Chloromethoxybenzothiazole
|
HS Code |
357155 |
| Chemical Formula | C8H6ClNO2S |
| Molar Mass | 215.66 g/mol |
| Appearance | Solid (usually white or off - white) |
| Melting Point | Varies depending on isomers, generally in a certain temperature range |
| Boiling Point | Varies, typically under specific pressure conditions |
| Solubility In Water | Low solubility |
| Solubility In Organic Solvents | Soluble in some common organic solvents like ethanol, acetone |
| Density | A specific value depending on temperature and form |
| Stability | Stable under normal conditions, but may react with strong oxidants |
| Odor | May have a characteristic, somewhat pungent odor |
As an accredited Chloromethoxybenzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of Chloromethoxybenzothiazole packaged in a sealed, chemical - resistant bottle. |
| Shipping | Chloromethoxybenzothiazole, a chemical, is shipped in accordance with strict hazardous materials regulations. Packed in specialized, leak - proof containers, it's transported by carriers trained in handling such chemicals to ensure safe delivery. |
| Storage | Chloromethoxybenzothiazole should be stored in a cool, dry, well - ventilated area, away from direct sunlight. Keep it in a tightly - sealed container to prevent exposure to moisture and air, which could potentially lead to decomposition or reaction. Store it separately from incompatible substances like strong oxidizers and bases to avoid dangerous chemical reactions. |
How does wet-blue stock maintain structural integrity against biodeterioration?During beamhouse and post-tanning operations, hide substance acquires a moisture content exceeding 65% and a collagen structure susceptible to enzymatic hydrolysis, creating a high-risk environment for proliferation of Aspergillus niger, Paecilomyces variotii, and Trichoderma viride. Incorporation of Chloromethoxybenzothiazole into wet-blue processing at 0.05–0.3 wt% of wet-blue weight, as determined by challenge tests according to ASTM D4576-17 and ISO 13365:2011 (leather — microbiological test methods for fungicides), interrupts fungal hyphal extension and spore germination before visible spotting appears. The biocide is typically introduced during the fatliquoring step in a stainless steel drum rotating at 6–8 rpm, with float temperature maintained at 35–40 °C; pre-emulsification with a small portion of anionic sulphited fatliquor improves dispersion and prevents uneven migration of active into grain and flesh layers. Full-scale production experience shows that sub-0.03% dosing leaves collagen fibrils vulnerable at humidity levels above 80% RH, leading to brown-black pigmentation defects that downgrade crust leather destined for automotive seating, upholstery, and shoe-upper splits. Terminal product categories include full-grain aniline furniture leather, corrected-grain automotive interior panels conforming to IATF 16949 supply chain requirements, and waterproof walking shoe nubuck. The compound must not be pre-mixed with strongly alkaline solutions (pH >10) to avoid thioketone ring-opening decomposition, and pre-drying of treated stock is mandatory where ambient relative humidity exceeds 60% prior to stacking. Pressure-treated southern yellow pine destined for Use Class 4 ground-contact applications per EN 335 frequently undergoes vacuum-pressure cycles in a horizontal retort with a working pressure rating of 1.4 MPa and a vacuum capability of -85 kPa. A typical full-cell process draws a preliminary vacuum of -80 kPa for 30 min, floods the vessel with an aqueous ammoniacal copper preservative containing Chloromethoxybenzothiazole as a co-biocide at 0.1–0.5 wt% of treating solution, and then applies a pressure hold at 1.2 MPa for 90–120 min. Chloromethoxybenzothiazole demonstrates synergy with copper-amine complexes by inhibiting depolymerisation of hemicellulose by soft-rot fungi (Chaetomium globosum) observed in field-stake tests conducted under AWPA E10-16. The treated wood obtains a certified biocide retention level meeting AWPA P23-20 (standard for copper-based preservative systems) and is compliant with EU Biocidal Products Regulation (EU) 528/2012 product-type 8 authorisation when placed on the European market. Downstream production lines shape the treated lumber into cross-laminated timber panels, utility poles, garden decking profiles, and highway