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494356

Sigma-Aldrich

Bisphenol A glycerolate dimethacrylate

glycerol/phenol 1

Synonym(s):

2,2′-Bis[4-(3-methacryloxy-2-hydroxypropoxy)phenyl]propane, 2,2′-Bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane, 2,2-Bis[p -(3-methacryloxy-2-hydroxypropoxy)phenyl]propane, 2,2-Bis[p -[2-hydroxy-3-(methacryloxy)propoxy]phenyl]propane, Bisphenol A bis(2-hydroxy-3-methacryloxypropyl) ether

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About This Item

Linear Formula:
[H2C=C(CH3)CO2CH2CH(OH)CH2OC6H4-4-]2C(CH3)2
CAS Number:
1565-94-2
Molecular Weight:
512.59
MDL number:
MFCD00191825
UNSPSC Code:
12162002
PubChem Substance ID:
24872895
NACRES:
NA.23

composition

glycerol/phenol, 1

Quality Level

200

refractive index

n20/D 1.552 (lit.)

density

1.161 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)OCC(O)COc1ccc(cc1)C(C)(C)c2ccc(OCC(O)COC(=O)C(C)=C)cc2

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

InChI key

AMFGWXWBFGVCKG-UHFFFAOYSA-N

General description

Bisphenol A glycerolate dimethacrylate(BisGMA) is an advanced derivative of Bisphenol A(BPA). It is a conventional epoxy methacrylate that is widely used as a monomer in many applications due to the following properties:
  • Phenyl ring provides chemical resistance
  • Ether linkage allows flexibility
  • Hydroxyl group gives good adhesion
  • Methacrylate is the reactive site for crosslinking

Application

The Progress in Development of Dental Restorative Materials
Bisphenol A glycerolate dimethacrylate can be used:
  • As a crosslinking monomer in the preparation of zwitter ionic monolithic columns for liquid chromatography.
  • In the preparation of an antibacterial dental adhesive.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H317,H318,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

230.0 °F

Flash Point(C)

110 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV8438
MKCW7278
MKCV6596
MKCV1081
MKCT0675

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The journal of adhesive dentistry, 16(2), 123-128 (2013-10-09)
To assess the influence of adhesive restorations on hydrogen peroxide (H2O2) diffusion through enamel and dentin and its cytotoxicity to pulp (MDPC-23) cells. Sound and resin-restored enamel/dentin disks were stored in water for 24 h or 6 months and adapted
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The aim of this study was to evaluate the effect of camphorquinone concentration in physical-mechanical properties of experimental flowable composites in order to find the concentration that results in maximum conversion, balanced mechanical strength, and minimum shrinkage stress. Model composites
Bruno Albuquerque Carneiro et al.
The Journal of oral implantology, 40(2), 161-168 (2014-05-02)
The use of provisional resin implant-supported complete dentures is a fast and safe procedure to restore mastication and esthetics of patients soon after surgery and during the adaptation phase to the new denture. This study assessed stress distribution of provisional
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The Journal of oral implantology, 39(5), 559-573 (2011-07-20)
This study is a phase of a biomechanical study, a part of a research program concerned with the new concept of in situ tooth replication. The purpose of the study was to evaluate tooth replica under each of two possible
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