Bisphenol-A content of resin monomers and related degradation products.
Recently, it was reported that Bisphenol-A (BPA) was released from one fissure sealant (Delton) into saliva causing estrogenic activity in vitro. The aim of this study was to chemically analyze the BPA content of different fissure sealant resin monomers and their release of BPA under hydrolytic conditions. BPA content was first measured in commercially available monomers of bisphenol-A glycidyldimethacrylate (Bis-GMA), bisphenol-A dimethacrylate (Bis-DMA) and bisphenol-A diglycidylether (BADGE). Then, Bis-GMA-monomer and Bis-DMA-monomer in methanol were subjected to pH values of 0 to 11 for 30 minutes at 50 degrees C, to porcine liver esterase, and to pooled saliva for up to 24 hours. The BPA-content was determined by high-performance liquid chromatography (HPLC). Bis-GMA-monomer and BADGE-monomer from one manufacturer did not contain any detectable amounts of BPA (< or = 2 ppm); Bis-DMA and BADGE-monomer from a second manufacturer contained BPA quantities of 4-155 ppm. For Bis-GMA-monomer, no BPA could be detected under any hydrolytic conditions chosen (detection limit: < or = 1%). For Bis-DMA-monomer an increase of BPA was observed at pH 11, resulting in a conversion of approx. 100% Bis-DMA to BPA. When Bis-DMA was subjected to esterase, a conversion of 82.5% resulted after 24 h; saliva led to an 81.4% conversion of Bis-DMA after 24 h. Hence, we conclude that the results reported in the literature may be attributed to the Bis-DMA-content of the fissure sealant tested (Delton). No BPA-release is expected under physiologic conditions from fissure sealants based on Bis-GMA if pure base monomers are used.
Schmalz
G
G
Poliklinik für Zahnerhaltung und Parodontologie der Universität Regensburg, Germany. gottfried.schmalz@klinik.uni-regensburg.de
Preiss
A
A
Arenholt-Bindslev
D
D
D001559:Benzhydryl Compounds; D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003188:Composite Resins / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D004968:Estrogens, Non-Steroidal / Q000032:analysis*; D006801:Humans; D006868:Hydrolysis; D008689:Methacrylates / Q000737:chemistry*; D010636:Phenols / Q000032:analysis*; D010895:Pit and Fissure Sealants / Q000737:chemistry*; D012463:Saliva / Q000737:chemistry; D000098826:Bisphenol A Compounds
D001559:Benzhydryl Compounds; D017438:Bisphenol A-Glycidyl Methacrylate; D003188:Composite Resins; D004852:Epoxy Compounds; D004968:Estrogens, Non-Steroidal; D008689:Methacrylates; D010636:Phenols; D010895:Pit and Fissure Sealants; C002462:4,4'-isopropylidenediphenol dimethacrylate; D000098826:Bisphenol A Compounds; C019273:bisphenol A diglycidyl ether; C006780:bisphenol A