Degradable Thermosets Derived from an Isosorbide/Succinic Anhydride Monomer and Glycerol

Perry A. Wilbon, Jeremy L. Swartz, Nina R. Meltzer, Jacob P. Brutman, Marc A. Hillmyer, Jane E. Wissinger

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Isosorbide is a renewable chemical of considerable interest as a monomer and monomer precursor due to its potential use in replacements for fossil-fuel derived polymers. In the present study, a facile microwave-assisted condensation of isosorbide with succinic anhydride was developed that dramatically reduced the reaction time. The resulting isosorbide disuccinic acid derivative (I-S-2) was polymerized under solvent-free conditions with glycerol to produce a renewable, cross-linked polyester with high modulus and appreciable thermal stability. Inclusion of 13 wt % or more of low molar mass hydroxy-telechelic poly(ethylene oxide) (PEO) (Mn = 300 g/mol) produced materials with a notable decrease in modulus and glass transition temperature. Degradation studies at 50 °C in acidic and basic solutions demonstrated the ability of the I-S-2 thermosets to be readily hydrolyzable. Furthermore, the resulting aqueous degradation solutions can be concentrated and reheated to produce new materials, albeit with a reduction in tensile properties. These I-S-2/glycerol thermosets represent economic, sustainable materials with tunable mechanical properties.

Original languageEnglish (US)
Pages (from-to)9185-9190
Number of pages6
JournalACS Sustainable Chemistry and Engineering
Volume5
Issue number10
DOIs
StatePublished - Oct 2 2017

Bibliographical note

Funding Information:
This work was supported by the NSF under the Center for Sustainable Polymers, CHE-1413862. Part of this work was carried out in the College of Science and Engineering Polymer Characterization Facility, University of Minnesota, which has received capital equipment funding from the NSF through the UMN MRSEC program under Award Number DMR-1420013. We would also like to thank Dr. Erik Hagberg of ADM for providing the isosorbide used in this study.

Publisher Copyright:
© 2017 American Chemical Society.

Keywords

  • Glycerol
  • Isosorbide
  • Microwave-assisted reaction
  • Poly(ethylene oxide)
  • Renewable
  • Thermoset polymers

How much support was provided by MRSEC?

  • Shared

Reporting period for MRSEC

  • Period 4

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