Degradable and renewably-sourced poly(ester-thioethers) by photo-initiated thiol-ene polymerization

Leon M. Lillie, William B. Tolman, Theresa M. Reineke

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11 Scopus citations

Abstract

With the aim of preparing sustainable and degradable polymers from sugar-derived precursors, a family of five poly(ester-thioethers) were synthesized by photoinitiated thiol-ene polymerization of monomers incorporating d-glucaro-1,4:6,3-dilactone (GDL). Various dithiols were used to produce linear poly(ester-thioethers) of glucarodilactone 10-undecenoate (GDLU) to probe the effect of the dithiols on the observed mechanical performance and degradability. The samples exhibited glass transition (Tg) values from -8.7 to 19 °C. The polymers with the simplest dithiols, 1,2-ethanedithiol (EtDT) and 3,6-dioxa-1,8-octane-dithiol (DODT), were found to exhibit crystallinity, while the more structurally complex and rigid dithiol structures were found to produce amorphous materials. Due to the GDL units in the polymers, rapid degradation under basic aqueous conditions and stability in acidic and neutral conditions were observed. Tensile testing of these materials showed robust mechanical properties, including tunable moduli (0.011 to 0.29 GPa), strength (21 to 42 MPa), and ductility (410 to 590%).

Original languageEnglish (US)
Pages (from-to)3272-3278
Number of pages7
JournalPolymer Chemistry
Volume9
Issue number23
DOIs
StatePublished - Jun 21 2018

Bibliographical note

Funding Information:
This project was funded through the National Science Foundation under the Center for Sustainable Polymers (NSF project CHE-1413862).

Funding Information:
This project was funded through the National Science Foundation under the Center for Sustainable Polymers (NSF project CHE-1413862). The authors thank Jeffrey Ting for his creative assistance with our graphical abstract for this paper. This work was supported by the use of University of Minnesota’s Polymer Characterization Facility (UMN MRSEC, award number DMR-1420013). Mass spectrometry analysis was performed at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota, as well as The National Science Foundation (NSF, Award CHE-1336940). The content of this paper is the sole responsibility of the authors and does not represent endorsement by the MSL or NSF.

How much support was provided by MRSEC?

  • Shared

Reporting period for MRSEC

  • Period 5

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