Study on coloration of silk based on coupling reaction with a diazonium compound

This paper describes how coloration of silk can be achieved using a coupling reaction between a diazonium compound, made from Color Base Red G (C.I. 37105) and tyrosine residues in the silk protein fibroin. A pigment with an azo structure obtained from the reaction between the diazonium of Color Base Red G with p-methylphenol was synthesized and studied as a model compound for the coloration reaction. The colored materials were characterized using UV-vis, FT-Raman, FT-IR, 1H-NMR, and mass spectroscopy. Both the colored silk and the model compound gave yellow colors with absorption maxima in the region of 400 nm. The results suggest that the use of coupling reactions could be developed into a dyeing method for protein fibers or other protein materials that contain tyrosine residues. Because the chromophores are incorporated into the protein chains, such dyed silks should have good wet fastness properties.