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Photopolymerization initiated by p-diethylene glycol monomethyl ether cinnamyl formamide-based disulfide under 455 nm LED with minimized volume shrinkage

Yuhan Zhang,Nan Xiao,Yanjing Gao,Fang Sun

This study introduces a novel p -diethylene glycol monomethyl ether cinnamyl formamide-based disulfide monomer , N,N′ -(disulfanediylbis(2,1-phenylene)) bis(4-(4-(2-(2-methoxyethoxy)ethoxy) phenyl)-2-oxobut-3-enamide) (Mp-BSCF), designed to reduce the volume shrinkage of photosensitive resins and initiate monomer polymerization under 455 nm LED light irradiation. The photochemical properties and photoinitiation efficiency of Mp-BSCF are systematically investigated using UV–vis absorption spectroscopy , electron paramagnetic resonance (EPR) and real-time infrared spectroscopy . Although its weak absorption around 455 nm, Mp-BSCF can generate arylthiyl radicals under 455 nm LED irradiation, and then effectively initiate the polymerization of triethylene glycol dimethacrylate (TEGDMA)/A glycerolate dimethacrylate (Bis-GMA) system. Increasing Mp-BSCF addition enhances the final double bond conversion and maximum polymerization rate of the TEGDMA/Bis-GMA system, reaching up to 82.0 % and 2.02 % s −1 , respectively. Notably, Mp-BSCF significantly reduces the volume shrinkage of the photopolymerization system, with the addition of 10 % Mp-BSCF resulting in a 50 % reduction compared to the control system. This reduction is attributed to the dynamic reversible nature of the S S bond “breaking-recovery” and the intermolecular hydrogen bond interaction. Additionally, Mp-BSCF improves the thermal stability, friction resistance, and hardness of the TEGDMA/Bis-GMA photopolymerization system.