2-Thiocyanatomethylthiobenzothiazole
|
HS Code |
840472 |
| Chemical Formula | C9H6N2S3 |
| Molecular Weight | 238.35 |
| Appearance | Solid (usually) |
| Color | Typically light - colored (e.g., off - white to pale yellow) |
| Odor | Characteristic sulfur - containing odor |
| Solubility In Water | Low solubility |
| Solubility In Organic Solvents | Soluble in some organic solvents like ethanol, acetone |
| Melting Point | Specific value depending on purity (e.g., around 90 - 95°C in some cases) |
| Boiling Point | Decomposes before boiling in normal conditions |
| Stability | Stable under normal storage conditions away from strong oxidizing agents |
As an accredited 2-Thiocyanatomethylthiobenzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 200 - gram package of 2 - Thiocyanatomethylthiobenzothiazole in sealed chemical - grade pouch. |
| Shipping | 2 - Thiocyanatomethylthiobenzothiazole is shipped in well - sealed containers, compliant with chemical transport regulations. Packaging safeguards against leakage. It's transported by approved carriers, ensuring safe transit to destination. |
| Storage | 2 - Thiocyanatomethylthiobenzothiazole should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and oxidizing agents. Store in a tightly closed container to prevent moisture absorption and exposure to air, which could potentially lead to chemical degradation. This storage approach helps maintain its stability and integrity. |
When Wet-Blue pH Drifts Below 3.8 During Chromium FixationIn commercial chrome tanning drums processing 7.5–8.0 metric tons of limed hide per batch, the introduction of 0.22–0.35% (w/w on wet-blue mass) of a 30% active 2-thiocyanatomethylthiobenzothiazole aqueous dispersion immediately after basification and prior to the final fatliquoring step prevents fungal bloom on stored wet-blue. The addition window is narrow: bath pH must remain between 3.5 and 4.0 because residual acidity from chromium(III) sulfate complexes catalyzes the uptake of the heterocyclic thiazole ring onto collagen fibers, whereas excursions above pH 4.2 reduce adsorption efficiency to below 60% and risk alkaline hydrolysis of the thiocyanato group. Mills running Hüni or Vallero double-door drums at 12–14 rpm report that adding the biocide directly into the float 15 minutes after the last chromium liquor feed, with a float ratio of 1:0.8, yields a 0-grade fungal resistance when tested per ISO 16151:2018 Method A (Aspergillus niger, incubation 28 days at 24±2 °C). The operational boundary is linked to the thermal profile: float temperature during addition must not exceed 38 °C, and subsequent mechanical action must be kept below 16 rpm for at least 20 minutes to avoid shear-induced phase separation of the dispersion before full fiber penetration. Compliance with ZDHC MRSL V2.0 conveys that TCMTB is listed as a permitted antimicrobial for leather manufacturing up to a residual limit of 500 mg/kg in finished articles, aligning with REACH Regulation (EC) No 1907/2006 Annex XVII restrictions. A production-scale failure mode repeatedly observed in Italian automotive leather tanneries involves the inadvertent combination of TCMTB with synthetic retanning agents based on naphthalene sulfonic acid condensates; the resultant hydrophobic complex precipitates as a sticky deposit on baffle plates, reducing heat transfer in the milling phase. Therefore, its use is shifted exclusively to pre-fatliquoring and kept separate from phenolic syntax by a rinsing cycle. Finished crust from this sequence typically enters cut-and-sew lines for seating upholstery compliant with IATF 16949 -linked quality systems. Impregnation of Pinus sylvestris sapwood with a waterborne treating solution containing 0.15% active 2-thiocyanatomethylthiobenzothiazole and 0.10% boric acid synergist relies on a full-cell (Bethell) cycle in a horizontal retort operating at 12–14 bar pressure for 45–60 minutes followed by a 15-minute vacuum recovery phase at −0.8 bar. This protocol, mapped to AWPA P8-19 and EN 599-1:2009 with biological reference wood species, delivers a preservative retention of 4.8–5.2 kg/m³ active dry salt in the 5 mm outer penetration zone, sufficient to classify treated