(Hydroxyethyl)methacrylate

Synthesis

Hydroxyethylmethacrylate 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 hydroxyethylmethacrylate, it works as crosslinking agent.

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 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

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

Cosmetics

Hydroxyethylmethacrylate is the most common ingredient in cosmetic nail products, where it is used as a resin base and in polishes, primers, coats, and gels. Hydroxyethylmethacrylate is also a component of cosmetics glues for the application of eyelash and hair extensions.

As a known skin irritant, European Union regulations mandate labeling of products that contain Hydroxyethylmethacrylate, with limited compliance. Products are also restricted to professionals.

Other

In electron microscopy, later in light microscopy, hydroxyethylmethacrylate 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.

Hazards

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

References

References

1. (July 2013). "GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)".
2. "2-hydroxyethyl methacrylate_msds". ChemSrc: A Smart Chem-Search Engine.
3. 0-9771580-0-4; LCC# PN2068.B53 2005
4. (2017). "Three-dimensional printing of transparent fused silica glass". Nature.
5. (2020). "Highly Expandable Foam for Lithographic 3D Printing". ACS Applied Materials and Interfaces.
6. Symanzik, Cara. (2022). "Allergic contact dermatitis caused by 2-hydroxyethyl methacrylate and ethyl cyanoacrylate contained in cosmetic glues among hairdressers and beauticians who perform nail treatments and eyelash extension as well as hair extension applications: A systematic review". Contact Dermatitis.
7. Steunebrink, Iemke M.. (2024). "Presence of 2-hydroxyethyl methacrylate (HEMA) and other (meth)acrylates in nail cosmetics, and compliance with EU legislation: An online market survey". Contact Dermatitis.
8. (2006). "Paints and Coatings".
9. (1974). "Glycol Methacrylate in Light Microscopy a Routine Method for Embedding and Sectioning Animal Tissues". Stain Technology.