エチレングリコールジメタクリラート

Ethylene glycol dimethacrylate

HCID 7355CAS 97-90-5

基本情報

標準SMILES
C=C(C)C(=O)OCCOC(=O)C(=C)C
InChIKey
STVZJERGLQHEKB-UHFFFAOYSA-N
分子式
C10H14O4
平均分子量
198.22 g/mol
単同位体質量
198.08920893

概要

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.

名称と識別子

優先名称
Ethylene glycol dimethacrylate
IUPAC
2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate
現地名
エチレングリコールジメタクリラート
英語名
Ethylene dimethacrylate
分子式
C10H14O4
分子量
198.22

名称と別名

Ethylene glycol dimethacrylate97-90-5Ethylene dimethacrylateGlycol dimethacrylateETHYLENE METHACRYLATEDiglycol dimethacrylateEthanediol dimethacrylate1,2-Bis(methacryloyloxy)ethaneEthylenedimethyacrylateEthyldiol metacrylateEGDMASartomer SR 206
名称をさらに表示
エチレングリコールジメタクリラートジメタクリル酸エチレンエタン-1,2-ジオールビスメタクリラートエチレンジメタクリラートビス(メタクリル酸)エチレン1,2-エタンジオールジメタクリラートビスメタクリル酸エチレンジメタクリル酸エチレングリコールビス(メタクリル酸)1,2-エタンジイルジメタクリル酸1,2-エタンジイルビスメタクリル酸エタン-1,2-ジイルエチレングリコールビスメタクリラートメタクリル酸2-(メタクリロイルオキシ)エチルエチレンジメタクリレート二メタクリル酸エチレンエタン-1,2-ジオールビス(2-メチルアクリラート)ビス(2-メチルプロペン酸)エチレン1,2-ビス(メタクリロイルオキシ)エタンエタン-1,2-ジオールジメタクリラートビスメタクリル酸1,2-エタンジイル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

データベース識別子

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

物性

構造計算による物性

XLogP
1.9
極性表面積
52.6 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
7
重原子数
14

実験および物理化学的性質

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

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

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

SpringerMaterials PropertiesViscosity
LogP · 2 件

2.4

1.22

Density · 3 件

1.055 at 20 °C/20 °C

Relative density (water = 1): 1.05

1.055 @ 20°C

Viscosity3.03 mm²/s at 20 °C

物理化学的性質

融点
-40 °C · -40 °C
沸点
98 · 98-100 °C/5 mmHg (lit.)
比重(密度)
1.051 g/mL · 1.051 g/mL at 25 °C (lit.)
蒸気密度
1 · >1 (vs air)
蒸気圧
0.1 mm · <0.1 mm Hg ( 21.1 °C)
屈折率
20 · n20/D 1.454(lit.)

安全と法規制

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Regulatory Information · 4 件

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 件

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.

安全と保護具

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

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 件

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 件

... 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.

毒性情報

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 件

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 件

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 件

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.

法規制情報

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.

安全データ

F
8-19
wgk
1
tsca
TSCA listed
rtecs
OZ4400000
ridadr
UN 3334
毒性
LD50 orally in Rabbit: 3300 mg/kg

化学と産業

薬理情報

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 件

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.

用途と製造

Uses · 6 件

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 件

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 件

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 件

Printing and Related Support Activities

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

応用分野 · 5 件

用途歯科材料、アクリル樹脂

用途ゴム改質剤、皮革処理剤

用途有機合成原料。

説明The 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.

一般的な説明Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.

上流・下流製品情報

上流原料

サプライヤー50 社

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]
補足説明 · 2 件

定義本品は、次の化学式で表される有機化合物である。

定義ChEBI: 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.

関連反応

39 件

関連ノート

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