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2-Propenoic acid, isooctyl ester is a monofunctional acrylic ester containing a polymerizable acrylate group and a branched eight-carbon alkyl chain.
It is used primarily as a soft monomer and reactive diluent in pressure-sensitive adhesives, flexible acrylic polymers, coatings, sealers, inks, and radiation-curable formulations.
The branched hydrophobic group contributes low glass-transition temperature, flexibility, tack, water resistance, and compatibility with many organic monomers and polymer systems.
CHEMICAL IDENTITY AND COMMON NAMES
2-Propenoic acid, isooctyl ester is commonly known as isooctyl acrylate and is abbreviated as IOA.
Its principal registered structure is 6-methylheptyl prop-2-enoate, formed by esterifying acrylic acid with 6-methylheptan-1-ol.
Commercial monomer composition is influenced by the isooctyl alcohol feedstock.
Controlled grades can contain small amounts of neighboring branched-chain acrylates, residual isooctyl alcohol, acrylic acid, water, and higher-boiling esterification products.
Monomer assay and isomer distribution are therefore important procurement parameters.
2-Propenoic acid, isooctyl ester is distinct from 2-ethylhexyl acrylate.
Both substances have the formula C11H20O2 and a branched C8 alkyl group, but their branching positions, molecular structures, registry numbers, and polymer-performance profiles are different.
2-Ethylhexyl acrylate is identified by CAS Number 103-11-7.
The material is also distinct from linear n-octyl acrylate, CAS Number 2499-59-4.
Isooctyl methacrylate contains an additional methyl group on the polymerizable double bond and belongs to the methacrylate family rather than the acrylate family.
Synonyms and Common Names: Isooctyl acrylate, iso-octyl acrylate, isooctylacrylate, IOA, IO-AA, acrylic acid isooctyl ester, acrylic acid, isooctyl ester, acrylic acid iso-octyl ester, isooctyl ester of acrylic acid, isooctyl 2-propenoate, isooctyl prop-2-enoate, 6-methylheptyl acrylate, 6-methylheptylacrylate, 6-methylheptyl 2-propenoate, 6-methylheptyl prop-2-enoate, 6-methylheptan-1-yl prop-2-enoate, 2-Propenoic acid, 6-methylheptyl ester, 2-propenoic acid 6-methylheptyl ester, isooctyl acrylate monomer
TECHNICAL IDENTIFICATION
CAS Number: 29590-42-9
EC / EINECS Number: 249-707-8
EC Index Number: 607-244-00-2
Molecular Formula: C11H20O2
Molar Mass: 184.28 g/mol
Exact Mass: 184.1463 g/mol
IUPAC Name: 6-Methylheptyl prop-2-enoate
Chemical Class: Acrylic acid ester
Functional Group: Alpha,beta-unsaturated carboxylic ester
Monomer Functionality: Monofunctional
Polymerization Type: Addition polymerization through the carbon-carbon double bond
InChIKey: DXPPIEDUBFUSEZ-UHFFFAOYSA-N
SMILES: C=CC(=O)OCCCCCC(C)C
Common Abbreviation: IOA
Transport Identification: UN 3082
Transport Class: Class 9
Packing Group: III
Commercial Stabilizer: Commonly supplied with monomethyl ether of hydroquinone as a polymerization inhibitor
MOLECULAR STRUCTURE AND FUNCTIONALITY
2-Propenoic acid, isooctyl ester contains a highly reactive acrylate double bond conjugated with an ester carbonyl group.
Free radicals generated thermally, chemically, photochemically, or by high-energy radiation add to this double bond and propagate acrylic polymer chains.
The molecule contains only one polymerizable acrylate group.
It therefore contributes linear chain growth rather than directly creating the dense network structure produced by multifunctional diacrylates or triacrylates.
The long branched alkyl group increases hydrophobicity and molecular mobility.
When incorporated into an acrylic copolymer, this group lowers modulus, supports flexibility, reduces brittleness, and increases wetting and tack.
Poly(2-Propenoic acid, isooctyl ester) has a glass-transition temperature around -50 °C.
This low glass-transition temperature explains the importance of the monomer in pressure-sensitive and elastomeric acrylic compositions that must remain soft at room temperature and under cold-service conditions.
