Name | Glycidyl methacrylate |
Synonyms | GMA cp105 CP 105 blemmergma Glycidol methacrylate Glycidyl methacrylate Epoxypropyl methacrylate 2,3-Epoxypropyl methacrylate Methacrylic acid glycidyl ester oxiran-2-ylmethyl 2-methylprop-2-enoate (2R)-oxiran-2-ylmethyl 2-methylprop-2-enoate (2S)-oxiran-2-ylmethyl 2-methylprop-2-enoate 2-Propenoic acid,2-methyl-,2-oxiranylmethyl ester 2-Methyl-2-oxiranyl-2-propenoic acid Methyl ester Glycidyl Methacrylate OR Methacrylic acid 2,3-epoxypropyl ester |
CAS | 106-91-2 |
EINECS | 203-441-9 |
InChI | InChI=1/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3/t6-/m1/s1 |
InChIKey | VOZRXNHHFUQHIL-UHFFFAOYSA-N |
Molecular Formula | C7H10O3 |
Molar Mass | 142.15 |
Density | 1.075g/mLat 20°C |
Melting Point | -52°C |
Boling Point | 189°C(lit.) |
Flash Point | 169°F |
Water Solubility | 0.5-1.0 g/100 mL at 20 ºC |
Vapor Presure | 4.2hPa at 25℃ |
Appearance | Transparent liquid |
Color | Clear |
BRN | 2506 |
Storage Condition | 2-8°C |
Stability | Unstable. Light sensitive. May be stabilized with around 100ppm MEHQ. Refrigerate. |
Sensitive | Sensitive to heat |
Refractive Index | n20/D 1.449(lit.) |
MDL | MFCD00005137 |
Physical and Chemical Properties | Density 1.042 boiling point 189°C refractive index 1.449-1.451 flash point 76°C water-soluble 0.5-1.0g/100 mL at 20°C |
Use | Mainly used in acrylic powder coating, latex coating, textile leather finishing agent, adhesive, medicine and so on |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/38 - Irritating to eyes and skin. R43 - May cause sensitization by skin contact R60 - May impair fertility R45 - May cause cancer R68 - Possible risk of irreversible effects R39/26 - R34 - Causes burns |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S28 - After contact with skin, wash immediately with plenty of soap-suds. S28A - S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S53 - Avoid exposure - obtain special instructions before use. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
UN IDs | UN 2810 6.1/PG 3 |
WGK Germany | 2 |
RTECS | OZ4375000 |
TSCA | Yes |
HS Code | 29161490 |
Hazard Class | 8 |
Packing Group | III |
Reference Show more | 1. Donglin Han, Yuan Li, Xiangmei Liu, Bo Li, Yong Han, Yufeng Zheng, Kelvin Wai Kwok Yeung, Changyi Li, Zhenduo Cui, Yanqin Liang, Zhaoyang Li, Shengli Zhu, Xianbao Wang, Shuilin Wu, Rapid bacteria trapping and killing of metal-organic frameworks strengthene 2. [IF=6.141] Jianfeng Xu et al."Preparation and properties of high-performance fast-growing wood modified by exfoliated organo-montmorillonite in waterborne hyperbranched polyacrylate emulsion."Constr Build Mater. 2021 Sep;298:123868 3. [IF=4.821] Weihao Bao et al."Preparation and modeling study of novel carboxymethyl-β-cyclodextrin silica hybrid monolithic column for enantioseparations in capillary electrochromatography."Microchem J. 2021 Nov;170:106719 4. [IF=3.171] Xiaoyan Li et al."Wood composites modified with waterborne hyperbranched polyacrylate dispersed organo-montmorillonite emulsion and the permeability investigations by surface characterizations."Polym Composite. 2020 Sep;41(9):3798-3806 5. [IF=2.393] Jianfeng Xu et al."Enhancement of the physical and mechanical properties of wood using a novel organo-montmorillonite/hyperbranched polyacrylate emulsion."Holzforschung. 2021 Jun;75(6):545-554 6. [IF=1.713] Dianyu Yu et al."Immobilization of cellulase on magnetic nanoparticles for rice bran oil extraction in a magnetic fluidized bed."Int J Food Eng. 2021 Dec;: |
glycidyl methacrylate is a colorless transparent liquid; Relative density (25 °c) 1.078; Boiling point (0. lMPa) 189 ℃; Melting point -50 ℃; Flash Point (open) 84 ℃; Epoxy oxygen content of 11.2%; Bromine value of 112; Saponification value of 395; Insoluble in water; Soluble in organic solvents.
