Abdel-Basit Al-Odayni1, Randa Alfotawi2, Rawaiz Khan3, Waseem Sharaf Saeed1, Abdullah Al-Kahtani1, Taieb Aouak1, Ali Alrahlah4. 1. Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. 2. Maxillofacial Surgery Department, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia. 3. Engineer Abdullah Bugshan Research Chair for Dental and Oral Rehabilitation, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia. 4. Engineer Abdullah Bugshan Research Chair for Dental and Oral Rehabilitation, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia; Restorative Dental Sciences Department, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia. Electronic address: aalrahlah@ksu.edu.sa.
Abstract
OBJECTIVES: The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an alternative to BisGMA in dental resin composites. METHODS: The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via 1H- and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (WSP), and solubility (WSL) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation. RESULTS: Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the WSP was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in WSL. However, the WSL increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation. SIGNIFICANCE: The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites.
OBJECTIVES: The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an alternative to BisGMA in dental resin composites. METHODS: The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via 1H- and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (WSP), and solubility (WSL) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation. RESULTS:Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the WSP was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in WSL. However, the WSL increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation. SIGNIFICANCE: The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites.