(Hydroxyethyl)methacrylate

Last updated
(Hydroxyethyl)methacrylate
Hydroxyethyl methacrylate.svg
Hydroxyethyl methacrylate molecule ball.png
Names
Preferred 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
3D model (JSmol)
1071583
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.621 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-782-2
936557
KEGG
PubChem CID
RTECS number
  • OZ4725000
UNII
  • InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3 Yes check.svgY
    Key: WOBHKFSMXKNTIM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
    Key: WOBHKFSMXKNTIM-UHFFFAOYAH
  • O=C(OCCO)\C(=C)C
  • CC(=C)C(=O)OCCO
Properties
C6H10O3
Molar mass 130.143 g·mol−1
AppearanceColourless liquid
Density 1.07 g/cm3
Melting point −99 °C (−146 °F; 174 K) [1]
Boiling point 213 °C (415 °F; 486 K) [1]
miscible
log P 0.50 [2]
Vapor pressure 0.08 hPa
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Eye irritation
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H317, H319
P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Hydroxyethylmethacrylate (also known as glycol methacrylate) [3] [4] is the organic compound with the chemical formula H2C\dC(CH3)CO2CH2CH2OH. It is a colorless viscous liquid that readily polymerizes. Hydroxyethylmethacrylate is a monomer that is used to make various polymers.

Contents

Synthesis

Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are: [5]

Both these methods give also some amount of ethylene glycol dimethacrylate. During polymerization of hydroxyethylmethacrylate, it works as crosslinking agent. [5]

Properties

Hydroxyethylmethacrylate 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 [6] and 0.005 Pa⋅s at 30°C. [3] During polymerization, it shrinks by approximately 6%. [6]

Applications

Contact lenses

In 1960, O. Wichterle and D. Lím [7] described its use in synthesis of hydrophilic crosslinked networks, and these results had great importance for manufacture of soft contact lenses. [5] 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. [8]

Use in 3D printing

Hydroxyethylmethacrylate 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. [9] When combined with a suitable blowing agent such as BOC anhydride it forms a foaming resin which expands when heated. [10]

Other

In electron microscopy, later in light microscopy, hydroxyethylmethacrylate serves as an embedding medium. [4] [3]

When treated with polyisocyanates, polyhydroxyethylmethacrylate makes a crosslinked polymer, an acrylic resin, that is a useful component in some paints. [11]

Hazards

Hydroxyethylmethacrylate is a mild skin irritant and can cause allergic skin reactions. [3]

Related Research Articles

<span class="mw-page-title-main">Polyurethane</span> Polymer composed of a chain of organic units joined by carbamate (urethane) links

Polyurethane refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from a wide range of starting materials. This chemical variety produces polyurethanes with different chemical structures leading to many different applications. These include rigid and flexible foams, and coatings, adhesives, electrical potting compounds, and fibers such as spandex and polyurethane laminate (PUL). Foams are the largest application accounting for 67% of all polyurethane produced in 2016.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Polyethylene glycol</span> Chemical compound

Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH.

<span class="mw-page-title-main">Poly(methyl methacrylate)</span> Transparent thermoplastic, commonly called acrylic

Poly(methyl methacrylate) (PMMA) is the synthetic polymer derived from methyl methacrylate. It is used as an engineering plastic, and it is a transparent thermoplastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and brands Crylux, Hesalite, Plexiglas, Acrylite, Lucite, and Perspex, among several others. This plastic is often used in sheet form as a lightweight or shatter-resistant alternative to glass. It can also be used as a casting resin, in inks and coatings, and for many other purposes.

<span class="mw-page-title-main">Polyethylene terephthalate</span> Polymer

Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.

<span class="mw-page-title-main">Stereolithography</span> 3D printing technique

Stereolithography is a form of 3D printing technology used for creating models, prototypes, patterns, and production parts in a layer by layer fashion using photochemical processes by which light causes chemical monomers and oligomers to cross-link together to form polymers. Those polymers then make up the body of a three-dimensional solid. Research in the area had been conducted during the 1970s, but the term was coined by Chuck Hull in 1984 when he applied for a patent on the process, which was granted in 1986. Stereolithography can be used to create prototypes for products in development, medical models, and computer hardware, as well as in many other applications. While stereolithography is fast and can produce almost any design, it can be expensive.

<span class="mw-page-title-main">Methyl methacrylate</span> Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Ethylene glycol dimethacrylate</span> Chemical compound

Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)COOH. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Acrylic resin</span> Thermoplastic or thermosetting plastic

An acrylic resin is a thermoplastic or thermosetting plastic substance typically derived from acrylic acid, methacrylic acid and acrylate monomers such as butyl acrylate and methacrylate monomers such as methyl methacrylate. Thermoplastic acrylics designate a group of acrylic resins typically containing both a high molecular weight and a high glass transition temperature which exhibit lacquer dry capability. Acrylic resins designed for use in two component systems for crosslinking with isocyanate are referred to as polyols and are made with the monomers previously mentioned as well as hydroxy monomers such as hydroxy ethyl methacrylate. Acrylic resins are produced in different liquid carriers such as a hydrocarbon solvent or water in which case they are referred to as emulsions or dispersions and they are also provided in 100% solids bead form.

<span class="mw-page-title-main">Polyhydroxyethylmethacrylate</span> Chemical compound

Poly(2-hydroxyethyl methacrylate) (pHEMA) is a polymer that forms a hydrogel in water. Poly (PHEMA) hydrogel for intraocular lens (IOL) materials was synthesized by solution polymerization using 2-hydroxyethyl methacrylate (HEMA) as raw material, ammonium persulfate and sodium pyrosulfite (APS/SMBS) as catalyst, and triethyleneglycol dimethacrylate (TEGDMA) as cross-linking additive. It was invented by Drahoslav Lim and Otto Wichterle for biological use. Together they succeeded in preparing a cross-linking gel which absorbed up to 40% of water, exhibited suitable mechanical properties and was transparent. They patented this material in 1953.

