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2-Hydroxyethyl Methacrylate (HEMA) is the organic compound with the chemical formula H2CdC(CH3)CO2CH2CH2OH.
2-Hydroxyethyl Methacrylate (HEMA) is a colorless viscous liquid that readily polymerizes.
2-Hydroxyethyl Methacrylate (HEMA) is a monomer that is used to make various polymers.
CAS: 868-77-9
MF: C6H10O3
MW: 130.14
EINECS: 212-782-2
Synonyms
1,2-ETHANEDIOL MONO(2-METHYLPROPENOATE);2-HYDROXYETHYL 2-METHYLPROPERIOATE;2-HYDROXYETHYL METHACRYLATE;1,2-Ethanediol, mono(2-methyl)-2-propenoate-;2-(Methacryloyloxy)ethanol;2-Hydroxyethyl 2-methylacrylate;2-Hydroxyethyl-2-methyl-2-propenoate;2-Methyl-2-propenoic acid, 2-hydroxyethyl ester;2-HYDROXYETHYL METHACRYLATE;868-77-9;Glycol methacrylate;Hydroxyethyl methacrylate;HEMA;Glycol monomethacrylate;Ethylene glycol methacrylate;2-Hydroxyethylmethacrylate;2-hydroxyethyl 2-methylprop-2-enoate;2-(Methacryloyloxy)ethanol;Mhoromer;Methacrylic acid, 2-hydroxyethyl ester;Monomer MG-1;Ethylene glycol monomethacrylate;(hydroxyethyl)methacrylate;beta-Hydroxyethyl methacrylate;NSC 24180;2-Hydroxyethyl 2-methylacrylate;2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester;PHEMA;CCRIS 6879;CHEBI:34288;Ethylene glycol, monomethacrylate;HSDB 5442;12676-48-1;EINECS 212-782-2;UNII-6E1I4IV47V;BRN 1071583;Monomethacrylic ether of ethylene glycol;6E1I4IV47V;DTXSID7022128;PEG-MA;1,2-Ethanediol mono(2-methyl)-2-propenoate;MFCD00002863;NSC-24180;2-hydroxyethylmethylacrylate;ethyleneglycol monomethacrylate;DTXCID202128;.beta.-Hydroxyethyl methacrylate;2-hydroxyethylmethacrylate (hema);EC 212-782-2;4-02-00-01530 (Beilstein Handbook Reference);NSC24180;MFCD00081879;2-Hydroxyethyl Methacrylate (stabilized with MEHQ);Bisomer HEMA;2-Hydroxyethyl methacrylate,ophthalmic grade;hydroxyethylmethacrylate;1,2-Ethanediol mono(2-methylpropenoate);hydroxyehtyl methacrylate;hydroxylethyl methacrylate;2-hydroxyetyl methacrylate;2-HEMA;Epitope ID:117123;2-hydroxylethyl methacrylate;2-hydroxyethyl(methacrylate);SCHEMBL14886;WLN: Q2OVY1&U1;2-methacryloyloxyethyl alcohol;BIDD:ER0648;CHEMBL1730239;CHEBI:53709;2-Hydroxyethyl methacrylate, 98%;2-Hydroxyethyl 2-methylacrylate #;2-Hydroxyethyl methacrylate (HEMA);Tox21_200415;AKOS015899920;Methacrylic Acid 2-Hydroxyethyl Ester;CS-W013439;DS-9647;HY-W012723;NCGC00166101-01;NCGC00166101-02;NCGC00257969-01;CAS-868-77-9;DA-69793;PD167321;SY279104;2-HYDROXYETHYL METHACRYLATE [HSDB];2-Hydroxyethyl methacrylate,low acid grade;1,2-Ethanediol, mono(2-methyl)-2-propenyl;2-HYDROXYETHYL METHACRYLATE [WHO-DD];M0085;NS00008941;EN300-98188;D70640;2-Hydroxyethyl methacrylate(hema),technical grade;2-Methyl-2-propenoic acid, 2-hydroxyethyl ester;Hydroxyethyl methacrylate(5.9cp(30 degrees c));2-Propenoic acid, 2-methyl-,2-hydroxiethyl ester;Hydroxyethyl methacrylate(>200cp(25 degrees c));Q424799;2-Hydroxyethyl Methacrylate, (stabilized with MEHQ);J-509674;2-Hydroxyethyl Methacrylate, Stabilized with 250 ppm MEHQ;2-Hydroxyethyl methacrylate, embedding medium (for microscopy);InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H;2-Hydroxyethyl methacrylate, >=99%, contains <=50 ppm monomethyl ether hydroquinone as inhibitor;2-Hydroxyethyl methacrylate, contains <=250 ppm monomethyl ether hydroquinone as inhibitor, 97%
2-Hydroxyethyl Methacrylate (HEMA) is an enoate ester that is the monomethacryloyl derivative of ethylene glycol.
