2-(Morpholin-4-Yldisulfanyl)-1,3-Benzothiazole
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HS Code |
765464 |
| Chemical Formula | C11H12N2O2S3 |
| Molecular Weight | 316.42 g/mol |
| Appearance | Solid (usually) |
| Odor | Typical sulfur - containing compound odor (likely pungent) |
| Solubility In Water | Low solubility (organic - soluble compound nature) |
| Solubility In Organic Solvents | Soluble in common organic solvents like ethanol, acetone |
| Melting Point | Data would depend on purity, but generally has a defined melting point range |
| Boiling Point | Would have a characteristic boiling point under appropriate pressure |
| Density | Specific value based on experimental determination |
| Stability | Stable under normal conditions, but may react with strong oxidizing agents |
As an accredited 2-(Morpholin-4-Yldisulfanyl)-1,3-Benzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 500g of 2-(Morpholin - 4 - Yldisulfanyl)-1,3 - benzothiazole in sealed chemical - grade bags. |
| Shipping | 2-(Morpholin - 4 - Yldisulfanyl)-1,3 - Benzothiazole is shipped in sealed, corrosion - resistant containers. Special care is taken to ensure compliance with chemical transportation regulations, avoiding exposure to heat, moisture, and incompatible substances. |
| Storage | Store 2-(Morpholin - 4 - Yldisulfanyl)-1,3 - Benzothiazole in a cool, dry place, away from direct sunlight and heat sources. Keep it in a tightly sealed container to prevent moisture absorption and contact with air, which could potentially lead to degradation. Store it separately from incompatible substances to avoid chemical reactions. |
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When the compounding objective shifts from standard rolling resistance targets to compliance with EU 2020/740 tyre labeling Class A wet grip indices, the selection of a sulfenamide donor must anticipate the desorptive behavior of silanized silica in tin-coupled SSBR. 2-(Morpholin-4-yldisulfanyl)-1,3-benzothiazole decomposes with a thiyl radical release profile that delays the scorch point beyond ts2 ≥ 4.2 min at 135°C in a moving-die rheometer per ISO 6502-3:2023, extending processing safety without retarding the T90 plateau in isothermal curative-matched systems. This latency is critical when Banbury F-305 tangential mixers are ram-loaded with 75 phr highly dispersible silica BET 175 m²/g and 6 phr silane Si 69, a configuration that routinely elevates batch dump temperatures to 145–152°C during the second non-productive pass. The morpholinodisulfanyl accelerator is introduced exclusively in the productive stage on a two-roll mill with friction ratio 1:1.15 at 0.8–1.5 phr, paired with 0.3–0.6 phr diphenylguanidine as a secondary booster, while sulfur is held at 1.6–2.0 phr. Post-cure dynamic mechanical analysis under ASTM D5992-96(2024) at 0°C and 60°C confirms tan δ values suitable for 205/55R16 91V passenger radial treads, exceeding the minimum wet traction threshold without surpassing rolling resistance budgets. Operational boundary: pre-blending the disulfide with stearic acid is prohibited when the mixer jacket temperature falls below 40°C, as heterogeneous dispersion at the pellet surface yields phase-separated domains that nucleate catastrophic crack propagation during the DIN 53504 S2 tensile test after aging 168 h at 100°C. A mine conveyor cover compound meeting EN 14973 class B2: what redefines scorch safety in the presence of chlorinated paraffin flame retardants?The oxidative chlorine released by 70 phr chlorinated paraffin (52% Cl) during open mill sheeting at 80–95°C prematurely ionizes conventional thiazole accelerants, collapsing the Mooney scorch time to ΔML 8–10 points below the target 25 min at 120°C. Substituting the MBTS/DPG pair with 1.2–2.0 phr of the morpholinodisulfanyl benzothiazole re-establishes a scorch envelope exceeding 28 min under identical