Enhanced aminolysis of cyclic carbonates by β-hydroxyamines for fully biobased polyhydroxyurethanes

Baptiste Quienne (1) , Rinaldo Poli (2) , Julien Pinaud (1) , Sylvain Caillol (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 LCC - Laboratoire de chimie de coordination

The aminolysis of five-membered cyclic carbonates which results in polyhydroxyurethanes (PHUs) is one of the most promising synthetic pathway to achieve isocyanate-free polyurethanes (NIPUs), one of the main industrial challenges over the coming years. This study highlighted the higher reactivity of β-hydroxyamines toward cyclic carbonate in comparison to classical alkylamines through the determination of their reaction rate constants. The key role of the β-OH substituent in the aminolysis was enlighten by a DFT investigation. Polyfunctional alkylamine and β-hydroxyamine were then used for the synthesis of fully biobased PHU thermosets. The higher reactivity of β-hydroxyamines 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.

Mots clés: DFT; reactivity; β-hydroxyamines; cyclic carbonate; polyhydroxyurethanes; biobased polymers

Domaines: Polymères; Chimie théorique et/ou physique

Baptiste Quienne, Rinaldo Poli, Julien Pinaud, Sylvain Caillol. Enhanced aminolysis of cyclic carbonates by β-hydroxyamines for fully biobased polyhydroxyurethanes. Green Chemistry, 2021, 23 (4), pp.1678-1690. ⟨10.1039/d0gc04120c⟩. ⟨hal-03155254⟩