Bis-(P-Chrolopheny)-1.4-Diketopyrrolo(3.4-C)Pyrrole
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HS Code |
255408 |
| Chemical Formula | C18H8Cl2N2O2 |
| Molar Mass | 357.17 g/mol |
| Appearance | Red - violet powder |
| Solubility In Organic Solvents | Soluble in some organic solvents like DMF, DMSO |
| Melting Point | High melting point (above 300 °C in some cases) |
| Color In Solution | Intense red - violet color |
| Crystal Structure | Has a defined crystal structure with specific packing of molecules |
| Uv Vis Absorption | Shows characteristic absorption bands in the visible region |
| Thermal Stability | Good thermal stability up to certain temperatures |
| Photostability | Relatively good photostability |
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 | 1 kg of Bis-(P - Chrolopheny) - 1,4 - Diketopyrrolo(3,4 - C)Pyrrole in sealed chemical - grade packaging. |
| Shipping | Bis-(P - Chlorophenyl)-1,4 - Diketopyrrolo(3,4 - C)Pyrrole is shipped in well - sealed, corrosion - resistant containers. Special care is taken to prevent exposure during transit, following strict chemical shipping regulations. |
| Storage | **Storage of Bis-(P - Chlorophenyl)-1,4 - Diketopyrrolo(3,4 - C)Pyrrole** Store this chemical in a cool, dry place, away from direct sunlight. Keep it in a well - ventilated area, preferably in a closed container to prevent contact with air and moisture, which could potentially cause degradation. Avoid storing near heat sources or reactive substances to ensure its stability and integrity. |
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Bis-(p-chlorophenyl)-1,4-diketopyrrolo[3,4-c]pyrrole (C.I. Pigment Red 254, CAS 84632-65-5) exhibits a mid-shade red with a broad absorption envelope peaking near 560 nm. Millbase viscosity instability during solventborne high-shear dispersion on a horizontal bead mill—typically an Eiger Mini 50 or Netzsch LME 4 operating with 0.4–0.6 mm yttria-stabilized zirconia beads at tip speeds exceeding 10 m/s—has been traced to transient crystal lattice strain. When the pre-mix is held beyond 48 hours at pigment loadings above 35 wt% in a mixed xylene/butyl acetate medium, a thixotropic loop develops; rheograms from a cone-plate viscometer at 20°C show a hysteresis area expansion of up to 1,500 Pa/s. This rheological artifact, once carried into a 2K polyurethane topcoat, shifts the dry-film contrast ratio at 12 µm DFT from a target 98.5% to below 94% (EN ISO 6504-3). Consequently, dispersion dwell time and bead fill ratio must be delimited: 6–8 passes at a product throughput of 150–200 kg/h per litre of chamber volume, with a bead charge not exceeding 80% of the mill free volume. The resulting pigment concentrate, when let down into a hydroxyl-functional acrylic resin, achieves a Hegman gauge grind of 7.5 without auxiliary surfactant, transparency verified by transmission electron micrographs showing discrete primary particles below 70 nm. These parameters underpin robust tinting strength consistency in premium basecoat/clearcoat systems where colour difference ΔE*ab under D65 illuminant remains below 0.8 across production batches. What governs gloss retention in coil coating formulations exposed to QUV-B cycling?Polyvinylidene fluoride (PVDF)/acrylic dispersion coatings containing the pigment at a pigment volume concentration (PVC) between 8% and 12% are roll-applied onto 0.5 mm gauge hot-dip galvanized steel pretreated with chromium-free conversion layers. After peak metal temperature (PMT) curing at 249–254°C for 45–55 seconds, the 60° specular gloss metric (ISO 2813) reads 30–35 units at a dry film thickness of 20–22 µm. Accelerated weathering per ASTM G154 Cycle 1 (UVA-340 lamps, 0.89 W/m² at 340 nm, 8 h UV at 60°C Black Panel, 4 h condensation at 50°C) exposes a critical inflection at 1,200 hours: gloss loss accelerates beyond 2% per 100 hours unless the weight ratio of PVDF to acrylic is maintained above 70:30 and the crystal stabiliser—a hydroxybenzophenone UV absorber—is present at 1.0–1.5% on total binder solids. Below that ratio, photo-oxidative scission of the acrylic phase generates free carboxylic acid moieties that complex with surface aluminium from the pigment substrate, creating microscopically hydrophilic domains; these nucleate moisture ingress and promote chalking (chalk rating per ASTM D4214 falls from 10 to 6). Plant-floor data from a three-roll reverse coater line indicate that re-dispersion of