HYDROXYETHYL METHACRYLATE (GLYCOL METHACRYLATE)

Hydroxyethyl methacrylate (Glycol methacrylate) is the organic compound with the chemical formula H2C\dC(CH3)CO2CH2CH2OH.
Hydroxyethyl methacrylate (Glycol methacrylate) is a colorless viscous liquid that readily polymerizes.
Hydroxyethyl methacrylate (Glycol methacrylate) is a monomer that is used to make various polymers.

IUPAC name: 2-Hydroxyethyl 2-methylprop-2-enoate
CAS no:868-77-9
EC no:212-782-2
Formula:C6H10O3

Other names: 2-Hydroxyethyl methacrylate, 868-77-9, Glycol methacrylate, Hydroxyethyl methacrylate, HEMA, Glycol monomethacrylate, Ethylene glycol methacrylate, 2-Hydroxyethylmethacrylate, 2-(Methacryloyloxy)ethanol, 2-hydroxyethyl 2-methylprop-2-enoate, 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, 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, MFCD00002863, MFCD00081879, Bisomer HEMA, hydroxyethylmethacrylate, 1,2-Ethanediol mono(2-methylpropenoate), hydroxyehtyl methacrylate, hydroxylethyl methacrylate, HEMA [INCI], 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 2-methylacrylate #, Tox21_200415, AKOS015899920, Methacrylic Acid 2-Hydroxyethyl Ester, CS-W013439, DS-9647, HY-W012723, NCGC00166101-01, NCGC00166101-02, NCGC00257969-01, CAS-868-77-9, PD167321, SY279104, 1,2-Ethanediol, mono(2-methyl)-2-propenyl, M0085, NS00008941, EN300-98188, D70640, 2-Methyl-2-propenoic acid, 2-hydroxyethyl ester, Hydroxyethyl methacrylate(5.9cp(30 degrees c)), 2-Propenoic acid, 2-methyl-,2-hydroxiethyl ester, A904584, Q424799, J-509674, InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H

Synthesis
Hydroxyethyl methacrylate (Glycol methacrylate) was first synthesized around 1925.

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 Hydroxyethyl methacrylate (Glycol methacrylate), it works as crosslinking agent.

Properties
Hydroxyethyl methacrylate (Glycol methacrylate) is completely miscible with water and ethanol, but its polymer is practically insoluble in common solvents.
Its viscosity is 0.0701 Pa⋅s at 20°C and 0.005 Pa⋅s at 30°C.
During polymerization, it shrinks by approximately 6%.

Applications
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: 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.

Use in 3D printing
Hydroxyethyl methacrylate (Glycol methacrylate) 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.
Hydroxyethyl methacrylate (Glycol methacrylate) 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 it forms a foaming resin which expands when heated.

Other
In electron microscopy, later in light microscopy, Hydroxyethyl methacrylate (Glycol methacrylate) 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.

Molar mass: 130.143 g·mol−1
Appearance: Colourless liquid
Density: 1.07 g/cm3
Melting point: −99 °C (−146 °F; 174 K)

Boiling point: 213 °C (415 °F; 486 K)
Solubility in water: miscible
log P: 0.50
Vapor pressure: 0.08 hPa

XLogP3: 0.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 4

Exact Mass: 130.062994177 g/mol
Monoisotopic Mass: 130.062994177 g/mol
Topological Polar Surface Area: 46.5Å²
Heavy Atom Count: 9

Complexity: 118
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Hydroxyethyl methacrylate (Glycol methacrylate) is an enoate ester that is the monomethacryloyl derivative of ethylene glycol.
Hydroxyethyl methacrylate (Glycol methacrylate) has a role as a polymerisation monomer and an allergen.
Hydroxyethyl methacrylate (Glycol methacrylate) is functionally related to an ethylene glycol and a methacrylic acid.

Hydroxyethyl methacrylate (Glycol methacrylate) is a hydroxyester compound and a resin monomer used in desensitizing dentin.
By applying Hydroxyethyl methacrylate (Glycol methacrylate) locally to sensitive teeth, sensitive areas in the teeth get sealed and block the dentinal tubules at the dentin surface from stimuli that cause pain.
This prevents excitation of the tooth nerve and relieves pain caused by tooth hypersensitivity.

Hydroxyethyl methacrylate (Glycol methacrylate) is an ester of methacrylic acid, soluble in water and has relatively low volatility.
Hydroxyethyl methacrylate (Glycol methacrylate) copolymerizes easily with a variety of monomers, incorporates cross-link sites, imparts corrosion, fogging and abrasion resistance, and the hydroxyl group improves adhesion.

