Objective

Synthesize a new BPA-free monomer for use in methacrylate-based materials and evaluate critical properties of resin and composite materials based on the monomer.

Methods

Bis-EFMA was synthesized through reaction between 9,9-bis[4-(2-hydroxyethoxy)-phenyl]fluorene and 2-(methacryloyloxy)ethyl isocyanate. Experimental Bis-EFMA-based resin (Bis-EFMA/TEGDMA = 50/50, wt./wt.) and composite were prepared. Critical properties were investigated according to standard or referenced methods Bis-GMA/TEGDMA (50/50, wt./wt.) resin system, Bis-GMA-based composite and 3 M ESPE Filtek™ Z250 were used as controls.

Results

FT-IR and ¹H NMR spectra confirmed the structure of Bis-EFMA monomer. Cured resin materials: Bis-EFMA-based and Bis-GMA-based resins had nearly the same degree of conversion (p > 0.05); Bis-EFMA-based resin had significantly lower shrinkage, water sorption and solubility, and cytotoxicity than Bis-GMA-based resin (p < 0.05); flexural properties of Bis-EFMA-based resin were all higher than those of Bis-GMA-based resin (p < 0.05). Cured composite materials: There was no significant difference in conversion (p > 0.05); Bis-EFMA-based composite had significantly lower shrinkage and solubility (p < 0.05); water sorption of Bis-EFMA-based composite and Z250 were similar (p > 0.05), but lower compared to Bis-GMA-based composite (p < 0.05); Bis-EFMA-based composite had the deepest curing depth (p < 0.05); Before water immersion, there was no significant difference in flexural strength between Bis-EFMA-based composite and each control composite (p > 0.05), while FS became lower than that of Z250 (p < 0.05), but higher than that of Bis-GMA-based composite (p < 0.05) after water immersion; Flexural modulus of Bis-EFMA-based composite and Z250 were nearly the same (p > 0.05), higher than that of Bis-GMA-based composite (p < 0.05); Bis-EFMA-based composite showed less cytotoxicity than Bis-GMA-based composite and Z250 (p < 0.05).

Significance

Bis-EFMA has potential as a substitute for Bis-GMA to prepare Bis-GMA-free dental composites.

中文翻译：

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9,9-双[4-（2-羟基乙氧基）苯基]芴衍生的二甲基丙烯酸酯单体的无Bis-GMA牙科复合材料的制备和表征

客观的

合成一种新的不含BPA的单体，用于基于甲基丙烯酸酯的材料，并评估基于该单体的树脂和复合材料的关键性能。

方法

通过9,9-双[4-（2-羟基乙氧基）-苯基]芴与2-（甲基丙烯酰氧基）乙基异氰酸酯之间的反应合成Bis-EFMA。制备实验性的基于Bis-EFMA的树脂（Bis-EFMA / TEGDMA = 50/50，wt./wt。）和复合材料。根据标准或参考方法研究了关键性能，将Bis-GMA / TEGDMA（50/50，wt./wt。）树脂体系，基于Bis-GMA的复合材料和3 M ESPE Filtek™Z250用作对照。

结果

FT-IR和¹ H NMR光谱证实了Bis-EFMA单体的结构。固化树脂材料：Bis-EFMA基树脂和Bis-GMA基树脂具有几乎相同的转化度（p>  0.05）；与基于Bis-GMA的树脂相比，基于Bis-EFMA的树脂的收缩率，吸水率和溶解度以及细胞毒性显着更低（p <0.05）；Bis-EFMA基树脂的弯曲性能均高于Bis-GMA基树脂（p <0.05）。固化的复合材料：转化率无显着差异（p  > 0.05）；Bis-EFMA基复合材料的收缩率和溶解度显着降低（p  <0.05）；Bis-EFMA基复合材料和Z250的吸水率相似（p > 0.05），但低于基于Bis-GMA的复合材料（p <  0.05）；Bis-EFMA基复合材料的固化深度最深（p  <0.05）；浸水前，基于Bis-EFMA的复合材料与每个对照复合材料的抗弯强度没有显着差异（p  > 0.05），而FS低于Z250（p  <0.05），但高于Bis-浸水后基于GMA的复合材料（p  <0.05）；Bis-EFMA基复合材料和Z250的弯曲模量几乎相同（p  > 0.05），高于Bis-GMA基复合材料的弯曲模量（p  <0.05）；基于Bis-EFMA的复合材料的细胞毒性比基于Bis-GMA的复合材料和Z250（p ＜0.05）。

意义

Bis-EFMA有潜力替代Bis-GMA来制备不含Bis-GMA的牙科复合材料。