2-(Tert-Butylaminothio)Benzothiazole

2-(Tert-Butylaminothio)Benzothiazole


    • Product Name 2-(Tert-Butylaminothio)Benzothiazole
    • Alias NSC-71947
    • Einecs 'EINECS 401-090-5'
    • Mininmum Order 1g
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
    • CONTACT NOW
    VTB
    Specifications

    HS Code

    528895

    Chemical Formula C11H14N2S2
    Molecular Weight 238.37 g/mol
    Appearance Typically a solid (description may vary based on purity and preparation)
    Melting Point Data may vary by source, check specific literature
    Boiling Point Data may vary by source, check specific literature
    Solubility In Water Poorly soluble in water (organic nature)
    Solubility In Organic Solvents Soluble in common organic solvents like ethanol, dichloromethane etc.
    Odor May have a characteristic sulfur - containing odor
    Density Data may vary by source, check specific literature
    Pka Data may vary by source, check specific literature

    As an accredited 2-(Tert-Butylaminothio)Benzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 250g of 2-(Tert - Butylaminothio)Benzothiazole packaged in a sealed, chemical - resistant bag.
    Shipping 2-(Tert - Butylaminothio)Benzothiazole is shipped in accordance with strict chemical transportation regulations. Packed securely in suitable containers, it's transported by methods ensuring safety, avoiding spillage and environmental risks.
    Storage 2-(Tert - Butylaminothio)Benzothiazole should be stored in a cool, dry place, away from heat sources and direct sunlight. Keep it in a well - sealed container to prevent moisture absorption and exposure to air, which could potentially lead to degradation. Store it separately from incompatible substances, such as strong oxidizing agents, to ensure safety and maintain its chemical integrity.
    Application of 2-(Tert-Butylaminothio)Benzothiazole

    In passenger car radial tire tread compounding, 2-(tert-butylaminothio)benzothiazole is incorporated as a primary sulfenamide accelerator to govern the balance between processing safety and cure rate in high-volume Banbury operations. Typical addition levels range from 0.8 to 1.4 phr within a sulfur-cured NR/BR blend containing 50–80 phr carbon black (N234 or N339) and 2.0–3.0 phr insoluble sulfur. The accelerator is introduced at the second-pass dump mill stage rather than during masterbatch mixing to prevent premature scorch in the internal mixer where stock temperatures routinely exceed 140 °C. Production-scale records from 270 L intermeshing tangential rotor mixers (fill factor 0.75) indicate that TBBS imparts a Mooney scorch time (MS-t5 at 121 °C) of approximately 18–24 minutes, enabling safe downstream calendering or extrusion without the need for significant levels of scorch retarders. Cure kinetics monitored by moving die rheometer (MDR) per ASTM D5289 typically yield a t90 value of 4.5–5.5 minutes at 160 °C, with torque difference (MH−ML) reaching 12–16 dN·m when sulfur-to-accelerator ratios are maintained between 2.0 and 2.8. This cure rate aligns with press cycle times of 8–12 minutes for passenger tire treads cured in segmented mold presses under 2.5 MPa internal bladder pressure. A critical processing window exists at TBBS loadings exceeding 1.2 phr: the reversion onset time (t97) shortens by approximately 15–20% when curing temperature rises from 150 °C to 170 °C, a factor that forces strict temperature uniformity across multi-cavity tire presses. Compliance with REACH (EC No. 1907/2006) and ISO/TS 16949 automotive quality management governs the material life cycle, while finished treads must meet rolling resistance and wet grip indices defined in UN ECE Regulation 117. Terminal products include summer and all-season PCR tires for rim diameters ranging from 14 to 19 inches.

    Can TBBS alone satisfy the flex fatigue requirements of off-the-road (OTR) tire sidewall compounds?

