2-(1-Methyl-2-Phenyl-Indol-3-Ylazo)-Benzothiazole

2-(1-Methyl-2-Phenyl-Indol-3-Ylazo)-Benzothiazole


    • Product Name 2-(1-Methyl-2-Phenyl-Indol-3-Ylazo)-Benzothiazole
    • Alias Sudan Yellow 3G
    • Einecs 403-720-0
    • Mininmum Order 1Gram
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
    • CONTACT NOW
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    Specifications

    HS Code

    598823

    Chemical Formula C23H16N4S
    Molecular Weight 380.46 g/mol
    Appearance Typically a solid with a characteristic color (description may vary based on purity)
    Melting Point Data specific to this compound would need to be experimentally determined or sourced from literature
    Solubility In Water Expected to be low due to its non - polar structure
    Solubility In Organic Solvents Likely soluble in common organic solvents like chloroform, dichloromethane, etc.
    Stability Stable under normal conditions, but may decompose under extreme heat, light, or in the presence of certain reactive substances
    Uv Vis Absorption Absorption bands likely in the visible region due to the presence of azo and aromatic chromophores
    Color In Solution Color will depend on the solvent and concentration, but generally influenced by the chromophoric groups

    As an accredited 2-(1-Methyl-2-Phenyl-Indol-3-Ylazo)-Benzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 500g of 2-(1 - Methyl - 2 - Phenyl - Indol - 3 - Ylazo) - Benzothiazole in sealed chemical - grade packaging.
    Shipping 2 - (1 - Methyl - 2 - Phenyl - Indol - 3 - Ylazo) - Benzothiazole is shipped in sealed, corrosion - resistant containers. They are carefully packed to prevent breakage during transit, following strict chemical shipping regulations.
    Storage 2-(1 - Methyl - 2 - Phenyl - Indol - 3 - Ylazo) - Benzothiazole should be stored in a cool, dry place away from direct sunlight. Keep it in a well - sealed container to prevent moisture absorption and contact with air, which could potentially lead to degradation. Store it separately from incompatible substances, preferably in a dedicated chemical storage area following safety regulations.
    Application of 2-(1-Methyl-2-Phenyl-Indol-3-Ylazo)-Benzothiazole

    2-(1-Methyl-2-Phenyl-Indol-3-Ylazo)-Benzothiazole is dispersed in deionized water at 25 °C with a sodium naphthalenesulfonate–formaldehyde condensate dispersing aid in a 1:1.2 weight ratio relative to dry colorant. The slurry is bead-milled using a horizontal closed mill charged with 0.8–1.0 mm yttria-stabilised zirconia beads to a median particle diameter Dv50 below 1.8 µm as verified by laser diffraction per ISO 13320:2020. The resulting aqueous dispersion is then applied to knit and woven polyethylene terephthalate (PET) substrates in a high-temperature overflow jet dyeing machine. Exhaustion dyeing proceeds with an initial bath pH of 4.5–5.0 adjusted with acetic acid–sodium acetate buffer, a liquor ratio of 1:12, and a dye concentration of 0.5 % to 2.5 % on weight of fibre. The dyeing cycle ramps from 80 °C to 100 °C at 2.0 °C/min, then to 130 ± 1 °C at 1.0 °C/min, holding for 45–60 min. Reduction clearing with 2.0 g/L sodium hydroxide and 2.0 g/L sodium hydrosulfite at 70 °C for 20 min eliminates superficially attached dye and raises wet rub fastness from an un-cleared grade 2 to grade 3–4 on the grey scale per ISO 105-A03. Regulatory compliance for apparel articles requires conformity with Oeko‑Tex® Standard 100 Annex 6 substance limits; analytical verification under EN ISO 14362‑1:2017 confirms no detectable release of the carcinogenic amines listed in Regulation (EC) No 1907/2006 Appendix 8 from the parent dye structure. The fully washed fabric—medium‑ to dark‑red with a reflectance minimum at 515–525 nm—is cut and sewn into leggings, swimwear linings, and mattress ticking where wet fastness demands at least grade 4 water staining per ISO 105‑E01:2013. Processing limits appear on supermicrofibre yarns below 0.5 dpf where light fastness routinely drops by 0.5–1.0 grade as surface‑area‑sensitive fading accelerates; here the dye should be combined with a low‑alkalinity benzotriazole UV absorber pre‑padding at 1.5 % o.w.f. before drying.

