2-Ethyl-2-[[(1-oxoallyl)oxy]methyl]-1,3-propandiyldiacrylat
TMPTA · 1,1,1-TRIMETHYLOL PROPANE TRIACRYLATE · 2-((acryloyloxy)Methyl)-2-ethylpropane-1,3-diyl diacrylate · HEXAGLYCERINE TRIACRYLATE · sr351 · TTMPTA · ogumontt200 · Trimethylpropane triacrylate
![Molekülstruktur von 2-Ethyl-2-[[(1-oxoallyl)oxy]methyl]-1,3-propandiyldiacrylat](/img/chemical/27423.png)
Identifikatoren & physikalische Daten
| CAS No. | 15625-89-5 |
|---|---|
| Summenformel | C15H20O6 |
| Durchschnittliche Molmasse | 296,31 g/mol |
| Monoisotopische Masse | 296,12598836 g/mol |
| SMILES | C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C |
| InChIKey | DAKWPKUUDNSNPN-UHFFFAOYSA-N |
| PubChem CID | 27423 |
| ChEMBL | CHEMBL1886556 |
| ChEBI | CHEBI:35028 |
| EC No. | 239-701-3 |
| DTXSID | DTXSID0027773 |
| Lokaler Name | 2-Ethyl-2-[[(1-oxoallyl)oxy]methyl]-1,3-propandiyldiacrylat |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 78,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 13 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 364 |
| Polymers | Plastics & Rubber -> (Meth)acrylates |
| Kosmetika | Cosmetics ingredient -> Other (Specify) |
| LogP (Verteilungskoeffizient) | log Kow = 2.75 |
| Geruch | Acrylic or pungent odor |
| Dichte | 1.11 g/cu cm at 20 °C1.1 g/mL at 25 °C (lit.) |
| Color/Form | Viscous, colorless to tan liquid |
| Löslichkeit | Insoluble in waterMiscible with water. |
| Siedepunkt | BP: >200 °C at 1 mm Hg>200°C |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Brechungsindex | Index of refraction = 1.4735 at 20 °Cn20/D 1.474(lit.) |
| Physical Description | LiquidDry PowderCBI[IUCLID] Colorless liquid with a pungent odorHygroscopicTan or amber in color if impure[NTP] Clear or yellow liquid with a pungent odor[Alfa Aesar MSDS] |
| Collision Cross Section | 165.9 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID0027773] |
| Schmelzpunkt | -66°C |
| Dampfdichte | >1 (vs air) |
| Dampfdruck | <0.01 mm Hg ( 20 °C) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Refrigerator |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 0[at 20 ℃] |
| Wichte | 1.1 |
| Farbe | Colorless to Light yellow to Light orange |
| Henry-Konstante | 1.6×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Kosmetik-Inhaltsstoffe Funktionen | FILM FORMINGHAIR CONDITIONINGHAIR FIXING |
| InChI | 1S/C15H20O6/c1-5-12(16)19-9-15(8-4,10-20-13(17)6-2)11-21-14(18)7-3/h5-7H,1-3,8-11H2,4H3 |
| InChIKey | DAKWPKUUDNSNPN-UHFFFAOYSA-N |
| SMILES | CCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C |
| LogP (Verteilungskoeffizient) | 4.35 at 20℃ |
| CAS Datenbank | 15625-89-5(CAS DataBase Reference) |
| NIST chemische Informationen | TMPTA (Trimethylol propane triacrylate)(15625-89-5) |
| EPA chemische Informationen | Trimethylolpropane triacrylate (15625-89-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315: Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.1% (4 of 3852) of reports.H315 (99.9%): Causes skin irritation [Warning Skin corrosion/irritation] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl esterHazard Traits - Carcinogenicity2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] 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: 04-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15232Trimethylolpropane triacrylate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Propenoic acid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl ester: Human health tier II assessment |
| Gefahrenübersicht | Allergic contact dermatitis reported in workers exposed to UV-cured coatings and textile inks[Kanerva, p. 1745] Labeled in the EU as causing skin and eye irritation with the potential to cause skin sensitization[IUCLID] May spontaneously polymerize on exposure to heat or light (stabilized with monomethyl ester of hydroquinone)[NTP] Occupational asthma confirmed in a worker exposed for 20 years in a kiosk to a tint containing trimethylolpropane triacrylate from a thermal printer[Reference #1] |
| Hazard Classes and Categories | Skin Irrit. 2 (99.9%)Eye irritation - category 2Skin corrosion/irritation - Category 2 |
Anwendungen & Verwendung
Beschreibung
Trimethylolpropane triacrylate (TMPTA) is a multifunctional acrylie monomer. It reacts with propyleneimine to form polyfunctional aziridine. Sensitization was observed in a textile fabric printer. Patch tests were positive with the polyfunctional aziridine hardener, but were negative to TMPTA. TMPTA caused contact dermatitis in an optic-fiber manufacturing worker and was reported as a sensitizer in a floor top coat or in photopolymerizable inks.
Verwenden
Trimethylolpropane triacrylate has important properties like low volatility, resistance against weather, chemical, water and abrasion, and immediate curing property. The above mentioned properties prompted its use in the production of adhesives, plastics, sealant chemicals, paint additives, photosensitive chemicals, ink and toner. It finds application in alkyd coatings, dental polymers, compact discs, hardwood floors, concrete polymers, screen printing, elastomers, automobile headlamps, acrylics and plastic components for the medical industry.
Herstellung & Synthese
synthetische
Synthesis of trimethylolpropane triacrylate: 2.44 kg of trimethylolpropane, 3.93 kg of acrylic acid, 0.5 kg of an acid ion exchanger (Lewatit 3333 of BAYER AG), 9 g of hydroquinone and 1.5 liters of petroleum ether (boiling range 60° to 70° C) were heated under a water separator, whilst stirring, in a 10 liter three-necked flask equipped with a stirrer, water separator and gas inlet tube. At the same time, a constant stream of air saturated with allyl alcohol was passed through the flask at a rate of 2 liters/hour. In total, 16 ml of allyl alcohol were introduced into the esterification mixture in this way. After 80 hours, the reaction mixture had an acid number of 32 and the boiling point had risen to 72° C. The petroleum ether was distilled off, remnants being removed by applying a vacuum of 0.2 mm Hg at a product temperature of 40° C. The esterification catalyst was separated off by filtration and was kept for further use. The trimethylolpropane triacrylate obtained in practically quantitative yield was pale yellowish and clear. The viscosity corresponded to a time of outflow of 20 seconds measured in a DIN cup 4 at 20° C. The product showed no change even on storage for 4 months at 60° C. When used in a UV light-curing printing ink which contained a photoinitiator, the product polymerised at high speed.Literature source US04059721