Ethylene glycol dimethacrylate

Last updated
Ethylene glycol dimethacrylate [1]
Ethylene glycol dimethylacrylate Structural Formula V1.svg
Ethylene-glycol-dimethacrylate-3D-balls.png
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 and one equivalent of ethylene glycol. [2]

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]

Related Research Articles

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Polyethylene</span> Most common thermoplastic polymer

Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging (plastic bags, plastic films, geomembranes and containers including bottles, etc.). As of 2017, over 100 million tonnes of polyethylene resins are being produced annually, accounting for 34% of the total plastics market.

<span class="mw-page-title-main">Polyethylene glycol</span> Chemical compound

Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH.

<span class="mw-page-title-main">Copolymer</span> Polymer derived from more than one species of monomer

In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are sometimes called bipolymers. Those obtained from three and four monomers are called terpolymers and quaterpolymers, respectively. Copolymers can be characterized by a variety of techniques such as NMR spectroscopy and size-exclusion chromatography to determine the molecular size, weight, properties, and composition of the material.

<span class="mw-page-title-main">End group</span> Functional group at the extremity of an oligomer or other macromolecule

End groups are an important aspect of polymer synthesis and characterization. In polymer chemistry, they are functional groups that are at the very ends of a macromolecule or oligomer (IUPAC). In polymer synthesis, like condensation polymerization and free-radical types of polymerization, end-groups are commonly used and can be analyzed by nuclear magnetic resonance (NMR) to determine the average length of the polymer. Other methods for characterization of polymers where end-groups are used are mass spectrometry and vibrational spectrometry, like infrared and raman spectroscopy. These groups are important for the analysis of polymers and for grafting to and from a polymer chain to create a new copolymer. One example of an end group is in the polymer poly(ethylene glycol) diacrylate where the end-groups are circled.

<span class="mw-page-title-main">Radical polymerization</span> Polymerization process involving free radicals as repeating units

In polymer chemistry, free-radical polymerization (FRP) is a method of polymerization by which a polymer forms by the successive addition of free-radical building blocks. Free radicals can be formed by a number of different mechanisms, usually involving separate initiator molecules. Following its generation, the initiating free radical adds (nonradical) monomer units, thereby growing the polymer chain.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Polyhydroxyethylmethacrylate</span> Chemical compound

Poly(2-hydroxyethyl methacrylate) (pHEMA) is a polymer that forms a hydrogel in water. Poly (PHEMA) hydrogel for intraocular lens (IOL) materials was synthesized by solution polymerization using 2-hydroxyethyl methacrylate (HEMA) as raw material, ammonium persulfate and sodium pyrosulfite (APS/SMBS) as catalyst, and triethyleneglycol dimethacrylate (TEGDMA) as cross-linking additive. It was invented by Drahoslav Lim and Otto Wichterle for biological use. Together they succeeded in preparing a cross-linking gel which absorbed up to 40% of water, exhibited suitable mechanical properties and was transparent. They patented this material in 1953.

<span class="mw-page-title-main">Captodative effect</span>

The captodative effect is the stabilization of radicals by a synergistic effect of an electron-withdrawing substituent and an electron-donating substituent. The name originates as the electron-withdrawing group (EWG) is sometimes called the "captor" group, whilst the electron-donating group (EDG) is the "dative" substituent. Olefins with this substituent pattern are sometime described as captodative. Radical reactions play an integral role in several chemical reactions and are also important to the field of polymer science.