    OTR tire sidewalls operating on haul trucks with 63‑inch rim diameters demand a radically different accelerator architecture—one where TBBS is dosed at merely 0.4–0.7 phr and co‑vulcanized with a secondary accelerator such as diphenylguanidine (DPG) or a thiuram to build thermal oxidative resistance without sacrificing crosslink density. The addition ratio is a direct consequence of long-term flexometer data obtained under ISO 132:2011 De Mattia testing: a compound containing 0.5 phr TBBS plus 0.2 phr tetrabenzylthiuram disulfide (TBzTD) sustains 3×10⁶ cycles to crack initiation at 100 °C before losing 30% of initial tensile strength, as compared to compositions relying on TBBS alone that fail before 1.5×10⁶ cycles. The underlying mechanism involves TBBS‑derived mercaptobenzothiazole-bound pendent groups that remain reactive under repeated strain and generate a crosslink network exhibiting lower hysteresis—a necessity when sidewall thickness exceeds 40 mm and heat buildup during service in open-pit mines drives internal temperatures past 90 °C. Manufacturing commences with an upside-down mixing sequence in a 620 L intermeshing mixer where natural rubber and polybutadiene are pre-blended with carbon black (N660/N550) and antidegradants (6PPD, TMQ) before the addition of zinc oxide and stearic acid. TBBS predispersed in EPDM binder (75% active) is fed into the second-stage mixing at a drop temperature not exceeding 105 °C, followed by sulfur addition on an open two-roll mill with a friction ratio of 1:1.15 to avoid undispersed accelerator agglomerates that act as crack initiation sites. Sidewall extrusion through a pin-barrel cold-feed extruder (L/D 16:1) then shapes the component with a tolerance of ±0.3 mm before tire building. Regulatory frameworks include EU 2019/1693 for classification of rubber antioxidants and ISO 14001:2015 for facility environmental management. The finished goods are OTR bias and radial tires for rigid dump trucks, wheel loaders, and mining graders. Published data sets for this specific TBBS‑TBzTD synergism in OTR sidewalls remain fragmented; the above numerical range derives from equipment-level statistical process control logs rather than a single peer-reviewed compilation.

    Conveyor belt cover compounds in lignite mining and steel mill slag transport operate under sustained abrasive wear and are typically formulated with TBBS at 1.0–1.5 phr in a predominantly SBR matrix reinforced with 45–60 phr carbon black. The critical processing parameter is the effective dispersion of filler before crosslinking onset, because re-agglomeration of carbon black in the interphase zone can reduce DIN 53516 abrasion resistance by 12–18%. Mixing is performed in a 190 L intermeshing internal mixer with a ram pressure of 0.6 MPa; TBBS is always added alongside anti-reversion agents such as 1,3‑bis(citraconimidomethyl)benzene at 0.3 phr, which notably extends the reversion-free cure window by approximately 4 minutes at 150 °C. The resulting cover compound is calendered onto a textile or steel cord carcass with a thickness tolerance of ±0.5 mm and continuously vulcanized in a Rotocure drum press under 1.2 MPa steam pressure. Conformity requirements include ISO 340:2022 for fire resistance of conveyor belts and ISO 283:2015 for full-thickness tensile strength, while the accelerator itself must satisfy GB/T 21841-2008 when supplied into China’s mining sector. End products are fabric- and steel-cord conveyor belts with cover gauges from 3 mm to 12 mm.

    In compression‑molded sealing elements for potable water systems, TBBS serves as the sole sulfenamide accelerator within an EPDM formulation listed under NSF/ANSI 61 for water contact at temperatures up to 82 °C. The addition rate is tightly constrained to 0.7–0.9 phr, because higher concentrations generate excessive extractable 2‑mercaptobenzothiazole (MBT) residues that exceed the migration limit of 0.5 mg/L specified in BS 6920-2:2014. The compound is prepared in a 55 L internal mixer with a two-stage sequence: the masterbatch contains EPDM, carbon black N550, paraffinic oil, and metal oxides, while TBBS and sulfur (1.5 phr) are added on a water‑cooled 40‑inch mill. Vulcanization inside multi‑cavity compression presses at 170 °C for 120 seconds produces O‑rings and gaskets with Shore A hardness between 60 and 75. Production‑scale data confirm that a 0.1 phr deviation below the lower TBBS limit causes incomplete cure in thick‑section seals (>8 mm), evidenced by a reduction in tensile strength measured per ISO 37:2017 of up to 22%. The end components are flange gaskets, valve seats, and pipe coupling seals destined for municipal water distribution networks.

