Bis-GMA

Bis-GMA
Names
	Other names Bowen monomer
Identifiers
CAS Number	1565-94-2;
ECHA InfoCard	100.014.880
CompTox Dashboard (EPA)	DTXSID7044841 ;
Properties
Chemical formula	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).
	Infobox references

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.
Ahovuo-Saloranta, A; Forss, H; Walsh, T; Hiiri, A; Nordblad, A; Mäkelä, M; Worthington, HV (28 March 2013). "Sealants for preventing dental decay in the permanent teeth". The Cochrane Database of Systematic Reviews (3): CD001830. PMID 23543512.
Robert G. Craig, Dieter Welker, Josef Rothaut, Klaus Georg Krumbholz, Klaus‐Peter Stefan, Klaus Dermann, Hans‐Joachim Rehberg, Gertraute Franz, Klaus Martin Lehmann, Matthias Borchert (2006). "Dental Materials". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_251.pub2.CS1 maint: uses authors parameter (link)
LaBauve JR, Long KN, Hack GD, Bashirelahi N (2012). "What every dentist should known about bisphenol A". General Dentistry. 60 (5). 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.
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–n/a. doi:10.1002/jbm.b.31645.

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[1] "bis-GMA". PubChem. Retrieved 21 April 2017.

[Cochrane2013-2] Ahovuo-Saloranta, A; Forss, H; Walsh, T; Hiiri, A; Nordblad, A; Mäkelä, M; Worthington, HV (28 March 2013). "Sealants for preventing dental decay in the permanent teeth". The Cochrane Database of Systematic Reviews (3): CD001830. PMID 23543512.

[Ull-3] Robert G. Craig, Dieter Welker, Josef Rothaut, Klaus Georg Krumbholz, Klaus‐Peter Stefan, Klaus Dermann, Hans‐Joachim Rehberg, Gertraute Franz, Klaus Martin Lehmann, Matthias Borchert (2006). "Dental Materials". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_251.pub2.CS1 maint: uses authors parameter (link)

[Labauve2012-4] LaBauve JR, Long KN, Hack GD, Bashirelahi N (2012). "What every dentist should known about bisphenol A". General Dentistry. 60 (5). PMID 23032231.

[Soderholm1999-5] 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.

[6] 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–n/a. doi:10.1002/jbm.b.31645.