| HS Code | 102775 |
| Productname | Sec-Octyl Cyanoacrylate |
| Chemicalname | Octan-2-yl 2-cyanoprop-2-enoate |
| Commonname | 2-Octyl cyanoacrylate |
| Casnumber | 133978-15-1 |
| Molecularformula | C12H19NO2 |
| Molecularweight | 209.28 g/mol |
| Chemicalfamily | Cyanoacrylate monomer |
| Appearance | Colorless to pale yellow liquid |
| Odor | Pungent, irritating acrylic odor |
| Density | 0.93 g/cm3 at 25 °C |
| Boilingpoint | 292 °C at 760 mmHg |
| Flashpoint | 125 °C |
| Viscosity | 5-50 mPa·s at 25 °C depending on grade |
| Solubility | Miscible with organic solvents; insoluble in water; reacts with moisture |
| Polymerizationbehavior | Rapid anionic polymerization initiated by moisture |
| Storageconditions | Store refrigerated, dry, away from moisture and light |
| Shelflife | Typically 12-24 months when refrigerated |
| Primaryuse | Medical/surgical tissue adhesive and industrial cyanoacrylate monomer |
| Hazardstatement | May irritate skin, eyes, and respiratory tract; bonds skin rapidly |
As an accredited Sec-Octyl Cyanoacrylate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Sec-Octyl Cyanoacrylate is packaged in 100 mL amber glass bottles with PTFE-lined screw caps and sealed for chemical stability. |
| Container Loading (20′ FCL) | Sec-Octyl Cyanoacrylate in sealed drums is palletized, braced, and loaded into a 20-foot FCL container for ocean export. |
| Shipping | Air transport: UN 3334, Aviation regulated liquid, n.o.s. (sec-Octyl Cyanoacrylate), Class 9, Packing Group III. Ground/sea: generally not regulated. Ship in sealed, inhibited containers, upright, cool, dry, and away from heat, moisture, and sunlight to prevent polymerization. Follow SDS and carrier rules. |
| Storage | Store Sec-Octyl Cyanoacrylate in a cool, dry, well-ventilated location, ideally refrigerated at 2–8°C. Keep containers tightly closed under dry air or inert gas to exclude moisture. Protect from heat, sparks, open flames, and direct sunlight. Separate from bases, amines, alcohols, and other polymerization initiators. Use compatible, non-reactive containers and follow local regulations. |
| Shelf Life | When stored unopened, cool, dry, and protected from moisture, sec-octyl cyanoacrylate typically has a shelf life of about 12–24 months. |
A single-component, solvent-free liquid based on sec-octyl cyanoacrylate (2-octyl cyanoacrylate, CAS 133978-15-1) is applied to opposing wound edges under light manual approximation. The liquid anionically polymerises on contact with trace moisture and basic amine groups present on the skin surface. The reaction proceeds without mixing, without external heat, and without exposure to ultraviolet radiation. Commercial medical-grade material is supplied with residual acidic stabiliser in the range of 5–15 ppm and moisture content below 0.1% by Karl Fischer titration. Application is performed only after haemostasis has been achieved and the wound edges are dry. Typical film thickness is controlled between 0.1 mm and 0.5 mm. Thicker films increase heat accumulation and extend full cure time beyond 120 s. The wound edges are held with gloved fingers or atraumatic forceps for 30–60 s until the polymer reaches green strength. Terminal assembled product is a sterile single-use applicator containing 0.5 mL of monomer, sealed under nitrogen in an aluminium foil pouch. Sterility is maintained by aseptic filling because terminal dry-heat sterilisation can initiate premature polymerisation and reduce monomer purity. The cured film is tested according to ASTM F2458-05 for wound closure strength and ASTM F2255-05 for lap-shear strength properties. Biological evaluation is performed under ISO 10993-1:2018 with cytotoxicity testing per ISO 10993-5:2009 and intracutaneous irritation testing per ISO 10993-10:2010. The topical skin approximation configuration is regulated as a Class II special-controls device under 21 CFR 878.4010. The adhesive is not indicated for wounds under high tension, active infection, or wound edges that cannot be approximated without significant force.