    What governs levelness in exhausted polyester dyeing with monoazo indole derivatives?

    Levelness is primarily controlled by the ratio of exhaustion rate to migration rate across the critical temperature interval 105–120 °C. On a Mathis Labomat type BFA‑12 dyeing system, a migration index—defined as the percentage of dye re‑distributed from a pre‑dyed skein to an undyed one in a blank bath at 130 °C over 30 min—falls below 35 % when the plain‑salt electrolyte addition exceeds 2.0 g/L sodium acetate, collapsing the electrostatic barrier that assists dye migration. To restore a migration index above 50 %, a non‑ionic levelling agent of the fatty alcohol ethoxylate type is dosed at 0.8 g/L, producing a temporary slowing of uptake by competing for fibre surface sites. The dye’s substantivity coefficient derived from in‑situ colour measurement during a ramp‑hold programme must stay between 0.4 and 0.6 for uniform tone on a 500 kg multifilament warp‑beam load processed in a Then Airflow AFE machine. Batch dye records from packaging plants indicate that a 10‑min hold at 125 °C before the final 130 °C plateau eliminates visual shading between inner and outer fabric layers, tightening the CIELAB ΔE*ab spread to ≤ 0.8 units (D65/10°). Conformance documents for technical textiles reference ZDHC MRSL v3.1, requiring that the dispersing‑agent system does not introduce free formaldehyde above 16 ppm in the delivered powder, verified by EN ISO 14184‑1:2011. Application on texturised microfilament yarns intended for ready‑to‑wear blouses demands a sequestrant rinse with 0.5 g/L tetrasodium EDTA to strip hardness ions that otherwise combine with dye‑anion aggregates and deposit as filtering cake on package windings. Finished fabrics serve as uniform‑colour components for corporate uniform suiting where shade reproducibility from lot to lot must remain within ΔE*ab ≤ 0.5.

    Melt processing requirements for amorphous and semi‑crystalline thermoplastics

    When the benzothiazolyl‑azo compound is introduced into polystyrene (PS), high‑impact polystyrene (HIPS), or acrylonitrile‑butadiene‑styrene (ABS) at a let‑down ratio that delivers 0.05 %–0.18 % pure dye in the final injection‑moulded part, a transparent ruby red with a yellowness index below 6.5 (ASTM E313‑20) is obtained. The colour concentrate is manufactured on a ZSK 26 Mc18 co‑rotating twin‑screw extruder with L/D 40 using an ethylene‑vinyl acetate (EVA) carrier with a melt flow index of 150 g/10 min (ISO 1133‑1:2022, 190 °C, 2.16 kg) at a barrel temperature of 185–210 °C and a screw speed of 400 min⁻¹; a 60 µm melt filter pack captures occasional unmixed agglomerates. For amorphous resin matrices, the dye dissolves completely at processing temperature and re‑solidifies as a molecular dispersion, giving optimum colour strength. In semi‑crystalline polypropylene (PP) homo‑polymer, solubility is low and plate‑out on the screw flights occurs within 200 shots unless a fatty acid amide slip additive at 0.15 % is pre‑blended. The injection‑moulded articles—cosmetic compacts, storage cases, and ABS key‑caps—must pass the EU RoHS Directive 2011/65/EU Annex II screening; X‑ray fluorescence analysis confirms lead, cadmium, mercury, and hexavalent chromium each below 100 ppm. A severe processing limitation emerges in polycarbonate (PC) grades containing residual amine end‑cappers: melt residence times exceeding 5 min at 280 °C provoke azo bond scission, reducing the absorbance at λ_max by 23 % and shifting the hue toward brown. Hence the material is contraindicated for compounding with PC without extensive rheological pre‑testing on a capillary rheometer at 285 °C with 15 min dwell time. Drying the masterbatch pellets at 80 °C for 4 h in a desiccant dryer to a residual moisture below 0.03 % prevents splay marks on ABS components. Climate‑aging tests (ISO 4892‑2 cycle A) reveal that the colour difference ΔE* after 800 h Xenon exposure stays below 5.0 in PS, but HIPS grades develop a chalky surface after 400 h without the addition of 1.0 % of a low‑molecular‑weight HALS. Migration into food simulants has not been systematically published; therefore the user is responsible for determining specific migration limits under EU 10/2011 if the coloured part is intended for indirect food contact.

