1,4-Dioxo-3,6-Diphenylpyrrolo[3,4-C]Pyrrole
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HS Code |
777950 |
| Chemical Formula | C20H10N2O2 |
| Molar Mass | 310.31 g/mol |
| Appearance | Solid (usually a colored solid, often red - violet) |
| Melting Point | High melting point (specific value would require experimental determination) |
| Solubility In Water | Low solubility in water (hydrophobic compound) |
| Solubility In Organic Solvents | Soluble in some organic solvents like chloroform, dichloromethane |
| Crystal Structure | Typically forms well - defined crystals with a specific packing arrangement |
| Uv Vis Absorption | Exhibits characteristic absorption bands in the visible region (useful for color - based applications) |
| Fluorescence Properties | May show fluorescence depending on environmental conditions |
| Thermal Stability | Relatively stable under normal thermal conditions but may decompose at high temperatures |
As an accredited 1,4-Dioxo-3,6-Diphenylpyrrolo[3,4-C]Pyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 10 grams of 1,4 - Dioxo - 3,6 - Diphenylpyrrolo[3,4 - c]Pyrrole in sealed chemical - grade bags. |
| Shipping | 1,4 - Dioxo - 3,6 - Diphenylpyrrolo[3,4 - c]Pyrrole is shipped in sealed, corrosion - resistant containers. Adequate cushioning is used to prevent breakage. Shipment follows strict chemical transportation regulations to ensure safety. |
| Storage | 1,4 - Dioxo - 3,6 - Diphenylpyrrolo[3,4 - c]Pyrrole should be stored in a cool, dry place, away from direct sunlight and heat sources. 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 any chemical reactions. |
A Primer on Ketopyrrole Chemistry and Coating DurabilityIncorporation of 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) into high-performance coating systems introduces a distinct set of rheological and photochemical considerations. The molecule’s rigid, planar chromophore, characterized by a diketopyrrolopyrrole core, necessitates high-shear dispersion to overcome strong intermolecular hydrogen bonding forces that otherwise manifest as aggregate-induced color drift. During mill-base processing on a horizontal bead mill charged with 0.4–0.6 mm yttria-stabilized zirconia media, a disc peripheral speed of 10–12 m/s is maintained to achieve a Hegman grind below 5 µm. Operators note that failure to control mill-base temperature below 55 °C during this operation leads to a transient increase in viscosity, a phenomenon traced to partial solubilization of the pigment surface layer in high-polarity solvent blends containing methoxypropyl acetate. Once fully dispersed, the pigment exhibits exceptional resistance to crystal growth, a property verified through long-term storage trials where delta-E values remain below 0.5 units after 12 months at 40 °C, measured according to ISO 2814:1973. Solventborne OEM Clearcoat Compatibility: How Application Conditions Influence Wet-Layer ReflowThe combination of a DPP-based basecoat with a high-solids clearcoat demands analysis of interfacial migration potential, particularly under bake conditions deviating from the 140 °C standard. At a pigment volume concentration (PVC) of 4.2%, the sublimation onset temperature of the Cl-substituted derivative reaches 368 °C, eliminating bleed concerns during standard OEM cycles. Formulations for mid-coat systems typically target a mass solids content of 18–22% and a pigment-to-binder ratio (P:B) of 0.35:1. The dry film thickness (DFT) for an automotive basecoat anchored at 12–15 µm achieves full hiding, with spectral reflectance curves revealing 91% absorption across the 500–540 nm band, resulting in a highly saturated red masstone. Process engineers in OEM tier-one lines calibrate the electrostatic bell speed to 28,000–32,000 rpm to ensure uniform metallic flake orientation without perturbing the DPP chromophore orientation, which remains isotropic in the cured film. Adhesion tested under cross-hatch (ISO 2409:2020) after 240 hours of constant condensation (ISO 6270-2:2017) produces a Gt 0 rating on electrocoated steel panels. The applicable