860 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS oxidation NH2 NH p - Phenylenediamine Quinonediimine coupling NH 2 r• r• Bandrowski's Base Green Component purple further 1 coupling Brown Polymer Figure 9. Role of resorcinol in oxidative dyeing wide band of light absorption in the visible region, giving an overall brown shade. The competitive coupling of resorcinol and PPD leading to differently colored dominant products is shown in Fig. 9. In addition, the hetero coupling reaction reduces the extent of PPD self-coupling which produces the purplish shade. CONCLUSIONS The major specific product of p-phenylenediamine and resorcinol cooxidation was separated and identified. Spectroscopic data show it to be a trinuclear species with two PPD and one resorcinol unit in it. This green-colored dye component can balance purple shades in oxidative hair dyeing. ACKNOWLEDGMENT The authors wish to thank Dr. G. Subba Rao, of the National Insti- tutes of Health, for the preparation of mass spectra and for helpful dis- cussions. (Received May 16, 1972) REFERENCES (1) Bandrowski, E., Uber die Oxydation des Paraphenylendiamins und des Paramidophenols, Monatsh. Chem., 10, 123-8 (1889). (2) Bandrowski, E., Uber die Oxydation des Paraphenylenediamins, Chem. Bet., 27, 480-6 (1894). (3) Erdmann, E., Oxydationsprodukte des p-phenylendiamins, Ibid., 37, 2906-13 (1904). (4) Willstatter, R., and Mayer, E., Uber chinondiimid, Ibid., $7• 1499-1507 (1904).

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