Issue 3, 2020

Fully bio-derived CO2 polymers for non-isocyanate based polyurethane synthesis

Abstract

The synthesis of partly carbonated polybutadienes (PC-PBDs) was developed starting from partly epoxidized polybutadienes (PE-PBDs) and CO2 as renewable feedstock. The latter is a versatile polymer precursor for post-functionalization. A screening of metal-free catalysts demonstrated superior performance of bis(triphenylphosphine)iminium chloride (PPN-Cl) relative to tetra-n-butylammonium bromide (TBAB), giving >99% epoxide conversion and >99% chemoselectivity. Initial higher activities were found for PPN-Br. PPN-X (X = Cl, Br, I) catalyst activities increase in the order Br > Cl > I. Investigation of the polymer microstructures under different reaction conditions revealed that 1,2-vinyl and 1,2-cyclic epoxides are the most reactive moieties towards CO2 followed by cis- and trans epoxides, respectively. Subsequently performed non-isocyanate polyurethane (NIPU) cross-linking reactions using (bio-derived) diamines demonstrated the capability of these PC-PBDs as a modular feedstock for the synthesis of tunable hybrid NIPU thermosets.

Graphical abstract: Fully bio-derived CO2 polymers for non-isocyanate based polyurethane synthesis

Supplementary files

Article information

Article type
Paper
Submitted
08 Oct 2019
Accepted
13 Jan 2020
First published
14 Jan 2020

Green Chem., 2020,22, 969-978

Fully bio-derived CO2 polymers for non-isocyanate based polyurethane synthesis

S. Dechent, A. W. Kleij and G. A. Luinstra, Green Chem., 2020, 22, 969 DOI: 10.1039/C9GC03488A

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