Synthesis and Application of UV-curable Phosphorous-containing Acrylated Epoxidized Soybean Oil-based Resins

Abstract

A novel phosphorous-containing acrylated epoxidized soybean oil-based (P-AESO) resin was developed via the ring-opening reaction of epoxidized soybean oil (ESO) with diphenylphosphinic chloride (DPPC), followed by acrylation of the resulting groups. The chemical structure was characterized by Fourier transform infrared spectroscopy (FT-IR), and 1H nuclear magnetic resonance (1H NMR). Subsequently, the viscosity and volumetric shrinkage of the obtained P-AESO resins were studied. Then the oligomer was formulated into UV-curable coatings, and the mechanical, thermal, and coating properties of the resulting UV-cured bioresins were studied by tensile testing, dynamic mechanical thermal analysis (DMA), thermogravimetric analysis (TGA) coupled with FT-IR spectroscopy (TGA-FT-IR), hardness, adhesion, pencil hardness and chemical resistance. Furthermore, the UV-curing behavior of the P-AESO resin was determined by real-time realtime infrared (RT-IR). Meanwhile, compared with coating from acrylated epoxidized soybean oil (AESO), the P-AESO system coatings showed better volumetric shrinkage, excellent adhesion, and enhanced thermal and glass transition temperature (Tg) while maintaining reasonably final C=C conversions and cross-link density. For instance, the obtained P-AESO/trimethylolpropanetriacrylate (TMPTA) 20 material possessed a volumetric shrinkage of 4.1%, Tg of 115.6°C, char yield of 9.47%, and final C=C conversions of 81.4% respectively, which exhibited superior values than that of the AESO/TMPTA20 material. The improvement of the P-AESO coating performances could contribute to the architectures that combined the structural features of phosphorous-containing rigid benzene. The developed P-AESO resin is promising for applications in the UV-curable coatings.

Keywords

• biobased
• UV-curable coatings
• acrylated epoxidized soybean oil
• diphenylphosphinic chloride