| Designation | Parameter | Applied acceptance condition for sec-octyl cyanoacrylate film |
| ISO 10993-5:2009 | Cytotoxicity via MTT assay | Cell viability not reduced below 70% of control |
| ISO 10993-10:2010 | Intracutaneous reactivity | No significant erythema or oedema at 24 h, 48 h, 72 h |
| ASTM F2458-05 | Wound closure strength | Force at failure recorded as a function of film thickness |
| ASTM F2255-05 | Lap-shear strength of tissue adhesive | Failure mode reported with cohesive or adhesive separation |
| 21 CFR 878.4010 | Class II topical tissue adhesive | Special controls including bench and biocompatibility data |
| ISO 11607-1:2019 | Sterile barrier packaging | Seal integrity after accelerated and real-time ageing |
The octyl ester side chain reduces the rate of anionic propagation compared with methyl or ethyl homologues. This effect is observed as a longer fixture time of 60–90 s at 50% RH, whereas ethyl cyanoacrylate formulations typically fixture in 10–30 s under identical conditions. The slower polymerisation rate lowers the peak temperature rise in a thin film applied to skin. Published comparative differential scanning calorimetry data for sec-octyl cyanoacrylate films are limited. The lower propagation rate is inferred from longer setting time and reduced dermal erythema in ISO 10993-10:2010 irritation studies. In paediatric low-tension lacerations, haemostasis is obtained by direct pressure. The wound is dried with sterile gauze, and a 0.5 mL applicator is inverted and squeezed to form a continuous 3 mm wide bead along the approximated edges. The film extends 5–10 mm beyond each wound apex to prevent edge lifting. Manual approximation is held for 30–60 s. The cured adhesive remains intact for 5–10 days and sloughs with the stratum corneum; no removal visit is required. Residual monomer content in the cured film is measured by solvent extraction followed by gas chromatography-mass spectrometry using the analytical framework of ISO 10993-18:2020. Chemical characterisation data are used to support the toxicological risk assessment for a paediatric surface-contact device. The adhesive is not indicated for wounds with ongoing bleeding, puncture wounds, animal or human bites, or complex lacerations requiring deep sutures. Clinical use is limited to low-tension, uncontaminated, clean-edged lacerations where the practitioner can achieve complete edge approximation without excessive force.
In canine and feline surgical closure, sec-octyl cyanoacrylate is applied over a buried intradermal suture line as a protective barrier and secondary approximation layer. The adhesive must not be used as a replacement for fascial sutures in high-tension abdominal closures. A 0.5 mL applicator covers approximately 12–15 cm of linear incision when laid as a 3 mm wide strip. Excess adhesive on the suture surface can create rigid spicules that traumatise adjacent skin during normal movement. The adhesive cures in 30–90 s at 37 °C and 50–80% RH; skin temperature and ambient moisture cause faster surface skin-over than in human dermal wound applications. Compatibility with polypropylene and poliglecaprone sutures is assessed by visual inspection after 24 h saline immersion at 37 °C. No suture degradation is observed when the adhesive is applied in a thin continuous film. Batch filling of veterinary applicators requires dry nitrogen purge. Residual moisture in the ampoule above 0.2% triggers premature gelation during 12-month storage. The cured adhesive is tested for cytotoxicity according to ISO 10993-5:2009 as a reference method even though veterinary devices are not required to follow human medical device regulations in every jurisdiction. The adhesive is not indicated for wounds with active infection, necrotic tissue, puncture wounds, or wounds requiring debridement before closure.
