Bio-catalyzed coloration of cellulose fibers

Cotton fabrics were dyed with dyes generated in situ by laccase-catalyzed oxidative coupling of the colorless 2,5-diaminobenzenesulfonic acid (2,5-DABSA) and 1-hydroxyphenol (catechol). The enzymatic oxidation of the dye intermediates led to cross-coupling reaction products when the reaction was conducted with an excess of catechol. At least fourfold excess of catechol was necessary to achieve satisfactory dye fixation on cotton. Formation of the same colored product using either an equimolar ratio of the reagents or tenfold excess of catechol was observed. Most probably, homo-molecular reactions predominate over the cross-coupling at equimolar ratio of the precursors, while with an excess of catechol, the cross-coupling occurs in higher yield. The reaction was followed using UV-Vis spectroscopy, HPLC, FTIR and MALDI-TOF MS. A reaction pathway for laccase-induced cross-coupling of catechol and 2,5-DABSA yielding a major colored product was proposed.