2-[[(4-Ethenylphenyl)Methyl]Thio] Benzothiazole
|
HS Code |
773300 |
| Chemical Formula | C18H15NS2 |
| Molecular Weight | 309.45 |
| Appearance | Solid (usually) |
| Physical State At Room Temperature | Solid |
| Melting Point | Data may vary depending on purity |
| Boiling Point | Data may vary depending on purity |
| Solubility In Water | Low solubility (organic compound, likely insoluble) |
| Solubility In Organic Solvents | Soluble in common organic solvents like chloroform, toluene |
| Density | Data may vary depending on form and purity |
| Color | Typically colorless to light - colored solid |
As an accredited 2-[[(4-Ethenylphenyl)Methyl]Thio] Benzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 2 - [(4 - Ethenylphenyl)Methyl]Thio Benzothiazole in a sealed chemical - grade pouch. |
| Shipping | 2 - [(4 - Ethenylphenyl)Methyl]Thio Benzothiazole is shipped in well - sealed containers, following strict chemical transport regulations. Packing ensures protection from environmental factors during transit to prevent any damage or leakage. |
| Storage | Store 2 - [(4 - Ethenylphenyl)Methyl]Thio Benzothiazole in a cool, dry, well - ventilated area. Keep it away from heat sources, flames, and oxidizing agents. Store in a tightly closed container to prevent exposure to air and moisture, which could potentially cause degradation. Avoid storing near incompatible substances. |
In rubber compounding, the persistent migration of unbound accelerators such as 2‑mercaptobenzothiazole (MBT) to the vulcanisate surface generates a well‑documented failure chain: surface bloom reduces autohesion in multi‑component assembly, contaminates adjacent polyurethane or textile layers, and elevates extractable polycyclic aromatic hydrocarbon (PAH) levels beyond permissible limits under EU Regulation 1907/2006 Annex XVII Entry 50. 2‑[[(4‑Ethenylphenyl)Methyl]Thio] Benzothiazole addresses this through a mechanism in which the para‑styrenic pendant group covalently grafts onto diene rubber backbones during the initial high‑shear mastication phase, anchoring the benzothiazole heterocycle to the polymer network before elemental sulphur crosslinking is initiated. On a typical 270‑L intermeshing tangential Banbury mixer with a fill factor of 0.75 and rotor speed held at 35–45 rpm, the monomer is introduced at 0.8–2.5 phr during the masterbatch stage together with carbon black (N330 or N234 grades), zinc oxide (4.0 phr), stearic acid (2.0 phr), and a stabilised grade of the monomer carrying 35–55 ppm monomethyl ether hydroquinone (MEHQ) inhibitor. Dump temperature must remain strictly below 145 °C; excursions beyond 150 °C trigger runaway vinyl homopolymerisation that manifests as hard, discrete gel particles in the subsequent extrudate, a failure mode confirmed by optical microscopy of thin‑sectioned uncured sheets. After dumping, the masterbatch is accelerated on a two‑roll mill at 60 °C with sulphur (1.5–2.2 phr) and N‑cyclohexyl‑2‑benzothiazolesulfenamide (CBS) at a reduced 0.4–0.8 phr to provide a dual‑kinetic cure profile. Vulcanisation is conducted in a multi‑daylight press at 160 °C to a rheometer‑determined t₉₀ plus 3 min, typically 8–14 min total cycle time. Post‑cure acetone extraction per ASTM D297 Section 18 quantifies non‑network thio‑compounds; formulations substituting 1.8 phr of this monomer for an equimolar sulphur‑equivalent of MBT reduce 24 h Soxhlet extractables from an industry‑average 2.9–3.6 % by mass down to 0.4–0.7 %, effectively eliminating bloom under ISO 1431‑1:2004 static ozone exposure at 50 pphm and 40 °C for 96 h. A comparative summary of tensile retention and surface defect density is presented in the following table.
