Microwave-Assisted Synthesis of a New Hydantoin Monomer for Antibacterial Polymeric Materials

Abstract

11-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)undecyl acrylate was synthesized in a two-step procedure using microwave irradiation. Poly(acrylates) containing fluorinated and hydantoin (5,5-dimethylimidazolidine-2,4-dione) moieties were prepared by free radical polymerization of 2-(perfluorooctyl)ethyl acrylate and the synthesized monomer with the aim of obtaining low surface energy polymeric materials with properties of contact-active biocides. Polymeric films were treated with a bleaching solution in order to convert the hydantoin units to N-halamines, well-known contact-active biocides. The reversibility of the chlorination reaction, necessary to impart a renewable biocide effect, was investigated by Fourier Transform-Attenuated Total Reflection. Preliminary biological tests conducted against Bacillus megaterium demonstrated the effective biocide properties of the prepared materials.