Synthesis of 2,5-furandicarboxylic acid-based heat-resistant polyamides under existing industrialization process

Abstract

As a bio-based material, 2,5-furandicarboxylic acid (FDCA) has been used widely as alternative material to terephthalic acid to produce polyesters or polyamides. In this study, PA10T/10F with melting point higher than 280 °C was produced under existing industrialization process (prepolymerization+solid state polymerization (SSP)), viscosity of which was affected greately by decarboxylation of FDCA. TGIR technique was used to study decarboxylation, and 1,10-decanediamine, CO2, H2O and furan derivates can be found, verifying decarboxylation scheme. 1H NMR, 13C NMR and 2D NMR analysis showed that nearly half of the feeding FDCA monomers decarboxylates during SSP, instead of entering the polyamide chain, leading to the lower furan moiety ratio in polymers compared to that of feeding ratio. However, thermal stability of PA10T/10F polyamide is comparable to PA10T homopolymer, which indicates that FDCA can be a promising base material for heat-resistant polyamide production.