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 language | English (US) |
|---|---|
| Pages (from-to) | 9185-9190 |
| Number of pages | 6 |
| Journal | ACS Sustainable Chemistry and Engineering |
| Volume | 5 |
| Issue number | 10 |
| DOIs | |
| State | Published - Oct 2 2017 |
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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 journal › Article
}
TY - JOUR
T1 - Degradable Thermosets Derived from an Isosorbide/Succinic Anhydride Monomer and Glycerol
AU - Wilbon, Perry A.
AU - Swartz, Jeremy L.
AU - Meltzer, Nina R.
AU - Brutman, Jacob P.
AU - Hillmyer, Marc A.
AU - Wissinger, Jane E.
PY - 2017/10/2
Y1 - 2017/10/2
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.
KW - Glycerol
KW - Isosorbide
KW - Microwave-assisted reaction
KW - Poly(ethylene oxide)
KW - Renewable
KW - Thermoset polymers
UR - http://www.scopus.com/inward/record.url?scp=85030480605&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85030480605&partnerID=8YFLogxK
U2 - 10.1021/acssuschemeng.7b02096
DO - 10.1021/acssuschemeng.7b02096
M3 - Article
AN - SCOPUS:85030480605
VL - 5
SP - 9185
EP - 9190
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
SN - 2168-0485
IS - 10
ER -