Bis-GMA (bisphenol A-glycidyl methacrylate) is a

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...

commonly used in

dental composite Dental composite resins (better referred to as "resin-based composites" or simply "filled resins") are dental cements made of synthetic resins. Synthetic resins evolved as restorative materials since they were insoluble, of good tooth-like appea ...

dental sealant Dental sealants (also termed pit and fissure sealants, or simply fissure 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 h ...

s. and

dental cement 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 u ...

. It is the

diester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are ...

derived from

methacrylic acid Methacrylic acid, abbreviated MAA, is an organic compound. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced indu ...

and the

bisphenol A diglycidyl ether Bisphenol A diglycidyl ether (commonly abbreviated BADGE or DGEBA) is an organic compound used as constituent of epoxy resins. The compound is a colorless solid (commercial samples can appear yellow) that melts slightly above room temperature. P ...

. 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 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 s ...

. However, no negative health effects of bis-GMA use in dental resins have been found.

Composition

Saliva Saliva (commonly referred to as spit) is an extracellular fluid produced and secreted by salivary glands in the mouth. In humans, saliva is around 99% water, plus electrolytes, mucus, white blood cells, epithelial cells (from which DNA can be ...

esterase An esterase is a hydrolase enzyme that splits esters into an acid and an alcohol in a chemical reaction with water called hydrolysis. A wide range of different esterases exist that differ in their substrate specificity, their protein structure ...

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

Safety

Composition

References

Further reading