coatings compliance framework references REACH Annex XVII entry 72, and the cured film meets VOC zone limits for solvent emissions as outlined in Directive 2004/42/EC. Terminal product categories encompass passenger vehicle exterior body panels, two-wheeler ABS fairing components, and aerospace interior laminates where FAR/JAR 25.853(a) vertical burn certification is required. In coils coated on high-speed continuous lines with a line speed exceeding 80 m/min, the addition of 2.8 wt% DPP into a polyester-melamine topcoat yields a weathering performance threshold that diverges sharply from phthalocyanine-based alternatives. Published data for this specific configuration is limited, but isolated field reports indicate that interfacial delamination between the primer and topcoat becomes detectable after 2,000 hours of QUV-B 313 nm irradiation (ASTM G154-23 cycle 1) when the pigment loading exceeds 3.5%, attributed to photocatalytic activity at the pigment-binder interface. The critical compliance standard is EN 13523-10:2017, and the resulting coated metal finds application in architectural cladding profiles with a 25-micron topcoat system designed for warranty periods up to 30 years in non-coastal environments. Equipment monitoring on a roll coater with a three-roll reverse applicator requires control of the pick-up roll gap to ±2 µm to counteract viscosity fluctuations induced by rapid solvent evaporation from the high-surface-area pigmented wet film. When Powder Coating Gel Times Drop Below Two MinutesA pre-mix of 2.0% DPP compounded into a saturated carboxylated polyester resin matrix with triglycidyl isocyanurate (TGIC) at a 93:7 ratio is extruded on a co-rotating twin-screw extruder with an L/D ratio of 44:1. The barrel temperature profile is set sharply from 85 °C in zone 1 to 110 °C in zone 8, with a screw speed of 400 rpm preventing excessive shear heating that prematurely triggers the TGIC ring-opening reaction. The resulting extrudate is chipped, ground in an air classifying mill to a particle size distribution with a median (d50) of 35 µm, and electrostatically sprayed onto a substrate pre-heated to 180 °C. Gel time determination via ISO 8130-6:2021 at 200 °C shows a reduction from the 140-second neat resin baseline down to 95 seconds, a catalytic effect of the DPP surface groups that requires careful management of line speeds in high-volume continuous coating ovens. The Qualicoat Class 2 specification governs approved powder composition, and final coated architectural extrusions for window frames and curtain wall mullions undergo specific Florida exposure for 5 years as part of the certification process. The lack of volatile organic compounds simplifies compliance with the Industrial Emissions Directive (2010/75/EU); terminal assembly lines integrate these colored powders onto cyclone recovery systems achieving 98% transfer efficiency. Operators in injection molding bays note that pre-colored compound in polypropylene homopolymer destined for thin-walled food containers requires pre-drying at RH less than 30% when the DPP masterbatch carrier is a low-molecular-weight polyethylene wax, to prevent splay defects at gate entry points. The melt temperature is maintained at 230 °C during plastication, and the pigment’s thermal stability, confirmed by thermogravimetric analysis in nitrogen atmosphere with a 1% mass loss at 418 °C, surpasses the processing window for HDPE (180–220 °C) and PP (230–260 °C) extrusion blow molding. A typical let-down ratio of 1:25 from a 40% pigment loading masterbatch yields a vibrant red in polypropylene bottle caps, tested for migration under European Plastics Regulation (EU) 10/2011 with simulant D1 (ethanol 50% v/v) for 10 days at 40 °C showing specific migration limits below the 10 mg/kg food simulant threshold. The compliance path relies on positive-list inclusion and specific migration testing per EN 1186-1:2002; the downstream product register consists of beverage closures, cosmetics jars, and toy parts where toy safety standard EN 71-3:2019+A1:2021 is enforced. High-Shear