oven-loft overspray back into the recirculation system elevates the coarse particle fraction (> 5 µm, measured optically on a Fineness of Grind gauge) by 300–500 ppm, which translates into a measurable drop in distinctness-of-image (DOI) from 85 to 72 on the Byk Wavescan. Therefore, filter bags rated at 25 µm absolute must be changed every 3,000 running metres of coil. Polyolefin fibre melt-spinning: a narrow processing window for clarity and spinnabilityIn polypropylene staple fibre for nonwoven hygiene applications, the pigment is compounded as a 40% masterbatch in a polypropylene homopolymer carrier with a melt flow index (MFI, 230°C/2.16 kg) of 25–30 g/10 min. The twin-screw extruder—typically a co-rotating ZSK 26 Mc18 with L/D 40—operates at screw speed 350 rpm and barrel temperature profile 180→220→230→230→230→220°C. Downstream, the let-down ratio is 1:25, yielding a final pigment loading of 1.6% in the filament. Spinning is conducted through spinnerets with 0.3 mm diameter holes at a take-up velocity of 2,000 m/min. When extrusion temperature exceeds 235°C in the die zone, gas chromatography-mass spectrometry detects trace 4-chlorophenyl fragments from incipient sublimation of pigment molecules; these recondense on the spinneret face and cause filament breaks exceeding 3 per tonne per hour. Conversely, if the masterbatch carrier MFI falls below 20 g/10 min, melt inhomogeneity generates pigment agglomerates visible as black specks in the final nonwoven at a count exceeding 5 per m² under incident light. Tight control of the peroxide vis-breaking step in the carrier resin—targeting a polydispersity index < 3.5—eliminates this defect. Fibre grade denier filaments so produced, with a tenacity of 2.5–2.8 cN/dtex, achieve a lightness L* value > 90 and a colorimetric purity suitable for deep red diaper leg cuffs without bronzing. Migration fastness under ISO 105-C06 test A1S (40°C, 30 min, 4 g/L ECE phosphate reference detergent) registers ≥ grade 5. For solventborne gravure ink printed on corona-treated biaxially oriented polypropylene (BOPP) film at 150 m/min, let-down of a predispersed nonionic-wet pigment chip (20% pigment on nitrocellulose/plasticizer carrier) into a 1:1 ethanol/ethyl acetate diluent must account for equilibrium solubility of the binder. At 15°C, the pigment’s crystalline habit exhibits a tendency to nucleate styrene-maleic anhydride resin complexation, causing a rapid ink-body bodying effect; viscosity measured on a Shell Cup #2 rises from 22 seconds to 35 seconds within 30 minutes. The remedy is a pre-wetting step with 2 wt% (on pigment) of a hyperdispersant having a pigment-affinitive anchor group of the aromatic ρ-chlorobenzyl type and solvation chains of poly(hydroxystearic acid), combined with pH buffering to 6.8–7.2 using triethanolamine. Print fidelity assessed by a spectrophotometer (X-Rite eXact) on a laminated confectionery packaging structure (reverse-printed ink between OPP and aluminium foil) showed ΔE ≤ 1.1 over 10,000 linear metres, with no tone compression in the magenta region. The printed article meets the Swiss Ordinance RS 817.023.21 Annex 2 negative list for food-contact colourants, obviating the need for an additional functional barrier. Table I: Accelerated weathering protocol comparison for architectural façade coatings
Data sourced from a silicone-modified polyester powder coating cured at 200°C for 12 minutes. The sharp drop under QUV-B 313 is attributed to the pigment’s sensitised photo-reduction at wavelengths below 320 nm, generating semiquinone radical intermediates that abstract hydrogen from the binder. Hence, the pigment is recommended for applications where the clearcoat contains a UV absorber extending through the sensitive UV-B region, specifically a hydroxyphenyl-triazine class compound with extinction coefficient > 150,000 L mol⁻¹ cm⁻¹ at 315 nm. What limits the doping ratio in conjugated polymer blends for organic field-effect transistors?The chlorinated DPP chromophore serves as a strong electron acceptor when copolymerised with thienothiophene donors, but the small-molecule pigment itself can function as a crystalline p-type semiconductor. Spin-coated thin films from a 0.5 wt% solution in anhydrous 1,2-dichlorobenzene onto octadecyltrimethoxysilane-treated SiO₂/Si substrates (capacitance density 11.5 nF/cm²) exhibit a field-effect mobility of 0.04–0.1 cm²/V·s in bottom-gate top-contact configuration after thermal