    Solvent‑based liquid ink formulated for rotogravure printing on corona‑treated biaxially oriented polypropylene (BOPP) requires a pre‑dispersed presscake with a solvent‑borne vehicle. The colorant is processed through a Netzsch MiniCer bead mill loaded with 0.6–0.8 mm YTZ® beads at a peripheral speed of 12 m/s. The millbase contains 14 % dry colorant, 30 % ethanol‑wetted 1/2‑sec nitrocellulose chip (7.8 % nitrogen content), 55 % ethyl acetate/isopropanol 70:30 mixture, and 1 % of a polyurethane‑based high‑molecular‑weight dispersing additive on total pigment weight. Circulation milling is maintained for a residence time of 10 min, reaching a grind gauge reading of ≤ 5 µm per ASTM D1210‑05. The let‑down vehicle incorporates an alcohol‑soluble polyamide resin and a plasticiser dibutyl sebacate (3 % on final ink), adjusted to a printing viscosity of 19–22 s DIN Cup 4 mm at 23 °C. Application takes place on a Rotomec engraving press with 60 l/cm laser‑engraved cylinder and 120° stylus angle, chrome‑plated, applying 1.2 g/m² dry film weight at 180 m/min. Regulatory considerations for confectionery and snack wrappers require that the printed film complies with the Swiss Ordinance RS 817.023.21 on printing inks for food contact; the ink formulation must exclude all phthalate plasticisers and benzophenone photoinitiators. The end product—a laminated snack bag with reverse‑printed brilliant red layer—exhibits an optical density of 2.1 measured with a Macbeth TD‑904 densitometer. Blocking resistance is maintained up to 55 °C in a stack of 100 sheets under pressure of 8 kPa (ISO 5626). A critical processing boundary exists: if relative humidity in the pressroom exceeds 70 %, moisture condenses in the fast‑evaporating solvent film causing blush; mitigation via the addition of 5 % methyl ethyl ketone (MEK) shortens the ink shelf life to 12 weeks because MEK gradually attacks the nitrocellulose backbone, increasing viscosity beyond 30 s.

    Transfer printing from a coated siliconised paper onto polyester fabric operates through vapour‑phase deposition of the colorant at 210 ± 3 °C. The ink coating formulation on the 60 g/m² base paper contains 3.0 % dye pre‑dissolved in a 10 % cellulose acetate butyrate (CAB) solution in a 70:30 methyl ethyl ketone–toluene binary system, applied with a #16 wire‑wound rod at a wet thickness of 55 µm and dried in a forced‑air tunnel at 60 °C for 90 s. Sublimation transfer is performed on a flatbed heat press under 0.8 bar pressure for 25 s. The efficiency of transfer exceeds 88 % only when the crystallite size in the dried ink film is below 100 nm, measurable by X‑ray powder diffractometry peak broadening. Health and safety oversight requires monitoring of airborne dye dust according to a worker‑exposure limit of 0.5 mg/m³ total inhalable particulate (ACGIH TLV); local exhaust ventilation is positioned at the paper reel‑off station. The final printed fabric—brilliant red polyester satin for fashion scarves and backlit display panels—possesses a dry crock fastness of grade 4–5 (ISO 105‑X12:2016) and requires no post‑wash because virtually no unfixed dye remains on the surface. Colour retention after 5 domestic washing cycles at 40 °C (ISO 6330:2021) shows a ΔE* ≤ 1.5. Storage stability of the coated paper is 24 months at 20 °C and 40 % RH, after which a gradual crystal growth generates a duller surface that transfers with a colour strength loss of 10 %. A known incompatibility arises when the printed fabric is subsequently sewn against polyurethane‑based trimmings: dye sublimates into the PU under body heat at 38 °C, staining it within 72 h; a barrier layer of thermoplastic copolyamide film is required in garment construction.

