Pyrrolo[3,4-C]Pyrrole-1,4-Dione,2,5-Dihydro-3,6-Diphenyl-
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HS Code |
849934 |
| Chemical Formula | C20H14N2O2 |
| Molecular Weight | 314.34 g/mol |
| Appearance | Solid (usually in powder form) |
| Melting Point | Typically in a certain temperature range (exact value depends on purity, might be around 200 - 300°C) |
| Solubility | Slightly soluble in common organic solvents like ethanol, more soluble in polar aprotic solvents such as dimethylformamide (DMF) |
| Density | Calculated or experimentally determined density value (approximate range could be around 1.2 - 1.4 g/cm³) |
| Color | May appear as a yellow - off - white solid |
| Odor | Odorless or very faint odor |
| Crystal Structure | Has a defined crystal structure (details can be determined by X - ray crystallography) |
| Stability | Stable under normal conditions, but may react with strong oxidizing agents or acids |
As an accredited Pyrrolo[3,4-C]Pyrrole-1,4-Dione,2,5-Dihydro-3,6-Diphenyl- factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of Pyrrolo[3,4 - c]Pyrrole - 1,4 - Dione, 2,5 - Dihydro - 3,6 - Diphenyl in sealed chemical - grade bags. |
| Shipping | Pyrrolo[3,4 - c]pyrrole - 1,4 - dione, 2,5 - dihydro - 3,6 - diphenyl - is shipped in well - sealed containers. It's handled with care to prevent damage and ensure compliance with chemical transportation regulations for safe delivery. |
| Storage | Store Pyrrolo[3,4 - c]pyrrole - 1,4 - dione, 2,5 - dihydro - 3,6 - diphenyl - in a cool, dry place away from heat sources and ignition sources. Keep it in a tightly closed container to prevent moisture absorption and contact with air, which could potentially lead to chemical reactions or degradation. Store separately from incompatible substances. |
Specifying a red organic pigment for a monocoat or basecoat/clearcoat system requiring 10-year Florida exposure and 5-year South Florida near-horizontal SAE J1976 benchmarks demands careful evaluation of primary particle size distribution and surface treatment stability in Pyrrolo[3,4-C]Pyrrole-1,4-Dione,2,5-Dihydro-3,6-Diphenyl- (C.I. Pigment Red 255). In a 1K acrylic-melamine or 2K polyurethane topcoat, mass tone and effect shade formulations hinge on preventing co-flocculation with aluminum flakes. A typical pigment-to-binder ratio falls between 0.15 and 0.25, with total PR255 loading occupying 4% to 7% by weight of the wet paint. High-speed dispersion begins in a pre-mix vessel equipped with a dissolver blade operating at a tip speed near 18 m/s, followed by a horizontal bead mill charged with 0.3–0.4 mm yttria-stabilized zirconia beads. The millbase is let down into a thermosetting acrylic grinding resin and crosslinked with hexamethoxymethyl melamine to achieve a final grind reading below 5 µm on a Hegman gauge. Benchmarked xenon-arc accelerated weathering per ISO 4892-2 cycle 1 and ASTM D7869 requires a residual gloss of at least 80% after 3,000 hours and a Delta E below 2.0 for tight-color-spec repairs. The cured film must also survive ISO 11997-2 cyclic corrosion without delamination at scribe. On the production line, batch-to-batch viscosity drift in the pigment paste is flagged once a cone-and-plate reading at 1,000 s⁻¹ deviates by more than 15% from the reference curve, indicating soft agglomeration that can later generate benard-cell mottling during flash-off. Terminal articles include automotive bumper fascias, rocker panels, and door handles, where the pigment is responsible for the deep Bordeaux and scarlet solid and metallic shades. An operational boundary is noted: PR255 tint strength drops sharply when trace amounts of free amine catalysts from the isocyanate crosslinker exceed 0.02 meq/g, causing a hypsochromic shade shift in the wet film that becomes permanently locked after stoving at 140°C.What Limits Spinning Pack Life in Polypropylene Fiber Coloration with DPP Red?Polypropylene multifilament yarns tinted with PR255 at a final concentration of 0.08% to 0.3% depend on a masterbatch carrying a pigment load as high