A facile method to synthesis of a highly acrylated epoxidized soybean oil with low viscosity: Combined experimental and computational approach

This investigation deals with the introduction of an efficient technique to acrylate almost all of the epoxide groups on epoxidized soybean oil (ESO) and synthesize a highly acrylated ESO (AESO) by using viscosity control agents (VCAs). The effect of chemical structure, content, and addition step of VCAs (i.e. glycidyl neodecanoate, glycidyl hexanoate, and glycidyl acetate) on the reaction rate and viscosity was examined. Spectroscopy and analytical analyses as well as viscosity monitoring were employed to assess the acrylation reaction comprehensively. The intermolecular interactions were visualized by molecular dynamics simulation and quantified via the calculation of cohesion energy density to justify the viscosity changes during the reactions. Results demonstrated that the rate of ring-opening reaction is impaired by viscosity severely. Subsequently, the know-how for preparing the AESO with an acrylation degree of 3.5 via optimum reaction conditions was presented. Accordingly, this attempt indicated that the AESO diluted by acrylated glycidyl neodecanoate can be considered a promising oligomer along with other prominent diluents such as trimethylolpropane triacrylate and hexanediol diacrylate to prepare industrial light/UV-curable coatings with perfect performance (gel fraction: 97%, MEK double rub resistance: 75, Tg: 47 ?C, hardness: 123, cross-cut adhesion: 4B, gloss: 97.5%, and water contact angle: 89?).