Dispersion Pathways in Waterborne Acrylic Wall PaintsThe aggressive colloidal stabilization required for DPP in a latex paint formulation starts with a predispersion step where the pigment powder is incorporated into an aqueous phase containing a nonionic wetting agent at a concentration of 20% on pigment weight. By using an alkylphenol ethoxylate-free surfactant with an HLB of 13.5, the formulator achieves a mill-base with a solids content of 45%. A high-speed dissolver fitted with a saw-tooth blade creates a vortex that feeds the agglomerates into the shear zone; the tip speed is held at 18 m/s for 20 minutes, resulting in a fineness of grind below 10 µm. In the letdown stage, this concentrate is stirred into a styrene-acrylic copolymer emulsion with a minimum film-forming temperature of 8 °C. The critical control parameter emerges during thickener addition: associative polyurethane thickeners (HEUR) interact with the DPP particle surface and elevate the low-shear Brookfield viscosity beyond 120 KU (Stormer), necessitating a shift to high-molecular-weight HEC for sag control. The end formulation meets the limit for formaldehyde emission under the German AgBB scheme after 28-day chamber testing. Terminal application sites include interior high-traffic public spaces such as hospitals and educational facilities where volatile organic compound ceilings under the LEED v4.1 Low-Emitting Materials credit apply. The paint’s scrub resistance, measured on a Gardner scrub machine per ASTM D2486-17, exceeds 15,000 cycles before film breakthrough, a performance metric attributed to the hard pigment’s role in reinforcing the coalesced binder matrix.
Continuous inkjet printing with a binary array printhead demands extremely tight particle size control to avoid nozzle clogging, a common failure mode where DPP aggregates larger than 0.5 µm bridge across the 35 µm nozzle orifice. The starting ink dispersion process uses a recirculation bead mill operating with 0.1 mm ceramic beads until the particle size distribution reveals a d99 of 0.3 µm, verified by dynamic light scattering. Butanone-based ink with a viscosity of 4 cP at 40 °C contains 3.5 wt% DPP, and the ink’s resistivity is adjusted to 1,200 Ω·cm using a soluble electrolyte salt for proper droplet deflection. The key print reliability test involves deciphering 20 million characters printed onto HDPE cable sheathing without a single nozzle-out. The printed codes must survive tetrachloroethylene dip testing per SAE AS5942C to verify permanence on under-hood automotive wire harnesses; the final compliant production ink has a pot life exceeding 8 months in sealed, damped cartridges under constant recirculation. The signal integrity of QR codes rated to ANSI X3.182-1990 grade B or better forms the core quality metric for packaging serialization in pharmaceutical track-and-trace systems under EU Falsified Medicines Directive (2011/62/EU). Acceptability of Oxygen Transmission Rates in DPP-Colored PET BottlesIncorporation of DPP at 0.8% into monolayer polyethylene terephthalate bottles for edible oil introduces an amorphous haze zone at the bottle base where the cooling rate in the injection stretch blow mold was lowest. The carbonyl groups in the DPP molecule serve as a nucleating agent that accelerates crystallization, reducing the oxygen transmission rate (OTR) from 0.035 cc/pkg/day to 0.028 cc/pkg/day measured on a Mocon Ox-Tran unit at 23 °C and 50% RH per ASTM D3985-17. Processors on a two-stage SBO machine adjust the preform temperature zone settings by +3 °C to compensate for the increased stress-whitening tendency around the gate region. The material complies with U.S. FDA 21 CFR 178.3297 on colorants for polymers, and the final bottle, subjected to drop impact testing at 4 °C per ISTA 1A protocol, exhibits no change in breakage rate relative to uncolored controls. Downstream filling lines running at 600 bottles/minute require no label adhesive changes, as the surface energy of the colored PET, measured by contact angle goniometry with diiodomethane, remains at 42 dynes/cm.