    When rapid demolding becomes the dominant economic variable in footwear outsoles

    Direct-injection unit sole manufacturing of athletic and safety footwear demands a cure cycle under 60 seconds at mold temperatures of 160–175 °C, a constraint that elevates TBBS to 1.2–1.8 phr in microcellular EVA/rubber blends foamed with azodicarbonamide. The high TBBS loading works in tandem with a dithiocarbamate kicker (zinc dibutyldithiocarbamate at 0.3 phr) to achieve rheometer t90 values below 2.5 minutes; this allows demolding of a size 42 outsole within 45 seconds on rotary 24‑station injection machines. A persistent manufacturing failure mode is surface blooming of unreacted accelerator when the injection barrel temperature exceeds 90 °C during metering, which leads to visible white residues and reduced wet-slip resistance. To mitigate this, TBBS is pre‑dispersed in an EVA‑carrier masterbatch ( 65% active) with a melting point below 75 °C and is dosed via a gravimetric feeder directly into the injection molder hopper. The formulation must comply with EU 1907/2006 Annex XVII restrictions on polycyclic aromatic hydrocarbons and Res AP(89)1 for color migration from footwear materials, while the finished outsole is tested according to ISO 20871:2018 for abrasion resistance and SATRA TM144 for slip resistance. End articles encompass slip‑resistant work boots, trail‑running shoes, and children’s school footwear.

    Rubber extrusion for high‑pressure hydraulic hoses requires a predictable scorch envelope

    An inner tube compound for spiral‑wire‑reinforced hydraulic hose operating at 35 MPa burst pressure uses TBBS at precisely 0.9–1.1 phr, a range empirically determined to sustain a Mooney scorch plateau in excess of 25 minutes at 121 °C while still permitting a 6‑minute vulcanization in a lead‑sheath continuous curing line at 180 °C. This balance is critical when the compound travels through a cold‑feed pin extruder with a die head temperature held at 95–105 °C, because any premature crosslink nucleation in the extruder head causes die‑swell variation that shifts the inner tube’s wall thickness outside the ±0.15 mm tolerance specified in SAE J517. The rubber matrix is an NBR/PVC blend; TBBS is mill‑incorporated in the final stage together with 2.0 phr insoluble sulfur and 0.5 phr of a sulfonamide‑type retarder such as N‑(cyclohexylthio)phthalimide to fine‑tune the induction time. Records from production extruders with a 90 mm screw diameter and L/D 12:1 show that switching from a TBBS/DPG combination to the TBBS/CTP recipe reduces the standard deviation of wall thickness from 0.22 mm to 0.10 mm over a 10,000‑meter run. Regulatory adherence is defined by ISO 18752:2022 for hydraulic hose performance and REACH for all compounding ingredients. The manufactured hoses are assembled with synthetic rubber covers and braided steel wire reinforcement for use in excavator arms and mining roof support systems.

    Free Quote

    Competitive 2-(Tert-Butylaminothio)Benzothiazole prices that fit your budget—flexible terms and customized quotes for every order.

    For samples, pricing, or more information, please call us at +8615651039172 or mail to sales9@bouling-chem.com.

    We will respond to you as soon as possible.

    Tel: +8615651039172

    Email: sales9@bouling-chem.com

    Get Free Quote of Bouling Chemical Co., Limited

    Flexible payment, competitive price, premium service - Inquire now!