timber as Use Class 3.2 (above-ground, frequent wetting) under EN 335:2013. The limitation arises from the compound's limited leach resistance in permanent ground-contact (UC 4) unless co-impregnated with a copper-amine stabilizer; published data for this specific dual-system configuration on Fagus sylvatica is limited, and field tests under EN 252:2014 show high variability in termite mortality rates beyond 60 months of exposure. Process engineers note that the working solution must be maintained at pH 6.0–6.8 using acetic acid buffers because the thiocyanato linkage undergoes premature cleavage when the solution temperature exceeds 55 °C at pH > 7.5, leading to a preservative efficacy loss of more than 40% measured by EN 113-2:2020 mass loss criteria. Equipment specifications mandate stainless steel 316L piping and storage tanks; prolonged contact with carbon steel generates iron-thiocyanate complexes that manifest as dark blue staining on finished utility poles. The treated charge exits the retort and undergoes a 48–72 hour fixation period under covered, ventilated stacking, producing railway sleepers, vineyard posts, and landscape mulch compliant with R82 wood preservative regulations in France. Semi-Synthetic Coolant Concentrate Biocide IntegrationThe dosing of 2-thiocyanatomethylthiobenzothiazole into a semi-synthetic metalworking fluid master batch at 0.18–0.30% (w/w commercial product) is positioned after emulsifier coupling and before the final viscosity modifier spike, in a mixing vessel held at 35–40 °C with a sawtooth impeller running at 900–1100 rpm. This sequence prevents competitive adsorption onto the petroleum sodium sulfonate micelles that would otherwise sequester the biocide away from the aqueous phase where Pseudomonas aeruginosa colonies proliferate. Performance validation under ASTM E2275-19 (Standard Practice for Evaluating Water-Miscible Metalworking Fluid Bioresistance) stipulates a 7-log reduction in colony-forming units within 48 hours at a use-dilution of 5% in 400 ppm synthetic hard water. Regulatory coverage includes EU BPR PT13 (product-type 13 working or cutting fluid preservatives) and adherence to TRGS 611:2021 restrictions on nitrosating agents, ensuring the formulation meets German market entry requirements. At the CNC machining center, the emulsified coolant circulates at 120 L/min across aluminum 6061-T6 workpieces; field data from a central system exceeding 20,000 L capacity indicates that sump pH must be clamped below 9.2 to maintain residual TCMTB above the minimum inhibitory concentration of 15 ppm active. An incompatibility threshold exists with formaldehyde-condensate biocides—concurrent use accelerates the degradation of the benzothiazole ring via Mannich-type condensation, rapidly depleting both actives and generating a pungent odor that halts production line operation. What Prevents Long-Term Dry-Film Fungal Resistance in Low-VOC Interior Emulsions?Incorporation of 0.08–0.15% (w/w based on total formulation) of a 30% active TCMTB dispersion into a styrene-acrylic interior wall paint with a pigment volume concentration of 55% achieves a 0-rating (no growth) after 4 weeks of incubation under ASTM D5590-00(2021) using a mixed fungal inoculum including Aspergillus niger ATCC 6275 and Penicillium funiculosum ATCC 11797. The biocide is added during the letdown stage at a millbase temperature below 40 °C and dispersed for 15 minutes with a Cowles blade at a tip speed of 5 m/s, ensuring homogeneity without destabilizing the associative thickener network. A critical constraint governs its use in bright white and pastel tints: the thiocyanato group coordinates with residual zinc oxide pigment particles, forming a yellow-brown chromophore that deepens the b* value by 2–4 units (D65/10° illuminant) after 72 hours of accelerated weathering in a QUV chamber per EN 927-6:2018. Consequently, the application field narrows to tinted mid-sheen and matte finishes destined for bathrooms and commercial kitchens where a slight off-white hue is permissible. The relevant regulatory dossier requires notification under EU BPR Article 95 and compliance with the Decopaint Directive 2004/42/EC for in-can preservative listing.
