Trimethylolpropane triacrylate
Chemical compound
From Wikipedia, the free encyclopedia
Trimethylolpropane triacrylate (TMPTA) is a trifunctional acrylate ester monomer derived from trimethylolpropane, used in the manufacture of plastics, adhesives, acrylic glue, anaerobic sealants, and ink. It is useful for its low volatility and fast cure response. It has the properties of weather, chemical and water resistance, as well as good abrasion resistance. End products include alkyd coatings,[3] compact discs, hardwood floors, concrete and cementitious applications,[4][5][6] Dental composites, photolithography, letterpress, screen printing, elastomers, automobile headlamps, acrylics and plastic components for the medical industry.
| |
| Names | |
|---|---|
| Preferred IUPAC name
2-Ethyl-2-{[(prop-2-enoyl)oxy]methyl}propane-1,3-diyl di(prop-2-enoate) | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.036.077 |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties[1] | |
| C15H20O6 | |
| Molar mass | 296.319 g·mol−1 |
| Appearance | Liquid |
| Density | 1.109 (20°C) |
| Melting point | -20°C |
| Boiling point | 390°C |
| 500 mg/L (20°C) | |
| Hazards | |
| GHS labelling: | |
   [2] | |
| H315, H317, H319, H351, H410[2] | |
| Flash point | 194.5°C |
| 385°C | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Other uses
As the molecule has acrylic functionality, it is capable of doing the Michael reaction with an amine. This allows its use in epoxy chemistry where its use speeds up the cure time considerably[7][8]
TMPTA can be used as a vulcanization booster for specialty rubbers such as ethylene propylene rubber, EPDM rubber, silicone rubber, polyurethane, ethylene/vinyl acetate (EVA) copolymer and chlorinated polyethylene elastomer (CPE). Typically, the vulcanization process is catalyzed with organic peroxides (such as DCP or BPO) however some rubbers are difficult to fully vulcanize using only peroxide catalysts. This usually results in longer curing times and lower yields, compromising mechanical and physical properties. Adding TMPTA has greatly improved the kinetics of vulcanization: for example, when using DCP for curing, if 1 to 4% TMPTA additive is used as a curing agent, not only the curing time is greatly reduced, but the overall chemical and mechanical properties are improved.[9]
Safety
TMPTA's classification got worse over time; in November 2023 all mixtures containing ≥ 1% by weight of TMPTA had been classified as carcinogen category 2 (H351).[10] To overcome this problem, ethoxylated versions (EOTMPTA) were launched on the market, registred on ECHA with a range going from 1 to 6.5 moles of ethoxylation.[11]