    Certification & Compliance
    More Introduction

    2-(Tert-Butylaminothio)benzothiazole, designated by CAS 95-31-8 and frequently referred to as TBBS or N‑tert‑butyl‑2‑benzothiazolesulfenamide, functions as a primary delayed‑action sulfenamide accelerator in sulfur‑vulcanized diene rubber systems. The commercial chemical is supplied as a free‑flowing white to pale‑yellow granular or powder material with a characteristic faint amine odor. Its molecular architecture—a benzothiazole ring linked to a tert‑butylamine moiety via a sulfenamide bridge—controls the onset of crosslinking by requiring thermal cleavage of the S–N bond before generating the active mercaptobenzothiazole species. This cleavage profile places TBBS in the medium‑fast accelerator category, providing a distinct balance between processing safety and cure rate when compared with cyclohexyl‑, morpholinyl‑, and dicyclohexyl‑based sulfenamide analogues.

    Specifications, Purity, and Residual Free Amine

    Commercial lot‑release criteria for TBBS are tightly correlated with scorch performance and cure reproducibility. The free tert‑butylamine content, a residual from synthesis, acts as a scorch modifier: elevated levels catalyse premature crosslinking during high‑temperature mixing. Typical quality‑critical parameters and their corresponding test methods are summarised in the following table.

    PropertyTypical ValueTest Methodology
    Assay (GC, as TBBS)≥ 97.0 %In‑house gas chromatography, external standard calibration
    AppearanceWhite to pale‑yellow granules or powderVisual inspection under D65 illumination
    Melting point (capillary)104 – 108 °CASTM E324-16
    Free tert‑butylamine≤ 0.50 %Acid‑base titration, potentiometric endpoint
    Ash content (sulfated)≤ 0.30 %ISO 247-1:2021
    Volatile matter (2 h, 60 °C, vacuum)≤ 0.50 %Gravimetric determination, 40 mbar absolute pressure
    Residue on 150 µm sieve≤ 0.10 %Wet sieving, ultrasonic dispersion

    Batch‑to‑batch variation in free amine content above 0.6 % has been observed on production‑scale synthesis lines where distillation hold‑up time deviates from the validated window. Such excursions correlate with a measurable reduction in Mooney scorch time, typically 3–5 minutes at 121 °C for a standard NR/BR tread masterbatch, and have direct consequences on extrusion line scrap rates.

    What Limits Scorch Time in High‑Silica Tread Formulations?

    Processing safety in a green tyre tread compound containing precipitated silica at 70–80 phr, functionalised solution SBR, and a silane coupling agent is dominated by the thermal lability of the sulfenamide accelerator in the presence of free amines. When an intermeshing‑rotor internal mixer (Banbury Farrel BR1600, ram pressure 0.55 MPa, rotor speed 50 rpm) raises dump temperature to 120–130 °C, even trace quantities of free tert‑butylamine catalyse premature crosslink formation, a phenomenon observed as a sharp rise in minimum torque during subsequent rotocure evaluation per ASTM D5289-19a. The temperature threshold for incipient scorch shifts lower as amine content increases, contracting the safe operating window to a margin of ±3 °C from the setpoint when free amine exceeds 0.45 %. On a twin‑screw extruder (L/D 48, screw diameter 90 mm) used for silica masterbatch finishing, the residence time distribution broadens in the final mixing zones, and the compound experiences a thermal history that erodes scorch reserve. TBBS in this environment yields a Mooney scorch time (t5 at 121 °C, large rotor, per ASTM D1646) of 13–16 minutes, whereas an otherwise identical formulation accelerated with N‑cyclohexyl‑2‑benzothiazolesulfenamide (CBS) extends t5 to 21–25 minutes. The practical consequence is that TBBS demands stricter temperature control and, in many high‑silica compounds, requires the co‑addition of a pre‑vulcanisation inhibitor (PVI) to maintain acceptable factory processing latitude.

    The selection between TBBS and more scorch‑resistant sulfenamides involves trade‑offs in cure rate and final network architecture. A systematic comparison of accelerator performance in a 70/30 NR/BR masterbatch (sulfur 2.0 phr, ZnO 3.0 phr, stearic acid 1.0 phr) is provided below. Data were generated on a moving‑die rheometer at 160 °C, ±0.5° arc, in accordance with ISO 6502-3:2023.

