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Abstract
Utilisation of bio-derived platform molecules in polymer synthesis has advantages which are, broadly, twofold; to digress from crude oil dependence of the polymer industry and secondly to reduce the environmental impact of the polymer synthesis through the inherent functionality of the bio-derived platform molecules. Bulk polymerisation of bio-derived unsaturated di-acids has been employed to produce unsaturated polyester (UPEs) which have been analysed by GPC, TGA, DSC and NMR spectroscopy, advancing on the analysis previously reported. UPEs from the diesters of itaconic, succinic, and fumaric acids were successfully synthesised with various diols and polyols to afford resins of MN 480–477,000 and Tg of −30.1 to −16.6 °C with solubilities differing based on starting monomers. This range of properties allows for many applications and importantly due to the surviving Michael acceptor moieties, solubility and cross-linking can be specifically tailored, post polymerisation, to the desired function. An improved synthesis of itaconate and succinate co-polymers, via the initial formation of an itaconate bis-diol, is also demonstrated for the first time, resulting in significantly improved itaconate incorporation.
Highlights
Unsaturated polyesters (UPEs) are a large family of polymers with a wide range of applications stemming from their ability to undergo various post-polymerisation reactions
Bio-derived platform molecules 1–3 and various polyols 4–7 used for synthesis of unsaturated polyesters (UPEs)
dimethyl itaconate (DMI) and dimethyl succinate (DMS) were purchased from Fluka (Buchs, Switzerland); dimethyl fumarate (DMFu), 1,3-propanediol, Ti(IV) tetra-tert-butoxide, dimethyl maleate (DMM), ethyl lactate, magnesium oxide, DMSO-d6 and CDCl3 were purchased from Sigma-Aldrich
Summary
Unsaturated polyesters (UPEs) are a large family of polymers with a wide range of applications stemming from their ability to undergo various post-polymerisation reactions. A wide variety of compounds have been incorporated into the oligomers alongside the itaconate moiety such as; alcohols (e.g., 1,4-butanediol [10], ethylene glycol [10], trimethylolpropane [9], sorbitol [9], isosorbide [18] or isoamyl alcohol [12]); epoxides [19] (e.g., propylene oxide, glycidyl ether, styrene oxide or epichlorohydrin [20]); and other di-acids (e.g., succinic [9,18,21], maleic [1,16] or fumaric [22]); and this helps introduce extra functionality. The investigation into use of alternative di-acid monomers or alternative diols and polyols and co-polymer synthesis is reported including the successful achievement of
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