// Workers AI · dad joke modeWhat did (Hydroxyethyl)methacrylate say? I'm bonded to you.
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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 | |
| Identifiers | |
3D model (JSmol) |
|
| 1071583 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.011.621 |
| EC Number |
|
| 936557 | |
| KEGG | |
PubChem CID |
|
| RTECS number |
|
| UNII | |
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)[1] |
| Boiling point | 213 °C (415 °F; 486 K)[1] |
| miscible | |
| log P | 0.50[2] |
| Vapor pressure | 0.08 hPa |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Eye irritation |
| GHS labelling: | |
 | |
| 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).
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Hydroxyethylmethacrylate (also known as glycol methacrylate or HEMA)[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
[edit]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 approaches also yield small amounts of ethylene glycol dimethacrylate, a polymer crosslinking agent.[5]
Properties
[edit]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
[edit]Contact lenses
[edit]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
[edit]Hydroxyethylmethacrylate lends itself well to applications in sterolithography 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 an organic carbonate (e.g BOC anhydride) it forms a foaming resin which expands when heated.[10]
Cosmetics
[edit]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
[edit]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 paints.[13]
Hazards
[edit]Hydroxyethylmethacrylate is mildly toxic to humans but is a potent allergen.[3][12]
References
[edit]- 1 2 "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.
- ↑ "2-hydroxyethyl methacrylate_msds". ChemSrc: A Smart Chem-Search Engine.
- 1 2 3 4 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.
- 1 2 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.
- 1 2 3 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.
- 1 2 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.
- 1 2 3 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.