The improved production of a polar curable monomer, isosorbide
monomethacrylate (MISD), with methacrylic anhydride (MAAH) as an acyl
donor, was performed. A sustainable and cheap catalyst, potassium
acetate (CH3COOK), was used for a solvent-free synthesis,
requiring only the equimolar amount of reagents (no excess). The production
included the quantitative separation of the secondary product, methacrylic
acid (MAA), preventing the reaction batch from the purification process
(neutralization of MAA), and gaining a usable reagent. The synthesis
resulted in a sufficient yield of MISD (61.8%) obtained by the liquid–liquid
extraction process (LLE), which is a significant improvement in the
process, avoiding the flash chromatography step in the isolation of
MISD. The purity of synthesized and isolated MISD via the LLE was
confirmed by 1H NMR, MS, and FTIR analyses. The thermal
analyses, namely, DSC and TGA, were used to characterize the curability
and thermal stability of MISD. The activation energy of MISD’s
curing was calculated (E
a = 94.6 kJ/mol)
along with the heat-resistant index (T
s = 136.8). The polar character of isosorbide monomethacrylate was
investigated in a mixture with epoxidized acrylated soybean oil (EASO).
It was found that MISD is entirely soluble in EASO and can modify
the rheological behavior and surface energy of EASO-based resins.
The apparent viscosity of EASO at 30 °C (ηapp = 3413 mPa·s) decreased with the 50% content of MISD significantly
(ηapp = 500 mPa·s), and the free surface energy
value of EASO (γS = 42.2 mJ/m2) also increased
with the 50% content of MISD (γS = 48.7 mJ/m2). The produced MISD can be successfully used as a diluent
and the polarity modifier of curable oil-based resins.