A polymerizable difunctional photoinitiator featuring a bio-based group and its photoinitiating properties

Abstract

A polymerizable difunctional photoinitiator 2-methylene-succinic acid bis-{2-[4-(2-hydroxy-2-methylpropionyl)phenoxy]ethyl} ester (IAHHMP) based on the commercial photoinitiator 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropanone (HHMP) and a biorenewable itaconic acid is synthesized by esterification. The structure is confirmed by ultraviolet spectroscopy, Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy (1H NMR, 13C NMR) and thermogravimetric analysis. The photopolymerization behaviour of the photoinitiator is investigated using photo-differential scanning calorimetry and compared with that of two commercial photoinitiators, HHMP (or photoinitiator 2959) and 1-hydroxycyclohexyl phenyl ketone (or photoinitiator 184). The results show that IAHHMP has a strong UV absorption capacity at 245~300 nm and can initiate polymerization of monomers containing a double bond. The relative migration of IAHHMP is less than that of the systems containing an HHMP or 1-hydroxycyclohexyl phenyl ketone photoinitiator. Therefore, IAHHMP is expected to have potential applications in more environmentally friendly materials, such as in food and medical packaging.