N-Tertiarybutyl-2-Benzothiazole Sulfenamide

N-Tertiarybutyl-2-Benzothiazole Sulfenamide


    • Product Name N-Tertiarybutyl-2-Benzothiazole Sulfenamide
    • Alias TBBS
    • Einecs 252-104-2
    • Mininmum Order 25KGS
    • 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

    116838

    Chemical Formula C11H14N2S2
    Molecular Weight 238.37
    Appearance White to off - white powder
    Odor Characteristic odor
    Melting Point 104 - 110 °C
    Solubility In Organic Solvents Soluble in common organic solvents like benzene, toluene
    Insolubility In Water Insoluble in water
    Density 1.26 - 1.32 g/cm³
    Flash Point Approx. 199 °C
    Stability Stable under normal conditions, but may decompose on exposure to heat, light or strong acids

    As an accredited N-Tertiarybutyl-2-Benzothiazole Sulfenamide factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 25 - kg bags packaging for N - Tertiarybutyl - 2 - Benzothiazole Sulfenamide chemical.
    Shipping N - Tertiarybutyl - 2 - Benzothiazole Sulfenamide is shipped in well - sealed containers. It must be transported in accordance with hazardous chemical regulations, ensuring proper handling to prevent spills and exposure during transit.
    Storage N - Tertiarybutyl - 2 - Benzothiazole Sulfenamide should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, ignition sources, and incompatible substances like strong acids and bases. Store in tightly - sealed containers to prevent moisture absorption and degradation, ensuring its quality and stability during storage.
    Application of N-Tertiarybutyl-2-Benzothiazole Sulfenamide

    The hot-feed extrusion line for PCR tread cap compounds demands a sulfenamide accelerator that exhibits a pronounced induction period at typical extrusion head temperatures of 105–120°C while still reaching t90 within the 10–15 bar press cure window. N-tertiarybutyl-2-benzothiazole sulfenamide (TBBS) in a solution-polymerized SBR / high-cis BR blend with N330 carbon black at 70–80 phr loading delivers a Mooney scorch time (MS-t5, 135°C) exceeding 18 minutes and a rheometer cure rate consistent with post-vulcanization stabilization demands. The formulation must satisfy UN ECE R117.02 limits for rolling resistance, wet grip, and external noise, with tread wear indicators validated per ISO 23794:2015. Regulatory compliance extends to EU Tyre Labeling Regulation (EC) No. 1222/2009 class thresholds and REACH Annex XVII restrictions on polycyclic aromatic hydrocarbons originating from extender oils. TBBS is typically charged at 1.3–1.8 phr together with 1.8–2.2 phr insoluble sulfur and a secondary accelerator such as diphenylguanidine at 0.15–0.3 phr to flatten the cure plateau. Downstream, the compound is processed through a 120°C dump tangential rotor internal mixer, followed by a twin-roller sheet-off mill with hip control of 6–8 mm before being fed into a cold-feed pin-barrel extruder with a 14:1 L/D screw. Curing occurs in a segmented mold press at 160°C for 12–14 minutes, producing the finished tread ring that is later buffed for retreading or bonded directly onto the green casing.

    In the construction of all-steel radial truck tires, the wedge and shoulder base compounds adjacent to the belt edge must maintain adhesion to brass-coated steel cord through protracted low-temperature cure cycles and resist oxidative aging-driven modulus creep under 100–110°C service conditions. TBBS at 0.9–1.3 phr in a NR/BR 70/30 base accomplishes a crosslink density, measured by equilibrium swelling per ISO 1817:2015, of (4.8–5.6) × 10−5 mol/cm³ when paired with 2.5 phr sulfur and a cobalt adhesion promoter at 0.8 phr. The compound must comply with ASTM D2229-13 for steel cord adhesion and FMVSS 119 endurance test protocols at 120% rated load. The mixing history involves a primary stage in an intermeshing mixer ramped to 145°C dump temperature, followed by a 95°C secondary stage where curatives are introduced. The green apex is extruded through a 90 mm cold-feed vented extruder operating at 45 rpm screw speed and subsequently calendered onto the bead bundle before the building drum stage. The terminal product is a 315/80R22.5 tire with a retreadable casing rating validated by a 1.5-million cycle drum fatigue run.

