Synthesis of a Fully Blobased Polyfunctional Vinyl Oligomer and Their UV Cured Films Prepared via Thiol-ene Coupling

摘要

In this paper, a fully bio-based vinyl oligomer with high functionalities was successfully prepared from rapeseed oil by three modification steps: epoxidation of rapeseed oil, solvent-free and catalyst-free ring opening by 10-undecylenic acid followed by esterification with 10-undecenoyl chloride. Then, the renewable polymers were prepared by photo-polymerization of these modified vegetable oils with typical thiol monomers: pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate) and 1,2-ethanedithiol. The synthesis of the vinyl oligomer was monitored by nuclear magnetic resonance and Fourier-transform infrared spectroscopy. The average number of the carbon-carbon double bonds of the resulting vinyl oligomer is high to be 7.2. The kinetic of thiol-ene photo-polymerization of vegetable oil- based vinyl oligomer was studied by FTIR-ATR analyses. In addition, the thermo-physical properties, thermal stability and solvent resistance of these UV cured films were characterized. The polymers from 1,2-ethanedithiol exhibit higher gel content, storage modulus and glass transition temperature than those from other thiol monomers due to the high crosslinking densities of the resulting polymers. All polymers show excellent thermal stability up to 290°C. The resulting polymers exhibit thermo-physical properties, excellent water resistance and thermals stability, which is promising to find application in coatings and adhesives.