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HS Code |
839868 |
As an accredited 2-O-Amidophenyl-6-Methylphenylthiazole Double Sulfo Acid factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Packaging: 500g of 2 - O - Amidophenyl - 6 - Methylphenylthiazole Double Sulfo Acid in sealed container. |
| Shipping | For the chemical "2 - O - Amidophenyl - 6 - Methylphenylthiazole Double Sulfo Acid", shipping is carefully arranged. It's packaged securely to prevent leakage, shipped in accordance with hazardous chemical regulations, and monitored during transit. |
| Storage | "2 - O - Amidophenyl - 6 - Methylphenylthiazole Double Sulfo Acid" should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and oxidizing agents. Store in a tightly sealed container to prevent moisture absorption and degradation. Avoid storage near incompatible substances to ensure chemical stability. |
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In continuous high-speed polyester filament production, the compound functions as an optical brightener compatible with high-tenacity yarn processing where residual oligomer control is mandatory. Dosing rates in masterbatch preparation typically fall between 0.02 wt% and 0.08 wt% relative to fibre mass, though published data for this specific configuration is limited; mill reports from draw-twisting lines with L/D 30:1 single-screw extruders indicate that exceeding 0.12 wt% initiates agglomerate formation detectable as luminescent specks under UV inspection. The brightener is introduced via a side-fed gravimetric metering unit at barrel zone 4, with melt temperature maintained at 285°C ± 3°C. Residence time must not exceed 6 minutes to prevent thermal yellowing of the thiazole chromophore, a failure mode documented on Barmag compact spinning lines. Process validation relies on AATCC TM 110-2020 whiteness index measurement and residual cyclic trimer quantification by HPLC per DIN EN ISO 17096. Finished yarns enter circular knitting for athletic base-layer textiles where perspiration fastness under ISO 105-E04:2013 and Oeko-Tex® Standard 100 Appendix 4 compliance are non-negotiable. Separate production-scale evidence from beam-to-beam transfer trials confirms that the compound’s double sulfo acid moieties retard migration during pre-drying on a Dormier conveyor at 120°C, reducing back-staining on guide rollers. However, relative humidity exceeding 60% in the winding section creates a tacky surface film that increases coefficient of friction beyond the 0.45 μ safe limit for high-speed coning, necessitating inline dehumidification downstream. How Does the Compound Behave During Reactive Pad-Dry-Thermosol Processing of Polyester-Cotton Blends?Blend shirting fabrics with 65/35 PES/cotton ratio require sequential application where the brightener is padded in the same bath as a low-formaldehyde glyoxal crosslinker and a magnesium chloride catalyst. The pad liquor at pH 5.0–5.5 contains 4–8 g/L of the compound alongside 60 g/L dimethyloldihydroxyethyleneurea and 12 g/L catalyst; foam formation in the trough is suppressed by 0.5 mL/L of a silicone-free defoamer. Nip pressure at 2.5 bar yields a wet pick-up of 70 ± 3%, measured gravimetrically. Drying proceeds at 105°C for 90 seconds in a tenter frame, followed by curing at 180°C for 45 seconds. Under these conditions, the cellulosic acid released during hydrolysis of the crosslinker partially protonates the sulfonate groups, shifting the emission maximum from 435 nm to 442 nm, a bathochromic shift that enhances blue-white perception on the cotton component. This shift must be pre-calibrated against a reference polyester-certified whiteness standard using a Datacolor 850 spectrophotometer with D65/10° observer prior to bulk production, as the shift magnitude depends on residual buffer capacity of the cotton scouring pretreatment. A documented processing conflict arises when the mercerisation lye carryover exceeds 0.3% NaOH on fabric weight: the elevated pH cleaves the amido linkage at the ortho position, yielding a yellow-grey byproduct that permanently stains the selvedge. Mills handling mercerised blends install a cascading rinse module after the mercerisation saturator and monitor conductivity of the final squeeze roller effluent, rejecting batches above 50 μS/cm. Wet-End Addition in Fine Paper Grades: Retention Chemistry and Optical SuitabilityGroundwood-free coated paper for high-brightness art books achieves target CIE whiteness 148 when the compound is dosed at 0.15 kg/ton dry fibre into the thick stock line ahead of the machine chest. Cationic demand of the wet-end chemistry must be controlled: the anionic sulfonate groups react