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

摘要

The amine functionalization of an acrylamide copolymer was achieved via Hofmann degradation. The starting material, poly(acrylamide-co-methyl methacrylate), was synthesized by radical precipitation polymerization. Using this copolymer, Hofmann degradation at 0 degrees C in a water-dioxane mixture was done using sodium hypochlorite and NaOH. The resulting hydrogel could be dissolved in water-tetrahydrofuran mixtures, and the cast film had a water content of 73%. It was found that the conversion 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 acrylamide units since it was a random copolymer. Further modification of this polymer by reacting the amine group is considered to obtain the desired properties for biomedical applications. (C) 1996 John Wiley & Sons, Inc. [References: 19]