Synthesis and Antibacterial Activities of Water-Soluble Methacrylate Polymers Containing Quaternary Ammonium Compounds

Abstract

New water-soluble methacrylate polymers with pendant quaternary ammonium (QA) groups were synthesized and used as antibacterial materials. The polymers with pendant QA groups were obtained by the reaction of the alkyl halide groups of a previously synthesized functional methacrylate homopolymer with various tertiary alkyl amines containing 12-, 14-, or 16-carbon alkyl chains. The structures of the functional polymer and the polymers with QA groups were confirmed with Fourier transform infrared and H-1 and C-13 NMR. The degree of conversion of alkyl halides to QA sites in each polymer was determined by H-1 NMR to be over 90% in all cases. The number-average molecular weight and polydispersity of the functional polymer were determined by size exclusion chromatography to be 32,500 g/mol and 2.25, respectively. All polymers were thermally stable up to 180 degrees C according to thermogravimetric analysis. The antibacterial activities of the polymers with pendant QA groups against Staphylococcus aureus and Escherichia coli were determined with broth-dilution and spread-plate methods. All the polymers showed excellent antibacterial activities in the range of 32-256 mu g/mL. The antibacterial activity against S. aureus increased with an increase in the alkyl chain length for the ammonium groups, whereas the antibacterial activity against E. coli decreased with increasing alkyl chain length. (c) 2006 Wiley Periodicals, Inc