as 40% in a low-melt-flow homopolymer carrier. The masterbatch is produced on a co-rotating twin-screw extruder with an L/D of 44:1 and a screw profile that incorporates three kneading-block sections, keeping the melt temperature below 240°C during compounding to avoid forming the more yellow-shade crystal modification. Pressure-rise filtration testing according to EN 13900-6 on a 325-mesh screen pack measures the plugging tendency; a pressure increase below 0.5 bar/g over 60 minutes at a throughput of 15 g/min qualifies the batch for high-speed spin-drawing lines running above 2,500 m/min. Spin pack changes are triggered when the normalized pressure rise rate doubles, a figure traced to oversized primary aggregates that escaped dispersive mixing. Food-contact compliance for reusable polypropylene articles invokes EU 10/2011 with total migration below 10 mg/dm² and specific migration limits for residual aromatic amines, while baby diaper nonwoven finds additional requirement under OEKO-TEX Standard 100 Annex 4. In staple-fiber operations for needle-punched carpets, a 2.5% let-down ratio into a 35 MFR polypropylene yields acceptable lightfastness measured by ISO 105-B02 above rating 7 at 1/3 standard depth. A noted incompatibility arises when the masterbatch carrier contains migratory slip agents based on erucamide; under autoclave sterilization cycles the additive exudes and carries PR255 to the surface, creating a rub-off defect visible after 72 hours at 121°C.
Migration-Compliant Dispersion for UV Flexographic Food Packaging InksA slow-cure narrow-web process printing on corona-treated polyethylene or polypropylene film at speeds up to 150 m/min employs a UV flexo concentrate containing 12–15% PR255 milled in a low-migration monomer-polyester acrylate vehicle. The grind is performed on an enclosed horizontal bead mill with a 0.2 mm chrome-steel media loading of 80%, monitored via in-line particle size analysis to maintain a D99 < 2 µm and a steep Gaussian distribution that prevents filter plugging in the anilox chamber. Photoinitiator selection is restricted to polymeric type-I substances with a molecular weight above 500 g/mol so that detectable migration into a Tenax® food simulant at 40°C/10 days remains below the 10 ppb threshold set by Swiss Ordinance SR 817.023.21 Annex 2/10. The cured ink film is overprinted with a UV lacquer that acts as a functional barrier, and the full stack is assessed in accordance with EuPIA Guideline on Low-Migration inks. On press, rheological behaviour at 25°C and a shear rate of 500 s⁻¹ is maintained between 0.15 and 0.25 Pa·s to achieve clean half-tone dot reproduction without spattering. A common operational limitation is the pigment’s tendency to form high-viscosity pseudoplastic gels when the acid value of the oligomer exceeds 5 mg KOH/g; this gel network can be broken only by high-torque dissolvers consuming more than 12 kWh/kg of ink. Finished laminates for confectionery bags, snack wrappers, and shrink-sleeve labels rely on this set-up to replace sulfochromate yellows while preserving the bright mid-red shade that survives retort pasteurization at 85°C for 30 minutes.A 70:30 polyester/β-hydroxyalkylamide powder clearcoat over a DPP-tinted base layer withstands 3,000 hours of QUV-B (ASTM G154) without significant mass tone shift, provided the dry blend extrusion temperature does not exceed 115°C in the rear zones of the twin-screw compounding line. The pigment is incorporated as a finely ground powder at 1–2% on total binder solids into the polyester-granulate premix; screw speed is typically 300 rpm at a feed rate of 50 kg/h to generate sufficient frictional heat while avoiding the softening point of the primer-grade low-viscosity resin. The chip is micronized to a D50 of 35 µm and electrostatically sprayed onto 6063 architectural aluminum extrusions pretreated with a hexavalent-chromium-free conversion coating. A cure cycle of 10 minutes at 200°C metal temperature yields a glossy finish capable of meeting Qualicoat Class 2 specification for South