Bis-GMA

Bis-GMA
Names
	Preferred IUPAC name Propane-2,2-diylbis[4,1-phenyleneoxy(2-hydroxypropane-3,1-diyl)] bis(2-methylprop-2-enoate)
	Other names Bowen monomer; Silux; Delton; NuvaSeal; Retroplast
Identifiers
CAS Number	1565-94-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	14549;
ECHA InfoCard	100.014.880
EC Number	216-367-7;
PubChem CID	15284;
UNII	454I75YXY0 ;
CompTox Dashboard (EPA)	DTXSID7044841 ;
	InChI InChI=1S/C29H36O8/c1-19(2)27(32)36-17-23(30)15-34-25-11-7-21(8-12-25)29(5,6)22-9-13-26(14-10-22)35-16-24(31)18-37-28(33)20(3)4/h7-14,23-24,30-31H,1,3,15-18H2,2,4-6H3 Key: AMFGWXWBFGVCKG-UHFFFAOYSA-N;
	SMILES CC(=C)C(=O)OCC(COC1=CC=C(C=C1)C(C)(C)C2=CC=C(C=C2)OCC(COC(=O)C(=C)C)O)O;
Properties
Chemical formula	C29H36O8
Molar mass	512.599 g·mol−1
Appearance	colorless oil
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H317, H318, H319
Precautionary statements	P261, P264, P272, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P337+P313, P362, P363, P501
	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, highly viscous bis-GMA is mixed with aluminosilicate particles, crushed quartz and other related acrylates; changes to component ratios lead to different physical properties in the end product.^[4] Bis-GMA was incorporated into composite dental resins in 1962 by Rafael Bowen.^[3] Until matrix development work in the early 2000s, bis-GMA and related methacrylate monomers were the only options for organic matrix composition.^[5]

^ CID 15284 from PubChem. Retrieved 27 May 2022.
^ 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. 2017 (7): CD001830. doi:10.1002/14651858.CD001830.pub5. PMC 6483295. PMID 28759120.
^ ^a ^b Craig RG, Welker D, Rothaut J, Krumbholz KG, Stefan KP, Dermann K, Rehberg HJ, Franz G, Lehmann KM, Borchert M (2006). "Dental Materials". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_251.pub2. ISBN 978-3-527-30673-2.
^ Zimmerli B, Strub M, Jeger F, Stadler O, Lussi A (November 2010). "Composite Materials: Composition, properties and clinical applications" (PDF). Schweiz Monatsschr Zahnmed. 120 (11): 972–9. PMID 21243545. Retrieved 28 May 2022.
^ Fugolin AP, Pfeifer CS (21 July 2017). "New Resins for Dental Composites". Journal of Dental Research. 96 (10): 1085–91. doi:10.1177/0022034517720658. PMC 5582688. PMID 28732183.

[1] CID 15284 from PubChem. Retrieved 27 May 2022.

[:0-2] 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. 2017 (7): CD001830. doi:10.1002/14651858.CD001830.pub5. PMC 6483295. PMID 28759120.

[Ull-3] Craig RG, Welker D, Rothaut J, Krumbholz KG, Stefan KP, Dermann K, Rehberg HJ, Franz G, Lehmann KM, Borchert M (2006). "Dental Materials". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_251.pub2. ISBN 978-3-527-30673-2.

[4] Zimmerli B, Strub M, Jeger F, Stadler O, Lussi A (November 2010). "Composite Materials: Composition, properties and clinical applications" (PDF). Schweiz Monatsschr Zahnmed. 120 (11): 972–9. PMID 21243545. Retrieved 28 May 2022.

[5] Fugolin AP, Pfeifer CS (21 July 2017). "New Resins for Dental Composites". Journal of Dental Research. 96 (10): 1085–91. doi:10.1177/0022034517720658. PMC 5582688. PMID 28732183.

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