    Flame-Retardant Conveyor Belt Cover Stock: TBBS Acceleration Against High-Loading Carbon Black and Antimony Trioxide

    Underground mining conveyor belts subject to MSHA 30 CFR Part 14 and EN 14973:2015 Category B1 drum friction ignition resistance demand cover compounds that retain tensile strength exceeding 18 MPa (measured per ISO 37:2017) despite the antagonistic effect of 15–25 phr chlorinated paraffin and 8 phr antimony trioxide on sulfur vulcanization. TBBS functions here as a primary accelerator at 0.8–1.2 phr, selected over benzothiazyl disulfide (MBTS) to narrow the ts2 – t90 delta and reduce unreacted curative bloom on the belt surface after continuous 185°C rotary cure drum processing. The formulation includes N220 carbon black at 50 phr, a brominated phosphate ester plasticizer, and 2.0 phr sulfur donor to foster monosulfidic crosslinks that limit flammability smoke density to below 400 on the ISO 5659-2 specific optical density scale. A blending cycle in a 270 L intermeshing mixer with ram pressure of 0.6 MPa concludes at a drop temperature not exceeding 125°C; TBBS is added upside-down to prevent pre-scorch in the high-fill-factor chamber. The cover stock is applied by a co-extrusion calender train onto a steel-cord carcass and vulcanized continuously under a 1.8 MPa pressure belt at 170°C, generating 2,400 mm wide finished belt rolls with K3 fire resistance classification for use in potash and coal drift conveyors.

    When Dynamic Stiffness and Fatigue Life Govern Rubber-Metal Bonded Suspension Bushings

    The conflicting requirement in automotive suspension bushings—low dynamic-to-static stiffness ratio (Kdyn/Kstat ≤ 1.35) and 4-million cycle endurance under ±12 mm displacement—places severe constraints on accelerator selection. TBBS at 1.5 phr in a NR/BR 60/40 compound with N550 carbon black at 40 phr and a processing oil level of 5 phr yields a crosslink structure, analyzed via ASTM D6814-02 dynamic mechanical analysis, that minimizes Payne-effect amplitude at 0.5% strain. The compound is formulated to comply with ASTM D2000 M4BG 714 classification and must demonstrate less than 15% stress relaxation after 168 h at 70°C as per ISO 3384-1:2019. Production involves a two-pass internal mixing strategy with a first pass discharged at 130°C incorporating all ingredients except curatives, and a second pass on a 1,500 mm two-roll mill with a friction ratio of 1.25:1 where TBBS and zinc oxide paste are sheeted at 80°C. Injection molding is performed on a horizontal press with a clamping force of 400 tonnes, a barrel temperature profile of 85/90/95°C, and a mold temperature of 155°C for 7 minutes. Finished components are post-cured in an air oven for 4 h at 100°C to decompress residual free sulfur near the metal interface bond.

    How Does TBBS Modulate Crosslink Density Distribution in High-Damping Natural Rubber Bridge Bearings?

    Seismic isolation bearings fabricated to EN 15129:2018 and AASHTO LRFD 18th Ed. require a damping ratio of 12–18% at 100% shear strain, a property governed by the homogeneity of sulfur crosslink lengths within a high-modulus NR formulation. TBBS-dominant vulcanization systems at 1.8 phr with 3.5 phr sulfur and a 0.4 phr thiuram retarder create an initial distribution skewed toward polysulfidic linkages; controlled reversion during the 180-minute low-temperature cure at 140°C reshuffles these toward di- and monosulfidic bonds, as quantified by thiol-amine chemical probe analysis per ISO 24453:2008 (informative Annex C). The mixing process in a 190 L tangential mixer with a 0.75 fill factor employs a 40 rpm rotor speed to avoid excessive shear heating, delivering a masterbatch that is further refined on a 660 mm open mill with a coolant bath holding the stock below 90°C. Laminated bearing pads are compression-molded under 15 MPa in a multi-daylight press with cavity sizes up to 900 mm × 900 mm. The terminal product carries a 60-year design life verified by ISO 22762-1:2018 aging protocol 70°C/28 days with property retention testing conducted at −10°C, 23°C, and 40°C.