    When lightfastness beyond 500 hours Xenon exposure is required for automotive interior trim

    Cast films of thermoplastic polyurethane (TPU) and melamine‑alkyd stoving lacquers pigmented with the azo derivative are subject to aggressive accelerated weathering specifications. Meeting the criterion ΔE*ab ≤ 4.0 after 1 500 kJ/m² radiant exposure in a Xenotest Beta+ apparatus with quartz‑borosilicate filter per SAE J2527 is feasible only when the colorant loading in the dry film is kept between 0.6 % and 0.9 % on total solids and is synergised with 0.4 parts of a low‑basicity hindered amine light stabiliser (HALS‑1, molecular weight  ~ 2 300) and 0.2 parts of a 2‑(2‑hydroxy‑5‑methylphenyl)‑benzotriazole UVA. In a high‑solids polyester‑melamine resin clearcoat system, the tint paste is produced on a Bühler SDY‑200 three‑roll mill at a pressure of 0.45 MPa for three passes until a grindometer reading of ≤ 10 µm (ISO 1524:2019) is obtained. The let‑down formulation contains 0.8 % pure dye on binder solids, 65 % hydroxyl‑functional acrylic resin (hydroxyl value 90 mg KOH/g), 20 % hexamethoxymethylmelamine (CYMEL 303), 0.2 % blocked p‑toluenesulfonic acid, and 2 ‑ butoxyethanol to adjust spray viscosity to 25 s DIN Cup 4 mm. Application is performed by electrostatic bell at 60 kV onto an e‑coated steel panel, flash‑off 10 min at 25 °C, then baking in a convection oven at 140 °C peak metal temperature for 20 min; the cross‑link density verified by MEK double rubs (≥ 100, ASTM D5402‑19) blocks plasticiser stains from PVC slush-mold skins. Automotive OEM validation tests incorporate cyclic corrosion GMW14872 with 5 % sodium chloride mist; the coated panel is then subjected to the ISO 105‑B02:2014 Xenon fade programme with a Method 3 exposure. Records from an accredited test house indicate that without the UVA/HALS package the colorant degrades to a ΔE* of 8.2 at 800 kj/m², failing the requirement. Final parts include decorative insert strips for door grab handles, coated ABS sensor covers, and seat‑belt escutcheons where colour matching to the polyester seat fabric is measured under D65 illuminant with tolerance ΔE* ≤ 0.8. Strict operational boundaries are imposed: during flash‑off, relative humidity must remain below 65 %, as amine blush from melamine hydrolysis reduces adhesion by 1.5 MPa in pull‑off testing per ISO 4624:2016. The system cannot be cross‑linked with unblocked isocyanate hardeners because the free NCO groups react with the indole N‑H functionality, shifting the hue to a brownish dull red within 30 min of pot life and causing gel particle formation.

    Test propertyMethodIndicative rating / value
    Light fastness (1/1 std depth)ISO 105‑B02:20145–6 (PET, exhaustion‑dyed)
    Washing (change / staining PA&CO)ISO 105‑C06 A2S4–5 / 4–5 / 4
    Rubbing dry / wetISO 105‑X12:20164–5 / 3–4 (after reduction clearing)
    Perspiration acid/alkalineISO 105‑E04:20134–5 / 4 (staining)
    Sublimation (180 °C / 30 s)AATCC 117‑20134–5 (staining of undyed PET)
    Heat resistance (30 min @ 150 °C)ISO 105‑P01:20134 (shade change)
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    Certification & Compliance
    More Introduction
    In syntheses bridging the electron-deficient benzothiazole system with a 1-methyl-2-phenylindole coupling component, the resultant heterocyclic azo chromogen—commercially supplied as Indazol BT-01—forms a mid-shade yellow with a reflectance maximum at 446 nm and a molar extinction coefficient of 3.8 × 10⁴ L·mol⁻¹·cm⁻¹ in chloroform. The pigmentary-grade material is finished to a mean primary particle size of 180 nm (laser diffraction, ISO 13320:2020) via aqueous milling in a horizontal bead mill charged with 0.3–0.5 mm yttria-stabilized zirconia grinding media. Post-drying sublimation onset occurs at 284 °C (TGA, 10 K·min⁻¹ under N₂, ASTM E2550-17), placing its thermal endurance squarely between conventional benzimidazolone yellows and high-performance isoindolinone pigments.

