Ethylene glycol dimethacrylate

HCID 7355CAS 97-90-5

Basic information

Standard SMILES
C=C(C)C(=O)OCCOC(=O)C(=C)C
InChIKey
STVZJERGLQHEKB-UHFFFAOYSA-N
Molecular formula
C10H14O4
Average molar mass
198.22 g/mol
Monoisotopic mass
198.08920893

Overview

Ethylene glycol dimethacrylate is the enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol. It has a role as a cross-linking reagent, an allergen and a polymerisation monomer. It is functionally related to a methacrylic acid and an ethylene glycol.

Names & identifiers

Preferred name
Ethylene glycol dimethacrylate
IUPAC
2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate
English name
Ethylene dimethacrylate
Molecular formula
C10H14O4
Molecular weight
198.22

Names & synonyms

Ethylene glycol dimethacrylate97-90-5Ethylene dimethacrylateGlycol dimethacrylateETHYLENE METHACRYLATEDiglycol dimethacrylateEthanediol dimethacrylate1,2-Bis(methacryloyloxy)ethaneEthylenedimethyacrylateEthyldiol metacrylateEGDMASartomer SR 206
Show more names
EDMAEthylene glycol dimethylacrylateGLYCOL HEMA-METHACRYLATEethane-1,2-diyl bis(2-Methylacrylate)Ethylene Glycol Dimethacrylate (stabilized with HQ)sr206TGM 1
Ageflex EGDMMethacrylic acid, ethylene esterEthylene glycol bis(methacrylate)1,2-Ethanediol dimethacrylateEthyldiol methacrylateMethacrylic acid ethylene esterSR 206DTXSID1026615

Database identifiers

CAS
97-90-5
PubChem CID
7355
DTXSID
DTXSID1026615
ChEMBL
CHEMBL1709582
ChEBI
CHEBI:53436
UNII
7BK5G69305
EC Number
202-617-2
Nikkaji
J38.144F

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
7
Heavy atoms
14

Experimental & physicochemical properties

PolymersPlastics & Rubber -> (Meth)acrylates
Cosmetics · 2 items

Cosmetic ingredients (Ethylene glycol dimethacrylate) -> CIR (Cosmetic Ingredient Review)

Cosmetic ingredients (Glycol Dimethacylate) -> CIR (Cosmetic Ingredient Review)

SpringerMaterials PropertiesViscosity
LogP · 2 items

2.4

1.22

Density · 3 items

1.055 at 20 °C/20 °C

Relative density (water = 1): 1.05

1.055 @ 20°C

Viscosity3.03 mm²/s at 20 °C

Physicochemical properties

Melting point
-40 °C · -40 °C
Boiling point
98 · 98-100 °C/5 mmHg (lit.)
Density
1.051 g/mL · 1.051 g/mL at 25 °C (lit.)
vapor density
1 · >1 (vs air)
vapor pressure
0.1 mm · <0.1 mm Hg ( 21.1 °C)
refractive index
20 · n20/D 1.454(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P271, P272, P280, P302+P352, P304+P340, P319, P321, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1326) of reports.

Warning

H317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Hazard information

Regulatory Information · 4 items

Chemical: 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester

2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 05-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14351

Ethylene glycol dimethacrylate: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible.
Hazards Summary · 1 item

Allergic contact dermatitis reported in dental technicians, dental assistants, and a manufacturing worker (making rear-view mirrors) ; [Kanerva, p. 1749] A lachrymator; [CHEMINFO] An eye and respiratory tract irritant; Not a sensitizer in one study of guinea pigs; Emergency treatment: Acrylates, multifunctional; [HSDB] May polymerize; An eye and respiratory tract irritant; May cause skin sensitization; [ICSC] Danger of skin sensitization; [MAK] An irritant; May cause skin sensitization; [Aldrich MSDS]

TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.
Chemical DangersThe substance may polymerize.
Physical DangersVapours are uninhibited and may polymerize, causing blockage of vents.

Safety & protection

Fire FightingUse water, foam, powder, carbon dioxide.
First Aid Measures · 4 items

Fresh air, rest.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth.

Safe StorageStore only if stabilized. Cool. Refer to the manufacturer's instructions for proper storage conditions.
Storage Conditions · 1 item

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

Spillage DisposalCollect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures · 3 items

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxicology

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
ICSC Environmental DataThe substance is harmful to aquatic organisms.
TSCA Test Submissions · 1 item

The ability of ethylene dimethacrylate to induce mutations at the TK gene locus in L5178Y mouse lymphoma cells was evaluated in vitro. Cells were exposed to test article at concentrations ranging from 31.3 to 800 nl/ml both with and without Aroclor-induced rat liver S9 metabolic activation. In the presence of activation, a 2.4 to 10 fold increase in mutation frequency was observed in cells exposed to concentrations ranging from 400 to 700 nl/ml, while the percent relative growth decreased from 78.3 to 33.6%. In the absence of activation, exposure to concentrations of up to 800 nl/ml caused high toxicity but no increase in mutation rate.

Human Toxicity Excerpts · 1 item

BIOLOGICALLY, METHACRYLATES RESEMBLE ACRYLATES, EXCEPT FOR LOWER REACTIVITY & THUS DECR TOXICITY. THIS IS PROBABLY DUE TO STERIC HINDRANCE BY ITS METHYL GROUP & IN TURN DECR RATES OF MEMBRANE TRANSPORT & SYSTEMIC TRANSLOCATION. /METHACRYLIC ESTERS/

Non-Human Toxicity Excerpts · 1 item

TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING ETHYLENE METHACRYLATE, WERE SCANNED FOR THEIR ABILITY TO INDUCE CONTACT SENSITIVITY, USING 5 DIFFERENT SENSITIZATION PROTOCOLS. CONTACT REACTIONS OF VARYING INTENSITIES WERE PRODUCED TO ALL THE MONO-, DI-, AND TRIACRYLATES TESTED. METHACRYLATES DID NOT SENSITIZE GUINEA PIGS.

Regulatory information

TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

Safety data

F
8-19
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
OZ4400000
ridadr
UN 3334

Chemistry & industry

Pharmacology

Metabolism/MetabolitesSMALL QUANTITIES OF METHACRYLATES MAY READILY BE METABOLIZED BY SAPONIFICATION INTO THE ALCOHOL AND METHACRYLIC ACID. THE LATTER MAY FORM AN ACETYL-COENZYME A DERIVATIVE, WHICH THEN ENTERS THE NORMAL LIPID METABOLISM. /METHACRYLATES/
MeSH Pharmacological Classification · 1 item

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.

Uses & manufacturing

Uses · 6 items

CIR ingredient: Ethylene glycol dimethacrylate

CIR ingredient: Glycol Dimethacylate

In polymers for dental restorative resins; in synthetic wound dressings; as rate-controlling barrier in slow release capsules; in acrylic nail preparation; as curing agent for acrylics and rubbers; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

/SRP/: IN POLYMERS FOR DENTAL RESTORATIVE RESINS; IN SYNTHETIC WOUND DRESSINGS; AS RATE-CONTROLLING BARRIER IN SLOW RELEASE CAPSULES; IN ACRYLIC NAIL PREPN.

CROSSLINKING AGENT FOR THERMOSET & UV CURABLE ACRYLICS.

U.S. Production · 3 items

2023: 2,500,000 - <4,000,000 lb

(1979) PROBABLY GREATER THAN 4.54X10+6 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

Consumer UsesMonomers
Industry UsesIntermediate
Methods of Manufacturing · 2 items

TRANSESTERIFICATION OR ESTERIFICATION OF ETHYLENE GLYCOL WITH AN EXCESS OF EITHER METHYL METHACRYLATE OR METHACRYLIC ACID

The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/

General Manufacturing Information · 2 items

Printing and Related Support Activities

2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester: ACTIVE

Applications · 4 items

DescriptionIt is mainly applied in the field of organic synthesis, such as a crosslinking agent for fabricating resin, resin processing, fabricating adhesives and coatings, rubber resin modifier, anaerobic adhesive, and plastic paste. Specifically, this chemical can be used as the raw material to prepare a copolymer that has been demonstrated to act as a biocompatible interface between glucose biosensors and tissue in the rat.1 Moreover, this compound may be involved in the preparation of poly(2-vinyl-4,4-dimethylazlactone-co-acrylamide-co-ethylene dimethacrylate) for designing the porous support for high throughput reactors.2 In addition, the bulk polymerization of this chemical and glycidyl methacrylate results in the formation of porous monolith as a stationary phase in dye-affinity chromatography.3

DescriptionThe crosslinking agent of acrylic resins, ethyleneglycol dimethacrylate (EGDMA), is employed to optimize the dilution of high-viscosity monomers and to link together the macromolecules costituting the polymer. It caused contact dermatitis in dental technicians and dental assistants. A case was also reported in a car rear-view mirror manufacturer.

UsesEthylene glycol dimethacrylate is used as a functional monomer for polymers and as a cross linking agent between the molecular chains of polymers and elastomers. It is also used in free radical copolymer cross linking reactions. It acts as an intermediate in the production of hydroxyapatite and poly methyl methacrylate composites. It is also used in dentaI composites, sealants, prostheses, adhesives, artificiaI nails, printing inks, etc.

General DescriptionEthylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南万多鑫化工有限公司0531-88770993 13905318421 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Ethylene glycol dimethacrylate is the enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol. It has a role as a cross-linking reagent, a polymerisation monomer and an allergen. It is functionally related to an ethylene glycol and a methacrylic acid.

Related reactions

39 records

Linked notes

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