Enhanced aminolysis of cyclic carbonates by β-hydroxylamines for the production of fully biobased polyhydroxyurethanes - Archive ouverte HAL Access content directly
Journal Articles Green Chemistry Year : 2021

Enhanced aminolysis of cyclic carbonates by β-hydroxylamines for the production of fully biobased polyhydroxyurethanes

Abstract

The aminolysis of five-membered cyclic carbonates, which results in polyhydroxyurethanes (PHUs), is one of the most promising synthetic pathways to achieve isocyanate-free polyurethanes (NIPUs), one of the main industrial challenges over the coming years. This study highlights the higher reactivity of β-hydroxylamines toward cyclic carbonates compared to classical alkylamines through the determination of their reaction rate constants. The key role of the β-OH substituent in the aminolysis was revealed by DFT investigation. Polyfunctional alkylamine and β-hydroxyamine were then used for the synthesis of fully biobased PHU thermosets. The higher reactivity of β-hydroxylamines was confirmed by the gelation time gap between the two formulations studied. After curing, the thermal and thermo-mechanical properties of the thermosets were compared.
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Dates and versions

hal-03148901 , version 1 (22-02-2021)

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Baptiste Quienne, Rinaldo Poli, Julien Pinaud, Sylvain Caillol. Enhanced aminolysis of cyclic carbonates by β-hydroxylamines for the production of fully biobased polyhydroxyurethanes. Green Chemistry, 2021, 23 (4), pp.1678-1690. ⟨10.1039/D0GC04120C⟩. ⟨hal-03148901⟩
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