Radical polymerization of new functional monomers derived from methacryloyl isocyanate and urea

Abstract

The two new functional monomers, UMAI and UDMAI, having amide groups were prepared on reaction of methacryloyl isocyanate (MAI) with urea at low temperature. The monomers thus obtained were characterized by elemental analysis, as well as infrared, ultraviolet, 1H and 13C-NMR (nuclear magnetic resonance) spectra. Radical polymerization of UMAI monomer was studied in terms of the rate of polymerization, solvent effect, thermal properties, solubility, and polymer modifications. The rate of polymerization for UMAI is larger than that of polymerization for bisphenol A-MAI (BPA-MAI), irrespective of the polymerization method. The rate of thermal polymerization of UDMAI was three times that of UMAI. Copolymerization of UMAI (M1) and methyl methacrylate (M2) in dimethylsulfoxide (DMSO) at 90°C also proceeded. The monomer reactivity ratio was calculated to be r1 = 0.28 ± 0.05, r2 = 3.50 ± 0.08, according to the Kelen-Tudos method. The thermal properties of polyUMAI (PUMAI) for glass transition temperature (Tg) and 10% weight loss temperature (T) could be enhanced by reaction with sulfonyldiphathalic anhydride. The solubility of PUMAI could be improved by introducing N-alkylation because of reducing the association of hydrogen bonds. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 1789–1796, 1999