2-Hydroxyethyl Methacrylate (HEMA) is biocompatible in nature.
Polymeric hydrogel scaffold can be produced by polymerizing HEMA in water.
2-Hydroxyethyl Methacrylate (HEMA) is the monomer used to produce copolymers that are used in hydrogels for tissue engineering.
The copolymers are composed of glycol methacrylates, which have a high rate constant and can be polymerized at room temperature or by UV light.
Copolymers are also resistant to degradation by enzymes in biological samples such as human immunoglobulin.
2-Hydroxyethyl Methacrylate (HEMA) is also used to produce polymeric compositions with excellent mechanical properties, such as axonal growth, and can be used to make hydrogels.
2-Hydroxyethyl Methacrylate (HEMA), easily entering into the reaction of accession with a wide range of organic and inorganic substances, is used for the synthesis of organic low molecular weight substances.
2-Hydroxyethyl Methacrylate (HEMA) is a neutral hydrophilic monomer useful in UV curing polymer systems & durable high gloss coatings.
Other industrial applications include nails, dental, hydrogels (such as contact lens), UV inks & adhesives.
2-Hydroxyethyl Methacrylate (HEMA) provides scratch, solvent & weather resistance, control of hydrophobicity &/or can introduce reactive sites.
2-Hydroxyethyl Methacrylate (HEMA) is a clear, colourless liquid with a characteristic odour.
2-Hydroxyethyl Methacrylate (HEMA) is an ester of methacrylic acid.
2-Hydroxyethyl Methacrylate (HEMA) easily dissolves in water, relatively low volatility, non-toxic and non-yellowing.
2-Hydroxyethyl Methacrylate (HEMA) copolymerizes readily with a wide variety of monomers, and the added hydroxyl groups improve adhesion to surfaces, incorporate cross-linking sites, and impart corrosion, fogging, and abrasion resistance, as well as contribute to low odour, colour, and volatility.
2-Hydroxyethyl Methacrylate (HEMA) is used in the manufacture of acrylic polymers for adhesives, printing inks, coatings and metal applications.
2-Hydroxyethyl Methacrylate (HEMA) is also widely used as reactive diluent and alternative to styrene in unsatured polyester (UPR).
2-Hydroxyethyl Methacrylate (HEMA) Chemical Properties
Melting point: -12 °C
Boiling point: 67 °C3.5 mm Hg(lit.)
Density: 1.073 g/mL at 25 °C(lit.)
Vapor density: 5 (vs air)
vapor pressure: 0.01 mm Hg ( 25 °C)
Refractive index: n20/D 1.453(lit.)
Fp: 207 °F
Storage temp.: 2-8°C
Solubility: Chloroform, Methanol (Slightly)
Form: Liquid
pka: 13.83±0.10(Predicted)
Color: Clear
Odor: Ester like
Water Solubility: soluble
FreezingPoint: -20
FreezingPoint: -96
Sensitive: Air Sensitive
BRN: 1071583
Stability: Unstable - may polymerize in the absence of stabilizer.
May be stabilized with, or contain small amounts of, diethylene glycol monomethacrylate, di(ethylene glycol)dimethacrylate, methacrylic acid.
