Trimethylolpropane triacrylate

Last updated
Trimethylolpropane triacrylate
Trimethylolpropane triacrylate.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
    Key: DAKWPKUUDNSNPN-UHFFFAOYSA-N
  • InChI=1/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
    Key: DAKWPKUUDNSNPN-UHFFFAOYAU
  • CCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C
Properties [1]
C15H20O6
Molar mass 296.319 g·mol−1
AppearanceLiquid
Density 1.109 (20°C)
Melting point -20°C
Boiling point 390°C
500 mg/L (20°C)
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg [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).

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.

Contents

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 overtime; 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]

See also

References

  1. ↑ "Scientific properties". www.echa.eu. Retrieved 2025-03-21.
  2. 1 2 "Summary of Classification and Labelling,". www.echa.eu. Retrieved 2025-03-21.
  3. ↑ Wang, Qianhe (January 2019). "PhD Dissertation Acrylated Alkyds". University of Akron.
  4. ↑ Rengaraju, Sripriya; Al-Tabbaa, Abir (2023). "Life Cycle Assessment (LCA) of Microcapsule based self-healing in concrete". MATEC Web of Conferences. 378: 06004. doi: 10.1051/matecconf/202337806004 . ISSN   2261-236X.
  5. ↑ Lin, Xiuju; Liao, Bing; Zhang, Jingfei; Li, Simin; Huang, Jianheng; Pang, Hao (2019-06-20). "Synthesis and characterization of high-performance cross-linked polycarboxylate superplasticizers" . Construction and Building Materials. 210: 162–171. doi:10.1016/j.conbuildmat.2019.03.185. ISSN   0950-0618. S2CID   139394654.
  6. ↑ Ma, Yihan; Lei, Lei; Sha, Shengnan; Liu, Yi; Shi, Caijun (2023-06-01). "Synthesis of a cross-linked polycarboxylate ether superplasticizer and its effects on the properties of cement paste containing montmorillonite" . Cement and Concrete Research. 168: 107136. doi:10.1016/j.cemconres.2023.107136. ISSN   0008-8846. S2CID   257440284.
  7. ↑ "Epoxy Polyacrylate Resins". www.hexion.com. Retrieved 2020-02-12.
  8. ↑ "Low Viscosity, Fast Curing Epoxy Acrylate Oligomers". www.pcimag.com. Retrieved 2020-02-12.
  9. ↑ "TMPTA, use in rubbers". www.longchangchemical.com. Retrieved 2025-03-31.
  10. ↑ "TMPTA ALTERNATIVES FOR INDUSTRIAL COATINGS" (PDF). sartomer.arkema.com. Retrieved 2025-03-31.
  11. ↑ "Substance infocard". www.echa.eu. Retrieved 2025-03-31.
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