Novel polyurethane produced from canola oil based poly(ether ester) polyols: Synthesis, characterization and properties

Abstract

Two novel bio-based poly(ether ester) polyols (Liprol™ 270 and Liprol™ 320) with high functionality and low viscosity were synthesized from canola oil. A simple, two-step reaction sequence of epoxidation followed by hydroxylation and transesterification with 1,3-propanediol or 1,2-propanediol was used resulting in a versatile, low cost process. The chemical structures of the low molecular weight compounds in the polyols produced were identified by liquid chromatography–mass spectrometry (LC–MS) while the distribution of oligomers was elucidated by size exclusion chromatography (SEC). The feasibility of utilizing these polyols for the production of polyurethanes (PUs) was demonstrated by reacting them with commercial petrochemical derived diisocyanate. The physical properties of the PUs prepared were characterized by FTIR, dynamic mechanical analysis (DMA), modulated differential scanning calorimetry (MDSC), and thermo gravimetric analysis (TGA). It was found that Liprol derived PUs had high glass transition temperatures, good hydrolytic stability and alkali resistance, and formed highly cross-linked networks. This work is the first that establishes the production of polyols and their corresponding PUs from vegetable oil starting materials whose glycerol backbone was removed explicitly during the polyol synthesis reaction.