ISOBORNYL METHACRYLATE

IBOMA (Iso Bornyl Methacrylate)  = Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate

CAS Number: 7534-94-3
EC  Number: 231-403-1
PubChem CID :     904857
Molecular Formula : C14H22O2
Molecular Weight  : 222.32

Isobornyl methacrylate is a colorless transparent liquid. 
Isobornyl methacrylate is a monomer that unifies hardness and flexibility. 
Due to Isobornyl methacrylates molecular structure, its polymer has excellent high gloss, sharp image, scratch resistance, medium resistance and weather resistance, and Its hygroscopicity is significantly lower than that of MMA (methyl methacrylate). 
In addition, IBOMA-added acrylic resin has good compatibility with polyester, alkyd and many volatile paint film-forming substances.

Density of Isobornyl methacrylate is 0.980 at 25 °C.
Vapor Pressure of Isobornyl methacrylate is 0.11 [mmHg].
Henry's Law Constant of Isobornyl methacrylate is 2.4X10-4 atm-cu m/mol at 25 °C.
Stability of Isobornyl methacrylate is storage of this product at elevated temperatures (>30 °C or >85 °F) reduces the shelf-life. 
The typical shelf-life for this product is 12 months.

Isobornyl methacrylate is a reactive solvent with low vapor pressure. 
Isobornyl methacrylate facilitates the free radical polymerization by forming a polymer with high glass transition temperature (Tg).
Isobornyl methacrylate, abbreviated IBOMA, is an organic compound. 
This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. 

Isobornyl methacrylate is soluble in warm water and miscible with most organic solvents. 
Isobornyl methacrylate is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA) and poly(methyl methacrylate) (PMMA). 
The methacrylates have numerous uses, most notably in the manufacture of polymers with trade names such as Lucite and Plexiglas. 
Isobornyl methacrylate occurs naturally in small amounts in the oil of Roman chamomile.

Isobornyl methacrylate is a versatile hydrophobic monomer with a good combination of hardness and flexibility that can improve the chemical and water resistance of polymer systems.
Isobornyl methacrylate was synthesized by direct esterification of camphene and methacrylic acid.
Isobornyl methacrylate is a reactive solvent with low vapor pressure. 
It facilitates the free radical polymerization by forming a polymer with high glass transition temperature (Tg).

Typical Properties of Iso Bornyl Methacrylate
Molecular Formula: C14H22O2
Molecular Weight: 222.328
Refractive Index : 1.475
Color (APHA) : <75
Inhibitor    : MeHQ – 120-180 ppm
Toxic Substance Control Act List : Listed
Specific Gravity : 0.980 g/mL

Methyl acrylate is used in the composition of polymers and copolymers, with a wide range of industrial applications, such as:
- acrylic and modacrylic fibers
- resins and dispersions for paints, varnishes and inks,
glues and adhesives
- aqueous dispersions for non-woven fabrics, textiles
and paper
- cleaning and waxing products
- plastic and synthetic resins
- synthetic rubbers and latexes
- organic synthesis 

Polymerization of Iso Bornyl Methacrylate
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. /methacrylates/

Use and Manufacturing of Iso Bornyl Methacrylate
Used as monomer (i.e. for its homopolymer) and in plastics for repeated use in contact with food; [HSBD]
Industrial Processes with risk of exposure
-Plastic Composites Manufacturing [Category: Industry]

Isobornyl methacrylate is a minor monomer limited to use only in plastic articles intended for repeated use in contact with food.

Industry Uses
-Intermediates

Household Products
Information on 2 consumer products that contain Isobornyl methacrylate in the following categories is provided:
-Auto Products
-Home Maintenance

Methods of Manufacturing of Iso Bornyl Methacrylate
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.

Isobornyl methacrylate (IBMA), a bulky hydrophobic methacrylate, undergoes very fast polymerization, in bulk, with Cu(I)Br/N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA)/ethyl-2-bromoisobutyrate system, at ambient temperature. 
IBMA also undergoes a spontaneous initiator-free polymerization, at ambient temperature, with Cu(I)Br/PMDETA catalytic system in dimethyl sulfoxide-water mixtures. The rate of the polymerization is seen to increase with the water content up to 80 mol % of water. 
A possible intervention of air in initiation is proposed. 
The active Cu(0) formed by the disproportionation of Cu(I) species in aqueous medium probably plays a vital role for a possible air-initiation of IBMA via single electron transfer-living radical polymerization (SET-LRP) mechanism. 
A high tolerance level to water under SET-LRP conditions is demonstrated. 
The poly(IBMA) samples obtained exhibit low molecular weight distributions (1.1-1.3). 
Similar behavior was not observed with other common methacrylates such as methyl methacrylate, t-butyl methacrylate, cyclohexyl methacrylate, and benzyl methacrylate.

