612 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Table I Para-Phenylenediamine Derivatives Color Compound Patent on Hair a Depth of Shade Solubility Fades (Darkest at pH 9.7 After to (g/100 (in Lightest) ml) hours) p-Phenylenediamine F.P. 158,558 Black with red 3 cast p-Toluylenediamine G.P. 47,349 Medium brown 6 sulfate Chloro-p-phenylene U.S.P. 1,434,449 Red brown 5 diamine sulfate Nitro-p-phenylene G.P. 211,567 Dark red ... diamine 1,2,4-Triaminobenzene G.P. 514,003 Deep black 1 dihydrochloride p-Aminodimethylaniline G.P. 47,349 Oxford grey 4 p-Aminodiphenylamine G.P. 92,006 Blue black 2 p-Aminoacetanilide ... No color 7 4.27 6 11.9 6 7.75 38 0.23 30 9.78 30 1.97 8 0.10 24 ...... Derivative used at a concentration of 0.025 moles/1. Table II Ortho-Phenylenediamine Derivatives Depth Color Compound Patent on Hair a of Shade Solubility Fades (Darkest at pH 9.7 After to (g/100 (in Lightest) ml) hours) o-Phenylenediamine 3,4-Toluylenediamine o-Toluylenediamine 4-Chloro-o-phenylene diamine 4- Nitro-o-phenylene diamine 5-Chloro, 3-nitro o-phenylencdiamine G.P. 213,581 Yellow G.P. 213,581 Golden brown G.P. 213,581 Golden grey brown U.S.P. 1,536,725 Brown gold G.P. 190,622 Red orange Orange 3.56 4 2.49 6 2.29 10 0.91 6 0.03 42 0.03 14 Derivative used at a concentration of 0.025 moles/1.

HAIR COLORING WITH OXIDATION DYE INTERMEDIATES 613 Table III Para-Aminophenol Derivatives Color Compound Patent on Hair a Depth of Shade Solubility Fades (Darkest at pH 9.7 After to (g/100 (in Lightest) ml) hours) p-Aminophenol 4-Amino-2-methyl phenol sulfate 4-Amino-3-methyl phenol 4-Amino-2-nitro phenol 2,4-Diaminophenol hydrochloride (areidol) p-Methylamino phenol sulfate (metol) G.P. 51,073 Golden brown G.P. 80,814 Red brown G.P. 80,814 Light grey brown U.S.P. 1,466,747 Red brown G.P. 80,814 Light red brown G.P. 80,814 No color 2 0.63 12 1 1.17 14 5 0.43 10 3 2.97 10 4 7.46 2 6 5.58 Derivative used at a concentration of 0.025 moles/1. Table IV Ortho-Aminophenol Derivatives Color on Compound Patent Hair a Depth of Shade Solubility Fades (Darkest at pH 9.7 After to (g/100 (in Lightest) ml) hours) o-Aminophenol G.P. 103,505 Golden orange 4-Chloro-2-amino G.P. 103,505 Grey yellow phenol 4-Nitro-2-amino G.P. 103,505 Golden brown phenol 5-Nitro-2-amino U.S.P. 1,416,646 Bright yellow phenol 4,6-dinitro-2-amino- G.P. 103,505 Dark orange phenol 6-Chloro-4-nitro-2- ... Dark orange aminophenol hydrochloride 3 0.95 2 5 1.19 10 6 3.47 10 4 0.99 4 1 0.1325øc' 12 2 1.49 28 Derivative used at a concentration of 0.025 moles/1.