Glycidyl methacrylate
[CAS# 106-91-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polycyclic compound
• Name: Glycidyl methacrylate
• Synonyms: 2,3-Epoxypropyl methacrylate; Methacrylic acid 2,3-epoxypropyl ester
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• CAS Registry Number: 106-91-2
• EC Number: 203-441-9
• SMILES: CC(=C)C(=O)OCC1CO1

Properties

• Density: 1.042
• Boiling point: 189 °C
• Refractive index: 1.449-1.451
• Flash point: 76 °C
• Water solubility: 0.5-1.0 g/100 mL at 20 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Risk Statements: H302+H332-H302-H311-H312-H314-H315-H317-H318-H319-H332-H335-H341-H350-H360-H370-H372
• Safety Statements: P203-P260-P261-P262-P264-P264+P265-P270-P271-P272-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P308+P316-P316-P317-P318-P319-P321-P330-P332+P317-P333+P317-P337+P317-P361+P364-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Germ cell mutagenicity	Muta.	2	H341
Carcinogenicity	Carc.	1B	H350
Reproductive toxicity	Repr.	1B	H360
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	1	H370
Skin sensitization	Skin Sens.	1A	H317
Reproductive toxicity	Repr.	1A	H360F
Reproductive toxicity	Repr.	1B	H360F
Acute toxicity	Acute Tox.	3	H301
Skin corrosion	Skin Corr.	1	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Reproductive toxicity	Repr.	1B	H360Df
Reproductive toxicity	Repr.	1A	H360
Reproductive toxicity	Repr.	1B	H360F

• Transport Information: UN 2810

Discovery and Applications

Glycidyl methacrylate (GMA) is a versatile chemical compound with the molecular formula C₇H₁₀O₃, characterized by the presence of both an epoxide group and a methacrylate group. This dual functionality makes GMA a valuable monomer in various polymerization reactions, leading to its widespread use in the production of specialty polymers, coatings, adhesives, and composites.

The discovery of glycidyl methacrylate can be traced back to the mid-20th century when researchers were exploring new monomers for use in polymer chemistry. The compound was identified as particularly promising due to its reactive epoxide group, which allows it to undergo copolymerization with a wide range of other monomers, and its methacrylate group, which provides a site for radical polymerization. This unique combination of properties has made GMA an important building block in the synthesis of functional polymers.

One of the primary applications of glycidyl methacrylate is in the production of epoxy resins. When GMA is copolymerized with other monomers, it forms polymers with reactive epoxide groups that can be further cross-linked using curing agents. These epoxy-based polymers are widely used in the coatings industry, particularly for protective coatings on metals and other surfaces. The high reactivity of the epoxide groups in GMA-based polymers allows for strong adhesion to substrates and excellent resistance to chemicals and environmental factors.

Glycidyl methacrylate is also used in the production of acrylic resins, which are employed in a variety of applications, including adhesives, sealants, and composites. The presence of the methacrylate group in GMA enables its copolymerization with other acrylic monomers, resulting in resins with enhanced mechanical properties and durability. These acrylic resins are often used in the automotive and aerospace industries, where they provide lightweight, high-performance materials for coatings, structural components, and adhesives.

In addition to its use in coatings and adhesives, glycidyl methacrylate is utilized in the synthesis of ion exchange resins, which are important in water treatment and purification processes. The reactive epoxide group in GMA allows for the introduction of functional groups that can selectively bind to ions, making these resins effective in removing contaminants from water. This application highlights the versatility of GMA in creating polymers with specific and tailored functionalities.

Furthermore, GMA is employed in the development of biomedical materials, particularly in the fabrication of hydrogels and drug delivery systems. The ability of GMA to undergo copolymerization with hydrophilic monomers allows for the creation of hydrogels with controlled swelling properties and biocompatibility. These materials are used in wound dressings, tissue engineering, and as carriers for controlled drug release.

The handling of glycidyl methacrylate requires careful attention to safety, as the compound is known to be a skin sensitizer and can cause irritation upon contact. Proper protective equipment and handling procedures are essential when working with GMA to minimize exposure and potential health risks.

Overall, the discovery and application of glycidyl methacrylate have had a significant impact on the field of polymer chemistry, enabling the development of a wide range of high-performance materials with applications across numerous industries.

References

2014. Preparation of a novel weak cation exchange/hydrophobic interaction chromatography dual-function polymer-based stationary phase for protein separation using “thiol-ene click chemistry”. Analytical and Bioanalytical Chemistry, 407(6), 1729-1740.
DOI: 10.1007/s00216-014-8400-9

2012. Equilibrium and kinetics study on hexavalent chromium adsorption onto diethylene triamine grafted glycidyl methacrylate based copolymers. Journal of Hazardous Materials, 217-218, 315-322.
DOI: 10.1016/j.jhazmat.2011.12.079

2007. Living Radical Polymerizations with Germanium, Tin, and Phosphorus Catalysts − Reversible Chain Transfer Catalyzed Polymerizations (RTCPs). Journal of the American Chemical Society, 129(42), 12628-12629.
DOI: 10.1021/ja0755820