Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and (Hydroxyethyl)methacrylate: Difference between pages

| Watchedfields = changed

| verifiedrevid = 477182661

| ImageAlt = Skeletal formula of Hydroxyethyl methacrylate

| ImageFile1 = Hydroxyethyl methacrylate molecule ball.png

| ImageAlt1 = Ball-and-stick model of the hydroxyethyl methacrylate molecule

| PIN = 2-Hydroxyethyl 2-methylprop-2-enoate

| OtherNames = HEMA; hydroxyethylmethacrylate; glycol methacrylate; glycol monomethacrylate; hydroxyethyl methacrylate; ethylene glycol methacrylate; 2-(methacryloyloxy)ethanol

| EINECS = 212-782-2

| PubChem = 13360

| ChEMBL = 1730239

| RTECS = OZ4725000

| Beilstein = 1071583

| Gmelin = 936557

}}

| C=6 | H=10 | O=3

| Appearance = Colourless liquid

| Density = 1.07{{nbsp}}g/cm{{sup|3}}

| MeltingPtC = −99

| MeltingPt_ref = <ref name="gps">{{cite web|title=GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)|url=http://corporate.evonik.com/_layouts/Websites/Internet/DownloadCenterFileHandler.ashx?fileid=1091|date=July 2013}}</ref>

| BoilingPtC = 213

| BoilingPt_ref =<ref name=gps/>

| Solubility = miscible

| LogP = 0.50<ref name="chemsrc">{{cite web|title=2-hydroxyethyl methacrylate_msds |publisher=ChemSrc: A Smart Chem-Search Engine |url=https://www.chemsrc.com/en/cas/868-77-9_1092316.html }}</ref>

| VaporPressure = 0.08{{nbsp}}hPa

}}

| Section3 =

}}

| MainHazards = Eye irritation

| FlashPtC = 97

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|317|319}}

| PPhrases = {{P-phrases|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''')<ref name=Gerrits_1996/><ref name=Cole_1974/> is the [[organic compound]] with the chemical formula {{chem|H2C\dC(CH3)CO2CH2CH2OH}}. It is a colorless viscous liquid that readily polymerizes. Hydroxyethylmethacrylate is a [[monomer]] that is used to make various [[polymer]]s.

==Synthesis==

Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are:<ref name=Macret_1982/>

* reaction of [[methacrylic acid]] with [[ethylene oxide]];

* [[esterification]] of methacrylic acid with a large excess of [[ethylene glycol]].

Both these methods give also some amount of [[ethylene glycol dimethacrylate]]. During polymerization of hydroxyethylmethacrylate, it works as [[crosslinking agent]].<ref name=Macret_1982/>

==Properties==

Hydroxyethylmethacrylate is completely miscible with water and ethanol, but [[Polyhydroxyethylmethacrylate|its polymer]] is practically insoluble in common solvents. Its [[viscosity]] is 0.0701 [[pascal-second|Pa⋅s]] at 20°C<ref name=Rosenberg_1960/> and 0.005 Pa⋅s at 30°C.<ref name=Gerrits_1996/> During polymerization, it shrinks by approximately 6%.<ref name=Rosenberg_1960/>

==Applications==

===Contact lenses===

In 1960, [[Otto Wichterle|O. Wichterle]] and D. Lím<ref name=Wichterle_1960/> described its use in synthesis of hydrophilic crosslinked networks, and these results had great importance for manufacture of soft [[contact lenses]].<ref name=Macret_1982/> [[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.<ref>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</ref>

===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.<ref>{{cite journal |last1=Kotz |first1=Frederik |last2=Arnold |first2=Karl |last3=Bauer |first3=Werner |last4=Schild |first4=Dieter |last5=Keller |first5=Nico |last6=Sachsenheimer |first6=Kai |last7=Nargang |first7=Tobias M. |last8=Richter |first8=Christiane |last9=Helmer |first9=Dorothea |last10=Rapp |first10=Bastian E. |year=2017 |title=Three-dimensional printing of transparent fused silica glass |journal=Nature |language=en |volume=544 |issue=7650 |pages=337–339 |doi=10.1038/nature22061 |issn=0028-0836 |pmid=28425999 |doi-access=free|bibcode=2017Natur.544..337K }}</ref> When combined with a suitable [[blowing agent]] such as [[Di-tert-butyl_dicarbonate|BOC anhydride]] it forms a foaming resin which expands when heated.<ref>{{cite journal|last1=Wirth |first1=D. |year= 2020|title=Highly Expandable Foam for Lithographic 3D Printing |journal=ACS Applied Materials and Interfaces |volume=12 |issue=16 |pages=19033–19043 |doi=10.1021/acsami.0c02683 |pmid=32267677 |s2cid=215603770 }}</ref>

