Allyl methacrylate = AMA

CAS Number: 96-05-9
EC Number: 202-473-0
Molecular Weight: 126.15

Allyl methacrylate (AMA) is an acrylic monomer with two types of vinyl groups which include methacrylic and allylic based double bonds. 
Allyl methacrylate is mainly utilized as a cross-linking agent to increase the hardness of the base material. 
Allyl methacrylate also facilitates an improvement in the heat resistant property of the resin.

Allyl Methacrylate (AMA) is an ester of Methacrylic acid and is used as a raw material component in the synthesis of polymers. 
Allyl Methacrylate (AMA) is a monomer of dual allylic and methacrylic functionalities consisting of a methacrylate group with a characteristic high reactivity and a cyclic hydrophobic group. 

Allyl Methacrylate (AMA) forms homopolymers and copolymers. 
Copolymers of Allyl Methacrylate (AMA) which can be prepared with (meth)acrylic acid and its salts, amides, and esters, etc.

Allyl Methacrylate (AMA) is a very useful starting material for chemical synthesis since Allyl methacrylate easily undergoes addition reactions with a wide spectrum of organic and inorganic compounds.

Allyl methacrylate is a low viscosity liquid monomer with dual allylic and methacrylic functionalities. 
Allyl methacrylate offers excellent second stage crosslinking, chemical and heat resistance, hardness, and low shrinkage. 

Allyl methacrylate forms homopolymers and copolymers. 
Allyl methacrylate is also a very useful feedstock for chemical syntheses, because Allyl methacrylate readily undergoes addition reactions with a wide variety of organic and inorganic compounds.

Allyl methacrylate, AMA was polymerized by chemical initiator and by γradiation under different conditions. 
The polymer obtained is mostly gel type with some soluble fractions at lower conversions. 

Arrhenius activation energy is 82.3 kJ/mol for chemical initiated polymerization.
The polymer was characterized by FT-IR, NMR, DSC, TGA, XPS, XRD, DLS, and MS methods. 

Allyl methacrylate was found that about 98-99% of allyl side groups retained as pendant even after completion of the polymerization, while 1-2% may give crosslinking and/or cyclization that yields lactones and anhydrides. 
The spectroscopic and thermal results of the work showed that the reaction is not cyclopolymerization, but may have end group cyclization. 

Molecular weight of 1.1x106 was measured by DLS.
Therefore, insolubility is due to the high molecular weight of polymer, even in the early stage of polymerization rather than crosslinking. 

The Tg of PAMA was observed as 94ºC before curing, upon curing at 150- 200ºC, Tg increased to 211ºC as measured by DSC. 
The thermal treatment of polymer at about 350ºC gave anhydride by linkage type degradation, following side group cyclization. 

The XPS analysis showed the presence of radical fragments of AIBN and CCl4 associated with oligomers. 
The MS and TGA thermograms showed two or three stage degradations depending on solubility. 

The first stage was mostly linkage type degradation for the fragmentation of pendant allyl groups at 225- 350ºC. 
In the second stage, at 395-515ºC, the degradation is random scission and depolymerization. 

AMA is a low viscosity liquid monomer with dual allylic and methacrylic functionalities, offering chemical and heat resistance, adhesion, hardness, excellent second stage cross-linking and low shrinkage.

Random copolymers of methyl methacrylate (MMA) butyl methacrylate (BMA) and allyl methacrylate (AMA) were prepared via atom transfer radical polymerization (ATRP). 
Allyl methacrylate is a bifunctional monomer with two double bonds of different reactivity: a highly reactive methacrylate double bond and an allyl ester double bond of lower reactivity. 

In order to obtain linear polymers with pendant allyl ester groups, the copolymerization conditions have to be optimized with respect to the concentration of AMA, the catalyst system applied - especially the ligand - and the temperature. 
By means of kinetic studies the reaction parameters for a controlled polymerization were determined. 

The results obtained show that the higher the temperature and the amount of AMA is the higher is the probability of irregular chain growth and side reactions induced by the pendant allyl ester groups such as hydrogen abstraction from the allyl position or radical addition to the allyl ester double bond. 
The random copolymers were photochemically crosslinked by using 2,2-dimethoxy-2-phenylacetophenone as photoinitiator. 

The thermal properties of linear and crosslinked polymers were determined. 
The glass transition temperatures of both show no significant difference at low AMA content and thus low crosslinking densities.

Allyl methacrylate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
Allyl methacrylate is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Allyl methacrylate is an important crosslinking agent, can supply double functional radicaleffective crosslinking in the second phase, and has well drug-fast, impact intension, adhesive force, rigidity and low shrinkability. 
Allyl methacrylate is used as dentistry material, industrial paint, organosilicon intermediate, light stability agent, optical macromolecule, elastomer, part of ethylene species and acrylic ester species polymer system.

