1,4-Diketo-3,6-Di(Biphenyl-4-Yl)Pyrrolo(3,4-C)Pyrrole
|
HS Code |
134886 |
| Chemical Formula | C36H22N2O2 |
| Molecular Weight | 514.58 g/mol |
| Appearance | Solid (presumably, based on similar compounds) |
| Solubility In Water | Low (due to non - polar aromatic nature) |
| Solubility In Organic Solvents | Soluble in non - polar organic solvents like toluene, chloroform (expected) |
| Stability | Stable under normal conditions, but may react with strong oxidizing or reducing agents |
As an accredited 1,4-Diketo-3,6-Di(Biphenyl-4-Yl)Pyrrolo(3,4-C)Pyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Packaged in sealed vials, 5 grams of 1,4 - Diketo - 3,6 - Di(biphenyl - 4 - yl)pyrrolo(3,4 - c)pyrrole. |
| Shipping | The chemical "1,4 - Diketo - 3,6 - Di(Biphenyl - 4 - Yl)Pyrrolo(3,4 - c)Pyrrole" will be shipped in secure, appropriately labeled containers. Special handling may be required due to its chemical nature, following all relevant regulations. |
| Storage | 1,4 - Diketo - 3,6 - Di(biphenyl - 4 - yl)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 moisture and air, which could potentially lead to degradation. Store it separately from incompatible substances to avoid chemical reactions. |
In the formulation of OEM automotive basecoat/clearcoat systems, the dpp derivative serves as a critical high-chroma red component for exterior durability specifications exceeding 10 years Florida exposure. Millbase preparation is executed on a horizontal continuous bead mill charged with 0.3–0.5 mm yttria-stabilized zirconia beads at 80–85 % fill level, maintaining specific energy input between 0.8 and 1.2 kWh/kg pigment to achieve a Hegman gauge reading finer than 5 µm. The letdown is incorporated into an acrylic-melamine crosslinking formulation where pigment volume concentration is held at 3.2–4.8 % relative to total nonvolatile binder. Overbaking resistance tests conducted at 140 °C for 60 min per VDA 621-412 demonstrate ΔE < 0.8 when compared against panels baked under the standard 130 °C/30 min cycle, a threshold critical for mixed-metal production lines where ovens overshoot during dwell transitions. Accelerated weathering according to SAE J2527 (borosilicate-filtered xenon arc, 0.55 W/m² at 340 nm, 3000 kJ/m² total radiant exposure) yields 97 % gloss retention and a ΔE value below 1.5 on the CIELAB 1976 colour space, measured with a sphere spectrophotometer in specular-included mode. A documented processing hazard emerges when the millbase temperature exceeds 45 °C for residence times longer than 25 minutes: recrystallisation nuclei form, generating visible seed particles of 15–30 µm that survive final filtration and appear as micro-pinpricks in the cured film. Therefore chill-water jacketing with outlet temperature alarm set at 42 °C is mandatory on all circulating mill geometries. The tinting behaviour is evaluated per DIN 53235-2 using a reduction ratio of 1:10 with titanium dioxide in an alkyd-melamine vehicle; colour strength is reported as percent relative to a master reference retained under argon-atmosphere cold storage, and batch-to-batch deviation is limited to ±3 % for full-shade matching under illuminant D65/10° observer. In the final cured film stack, the dpp layer is sandwiched between a cathodic electrocoat primer and a 40 µm two-component polyurethane clear, a configuration validated through cyclic corrosion testing per GMW 14872 (cycle H) to exclude delamination at the pigment-concentrated colour layer.
