Synthesis of Reactive Polymeric Dyes as Textile Auxiliaries

Abstract

Abstract New polymeric materials containing amino‐substituted azobenzene chromophores and reactive functional groups and characterized by some hydrophilicity were prepared with the aim of investigating alternative textile dyeing routes. The indicated materials were obtained either by copolymerization of suitable monomers or by modification of preformed polymers. In both cases commercial 4‐amino‐2′,3‐dimethylazobenzene (FG) was used as chromogenic compound. According to the first synthetic strategy, the methacrylamido derivative of FG was copolymerized by free radical initiation with different monomers, such as methyl methacrylate, glycidyl methacrylate, N ‐ tert ‐butylacrylamide, methacrylic acid, N ‐vinyl‐2‐pyrrolidinone, and vinyl acetate. Reaction of FG with preformed polymers containing epoxy groups generally afforded crosslinked materials. On the other hand, low FG loading extents were recorded by amidation of polymers containing carboxylic groups. Indeed, almost quantitative conversions were obtained only in the reaction of FG with anhydride containing polymers. The chemical structure, molecular weight properties, and the physical‐chemical characteristics of all synthesized polymeric dyes were thoroughly investigated. Some very preliminary dyeing tests of different cloth types with the prepared polymeric dyes were also performed. UV absorption spectrum of poly(FGMAA) and poly(FGMAA‐ co ‐MMA) in chloroform at 25 °C (FGMAA = 4‐methacrylamido‐2′,3‐dimethylazobenzene). magnified image UV absorption spectrum of poly(FGMAA) and poly(FGMAA‐ co ‐MMA) in chloroform at 25 °C (FGMAA = 4‐methacrylamido‐2′,3‐dimethylazobenzene).