    Comparative vulcanizate properties of a high-damping NR bearing compound across TBBS / sulfur ratio variation at 3.0 total sulfur donor equivalents
    TBBS/Sulfur (phr/phr)ts2 (min) @ 140°C (ISO 6502)t90 (min)Hardness (IRHD, ISO 48-4)Effective damping (%) @ 100% shear
    1.5/3.018.5756213.2
    1.8/3.521.06515.7
    2.0/3.519.0686714.4

    The Role of TBBS in Co-Curing Rubber Foxing Tape and Canvas Footwear Constructions

    Canvas vulcanized footwear subjected to EN ISO 20347:2012 occupational footwear requirements and SATRA TM144 sole-to-upper bond strength demands must achieve a 3.5 N/mm minimum peel force along the foxing tape perimeter after aging in a 100°C air oven for 24 h. A marginal addition of TBBS at 0.5–0.7 phr in a NR/SBR 80/20 blend with precipitated silica (15 phr) and N330 black (20 phr) ensures the open mill compound maintains a Mooney ML(1+4) @ 100°C of 55–65 for calendar sheeting onto cotton duck at 90°C. The foxing tape is frictioned onto the canvas upper and assembled with a pre-molded crepe rubber outsole; vulcanization occurs inside an autoclave operating at 0.45 MPa steam pressure for 60 minutes at 135°C. The built-in cure induction provided by TBBS avoids margin flash premature crosslinking that would otherwise block the canvas weft penetration necessary to pass SATRA TM404 stitch tear resistance. The finished footwear type is a lightweight safety clog with static dissipative properties tested per EN 61340-5-1.

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    Certification & Compliance
    More Introduction

    N-Tertiarybutyl-2-benzothiazole sulfenamide (TBBS, CAS 95-31-8) is a primary sulfenamide vulcanization accelerator characterized by a delayed onset of crosslinking combined with a fast cure rate once the reaction is initiated. Commercially distributed under trade designations including Santocure® NS, Vulkacit® NZ, and Rhenogran® TBBS-80, the product is supplied as light-yellow to white granules or powder with a melting range of 104–110 °C and an active content typically not less than 96 % when determined by HPLC per ISO 11235. Its chemical structure—a benzothiazole ring substituted with a tert-butylamine sulfenamide moiety—provides a balance of processing safety and cure efficiency that differentiates it from cyclohexyl-substituted CBS and dicyclohexyl-substituted DCBS, both of which exhibit either a shorter scorch reserve or slower cure development in sulfur-cured polyisoprene and diene elastomer systems.

    What Distinguishes TBBS from Other Sulfenamide Accelerators?

    The accelerator’s scorch delay and vulcanization rate are governed by the thermal stability of the sulfenamide bond. TBBS undergoes homolytic cleavage more slowly than CBS (N-cyclohexyl-2-benzothiazole sulfenamide), extending Mooney scorch time t5 at 135 °C by approximately 30–50 % in a fully compounded NR/BR tread stock. Relative to DCBS (N,N-dicyclohexyl-2-benzothiazole sulfenamide), TBBS initiates crosslinking at a significantly lower temperature, reaching 90 % cure (t90) at 160 °C in 5–7 min versus 8–10 min for DCBS under identical rotorless rheometer conditions (ASTM D5289). This characteristic renders TBBS particularly suited for tire curing cycles operating at 150–170 °C where productivity and blowout resistance are critical. In contrast, the morpholine-substituted sulfenamide MBS yields an even faster cure but suffers from pronounced reversion in high-sulfur NR compounds above 160 °C, a limitation that TBBS mitigates through more controlled crosslink density evolution.

    In passenger tire tread formulations based on 60–80 phr carbon black (N234) in NR/BR blends, TBBS is charged at 0.5–1.2 phr in combination with 2.0–2.5 phr sulfur and often a secondary thiuram accelerator such as tetrabenzylthiuram disulfide at 0.1–0.3 phr. Processing on a tangential internal mixer (Banbury type, ram pressure 0.4 MPa) with dump temperatures maintained below 120 °C preserves the accelerator’s scorch reserve, enabling subsequent extrusion and calendar forming without premature vulcanization. Rheometer traces (ASTM D5289 at 160 °C, 0.5° arc) show a minimum torque ML of 2.5–3.0 dN·m and a plateau maximum MH of 18–22 dN·m, with a cure rate index (t90 – ts2) of 2.5–3.5 min. The resulting vulcanizate exhibits a tensile strength of 20–24 MPa (ISO 37:2017, type 2 dumbbell) and DIN abrasion loss below 120 mm³ (ISO 4649).

