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

Von Wiley-VCH zur Verfügung gestellt

Naturally: Biobased β-elemene was probed as a renewable precursor for the synthesis of non-isocyanate based polyurethane coatings. Conversion of this terpene into its bis-cyclic carbonate was examined, followed by polycondensation with commercially relevant diamines thereby providing oligourethanes as pre-polymers. One of these was tested extensively and found to be potentially suitable as a starting point for new coating formulations using a dual curing approach.


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≤Mn ≤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.

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