chain or branched and are, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl. Analogous conditions apply to substituted alkyl groups and alkoxy groups. Examples of substituted alkyl groups are hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, methoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, carboxymethyl, 2-carboxyethyl, 2-ethoxycarbonylethyl, 2-cyano-ethyl and methoxycarbonylmethyl.
Unsubstituted and substituted (C.sub.1 -C.sub.4)-alkyl groups are preferred.
Substituted phenyl can carry 1, 2 or 3 identical or different substituents. Examples of suitable substituents are hydroxyl, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -(C.sub.1 -C.sub.4)-alkoxy, hydroxy-(C.sub.1 -C.sub.4)-alkyl, fluorine, chlorine or bromine. Pyridyl can be 2-pyridyl, 3-pyridyl or 4-pyridyl.
The radicals R.sup.3 can be located in any desired positions on the naphthalene framework. Where two radicals R.sup.3 are present, they can be identical or different.
R.sup.1 is preferably hydrogen, methyl, ethyl, hydroxymethyl, hydroxyethyl, carboxymethyl or benzyl.
R.sup.2 is preferably hydrogen, methyl, ethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl or phenyl.
In compounds in which n is other t

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