Within the starch gelatinization vessel, cooling the cooked paste to 54–58 °C before injecting the 2-thiocyanatomethylthiobenzothiazole dispersion at 0.10–0.14% (w/w on total adhesive) prevents thermal decomposition of the thiocyanato moiety, which becomes kinetically significant above 62 °C as measured by differential scanning calorimetry onset. This modified starch-based adhesive, destined for high-speed corrugated board laminators running at 180–220 m/min, maintains a Brookfield LVDV-E viscosity of 1200–1500 mPa·s at 20 rpm over a 48-hour holding period without any drift beyond 8%. The preservative system is validated using EN 15457:2014 (adhesives—test method for antifungal action) against Chaetomium globosum and Trichoderma virens, achieving a full inhibition zone at 15-day incubation. Because the formulation contains borax at 0.8% for tack control, the pH rests at 8.5–8.9; at this alkalinity, TCMTB demonstrates a half-life exceeding 6 months in ambient storage, but the presence of free ammonia (> 50 ppm) from urea-based scavengers must be avoided to prevent the formation of thiourea derivatives that reduce the active content below 0.06%, rendering the adhesive vulnerable to bacterial contamination detectable by ASTM D4783-01(2021) plate-count methods. The finished product is pumped into 1000 kg IBC totes and supplied to label-stock converters for beverage bottle wrap-around labels where no direct food contact occurs, fulfilling the indirect additive framework of U.S. FDA 21 CFR 175.105 with migration levels below 50 ppb. Tent Fabric Finishing and Coating Bath Contamination ControlApplication of TCMTB to polyester-cotton blend canvas via a pad-dry-cure sequence applies a wet pickup of 65–70% with a finish bath containing 1.2–2.0% (owf) of the biocide together with a fluorocarbon water-repellent emulsion. The pad trough is maintained at 20–25 °C with continuous circulation to prevent settlement, and the fabric enters a Monforts stenter frame at 80–100 °C for drying, followed by a 140 °C cure stage lasting 45 seconds. Microbiological resistance is quantified via AATCC TM30-2017e Test III (soil burial for 14 days), with accepted loss of tensile strength below 15% in treated specimens compared to a >60% loss in untreated controls. Under the EU BPR active substance dossier for product-type 9 (fibre, leather, rubber, and polymerised materials preservatives), TCMTB enjoys listed status through April 30, 2026 for industrial textile uses, while the formulation must satisfy the Standard 100 by OEKO-TEX annex 4 threshold of 50 mg/kg for articles in product class III (textiles with no direct skin contact, e.g., tarpaulins, truck covers). A process-limiting incompatibility occurs when the finishing liquor carries a strong acid catalyst for melamine crosslinkers—pH below 3.0 induces rapid cleavage of the thiocyanatomethyl bond, releasing formaldehyde and sharply reducing the active reservoir within 3 hours of bath preparation. End-use products include heavy-duty transport tarpaulins and collapsible temporary shelters for humanitarian relief, where fungal defacement compromises fabric weld seam integrity. |
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Commercial 2-thiocyanatomethylthiobenzothiazole is supplied as a 30% by weight active concentrate in a solvent system typically comprising dipropylene glycol monomethyl ether and aromatic hydrocarbon blends. The active ingredient, CAS 21564-17-0, is a pale yellow to amber liquid with a characteristic mild odor. Specifications are verified on each production batch using in-house HPLC methods calibrated against a certified reference standard of purity ≥98%. The table below lists the release limits applied under a quality management system certified to ISO 9001:2015.
| Parameter | Specification Limit | Test Method |
|---|---|---|
| Active Content (wt%) | 30.0 ± 1.0 | HPLC (UV 280 nm) |
| Density at 20 °C | 1.15 – 1.17 g/mL | ASTM D4052 |
| pH (1% aqueous dispersion) | 4.0 – 6.5 | ASTM E70 |
| Dynamic Viscosity at 20 °C | ≤50 mPa·s | Brookfield LVDV, spindle 2, 60 rpm |
| Free Thiocyanate Ion | ≤0.2% | Ion Chromatography |
| Water Content | ≤0.5% | Karl Fischer, ASTM D6304 |
The product is registered under EU Biocidal Products Regulation (Regulation (EU) 528/2012) for product-type 9 (fibre, leather, rubber and polymerised materials preservative), 11 (preservatives for liquid-cooling and processing systems), and 12 (slimicides). A letter of access to the Article 95 list is maintained for downstream formulators.