Hydroxyethyl methacrylate (Glycol methacrylate) is Functional monomer for thermoset coating, textile treatment agent, adhesives, paper processing material, polymer modifier. Tg: 55

Hydroxyethyl methacrylate (Glycol methacrylate)
Hydroxyethyl methacrylate (Glycol methacrylate).
Hydroxyethyl methacrylate (Glycol methacrylate) is a clear, colourless liquid with a characteristic odour.
Hydroxyethyl methacrylate (Glycol methacrylate) is an ester of methacrylic acid.
Hydroxyethyl methacrylate (Glycol methacrylate) easily dissolves in water, relatively low volatility, non-toxic and non-yellowing.

Hydroxyethyl methacrylate (Glycol methacrylate) 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.

Hydroxyethyl methacrylate (Glycol methacrylate) is used in the manufacture of acrylic polymers for adhesives, printing inks, coatings and metal applications. Hydroxyethyl methacrylate (Glycol methacrylate) is also widely used as reactive diluent and alternative to styrene in unsatured polyester (UPR).

Hydroxyethyl methacrylate (Glycol methacrylate) is also used in high performance coatings for glass to guard against scratching and weathering.
Hydroxyethyl methacrylate (Glycol methacrylate) is found in paint resins and binders for textiles and paper.
Hydroxyethyl methacrylate (Glycol methacrylate) is also found in metal coatings as an adhesion promoter

Hydroxyethyl methacrylate (Glycol methacrylate) refers to a chemical substance that is a monomer hydroxyester compound used to desensitize dentin structures and make polymers.
Hydroxyethyl methacrylate (Glycol methacrylate) is a clear, colorless liquid with a characteristic odor.
These polymers are hydrophobic in nature, making them excellent for water-blocking corrosion prevention mechanisms.

Hydroxyethyl methacrylate (Glycol methacrylate) is the organic compound with the formula H2C=C(CH3)CO2CH2CH2OH.
Hydroxyethyl methacrylate (Glycol methacrylate) is a colorless viscous liquid that readily polymerizes.
Hydroxyethyl methacrylate (Glycol methacrylate) is a monomer that is used to make various polymers.

Hydroxyethyl methacrylate (Glycol methacrylate) is a hydroxyester compound and a resin monomer used in desensitizing dentin.
By applying Hydroxyethyl methacrylate (Glycol methacrylate) locally to sensitive teeth, sensitive areas in the teeth get sealed and block the dentinal tubules at the dentin surface from stimuli that cause pain. This prevents excitation of the tooth nerve and relieves pain caused by tooth hypersensitivity.

Hydroxyethyl methacrylate (Glycol methacrylate) is an enoate ester that is the monomethacryloyl derivative of ethylene glycol.
Hydroxyethyl methacrylate (Glycol methacrylate) has a role as a polymerisation monomer and an allergen. It derives from an ethylene glycol and a methacrylic acid.

Hydroxyethyl methacrylate (Glycol methacrylate) is a colorless viscous liquid that readily polymerizes. Hydroxyethyl methacrylate (Glycol methacrylate) is a monomer that is used to make various polymers.
Hydroxyethyl methacrylate (Glycol methacrylate) stabilized with MEHQ.

Hydroxyethyl methacrylate (Glycol methacrylate): An enoate ester that is the monomethacryloyl derivative of ethylene glycol.

Chemical Role(s): polymerisation monomer
Any compound used as a monomer for a polymerisation process.
The term is generally used in relation to industrial polymerisation processes.

Hydroxyethyl methacrylate (Glycol methacrylate) has functional parent ethylene glycol
Hydroxyethyl methacrylate (Glycol methacrylate) has functional parent methacrylic acid
Hydroxyethyl methacrylate (Glycol methacrylate) has role allergen
Hydroxyethyl methacrylate (Glycol methacrylate) has role polymerisation monomer
Hydroxyethyl methacrylate (Glycol methacrylate) is a enoate ester

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.

When treated with polyisocyanates, poly makes a crosslinked polymer, an acrylic resin, that is a useful component in some paints

Use in 3D printing
Hydroxyethyl methacrylate (Glycol methacrylate) 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.
When combined with a suitable blowing agent such as BOC Anhydride it forms a foaming resin which expands when heated.

Why is it used in cosmetics and personal care products?
Methacrylate ester monomers are used in nail enhancement products to build or lengthen the nail.