===Other===

In [[electron microscopy]], later in [[light microscope|light microscopy]], hydroxyethylmethacrylate serves as an embedding medium.<ref name=Cole_1974/><ref name=Gerrits_1996/>

When treated with [[polyisocyanate]]s, polyhydroxyethylmethacrylate makes a crosslinked polymer, an [[acrylic resin]], that is a useful component in some paints.<ref>{{Ullmann | last1 = Stoye | first1 = D. | last2 = Funke | first2 = W. | last3 = Hoppe | first3 = L. | last4 = Hasselkus | first4 = J. R. | last5 = Curtis | first5 = L. G. | last6 = Hoehne | first6 = K. | last7 = Zech | first7 = H. J. | last8 = Heiling | first8 = P. | last9 = Yamabe | first9 = M. | last10 = Dören | first10 = K. | last11 = Schupp | first11 = H. | last12 = Küchenmeister | first12 = R. | last13 = Schmitthenner | first13 = M. | last14 = Kremer | first14 = W. | last15 = Wieczorrek | first15 = W. | last16 = Gempeler | first16 = H. | last17 = Schneider | first17 = W. | last18 = White | first18 = J. W. | last19 = Short | first19 = A. G. | last20 = Blank | first20 = W. J. | last21 = Calbo | first21 = L. J. | last22 = Plath | first22 = D. | last23 = Wagner | first23 = F. | last24 = Haller | first24 = W. | last25 = Rödder | first25 = K. M. | last26 = Streitberger | first26 = H. J. | last27 = Urbano | first27 = E. | last28 = Laible | first28 = R. | last29 = Meyer | first29 = B. D. | last30 = Bagda | first30 = E. | display-authors = 3 | year = 2006 | title= Paints and Coatings | doi = 10.1002/14356007.a18_359.pub2 | isbn = 3-527-30673-0 }}</ref>

==Hazards==

Hydroxyethylmethacrylate is a mild [[skin irritant]] and can cause allergic skin reactions.<ref name=Gerrits_1996/>

==References==

{{reflist|refs=

<ref name="Cole_1974">{{cite journal |last1=Cole |first1=Madison B. |last2=Sykes |first2=Stephen M. |year=1974 |title=Glycol Methacrylate in Light Microscopy a Routine Method for Embedding and Sectioning Animal Tissues |url=http://www.tandfonline.com/doi/full/10.3109/10520297409117016 |journal=Stain Technology |language=en |volume=49 |issue=6 |pages=387–400 |doi=10.3109/10520297409117016 |issn=0038-9153 |pmid=4142140}}</ref>

<ref name=Gerrits_1996>{{cite journal|last1=Gerrits |first1=P. O. |last2=Horobin |first2=R. W. |year=1996

|title =Glycol Methacrylate Embedding for Light Microscopy: Basic Principles and Trouble-Shooting

|journal=Journal of Histotechnology

|volume =19

|issue =4

|pages =297–311

|doi =10.1179/his.1996.19.4.297

}}</ref>

<ref name=Macret_1982>{{cite journal|last1=Macret |first1=M. |last2=Hild |first2=G. |year=1982

|title = Hydroxyalkyl methacrylates: Kinetic investigations of radical polymerizations of pure 2-hydroxyethyl methacrylate and 2, 3-dihydroxypropyl methacrylate and the radical copolymerization of their mixtures

|journal=Polymer

|volume =23

|issue =1

|pages =81–90

|doi =10.1016/0032-3861(82)90020-9

|pmid =

|url =

}}</ref>

<ref name=Rosenberg_1960>{{cite journal|last1=Rosenberg |first1=M. |last2=Bartl |first2=P. |last3=Lesko |first3=J. |year =1960

|title =Water-soluble methacrylate as an embedding medium for the preparation of ultrathin sections

|journal=Journal of Ultrastructure Research

|volume =4

|issue =3–4

|pages =298–303

|doi =10.1016/s0022-5320(60)80024-x

|pmid =13743397

}}</ref>

<ref name=Wichterle_1960>{{cite journal|last1=Wichterle |first1=O. |last2=Lím |first2=D. |year=1960

|title =Hydrophilic gels for biological use

|journal=Nature

|volume =185

|issue =4706

|pages =117–118

|doi =10.1038/185117a0

|bibcode=1960Natur.185..117W

|pmid =

|s2cid =4211987

|url =

}}</ref>

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{{DEFAULTSORT:Hydroxyethylmethacrylate}}

[[Category:Methacrylate esters]]

[[Category:Monomers]]