Readily Degradable and Recyclable High Molecular Weight Thiosalicylic Acid-based Copolyesters
RESEARCH ARTICLE|Updated:2025-07-14
|
Readily Degradable and Recyclable High Molecular Weight Thiosalicylic Acid-based Copolyesters
Chinese Journal of Polymer ScienceVol. 43, Issue 6, Pages: 924-932(2025)
Affiliations:
a.State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
b.State Key Laboratory of Baiyunobo Rare Earth Resource Researches and Comprehensive Utilization, Baotou Research Institute of Rare Earths, Baotou 014030, China
Yao, G.; Ren, F. P.; Chen, F.; Cao, L. Y.; Xian, J.; Pan, X. B.; Cao, H. Z.; Wu, J. C. Readily degradable and recyclable high molecular weight thiosalicylic acid-based copolyesters. Chinese J. Polym. Sci. 2025, 43, 924–932
Ge Yao, Fang-Ping Ren, Fei Chen, et al. Readily Degradable and Recyclable High Molecular Weight Thiosalicylic Acid-based Copolyesters[J]. Chinese Journal of Polymer Science, 2025, 43(6): 924-932.
Yao, G.; Ren, F. P.; Chen, F.; Cao, L. Y.; Xian, J.; Pan, X. B.; Cao, H. Z.; Wu, J. C. Readily degradable and recyclable high molecular weight thiosalicylic acid-based copolyesters. Chinese J. Polym. Sci. 2025, 43, 924–932DOI: 10.1007/s10118-025-3262-5.
Ge Yao, Fang-Ping Ren, Fei Chen, et al. Readily Degradable and Recyclable High Molecular Weight Thiosalicylic Acid-based Copolyesters[J]. Chinese Journal of Polymer Science, 2025, 43(6): 924-932.DOI: 10.1007/s10118-025-3262-5.
Readily Degradable and Recyclable High Molecular Weight Thiosalicylic Acid-based Copolyesters
A new monomer of thiosalicylic methyl glycolide was synthesized using a one-pot method
and high-molecular-weight poly(thiosalicylic methyl glycolide) (Mn up to 300 kDa) was obtained via the ring-opening polymerization of TSMG. PTSMG exhibits good closed-loop recyclability and hydrolytic degradability
which provide a potential solution to the current plastic pollution problem.
Abstract
Most commercial plastics cannot easily degrade
which raises a number of sustainability issues. To address the current problem of plastic pollution
the research and development of easily degradable and recyclable polymers has become an attractive subject. Herein
a new monomer of thiosalicylic methyl glycolide (TSMG) was synthesized using one-pot method and high molecular weight poly(thiosalicylic methyl glycolide) (PTSMG
M
n
up to 300 kDa) can be obtained
via
the ring-opening polymerization (ROP) of TSMG. PTSMG exhibits good closed-loop recyclability and hydrolytic degradability
where PTSMG can generate pristine monomers through sublimation thermal depolymerization conditions due to the presence of thiophenol ester bond in the polymer chains
and can be degraded rapidly in aqueous solution
which provides a potential solution to the current plastic pollution problem.
关键词
Keywords
references
Tang, X.; Chen, E. Y. X. Toward infinitely recyclable plastics derived from renewable cyclic esters. Chem 2019 , 5 , 284−312 ..
Idrees, M.; Jeelani, S.; Rangari, V. Three-dimensional-printed sustainable biochar-recycled PET composites. ACS Sustainable Chem. Eng. 2018 , 6 , 13940−13948..
Joo, S.; Cho, I. J.; Seo, H.; Son, H. F.; Sagong, H. Y.; Shin, T. J.; Choi, S. Y.; Lee, S. Y.; Kim, K. J. Structural insight into molecular mechanism of poly(ethylene terephthalate) degradation. Nat. Commun. 2018 , 9 , 382..
Yan, Q.; Li, C.; Yan, T.; Shen, Y.; Li, Z. Chemically recyclable thermoplastic polyurethane elastomers via a cascade ring-opening and step-growth polymerization strategy from bio-renewable δ -caprolactone. Macromolecules 2022 , 55 , 3860−3868..
Hong, M.; Chen, E. Y. X. Chemically recyclable polymers: a circular economy approach to sustainability. Green Chem. 2017 , 19 , 3692−3706..
Martin, R. T.; Camargo, L. P.; Miller, S. A. Marine-degradable polylactic acid. Green Chem. 2014 , 16 , 1768−1773..
Li, Z.; Zhao, D.; Shen, Y.; Li, Z. Ring-opening polymerization of enantiopure bicyclic ether-ester monomers toward closed-loop recyclable and crystalline stereoregular polyesters via chemical upcycling of bioplastic. Angew. Chem. Int. Ed. 2023 , 62, e202302101..
