(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;
ChEBI	CHEBI:34288 ;
ChemSpider	12791 ;
ECHA InfoCard	100.011.621
KEGG	C14530 ;
UNII	6E1I4IV47V ;
	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	130.14 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]
log P	0.50[2]
Vapor pressure	0.08 hPa
Hazards
Main hazards	Eye irritation
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Hydroxyethylmethacrylate or HEMA is the monomer that is used to make the polymer polyhydroxyethylmethacrylate. The polymer 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]

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.^[4]

References

1 2 "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
↑ Kotz (20 April 2017). "Three-dimensional printing of transparent fused silica glass". Nature. Retrieved 27 April 2017.

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[gps-1] 1 2 "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] Kotz (20 April 2017). "Three-dimensional printing of transparent fused silica glass". Nature. Retrieved 27 April 2017.