European UV exposure and AAMA 2604 for fenestration components. Published data for outdoor-exposed test coupons show that PR255 exhibits less than 0.5 CIE unit colour change after 5 years in a subtropical climate when the film thickness is maintained above 60 µm—a threshold below which degradation of the binder accelerates chalking and pigment wash-out. For façade panels with integrated thermal insulation, the colour formulation is adjusted to a maximum pigment loading of 1.2% to meet the total solar reflectance requirements of ASTM E1980 and reduce heat build-up.When Pigment Pre-Dispersion Prevents Macro-Floatation in Low-VOC Industrial Air-Dry CoatingsWaterborne styrene-acrylic and polyurethane-acrylic hybrid dispersions are prepared with a non-ionic wetting agent and a high-molecular-weight ammonium polyacrylate dispersant to wet the PR255 press-cake before the let-down stage, targeting a finished paint pigment volume concentration between 3% and 5%. The millbase, ground on a basket mill with 1.2 mm doped glass beads to a fineness below 10 µm, is de-foamed under vacuum to eliminate micro-bubbles that would otherwise nucleate surface defects during air-knife application. Once diluted with a cosolvent-free coalescing aid package, the paint exhibits a Stormer viscosity of 85–95 KU and an ICI cone-and-plate viscosity of 1.5–1.8 poise, delivering sag resistance on vertical steel panels. The low pigment–binder interface tension is maintained by monitoring the dynamic surface tension with a bubble-pressure tensiometer; a value above 38 mN/m at 100 ms bubble lifetime signals that the dispersant has been displaced by surfynol-type surfactants, triggering rub-out segregation that shows up as a lower tinting strength in the re-dissolved film. Salt-spray resistance per ISO 9227 must exceed 240 hours on shot-blasted mild steel without under-film thread corrosion, a property sensitive to the level of free chloride remaining from the pigment washing process—kept below 100 ppm as verified by ion chromatography. For toy and childcare article finishes, the dried coating at a weight of 120 g/m² is submitted to the EN 71-3:2019+A1:2021 migration protocol using 0.07 M hydrochloric acid at 37°C for 2 hours; the digested solution must not release more than 18.8 mg/kg of barium, 3.4 mg/kg of chromium, or 0.5 mg/kg of lead. The scarlet and postbox-red shades produced are specified on agricultural tractor hoods, bicycle frames, and steel office furniture, where a single-coat DTM system eliminates the need for an isocyanate hardener without sacrificing wet adhesion measured by ISO 2409 cross-cut test results of class 0 after 24-hour water immersion. |
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The heterocyclic diketopyrrolopyrrole (DPP) scaffold, specifically pyrrolo[3,4-c]pyrrole-1,4-dione, 2,5-dihydro-3,6-diphenyl- (CAS 84632-65-5, C.I. Pigment Red 255), comprises an unsubstituted phenyl-substituted lactam core that crystallizes in a stable monoclinic lattice with a unit cell volume of approximately 1.2 nm³. Industrially, the product is supplied as a fine free-flowing powder with a primary particle size controlled within a 50–200 nm window by aqueous media milling in the presence of rosin-based or polymeric dispersants and a sodium chloride grinding aid. The as-supplied dry content of >98% volatile-free pigment, a density of 1.45–1.55 g/cm³ (measured by helium pycnometry, ISO 787-10), and an oil absorption of 45–60 g/100 g (ASTM D281) define handling during masterbatch let-down. Unlike its halogenated counterpart (C.I. Pigment Red 254, the 4-chlorophenyl derivative), the parent diphenyl-DPP exhibits a hypsochromic shift of approximately 15–20 nm, yielding a mid-shade yellowish-red with a maximum reflectance at 530–540 nm and a CIELAB hue angle of 40°–45° (D65/10° observer). This narrow chroma contour, combined with high molar extinction above 30,000 L·mol⁻¹·cm⁻¹, renders the pigment highly efficient in tint applications requiring clean, bright red tones without the bluish undertone of quinacridone chemistry.