The monomer can be copolymerized with acrylic acid, methacrylic acid, hydroxy-functional acrylates, acrylamides, vinyl acetate, styrene, methyl methacrylate, and other acrylic or vinyl monomers.
Soft, hard, polar, and crosslinkable comonomers are combined to control tack, peel adhesion, cohesion, shear resistance, chemical resistance, and service temperature.
PRODUCTION AND COMMERCIAL FORM
2-Propenoic acid, isooctyl ester is produced by the controlled esterification of acrylic acid with isooctyl alcohol.
The principal alcohol associated with the registered structure is 6-methylheptan-1-ol.
Industrial esterification uses an acid catalyst, a polymerization inhibitor, controlled heating, and continuous or staged removal of the reaction water.
Inhibition remains active throughout the heated process because acrylic monomers can polymerize rapidly when exposed to excessive temperature, free radicals, peroxide contamination, or inhibitor depletion.
The crude reaction mixture contains the desired ester, unreacted alcohol, residual acrylic acid, water, catalyst residues, light components, and higher-boiling by-products.
Purification can include phase separation, washing, neutralization, removal of light components, and reduced-pressure distillation.
Reduced-pressure operation limits thermal exposure during separation.
The purified monomer is adjusted to the specified inhibitor concentration before packaging.
Commercial forms include technical monomer, high-purity monomer, controlled-isomer grades, and stabilized monomer intended for polymer, adhesive, coating, or radiation-curing production.
The inhibitor is a functional component of the supplied monomer rather than an incidental impurity.
Its identity and concentration influence storage stability, polymerization induction time, color, and processing requirements.
PHYSICAL AND CHEMICAL PROPERTIES
Appearance: Clear colorless liquid
Physical State: Liquid
Molecular Formula: C11H20O2
Molar Mass: 184.28 g/mol
Density: 0.88 g/cm³ at 25 °C
Boiling Point: 196.8 °C
Reduced-Pressure Boiling Point: Approximately 125 °C at 20 mmHg
Flash Point: 91 °C, closed cup
Vapour Pressure: 0.1333 kPa at 25 °C
Relative Vapour Density: 6.4, with air equal to 1
Water Solubility: 12.44 mg/L at 23.1 °C
Water Affinity: Very low
Partition Coefficient: log Pow 3.93 at 25 °C
Kinematic Viscosity: Approximately 2 mm²/s at 25 °C
Refractive Index: Approximately 1.437 at 20 °C
Hydrogen-Bond Acceptors: 2
Hydrogen-Bond Donors: 0
Polymerization Behaviour: Readily undergoes exothermic free-radical polymerization
Thermal Decomposition: Produces acrid and irritating decomposition products, including acrylic compounds
Stability: Stable under controlled cool storage with an effective inhibitor system
Light Sensitivity: Protected storage is required to limit unintended initiation and inhibitor degradation
Combustibility: Combustible liquid
Environmental Behaviour: Very toxic to aquatic organisms
FUNCTIONAL CHARACTERISTICS
Soft-monomer performance
2-Propenoic acid, isooctyl ester introduces a flexible, low-polarity C8 side chain into acrylic polymers.
This structure increases segmental mobility and produces soft polymers with low glass-transition temperature.
The monomer supports tack and substrate wetting in pressure-sensitive adhesives.
Its flexibility enables adhesive contact with irregular, textured, curved, and low-energy surfaces.
Cohesive strength is normally developed through harder comonomers, polar monomers, controlled molecular weight, branching, or crosslinking.
The balance between 2-Propenoic acid, isooctyl ester and these structural components determines peel adhesion, shear resistance, holding power, and removability.
Reactive-diluent function
2-Propenoic acid, isooctyl ester has low viscosity and can reduce the application viscosity of acrylate oligomers and high-solids resin systems.
Unlike a conventional volatile solvent, it becomes chemically incorporated into the cured polymer.
Its monofunctional structure produces a softer and less densely crosslinked network than multifunctional reactive diluents.
This characteristic can improve flexibility, impact response, adhesion, and resistance to cracking while reducing hardness and cure-network density.
Hydrophobic modification
The branched alkyl group gives 2-Propenoic acid, isooctyl ester very low water solubility.