Can copolymerisation of styrenic benzothiazole monomers improve the weatherability of thermoplastic styrenic block copolymers?Solution‑polymerised styrene‑butadiene‑styrene (SBS) triblock copolymers, when formulated for soft‑touch automotive interior skins and clear sealant overlayers, lose elongation‑at‑break and exhibit surface tackification under ISO 4892‑2 Xenon‑arc accelerated weathering (Method A, cycle 1, 102 min dry/18 min water spray) within 400–600 h because the unsaturated polybutadiene mid‑block lacks intrinsic UV‑absorbing chromophores. Grafting 2–5 wt% of 2‑[[(4‑ethenylphenyl)methyl]thio] benzothiazole onto the polybutadiene segment via a controlled solvent‑grafting protocol — anionic polymerisation in cyclohexane at 50 °C under 0.5 MPa argon, initiated by sec‑butyllithium (0.08 mmol/g polymer) and terminated with degassed methanol — covalently yields pendant benzothiazole moieties whose n→π* and π→π* transitions in the 290–340 nm range act as sacrificial photon absorbers. Subsequent hydrogenation of the butadiene block (selective Co‑based catalyst, 3.0 MPa H₂, 80 °C) to produce a styrenic‑benzothiazole‑functional SEBS results in a material that retains 92 % of its initial ultimate tensile strength after 1,500 h of ISO 4892‑2 exposure, compared with 67 % for an identically hydrogenated, non‑functionalised control. The functionalised granules are melt‑processed on a co‑rotating twin‑screw extruder (L/D 44, screw speed 250 rpm) with barrel zones set at 160–200 °C and an in‑line melt filter fitted with 40‑μm screens to trap microgel residues that occasionally arise if O₂ ingress during solvent stripping exceeds 10 ppm. Injection moulding into 2‑mm plaques for adhesive interlayer testing according to ISO 11339:2010 (T‑peel, 200 mm/min) confirms that the pendant benzothiazole additionally coordinates with chromium‑oxide‑passivated aluminium foil, boosting peel strength from 1.8 N/mm to 3.1 N/mm after 85 °C/85 % RH conditioning for 500 h. The processing limit is sharp: at incorporation levels above 6 wt%, dynamic mechanical analysis reveals a 14 °C depression of the polybutadiene‑block glass transition temperature because the bulky benzothiazole pendant disrupts microphase separation, thereby reducing the rubbery plateau modulus from 5.2 MPa to 3.8 MPa — an unacceptable softening for structural hot‑melt applications.Formulating a low‑migration adhesion promoter for free‑radically cured coatings intended for post‑formed aluminium‑magnesium alloy sheet (EN AW‑5182) requires navigating the conflict between efficient co‑cure with acrylate matrices and the inherent chain‑transfer activity of the thioether bridge. In a typical UV‑curable clearcoat base composed of bisphenol‑A epoxy diacrylate (45 wt%), trimethylolpropane triacrylate (25 wt%), and isobornyl acrylate (23 wt%), the benzothiazole‑functional styrenic monomer is pre‑dissolved at 3.0–5.0 wt% under yellow‑filtered light. The addition of 2.5 wt% 2‑hydroxy‑2‑methylpropiophenone and 0.8 wt% bis(2,4,6‑trimethylbenzoyl)‑phenylphosphine oxide ensures through‑cure of a 25‑μm wet film on aluminium Q‑panels using a medium‑pressure mercury arc lamp delivering 800 mJ/cm² UVA (measured by a calibrated EIT UV Power Puck). The benzothiazole heterocycle forms a coordinative bond with unoxidised Al³⁺ sites at the coating‑metal interface; X‑ray photoelectron spectroscopy (XPS) depth profiling of delaminated fracture surfaces after 1,000 h of neutral salt spray (ISO 9227:2022, 5 % NaCl, 35 °C) locates thio‑functional fragments within 3–7 nm of the metal oxide layer, suggesting true chemical anchoring. Consequently, cross‑hatch adhesion (ISO 2409:2020) remains at class 0 after the exposure, while an equivalent formulation devoid of the monomer drops to class 3 by 720 h. Worth noting is the rheological penalty: the monomer elevates the uncured varnish viscosity from 1.2 Pa·s to 2.9 Pa·s at 25 °C and 10 s⁻¹ because the planar benzothiazole ring raises the free‑volume demand; this demands heated roll‑coater application at 40 °C to restore a process‑compatible 1.0–1.4 Pa·s range and may require reformulation of the diluent balance if retrofitting onto existing ambient‑temperature coating lines. Post‑cure, immersion in boiling 3 % acetic acid for 2 h (simulating