Methylacrylate ester monomers are relatively small chemical compounds.
They are produced by reacting methacrylic acid with the appropriate alcohol.
For example, Butyl Methacrylate is prepared from the reaction of methacrylic acid and butyl alcohol.
Many of the methacrylate ester monomers are used in dentistry as resins, adhesives and restorative materials.

Hydroxyethyl methacrylate (Glycol methacrylate) 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.
Hydroxyethyl methacrylate (Glycol methacrylate) provides scratch, solvent & weather resistance, control of hydrophobicity &/or can introduce reactive sites.

Global Hydroxyethyl methacrylate (Glycol methacrylate) Market is classified on the basis of product type, applications and geography.
Hydroxyethyl methacrylate (Glycol methacrylate) or Hydroxyethyl methacrylate (Glycol methacrylate) is a chemical compound which is a monomer.
Hydroxyethyl methacrylate (Glycol methacrylate) is basically a clear and colourless liquid.
Hydroxyethyl methacrylate (Glycol methacrylate) is primarily used to make a wide range of polymers based products.

The factors that propel the growth of the Hydroxyethyl methacrylate (Glycol methacrylate) Market include increasing demand and wide range of applications.
On the other hand, there are certain factors that may hamper the growth of the market such as skin irritation, sore throat, cough, etc.

Hydroxyethyl methacrylate (Glycol methacrylate) Market is classified on the basis of product type as 97% Hydroxyethyl methacrylate (Glycol methacrylate), 95% Hydroxyethyl methacrylate (Glycol methacrylate), and others.
Based on applications, the global market is segmented asadhesives, paints & coating, contact lenses, printing inks and others.

Hydroxyethyl methacrylate (Glycol methacrylate) is perhaps the most widely studied and used neutral hydrophilic monomer.
The monomer is soluble, its homopolymer is water-insoluble but plasticized and swollen in water.
This monomer is the basis for many hydrogel products such as soft contact lenses, as well as polymer binders for controlled drug release, absorbants for body fluids and lubricious coatings.

Hydroxyethyl methacrylate (Glycol methacrylate); aka. Hydroxyethyl methacrylate (Glycol methacrylate), CAS# 868-77-9) is perhaps the most widely studied and used neutral hydrophilic monomer.
This bifunctional monomer, which contains both acrylate and hydroxyl functionality, is produced from the esterification of methacrylic acid by ethylene glycol or from ethylene oxide via a ring-opening process.
The Hydroxyethyl methacrylate (Glycol methacrylate) monomer is water soluble, while its homopolymer is water-insoluble but plasticized and swollen in water.

APPLICATIONS
Hydroxyethyl methacrylate (Glycol methacrylate) is often used to increase the hydrophobicity or surface adhesion of polymers and polymer-based materials such as specialty coatings, resins, adhesives, printing inks, and acrylic plastics.
As a co-monomer with other acrylic ester monomers, Hydroxyethyl methacrylate (Glycol methacrylate) can be used to control hydrophobicity or introduce reactive sites.
In biomedical applications, the monomer is the basis for many hydrogel products such as soft contact lenses, polymer binders for controlled drug release, absorbents for body fluids, and for lubricious coatings.

The Hydroxyethyl methacrylate (Glycol methacrylate) polymer is used in certain contact lenses where it has the additional advantage of being rigid and easy to shape with grinding tools when it is dry and then becomes flexible when it absorbs water.
While Hydroxyethyl methacrylate (Glycol methacrylate) is available in a variety of industrial grades useful for coatings, adhesives and plastics, well-characterized, higher purity material prepared using well-documented processes is required for biomedical applications.

Abstract and Figures
Because Hydroxyethyl methacrylate (Glycol methacrylate) is very important in macromolecular chemistry.
This paper reviews the main properties of the polymers or copolymers prepared from it by summarizing the information published in articles or patients.

Human Health
The acute toxicity of Hydroxyethyl methacrylate (Glycol methacrylate) is low (Oral LD50 > 4000 mg/kg; Dermal LD50 > 3000 mg/kg).
Hydroxyethyl methacrylate (Glycol methacrylate) is not more than slightly irritating to skin, and moderately irritating to eyes.
Hydroxyethyl methacrylate (Glycol methacrylate) is hydrolyzed to methacrylic acid and ethylene glycol.
While other acrylates and methacrylates have been shown to cause nasal lesions on inhalation after hydrolysis to Methacrylic Acid (MAA) (discussed in SIAM 11), this effect has not been observed for Hydroxyethyl methacrylate (Glycol methacrylate)

Hydroxyethyl methacrylate (Glycol methacrylate) is used industrially as a monomer for synthesis of polymers, and for dental prosthetics. It is also used in geotechnical grouting in construction work.

