How Does the Hydrogen Bonding Interaction Influence the Properties of Furan-Based Epoxy Resins

A biobased epoxy 2,5-bis[(2-oxiranylmethoxy)methyl]-furan (BOF) together with its petroleum-based analogues, 1,4-bis[(2-oxiranylmethoxy)methyl]-benzene (p-BOB) and 1,3-bis[(2-oxiranylmethoxy)methyl]-benzene (m-BOB), have been synthesized. After their chemical structures were identified by nuclear magnetic resonance (1H NMR and 13C NMR), they were cured by the petroleum-based 4,4′-diaminodiphenylmethane and biobased 5,5′-methylenedifurfurylamine, respectively. Thermal and mechanical properties of the cured resins were investigated by differential scanning calorimetry, thermogravimetric analyzer and dynamic mechanical analysis. Especially, hydrogen bonding interactions in the different cured systems were studied by Fourier transform infrared spectroscopy. Based on the structure–properties relationship investigation, it could be concluded that it was the hydrogen bonding interaction playing a key role in determining the thermal properties of the furan-based epoxy resins.