GLYCIDYL METHACRYLATE

GLYCIDYL METHACRYLATE = GMA

CAS Number: 106-91-2
EC Number: 203-441-9
Chemical formula: C7H10O3
Molar mass: 142.1546 g/mol

Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol.
Containing both an epoxide and an acrylate groups, the molecule is bifunctional.

Glycidyl methacrylate is a common monomer used in the production 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 used to prepare a range of composites.

Glycidyl methacrylate (GMA) is an is an epoxy-functional monomer/ acrylic monomer ester with the molecular formula C7H10O3, CAS 106-91-2.
Glycidyl methacrylate has a sharp odour that may be troublesome.

Glycidyl methacrylate 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.

Glycidyl Methacrylate (GMA) is a clear, colorless liquid with a strong ester and fruity odor.
Glycidyl methacrylate comprised of a polymerizable methacrylate functional group on one end and a reactive epoxy group on the other end.

Glycidyl methacrylate is slightly miscible with water, soluble in most organic solvents and has relatively low volatility.
Glycidyl methacrylate vapor is heavier than air.

Glycidyl methacrylate copolymerizes readily with a wide variety of functional groups such as phenols, ketones, acids and amines.
The added epoxy group imparts properties such as durability, mechanical strength, optical transparency, and adhesiveness.

Glycidyl Methacrylate (GMA) is an ester of Methacrylic Acid and Glycidol.
The characteristic of the property of Glycidyl Methacrylate (GMA) is Glycidyl methacrylate dual functionality – due to the methacrylic and epoxy groups.

This gives Glycidyl methacrylate the possibility to combine the chemical properties of acrylates, reacting with styrene, by acrylates or by ethylene, and epoxies.
The epoxy group of Glycidyl Methacrylate (GMA) is capable of different chemical transformations both in the monomer and in the polymers.

Glycidyl Methacrylate (GMA) reacts with different substances (amines, phenols, ketones, carbonaceous acids, which contain halogen and others).
Glycidyl methacrylate makes it possible to synthesize many new chemical connections.
Small additives of Glycidyl Methacrylate (GMA) and its derivatives to different polymeric materials improve their mechanical, optical, adhesive characteristics, chemical, and atmospheric durability.

Physical Description of Glycidyl methacrylate:
Glycidyl methacrylate is a colorless liquid with a fruity odor.
Floats on water.

Application of Glycidyl methacrylate:
Glycidyl methacrylate (GMA) is an epoxy-functional monomer generally used to derivatize polymers.
Glycidyl methacrylate can also undergo polymerization to form poly (glycidyl methacrylate).

Glycidyl Methacrylate can be homopolymerized into PolyGMA or co-polymerized with styrene to form Styrene-GMA co- polymers to form a variety of latexes.
These products exhibit high flexibility, good weatherability, and UV stability.

GMA is readily converted to PolyGMA and used in a variety of block polymerizations.
Polymers containing GMA exhibit the following characteristics.

Mechanical strength, flexibility, durability, toughness
Weather resistance, moisture resistance
Crosslinking sites, epoxy group reacts readily with phenols, ketones and eaters.

Corrosion and abrasion resistance, as well as optical improvement while contributing to low odor, color, and volatility.
Glycidyl Methacrylate monomer is also used in the manufacture of paints, varnishes,
coatings, adhesives and sealants, fibers, thermoplastics, epoxies, and powder coatings.

Glycidyl Methacrylate (GMA) is used for improving the quality and reaching the optimum performance properties of varnishes and paints, natural rubbers, latexes, sealing compounds, industrial protective coatings, synthetic fibers, paper, thermoplastics, structural and ion-exchange materials, used in polygraphy, automobile construction, radio engineering and microelectronics, biotechnology and in medicine.

Uses of Glycidyl methacrylate:
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).

Arpadis is one of the largest chemical distributor in Europe.
Arpadis is handling the storage, transport, export & import formalities of Glycidyl Methacrylate globally.

Chemical intermediate for polymers; monomer and diluent in epoxy resin formulations; Used in Japan as an intermediate for resins and other chemicals; Also used in emulsions for impregnating paper and textiles, in paint coatings, and adhesive applications

Glycidyl methacrylate (GMA) 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.

