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2,2'-Ethylendioxydiethyldimethacrylat
TEGDMA · Ethy · TEDMA · TRGDMA · Triethylene dimethacrylate · Triethylene glycol diMethacryla · 2,2'-ethylenedioxydiethyl dimethacrylate · (ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl) bis(2-Methylacrylate)
Identifikatoren & physikalische Daten
| CAS No. | 109-16-0 |
|---|---|
| Summenformel | C14H22O6 |
| Durchschnittliche Molmasse | 286,32 g/mol |
| Monoisotopische Masse | 286,14163842 g/mol |
| SMILES | C=C(C)C(=O)OCCOCCOCCOC(=O)C(=C)C |
| InChIKey | HWSSEYVMGDIFMH-UHFFFAOYSA-N |
| PubChem CID | 7979 |
| ChEMBL | CHEMBL3187544 |
| EC No. | 203-652-6 |
| DTXSID | DTXSID3029607 |
| Lokaler Name | 2,2'-Ethylendioxydiethyldimethacrylat |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 71,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 13 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 314 |
| LogP (Verteilungskoeffizient) | log Kow = 1.88 |
| Dichte | 1.072 at 25 °C1.09 @ 20°C1.092 g/mL at 25 °C(lit.) |
| Löslichkeit | > 10% in acetone> 10% in ethanol> 10% in ether> 10% in petroleum etherChloroform, Methanol3.6g/L at 20℃ |
| Siedepunkt | 155 °C @ 0.13 kPa170-172 °C5 mm Hg(lit.) |
| Polymerization | METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/ |
| Dampfdruck | 0.00094 [mmHg]0.077Pa at 20℃ |
| Brechungsindex | Index of refraction: 1.4595 at 25 °Cn20/D 1.461(lit.) |
| Physical Description | Liquid[Aldrich MSDS] |
| Schmelzpunkt | -52°C |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Oil |
| Farbe | Colourless to Pale Yellow |
| Wichte | 1.092 |
| BRN | 1797351 |
| Henry-Konstante | 5.8×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Light Sensitive |
| Kosmetik-Inhaltsstoffe Funktionen | NAIL CONDITIONING |
| InChI | 1S/C14H22O6/c1-11(2)13(15)19-9-7-17-5-6-18-8-10-20-14(16)12(3)4/h1,3,5-10H2,2,4H3 |
| InChIKey | HWSSEYVMGDIFMH-UHFFFAOYSA-N |
| SMILES | CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C |
| LogP (Verteilungskoeffizient) | 2.3 at 20℃ |
| CAS Datenbank | 109-16-0(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propenoic acid, 2-methyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester(109-16-0) |
| EPA chemische Informationen | Triethylene glycol dimethacrylate (109-16-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 49% (262 of 535) of reports. |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 2-methyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester2-Propenoic acid, 2-methyl-, 1,1'-[1,2-ethanediylbis(oxy-2,1-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-ethanediylbis(oxy-2,1-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: 24-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/138212-Propenoic acid, 2-methyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | PEC / SN / Other assessments - Common skin sensitisersâhazard classification: Health |
| Gefahrenübersicht | Allergic contact dermatitis reported in dental technicians[Kanerva, p. 1744] May polymerize on exposure to lightAn irritantMay cause skin sensitization[Aldrich MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (21.1%)Skin Sens. 1 (43.7%)Eye Irrit. 2 (21.1%)STOT SE 3 (16.1%)Skin sensitization - Category 1BHazardous to the aquatic environment (Acute) - Category 3Skin Sens. 1B |
| Skin, Eye, and Respiratory Irritations | Methacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/ |
| 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/ |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 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. |
| Protective Action Criteria (PAC) | 33 [mg/m3]360 [mg/m3]2100 [mg/m3] |
| Personal Protective Equipment (PPE) | SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE BY THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 250(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that triethylene glycol dimethacrylate will have moderate mobility in soil(SRC). Volatilization of triethylene glycol dimethacrylate should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.7X10-12 atm-cu m/mole(SRC), using a recommended regression equation(4). Volatilization from dry soil surfaces(SRC) is not expected based on an estimated vapor pressure of 9.4X10-4 mm Hg(SRC), determined from a fragment constant method(5). Insufficient data are available to determine the rate or importance of biodegradation of triethylene glycol methacrylate in soil(SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 250(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(1), indicates that triethylene glycol dimethacrylate may adsorb to suspended solids and sediment in