1,4-Diketo-3,6-Bis(4-Biphenylyl)Pyrrolo[3,4-C]Pyrrole
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HS Code |
976633 |
| Chemical Formula | C36H22N2O2 |
| Molecular Weight | 514.57 g/mol |
| Appearance | Solid |
| Melting Point | Data needed |
| Boiling Point | Data needed |
| Solubility In Water | Insoluble |
| Solubility In Organic Solvents | Soluble in some organic solvents like dichloromethane |
| Density | Data needed |
| Vapor Pressure | Data needed |
| Uv Vis Absorption | Absorbs in visible and near - UV regions |
| Fluorescence Properties | May exhibit fluorescence depending on environment |
As an accredited 1,4-Diketo-3,6-Bis(4-Biphenylyl)Pyrrolo[3,4-C]Pyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 1,4 - Diketo - 3,6 - Bis(4 - Biphenylyl)Pyrrolo[3,4 - c]Pyrrole in sealed chemical - grade container. |
| Shipping | 1,4 - Diketo - 3,6 - Bis(4 - Biphenylyl)Pyrrolo[3,4 - c]Pyrrole will be shipped in specialized, leak - proof containers. Adequate cushioning ensures protection during transit. Shipment follows strict chemical transportation regulations. |
| Storage | 1,4 - Diketo - 3,6 - Bis(4 - Biphenylyl)Pyrrolo[3,4 - c]Pyrrole should be stored in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent exposure to air and moisture, which could potentially degrade the chemical. Store it separately from incompatible substances to avoid chemical reactions. |
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In polypropylene spunbond nonwoven manufacturing, continuous filtration processes expose even nominally heat-stable organic pigments to prolonged residence at 220–250 °C. C.I. Pigment Red 264 reduces screen-pack pressure build-up when masterbatch prepared on a co-rotating twin-screw extruder (L/D 44:1, screw diameter 32 mm) employs a pre-dispersed pigment presscake dewatered to <0.3 wt% residual moisture. A loading range of 0.12–0.35 wt% in the final nonwoven yields red shade depths matching standard references for hygiene top-sheet and agricultural cover stock. Compliance for skin-contact applications is verified through OEKO-TEX® Standard 100 Annex 4, while migration into simulants under EU Regulation 10/2011 articles 17–18 must remain below the specific migration limit of 10 mg kg−1 for non-evaluated substances. High-speed spunbond lines (throughput 200–350 kg h−1) benefit from the pigment’s half-life exceeding 20 min at 290 °C (isothermal TGA, ISO 11358-1:2014), minimising discolouration when beam temperatures drift during line stoppages. Why does pigment pre-dispersion govern filter service life in PA6 fiber spin-dyeing?Batch-to-batch variation in primary particle size and aggregate structure directly modulates spin-pack pressure rise in polyamide 6 dope-dye lines operating at 260–275 °C. Granular masterbatch produced on a co-kneader (40 mm screw, 18 L/D) containing 5–7 wt% pigment in a low-viscosity PA6 carrier (RV 2.4) is let down to 0.18–0.45 wt% final pigment content. Melt filtration through sintered metal media of 20 µm absolute rating monitors pressure coefficients below 0.8 bar h−1 when agglomerates are milled to a mean particle size d50 ≤ 0.6 µm (ISO 13320-1:2020 laser diffraction). Regulatory compliance for textile applications references OEKO-TEX® Standard 100 class I for baby-wear and REACH Annex XVII entry 43 for azo-amine restrictions. Finished articles span tricot warp-knit automotive headlining and solution-dyed carpet yarns, where lightfastness is confirmed to blue wool scale 7–8 after 300 h xenon arc exposure per ISO 105-B02:2014. Deviations in screw recovery time beyond 12 s during injection-moulded chip production can elevate compound melt temperature by 4–7 °C, a shift that remains within the pigment’s thermostability window provided hold-up time at the spinning beam does not exceed 8 min. Premixing C.I. Pigment Red 264 into a polyester-hydroxyalkylamide (HAA) powder coating system demands dry-blend homogeneity after extrusion through a ZSK 40 twin-screw compounder (barrel zones 80–110 °C) followed by cryogenic milling to d50 30–38 µm. A dosage of 6–12 wt% in a 50:50 polyester-epoxy hybrid formulation achieves full hiding at 60–80 µm film thickness, while retaining gloss >85 at 60° (ISO 2813:2014). Architectural powder coatings destined for aluminium curtain-wall extrusions are qualified against Qualicoat Class 2 (2019 Edition) and AAMA 2604-20 specifications, requiring 5-year Florida weathering with ΔE*ab not exceeding 5.0 units. The pigment’s low specific conductivity (<50 µS cm−1, DIN 53214) minimises back-ionisation during corona-charged electrostatic spraying on vertical profiles. Pre-bake oven ramp-rate below 8 K min−1 between 120 and 160 °C is necessary to avoid micro-bubbling in coat weights above 120 µm. Rheological thresholds in solventborne automotive OEM basecoat applicationsDisplacement of diketo-pyrrolo-pyrrole bis-biphenyl into a CAB-acrylic continuous phase via horizontal bead mill (net power absorbed 0.6–0.9 kW per kg dispersion) raises the yield stress of the basecoat to a range compatible with high-speed laser scanning of flop indices. A pigment-to-binder ratio of 0.30:1–0.55:1 at 4–8 wt% pigment on total non-volatile matter stabilises the metallic aluminium flake orientation necessary for travel values below 1.2 units (DIN 6175-2). The colour-constant hue shift between glazing and flash-off—quantified as ΔH*ab < 0.8 after 30 min ambient flash—is retained only when the let-down stage avoids shear rates exceeding 500 s−1. Compliance with interior cabin emissions is demonstrated via headspace sampling according to VDA 278:2021, with fogging condensate mass below 2.0 mg (DIN 75201:2020 method B). Production topcoats meet Global Automotive Materials Specification GMW14872 for delamination resistance after 10-day immersion at 40 °C in deionised water. Cross-hatch adhesion on electrocoat primers (ISO 2409:2020) must remain Gt 0 irrespective of oven over-bake of +15 °C above the nominal 140 °C cure schedule. When processing polycarbonate at melt temperatures above 310 °CResidual moisture in polycarbonate pellets—a critical variable when injection-moulding LED lens holders and automotive interior switch bezels—must be held below 0.015 wt% by pre-drying at 120 °C for 4–6 h in a desiccant dryer with dew point ≤ −40 °C (ASTM D7191-18). Under these conditions, a masterbatch at 1:25 dilution can deliver a finished resin dye loading of 0.08–0.25 wt% without hydrolytic chain scission, as demonstrated by a retained melt volume-flow rate within ±6% of virgin resin (ISO 1133-1:2022, 300 °C/1.2 kg). The pigment exhibits chromatic stability in polycarbonate for hold-up times up to 10 min at 330 °C when the screw back-pressure is set between 80 and 120 bar; prolonged residence beyond 14 min at 340 °C triggers a perceptible yellowness index shift exceeding +2.0 YI (ASTM E313-20). Regulatory benchmarks include RoHS Directive 2011/65/EU Annex II for Pb, Cd, Hg and Cr(VI) content at levels below 100 mg kg−1 and compliance with the halogen-free threshold of 900 ppm Cl and 900 ppm Br (IEC 61249-2-21:2003). Finished thin-wall parts thinner than 1.2 mm achieve UL 94 V-0 rating only when compound total organic pigment loading does not exceed 0.15 wt%, as flame-retardant dilution effects become measurable in cone calorimeter testing (ISO 5660-1:2015). Migration-resistant flexible PVC compounds for medical tubingPlasticized PVC dry blends processed via counter-rotating twin-screw extrusion (screw diameter 56 mm, L/D 30:1) incorporate C.I. Pigment Red 264 at 0.20–0.60 wt% in formulations using DOTP instead of DEHP, maintaining durometer 80–85 Shore A. No measurable bloom is detected after 72 h at 50 °C and 95% RH in a Kesternich condensation test (DIN 50018:2022), confirming the pigment’s compatibility with calcium-zinc stabiliser packages. Biocompatibility batches are screened for cytotoxicity via extract dilution per ISO 10993-5:2009 and acute systemic toxicity per USP <88> Biological Reactivity Tests, Class VI (121 °C extraction). The finished article portfolio includes blood-storage bag pigtail connectors, CPAP mask cushions and enteral feeding tubes that require gamma-sterilisation tolerance to 50 kGy (ISO 11137-1:2006), after which colour shift measured against unirradiated controls remains below ΔE*ab 1.8. No extractable free primary aromatic amine above the 0.1 mg kg−1 analytical detection limit is recorded, satisfying the infant nutritional appliance restriction in EU 1935/2004 Article 3.
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1,4-Diketo-3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole, registered as Colour Index Pigment Red 264 (CAS 84632-65-5), constitutes a high-molecular-weight iteration of the diketopyrrolopyrrole (DPP) chromophore family. The compound assembles from a central pyrrolo[3,4-c]pyrrole ring system flanked by two para-biphenyl substituents, yielding a molecular formula C₃₂H₂₀N₂O₂ and a relative molecular mass of 464.52 g/mol. In comparison to the more broadly adopted PR254 (4-chlorophenyl derivative) and PR255 (phenyl-terminated homologue), the extended aromatic periphery of PR264 introduces measurable deviations in crystal packing, hypsochromic spectral displacement, and thermal nucleation behaviour when dispersed in semicrystalline polymer matrices. X-ray powder diffractometry (Cu Kα, 1.5418 Å) resolves a unit cell volume approximately 8–12% larger than that of PR255, a consequence of the biphenyl longitudinal axis enforcing a less dense intermolecular arrangement along the crystallographic c-direction. This crystal metric manifests directly in the reflectance profile, where the mass-tone λmax shifts to 518 ± 2 nm from the 538 nm typical of PR254, altering the CIELAB hue angle (hab, D65/10°) into the 25°–28° range—a core requirement for high-chroma rubine and bordeaux automotive finishes.
The bathochromic contraction in PR264 relative to the 4-chlorophenyl reference is not primarily a solution-state solvatochromic event but a solid-state excitonic coupling phenomenon. Single-crystal microspectrophotometry demonstrates that the intermolecular hydrogen-bonding network—between lactam N–H and carbonyl oxygen across adjacent molecules—retains a periodicity of 2.90–2.95 Å, nearly identical across the DPP series. The divergence arises from the torsion angle adopted by the biphenyl terminal ring; solid-state 13C CP/MAS NMR indicates a dihedral angle of 28°–32° between the two phenyl planes in the biphenyl substituent, which disrupts end-to-end exciton delocalisation pathways. Consequently, the spectral full width at half maximum (FWHM) narrows by 8–12 nm compared to PR254, enhancing the pigment's saturation in tint applications. When reduced with TiO₂ (rutile grade, 20:1 ratio) in an alkyd-melamine stoving enamel and measured under D65 illumination, the resulting chroma C* value reaches 72–74, versus 65–68 for an equivalent PR254 reduction, as per ASTM D5326-94a procedures. This optical fingerprint makes PR264 uniquely suited for shading deep-shade metallic clears where a scarlet influence must be suppressed.
Industrial pigment finishing of PR264 typically proceeds through a salt-grinding or acid-pasting route, followed by solvent-mediated Ostwald ripening to regulate crystallite aspect ratio. The product's commercial viability in thin-film coating systems (10–15 µm dry film thickness) demands a median particle diameter (d₅₀) in the range 0.08–0.12 µm as determined by laser diffraction (ISO 13320, Mie theory). Specific surface area, measured by nitrogen adsorption (BET, ISO 9277), is maintained between 30 and 50 m²/g, with an oil absorption (ISO 787-5) of 45–55 g/100g. Processing on a horizontal bead mill (e.g., Netzsch LME 4, filled to 80% with 0.3–0.4 mm yttria-stabilised zirconia beads) brings the PSD to the sub-100 nm corridor after 6–8 passes. However, a conflict emerges when specific energy input exceeds 10 kWh/kg dispersion. Transmission electron microscopy reveals that such conditions generate lattice defects—edge dislocations and incipient amorphisation—which act as photoactive trap states. In accelerated weathering per SAE J2527 (Xenon arc, 0.55 W/m² at 340 nm), panels containing overmilled pigment exhibit a ΔE*ab shift of >1.5 after 1500 kJ/m², whereas the properly conditioned material stays below 0.8 ΔE*. Dispersion rheology at application viscosity (25–30 seconds DIN 4 cup) confirms that a Casson yield stress of 8–12 Pa (ISO 3219, cone-plate 1°, 25 °C) is necessary to maintain metallic flake orientation in waterborne basecoats. If the yield stress crosses 20 Pa, mottling and seeding defects become visible at 5 m observation distance under overcast daylight.
In coil coating operations subjected to peak metal temperatures of 240–260 °C for 40–60 seconds, thermal degradation of the chromophore must remain below a critical threshold. Mass-tone drawdowns on chromated aluminium, baked in a conveyor oven calibrated to ASTM D2454, yield a ΔE*ab (ASTM D2244, 10° observer, D65) of less than 0.5 when the dwell time does not exceed 50 seconds at 260 °C. For engineering plastics, gravimetric masterbatches processed on a co-rotating twin-screw extruder (L/D 44:1, Berstorff ZE 40) introduce the pigment via a side feeder at barrel zone 6 (melt temperature 220–230 °C) to restrict residence time. Injection-moulded HDPE plaques (Lupolen 5261Z, 1.0% pigment) tested per ISO 787-21 for 5 minutes at 300 °C deliver ΔE* < 1.0, with no visible plate-out on the mould surface after 2,000 cycles. In flexible PVC calendered at 170 °C, migration fastness evaluated per DIN EN 20105-A03 (contact with white PVC-P, 24 h at 80 °C under 1 kg/cm²) scores the highest rating of 5, confirming the absence of diffusive colour transfer.
| Parameter | Test Method | PR255 (C.I. 561050) | PR254 (C.I. 56110) | PR264 (This Product) |
|---|---|---|---|---|
| Relative molecular mass (g/mol) | – | 288.30 | 357.30 | 464.52 |
| Specific surface area (BET, m²/g) | ISO 9277 | 60–80 | 30–60 | 25–50 |
| Oil absorption (g/100g) | ISO 787-5 | 40–50 | 40–55 | 45–55 |
| Mass-tone λmax (nm, pressed powder) | Reflectance, D65/10° | 540 ± 2 | 538 ± 2 | 518 ± 2 |
| Lightfastness (full shade, Blue Wool Scale) | ISO 105-B02 | 7–8 | 7–8 | 7–8 |
| Weatherfastness (2-year Florida, mass tone, ΔE*) | ISO 2810 | 3–4 | 4–5 | 4–5 |
| Heat stability limit in HDPE (°C, 5 min) | ISO 787-21 | 280 | 300 | 300 |
| Migration fastness (PVC-P, contact bleed) | DIN EN 20105-A03 | 5 | 5 | 5 |
| Typical d₅₀ for automotive basecoat (µm) | ISO 13320 | 0.05–0.08 | 0.06–0.10 | 0.08–0.13 |
Aqueous presscake of PR264, harvested at 30–35 wt% solids from a membrane filter press, is frequently flushed directly into a long-oil alkyd or acrylic polyol to produce a chip-free single-pigment concentrate. In a Z-arm mixer (List CRP 250), water displacement initiates at 80–90 °C under a vacuum gradient that must reach at least −0.8 bar within the first 20 minutes. Trials in which vacuum is omitted or delayed result in persistent microfoam—bubble diameters 10–50 µm as visualised by a Hegman grind gauge (ISO 1524). The rheological consequence manifests in a three-interval thixotropy test (3ITT, ISO 3219-2): after a pre-shear at 100 s⁻¹ for 60 seconds followed by rest at 0.1 s⁻¹, the structure recovery ratio rises from the expected 75–80% to approximately 95% within 300 seconds, indicating irreversible bridging among pigment aggregates via entrapped air–water interfaces. This rheological hardening escalates basecoat sag resistance beyond 120 µm wet film thickness (as measured with a Byk-Gardner anti-sag meter) but degrades leveling, yielding a long-wave orange peel rating (LW, BYK Wavescan) above 20 after clearcoat application. Concentrate batches with residual moisture exceeding 2.5% (Karl Fischer titration, ASTM D4017) also exhibit a >50% increase in steady-shear viscosity (measured at 1000 s⁻¹) after 24-hour storage at 23 °C, an effect reversible only through high-shear redispersion on a triple-roll mill.
The biphenyl-terminated homologue differs from PR254 in nucleating efficiency when embedded in low-density polyethylene. During isothermal crystallisation at 100 °C, monitored by differential scanning calorimetry (ISO 11357-7, heat-flow rate 10 K/min cooling), PR264 shortens the crystallisation half-time (t½) of LDPE by only 15–20% relative to the unfilled resin, whereas PR254 accelerates nucleation by 30–40%. The attenuated nucleation is attributed to the larger cross-sectional area of the biphenyl group hindering epitaxial alignment of polyethylene chains on the pigment crystal faces. In injection-moulded polypropylene plaques, this translates to a 5–7% lower differential shrinkage (measured per ISO 294-4) in comparison to the 4-chlorophenyl variant, reducing the risk of edge-warp in large-area automotive interior trims where dimensional tolerance is held to ±0.3 mm.
Purified via train sublimation under a 10⁻³ Pa vacuum and high-purity nitrogen carrier gas, 1,4-diketo-3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole attains a purity exceeding 99.95% (HPLC area-percent at 254 nm). This electronic-grade variant has been evaluated in bottom-gate top-contact organic field-effect transistors fabricated on octadecyltrichlorosilane-treated silicon dioxide (gate dielectric thickness 300 nm). Under nitrogen atmosphere, annealed devices (150 °C for 30 minutes) exhibit an electron mobility of 1×10⁻³ cm²/Vs and a hole mobility of 8×10⁻⁴ cm²/Vs, with an on/off current ratio of 5×10³. Photoelectron yield spectroscopy determines the ionisation potential at 5.4 eV, and optical absorption onset places the solid-state band gap near 1.9 eV. In contrast, the 4-chlorophenyl analogue (PR254) shows negligible electron current under the same device architecture, a divergence attributed to the deeper lowest unoccupied molecular orbital stabilised by the extended conjugation of the biphenyl moiety. Published charge-transport data for this exact DPP derivative remain limited, and the charge-carrier mobility can vary by an order of magnitude depending on the dielectric surface treatment and film morphology.
