OBJECTIVE The use of the BisGMA as base monomer in dental composites has been questioned because of bisphenol A (BPA) is used as raw material in its synthesis, and BPA possess estrogenic potential associated to several health problems. This study describes the synthesis of the trimethacrylate tris(4-hydroxyphenyl)methane triglycidyl methacrylate (TTM) monomer and evaluate its effect when used as base monomer in the formulation of experimental photopolymerizable composite resins. METHODS The TTM monomer was synthesized by a nucleophilic acyl substitution. Its chemical structure was confirmed via 1H and 13C NMR spectroscopy and FTIR spectroscopy. Experimental composite resins were formulated by mixing TTM, triethyleneglycol dimethacrylate (TEGDMA) and inorganic fillers. A BisGMA/TEGDMA based composite resin was prepared and used as control to compare several physicochemical properties. Cell viability assay was used for cytotoxicity evaluation. RESULTS TTM was successfully synthesized with quantitative yields. The results showed that the TTM-based composite resin had similar values of flexural strength, elastic modulus, degree of conversion and polymerization shrinkage than the control (p > 0.05). Water sorption and solubility were statistically significantly higher than the control (p < 0.05), however they complied the requirements stablished by the ISO 4049. Finally, this study shows there were no statistically significant differences for the biocompatibility outcomes (p = 0.345). SIGNIFICANCE TTM monomer could be potentially useful in the formulation of BisGMA free composite resins, which could mean to minimize the human exposure to BPA.

中文翻译：

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基于新型三甲基丙烯酸酯单体的不含BisGMA的牙科复合树脂的制备和评估。

目的由于双酚A（BPA）被用作合成原料，因此BisGMA在牙科复合材料中用作基础单体受到质疑，BPA具有与若干健康问题相关的雌激素潜力。这项研究描述了三甲基丙烯酸三（4-羟苯基）甲烷甲基丙烯酸三缩水甘油酯（TTM）单体的合成，并评估了其在配制可光聚合复合树脂实验中用作基础单体时的效果。方法通过亲核酰基取代合成TTM单体。通过1H和13C NMR光谱和FTIR光谱确认了其化学结构。通过混合TTM，三乙二醇二甲基丙烯酸酯（TEGDMA）和无机填料来配制实验性复合树脂。制备了基于BisGMA / TEGDMA的复合树脂，并将其用作对照以比较几种物理化学性质。细胞活力测定用于细胞毒性评估。结果成功地合成了TTM，定量收率。结果表明，与对照相比，基于TTM的复合树脂具有相似的抗弯强度，弹性模量，转化度和聚合收缩率值（p> 0.05）。吸水率和溶解度在统计学上显着高于对照组（p <0.05），但符合ISO 4049规定的要求。最后，该研究表明，生物相容性结果无统计学差异（p = 0.345）。意义TTM单体可能在配制不含BisGMA的复合树脂时可能有用，