retort‑pouch sterilisation) extracts less than 0.02 mg/dm² of organic nitrogen‑ containing species, placing the coating well under the overall migration limit of 10 mg/dm² specified in Regulation (EU) No 10/2011 for plastic food‑contact materials.Selective metal sorption resins via suspension copolymerisationThe donor character of the endocyclic sulphur and the conjugated nitrogen in benzothiazole creates a soft Lewis‑base pocket that discriminates precious metal chloro‑complexes — [AuCl₄]⁻, [PdCl₄]²⁻ — over base‑metal cations present in printed‑circuit‑board leachates. Monodisperse crosslinked beads incorporating 2‑[[(4‑ethenylphenyl)methyl]thio] benzothiazole are prepared by aqueous suspension copolymerisation: the organic phase containing 18–25 wt% functional monomer, 18–22 wt% divinylbenzene (technical grade, 80 % DVB isomers), 45–55 wt% styrene, and 6–10 wt% methyl isobutyl carbinol porogen together with 0.3 wt% azobisisobutyronitrile is dispersed into a 10‑fold excess of deionised water containing 0.15 wt% poly(vinyl alcohol) (degree of hydrolysis 87–89 %, 4 % aqueous solution viscosity 25 mPa·s) in a baffled reactor agitated at 280 rpm. Polymerisation proceeds for 14 h at 75 °C under nitrogen, yielding spherical beads of 300–600 μm after sieving. The resultant resin is conditioned with 1.0 M HCl and loaded with a simulated waste‑water containing 120 mg/dm³ Au(III) at pH 1.8 in the presence of 2.5 g/dm³ Cu(II) and 1.8 g/dm³ Ni(II). After 4 h batch equilibration on an orbital shaker at 25 °C, inductively coupled plasma‑optical emission spectrometry (ICP‑OES per ISO 11885:2007) reveals a gold uptake of 98–127 mg/g dry resin at saturation, with selectivity coefficients αAu/Cu exceeding 350 and αAu/Ni exceeding 600. Dynamic column breakthrough measurements on a 10‑cm‑bed (internal diameter 1.2 cm, flow rate 4 BV/h) match the equilibrium data to within 10 % until 85 % breakthrough, after which intra‑particle diffusion limitations cause tailing. Regeneration is accomplished with 0.5 M thiourea in 0.1 M HCl, which strips 97 % of loaded gold in 6 bed volumes, although cumulative capacity loss of 4–6 % per cycle over 10 regeneration runs has been attributed to partial oxidation of the thioether bridge to sulfoxide, observable as a shift in the S 2p XPS binding energy from 163.5 eV to 166.1 eV. This limits operational lifetime to approximately 15–20 cycles before a measurable drop in breakthrough volume requires fresh resin make‑up, a factor that must be cost‑modelled against the spot price of Au when evaluating commercial deployment.When benzothiazole‑functional styrenics are copolymerised into vinyl ester resinsHigh‑cross‑link‑density vinyl ester resins derived from bisphenol‑A epoxy and methacrylic acid exhibit severe shrinkage‑stress cracking during post‑cure of thick‑section castings (> 15 mm) intended for chlor‑alkali cell covers and flue‑gas desulphurisation (FGD) duct liners. Substituting 12–18 wt% of the styrene reactive diluent with 2‑[[(4‑ethenylphenyl)methyl]thio] benzothiazole in a standard commercial bisphenol‑A epoxy vinyl ester (acid number ≤ 8 mg KOH/g, styrene content 42 %) and catalysing with methyl ethyl ketone peroxide (1.5 wt%) plus cobalt octoate (0.2 wt%, 6 % Co) at ambient temperature, followed by a programmed oven ramp (25 °C hold 4 h, ramp to 100 °C at 0.2 °C/min, hold 3 h, ramp to 150 °C at 0.1 °C/min, hold 2 h), yields a cured network in which the benzothiazole pendant participates through its vinyl group and also contributes secondary thio‑ether bridging upon radical‑mediated hydrogen‑abstraction from the methylene‑thio spacer at ≥ 125 °C. The result is a 7–12 °C increase in glass transition temperature measured by dynamic mechanical analysis (tensile mode, 1 Hz, 3 °C/min) from a baseline of 132 °C to 141–144 °C, and a reduction in the coefficient of linear thermal expansion below 60 °C from 68 μm/m·°C to 54 μm/m·°C (ASTM E831‑19). Simultaneously, the benzothiazole rings exhibit an unexpected scavenging effect towards acidic permeants: after 28‑day immersion in 15 % hydrochloric acid at 70 °C under ISO 175:2010, the modified resin shows a mass uptake of only 0.37 % versus 1.12 % for the unmodified control, and its tensile strength retention (ISO 527‑2, Type 1B) increases by 14 