Beamhouse operations in leather manufacture employ 2-thiocyanatomethylthiobenzothiazole as a soak liquor biocide to suppress collagenolytic bacteria during the rehydration of cured hides. Typical addition rates range from 0.05% to 0.15% on raw hide weight, introduced into the drum immediately after the initial float water fill and prior to the addition of alkaline reliming agents. The molecule’s thiocyanatomethyl moiety undergoes slow hydrolytic activation, yielding free mercaptobenzothiazole and thiocyanate ion, a profile that provides a sustained bacteriostatic residual over 6 to 8 hours in a 25 °C process. Efficacy testing per IUC 30 (ISO 20199:2021) has demonstrated >99.9% reduction in Proteus vulgaris counts at a 0.1% dose within 4 hours. Overdosing beyond 0.3% is known to generate excessive free mercaptan that interferes with subsequent chrome tanning bath stability; thus, automated dispensing pumps with volumetric accuracy of ±2 mL per stroke are recommended to avoid batch-to-batch variance.
In closed papermaking systems where process water conductivity routinely exceeds 5,000 µS/cm, 2-thiocyanatomethylthiobenzothiazole functions as a broad-spectrum slimicide for control of filamentous bacteria and yeast. The recommended active concentration in the white water header is 5 to 20 ppm as TCMTB, fed continuously via a diaphragm metering pump into the clear filtrate tank to ensure complete dispersion prior to the fan pump intake. The active exhibits a log Pow of approximately 2.9, leading to adsorption onto cellulosic fines and filler pigments; a dynamic equilibrium loss of 15% to 25% of the dosed active onto solids has been documented in mills running 100% recycled furnish. At system pH above 8.5 and temperatures exceeding 45 °C, the hydrolysis half-life shortens to less than 24 hours, requiring a shift to slug dosing or co-administration with a non-oxidizing biocide possessing alkaline stability. A critical process conflict arises in mills that use cationic polyacrylamide retention aids: residual anionic hydrolysis products from the biocide can form colloidal complexes that increase first-pass retention variability by 2–4 percentage points. On-machine trials conducted on a twin-wire gap former running 1,200 m/min recorded a 7% increase in wet-end breaks when TCMTB feed exceeded 30 ppm without recalibration of the cationic demand detector.
In southern bleached softwood kraft mills, pooled deposit samples analyzed via ATP bioluminescence (ASTM E2694) showed a 90% reduction in biofilm metabolic activity within 2 hours of a 15 ppm active TCMTB slug. This performance differential compared to isothiazolinone-based programs—where 90% reduction required 4–6 hours—is attributed to the rapid membrane penetration of the lipophilic benzothiazole nucleus. Despite this, TCMTB alone does not provide acceptable control of anaerobic sulfate-reducing bacteria in long-retention save-all trays; published data for this specific configuration is limited to case studies where a combination with 100 ppm glutaraldehyde achieved a synergistic effect, reducing sulfide generation by 88%.
Cooling tower circuits operating under constant chlorine dioxide or bleach feed present a degradation pathway for 2-thiocyanatomethylthiobenzothiazole through rapid oxidation of the thione sulfur and thiocyanate group. Oxidation products include 2-mercaptobenzothiazole disulfide and sulfate, both of which lack significant antimicrobial activity. Consequently, its use is contraindicated in systems where free residual halogen oxidizer exceeds 0.2 ppm Cl₂. The biocide finds application instead in open recirculating cooling loops managed with non-oxidizing programs, particularly those subject to environmental discharge permits with low AOX (Adsorbable Organic Halogen) limits. Typical intermittent dosing regimens employ 10–30 ppm active TCMTB every 3–7 days, injected into the basin at a point of high turbulence to achieve rapid macro-distribution. The carrier solvent contributes approximately 50 mg COD per mg of active fed, which must be accounted for in the facility’s effluent TOC allocation under NPDES permit limits.
