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 (Mn =30 kg mol(-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 °C. The TA- and FDCA-based polyesters have high Tg (105 °C and 94 °C, resp.) and Tm (284 °C and 250 °C, resp.) values. Its reactivity, stability, and ability to afford high Tg and Tm polyesters make XII a promising diol for the synthesis of engineering polymers.
Food and Biobased Research, Wageningen University and Research Center, Bornse Weilanden 9, 6708 WG, Wageningen (The Netherlands); Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, Den Dolech 2, 5600 MB, Eindhoven (The Netherlands); Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX, Eindhoven (The Netherlands).
Jing
J
Wu
Pieter
P
Eduard
Shanmugam
S
Thiyagarajan
Bart A J
BA
Noordover
Daan S
DS
van Es
Cor E
CE
Koning
D002241:Carbohydrates / Q000737:chemistry*; D004738:Engineering; D006018:Glycols / Q000737:chemistry*; D010969:Plastics / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry*
D002241:Carbohydrates; D006018:Glycols; D010969:Plastics; D011091:Polyesters
carbohydrates; polymers; renewable resources; solid-state post condensation; thermal properties