Synthesis, Processing, and Performance of a Furan-Based Glycidyl Amine Epoxy Resin

Furan diepoxy (FDE), a diglycidyl amine with a pendant furan, was synthesized using a 1:10 furfuryl amine/epichlorohydrin ratio. Aliquots were taken during the synthesis and characterized using gel permeation chromatography (GPC) and Fourier transform infrared spectroscopy (FTIR). Two significant products, FDE and α-chlorohydrin FDE, formed simultaneously with increasing reaction time. Eventually, α-chlorohydrin FDE became the main product. Purified FDE and α-chlorohydrin FDE were cured with an amine to investigate the network formation using differential scanning calorimetry (DSC), FTIR, and ¹H and ¹³C-{¹H} nuclear magnetic resonance (NMR). Dynamic mechanical analysis (DMA) was conducted to measure the thermomechanical properties and create a structure-property relationship. Compared to purified FDE, which had a storage modulus (<i>E</i>') at 25 °C of 2.9 GPa and a <i>T</i> _g of 80 °C, α-chlorohydrin FDE had increased <i>E</i>' at 25 °C of 4.4 GPa and <i>T</i> _g of 129 °C. The improved properties resulted from α-chlorohydrin FDE forming new cross-links via ring-opening of the furan.