Ethylene glycol dimethacrylate

Last updated
Ethylene glycol dimethacrylate [1]
Skeletal formula Ethylene glycol dimethylacrylate Structural Formula V1.svg
Skeletal formula
Ball-and-stick model Ethylene-glycol-dimethacrylate-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
Ethane-1,2-diyl bis(2-methylprop-2-enoate)
Other names
Methacrylic acid, ethylene ester; 1,2-Bis(methacryloyloxy)ethane; 1,2-Ethanediol dimethacrylate; Diglycol dimethacrylate; Ethanediol dimethacrylate; Ethylene dimethacrylate; Ethylene glycol bis(methacrylate); Ethylene glycol dimethacrylate; Ethylene methacrylate; 2-(Methacryloyloxy)ethyl methacrylate
Identifiers
3D model (JSmol)
AbbreviationsEGDMA
1776663
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.380 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-617-2
637376
PubChem CID
RTECS number
  • OZ4400000
UNII
  • InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3 Yes check.svgY
    Key: STVZJERGLQHEKB-UHFFFAOYSA-N Yes check.svgY
  • CC(=C)C(=O)OCCOC(=O)C(=C)C
Properties
C10H14O4
Molar mass 198.218 g·mol−1
Density 1.051 g/mL
Melting point −40 °C (−40 °F; 233 K)
Boiling point 98 to 100 °C (208 to 212 °F; 371 to 373 K) (5 mmHg)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H317, H319, H335, H412
P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Flash point 101 °C (214 °F; 374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid with ethylene glycol. It is a colorless viscous liquid. [2] It is sometimes called ethylene dimethacrylate. [3]

Contents

Polymerization

Containing a pair of reactive alkene groups, EGDMA is a crosslinking agent. Like other acrylates, it is susceptible free radical polymerization. When used with methyl methacrylate, it leads to gel point at relatively low concentrations because of the nearly equivalent reactivities of all the double bonds involved. As a monomer, It is used to prepare hydroxyapatite/poly methyl methacrylate composites.

Preparation

EGDMA is also synthesized by esterification of methacrylic acid with ethylene glycol:

2 H2C=C(CH3)CO2H + HOCH2CH2OH → H2C=C(CH3)CO2CH2CH2O2C(CH3)C=CH2 + 2 H2O

It also forms inadvertently in the hydroxyethylation of methacrylic acid, which is usually intended to give (hydroxyethyl)methacrylate:]]:

2 H2C=C(CH3)CO2H + CH2CH2O → H2C=C(CH3)CO2CH2CH2O2C(CH3)C=CH2 + H2O

Safety

Its toxicity profile has been fairly well studied. [4]

References

  1. "Ethylene glycol dimethacrylate". Sigma-Aldrich.
  2. Bielstein 2, IV, 1532
  3. PubChem. "Ethylene glycol dimethacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-16.
  4. Bielecka-Kowalska, Anna; Czarny, Piotr; Wigner, Paulina; Synowiec, Ewelina; Kowalski, Bartosz; Szwed, Marzena; Krupa, Renata; Toma, Monika; Drzewiecka, Malgorzata; Majsterek, Ireneusz; Szemraj, Janusz; Sliwinski, Tomasz; Kowalski, Michał (March 2018). "Ethylene glycol dimethacrylate and diethylene glycol dimethacrylate exhibits cytotoxic and genotoxic effect on human gingival fibroblasts via induction of reactive oxygen species" . Toxicology in Vitro. 47: 8–17. doi:10.1016/j.tiv.2017.10.028.