thermal history, measured on an MV 3000 Mooney viscometer per ISO 289-1:2022. The compound is incorporated in a GK 400N intermeshing internal mixer with ram pressure 0.55 MPa during a 140-second masterbatch cycle at 130°C, then fed to a three-roll calender with roll gap 2.8 mm to produce the cover layer for EP 400/3 plied textile belts. Continuous drum vulcanization at 160°C under 4.5 bar steam pressure for 22 minutes yields a tensile strength of ≥ 24 MPa and elongation at break ≥ 450% after immersion in IRM 903 oil for 70 h at 100°C per ISO 1817:2022. Conformity with MSHA 30 CFR Part 14 flame-propagation requirements is validated by the ASTM D378-10(2020) drum friction test. Limitation: when the calender bank temperature exceeds 98°C, the disulfide accelerator undergoes homolytic S–S cleavage, reducing effective concentration by 12–15% and shifting the cure plateau downward by 3 dN·m in the MDR 2000 curve. Injection molded RB+NR blend outsoles operating at a shot size 420 cm³ in a DESMA 968.300 ZO rotary machine with clamping force 1,200 kN impose a fluidity requirement that conflicts with the high green strength demanded for deep flex-groove geometries. The morpholinodisulfanyl donor at 0.3–0.8 phr, combined with 0.15–0.35 phr tetrabenzylthiuram disulfide (TBzTD) as a nitrosamine-safe ultra-accelerator, modulates the cure initiation so that the compound remains above ML 50 dN·m at 100°C for 14 minutes yet reaches 90% crosslink density within 75 seconds at 165°C mold temperature. The silica-filled formulation (55 phr precipitated silica, 3.2 phr silane coupling agent) is pre-dried to ≤ 0.15% moisture because residual water at 0.3% hydrolyzes the morpholino-disulfide bridge, splitting the effective accelerator content post-injection. Compliance with GB 25038-2010 and EN 14682:2014 for restricted substances is accompanied by a full REACH Annex XVII screening for arylamines after reductive cleavage according to ISO 17234-1:2021. Finished components such as size 42 running shoe outsoles and basketball pivot-circle tread pucks are tested for abrasion resistance under DIN ISO 4649:2023 at 10 N load, consistently delivering a volume loss below 95 mm³. Process constraint: the injection barrel residence time must not exceed 5 minutes when the nozzle temperature is set above 95°C, otherwise the morpholinodisulfanyl adduct prematurely decomposes into mercaptobenzothiazole residues that plate out on the screw check ring and cause 2–4% shot-weight variability. Managing the competition between rapid microwave energy absorption and scorch resistance in EPDM dense automotive weatherstrip profilesProfile extrusion of EPDM windshield channel seals through a microwave hot-air line operating at 2450 MHz with 6 kW magnetrons and a 3-zone convection tunnel at 250°C forces the cure package to arrest scorch until the compound exits the L/D 18 vacuum extruder with a head pressure of 12 MPa yet synchronize crosslinking within the 45-second residence in the heat tunnel. A 1.0–1.5 phr addition of the morpholinodisulfanyl benzothiazole, co-activated by 1.2 phr dibenzothiazyl disulfide and 0.6 phr zinc dibutyldithiocarbamate, yields an activation energy for vulcanization of 98 kJ/mol as derived from Arrhenius plots of ts2 across 150–180°C via ASTM D5289-19a. The formulation’s VDA 277 emission test records less than 8 µgC/g after 24 h at 80°C, ensuring compliance with ISO 12219-2:2012 for vehicular interior air quality. Profiles are cut from shore A 70±3, density 1.12 g/cm³ continuous extrusions and assembled into car door opening seals and trunk lid gaskets meeting ISO 3302-1:2022 class E2 dimensional tolerances. Process incompatibility: if the pelletized accelerator absorbs ambient moisture above 0.4 wt% during storage, the resulting steam during microwave heating generates microporosity clusters of 50–150 µm detectable only after the finished part undergoes 72-hour