GLYCIDYL METHACRYLATE
Glycidyl Methacrylate; 106-91-2; Description and uses: Small additives GMA (glycidyl methacrylate) and its derivatives to different polymeric materials improve their mechanical, optical, adhesive characteristics, chemical and atmospheric durability. GMA (glycidyl methacrylate) is used for an improvement in the quality and reaching of the optimum performance properties of varnishes and paints, natural rubbers, latexes, sealing compounds, industrial protective coatings, synthetic fibers, paper, thermoplastics, electros-laminate, structural and ion-exchange materials, used in polygraphy, automobile construction, to radio engineering and to microelectronics, biotechnology and to medicine. Characteristic property GMA is its dual functionality - due to the methacrylic and epoxy groups. This gives to it the possibility to combine the chemical properties of acrylates, reacting with styrene, by acrylates or by ethylene, and epoxies. Epoxy group GMA is capable of different chemical transformations both in the monomer and in the polymers. Its ability easily to react with different substances (amines, phenols, ketones, carbonaceous acids, which contain halogen and other.) it makes it possible to synthesize many new chemical connections.
Synonym: 2,3-Epoxypropylmethacrylate; oxiran-2-ylmethyl 2-methylprop-2-enoate.Other names: glycidyl methacrylate, 2,3-epoxypropyl methacrylate, 2-((Methacryloxy)methyl)oxirane
Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol, it is a common monomer used in the creation of epoxy resins.
While typical home epoxies contain diglycidyl ether of bisphenol A (DGEBA), glycidyl methacrylate is instead used to provide epoxy functionalization to polyolefins and other acrylate resins
Glycidyl methacrylate is a colorless liquid with a fruity odor. Floats on water
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 derives from a methacrylic acid and a glycidol.
Glycidyl methacrylate (GMA) is an is an epoxy-functional monomer/ acrylic monomer ester with the molecular formula C7H10O3, CAS 106-91-2. It has a sharp odour that may be troublesome.
It is a common monomer used in the creation of epoxy resins. Glycidyl methacrylate is used to provide epoxy functionalization to polyolefins and other acrylate resins.
Production
Glycidyl methacrylate is produced from methacrylic acid and glycidol. Glycidol contain both epoxide and alcohol functional groups.
Uses
Glycidyl methacrylate is used in the production of polymer coatings and finishes, adhesives, plastics and elastomers.
GMA can also undergo polymerization to form poly (glycidyl methacrylate).
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.
Uses
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.
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)
Synthesis, p. 1019, 1986
Tetrahedron, 48, p. 5099, 1992 DOI: 10.1016/S0040-4020(01)90120-6
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
106-91-2
Name: Glycidyl methacrylate
CAS: 106-91-2
Molecular Formula: C7H10O3
Molecular Weight: 142.152
CAS: 106-91-2
106-91-2 - Names and Identifiers
Name: Glycidyl methacrylate
Synonyms: 2,3-Epoxypropyl methacrylate
Methacrylic acid glycidyl ester
oxiran-2-ylmethyl 2-methylprop-2-enoate
(2S)-oxiran-2-ylmethyl 2-methylprop-2-enoate
(2R)-oxiran-2-ylmethyl 2-methylprop-2-enoate
2-Propenoic acid,2-methyl-,2-oxiranylmethyl ester
Epoxypropyl methacrylate
GMA
CAS 106-91-2
EINECS 203-441-9
106-91-2 - Physico-chemical Properties
Molecular Formula: C7H10O3
Molar Mass: 142.152 g/mol
Density 1.095g/cm3
Boling Point: 189°C at 760 mmHg
Flash Point:76.1°C
Solubility:0.5-1.0 g/100 mL at 20℃
