Synthesis and Properties Investigation of Thiophene-aromatic Polyesters: Potential Alternatives for the 2,5-Furandicarbo
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ARTICLE
POLYMER SCIENCE
https://doi.org/10.1007/s10118-020-2438-2 Chinese J. Polym. Sci.
Synthesis and Properties Investigation of Thiophene-aromatic Polyesters: Potential Alternatives for the 2,5-Furandicarboxylic Acid-based Ones Jing-Gang Wanga, Xiao-Qin Zhanga, Ang Shena,b, Jin Zhua, Ping-An Songc, Hao Wangc, and Xiao-Qing Liua* a Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China b University of Chinese Academy of Sciences, Beijing 100049, China c University of Southern Queensland, Springfield, QLD 4300, Australia
Electronic Supplementary Information Abstract In order to explore new substitutes for 2,5-furandicarboxylic acid (FDCA) or poly(ethylene 2,5-furandicarboxylate) (PEF) and try to develop more ideal bio-based polyesters, several thiophene-aromatic polyesters (PETH, PPTH, PBTH, and PHTH) were synthesized from dimethyl thiophene-2,5-dicarboxylate (DMTD) and different diols, including ethylene glycol, 1,3-propanediol, 1,4-butanediol, and 1,6-hexanediol. The chemical structures of obtained polyesters were confirmed by nuclear magnetic resonance spectroscopy (1H-NMR and 13C-NMR). Determined by GPC measurement, their average molecular weight (Mw) varied from 5.22 × 104 g/mol to 7.94 × 104 g/mol with the molar-mass dispersity of 1.50−2.00. Based on the DSC and TGA results, the synthesized polyesters PETH, PPTH, and PBTH displayed comparable or even better thermal properties when compared with their FDCA-based analogues. From PETH to PHTH, their Tg varied from 64.6 °C to −1 °C while T5% ranged from 409 °C to 380 °C in nitrogen atmosphere. PETH showed elongation at break as high as 378%, tensile strength of 67 MPa, and tensile modulus of 1800 MPa. Meanwhile, the CO2 and O2 barrier of PETH was 12.0 and 6.6 folds higher than those of PET, respectively, and similar to those of PEF. Considering the overall properties, the synthesized thiophene-aromatic polyesters, especially PETH, showed great potential to be used as an excellent bio-based packaging material in the future. Keywords 2,5-Thiophenedicarboxylic acid (TDCA); 2,5-Furandicarboxylic acid (FDCA); Bio-based polyesters; Barrier properties Citation: Wang, J. G.; Zhang, X. Q.; Shen, A.; Zhu, J.; Song, P. A.; Wang, H.; Liu, X. Q. Synthesis and properties investigation of thiophene-aromatic polyesters: potential alternatives for the 2,5-furandicarboxylic acid-based ones. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-020-2438-2
INTRODUCTION With the rapid development of biotechnology and chemical industry, a large quantity of bio-based monomers, such as ethylene diol,[1] succinic acid,[2] adipic acid,[3] lactic acid,[4] isosorbide,[5] and dodecanedioic acid (DDCA),[6] have been produced and used as the feedstock for polymer synthesis. This strategy has attracted more and more attention due to the increasing concern on fossil resource depletion and serious environmental pollution.[7,8] Compared with the common petroleum-based engineering plastics including polycarbonate (PC), poly(eth
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