Incorporation into a copolymer increases hydrophobic character and can improve resistance to water whitening, moisture uptake, and aqueous exposure.
High hydrophobicity also affects emulsion polymerization.
Stable polymerization requires suitable emulsifier selection, droplet control, monomer transport, initiation strategy, and agitation.
Low-temperature flexibility
The low glass-transition temperature of poly(2-Propenoic acid, isooctyl ester) helps acrylic polymers remain flexible and tacky at reduced temperatures.
This characteristic is useful in outdoor labels, cold-chain packaging, flexible films, automotive tapes, construction adhesives, and other products exposed to temperature cycling.
Polymerization and curing response
2-Propenoic acid, isooctyl ester can be polymerized by solution, emulsion, suspension, bulk, ultraviolet, electron-beam, and controlled-radical processes.
Initiator type, temperature, oxygen content, inhibitor concentration, chain-transfer chemistry, and monomer feed rate influence conversion and molecular-weight distribution.
Oxygen and the storage inhibitor suppress premature polymerization during handling.
During intentional polymerization, the formulation and reactor procedure overcome or remove this inhibition in a controlled manner.
Residual monomer control
Unreacted 2-Propenoic acid, isooctyl ester can affect odor, migration, skin sensitization, emissions, and regulatory suitability.
High conversion, appropriate post-curing, stripping, devolatilization, and controlled drying reduce residual monomer in the finished polymer.
APPLICATIONS AND INDUSTRIES
Pressure-sensitive tapes and labels
2-Propenoic acid, isooctyl ester is an important soft monomer for acrylic pressure-sensitive adhesives.
It provides inherent tack, flexibility, substrate wetting, and low-temperature adhesion.
Applications include packaging tapes, masking systems, double-sided tapes, transfer adhesives, graphic films, protective films, permanent labels, removable labels, and industrial mounting products.
The final adhesive composition balances the monomer with polar comonomers and crosslinking chemistry to establish the required peel, shear, tack, aging, and removability profile.
Waterborne, solvent-borne, bulk-polymerized, and radiation-cured pressure-sensitive adhesive technologies can incorporate 2-Propenoic acid, isooctyl ester.
The appropriate grade is selected according to polymerization route, inhibitor tolerance, residual-monomer requirement, coating method, and finished adhesive specification.
Medical and skin-contact adhesives
Copolymers based on 2-Propenoic acid, isooctyl ester are used in specialized pressure-sensitive adhesives designed for contact with skin.
The low-modulus polymer can conform to body movement while maintaining adhesion under controlled moisture and wear conditions.
Applications include medical tapes, wound-care constructions, diagnostic electrodes, ostomy components, wearable-device adhesives, and transdermal delivery systems.
Formulations are engineered for adhesion, painless removal, breathability, skin compatibility, drug compatibility, and controlled wear time.
Medical-grade production places strict limits on residual monomer, extractable substances, processing aids, catalyst residues, odor, and contamination.
Biocompatibility, sterilization response, packaging compatibility, and application-specific regulatory documentation form part of the finished adhesive qualification.
Waterborne acrylic dispersions
2-Propenoic acid, isooctyl ester is used as a soft hydrophobic monomer in acrylic latexes and emulsion polymers.
It can be combined with hard and functional monomers to produce dispersions with controlled film formation, tack, flexibility, and water resistance.
These dispersions are used in waterborne adhesives, flexible coatings, paper and film treatments, construction binders, and specialty polymer emulsions.
The monomer’s limited water solubility makes emulsifier architecture, particle nucleation, feed strategy, temperature, and reactor mixing important formulation variables.
Solution and hot-melt acrylic adhesives
Solution polymerization of 2-Propenoic acid, isooctyl ester produces acrylic polymers that can be coated from compatible organic media.
Molecular weight and polymer composition are adjusted to achieve coating viscosity, drying behavior, tack, cohesion, and resistance to creep.
Solvent-free and hot-melt pressure-sensitive systems can use prepolymers or syrup polymers containing 2-Propenoic acid, isooctyl ester.
Subsequent thermal, chemical, ultraviolet, or electron-beam crosslinking develops the required shear strength and temperature resistance.
Energy-curable inks, coatings, and adhesives
2-Propenoic acid, isooctyl ester functions as a monofunctional reactive diluent in ultraviolet- and electron-beam-curable formulations.
