COLORING WITH SEMIPERMANENT DYES 395 be enhanced by the introduction of halogen or alkyl groups into the dye molecule. Eighty indophenol or indamine dyes were prepared using, where applicable, intermediates that are commonly used in permanent hair dyeing and their halogen or alkyl substitution products. These dyes were evaluated for their substantivity to human hair, their fastness to light, and the stability to storage of the dye solutions. Ten of these dyes passed these fastness tests, but with these a full range of colors could not be obtained. It is hoped that further work with this series of dyes might ultimately lead to the ideal semipermanent hair color. (Received November 16, 1970) SUPPLEMENT NO. 1 Results a of Tests on p-Aminodimethylaniline Plus: Number and Compound Depth of Hours to Shade Fade Ageing Color on Hair 1. Phenol P F-4 2. Catechol P P-10 3. Resorcinol P F-6 4. Pyrogallol P F-4 5. 3,5-Dimethylphenol P F-1 6. 2,6-Dimethylphenol P F-3 7. 2,5-Dimethylphenol P F-7 8. 0-Aminophenol P P-10 9. m-Aminophenol P F-7 10. 2-Hydroxy-4-a•ninotoluene P F-5 11. 2-Amino-4-nitrophenol P P-14 12. 2-Amino-5-nitrophenol P F-5 13. 2-Amino-4,6-nitrophenol P P-17 14. Aniline P P-10 15. 0-Phenylenediamine P F-6 16. m-Phenylenediamine P F-3 17. m-Toluylenediamine P F-3 18. 2,4-Dianfinoanisol P F-4 19. Nitro-m-phenylenediamine P F-3 F Gray-blue F Light ash P Light ash P Dull gray-green F Dull green-gray F Dark blue F Dark bright blue F Yellow-blonde F Dark-gray F Purple-gray P Good yellow-brown P Bright yellow P Good dark orange F Medium blue-gray F Dark gold F Medium dark blue F Dark gray F Dark blue P Dark yellow means passed and F means failed.

396 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS SUPPLEMENT NO. 2: Results• of Tests on p-Aminoacetanilidc Plus: Number and Compound Depth of Hours to Shade Fadc Ageing Color on Hair 1. Phenol P F-3 F Light red-brown 2. Catechol P P-12 F Gray-brown 3. Resorcinol F No color 4. Pyrogallol F No color 5. 3,5-Dimethylphenol F No color 6. 2,6-Dimethylphenol P F-8 P Red-blonde 7. 2,5-Dimethylphenol P F-8 P Dark red-gray 8. 0-Aminophenol P F-5 P Gold 9. m-Aminophenol F No color 10. 2-Hydroxy-4-aminotoluene F No color 11. 2-Amino-4-nitrophenol P P-16 P Very dark orange 12. 2-Amino-5-nitrophenol P P-12 P Good bright yellow 13. 2-Amino-4,6-dinitrophenol P P-23 P Dark rcd-orange 14. Aniline P F-4 F Medium dark gray 15. 0-Phenylenediamine P F-1 F Dark gray-brown 16. m-Phenylenediamine P F-5 F Dark red 17. m-Toluylenediamine P F-4 F Medium gray-brown 18. 2,4-Diaminoanisol P P-20 F Gray-brown 19. Nitro-m-phenylenediamine P F-2 P Bright yellow SUPPLEMENT NO. 3: Results ,* of Tests on p-Aminophenol Plus: 1. Phenol P P-18 F Medium gray-blonde 2. Catechol P P-18 F Gray-brown 3. Resorcinol P P-12 F Light green-blonde 4. Pyrogallol P P-14 F Medium brown 5. 3,5-Dimethylphenol P F-8 F Golden blonde 6. 2,6-Dimethylphenol P P-14 F Medium red-brown 7. 2,5-Dimethylphenol P P-10 F Red 8. 0-Aminophenol P F-2 F Medium browu 9. m-Aminophenol P P-14 P Ash blonde 10. 2-Hydroxy-4-a•ninotoluene P P-27 F Dark red-orange 11. 2-Amino-4-nitrophenol P F-5 F Medimn brown 12. 2-Amino-5-nitrophenol P P-11 P Dark yellow 13. 2-Amino-4,6-dinitrophenol P P-33 P Dark red-orange 14. Aniline P P-13 P Golden brown 15. 0-Phenylenediamine P F-8 F Golden blonde 16. m-Phenylenediamine P P-13 F Medium ash brown 17. m-Toluylenediamine P F-5 F Dark red-brown 18. 2,4-Diaminoanisol P F-4 F Dark red-brown 19. Nitro-m-phenylenediamine P F-9 P Dark yellow means passed and F means failed.