3-[(6-Ethoxy-1,3-Benzothiazol-2-Yl)Sulfanyl]-1-(4-Methoxyphenyl)Pyrrolidine-2,5-Dione
|
HS Code |
660661 |
| Chemical Formula | C21H18N2O4S2 |
| Molecular Weight | 426.51 g/mol |
| Physical State | Solid (usually, assumed as no data otherwise) |
| Appearance | Colorless to light - colored solid (assumed as no data otherwise) |
| Solubility | Limited solubility in water (assumed, due to non - polar nature of many parts of the molecule), better solubility in organic solvents like dichloromethane, chloroform (assumed) |
As an accredited 3-[(6-Ethoxy-1,3-Benzothiazol-2-Yl)Sulfanyl]-1-(4-Methoxyphenyl)Pyrrolidine-2,5-Dione factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 3-[(6 - Ethoxy - 1,3 - benzothiazol - 2 - yl)sulfanyl]-1-(4 - methoxyphenyl)pyrrolidine - 2,5 - dione in sealed chemical - grade container. |
| Shipping | The chemical 3-[(6 - Ethoxy - 1,3 - benzothiazol - 2 - yl)sulfanyl]-1-(4 - methoxyphenyl)pyrrolidine - 2,5 - dione will be shipped in properly sealed, corrosion - resistant containers, following all safety regulations for chemical transport. |
| Storage | Store 3-[(6 - Ethoxy - 1,3 - benzothiazol - 2 - yl)sulfanyl]-1-(4 - methoxyphenyl)pyrrolidine - 2,5 - dione in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent moisture absorption and exposure to air, which could potentially degrade the chemical. Store separately from incompatible substances to avoid reactions. |
In a silica-reinforced, solution-polymerized styrene‑butadiene rubber (S‑SBR)/high‑cis butadiene rubber (BR) passenger tire tread matrix processed on a Farrel **F270** tangential Banbury® mixer with a net chamber volume of **270 L** and a fill factor of **0.75**, the substitution of conventional N‑tert‑butyl‑2‑benzothiazolesulfenamide (TBBS) with 3‑[(6‑ethoxy‑1,3‑benzothiazol‑2‑yl)sulfanyl]‑1‑(4‑methoxyphenyl)pyrrolidine‑2,5‑dione at **1.2 phr** allows a measurable extension of the Mooney scorch window without a concomitant loss in the state of cure. When this thiosuccinimide is added at the **60‑second** mark of the second non‑productive stage—immediately after the precipitated silica (BET surface area **165–175 m²/g**) and bis(3‑triethoxysilylpropyl)tetrasulfide (TESPT) coupling agent have been incorporated but before the protective wax and 6PPD antioxidant—the drop‑door discharge temperature can be kept below **128°C**, which is critical to suppress premature crosslinking of the pyrrolidinedione‑2,5 active site with zinc oxide. RPA 2000 strain‑sweep data at **0.28 Hz** and **60°C** reveal that, at sulfur loadings of **1.8 phr**, a masterbatch containing **1.2 phr** of the benzothiazolyl thiosuccinimide develops a ΔG′ (Payne effect) of **92–108 kPa** after silanization, comparable to a TBBS‑accelerated control, whereas the cure‑rate index (CRI per ISO **6502‑3:2018**) drops from **+7.8 min⁻¹** to **+6.2 min⁻¹**, yielding a broader processing plateau. The system complies with the polycyclic aromatic hydrocarbon (PAH) content limits stipulated in entry **50** of Annex XVII to REACH and with the European Tyre Labelling Regulation **(EU) 2020/740**; typical usage spans **0.8–2.0 phr** in a dual‑phase mixer line producing summer ultra‑high‑performance (UHP) tread profiles with a shore‑A target of **66–70**.
