COLORING WITH SEMIPERMANENT DYES Table VIII Phenols Used for Coupling with the Para Compounds 391 1. Phenol 2. Catechol 3. Resorcinol 4. Pyrogallol 5. 3,5-Ditnethylphenol 6. 2,6-Dimethylphenol 7. 2,5-Dimethylphenol 0H OH OH (CH•) 2 (CH,•)2 {OH (CH•)• OH OH OH OH OH (CHa),• (CH3h Table IX Aminophenols Used for Coupling with the Para Compounds 8. 0-Aminophenol 9. m-Aminophenol 10. 2-Hydroxy-4-aminotoluene 11. 2-Amino-4-nitrophenol 12. 2-Amino-5-nitrophenol 13. 2-Amino-4,6-dinitrophenol OH NH• CHa NO,, 0H OH NO, NO` OH NH,• NO`

392 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Table X Phenylmnines Used for Coupling with the Para Cronpounds 14. Aniline 15. 0-Phenylenedia•nine 16. m-Phenylenedimnine 17. m-Toluylenediamine 18. 2,4-Dimninoanisol 19. Nitro-m-phenylenedimnine NH2 NH2 NHz 0CHa NHz NH•z NH2 NH• CH,• NH,• NH• N02 Ntt,2 NH2 Experimental Results Of the possible 95 indophenols or indamine dyes that can be prepared from the intermediates listed, 80 have been made and tested, including all possible 19 each from p-aminodimethylaniline, p-aminoacetanilide, and p-aminophenol. The results of the substantivity, light fastness, and ageing tests, and a description of the color produced on dyeing hair are summarized in the tables given in the supplements to this paper. A com- plete range of colors can be obtained with these dyes. Of the 80 dyes tested, 8 failed the substantivity test. Of the 72 remaining dyes, 42 failed the light fastness test, and 50 failed the ageing test. This is possible be- cause 32 dyes failed both the light fastness and ageing tests. Ten of the dyes passed all three of these tests and varied, in the shades produced on hair, from a yellow, to an orange, to a pink, and to several shades of brown. All of the blue or gray shades, in this series, failed to pass either the ageing or light fastness tests or both. The presumed structures of the dyes that passed these three tests are shown in Table XI. Dye number D-1 cannot be included in the above table and so its presumed structure is given separately.