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Polar-functionalized polyolefins are high-value materials with improved properties. However, their feedstocks generally come from non-renewable fossil products; thus, it requires the development of renewable bio-based monomers to produce functionalized polyolefins. In this contribution, via the Pd-catalyzed telomerization of 1,3-butadiene and three types of bio-based alcohols (furfuryl alcohol, tetrahydrofurfuryl alcohol, and solketal), 2,7-octadienyl ether monomers including OC8-FUR , OC8-THF, and OC8-SOL were synthesized and characterized, respectively. The copolymerization of these monomers with ethylene catalyzed by phosphine-sulfonate palladium catalysts was further investigated. Microstructures of the resultant copolymers were analyzed by NMR and ATR-IR spectroscopy, revealing linear structures with incorporations of difunctionalized side chains bearing both allyl ether units and polar cyclic groups. Mechanical property studies exhibited better strain-at-break of these copolymers compared to the non-polar polyethylene, among which the copolymer E-FUR with the incorporation of 0.3 mol% displayed the highest strain-at-break and stress-at-break values of 940% and 35.9 MPa, respectively.

Polar-Functionalized Polyethylenes Enabled by Palladium-Catalyzed Copolymerization of Ethylene and Butadiene/Bio-Based Alcohol-Derived Monomers