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1,4-Dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole, supplied as DiketoPyrrolo 255‑1, is a highly crystalline diketopyrrolopyrrole (DPP) pigment offering a bright mid‑shade red with strong masstone opacity and a blue‑undertone in reductions. The product’s primary particle size is controlled between 30 and 60 nm, with a surface area of 62–74 m²/g determined via nitrogen BET adsorption (ASTM D5604‑96). X‑ray diffraction data confirm ordered planar stacking along the [0 k l] axis, contributing to its exceptionally low solubility in common organic solvents (<10 mg/L in xylene, n‑butanol, and ethyl acetate at 25°C). Three distinct aggregation profiles are available: a standard opacifying grade (255‑1‑OP), a micronized grade for high‑gloss films (255‑1‑MT), and a surface‑treated variant incorporating a polyalkylene oxide adlayer to suppress flocculation in low‑PVC alkyd systems.
The 255‑1 pigment withstands peak processing temperatures of 320°C for a dwell time of 90 s in low‑density polyethylene without color shift exceeding ΔE*ab 1.5 units, as measured per CIEDE2000 (ISO/CIE 11664‑6:2014) on injection‑molded plaques. Long‑term heat stability testing on a Leistritz ZSE‑27 twin‑screw extruder (L/D 40:1, screw speed 250 rpm) over seven recycle loops in a polypropylene homopolymer (MFR 12 g/10 min at 230°C/2.16 kg, ISO 1133‑1:2022) confirmed a ΔE of 1.8 after the seventh pass. In comparison, C.I. Pigment Red 170 (naphthol AS) degrades rapidly under identical conditions, exhibiting a ΔE of 8.4 by the third pass. The DPP backbone lacks labile azo or azomethine linkages, and the central diketopyrrolopyrrole ring exhibits no measurable homolytic cleavage below 420°C as shown by TGA‑MS in nitrogen. For processing with engineering thermoplastics such as polyamide 66 (melting point 262°C), a barrel temperature profile of 270–300°C is recommended, and residence time must not exceed 4 minutes to avoid sublimation-induced plate‑out on die lips. Published data for this specific configuration in polycarbonate at 0.2 wt% loading and 300°C extrusion is limited, but lab‑scale trials indicate a threshold of 310°C before a greenish shift becomes detectable.
The 255‑1‑OP grade exhibits an opacity of 98.7% at a film thickness of 45 μm in a 3‑layer co‑extruded cast polypropylene film, measured according to ISO 2471:2008. This makes it suitable for inside‑the‑package applications where rapid visual identification of product integrity is required. Migration kinetics through the film were evaluated according to the European Union’s plastics migration model as referenced in Commission Regulation (EU) No. 10/2011, Annex V; under worst‑case simulant D2 (vegetable oil) at 40°C for 10 days, specific migration of the pigment was below the analytical detection limit of 0.01 mg/kg using HPLC‑Diode Array Detection. The pigment is enumerated in the Swiss Ordinance on Materials and Articles (SR 817.023.21) with positive listing under specific migration limits. Differences from conventional red iron oxide or chromium‑based pigments in food contact are conspicuous: iron oxide pigments typically require loading rates of 3–5 wt% to achieve comparable opacity, whereas 255‑1‑OP reaches the same visual coverage at 0.8–1.2 wt%, reducing the total additive mass and consequently the potential for migration of any accompanying trace impurities. The product is incompatible with polyvinyl chloride (PVC) compounds that contain high levels of epoxidized soybean oil (ESBO) above 5 phr, as the oxirane groups catalyze partial ring‑opening at the diketone moiety over extended service life at 80°C; this manifests as a loss of chroma of 2–3 CIELAB units after 500 hours.
