Bis-(P-Chrolopheny)-1,4-Diketopyrrolo(3,4-C)Pyrrole
|
HS Code |
418303 |
| Chemical Formula | C18H8Cl2N2O2 |
| Molar Mass | 355.17 g/mol |
| Appearance | Red - violet solid |
| Melting Point | Above 300 °C (decomposes) |
| Solubility In Water | Insoluble |
| Solubility In Organic Solvents | Soluble in some polar organic solvents like N,N - dimethylformamide |
| Crystal Structure | Typically forms crystalline solids |
| Optical Property | Highly colored, used as a pigment with strong light - fastness |
| Thermal Stability | Good thermal stability up to decomposition temperature |
| Electrical Property | Generally considered an insulator |
As an accredited Bis-(P-Chrolopheny)-1,4-Diketopyrrolo(3,4-C)Pyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 500g of Bis-(P - Chrolopheny) - 1,4 - Diketopyrrolo(3,4 - C)Pyrrole in airtight plastic bags. |
| Shipping | Bis-(P -Chlorophenyl)-1,4 -Diketopyrrolo(3,4 -C)Pyrrole is shipped in secure, sealed containers. Compliance with chemical shipping regulations is ensured to prevent leakage and maintain product integrity during transit. |
| Storage | Bis-(P - Chlorophenyl)-1,4 - Diketopyrrolo(3,4 - C)Pyrrole 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 to avoid chemical reactions. |
When Temperature Swings Exceed ±3°C Around the Glass Transition of a Clearcoat MatrixIn monocoat and basecoat/clearcoat systems for automotive exterior finishes, bis-(p-chlorophenyl)-1,4-diketopyrrolo(3,4-c)pyrrole (C.I. Pigment Red 254) is typically dispersed in a saturated polyester or acrylic polyol resin at a pigment-to-binder ratio of 0.15:1 to 0.35:1. The millbase, prepared on a horizontal bead mill with 0.6–0.8 mm yttria-stabilized zirconia beads at a fill ratio of 75–80%, is processed to a fineness of grind below 5 µm as measured per ISO 1524:2020. The fully let-down paint is applied by high-speed rotary bell atomizers at a dry-film thickness of 12–18 µm for basecoat and 35–45 µm for clearcoat, then baked at 140°C for 30 minutes. Panels subjected to accelerated weathering under SAE J2527 (Xenon arc, borosilicate inner and outer filters, 0.55 W/m² at 340 nm, continuous light cycle with intermittent water spray) exhibit DE* < 1.0 after 5000 hours when the formulation incorporates a hindered amine light stabilizer package comprising 1.0 wt% bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate and 0.5 wt% 2-(2-hydroxy-3,5-di-tert-amylphenyl)benzotriazole. Micro-cracking at the clearcoat/pigmented layer interface is observed during field service in Scandinavia and the Middle East when the crosslink density of the clearcoat, expressed as a glass transition temperature measured by dynamic mechanical analysis (DMA, ASTM E1640-18), drops below 85°C; the phenomenon is traced to cyclic moisture ingress and thermal expansion coefficient mismatch between the DPP particle surface and the surrounding melamine-crosslinked matrix. Production trials on a 3800-ton injection molding clamp line for body-colored bumper fascias revealed that pre-drying the compounded thermoplastic olefin masterbatch containing 4.5 wt% PR254 at 90°C for 4 hours in a desiccant dryer with a dew point of ≤ -40°C eliminated splay defects entirely.Volatile organic compound legislation, specifically the China GB 24409-2020 limits for passenger vehicle coatings and the EU Directive 2004/42/EC Phase II, has pushed a shift toward waterborne basecoats. In an aqueous polyurethane dispersion (PUD) with a minimum film formation temperature of 12°C, the pigment is compatibilized via a styrene-maleic acid copolymer dispersant with an acid value of 190–210 mg KOH/g, dosed at 12% on pigment weight. The let-down shear stability, assessed by a cone-and-plate rheometer sweep from 0.1 s⁻¹ to 1000 s⁻¹, must show no inflection point associated with flocculation; a rise in viscosity exceeding 15% at low shear after 7 days of storage at 50°C indicates inadequate steric stabilization and is cause for batch rejection.What Happens When a Diketopyrrolopyrrole Red Endures Polypropylene Fiber Spinning Above 285°C?Mass-coloration of polypropylene multifilament yarns for outdoor upholstery and geotextile color coding exploits the exceptional thermal stability of P.R. 254. In a single-screw extruder with a 30:1 L/D ratio and a Maddock mixing section, a masterbatch containing 30 wt% pigment in a metallocene-catalyzed polypropylene random copolymer (MFR 25 