390 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS three phenyl groups in its structure. In order to determine whether Bandrowski's base is also formed when sodium hypoch!orite is used as the oxidizing agent p-phenylenediamine was subjected to the treatment shown above, except that the solution was acidified to a pH of 6.0 before filtering. A 62% yield of oxidation product was obtained which, upon reprecipitation from a pyridine solution by the addition of a large amount of water, melted at 236øC. Bandrowski's base that had been prepared by the slow oxidation of an alkaline solution of p-phenylenedi- amine with hydrogen peroxide and reprecipitated in the same way melted at 236øC. The mixed melting point was also 236øC, indicating that the two compounds were the same. Intermediates used in Preparation of Indophenols and lndamines Two types of compounds were used for the formation of indophenols and indamines. The first were para-substituted compounds which, in order to discourage the formation of products having more than two phenyl rings, contain only one free amino group. These were coupled with phenols that have the position para to the hydroxy group free with aminophenols that have the position para to the hydroxy or the amino group free and with phenyl amines that have the position para to the amino group free. There are a great many para compounds that can be used but, in order to limit the scope of this paper, the five listed in Table VII are the only ones considered. For the same reason the phenols used are limited to those listed in Table VIII the aminophenols to those in Table IX and the phenylamines to those in Table X. Table VII Para Compounds used in Indophenol and Indamine Formation A. p-Aminodimethylaniline B. p-Aminoacetanilide C. p-Aminophenol D. 2,6-Di•nethyl-p-aminophenol HCI E. 2,6-Dibrorno-p-aminophenol (CH3)2N•NH2 HO•NH2 gr HO•NH2 Br CH,•C0••NH2 (CHa) H0•NH,2HC1 (CH•)

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`