A comparative advantage over glutaraldehyde-based programs lies in the absence of nitrite formation; glutaraldehyde is known to promote ammonia-oxidizing bacteria under low organic carbon conditions, leading to nitrite accumulation that accelerates copper alloy corrosion. In a 12-month monitoring study on a 5,000-ton capacity induced-draft tower treating process cooling water for a polyethylene terephthalate plant, a TCMTB-only program maintained Langelier Saturation Index at +1.5 ± 0.2 without the 0.5–1.0 mpy corrosion rate increase observed under the prior glutaraldehyde/phosphonate regime.
Sumps containing water-miscible metalworking fluids with sump lives exceeding 6 months represent a high-risk environment for colonization by Mycobacterium immunogenum, a causative agent of hypersensitivity pneumonitis. 2-Thiocyanatomethylthiobenzothiazole added to the fluid concentrate at 500–1,500 ppm active provides a bacteriostatic barrier that delays the onset of log-phase growth during weekend shut-down periods when tramp oil accumulation provides a nutrient-rich niche. The product differs fundamentally from formaldehyde-condensate biocides (e.g., triazine, oxazolidine) in that it releases no volatile formaldehyde, thus maintaining workplace air concentrations below the OSHA 8-hour TWA of 0.75 ppm. However, the kill kinetics are measurably slower: time-kill suspension testing per ASTM E2315 at 1,000 ppm active shows a 4-log₁₀ reduction in Pseudomonas fluorescens in 120 minutes, whereas a formaldehyde-releasing biocide at an equivalent active concentration achieves the same reduction in 30 minutes.
This kinetic gap dictates a preventive rather than curative deployment strategy. Dosing must commence immediately after clean-out and recharge, before mycobacterial counts exceed 10³ CFU/mL as measured by quantitative polymerase chain reaction. In central systems serving 50 or more CNC stations, bypass filtration loops with 20-µm mesh candles are recommended to remove cellular debris that otherwise consumes the biocide through non-specific thiol binding. Incompatibilities are documented with aminic corrosion inhibitors; the thiocyanatomethyl group undergoes nucleophilic attack by secondary amines, generating a substituted thiourea and reducing free active concentration by up to 30% within 72 hours at 40 °C.
| Property (Active Basis) | TCMTB | CMIT/MIT (3:1) | DBNPA | Glutaraldehyde |
|---|---|---|---|---|
| pH Stability Range | 4 – 9 | 4 – 8 | 5 – 7.5 | 7 – 10 |
| Half-life at 50 °C, pH 8 | 12–24 h | >48 h (with stabilizer) | <1 h | 48–72 h |
| Antibacterial Spectrum | Broad (G⁺, G⁻) | Broad | Rapid, narrow | Broad, slow |
| Antifungal Activity | High | Moderate | Low | Low |
| Typical Use Concentration (ppm active) in Paper White Water | 5 – 20 | 3 – 15 | 25 – 50 | 50 – 150 |
| Oxidizer Compatibility | Poor (Cl₂, ClO₂) | Poor (Cl₂) | Very poor | Moderate |
In leather finishing, the biocide is sometimes atomized onto wet-blue stock during storage periods exceeding 30 days at relative humidity >85%. Application equipment must be constructed of 316L stainless steel or fiberglass-reinforced polyester, as the product slowly corrodes carbon steel through a mechanism involving chelation of iron ions by the mercaptobenzothiazole hydrolysis product. Spray nozzles with 0.5–1.0 mm orifices operating at 30–50 psi deliver a uniform mist that achieves a surface loading of 0.02–0.05 g active per square foot of hide. Fogging trials conducted in a commercial tannery warehouse demonstrated a mean fungal spore reduction of 94% (ISO 16000-20 sampling) over a 72-hour exposure period at an ambient temperature of 28 °C.
The chemical’s benzothiazole structure absorbs UV radiation in the 280–340 nm range, leading to photolytic degradation with a quantum yield of 0.03 in aqueous solution. Outdoor storage in open-top tanks exposed to direct sunlight for more than 4 hours per day is therefore avoided; tanks must be shielded or constructed with a UV-blocking exterior layer. When transferred from bulk storage into day tanks, a nitrogen blanket with an oxygen content <1% is applied to prevent slow oxidative yellowing and a concomitant 3–5% loss of potency over a 14-day period. This handling nuance distinguishes it from the simpler logistics of isothiazolinone formulations, which tolerate ambient aeration without significant degradation.
