Epoxy derived from heteroaromatic
compounds and its properties are seldom reported. In this work, two
model epoxy monomers (EP-B and EP-F) were synthesized from isophthalic
acid and 2,5-furandicarboxylic acid. After curing with 4,4-diaminodiphenylmethane
(DDM) in a stoichiometric quantity of 2:1, their properties were comparatively
investigated, especially the formation and role of hydrogen bonding
in them were identified. Results obtained from differential scanning
calorimetry (DSC), dynamic thermomechanical analysis (DMA), fluorescence
emission spectra, and static contact angle measurements showed that
the cured EP-F/DDM system exhibited unexpected performance in higher
glass transition temperature (T
g), fluorescence
intensity, and hydrophilicity. And temperature-dependent Fourier transform
infrared (FT-IR) analysis further confirmed that it was the more hydrogen
bonding in the cured EP-F/DDM, involved with the oxygen heteroatoms
in the furan ring, which led to its better properties. This work gives
us some new insights into the role of electronegative heteroatoms
in epoxy resin synthesized from heteroaromatic compounds.