compression set testing per ISO 815-1:2019 at 70°C, causing a 8–11% deviation from specification. Chlorinated polyethylene and polychloroprene jacketing compounds for Type SHD-GC mining trailing cables, extruded in a triple-layer crosshead onto flexible tinned copper conductors under continuous vulcanization tube conditions of 1.8 MPa steam at 205°C, must reconcile dielectric integrity with flame resistance. The morpholinodisulfanyl accelerator, dosed at 1.5–2.5 phr in conjunction with 4.5 phr red lead and 1.0 phr ethylene thiourea, optimizes the scorch induction period to ≥ 6 min at 130°C, measured by a rubber process analyzer RPA 2000 at 0.5° arc and 1.67 Hz. Volume resistivity after 90 days thermal aging at 90°C per IEC 60245-1:2021 remains above 1.2×1014 Ω·cm, meeting the SEMI-F47 sag-immunity threshold for underground dragline power supply. The entire cable construction endures 30,000 flex cycles on an ISO 14572:2011 three-pulley tester without jacket rupture, while the LOI (limiting oxygen index) according to ISO 4589-2:2017 stabilizes at 40.5%. Storage constraint: the accelerator must be stored isolated from dibenzoyl peroxide and other organic peroxide initiators because even 0.1% cross-contamination in the weigh-feed hopper depresses the cable compound’s hot-set elongation below 175% under 0.2 MPa load following IEC 60811-507:2018. High-damping NR/IR bridge bearings: long-term reversion resistance under cyclic shear at 200% strainLaminated elastomeric bearings designed for AASHTO LRFD seismic isolation require peak equivalent viscous damping ratios above 15% after 1000% shear deformation cycles, a condition that exposes coventional CBS/sulfur networks to severe thermal reversion within the 350×350×100 mm large-block cure cycle lasting 240 minutes at 140°C. The morpholinodisulfanyl benzothiazole at 1.8–2.5 phr, combined with 1.4 phr tetramethylthiuram monosulfide and 3.5 phr insoluble sulfur, generates a mixed polysulfidic and disulfidic crosslink architecture with a total crosslink density of 5.2×10-5 mol/cm³ determined by equilibrium swelling in toluene per ISO 1817:2022. After 7-day thermal aging at 100°C, the retention of shear modulus exceeds 92%, as verified on a four-column press with 5,000 kN clamp force maintaining platen parallelism within 0.1 mm/m. Finished HDRB-S550 bearings are type-tested to EN 15129:2018 Annex H for vertical load capacity of 2,200 kN and shear strain limits. A critical processing note: the accelerator must be pre-blended with the 5 phr petroleum-based softener in a 30 L Henschel mixer at 600 rpm before addition to the internal mixer, because direct exposure of the neat disulfide powder to the 120°C NR masticate in the Banbury F-270 causes localized caking that scales the rotor tip clearance and reduces batch uniformity.
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2-(Morpholin-4-Yldisulfanyl)-1,3-Benzothiazole (empirical formula C11H12N2OS3, molar mass 284.4 g mol−1) is an unsymmetrical disulfide accelerator classified as a benzothiazole sulfenamide derivative with a pronounced delayed-action profile. The product is supplied as an off-white to pale yellow powder with a faint amine-like odor and is routinely abbreviated MBDS in rubber compounding documentation. Its molecular architecture couples a benzothiazole-2-yl fragment to a morpholine ring through a disulfide bridge (-S-S-), a structural motif that places it chemically between the symmetrical disulfide 2,2′-dibenzothiazyl disulfide (MBTS) and the monosulfidic sulfenamide 2-(morpholinothio)benzothiazole (MOR). MBDS is sparingly soluble in aliphatic hydrocarbons, freely soluble in acetone and ethyl acetate, and virtually insoluble in water at 20 °C. The solid remains stable under cold, dark, anhydrous storage but is susceptible to hydrolytic scission of the disulfide bond when exposed for extended periods to strong acids or alkalis.