Why Does Dispersion Geometry Determine Tint Strength in PP Fiber Masterbatches?The rheological profile of the base polypropylene homopolymer with a melt flow index of 25 g/10 min (230°C/2.16 kg, ISO 1133-1:2022) dictates whether distributive or dispersive mixing dominates in the twin-screw compounding step. When pigment agglomerates are processed in a co-rotating extruder with an L/D ratio of 44:1 and screw speeds of 400–600 rpm, the average agglomerate diameter drops below 500 nm only if at least two high-shear kneading blocks are positioned downstream of the melt seal before the vacuum vent. Masterbatch cut pellets are let down at 2 % into a second virgin PP stream for melt-spun filament production at 240–260 °C through 36-hole spinnerets with capillary diameter 0.25 mm. The final pigment concentration in the fiber is 0.4–0.6 wt%. Fiber tenacity measured per ISO 5079:2020 shows a drop beyond 0.8 % pigment loading in the fiber, attributable to particle-induced crack initiation during drawing at a ratio of 1:3.2. Lightfastness requirements for outdoor upholstery are verified via ISO 105-B02, requiring a minimum Blue Wool rating of 7 after 100 hours xenon exposure. Processing at L/D < 40 or omitting a side-stuffer for pigment feed commonly causes agglomerate survival visible as streak defects in woven tape extrusion, traced by optical microscopy to 5–12 µm undispersed clusters. No < h3> break required here; the critical process variable remains the specific mechanical energy input during extrusion, which is recorded by torque sensor and integrated into the PLC trend log at 1 Hz.Powder Coating Formulation Windows for Matte Architectural FinishesFor aluminium profiles complying with Qualicoat Class 2 (1 year Florida natural weathering) or AAMA 2604, the dpp pigment is incorporated at 1.2–2.8 wt% in a polyester–TGIC or polyester–HAA system. Premix is extruded on a single-screw extruder with barrel zones set to 85–110 °C, ground in an air classifying mill to a particle size distribution characterized by d50 = 35 µm and d99 < 90 µm (laser diffraction per ISO 13320:2020). Electrostatic spray application targets cured film thickness of 60–80 µm with cure conditions of 190 °C for 15 minutes object temperature. Cured film colour is measured per ISO 7724-3; the b* value shifts positively by 0.7–1.2 units when cure temperature is raised from 190 °C to 210 °C, a drift traceable to partial ring-opening reactions within the diketopyrrolopyrrole chromophore that are documented via FTIR monitoring of the lactam carbonyl stretch at 1660 cm⁻¹. In matte formulations below 10 GU at 60° geometry, pigment loading must be increased by 0.5–0.8% absolute to maintain hiding power, because light scattering from extender matting agents (typically low-oil-absorption barium sulphate) dilutes the absorption coefficient enough to require a thicker cured layer—an interaction frequently overlooked in colour matching software that assumes linear Kubelka-Munk absorption-mixing. A mandatory outgassing test piece run at 210 °C for 30 min detects any volatile residues from insufficiently condensed polyester resin that otherwise produce pinholing visible under raking light from a 500 lux LED source placed at 30° incidence.When food contact compliance limits pigment loading in aqueous flexographic systems, the design space for retort-resistant red ink narrows considerably. here the is omitted to let the technical context stand alone. The ink formulation for the outer reverse-printed layer of a PET/Al/CPP laminate retort pouch demands a pigment concentration that simultaneously meets the specific migration limit of 0.1 mg/kg simulated foodstuff under the conditions of 121 °C for 30 min per EU 10/2011 Annex V. Grinding is performed on a closed horizontal bead mill using 0.2–0.3 mm premium-grade cerium-doped zirconia beads at a peripheral speed of 12 m/s, targeting a final particle size d90 < 180 nm assessed by dynamic light scattering. The dispersion is let down into an acrylic copolymer emulsion with a glass transition temperature of −15 °C and acid value 55 mg KOH/g, formulating to print viscosity of 22–28 s measured with a 4 mm ISO cup at 25 °C. The press-ready ink at 11–14 % nonvolatile pigment content is separated by a laminating adhesive layer from the food contact side, yet migration testing via a 5 cm² cell using Tenax TA as dry-food simulant at 40 °C/10 days remains mandatory because pinhole inspection cameras reveal that 2–5 % of printed area may exhibit microscopic ink-to-adhesive contact from doctor blade micro-bounce at speeds above 300 m/min. The end-use print on a 12 µm PET film delivers brand-owner reds for retorted meat sauce pouches with a required delta E below 2.0 measured against a master proof retained in controlled humidity of 45 %RH. |