Vapor Presure:0.582mmHg at 25°C
Refractive Index:1.457
EC / List no.: 203-441-9
CAS no.: 106-91-2
Mol. formula: C7H10O3
1-Propanol, 2,3-epoxy-, methacrylate
2,3-epoxypropyl methacrylate
2,3-Epoxypropyl methacrylate
2,3-epoxypropyl methacrylate
2,3-epoxypropyl methacrylate; glycidyl methacrylate
2,3-Epoxypropyl methacrylic acid ester
2-((Methacryloxy)methyl)oxirane
2-Propenoic acid, 2-methyl-, 2-oxiranylmethyl ester
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester
Acriester G
Blemmer G
Other
Blemmer GMA
Glycidol methacrylate
Glycidyl alpha-methyl acrylate
Glycidyl methacrylate
glycidyl methacrylate
Light Ester G
Methacrylic acid, 2,3-epoxypropyl ester
methacrylic acid, 2,3-epoxypropyl ester
SR 379
Translated names
(oxiranylmetyl)-metakrylát (sk)
2,3-epoksipropil metakrilat (sl)
2,3-epoksipropil-metakrilat (hr)
2,3-epoksipropilmetakrilatas (lt)
2,3-epoksipropilmetakrilāts (lv)
2,3-epoksypropylmetakrylat (no)
2,3-epoksüpropüülmetakrülaat (et)
2,3-epossipropile metacrilato (it)
2,3-epoxipropil metacrilat (ro)
2,3-epoxipropil-metakrilát (hu)
2,3-epoxipropylmetakrylat (sv)
2,3-epoxypropyl-methakrylát (cs)
2,3-epoxypropylmethacrylaat (nl)
2,3-epoxypropylmethacrylat (da)
2,3-Epoxypropylmethacrylat (de)
2,3-епоксипропил метакрилат (bg)
ester 2,3-epoksypropylowy kwasu metakrylowego (pl)
glicidil metacrilat (ro)
glicidil metacrilato (it)
glicidil metakrilat (sl)
glicidil-metakrilat (hr)
glicidil-metakrilát (hu)
glicidilmetakrilatas (lt)
glicidilmetakrilāts (lv)
glycidyl-metakrylát (sk)
glycidyl-methakrylát (cs)
glycidylmetakrylat (no)
glycidylmetakrylat (sv)
glycidylmethacrylaat (nl)
glycidylmethacrylat (da)
Glycidylmethacrylat (de)
Glysidyylimetakrylaatti (fi)
Glütsidüülmetakrülaat (et)
metacrilato de 2,3-epoxipropilo (es)
metacrilato de 2,3-epoxipropilo (pt)
metacrilato de glicidilo (es)
metacrilato de glicidilo (pt)
metakrylan 2,3-epoksypropylu (pl)
metakrylan glicydowy (pl)
méthacrylate de 2,3-époxypropyle (fr)
méthacrylate de glycidyle (fr)
μεθακρυλικός 2,3-εποξυπροπυλεστέρας μεθακρυλικός γλυκυδυλεστέρας (el)
глицидил метакрилат (bg)
CAS names
2-Propenoic acid, 2-methyl-, 2-oxiranylmethyl ester
IUPAC names
(2,3-Epoxy-propyl)-methacrylat
(2S)-oxiran-2-yl]methyl 2-methylprop-2-enoate
(oxiran-2-yl)methyl 2-methylprop-2-enoate
2,3-Epoxypropyl methacrylate
2,3-epoxypropyl methacrylate
2,3-epoxypropyl methacrylate
2,3-epoxypropyl methacrylate/glycidyl methacrylate
2,3-epoxypropyl methacrylate/glycidyl methacrylate
2,3-epoxypropyl methacrylate; glycidyl methacrylate
2,3-Epoxypropylmethacrylat
2-Oxiranylmethyl 2-methylacrylate, Glycidyl methacrylate
2-propenoic acid, 2-methyl-,2-oxiranylmethyl ester
GLYCIDYL METHACRYLATE
Glycidyl Methacrylate
Glycidyl methacrylate
glycidyl methacrylate
Glycidyl Methacrylate
Glycidyl methacrylate
Glycidyl Methacrylate (stabilized with MEHQ)
glycidylmethacrylate
GMA
Methacrylsäure-2,3-epoxypropylester
oxiran-2-yl methyl 2-methylprop-2-enoate
oxiran-2-ylmethyl 2-methylprop-2-enoate
oxiran-2-ylmethyl methacrylate
Trade names
2,3-epoxypropyl methacrylate
ACRYESTER G
Glycidyl methacrylate
glycidyl methacrylate
GMA
(±)-Glycidyl methacrylate
106-91-2 [RN]
2,3-EPOXYPROPYL METHACRYLATE
2,3-Epoxypropyl methacrylic acid ester
2-[(Methacryloyloxy)methyl]oxirane
203-441-9 [EINECS]
2-Methyl-2-propenoic acid oxiranylmethyl ester
2-Oxiranylmethyl methacrylate [ACD/IUPAC Name]
2-Oxiranylmethylmethacrylat [German] [ACD/IUPAC Name]
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester [ACD/Index Name]
Allyl glycidyl ether [UN2219] [Flammable liquid]
Glycidol methacrylate
Glycidyl methacrylate [Wiki]
Glycidyl α-methylacrylate
GMA