annealing at 150°C for 1 hour under nitrogen (O₂ < 1 ppm). However, at doping ratios above 2 wt% in a poly(3-hexylthiophene) (P3HT) matrix, X-ray diffraction shows disruption of the (100) lamellar stacking of P3HT; the coherence length drops from 12 nm to below 4 nm, and the on/off current ratio collapses from 10⁴ to 10². This is accompanied by an increase in off-current leakage from the gate dielectric, likely due to conductive pathways formed at grain boundaries of the DPP pigment crystallites that bridge source and drain electrodes. The practical outcome is that only ultralow loadings—0.1–0.5 wt%—are viable for tuning threshold voltage in photosensor transistors with a specific detectivity of 2 × 10¹¹ Jones at 600 nm. Encapsulation with a parylene-C layer deposited via Gorham process is mandatory to mitigate rapid mobility degradation upon exposure to ambient air; unencapsulated devices lose 50% of initial mobility within 24 hours at 50% RH. Table II: Critical processing parameters across application segments
In coil coating topcoats manufactured on a multi-roll coater running at 120 m/min, the pigment’s inherent hard texture (Mohs hardness approx. 2.5–3.0) necessitates that the grinding phase not be omitted in favour of a simple high-speed dissolver. Attempts to bypass bead milling yield a particle size distribution where the d90 remains above 1.5 µm; during roll-nip application, such aggregates orient parallel to the metal strip, creating a shade-dependent colour-flop that violates the accepted ΔEₐ₆ constraint of 0.7 under a BYK-mac multi-angle spectrophotometer at 15°, 45°, 75° specular. Consequently, mills are operated with a specific energy input of 0.8–1.2 kWh/kg of pigment. The resulting colouristic properties: tinting strength (ISO 787-24) reaches 100% of standard after 6% addition to a white alkyd-melamine test medium, corresponding to a Kubelka-Munk K/S value of 2.8 at 560 nm. For long-oil alkyd decorative paints tinted through point-of-sale dispensers, pre-dispersion as a surfactant-coated universal tinter is mandatory. The tinter paste, containing 25% pigment by weight, 15% alkylpolyglucoside-based nonionic dispersant, and the balance propylene glycol/water, must maintain a Hegman reading ≥ 7 after 12 months storage at 40°C. Cylinder test data (1 litre can, ICI cone-and-plate rheometer) reveal that without the addition of 0.3 wt% of a hydrophobic fumed silica (BET surface area 130 m²/g), sedimentation forms a hard pack that cannot be re-incorporated by mechanical shakers. Once integrated into the alkyd paint at a ratio of 1:50, the brush-out on primed wood exhibits an opacity of 95% at 10 m²/L (ISO 6504). Migration fastness under EN 71-3 (toy safety) demonstrates extractable element content below detection limits, confirming no release of chlorinated aromatic amines or free 4-chloroaniline. The compound is listed on the European Inventory of Existing Commercial Chemical Substances under EC number 617-974-8 and carries a REACH registration covering uses as a colourant in professional and consumer coating applications. |
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Bis-(P-Chrolopheny)-1.4-Diketopyrrolo(3.4-C)Pyrrole constitutes a chlorinated aryl-substituted derivative within the 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) pigment class, distinguished by the presence of para-chlorine atoms on both pendant phenyl rings. The compound crystallizes in a monoclinic lattice system, with the electron-withdrawing chlorine substituents modifying the intermolecular hydrogen-bonding network between adjacent lactam NH and carbonyl oxygen units. This perturbation of the solid-state packing arrangement relative to the unsubstituted phenyl-DPP analogue produces measurable shifts in both the visible absorption maximum and the sublimation enthalpy. Commercial production typically follows the base-catalyzed condensation of 1.0 mole equivalent of succinic acid dialkyl ester with 2.0 mole equivalents of p-chlorobenzonitrile in a tertiary alcohol medium—most commonly tert-amyl alcohol—at reflux temperatures between 120 °C and 135 °C, utilizing sodium or potassium tert-alkoxide as the condensation agent. Post-synthesis particle conditioning via salt milling, acid pasting, or solvent-mediated Ostwald ripening determines the final crystallite dimensions, which in turn govern tinctorial strength, opacity/transparency balance, and rheological behavior during dispersion.