Isobornyl methacrylate can be analyzed by this reverse phase (RP) HPLC method with simple conditions. 
The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. 
For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. 
Smaller 3 µm particles columns available for fast UPLC applications. 
This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation. 
Isobornyl methacrylate also suitable for pharmacokinetics.

The cyclic group of isobornyl methacrylate allows it to react in free radical polymerization while also acting as an excellent diluent.
Isobornyl methacrylate (IBOMA) is a monomethacrylate monomer with low viscosity that has been studied as diluent in coatings resins and for polymer purposes 8,9, and showed lower water absorption and greater resistance to degradation. 
These particular properties characteristics may increase the durability of the polymer in the oral medium. 

The molecular weight of IBOMA is similar to the TEGDMA, however the mainly difference is regarding the hydrolytic degradation, especially because IBOMA during the enzymatic hydrolysis process leads to the formation of only one molecule of methacrylic acid, showing lower cytotoxicity than TEGDMA that can lead to two methacrylic acid molecules originated from the enzymatic hydrolysis process.
Additionally, IBOMA has a unique behavior of being less susceptible to water diffusion water then TEGDMA which makes polymer formed by IBOMA more water stable.

IBOMA has an excellent combination of flexibility and hardness. 
The polymer has high-gloss, abrasion resistance, chemical resistance, and weather ability. 
It's application areas include high-solid acrylic resins, powder coatings, and Tg acrylic resins.
Isobornyl methacrylate (IBOMA) is a highly reactive monofunctional methacrylate monomer, it can be used as a low viscosity diluent for ultraviolet radiation cured system.

PERFORMANCE HIGHLIGHTS of Iso Bornyl Methacrylate
-Good adhesion
-Good toughness
-Excellent abrasion resistance
-Good water and heat resistance

SUGGESTED APPLICATIONS of Iso Bornyl Methacrylate
-Adhesives
-Coatings
-Photoresists,Solder masks
-Inks

Isobornyl methacrylate (IBOMA) should be stored in a cool, shaded area away from direct sunlight and heat sources. 
The shelf life under normal condition is 360 days max.

Physicochemical Properties of Iso Bornyl Methacrylate
Isobornyl methacrylate (IBOMA) is liquid at room temperature. 
In a melting point study, the measured melting point was not detected, but a relaxation peak and an endothermic Specific heat capacity (Cp)-step was shown at -94 °C,
characteristics for a glass transition (i.e., the test item solidifies amorphously in the glassy state). 
The measured boiling point value is 258°C; measured vapor pressure is 0.012 hPa at 25°C; measured water solubility is 5.44 mg/L at 20°C; measured octanol log Kow values is 5.09. 

Isobornyl methacrylate is a monomer of copolymerization.
Isobornyl methacrylate is used in the fields of modified powder coating ,adhesives and specialty plastic,introducing good impact resistance and scratch resistance.
Polymerization may be initiated by contamination with peroxides, azo compounds, heavy metal ions, tert. Amines, S compounds. 
Polymerization is also induced by light. 
Atmospheric oxygen saturation  in the monomer is necessary for stability. 
Storage temperatures should not exceed 35°C.

First-aid measures of Iso Bornyl Methacrylate
Eye Contact
Rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes. 
Get medical attention.

Skin Contact 
Wash off immediately with plenty of water for at least 15 minutes. 
If skin irritation persists,call a physician.

Inhalation 
Remove to fresh air. 
If not breathing, give artificial respiration. 
Get medical attentio nif symptoms occur.

Ingestion 
Clean mouth with water and drink afterwards plenty of water.

Substance identity

EC / List no.: 231-403-1
CAS no.: 7534-94-3

Hazard classification & labelling of Iso Bornyl Methacrylate
Warning! According to the classification provided by companies to ECHA in REACH registrations this substance is harmful to aquatic life with long lasting effects, causes serious eye irritation, causes skin irritation and may cause respiratory irritation.

About Iso Bornyl Methacrylate
Iso Bornyl 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.
Iso Bornyl Methacrylate is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses of Iso Bornyl Methacrylate
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
Other release to the environment of Iso Bornyl Methacrylate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).

Article service life of Iso Bornyl Methacrylate
Other release to the environment of this substance is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment). 

Iso Bornyl Methacrylate can be found in complex articles, with no release intended: vehicles, machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines) and electrical batteries and accumulators. This substance can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones), stone, plaster, cement, glass or ceramic (e.g. dishes, pots/pans, food storage containers, construction and isolation material), fabrics, textiles and apparel (e.g. clothing, mattress, curtains or carpets, textile toys), leather (e.g. gloves, shoes, purses, furniture), metal (e.g. cutlery, pots, toys, jewellery), paper (e.g. tissues, feminine hygiene products, nappies, books, magazines, wallpaper), rubber (e.g. tyres, shoes, toys) and wood (e.g. floors, furniture, toys).

