(Hydroxyethyl)methacrylate
Names | |
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IUPAC name
2-Hydroxyethyl 2-methylprop-2-enoate
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Other names
HEMA; hydroxyethylmethacrylate; glycol methacrylate; glycol monomethacrylate; hydroxyethyl methacrylate; ethylene glycol methacrylate; 2-(methacryloyloxy)ethanol
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Identifiers | |
3D model (JSmol)
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1071583 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.011.621 |
EC Number |
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936557 | |
KEGG | |
PubChem CID
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RTECS number |
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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)[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: | |
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 or HEMA is the organic compound with the formula HOCH2CH2O2CC(Me)=CH2. It is a colorless viscous liquid that readily polymerizes. HEMA is a monomer that is used to make various polymers.
Applications
Polyhydroxyethylmethacrylate is hydrophobic; however, when the polymer is subjected to water it will swell due to the molecule's hydrophilic pendant group. Depending on the physical and chemical structure of the polymer, 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 successfully used in the manufacture of soft contact lenses[3]
When treated with polyisocyanates, poly(HEMA) makes a crosslinked polymer, an acrylic resin. that is a useful component in some paints.[4]
Use in 3D printed glass
HEMA is also used as the monomeric matrix in which 40 nm silica particles are suspended for 3D glass printing.[5]
References
- ^ "2-hydroxyethyl methacrylate_msds".
- ^ a b "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.
- ^ 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
- ^ Stoye, D.; Funke, W.; Hoppe, L.; Hasselkus, J. R.; Curtis, L. G.; Hoehne, K.; Zech, H. J.; Heiling, P.; Yamabe, M.; Dören, K.; Schupp, H.; Küchenmeister, R.; Schmitthenner, M.; Kremer, W.; Wieczorrek, W.; Gempeler, H.; Schneider, W.; White, J. W.; Short, A. G.; Blank, W. J.; Calbo, L. J.; Plath, D.; Wagner, F.; Haller, W.; Rödder, K. M.; Streitberger, H. J.; Urbano, E.; Laible, R.; Meyer, B. D.; Bagda, E. (2006). "Paints and Coatings". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a18_359.pub2. ISBN 3527306730.
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suggested) (help) - ^ Kotz (20 April 2017). "Three-dimensional printing of transparent fused silica glass". Nature. 544 (7650): 337–339. doi:10.1038/nature22061. PMID 28425999.