Méthacrylate de 2-oxiranylméthyle [French] [ACD/IUPAC Name]
Methacrylic acid 2,3-epoxypropyl ester
Methacrylic acid, 2,3-epoxypropyl ester
MFCD00005137 [MDL number]
oxiran-2-ylmethyl methacrylate
R8WN29J8VF
Sartomer 379
sy-monomer g
UNII:R8WN29J8VF
(oxiran-2-yl)methyl 2-methylprop-2-enoate
[106-91-2]
1-Allilossi-2,3 epossipropano [Italian]
1-Propanol, 2,3-epoxy-, methacrylate
2-((Methacryloxy)methyl)oxirane
2,3-Epoxypropanol methacrylate
2,3-Epoxypropylmethacrylate
203-442-4 [EINECS]
2-methyl-2-propenoic acid [(2R)-2-oxiranyl]methyl ester
2-Methyl-acrylic acid oxiranylmethyl ester
2-Oxiranylmethyl 2-methylacrylate
2-Propenoic acid, 2-methyl-, 2-oxiranylmethyl ester
5-17-03-00012 [Beilstein]
95%, stab. with100 ppm MEHQ
Acriester G
AGE
Allil-glicidil-etere
Allyl 2, 3-epoxypropyl ether
Allylglycidaether [German]
Denacol EX 111
Epiol A
glycidyl methacrylate 95%
glycidyl methacrylate, 97%, stabilized
Glycidyl α-methylacrylate
glycidylmethacrylate
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132844
Jsp000614
methacrylic acid glycidyl ester
oxiran-2-ylmethyl 2-methylacrylate
oxiran-2-ylmethyl 2-methylprop-2-enoate
OXIRANYLMETHYL-2-METHYL-2-PROPENOATE
Oxyde d'allyle et de glycidyle
Propane, 1-(allyloxy)-2,3-epoxy- (8CI)
Santolin XI
SR-379
VS-02747
WLN: T3OTJ B1OVY1 & U1
GLYCIDYL METHACRYLATE
106-91-2
2,3-Epoxypropyl methacrylate
SY-Monomer G
Glycidol methacrylate
Acriester G
Blemmer G
Blemmer GMA
Light Ester G
glycidylmethacrylate
oxiran-2-ylmethyl 2-methylprop-2-enoate
Methacrylic Acid Glycidyl Ester
2-((Methacryloxy)methyl)oxirane
Methacrylic acid, 2,3-epoxypropyl ester
Glycidyl alpha-methylacrylate
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester
CP 105
Polyglycidyl methacrylate
NSC 24156
Glycidyl alpha-methyl acrylate
oxiran-2-ylmethyl methacrylate
1-Propanol, 2,3-epoxy-, methacrylate
CCRIS 2626
HSDB 494
EINECS 203-441-9
SR 379
Glycidyl methacrylate(GMA)
2,3-Epoxypropyl methacrylic acid ester
BRN 0002506
2,3-Epoxypropanol methacrylate
Glycidyl .alpha.-methylacrylate
DTXSID0025361
2-Propenoic acid, 2-methyl-, 2-oxiranylmethyl ester
MFCD00005137
(oxiran-2-yl)methyl 2-methylprop-2-enoate
DSSTox_CID_5361
DSSTox_RID_77762
DSSTox_GSID_25361
GMA
oxiran-2-ylmethyl 2-methylacrylate
Methacrylic acid,3-epoxypropyl ester
WLN: T3OTJ B1OVY1 & U1
Glycidyl methacrylate, 97%, stabilized
CAS-106-91-2
25067-05-4
Acryester G
glycidyl-methacrylate
PubChem23289
ACMC-20dh4k
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester, homopolymer
methacrylic acid glycidyl
2-Propenoic acid, 2-methyl-, (2R)-oxiranylmethyl ester
EC 203-441-9
NCIOpen2_000036
SCHEMBL15617
5-17-03-00035 (Beilstein Handbook Reference)
KSC175C8B
methacrylic acid-glycidyl ester
CHEMBL1333073
CTK0H5180
KS-00000BXD
CHEBI:132844
130463-96-6
NSC24156
NSC67195
Tox21_201494
Tox21_303145
2-Oxiranylmethyl 2-methylacrylate #
ANW-15457
BBL010914
LS-411
NSC-24156
NSC-67195
SBB081273
SR-379
STK801798
AKOS000276065
AKOS016041668
MCULE-2297059991
Glycidyl methacrylate, >=97.0% (GC)
NCGC00091055-01
NCGC00091055-02
NCGC00256974-01
NCGC00259045-01
VS-02747
2-methyl-acrylic acid oxiranylmethyl ester
Oxiran-2-ylmethyl methacrylate 106-91-2
Epoxypropyl methacrylate,5 cp(25 degrees c)
FT-0609742
Glycidyl Methacrylate (stabilized with MEHQ)
M0590
ST50330616
Glycidyl Methacrylate, (stabilized with MEHQ)
2-methyl-acrylic acid oxiran-2-yl-methyl ester
Glycidyl methacrylate, purum, >=97.0% (GC)
Q2013175
W-108764
Glycidyl methacrylate, stab. with 100ppm 4-methoxyphenol
2-Propenoic acid, 2-methyl-, 2-oxiranylmethyl ester, homopolymer
Glycidyl methacrylate, 97%, contains 100 ppm monomethyl ether hydroquinone as inhibitor
