106-91-2 Usage
Description
Glycidyl methacrylate (GMA) is a polyfunctional monomer that is a colorless liquid with a fruity odor and has the ability to float on water. It acts as an adhesion-promoting crosslinking co-monomer for acrylic and vinyl resins and is also a reactive colorless diluent. GMA is soluble in ethanol, acetone, diethyl ether, and benzene.
Uses
Used in Coatings and Adhesives Industry:
Glycidyl methacrylate is used as a monomer for the preparation of epoxy resins, providing epoxy functionalization to polyolefins and other acrylate resins. It is utilized in the production of polymer coatings and finishes, adhesives, plastics, and elastomers.
Used in Biocompatible Hydrogels:
Glycidyl methacrylate dextran has been reported to be used as a biocompatible hydrogel, offering potential applications in the medical and pharmaceutical fields.
Used in Sorbent Production:
In situ polymerization of GMA with trimethylolpropane trimethacrylate is employed to form macroporous sorbents, which can be used in various industrial and environmental applications for the absorption and separation of different substances.
Used in Polymer Modification:
GMA may be grafted onto polypropylene, enhancing its properties and expanding its range of applications in the plastics industry.
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.
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)90120-6Synthesis, p. 1019, 1986 DOI: 10.1055/s-1986-31856
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
Check Digit Verification of cas no
The CAS Registry Mumber 106-91-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 106-91:
(5*1)+(4*0)+(3*6)+(2*9)+(1*1)=42
42 % 10 = 2
So 106-91-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3/t6-/m1/s1
106-91-2Relevant articles and documents
Environmentally benign synthesis of vinyl ester resin from biowaste glycerin
Shah, Priyank N.,Kim, Namjoon,Huang, Zhuangrong,Jayamanna, Mahesh,Kokil, Akshay,Pine, Alex,Kaltsas, Jarmin,Jahngen, Edwin,Ryan, David K.,Yoon, Seongkyu,Kovar, Robert F.,Lee, Yongwoo
, p. 38673 - 38679 (2015)
We present here for the first time a novel environmentally benign protocol for the synthesis of vinyl ester resin (VER). Our synthetic strategy utilizes a commercial waste material, glycerin, from biodiesel manufacturing and converts it into a widely utilized resin. The VER was synthesized using bisphenol A (BPA) and glycidyl methacrylate (GMA) as precursors. GMA was synthesized via a multistep synthetic protocol using glycerin obtained from a biodiesel manufacturing waste stream. The structure of the intermediates was confirmed by 1H NMR, HPLC and FT-IR spectroscopy.
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Iwakura et al.
, p. 570,572 (1961)
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(Methyl) acrylic acid ether hydroxyl alkane ester synthesis method
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Paragraph 0027, (2019/08/07)
The invention relates to the field of organic synthesis and discloses an (methyl) acrylic acid ether hydroxyl alkane ester synthesis method. The method includes steps: subjecting methyl acrylic acid and epoxy chloropropane to reaction to generate acrylic ester with an epoxy group; subjecting the epoxy group to positioning and ring opening to enable a hydroxyl at 2-site carbon and a sterically hindered ether bond at a 3 site; subjecting to reaction with a primary alcohol compound to generate a target product. The method has advantages that side reactions in a synthesizing process are less, polymer crystallinity can be changed, mechanical performances such as tensile strength of a polymer are enhanced, and the hydrophilic performance can be changed.
Glycidyl methacrylate or glycidyl acrylate manufacturing method
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Paragraph 0066-0068, (2017/04/07)
The invention relates to a manufacturing method of glycidyl methacrylate or glycidyl acrylate. The invention provides glycidyl (meth)acrylate with low impurity content. The manufacturing method of glycidyl (meth)acrylate comprises a step of reacting epichlorohydrin and (meth)acrylic acid alkali metal salt or (meth)acrylic acid in the presence of catalyst and a step of washing the reaction liquid obtained through the reaction at the temperature ranging from minus 13 DEG C to 20 DEG C.