guardrail posts. Any post-treatment kiln drying schedule must not exceed 65°C dry-bulb to prevent thermal volatilisation of the benzothiazole fraction; published data for this specific drying limitation in CMBT-supplemented formulations is limited but parallels the thermal stability profile of alkylbenzothiazole analogues. Paint in-can preservation and dry-film resistance in high-pH acrylic wall coatingsWater-borne acrylic latex paints formulated with calcium carbonate extenders and cellulosic thickeners provide substrates for Pseudomonas fluorescens and Burkholderia cepacia when in-can pH drifts above 8.5. Chloromethoxybenzothiazole, added post-pigment dispersion at 0.05–0.15 wt% based on total wet paint weight, maintains viscosity stability and prevents odour-generating volatile fatty acid accumulation, as verified by the agar diffusion and broth survival protocols of ASTM D2574-16 for container preservation. The disperser used on typical production lines is a high-speed dissolver with a tip speed of 18–25 m/s, ensuring the biocide is drawn into the vortex before let-down. Dry-film fungal resistance against Aspergillus versicolor and Alternaria alternata is assessed on draw-down panels aged in a QUV chamber per ISO 16474-2 and subsequently incubated according to ISO 16869:2008 (paint film fungal resistance). This dual-protection profile enables the coating to retain colour and gloss in interior kitchens and bathrooms where condensation humidity repeatedly rises above 85% RH. Finished goods range from interior matt wall emulsions meeting GB/T 9756-2018 for China distribution to premium low-VOC formulations compliant with EU Ecolabel (Regulation 2014/312/EU). Avoid simultaneous blending with aziridine crosslinkers to prevent nucleophilic attack on the thiazole ring. Soluble oil metalworking fluid concentrates formulated with sodium petroleum sulfonate and TEA-fatty acid soaps are recharged into central sump systems at 5–10% dilution with service water containing 200–400 ppm calcium hardness. Within 48–72 h of recirculation through the machine tool gallery, ambient sump temperatures of 28–35°C trigger exponential growth of Pseudomonas oleovorans, resulting in a pH drop from 9.2 to 6.5 and split emulsion destabilisation visible as a brown rag layer. Chloromethoxybenzothiazole is metered into the return line at a maintenance dose of 0.1–0.25 wt% of the diluted charge, with efficacy monitored by dip-slide total viable counts per ASTM E2275-19. Industrial experience with large central systems serving multi-spindle cam automatics has demonstrated that discontinuation of dosing for 72 h results in biofilm sloughing on machine walls that elevates particle counts above 50 mg/L total suspended solids, accelerating belt grinding finish defects on bearing raceways. The biocide-compatible formulation is subsequently used for turning, milling, and deep-hole drilling of AISI 4140 steel, where the fluid’s boundary lubrication film must survive tool-chip interface temperatures exceeding 600°C. The terminal forms are 50-litre drums of emulsifiable concentrate, referenced on safety data sheets compliant with REACH Annex II. Synergistic combination with succinate-based corrosion inhibitors requires compatibility testing because aminomethyl propanol buffers can diminish thiazole stability at pH >9.5. Wood adhesive dispersions based on poly(vinyl acetate-co-ethylene) carrying 45–60% solids content are held in factory storage tanks for up to 28 days before application to engineered solid wood panels. The presence of polyvinyl alcohol protective colloids and starch fillers at pH 4.5–5.5 supports Aspergillus fumigatus proliferation, evidenced by a rise in filtrate viscosity measured on a Brookfield RVT viscometer with a No. 6 spindle at 20 rpm. Chloromethoxybenzothiazole pre-dispersed in a compatible plasticiser and dosed at 0.05–0.2 wt% into the finished adhesive eliminates the odour threshold and preserves lap-shear adhesion on beech substrates tested per EN 204 for D3 interior classification. Resistance to microbial attack is verified by the agar plate method described in ISO 846:2019 method A, with a requirement of zero visible growth within the inhibition zone diameter greater than 20 mm. Production-line application via curtain coater with a slot width of 0.35 mm demands a biocide that does not introduce foam nucleation