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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 237
実験および物理化学的性質
Cosmetics
Cosmetic ingredients (Ethylene glycol dimethacrylate) -> CIR (Cosmetic Ingredient Review)
Cosmetic ingredients (Glycol Dimethacylate) -> CIR (Cosmetic Ingredient Review)
LogP
2.4
1.22
Density
1.055 at 20 °C/20 °C
Relative density (water = 1): 1.05
1.055 @ 20°C
Solubility
> 10% in benzene
> 10% in ethanol
> 10% in ligroin
Solubility in water, g/l at 20 °C: 1.1 (slightly soluble)
Boiling Point
260
260 °C
260 °C @760 [mm Hg]
Melting Point
-40 °C
-40 °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.)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 5 g/l · <5g/l
- 外見
- 液体
- 色
- 無色~淡黄色
- 水溶解度
- 溶ける
- BRN
- 1776663 · 1776663
- 安定性
- 不安定 - 光にさらされると重合する可能性があります。強酸、強酸化剤、強塩基とは相容れない。
- 化粧品成分の機能
- 爪のコンディショニング
- 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 データベース
- 97 · 97-90-5(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester(97-90-5)
- EPAの化学物質情報
- Ethylene glycol dimethacrylate (97-90-5)
安全と法規制
GHS分類
GHS Classification
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
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
Hazards Summary
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]
Hazard Classes and Categories
Skin Sens. 1 (> 99.9%)
Specific target organ toxicity (single exposure) - category 3
Skin sensitization - Category 1
Skin sensitization - Category 1B
STOT SE 3
安全と保護具
First Aid Measures
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.
Storage Conditions
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/
Preventive Measures
... 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
TSCA Test Submissions
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
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
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
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
- hs_code
- 29161490
- risk_code
- 37-43
- 化審法
- (2)-1056, (2)-1059
- 消防法
- 危-4-3-III
- hazard_code
- Xi
- safety_code
- 24-37-36/37
- Hazard Classifications
- Skin Sens. 1STOT SE 3
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 97-90-5(Hazardous Substances Data)
化学と産業
薬理情報
MeSH Pharmacological Classification
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
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
2023: 2,500,000 - <4,000,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+6 G
(1981) PROBABLY GREATER THAN 2.27X10+6 G
Methods of Manufacturing
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
Printing and Related Support Activities
2-Propenoic acid, 2-methyl-, 1,1'-(1,2-ethanediyl) ester: ACTIVE
応用分野
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
補足説明
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
関連ノート
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