Copolymers of a new methacrylate monomer bearing oxime ester and ether with methyl methacrylate: Synthesis, characterization, monomer reactivity ratios, and biological activity



The free-radical copolymerization of 2-metil-1-{[(1-{4-[(4-nitrobenzil)oksi]fenil}etilidene)amino]oksi}prop-2-en-1-on (NBOEMA) with methyl methacrylate (MMA) was carried out in 1,4-dioxane at 65 ± 1°C. The copolymers were analyzed by Fourier transform infrared spectroscopy, 1H-NMR, 13C-NMR, and gel permeation chromatography (GPC). Elemental analysis was used to determine the molar fractions of NBOEMA and MMA in the copolymers and for the characterization of the compounds. The monomer reactivity ratios were calculated according to the general copolymerization equation with the Kelen–Tudos and Fineman–Ross linearization methods. The polydispersity indices of the polymers, determined with GPC, suggested a strong tendency for chain termination by disproportionation. The thermal behaviors of the copolymers with various compositions were investigated by differential scanning calorimetry and thermogravimetric analysis. The glass-transition temperature of the copolymers increased with increasing NBOEMA content in the copolymers. Also, the apparent thermal decomposition activation energies were calculated by the Ozawa method with a Shimadzu TGA 60H thermogravimetric analysis thermobalance. All of the products showed moderate activity against different strains of bacteria and fungi. The photochemical properties of the polymers were investigated by UV spectroscopy. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010