Synthesis and structural characterization of bio-based bis(cyclic carbonate)s for the preparation of non-isocyanate polyurethanes

Abstract

Bio-based cyclic carbonates are of significant research interest as monomers for non-isocyanate polyurethane (NIPU) synthesis. This research describes the synthesis of a series of five-membered bis(cyclic carbonate)s using bio-based polyether polyols (PO3G) with different molecular weights (250, 650 and 1000 g mol⁻¹) and carbon dioxide as green feedstocks. The utilization of CO₂ as a source of carbon in the chemical reaction is in agreement with the sustainable chemical industry. Furthermore, in order to support the green and sustainable polymer chemistry approach, the syntheses were attempted under solvent-free conditions. The implemented synthetic methods are focused on the design of processes and final products that minimize negative environmental impact. Detailed chemical structure analysis of synthesized products was performed using a combination of spectroscopy techniques (ATR-FTIR as well as 1D and 2D NMR techniques), mass spectrometry (MALDI-TOF MS) and chromatography analysis (SEC). The formation of the main product with two terminal cyclic carbonates was confirmed and the formed side products were also identified, characterized and quantified. Finally, as a proof of concept, the synthesized bis(cyclic carbonate)s were successfully used for the preparation of NIPU thermosets. Chemical and mechanical properties of the produced materials suggest their high potential for future applications, e.g. as sound absorbing materials.