Substitution at the para-position of the peripheral phenyl rings with chlorine atoms introduces an electronic perturbation that is fundamentally different in character from the electron-donating effects exerted by methyl, tert-butyl, or methoxy groups commonly employed in other commercial DPP pigments. The Hammett σp constant for chlorine (+0.23) reflects a moderate electron-withdrawing inductive influence, which slightly reduces the electron density on the central DPP bicyclic lactam system. This manifests spectroscopically as a hypsochromic shift of 3–7 nm in the principal absorption band compared to the unsubstituted phenyl-DPP parent structure, depending on crystallite size and measurement geometry. More significantly, the chlorine atoms participate in non-covalent halogen-bonding interactions within the crystal lattice, increasing the lattice energy and elevating the thermal decomposition onset. Differential scanning calorimetry under nitrogen purge at 10 K/min heating rate typically registers a single endothermic event above 380 °C corresponding to simultaneous melting and decomposition, approximately 15–25 °C higher than the equivalent transition for the p-methylphenyl analogue. The absence of a discrete melting point below the decomposition threshold—a characteristic shared across the DPP family—necessitates dispersion in the finished article rather than dissolution processing.
Comparative evaluation against Pigment Red 254 (the p-chlorophenyl DPP, C.I. 56110) and Pigment Red 255 (the p-phenyl DPP) reveals that the chloro substituent imparts a marginally yellower masstone accompanied by enhanced opacity in full-shade applications, attributable to the higher refractive index conferred by the chlorine atomic polarizability. In reduction with titanium dioxide (TiO₂, rutile grade, 1:10 ratio by mass), the chlorinated variant exhibits a cleaner, slightly bluer undertone compared to the brominated analogue, making it suitable for formulations demanding chromatic purity in pastel shades without recourse to shading pigments that may compromise weatherability. Published data for this specific configuration in certain niche application environments—particularly long-term immersion in aggressive chlorinated water media—is limited; therefore, qualification testing per application-specific protocols remains mandatory.
For digital inkjet applications requiring sub-micron pigment particles to prevent nozzle clogging in piezo-electric printheads with orifice diameters of 20–50 µm, the primary particle size must be reduced below 200 nm and maintained in a de-aggregated state throughout the ink service life. Bead-milling of the crude pigment in aqueous or solvent-borne media using yttria-stabilized zirconia grinding media of 0.3–0.4 mm diameter, operated at agitator tip speeds of 10–14 m/s, can achieve a D50 particle size of 80–120 nm as determined by dynamic light scattering (ISO 22412:2017). The specific surface area, measured by nitrogen adsorption according to BET methodology (ISO 9277:2022), increases from approximately 8–12 m²/g for presscake-grade material to 55–75 m²/g for finished inkjet-grade dispersions. This surface area expansion proportionally increases the demand for polymeric dispersant adsorption; insufficient dispersant concentration leads to bridging flocculation manifested as a time-dependent viscosity increase during accelerated storage testing at 60 °C over 28 days. A dispersant-to-pigment mass ratio of 0.35:1 to 0.55:1, utilizing structured acrylic block copolymer dispersants with pigment-affinic anchoring groups, has been observed to yield Newtonian flow behavior at shear rates relevant to piezo-electric drop ejection (10⁴–10⁵ s⁻¹).
