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156329

Sigma-Aldrich

Bisphenol A dimethacrylate

>98%

Synonym(s):

2,2-Bis(4-hydroxyphenyl)propane dimethacrylate, 2,2-Bis(4-methacryloxyphenyl)propane, 2,2-Bis(4-methacryloyloxyphenyl)propane, 4,4′-Isopropylidenediphenol dimethacrylate, BPADMA

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About This Item

Linear Formula:
[H2C=C(CH3)CO2C6H4]2C(CH3)2
CAS Number:
Molecular Weight:
364.43
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

Assay

>98%

form

solid

mp

72-74 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)Oc1ccc(cc1)C(C)(C)c2ccc(OC(=O)C(C)=C)cc2

InChI

1S/C23H24O4/c1-15(2)21(24)26-19-11-7-17(8-12-19)23(5,6)18-9-13-20(14-10-18)27-22(25)16(3)4/h7-14H,1,3H2,2,4-6H3

InChI key

QUZSUMLPWDHKCJ-UHFFFAOYSA-N

General description

Bisphenol A dimethacrylate (BPA-DMA) is a key monomer, available in solid form with an assay of >98%, widely used in material science, particularly in the formulation of polymers and composite materials. BPA-DMA is primarily utilized as a crosslinking agent in the production of various thermosetting polymers. In dental applications, BPA-DMA is often incorporated into composites and adhesives due to its excellent bonding properties and ability to form durable, wear-resistant materials.

Application

Bisphenol A dimethacrylate (BPA-DMA) can be used as:
  • A template in the synthesis of molecularly imprinted polymers (MIPs). The use of BPA-DMA allows for the formation of specific cavities in the polymer matrix that match the shape and functional groups of BPA, enhancing the selectivity and affinity of the resulting polymer for its target analyte.
  • A co-monomer in the synthesis of photopolymerized monoliths for capillary electrochromatography.
  • A key component in the production of bisphenol A-glycidyl methacrylate (Bis-GMA), which is widely used in dental restorative materials due to its mechanical properties and potential for additional functionalities like antibacterial activity.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Alain Pefferkorn et al.
Dental materials : official publication of the Academy of Dental Materials, 24(12), 1647-1654 (2008-05-13)
The elaboration of efficient dental resins requires a high degree of internal cohesion and a strong organization of the filler/matrix systems, and a good compatibility between the organic and inorganic constituents of the composite. Combining fractal aerosils and polymer constitutes
Jane C Atkinson et al.
Dental materials : official publication of the Academy of Dental Materials, 18(2), 128-135 (2002-01-05)
This study investigated the stability of compounds of dental sealant materials in a salivary matrix. Various amounts of bisphenol A (BPA), bisphenol A dimethacrylate (BIS-DMA) or triethylene-glycol dimethacrylate (TEGDMA) were added to whole salivary samples, and stored at -70 degrees
Faisal D Al-Qarni et al.
Journal of dentistry, 78, 91-99 (2018-08-29)
The objectives were to develop a calcium (Ca) and phosphate (P) ion-rechargeable and protein-repellent adhesive containing nanoparticles of amorphous calcium phosphate (NACP) and 2-methacryloyloxyethyl phosphorylcholine (MPC), and investigate the MPC effects on ion recharge and re-releases for the first time.
R E Smith et al.
Biochimica et biophysica acta, 1550(1), 100-106 (2001-12-12)
The dental restorative monomer, BISGMA (2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane), and bisphenol A diglycidyl ether (BADGE) increase the velocity of the reaction catalyzed by pancreatic cholesterol esterase (CEase, bovine). The metabolite of these monomers, bisphenol A bis(2,3-dihydroxypropyl) ether, and a common plasticizer, di-2-ethylhexyl phthalate
Stomatitis and perioral dermatitis caused by epoxy diacrylates in dental composite resins.
L Kanerva et al.
Journal of the American Academy of Dermatology, 38(1), 116-120 (1998-02-03)

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