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.

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

Glycidyl methacrylate dextran (GMA) 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.

Industry Uses of Glycidyl methacrylate:
Adhesives and sealant chemicals
Intermediates
producing resin for paint/coating and adhesive

Consumer Uses of Glycidyl methacrylate:
Adhesives and sealants
Paints and coatings

Methods of Manufacturing of Glycidyl methacrylate:

Reaction of methacrylic acid with glycidol:
The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol.

Epichlorohydrin + methacrylic acid (esterification)

General Manufacturing Information of Glycidyl methacrylate:

Industry Processing Sectors of Glycidyl methacrylate:
Adhesive manufacturing
All other basic organic chemical manufacturing
Paint and coating manufacturing
Plastic material and resin manufacturing

Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates.
None the less, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper.

Analytic Laboratory Methods of Glycidyl methacrylate:
The electron-impact and methane chem-ionization mass spectra of selected acrylate and methacrylate monomers, including glycidyl methacrylate, commonly used in dental Materials are reported and discussed.

The two ionization modes complement each other, and together the mass spectra offer adequate information for identification purposes.
The application of the mass spectral method is demonstrated on resin-based dental materials with identification of the monomer content.

Thin-layer chromatography TLC, polarography, and spectrometry are used for soln measurements.
Methacrylates in air have been analyzed by TLC, polarography, and colorimetry.

Polarography has been used for determination of any residual monomer in the polymer.
A variety of spectroscopic techniques, eg, NMR, IR, and Raman spectroscopy also have been used, particularly for analysis of surgical cements and dental restorative resins.

Polymerization of Glycidyl methacrylate:
Heat, peroxides, and caustics all cause polymerization.

Metabolism/Metabolites of Glycidyl methacrylate:
Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid.
The latter may form an acetyl-coenzyme derivative, which then enters the normal lipid metabolism.

Handling Precautions of Glycidyl methacrylate:
Before using this product, consult the Safety Data Sheet (SDS) for details on product hazards, recommended handling precautions and product storage.

Storage of Glycidyl methacrylate:
Consult the Safety Data Sheet (SDS).
The monomer shelf life informs how long the material will remain stable under normal conditions.
Never store expired material.

To prevent polymerization, Glycidyl Methacrylate (GMA) should always be stored in air, and never under inert gases.
For the stabilizer to work effectively, oxygen is required.
Glycidyl methacrylate must contain a stabilizer.

Storage temperature should not exceed 35 °C.
Under these conditions, the storage stability of one year can be expected.
To minimize the likelihood of congestion, the storage procedure should strictly follow the principle of “first come, first come”.

For a long shelf life of more than 4 weeks, Glycidyl methacrylate is advisable to replenish the oxygen content.
Over time, the content of ethylene glycol diacrylate slowly increases.
If this component is relevant to your process, Glycidyl Methacrylate (GMA) should be used within 12 months of receipt.

The preferred material for tanks and pipes is stainless steel.
Carbon steel is also used, although rust formation may occur, which will lead to a problem with product quality (color).
Iron (III) -ion has been shown to be a weak initiator of polymerization.

If carbon steel is to be used, special treatment should be used to prepare the tank for use.
Storage tanks, pumps, and pipes must be earthed.

Store containers with Glycidyl Methacrylate (GMA) tightly closed in a cool, dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.

Store only if stabilized.
Cool.
Well closed.
Keep in the dark.
Separated from strong oxidants, strong bases and strong acids.
Separated from food and feedstuffs.
Store in an area without drain or sewer access.
Provision to contain effluent from fire extinguishing

Glycidyl methacrylate is a common monomer used in the production of epoxy resins.

KEYWORDS:
106-91-2, 203-441-9, GMA, 2 3-Epoxypropyl methacrylate, Glycidol methacrylate, SY-Monomer G, oxiran-2-ylmethyl 2-methylprop-2-enoate, Blemmer G, Blemmer GMA, Light Ester G

Storage Conditions of Glycidyl methacrylate:
Temp during storage must be kept low to minimize formation of peroxides and other oxidation products.

