Novel guaiacol-based high-performance dimethacrylate containing fluorenyl cardo structure for dental restorative resins

IF 3.3 2区医学 Q2 ENGINEERING, BIOMEDICAL

Journal of the Mechanical Behavior of Biomedical Materials Pub Date : 2025-04-25 DOI:10.1016/j.jmbbm.2025.107032

Yinan Sun , Lihua Hong , Lin Sun , Chengji Zhao

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引用次数: 0

Abstract

In dentistry, the use of bisphenol A glycidyl methacrylate (Bis-GMA) is being questioned since bisphenol A is regarded as an endocrine disruptor. As alternative candidates to Bis-GMA, bio-based dental resins face the crucial challenge of low mechanical strength and high water sorption. In this study, a novel guaiacol-based dimethacrylate containing fluorenyl cardo-structure was developed to effectively improve the hydrophobicity, enhance the mechanical properties, and reduce the polymerization shrinkage of bio-based dental restorative resins. Therefore, 9, 9-bis(3-methoxy-4-glycerolate methacrylate)fluorene (BMHF-GMA) was synthesized from a new guaiacol-based bisphenol, 9, 9-bis(3-methoxy-4-phenol)fluorene (BMHF), which is a lower estrogenic activity bisphenol monomer than commercial bisphenols from the results of cell proliferation test. The experimental dental resin (5 MHMA5T) was prepared containing BMHF-GMA and triethylene glycol dimethacrylate in a 1:1 ratio. The control group (5B5T) replaced BMHF-GMA completely with Bis-GMA. Evaluation of both dental resins revealed that 5 MHMA5T possessed comparable double bond conversion (>50 % in 20 s), better volumetric polymerization shrinkage (7.19 ± 0.09 %), shrinkage stress (0.92 ± 0.01 MPa in 1200 s), water sorption (39.9 ± 0.52 μg mm⁻³), water solubility (0.99 ± 0.04 μg mm⁻³) and lower cytotoxicity compared with 5B5T. 5 MHMA5T had superior mechanical properties (flexural strength: 122.30 ± 5.00 MPa; flexural modulus: 3.49 ± 0.02 GPa; Vickers hardness number: 25.21 ± 0.56 HV). Especially, after water immersion, it still maintained adequate mechanical properties (flexural strength: 97.34 ± 5.00 MPa; flexural modulus: 2.92 ± 0.02 GPa; Vickers hardness number: 19.33 ± 0.61 HV). Therefore, the new dimethacrylate BMHF-GMA shows great potential in complex and wet oral environments and offers a promising alternative to Bis-GMA in dental restorative resins.

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新型的以愈创木酚为基础的含氟烯基cardo结构的高性能牙体修复树脂二甲基丙烯酸酯

在牙科中，双酚A缩水甘油酯甲基丙烯酸酯（Bis-GMA）的使用受到质疑，因为双酚A被认为是一种内分泌干扰物。作为Bis-GMA的替代品，生物基牙科树脂面临着低机械强度和高吸水性的关键挑战。本研究制备了一种新型的愈创木酚基含氟烯基心脏结构的二甲基丙烯酸酯，有效地改善了生物基牙科修复树脂的疏水性，提高了力学性能，减少了聚合缩水率。因此，以一种新的愈创木酚基双酚为原料合成了9,9 -双（3-甲氧基-4-甘油甲基丙烯酸酯）芴（BMHF），该双酚单体的细胞增殖试验结果表明，它是一种雌激素活性低于市售双酚的双酚单体。以BMHF-GMA和三甘醇二甲基丙烯酸酯为原料，以1:1的比例制备实验牙用树脂（5 MHMA5T）。对照组（5B5T）用Bis-GMA完全替代BMHF-GMA。对两种牙用树脂的评价表明，与5B5T相比，5 MHMA5T具有相当的双键转化率（20 s内达到50%）、更好的体积聚合收缩率（7.19±0.09%）、收缩应力（1200 s内达到0.92±0.01 MPa）、吸水性（39.9±0.52 μg mm−3）、水溶性（0.99±0.04 μg mm−3）和更低的细胞毒性。5 MHMA5T具有优异的力学性能(抗弯强度：122.30±5.00 MPa；弯曲模量：3.49±0.02 GPa；维氏硬度值：25.21±0.56 HV)。特别是浸水后，仍能保持良好的力学性能(抗折强度：97.34±5.00 MPa；弯曲模量：2.92±0.02 GPa；维氏硬度值：19.33±0.61 HV)。因此，新型二甲基丙烯酸酯BMHF-GMA在复杂和潮湿的口腔环境中显示出巨大的潜力，是一种有希望替代Bis-GMA的口腔修复树脂。

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来源期刊

Journal of the Mechanical Behavior of Biomedical Materials 工程技术-材料科学：生物材料

CiteScore

7.20

自引率

7.70%

发文量

505

审稿时长

46 days

期刊介绍： The Journal of the Mechanical Behavior of Biomedical Materials is concerned with the mechanical deformation, damage and failure under applied forces, of biological material (at the tissue, cellular and molecular levels) and of biomaterials, i.e. those materials which are designed to mimic or replace biological materials. The primary focus of the journal is the synthesis of materials science, biology, and medical and dental science. Reports of fundamental scientific investigations are welcome, as are articles concerned with the practical application of materials in medical devices. Both experimental and theoretical work is of interest; theoretical papers will normally include comparison of predictions with experimental data, though we recognize that this may not always be appropriate. The journal also publishes technical notes concerned with emerging experimental or theoretical techniques, letters to the editor and, by invitation, review articles and papers describing existing techniques for the benefit of an interdisciplinary readership.