Self-Sterilizing Materials. 1. Controlled Release of Biguanide Biocides from Polymeric Materials

Abstract

An acrylate monomer with a pendant biguanide, N'-4-(2-acryloyl- oxyethyl)phenyl-N5-4-chlorophenylbiguanide hydrochloride (2), when incor porated covalently into cross-linked polyacrylamide matrices was found to hydrolyzed in water to release N1-4-(2-hydroxyethyl)phenyl-N5-chlorophenylbi guanide hydrochloride (1). When the degree of cross-linking was high, the release was approximately zero-order at least over a period of one week. In con trast to 2, methacrylate and acrylamide monomers with pendant biguanide groups were strongly resistant to hydrolysis. Detailed release profiles from various cross-linked polyacrylamide films containing covalently or non- covalently bound biguanide compounds indicate that the rate of release can be tailored to specific delivery needs.