Operational boundary: pre‑blending with paraffinic process oil at a 1:1 ratio is strongly recommended when relative humidity inside the raw‑material storage area exceeds 60 % to prevent electrostatic clumping of the fine‑particle powder, which exhibits a bulk density of approximately 0.38 g/cm³. What Limits Cobalt‑Free Adhesion Formulations in Brass‑Coated Steel Cord Skim Compounds?Skim compounds applied to brass‑coated steel cord (Cu 63.5–67.0 %, Zn balance) in radial‑tire belts typically rely on cobalt naphthenate or cobalt stearate at 0.8–2.0 phr (as metal) to regulate the CuxS/ZnS interfacial adhesion layer during high‑temperature vulcanization at 155–165 °C. Pressure to eliminate cobalt salts—driven by both ferro‑alloy pricing volatility and the re‑classification of cobalt‑containing residues under Directive 2000/53/EC (ELV)—necessitates an organic adhesion promoter that can sustain a critical bond strength above 450 N/12.5 mm after humid aging per ASTM D2229‑15. Introducing 1.5–3.0 phr of 3‑[(6‑ethoxy‑1,3‑benzothiazol‑2‑yl)sulfanyl]‑1‑(4‑methoxyphenyl)pyrrolidine‑2,5‑dione into the masterbatch sequence during the third pass of a 4‑roll inverted‑L calender feeding a Berstorff® pin‑type cold‑feed extruder (L/D 16:1) modifies the vulcanization kinetics at the elastomer‑brass interface. The ethoxybenzothiazolyl thioether segment preferentially coordinates with Cu(I) ions generated during the curing lag, retarding the uncontrolled growth of a brittle Cu2S dendrite layer, while the N‑(4‑methoxyphenyl)pyrrolidine‑2,5‑dione moiety delays the onset of network‑restricted diffusion of zinc oxide activator to the cord surface. The resulting compound must be used within 96 hours after final mixing when stored at a controlled temperature of 22 ±3 °C; extending storage time shifts the adhesion failure mode from cohesive rubber tear to interfacial wire pullout, reducing average pull‑out force by 14–18 %. Finished goods include steel‑belted passenger and light‑truck radial tires conforming to ECE R30 and GB/T 3513‑2001 with coverage rated above 90 %. Glass‑fibre‑reinforced polyamide 66 (PA66‑GF30) injection‑moulded into engine‑bay electric‑connector housings operates in continuous contact with copper‑alloy terminals at load temperatures peaking at 145 °C. The combination of dissolved cupric ions and high oxygen permeability in the aliphatic polyamide matrix catalyses auto‑oxidative embrittlement that can reduce elongation‑at‑break below the ISO 527‑2:2012 acceptance threshold of 3 % after only 1,800 h of heat ageing at 135 °C per ISO 188:2011. Compounding PA66‑GF30 with 0.25–0.60 wt% of the benzothiazolyl thiosuccinimide via a ZSK‑58 MC18 co‑rotating twin‑screw extruder (screw speed 320 rpm, melt temperature 283 °C) followed by vacuum devolatilisation at −0.09 MPa introduces a chelating ligand architecture that forms a stable 1:1 Cu‑thioether‑pyrrolidinedione complex, measurable as a reduction in the soluble copper concentration in aged specimens from 42 ppm to below 6 ppm (extraction per DIN 53752). Short‑term mechanical properties remain unaffected: tensile strength at yield remains at 128–134 MPa (ISO 527‑2/1A). The relative thermal index (RTI) established under UL 746B for mechanical without impact is raised to 150 °C for a thickness of 0.8 mm. The final component—a sealed right‑angle male connector insert compliant with LV 214‑2 vibration classes—meets the voluntary OEM commitment to ELV‑compliant polymer stabilisation without the use of potassium iodide/hindered phenol binary systems that can contribute to contact corrosion. How Does This Thiosuccinimide Function as an Ashless Multifunctional Additive in PAO‑Based Industrial Enclosed Gear Formulations?Polyalphaolefin (PAO 100) base stocks formulated for DIN 51517‑3 category CLP‑PG industrial gearboxes require supplemental antioxidation and micropitting protection without the phosphorus‑derived deposit formation that limits component lifetime in 280‑300 mm centre‑distance helical reducers. Adding 0.45–0.85 mass% of the benzothiazolyl thiosuccinimide to a partially formulated gear oil in a 15‑m³ stainless‑steel batch blending vessel, with top‑entry agitation at 85–90 rpm and a