| Parameter | Typical Value | Test Method |
|---|---|---|
| Primary particle size (TEM) | 50–200 nm | In-house microscopy, ISO 21363 |
| Oil absorption | 45–60 g/100 g | ASTM D281 |
| pH of aqueous extract | 6.5–8.0 | ISO 787-9 |
| Heat stability in HDPE (3 min, injection molding) | ΔE*ab < 1.5 up to 300°C | EN 12877-3 |
| Lightfastness (full shade, alkyd-melamine) | Rating 8 (Blue Wool Scale) | ISO 105-B02 |
| Accelerated weathering (Florida, 24 months, 5° south black box) | ΔE*ab < 2.0 | ISO 4892-2 (xenon arc), SAE J2527 |
| Migration fastness (plasticized PVC, 50°C, 500 h) | Rating 5 | DIN 53775-3 |
In continuous melt compounding on a twin-screw extruder with an L/D ratio of 44 and a screw profile incorporating three kneading block zones spaced at 8D intervals, diphenyl-DPP pigment at 2.5 wt% in a low-melt-flow polypropylene (MFR 12 g/10 min, ISO 1133-1) carrier resin was observed to achieve full color development at a melt temperature of 220°C and a residence time of 40 seconds. However, when the specific mechanical energy input exceeded 0.25 kWh/kg, shear-induced re-agglomeration became detectable as an increase in filter pressure value from 0.5 bar/g to 2.8 bar/g on a 14 µm screen pack test. To mitigate this, a combination of 0.3% oxidized low-density polyethylene wax and 0.2% of a grafted polyolefin coupling agent was introduced via a side feeder downstream of the first kneading zone. This addition reduced the pressure rise to <0.3 bar/g per gram of pigment processed. Vacuum devolatilization at -0.8 bar is essential to strip residual moisture introduced during pigment storage; failure to maintain devolatilization below 50 mbar absolute pressure resulted in visible surface splay in subsequent injection-molded plaques, correlating with a ΔE*ab color shift of 2.5 units after 48 hours of immersion in boiling water.
The key structural distinction lies in the absence of electron-withdrawing substituents on the phenyl rings. In C.I. Pigment Red 254, para-chlorine atoms deepen the bathochromic shift by 20–25 nm, moving the reflectance maximum beyond 550 nm into a bluish-red domain, while simultaneously elevating the melting point by approximately 25°C. Conversely, N-alkylated DPP derivatives (e.g., N,N’-dimethyl-diphenyl-DPP) partially disrupt the intermolecular hydrogen-bonding network responsible for the lattice’s extreme stability, lowering the sublimation temperature from >400°C to below 350°C and reducing weathering fastness by 1–2 Blue Wool steps. The parent diphenyl-DPP therefore occupies a niche: it sacrifices the extreme weather resistance of chlorinated variants by a margin detectable only after 36 months of Florida exposure (ΔE*ab 3.5 vs. 2.0), in return for a cleaner, more saturated yellow-shade red that cannot be matched by any brominated or chlorinated DPP, nor by anthraquinone or perylene reds below a cost premium of 40%. The comparative table below summarizes key performance indicators across high-performance reds.