Physical-Chemical Properties of Allyl methacrylate:
Allyl methacrylate is a clear, colorless liquid with a melting point of -75 °C, boiling point of 141 °C, and measured vapor pressure of 7.7 hPa (5.77 mmHg) at 25 °C. 
The measured octanol-water partition coefficient (log Kow ) is 2.15 at 25°C, and water solubility is 2200 mg/L.

General Manufacturing Information of Allyl methacrylate:

Industry Processing Sectors of Allyl methacrylate:
All other chemical product and preparation manufacturing
Paint and coating manufacturing
Plastic material and resin manufacturing

Alkyl mercury compounds have been used as seed disinfectants and for fungicides. 
They have also been used in organic synthesis.

Benefits of Allyl methacrylate:
Chemical resistance
Heat resistance
Low shrinkage

Applications areas of Allyl methacrylate:
Allyl Methacrylate (AMA) is water-insoluble, with low volatility. 
Allyl methacrylate is used in oil additives as flow improver, in-floor waxes, textile and metal coatings, paint, varnishes, pressure-sensitive adhesives, low temperature caulks, and sealants.

Allyl methacrylate is applied in the production of:
Architectural Coatings
Automotive Coatings
Construction Coatings
Industrial Coatings
Dental Composites
Optical Polymers
UV Inkjet Inks

Uses of Allyl methacrylate:
Allyl methacrylate is used as a monomer, intermediate, and cross-linking agent (contact lenses); Also used in acrylic coatings.
Allyl methacrylate is used mainly in closed system processing as a co-monomer (rigid plastics) and cross linker (silanes).
Also used in coatings, photoresists, adhesives, dental composites, floor polishes, and vulcanized rubber.

Cross-linking agent with methacrylate esters in contact lenses and with alkyl acrylates in pressure-sensitive adhesives; in curable acrylic coatings; for preparing mucilages and thickening agents for aqueous systems
As monomer and intermediate

Uses at industrial sites of Allyl methacrylate:
Allyl methacrylate is used in the following products: polymers, coating products and lubricants and greases.
Allyl methacrylate has an industrial use resulting in manufacture of another substance (use of intermediates).

Allyl methacrylate is used in the following areas: formulation of mixtures and/or re-packaging.
Allyl methacrylate is used for the manufacture of: chemicals, and plastic products.
Release to the environment of this substance can occur from industrial use: for thermoplastic manufacture, as an intermediate step in further manufacturing of another substance (use of intermediates) and in the production of articles.

Industry Uses of Allyl methacrylate:

Consumer Uses of Allyl methacrylate:
Paints and coatings

Widespread uses by professional workers of Allyl methacrylate:
Allyl methacrylate is used in the following products: fillers, putties, plasters, modelling clay, polymers and coating products.
Allyl methacrylate has an industrial use resulting in manufacture of another substance (use of intermediates).

Allyl methacrylate is used in the following areas: formulation of mixtures and/or re-packaging.
Allyl methacrylate is used for the manufacture of: chemicals, plastic products and.
Other release to the environment of this substance is likely to occur from: indoor use.

Manufacture of Allyl methacrylate:
Release to the environment of Allyl methacrylate can occur from industrial use: manufacturing of the Allyl methacrylate.

Storage Conditions of Allyl 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 methacryclic esters may be stored in mild steel, stainless steel, or aluminum. 

Formulation or re-packing of Allyl methacrylate:
Allyl methacrylate is used in the following products: polymers.
Allyl methacrylate has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of this substance can occur from industrial use: formulation of mixtures.

Methods of Manufacturing of Allyl methacrylate:
Alcoholysis of methyl methacrylate by allyl alcohol in the presence of sodium methylate and hydroquinone, a polymerization inhibitor; also can be made by esterification of the acid by allyl alcohol. 
Hydroquinone can be removed by distillation or washing with 5% sodium hydroxide.

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.

Analytic Laboratory Methods of Allyl methacrylate:
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.

Metabolism/Metabolites of Allyl methacrylate:
Allyl methacrylate, was metabolized to acrolein. 
This metabolic pathway can explain the high potency of allyl methacrylate to deplete glutathione despite its low intrinsic chemical reactivity.

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. 
They are also likely to be hydrolyzed via carboxylesterases. 
The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity.

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

Preparation of Allyl methacrylate:
Allyl methacrylate can be synthesized by the reaction of acrylamide and allyl alcohol under the action of concentrated acid and H2O2. 
Allyl methacrylate can also be obtained by transesterification of allyl acetate and methyl methacrylate.