g/10 min at 230°C/2.16 kg, ISO 1133-1:2022) is let down to 0.4 wt% final pigment concentration. Barrel zone temperatures are profiled from 210°C (feed) to 285°C (metering) to 280°C (spin pack). The melt is filtered through a 25 µm absolute-rated sintered metal fiber filter disc before passing through a spinneret with 0.3 mm orifices to create 120-denier/48-filament partially oriented yarn (POY). A residence time exceeding 7 minutes in the melt phase at 295°C triggers a hue shift toward a bluish maroon—observable as a Δa* drift of +0.8 units in CIELAB color space—attributed to partial sublimation of trace 4-chlorobenzonitrile reformation byproducts rather than chromophore decomposition. To arrest this drift, a purge protocol involving a linear low-density polyethylene (LLDPE) with a melt index of 0.5 g/10 min is run for 20 minutes at 260°C between color changes.For compliance with Oeko-Tex Standard 100, Annex 4, Class I (articles for babies), the extracted 4-chloroaniline concentration must fall below the 20 mg/kg detection limit when assayed via EN 14362-1:2017 (reductive cleavage with sodium dithionite, GC-MS analysis). This imposes a specification on the incoming pigment that primary aromatic amine residuals remain below 50 ppm. The fabric after 1000 hours of weathering per ISO 105-B04:2023 (Xenon arc, 42 W/m², 300–400 nm) shall exhibit a grey scale rating of at least 4–5 and a lightfastness of 7–8 on the blue wool scale, values routinely achievable without additional UV absorbers when the fiber denier exceeds 150.Powder Coating Extrusion and the Critical ±5% Pigment Loading WindowIn triglycidyl isocyanurate (TGIC)-cured polyester powder coatings for architectural aluminum profiles (Qualicoat Class 2), the diketopyrrolopyrrole pigment is pre-mixed with a carboxylated polyester resin (acid value 32–36 mg KOH/g) at loadings between 1.2% and 3.8% by weight of total formulation. The premix is fed into a co-rotating twin-screw extruder with 25 mm screw diameter and 40:1 L/D, operating at a screw speed of 400 rpm and a barrel temperature of 120°C (+5°C in the second heating zone), to ensure a melt temperature measured at the die of 112–116°C. When pigment loading surpasses 4.2%, the melt viscosity increases disproportionately, causing a 15–20 A spike in extruder motor load and the appearance of microgels detectable on a polished, isopropanol-washed panel after curing at 200°C for 10 minutes as pinpoint craters surrounded by a raised rim. The finished powder, sieved through a 140 µm rotary sifter, is applied electrostatically with a corona gun at 60–80 kV to a 60–90 µm dry-film thickness. Florida exposure (5° south, direct weather, ISO 2810) for 3 years produces ΔE < 3.0 only if the TGIC-to-resin ratio is kept at 93:7 and the degassing agent (benzoin) is dosed at 0.3–0.5% to prevent pinhole corrosion initiation points.The pigment’s limited dispersibility in high-viscosity, low-shear powder melt poses a specific bottleneck. A separate investigation on a 16 mm parallel twin-screw lab extruder equipped with a slit die rheometer revealed that substituting 20% of the DPP red with a quinacridone magenta (C.I. Pigment Violet 19) lowered the zero-shear viscosity at 130°C by 22% while maintaining the same spectral reflectance at 560 nm, thus allowing continuous operation without torque-limiter trips. Certification under Qualicoat 3.0 requires the cured film to withstand 3000 hours of acetic acid salt spray testing (ISO 9227) with less than 1 mm creepage at the scribe, a criterion that demands a fully encapsulated pigment surface completely wetted by the polyester backbone.Beyond the purely decorative, a specific requirement arises in electrical insulation powder coatings for busbar epoxy-polyester hybrid systems. Here, the dielectric strength measured according to IEC 60243-1 at 500 V/s ramp must remain above 35 kV/mm after immersion in 90°C deionized water for 1000 hours. Ionic residues on the pigment surface, primarily sodium and chloride ions measured by conductometric extraction per DIN 53780-1, shall not exceed 150 µS/cm to avoid catastrophic dielectric failure. This necessitates a final pigment washing step with deionized water of conductivity less than 2 µS/cm until the filtrate conductivity matches the inlet water.Does Migration into Fatty Food Simulants Limit This DPP Chromophore in Rigid PVC Food-Contact Articles?Incorporating