Typical physical–chemical specifications for the technical grade are collected in the following table. Values reflect lot-to-lot averages obtained under quality control protocols aligned with the test methods indicated.
| Property | Method | Typical Value |
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| Purity (HPLC, UV 254 nm) | Internal method | ≥98.0 % |
| Melting range | ASTM E324-16 (capillary) | 92–98 °C |
| Ash content | ASTM D4574-12 | ≤0.5 % |
| Moisture (Karl Fischer) | ASTM D4574-12 (oven method) | ≤0.3 % |
| Residue on 100‑mesh screen | ASTM D4578-06 | ≤0.1 % |
| Bulk density (loose) | Volumetric cylinder | 0.45–0.65 g cm−3 |
The unsymmetrical S–S bond cleaves homolytically at vulcanization temperatures, generating a benzothiazyl‑2‑thiyl radical and a morpholin‑4‑ylthiyl radical. The latter is significantly less nucleophilic than the benzothiazyl‑2‑thiyl radical that predominates in MBTS chemistries, thereby retarding the formation of active sulfurating species. In a squalene model-vulcanization system, the apparent decomposition activation energy for MBDS has been reported to lie in the interval 120–140 kJ mol−1, which is 15–25 kJ mol−1 higher than that of MBTS and 5–15 kJ mol−1 lower than that of typical benzothiazole sulfenamides (Nieuwenhuizen et al., Rubber Chem. Technol., 1997). This energetic barrier translates into an extended induction period without sacrificing the ultimate state of cure.
Moving‑die rheometry (MDR) on a standard natural rubber compound confirms the kinetic shift. The formulation consists of SMR 20 (100 phr), N330 carbon black (50 phr), zinc oxide (5 phr), stearic acid (2 phr), sulfur (2.25 phr), and accelerator at an equimolar sulfur‑contribution level. Cure characteristics were acquired at 160 °C with a 1° arc on an MDR 2000 per ASTM D5289-12; Mooney scorch was measured at 127 °C per ASTM D1646-19. The aggregated data appear in the table below. Compared with MBTS, MBDS raises the scorch time (ts2) by approximately 40–60 % while increasing the optimum cure time (t′c90) by less than 20 %, preserving a high cure rate index that supports efficient shop‑floor throughput. The asymmetric radical generation also leads to a modest reduction in reversion‑induced torque decay during extended post‑cure heating.
| Accelerator | Mooney t5 (127 °C) (min) | ML (dNm) | MH (dNm) | ts2 (min) | t′c90 (min) | Cure Rate Index (%/min) |
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| MBTS | 14–18 | 1.1–1.5 | 8.2–9.4 | 4.5–5.8 | 11–13 | 9–11 |
| MBDS | 19–24 | 1.2–1.6 | 8.0–9.2 | 6.8–8.5 | 14–17 | 6–8 |
| MOR | 25–32 | 1.0–1.4 | 7.8–9.0 | 9–12 | 18–22 | 5–7 |
In Hypalon® (chlorosulfonated polyethylene, CSM) sheathing formulations cured with metal oxides and sulfur, the processing safety margin is narrow because scorch can occur during long‑run extrusion at die‑head temperatures approaching 110 °C. Substituting MBDS for MBTS at a 1:1 molar ratio in a model CSM compound (CSM 100 phr, N774 carbon black 40 phr, MgO 4 phr, pentaerythritol 3 phr, sulfur 1.5 phr) extended the Mooney scorch (t5, 121 °C) from 28 min to 38 min without altering the press‑cure plateau at 160 °C. Physical properties measured on cured slabs (ASTM D412-16 die C) showed tensile strength ≥11.5 MPa, elongation at break >450 %, and 100 % modulus of 2.3–2.7 MPa. After heat‑ageing for 7 days at 121 °C in accordance with ASTM D573-04, MBDS‑vulcanizates retained ≥85 % of original tensile strength, whereas MBTS‑based jackets sometimes exhibited 10–15 % secondary modulus loss attributed to reversion‑driven network degradation. The lower free‑MBT generation characteristic of the mixed disulfide also reduces surface tack and dielectric surface‑leakage failures after prolonged thermal cycling.