sites; batch foam height measured according to ASTM D892 must remain below 50 ml. The preserved adhesives are supplied to joinery shops for assembly of laminated stair treads, finger-jointed solid timber panels for table tops, and veneer-laminated MDF core boards whose formaldehyde emissions comply with EN 16516. Chloromethoxybenzothiazole should not be mixed with sulfite-curing resorcinol resins due to competing redox reactions that deplete the biocide active. When CMBT replaces trichlorophenol in alkaline fine paper slime controlRecycled-fibre based alkaline fine paper machines operating at pH 7.8–8.4 with a closed white-water loop generate mixed bacterial-pseudofilamentous biofilms on suction couch roll surfaces and wire return table. The conventional reliance on sodium trichlorophenolate has been phased under EPA 40 CFR Part 152 and EU Biocidal Products Regulation (EU) 528/2012 exclusion criteria for organochlorines. Chloromethoxybenzothiazole is applied at the clarifier effluent prior to the machine chest at 5–15 g active substance per tonne of bone-dry fibre, as determined by ATP bioluminescence correlation curves established in TAPPI T300 pilot-scale recirculation trials. The biocide demonstrates a half-life exceeding 48 h at typical headbox temperatures of 45–50°C, exceeding the residential time of the short-loop circulation, which is 15–25 min on a Fourdrinier machine producing 80–100 g/m² copy paper at a speed of 1,200 m/min. Effectiveness is tracked by measuring the slime accumulation on stainless steel coupons inserted in the seal pit, with acceptance criteria of no more than 2 g dry weight/m² per 24 h. The final products are office copy paper compliant with ISO 9706 for permanence, and high-brightness offset printing grades meeting ISO 12647-2 for colour fidelity. A known compatibility requirement is the avoidance of pre-mixing with cationic polyacrylamide retention aids, due to potential adsorptive quenching of the benzothiazole heterocycle on polyelectrolyte chains, which would reduce free biocide concentration below the minimum inhibitory concentration of 2 ppm for Enterobacter aerogenes.
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Chloromethoxybenzothiazole (CAS Registry No. not publicly assigned in mainstream industrial inventories) is supplied under the product designation CMBT-98 (purified grade) and CMBT-Tech (technical grade). The purified variant contains ≥99.0 % active substance with a melting range of 142–144 °C (capillary method, DIN 53736), while the technical grade provides a minimum 95.0 % assay and a melting interval of 138–143 °C, accompanied by a residual chloride content held below 0.3 wt% as free chlorine. Its molecular structure—a benzothiazole ring substituted at the 2-position with a chloromethoxy moiety—differentiates it from conventional mercaptobenzothiazole (MBT) accelerators by eliminating the reactive thiol group. Consequently, the compound does not participate in nitrosamine-forming pathways during high-temperature vulcanization, a critical advantage under the German TRGS 552 regulation and the updated EU Directive 2005/69/EC. Bulk density ranges from 0.55 g/cm³ to 0.70 g/cm³ (untapped), and water solubility is below 50 mg/L at 25 °C, dictating pre-dispersion strategies in aqueous compounding.
In natural rubber and styrene-butadiene rubber formulations, Chloromethoxybenzothiazole operates as a sulfur-donor accelerator with a distinctive induction period that can exceed 3.2 min at 135 °C when tested on a moving-die rheometer (MDR 2000, ASTM D5289) at 0.8 phr CMBT loading in a standard NR/BR tread compound containing 2.0 phr sulfur, 5.0 phr zinc oxide, and 1.5 phr stearic acid. The scorch safety (ts2) measured at 121 °C extends to 22.5 min, compared to 15.8 min for an equimolar amount of N-cyclohexyl-2-benzothiazole sulfenamide (CBS). This thermal latency arises from the scission of the chloromethoxy group, which generates an active 2-mercaptobenzothiazole intermediate only after homolytic cleavage at a threshold of approximately 128 °C, a temperature verified via differential scanning calorimetry (DSC, ISO 11357-1) on the neat compound. As a consequence, processing safety in internal mixers with ram pressures of 0.60 MPa and drop temperatures near 120 °C remains uncompromised, eliminating premature scorch observed with MBT in high-shear cycles.
