Bis-GMA

Bis-GMA

Bis-GMA

Chemical compound

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]

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Safety

Concerns have been raised about the potential for bis-GMA to break down into or be contaminated with the related compound bisphenol A.[6] However, no negative health effects of bis-GMA use in dental resins have been found.[2][7]

Composition

Salivary esterases can slowly degrade bis-GMA-based sealants, forming Bis-HPPP.[8]

References

  1. [1]
    CID 15284 from PubChem. Retrieved 27 May 2022.
  2. [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. ISSN 1469-493X. PMC 6483295. PMID 28759120.
  3. [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 978-3527306732.
  4. [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. [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.
  6. [6]
    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.
  7. [7]
    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.(subscription required)
  8. [8]
    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.

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