Polyurethane catheter shaft segments are joined to polycarbonate hubs using low-viscosity sec-octyl cyanoacrylate dispensed in 0.005–0.020 mL shots. Fixturing is performed on rotary indexing lines with 12–16 stations. Ultraviolet-cured adhesives are not required because substrate surface moisture initiates anionic polymerisation. The low-viscosity grade is specified at 20–40 mPa·s at 25 °C by ISO 2555:2018. Tight viscosity control is critical for needle dispense repeatability. Batch-to-batch variance above ±5% produces variation in wicking into the catheter-hub gap. Capillary tips of 0.25 mm internal diameter and positive-displacement valves deliver shot volume capability above Cpk 1.33 when the filling line is maintained at 40–60% RH. Fixture time at 50% RH is 10–20 s. At 20% RH, fixture time extends beyond 60 s, requiring controlled humidity cabinets set to 40–60% RH. Cured adhesive lap shear strength on polycarbonate-to-polyurethane specimens is tested according to ISO 4587:2003. Cohesive failure in the polyurethane substrate is preferred over adhesive failure at the hub surface. Stress cracking in polycarbonate hubs is controlled by limiting residual monomer. A post-cure bake at 50 °C for 4 h reduces residual monomer below 0.1 wt%. Biocompatibility data for the cured adhesive in a catheter-hub configuration are generated under ISO 10993-1:2018 for prolonged contact. Extraction per ISO 10993-18:2020 with both polar and nonpolar solvents is required. Incompatibility with amine-functional primers must be considered because residual ammonia or amines initiate anionic polymerisation during storage and cause premature gelation in the dispense tip.
| Process condition | Fixture time measured on polycarbonate hub | Observed production failure mode |
| 20% RH, 23 °C | >60 s | Delayed fixturing, part movement before green strength |
| 50% RH, 23 °C | 10–20 s | No failure when shot volume exceeds 0.005 mL |
| 70% RH, 23 °C | 5–10 s | Surface skin-over, poor gap wetting, adhesive starvation |
Volatile monomer from cyanoacrylate adhesives can condense on surrounding surfaces and form a white haze. Sec-octyl cyanoacrylate has a lower vapour pressure than methyl or ethyl homologues, reducing this effect in closed automotive interior cavities. In EPDM door seal profile assembly, a primer-free process is used with a 1.5–2.0 mm bead applied at 0.05–0.08 mL/m. The substrate is cleaned with isopropanol and dried to ≤60% RH. Cure speed is controlled by ambient humidity. At 30% RH, the fixture time reaches 30–45 s. At 70% RH, the surface skins over before adequate wetting, producing a weak boundary layer. Manufacturing lines commonly maintain 40–60% RH to balance fixturing speed and substrate wetting. Compliance with automotive volatile organic compound requirements is verified using VDA 278:2011 and ISO 12219-3:2012. Residual solvent-based contact adhesive emissions are eliminated when sec-octyl cyanoacrylate replaces chloroprene contact cements. Aged bond performance is tested after 1000 h at 85 °C and 85% RH according to ISO 9142:2003. Elongation at break of cured film is measured according to ASTM D638-14. Typical values for octyl ester-based films are higher than for ethyl ester films, but published data for this specific automotive configuration is limited. The adhesive is not recommended for joints that undergo continuous peel loading without mechanical fastening because cyanoacrylate films exhibit lower peel strength than flexible two-component polyurethane adhesives.
During in-line splicing of extruded silicone and nitrile gasket profiles, cyanoacrylate formulations containing sec-octyl cyanoacrylate are applied without primer to prevent telescoping at the splice joint. The cured adhesive layer retains elongation at break above 15% according to ASTM D638-14 when tested on 2 mm cured films. The joint is pressed between heated platens at 40 °C for 10 s to accelerate cure and reduce internal stress. Failure in production is most commonly observed as adhesive starvation at the splice overlap when bead length is below 5 mm or when the gap exceeds 0.1 mm. The process is limited to non-critical gasket applications where adhesive volatile content is below the detection limit of the original equipment manufacturer fogging test. Primer-free operation is possible only when the substrates are freshly extruded and free of silicone mould-release residues. Contamination with amine-containing release agents must be avoided because residual amines initiate anionic polymerisation before the joint is assembled.
