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Polymerization of three cyclic ketene acetals: i.e., 5,6-benzo-2-methylene-1,3-dioxepane (BMDO), 2-methylene-4-phenyl-1,3-dioxolane (MPDO) and 4,7-dimethyl-2-methylene-1,3-dioxepane (DMMDO) were carried out in the presence of ethyl α-bromobutyrate/CuBr/2,2'-bipyridine respectively. The structures ofpoly(BMDO), poly(MPDO) and poly(DMMDO)were characterized by 1H and 13C-NMR spectra. The effects of monomer structure on the behavior of atom transfer free radical ring-opening polymerization were investigated and the mechanism of controlled free radical ring-opening polymerization was discussed.