Widespread uses by professional workers of Iso Bornyl Methacrylate
Iso Bornyl Methacrylate is used in the following products: coating products.
Iso Bornyl Methacrylate is used in the following areas: building & construction work.
Iso Bornyl Methacrylate is used for the manufacture of: .
Other release to the environment of Iso Bornyl Methacrylate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).

Formulation or re-packing of Iso Bornyl Methacrylate
Iso Bornyl Methacrylate is used in the following products: adhesives and sealants and polymers.
Release to the environment of Iso Bornyl Methacrylate can occur from industrial use: formulation of mixtures and formulation in materials.

Uses at industrial sites of Iso Bornyl Methacrylate
Iso Bornyl Methacrylate is used in the following products: polymers, adhesives and sealants and inks and toners.
Iso Bornyl Methacrylate is used for the manufacture of: and plastic products.
Release to the environment of Iso Bornyl Methacrylate can occur from industrial use: for thermoplastic manufacture, as an intermediate step in further manufacturing of another substance (use of intermediates), in the production of articles, of substances in closed systems with minimal release, in processing aids at industrial sites, as processing aid and as processing aid.

Manufacture of Iso Bornyl Methacrylate
Release to the environment of Iso Bornyl Methacrylate can occur from industrial use: manufacturing of the substance.

Synonyms:
ISOBORNYL METHACRYLATE
7534-94-3
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl methacrylate
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl methacrylate(relative)
Ageflex IBOMA
Sipomer IBOMA
ISOBORNYL 2-METHYL-2-PROPENOATE
DSSTox_CID_7653
[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate
DSSTox_RID_78543
DSSTox_GSID_27653
28854-39-9
Acryester
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, rel-, homopolymer
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-, homopolymer
CAS-7534-94-3
Light Ester IB-X
NK Ester IB
Eternal EM 90
IBXMA
64114-51-8
HSDB 6088
Methacrylic acid, isobornyl ester
2-Propenoic acid, 2-methyl-, 1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, exo-
EM 90
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, rel-
EINECS 231-403-1
SR 423
Isobornyl 2-methyl-2-propenoate homopolymer
EC 231-403-1
SCHEMBL7173571
CHEMBL3183838
Tox21_202201
Tox21_303579
ZINC12363773
CS-W014235
DS-4821
NCGC00257409-01
NCGC00259750-01
D70305
854I399
A852243
Methacrylic acid (1R,4R)-bornane-2alpha-yl ester
Q27256271
UNII-33GSY5DKCQ component IAXXETNIOYFMLW-GYSYKLTISA-N
(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, rel-
2-Propenoic acid, 2-methyl-, 1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, exo-
Acryester
Ageflex IBOMA
Eternal EM 90
exo-1,7,7-Trimethylbicyclo(2.2.1)hept-2-yl methacrylate
Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
Exo-1,7,7-trimethylbicyclo[[]2.2.1]hept-2-yl methacrylate
IBXMA
Isobornyl methacrylate
Light Ester IB-X
Methacrylic acid, isobornyl ester
NK Ester IB
Sipomer IBOMA
SR 423
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-
(1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate
(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-methylprop-2-enoate
(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-enoate
1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-methylprop-2-enoate
2-Methyl-2-propenoic acid exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester
2-Propenoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo[ 2.2.1]hept-2-yl ester, rel-(7534-94-3)
[(1R,4R,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate
Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
IBOMA
iso-Bornyl methacrylate
ISOBORNYL METHACRILATE
ISOBORNYL METHACRYLATE
Isobornyl methacrylate
isobornyl methacrylate
Isobornyl methacrylate
Isobornyl Methacrylate (IBOMA)
Isobornyl Methacrylate (stabilized with MEHQ)
Isobornylmethacrylate
MAISOBOR
2-Methyl-2-propenoic acid exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester
ACRYESTER IBX
ethacrylate d'exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yle
Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate
Exo-1,7,7-Trimethylbicyclo[2.2.1]hept-2-ylmethacrylat
IBOMA
IBXMA
Iso-Bornyl methacrylate
Isoborneol, methacrylate
Isobornyl methacrylate
Isobornyl Methacrylate (IBOMA)
Metacrilato de exo-1,7,7-trimetilbiciclo[2.2.1]hept-2-ilo
Methacrylate, isobornyl
Methacrylic acid, isobornyl ester
VISIOMER® IBOMA
1271432-81-5
1271432-81-5
1467081-31-7
1467081-31-7
7390-97-8
7390-97-8
7534-94-3