Segmented epoxy-based non-isocyanate polyurethanes with thermoreversible Diels-Alder junctions.
- 1Department of Applied Chemistry, University of Debrecen Egyetem tér 1 H-4032 Debrecen Hungary [email protected] +36-52-512-900, ext. 22455.
- 2Department of Solid State Physics, University of Debrecen Bem tér 18/b H-4026 Debrecen Hungary.
Abstract
The development of non-isocyanate polyurethanes (NIPUs) has attracted increasing attention as a sustainable alternative to conventional polyurethane chemistry due to the elimination of toxic isocyanates while maintaining the versatility of segmented polymer architectures. In this work, a novel synthetic strategy for the preparation of segmented NIPUs was developed using epoxide chemistry. The soft and hard segment precursors were obtained by epoxidation from polytetramethylene ether glycol (PTMEG, M n = 2000 g mol⁻¹), polycaprolactone diol (PCD, M n = 2000 g mol⁻¹), and from a hydroxy-urethane derived from furfurylamine, respectively. Polymerization was carried out in two consecutive steps. Initially, the epoxidized soft- and hard-segment precursors were reacted with 1,6-hexamethylenediamine to form furan-terminated prepolymers containing secondary hydroxyl groups. Subsequently, chain extension was achieved through thermoreversible Diels-Alder coupling with bismaleimide, yielding segmented polyurethane networks. Synthesized NIPUs were characterized via FTIR, NMR, and MALDI-TOF MS, and their structure-property relationships were investigated using DSC, DMA, SEM, swelling, and tensile tests. Owing to the incorporation of thermoreversible Diels-Alder linkages, the prepared polymer networks also exhibited intrinsic self-healing capability. The proposed synthetic approach provides a straightforward and environmentally benign route toward segmented non-isocyanate polyurethanes offering broad opportunities for tailoring material performance through molecular design.
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BibTeX
@article{lakatos2026segmented,
title = {{Segmented epoxy-based non-isocyanate polyurethanes with thermoreversible Diels-Alder junctions.}},
author = {Csilla Lakatos and Katalin Czifrák and Lajos Nagy and Csaba Cserháti and Sándor Kéki},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra08436b},
url = {https://europepmc.org/article/MED/42910042},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Segmented epoxy-based non-isocyanate polyurethanes with thermoreversible Diels-Alder junctions.
AU - Csilla Lakatos
AU - Katalin Czifrák
AU - Lajos Nagy
AU - Csaba Cserháti
AU - Sándor Kéki
PY - 2026
DA - 2026/10/21
JO - RSC advances
DO - 10.1039/d6ra08436b
UR - https://europepmc.org/article/MED/42910042
AB - The development of non-isocyanate polyurethanes (NIPUs) has attracted increasing attention as a sustainable alternative to conventional polyurethane chemistry due to the elimination of toxic isocyanates while maintaining the versatility of segmented polymer architectures. In this work, a novel synthetic strategy for the preparation of segmented NIPUs was developed using epoxide chemistry. The soft and hard segment precursors were obtained by epoxidation from polytetramethylene ether glycol (PTMEG, M n = 2000 g mol⁻¹), polycaprolactone diol (PCD, M n = 2000 g mol⁻¹), and from a hydroxy-urethane derived from furfurylamine, respectively. Polymerization was carried out in two consecutive steps. Initially, the epoxidized soft- and hard-segment precursors were reacted with 1,6-hexamethylenediamine to form furan-terminated prepolymers containing secondary hydroxyl groups. Subsequently, chain extension was achieved through thermoreversible Diels-Alder coupling with bismaleimide, yielding segmented polyurethane networks. Synthesized NIPUs were characterized via FTIR, NMR, and MALDI-TOF MS, and their structure-property relationships were investigated using DSC, DMA, SEM, swelling, and tensile tests. Owing to the incorporation of thermoreversible Diels-Alder linkages, the prepared polymer networks also exhibited intrinsic self-healing capability. The proposed synthetic approach provides a straightforward and environmentally benign route toward segmented non-isocyanate polyurethanes offering broad opportunities for tailoring material performance through molecular design.
SN - 2046-2069
ER -