P.R. 254 into unplasticized suspension PVC for blow-molded bottles and calendered sheet intended for repeated contact with aqueous, acidic, and fatty foods demands rigorous compliance with (EU) No 10/2011 on plastic materials and articles intended to come into contact with food. The specific migration limit (SML) for the pigment is not listed individually in Annex I; however, the overall migration limit of 10 mg/dm² of food contact surface area (article 12) applies. Testing according to BS EN 1186-1:2002 with simulant D1 (ethanol 50% v/v) for 10 days at 40°C must yield an overall migration below the limit. The pigment is dosed at 0.05–0.2 wt% in the PVC compound, which is stabilized with a calcium–zinc system at 2.5 phr to avoid heavy metal contamination, and processed on a counter-rotating conical twin-screw extruder with a melt temperature at the adapter of 178–182°C. Color shift toward an orange-red during processing indicates partial dehydrochlorination catalyzed by residual acidic surface groups on the pigment; this is suppressed by adding 0.3 phr of epoxidized soybean oil (ESBO) as an acid scavenger, which itself is subject to an SML of 30 mg/kg for foods for infants and young children.The purity specification for the pigment in food-contact applications includes a primary aromatic amine sum below 10 mg/kg (detection by spectrophotometric method after diazotization and coupling per EUR 24815 EN, 2011), a polychlorinated biphenyl (PCB) content below 25 mg/kg, and a 4-chloroaniline content below 5 mg/kg. A recent enforcement case in a European member state identified a consignment where accelerated testing in 95% ethanol at 60°C for 4 hours yielded extracted matter exceeding the limit by 3.2 mg/dm², traced to low-molecular-weight oligomeric dispersant that had not been fully removed during the pigment finishing step. The corrective action implemented by the toll manufacturer involved a hot isopropanol slurry wash at 70°C for 2 hours followed by filtration through a 0.5 µm membrane before tray drying at 80°C under vacuum. The resulting product exhibited a volatile matter of 0.18% at 105°C (ISO 787-2:1981) and a residue on a 45 µm sieve of less than 0.01%.When UV Flexo Ink Rheology Must Remain Newtonian Through a 1200 m/min Press RunNarrow-web UV flexographic printing of self-adhesive labels on polypropylene facestock at speeds exceeding 1000 m/min requires a cyanide-free, low-migration red meeting the Nestlé Guidance Note on Packaging Inks (February 2022 revision) and Swiss SR 817.023.21, Annex 6, part A. A triacrylate monomer-based UV ink vehicle (oligomer: trimethylolpropane triacrylate, viscosity 180 mPa·s at 25°C) is loaded with 18–22 wt% of the predispersed DPP pigment paste, which itself is prepared by passing a 35 wt% pigment in ethoxylated trimethylolpropane triacrylate through a triple-roll mill with a front roll temperature maintained at 28–30°C and an apron nip gap of 10 µm. The final ink’s viscosity, measured with a Laray falling-rod viscometer at 2500 s⁻¹, is adjusted to 0.45–0.65 Pa·s by adding the reactive diluent hexanediol diacrylate. On-press, the ink is transferred through an anilox roller with a cell volume of 3.5–4.5 cm³/m² (hexagonal cell geometry, 60 lines/cm) and cured by a gallium-doped mercury vapor lamp array delivering a peak irradiance of 1.8 W/cm² in the UVA band. Radiant energy required for through-cure, determined by a radiometer conforming to ISO 12647-6:2020, must accumulate to at least 120 mJ/cm²; incomplete curing leaves unreacted monomer residues that subsequently migrate through the pressure-sensitive adhesive layer into the packaged chocolate, detected by GC-MS headspace analysis using a Tenax TA trap at 30°C for 30 minutes.A pigment-specific failure mode manifests as build-up of dry, unrewetted pigment agglomerates on the doctor blade chamber, causing streaks visible as 0.2–0.8 mm wide unprinted lines on the substrate. This is mitigated by incorporating 1.5–2.0% of a high-molecular-weight hyperdispersant with an amine anchoring group (amine value 20–25 mg KOH/g) and maintaining the chamber seal solvent (ethoxy propanol) flowrate at 150 mL/hour. In-line spectrophotometric closed-loop color control (X-Rite ColorCert) with a D50/2° observer monitors L*a*b* values; a ΔE2000 exceeding 1.5 triggers an audible alarm and an automatic viscosity adjustment through solvent metering.
