Glycidyl methacrylate

Synonym(s):2,3-Epoxypropyl methacrylate;GMA;Methacrylic acid 2,3-epoxypropyl ester

CAS NO.：106-91-2
Empirical Formula: C7H10O3
Molecular Weight: 142.15
MDL number: MFCD00005137
EINECS: 203-441-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-07-02 17:04:22

What is Glycidyl methacrylate?

Description

Glycidyl Methacrylate (GMA) is a clear, colorless liquid with a potent ester and fruity odor. It comprises a polymerizable methacrylate functional group on one end and a reactive epoxy group on the other. It is slightly miscible with water, soluble in most organic solvents, and has relatively low volatility. Its vapor is heavier than air. It copolymerizes readily with various functional groups, such as phenols, ketones, acids, and amines. The added epoxy group imparts durability, mechanical strength, optical transparency, and adhesiveness.

Chemical properties

Glycidyl methacrylate (GMA) is a colorless liquid with a fruity odor. Floats on water. (USCG, 1999)

Glycidyl methacrylate is a polyfunctional monomer. It acts as an adhesion promoting crosslinking co-monomer for acrylic and vinyl resins. It is also a reactive colorless diluent. GMA is soluble in ethanol, acetone, diethyl ether, benzene.

The Uses of Glycidyl methacrylate

Glycidyl methacrylate (GMA) is a common monomer used in the creation of epoxy resins. It is used to provide epoxy functionalization to polyolefins and other acrylate resins.
Glycidyl methacrylate is used in the production of polymer coatings and finishes, adhesives, plastics and elastomers.
Glycidyl methacrylate dextran has been reported to be used as a biocompatible hydrogel. In situ polymerization of GMA with trimethylolpropane trimethacrylate to form macroporous sorbents has also been reported. GMA may also be grafted onto polypropylene.

The Uses of Glycidyl methacrylate

Glycidyl methacrylate is commonly used as a monomer for the preparation of epoxy resins. It is also used to provide epoxy functionalization to polyolefins and other acrylate resins. Further, it is also useful as an epoxy resin additive for paint coating formulations and adhesive applications.

Preparation

Glycidyl methacrylate is produced from methacrylic acid and glycidol. Glycidol contain both epoxide and alcohol functional groups.It is an enoate ester and an epoxide. It derives from a methacrylic acid and a glycidol.

definition

ChEBI: Glycidyl methacrylate is an enoate ester obtained by formal condensation of the carboxy group of methacrylic acid with the hydroxy group of glycidol. It is an enoate ester and an epoxide. It is functionally related to a methacrylic acid and a glycidol.

Reactions

Glycidyl methacrylate (GMA) is a kind of functional monomer. Its active vinyl and epoxy groups could be grafted with polyolefin and reacted with the polar groups such as amine, hydroxyl and carboxyl group, respectively. It can also undergo polymerization to form poly (glycidyl methacrylate).

Synthesis Reference(s)

Tetrahedron, 48, p. 5099, 1992 DOI: 10.1016/S0040-4020(01)90120-6
Synthesis, p. 1019, 1986 DOI: 10.1055/s-1986-31856

General Description

Colorless liquid with a fruity odor. Floats on water.

Air & Water Reactions

Flammable. Slightly water soluble.

Reactivity Profile

Epoxides, such as Glycidyl methacrylate, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Health Hazard

The liquid irritates eyes about as much as soap. Prolonged contact with skin produces irritation and dermatitis.

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors are generated when heated

Flammability and Explosibility

Flammable

Properties of Glycidyl methacrylate

Melting point:	-52°C
Boiling point:	189 °C(lit.)
Density	1.075 g/mL at 20 °C
vapor pressure	4.2hPa at 25℃
refractive index	n20/D 1.449(lit.)
Flash point:	169 °F
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Liquid
color	Clear
Water Solubility	0.5-1.0 g/100 mL at 20 ºC
BRN	2506
Stability:	Unstable. Light sensitive. May be stabilized with around 100ppm MEHQ. Refrigerate.
CAS DataBase Reference	106-91-2(CAS DataBase Reference)
IARC	2A (Vol. 125) In prep.
NIST Chemistry Reference	2-Propenoic acid, 2-methyl-, oxiranylmethyl ester(106-91-2)
EPA Substance Registry System	Glycidyl methacrylate (106-91-2)

Safety information for Glycidyl methacrylate

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08
GHS Hazard Statements	H302:Acute toxicity,oral H311:Acute toxicity,dermal H314:Skin corrosion/irritation H317:Sensitisation, Skin H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H341:Germ cell mutagenicity H350:Carcinogenicity H372:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes	P202:Do not handle until all safety precautions have been read and understood. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.