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Ethylene glycol dimethacrylate

HCID 7355
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Basic information

CAS
97-90-5
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

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
Formal charge
0
Complexity
237

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
Solubility · 4 items

> 10% in benzene

> 10% in ethanol

> 10% in ligroin

Solubility in water, g/l at 20 °C: 1.1 (slightly soluble)

Flash Point101 °C c.c.
Boiling Point · 3 items

260

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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 Requirements

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

Related reactions

39 records
New reaction record
HRID 23004 reaction equation
HRID 23004As reactantuspto-grants-2005_02
HRID 323845 reaction equation
HRID 323845As reactantuspto-grants-2001_04
HRID 323846 reaction equation
HRID 323846As reactantuspto-grants-2001_04
HRID 323847 reaction equation
HRID 323847As reactantuspto-grants-2001_04
HRID 323848 reaction equation
HRID 323848As reactantuspto-grants-2001_04
HRID 323849 reaction equation
HRID 323849As reactantuspto-grants-2001_04
HRID 323912 reaction equation
HRID 323912As productuspto-grants-2001_04
HRID 342365 reaction equation
HRID 342365As reactantuspto-grants-1999_01
Page 1 of 5

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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ChEMBL
CHEMBL1709582
ChEBI
CHEBI:53436
UNII
7BK5G69305
EC Number
202-617-2
Nikkaji
J38.144F

260 °C

260 °C @760 [mm Hg]

DecompositionWhen heated to decomp it emits acrid smoke and irritating fumes.
Melting Point · 2 items

-40 °C

-40 °C

Vapor DensityRelative vapor density (air = 1): 6.8

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.)
Flash point
230 °F · >230 °F
storage temp.
30 °C · Store below +30°C.
solubility
5 g/l · <5g/l
form
Liquid
color
Colorless to pale yellow
Viscosity
3.06 mm2/s · 3.06mm2/s
Water Solubility
soluble
α-end
methacrylate
Ω-end
methacrylate
BRN
1776663 · 1776663
Stability
Unstable - may polymerize upon exposure to light. Incompatible with strong acids, strong oxidizing agents, strong bases.
Cosmetics Ingredients Functions
NAIL CONDITIONING
Cosmetic Ingredient Review (CIR)
Ethylene dimethacrylate (97-90-5)
InChI
1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
InChIKey
STVZJERGLQHEKB-UHFFFAOYSA-N
SMILES
CC(=C)C(=O)OCCOC(=O)C(C)=C
LogP
2.4 at · 2.4 at 20℃
CAS DataBase Reference
97 · 97-90-5(CAS DataBase Reference)
Indirect Additives used in Food Contact Substances
ETHYLENE GLYCOL DIMETHACRYLATE
FDA 21 CFR
177.101 · 177.1010; 177.2600
EWG's Food Scores
3 · 3-6
FDA UNII
7 BK5G69305 · 7BK5G69305
NIST Chemistry Reference
2 · 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester(97-90-5)
EPA Substance Registry System
Ethylene glycol dimethacrylate (97-90-5)
Cosmetics Info
Glycol HEMA-Methacrylate
UNSPSC Code
12352108 · 12352108
NACRES
23 · NA.23
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317-H335
Precautionary statements
261 · P261-P271-P272-P280-P302+P352-P304+P340+P312
target organs
Respiratory system
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi
Risk Statements
37 · 37-43
Safety Statements
24 · 24-37-36/37
RIDADR
3334 · UN 3334
WGK Germany
1 · 1
RTECS
4400000 · OZ4400000
F
8 · 8-19
TSCA
TSCA listed
HS Code
29161490 · 29161490
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
1 STOT · Skin Sens. 1STOT SE 3
Hazardous Substances Data
97 · 97-90-5(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 3300 mg/kg
REACH Registrations
Active
Section 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.
Hazard Classes and Categories · 5 items

Skin Sens. 1 (> 99.9%)

Specific target organ toxicity (single exposure) - category 3

Skin sensitization - Category 1

Skin sensitization - Category 1B

STOT SE 3

Skin, Eye, and Respiratory IrritationsIrritating to eyes & respiratory system.

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.

Eye PreventionWear face shield.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionSTRICT HYGIENE!
Ingestion PreventionDo not eat, drink, or smoke during work.

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
hs_code
29161490
Toxicity
LD50 orally in Rabbit: 3300 mg/kg
risk_code
37-43
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
24-37-36/37
Storage Class
10 - Combustible liquids
target organs
Respiratory system
Hazard statements
H317-H335
REACH Registrations
Active
Hazard Classifications
Skin Sens. 1STOT SE 3
Precautionary statements
P261-P271-P272-P280-P302+P352-P304+P340+P312
Hazardous Substances Data
97-90-5(Hazardous Substances Data)

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

Methacrylic acid
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.