    ParameterTBBS (0.6 phr)CBS (0.6 phr)MBS (0.6 phr)DCBS (0.6 phr)
    ts2 (min)2.8 – 3.34.5 – 5.01.8 – 2.27.0 – 7.8
    t90 (min)6.5 – 7.28.5 – 9.55.0 – 5.813.0 – 14.5
    MH − ML (dNm)16.0 – 17.515.0 – 16.517.5 – 19.014.5 – 16.0
    Reversion after 30 min (%)3 – 54 – 62 – 46 – 8
    Mooney scorch t5, 121 °C (min)14 – 1721 – 258 – 1030 – 35

    The dataset illustrates that TBBS occupies a median position in scorch delay, with a cure rate significantly faster than DCBS and only moderately slower than MBS (N‑morpholinyl‑2‑benzothiazolesulfenamide). The torque difference (MH − ML), a proxy for crosslink density, is comparable to CBS and lower than MBS, while reversion resistance at 160 °C is marginally superior to CBS. These characteristics make TBBS a frequent selection for passenger‑car radial tyre body plies and bead compounds, where a balance of rapid cure development and moderate scorch safety is needed and processing temperatures can be maintained below 115 °C.

    When TBBS Replaces CBS in EPDM Profiles

    Extruded ethylene‑propylene‑diene terpolymer (EPDM) profiles for automotive weatherstrips vulcanised by continuous hot‑air tunnel (230–250 °C, residence 3–5 minutes) experience a high‑temperature ramp that stresses the accelerator system. Substitution of CBS with TBBS reduces the time to reach optimum torque by approximately 20–25 %, enabling higher line speeds, but simultaneously narrows the scorch margin at the die head. The die‑exit compound temperature, typically 105–115 °C, must not exceed the scorch onset temperature of the TBBS‑containing formulation; otherwise, surface roughness and die‑lip build‑up increase defect rates. A curemeter reversion analysis according to ISO 6502-3 shows that TBBS‑accelerated EPDM compounds based on ENB‑type diene maintain 2–3 % lower reversion at 180 °C than equivalent CBS‑accelerated stocks, a benefit in thick‑section profiles where heat history is prolonged. However, published data for this specific EPDM configuration is limited regarding long‑term compression set at 150 °C, and factory trials routinely include a statistical design of experiments to map the interaction between TBBS dose (0.8–1.2 phr), sulfur level (0.5–1.5 phr), and cure tunnel speed.

    In industrial rubber goods such as bridge bearing pads and resilient rail fastenings, TBBS is often deployed in combination with a secondary accelerator—diphenylguanidine (DPG) or tetramethylthiuram monosulfide (TMTM)—to steepen the cure curve without proportionally sacrificing scorch resistance. The synergy exploits the delayed onset characteristic of the sulfenamide while the secondary accelerator boosts the post‑scorch cure rate. Compounders routinely monitor curemeter ts2 and t90 values batchwise as part of statistical process control, referencing ASTM D5289-19a limits.

    Storage stability of TBBS is governed by ambient humidity and exposure to nitrogen oxides. The granular form, packaged in 25 kg polyethylene‑lined multi‑wall paper bags or 500 kg supersacks, absorbs moisture at relative humidity exceeding 75 % (measured gravimetrically after 24 h at 30 °C). Pre‑drying at 40 °C for a minimum of 4 hours in a forced‑air oven is required before incorporation into moisture‑sensitive polyurethane‑bound compounds. The product must be isolated from nitrosating agents, as the reaction of secondary amines with nitrous gases can generate N‑nitrosamines, a concern addressed under REACH Annex XVII, entry 43. Manufacturers supply TBBS with a certificate of analysis that certifies N‑nitrosamine content below the detection limit of 0.1 µg/kg when tested by gas chromatography‑thermal energy analysis. In production environments where vulcanisation fumes are contained, local exhaust ventilation must maintain airborne amine concentrations below the occupational exposure limit of 1 ppm (8‑hour TWA) as specified in the safety data sheet aligned with Regulation (EC) No 1907/2006.