It reduces viscosity, participates in curing, increases flexibility, and improves wetting and adhesion on suitable substrates.
Applications include digital printing inks, inkjet inks, overprint systems, flexible coatings, laminating adhesives, and photopolymer formulations.
The monomer is combined with acrylate oligomers, multifunctional crosslinkers, pigments, photoinitiators, and additives.
Its monofunctional nature moderates crosslink density and shrinkage.
Formulators balance this effect against cure speed, hardness, solvent resistance, migration, surface cure, and residual-monomer requirements.
Flexible coatings and sealers
2-Propenoic acid, isooctyl ester can be incorporated into copolymers for flexible protective coatings, sealers, membranes, and surface treatments.
The monomer contributes elasticity, water resistance, film formation, and adhesion.
Construction applications include selected concrete sealers, flexible coatings, crack-bridging binders, and adhesive or sealing compositions.
The polymer architecture is adjusted for substrate penetration, weathering, abrasion resistance, dirt pickup, elongation, and chemical resistance.
Textile, nonwoven, and flexible-substrate binders
Acrylic copolymers containing 2-Propenoic acid, isooctyl ester can be used as flexible binders and coatings for textiles, nonwovens, paper, polymer films, and composite substrates.
The soft segment supports drape, flexibility, bonding, and resistance to cracking during repeated bending.
Binder formulations can be crosslinked to improve washing resistance, blocking resistance, dimensional stability, and durability.
Monomer selection also influences handle, surface tack, water resistance, and adhesion to fibers or films.
Automotive, electrical, and electronic adhesive systems
Pressure-sensitive copolymers containing 2-Propenoic acid, isooctyl ester are used in tapes and films for automotive, electrical, and electronic assembly.
Applications include wire and cable products, foam tapes, vibration-control constructions, protective films, membrane switches, insulation components, and die-cut adhesive parts.
The low-temperature flexibility of the monomer supports adhesion during thermal cycling.
Electronic and optical applications additionally control ionic contamination, residual monomer, outgassing, extractables, color, haze, and compatibility with sensitive surfaces.
Specialty acrylic polymers and elastomers
2-Propenoic acid, isooctyl ester is used in the synthesis of soft acrylic homopolymers, random copolymers, graft polymers, and block copolymers.
These materials can function as elastomeric segments, tacky phases, flexible modifiers, or hydrophobic polymer domains.
Controlled polymerization enables adjustment of molecular weight, architecture, branching, end groups, and block composition.
Specialty uses include polymer research, functional materials, surface-modifying polymers, and tailored adhesive or coating intermediates.
GRADE SELECTION AND PRODUCT SUITABILITY
Identity: CAS Number 29590-42-9 distinguishes 2-Propenoic acid, isooctyl ester from 2-ethylhexyl acrylate and n-octyl acrylate
Monomer Assay: Defines the concentration of the principal acrylate ester
Isomer Profile: Controls the proportions of the registered isooctyl structure and other branched-chain components
Inhibitor Type: Commonly monomethyl ether of hydroquinone
Inhibitor Concentration: Selected for storage stability and the intended polymerization process
Residual Acrylic Acid: Controlled for color, stability, corrosion, polymerization, and formulation balance
Residual Isooctyl Alcohol: Controlled for odor, conversion, polymer properties, and volatile content
Water Content: Controlled for solution, bulk, energy-curing, and moisture-sensitive processes
Color: Important for transparent adhesives, clear coatings, optical films, and pale polymers
Heavy Components: Controlled to limit haze, color, gel formation, and deposits
Peroxide Content: Controlled because radical-forming contamination can initiate polymerization
Density and Refractive Index: Useful for identity, batch consistency, and incoming quality control
Polymer Content: Controlled to prevent haze, particles, filter blockage, and unstable storage
Packaging Atmosphere: Matched to the inhibitor system and acrylic-monomer storage procedure
Pressure-sensitive adhesive grades prioritize isomer consistency, low color, controlled residual acid, and reproducible homopolymer softness.
Changes in branched-isomer distribution can alter solution viscosity, polymer glass-transition temperature, tack, and cohesive strength.
