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Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s.

ABSTRACT: Conversion of β-elemene into new β-elemene dicarbonates through epoxidation and halide salt-catalyzed CO₂ cycloaddition reactions is reported. Step-growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)s with 1.3≤M_n ≤6.3 kDa and 1.3≤Ð≤2.1, and with glass transition temperatures ranging from -59 to 84 °C. The preparation of one selected polyhydroxyurethane material, obtained in the presence of Jeffamine® D-2010 was scaled-up to 43 g. The latter, when combined in a formulation using Irgacure® 2100 and Laromer® LR 9000 allowed the preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanes towards the preparation of commercially relevant materials.

SUBMITTER: Maquilon C

PROVIDER: S-EPMC9541927 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Renewable Beta-Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s.

Maquilón Cristina C Brandolese Arianna A Alter Christian C Hövelmann Claas H CH Della Monica Francesco F Kleij Arjan W AW

ChemSusChem 20220725 17

Conversion of β-elemene into new β-elemene dicarbonates through epoxidation and halide salt-catalyzed CO<sub>2</sub> cycloaddition reactions is reported. Step-growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)s with 1.3≤M<sub>n</sub> ≤6.3 kDa and 1.3≤Ð≤2.1, and with glass transition temperatures ranging from -59 to 84 °C. The preparation of one se ...[more]

PMID: 35757910

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