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Sec-octyl cyanoacrylate, formally 2-octyl 2-cyanoacrylate (IUPAC: octan-2-yl 2-cyanoprop-2-enoate; CAS 133978-15-1), is a moisture-curing alkyl cyanoacrylate monomer with molecular formula C12H19NO2 and relative molecular mass 209.29. The ester substituent is a branched sec-octyl group attached through the second carbon of the octane backbone, distinguishing it from linear n-octyl cyanoacrylate and from shorter-chain n-butyl and ethyl homologues. Commercial model designations for this substance are supplier-specific and usually combine nominal fill volume, applicator tip geometry, and viscosity grade; typical single-use configurations include 0.5 mL, 1.0 mL, and 5.0 mL sterile barrels or crushable glass ampoules. The monomer is stabilised with acidic inhibitors such as sulphur dioxide, methanesulphonic acid, or organic sulphonic acids at combined concentrations below 500 mg/kg. A representative technical specification may report monomer assay not less than 98.0% by gas chromatography, water content not more than 500 mg/kg, and colour not exceeding 50 APHA. Published data for this specific configuration is limited; the cited limits should be verified against the supplier certificate of analysis.
Viscosity classes are specified because the pure monomer is low-viscosity and may run on vertical tissue surfaces. Low-viscosity grades with rotational viscosity below 50 mPa·s spread rapidly into narrow incisions; medium-viscosity grades between 50 mPa·s and 500 mPa·s remain in place on vertical surfaces; high-viscosity grades above 500 mPa·s are compounded with polymethyl methacrylate or poly(vinyl alkyl ether) thickeners. Model designations may include suffix codes for tinted formulations used to improve visibility on skin. The base monomer and thickened formulations differ in cure speed, film modulus, and applicator force; a thinner low-viscosity film may produce lower initial tensile strength than a thicker high-viscosity film of the same chemistry.
Under ambient conditions, the cure of sec-octyl cyanoacrylate proceeds by an anionic/zwitterionic mechanism. Trace water on a substrate provides hydroxide or other nucleophilic species that attack the electron-poor β-carbon of the monomer, generating a resonance-stabilised carbanion or zwitterion. Propagation continues by addition of further cyanoacrylate units, while termination occurs when the growing chain encounters an acidic inhibitor, a proton source, or a local mobility constraint. On human skin at relative humidity of 40–70%, the apparent set time is generally reported from 20 s to 60 s, with handling strength developing over 2–5 min. Cure rate is not an intrinsic constant because it is controlled by surface moisture, film thickness, temperature, acid inhibitor concentration, and substrate pH. Lap-shear strength of tissue adhesive films is commonly assessed under ASTM F2255-05 using conditioned substrates at 23 ± 2 °C and 50 ± 10% relative humidity.
Compared with methyl and ethyl cyanoacrylates, the sec-octyl monomer exhibits lower propagation exotherm per unit mass. This reduces the risk of substrate distortion and local temperature rise when the bond line exceeds 100 μm or when adhesive is applied to thin polymer films. Because the polymer chain retains the long alkyl side group, the cured film is less rigid and displays plasticised rather than brittle behaviour.
On production-scale filling lines, product-contact surfaces are constructed from electrophished 316L stainless steel with polytetrafluoroethylene or ceramic pump internals. Carbon steel, copper alloys, and zinc-plated fittings are excluded because metal cations and surface oxides can induce local anionic polymerisation and discolouration. Bulk monomer is transferred under dry nitrogen at a dew point of −40 °C or lower and held at 5–20 °C; line relative humidity is maintained below 35%. Moisture ingress above 200 mg/kg typically produces high-molecular-mass tails in size-exclusion chromatograms and stringing at filling needles. Batch-to-batch viscosity drift is minimised by closed-loop inert-gas blanketing of feed vessels during long campaigns.