<span class="mw-page-title-main">Janus particles</span> Type of nanoparticle or microparticle

Janus particles are special types of nanoparticles or microparticles whose surfaces have two or more distinct physical properties. This unique surface of Janus particles allows two different types of chemistry to occur on the same particle. The simplest case of a Janus particle is achieved by dividing the particle into two distinct parts, each of them either made of a different material, or bearing different functional groups. For example, a Janus particle may have one half of its surface composed of hydrophilic groups and the other half hydrophobic groups, the particles might have two surfaces of different color, fluorescence, or magnetic properties. This gives these particles unique properties related to their asymmetric structure and/or functionalization.

<span class="mw-page-title-main">Multiphoton lithography</span> Technique for creating microscopic structures

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<span class="mw-page-title-main">Glycidyl methacrylate</span> Chemical compound

Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol. Containing both an epoxide and an acrylate groups, the molecule is bifunctional. It is a common monomer used in the production of epoxy resins. While typical home epoxies contain diglycidyl ether of bisphenol A (DGEBA), glycidyl methacrylate is instead used to provide epoxy functionalization to polyolefins and other acrylate resins. Glycidyl methacrylate is produced by several companies worldwide, including Dow Chemical. It is used to prepare a range of composites.

<span class="mw-page-title-main">Methacrylic anhydride</span> Chemical compound

Methacrylic anhydride is a liquid which reacts with water exothermically.

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<span class="mw-page-title-main">Acrylonitrile styrene acrylate</span> Chemical compound

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Bis-GMA is a resin commonly used in dental composite, dental sealants. and dental cement. It is the diester derived from methacrylic acid and the bisphenol A diglycidyl ether. Bearing two polymerizable groups, it is prone to form a crosslinked polymer that is used in dental restorations. For dental work, highly viscous bis-GMA is mixed with aluminosilicate particles, crushed quartz and other related acrylates; changes to component ratios lead to different physical properties in the end product. Bis-GMA was incorporated into composite dental resins in 1962 by Rafael Bowen. Until matrix development work in the early 2000s, bis-GMA and related methacrylate monomers were the only options for organic matrix composition.

Covalent adaptable networks (CANs) are a type of polymer material that closely resemble thermosetting polymers (thermosets). However, they are distinguished from thermosets by the incorporation of dynamic covalent chemistry into the polymer network. When a stimulus (for example heat, light, pH, ...) is applied to the material, these dynamic bonds become active and can be broken or exchanged with other pending functional groups, allowing the polymer network to change its topology. This introduces reshaping, (re)processing and recycling into thermoset-like materials.

<span class="mw-page-title-main">Hydroxyethyl acrylate</span> Organic chemical-monomer

Hydroxyethyl acrylate is an organic chemical and a aliphatic compound. It has the formula C5H8O3 and the CAS Registry Number 818–61–1. It is REACH registered with an EU number of 212–454–9. It has dual functionality containing a polymerizable acrylic group and a terminal hydroxy group. It is used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.

References

  1. 1 2 "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)". July 2013.
  2. "2-hydroxyethyl methacrylate_msds". ChemSrc: A Smart Chem-Search Engine.
  3. 1 2 3 4 Gerrits, P. O.; Horobin, R. W. (1996). "Glycol Methacrylate Embedding for Light Microscopy: Basic Principles and Trouble-Shooting". Journal of Histotechnology. 19 (4): 297–311. doi:10.1179/his.1996.19.4.297.
  4. 1 2 Cole, Madison B.; Sykes, Stephen M. (1974). "Glycol Methacrylate in Light Microscopy a Routine Method for Embedding and Sectioning Animal Tissues". Stain Technology. 49 (6): 387–400. doi:10.3109/10520297409117016. ISSN   0038-9153. PMID   4142140.
  5. 1 2 3 Macret, M.; Hild, G. (1982). "Hydroxyalkyl methacrylates: Kinetic investigations of radical polymerizations of pure 2-hydroxyethyl methacrylate and 2, 3-dihydroxypropyl methacrylate and the radical copolymerization of their mixtures". Polymer. 23 (1): 81–90. doi:10.1016/0032-3861(82)90020-9.
  6. 1 2 Rosenberg, M.; Bartl, P.; Lesko, J. (1960). "Water-soluble methacrylate as an embedding medium for the preparation of ultrathin sections". Journal of Ultrastructure Research. 4 (3–4): 298–303. doi:10.1016/s0022-5320(60)80024-x. PMID   13743397.
  7. Wichterle, O.; Lím, D. (1960). "Hydrophilic gels for biological use". Nature. 185 (4706): 117–118. Bibcode:1960Natur.185..117W. doi:10.1038/185117a0. S2CID   4211987.
  8. 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
  9. Kotz, Frederik; Arnold, Karl; Bauer, Werner; Schild, Dieter; Keller, Nico; Sachsenheimer, Kai; Nargang, Tobias M.; Richter, Christiane; Helmer, Dorothea; Rapp, Bastian E. (2017). "Three-dimensional printing of transparent fused silica glass". Nature. 544 (7650): 337–339. Bibcode:2017Natur.544..337K. doi: 10.1038/nature22061 . ISSN   0028-0836. PMID   28425999.
  10. Wirth, D. (2020). "Highly Expandable Foam for Lithographic 3D Printing". ACS Applied Materials and Interfaces. 12 (16): 19033–19043. doi:10.1021/acsami.0c02683. PMID   32267677. S2CID   215603770.
  11. 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. ISBN   978-3527306732.