Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers

Fortman, David J.; Brutman, Jacob P.; Cramer, Christopher J.; Hillmyer, Marc A.; Dichtel, William R.

doi:10.1021/jacs.5b08084

Cited by 811Polymer composites and self-healingCarbon dioxide utilization in catalysisEpoxy Resin Curing Processes

Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers

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Fortman, David J., Brutman, Jacob P., Cramer, Christopher J., Hillmyer, Marc A., Dichtel, William R.·2015·Journal of the American Chemical Society

DOI 10.1021/jacs.5b08084

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Abstract

Vitrimers are polymer networks whose cross-links undergo associative exchange processes at elevated temperature, usually in the presence of an embedded catalyst. This design feature enables the reshaping of materials with mechanical properties similar to thermoset resins. Here we report a new class of vitrimers consisting of polyhydroxyurethanes (PHUs) derived from six-membered cyclic carbonates and amines. PHU networks relax stress and may be reprocessed at elevated temperature and pressure in the absence of an external catalyst. The as-synthesized networks exhibit tensile properties comparable to those of leading thermosets and recover ca. 75% of their as-synthesized values following reprocessing. Stress relaxation occurs through an associative process involving nucleophilic addition of free hydroxyl groups to the carbamate linkages and exhibits an Arrhenius activation energy of 111 ± 10 kJ/mol, which is lower than that observed for molecular model compounds (148 ± 7 kJ/mol). These findings suggest that transcarbamoylation is activated by mechanical stress, which we attribute, on the basis of DFT calculations, to the twisting of N lone pairs out of conjugation with the carbonyl π orbitals. PHU vitrimers are a promising new class of repairable networks because of their outstanding mechanical properties, avoidance of toxic isocyanate monomers, and catalyst-free repair processes.

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Authors: Fortman, D. J., Brutman, J. P., Cramer, C. J., Hillmyer, M. A., & Dichtel, W. R.
Affiliations: Cornell University (US)
University of Minnesota (US)
Corresponding author: Cramer, Christopher J.
Hillmyer, Marc A.
Dichtel, William R.
ORCID: Fortman, David J.
Cramer, Christopher J.
Hillmyer, Marc A.
Dichtel, William R.
Venue: Journal of the American Chemical Society
Publisher: American Chemical Society (ACS)
Published: 2015-10-23
Volume: 137
Issue: 44
Pages: 14019-14022
ISSN: 0002-7863 (ISSN-L)
1520-5126
DOI: 10.1021/jacs.5b08084
OpenAlex: W2237595662
Cited by: 811
References: 38
Citations by year: 2026: 49 · 2025: 88 · 2024: 90 · 2023: 91 · 2022: 109 · 2021: 78 · 2020: 95 · 2019: 91 · 2018: 49 · 2017: 50 · 2016: 21
FWCI: 25.65
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: other-oa
pubs.acs.org/page/policy/authorchoice_termsofuse.html (vor, 10 d)
Locations: Journal of the American Chemical Society (publishedVersion, other-oa)
PubMed (publishedVersion)
Funders: Division of Materials Research (DMR-1120296)
Division of Chemistry (CHE-1413862)
Topics: Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
Physical Sciences › Engineering › Mechanical Engineering › Epoxy Resin Curing Processes
Keywords: vitrimers, polyhydroxyurethanes, cyclic carbonates, stress relaxation, carbamate linkage, reprocessability, DFT calculations

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Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers

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