Synthesis of new hybrid monomers and oligomers containing cationic and radical polymerizable vinyl groups and their photoinitiated polymerization

Abstract

New hybrid vinyl monomers with both cationic- and radical-polymerizable vinyl groups were synthesized by the reaction of bis[1-(chloromethyl)-2-(vinyloxy)ethyl]terephthalate (3) with unsaturated carboxylic acids using 1,8-diazabicyclo[5.4.0]-undecene-7 (DBU) as a base. The reaction of 3 with methacrylic acid 4a was carried out using DBU in DMSO at 70°C for 24 h to give an 86% yield of the hybrid vinyl monomer (5a). Polycondensation of 3 with unsaturated dicarboxylic acids was also performed using DBU to give hybrid vinyl oligomers with radical polymerizable C = C groups (VR) in the main chain and cationic polymerizable vinyl ether moieties (VC) on the side chain. The photopolymerization of these hybrid vinyl compounds proceeded smoothly in bulk using either a cationic photoinitiator such as a sulfonium salt or a radical photoinitiator such as acyl phosphine oxide under UV irradiation. © 1996 John Wiley & Sons, Inc.