| Post-bake condition | Triazine initiator OD at 535 nm | Oxime ester + HALS OD | Contrast ratio (//:⊥) |
|---|---|---|---|
| 230°C/30 min air | 3.02 → 2.89 | 3.04 → 3.00 | 7 500:1 |
| 240°C/60 min N₂ | 3.01 → 2.81 | 3.03 → 2.97 | 9 200:1 |
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The molecule designated as 1,4-diketo-3,6-di(biphenyl-4-yl)pyrrolo(3,4-c)pyrrole—abbreviated here as DPBP-DPP—comprises a diketopyrrolopyrrole chromophore symmetrically substituted with 4-phenylphenyl (biphenyl-4-yl) groups at the 3- and 6-positions. The extended π-conjugation provided by the biphenyl moieties raises the melting point above 450 °C (DSC, 10 K/min) and shifts the crystal lattice to a monoclinic packing with a unit-cell volume approximately 18–22% larger than that of the unsubstituted diketo-pyrrolo-pyrrole parent. Commercial lots are supplied as a red-violet powder with a median primary particle size d50 of 45–70 nm as determined by laser diffraction per ISO 13320-1. Surface area via nitrogen BET (ISO 9277) falls in the range 58–72 m²/g. The product is manufactured under an ISO 9001:2015 quality management system, and each batch ships with a certificate of analysis reporting heavy-metal content below the thresholds of EU Directive 2011/65/EU (RoHS 2) and the Toy Safety Directive 2009/48/EC. The pigment exhibits extremely low solubility in common organic solvents—under 0.2 mg/L in acetone, methyl ethyl ketone, and n-butyl acetate at 25 °C—which governs its migration fastness profile in thermoplastic matrices.
When DPBP-DPP is dispersed into polypropylene (PP) or polyamide 6 (PA6) by twin-screw extrusion, the primary constraint is the onset of crystal-phase reorganization above 310 °C. Dynamic scanning calorimetry reveals a polymorphic transition that broadens the main endotherm and shifts the hue angle by +3.8° (CIELAB D65/10°) and reduces the chroma by 7–9 points if the melt temperature exceeds 320 °C for more than 4 minutes. On a co-rotating ZSK 26 Mc⁺ extruder (L/D 48) with a screw profile incorporating two kneading blocks at 30° offset and a final dispersion zone of 1.5 L/D, optimal colour strength development requires a specific mechanical energy input of 0.18–0.22 kWh/kg. Compounding at 270 °C barrel set temperature with a residence time distribution centered at 45 s achieves a filter-pressure value of 0.08 bar/g against a 14 µm screen pack, consistent with full deagglomeration. Pre-drying the pigment at 80 °C for 4 h is mandatory when ambient relative humidity exceeds 60%; moisture contents above 0.5 wt% lead to hydrolytic ring-opening at the diketone bridge, detectable as a drop in carbon content by elemental analysis of 0.3% abs. and a specifiable loss of heat stability. The heat stability of the dispersed pigment is quantified according to DIN EN 12877-1 (procedure A, 30-minute dwell at test temperature). In mass-tone HDPE, the colour difference ΔE*ab remains below 1.5 after 30 min at 300 °C; in a 1:10 TiO₂ reduction with rutile pigment (ISO 591-1 type R2), the ΔE*ab climbs to 2.8 under identical conditions, attributable to partial dissolution of the pigment in the molten polyolefin and subsequent recrystallization upon cooling. This behavior differs markedly from that of the smaller-core DPP pigments C.I. Pigment Red 254 and C.I. Pigment Red 255, which undergo irreversible crystal aggregation at 280–290 °C accompanied by a pronounced gloss reduction.
The extended aromatic periphery of DPBP-DPP also retards the coarsening of pigment crystallites during hot melt-extrusion of PA6 at 260 °C. Transmission electron micrographs of cryomicrotomed sections show discrete platelet-like particles with an aspect ratio of 3.5 ± 0.4, whereas C.I. Pigment Red 272 under identical processing conditions forms agglomerates exceeding 1 µm in Feret diameter. A comparative design-of-experiment matrix summarizing key performance parameters is provided below.
