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Sigma-Aldrich

2-Hydroxyethyl acrylate

96%, contains 200-650 ppm monomethyl ether hydroquinone as inhibitor

Synonym(s):

Ethylene glycol monoacrylate

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About This Item

Linear Formula:
CH2=CHCOOCH2CH2OH
CAS Number:
818-61-1
Molecular Weight:
116.12
Beilstein/REAXYS Number:
969853
EC Number:
212-454-9
MDL number:
MFCD00002865
UNSPSC Code:
12162002
PubChem Substance ID:
24857612
NACRES:
NA.23

vapor density

>1 (vs air)

Quality Level

100

vapor pressure

<0.1 mmHg ( 20 °C)

assay

96%

form

solid

contains

200-650 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.45 (lit.)

bp

90-92 °C/12 mmHg (lit.)

density

1.011 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OCCOC(=O)C=C

InChI

1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2

InChI key

OMIGHNLMNHATMP-UHFFFAOYSA-N

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General description

2-Hydroxyethyl acrylate (HEA) is a monomer that is widely used in the field of material synthesis for the production of various types of polymers, such as hydrogels, coatings, adhesives, and thermosets. Its versatility lies in its ability to copolymerize with a variety of monomers, resulting in a wide range of polymer properties and applications. Its main use is in the production of hydrogels, which are highly absorbent and can be used in wound dressings, contact lenses, drug delivery systems, and other biomedical applications. Additionally, 2-hydroxyethyl acrylate-based coatings and adhesives are used in various surface modification and bonding applications, owing to their excellent adhesion, flexibility, and chemical resistance properties.

Application

Porous hydrogels can be prepared by copolymerization of 2-hydroxyethyl acrylate and a cross linking agent. 2-hydroxyethyl acrylate may be used in the synthesis of amphilic block copolymers by nitroxide mediated living radical polymeration. Also, it may be used to prepare tuned poly(hydroxyethyl acrylate) by atom transfer radical polymerization.

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Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

213.8 °F - closed cup

flash_point_c

101 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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J M Boothby et al.
Soft matter, 13(24), 4349-4356 (2017-05-04)
Materials that change shape are attractive candidates to replace traditional actuators for applications with power or size restrictions. In this work, we design a polymeric bilayer that changes shape in response to both heat and water by the incorporation of
Tugba Ozdemir et al.
ACS biomaterials science & engineering, 2(12), 2217-2230 (2016-12-19)
Current treatments for chronic xerostomia, or "dry mouth", do not offer long-term therapeutic benefits for head and neck cancer survivors previously treated with curative radiation. Towards the goal of creating tissue-engineered constructs for the restoration of salivary gland functions, we
Atom transfer radical polymerization of tert-butyl acrylate and preparation of block copolymers.
Davis KA and Matyjaszewski K
Macromolecules, 33(11), 4039-4047 (2000)
J C Tiller et al.
Journal of controlled release : official journal of the Controlled Release Society, 103(2), 355-367 (2005-03-15)
Bitelechelic polydimethylsiloxanes (PDMS) and 2-hydroxyethylacrylate (HEA)/acrylic acid(AA) were photopolymerized to give nanophase separated amphiphilic 20-mum-thin coatings covalently attached to glass. The coatings quickly take up the antimicrobial surfactant cetyltrimethylammonium chloride (CTAC). After a 30 min loading period the release of
Richard Hoogenboom et al.
Macromolecular rapid communications, 30(23), 2042-2048 (2009-12-01)
Poly(2-hydroxyethyl acrylate) (PHEA) is an interesting biomaterial with similar biocompatibility as the widespread used poly(2-hydroxyethyl methacrylate). Poly(2-hydroxypropyl acrylate) (PHPA) is a less frequently studied polymer that exhibits thermoresponsive behavior in water. Therefore, copolymers of HEA and HPA are interesting thermoresponsive
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Articles

Continuous Flow Manufacturing for Monomer Synthesis

The manufacture of monomers for use in ophthalmic applications is driven by the need for higher purity, improved reliability of manufacturing supply, but ultimately by the need for the increased comfort, convenience, and safety of contact lens wearers. Daily wear contact lenses have the potential to fill this need for many customers; however, their widespread use is constrained by higher costs compared to weekly- or monthly-based lenses. New approaches that improve cost structure and result in higher quality raw materials are needed to help make contact lenses more affordable and accelerate growth of the contact lens market.

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