丙烯酰胺和甲基丙烯酰胺作为牙科胶粘剂的替代单体。
Acrylamides and methacrylamides as alternative monomers for dental adhesives.
机构信息
Dental Materials Laboratory, School of Dentistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil.
Organic Chemistry Department, Chemistry Institute, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil.
出版信息
Dent Mater. 2018 Nov;34(11):1634-1644. doi: 10.1016/j.dental.2018.08.296. Epub 2018 Sep 7.
OBJECTIVE
Synthesize and characterize a methacrylamide monomer for adhesive system and evaluate the physicochemical properties of the adhesive resin.
METHODS
The liquid methacrylamide monomer N,N',N″-(nitrilotris(ethane-2,1-dyil)tris(2-methylacrylamide) (TMA) was prepared by reaction of methacrylic anhydride and tris(2-aminoethyl)amine with 60% yields. The TMA structure was analyzed by H NMR, C NMR, ATR-FTIR and UHPLC-QTOF-MS. Experimental adhesive resin containing bisphenol-A glycidyl methacrylate (BISGMA), 2-hydroxyethylacrylamide (HEAA), 2-hydroxyethylmethacrylate (HEMA) and TMA were formulated. Polymerization kinetics of neat TMA and experimental adhesive resin (TMA33%/HEAA66%, TMA50%/HEAA50%, TMA66%/HEAA33%, TMA50%/HEMA50%, BisGMA/HEAA/TMA and BisGMA/HEMA) were evaluated using Differential Scanning Calorimetry. Physiochemical properties for BisGMA/HEAA/TMA and BisGMA/HEMA adhesives were evaluated by cytotoxicity, ultimate tensile strength (UTS), softening in solvent (ΔKHN), contact angle (θ), microtensile bond strength (μTBS) and failure analysis. A primer was also formulated with HO/HEAA/AMPS (2-acrylamido-2-methylpropane sulfonic acid) and the pH value was verified and compared to commercial primer.
RESULTS
Adhesive resin with only HEAA and TMA (TMA33%/HEAA66%, TMA50%/HEAA50%, TMA66%/HEAA33%) showed lower conversion and polymerization rate after 40s of light activation. Conversion up to 60% was found for BisGMA/HEAA/TMA and BisGMA/HEMA adhesive resin without significant difference between groups, p>0.05. Cytotoxicity, UTS, μTBS, ΔKHN and θ showed no statistical difference, p>0.05, between BisGMA/HEAA/TMA and BisGMA/HEMA adhesive resin.
SIGNIFICANCE
In this study, the proposed synthetic route resulted in a tris(methacrylamide). A new primer composed without acrylates or methacrylates was formulated for 3-step etch-and-rinse adhesive system without the presence of HEMA monomer. Physicochemical properties and cell viability of BisGMA/HEAA/TMA adhesive resin represents an alternative adhesive resin without HEMA monomer.
目的
合成并表征一种用于胶粘剂体系的甲基丙烯酰胺单体，并评估胶粘剂树脂的物理化学性质。
方法
通过丙烯酰基三甲胺与三（2-氨基乙基）胺反应，以 60%的产率制备液体甲基丙烯酰胺单体 N，N'，N"-(亚乙基三（乙二胺）三（2-甲基丙烯酰胺）（TMA）。通过 1H NMR、13C NMR、ATR-FTIR 和 UHPLC-QTOF-MS 分析 TMA 结构。配制含有双酚 A 缩水甘油甲基丙烯酸酯（BisGMA）、2-羟乙基丙烯酰胺（HEAA）、2-羟乙基甲基丙烯酸酯（HEMA）和 TMA 的实验性胶粘剂树脂。通过差示扫描量热法评估纯 TMA 和实验性胶粘剂树脂（TMA33%/HEAA66%、TMA50%/HEAA50%、TMA66%/HEAA33%、TMA50%/HEMA50%、BisGMA/HEAA/TMA 和 BisGMA/HEMA）的聚合动力学。通过细胞毒性、极限拉伸强度（UTS）、溶剂软化（ΔKHN）、接触角（θ）、微拉伸粘结强度（μTBS）和失效分析评估 BisGMA/HEAA/TMA 和 BisGMA/HEMA 胶粘剂的物理化学性能。还配制了一种含有 HO/HEAA/AMPS（2-丙烯酰胺基-2-甲基丙磺酸）的底漆，并验证了其 pH 值并与商业底漆进行了比较。
结果
在光激活 40s 后，仅含 HEAA 和 TMA（TMA33%/HEAA66%、TMA50%/HEAA50%、TMA66%/HEAA33%）的胶粘剂树脂转化率和聚合速率较低。BisGMA/HEAA/TMA 和 BisGMA/HEMA 胶粘剂树脂的转化率均达到 60%，各组间无显著差异，p>0.05。细胞毒性、UTS、μTBS、ΔKHN 和θ在 BisGMA/HEAA/TMA 和 BisGMA/HEMA 胶粘剂树脂之间无统计学差异，p>0.05。
意义
在这项研究中，提出的合成路线得到了三（甲基丙烯酰胺）。为 3 步酸蚀-冲洗型胶粘剂体系配制了不含丙烯酸盐或甲基丙烯酸盐的新型底漆，其中不含有 HEMA 单体。BisGMA/HEAA/TMA 胶粘剂树脂的物理化学性能和细胞活力代表了一种不含 HEMA 单体的替代胶粘剂树脂。
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