COLORING WITH SEMIPERMANENT DYES SUPPLEMENT No. 4 Results• of Tests on 2,6-Dimethyl-p-Aminophenol Hydrochloride Plus: 397 Number and Compound Depth of Hours to Shade Fade Ageing Color on Hair 1. Phenol P P-10 P Medium red-gray 2. Catechol P F-6 P Medium red-gray 3. Resorcinol P F-8 F Pink-gray 4. Pyrogallol P F-8 F Very light pink 5. 3,5-Dimethylphenol P P-10 F Red-brown 6. 2,6-Dimethylphenol P F-5 F Red-gray 7. 2,5-Dimethylphenol P F-6 F Red-gray 8. o-Aminophenol P F-2 F Dark yellow-brown 9. m-Aminophenol P F-8 F Light red-brown 10. 2-Hydroxy-4-aminotoluene P P-10 F Red-brown 14. Aniline P F-4 F Medium pink 15. 0-Phenylenediamine F No color 16. m-Phenylenediamine P F-6 F Red-gray 18. 2,4-Diaminoanisol F No color Results• of Tests on 2,6-Dibromo-p-Aminophenol Plus: 1. Phenol F No color 2. Catechol P P-11 F Medium ash brown 6. 2,6-Dimethylphenol P P-10 F Light green-gray 8. 0-Aminophenol P F-3 F Golden blonde 9. m-Aminophenol F No color 10. 2-Hydroxy-4-aminotoluene P P-15 F Light gray 14. Aniline F No color 16. m-Phenylenediamine P F-8 F Very light gray 17. m-Toluylenediamine P F-4 F Green-blue-gray means passed and F means failed. I•EFERENCES (1) Hcald, R. C., Methods of dyeing hair without the use of an oxidizing agent, Amer. Per[urn., 78, 40 (1963). (2) Clairol, British Patent 1,150,445 (April 30, 1969). (3) Augustin, H., et al., U.S. Patent 3,445,567 (May 27, 1969). (4) Holtzman, H., and Schwartz, M., U. $. Patent 3,446,569 (May 27, 1969). (5) Kalopissis, G., and Bugoul, A., British Patent 1,164,824 (Septetnber 24, 1969). (6) Seetnuller, J. R., U.S. Patent 3,134,721 (May 26, 1964). (7) Corbett, J. F., British Patent 1,063,979 (April 5, 1967). (8) Charle, R., and Lantz, R., U.S. Patent 3,167,478 (January 26, 1965). (9) Kalopissis, G., U.S. Patent 3,485,568 (December 23, 1969). (10) Societe Monsavon-L'Oreal, British Patent 758,743 (October 10, 1956). (11) Milos, Z. B., and Brunner, W. H., U.S. Patent 3,168,441 (February 2, 1965). (12) Lyons, J. R., U.S. Patent 3,480,377 (November 25, 1969). (13) McLaughlin, T. P., U.S. Pate•t 3,369,970 (February 20, 1968).

398 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS (14) Therachemie Chemisch Therapeutische G.M.B.H., British Patent 909,700 (October 31, 1962). (15) Austin, W. E., British Patent 1,035,347 (July 6, 1966). (16) Sardo, F., Shampoo hair coloring compositions for direct dycing of human hair, J. Soc. Cosmet. Chem., 20, 595 (1969). (17) Brunner, W. H., U.S. Patent 3,251,744 (May 17, 1966). (18) Feit, J. A., and Felt, A. J., u.s. Patent 3,041,244 (June 26, 1962). (19) Therachemie Chemiscb Therapeutische Gesellschaft M.B.H., British Patent 1,023,327 (March 23, 1966). (20) Clairol Incorporated, British Patent, 1,097,271 (January 3, 1968). (21) Turner Hall Corporation, British Patent 951,021 (March 4, 1964). (22) Brown, F. G., British Patent 1,113,661 (May 15, 1968). (23) Randebrock, R. E., U.S. Patent 3,415,606 (December 18, 1968). (24) Alexander, P., British Patent 906,526 (September 26, 1962). (25) Lerner, L. L., and Oberstar, H. E., U.S. Patent 3,352,755 (November 14, 1967). (26) Lange, F. W., Canadian Patent 823,629 (September 23, 1969). (27) Brechner, S., U.S. Patent 3,194,735 (July 13, 1965). (28) Peters, L., and Stevens, C. R., U.S. Patent 3,261,754 (July 19, 1966). (29) Zviak, C., and Chilardi, C., British Patent 1,174,741 (December 17, 1969). (30) Clairol International S.A., British Patent 979,405 (January 1, 1965). (31) Tucker, H. H., U.S. Patent 2,890,094 (January 9, 1959). (32) Wilmsmann, H., A comparison of hair and textile coloring, Amer. Perjure., 75, No. 5, 41 (1960). (33) Color Index, The Society of Dyers & Colourists, The American Association of Textile Chemists & Colorists, 2nd Ed., 1956. (34) Tbirtle, J. R., Eastman Kodak Organic Chemical Bull., 40, No. l (1968). (35) Sahninen, I. F., U.S. Patent 2,367,531 (January 16, 1945). (36) Karrer, P., Organic Chernistry, Elsevier Publishing Co., New York, 1946, p. 568. (37) Vittum, P. W., and Brown, G. H., J. Amer. Chem. Soc., 6'8, 2235 (1946). (38) Vittum, P. W., and Brown, G. H., Ibid., 69, 152 (1947).