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疏水改性的异山梨醇二甲基丙烯酸酯作为一种不含双酚A（BPA）的牙科填充材料。

Hydrophobically Modified Isosorbide Dimethacrylates as a Bisphenol-A (BPA)-Free Dental Filling Material.

作者信息

Marie Bilal, Clark Raymond, Gillece Tim, Ozkan Seher, Jaffe Michael, Ravindra Nuggehalli M

机构信息

Interdisciplinary Program in Materials Science and Engineering, New Jersey Institute of Technology, Newark, NJ 07012, USA.

Ashland Specialty Ingredients, Bridgewater, NJ 08807, USA.

出版信息

Materials (Basel). 2021 Apr 22;14(9):2139. doi: 10.3390/ma14092139.

DOI:10.3390/ma14092139
PMID:33922355
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8122847/
Abstract

A series of bio-based hydrophobically modified isosorbide dimethacrylates, with , , and benzoate aromatic spacers (ISBGBMA), are synthesized, characterized, and evaluated as potential dental restorative resins. The new monomers, isosorbide 2,5-bis(4-glyceryloxybenzoate) dimethacrylate (ISB4GBMA), isosorbide 2,5-bis(3-glyceryloxybenzoate) dimethacrylate (ISB3GBMA), and isosorbide 2,5-bis(2-glyceryloxybenzoate) dimethacrylate (ISB2GBMA), are mixed with triethylene glycol dimethacrylate (TEGDMA) and photopolymerized. The resulting polymers are evaluated for the degree of monomeric conversion, polymerization shrinkage, water sorption, glass transition temperature, and flexural strength. Isosorbide glycerolate dimethacrylate (ISDGMA) is synthesized, and Bisphenol A glycerolate dimethacrylate (BisGMA) is prepared, and both are evaluated as a reference. Poly(ISBGBMA/TEGDMA) series shows lower water sorption (39-44 µg/mm) over Poly(ISDGMA/TEGDMA) (73 µg/mm) but higher than Poly(BisGMA/TEGDMA) (26 µg/mm). Flexural strength is higher for Poly(ISBGBMA/TEGDMA) series (37-45 MPa) over Poly(ISDGMA/TEGDMA) (10 MPa) and less than Poly(BisGMA/TEGDMA) (53 MPa) after immersion in phosphate-buffered saline (DPBS) for 24 h. Poly(ISB2GBMA/TEGDMA) has the highest glass transition temperature at 85 °C, and its monomeric mixture has the lowest viscosity at 0.62 Pa·s, among the (ISBGBMA/TEGDMA) polymers and monomer mixtures. Collectively, this data suggests that the ortho ISBGBMA monomer is a potential bio-based, BPA-free replacement for BisGMA, and could be the focus for future study.

摘要

合成了一系列具有间苯二甲酸酯、对苯二甲酸酯和邻苯二甲酸酯芳香间隔基的生物基疏水改性异山梨醇二甲基丙烯酸酯（ISBGBMA），并对其进行了表征，作为潜在的牙科修复树脂进行了评估。新单体异山梨醇2,5-双（4-甘油氧基苯甲酸酯）二甲基丙烯酸酯（ISB4GBMA）、异山梨醇2,5-双（3-甘油氧基苯甲酸酯）二甲基丙烯酸酯（ISB3GBMA）和异山梨醇2,5-双（2-甘油氧基苯甲酸酯）二甲基丙烯酸酯（ISB2GBMA）与三乙二醇二甲基丙烯酸酯（TEGDMA）混合并光聚合。对所得聚合物的单体转化率、聚合收缩率、吸水率、玻璃化转变温度和弯曲强度进行了评估。合成了异山梨醇甘油酯二甲基丙烯酸酯（ISDGMA），制备了双酚A甘油酯二甲基丙烯酸酯（BisGMA），并将两者作为参考进行了评估。聚（ISBGBMA/TEGDMA）系列的吸水率（39 - 44 μg/mm）低于聚（ISDGMA/TEGDMA）（73 μg/mm），但高于聚（BisGMA/TEGDMA）（26 μg/mm）。在磷酸盐缓冲盐水（DPBS）中浸泡24小时后，聚（ISBGBMA/TEGDMA）系列的弯曲强度（37 - 45 MPa）高于聚（ISDGMA/TEGDMA）（10 MPa），低于聚（BisGMA/TEGDMA）（53 MPa）。在（ISBGBMA/TEGDMA）聚合物和单体混合物中，聚（ISB2GBMA/TEGDMA）的玻璃化转变温度最高，为85℃，其单体混合物的粘度最低，为0.62 Pa·s。总体而言，这些数据表明邻位ISBGBMA单体是一种潜在的生物基、不含双酚A的BisGMA替代品，可能是未来研究的重点。

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