Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies
Lesly Dasilva Wandji Djouonkep,
Arnaud Kamdem Tamo,
Ingo Doench,
Naomie Beolle Songwe Selabi,
Emmanuel Monga Ilunga,
Arnaud Regis Kamgue Lenwoue,
Mario Gauthier,
Zhengzai Cheng,
Anayancy Osorio-Madrazo
Affiliations
Lesly Dasilva Wandji Djouonkep
Institute of Fine Organic Chemistry and New Organic Materials, Wuhan University of Science and Technology, Wuhan 430081, China
Arnaud Kamdem Tamo
Laboratory for Bioinspired Materials—BMBT, Institute of Microsystems Engineering—IMTEK, University of Freiburg, 79110 Freiburg, Germany
Ingo Doench
Laboratory for Bioinspired Materials—BMBT, Institute of Microsystems Engineering—IMTEK, University of Freiburg, 79110 Freiburg, Germany
Naomie Beolle Songwe Selabi
Institute of Advanced Materials and Nanotechnology, Wuhan University of Science and Technology, Wuhan 430081, China
Emmanuel Monga Ilunga
Institute of Advanced Materials and Nanotechnology, Wuhan University of Science and Technology, Wuhan 430081, China
Arnaud Regis Kamgue Lenwoue
National Engineering Laboratory of Petroleum Drilling Technology, Department of Petroleum Engineering, Leak Resistance & Sealing Technology Research Department, Yangtze University, Wuhan 430100, China
Mario Gauthier
Institute of Fine Organic Chemistry and New Organic Materials, Wuhan University of Science and Technology, Wuhan 430081, China
Zhengzai Cheng
Institute of Fine Organic Chemistry and New Organic Materials, Wuhan University of Science and Technology, Wuhan 430081, China
Anayancy Osorio-Madrazo
Laboratory for Bioinspired Materials—BMBT, Institute of Microsystems Engineering—IMTEK, University of Freiburg, 79110 Freiburg, Germany
In this work, the feasibility of replacing petroleum-based poly(ethylene terephthalate) (PET) with fully bio-based copolyesters derived from dimethyl 2,5-thiophenedicarboxylate (DMTD), dimethyl 2,5-dimethoxyterephthalate (DMDMT), and polysaccharide-derived 1,6-hexanediol (HDO) was investigated. A systematic study of structure-property relationship revealed that the properties of these poly(thiophene–aromatic) copolyesters (PHS(20–90)) can be tailored by varying the ratio of diester monomers in the reaction, whereby an increase in DMTD content noticeably shortened the reaction time in the transesterification step due to its higher reactivity as compared with DMDMT. The copolyesters had weight-average molar masses (Mw) between 27,500 and 38,800 g/mol, and dispersity Đ of 2.0–2.5. The different polarity and stability of heterocyclic DMTD provided an efficient mean to tailor the crystallization ability of the copolyesters, which in turn affected the thermal and mechanical performance. The glass transition temperature (Tg) could be tuned from 70–100 °C, while the tensile strength was in a range of 23–80 MPa. The obtained results confirmed that the co-monomers were successfully inserted into the copolyester chains. As compared with commercial poly(ethylene terephthalate), the copolyesters displayed not only enhanced susceptibility to hydrolysis, but also appreciable biodegradability by lipases, with weight losses of up to 16% by weight after 28 weeks of incubation.