the water(SRC). Triethylene glycol dimethacrylate will be non-volatile from water surfaces(1,SRC) based on an estimated Henry's Law constant of 1.7X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF value of 16(1,SRC), from an experimental log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Base catalyzed half-lives for triethylene glcycol dimethacrylate have been estimated(SRC), through a structure estimation method(5), to be 1.6 years and 16 years at pHs of 8 and 7, respectively(5,SRC). Insufficient data are available to determine the rate or importance of biodegradation of triethylene glycol methacrylate in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylene glycol dimethacrylate, which has an estimated vapor pressure of 9.4X10-4 mm Hg at 25 °C(2,SRC), would exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triethylene glycol dimethacrylate is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be about 5.7 hours(3,SRC). Vapor-phase triethylene glycol dimethacrylate is also degraded in the atmosphere by reaction with atmospheric ozone(SRC)the half-life for this reaction in air is estimated to be about 12 hours(3,SRC). Particulate-phase triethylene glycol dimethacrylate may be physically removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Toxizitätsübersicht | Based on available data, the CIR Expert Panel concluded that...Triethylene Glycol Dimethacrylate is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.Safe for use in cosmetics, with qualifications |
| Soil Adsorption/Mobility | The Koc of triethylene glycol dimethacrylate is estimated as approximately 250(SRC), using an experimental log Kow of 1.88(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that triethylene glycol dimethacrylate has medium mobility in soil(SRC). |
| 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/Seven patients were occupationally sensitized to dental composite resin products (DCR): 6 dental nurses and 1 dentist. All had a positive patch test to their DCR. Two independent types of allergy were seen: (a) aromatic epoxy acrylate and/or (b) aliphatic acrylates. Four out of 5 patients reacted to BIS-GMA, the most widely used aromatic epoxy acrylate in DCR, but not the dentist. She and 2 dental nurses were allergic to aliphatic acrylates, including triethylene glycol dimethacrylate (TREGDMA) and triethylene diglycol diacrylate (TREGDA). Four patients were allergic to epoxy resin (ER) (containing mainly MW 340), possibly an impurity in some DCR. Two patients were also allergic to methyl methacrylate (MMA): the dentist had been exposed to MMA but the nurses exposure was uncertain. One patient was also allergic to rubber gloves, 2 to rubber chemicals but not their gloves, and 5 to disinfectants used. Diagnosis was delayed as long as 13 yr in spite of previous patch testing. Dermatologists need to use the patients own DCR and the methacrylate series for patch testing. Dental personnel need to know about the risks of DCR, and use no touch techniques and protective gloves.Epoxy and acrylic resins have numerous industrial applications but are also widely used in the household environment. These compounds are presently one of the most important sources of occupational contact dermatitis. Contact sensitization to epoxy resins is usually caused by the resin itself but hardeners or other additives, such as reactive diluents, plasticizers, fillers and pigments, can occasionally be responsible. Since completely cured epoxy resins are not sensitizers, epoxy resin sensitization is always due to the presence, in the final polymer, of uncured allergenic low molecular weight oligomers. Acrylates are now considered the fourth most common cause of contact sensitization due to resins. Unpolymerized monomers of acrylic compounds are known to be responsible for the contact allergy. Accelerators, inhibitors and catalysts, which are usually added to the acrylates to promote the polymerization process, can also sensitize. Both allergic and irritant contact dermatitis may be caused by exposure to epoxy or acrylic resins and their additives. Contact urticaria, allergic or irritant airborne contact dermatitis caused by volatile compounds, onychia and paronychia can also occur. From January of 1984 to May of 1992 we detected 39 cases of occupational allergic contact dermatitis to epoxy resin system substances and 11 cases of occupational contact sensitization to acrylic compounds. In our experience, the electronics industry as well as paint and glue related activities were the most important sources of epoxy sensitization. Dental materials and anaerobic sealants were found to be the most frequent acrylate sensitizers. /Epoxy & acrylic resins/ |
