Semi-Aromatic Polyesters Based on a Carbohydrate-Derived Rigid Diol for Engineering Plastics

New carbohydrate-based polyesters were prepared from isoidide- 2,5-dimethanol (extended isoidide, XII) through melt polymerization with dimethyl esters of terephthalic acid (TA) and furan-2,5-dicarboxylic acid (FDCA), yielding semi-crystalline prepolymers. Subsequent solid-state post-condensation (SSPC) gave high molecular weight (M-n = 30 kgmol(-1) for FDCA) materials, the first examples of high Mn, semi-aromatic homopolyesters containing isohexide derivatives obtained via industrially relevant procedures. NMR spectroscopy showed that the stereo-configuration of XII was preserved under the applied conditions. The polyesters are thermally stable up to 380 degrees C. The TA-and FDCA-based polyesters have high T-g (105 degrees C and 94 degrees C, resp.) and T-m (284 degrees C and 250 degrees C, resp.) values. Its reactivity, stability, and ability to afford high T-g and T-m polyesters make XII a promising diol for the synthesis of engineering polymers.