Bis-GMA

Summary

Bis-GMA
MethmethacrylateBPA-glyc.png
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
  • 1565-94-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 14549
ECHA InfoCard 100.014.880 Edit this at Wikidata
EC Number
  • 216-367-7
  • 15284
UNII
  • 454I75YXY0 checkY
  • DTXSID7044841 Edit this at Wikidata
  • 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
  • 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
C29H36O8
Molar mass 512.599 g·mol−1
Appearance colorless oil
Hazards
GHS pictograms GHS05: CorrosiveGHS07: Exclamation mark
GHS Signal word Danger
H315, H317, H318, H319
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, 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] 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

  1. ^ "bis-GMA". PubChem. Retrieved 21 April 2017.
  2. ^ 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.
  3. ^ a b 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)
  4. ^ 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.
  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. PMID 10036843.
  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. 94 (1): 230–7. doi:10.1002/jbm.b.31645. PMID 20524199.