Application:
In plastic industry, Hydroxyethyl methacrylate (Glycol methacrylate) is used for the production of acrylic acid resin.
In coating industry, Hydroxyethyl methacrylate (Glycol methacrylate) can be used for the production of double-component coating with epoxy resin, diisocynate, melamino-formaldehyde resin.

In the oil industry, Hydroxyethyl methacrylate (Glycol methacrylate) can be used as additive for cleaning of lubricant.
In the electronic industry, Hydroxyethyl methacrylate (Glycol methacrylate) is used as dehydrating agent of electron microscope.

In textile industry, Hydroxyethyl methacrylate (Glycol methacrylate) is used as the adhesive for the production of fabric.
In analytical chemistry, Hydroxyethyl methacrylate (Glycol methacrylate) is used as chemical reagent.
In addition, Hydroxyethyl methacrylate (Glycol methacrylate) can also be used for fiber treatment agent, adhesive, photosensitive resin, medical macromolecular material, ect.

Using sodium dodecyl sulfate (SDS) as the single surfactant Hydroxyethyl methacrylate (Glycol methacrylate), extremely water-soluble) was polymerized at 60°C in aqueous medium to obtain latexes with average particle diameter below 80 nm and the extrapolated kp value was estimated to be 200±20 (L/mol-s).

Values of monomer concentration in particles ([M]) used in this calculation were obtained by interpolating the literature available partition data of Hydroxyethyl methacrylate (Glycol methacrylate) between the gel phase (i.e., poly(Hydroxyethyl methacrylate (Glycol methacrylate)) and the water phase.
The [M] values (< 1.00 mol/L) are much lower than those for the sparely-soluble monomer (3 to 4 mol/L), and the [M] values decrease with increasing conversion

Hydroxyethyl methacrylate (Glycol methacrylate) : Chemical Properties and Applications in Biomedical Fields
Hydroxyethyl methacrylate (Glycol methacrylate) is a monomer with numerous applications.
More than 1500 publications have been devoted to this product since 1967,2000 publications or patents mention the corresponding polymer, and a greater number of works involve copolymers incorporating this monomer.

Hydroxyethyl methacrylate (Glycol methacrylate)
Hydroxyethyl methacrylate (Glycol methacrylate) replaces part of the water and is a small molecule (molecular weight: 130 g/mol) soluble in water due to the presence of a hydroxyl group in its structure.

Polymeric Formulations
Hydroxyethyl methacrylate (Glycol methacrylate) is made by polymerizing Hydroxyethyl methacrylate (Glycol methacrylate) monomer with a cross-linker such as ethylene glycol dimethacrylate (EGDMA).
Most of the hydrophilic behavior of Hydroxyethyl methacrylate (Glycol methacrylate) is due to the presence of the hydroxyl group (OH) at the end of the monomer.
At this location in the resultant polymer, hydrogen bonding with water molecules occurs, causing them to be drawn into the polymer matrix.
The result is that contact lenses made from pHydroxyethyl methacrylate (Glycol methacrylate) contain approximately 40% water in the fully hydrated state.

Hydroxyethyl methacrylate (Glycol methacrylate)
Hydroxyethyl methacrylate (Glycol methacrylate) is an ester of Methacrylic acid and is used as a raw material component in the synthesis of polymers.
Hydroxyethyl methacrylate (Glycol methacrylate) forms a homopolymer and copolymers.
Copolymers of Hydroxyethyl methacrylate (Glycol methacrylate) can be prepared with (meth)acrylic acid and its salts, amides, and esters, as well as (meth)acrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, and other monomers.

Hydroxyethyl methacrylate (Glycol methacrylate), 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.

Hydroxyethyl methacrylate (Glycol methacrylate) is an important vinyl monomer that can be easily polymerized.
The pendant hydroxyl groups make the polymer fully water soluble, whereas lightly crosslinked Hydroxyethyl methacrylate (Glycol methacrylate) forms hydrogels which absorb noticeable amounts of water.

Hydroxyethyl methacrylate (Glycol methacrylate) is frequently copolymerized with other monomers to modify its properties.
Due to its low toxicity and hydrophilic character, it has found numerous applications in biomedicine, including contact lenses, drug delivery systems, and dental adhesives.
Another important application of Hydroxyethyl methacrylate (Glycol methacrylate) are isocyanate-free vinyl ester urethane compositions for adhesives, sealants and coatings.
The use of Hydroxyethyl methacrylate (Glycol methacrylate) as a capping agent reduces the toxicity of the prepolymers and increases the low shear viscosity efficiency.