Bis-GMA

Last updated
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 OOjs UI icon edit-ltr-progressive.svg
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
Appearancecolorless oil
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
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. [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]

Contents

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]

Related Research Articles

<span class="mw-page-title-main">Tooth decay</span> Deformation of teeth due to acids produced by bacteria

Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complications may include inflammation of the tissue around the tooth, tooth loss and infection or abscess formation.

Dental products are specially fabricated materials, designed for use in dentistry. There are many different types of dental products, and their characteristics vary according to their intended purpose.

<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation of phenol and acetone, and has a global production scale which is expected to reach 10 million tonnes in 2022.

<span class="mw-page-title-main">Bridge (dentistry)</span> Dental restoration for missing teeth

A bridge is a fixed dental restoration used to replace one or more missing teeth by joining an artificial tooth definitively to adjacent teeth or dental implants.

Dental restoration, dental fillings, or simply fillings are treatments used to restore the function, integrity, and morphology of missing tooth structure resulting from caries or external trauma as well as to the replacement of such structure supported by dental implants. They are of two broad types—direct and indirect—and are further classified by location and size. A root canal filling, for example, is a restorative technique used to fill the space where the dental pulp normally resides.

Dental sealants are a dental treatment intended to prevent tooth decay. Teeth have recesses on their biting surfaces; the back teeth have fissures (grooves) and some front teeth have cingulum pits. It is these pits and fissures that are most vulnerable to tooth decay because food and bacteria stick in them and because they are hard-to-clean areas. Dental sealants are materials placed in these pits and fissures to fill them in, creating a smooth surface which is easy to clean. Dental sealants are mainly used in children who are at higher risk of tooth decay, and are usually placed as soon as the adult molar teeth come through.

<span class="mw-page-title-main">Dental composite</span> Substance used to fill cavities in teeth

Dental composite resins are dental cements made of synthetic resins. Synthetic resins evolved as restorative materials since they were insoluble, of good tooth-like appearance, insensitive to dehydration, easy to manipulate and inexpensive. Composite resins are most commonly composed of Bis-GMA and other dimethacrylate monomers, a filler material such as silica and in most applications, a photoinitiator. Dimethylglyoxime is also commonly added to achieve certain physical properties such as flow-ability. Further tailoring of physical properties is achieved by formulating unique concentrations of each constituent.

<span class="mw-page-title-main">Bis-HPPP</span> Chemical compound

2,2-Bis[4(2,3-hydroxypropoxy)phenyl]propane (bis-HPPP) is an organic compound that is formed when the dental composite material bis-GMA is degraded by salivary esterases. It is also called BADGE·2H2O in reference to it being the hydrolysed form of BADGE, which is used in the formation of epoxy resins. Structurally, it is a di-ether of bisphenol A.

<span class="mw-page-title-main">Temporary crown</span>

A temporary crown is a temporary (short-term) crown used in dentistry. Like other interim restorations, it serves until a final (definitive) restoration can be inserted. Usually the temporary crown is constructed from acrylic resins (monomethacrylate-based/polymethacrylate-based) or, chemical-cure/light cure composite (dimethacrylate-based), although alternative systems using aluminium crown forms are occasionally used. Temporary crowns function to protect the tooth, prevent teeth shifting, provide cosmetics, shape the gum tissue properly, and prevent sensitivity.

Synthetic resins are industrially produced resins, typically viscous substances that convert into rigid polymers by the process of curing. In order to undergo curing, resins typically contain reactive end groups, such as acrylates or epoxides. Some synthetic resins have properties similar to natural plant resins, but many do not.

<span class="mw-page-title-main">Glass ionomer cement</span> Material used in dentistry as a filling material and luting cement

A glass ionomer cement (GIC) is a dental restorative material used in dentistry as a filling material and luting cement, including for orthodontic bracket attachment. Glass-ionomer cements are based on the reaction of silicate glass-powder and polyacrylic acid, an ionomer. Occasionally water is used instead of an acid, altering the properties of the material and its uses. This reaction produces a powdered cement of glass particles surrounded by matrix of fluoride elements and is known chemically as glass polyalkenoate. There are other forms of similar reactions which can take place, for example, when using an aqueous solution of acrylic/itaconic copolymer with tartaric acid, this results in a glass-ionomer in liquid form. An aqueous solution of maleic acid polymer or maleic/acrylic copolymer with tartaric acid can also be used to form a glass-ionomer in liquid form. Tartaric acid plays a significant part in controlling the setting characteristics of the material. Glass-ionomer based hybrids incorporate another dental material, for example resin-modified glass ionomer cements (RMGIC) and compomers.

