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

doi:10.1021/acssuschemeng.7b02096

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 journal › Article › peer-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) (M_n = 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 language	English (US)
Pages (from-to)	9185-9190
Number of pages	6
Journal	ACS Sustainable Chemistry and Engineering
Volume	5
Issue number	10
DOIs	https://doi.org/10.1021/acssuschemeng.7b02096
State	Published - 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

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UN SDGs

This output contributes to the following Sustainable Development Goal(s)

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1 Finished
1 Active

MRSEC IRG-3: Hierarchical Multifunctional Macromolecular Materials
Reineke, T. M., Bates, F. S., Dorfman, K., Dutcher, C. S., Hillmyer, M. A., Lodge, T., Morse, D. C., Siepmann, I., Barreda, L. & Ganewatta, M. S.
1/1/98 → …
Project: Research project
University of Minnesota MRSEC (DMR-1420013)
Lodge, T.
11/1/14 → 10/31/20
Project: Research project

Cite this

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title = "Degradable Thermosets Derived from an Isosorbide/Succinic Anhydride Monomer and Glycerol",

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.",

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author = "Wilbon, {Perry A.} and Swartz, {Jeremy L.} and Meltzer, {Nina R.} and Brutman, {Jacob P.} and Hillmyer, {Marc A.} and Wissinger, {Jane E.}",

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: {\textcopyright} 2017 American Chemical Society.",

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AU - Brutman, Jacob P.

AU - Hillmyer, Marc A.

AU - Wissinger, Jane E.

N1 - 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.

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N2 - 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.

AB - 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.

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KW - Renewable

KW - Thermoset polymers

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

Abstract

Bibliographical note

Keywords

How much support was provided by MRSEC?

Reporting period for MRSEC

UN SDGs

Access

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MRSEC IRG-3: Hierarchical Multifunctional Macromolecular Materials

University of Minnesota MRSEC (DMR-1420013)

Cite this