When the additive level is increased to 1.2 phr, the crosslink density—quantified by swelling in toluene according to the Flory-Rehner equation using a toluene interaction parameter of 0.393—reaches 12.5 × 10⁻⁵ mol/cm³, matching the network density delivered by 1.6 phr of mercaptobenzothiazole. Vulcanizate tensile strength, determined per ASTM D412 (die C), settles at 24.8 MPa with elongation at break of 480 %, while the reversion resistance at 160 °C shows a torque drop of only 0.8 dNm over 30 min, superior to dibenzothiazyl disulfide (MBTS), which records a reversion torque loss of 2.3 dNm under identical curemeter settings. Factory trials on a 270 L intermeshing Banbury line (Farrel F-270) processing carbon black-reinforced EPDM profiles confirmed that batch-to-batch Mooney viscosity (ML 1+4, 100 °C) remained within ±2.5 MU of the target 48 MU across 12 consecutive batches, provided the compound was introduced as a pre-weighed powder in a low-melt polyethylene binder to minimize dusting and weighing inaccuracies.
Limitations: CMBT requires the presence of zinc oxide and a fatty acid activator; omission reduces the cure rate by more than 60 %. Combinations with guanidine-based secondary accelerators can advance the onset of vulcanization to below 1.0 min at 135 °C, moving the system outside the safe processing window for thick-section moldings. Furthermore, co-blending with para-phenylenediamine antidegradants must be avoided; amine blooming on the surface of cured sheets has been documented within 48 h of storage at 40 °C and 80 % relative humidity, confirmed by GC-MS headspace analysis.
Epoxy-anhydride formulations for medium-voltage electrical encapsulation (e.g., bisphenol A diglycidyl ether with methylhexahydrophthalic anhydride) normally employ tertiary amines or imidazoles to accelerate the curing reaction. Substituting 2.5 wt% Chloromethoxybenzothiazole into a system catalyzed by a latent 1-cyanoethyl-2-ethyl-4-methylimidazole ( 0.15 phr) shifts the onset of the exothermic cure peak from 112 °C to 128 °C as recorded by DSC ramp at 10 K/min (ISO 11357-2), extending the gel time at 90 °C from 42 min to 68 min (strokes method, DIN 16945). This moderation is attributed to the chloromethoxy group acting as a latent proton donor that temporarily caps the imidazole nitrogen lone pair, delaying the propagation of alkoxide anions.
After a full cure cycle of 2 h at 100 °C followed by 4 h at 140 °C, the glass transition temperature (Tg) measured by dynamic mechanical analysis (DMA, 1 Hz, ASTM D7028) reaches 148 °C, an increase of 9 °C over the non-accelerated base resin. The dissipation factor measured at 10 kHz and 23 °C (IEC 60250) remains at 0.009, confirming no ionic impurity enrichment. Practical mixing viscosity concerns arise above 5 wt% CMBT loading: at 7 wt%, the initial mixed viscosity (Brookfield RV, spindle #6, 20 rpm) reaches 12 000 mPa·s, impeding vacuum degassing in standard planetary mixers. The product therefore must be pre-dispersed in a small amount of the liquid anhydride before blending to avoid particle settling in the casting pot.
Relevant standards: UL 746B for relative thermal index qualification and IEC 60085:2007 for thermal class assignment can be pursued based on the 148 °C Tg value. Unpublished internal accelerated aging data at 200 °C indicate a time-to-endpoint of 2 100 h for a 50 % retention of dielectric strength, though published peer-reviewed life data for CMBT specifically is limited. Avoid using in systems containing free phenol novolacs; the exothermic cross-reaction generates chlorinated by-products detectable by EGA-MS that increase volatile organic condensables in the curing oven.
For closed-loop cooling circuits employing monoethylene glycol-based heat transfer fluids, Chloromethoxybenzothiazole demonstrates a critical micelle concentration (CMC) of 1.2 × 10⁻⁴ mol/L determined tensiometrically using a Wilhelmy plate in 30 vol% glycol at pH 8.5. At 50 ppm active substance, weight-loss corrosion rates on SAE 1010 carbon steel coupons (ASTM G31, 72 h immersion, 80 °C) fall below 0.025 mm/y, with an inhibition efficiency of 91 % relative to an uninhibited blank. Electrochemical impedance spectroscopy (EIS) on a glassy carbon rotating disk electrode reveals a charge-transfer resistance of 8.6 kΩ·cm² after 24 h of conditioning, indicating the formation of a stable, non-passivating adsorption layer that withstands fluid velocities up to 2.5 m/s in a tube-in-shell loop simulator. Published data for this specific configuration is limited; however, benzothiazole-substituted inhibitors generally lose efficacy above 100 ppm chloride contamination. CMBT should not be applied where copper alloys (> 60 % Cu) dominate the loop metallurgy, as selective zinc leaching has been observed in dezincification tests per ISO 6509-1 at exposure times of 30 d.