Kim, H. J.; Reddi, Y.; Cramer, C. J.; Hillmyer, M. A.; Ellison, C. J. Readily degradable aromatic polyesters from salicylic acid. ACS Macro Lett. 2020 , 9 , 96−102..
Kim, H. J.; Hillmyer, M. A.; Ellison, C. J. Enhanced polyester degradation through transesterification with salicylates. J. Am. Chem. Soc. 2021 , 143 , 15784−15790..
Hong, M.; Chen, E. Y. Completely recyclable biopolymers with linear and cyclic topologies via ring-opening polymerization of gamma-butyrolactone. Nat. Chem. 2016 , 8 , 42−49..
Li, Z.; Shen, Y.; Li, Z. Ring-opening polymerization of lactones to prepare closed-loop recyclable polyesters. Macromolecules 2024 , 57 , 1919−1940..
Tu, Y. M.; Wang, X. M.; Yang, X.; Fan, H. Z.; Gong, F. L.; Cai, Z.; Zhu, J. B. Biobased high-performance aromatic-aliphatic polyesters with complete recyclability. J. Am. Chem. Soc. 2021 , 143 , 20591−20597..
Li, L. G.; Wang, Q. Y.; Zheng, Q. Y.; Du, F. S.; Li, Z. C. Tough and thermally recyclable semiaromatic polyesters by ring-opening polymerization of benzo-thia-caprolactones. Macromolecules 2021 , 54 , 6745−6752..
Li, M. Q.; Luo, Z. X.; Yu, X. Y.; Tian, G. Q.; Wu, G.; Chen, S. C.; Wang, Y. Z. Ring-opening polymerization of a seven-membered lactone toward a biocompatible, degradable, and recyclable semi-aromatic polyester. Macromolecules 2023 , 56 , 2465−2475..
Li, C.; Wang, L.; Yan, Q.; Liu, F.; Shen, Y.; Li, Z. Rapid and controlled polymerization of bio-sourced delta-caprolactone toward fully recyclable polyesters and thermoplastic elastomers. Angew. Chem. Int. Ed. 2022 , 61 , e202201407..
Wang, Y.; Zhu, Y.; Lv, W.; Wang, X.; Tao, Y. Tough while recyclable plastics enabled by monothiodilactone monomers. J. Am. Chem. Soc. 2023 , 145 , 1877−1885..
Wan, Y.; He, J.; Zhang, Y. An arbitrarily regulated monomer sequence in multi-block copolymer synthesis by frustrated lewis pairs. Angew. Chem. Int. Ed. 2023 , 62 , e202218248..
Sun, Y.; An, Z.; Gao, Y.; Hu, R.; Liu, Y.; Lu, H.; Lu, X. B.; Pang, X.; Qin, A.; Shen, Y.; Tao, Y.; Wang, Y. Z.; Wang, J.; Wu, G.; Wu, G. P.; Xu, T. Q.; Zhang, X. H.; Zhang, Y.; Zhang, Z.; Zhu, J. B.; Hong, M.; Li, Z. New sustainable polymers with on-demand depolymerization property. Sci. China Chem. 2024 , 67 , 2803−2841..
Zhu, Y.; Li, M.; Wang, Y.; Wang, X.; Tao, Y. Performance-advantaged stereoregular recyclable plastics enabled by aluminum-catalytic ring-opening polymerization of dithiolactone. Angew. Chem. Int. Ed. 2023 , 62, e202302898..
Xiong, W.; Chang, W.; Shi, D.; Yang, L.; Tian, Z.; Wang, H.; Zhang, Z.; Zhou, X.; Chen, E. Q.; Lu, H. Geminal dimethyl substitution enables controlled polymerization of penicillamine-derived β -thiolactones and reversed depolymerization. Chem 2020 , 6 , 1831−1843..
Shi, C.; Mcgraw, M.; LI, Z.; Cavallo, L.; Falivene, L.; Chen, E. Y.-X. High-performance pan-tactic polythioes ters with intrinsic crystallinity and chemical recyclability. Sci. Adv. 2020 , 6 , eabc0495..
Li, J.; Liu, F.; Liu, Y.; Shen, Y.; Li, Z. Functionalizable and chemically recyclable thermoplastics from chemoselective ring-opening polymerization of bio-renewable bifunctional alpha-methylene-delta-valerolactone. Angew. Chem. Int. Ed. 2022 , 61 , e202207105..
Li, Z.; Zhao, D.; Huang, B.; Shen, Y.; Li, Z. Chemical upcycling of poly(3-hydroxybutyrate) (P3HB) toward functional poly(amine- alt -ester) via tandem degradation and ring-opening polymerization. Macromolecules 2022 , 55 , 9697−9704..
