Synthesis and photopolymerizations of new methacrylate crosslinkers and antibacterial quanternary ammonium monomers

Abstract

In the first part of this work, new amine monomers were synthesized from the reaction of 3-(acryloyloxy)-2-hydroxypropylmethacrylate (AHM), acrylamide and methacrylamide with various amines and then reacted with various alkylhalides to give six new quaternary ammonium monomers. The photopolymerization of the monomers was investigated by photo-DSC at 30 0C. The reactivities of quaternary ammonium monomers were highly depended on monomer structures. The antibacterial activities of the synthesized amine and quaternary ammonium monomers, their homopolymers and copolymers with 2-hydroxyethylmethacrylate (HEMA) were investigated using S. aureus and E. Coli. It was found that as the alkyl chain length increased, the antibacterial activities of methacrylamide-pyridine QACs increased.In the second part of this work, three new ester-linked diacid monomers and two ether-linked diacid monomers were synthesized from the reaction of succinyl chloride, adipoyl chloride and dodecanedioyl dichloride with tert-butyl ?-hydroxymethyl acrylate and Bisphenol A and triethyleneglycol with tert-butyl ?-bromomethyl acrylate followed by hydrolysis of t-butyl groups with CF3COOH. The structure-reactivity relationship of the monomers was investigated using photo-DSC. TBHMA-Succinyl diacid monomer had highest reactivity and conversion at 40 0C. All monomers showed higher rates of polymerization at 60 0C than the those of 40 0C. Incorporation of 2 per cent crosslinker to HEMA increased the rate of polymerization.