Incorporation of the chlorinated DPP pigment into polyetherimide (PEI), polyetheretherketone (PEEK), or polyphenylene sulfide (PPS) matrices—all of which demand melt processing temperatures between 310 °C and 400 °C—poses a thermal stress that approaches the pigment's degradation threshold. Thermogravimetric analysis conducted per ASTM E2550-21 at 10 °C/min under nitrogen reveals an onset of mass loss at approximately 385–395 °C for the optimized crystal polymorph, but sustained isothermal exposure at 340 °C for 30 minutes can induce 1.5–3.0 % mass loss accompanied by a perceptible darkening of the masstone due to incipient thermal decomposition products. Compounding on twin-screw extruders with L/D ratios of 40:1 or greater must therefore balance dispersive mixing intensity against residence time; barrel temperature profiles should be configured such that the melt temperature measured at the die exit does not exceed 330 °C for formulations containing this pigment. Screw designs incorporating forward-conveying elements through the melting zone, with kneading blocks restricted to the dispersion zone downstream of complete polymer plastication, reduce the probability of localized viscous heating sufficient to trigger pigment degradation. Injection molding clamp force settings above 1,500 kN on tools with hot-runner systems must account for the potential accumulation of degraded pigment residue at dead spots within the manifold, which may intermittently release as visible specks in molded parts. Purging with a commercial glass-fiber-reinforced purging compound at 20–30 shot intervals during extended production runs mitigates this accumulation.
A further processing consideration unique to the chlorinated DPP structure involves its interaction with polyamide matrices. The amide linkages in polyamide 6 and polyamide 66 can participate in hydrogen-bond exchange with the lactam functionalities of the pigment surface, leading to a viscosity increase during compounding that is more pronounced than that observed with phthalocyanine or quinacridone pigments at equivalent loading. Rotational rheometry on polyamide 66 compounds containing 0.5 wt% chlorinated DPP pigment, measured at 285 °C under oscillatory shear at 1 Hz, has shown complex viscosity elevations of 12–18 % relative to unfilled polymer, compared to 5–8 % for an equivalent loading of Pigment Red 254 of coarser particle size distribution. This rheological perturbation must be accounted for in mold-filling simulations, particularly for thin-wall sections below 1.0 mm thickness where increased viscosity can extend fill times beyond processing window tolerances.
Pre-drying of the pigment powder before compounding is mandatory when ambient relative humidity exceeds 60 % at 23 °C. Moisture adsorbed on the high-surface-area pigment particles—typically 1.5–3.0 wt% as determined by Karl Fischer titration (ISO 15512:2019)—hydrolyzes the lactam rings at melt processing temperatures, generating degradation byproducts that manifest as both color shift and plate-out on mold surfaces. Drying in a vacuum oven at 80–90 °C for a minimum of 8 hours, or in a desiccant dryer with a dew point below −40 °C for 4–6 hours, reduces moisture content below 0.3 wt%, after which the pigment should be immediately compounded or stored in sealed, desiccated containers.
| Property / Test Condition | Bis-(P-Chrolopheny)-DPP | Pigment Red 254 (Unsubstituted Phenyl-DPP) | Test Method |
|---|---|---|---|
| Masstone ΔE* after 3,000 hrs Xenon arc | 1.8–2.5 | 2.0–2.8 | ISO 16474-2:2013, Method A, Cycle 1 |
| 1:10 TiO₂ reduction ΔE* after 2,000 hrs | 0.9–1.6 | 1.5–2.3 | ISO 16474-2:2013, Method A, Cycle 1 |
| Gloss retention at 60° after 2,000 hrs (%) | 82–90 | 78–86 | ISO 2813:2014 |
| Alkyd-melamine bake (30 min at 140 °C), overbake ΔE* | ≤ 0.5 | ≤ 0.7 | ASTM D2244-23 |
| Acrylic-polyurethane 2K, QUV-B 313, Δb* after 1,500 hrs | +0.3 to +0.8 | +0.5 to +1.2 | ASTM G154-23, Cycle 2 |
The enhanced photostability of the chlorinated DPP relative to the parent phenyl-DPP structure is attributed to the electron-withdrawing character of the chlorine substituents, which lowers the energy of the highest occupied molecular orbital (HOMO) and thereby reduces the susceptibility of the excited-state chromophore to oxidative attack by singlet oxygen generated during photo-exposure. This mechanistic interpretation is consistent with the observation that brominated DPP analogues, despite possessing even greater atomic polarizability, exhibit inferior lightfastness due to the weaker C–Br bond dissociation energy facilitating homolytic cleavage pathways that initiate chromophore destruction. The chlorinated derivative thus occupies a unique position in the weatherability hierarchy: superior to methyl- and unsubstituted phenyl-DPP grades, marginally superior to the p-chlorophenyl grade (C.I. Pigment Red 254) in certain binder systems, and inferior only to the exceptionally durable p-trifluoromethylphenyl-DPP variants that are not yet widely commercialized outside aerospace coating applications.
