Fluorinated bis-GMA as potential monomers for dental restorative composite materials

作者: Rohit Srivastava , Joanna Wolska , Justyna Walkowiak-Kulikowska , Henryk Koroniak , Yuyu Sun

DOI: 10.1016/J.EURPOLYMJ.2017.03.027

关键词: ShrinkageChemical structureMethacrylateCopolymerBisphenolPolymer chemistryMonomerMaterials sciencePolymerizationFourier transform infrared spectroscopy

摘要: Abstract Bisphenol A-glycidyl methacrylate (bisGMA) is one of the most widely used monomers in preparation dental restorative composite resins. However, this monomer has high viscosity and hydrophilicity, leading to volume shrinkage water content resulting restoratives after polymerization. We hypothesized that hydrophilicity could be dramatically reduced by transforming hydroxyl groups bisGMA into fluorinated esters. To test hypothesis, we synthesized a new analogue (perFB-bisGMA) through esterification with perfluorobutyryl chloride. The chemical structure perFB-bisGMA was confirmed NMR FTIR studies. PerFB-bisGMA had much lower higher hydrophobicity than bisGMA. BisGMA were copolymerized light-initiated With increase content, mechanical properties copolymers not negatively affected, yet polymerization reduced, copolymer increased, suggesting esters attractive candidates copolymerize for applications.

参考文章(44)
S KALACHANDRA, M SANKARAPANDIAN, H. K SHOBHA, D. F TAYLOR, J. E MCGRATH, Influence of hydrogen bonding on properties of BIS-GMA analogues Journal of Materials Science: Materials in Medicine. ,vol. 8, pp. 283- 286 ,(1997) , 10.1023/A:1018508227774
Mei Yin, Sen Guo, Fang Liu, Jingwei He, Synthesis of fluorinated dimethacrylate monomer and its application in preparing Bis-GMA free dental resin Journal of the Mechanical Behavior of Biomedical Materials. ,vol. 51, pp. 337- 344 ,(2015) , 10.1016/J.JMBBM.2015.07.025
Shuang Yuan, Fang Liu, Jingwei He, Preparation and Characterization of Low Polymerization Shrinkage and Bis-GMA-Free Dental Resin System Advances in Polymer Technology. ,vol. 34, ,(2015) , 10.1002/ADV.21503
Delphine Truffier-Boutry, Sophie Demoustier-Champagne, Jacques Devaux, Jean-Jacques Biebuyck, Michèle Mestdagh, Philippe Larbanois, Gaëtane Leloup, A physico-chemical explanation of the post-polymerization shrinkage in dental resins Dental Materials. ,vol. 22, pp. 405- 412 ,(2006) , 10.1016/J.DENTAL.2005.04.030
Zohaib Khurshid, Muhammad Zafar, Saad Qasim, Sana Shahab, Mustafa Naseem, Ammar AbuReqaiba, None, Advances in Nanotechnology for Restorative Dentistry. Materials. ,vol. 8, pp. 717- 731 ,(2015) , 10.3390/MA8020717
W.D Cook, M Forrest, A.A Goodwin, A simple method for the measurement of polymerization shrinkage in dental composites. Dental Materials. ,vol. 15, pp. 447- 449 ,(1999) , 10.1016/S0109-5641(99)00073-1
William J. Bailey, Matrices that expand on curing for high strength composites and adhesives Materials Science and Engineering A-structural Materials Properties Microstructure and Processing. ,vol. 126, pp. 271- 279 ,(1990) , 10.1016/0921-5093(90)90133-N