新型抗菌型丙烯酸单体的合成及在牙科修复树脂中的应用

制备了2种具有抗菌活性的丙烯酸酯类单体6-溴己酸-2-(2-甲基丙烯酰氧)乙基酯吡啶盐(MEBH-Py)和11-溴十一酸-2-(2-甲基丙烯酰氧)乙基酯吡啶盐(MEBU-Py), 分别将其添加到牙科修复树脂Single Bond Ⅱ纳米黏结剂中共聚, 得到具有抗菌活性的改性黏结剂. MEBH-Py和MEBU-Py具有较好的热稳定性; 以大肠杆菌JM05(E. coli JM05)为受试菌, MEBH-Py和MEBU-Py的最小抑菌浓度分别为6和1 mg/mL, 改性黏结剂固化后表面抗菌效率可达98%; 抗菌单体溶出少, 并向表面富集.

Synthesis of New Antibacterial Acrylic Monomer and Its Application in Dental Restoration Resin-based

Two acrylic monomers 2-(methacryloyloxy) ethyl 6-bromohexanoate pyridinium(MEBH-Py) and 2-(methacryloyloxy) ethyl 11-bromoundecanoate pyridinium(MEBU-Py) with antibacterial property were synthesized and copolymerized with the commercial dental restorative resin Single Bond Ⅱ adhesive(3M ESPE dental products) to prepare modified binding agent with antibacterial activity to prevent second caries. The two monomers had good solubility in common solvents such as water, methanol. They could be dissolved in methyl methacrylate, hydroxyethyl methacrylate and other common dental resin. The results showed the two monomers could be copolymerized with commercial resin based restoratives. The monomers MEBH-Py and MEBU-Py got decomposed at 267.6 and 247.9 ℃ respectively and the minimal inhibitory concentration(MIC) of MEBH-Py and MEBU-Py were 6 and 1 mg/mL for E. coli JM05, respectively. The surface antibacterial efficiency for E. coli JM05 of the modified cured systems containing 1.49%—5.58% monomers were all up to 98%. The residual unpolymerized MEBH-Py or MEBU-Py were detected scarcely in the solution dipped out of the modified binder by UV-Vis analysis. The pyridinium salt groups were enriched on the surface of the modified binder by X-ray photoelectron spectroscopy(XPS) which could be the reason of high antibacterial efficiency while low content of MEBH-Py or MEBU-Py. Thus, the two monomers have good thermal stability, good bactericidal activity and polymerizable property; they may be used in many other fields to achieve antibacterial materials.