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通过硫醇-烯点击聚合制备的含1,2,3-三唑鎓官能化POSS添加剂的杀菌牙科纳米复合材料。

Bactericidal dental nanocomposites containing 1,2,3-triazolium-functionalized POSS additive prepared through thiol-ene click polymerization.

作者信息

Burujeny Saeed Beigi, Yeganeh Hamid, Atai Mohammad, Gholami Hoshyar, Sorayya Marziyeh

机构信息

Iran Polymer and Petrochemical Institute, P.O. Box 14965/115, Tehran, Iran; Biomedical Engineering Department, Faculty of Engineering, Islamic Azad University, Central Tehran Branch, Tehran, Iran.

Iran Polymer and Petrochemical Institute, P.O. Box 14965/115, Tehran, Iran.

出版信息

Dent Mater. 2017 Jan;33(1):119-131. doi: 10.1016/j.dental.2016.11.001. Epub 2016 Nov 23.

Abstract

OBJECTIVE

Deterioration of mechanical strength for the dental composite containing ionic bactericidal compounds restricts the widespread utilization of this class of useful materials. This problem is originated from the reduction of the intermolecular interaction of polymeric network due to plasticization effect of absorbed water molecules penetrated between the chain segments. The main goal of this study is the synthesis of the highly efficient bactericidal additive with low hydrophilicity and consequently the least adverse effect on the final mechanical strength of the dental composite.

METHODS

The bactericidal 1, 2, 3-triazolium functional groups were chemically anchored on the surface of hydrophobic POSS nanoparticles (Triazolium-POSS) and incorporated into a dental restorative system composed of a ternary thiol-allyl ether-methacrylate resin and glass fillers. A similar system was also prepared, in which the POSS additive was replaced with quaternized dimethyl aminoethyl methacrylate monomer (DMAEMA-BC). The chemical structure of POSS derivatives was evaluated by HNMR and FTIR spectra. The water uptake of dental composites was evaluated at days 1 and 14 after immersion into water. The bactericidal activity of composite specimens against Streptococcus mutans (ATCC 35668) was determined based on ASTM E 2180 - 07. The flexural properties of samples were investigated through three-point bending assay and the shrinkage-strain of photo-cured resins was measured using the bonded-disk technique. The degree of conversion (DC %) of methacrylate functions was followed by FTIR spectroscopy. MTT assay was performed to investigate the cytocompatibility of samples.

RESULTS

Regardless of the partial increase in water uptake for Triazolium-POSS-containing sample, this parameter was much favor than the composite made from DMAEMA-BC. Therefore, the lower decline in flexural properties was recorded under the wet condition for the former system. Incorporation of Triazolium-POSS had no significant effect on shrinkage strain and cytocompatibility of composite specimen, meanwhile, a higher degree of conversion of methacrylate functional groups was recorded. The Triazolium-POSS-containing nano composite showed significantly higher bactericidal activity against Streptococcus mutans than another studied model system.

SIGNIFICANCE

The new derivative of bactericidal POSS nanoparticles decorated with 1, 2, 3-Triazolium moieties is a highly efficient bactericidal compound. If Triazolium-POSS is incorporated into a proper dental resin formulation, it can provide a strong bactericidal activity for dental materials; in the meantime, it leads to minimum deterioration of their mechanical strength due to its low water uptake.

摘要

目的

含有离子杀菌化合物的牙科复合材料的机械强度下降限制了这类有用材料的广泛应用。这个问题源于水分子渗透到链段之间产生的增塑作用,导致聚合物网络分子间相互作用降低。本研究的主要目标是合成具有低亲水性的高效杀菌添加剂,从而对牙科复合材料的最终机械强度产生最小的不利影响。

方法

将杀菌性的1, 2, 3 - 三唑鎓官能团化学锚定在疏水性倍半硅氧烷纳米颗粒(三唑鎓 - POSS)表面,并将其掺入由三元硫醇 - 烯丙基醚 - 甲基丙烯酸酯树脂和玻璃填料组成的牙科修复体系中。还制备了一个类似的体系,其中POSS添加剂被季铵化的甲基丙烯酸二甲氨基乙酯单体(DMAEMA - BC)取代。通过HNMR和FTIR光谱对POSS衍生物的化学结构进行了评估。在浸入水中1天和14天后评估牙科复合材料的吸水率。基于ASTM E 2180 - 07测定复合样品对变形链球菌(ATCC 35668)的杀菌活性。通过三点弯曲试验研究样品的弯曲性能,并使用粘结盘技术测量光固化树脂的收缩应变。通过FTIR光谱跟踪甲基丙烯酸酯官能团的转化率(DC%)。进行MTT试验以研究样品的细胞相容性。

结果

尽管含三唑鎓 - POSS的样品吸水率有部分增加,但该参数比由DMAEMA - BC制成的复合材料更有利。因此,对于前一个体系,在潮湿条件下记录到的弯曲性能下降更低。掺入三唑鎓 - POSS对复合样品的收缩应变和细胞相容性没有显著影响,同时,记录到甲基丙烯酸酯官能团的转化率更高。含三唑鎓 - POSS的纳米复合材料对变形链球菌的杀菌活性明显高于另一个研究的模型体系。

意义

用1, 2, 3 - 三唑基团修饰的杀菌性POSS纳米颗粒的新衍生物是一种高效杀菌化合物。如果将三唑鎓 - POSS掺入合适的牙科树脂配方中,它可以为牙科材料提供强大的杀菌活性;同时,由于其低吸水率,它导致其机械强度的劣化最小。

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