(Hydroxyethyl)methacrylate
chemical compound
Hydroxyethylmethacrylate (also known as glycol methacrylate or HEMA) is the organic compound with the chemical formula H2C=C(CH3)CO2CH2CH2OH. It is a colorless viscous liquid that readily polymerizes, i.e. it is a monomer that is used to make various polymers.
Synthesis
Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are:
reaction of methacrylic acid with ethylene oxide:
H2C=C(CH3)CO2H + CH2CH2O → H2C=C(CH3)CO2CH2CH2OH
esterification of methacrylic acid with a large excess of ethylene glycol.
H2C=C(CH3)CO2H + HOCH2CH2OH → H2C=C(CH3)CO2CH2CH2OH + H2O
Both approaches also yield small amounts of ethylene glycol dimethacrylate, a polymer 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 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.
The public source identifies “(Hydroxyethyl)methacrylate” as chemical compound. This brief keeps that definition visible, then builds a research path around Hydroxyethyl, methacrylate and chemical.
Why this record matters
A short description can identify a subject without explaining its stakes. For “(Hydroxyethyl)methacrylate”, the useful work is to connect “chemical compound” to the records capable of establishing context and consequence.
The date and method of observation matter as much as the stated conclusion, especially where classification or consensus has changed. The source revision retrieved here is dated Jul 14, 2026. The linked authority identifier is Q424799. None of the 0 selected statements returned an explicit reference. The first chronological checks are 1925 and 1960.
Current terminology should not be projected backward without checking the classification used when the underlying evidence was created. The source lead contains qualifying language; that uncertainty should survive quotation, summary and reuse. Authority statements aid reconciliation but still require their own references, qualifiers and ranks to be checked.
How to read it
Check terminology, classification and the date of the cited evidence. Scientific names and technical consensus can change while older records retain historical value.
- Current terminology
- Classification context
- Finding cited technical literature
Primary datasets, specimen catalogues, standards bodies and the most recent peer-reviewed literature.
Three-step research path
- Establish the record: confirm the title “(Hydroxyethyl)methacrylate”, its source revision and the description used here.
- Expand the search: follow (Hydroxyethyl)methacrylate primary sources, (Hydroxyethyl)methacrylate archive and Hydroxyethyl research across catalogues and specialist indexes.
- Test the account: compare the strongest cited source with the responsible institution’s current record and note any disagreement.
Questions for further research
- Which source most directly establishes the central claim about “(Hydroxyethyl)methacrylate”?
- Has classification or technical consensus changed since the cited source?
- Which observation, specimen, dataset or publication supports the account?
Search terms from this dossier
This entry incorporates text from “(Hydroxyethyl)methacrylate” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.