Ring-opening metathesis polymerization as a route to controlled copolymers of ethylene and polar monomers: Synthesis of ethylene-vinyl chloride-like copolymers

A series of ethylene-vinyl chloride-like copolymers were prepared by ring-opening metathesis polymerization (ROMP). The route to these materials included the bulk polymerization of 5-chlorocyclooctene and 5,6-dichlorocyclooctene with the first-generation Grubbs' catalyst, followed by diimide hydrogenation of the resulting unsaturated polymers. In addition, the amount of chlorine in these materials was varied by the copolymerization of 5-chlorocyclooctene with cyclooctene. These materials were fully characterized by NMR (¹H and ¹⁸C), gel permeation chromatography, and Fourier transform infrared spectroscopy. Finally, hydroboration was carried out on the ROMP product of 5-chlorocyclooctene to yield a polymer, which was effectively a vinyl alcoholvinyl chloride-ethylene terpolymer.