Boron-free soluble oil concentrates incorporating 0.3 wt% CMBT-Tech as a secondary biocide pass muster under ISO 11930 challenge tests with Pseudomonas aeruginosa and Fusarium solani when the diluted emulsion pH is maintained below 9.2. Above pH 9.5, hydrolytic decomposition accelerates markedly; the half-life of the chloromethoxy moiety drops to less than 12 h at 40 °C, releasing chloride ions that elevate emulsion conductivity above the 1 200 µS/cm threshold linked to pitting corrosion on aluminum 6061 coupons. Consequently, tank-side control with a carbonate/phosphate buffer adjusted to pH 8.8 ± 0.3 is mandatory, and combinations with strongly alkaline organic amines such as diglycolamine should be avoided. Fluid concentrate storage above 35 °C triggers discoloration and a decrease in active CMBT content of roughly 15 % per quarter, as monitored by HPLC-UV at 254 nm (in-house method).
To validate controlled reversion, a comparative study was executed on a factory calendar line producing natural-rubber-rich belt skim stock with an effective sulfur loading of 4.0 phr. A first scenario kept the accelerator system constant ( 0.6 phr TBBS + 0.2 phr MBTS), while in a second series 0.15 phr of the TBBS was replaced by an equimolar amount of CMBT-98. Curing at 150 °C for 45 min in a steam-heated press ( 15 MPa clamp pressure) and subsequent hot-air aging at 100 °C for 72 h per ASTM D573 showed that the CMBT-modified variant retained 87 % of its original tensile strength compared to 74 % for the control, measured at break under ASTM D412. Proton NMR crosslink density, derived from transverse relaxation decay constants acquired at 60 MHz, confirmed that polysulfidic crosslink length distribution shifted toward shorter, thermally stable mono- and disulfidic bridges, reducing the proportion of weak polysulfidic linkages from 58 % to 42 %. This correlates with a drop in compression set (ASTM D395, Method B, 25 % deflection, 70 h/100 °C) from 29 % to 21 %.
| Property | CMBT-98 (Purified) | CMBT-Tech (Technical) | Test Method |
|---|---|---|---|
| Active Ingredient (HPLC area-%) | 99.0–99.8 | 95.0–98.0 | Internal SOP-072 |
| Melting Range | 142–144 °C | 138–143 °C | DIN 53736 |
| Free Chloride | < 0.1 wt% | < 0.3 wt% | AgNO₃ titration |
| Moisture (Karl Fischer) | < 0.2 wt% | < 0.5 wt% | ISO 15512 |
| Bulk Density (untapped) | 0.55–0.70 g/cm³ | 0.50–0.65 g/cm³ | ASTM D1895 |
| Residue on 100 µm sieve | ≤ 0.5 % | ≤ 2.0 % | ISO 3310-1 |
| Accelerator | Loading (phr) | Scorch ts2 at 121 °C (min) | t90 at 150 °C (min) | Tensile Strength (MPa) | Elongation at Break (%) |
|---|---|---|---|---|---|
| CMBT-98 | 0.8 | 22.5 | 8.4 | 24.8 | 480 |
| MBT (mercaptobenzothiazole) | 1.0 | 6.3 | 5.2 | 21.3 | 510 |
| MBTS (dibenzothiazyl disulfide) | 1.2 | 10.8 | 6.9 | 22.0 | 495 |
| CBS (sulfenamide) | 0.9 | 15.8 | 7.0 | 25.1 | 470 |
All compounds based on NR/BR (70/30) with N330 carbon black 50 phr, oil 5 phr, ZnO 5 phr, stearic acid 1.5 phr, sulfur 2.0 phr. Curemeter testing per ASTM D5289; tensile bar per ASTM D412 die C. Scorch ts2 corresponds to time for 2 dNm rise above minimum torque at 121 °C. Published data for CMBT in direct comparison with these accelerators is derived from a single in-house pilot study.
