Synthesis of Bio-based Polyurethanes and Polyimines for Industrial Applications

Candidate: Tristan Calayan
Supervisor: Dr. Guerino Sacripanto and Dr. Robert Gossage

ABSTRACT

A novel fully bio-based polyurethane and an imine oligomer were synthesized using mild conditions, sustainable substrates, and safe chemistry design resulting in unique thermal and structural properties. Using rosin-based substrates such as acrylicpimaric acid, a polyester-type polyol was successfully synthesized following the 12 Principles of Green Chemistry: non-toxic reactions, solvent-free conditions, benign by-products, use of catalysis, presence of bio-based feedstocks and biodegradation mechanism study through pyrolysis. Cardanol as a second bio-based substrate resulted in a novel sustainable precursor for potential isocyanate synthesis. A potential oligomer for a covalent adaptable network using associative dynamic reversible linkages was synthesized using Schiff Base condensation of aldehydes and amines in moderate yields. The synthesized compounds and polymers were successfully characterized using nuclear magnetic resonance (NMR) and Fourier transfer infrared (FTIR) spectroscopy, high-resolution mass spectrometry (HR-MS), differential scanning calorimetry (DSC), gel permeation chromatography (GPC), acid value (AV), melting point (mp) and hydroxyl value (OH). These novel materials can potentially apply in industrial applications as foams, hydrogels and carbon-polymer composites for commercial bio-based plastics.