| Artificial Pollution Sources | Triethylene glycol dimethacrylate's production and use as an cross-linking agent for hard contact lenses(1) and dental materials(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF value of 16 was calculated for triethylene glycol dimethacrylate(SRC), using an experimental log Kow of 1.88(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for triethylene glycol dimethacrylate is estimated as 1.7X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that triethylene glycol dimethacrylate will be essentially nonvolatile from water surfaces(2,SRC). Triethylene glycol dimethacrylate's values for vapor pressure, 9.4X10-4 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC). |
| Non-Human Toxicity Excerpts | TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING TRIETHYLENE GLYCOL DIMETHACRYLATE, 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.The objective of this study were to determine the cytotoxic concentrations of 11 components of resin composites on monolayers of cultured Balb/c 3T3 fibroblasts, to study the inhibitory effects of these components on DNA synthesis, total protein content, and protein synthesis, and to determine whether effects were reversible when the components were withdrawn from the medium. These data were reported as concentrations which inhibited 10% (ID10) and 50% (ID50) of a particular metabolic process as well as the range of concentrations over which cell metabolism was irreversibly inhibited. For any individual component, the ID50 values for all three metabolic parameters were of the same magnitude. The same was true for the ranges of irreversibility. Ethoxylated Bis-phenol A dimethacrylate (E-BPA) was the most toxic molecule of the group (ID50 being between 1 and 10 mumol/l). The ID50 concentrations for three of the components, including Bis-GMA, UDMA, TEGDMA, and Bis-phenol A, ranged between 10 and 100 mumol/l, while the ID50 values of three components (N,N dihydroxyethyl-p-toluidine, camphoroquinone, and N,N-dimethylaminoethyl methacrylate) were above 100 mumol/l. The concentrations to which the cells and tissues are exposed in vivo are not known. This study should help to identify the concentrations of organic composite components which pose clinical cytotoxic hazards. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of triethylene glycol dimethacrylate with photochemically produced hydroxyl radicals has been estimated as 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 5.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the vapor-phase reaction of triethylene glycol dimethacrylate with atmospheric ozone has been estimated as 2.3X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). The base-catalyzed hydrolysis rate constant for triethylene glycol dimethacrylate can be estimated(SRC), through a structure estimation method(2), to be 1.4X10-2 L/mol-sec at pH greater than 8this corresponds to half-lives of 1.6 and 16 years at pHs of 8 and 7, respectively(2,SRC). |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 12,201 workers (2,704 of these are female) are potentially exposed to triethylene glycol dimethacrylate in the USA(1). Occupational exposure may be through inhalation and dermal contact with this compound(SRC). |
| Environmental Water Concentrations | SURFACE WATER: Triethylene glycol dimethacrylate was found in the Delaware River at 35, 0.5, 0.1, and 5 ppb in Northeast Sewage Treatment plant effluent, river mile 106, river mile 108, and in Torresdale Water Treatment Plant influent, respectively(1). |
| F | 8-19 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3334 |
| Zollcode | 29161900 |
| RTECS-Nr. | OZ4100000 |
| R-Sätze (R) | 36/37/38-43 |
| Toxizität | LD50 oral in rat: 10837mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-28-36/37 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 109-16-0(Hazardous Substances Data) |
| Gefahrenklasse | Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
Triethylene glycol dimethacrylate was employed to optimize the dilution of high-viscosity monomers and to link together the macromolecules constituting the polymer, to make their three-dimentional structure more rigid. It is also a crosslinking agent of acrylic resins, used in sealents or in dental bonding resins. These are mainly used in dentistry, by dental technicians and dentists.
Verwenden
Esters of acrylic acid and methacrylic acid, more commonly known as acrylates and methacrylates are key raw materials in the coatings and printing industry, and in food packaging.