Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group.

Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group.
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DOI:
10.1002/jbm.b.31987
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发表时间:
2012-02
期刊:
Journal of biomedical materials research. Part B, Applied biomaterials
影响因子:
--
通讯作者:
Spencer P
Spencer P
中科院分区:
其他
文献类型:
--
作者:
Park J;Ye Q;Singh V;Kieweg SL;Misra A;Spencer P

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合成、表征了一种新型甘油基二甲基丙烯酸酯单体与芳香族羧酸,2-((1,3-双(甲基丙烯酰氧基)丙-2-基氧基)羰基)苯甲酸(BMPB),并进行了表征,并建议作为牙本质粘合剂的可能的牙科共聚单体。除了 BMPB 之外,还含有甲基丙烯酸 2-羟乙酯 (HEMA) 和 2,2-双[4-(2-羟基-3-甲基丙烯酰氧基丙氧基)苯基]丙烷 (BisGMA) 的牙本质粘合剂与 0、5、10 和 15 wt% 的水一起配制,以模拟湿润的口腔条件并进行光聚合。对粘合剂的粘度、实时光聚合行为、动态力学分析和微尺度 3D 内部形态进行了表征,并与 HEMA/BisGMA 对照进行了比较。在潮湿条件下配制时,实验粘合剂的粘度 (0.04–0.07 Pa s) 低于对照粘合剂 (0.09–0.12 Pa s)。与对照胶粘剂(分别为 123–135°C、67–71%、15–26 MPa 和空隙)相比,实验粘合剂显示出更高的玻璃化转变温度(146–157°C)、转化度(78–89%)和橡胶模量(33–36 MPa),并且改善了水混溶性(无空隙)。这些粘合剂的增强性能表明,合成简单、直接的 BMPB 是一种有前途的牙科修复材料光固化共聚单体。
A new glycerol-based dimethacrylate monomer with an aromatic carboxylic acid, 2-((1,3-bis(methacryloyloxy)propan-2-yloxy)carbonyl)benzoic acid (BMPB), was synthesized, characterized, and proposed as a possible dental co-monomer for dentin adhesives. Dentin adhesives containing 2-hydroxyethyl methacrylate (HEMA) and 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA) in addition to BMPB were formulated with water at 0, 5, 10, and 15 wt % to simulate wet, oral conditions, and photo-polymerized. Adhesives were characterized with regard to viscosity, real-time photopolymerization behavior, dynamic mechanical analysis, and microscale 3D internal morphologies and compared with HEMA/BisGMA controls. When formulated under wet conditions, the experimental adhesives showed lower viscosities (0.04–0.07 Pa s) as compared to the control (0.09–0.12 Pa s). The experimental adhesives showed higher glass transition temperature (146–157°C), degree of conversion (78–89%), and rubbery moduli (33–36 MPa), and improved water miscibility (no voids) as compared to the controls (123–135°C, 67–71%, 15–26 MPa, and voids, respectively). The enhanced properties of these adhesives suggest that BMPB with simple, straight-forward synthesis is a promising photocurable co-monomer for dental restorative materials.
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