Pentaerythritol tetraacrylate
Pentaerythritol tetraacrylate (PETA or sometimes PETRA) is an organic compound. It is a tetrafunctional acrylate ester used as a monomer in the manufacture of polymers.[1] As it is a polymerizable acrylate monomer it is nearly always supplied with a polymerisation inhibitor such as MEHQ (monomethyl ether hydroquinone)added.
![]() | |
Names | |
---|---|
IUPAC name
[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate | |
Identifiers | |
3D model (JSmol) |
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.023.313 ![]() |
EC Number |
|
PubChem CID |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C17H20O8 | |
Molar mass | 352.339 g·mol−1 |
Hazards | |
GHS pictograms | ![]() |
GHS Signal word | Warning |
H315, H317, H319 | |
P261, P264, P272, P280, P302+352, P305+351+338, P321, P332+313, P333+313, P337+313, P362, P363, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Uses
PETA is part of a family of acrylates used in epoxy resin chemistry and Ultraviolet cure of coatings. Similar monomers used are 1,6-Hexanediol diacrylate and TMPTA trimethylol propane triacrylate. It is a derivative of pentaerythritol[2] One of the key uses of the material is in polymeric synthesis where it can form micelles and block copolymers.[3][4] The molecule's acrylate group functionality enables the molecule to do the Michael reaction with amines. It is therefore sometimes use in epoxy chemistry enabling a large reduction in cure time.[5] As the molecule has 4 functional acrylate groups it confers high cross-link density. Ethoxylation maybe used to produce ethoxylated versions which it find use in electron beam curing.[6] The material also has pharmaceutical uses[7]
External Websites
References
- "Pentaerythritol tetraacrylate". webbook.nist.gov. Archived from the original on 2021-02-08. Retrieved 2020-03-17.
- Marrian, S. F. (1948-08-01). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews. 43 (1): 149–202. doi:10.1021/cr60134a004. ISSN 0009-2665. Archived from the original on 2021-02-08. Retrieved 2020-03-17.
- petrov, P (2008). "Wormlike morphology formation and stabilization of Pluronic P123 micelles by solubilization of pentaerythritol tetraacrylate". The Journal of Physical Chemistry. B 112(30): 8879–8883.
- Petrov, Petar; Bozukov, Metodi; Burkhardt, Markus; Muthukrishnan, Sharmila; Müller, Axel H. E.; Tsvetanov, Christo B. (2006-05-31). "Stabilization of polymeric micelles with a mixed poly(ethylene oxide)/poly(2-hydroxyethyl methacrylate) shell by formation of poly(pentaerythritol tetraacrylate) nanonetworks within the micelles". Journal of Materials Chemistry. 16 (22): 2192–2199. doi:10.1039/B517028A. ISSN 1364-5501. Archived from the original on 2020-03-17. Retrieved 2020-03-17.
- "Epoxy Polyacrylate Resins". www.hexion.com. Archived from the original on 2020-02-13. Retrieved 2020-03-17.
- Chowdhury, Rajesh (2007). "Electron-beam-induced crosslinking of natural rubber/acrylonitrile–butadiene rubber latex blends in the presence of ethoxylated pentaerythritol tetraacrylate used as a crosslinking promoter". Journal of Applied Polymer Science. 103 (2): 1206–1214. doi:10.1002/app.25383. ISSN 1097-4628. Archived from the original on 2020-03-17. Retrieved 2020-03-17.
- Wong, Rachel Shet Hui; Ashton, Mark; Dodou, Kalliopi (2016-10-01). "Analysis of residual crosslinking agent content in UV cross-linked poly(ethylene oxide) hydrogels for dermatological application by gas chromatography". Journal of Pharmaceutical Analysis. 6 (5): 307–312. doi:10.1016/j.jpha.2016.04.004. ISSN 2095-1779. Archived from the original on 2020-03-17. Retrieved 2020-03-17.