(Hydroxyethyl)methacrylate

(Hydroxyethyl)methacrylate
Names
	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
CAS Number	868-77-9 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1071583
ChEBI	CHEBI:34288 ;
ChEMBL	ChEMBL1730239;
ChemSpider	12791 ;
ECHA InfoCard	100.011.621
EC Number	212-782-2;
Gmelin Reference	936557
KEGG	C14530 ;
PubChem CID	13360;
RTECS number	OZ4725000;
UNII	6E1I4IV47V ;
CompTox Dashboard (EPA)	DTXSID7022128 ;
	InChI InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 Key: WOBHKFSMXKNTIM-UHFFFAOYSA-N ; InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 Key: WOBHKFSMXKNTIM-UHFFFAOYAH;
	SMILES O=C(OCCO)\C(=C)C; CC(=C)C(=O)OCCO;
Properties
Chemical formula	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]
Solubility in water	miscible
log P	0.50[2]
Vapor pressure	0.08 hPa
Hazards
Main hazards	Eye irritation
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H317, H319
GHS precautionary statements	P261, P264, P272, P280, P302+352, P305+351+338, P321, P332+313, P333+313, P337+313, 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).
	verify (what is ?)
	Infobox references

Hydroxyethylmethacrylate or HEMA is the organic compound with the formula H₂C=C(CH₃)CO₂CH₂CH₂OH. 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 printing

HEMA 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.[5] When combined with a suitable blowing agent such as BOC Anhydride it forms a foaming resin which expands when heated.[6]

References

"GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.
"2-hydroxyethyl methacrylate_msds".
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.; et al. (2006). "Paints and Coatings". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a18_359.pub2.
Kotz (20 April 2017). "Three-dimensional printing of transparent fused silica glass". Nature. 544 (7650): 337–339. doi:10.1038/nature22061. PMID 28425999.
Wirth, D. (8 April 2020). "Highly Expandable Foam for Lithographic 3D Printing". ACS Appl. Mater. Interfaces. 12 (16): 19033–19043. doi:10.1021/acsami.0c02683. PMID 32267677.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[gps-1] "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.

[chemsrc-2] "2-hydroxyethyl methacrylate_msds".

[3] 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

[4] 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.

[5] Kotz (20 April 2017). "Three-dimensional printing of transparent fused silica glass". Nature. 544 (7650): 337–339. doi:10.1038/nature22061. PMID 28425999.

[6] Wirth, D. (8 April 2020). "Highly Expandable Foam for Lithographic 3D Printing". ACS Appl. Mater. Interfaces. 12 (16): 19033–19043. doi:10.1021/acsami.0c02683. PMID 32267677.