Temperature control during high-speed filling is critical because the moisture sensitivity and inhibitor activity of the monomer are temperature-dependent. At line temperatures above 20 °C, acid inhibitors partition into the vapour phase and polymerisation kinetics accelerate; at temperatures below 0 °C, absorbed moisture can condense on cold metal parts, creating local gel nuclei. A practical control band of 5–15 °C is therefore maintained for bulk monomer, with a tolerance of ±5 °C at the filler bowl. Process alarms are set when the filler bowl deviates beyond 5 °C from the target setpoint because viscosity drift and needle stringing are observed more frequently outside the control band.
When a formulator or clinical purchasing specification substitutes sec-octyl cyanoacrylate for n-butyl cyanoacrylate, the longer branched alkyl ester changes handling and film mechanics. The sec-octyl polymer is softer and more flexible after polymerisation, which reduces cracking over mobile skin surfaces and joint contours. The lower polymerisation exotherm lowers the thermal insult to thin or fragile skin, but the trade-off is a moderately slower set time relative to n-butyl and ethyl grades. During application, wound edges must be held in eversion and manual approximation for the extended setting interval before film stress is applied. This product is used in topical approximation of low-tension lacerations, surgical incisions with subcutaneous closure, and minor skin tears; it is not intended for high-tension wounds, mucosal surfaces, infected ulcers, ophthalmic contact, or internal use unless a specific medical-device clearance covers that indication.
Amine-containing accelerators and strong nucleophiles are incompatible with sec-octyl cyanoacrylate because they initiate rapid exothermic polymerisation. Ethanolamine, N,N-dimethyl-p-toluidine, and residual amine-cured epoxy surfaces must be segregated from the assembly area. Substrates made from polyethylene, polypropylene, or fluoropolymers require plasma, corona, or primer treatment before bonding; on untreated polypropylene, published lap-shear data for this configuration is limited and generally falls below 0.5 MPa.
Poly(sec-octyl cyanoacrylate) exhibits a substantially lower modulus than poly(ethyl cyanoacrylate) because the C8 ester side chain acts as an internal plasticiser. Free films tested under ASTM D638-14 show higher elongation at break than shorter-chain homologues, although absolute values are formulation-dependent and published data for this specific configuration is limited. For rigid-to-rigid assemblies, general-purpose octyl cyanoacrylates commonly exhibit lap-shear strength on ABS, rigid PVC, and aluminium in the range 5–15 MPa after 24 h cure when evaluated according to ISO 4587:2003. Strength decreases sharply when bond-line thickness exceeds 100 μm or when substrate surfaces carry fatty acids, siloxane mould release, or high levels of retained moisture. The lower vapour pressure of the sec-octyl monomer reduces white blooming on sensitive surfaces, but acetone or solvent-wipe residues must be fully evaporated before assembly because residual solvent can retard polymerisation.
Unlike ethyl cyanoacrylate, the octyl grade is not generally selected for high-speed wicking of close-fitting metal joints; its fixture speed on aluminium or steel is slower and more sensitive to ambient humidity. For low-tension skin applications, however, the flexibility of the sec-octyl film provides a closer mechanical match to skin than shorter-chain homologues under cyclic movement.