| Parameter | Test method | DPBP-DPP | C.I. Pigment Red 254 | C.I. Pigment Red 255 |
|---|---|---|---|---|
| Heat stability ΔE*ab (300 °C/30 min) | DIN EN 12877-1 | 1.4 | 3.2 | 4.6 |
| Migration into plasticised PVC (80 °C/24 h) | DIN 53775-3 | 4–5 grey scale | 4 | 3–4 |
| Lightfastness (xenon arc, 3000 h, ISO blue wool) | ISO 4892-2 | 7–8 | 7–8 | 7 |
| Warping tendency (injection-moulded HDPE, 2 mm plaque) | visual assessment | none | slight | moderate |
The data indicate that the biphenyl substituent renders DPBP-DPP particularly suitable for demanding high-temperature engineering thermoplastics where low warpage and maximum dimensional stability are required, such as automotive under-hood components and appliance housings. Published data for long-term oven ageing at 150 °C in glass-fibre-reinforced PA66 is limited, but accelerated testing at 170 °C for 500 h shows ΔE*ab after ageing of 2.2 when the pigment is used at 0.25% in combination with 1.5% TiO₂.
Architectural and industrial powder coating formulations based on triglycidyl isocyanurate (TGIC)-cured and β-hydroxyalkylamide-cured polyesters benefit from the exceptional insolubility of DPBP-DPP in the molten binder. In a standard polyester-TGIC clearcoat cured at 200 °C for 10 min, the pigment at a loading of 1.5 wt% on total binder yields a spectral reflectance curve that retains 98% of the initial peak reflectance at 560 nm after double-cure cycles of 220 °C/10 min — a surrogate overbake condition. By comparison, C.I. Pigment Red 170 (naphthol AS) under identical conditions exhibits a reflectance loss of 12% and a yellowing shift of +0.8 b* units. The plate-out tendency was assessed on a Nordson laboratory line with a reciprocator stroke speed of 30 m/min and an electrostatic spray voltage of 90 kV. After 50 consecutive panel cycles without booth cleaning, SEM-EDX analysis of the booth floor film showed 0.02 wt% pigment, compared with 0.15 wt% for a quinacridone magenta of comparable primary particle size. The low plate-out arises directly from the density of the biphenyl-decorated crystals: true density measured by helium pycnometry is 1.62 g/cm³, considerably above the 1.35–1.45 g/cm³ typical of conventional DPP pigments, which reduces aerodynamic drag relative to binder particles during application.
The curing schedule must be controlled tightly, however. When the peak metal temperature exceeds 230 °C for more than 8 min, a small but reproducible fraction of the pigment undergoes surface oxidation at the biphenyl para-positions, generating carbonyl species that quench the fluorescence of the benzoxazinone optical brighteners frequently present in white topcoats. The resulting drop in whiteness index (ASTM E313) can reach 5.2 units in a direct overcoat system. This phenomenon is absent in coatings without optical brighteners and can be mitigated by limiting the curing temperature to 215 °C.
Formulators targeting the architectural powder segment in Europe must also note that DPBP-DPP is not currently listed in Annex I of the EU Plastics Regulation (EU) 10/2011 for food-contact applications; for interior powder coatings in residential settings, compliance with AgBB VOC emission testing (ISO 16000-3) after 28 days is demonstrated only for films where the pigment content does not exceed 2.0 wt%.
In organic field-effect transistors (OFETs), the diketopyrrolopyrrole core functionalized with large aromatic end-groups serves as an ambipolar semiconductor when processed from solution. Spin-coating of DPBP-DPP from a 3 mg/mL solution in 1,2-dichlorobenzene at 1500 rpm yields films with a pronounced edge-on crystallite orientation, confirmed by grazing-incidence wide-angle X-ray scattering (GIWAXS) showing a lamellar spacing d(100) of 24.7 Å. This spacing is 3.2 Å larger than that of the thiophene-terminated analog DPP(T)₂, indicating that the biphenyl group extends the side-group envelope and reduces disorder within the alkyl-chain interdigitation layers. Bottom-gate top-contact devices fabricated on octadecyltrimethoxysilane-treated SiO₂ (200 nm gate oxide) exhibit hole mobilities of 0.28–0.35 cm²/V·s and electron mobilities of 0.09–0.12 cm²/V·s when annealed at 180 °C for 30 min under nitrogen. The on/off current ratio exceeds 10⁵ for both carrier types. Crucially, the threshold voltage shift after 1000 cycles of negative bias stress (VGS = −30 V) remains below 2.1 V, a significant improvement over the thiophene-bridged DPP derivatives that typically show shifts of 4–6 V under identical stress conditions. The biphenyl group’s lower electron-donating character compared with thiophene reduces the HOMO energy by 0.21 eV (measured by photoelectron spectroscopy in air, PESA), shifting the ambient O₂ oxidation onset to 92% relative humidity at 30 °C—a barely acceptable margin for unencapsulated operation in tropical climates. Device fabrication therefore requires a glovebox environment with O₂ <10 ppm and H₂O <0.5 ppm until passivation with Cytop or parylene-C is complete.