Radiation-curing grades prioritize low color, low water, controlled inhibitor concentration, low residual alcohol, and compatibility with photoinitiators and oligomers.
The inhibitor level must provide storage protection without creating excessive cure delay.
Emulsion-polymerization grades require consistent hydrophobicity, monomer assay, feedstock composition, and residual acid.
These parameters affect emulsion stability, nucleation, conversion, coagulum formation, and residual monomer.
Medical, electronic, and optical applications require additional control of extractables, ionic impurities, residual monomer, odor, color, particles, and trace contaminants.
The purchase specification connects these limits directly with the intended finished product and processing route.
FORMULATION AND PROCESS CONSIDERATIONS
2-Propenoic acid, isooctyl ester is introduced into polymerization systems through batch, semibatch, continuous-feed, or pre-emulsified addition.
Controlled feed limits heat generation, manages instantaneous monomer concentration, and supports molecular-weight and particle-size control.
Free-radical polymerization is strongly exothermic.
Reactor cooling, agitation, initiator addition, temperature monitoring, emergency inhibition, pressure relief, and monomer-feed interlocks are central process controls.
Solution polymerization requires compatibility among the monomer, solvent, initiator, chain-transfer agent, and developing polymer.
Solids content and molecular weight are balanced against heat removal, viscosity, coating requirements, and solvent recovery.
Emulsion polymerization requires effective distribution of the water-insoluble monomer.
Pre-emulsification, seed latex, surfactant selection, redox or thermal initiation, and staged feeding help control particle nucleation and coagulum.
Radiation-curable formulations use 2-Propenoic acid, isooctyl ester to reduce viscosity and soften the cured network.
The formulation balances monomer concentration with oligomer functionality, pigment loading, photoinitiator absorption, film thickness, oxygen inhibition, lamp output, line speed, and post-cure requirements.
Multifunctional acrylates or other crosslinking systems increase cohesion, hardness, heat resistance, and solvent resistance.
Excessive crosslink density reduces tack, elongation, conformability, and low-temperature performance.
Inhibitor concentration is included in polymerization calculations.
Processes with sensitive initiation kinetics account for the inhibitor induction period without compromising storage protection before charging.
Residual monomer is reduced through high conversion, controlled post-polymerization, devolatilization, vacuum treatment, stripping, drying, or extended radiation exposure.
The selected method preserves polymer structure while meeting odor, migration, and exposure requirements.
QUALITY, SPECIFICATIONS AND DOCUMENTATION
A commercial specification for 2-Propenoic acid, isooctyl ester can include appearance, monomer assay, isomer distribution, color, density, refractive index, water content, acidity, inhibitor concentration, residual alcohol, light components, heavy components, and polymer content.
Gas-chromatographic analysis is used to establish monomer purity and the distribution of volatile organic components.
Acidity, water, color, refractive index, density, and inhibitor concentration provide complementary batch-control information.
The certificate of analysis records the controlled release parameters for the delivered batch.
Technical and safety documentation describes polymerization behavior, inhibitor management, handling conditions, transport classification, packaging, and emergency measures.
Application-oriented documentation can include residual-monomer data, impurity profile, chemical-inventory status, restricted-substance declarations, and information relevant to medical, electronic, optical, or low-emission formulations.
SAFETY AND REGULATORY CONSIDERATIONS
2-Propenoic acid, isooctyl ester irritates the eyes, skin, and respiratory tract.
Repeated or prolonged skin exposure can cause allergic sensitization and cross-sensitization to other acrylates.
Swallowing creates an aspiration hazard because the low-viscosity liquid can enter the lungs.
Aspiration can cause serious chemical pneumonitis.
The vapour is heavier than air and can accumulate in low or poorly ventilated areas.
The liquid is combustible, and vapour-air mixtures can become hazardous at elevated temperature.
Heating, ultraviolet exposure, peroxide contamination, free-radical initiators, loss of inhibitor, and prolonged storage at excessive temperature can initiate polymerization.
Uncontrolled polymerization releases heat, increases pressure, and can rupture inadequately vented equipment or packaging.
2-Propenoic acid, isooctyl ester is very toxic to aquatic organisms and can cause long-lasting environmental effects.
The material is prevented from entering drains, soil, surface water, and uncontrolled wastewater systems.