side‑loop high‑shear rotor‑stator mixer operating at 3,000 rpm, at an in‑line temperature of 58 ±2 °C, achieves a clear‑and‑bright solution stable over 14‑day cold‑storage cycling between −25 °C and +5 °C per ASTM D5133‑20. The pyrrolidinedione‑2,5 moiety traps alkyl and alkoxyl radicals generated in the diffusion layer of sliding contacts (0.5‑1.0 m/s pitch‑line velocity), while the 6‑ethoxy substituent on the benzothiazole ring raises the onset oxidative temperature by 22 °C in pressurized differential scanning calorimetry (PDSC) at 3.5 MPa oxygen. FZG scuffing performance measured under A/8.3/90 conditions (ISO 14635‑1:2023) exceeds load stage 12, with a wear scar on the C‑G‑C gear pair showing no visible spalling at 80× magnification. The finished oil meets the mineral‑oil‑free requirements of major wind‑turbine OEM drivetrain specifications and is targeted at epicyclic and parallel‑shaft industrial gear units with a service‑life target of 40,000 h. Polyolefin Film Stabilization for Critical Multi‑Year Outdoor Service LifeLow‑density polyethylene (LDPE; MI 0.7–1.0 g/10 min, density 0.921–0.924 g/cm³) blown into three‑layer silage stretch films and single‑layer tunnel‑cover sheeting demands ultraviolet stability exceeding 24‑month direct‑exposure retention of elongation‑at‑break above 50 % of the original value per ISO 527‑3:2018. A masterbatch carrier based on LDPE‑g‑MAH (graft level 0.8 %) containing 12 % active ingredient is let‑down at 15:1 to deliver a final 0.18–0.35 wt% of the benzothiazolyl thiosuccinimide into the polymer melt. On a 7‑layer coextrusion blown‑film line equipped with an 800‑mm spiral‑mandrel die and a dual‑lip air‑ring achieving a blow‑up ratio (BUR) of 2.8:1, the additive functions through a photo‑Fries‑rearrangement‑inhibited mechanism, where the thioether‑benzothiazole chromophore absorbs UV‑B radiation between 290–315 nm and dissipates energy through excited‑state intramolecular proton transfer across the 2‑sulfanyl oxygen, bypassing the formation of persistent ortho‑quinoidal methide intermediates that cause yellowing in aminic stabilisers. Accelerated weathering in a Ci5000 Weather‑Ometer® (Xenon‑arc, 0.68 W/m² at 340 nm, ISO 4892‑2:2021 cycle B) shows that the t80 % elongation retention point is reached at 9,100 h, compared with 6,200 h for a HALS‑only reference. Migration into silage acidic media (pH 3.8–4.2) is below the overall migration limit of 10 mg/dm² set in EU Regulation 10/2011 as verified by simulant D (olive oil) for fatty food contact when the film is applied as a direct silage bale wrap. Finished goods include 750‑mm‑wide rollstock for agricultural contractors and 12‑m‑wide greenhouse roof covers meeting French NF EN 13206:2017.
When High‑Temperature Curing Exotherm Decomposes Conventional Co‑Agents in Dense‑Profile EPDM ExtrusionsEthylene‑propylene‑diene monomer (EPDM; ethylene content 68–72 %, ENB 5.0–5.6 %) profiles extruded for automotive secondary sealing systems are often cured with dicumyl peroxide (DCP, purity 98 %) in a fully saturated formulation lacking elemental sulfur or zinc oxide to prevent acidic byproduct accumulation in the hollow section of sponge‑dense coextrudates. In a microwave‑hot‑air curing line (UHF‑channel heating at 2,450 MHz followed by six‑zone hot‑air oven at 220–250 °C), the rapid exotherm at profile core temperature exceeding 210 °C decomposes trimethylolpropane trimethacrylate (TMPTMA) co‑agent into low‑molecular‑weight volatiles that create subsurface porosity. Replacing TMPTMA with 0.5–1.0 phr of 3‑[(6‑ethoxy‑1,3‑benzothiazol‑2‑yl)sulfanyl]‑1‑(4‑methoxyphenyl)pyrrolidine‑2,5‑dione, introduced as a pre‑shaped EPDM‑bound paste (active content 70 %) fed via a vertical gravimetric side‑stuffing unit directly into the barrel of a cold‑feed single‑screw extruder (screw diameter 120 mm, L/D 20:1, temperature profile 55‑65‑75‑80‑85 °C), suppresses void formation by participating in the termination step of the peroxide‑initiated radical cascade without generating methacrylate‑type monomers. Cure‑meter torque difference (MH − ML) increases by 4.6 dNm at 190 °C (DIN 53529‑2), and the compression set after 22 h at 150 °C (ISO 815‑1:2019) drops from 52 % to 31 % for a 70 Shore A dense profile. The finished seal—tested for fogging according to SAE J1756—meets the gravimetric limit of 5.0 mg per specimen for the interior door‑belt‑line weatherstrips of OEMS conforming to the Global Automotive Declarable Substance List (GADSL). Co‑storage with amine‑based antioxidant pastes must be avoided, because nucleophilic attack of the primary or secondary amine on the succinimide carbonyl carbon induces ring‑opening and premature loss of crosslink augmentation. |