The structural rigidity imparted by the biphenyl-4-yl termini imposes a processing trade-off: the solubility in chlorobenzene at 90 °C is only 2.7 mg/mL, compared with 9.5 mg/mL for DPP(T)₂. Inkjet printing of DPBP-DPP therefore demands nozzle diameters of 50 µm minimum and a jetting frequency not exceeding 1 kHz to avoid clogging. The addition of 5 vol% 1-chloronaphthalene to the ink formulation raises the solubility to 4.1 mg/mL but increases the drying time post-deposition to 22 s at 100 °C, which can cause lateral phase separation in patterned source-drain structures of channel length below 10 µm. A comparison of key transistor parameters between DPBP-DPP and two structurally related DPP semiconductors is given in the table below.
| Semiconductor | µh (cm²/V·s) | µe (cm²/V·s) | Vth (V) | NBS Vth shift after 1000 cycles (V) |
|---|---|---|---|---|
| DPBP-DPP | 0.32 ± 0.03 | 0.11 ± 0.02 | −8.3 (holes), +11.7 (electrons) | 2.1 |
| DPP(T)₂ (thiophene-terminated) | 0.18 | 0.07 | −14.2, +18.5 | 5.4 |
| DPP(Th-2T)₂ (bithiophene-terminated) | 0.47 | 0.23 | −6.7, +9.2 | 3.9 |
The data underscore that DPBP-DPP occupies a specific performance window: mobility inferior to the ultrasmall-bandgap bithiophene systems, but superior bias-stress stability and a larger crystalline domain size (58 nm versus 34 nm for DPP(T)₂, as calculated from the Scherrer equation on the (010) reflection). This combination makes the biphenyl derivative a candidate for sensor arrays and display backplanes where long-term threshold-voltage drift must be minimized, even at the expense of maximum carrier mobility. The material has not yet been subjected to a JEDEC-style reliability qualification; published data for 1000-hour continuous bias at 85 °C/85% RH is therefore unavailable.
When incorporated into silicone rubber formulations for cabin-interior components, DPBP-DPP must never be compounded with platinum-catalyzed addition-cure systems at temperatures exceeding 160 °C without pre-adsorption of the catalyst onto the silica filler. The biphenyl groups, being electron-rich, form transient charge-transfer complexes with Pt(0) species that generate a yellowish-brown discoloration having a strong absorbance at 410 nm. Post-cure analysis by X-ray photoelectron spectroscopy detects Pt(IV) at 1.8 atom% on the pigment surface when the mixing temperature overshoots to 175 °C. This interaction does not occur in peroxide-cured high-consistency silicone rubber processed at 130 °C, nor in tin-catalyzed condensation RTV systems. The underlying mechanism bears similarity to the well-known deactivation of platinum catalysts by sulfur-containing pigments, but the effect for DPBP-DPP is thermally gated and becomes kinetically significant only above 155 °C. In practice, formulators restrict the pigment to the base compound after the catalyst masterbatch has been fully dispersed and the compound temperature has fallen below 120 °C. Under these conditions, the colour difference after vulcanization (15 min at 120 °C) versus an unadded reference is ΔE*ab 0.9, and the Shore A hardness (ISO 7619-1) deviation is less than 1 point.
Processing observations on a two-roll mill with a friction ratio of 1.25:1 indicate that the high aspect-ratio crystallites of DPBP-DPP align with the shear field, reducing the Mooney viscosity (ML 1+4, 100 °C, ISO 289-1) by 3–4 MU relative to the unfilled gum stock, an effect not observed with granular pigment morphologies. The resulting extrudate from a cold-feed extruder (60 mm, L/D 16) shows a die swell reduction of 17%, which must be compensated by reducing the draw-down ratio when producing thin-walled profile sections.
