HOFMANN DEGRADATION OF ACRYLAMIDE COPOLYMER - SYNTHESIS OF AMINE FUNCTIONALIZED THERMOPLASTIC HYDROGEL

The amine functionalization of an acrylamide copolymer was achieved vi a Hofmann degradation. The starting material, poly(acrylamide-co-methy l methacrylate), was synthesized by radical precipitation polymerizati on. Using this copolymer, Hofmann degradation at 0 degrees C in a wate r-dioxane mixture was done using sodium hypochlorite and NaOH. The res ulting hydrogel could be dissolved in water-tetrahydrofuran mixtures, and the cast film had a water content of 73%. It was found that the co nversion to primary amine was lower, and the extent of a side reaction was higher, compared to those of an acrylamide homopolymer. This was presumed to be due to the lack of the neighboring group effect among a crylamide units since it was a random copolymer. Further modification of this polymer by reacting the amine group is considered to obtain th e desired properties for biomedical applications. (C) 1996 John Wiley & Sons, Inc.