Abstract
A general procedure was developed for the synthesis of 1,1 disubstituted electron deficient olefin monomers. The formation of the phenylselenide precursor, followed by hydrogen peroxide oxidation produced the monomers in good yields and purity. Acidic by-products of the oxidation reaction act as stabilizers to prevent polymerization of these base sensitive monomers. The dicyanoacrylate ester of butanediol, diethyl methylenemalonate, N,N diethyl 2-cyanoacrylamide, and 2′-octyl 2-cyanoacrylate were prepared by this method. These monomers were polymerized alone and copolymerized with ethyl 2-cyanoacrylate (ECA) in THF with pyridine as the initiator. Gel permeation chromatography and thermogravimetric analysis were utilized to study some of the polymer properties. The ECA homopolymer yielded the polymer with the highest degree of polymerization, while the diethyl methylenemalonate homopolymer possessed the highest decomposition temperature.
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