Synthesis and characterization of itaconic-based epoxy resins

A trifunctional epoxy resin from itaconic acid (TEIA) was synthesized from a renewable resource-based itaconic acid by allylation of itaconic acid to form diallyl itaconate by using m-chloroperoxybenzoic acid as oxidizing agents followed by epoxidation of allylic CC bond of diallyl itaconate methylhexahydropthalic anhydride as curing agent in the presence of 2-methyl imidazole as a catalyst. The chemical structure of the synthesized resins was confirmed by Fourier transform infrared and nuclear magnetic resonance (H-1-NMR and C-13-NMR) spectroscopy analysis. The mechanical, thermal, and rheological performances of the TEIA were also investigated and compared with diglycidyl ether of bisphenol A and a plant-based epoxidized soybean oil bioresin cured with the same curing agent. The higher epoxy value of 1.02, lower viscosity (0.96Pas at 25 degrees C), higher mechanical, and higher curing reactivity toward methylhexahydropthalic anhydride of TEIA as compared with epoxidized soybean oil and comparable with diglycidyl ether of bisphenol A demonstrated significant evidence to design and develop a novel bio-based epoxy resin with high performance to substitute the petroleum-based epoxy resin.