Polyester resins are synthetic resins formed by the reaction of dibasic organic acids and polyhydric alcohols. Maleic anhydride is a commonly used raw material with diacid functionality in unsaturated polyester resins. Unsaturated polyester resins are used in sheet moulding compound, bulk moulding compound and the toner of laser printers. Wall panels fabricated from polyester resins reinforced with fiberglass—so-called fiberglass reinforced plastic (FRP)—are typically used in restaurants, kitchens, restrooms and other areas that require washable low-maintenance walls. They are also used extensively in cured-in-place pipe applications. Departments of Transportation in the USA also specify them for use as overlays on roads and bridges. In this application they are known AS Polyester Concrete Overlays (PCO). These are usually based on isophthalic acid and cut with styrene at high levels—usually up to 50%. Polyesters are also used in anchor bolt adhesives though epoxy based materials are also used. Many companies have and continue to introduce styrene free systems mainly due to odor issues, but also over concerns that styrene is a potential carcinogen. Drinking water applications also prefer styrene free. Most polyester resins are viscous, pale coloured liquids consisting of a solution of a polyester in a reactive diluent which is usually styrene, but can also include vinyl toluene and various acrylates.

<span class="mw-page-title-main">(Hydroxyethyl)methacrylate</span> Chemical compound

Hydroxyethylmethacrylate is the organic compound with the chemical formula H2C\dC(CH3)CO2CH2CH2OH. It is a colorless viscous liquid that readily polymerizes. Hydroxyethylmethacrylate is a monomer that is used to make various polymers.

Solution polymerization is a method of industrial polymerization. In this procedure, a monomer is dissolved in a non-reactive solvent that contains a catalyst or initiator.

Catalytic chain transfer (CCT) is a process that can be incorporated into radical polymerization to obtain greater control over the resulting products.

<span class="mw-page-title-main">Living free-radical polymerization</span>

Living free radical polymerization is a type of living polymerization where the active polymer chain end is a free radical. Several methods exist. IUPAC recommends to use the term "reversible-deactivation radical polymerization" instead of "living free radical polymerization", though the two terms are not synonymous.

<span class="mw-page-title-main">Graft polymer</span> Polymer with a backbone of one composite and random branches of another composite

In polymer chemistry, graft polymers are segmented copolymers with a linear backbone of one composite and randomly distributed branches of another composite. The picture labeled "graft polymer" shows how grafted chains of species B are covalently bonded to polymer species A. Although the side chains are structurally distinct from the main chain, the individual grafted chains may be homopolymers or copolymers. Graft polymers have been synthesized for many decades and are especially used as impact resistant materials, thermoplastic elastomers, compatibilizers, or emulsifiers for the preparation of stable blends or alloys. One of the better-known examples of a graft polymer is a component used in high impact polystyrene, consisting of a polystyrene backbone with polybutadiene grafted chains.

<span class="mw-page-title-main">Allyl glycidyl ether</span> Chemical compound

Allyl glycidyl ether is an organic compound used in adhesives and sealants and as a monomer for polymerization reactions. It is formally the condensation product of allyl alcohol and glycidol via an ether linkage. Because it contains both an alkene and an epoxide group, either group can be reacted selectively to yield a product where the other functional group remains intact for future reactions.

Functionalized polyolefins are olefin polymers with polar and nonpolar functionalities attached onto the polymer backbone. There has been an increased interest in functionalizing polyolefins due to their increased usage in everyday life. Polyolefins are virtually ubiquitous in everyday life, from consumer food packaging to biomedical applications; therefore, efforts must be made to study catalytic pathways towards the attachment of various functional groups onto polyolefins in order to affect the material's physical properties.

<span class="mw-page-title-main">Heather Maynard</span> American chemist

Heather D. Maynard is the Dr Myung Ki Hong Professor in Polymer Science at the University of California, Los Angeles. She works on protein-polymer conjugates and polymeric drugs. Maynard is a Fellow of the Royal Society of Chemistry and the American Association for the Advancement of Science.

<span class="mw-page-title-main">Pentaerythritol tetraacrylate</span> Chemical compound

Pentaerythritol tetraacrylate is an organic compound. It is a tetrafunctional acrylate ester used as a monomer in the manufacture of polymers. As it is a polymerizable acrylate monomer, it is nearly always supplied with an added polymerisation inhibitor, such as MEHQ.

References

  1. "Ethylene glycol dimethacrylate". 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.