Under accelerated weathering per ISO 4892‑2:2013 (xenon‑arc, Method A, black standard temperature 65°C, 0.51 W/m² at 340 nm), both the opacifying and micronized forms of 255‑1 display a ΔE of less than 1.0 after 3000 hours in a full‑tone alkyd‑melamine rigid PVC‑free coil coating at 10% pigment volume concentration (PVC). This photostability surpasses that of C.I. Pigment Violet 19 (β‑quinacridone), which under identical exposure conditions reaches ΔE 5.2 owing to photo‑oxidation of the linear trans‑quinacridone moiety, and outperforms C.I. Pigment Red 179 (perylene maroon) whose surface‑state‑controlled fading leads to a ΔE of 3.0 after 2000 hours. While both DPP and perylene pigments rely on extended π‑conjugated polycyclic systems, DPP’s symmetry‑forbidden vibrational relaxation pathways reduce excited‑state reactivity toward singlet oxygen, lessening the need for hindered amine light stabilizer (HALS) adjuvants. The 255‑1‑MT grade additionally benefits from a dense siloxane‑based inorganic coating (surface treatment amount 2.8 wt% as determined by TGA residue) that reduces photocatalytic activity at the crystal edge sites, as confirmed by ESR spectroscopy detecting <1×1012 spins/cm² after 500 hours of UV‑A exposure. In contrast, untreated C.I. Pigment Red 254 (diketo-pyrrolo-pyrrole) of similar particle size generates detectable hydroxyl radicals under the same conditions unless post‑treated with a proprietary phenolic antioxidant wash.
| Parameter | 255‑1‑OP | 255‑1‑MT | Test Method |
|---|---|---|---|
| Oil absorption (g/100 g) | 35–42 | 28–34 | ISO 787‑5:1980 |
| pH of aqueous extract | 6.5–7.5 | 6.0–7.0 | ISO 787‑9:1981 |
| Residue on 325 mesh (45 µm) | <0.1 % | <0.05 % | ISO 787‑7:2009 |
| Heat stability (HDPE, 300°C/5 min) | ΔE 1.5 | ΔE 1.2 | EN 12877‑2:2000 |
| Specific gravity | 1.55–1.60 | 1.56–1.62 | ISO 787‑10:1993 |
For thin‑film ink systems, the micronized grade 255‑1‑MT provides a jetness‑enhanced optical appearance without the need for carbon black shading. Viscosity profiles were measured on a Bohlin Gemini rotational rheometer (cone‑and‑plate geometry, 2°, 60 mm, gap 40 µm) using a nitrocellulose‑polyamide varnish of solids content 25 wt% at 25°C. At a constant shear rate of 500 s⁻¹, the Brookfield‑equivalent viscosity increased by only 15 mPa·s upon addition of 4% pigment, indicating minimal thixotropic build‑up. This differs markedly from C.I. Pigment Red 48:2 (calcium salt of BONA) where the same loading raises viscosity by 85 mPa·s due to surfactant‑extractable surface layers. The low‑tack rheology allows gravure presses (Cerutti R960, cylinder speed 250 m/min) to operate without plate‑out for runs exceeding 10,000 linear meters.
Total solar reflectance (TSR) measured in accordance with ASTM E903‑12 using a Laboratory Reflectometer (Device & Services, Model 15R) on a dry film of 150 µm thickness over a black substrate (reflectance <5%) recorded a TSR of 42.8% for a coating pigmented solely with 255‑1‑OP. Blending with titanium dioxide (rutile, 0.2 µm diameter) at a 1:2 pigment ratio pushes TSR to 72.3%, reducing the surface temperature of a galvanized steel panel by 11°C under 1000 W/m² irradiance. While C.I. Pigment Black 30 (chrome‑iron‑nickel spinel) is the traditional near‑infrared transparent black, the DPP pigment offers an alternative deep‑red aesthetic that retains high NIR reflectance selectively in the 700–1400 nm range. The extinction coefficient in the near‑infrared drops to 0.02 L·g⁻¹·cm⁻¹ at 800 nm, enabling 95% transmission of NIR radiation through the colorant layer. This selectivity is a direct consequence of the narrow HOMO–LUMO gap (2.1 eV as determined by cyclic voltammetry) and the absence of low‑energy charge‑transfer transitions. Coatings thus formulated can meet California Title 24 reflectivity standards for steep‑sloped roofs while maintaining the desired chromaticity coordinates.
