A concise series of renewable vinyl compounds has been prepared from benign biosourced precursors, vanillin and eugenol, in fair overall yield. These were evaluated against styrene as reactive diluents in a renewable high-performance vinyl ester resin thermoset: dimethacrylated-epoxidized-sucrose-soyate (DMESS). Each diluent contained a 1,2-dimethoxybenzene or veratrole core structure that connotes a decreased vapor pressure and thereby reduced exposure hazard. Viscosities for formulations (10, 20, and 30% by weight of diluents) with styrene and all three veratrole-diluents were evaluated. Veratrole-diluents were comparable to styrene at similar molar concentration. Thermosets formulated with 30% by weight of diluents were prepared and characterized by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and dynamic mechanical thermal analysis (DMTA); the most promising thermoset was prepared using 3-allyl-1,2-dimethoxy-5-vinylbenzene-diluted-DMESS and closely matched the performance of the styrene-diluted thermoset in terms of thermal stability, glass transition temperature, toughness, and tensile strength.

A series of renewable novel bicyclic AB type polyester precursors have been prepared in good overall yield from lignocellulosic biomass. These advancements take full advantage of the differing oxidation states of functional groups in 5-(hydroxymethyl)furfural by chemoselective preparation of furanic hydroxy esters and applying benzyne-Diels–Alder cycloaddition/aromatization strategies.

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