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.
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