A facile method to synthesis of a highly acrylated epoxidized soybean oil with low viscosity: Combined experimental and computational approach. (November 2022)

• Record Type: Journal Article
• Authors: Baghban, Sahar Abdollahi; Ebrahimi, Morteza; Khorasani, Manoucher
• Is Part Of: Polymer testing. Volume 115(2022)
• Publication Date: 2022-11
• Subjects: Acrylated epoxidized soybean oil (AESO) -- Degree of acrylation -- Glycidyl neodecanoate -- Light-curing -- Hydrogen bond -- Molecular dynamics simulation -- Viscosity; Polymers -- Testing -- Periodicals; Polymères -- Tests -- Périodiques; 620.1920287
• DOI: 10.1016/j.polymertesting.2022.107727
• Languages: English
• ISSNs: 0142-9418

Abstract

Abstract: 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°). Highlights: A highly acrylated epoxidized soybean oil was attained via an efficient technique. The importance of viscosity on the rate of acrylation reaction was assessed. Glycidyl neodecanoate agent was employed to reduce the intermolecular interactions to facilitate the acrylation. The impact of hydroxyl group formation on elevating the hydrogen bonding and viscosity of AESO derivatives was visualized and quantified by using molecular dynamic simulation. The performance of AESO diluted by glycidyl neodecanoate in eco-friendly light/UV-curable coatings was investigated.