Synthesis and challenges of fluorinated divinyl urethane monomers as a strategy for masking hydrolytic sensitive methacrylate groups in resin composites.
Michael Lagowski, Zach Gouveia, Meilin Yang, Yoav Finer, J Paul Santerre
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引用次数: 0
Abstract
Objective: The biodegradation of methacrylate (MA)-based dental restoratives has been suggested to contribute to a loss of adhesion and subsequent detachment, or secondary caries, both major causes of restoration failure. Previous studies have demonstrated that intermolecular interactions between resin monomers may affect the hydrolytic-susceptibility of composites. Altering the intermolecular interactions by shielding or masking the hydrolytically-susceptible ester groups found in MA monomers could be an effective strategy to mitigate the biodegradation of resin composites. The objective of this work was to assess whether shielding/masking MAs using fluorinated groups could improve the biostability of experimental composites.
Methods: Eight fluorinated monomers (FM) were synthesized, characterized (1H NMR), and formulated into experimental resin composites (FC, 65 wt%, microfill). FCs were assessed for interactions with water (water contact angle, water sorption, gel fraction), mechanical properties (both compressive and flexural strength and modulus), cytocompatibility, resistance to biodegradation using simulated human salivary esterase (SHSE) and compared to a control composite (CC) without FM.
Results: Integration of FMs was found to generally decrease both the physical and mechanical properties under all incubation conditions when compared to the CC. Additionally, all FCs had a negative influence on composite biodegradation following immersion in SHSE when compared to the CC.
Significance: Shielding/masking MA-esters inherently inserts molecular spaces between the polymer chains within the resin network, and shielding is likely not possible while also maintaining the necessary cohesive forces that regulate the physical and mechanical properties of resin composites. Novel dental resin development should seek to remove/replace vulnerable ester-containing MAs rather that adopting a shielding/masking approach.
目的：有人认为，甲基丙烯酸酯（MA）基牙科修复体的生物降解会导致粘附力丧失、随后脱落或继发龋齿，而这两种情况都是修复体失效的主要原因。以往的研究表明，树脂单体之间的分子间相互作用可能会影响复合材料的水解敏感性。通过屏蔽或掩盖 MA 单体中易水解的酯基来改变分子间相互作用可能是减轻树脂复合材料生物降解的有效策略。这项工作的目的是评估使用含氟基团屏蔽/掩蔽 MA 是否能改善实验复合材料的生物稳定性：方法：合成了八种含氟单体（FM），对其进行了表征（1H NMR），并将其配制成实验性树脂复合材料（FC，65 wt%，微填充）。评估了 FM 与水的相互作用（水接触角、水吸附、凝胶分数）、机械性能（抗压、抗弯强度和模量）、细胞相容性、使用模拟人唾液酯酶（SHSE）的抗生物降解性，并与不含 FM 的对照复合材料（CC）进行了比较：结果：与 CC 相比，在所有培养条件下，加入调频材料会普遍降低物理和机械性能。此外，与 CC 相比，在 SHSE 中浸泡后，所有 FC 对复合材料的生物降解都有负面影响：意义：MA-酯的屏蔽/掩蔽本质上是在树脂网络中的聚合物链之间插入分子空隙，屏蔽可能无法同时保持调节树脂复合材料物理和机械性能的必要内聚力。新型牙科树脂的开发应设法去除/替代易受影响的含酯 MA，而不是采用屏蔽/掩蔽方法。
期刊介绍：
Dental Materials publishes original research, review articles, and short communications.
Academy of Dental Materials members click here to register for free access to Dental Materials online.
The principal aim of Dental Materials is to promote rapid communication of scientific information between academia, industry, and the dental practitioner. Original Manuscripts on clinical and laboratory research of basic and applied character which focus on the properties or performance of dental materials or the reaction of host tissues to materials are given priority publication. Other acceptable topics include application technology in clinical dentistry and dental laboratory technology.
Comprehensive reviews and editorial commentaries on pertinent subjects will be considered.
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