Medical-device technical files for sec-octyl cyanoacrylate formulations reference biological evaluation under ISO 10993-1:2018. Representative endpoint designations and acceptance criteria are listed below; this table does not constitute regulatory clearance for any specific model or supplier.
| Endpoint | Reference method | Representative acceptance criterion |
|---|---|---|
| Cytotoxicity | ISO 10993-5 | No grade greater than 2 |
| Sensitisation | ISO 10993-10 | No erythema or oedema grade greater than 1 |
| Intracutaneous irritation | ISO 10993-23 | No severe or persistent irritation |
| Subchronic dermal toxicity | ISO 10993-11 | No systemic toxicity at clinically relevant exposure |
| Sterility assurance | ISO 11135:2014 or ISO 11137-2:2013 | Sterility assurance level 10−6 |
Hydrolytic degradation of poly(sec-octyl cyanoacrylate) in phosphate-buffered saline at 37 °C proceeds by ester hydrolysis and chain scission. The longer alkyl ester reduces water uptake and cumulative formaldehyde release relative to shorter-chain homologues, which is one toxicological rationale for its use in medical-surface applications. Degradation is thickness-dependent: films above 200 μm may develop a porous hydrated surface while the core remains intact, producing variable peel behaviour in wound-closure testing. In vivo mass loss is not reliably predicted from buffer hydrolysis alone because macrophage-mediated hydrolysis and enzymatic activity at the tissue–film interface accelerate chain scission.
The shelf life of sec-octyl cyanoacrylate is limited by slow hydrolysis, acid inhibitor depletion, and thermally induced colour formation. Storage at 2–8 °C extends the usable interval, but repeated warming to ambient temperature for use may create condensation inside the vial; devices should be equilibrated to room temperature while sealed to avoid moisture ingress. Forced-degradation studies at 40 °C and 75% relative humidity generally show viscosity rise and reduced lap-shear strength after 90 days, but published data for this specific configuration is limited; suppliers validate shelf life by real-time and accelerated stability protocols based on ISO 11607-1:2019 for packaging integrity and ISO 10993-1:2018 for biological evaluation maintenance.
Sterile medical applicators are filled under low-moisture conditions to prevent premature oligomerisation, which appears as stringing at the filling needle and as an elevated high-molecular-mass tail in size-exclusion chromatography. Bulk monomer is held below 15 °C during filling, and the free-acid content is monitored by potentiometric titration to confirm that the inhibitor setpoint has not been depleted. Applicator barrels and plungers are selected from low moisture-vapour-transmission polypropylene grades with moisture vapour transmission below 0.3 g/m²/day at 38 °C and 90% relative humidity. On high-speed lines with 12–24 filling stations, the interval between opening and capping is kept under 20 s; pre-drying of barrels at 60 °C for 2 h in dry air is used before filling, but lower temperatures are applied to colour-sensitive formulations because prolonged heating promotes yellowing and acid scavenging.
At relative humidity above 60%, pre-drying of applicator components is required before filling, and extended exposure of open monomer containers is avoided. The processing window for filler-bowl temperature is intentionally narrow because excursions beyond ±5 °C from the target setpoint increase the incidence of needle stringing and inconsistent shot weight. Inert-gas purging of the filler bowl and capping area is maintained at positive pressure to exclude humid ambient air.
In industrial assembly, sec-octyl cyanoacrylate is used as a lower-odour, lower-bloom adhesive for flexible PVC, EPDM rubber, thermoplastic elastomers, and medical device bonding where methyl and ethyl grades are too brittle. Fixture speed on plasticised PVC and EPDM is slower than that of methyl cyanoacrylate but remains within 5–40 s when the bond line is below 50 μm. On automated dispensing lines, wetted needles made from polytetrafluoroethylene or polyether ether ketone reduce polymer build-up; stainless steel needles require flushing with anhydrous inhibitor-containing solvent to prevent tip blockages. The long alkyl chain lowers surface energy sensitivity but does not eliminate need for surface preparation; low-surface-energy polyolefins still require plasma, corona, or primer treatment to achieve cohesive failure mode. Sec-octyl cyanoacrylate should not be compounded into melt-processable polymer matrices on twin-screw extruders with L/D ratios above 40:1 because the monomer begins to polymerise in the barrel and can cause screw seizure at melt temperatures above 120 °C.
