HAIR COLORING WiTH OXIDATION DYE INTERMEDIATES (315 Table V I Meta-Phenylenediamine Derivatives Alone and with p-Aminodiphenylamine Compound Patent Alone Solubility at pH 9.7 Color on Hair (g/100 (from 0.025 M ml) Solution) Mixed Solution with P.A.D.A. Fades After (in Color on Hair a hours) m-Phenylenediamine G.P. 255,858 42.8 Very light grey Blue black 12 Chloro-m-phenylene G.P. 255,858 diamine Nitro-m-phenylene G.P. 255,858 diamine m-Toluylenediamine G.P. 255,858 2,4-Diaminoanisol sulfate 4-Methoxy-O- methyl-m-phenyl- enediamine 1,3,5-Triamino- benzenetrihydro- chloride 2,4,0-Triamino toluene trihydro- chloride p-Aminodiphenyl- amine (alone) G.P. 228,245 G.P. 230,630 1.19 Very light red Grey black 22 grey brown 1.71 Bright yellow Golden brown 28 4.00 Very light Blue black 24 yellow brown 14.7 Light grey Black 18 brown 1.10 Medium grey Black 16 brown 8.63 No color Dark brown 12 13.4 No color Grey brown 20 Brown black 14 Solutions were 0.01 34r in both components. with p-phenylenediamine (P.P.D.) p-aminodiphenylamine (P.A.D.A.), or p-aminophenol (P.A.P.). The properties of eight m-phenylene diamine derivatives dyed alone and mixed with P.A.D.A. are given in Table VI. With the exception of nitro-m-phenylenediamine the colors given with m-phenylenediamine derivatives, when dyed alone, were so light that no fadeometer tests were run. Hair dyed with nitro-m- phenylenediamine faded after an exposure of two hours. The results of dyeing hair with equimolar quantities of m-phenylene- diamine derivatives mixed with P.P.D. or P.A.P. are given in Table VII. It is apparent that m-phenylenediamine, m-toluylenediamine, 2,4,-di- aminoanisol sulfate and 4-methoxy-6-methyl-m-phenylenediamine all were effective in giving a blue-black color when mixed with P.P.D. which was many times darker and showed a tenfold increase in light fastness compared with that of p-phenylenediamine alone. This illustrates the

616 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Table VII Meta-phenylenediamine Derivatives Mixed with p-Phenylenediamine or p-Aminophenol Compound Mixed Solution with Mixed Solution with P.P.D. P.A.P. Fades Fades After After (in (in Color on Hair a (hours) Color on Hair a hours) m-Phenylenediamine Chloro-m-phenylene diamine Nitro-m-phenylene diamine m-Toluylenediamine 2,4-Diaminoanisol sulphate 4-Methoxy-6-methyl-m-phenylene- diamine 1,3,5-Triaminobenzene trihydrochloride 2,4,6-Triaminotoluene trihydrochloride p-Phenylenediamine (alone) p-Aminophenol (alone) Blue black 42 Red with a 2 grey cast Black with a 20 Light grey 6 red cast Yellow 20 Bright 2 brown yellow Black with a 50 Dark red 16 purple east Black 50 Orange red 8 Black 46 Orange red 4 Red brown 14 Light grey 18 brown Grey brown 22 Light golden 6 Brown Dark brown 4 ...... ...... Light golden 4 brown Solutions were 0.01 M in both components. Table VIII Meta-Aminophenol Derivatives Alone and with p-Aminodiphenylamine Mixed Solution with Alone P.A.D.A. Solubility Fades at pH 9.7 Color on Hair After (g/100 (from 0.025 M Color on Compound Patent ml) Solution) Hair • hours) m-Aminophenol G.P. 210,643 3.85 No color Blue black 3,5-Diaminophenol ... 3.57 No color Red brown hydroehlorid e black Diethyl-m-amino- U.S.P. 3,216,899 0.20 Very light Dark red phenol grey brown brown p-Amino-0-eresol (4- U.S.P. 3,210,252 0.65 Golden Dark grey amino-2-hydroxy- blonde purple 1-methylbenzene) p-Aminodiphenyl- . ........ Brown black amine (alone) 28 28 5 8 14 Solutions were 0.01 M in both components.