Syntheses and Characterization of Bio-Derived Polyurethanes and Imine-Networks for Industrial Applications in Foam and Fiber Composites

Novel cardanol based plasticizers, rosin-derived polyester-polyol and diisocyanate useful for the preparation of fully bio derived polyurethane compositions were synthesized following the 12 Principles of Green Chemistry. The plasticizers were synthesized from esterification of hydrogenated cardanol and bio-derived succinic acid with high conversion and with the required hydrophobic and low viscosity properties. The polyester-polyol was synthesized from acrylpimaric acid and biobased 1,3-propanediol resulting in a low molecular weight polyol with a hydroxyl value and thermal properties required for polyurethane applications. The diisocyante, was derived from acrylpimaric acid utilizing the Curtius rearrangement process. A novel imine oligomer was also synthesized in moderate yields using mild conditions, resulting in unique thermal and structural properties useful as a potential substrate for covalent adaptable network. All novel synthesized materials were characterized using nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) spectroscopy, high-resolution mass spectrometry (HR-MS), and differential scanning calorimetry (DSC).