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A novel reactive dyeing method for silk fibroin with aromatic primary amine-containing dyes based on the Mannich reaction

Weiguo Chen,Pu Gao,Hua Jiang,Zhihua Cui

Chemical modification of silk fibroin is a useful method for improving its performance. There are many existing methods of protein modification, some of which are limited for application to silk by the disadvantages of severe reaction conditions, poor reaction selectivity and problems with characterization of the product. In this paper, a series of dyes containing aromatic primary amine groups was designed and synthesized for modification of silk fibroin via the Mannich reaction. This three-component Mannich modification showed several advantages, such as mild reaction conditions, good selectivity, easy characterization and high fastness. In particular, the degree of modification could be established visually according to the color yield and the color fixation on silk fibroin. Therefore, the Mannich reaction of silk with dyes containing aromatic primary amine groups may become a novel reactive dyeing method. Studies of structure-performance relationships showed that suitable dyes for dyeing of silk should meet the following criteria: (1) High nucleophilicity of the aromatic primary amine group. (2) No high electron cloud density center around the amino group.