Storage temp below 30 °C are recommended for the polyfunctional methacrylates.
The methacrylate monomers should not be stored for longer than one year.

Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months.
Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark.
The methacrylic esters may be stored in mild steel, stainless steel, or aluminum.

Reactivity Alerts of Glycidyl methacrylate:
Polymerizable

Reactivity Profile of Glycidyl methacrylate:
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.

Disposal Considerations of Glycidyl methacrylate:
Dispose in accordance with all local, state (provincial) and federal regulations.

Empty containers may contain hazardous residues.
This material and Glycidyl methacrylate container must be disposed in a safe and legal manner.

Safety of Glycidyl methacrylate:
Avoid contact with skin and eyes.

Avoid inhalation of vapour or mist.
Avoid exposure - obtain special instructions before use.

Keep away from sources of ignition - No smoking.
Take measures to prevent the build up of electrostatic charge.

Production of Glycidyl methacrylate:
Glycidyl methacrylate is produced from methacrylic acid and glycidol.
Glycidol contain both epoxide and alcohol functional groups.

First Aid of Glycidyl methacrylate:
EYES: First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.

Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital.

Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.

Be prepared to transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.

DO NOT INDUCE VOMITING.
IMMEDIATELY transport the victim to a hospital.

Fire Fighting of Glycidyl methacrylate:
Fires involving this chemical can be controlled using a dry chemical, carbon dioxide or Halon extinguisher.

Isolation and Evacuation of Glycidyl methacrylate:
As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above.

FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Spillage Disposal of Glycidyl methacrylate:
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance.

Collect leaking and spilled liquid in covered containers as far as possible.
Do NOT let this chemical enter the environment.

Disposal Methods of Glycidyl methacrylate:
At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision.
Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures of Glycidyl methacrylate:
Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop.

This danger should be borne in mind when designing plant.
Awareness of the dangers and of good engineering design are essential to safety.

Employees should be instructed about the necessity of cleansing the skin if Glycidyl methacrylate is contaminated by materials which are irritants or skin-absorbed.
With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided.

The scientific literature for the use of contact lenses in industry is conflicting.
The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses.
However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye.

In those specific cases, contact lenses should not be worn.
In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing.
Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.
Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Nonfire Spill Response of Glycidyl methacrylate:
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material.
Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal.

Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution.
Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should store this material in a refrigerator.

Identifiers of Glycidyl methacrylate:
CAS Number: 106-91-2
ChEBI: CHEBI:132844
ChemSpider: 7549
ECHA InfoCard: 100.003.130
PubChem CID: 7838
UNII: R8WN29J8VF
CompTox Dashboard (EPA): DTXSID0025361
InChI:
InChI=1S/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3
Key: VOZRXNHHFUQHIL-UHFFFAOYSA-N
InChI=1/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3
Key: VOZRXNHHFUQHIL-UHFFFAOYAT
SMILES: CC(=C)C(=O)OCC1CO1

Properties of Glycidyl methacrylate:
Chemical formula: C7H10O3
Molar mass: 142.1546 g/mol
Appearance: colorless liquid
Density: 1.07 g/cm3
Boiling point: 189.0 °C (372.2 °F; 462.1 K)
Solubility in water: ca 50g/l

Quality Level: 200
assay: ≥97.0% (GC)
form: liquid
contains: ~0.01% hydrochinone monomethylether as stabilizer
refractive index:
n20/D 1.449 (lit.)
n20/D 1.450
bp: 189 °C (lit.)
density:
1.075 g/mL at 20 °C
1.042 g/mL at 25 °C (lit.)
SMILES string: CC(=C)C(=O)OCC1CO1
InChI: 1S/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3
InChI key: VOZRXNHHFUQHIL-UHFFFAOYSA-N

Molecular Weight: 142.15
XLogP3-AA: 0.8
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 4
Exact Mass: 142.062994177
Monoisotopic Mass: 142.062994177
Topological Polar Surface Area: 38.8 Å²
Heavy Atom Count: 10
Formal Charge: 0
Complexity: 162
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count   0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Names of Glycidyl methacrylate:

IUPAC name of Glycidyl methacrylate:
oxiran-2-ylmethyl 2-methylprop-2-enoate

Other names of Glycidyl methacrylate:
glycidyl methacrylate
2,3-epoxypropyl methacrylate
2-((Methacryloxy)methyl)oxirane

Synonyms of Glycidyl methacrylate:
GLYCIDYL METHACRYLATE
106-91-2
2,3-Epoxypropyl methacrylate
Glycidol methacrylate
SY-Monomer G
oxiran-2-ylmethyl 2-methylprop-2-enoate
Blemmer G
Blemmer GMA
Light Ester G
oxiran-2-ylmethyl methacrylate
glycidylmethacrylate
2-((Methacryloxy)methyl)oxirane
Methacrylic acid, 2,3-epoxypropyl ester
Glycidyl alpha-methylacrylate
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester
CP 105
NSC 24156
Methacrylic Acid Glycidyl Ester
Polyglycidyl methacrylate
poly(glycidyl methacrylate)
1-Propanol, 2,3-epoxy-, methacrylate
Glycidyl methacrylate(GMA)
2,3-Epoxypropanol methacrylate
Glycidyl .alpha.-methylacrylate
DTXSID0025361
Acriester G
NSC24156
NSC-24156
(oxiran-2-yl)methyl 2-methylprop-2-enoate
Glycidyl Methacrylate (stabilized with MEHQ)
DSSTox_CID_5361
25067-05-4
DSSTox_RID_77762
DSSTox_GSID_25361
GMA
2-Propenoic acid, 2-methyl-, 2-oxiranylmethyl ester
oxiran-2-ylmethyl 2-methylacrylate
Methacrylic acid,3-epoxypropyl ester
MFCD00005137
WLN: T3OTJ B1OVY1 & U1
CAS-106-91-2
Glycidyl alpha-methyl acrylate
CCRIS 2626
HSDB 494
EINECS 203-441-9
SR 379
2,3-Epoxypropyl methacrylic acid ester
BRN 0002506
Acryester G
glycidyl-methacrylate
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester, homopolymer
methacrylic acid glycidyl
EC 203-441-9
NCIOpen2_000036
oxiran-2-ylmethylmethacrylate
SCHEMBL15617
5-17-03-00035 (Beilstein Handbook Reference)
methacrylic acid-glycidyl ester
CHEMBL1333073
CHEBI:132844
NSC67195
Tox21_201494
Tox21_303145
2-Oxiranylmethyl 2-methylacrylate #
BBL010914
NSC-67195
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
CS-0063449
Epoxypropyl methacrylate,5 cp(25 degrees c)
FT-0609742
M0590
Glycidyl Methacrylate, (stabilized with MEHQ)
2-methyl-acrylic acid oxiran-2-yl-methyl ester
E75837
Glycidyl methacrylate, purum, >=97.0% (GC)
A801532
Q2013175
W-108764
Methacrylic Acid Glycidyl Ester (stabilized with MEHQ)
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
(±)-Glycidyl methacrylate
(oxiran-2-yl)methyl 2-methylprop-2-enoate
106-91-2
2,3-EPOXYPROPYL METHACRYLATE
2,3-Epoxypropyl methacrylic acid ester
2-[(Methacryloyloxy)methyl]oxirane
203-441-9
2-Methyl-2-propenoic acid oxiranylmethyl ester
2-Oxiranylmethyl methacrylate
2-Oxiranylmethylmethacrylat
2-Propenoic acid, 2-methyl-, oxiranylmethyl ester
Allyl glycidyl ether
Glycidol methacrylate
Glycidyl methacrylate
Glycidyl α-methylacrylate
GMA
Méthacrylate de 2-oxiranylméthyle
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
[106-91-2] [RN]
1-Allilossi-2,3 epossipropano
1-Propanol, 2,3-epoxy-, methacrylate
2-((Methacryloxy)methyl)oxirane
2,3-Epoxypropanol methacrylate
2,3-Epoxypropylmethacrylate
203-442-4
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]
Acriester G
AGE
Allil-glicidil-etere
Allyl 2, 3-epoxypropyl ether
Allylglycidaether
Denacol EX 111
Epiol A
Glycidyl α-methylacrylate
glycidylmethacrylate
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