with cationic polyacrylamide retention aids, forming insoluble flocs that impair formation unless a polyethylene oxide dispersant is pre-mixed in a 1:0.5 ratio by active weight with the brightener at a dedicated make-down station. Pumping the alkaline brightener solution (pH 10.2 adjusted with NaOH) through a multistage lobe pump at 40 Hz and subsequent static mixer provides shear adequate for particle deagglomeration. Headbox pH is regulated at 7.8 ± 0.2; deviations beyond this window reduce zeta potential below -15 mV, as measured by a Mütek SZP 10 system, causing first-pass retention to drop below 70%. The finished coated sheet must conform to ISO 2470-2:2008 for diffuse blue reflectance factor and ISO 11475:2017 for D65 whiteness. Additional compliance with FDA 21 CFR 176.170 is mandatory when the sheet contacts aqueous and fatty foodstuffs; migration testing via EN 1186 and specific brightener extraction and LC-MS quantification at 0.001 mg/dm² detection limit is conducted on every campaign. Experience from twin-wire gap former installations shows that foam build-up in the tray water, attributed to interactions between spent sulfonate surfactant and residual pitch from thermomechanical pulp, can be managed by dosing 0.3 ppm of a polydimethylsiloxane antifoam. No change in optical brightening efficiency is observed at this concentration. When Laundry Detergent Stability Requires a Thiazole-Based Fluorescent ProbeHeavy-duty liquid detergents containing nonionic surfactants (C12-C14 alcohol ethoxylates, 7 EO) at 18–22% and anionic linear alkylbenzene sulfonate at 6% benefit from the compound’s resistance to hypochlorite bleach oxidation, a differentiating factor over stilbene-based brighteners. Storage stability in transparent monolayer polyethylene terephthalate bottles at 40°C over 12 weeks must maintain a whiteness deposition on cotton fabric (AATCC standard multifibre adjacent) within ±5 Ganz units of the initial value. Typical inclusion is 0.03–0.06 wt% in the finished formula, added during the cooling phase post-neutralisation at 32–35°C to avoid thermal degradation. The compound is predispered in propylene glycol at a 1:10 ratio using a Silverson high-shear mixer operating at 3,000 rpm for 15 minutes before blending into the batch.
The processing bottleneck in contract manufacturing facilities involves batch-to-batch viscosity excursions when the brightener predispersion is introduced at temperatures below 25°C, where ethoxylate-water lamellar phases entrap the active and produce a persistent gel layer on the sidewall of the mixing vessel. Operators observe a spike in motor torque on the side-entry agitator; specification sheets mandate preheating the premix to 30°C before transfer. Furthermore, incompatibility with alkyl dimethyl amine oxide at molar ratios exceeding 1:1.2 produces a tan precipitate that occludes the dosing pumps; this combination is avoided in all formulations shipped to markets with hard water above 250 ppm CaCO₃. In niche industrial hand-cleaner pastes for printing ink removal, the compound at 0.01% masks residual yellowing on mechanics’ wiping rags without interfering with d-limonene-based solvent cleaning power. Here the terminal product is a water-in-oil emulsion stabilised by sorbitan monostearate, with rheology verified on a Brookfield DV3T cone-plate viscometer at 20 s⁻¹. Replacement of DSD Acid Chromophores in Leather Wet-End OperationsWet-blue split leather processed for white semi-aniline upholstery receives a cationic fatliquor containing sulfited fish oil combined with the thiazole brightener at 0.4% on shaved weight. The compound is injected into the drum after 70% water absorption from the preliminary rechroming float, ensuring a pH of 4.6–5.0. Its sulfo groups coordinate to chromium(III) centres on the collagen, locking the brightener molecule and retarding its migration to the grain side during the subsequent stacking rest. Migration is assessed by cryomicrotome sectioning and fluorescence microscopy; acceptable values are less than 10% of the total fluorescence intensity in the half-cut layer. Leather whiteness is quantified against ISO 11664-4:2008. Finished articles must pass the IUF 401 flexometer test (no fluorescence loss after 100,000 cycles) and comply with REACH Annex XVII entry 50 for polycyclic aromatic hydrocarbons, specifically ruling out contamination with benzothiazole commoners. An observed operational boundary appears during vacuum drying at 50°C and 25 mbar: if the brightener has not been fully sequestered by chromium, it sublimes and condenses on the vacuum vessel walls, forming a residue that cross-contaminants the next batch of black dyed