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 journalArticle

10 Citations (Scopus)

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

Fingerprint

Isosorbide
Thermosets
Glycerol
Monomers
Polyethylene oxides
degradation
ethylene
fossil fuel
condensation
Degradation
mechanical property
Polyesters
polymer
Molar mass
replacement
glass
oxide
Tensile properties
Fossil fuels
Condensation

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

Cite this

Degradable Thermosets Derived from an Isosorbide/Succinic Anhydride Monomer and Glycerol. / Wilbon, Perry A.; Swartz, Jeremy L.; Meltzer, Nina R.; Brutman, Jacob P.; Hillmyer, Marc A.; Wissinger, Jane E.

In: ACS Sustainable Chemistry and Engineering, Vol. 5, No. 10, 02.10.2017, p. 9185-9190.

Research output: Contribution to journalArticle

Wilbon, Perry A. ; Swartz, Jeremy L. ; Meltzer, Nina R. ; Brutman, Jacob P. ; Hillmyer, Marc A. ; Wissinger, Jane E. / Degradable Thermosets Derived from an Isosorbide/Succinic Anhydride Monomer and Glycerol. In: ACS Sustainable Chemistry and Engineering. 2017 ; Vol. 5, No. 10. pp. 9185-9190.
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