Rapid copolymerization of canola oil derived epoxide monomers with anhydrides and carbon dioxide (CO2)

Abstract

A canola oil derived monomer, 1-decene, was converted to 1,2-epoxydecane with >90% yield. The ring opening copolymerization of 1,2-epoxydecane with carbon dioxide (CO₂) and different cyclic anhydrides including maleic, succinic, itaconic, phthalic and tetrahydrophthalic was carried out using a double metal cyanide (DMC) catalyst under microwave and conventional heating conditions. The microwave-assisted polymerizations were significantly faster than those observed under conventional heating conditions. The polycarbonates, copolymers with CO₂, were synthesized within minutes (∼30 min) under microwave conditions with high conversions (up to 99%), carbonate linkage (∼88%) and molecular weight (M_w ∼ 15 kDa). The polyesters, copolymers with anhydrides, were synthesized in ∼60 min with high ester content (up to 90%) and M_w (up to 17 kDa). The synthesized copolymers were characterized by Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (¹H NMR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) techniques. The configuration of double bonds in unsaturated polyesters such as poly(1-decene-co-maleate) was completely isomerized through post polymerization modification to enhance its activity as an unsaturated polyester resin (UPR) for different potential applications.