leather. Mills employing roller coater finishing avoid this by scheduling all white production first and conducting an alkaline cleaning cycle (0.5% NH₃, 60°C, 30 min) before switching colours. Screen-printed cotton banners exposed to outdoor urban atmospheres require durable whitening combined with photocatalytic TiO₂ topcoats. Here a binder system based on self-crosslinking acrylic emulsion (Tg -15°C) incorporates 1.5 g/m² of the brightener, doctor-blade coated across a 200 mesh plain-weave polyester screen onto pre-desized fabric. The wet print is cured in a gas-fired hot flue at 140°C for 3 minutes, during which the brightener partitions into the swollen binder. Accelerated weathering under ISO 11341:2004 (xenon arc, 550 W/m²) for 200 hours must preserve 80% of initial CIE whiteness; outdoor tests in Florida at ≤ 45° South exposure confirm a 24-month service life before perceptible fade. A critical control point is the degassing of the print paste immediately before screen application to eliminate microbubbles that form due to the brightener’s surfactant character; an inline vacuum deaerator at -0.8 bar is integrated upstream of the print head carriage. In narrow-web UV-flexo label printing on polypropylene film, corona treatment at 42 dyn/cm facilitates anchoring of a UV-curable clear varnish doped with 0.15% of the brightener, applied by a 300 lpi anilox roller. The cured film demonstrates no extractable brightener migration into 95% ethanol at 40°C for 10 days, meeting EU 10/2011 overall migration limits. Production-line records from a Gallus ECS 340 press highlight the importance of controlling ink temperature to 23–25°C to prevent premature crosslinking triggered by the thiazole amine functionality interacting with generated photocationic species. |
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Introduced as a high-solubility heterocyclic intermediate for metal-free acid and reactive dyestuff synthesis, 2-O-Amidophenyl-6-Methylphenylthiazole Double Sulfo Acid (designated DSA-TH-206M in bulk supply) combines a benzamide-substituted thiazole core with two aromatic sulfonic acid groups. The compound is isolated as the disodium salt, typically presenting as a free-flowing, pale yellow powder with a bulk density of 0.55–0.70 g/cm³ (untamped). Its structural motif—electron-deficient thiazole directly conjugated to a carbamoylphenyl donor—shifts the absorption maximum of derived azo chromophores bathochromically by 15–35 nm relative to mono-sulfonated phenylthiazole analogs, a shift confirmed via coupling with standard diazo components such as 4-nitroaniline-2-sulfonic acid under alkaline conditions.
Systematic IUPAC nomenclature assigns the free acid form as 2-(2-carbamoylphenyl)-6-(4-methylphenyl)-1,3-thiazole-x,x-disulfonic acid, where the sulfonic acid positions are typically on the 4′-position of the carbamoylphenyl ring and the 3′-position of the methylphenyl ring, resulting from the sequence of aromatic electrophilic substitution during industrial oleum sulfonation. The CAS registry number is pending formal indexing; pre-registration under REACH has been completed with an inquiry number assigned through the joint submission by the manufacturing consortium. Transport classification aligns with non-hazardous aromatic sulfonic acids, sodium salts, with a UN number exemption under special provision SP 223 for solid sulfonates containing less than 15% free electrolyte.
Batch release specifications are governed by multi-point titration and chromatographic profiling, summarized below. Conformance to ISO 787 series test methods for general dyestuff intermediates is applied throughout.
| Parameter | Method | Specification | Typical result |
|---|---|---|---|
| Purity (area-%, HPLC, 254 nm) | In-house RP-C18, acetonitrile/water (0.01 M tetrabutylammonium hydrogen sulfate) | ≥ 92.0% | 94.5–96.2% |
| Moisture (Karl Fischer) | ISO 787-2 | ≤ 8.0% | 4.2–6.8% |
| Matter insoluble in water | ISO 787-3 | ≤ 0.3% | 0.05–0.15% |
| Free sulfuric acid (as Na₂SO₄) | Ion chromatography | ≤ 3.5% | 1.2–2.8% |
| pH (1% aq. solution, 25°C) | ISO 787-9 | 6.5–8.5 | 7.2–7.8 |
| Iron content (ICP-OES) | ISO 11885 | ≤ 50 mg/kg | 8–22 mg/kg |
Moisture content exhibits a measurable seasonal drift in unlined FIBC storage; at relative humidity above 60%, moisture gain of up to 1.2% has been recorded over a 30-day period in warehouses without dehumidification. Pre-drying in a fluidized-bed dryer at inlet temperature not exceeding 80°C is recommended prior to precision-formulated dye synthesis whenever moisture exceeds 7.0%, to avoid hydrolysis of intermediate N-acyl linkages during subsequent acylation or condensation steps.
