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Ethylendimethacrylat
EGDMA · ETHYLENE GLYCOL DIMETHACRYLATE · EDMA · Ethylene glycol dimethylacrylate · GLYCOL HEMA-METHACRYLATE · ethane-1,2-diyl bis(2-Methylacrylate) · Ethylene Glycol Dimethacrylate (stabilized with HQ) · sr206
Identifikatoren & physikalische Daten
| CAS No. | 97-90-5 |
|---|---|
| Summenformel | C10H14O4 |
| Durchschnittliche Molmasse | 198,22 g/mol |
| Monoisotopische Masse | 198,08920893 g/mol |
| SMILES | C=C(C)C(=O)OCCOC(=O)C(=C)C |
| InChIKey | STVZJERGLQHEKB-UHFFFAOYSA-N |
| PubChem CID | 7355 |
| ChEMBL | CHEMBL1709582 |
| ChEBI | CHEBI:53436 |
| EC No. | 202-617-2 |
| DTXSID | DTXSID1026615 |
| Lokaler Name | Ethylendimethacrylat |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 237 |
| Polymers | Plastics & Rubber -> (Meth)acrylates |
| Kosmetika | Cosmetic ingredients (Ethylene glycol dimethacrylate) -> CIR (Cosmetic Ingredient Review)Cosmetic ingredients (Glycol Dimethacylate) -> CIR (Cosmetic Ingredient Review) |
| SpringerMaterials Properties | Viscosity |
| LogP (Verteilungskoeffizient) | 2.41.22 |
| Dichte | 1.055 at 20 °C/20 °CRelative density (water = 1): 1.051.055 @ 20°C1.051 g/mL at 25 °C (lit.) |
| Viscosity | 3.03 mm²/s at 20 °C |
| Löslichkeit | > 10% in benzene> 10% in ethanol> 10% in ligroinSolubility in water, g/l at 20 °C: 1.1 (slightly soluble)<5g/l |
| Flammpunkt | 101 °C c.c.>230 °F |
| Siedepunkt | 260260 °C260 °C @760 [mm Hg]98-100 °C/5 mmHg (lit.) |
| Decomposition | When heated to decomp it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -40 °C |
| Dampfdichte | Relative vapor density (air = 1): 6.8>1 (vs air) |
| Dampfdruck | <0.1 mm Hg ( 21.1 °C) |
| Brechungsindex | n20/D 1.454(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Colorless to pale yellow |
| BRN | 1776663 |
| Stabilität | Unstable - may polymerize upon exposure to light. Incompatible with strong acids, strong oxidizing agents, strong bases. |
| Kosmetik-Inhaltsstoffe Funktionen | NAIL CONDITIONING |
| 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 (Verteilungskoeffizient) | 2.4 at 20℃ |
| CAS Datenbank | 97-90-5(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester(97-90-5) |
| EPA chemische Informationen | Ethylene glycol dimethacrylate (97-90-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH317: 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.H317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 2-methyl-, 1,2-ethanediyl ester2-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/14351Ethylene glycol dimethacrylate: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. |
| Gefahrenübersicht | 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 irritantNot a sensitizer in one study of guinea pigsEmergency treatment: Acrylates, multifunctional[HSDB] May polymerizeAn eye and respiratory tract irritantMay cause skin sensitization[ICSC] Danger of skin sensitization[MAK] An irritant[Aldrich MSDS] |
| TSCA-Anforderungen | 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 Dangers | The substance may polymerize. |
| Physical Dangers | Vapours are uninhibited and may polymerize, causing blockage of vents. |
| Hazard Classes and Categories | Skin Sens. 1 (> 99.9%)Specific target organ toxicity (single exposure) - category 3Skin sensitization - Category 1Skin sensitization - Category 1BSTOT SE 3 |
| Skin, Eye, and Respiratory Irritations | Irritating to eyes & respiratory system. |
| Brandbekämpfung | Use water, foam, powder, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | 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. |
| Sichere Lagerung | Store only if stabilized. Cool. Refer to the manufacturer's instructions for proper storage conditions. |
| Lagerbedingungen | 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/ |
| Verschüttetes entsorgen | Collect 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 | ... 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 Prevention | Wear face shield. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | No 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 Prevention | Protective gloves. Protective clothing. |
| Exposure Prevention | STRICT HYGIENE! |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Unerwünschte Wirkungen | Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears. |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| 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. |
| F | 8-19 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3334 |
| Zollcode | 29161490 |
| RTECS-Nr. | OZ4400000 |
| R-Sätze (R) | 37-43 |
| Toxizität | LD50 orally in Rabbit: 3300 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24-37-36/37 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 97-90-5(Hazardous Substances Data) |
| Gefahrenklasse | Skin Sens. 1STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
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.