As a Non-Fullerene Acceptor in All-Polymer Indoor PhotovoltaicsWhile overwhelmingly deployed as a pigment, the same bis-(4-chlorophenyl)diketopyrrolopyrrole molecule possesses a planar conjugated core with an optical bandgap of approximately 2.1 eV (onset of absorption at 590 nm in thin film) and a lowest unoccupied molecular orbital (LUMO) energy of −3.5 eV vs. vacuum as measured by cyclic voltammetry with ferrocene/ferrocenium internal standard, making it a candidate electron acceptor in bulk heterojunction solar cells. A blend of poly(3-hexylthiophene) (P3HT) as donor and the DPP molecule as acceptor, deposited from a 20 mg/mL chloroform solution by blade coating at a coating gap of 150 µm and a speed of 15 mm/s, yields a photoactive layer of 90–110 nm thickness. Under 1000 lux illumination from a 2700 K compact fluorescent lamp, devices with a structure ITO/PEDOT:PSS/active layer/Ca/Al exhibited a power conversion efficiency of 2.8% when thermally annealed at 120°C for 10 minutes, a process that increases the short-circuit current density from 15 µA/cm² to 28 µA/cm² by improving the phase-separated domain size to 20–30 nm as imaged by transmission electron microscopy. Published data for this specific configuration is limited, and the primary limitation remains the limited solubility of the unsubstituted DPP core in non-halogenated solvents; ortho-dichlorobenzene (ODCB) with 5% v/v 1-chloronaphthalene as a high-boiling additive improves film uniformity but introduces a hazardous waste stream incompatible with roll-to-roll manufacturing. The electrodes are thermally evaporated at a base pressure below 2 × 10⁻⁶ mbar to achieve a calcium thickness of 25 nm and aluminum 100 nm.In sensing and photodetection, the pigment’s absorption tail extending beyond 620 nm offers a narrowband response when combined with a dielectric mirror back reflector. A solution-processed organic photodetector with a device architecture glass/ITO/ZnO/PR254:P3HT/MoO₃/Ag (10 nm MoO₃ as hole transport layer) showed a dark current density of 2.1 nA/cm² at −0.1 V and a specific detectivity of 5 × 10¹¹ Jones at 580 nm, measured by a lock-in amplifier referenced to a calibrated silicon photodiode. The linear dynamic range exceeded 100 dB only when the device was encapsulated with an epoxy resin and a glass lid in a nitrogen glove box (<1 ppm O₂, <1 ppm H₂O), as ambient oxygen at > 100 ppm induced a rapid increase in the reverse bias current due to p-doping of the P3HT phase.A different functional application exploits the pigment’s irreversible thermal isomerization above 320°C. When dispersed at 2 wt% in a polycarbonate matrix and injection-molded at 310°C into 2 mm thick plaques, the color remains unchanged. The same plaque subjected to 340°C for 3 minutes develops a permanent shift toward an opaque brown (ΔE> 20) due to formation of quinoid degradation structure, which has led to its experimental use as an oxidative environment indicator in melt-processed engineering thermoplastics, although no commercial sensor product exists to date.
Aqueous Textile Pigment Printing Pastes and the Limiting Factor of Crockfastness after Industrial LaunderingA standard all-aqueous printing paste for 100% cotton knitted fabric intended for athletic wear comprises 4 wt% DPP pigment dispersion (nonionic surfactant, 30% solids, D₅₀ = 0.3 µm), 12 wt% of a soft polyacrylate binder with a glass transition temperature of −15°C, 1 wt% melamine-formaldehyde crosslinker, 0.5 wt% ammonium nitrate as acid-liberating catalyst, and the balance a rheology modifier blend (high-molecular-weight associative thickener and fumed silica) to achieve a viscosity of 35–45 Pa · s at a shear rate of 0.1 s⁻¹ (Brookfield RV, spindle #6). The paste is screen-printed through a 100 mesh/cm polyester monofilament screen with a squeegee durometer of 65 Shore A at a velocity of 0.5 m/s and a snap-off distance of 2.5 mm. Drying is performed in a hot-air stenter at 110°C for 3 minutes, followed by curing at 150°C for 4 minutes to achieve a crosslink density sufficient to withstand 50 home-laundering cycles per ISO 6330:2021 (Procedure 4A, 60°C cotton cycle, tumble dry). Wet crockfastness measured by AATCC TM8-2022 must deliver a rating of at least 4 (grey scale) on both warp and weft directions; typical results for this formulation are 4–5 in the as-printed state, degrading to 3 after 30 cycles when the binder film begins to micro-fracture, releasing pigment particles into the wash liquor as detected by a turbidity sensor (nephelometric turbidity units increase from 0.8 to 12 NTU).To meet the bluesign® System Substance List (BSSL) and ZDHC Manufacturing Restricted Substances List (MRSL) version 3.1, the pigment must contain less than 50 ppm each of ortho-phthalates, organotin compounds, and chlorinated benzenes, verified by a third-party test report using GC-MS selected ion monitoring. The pigment’s insolubility in water (<0.1 mg/L at 20°C, OECD TG 105 flask method) ensures that it is not absorbed through the skin, a critical parameter for apparel worn directly against the skin for prolonged periods as per OEKO-TEX Standard 100, Annex 6. The residual surfactant from the pigment dispersion can interfere with the binder film coalescence, softening it and reducing the glass transition temperature by 3–5°C, which is corrected by increasing the crosslinker addition by 0.2 wt% for every 0.1 wt% of surfactant detected by HPLC-ELSD in the finished paste. |
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| Property | Typical Range | Test Method |
| Volatile matter (2 h, 105 °C) | ≤ 0.5 % | ISO 787-2:1981 |
| Oil absorption | 38–48 g·100 g⁻¹ | ISO 787-5:1980 |
| Specific surface area (BET) | 52–68 m²·g⁻¹ | ISO 9277:2010 |
| pH of aqueous extract | 6.0–7.5 | ISO 787-9:1981 |
| Residue on sieve (45 µm) | ≤ 0.1 % | ISO 787-7:2009 |
| Heat stability in HDPE (5 min) | 300 °C (ΔE ≤ 1.0) | EN 12877-2:2000 |
| Lightfastness full shade (blue wool) | 8 | ISO 105-B02:2014 |
| Lightfastness 1:10 TiO₂ tint | 7–8 | ISO 105-B02:2014 |
| Regulation | Compliance Status / Citation |
| EU REACH | Registered; SVHC-free per Article 57 |
| FDA 21 CFR | Suitable under 178.3297 (colorants for polymers) with migration limits per FCN inventory |
| AP(89)1 | Permitted for food-contact plastics |
| RoHS III (EU 2015/863) | Below MCV thresholds for Pb, Hg, Cd, Cr(VI), PBBs, PBDEs, DEHP, BBP, DBP, DIBP |
| CONEG | Sum of Pb, Hg, Cd, Cr(VI) ≤ 100 ppm |
| EN 71-3:2019+A1:2021 | Migration limits satisfied for Category I–III toy materials |
