(Hydroxyethyl)methacrylate

changed 477182661 Hydroxyethyl methacrylate.svg 190px Skeletal formula of Hydroxyethyl methacrylate Hydroxyethyl methacrylate molecule ball.png 210px Ball-and-stick model of the hydroxyethyl methacrylate molecule 2-Hydroxyethyl 2-methylprop-2-enoate HEMA; hydroxyethylmethacrylate; glycol methacrylate; glycol monomethacrylate; hydroxyethyl methacrylate; ethylene glycol methacrylate; 2-(methacryloyloxy)ethanol correct chemspider 12791 correct FDA 6E1I4IV47V WOBHKFSMXKNTIM-UHFFFAOYAH correct chemspider 1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 correct chemspider WOBHKFSMXKNTIM-UHFFFAOYSA-N correct CAS 868-77-9 212-782-2 13360 1730239 O=C(OCCO)\C(=C)C CC(=C)C(=O)OCCO 1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 OZ4725000 correct EBI 34288 correct kegg C14530 1071583 936557 6 10 3 Colourless liquid 1.07g/cm3 −99 GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA) http://corporate.evonik.com/_layouts/Websites/Internet/DownloadCenterFileHandler.ashx?fileid=1091 July 2013 213 miscible Chloroform (poor) 0.502-hydroxyethyl methacrylate_msds ChemSrc: A Smart Chem-Search Engine https://www.chemsrc.com/en/cas/868-77-9_1092316.html 0.08hPa Eye irritation 97 07 Warning 315 317 319 261 264 272 280 302+352 305+351+338 321 332+313 333+313 337+313 362 363 501 Hydroxyethylmethacrylate (also known as glycol methacrylate or HEMA) is an organic compound with the chemical formula H2C\dC(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: reaction of methacrylic acid with ethylene oxide: H2C\dC(CH3)CO2H + CH2CH2O -> H2C\dC(CH3)CO2CH2CH2OH esterification of methacrylic acid with a large excess of ethylene glycol. H2C\dC(CH3)CO2H + HOCH2CH2OH -> H2C\dC(CH3)CO2CH2CH2OH + H2O Both approaches also yield small amounts of ethylene glycol dimethacrylate, a polymer crosslinking agent. 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 and 0.005 Pa⋅s at 30°C. During polymerization, it shrinks by approximately 6%. Applications Contact lenses In 1960, O. Wichterle and D. Lím described its use in synthesis of hydrophilic crosslinked networks, and these results had great importance for manufacture of soft contact lenses. Polyhydroxyethylmethacrylate is hydrophilic: it is capable of absorbing from 10 to 600% water relative to its dry weight. Because of this property, it was one of the first materials to be used in the manufacture of soft contact lenses.Blasco, Joe; Kehoe, Vincent J-R; The professional make-up artist : motion pictures, television, print, theatre; 0-9771580-0-4; LCC# PN2068.B53 2005 Use in 3D printing 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.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 en 544 7650 337–339 10.1038/nature22061 0028-0836 28425999 free 2017Natur.544..337K 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.Wirth D. 2020 Highly Expandable Foam for Lithographic 3D Printing ACS Applied Materials and Interfaces 12 16 19033–19043 10.1021/acsami.0c02683 32267677 215603770 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.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 https://onlinelibrary.wiley.com/doi/abs/10.1111/cod.14056 Contact Dermatitis en 86 6 480–492 10.1111/cod.14056 1600-0536Steunebrink 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 https://onlinelibrary.wiley.com/doi/abs/10.1111/cod.14441 Contact Dermatitis en 90 1 60–65 10.1111/cod.14441 1600-0536 free As a known skin irritant, European Union regulations mandate labeling of products that contain hydroxyethylmethacrylate, with limited compliance. Products are also restricted to professionals. Other In electron microscopy and light microscopy, hydroxyethylmethacrylate serves as an embedding medium. When treated with polyisocyanates, polyhydroxyethylmethacrylate makes a crosslinked polymer (an acrylic resin) that is a useful component in paints. 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. 3 2006 Paints and Coatings 10.1002/14356007.a18_359.pub2 3-527-30673-0 Hazards Hydroxyethylmethacrylate is mildly toxic to humans but is a potent allergen. References Cole Madison B. Sykes Stephen M. 1974 Glycol Methacrylate in Light Microscopy a Routine Method for Embedding and Sectioning Animal Tissues http://www.tandfonline.com/doi/full/10.3109/10520297409117016 Stain Technology en 49 6 387–400 10.3109/10520297409117016 0038-9153 4142140 subscription 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 10.1179/his.1996.19.4.297 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 10.1016/0032-3861(82)90020-9 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 10.1016/s0022-5320(60)80024-x 13743397 Wichterle O. Lím D. 1960 Hydrophilic gels for biological use Nature 185 4706 117–118 10.1038/185117a0 1960Natur.185..117W 4211987 Category:Methacrylate esters Category:Monomers Category:Hydroxyethyl compounds