percentage points. This is tempered by the fact that the monomer, with its rigid aromatic nucleus, lowers the room‑temperature pot‑life from 38 min to 22 min at 25 °C owing to an exotherm‑accelerated Trommsdorff‑Norrish gel effect driven by the higher local terminal double‑bond concentration; large‑volume pourings exceeding 25 kg therefore require active cooling of the mould jacket to 5 °C to avoid a runaway that would produce micro‑cracks visible by scanning acoustic microscopy at 15 MHz. To maintain a consistent interlaminar shear strength (> 35 MPa per ASTM D2344) in glass‑fibre‑reinforced laminates, the initiator package must be adjusted downward by 0.3 wt% for each 5 wt% increment of the functional monomer.In optoelectronic device encapsulation and advanced display patterning, a persistent obstacle is achieving a refractive index above 1.60 while retaining good dry‑etch resistance and low outgassing under high‑vacuum deposition of indium tin oxide. A photopatternable copolymer formulation developed for direct laser writing (405 nm) resolves this by co‑polymerising 8–15 wt% 2‑[[(4‑ethenylphenyl)methyl]thio] benzothiazole with methyl methacrylate‑co‑methacrylic acid backbone monomers and pentaerythritol tetraacrylate as cross‑linker in a 2‑methoxy‑1‑methylethyl acetate solution at 25 % solids. The benzothiazole chromophore possesses a calculated polarisability volume exceeding 28 ų based on the Lorentz‑Lorenz equation; ellipsometric measurement of spin‑cast films ( 1,500 rpm, 30 s, soft‑baked at 95 °C for 120 s) on silicon wafers provides a measured n = 1.618 at 589 nm (sodium D‑line) in the fully cured state after broadband UV flood exposure (3,000 mJ/cm²) and a 220 °C post‑exposure bake for 30 min under nitrogen. Pattern fidelity is evaluated by fabricating 5‑μm line‑and‑space arrays using a mask‑aligner and developing in 0.5 % aqueous sodium carbonate; edge roughness measured by critical‑dimension scanning electron microscopy remains below 45 nm (3σ) only when the monomer content is kept below 12 wt%, beyond which the dissolution‑rate differential between exposed and unexposed regions collapses because the benzothiazole acts as a competing deep‑UV absorber. Outgassing masses collected by gas chromatography‑mass spectrometry during a simulated vacuum bake (10⁻⁵ Pa, 200 °C, 2 h) show total volatile condensable material below 0.08 % of initial film weight when the post‑exposure curing ramp includes a 10‑min hold at 100 °C to drive off residual monomer, fulfilling the outgassing criterion of NASA ASTM E595 (collected volatile condensable material ≤ 0.1 %) for low‑earth‑orbit optomechanical assemblies. The chief processing bottleneck arises from the moderate oxygen inhibition of the styrenic unit; an overlay of nitrogen‑purged transparent polyethylene film during UV exposure is mandatory at web speeds below 2 m/min on roll‑to‑roll lines, otherwise the top 200–300 nm of the coating remain tacky and render subsequent metallisation adhesion to less than 2 N/25 mm (ASTM D3330, method B). |
Competitive 2-[[(4-Ethenylphenyl)Methyl]Thio] 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
Flexible payment, competitive price, premium service - Inquire now!
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | Off‑white to pale yellow crystalline powder | Visual / ISO 787‑1 |
| Purity (HPLC, 254 nm) | ≥ 97.0 area‑% | In‑house, C18 column, acetonitrile/water gradient |
| Melting range | 68–73 °C | DSC, 10 K/min, ASTM E1356 |
| Loss on drying (vacuum, 40 °C) | ≤ 0.5 wt% | ISO 803 |
| Residual 4‑vinylbenzyl chloride | ≤ 0.3 wt% | GC‑FID after methanol extraction |
| Sulfated ash | ≤ 0.1 wt% | ISO 6884 |
| Volatile N‑nitrosamines | ≤ 0.5 µg/kg | ISO 29941 (GC‑TEA) |
| Storage stability (unopened, 2–8 °C, N₂) | Purity drop < 1% over 12 months | Accelerated aging at 25 °C/60% RH (Arrhenius projection) |
| Accelerator System | Extractable MBT (µg per g compound) | Test Method | Visual Bloom After 14 Days at 40 °C |
|---|---|---|---|
| 1.5 phr CBS + 2.0 phr sulfur | 68.3 ± 4.1 | EN 14362‑1 (acetone, 16 h) | Heavy white bloom |
| 1.2 phr MBTS + 1.8 phr sulfur | 94.7 ± 5.3 | EN 14362‑1 | Moderate bloom |
| 2.5 phr copolymerized monomer (BT‑VB) + 2.0 phr sulfur | 0.8 ± 0.2 | EN 14362‑1 extended 48 h | None detected |