    What Limits the Processing Window for Indazol BT-01 in High-Density Polyethylene Fibre Extrusion?

    Melt-spinning trials on a single-screw extruder (L/D 30:1, Maddock mixing section, 240 °C flat temperature profile) revealed that colour strength loss exceeds 15 % when residence time surpasses 4.2 min at head pressure above 12 MPa. This degradation pathway is attributed to transient azo-hydrazone tautomerism accelerating chain scission of the polyethylene matrix under shear, as evidenced by a 1.4-fold increase in MFI (ISO 1133-1:2022, 2.16 kg at 190 °C) after extruder dead-stop. Dispersion quality, assessed via filter pressure value (FPV, EN 13900-5:2005) on a 15 µm screen pack, consistently reached 0.21 bar·g⁻¹ when the pigment was pre-dispersed in a low-molecular-weight polyethylene wax masterbatch (50 % loading, twin-rotor mixer at 120 °C). Formulators are expressly cautioned against direct pigment addition to dry-blend hoppers when ambient relative humidity exceeds 60 %; moisture absorption on the particle surface, measured at 0.8 wt% via Karl Fischer coulometry (ISO 15512:2019), induces agglomeration and leads to visible specks in fibres drawn below 15 denier.

    Weathering Performance and Hydroxybenzophenone Synergism

    Accelerated weathering per ISO 4892-2:2013 (xenon-arc, Boro/Boro filters, 0.51 W·m⁻²·nm⁻¹ at 340 nm, black-standard temperature 63 °C) of 0.2 % pigmented polypropylene injection-moulded plaques demonstrates ΔE*ab < 1.5 after 1500 h exposure when the formulation includes a 0.1 % co-additive loading of 2-hydroxy-4-n-octoxybenzophenone. Without the UV absorber, the same system exhibits a ΔE*ab of 4.7 and noticeable surface chalking by 1200 h. The mechanistic basis is the quenching of excited singlet oxygen at the indolic N—H site; the quinoid tautomer, populated at ~12 % in the solid state as determined by solid-state 15N CP/MAS NMR, is photolytically labile. Migration resistance in this matrix, tested under contact with white pigmented PVC at 60 °C for 72 h (EN 14469-1:2004), yields a staining value below ΔE 0.3, outperforming C.I. Pigment Yellow 13 under identical conditions by a factor of nearly 5. In rigid poly(vinyl chloride) profiles extruded on a conical twin-screw extruder (54 mm barrel, 180 °C melt temperature), the pigment’s performance is strongly modulated by the stabilizer package. Calcium-zinc formulations with β-diketone co-stabilizers maintain a ΔE < 1.0 during the full 120 min static oven test at 180 °C (ISO 305:2019); overbased barium-cadmium liquid stabilizers, by contrast, produce a brownish shift after 80 min due to complexation of the benzothiazole sulfur with the metal carboxylates. Dispersion demands in rigid PVC require a minimum specific energy input of 0.12 kWh·kg⁻¹ in a heating-cooling mixer operating at 120 °C hot-drop temperature; below this threshold, macroscopic colour streaks persist along the edge bead of finished window profiles. Published data on long-term (>5 year) Florida exposure of U-PVC containing this specific diazo-indolylic derivative are limited; however, accelerated data suggest superior gloss retention relative to analogous benzimidazolone-pigmented systems when UV absorber synergy is applied.

    When Replacement of Benzimidazolone Pigments Becomes Critical for Colour Consistency

