Abstract
With the aim of reducing human exposure to Bisphenol A (BPA) derivatives in dentistry, a fluorinated dimethacrylate monomer was synthesized to replace 2,2-bis[4-(2-hydroxy-3-methacryloy-loxypropyl)-phenyl]propane (Bis-GMA) as the base monomer of dental resin. After mixing with reactive diluent triethyleneglycol dimethacrylate (TEGDMA), fluorinated dimethacrylate (FDMA)/TEGDMA was prepared and compared with Bis-GMA/TEGDMA in physicochemical properties, such as double bond conversion (DC), volumetric shrinkage (VS), water sorption (WS) and solubility (WSL), flexural strength (FS) and modulus (FM). The results showed that, when compared with Bis-GMA based resin, FDMA-based resin had several advantages, such as higher DC, lower VS, lower WS, and higher FS after water immersion. All of these revealed that FDMA had potential to be used as a substitute for Bis-GMA. Of course, many more studies, such as biocompatibility testing, should be undertaken to prove whether FDMA could be applied in clinic.
Highlights
Since they were first applied in dentistry in the 1960s, light-curable methacrylate-based dental composites have been widely used in clinic because of their advantages, such as excellent aesthetic property and easy handling [1]
Bis-glycidyl methacrylate (GMA) is a predominant monomer used in commercial dental composites, and the dominance of Bis-GMA is attributed to its low volumetric shrinkage, high reactivity, good mechanical properties, low volatility and diffusivity into tissues [2,8]
High viscosity that is induced by the intermolecular interaction is not good for the dental resin system, because it can decrease the flexibility of the polymer chain and the mobility of the reactive monomer, leading to a decrease in double bond conversion (DC) [28,29,30]
Summary
Since they were first applied in dentistry in the 1960s, light-curable methacrylate-based dental composites have been widely used in clinic because of their advantages, such as excellent aesthetic property and easy handling [1]. Dental composites consist of a methacrylate-based resin matrix, a photoinitiation system, and silane coupling agent-treated fillers [2]. Bis-GMA is a predominant monomer used in commercial dental composites, and the dominance of Bis-GMA is attributed to its low volumetric shrinkage, high reactivity, good mechanical properties, low volatility and diffusivity into tissues [2,8]. Though it was reported that Bis-GMA could not hydrolyze into BPA [15,16,17], BPA was still detected to be released out of commercial Bis-GMA based dental composites [8,18]. With the aim of minimizing human exposure to BPA, using methacrylate monomers that are not derived from BPA might be an effective way
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