Although oxidation dyes are the most widely used commercial hair dyes, mechanisms for oxidation product formation and color development of oxidation hair dyes have not been completely elucidated. Moreover, because strong oxidizing agents have been employed in the coloring processes from a practical point of view, the coloring processes would likely result in complications including dye decomposition and polymerization reactions.
Herein, we investigated the oxidation products and the mechanism of color development of oxidation hair dyes under alkaline conditions by air, which is a mild oxidizing agent. The reactions of p-aminophenols as precursors with an equimolar amount of m-aminophenols or resorcinols afforded indophenols, which form 1 : 1 coupling products of both the precursor and coupler. The reaction products and acetylated products were isolated and analyzed by 1H/13C-NMR and high-resolution mass spectroscopy.
The indophenol formation process was explored using a visible spectrophotometer. The changes in the reaction rates and the visible spectra were discussed mainly on the basis of substituent effects. Furthermore, the fading of indophenols during the oxidation process could be suppressed by replacing ammonia with sodium carbonate as the alkaline agent.
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