Ethylene glycol dimethacrylate

Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.[2]

Ethylene glycol dimethacrylate[1]
Skeletal formula
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)
Abbreviations EGDMA
1776663
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.380
EC Number
  • 202-617-2
637376
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 checkY
    Key: STVZJERGLQHEKB-UHFFFAOYSA-N checkY
  • 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:
GHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)
Infobox references

EGDMA can be used in free radical copolymer crosslinking reactions. 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.

It is used as a monomer to prepare Hydroxyapatite/Poly methyl methacrylate composites. EGDMA can be used in free radical copolymer crosslinking reactions.

Its toxicity profile has been fairly well studied.[3] It is sometimes called ethylene dimethacrylate.[4]

References
  1. |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Ethylene glycol dimethacrylate at Sigma-Aldrich
  2. Bielstein 2, IV, 1532
  3. 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.
  4. PubChem. "Ethylene glycol dimethacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-16.
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