2,2-Bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane, commonly known as Bis-GMA, is a rigid, aromatic dimethacrylate monomer used in crosslinked polymer and resin systems. Two polymerizable methacrylate groups enable formation of covalent network junctions, while the aromatic bisphenol-derived core and pendant hydroxyl groups contribute to the characteristic structure and high viscosity of Bis-GMA.
Synonyms: Bis-GMA; Bisphenol A Glycerolate Dimethacrylate; Bisphenol A Glycidyl Methacrylate.
Bis-GMA is widely used as a resin-matrix monomer in dental-material research and in studies of photopolymerized dimethacrylate networks. Because of its high viscosity, it is commonly studied in mixtures with lower-viscosity reactive diluents such as other dimethacrylate monomers.
Final polymerization behavior and material properties depend on formulation composition, diluent selection, initiator system, degree of conversion, irradiation conditions, filler content when applicable, and network architecture.
Key Properties
- Rigid, aromatic difunctional dimethacrylate monomer
- CAS Number: 1565-94-2
- Appearance: colorless to light yellow viscous liquid
- FT-IR: conforms to structure
- Inhibitor: approximately 100 ppm MEHQ
- Refractive index: 1.55
- Behavior on heating: gels before boiling
- Catalog number: 03344
- Package size: 100 g
Applications
Crosslinked Polymer & Resin Networks
Bis-GMA is used as a difunctional crosslinking monomer in free-radical polymerization. Its two methacrylate groups can participate in network formation, with crosslink density and final properties determined by the complete formulation and degree of conversion.
Dental Resin & Composite Research
Bis-GMA is an established resin-matrix monomer in experimental and commercial dental composite chemistries. Research formulations frequently combine Bis-GMA with lower-viscosity dimethacrylate monomers to adjust handling, conversion, and network properties. Cat. 03344 should be evaluated according to the requirements of the intended research formulation rather than interpreted as a finished dental material.
Photopolymerization Research
Bis-GMA-containing formulations are widely studied in light-initiated polymerization. Conversion and resulting network properties depend on factors including photoinitiator chemistry, light intensity, wavelength, exposure time, temperature, formulation viscosity, and comonomer composition.
Dimethacrylate Network Structure Studies
Bis-GMA is frequently used as a model aromatic dimethacrylate in research examining relationships among monomer structure, hydrogen bonding, viscosity, polymerization conversion, shrinkage, and mechanical behavior in crosslinked resin networks.
Compatibility & Bonding Considerations
- Contains two polymerizable methacrylate groups capable of forming covalent network junctions
- Pendant hydroxyl groups support intermolecular hydrogen bonding and contribute to the high viscosity of Bis-GMA
- The rigid aromatic core influences the structure of resulting crosslinked networks
- Contains approximately 100 ppm MEHQ inhibitor, which should be considered when establishing polymerization conditions
- Lower-viscosity reactive diluents may be incorporated when formulation viscosity or conversion requires adjustment
- Final properties depend on monomer ratio, initiator system, conversion, filler content, and cure conditions
Bis-GMA is chemically distinct from bisphenol A and bisphenol A diglycidyl ether (BADGE). Although these compounds share bisphenol-derived structural features, they have different functional groups, molecular structures, CAS numbers, and intended chemical roles.
Application Tips
- Account for the high viscosity of Bis-GMA when preparing and mixing resin formulations
- Maintain consistent Bis-GMA-to-diluent ratios when comparing polymerization or material-property results
- Account for the approximately 100 ppm MEHQ inhibitor when establishing initiation and curing conditions
- For photopolymerization studies, control photoinitiator concentration, irradiation wavelength, irradiance, exposure time, and specimen thickness
- Characterize degree of conversion and final network properties experimentally rather than inferring performance from Bis-GMA content alone
Handling & Storage
- Store at 4°C
- Keep the container closed when not in use
- Use good laboratory ventilation during handling and formulation
- Avoid contact with skin and eyes
- Wear protective gloves and safety glasses during handling
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FAQ
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1. What is Bis-GMA used for?
Bis-GMA is a rigid aromatic dimethacrylate used in crosslinked resin systems. It is especially well established in dental-resin and composite research and is also used as a model monomer in studies of photopolymerized dimethacrylate networks.
2. Is Bis-GMA the same as bisphenol A?
No. Bis-GMA and bisphenol A are different chemical compounds. Bis-GMA, CAS Number 1565-94-2, contains polymerizable methacrylate groups. Bisphenol A, CAS Number 80-05-7, contains phenolic hydroxyl groups and does not have the same polymerizable methacrylate functionality.
3. Is Bis-GMA the same as bisphenol A diglycidyl ether (BADGE)?
No. Bis-GMA and bisphenol A diglycidyl ether are chemically distinct. BADGE contains reactive epoxide groups, whereas Bis-GMA contains two polymerizable methacrylate groups and pendant hydroxyl functionality.
4. Why is Bis-GMA highly viscous?
Bis-GMA contains a rigid aromatic core and pendant hydroxyl groups capable of intermolecular hydrogen bonding. These structural features contribute to its relatively high viscosity. Lower-viscosity dimethacrylate monomers are therefore often incorporated into experimental Bis-GMA formulations.
5. What inhibitor and package size are available for Cat. 03344?
Cat. 03344 contains approximately 100 ppm MEHQ inhibitor and is available in a 100 g package. For larger quantities, use the bulk-quote option.
Safety & Documentation
Use Bis-GMA with appropriate laboratory ventilation and personal protective equipment, including gloves and safety glasses. Refer to the product Safety Data Sheet (SDS) for complete handling, storage, first-aid, and disposal guidance.