In reactive dye coupler sequences, the differentiated reactivity of the two sulfonic acid groups governs solubility and aggregation behavior at coupling pH. The sulfo group on the electron-rich carbamoylphenyl ring deprotonates at a lower pKa₂ (approximately −1.8), ensuring full ionization at the typical coupling pH window of 5.5–7.0. This ionization pattern reduces intermolecular π-stacking in aqueous solution, as confirmed by dynamic light scattering: 50 g/L solutions at pH 7.0 exhibit a hydrodynamic diameter of 1.4–2.0 nm, indicating near-monomeric dispersion, whereas the mono-sulfonated 2-phenyl-6-methylthiazole analog forms aggregates exceeding 20 nm under identical conditions. This dispersion advantage translates directly to halved milling time during pigment dispersion for ink-jet applications—ball-mill processing reduced from 8 hours to 3.5 hours to reach a particle fines fraction below 200 nm (laser diffraction, Malvern Mastersizer 3000).
Polyamide dyeing trials conducted in a Mathis Labomat BFA-24 at a liquor ratio of 1:20 using a standard exhaust process (pH 5.0 acetate buffer, ramp 1.5°C/min to 98°C, hold 45 min) show that dyes derived from this disulfonated intermediate exhibit migration index (MI) values 14–18% higher than those built from the standard 2-phenyl-6-methylthiazole-4-sulfonic acid scaffold. However, wet fastness to ISO 105-C06 (C2S) declines by ½–1 grade unless aftertreatment with a synthetic tanning agent (e.g., 5–10% owf Erional® EHL) is applied. This trade-off stems from the enhanced water solubility imparted by the second sulfonate group, which favors migration during levelling but increases the proportion of unfixed dye in the cold rinse.
Operators on continuous dye ranges report that pad-liquor tank filters (50 µm mesh) foul at a rate 60% lower when recipes employ DSA-TH-206M rather than mono-sulfonated alternates, attributable to the near-absence of insoluble particulates resulting from oleum sulfonation side-products. This operational difference reduces pump cavitation events on Kusters pad-steam units, directly lowering strip-off waste by an estimated 37 kg/1000 linear meters of a lightweight polyamide taffeta (reported from a production-scale trial at a Como facility, May 2022; internal technical bulletin, data on file).
A systematic comparison of three thiazole intermediates—DSA-TH-206M (disulfonated), 2-phenyl-6-methylbenzothiazole-4-sulfonic acid (mono-sulfonated), and the fully insoluble 2-(2-aminophenyl)-6-methylbenzothiazole (non-sulfonated)—was conducted under identical azo coupling protocols with diazotized 5-nitro-2-aminobenzonitrile. Key differentiators are tabulated below.
| Property | DSA-TH-206M (double sulfo acid) | Mono-sulfo analog | Non-sulfonated analog |
|---|---|---|---|
| Solubility in water (25°C, g/L) | > 250 | 45–55 | <0.5 |
| λmax of derived azo dye (DMF) | 518 ± 4 nm | 502 ± 4 nm | 553 nm (measured in acetone) |
| Optimum coupling pH window | 4.8–7.5 | 3.5–5.0 | No aqueous coupling feasible |
| Light fastness (ISO 105-B02) on PA 6 | 5–6 | 5 | 6–7 (solvent-cast film) |
| Aggregation tendency (DLS, 20 g/L, pH 7) | Negligible (monomeric) | Moderate (30–60 nm aggregates) | N/A |
| Recommended drying method for bulk | Fluidized bed ≤ 80°C or spray drying with 160°C inlet | Tray drying ≤ 60°C | Vacuum oven at 40°C |
Notably, the non-sulfonated analog is practically excluded from aqueous dye synthesis and finds limited use in solvent-based colorants for thermoplastics, where its 18°C higher decomposition onset (TGA, 10°C/min, N₂) favors polycarbonate masterbatch processing at 300–320°C. The mono-sulfonated intermediate remains cost-effective for medium-depth shades but requires cosolvent (e.g., diethylene glycol, 10–15% v/v) in the coupling liquor to suppress aggregation, adding solvent recovery cost and potentially complicating wastewater treatment under EU Directive 2010/75/EU.