Transport classification is based primarily on environmental hazard.
The substance is commonly transported as UN 3082, environmentally hazardous substance, liquid, Class 9, Packing Group III.
FIRST AID
Eye Contact: Rinse immediately with clean water for at least 15 minutes, remove contact lenses when easily possible, and obtain medical attention.
Skin Contact: Remove contaminated clothing and wash the affected skin thoroughly with soap and water.
Skin Sensitization: Obtain medical assessment when redness, swelling, blistering, itching, or recurring dermatitis develops.
Inhalation: Move the affected person to fresh air, keep at rest, and obtain medical attention for coughing, breathing difficulty, dizziness, or persistent irritation.
Ingestion: Rinse the mouth, do not induce vomiting, and obtain immediate medical attention because of the aspiration hazard.
Aspiration: Urgent medical treatment is required if vomiting occurs or material may have entered the lungs.
Contaminated Clothing: Wash thoroughly before reuse and keep contaminated work clothing away from domestic areas.
FIRE-FIGHTING AND SPILL RESPONSE
Suitable extinguishing media include alcohol-resistant foam, dry chemical powder, carbon dioxide, and water spray.
Water spray is used to cool exposed containers and limit heat-driven polymerization.
A heated or polymerizing container is approached only under an established emergency procedure.
Personnel are withdrawn from areas threatened by pressure buildup, venting, container distortion, or rapidly increasing temperature.
Spilled liquid is contained with inert absorbent and collected in closed, compatible waste containers.
Sparks, flames, hot surfaces, and unnecessary personnel are removed from the area.
The spill is prevented from reaching drains or waterways.
Recovered material contaminated with absorbent, peroxide, initiator, metal salts, acids, alkalis, or other reactive substances is not returned to the original package.
Contaminated monomer is isolated for controlled disposal.
HANDLING AND STORAGE
2-Propenoic acid, isooctyl ester is handled in closed equipment with effective local exhaust ventilation.
Chemical-resistant gloves, protective clothing, and eye or face protection prevent direct exposure to the sensitizing monomer.
Transfer equipment is grounded and bonded.
Electrical installations and tools are selected for the combustible-liquid environment.
The monomer is stored only in stabilized form.
Containers are kept closed, cool, protected from direct sunlight, and separated from heat and ignition sources.
MEHQ-stabilized bulk monomer requires an oxygen-containing headspace for effective inhibition.
Fully oxygen-free inert blanketing is not used with this inhibition system.
Headspace composition, inhibitor concentration, temperature, and storage time are controlled together.
Storage and transfer systems exclude peroxides, free-radical initiators, oxidizing agents, reducing agents, strong acids, strong bases, amines, oxygen scavengers, rust, and other polymerization-promoting contaminants.
Dedicated lines, pumps, filters, and sampling equipment reduce cross-contamination.
Bulk installations incorporate temperature monitoring, recirculation arrangements, emergency cooling, pressure relief, and procedures for responding to an unexplained temperature increase.
Vents remain free of polymer and are directed to an appropriate controlled system.
The storage area is ventilated at low level because the vapour is heavier than air.
The area includes liquid containment and excludes direct access to drains or sewers.
PACKAGING AND PROCUREMENT CONSIDERATIONS
2-Propenoic acid, isooctyl ester can be supplied in compatible sealed bottles, pails, drums, intermediate bulk containers, and properly engineered bulk-storage systems.
Light-protective packaging supports inhibitor performance and product color.
The package maintains suitable headspace for the specified inhibitor system.
Bulk and large-container handling includes controlled recirculation or mixing that preserves dissolved oxygen without exposing the monomer to excessive heat or contamination.
A complete purchase specification identifies CAS Number 29590-42-9, required assay, isomer distribution, residual acrylic acid, residual isooctyl alcohol, water content, color, inhibitor identity and concentration, polymer content, packaging atmosphere, package size, and application.
This prevents substitution with 2-ethylhexyl acrylate, n-octyl acrylate, isooctyl methacrylate, or another C8 acrylate.
For grade selection, specifications, inhibitor requirements, application documentation, packaging, and supply planning for 2-Propenoic acid, isooctyl ester, contact Ataman Kimya at +90 216 577 10 10 or info@atamankimya.com.