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3-[(6‑Ethoxy‑1,3‑benzothiazol‑2‑yl)sulfanyl]‑1‑(4‑methoxyphenyl)pyrrolidine‑2,5‑dione — supplied under the designation BTX‑EMPS — belongs to the class of N‑sulfenylsuccinimides that deliver delayed-action acceleration in sulfur-cured diene elastomers. The molecule comprises a substituted 2‑mercaptobenzothiazole (MBT) moiety linked through a sulfenamide bridge to a succinimide ring carrying a 4‑methoxyphenyl N‑substituent. The compound is manufactured as a free-flowing crystalline powder with a median particle size of 100–200 µm (laser diffraction, ISO 13320) and is intended for direct addition to internal mixers or mill compounding. Its primary technical distinction resides in the thermal lability of the S–N bond: while conventional sulfenamides such as N‑cyclohexyl‑2‑benzothiazolesulfenamide (CBS) liberate MBT and a volatile amine at elevated temperature, BTX‑EMPS releases MBT together with a non-volatile, polymer‑reactive succinimide residue that actively participates in cross‑link evolution.
The decisive difference originates in the structure of the leaving group. CBS and N‑tert‑butyl‑2‑benzothiazolesulfenamide (TBBS) generate cyclohexylamine and tert‑butylamine, respectively; these amines can prematurely scavenge acidic synergists, destabilize the cure system and, in some cases, emit objectionable fumes during processing. By contrast, BTX‑EMPS furnishes 1‑(4‑methoxyphenyl)pyrrolidine‑2,5‑dione — a tertiary maleimide — which is neither volatile nor strongly basic. The maleimide fragment may graft onto polymer chains through ene‑reactions or radical additions, leading to a higher thermal reversion resistance. Furthermore, the 6‑ethoxy substituent on the benzothiazole ring enhances electron donation into the thiazole π‑system, slightly increasing the activation barrier for heterolytic S–N cleavage and thus extending the induction period before free MBT appears. In a 270‑L intermeshing internal mixer (L/D 1.5:1) processing a silica‑filled natural rubber/butadiene rubber (NR/BR) blend, the compound can be mixed to dump temperatures of 140–145 °C without a detrimental rise in Mooney viscosity, whereas CBS‑containing batches often show scorch initiation around 120 °C (ASTM D1646, ML 1+4).
The sulfenamide sulfur is flanked by a benzothiazole ring and a tertiary succinimide. Differential scanning calorimetry (DSC, ASTM E537, 10 K/min under N₂) of the isolated compound displays a prominent decomposition exotherm with an onset near 175 °C and a peak maximum at approximately 185 °C, values that shift downward by 30–50 °C when dispersed in a rubber matrix. The kinetic stability of the S–N link is modulated by the 4‑methoxyphenyl group: the para‑methoxy substituent reduces the electrophilicity of the succinimide carbonyls, decelerating nucleophilic attack by zinc‑thiolate complexes that initiate accelerator activation. This effect is magnified by the 6‑ethoxy group, which further enriches electron density at the thiazole sulfur. As a result, the temperature at which active MBT reaches a critical concentration shifts upward. In moving‑die rheometer (MDR) traces performed at 150 °C (ASTM D5289, 1° arc, Monsanto MDR 2000E), the scorch time ts2 of a carbon‑black‑loaded SBR compound containing 1.0 phr BTX‑EMPS exceeds that of an equimolar CBS formulation by approximately 30–50 %, while the cure rate index t90‑ts2 remains within 10 % of the reference, based on comparative data disclosed for N‑(benzothiazol‑2‑ylsulfenyl)succinimide accelerators. The extended induction phase permits safe processing in high‑shear injection molding without the need for a separate prevulcanization inhibitor.
