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Journal of Dental Research
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Biomaterials & Bioengineering

Analysis of the Degradation of a Model Dental Composite

P.J. Koin1, A. Kilislioglu2, M. Zhou3, J.L. Drummond4 and L. Hanley3,*

1 University of Illinois at Chicago, Departments of Bioengineering,
3 Chemistry, and
4 Restorative Dentistry, m/c 111, Chicago, IL 60607-7061, USA; and
2 Istanbul University, Department of Chemistry, Avcilar 34320, Istanbul, Turkey

Correspondence: * corresponding author, lhanley{at}uic.edu

Dental composites undergo material property changes during exposure to the oral environment and may release compounds of potential toxicity, such as bisphenol A. Degradation of dental composites was studied in a simplified overlayer model in which bisphenol A diglycidyl methacrylate (BisGMA) was covalently bound to a porous silicon oxide surface. It was hypothesized that the chemical structure of this overlayer would allow release of bisphenol A, BisGMA, and the decomposition products thereof, upon exposure to water for an extended period. Liquid chromatography mass spectrometry found leaching of intact BisGMA and several degradation products that contained the bisphenol A moiety from the overlayer into distilled water after 2 wks of aging. The absence of bisphenol A release from the overlayer reduces concerns regarding its potential health risk in dental composites. Nevertheless, health concerns might arise with respect to BisGMA and the leached degradation products, since they all contain the bisphenol A moiety. Abbreviations: BisGMA, bisphenol A diglycidyl methacrylate; HPLC, high-performance liquid chromatography; LCMS, liquid chromatography mass spectrometry; MA, methacrylic acid; MPS, 3-(trimethoxysilyl) propyl methacrylate; m/z, mass-to-charge ratio; and TIC, total ion chromatogram.

Key Words: hydrolysis • degradation • dental composite • liquid chromatography mass spectrometry

Journal of Dental Research, Vol. 87, No. 7, 661-665 (2008)
DOI: 10.1177/154405910808700712
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