Issue 31, 2023

Polyhydroxyurethane covalent adaptable networks: looking for suitable catalysts

Abstract

Various bases (DMAP, DBU, TBD, t-BuOK), acid (p-TSA), thiourea (TU) and organometallic Lewis acid (DBTDL) were investigated as potential catalysts for the preparation of polyhydroxyurethane covalent adaptable networks. Catalytic systems were first selected for their ability to promote cyclic carbonate aminolysis quantitatively (full conversion of cyclic carbonates) with few or no side reactions (urea formation). Selected PHU networks were extensively characterized using thermo-mechanical analysis (TGA, DSC, DMA and tensile test), rheology experiments (stress relaxation, frequency sweep), spectroscopy analysis (ATR-IR), swelling and reprocessing tests. Combining rheology, ATR-IR analysis and model molecular reactions, we suggest a catalyst-dependent exchange mechanism in which solely the organotin Lewis acid (DBTDL) was capable to promote transcarbamoylation in PHU efficiently with both secondary (major product of aminolysis) and primary alcohols and thus an efficient reprocessing.

Graphical abstract: Polyhydroxyurethane covalent adaptable networks: looking for suitable catalysts

Supplementary files

Article information

Article type
Paper
Submitted
23 máj 2023
Accepted
19 júl 2023
First published
24 júl 2023

Polym. Chem., 2023,14, 3610-3620

Polyhydroxyurethane covalent adaptable networks: looking for suitable catalysts

C. Bakkali-Hassani, D. Berne, P. Bron, L. Irusta, H. Sardon, V. Ladmiral and S. Caillol, Polym. Chem., 2023, 14, 3610 DOI: 10.1039/D3PY00579H

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