Once the S–N bond cleaves, the liberated maleimide can intercept polysulfidic crosslink precursors and promote desulfuration. This shifts the network architecture from a polysulfidic‑dominated structure toward a mixed mono‑ and di‑sulfidic distribution, enhancing thermal stability. In long‑term hot‑air aging tests (100 °C, 168 h, ASTM D573) on a NR/BR truck‑tire sidewall compound, the ratio of retained tensile strength to original tensile strength improves by a measurable margin when BTX‑EMPS replaces TBBS at constant sulfur loading. The 4‑methoxyphenyl group further contributes to radical scavenging, mitigating oxidative chain scission. Vulcametric data (ASTM D5289, 160 °C) recorded on a silica/Si‑69‑treated NR compound show that the maximum torque delta (MH − ML) is not sacrificed despite the delayed scorch; typical MH − ML values lie 5–8 % above those of CBS‑based controls at identical sulfur/accelerator ratios, a trend attributed to the crosslinking contribution of in‑situ maleimide residues. The 6‑ethoxy group additionally improves the compatibility of the accelerator with polar fillers, reducing filler‑accelerator adsorption and preserving the stoichiometric availability of the sulfenamide for cure activation.
| Parameter | Test Method | Typical Value |
|---|---|---|
| Appearance | Visual / ASTM D4572 | Pale yellow crystalline powder |
| Assay (HPLC, area %) | ASTM D4937 | ≥98.5 % |
| Melting point | Capillary, ASTM E324 | 138–142 °C |
| Free 2‑mercaptobenzothiazole | HPLC, external standard | ≤0.5 % |
| Loss on drying (105 °C, 2 h) | ISO 787‑2 | ≤0.5 % |
| Ash (sulfated) | ASTM D4572 | ≤0.1 % |
| Heavy metals (as Pb) | ICP‑OES, ASTM E1479 | ≤10 ppm |
| Solubility in acetone (25 °C) | Gravimetric | >100 g L⁻¹ |
Moisture sensitivity is moderate. When ambient relative humidity exceeds 60 %, the powder may adsorb surface moisture to levels above 0.2 wt%, which can generate porosity in extruded profiles and blistering during continuous hot‑air vulcanization. Plant‑scale experience with a 120‑mm cold‑feed pin‑barrel extruder (L/D 16:1) processing EPDM sponge compounds determined that moisture content above 0.15 % (Karl Fischer, ASTM D5460) correlated with a sharp increase in surface defects. Pre‑drying in a vacuum oven at 40–50 °C for a minimum of 2 h is therefore recommended when packaging integrity is compromised. The product is packaged in nitrogen‑flushed HDPE drums with a shelf life of 12 months when stored at or below 30 °C in the original sealed container.
The Hildebrand solubility parameter of BTX‑EMPS is estimated at 21–23 MPa¹⁄², placing it in a range that ensures high affinity for polar elastomers such as nitrile rubber (NBR), hydrogenated nitrile rubber (HNBR), and epoxidized natural rubber (ENR). In NBR compounds with 33 % acrylonitrile content, the accelerator disperses readily without blooming, and mixing in an internal mixer at 50 °C initial temperature yields dispersion ratings above 8 (DIN ISO 11345). In non‑polar SBR/BR tread recipes, adequate dispersion is achieved when the batch temperature reaches 100–110 °C during the masterbatch stage; below this threshold, retained accelerator agglomerates may act as stress concentrators, leading to a 5–8 % reduction in tensile strength per ASTM D412. The 6‑ethoxy substituent reduces the tendency to migrate to the surface; no noticeable whitening has been observed in long‑term storage of vulcanizates at 25 °C and 50 % relative humidity for over 90 days.
The succinimide ring is susceptible to alkaline hydrolysis. Contact with primary or secondary amines, as well as strong bases (NaOH, KOH), must be avoided because ring‑opening destroys the delayed‑action character and liberates 4‑methoxyaniline, a potent scorch promoter. For the same reason, BTX‑EMPS is incompatible with amine‑based antioxidants and certain light‑stabilized additive packages unless processing temperatures are kept below 100 °C. Co‑vulcanization systems employing thiuram disulfide ultra‑accelerators (such as TMTD) combined with BTX‑EMPS may exhibit a severely shortened scorch time owing to the rapid generation of zinc dithiocarbamates; such combinations should be reformulated with a 20 % reduction in thiuram dosage. The product is not classified as a substance of very high concern under REACH (EU 1907/2006, Annex XVII) and is listed on the TSCA inventory. During incorporation into rubber, standard industrial hygiene practices for fine organic dusts (local exhaust ventilation, particulate respirator) are recommended. Disposal must comply with regional regulations for sulfur‑containing organic chemicals. Published data on long‑term ecotoxicological endpoints for this exact derivative is limited; therefore, release into water or soil must be prevented by closed‑loop material handling.
