Enhanced Polyester Degradation through Transesterification with Salicylates

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Abstract

Polyesters constitute nearly 10% of the global plastic market, but most are essentially non-degradable under ambient conditions or in engineered environments. A range of degradable polyesters have been developed as more sustainable alternatives; however, limitations of practical degradability and scalability have hindered their viability. Here, we utilized transesterification approaches, including in situ polymerization-transesterification, between a salicylate and a polyester to incorporate salicylate units into commercial polyester backbones. The strategy is scalable and practically relevant given that high molar mass polymers can be obtained from melt-processing of commercial polyesters using common compounders or extruders. Polylactide containing sparse salicylate moieties shows enhanced hydrolytic degradability in aqueous buffer, seawater, and alkaline solutions without sacrificing the thermal, mechanical, and O2 barrier properties of the parent material. Additionally, salicylate sequences were incorporated into polycaprolactone and a derivative of poly(ethylene terephthalate), and those modified polymers also exhibited facile degradation behavior in alkaline solution, further expanding the scope of this approach. This work provides insights and direction for the development of high-performance yet more sustainable and degradable alternatives to conventional polyesters.

Original languageEnglish (US)
Pages (from-to)15784-15790
Number of pages7
JournalJournal of the American Chemical Society
Volume143
Issue number38
DOIs
StatePublished - Sep 29 2021

Bibliographical note

Funding Information:
We acknowledge our principal funding source, the National Science Foundation Center for Sustainable Polymers at the University of Minnesota, which is a National Science Foundation supported a Center for Chemical Innovation (CHE-1901635). We thank Yuheng Miao and Youngsu Shin for experimental support and Xiayu Peng, Derek Batiste, and C. Maggie Lau for helpful feedback. We also thank Dr. Chris Derosa for synthesizing PCL, Nicholas Van Zee for helping with DOSY NMR, and Dr. Lucie Fournier for helping with MALDI-TOF analysis.

Publisher Copyright:
© 2021 American Chemical Society.

PubMed: MeSH publication types

  • Journal Article

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