Cleanup Methods of Allyl methacrylate:
Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. 
Concentrations shall be lower than applicable environmental discharge or disposal criteria. 

Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. 
Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. 

Disposal Methods of Allyl methacrylate:
The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 
Recycle any unused portion of the material for Allyl methacrylate approved use or return it to the manufacturer or supplier. 

Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

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 Allyl methacrylate:
The scientific literature for the use of contact lenses by industrial workers is inconsistent. 
The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the Allyl methacrylate, 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 a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. 
Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. 
Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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 Allyl 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.

Antidote and Emergency Treatment of Allyl methacrylate:    
Immediate first aid: Ensure that adequate decontamination has been carried out. 
If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. 

Perform CPR as necessary. 
Immediately flush contaminated eyes with gently flowing water. 
Do not induce vomiting. 
If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. 

Keep patient quiet and maintain normal body temperature. 
Obtain medical attention. 

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 
Suction if necessary. 

Watch for signs of respiratory insufficiency and assist ventilations if necessary. 
Administer oxygen by nonrebreather mask at 10 to 15 L/min. 

Provide a low-stimulus environment. 
Monitor for shock and treat if necessary.

Anticipate seizures and treat if necessary.
For eye contamination, flush eyes immediately with water. 

Irrigate each eye continuously with 0.9% saline (NS) during transport.
Do not use emetics. 
For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool.
Treat frostbite by rapid rewarming.

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. 
Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. 

Consider drug therapy for pulmonary edema.
Monitor cardiac rhythm and treat arrhythmias if necessary.

Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. 
For hypotension with signs of hypovolemia, administer fluid cautiously. 

Consider vasopressors if patient is hypotensive with a normal fluid volume. 
Watch for signs of fluid overload.
Use proparacaine hydrochloride to assist eye irrigation.

Safety of Allyl methacrylate:
A Safety Data Sheet has been compiled for Allyl Methacrylate (AMA) that contains up-to-date information on questions relevant to safety.

Chemical Properties of Allyl methacrylate:
Purity: min. 98.0 %
Acid Value: max. 0.005 %
Water content: max. 0.05 %
Color APHA: max. 15

Physical Properties of Allyl methacrylate:
Appearance: colorless
Physical form: liquidi
Odor: pungent
Density: 0.930 - 0.940 at 20 °C
Boiling Point: 144 °C
Freezing Point: < - 60 °C
Flash point: 37.8 °C
Melting Point: < - 60 °C
Viscosity: 0.72 mPa ・ s at 25 °C
Vapor Point: 5mmHg at 25 °C
pH: No information

Properties of Allyl methacrylate:
Molecular Weight: 126.15    
XLogP3-AA: 1.7    
Hydrogen Bond Donor Count: 0    
Hydrogen Bond Acceptor Count: 2    
Rotatable Bond Count: 4    
Exact Mass: 126.068079557
Monoisotopic Mass: 126.068079557    
Topological Polar Surface Area: 26.3 Ų    
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 136
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Quality Level: 200
vapor pressure: 4.6 mmHg ( 20 °C)
assay: 98%
form: liquid
contains: 50-185 ppm MEHQ as inhibitor
refractive index: n20/D 1.436 (lit.)
bp: 59-61 °C/43 mmHg (lit.)
density: 0.938 g/mL at 25 °C (lit.)
storage temp.: 2-8°C
SMILES string: CC(=C)C(=O)OCC=C
InChI: 1S/C7H10O2/c1-4-5-9-7(8)6(2)3/h4H,1-2,5H2,3H3

Names of Allyl methacrylate:

Regulatory process names of Allyl methacrylate:
2-methyl-2-propenoic acid 2-propenyl ester
2-Propenoic acid, 2-methyl-, 2-propen-1-yl ester
2-Propenoic acid, 2-methyl-, 2-propenyl ester
Ageflex AMA
Allyl methacrylate
Allyl methacrylate
allyl methacrylate
allyl methacrylate; 2-methyl-2-propenoic acid 2-propenyl ester

