How to cite this article: Park J, Ye Q, Singh V, Kieweg SL, Misra A, Spencer P. 2012. Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group. J Biomed Mater Res Part B 2012:100B: 569–576.
Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group†
Article first published online: 24 NOV 2011
Copyright © 2011 Wiley Periodicals, Inc.
Journal of Biomedical Materials Research Part B: Applied Biomaterials
Volume 100B, Issue 2, pages 569–576, February 2012
How to Cite
Park, J., Ye, Q., Singh, V., Kieweg, S. L., Misra, A. and Spencer, P. (2012), Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group. J. Biomed. Mater. Res., 100B: 569–576. doi: 10.1002/jbm.b.31987
- Issue published online: 4 JAN 2012
- Article first published online: 24 NOV 2011
- Manuscript Accepted: 20 SEP 2011
- Manuscript Revised: 1 SEP 2011
- Manuscript Received: 31 MAY 2011
- National Institute of Dental and Craniofacial Research, National Institutes of Health, Bethesda. Grant Numbers: R01DE14392-09, R01DE014392-08S1.
- dentin adhesives;
- dental monomer;
- dynamic mechanical property;
- water miscibility
A new glycerol-based dimethacrylate monomer with an aromatic carboxylic acid, 2-((1,3-bis(methacryloyloxy)propan-2-yloxy)carbonyl)benzoic acid (BMPB), was synthesized, characterized, and proposed as a possible dental co-monomer for dentin adhesives. Dentin adhesives containing 2-hydroxyethyl methacrylate (HEMA) and 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA) in addition to BMPB were formulated with water at 0, 5, 10, and 15 wt % to simulate wet, oral conditions, and photo-polymerized. Adhesives were characterized with regard to viscosity, real-time photopolymerization behavior, dynamic mechanical analysis, and microscale 3D internal morphologies and compared with HEMA/BisGMA controls. When formulated under wet conditions, the experimental adhesives showed lower viscosities (0.04–0.07 Pa s) as compared to the control (0.09–0.12 Pa s). The experimental adhesives showed higher glass transition temperature (146–157°C), degree of conversion (78–89%), and rubbery moduli (33–36 MPa), and improved water miscibility (no voids) as compared to the controls (123–135°C, 67–71%, 15–26 MPa, and voids, respectively). The enhanced properties of these adhesives suggest that BMPB with simple, straightforward synthesis is a promising photocurable co-monomer for dental restorative materials. © 2011 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater 100B: 569–576, 2012.