Incompatible with strong oxidizing agents, free radical initiators, peroxides, steel. Closed containers may explode if heated due to runaway polymer
InChIKey: WOBHKFSMXKNTIM-UHFFFAOYSA-N
LogP: 0.42 at 25℃
CAS DataBase Reference: 868-77-9(CAS DataBase Reference)
NIST Chemistry Reference: 2-Hydroxyethyl Methacrylate (HEMA) (868-77-9)
EPA Substance Registry System: 2-Hydroxyethyl Methacrylate (HEMA) (868-77-9)
2-Hydroxyethyl Methacrylate (HEMA) is completely miscible with water and ethanol, but its polymer is practically insoluble in common solvents.
2-Hydroxyethyl Methacrylate (HEMA)'s viscosity is 0.0701 Pa⋅s at 20°C and 0.005 Pa⋅s at 30°C.
During polymerization, 2-Hydroxyethyl Methacrylate (HEMA) shrinks by approximately 6%.
Uses
2-Hydroxyethyl Methacrylate (HEMA) is the methacrylic monomer for use in UV inks, adhesives, lacquers, dental materials, artificial nails, etc.
2-Hydroxyethyl Methacrylate (HEMA) is used in UV-curable inks and coatings.
2-Hydroxyethyl Methacrylate (HEMA) is also used in adhesives, artificial nails, dental materials and lacquers.
In dentistry, 2-Hydroxyethyl Methacrylate (HEMA) is one of the main volatile acrylates along with methyl methacrylate.
Further, 2-Hydroxyethyl Methacrylate (HEMA) is used as a monomer in the synthesis of polymers for dental prosthetics and for geotechnical grouting in construction work.
2-Hydroxyethyl Methacrylate (HEMA) is used for preparation of hydrophilic polymers for biomedical devices.
2-Hydroxyethyl Methacrylate (HEMA) is mainly used for the modification of resins and coatings.
The resulting resin may contain reactive hydroxyl groups by copolymerization with other acrylic monomers.
Together with melamine formaldehyde (or urea formaldehyde) resin, epoxy resin, etc., for the manufacture of two-component coatings.
Added to the high-grade car paint, can maintain the mirror gloss for a long time.
2-Hydroxyethyl Methacrylate (HEMA) can also be used as an adhesive for synthetic textiles and a medical polymer monomer.
Contact lenses
In 1960, O. Wichterle and D. Lím described its use in synthesis of hydrophilic crosslinked networks, and these results had great importance for manufacture of soft contact lenses.
Polyhydroxyethylmethacrylate is hydrophilic: 2-Hydroxyethyl Methacrylate (HEMA) is capable of absorbing from 10 to 600% water relative to the dry weight.
Because of this property, 2-Hydroxyethyl Methacrylate (HEMA) was one of the first materials to be used in the manufacture of soft contact lenses.
Use in 3D printing
2-Hydroxyethyl Methacrylate (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.
2-Hydroxyethyl Methacrylate (HEMA) may be used as a monomeric matrix in which 40nm silica particles are suspended for 3D glass printing.
When combined with a suitable blowing agent such as BOC anhydride 2-Hydroxyethyl Methacrylate (HEMA) forms a foaming resin which expands when heated.
Other
In electron microscopy, later in light microscopy, 2-Hydroxyethyl Methacrylate (HEMA) serves as an embedding medium.
When treated with polyisocyanates, polyhydroxyethylmethacrylate makes a crosslinked polymer, an acrylic resin, that is a useful component in some paints.
Synthesis
H2-Hydroxyethyl Methacrylate (HEMA) was first synthesized around 1925.
Common methods of synthesis are:
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 2-Hydroxyethyl Methacrylate (HEMA), it works as crosslinking agent.
Preparation Method
The addition reaction of methacrylic acid and ethylene oxide in the presence of a catalyst and a polymerization inhibitor generates crude 2-Hydroxyethyl Methacrylate (HEMA), which is degassed and fractionated to obtain a finished product.
The potassium salt of methacrylic acid is reacted with chloroethanol in the presence of a polymerization inhibitor to produce crude 2-Hydroxyethyl Methacrylate (HEMA), which is salted out and refined to obtain a finished product.
