Hydroxyethylmethacrylate (also known as glycol methacrylate)[3][4] is the organic compound with the chemical formula H2C\dC(CH3)CO2CH2CH2OH. It is a colorless viscous liquid that readily polymerizes. Hydroxyethylmethacrylate is a monomer that is used to make various polymers.
Synthesis
Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are:[5]
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]
When treated with polyisocyanates, polyhydroxyethylmethacrylate makes a crosslinked polymer, an acrylic resin, that is a useful component in some paints.[11]
Hazards
Hydroxyethylmethacrylate is a mild skin irritant and can cause allergic skin reactions.[3]
^ abcdGerrits, 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.
^ abcMacret, 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.
^ abRosenberg, 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. PMID13743397.
^Blasco, Joe; Kehoe, Vincent J-R; The professional make-up artist : motion pictures, television, print, theatre; ISBN0-9771580-0-4; LCC# PN2068.B53 2005