The glycidyl methacrylate monomer is a bifunctional monomer, which has both a double bond and an epoxy group, and can participate in a free radical and an ionic polymerization reaction, and can undergo a crosslinking reaction through an epoxy group. First, methacrylic acid was reacted with anhydrous Na2 C03 or NaOH to form sodium methacrylate Salt. Then, glycidyl methacrylate was prepared by reacting methacrylic acid with propylene oxide in a quaternary ammonium salt catalyst and a small amount of polymerization inhibitor.
glycidyl methacrylate has been widely used in medicine, photosensitive materials and polymer synthesis and many other fields. In polymer synthesis, it is used as a cross-linking monomer and reactive diluent, and is also widely used in adhesives, flame retardant materials, insulating materials, water-absorbing materials, polymer capsules, solvent-based coatings, acrylic and polyester powder coatings, rubber modifier and resin modifier, etc.
plastic barrel packaging.
LogP | 0.96 at 25℃ |
(IARC) carcinogen classification | 2A (Vol. 125) In prep. |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
introduction | glycidyl methacrylate (Glycidyl Methacrylate, abbreviated GMA) is a monomer with both acrylate double bonds and epoxy groups. The double bond of acrylate has high reactivity and can undergo self-polymerization reaction or copolymerization with many other monomers; while epoxy groups can react with hydroxyl, amino, carboxyl or acid anhydride to introduce More functional groups bring more functionality to the product. Therefore, GMA has a wide range of applications in organic synthesis, polymer synthesis, polymer modification, composite materials, UV curable materials, coatings, adhesives, leather, chemical fiber papermaking, printing and dyeing, etc. |
application field | GMA is widely used in organic synthesis, polymer synthesis, polymer modification, composite materials, UV curable materials, coatings, adhesives, leather, chemical fiber papermaking, printing and dyeing, etc. GMA is used in powder coating: one of the main uses of GMA is to make powder coating matting resin for outdoor use. Due to its epoxy group, it has excellent powder coating leveling performance, weather resistance, salt spray resistance, high temperature resistance, and yellowing resistance. application of GMA in plastic modification: GMA can be grafted to polymer due to the existence of an acrylate double bond with high activity. GMA grafted POE is mainly used as polyester compatibilizer on the market. These functionalized polymers can be used as toughening agents to toughen engineering plastics or as compatibilizers to improve the compatibility of blend systems. Application of GMA in UV glue: Double bond is used for UV free radical monomer, free radical cation curing, because there are epoxy groups, so the curing speed is slow, but the bonding effect is better. GMA application in PCB ink: GMA can be used to produce PCB ink and green oil of acrylic system. Green oil is the circuit board ink. |
Synthesis method | The two-step method is to first carry out a ring-opening esterification reaction between methacrylic acid and epichlorohydrin under the action of a ring-opening catalyst to generate 2-hydroxy3-chloropropyl methacrylate. Then 2-hydroxy3-chloropropyl methacrylate is subjected to a closed-loop reaction of dehydrochlorination in the presence of sodium hydroxide solid or aqueous solution, or reflux in acetone solution of potassium carbonate to obtain the product. |
use | mainly used in powder coatings, but also used in thermosetting coatings, fiber treatment agents, adhesives, antistatic agents, vinyl chloride stabilizers, rubber and resin modifiers, ion exchange resins and adhesives for printing inks. Mainly used in acrylic powder coatings, latex coatings, textile leather finishing agents, adhesives, medicine, etc. GMA for short. Because its molecule contains carbon-carbon double bonds and epoxy groups, it can perform both free radical reactions and ionic reactions. Therefore, it has high reactivity and can carry out different reactions. It is an important fine chemical raw material. Commonly used in acrylic and polyester decorative powder coatings, industrial and protective topcoats, alkyd resins, adhesives, acrylic resin/emulsion synthesis, polyvinyl chloride coatings, substitutes for hydrogenated LER, plastic modifications, flame retardant materials, absorbent materials, polymer capsules, cross-linked monomers and reactive diluents |
Production method | It is obtained by the reaction of sodium methacrylate and epichlorohydrin. Raw material consumption quota: 780kg/t methacrylic acid, 690kg/t epichlorohydrin and 330kg/t sodium hydroxide. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |