Hydroxyethyl acrylate explained

Hydroxyethyl acrylate is an organic chemical and an aliphatic compound. It has the formula C5H8O3 and the CAS Registry Number 818–61–1. It is REACH registered with an EU number of 212–454–9.[1] It has dual functionality containing a polymerizable acrylic group and a terminal hydroxy group. It is used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.

Synthesis

There are a number of patents and synthesis papers to produce the material mostly aimed at reducing or removing heavy metals as catalysts. The traditional manufacturing process calls for the reaction of ethylene oxide with acrylic acid in the presence of a metal catalyst.[2]

Properties

The material is a clear water-white liquid with a mild but pungent ester like odor.[3] It has a low freezing point.

Applications

The most common use for the material is to be copolymerized with other acrylate and methacrylate monomers to make emulsion and other polymers including hydrogels.[4] [5] [6] [7] [8] Modification of rubbers and similar compounds is also a use for the material.[9] The resultant polymers may be used to manufacture pressure-sensitive adhesives.[10]

Toxicity

The toxicity of the material has been studied and is fairly well understood.[11] [12] [13]

See also

Notes and References

  1. Web site: PubChem . 2-Hydroxyethyl acrylate . 2023-02-17 . pubchem.ncbi.nlm.nih.gov . en.
  2. Huo . Fanglin . Lu . Yangcheng . 2022-10-15 . Green and high-efficiency synthesis of 2-hydroxyethyl acrylate with ion exchange resins as Cr(III) support and collector . Chemical Engineering Journal . en . 446 . 137130 . 10.1016/j.cej.2022.137130 . 249140875 . 1385-8947.
  3. Web site: 2-HYDROXY ETHYL ACRYLATE (HEA) . 2023-02-19 . atamankimya.com.
  4. Monleón Pradas . M. . Gómez Ribelles . J. L. . Serrano Aroca . A. . Gallego Ferrer . G. . Suay Antón . J. . Pissis . P. . 2001-05-01 . Porous poly(2-hydroxyethyl acrylate) hydrogels . Polymer . en . 42 . 10 . 4667–4674 . 10.1016/S0032-3861(00)00742-4 . 0032-3861.
  5. Schier . Jan E. S. . Hutchinson . Robin A. . 2016 . The influence of hydrogen bonding on radical chain-growth parameters for butyl methacrylate/2-hydroxyethyl acrylate solution copolymerization . Polymer Chemistry . en . 7 . 27 . 4567–4574 . 10.1039/C6PY00834H . 1974/26579 . 1759-9954. free .
  6. Vargün . Elif . Usanmaz . Ali . 2005-09-01 . Polymerization of 2-hydroxyethyl acrylate in bulk and solution by chemical initiator and by ATRP method . Journal of Polymer Science Part A: Polymer Chemistry . en . 43 . 17 . 3957–3965 . 10.1002/pola.20867 . 2005JPoSA..43.3957V . 0887-624X.
  7. Steinhauer . Wiktor . Hoogenboom . Richard . Keul . Helmut . Moeller . Martin . 2013-02-26 . Block and Gradient Copolymers of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Polymerization Kinetics, Thermoresponsive Properties, and Micellization . Macromolecules . en . 46 . 4 . 1447–1460 . 10.1021/ma302606x . 2013MaMol..46.1447S . 0024-9297.
  8. Steinhauer . Wiktor . Hoogenboom . Richard . Keul . Helmut . Moeller . Martin . 2010-09-14 . Copolymerization of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Kinetics and Thermoresponsive Properties . Macromolecules . en . 43 . 17 . 7041–7047 . 10.1021/ma101122b . 2010MaMol..43.7041S . 0024-9297.
  9. Chueangchayaphan . Wannarat . Tanrattanakul . Varaporn . Chueangchayaphan . Narong . Muangsap . Suchanya . Borapak . Warisara . 2017-06-21 . Synthesis and thermal properties of natural rubber grafted with poly(2-hydroxyethyl acrylate) . Journal of Polymer Research . en . 24 . 7 . 107 . 10.1007/s10965-017-1269-5 . 103796137 . 1572-8935.
  10. Iseki . Masashi . Suzuki . Yasuhito . Tachi . Hideki . Matsumoto . Akikazu . 2018-11-30 . Design of a High-Performance Dismantlable Adhesion System Using Pressure-Sensitive Adhesive Copolymers of 2-Hydroxyethyl Acrylate Protected with tert -Butoxycarbonyl Group in the Presence of Cross-Linker and Lewis Acid . ACS Omega . en . 3 . 11 . 16357–16368 . 10.1021/acsomega.8b02371 . 2470-1343 . 6643581 . 31458271.
  11. Tokumura . Fumio . Matsui . Tetsuya . Suzuki . Yasuko . Sado . Masashi . Taniguchi . Masaharu . Kobayashi . Ichiro . Kamiyama . Masashi . Suda . Shin . Nakamura . Atsushi . Yamazaki . Yuhiro . Yamori . Akira . Igarashi . Ryosuke . Kawai . Jun . Oka . Keiji . 2010-01-01 . The potential dermal irritating effect of residual (meth)acrylic monomers in pressure sensitive adhesive tapes . Drug and Chemical Toxicology . 33 . 1 . 1–7 . 10.3109/01480540903311043 . 0148-0545 . 20001660. 9253289 .
  12. Web site: CompTox Chemicals Dashboard . 2023-02-17 . comptox.epa.gov.
  13. Comparison of Subchronic Neurotoxicity of 2-Hydroxyethyl Acrylate and Acrylamide in Rats . 2023-02-17 . Toxicological Sciences. 1992 . 10.1093/toxsci/18.3.343. Moser . Virginia C. . Anthony . Douglas C. . Sette . William F. . MacPhail . Robert C. . 18 . 3 . 343–352 . 1597260 .

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