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| Names | |
|---|---|
| Preferred IUPAC name
2-Hydroxyethyl 2-methylprop-2-enoate | |
| Other names
HEMA; hydroxyethylmethacrylate; glycol methacrylate; glycol monomethacrylate; hydroxyethyl methacrylate; ethylene glycol methacrylate; 2-(methacryloyloxy)ethanol
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| Identifiers | |
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3D model (JSmol)
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| 1071583 | |
| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.011.621 |
| EC Number |
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| 936557 | |
| KEGG |
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PubChem CID
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| RTECS number |
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| UNII |
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CompTox Dashboard (EPA)
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| Properties | |
| C6H10O3 | |
| Molar mass | 130.143 g·mol−1 |
| Appearance | Colourless liquid |
| Density | 1.07 g/cm3 |
| Melting point | −99 °C (−146 °F; 174 K)[2] |
| Boiling point | 213 °C (415 °F; 486 K)[2] |
| miscible | |
| log P | 0.50[1] |
| Vapor pressure | 0.08 hPa |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Eye irritation |
| GHS labelling: | |
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| Warning | |
| H315, H317, H319 | |
| P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P501 | |
| Flash point | 97 °C (207 °F; 370 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Hydroxyethylmethacrylate (also known as glycol methacrylate)[3][4] is the organic compound with the chemical formula H2C=C(CH3)CO2CH2CH2OH. It is a colorless viscous liquid that readily polymerizes, i.e. it is a monomer that is used to make various polymers.
Synthesis
Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are:[5]
- reaction of methacrylic acid with ethylene oxide:
- H2C=C(CH3)CO2H + CH2CH2O → H2C=C(CH3)CO2CH2CH2OH
- esterification of methacrylic acid with a large excess of ethylene glycol.
- H2C=C(CH3)CO2H + HOCH2CH2OH → H2C=C(CH3)CO2CH2CH2OH + H2O
Both these methods give also some amount of ethylene glycol dimethacrylate. During polymerization of hydroxyethylmethacrylate, it works as crosslinking agent.[5]
Properties
Hydroxyethylmethacrylate is completely miscible with water and ethanol, but its polymer is practically insoluble in common solvents. Its viscosity is 0.0701 Pa⋅s at 20°C[6] and 0.005 Pa⋅s at 30°C.[3] During polymerization, it shrinks by approximately 6%.[6]
Applications
Contact lenses
In 1960, O. Wichterle and D. Lím[7] described its use in synthesis of hydrophilic crosslinked networks, and these results had great importance for manufacture of soft contact lenses.[5] Polyhydroxyethylmethacrylate is hydrophilic: it is capable of absorbing from 10 to 600% water relative to the dry weight. Because of this property, it was one of the first materials to be used in the manufacture of soft contact lenses.[8]
Use in 3D printing
Hydroxyethylmethacrylate lends itself well to applications in 3D printing as it cures quickly at room temperature when exposed to UV light in the presence of photoinitiators. It may be used as a monomeric matrix in which 40nm silica particles are suspended for 3D glass printing.[9] When combined with a suitable blowing agent such as BOC anhydride it forms a foaming resin which expands when heated.[10]
Cosmetics
Hydroxyethylmethacrylate is the most common ingredient in cosmetic nail products, where it is used as a resin base and in polishes, primers, coats, and gels. Hydroxyethylmethacrylate is also a component of cosmetics glues for the application of eyelash and hair extensions.[11][12]
As a known skin irritant, European Union regulations mandate labeling of products that contain Hydroxyethylmethacrylate, with limited compliance.[12] Products are also restricted to professionals.
Other
In electron microscopy, later in light microscopy, hydroxyethylmethacrylate serves as an embedding medium.[4][3]
When treated with polyisocyanates, polyhydroxyethylmethacrylate makes a crosslinked polymer, an acrylic resin, that is a useful component in some paints.[13]
Hazards
Hydroxyethylmethacrylate is a mild skin irritant and can cause allergic skin reactions.[3][12]
References
- ^ "2-hydroxyethyl methacrylate_msds". ChemSrc: A Smart Chem-Search Engine.