    Processing Window and Scorch Safety in Internal Mixers

    When batch temperatures exceed the critical threshold of 120 °C during the final mixing stage, TBBS undergoes homolytic S–N bond scission, yielding 2,2'-dithiobis(benzothiazole) (MBTS) and tert-butylamine. MBTS does not offer the same delayed scorch profile and accelerates the system solely through zinc–accelerator complexes, reducing the scorch safety margin by as much as 40 %—a shift that can manifest as a drop in Mooney scorch time t5 from 32 min to 19 min at 130 °C (ISO 289-1:2015). Consequently, compounding lines equipped with intermeshing twin-screw extruders (L/D 40) utilize controlled barrel zones: feed throat 40 °C, plastication zone 70 °C, and discharge 90 °C, to prevent accelerator degradation. In addition, the amine released acts as a secondary base, potentially increasing network crosslink density and elevating modulus, which may require sulfur level adjustment by 0.2–0.3 phr to maintain Shore A hardness within a 60–65 A specification. This decomposition pathway must be accounted for when scaling from laboratory two-roll mills (roll temperature 50 ±5 °C) to large-scale continuous mixing equipment.

    When CBS-type accelerators cause problematic surface bloom that compromises rubber-to-metal bond integrity in conveyor belt or tire cord applications, formulators replace CBS with TBBS. The tert-butyl group confers a lower solubility parameter difference in the hydrocarbon rubber matrix, reducing the thermodynamic driving force for migration to the surface. Bloom is commonly quantified by measuring the coefficient of friction after heat aging (70 °C for 7 days)—stock containing CBS at 1.0 phr often exhibits a drop in brass-plated steel cord adhesion pull-out force from 620 N to 450 N (ASTM D2229), while an equivalent TBBS-based formulation maintains adhesion above 580 N after aging. This stability makes TBBS the primary accelerator in steel cord skim compounds for radial passenger car tires, where adhesion retention under cyclic stress is validated per ASTM D1871 method B.

    Crosslinking Kinetics in NR/BR Black-Filled Compounds: Comparative Vulcanization Data

    CompoundAccelerator (phr)t5 at 135 °C (min)t35 (min)t90 at 160 °C (min)Tensile Strength (MPa)Elongation at break (%)300% Modulus (MPa)
    TBBS0.735406.523.148014.2
    CBS0.725306.122.547013.8
    DCBS0.748559.221.052011.5

    Formulation: NR (SMR CV60) 60, BR (Nd-catalyzed) 40, N234 carbon black 65, aromatic oil 10, ZnO 5, stearic acid 2, sulfur 2.25, accelerator 0.7. Cured specimens tested per ISO 37:2017; vulcanization kinetics captured via ASTM D5289.

    Auditing Incoming Raw Materials: Specification Ranges and Analytical Methods

    ParameterTypical RangeTest Method
    Assay (TBBS)≥ 96.0 %ISO 11235 (HPLC)
    Free amine as tert-butylamine≤ 0.5 %Acid-base titration, potentiometric
    Melting range104 – 110 °CDSC or capillary tube (ISO 3146)
    Loss on drying (60°C, vacuum)≤ 0.3 %Weight loss, 2 h at 60 °C, ≤20 mbar
    Ash content≤ 0.2 %ISO 247
    Residue on 150 µm sieve≤ 0.1 %Wet sieving

    When Migration Limits Dictate Accelerator Selection for Food Contact Goods

    FDA 21 CFR 177.2600 permits the use of TBBS in rubber articles intended for repeated contact with food, subject to migration limits established for the sum of aromatic amines and thiazoles. Under EU Commission Regulation (EU) 10/2011 on plastic materials and articles, applied to rubber by analogy in certain member states, a specific migration limit for TBBS of 0.5 mg/kg food simulant is enforced. To meet these limits, curative systems often shift from TBBS to lower-migratory accelerators such as ZDBC or ZDEC, but TBBS remains viable when the concentration is kept below 0.8 phr and the rubber article is subjected to a post-cure vacuum heat treatment at 110 °C for 4 h to reduce volatile accelerator residues. Extraction tests performed according to EN 12868 demonstrate that treated vulcanizates maintain a TBBS-specific migration below 0.1 mg/dm² into acetic acid 3 % simulant after 4 h at 40 °C.

    Storage stability demands moisture exclusion and temperature control. The product is hygroscopic; water uptake exceeding 0.5 % can catalyze hydrolysis to 2-mercaptobenzothiazole (MBT), drastically lowering scorch resistance. Drums must be resealed under nitrogen when held in high-humidity environments (RH > 60 %). Recommended storage temperature is 15–25 °C; prolonged exposure above 30 °C accelerates decomposition even in sealed containers, reducing the active content by 0.2 % per month as measured by HPLC. These constraints are critical at compounder sites using silo storage with pneumatic conveying, where temperature excursions have been documented to cause batch-to-batch Mooney viscosity variations of up to 8 MU.