Translated names of Allyl methacrylate:
2-Methyl-2-propionsäure 2-propenylester (de)
2-methylpropensyreprop-2-en-1-ylester (da)
2-metil-2-propeno rūgšties 2-propenilesteris (lt)
2-metil-2-propenoic acid 2-propenil ester (ro)
2-metil-2-propenojska kislina 2-propenil ester (sl)
2-metil-2-propenonska kiselina 2-propenil-ester (hr)
2-metil-2-propeīnskābes 2-propenilesteris (lv)
2-metil-2-propénsav-2-propenil-észter (hu)
2-metyl-2-propensyra-2-propenylester (sv)
2-metyl-2-propensyre-2-propenylester (no)
2-Metyyli-2-propeenihapon 2-propenyyliesteri (fi)
2-metüül-2-propeenhappe2-propenüülester (et)
2-μεθυλο-2-προπενοϊκό οξύ 2-προπενυλεστέρας (el)
2-метил-2-пропенова киселина 2-пропенил естер (bg)
alil metacrilat (ro)
Allil metakrilat (sl)
alil-metakrilat (hr)
alilmetakrilatas (lt)
alilmetakrilāts (lv)
allil-metakrilát (hu)
allyl-2-methylprop-2-enoát (cs)
allyl-methakrylát (cs)
allylmetakrylat (no)
allylmetakrylat (sv)
allylmethacrylaat (nl)
allylmethacrylat (da)
Allylmethacrylat (de)
Allyylimethakrylaatti (fi)
allüülmetakrülaat (et)
alyl-metakrylát (sk)
alylester kyseliny 2-metylpropénovej (sk)
ester prop-2-en-1-ylowy kwasu 2-metyloprop-2-enowego (pl)
metacrilato de alilo (es)
metacrilato de alilo (pt)
metacrilato di allile (it)
metakrylan allilu (pl)
méthacrylate d'allyle; 2-propénylester de l'acide 2-méthyl-2-propénoïque (fr)
éster do ácido 2-metil-2-propenóico e de 2-propenil (pt)
Μεθακρυλικός αλλυλεστέρας (el)
алил метакрилат (bg)

CAS names of Allyl methacrylate:
2-Propenoic acid, 2-methyl-, 2-propen-1-yl ester

IUPAC names of Allyl methacrylate:
2-methyl-2-propenoic acid 2-propenyl ester
2-Methyl-2-propionsäure 2-propenylester
2-Propenoic acid, 2-methyl-, 2-propenyl ester
allyl 2-methacrylate
Allyl methacrylate
allyl methacrylate
Allyl Methacrylate
Allyl methacrylate
Allyl Methacrylate (stabilized with MEHQ)
allyl methacrylate; 2-methyl-2-propenoic acid 2-propenyl ester
prop-2-en-1-yl 2-methylprop-2-enoate
prop-2-enyl 2-methylprop-2-enoate

Trade names of Allyl methacrylate:
2-Propenoic acid, 2-methyl-, 2-propenyl ester
Ageflex AMA
Allyl Methacrylat
Allyl methacrylate
Visomer AMA

Related Products of Allyl methacrylate:
Diethyl 5-Methyl-2,3-pyridinedicarboxylate
Diethyl (Acetylamino)(2-phenylethyl)malonate
4'-Deoxy Vincristine Sulfate (>75%)
1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinepropanoic Acid

Synonyms of Allyl methacrylate:
Ageflex AMA
2-Propenoic acid, 2-methyl-, 2-propenyl ester
Methacrylic acid, allyl ester
prop-2-enyl 2-methylprop-2-enoate
Allylester kyseliny methakrylove
Methacrylic Acid Allyl Ester
NSC 18597
prop-2-en-1-yl 2-methylprop-2-enoate
Allyl Methacrylate
2-Propenoic acid, 2-methyl-, 2-propen-1-yl ester
Allyl 2-methylacrylate
2-Propenoic acid, 2-methyl-, 2-propen-1-yl ester, homopolymer
HSDB 5297
EINECS 202-473-0
BRN 1747406
Allylester kyseliny methakrylove 
Allyl ester of Methacrylic acid
2-Methyl-2-propenyl 2-propenoate
methacrylic acid allyl
EC 202-473-0
2-Propenyl 2-methylpropenoate
Allyl Methacrylate, 
Methacrylic Acid Allyl Ester 
Allyl methacrylate, contains 50-185 ppm MEHQ as inhibitor, 98%
2-Methyl-2-propenoic acid 2-propenyl ester
2-Propenoic acid, 2-methyl-, 2-propen-1-yl ester
Allyl methacrylate
Méthacrylate d'allyle
Methacrylic acid, allyl ester (8CI)
2-Methyl-2-propenyl 2-propenoate
2-methylacrylic acid allyl ester
2-methylprop-2-enoic acid allyl ester
4-02-00-01529 [Beilstein]
Ageflex AMA
allyl 2-methylacrylate
allyl 2-methylprop-2-enoate
Allyl ester of methacrylic acid
Allyl methacrylate, stabilized with MEHQ
Allyl methacrylate|Methacrylic acid, allyl ester
Allylester kyseliny methakrylove
Methacrylic acid-allyl ester
prop-2-enyl 2-methylprop-2-enoate

allyl methacrylate

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