SYNTHESIS OF SOME NEW QUATERNARY DYES 413 With the help of these dyes, white hair is dyed red and blue respectively. In the present work (5), an attempt has been made to enrich and enlarge the field of application of anthraquinone dyes for cosmetic purposes by synthesizing and studying a few new dyes, corresponding to the three following series: (Series I) 0 OH A- (Series II) o ,, OH '• N--R• o (Series III) In the above, R• and R2 are lower alkyl residues which, in Series I and II, can also form part of a heterocyclic residue such as, for example, a morpholine or piperidine residue. In every case R3 is a lower alkyl residue A- is a halogen or methosulphate anion, and n is a whole number equal to 2 or 3. The following compounds may be mentioned specifically: Methyl[2-(fimethyl morpholinium) ethylamino-anthraquinone] sulphate, methyl[2-(fimethyl diethyl ammonium) ethylamino-anthraquinone] sulphate, methyl [2-(fitrimethyl ammonium) propylamino-anthraquinone] sulphate, methyl[1-hydroxy 4-(Froethyl piperidinium) propylamino-anthraquinone] sulphate,

414 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS methyl[1-hydroxy 4-(t•methyl morpholinium) ethylamino-anthraquinone] sulphate, and bismethyl [1-hydroxy 2,4-(ptrimethylammonium) phenylamino-anthraqui- none] sulphate. SYNTHESIS So far as Series I is concerned, the products are obtained either from 2-chloro-anthraquinone, by condensation with the corresponding tertiary- primary diamine and subsequent quaternization, or from 2-amino-anthra- quinone by the action of N,Ndiethylamino ethyl chloride, and quaterniza- tion. As regards Series II, the products are obtained from quinizarine by substi- tution of one of the OH groups by a t•amino ethyl morpholine or a 7amino propyl piperidine, followed by quaternization. Finally, with regard to Series III, the compound mentioned is synthesized from purpurine by the action of N,Ndimethyl pphenylene diamine, and subsequent quaternization. APPLICATION TO HAIR DYEING Hair dyeing is effected by the application, at normal temperature and in the usual manner, of an aqueous solution of dyes, in fairly large concentra- tions but generally from 0.05M to 0.2M. The pH of the solutions may vary within fairly wide limits, e.g. between 4 and 9. The tints obtained on white hair are respectively: For Series I • yellow to orange-yellow for Series II -- violet to purple-violet for Series III -- grey. The compounds of Series II were studied regarding resistance to sunlight. Work on the other two Series is in progress. These are based on evaluations similar to those perfected for textiles (6). In such evaluations, degrees of "fastness" or "resistance" are classified, by convention, in a certain order, from 1 to 8. More details are to be found elsewhere (7). It is quite clear that the transposition of this method from textiles to hair involves a certain arbitrary factor and that, in addition, the standard figures cannot have the same absolute significance for hair as for wool. In class II, a degree of fastness between 4 and 5 for a hair dye, can be regarded as excellent. In addition, studies on the physiological behaviour of some of these dyes, when in contact with the skin, have also been carried out. These studies