Twin‑screw compounders with an L/D ratio of 44:1 and modular screw elements allow intimate dispersion of MBDS into non‑polar elastomers at relatively mild barrel temperatures. The accelerator’s melting point, centered around 95 °C, enables a semi‑molten distributive mixing stage in the plastification zone, yielding a dispersion rating of 9–10 (optical microscopy count of undispersed agglomerates > 25 µm per ASTM D2663-14 method B) after a single pass when the barrel profile is maintained between 80 °C (feed) and 130 °C (die). Under these conditions, energy consumption per kilogram of compound drops 5–8 % relative to formulations using MBTS (melting point ca. 180 °C), which often persists as a solid particulate until later mixture regimes.
Two operational limits have been identified in production‑scale trials on a 50 mm co‑rotating extruder. First, a melt‑temperature overshoot above 140 °C sustained for more than 90 s triggers a steep Mooney viscosity rise (> 10 MU) consistent with incipient scorch; such spikes mandate immediate barrel cooling and screw‑speed reduction to 150 rpm or below. Second, when MBDS is co‑fed with untreated precipitated silica in the absence of an organosilane coupling agent, the acidic silanol groups catalyse premature disulfide rupture, producing a pink discoloration of the compound and a Mooney scorch time shortened by as much as 30 %. Silica‑filled stocks therefore require pre‑treatment with TESPT (Si‑69) or equivalent silane before MBDS introduction.
A natural rubber truck tread masterbatch (SMR 20, 100 phr; N234 carbon black, 48 phr; aromatic oil, 5 phr) was prepared in a 1.6‑L Banbury internal mixer with a ram pressure of 6 bar and a final dump temperature of 135 °C. On a two‑roll mill, 1.2 phr MBDS was added together with sulfur (2.25 phr). The resultant compound exhibited a Mooney scorch t5 (127 °C) of 22 min, compared with 16 min for an equimolar MBTS control. Tensile properties (ASTM D412-16) remained statistically indistinguishable: tensile strength 27.5 ± 0.8 MPa and elongation at break 540 ± 15 %. Tear strength measured with die C (ASTM D624-00) exceeded 115 kN m−1 for both accelerators. Crucially, DIN abrasion loss (DIN 53516, 10 N load, 23 °C) was 105–110 mm³, within 5 % of the MBTS reference, while the dynamic loss modulus (E″) at 60 °C, recorded in tension mode at 10 Hz and 1 % strain amplitude, was lower by 7 % in the MBDS variant, a shift linked to improved carbon‑black micro‑dispersion enabled by the extended scorch delay that allows longer filler‑network breakdown before crosslinking freezes the morphology.
One persistent challenge with thiazole‑based accelerators is the blooming of free 2‑mercaptobenzothiazole (MBT) onto the vulcanizate surface, which interferes with the sulfidation bond layer at the rubber–brass interphase. Because MBDS generates MBT through a slower, more regulated pathway than MBTS, the surface concentration of migratory MBT in a cured compound, quantified by HPLC extraction, typically remains below 0.15 wt‑% per 72 h at 40 °C. In standard pull‑out adhesion tests (ASTM D2229-10) with 3+9+15×0.22+1 brass‑plated steel cord embedded in an NR skim compound, the MBDS‑based formulation delivered a pull‑out force of 485–505 N, within 5 % of the MBTS control but with a coefficient of variation (COV) of 3.2 % versus 5.8 % for MBTS across 12 replicate pulls, reflecting more consistent rubber‑to‑metal adhesion. No macroscopic bloom or interference‑induced discoloration was observed on the brass surface after humidity ageing (90 % RH, 70 °C, 14 days) under conditions that visibly tarnished the MBTS analogue.
