Bis-GMA
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| Names | |
|---|---|
| Other names
Bowen monomer
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| Identifiers | |
| ECHA InfoCard | 100.014.880 |
| UNII | |
CompTox Dashboard (EPA)
|
|
| Properties | |
| C29H36O8 | |
| Molar mass | 512.599 g·mol−1 |
| Appearance | colorless oil |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Bis-GMA (bisphenol A-glycidyl methacrylate) is a resin commonly used in dental composite, dental sealants.[1][2] and dental cement. It is the diester derived from methacrylic acid and the bisphenol A diglycidyl ether. Bearing two polymerizable groups, it is prone to form a crosslinked polymer that is used in dental restorations.[3] For dental work, bis-GMA is mixed with aluminosilicate particles, crushed quartz and other related acrylates. Bis-GMA was incorporated into composite dental resins in 1962 by Rafael Bowen.[3]
Safety
Concerns have been raised about the potential for bis-GMA to break down into or be contaminated with the related compound bisphenol A.[4][4] However, no negative health effects of bis-GMA use in dental resins have been found.[5][2]
Composition
Salivary esterases can slowly degrade bis-GMA-based sealants, forming Bis-HPPP.[6]
References
- ^ "bis-GMA". PubChem. Retrieved 21 April 2017.
- ^ a b Ahovuo-Saloranta, Anneli; Forss, Helena; Walsh, Tanya; Nordblad, Anne; Mäkelä, Marjukka; Worthington, Helen V. (31 July 2017). "Pit and fissure sealants for preventing dental decay in permanent teeth". The Cochrane Database of Systematic Reviews. 7: CD001830. doi:10.1002/14651858.CD001830.pub5. ISSN 1469-493X. PMC 6483295. PMID 28759120.
- ^ a b "Dental Materials". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2006. doi:10.1002/14356007.a08_251.pub2. ISBN 978-3527306732.
{{cite encyclopedia}}: Cite uses deprecated parameter|authors=(help) - ^ a b LaBauve JR, Long KN, Hack GD, Bashirelahi N (2012). "What every dentist should known about bisphenol A". General Dentistry. 60 (5): 424–32. PMID 23032231.
- ^ Soderholm KJ, Mariotti A (February 1999). "Bis-GMA–based resins in dentistry: are they safe?". The Journal of the American Dental Association. 130 (2): 201–209. doi:10.14219/jada.archive.1999.0169. PMID 10036843.
- ^ Shokati, Babak; Tam, Laura Eva; Santerre, J. Paul; Finer, Yoav (2010). "Effect of salivary esterase on the integrity and fracture toughness of the dentin-resin interface". Journal of Biomedical Materials Research Part B: Applied Biomaterials: n/a. doi:10.1002/jbm.b.31645. PMID 20524199.