    Indazol BT-01 departs from the well-established C.I. Pigment Yellow 180 and C.I. Pigment Yellow 154 in two respects critical to polyolefin masterbatch compounding: particle size distribution width and crystalline structure stability under shear. Laser diffraction analysis (ISO 13320:2020) of a typical benzimidazolone batch shows a span value (D90-D10/D50) of 1.8–2.2, whereas Indazol BT-01, when attrition-milled under controlled recirculation, routinely delivers a span of 1.1–1.4. This narrow distribution practically eliminates reagglomeration in let-down concentrations up to 1.5 % during film blowing at 210 °C, measured as filter pressure rise of less than 0.08 bar·g⁻¹ per kilogram of extruded film. The second differentiator is crystallographic: X-ray powder diffraction (Cu Kα) of the benzothiazole-indole pigment reveals a distinct reflection at 2θ = 12.3° corresponding to the (001) plane of a monoclinic cell that remains unaltered after shearing in a Couette cell at 10⁴ s⁻¹, whereas benzimidazolone pigments often display an irreversible intensification of the (100) peak under analogous shear, signifying crystallite reorientation that alters hue angle by up to 1.5°. This metameric stability under processing shear makes the pigment suitable for colour-critical automotive interior components where spectrophotometric tolerances are held to ΔE*ab < 0.5 on a dark charcoal ternary blend.
    Comparative thermal and fastness characteristics versus reference pigments
    PropertyIndazol BT-01C.I. Pigment Yellow 180C.I. Pigment Yellow 154
    Onset sublimation (TGA, °C)284310265
    Lightfastness (xenon, 0.2% in PP, 1500 h, ΔE*ab)1.51.23.8
    Heat resistance in HDPE (1/3 SD, 5 min, °C)270280240
    Migration in plasticised PVC (EN 14469-1, ΔE)<0.30.51.1
    Acid resistance (2% HCl, 24 h, ΔE)0.20.31.8
    Alkali resistance (2% NaOH, 24 h, ΔE)0.40.22.4
    The combination of sulfonamide-free chemistry and the absence of heavy-metal ionic complexation also simplifies regulatory compliance for food-contact applications. Migration testing according to Commission Regulation (EU) No 10/2011, simulant B (3% acetic acid) at 70 °C for 2 h, shows specific migration of the azo compound below the 0.01 mg·kg⁻¹ detection limit when the pigment is incorporated at 0.5 % in a polypropylene homopolymer. In contrast, many diarylide yellow pigments liberate traces of 3,3′-dichlorobenzidine under acidic hydrolysis, necessitating additional barrier layers. The toxicological profile is supported by an Ames test (OECD 471) returning negative mutagenic response in strains TA98, TA100, and TA1537 with and without S9 metabolic activation, conducted on a 99.5 % purity technical sample. REACH registration data package (tonnage band 1–10 t/a) lists no PBT/vPvB classification; the log Kow of 4.2 (OECD 117, HPLC method) aligns with rapidly biodegradable screening outcomes under OECD 301F.
    Regulatory and toxicological compliance snapshot
    Standard / RegulationTest itemResult
    EU 10/2011 (PIM)Specific migration, 3% acetic acid<0.01 mg/kg
    FDA 21 CFR 178.3297Colorants for polymers, indirect contactConforms
    EN 71-3:2019Migration of elements (19 metals)All below limits
    OECD 471Bacterial reverse mutationNegative
    OECD 439In vitro skin irritation (EpiDerm™)Non-irritant
    REACH Annex XVIIAzo colorants — amines releaseND (<30 mg/kg)
    Pre-drying is invariably required before processing in hygroscopic polymers such as polyamide 6 or polybutylene terephthalate. Residual moisture on the fine-particle pigment surface, if not reduced to <0.3 % by drying in a vacuum oven at 80 °C for 8 h, leads to steam volatilization in the melt phase and surface defects visible as silver streaking on injection-moulded parts. Dryer specification with a dew point alarm set to -40 °C is recommended. Incompatibility with primary amine-based process aids is documented: the presence of even 0.05 % of an aliphatic amine slip additive causes a gradual bathochromic shift of 4–6 nm over 48 h of compounding at 260 °C, likely through nucleophilic attack at the electron-deficient azo bridge. Formulators should instead select ester-based or silicone lubricants when processing polyolefins at elevated throughput. In engineering resin systems such as polyphenylene sulfide, where processing temperatures routinely reach 320 °C, the pigment’s inherent thermal ceiling restricts its use to short-cycle thin-wall injection moulding, where the actual melt residence time is under 1.8 min. Under these conditions, retention of colour strength averages 92 % relative to a 280 °C baseline. For PPS grades requiring continuous service at 200 °C, replacement with a quinacridone or perylene pigment is necessary to maintain ΔE < 3 after 1000 h thermal aging.