Polymerizations of some diene monomers. Preparations and polymerizations of vinyl methacrylate, allyl methacrylate, N‐allylacrylamide, and N‐allylmethacrylamide

Vinyl methacrylate, allyl methacrylate, N‐allylacrylamide, and N‐allylmethacrylamide were prepared, and these monomers were polymerized in toluene by α,α‐azobisisobutyronitrile catalyst. Cyclization content of poly(vinyl methacrylate) was estimated by infrared spectroscopy to be 50–60% at low conversions, but at the high conversions, due to gelation the polymers were insoluble in the usual organic solvents. Allyl methacrylate did not produce any soluble polymer, even at a low conversion, in contrast with poly‐(vinyl methacrylate). Poly‐N‐allylacrylamide and poly‐N‐allylmethacrylamide were also insoluble in common solvents. It was assumed that the polymers from monomers containing the allyl group might form crosslinks as a result of allyl resonance stabilization.