In solventborne architectural stains, the pre‑wetted version (255‑1‑PW) containing 8 wt% of a non‑ionic dispersant is introduced directly into an aliphatic hydrocarbon/mineral spirit carrier. Dynamic laser light scattering (Zetasizer Nano ZS, backscatter angle 173°) after 48 hours aging at 50°C shows a D[90] value of 240 nm with no observable flocculation peak. This narrow particle size distribution eliminates the need for sand‑milling steps that are mandatory for coarser‑grade quinacridones, reducing energy consumption per batch by an estimated 30 kWh.
Coextrusion trials on a Davis‑Standard sheet line with three extruders feeding a feedback‑block and a 1.2 m width die identified a critical dependency between pigment loading in the polypropylene cap layer and interfacial adhesion to the polypropylene‑g‑maleic anhydride tie layer. At loadings above 1.8 wt%, the melt surface tension of the pigmented layer, as estimated by the pendent drop method at 230°C, drops below 28 mN/m, causing a viscosity mismatch that results in interfacial shark‑skin defects when the primary substrate throughput exceeds 60 kg/h. Maintaining product within the 1.2–1.7 wt% loading range preserved a surface gloss of 85 GU (60° glossmeter, ISO 2813:2014) and eliminated micro‑delamination as verified by scanning acoustic microscopy. The limitation is characteristic of high‑symmetry DPP molecules that pack densely at the surface layer, whereas asymmetrically substituted DPP analogs (e.g., 1,4‑dioxo‑3‑(4‑chlorophenyl)‑6‑phenylpyrrolo[3,4‑c]pyrrole) exhibit lower cohesive energy density and do not induce such rheological discontinuities under identical conditions.
| Test | 255‑1‑OP | C.I. Pigment Red 254 (untreated) | C.I. Pigment Red 170 (naphthol AS) | Standard |
|---|---|---|---|---|
| Light fastness (0–8 scale, 2000 h Xenotest) | 7–8 | 7 | 5–6 | ISO 105‑B02:2014 |
| Weather fastness (ISO 4892‑2, 2000 h, ΔE) | 1.0 | 1.4 | 8.7 | ISO 105‑A05 |
| Heat fastness (5 min at 300°C, ΔE vs. room‑temp reference) | 1.5 | 1.7 | >30 (decomposition) | EN 12877‑2 |
| Acid resistance (5% H₂SO₄, 24 h) | No change | Slight yellowing | Strong bleeding | EN 14469‑2 |
| Alkali resistance (1% NaOH, 24 h) | No change | ΔE 0.5 | ΔE 4.2 | EN 14469‑2 |
Pre‑drying is mandatory when the pigment powder has been stored in conditions with relative humidity exceeding 60% for more than 24 hours. The particle surface adsorbs 2.0–2.5 wt% moisture, and if not dried at 120°C for 2 hours in a fluidized‑bed dryer, the bound water flash‑evaporates during compounding and creates micro‑voids in the final molded part. These voids reduce flexural modulus by up to 8% (ASTM D790‑17, three‑point bend on 3.2 mm bars) and are detectable via micro‑CT scanning as pore volumes exceeding 0.05 mm³ in a 1 cm³ region. The same drying protocol is unnecessary for the pre‑coated 255‑1‑PW grade used in liquid applications.
In powder coating formulations cured at 200°C for 10 minutes (polyester‑TGIC chemistry), the 255‑1‑MT grade demonstrated an overbake resistance of 20 minutes at 220°C with only 0.6 ΔE deviation from the standard white‑reduced reference panel. This resilience allows powder coaters to re‑introduce coated workpieces for curing correction without the risk of dramatic color drift seen with monoazo reds. Published data for the specific application in ultra‑durable silicone‑polyester resin systems (reticulation at 250°C) remains sparse, suggesting pre‑production trials are advised when substrate metal temperature exceeds 240°C by more than 2°C. The pigment is incompatible with zinc‑rich epoxy primers that are subsequently overbaked above 300°C, as nascent ZnO catalyzes ring‑opening reactions resulting in a loss of tinting strength of ∼30% as confirmed by spectrophotometric absorbance reduction at 535 nm.