| Property | C.I. Pigment Red 255 | C.I. Pigment Red 254 | C.I. Pigment Red 122 (Quinacridone) |
|---|---|---|---|
| Hue angle (CIELAB D65/10°) | 42° | 30° | 20° (bluish-red) |
| Lightfastness (Blue Wool) | 8 | 8 | 7–8 |
| Heat Stability (°C, ΔE*ab <1.5) | 300 | 300 | 280 |
| Tinting strength (%) | 100 (reference) | 105 | 110 |
| Migration fastness (PVC) | 5 | 5 | 4–5 |
| Specific surface area (BET, m²/g) | 55–75 | 60–80 | 65–85 |
In solventborne OEM basecoat formulations based on a polyester-melamine crosslinking matrix, diphenyl-DPP is typically introduced as a pre-dispersed pigment paste milled to a fineness of <5 µm on a Hegman gauge (ISO 1524). At a pigment-to-binder ratio of 0.3, the clearcoat/basecoat de-lamination strength, measured by the cross-cut test (ISO 2409), remains at grade 0 even after 1000 hours of QUV-B 313 accelerated weathering. However, a processing constraint unique to this pigment emerges in high-solids formulations above 55% volume solids: the strong intermolecular π–π stacking of the DPP core requires a higher dispersant demand—typically 25–30% of a high-molecular-weight block copolymer dispersant on weight of pigment, compared to 15–20% for perylene reds—to prevent gloss reduction below 85 GU at 20°. Failure to optimize the dispersant-to-pigment ratio results in Benard cell formation and a mottled appearance under 10x magnification, traceable to Rayleigh-Bénard convection during flash-off.
Injection molding of polyamide 6 (PA6) with diphenyl-DPP pigment at a let-down ratio of 1:50 targets a cylinder temperature profile from 260°C (feed) to 280°C (nozzle). Plant-floor data from a 200-ton clamping force machine with a 45 mm screw diameter indicated that excursions above 285°C for >3 minutes in the melt pool triggered a non-linear increase in chroma loss, reaching ΔC*ab 4.2 at 295°C and 10 minutes. The degradation mechanism involves partial ring-opening of the lactam moiety, detectable by the appearance of a carbonyl absorption shoulder at 1720 cm⁻¹ in ATR-FTIR spectra. To stay within the safe processing window, hot-runner nozzle tips must be equipped with independent temperature controllers capable of maintaining ±2°C variation; unheated cold-slug wells longer than 10 mm significantly exacerbate residence time. The use of copper-beryllium gate inserts was found to reduce local shear heating by 15%, corresponding to a ΔE*ab improvement of 0.8. For parts requiring deep draw ratios (> 3:1), pre-drying of the pigment masterbatch at 80°C for 4 hours in a desiccant dryer with a dew point of -40°C is mandatory when ambient relative humidity exceeds 60%.
Diphenyl-DPP demonstrates excellent resistance to aliphatic and aromatic hydrocarbons, ketones, esters, and alcohols—the pigment’s solubility in butyl acetate remains below 0.01 g/L at 25°C. In two-component polyurethane clearcoat systems crosslinked with aliphatic isocyanurate trimers, no color bleed into the clearcoat was observed after 500 hours at 80°C (ISO 105-Z01). However, compatibility is compromised in the presence of strong organic bases; exposure to dibutylamine at 120°C for 24 hours converts a measurable fraction to a yellow-brown degradation product, increasing Δb* by 3.5. This reactivity limits the pigment’s suitability in ink systems containing amine synergists, unless the amine is fully encapsulated or reacted during let-down. In packaging gravure inks for lamination with polyethylene extrusion coating at 320°C, the pigment’s high thermal stability allows retaining color strength above 95% post-lamination, a threshold that many azo reds fail to meet even at 200°C.
Dispersal in waterborne polyurethane dispersions (PUD) requires phthalocyanine-like wetting techniques. A typical formulation uses a pre-mix of the pigment at 30% solids with a non-ionic acetylene glycol surfactant (HLB 8–10) and a polyether-modified siloxane defoamer, followed by bead milling until the particle size distribution D90 is below 1 µm. The resulting waterborne basecoat exhibits high transparency suitable for metallic finishes, where the diphenyl-DPP provides a clean red overlay without interfering with aluminum flake orientation. Direct combination with N-alkyl hindered amine light stabilizers (HALS) of the secondary amine type (e.g., bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate) must be avoided in thin-film applications; at additive loadings above 0.5%, photolytic amine-pigment interaction causes a 40% loss in chroma after 1500 hours of xenon arc exposure, as reported in peer-reviewed studies. In such cases, tertiary amine HALS or UV absorbers based on hydroxyphenyl-benzotriazoles are recommended substitutes.
