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Dental materials
Bis-GMA
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    Bis-GMA

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    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
    3D model (JSmol)
    ChemSpider
    ECHA InfoCard 100.014.880
    EC Number
    • 216-367-7
    PubChem CID
    UNII
    • 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 labelling:
    GHS05: CorrosiveGHS07: Exclamation mark
    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).

    Bis-GMA (bisphenol A-glycidyl methacrylate) is a resin commonly used in dental composite, dental sealants. 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. 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. Bis-GMA was incorporated into composite dental resins in 1962 by Rafael Bowen. Until matrix development work in the early 2000s, bis-GMA and related methacrylate monomers were the only options for organic matrix composition.

    Safety

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

    Composition

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

    Further reading


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