Evaluation of migration behavior in plasticized poly(vinyl chloride) (PVC-P) containing 35 phr di-2-ethylhexyl phthalate (DEHP) plasticizer, tested according to EN ISO 15701:2022 at 80 °C under a contact pressure of 5 kPa for 24 hours against a white PVC-P receptor sheet, yields a staining rating of 4–5 on the grey scale (ISO 105-A03:2019), indicating negligible plasticizer-mediated migration. This performance places the chlorinated DPP alongside the highest-performing organic pigments available for flexible PVC applications. The low migration tendency arises from the combination of high molecular weight (357.2 g/mol), strong intermolecular hydrogen bonding within the crystal lattice, and the relatively low solubility of the planar polycyclic structure in common plasticizers. In contrast, certain monoazo pigments of comparable shade but lower molecular weight (< 300 g/mol) can exhibit migration ratings as low as 2–3 under identical test conditions, limiting their suitability for applications involving prolonged flexible PVC contact with light-colored substrates.
Solvent resistance testing per DIN 53770-1—which involves 24-hour immersion of pigmented coatings in a graded series of organic solvents including ethanol, ethyl acetate, methyl ethyl ketone, toluene, and xylene—demonstrates that the chlorinated DPP pigment remains non-bleeding (rating 5) in alcohols and aliphatic hydrocarbons, with slight bleeding (rating 4) observed only in the most aggressive aromatic and ketone solvents. This profile supports use in solvent-borne industrial coatings where resistance to fuel splashes or cleaning solvents forms part of the end-use specification.
For powder coating applications cured at 180–200 °C for 10–15 minutes—typical polyester-TGIC or polyester-HAA chemistry—the compound's thermal robustness ensures minimal sublimation during cure. Sublimation fastness, assessed by heating a drawdown panel in a forced-air oven at 220 °C for 10 minutes with a white aluminum panel positioned 2 mm above the coating surface, shows no visible condensate on the receptor panel, equating to a rating of 5 per the industry-standard sublimation ladder protocol.
Regulatory compliance data confirm that the pigment contains no heavy metals above the threshold limits specified in EU Directive 94/62/EC (Packaging and Packaging Waste) as amended by 2004/12/EC—specifically, lead, cadmium, mercury, and hexavalent chromium are each below 100 ppm as determined by ICP-OES following microwave-assisted acid digestion per EN 16711-1:2015. The compound is listed on the Japanese Positive List for food contact materials (JHOSPA, amended 2020) under category IV pigments, and has been evaluated for compliance with the Swiss Ordinance RS 817.023.21 Annex 10. Registration under REACH (EC 1907/2006) has been completed for the > 1 tonne/annum import volume band; the substance is not classified as SVHC per the ECHA Candidate List as of the most recent published update.
Avoid combining this pigment with strongly nucleophilic amine-based additives—particularly aliphatic primary amines used as epoxy curing agents in two-component ambient-cure systems—as nucleophilic attack at the lactam carbonyl carbon can initiate ring-opening at temperatures as low as 60–70 °C, leading to progressive chromophore destruction over the coating service life. Tertiary amines and aromatic amines are substantially less aggressive, though compatibility should be confirmed through accelerated storage testing at 50 °C for 14 days with the fully formulated system.
