Synthesis and Biocidal Activities of Polymer. II. Bactericidal Activity of Homopolymer of AcDP and Copolymer of AcDP with MMA

Abstract

Abstract The bactericidal monomer 2,4,4′-trichloro-2′-acryloyloxydiphenyl ether (AcDP) was synthesized from 2,4,4′-trichloro-2′-hydroxydiphenyl ether (DP) and acryloyl chloride in the presence of triethylamine in dry THF at 20°C. The synthesized AcDP was identified by IR, 1H-NMR, and GC-MS spectra. The homopolymers of AcDP were obtained using benzoyl peroxide as a thermal initiator in toluene under different experimental conditions such as various initiator concentrations, polymerization temperatures, and polymerization times. The copolymer of AcDP and methyl methacrylate (MMA) was synthesized with a thermal initiator. Poly(AcDP) and poly(AcDP-co-MMA) were identified by IR and 1H-NMR spectra. The maximum weight-average molecular weights ( M w) of poly(AcDP)s and poly(AcDP-co-MMA)s were 6,700 and 15,600, respectively. The monomer reactivity ratios, r 1 (AcDP) and r 2 (MMA), determined by the Kelen–Tüdös method, were 0.26 and 1.12, respectively. The glass transition temperature and the decomposition temperature of poly(AcDP) were 73.4 and 348°C, respectively. The bactericidal activities of AcDP, poly(AcDP), and poly(AcDP-co-MMA) were studied using the agar dish test. The bactericidal activities of AcDP and its polymers as well as DP against Pseudomonas aeruginosa were very excellent compared to those of such control polymers as poly(MMA) and poly(ethylene-co-vinyl acetate). The bactericidal activities decreased in the order DP > AcDP > poly(AcDP) > poly(AcDP-co-MMA) against P aeruginosa.