<span class="mw-page-title-main">Luting agent</span>

A luting agent is an application of a dental cement connecting the underlying tooth structure to a fixed prosthesis. To lute means to glue two different structures together. There are two major purposes of luting agents in dentistry – to secure a cast restoration in fixed prosthodontics, and to keep orthodontic bands and appliances in situ.

<span class="mw-page-title-main">CAD/CAM dentistry</span>

CAD/CAM dentistry is a field of dentistry and prosthodontics using CAD/CAM to improve the design and creation of dental restorations, especially dental prostheses, including crowns, crown lays, veneers, inlays and onlays, fixed dental prostheses bridges, dental implant supported restorations, dentures, and orthodontic appliances. CAD/CAM technology allows the delivery of a well-fitting, aesthetic, and a durable prostheses for the patient. CAD/CAM complements earlier technologies used for these purposes by any combination of increasing the speed of design and creation; increasing the convenience or simplicity of the design, creation, and insertion processes; and making possible restorations and appliances that otherwise would have been infeasible. Other goals include reducing unit cost and making affordable restorations and appliances that otherwise would have been prohibitively expensive. However, to date, chairside CAD/CAM often involves extra time on the part of the dentist, and the fee is often at least two times higher than for conventional restorative treatments using lab services.

Adhesive dentistry is a branch of dentistry which deals with adhesion or bonding to the natural substance of teeth, enamel and dentin. It studies the nature and strength of adhesion to dental hard tissues, properties of adhesive materials, causes and mechanisms of failure of the bonds, clinical techniques for bonding and newer applications for bonding such as bonding to the soft tissue. There is also direct composite bonding which uses tooth-colored direct dental composites to repair various tooth damages such as cracks or gaps.

<span class="mw-page-title-main">Amalgam (dentistry)</span> Material used in dentistry for direct restorative procedures in the tooth

Dental amalgam is a liquid mercury and metal alloy mixture used in dentistry to fill cavities caused by tooth decay. Low-copper amalgam commonly consists of mercury (50%), silver (~22–32%), tin (~14%), zinc (~8%) and other trace metals.

Dental cements have a wide range of dental and orthodontic applications. Common uses include temporary restoration of teeth, cavity linings to provide pulpal protection, sedation or insulation and cementing fixed prosthodontic appliances. Recent uses of dental cement also include two-photon calcium imaging of neuronal activity in brains of animal models in basic experimental neuroscience.

<span class="mw-page-title-main">Glycidyl methacrylate</span> Chemical compound

Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol. Containing both an epoxide and an acrylate groups, the molecule is bifunctional. It is a common monomer used in the production of epoxy resins. While typical home epoxies contain diglycidyl ether of bisphenol A (DGEBA), glycidyl methacrylate is instead used to provide epoxy functionalization to polyolefins and other acrylate resins. Glycidyl methacrylate is produced by several companies worldwide, including Dow Chemical. It is used to prepare a range of composites.

Dental compomers, also known as polyacid-modified resin composite, are used in dentistry as a filling material. They were introduced in the early 1990s as a hybrid of two other dental materials, dental composites and glass ionomer cement, in an effort to combine their desirable properties: aesthetics for dental composites and the fluoride releasing ability for glass ionomer cements.

Anterior teeth are one of the most scrutinized teeth, the size and shape and color of the anterior upper teeth plays an important role in dental aesthetics and smile aesthetics. A few aesthetic anterior problems could be solved with composite restorations. For example, dental caries, tooth fracture, enamel defects and diastemas. Composite restoration can also improve aesthetic by changing shape, color, length and alignment of teeth.

Atraumatic restorative treatment (ART) is a method for cleaning out tooth decay from teeth using only hand instruments and placing a filling. It does not use rotary dental instruments to prepare the tooth and can be performed in settings with no access to dental equipment. No drilling or local anaesthetic injections are required. ART is considered a conservative approach, not only because it removes the decayed tissue with hand instruments, avoiding removing more tissue necessary which preserves as much tooth structure as possible, but also because it avoids pulp irritation and minimises patient discomfort. ART can be used for small, medium and deep cavities caused by dental caries.

References

  1. CID 15284 from PubChem . Retrieved 27 May 2022.
  2. 1 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. 1 2 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.
  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.
  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. 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. 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.

Further reading