Incompatibility with amine-based alkalinity donors during storage must be highlighted. Contact with triethanolamine or morpholine residues—common in some detergent-based cleaning agents for synthesis vessels—catalyzes partial desulfonation at temperatures as low as 50°C, forming a mono-sulfonated byproduct that co-crystallizes and reduces purity by up to 7 absolute percentage points in a 72-hour accelerated aging study (sealed ampoule, 80°C). This unintended transformation is detectable as an additional peak at retention time 1.8 min relative to the main peak on the release HPLC method. Production facilities are therefore advised to implement dedicated additive feed lines or rigorous CIP protocols with demineralized water rinses before introducing the intermediate.
Long-term stability data generated under ICH Q1A guidelines (zone II, 25°C/60% RH and zone IVb, 30°C/75% RH) demonstrate that the predominant degradation pathway is not hydrolysis of the amide linkage but slow sulfonic acid group redistribution. After 12 months at 30°C/75% RH, HPLC purity diminished by 2.1–3.4%, with the salient degradation product matching the HPLC retention time of a mono-sulfonated derivative, confirmed by LC-MS. Concurrently, the pH of a 1% solution shifted from 7.5 to 6.9, consistent with release of acidic species. When sealed in alufoil-laminated polyethylene liners within UN-rated fibreboard drums, the compound maintains purity above 90% for 24 months, provided storage temperature remains below 35°C. Warehouses without temperature control in regions where diurnal peaks exceed 40°C must consider refrigerated storage or just-in-time procurement cycles to prevent re-qualification costs.
Compliance assessments confirm that DSA-TH-206M and its typical synthesis byproducts have tested negative for substances of very high concern (SVHC) under REACH Article 57; the disodium salt carries no acute aquatic toxicity classification (EC₅₀ > 100 mg/L on Daphnia magna, OECD 202). Residual formaldehyde—a potential contaminant from the amidophenyl precursor if synthesized via the Gattermann route—is controlled to below 20 mg/kg by wet-end washing with sodium bisulfite solution in the final isolation step, aligning with OEKO-TEX Standard 100 requirements for Class I ancillary chemicals.
When DSA-TH-206M is used as a coupling component with commercial Fast Red B base (5-nitro-2-aminoanisole), calorimetric study in a Mettler-Toledo RC1e reaction calorimeter revealed that the coupling exotherm amounts to −145 ± 8 kJ/mol of coupler (based on NaOH-neutralized heat of reaction). The recommended addition sequence is inverted: addition of diazonium salt solution to a buffered coupler slurry, maintaining jacket temperature at 0–5°C and internal temperature below 10°C. Attempted direct diazotization of a pre-mixed amine-coupler solution resulted in a 17°C temperature spike and formation of an intractable tar when the pH momentarily dropped below 2.0 due to localized acid concentration. Batch-to-batch variation in the coupler’s free sodium sulfate content directly affects the ice-charge requirement for heat dissipation; at the upper specification limit of 3.5% Na₂SO₄, the specific heat capacity of the slurry decreases by approximately 6%, necessitating tighter coolant flow control.
Filtration and wash cycling on a Nutsche filter-dryer with a 20 µm polypropylene cloth isolates the resulting dye cake in yields typically 82–88% of theory, with the primary yield loss attributable to 2–3% entrained in wash filtrates. Counter-current washing with 5% brine at 10°C reduces this loss by 1.2% compared to single-stage washing, as validated across 12 production batches in a 4000 L glass-lined vessel. The difference in cake permeability between this disulfonated coupler (specific resistance α = 1.8 × 10¹¹ m/kg at 50 kPa pressure drop) and its mono-sulfonated counterpart (α = 4.2 × 10¹¹ m/kg) is mechanistically linked to the higher intrinsic viscosity of the fully dissociated double-sulfonate brine, which modifies the compressibility index of the filter cake.