Abstract
In this paper, a fully bio-based vinyl oligomer with high functionalities was successfully prepared by three steps: epoxidation of rapeseed oil, solvent-free and catalyst-free ring opening by 10-undecylenic acid, and esterification with 10-undecenoyl chloride. Then, the renewable polymers were prepared by photo-polymerization of these modified vegetable oils and 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 and thermal stability of UV-curable films were characterized. The resulting polymers exhibit excellent water resistance and thermals stability, which is promising to find application in coatings and adhesives.
Highlights
With the depletion of fossil resources and the increasing concerns toward environmental issue, much effort has been dedicated to develop polymeric materials from renewable resource as a replacement of petroleum based counterparts for a sustainable and environment-friendly society [1,2,3,4]
Undecenoyl Modified Rapeseed Oil-based Oligomer (UROO) was synthesized by three steps: epoxidation of Rapeseed oil (RO), solvent-free and catalyst-free ring opening by 10-undecylenic acid, and esterification with 10-undecenoyl chloride
The peaks at 5.35 ppm and 2.0 ppm corresponding to CH=CH- of RO disappear in the spectra of the Epoxidized Rapeseed Oil (ERO) and newly peaks corresponding to epoxy groups appear from 2.8 ppm to 3.2 ppm, indicating the successful epoxidation of RO
Summary
With the depletion of fossil resources and the increasing concerns toward environmental issue, much effort has been dedicated to develop polymeric materials from renewable resource as a replacement of petroleum based counterparts for a sustainable and environment-friendly society [1,2,3,4]. Highly branched vegetable oil derivatives with varying degrees of unsaturated double-bonds were successfully prepared by three steps: epoxidation of rapeseed oil, solvent-free and catalyst-free ring opening by 10-undecylenic acid, and esterification with 10-undecenoyl chloride. The renewable polymers were prepared by photo-polymerization of these modified vegetable oils and typical thiol monomers (pentaerythritol tetrakis (3-mercaptopropionate) (PETMP), pentaerythritol tris (3-mercaptopropionate) (PTMP) and 1, 2-ethanedithiol (EDT)). 2.3 Synthesis of The Rapeseed Oil Based Branched Polyols (UROP) The rapeseed oil polyols were prepared by ring-opening reaction between ERO with 10-undecylenic acid with a solvent-free and catalyst-free method. 2.4 Synthesis of the 10-Undecenoyl Modified Rapeseed Oil-based Oligomer (UROO) The rapeseed oil-based polyols (3.47 g, 0.002 mol) and triethylamine (1.6 g, 0.016 mol) were dissolved in ethyl acetate in a flask equipped with a magnetic stirrer and cooled in an ice bath, and 10-undecenoyl chloride (3.2 g, 0.016 mol) was added dropwise. The films were cured under the irradiation of a UV lamp (1700 μW/cm 365 nm) in air with 10 minutes
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