Trimethylolpropane Trimethacrylate
Basic information
- CAS
3290-92-4- Standard SMILES
C=C(C)C(=O)OCC(CC)(COC(=O)C(=C)C)COC(=O)C(=C)C- InChIKey
OKKRPWIIYQTPQF-UHFFFAOYSA-N- Molecular formula
- C18H26O6
- Average molar mass
- 338.4 g/mol
- Monoisotopic mass
- 338.17293854
Overview
Trimethylolpropane trimethacrylate is a carbonyl compound.
Names & identifiers
- Preferred name
- Trimethylolpropane Trimethacrylate
- IUPAC
- 2,2-bis(2-methylprop-2-enoyloxymethyl)butyl 2-methylprop-2-enoate
- English name
- Trimethylolpropane trimethacrylate
- Molecular formula
- C18H26O6
- Molecular weight
- 338.4
Names & synonyms
TRIMETHYLOLPROPANE TRIMETHACRYLATE3290-92-4Acryester TMPTMPTMAChemlink 30Blemmer PTTLight Ester TMPPerkalink 400NK Ester TMPTSartomer 350NK Ester M TMPTSartomer SR 350
Show more names
TMPMPTrihydroxymethylpropyl trimethylacrylatesr350blemmerpttTIMETHYLOLPROPANE TRIMETHACRYLATETrimethylolpropane trimethylacrylate2-Ethyl-2-((Methacryloyloxy)Methyl)propane-1,3-diyl bis(2-Methylacrylate)atm11td1500
Chemlink 3080Saret 515Monocizer TD 15001,1,1-Trimethylolpropane trimethacrylateSR 350ATM 11TMPT (crosslinking agent)TD 1500 S
Database identifiers
- CAS
3290-92-4- PubChem CID
- 18689
- DTXSID
DTXSID3027530- ChEMBL
CHEMBL1901244- ChEBI
CHEBI:35029- UNII
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 78.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 13
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 470
Experimental & physicochemical properties
PolymersPlastics & Rubber -> (Meth)acrylates
CosmeticsCosmetic ingredients (Trimethylolpropane Trimethacrylate) -> CIR (Cosmetic Ingredient Review)
Physical Description
Liquid; Dry Powder
Amber liquid with a musty odor; [AIHA] Yellow viscous liquid; [Alfa Aesar MSDS]
Collision Cross Section183.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3027530]
Physicochemical properties
- Melting point
- -25 °C · -25°C
- Boiling point
- 200 °C · >200°C 1mm
- Density
- 1.06 g/mL · 1.06 g/mL at 25 °C (lit.)
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 0.01 mm · <0.01 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.472(lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 22.3% (195 of 874) of reports.
H411 (76.7%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 874 reports by companies from 16 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 2-methyl-, 2-ethyl-2-[[(2-methyl-1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl ester
2-Propenoic acid, 2-methyl-, 1,1'-[2-ethyl-2-[[(2-methyl-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, 2-methyl-, 1,1'-[2-ethyl-2-[[(2-methyl-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)
REACH registered substance: Propylidynetrimethyl trimethacrylate (EC: 221-950-4)
2-Propenoic acid, 2-methyl-, 2-ethyl-2-(2-methyl-1-oxo-2-propenyl)oxymethyl-1,3-propanediyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A common skin sensitizer in dentistry; [Kanerva, p. 1392] May polymerize violently at >32 deg C, at >12 months of storage, or when exposed to light, free radicals, or oxidizing agents; [AIHA] A mild skin irritant; Causes ataxia, tremor, and dyspnea in intraperitoneal lethal-dose studies of rats; [RTECS] An irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAquatic Chronic 2 (76.7%)
Toxicology
Chemistry & industry
Uses & manufacturing
Uses
CIR ingredient: Trimethylolpropane Trimethacrylate
Used in UV-cured inks, coatings, adhesives, and dental sealants; [AIHA] Used in the chemical, paint, and polymer industries; Also used in adhesives, binding agents, cosmetics, vulcanizing agents, and crosslinking agents; [IUCLID]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
U.S. Production2023: 2,500,000 - <4,000,000 lb
Consumer UsesMonomers
Industry UsesIntermediate
Household ProductsInformation on 2 consumer products that contain Propylidynetrimethyl trimethacrylate in the following categories is provided:
General Manufacturing Information
Printing and Related Support Activities
2-Propenoic acid, 2-methyl-, 1,1'-[2-ethyl-2-[[(2-methyl-1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester: ACTIVE
Applications
UsesTrimethylolpropane trimethacrylate (TMPTMA) is used as an intermediate product for polymer synthesis in the chemical industry. It is a reactive trifunctional methacrylate suitable for use in a wide ranging number of polymer cross linking functions. TMPTMA is particularly useful as a co-agent in PVC plastisols, plasticizer systems and elastomers. Other applications include as an additive in water based emulsions, adhesives and UV/EB cured coatings.
General DescriptionTrimethylolpropane trimethacrylate is a carbonyl compound.
Preparation methods
synthesis of Trimethylolpropane trimethacrylate: 40.25g (0.3mol) of trimethylolpropane and 90.41g (1.05mol) of methacrylic acid were added to the reactor equipped with a reflux condenser, a water separator, a thermometer, a stirrer, and an air sampling device respectively to inhibit the polymerization. Agent 0.39g (prepared by hydroquinone: phenothiazine=2: 1 mass ratio), CZ zirconium-based solid acid catalyst 1.21g, with water agent 100ml (prepared by the volume ratio of toluene: cyclohexane=45: 55) ), be gradually warming up to 85 ± 5 ℃ while stirring, the flow velocity that keeps feeding air in the reactor is 7ml/min, at 90-100 ℃ temperature, reacted for 5 hours (when the water agent was brought out without reaction to generate water is the reaction end point), and the filter residue obtained by filtration of the reaction solution is a CZ zirconium-based solid acid catalyst (recovered and reused). Activated carbon 2g was added to the reaction mother liquor, the temperature was raised to 45±5°C with stirring, maintained for 15 minutes, filtered while hot, and the filtrate after the activated carbon was removed was evaporated under reduced pressure to obtain the target product trimethylolpropane trimethacrylate. 110g, the purity is 98.2%, the acid value is ≤0.5mg/g (the acid value detection method is determined according to the method of GB 1668-8), and the esterification rate is 98.2%.
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