Li, H.; Guillaume, S. M.; Carpentier, J. F. Polythioesters prepared by ring-opening polymerization of cyclic thioesters and related monomers. Chem. Asian J. 2022 , 17 , e202200641..
Yuan, J.; Xiong, W.; Zhou, X.; Zhang, Y.; Shi, D.; Li, Z.; Lu, H. 4-Hydroxyproline-derived sustainable polythioesters: controlled ring-opening polymerization, complete recyclability, and facile functionalization. J. Am. Chem. Soc . 2019 , 141 , 4928-4935..
Wang, Y.; Li, M.; Wang, S.; Tao, Y.; Wang, X. S-carboxyanhydrides: ultrafast and selective ring-opening polymerizations towards well-defined functionalized polythioesters. Angew. Chem. Int. Ed. 2021 , 60 , 10798−10805..
Ren, F.; Xian, J.; Jia, Z.; Chen, Z.; Fu, H.; Wang, R.; Chu, W. D.; Pan, X.; Wu, J. Tetrabutylammonium halides as selectively bifunctional catalysts enabling the syntheses of recyclable high molecular weight salicylic acid-based copolyesters. Angew. Chem. Int. Ed. 2023 , 62 , e202306759..
Zhang, D.; Wang, X.; Zhang, Z.; Hadjichristidis, N. Heteroatom substitution strategy modulates thermodynamics towards chemically recyclable polyesters and monomeric unit sequence by temperature switching. Angew. Chem. Int. Ed. 2024 , 63 , e202402233..
Zhu, Y.; Tao, Y. Stereoselective ring-opening polymerization of S-carboxyanhydrides using salen aluminum catalysts: a route to high-isotactic functionalized polythioesters. Angew. Chem. Int. Ed. 2024 , 63 , e202317305..
S Aksakal, S.; Aksakal, R.; Becer, C. R. Thioester functional polymers. Poly. Chem. 2018 , 9 , 4507−4516..
Ren, F.; Li, X.; Xian, J.; Han, X.; Cao, L.; Pan, X.; Wu, J. Bench-stable potassium complexes for living and isoselective ring-opening polymerization of rac -lactide. J. Polym. Sci. 2022 , 60 , 2847−2854..
Zhang, J.; Jian, C.; Gao, Y.; Wang, L.; Tang, N.; Wu, J. Synthesis and characterization of multi-alkali-metal tetraphenolates and application in ring-opening polymerization of lactide. Inorg. Chem. 2012 , 51 , 13380−13389..
Li, M.; Tao, Y.; Tang, J.; Wang, Y.; Zhang, X.; Tao, Y.; Wang, X. Synergetic organocatalysis for eliminating epimerization in ring-opening polymerizations enables synthesis of stereoregular isotactic polyester. J. Am. Chem. Soc. 2019 , 141 , 281−289..
Dove, A.; Pratt, R.; Lohmeijer, B.; Waymouth, R.; Hedrick, J. Thiourea-based bifunctional organocatalysis: supramolecular recognition for living polymerization. J. Am. Chem. Soc. 2005 , 127 , 13c798−13799..
Wang, J.; Zhu, Y.; Li, M.; Wang, Y.; Wang, X.; Tao, Y. Tug-of-War between two distinct catalytic sites enables fast and selective ring-opening copolymerizations. Angew. Chem. In. Ed. 2022 , 61 , e202208525..
Suzuki, M.; Watanabe, A.; Kawai, R.; Sato, R.; Matsuoka, S. I.; Kawauchi, S. Ring-opening polymerization of thiolactide by using thiol-amine combination. Polymer 2021 , 215 ..
Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) via Ring-opening Polymerization of Seven-Membered Cyclic Oxalate
Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature
Silk Sericin-inspired Poly-β-homoserine for Protein Protection
Chemoselective Ring-opening Copolymerization of CO2-based Lactones towards Functional Polyesters
Advances in Polymer-based Circularly Polarized Luminescent Materials
Related Author
Yue-Yuan Qian
Xiang-Bin Sun
Ya-Lei Liu
Zhi-Bo Li
Wen-Jing Li
Xiang-Qiang Pan
Jian Zhu
Zheng-Biao Zhang
Related Institution
Shandong Key Laboratory of High Performance Polyolefin Materials and Recycling; College of Polymer Science and Engineering, Qingdao University of Science and Technology
College of Chemistry, Chemical Engineering and Materials Science, Zaozhuang University
State Key Laboratory of Chemical Engineering and Low-carbon Technology, College of Chemical and Biological Engineering, Zhejiang University
Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University
State Key Laboratory of Bioreactor Engineering, Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology