Al-Kahtani Haifa Masfeer, Al-Odayni Abdel-Basit, Saeed Waseem Sharaf, Robaian Ali, Al-Kahtani Abdullah, Aouak Taieb, Alrahlah Ali
Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Engineer Abdullah Bugshan Research Chair for Dental and Oral Rehabilitation, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia.
Polymers (Basel). 2023 Mar 16;15(6):1481. doi: 10.3390/polym15061481.
This work aimed to synthesize a novel dimethacrylated-derivative of eugenol (Eg) (termed EgGAA) as potential biomaterial for certain applications such as dental fillings and adhesives. EgGAA was synthesized through a two-step reaction: (i) a mono methacrylated-eugenol (EgGMA) was produced via a ring-opening etherification of glycidyl methacrylate (GMA) with Eg; (ii) EgGMA was condensed with methacryloyl chloride into EgGAA. EgGAA was further incorporated in matrices containing BisGMA and TEGDMA (50:50 wt%) (TBEa), in which EgGAA replaced BisGMA as 0-100 wt% to get a series of unfilled resin composites (TBEa0-TBEa100), and by addition of reinforcing silica (66 wt%), a series of filled resins were also obtained (F-TBEa0-F-TBEa100). Synthesized monomers were analyzed for their structural, spectral, and thermal properties using FTIR, H- and C-NMR, mass spectrometry, TGA, and DSC. Composites rheological and DC were analyzed. The viscosity (, Pa·s) of EgGAA (0.379) was 1533 times lower than BisGMA (581.0) and 125 times higher than TEGDMA (0.003). Rheology of unfilled resins (TBEa) indicated Newtonian fluids, with viscosity decreased from 0.164 Pa·s (TBEa0) to 0.010 Pa·s (TBEa100) when EgGAA totally replaced BisGMA. However, composites showed non-Newtonian and shear-thinning behavior, with complex viscosity (*) being shear-independent at high angular frequencies (10-100 rad/s). The loss factor crossover points were at 45.6, 20.3, 20.4, and 25.6 rad/s, indicating a higher elastic portion for EgGAA-free composite. The DC was insignificantly decreased from 61.22% for the control to 59.85% and 59.50% for F-TBEa25 and F-TBEa50, respectively, while the difference became significant when EgGAA totally replaced BisGMA (F-TBEa100, DC = 52.54%). Accordingly, these properties could encourage further investigation of Eg-containing resin-based composite as filling materials in terms of their physicochemical, mechanical, and biological potentiality as dental material.
本研究旨在合成一种新型的丁香酚二甲基丙烯酸酯衍生物（称为EgGAA），作为牙科填充材料和粘合剂等特定应用的潜在生物材料。EgGAA通过两步反应合成：（i）甲基丙烯酸缩水甘油酯（GMA）与丁香酚通过开环醚化反应生成单甲基丙烯酸化丁香酚（EgGMA）；（ii）EgGMA与甲基丙烯酰氯缩合生成EgGAA。将EgGAA进一步掺入含有双酚A双甲基丙烯酸缩水甘油酯（BisGMA）和三乙二醇二甲基丙烯酸酯（TEGDMA）（质量比50:50）的基质（TBEa）中，其中EgGAA以0 - 100 wt%的比例取代BisGMA，得到一系列未填充的树脂复合材料（TBEa0 - TBEa100），并通过添加增强二氧化硅（66 wt%），还获得了一系列填充树脂（F - TBEa0 - F - TBEa100）。使用傅里叶变换红外光谱（FTIR）、氢和碳核磁共振（H - 和C - NMR）、质谱、热重分析（TGA）和差示扫描量热法（DSC）对合成的单体进行结构、光谱和热性能分析。对复合材料的流变学和转化率（DC）进行了分析。EgGAA的粘度（η，Pa·s）为0.379，比BisGMA（581.0）低1533倍，比TEGDMA（0.003）高125倍。未填充树脂（TBEa）的流变学表明为牛顿流体，当EgGAA完全取代BisGMA时，粘度从0.164 Pa·s（TBEa0）降至0.010 Pa·s（TBEa100）。然而，复合材料表现出非牛顿和剪切变稀行为，在高角频率（10 - 100 rad/s）下，复数粘度（η*）与剪切无关。损耗因子交叉点分别为45.6、20.3、20.4和25.6 rad/s，表明不含EgGAA的复合材料具有更高的弹性部分。转化率从对照的61.22%分别显著降至F - TBEa25和F - TBEa50的59.85%和59.50%，而当EgGAA完全取代BisGMA时（F - TBEa100，转化率 = 52.54%），差异变得显著。因此，这些性能可能会促使进一步研究含丁香酚的树脂基复合材料作为牙科材料在物理化学、机械和生物学潜力方面作为填充材料的应用。
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