- ^ a b "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.
- ^ a b c d Gerrits, P. O.; Horobin, R. W. (1996). "Glycol Methacrylate Embedding for Light Microscopy: Basic Principles and Trouble-Shooting". Journal of Histotechnology. 19 (4): 297–311. doi:10.1179/his.1996.19.4.297.
- ^ a b Cole, Madison B.; Sykes, Stephen M. (1974). "Glycol Methacrylate in Light Microscopy a Routine Method for Embedding and Sectioning Animal Tissues". Stain Technology. 49 (6): 387–400. doi:10.3109/10520297409117016. ISSN 0038-9153. PMID 4142140.
- ^ a b c Macret, M.; Hild, G. (1982). "Hydroxyalkyl methacrylates: Kinetic investigations of radical polymerizations of pure 2-hydroxyethyl methacrylate and 2, 3-dihydroxypropyl methacrylate and the radical copolymerization of their mixtures". Polymer. 23 (1): 81–90. doi:10.1016/0032-3861(82)90020-9.
- ^ a b Rosenberg, M.; Bartl, P.; Lesko, J. (1960). "Water-soluble methacrylate as an embedding medium for the preparation of ultrathin sections". Journal of Ultrastructure Research. 4 (3–4): 298–303. doi:10.1016/s0022-5320(60)80024-x. PMID 13743397.
- ^ Wichterle, O.; Lím, D. (1960). "Hydrophilic gels for biological use". Nature. 185 (4706): 117–118. Bibcode:1960Natur.185..117W. doi:10.1038/185117a0. S2CID 4211987.
- ^ Blasco, Joe; Kehoe, Vincent J-R; The professional make-up artist : motion pictures, television, print, theatre; ISBN 0-9771580-0-4; LCC# PN2068.B53 2005
- ^ Kotz, Frederik; Arnold, Karl; Bauer, Werner; Schild, Dieter; Keller, Nico; Sachsenheimer, Kai; Nargang, Tobias M.; Richter, Christiane; Helmer, Dorothea; Rapp, Bastian E. (2017). "Three-dimensional printing of transparent fused silica glass". Nature. 544 (7650): 337–339. Bibcode:2017Natur.544..337K. doi:10.1038/nature22061. ISSN 0028-0836. PMID 28425999.
- ^ Wirth, D. (2020). "Highly Expandable Foam for Lithographic 3D Printing". ACS Applied Materials and Interfaces. 12 (16): 19033–19043. doi:10.1021/acsami.0c02683. PMID 32267677. S2CID 215603770.
- ^ Symanzik, Cara; Weinert, Patricia; Babić, Željka; Hallmann, Sarah; Havmose, Martin S.; Johansen, Jeanne D.; Kezic, Sanja; Macan, Marija; Macan, Jelena; Strahwald, Julia; Turk, Rajka; van der Molen, Henk F.; John, Swen M.; Uter, Wolfgang (2022). "Allergic contact dermatitis caused by 2-hydroxyethyl methacrylate and ethyl cyanoacrylate contained in cosmetic glues among hairdressers and beauticians who perform nail treatments and eyelash extension as well as hair extension applications: A systematic review". Contact Dermatitis. 86 (6): 480–492. doi:10.1111/cod.14056. ISSN 1600-0536.
- ^ a b c Steunebrink, Iemke M.; de Groot, Anton; Rustemeyer, Thomas (2024). "Presence of 2-hydroxyethyl methacrylate (HEMA) and other (meth)acrylates in nail cosmetics, and compliance with EU legislation: An online market survey". Contact Dermatitis. 90 (1): 60–65. doi:10.1111/cod.14441. ISSN 1600-0536.
- ^ Stoye, D.; Funke, W.; Hoppe, L.; et al. (2006). "Paints and Coatings". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a18_359.pub2. ISBN 3-527-30673-0.
