Poly(alkylene oxide) ionomers. XI. Polymerization and copolymerization of methyl ω‐epoxyundecanoate and characterization of the polymers

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Abstract
Methyl 10‐undecenoate was epoxidized in nearly quantitative yield with m‐chloroperoxy‐benzoic acid to methyl 10,11‐epoxyundecanoate. The functional epoxide monomer was polymerized by the reaction product of triethylaluminum/water/acetylacetone (1.0/0.5/1.0) to a high molecular weight elastomer having pendent carboxyl groups, and a molecular weight distribution near the most probable distribution. With the same initiator system, methyl 10,11‐epoxyundecanoate was copolymerized with ethylene oxide, propylene oxide, 1‐butene oxide, 1‐hexene oxide, phenyl glycidyl ether, epichlorohydrin, and 4,4,4‐trichloro‐1‐butene oxide. The copolymers were typically high in molecular weight, elastomeric, and had methyl 10,11‐epoxyundecanoate incorporations similar to the initial feed ratio of comonomers. The new family of functional polymers were characterized by their infrared and NMR spectra, dilute solution viscosity and thermal transitions.