Pyrrolo3,4-Cpyrrole-1,4-Dione, 3,6-Bis4-(1,1-Dimethylethyl)Phenyl-2,5-Dihydro-
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HS Code |
350258 |
| Chemical Formula | C30H30N2O2 |
| Molecular Weight | 446.57 g/mol |
| Appearance | Solid (usually off - white to pale yellow) |
| Melting Point | Typically in the range of 200 - 250 °C (approximate, can vary depending on purity) |
| Boiling Point | Decomposes before boiling due to its heat - sensitive nature |
| Solubility | Soluble in some organic solvents like dichloromethane, chloroform, and toluene; poorly soluble in water |
| Density | Estimated density around 1.1 - 1.2 g/cm³ (approximate) |
| Uv Vis Absorption | Absorbs in the visible and near - UV regions, with characteristic peaks related to its conjugated π - system |
| Stability | Stable under normal conditions, but sensitive to strong oxidizing agents and high temperatures |
As an accredited Pyrrolo3,4-Cpyrrole-1,4-Dione, 3,6-Bis4-(1,1-Dimethylethyl)Phenyl-2,5-Dihydro- 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 in sealed chemical - grade packaging. |
| Shipping | The chemical "Pyrrolo[3,4 - c]pyrrole - 1,4 - dione, 3,6 - Bis[4 - (1,4 - Dimethylethyl)phenyl]-2,5 - Dihydro -" should be shipped in well - sealed, corrosion - resistant containers, following all hazardous chemical shipping regulations to ensure safety. |
| Storage | **Storage for Pyrrolo[3,4 - c]pyrrole - 1,4 - dione, 3,6 - Bis(4 - (1,1 - dimethylethyl)phenyl)-2,5 - dihydro -**: Store this chemical in a cool, dry place away from heat sources and direct sunlight. Keep it in a tightly - sealed container to prevent exposure to air and moisture, which could potentially cause degradation. Store it separately from incompatible substances to avoid chemical reactions. |
How Does Surface Treatment Modify Dispersion Rheology in Solventborne OEM Coatings?Commissioning a high-chroma orange pigment for original equipment manufacturing (OEM) multi-layer systems confronts the formulator with a specific trade-off between colour saturation and shear-stability during recirculating line supply. The diketopyrrolopyrrole chromogen 3,6-bis[4-(tert-butyl)phenyl]-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, corresponding to C.I. Pigment Orange 73, delivers a masstone close to reddish-orange with a high molar extinction coefficient, but the untreated pigment surface causes immediate thixotropic build in medium-solids acrylic-melamine resin blends. Plant-scale experience on horizontal bead mills equipped with 0.8–1.0 mm yttria-stabilised zirconia media confirms that a primary dispersion step at 28–32 wt% pigment loading in a branched polyester grinding resin (Acid Value 12–18 mg KOH/g) combined with 8–12% of a high-molecular-weight polyurethane-based hyperdispersant (amine value 22–26 mg KOH/g) is necessary to suppress mill-base viscosity spikes beyond 120 KU at 25°C. The adsorbed dispersant layer, routinely characterised via depletion isotherm analysis, shifts the isoelectric point to below pH 3.5, thereby preventing flocculation when the mill-base is let down into a butylated melamine binder system at a final pigment content of 4.2–5.8 wt% on total formula weight. Titania (rutile grade, ISO 591-1:2000 Type R2) is co-ground at a pigment-to-binder ratio maintained within 0.42–0.55 to guarantee solid-colour opacity and hiding power at dry film thickness as low as 18 µm. An operational bottleneck repeatedly observed in mid-size OEM batches is the exotherm during high-speed disperser pre-mix when the dispersant dosage falls below 9%; localised gelation at the pigment–vehicle interface raises torque demands beyond 45 N·m on a 75 kW dual-shaft dissolver and can derate throughput by up to 35% unless the feed sequence is re-ordered to pre-dissolve the dispersant in the grinding resin before pigment introduction. Regulatory requirements for volatile organic compounds (VOC) in premium automotive basecoats are typically met by aligning solvent selection with the EU Directive 2004/42/CE Phase II thresholds, while heavy-metal absence permits classification under End-of-Life Vehicle Directive 2000/53/EC. Accelerated weathering under SAE J2527 (xenon-arc, borosilicate inner and outer filters) for 4000 kJ/m² exposure retains ≥93% of the original 60° specular gloss compared to a non-exposed control, provided the clearcoat stack incorporates a hindered-amine light stabiliser package with a basicity constant pKb below 5.5 to avoid acid-base interaction with the pigment’s lactam nitrogen.Melt Processing Windows for Thin-Wall Polypropylene Injection MouldingFloor-trial records from polypropylene converter facilities indicate that thin-wall food-container lids (0.55–0.75 mm nominal thickness) coloured with C.I. Pigment Orange 73 demand an extraordinarily narrow processing corridor to avoid warpage caused by differential crystallisation speeds. The pigment, dosed as a single-pigment masterbatch at 35–40% concentration in a random copolymer PP carrier with a melt flow rate (MFR 230°C/2.16 kg, ISO 1133-1:2022) of 28–35 g/10 min, is let down to a final pigment content of 0.18–0.28 wt%. Differential scanning calorimetry data gathered on injection-moulded plaques (Mettler Toledo DSC 3+, heating rate 10 K/min) show that the diketopyrrolopyrrole nucleus acts as a heterogeneous nucleating agent, elevating the onset crystallisation temperature (Tc,onset) by 6–8°C relative to natural PP. This shift becomes process-critical because the temperature of the cooling water in the mould circuit must then be raised by 5–10°C to equalise shrinkage between the gate and the weld-line region; failure to adjust results in out-of-spec flatness deviations exceeding 1.2 mm across a 200×120 mm lid profile. A clamp force of 1200–1500 kN on a 50 mm reciprocating-screw machine with a 22:1 L/D ratio is adequate, but plastication temperature must be capped below 280°C because thermogravimetric analysis under nitrogen (TGA, 10 K/min) reveals an onset of mass loss at 298°C attributable to N-aryl bond scission. Food-contact compliance is demonstrable under Regulation (EU) No 10/2011 Annex I, with overall migration into 3% w/v acetic acid and 10% v/v ethanol below the 10 mg/dm² limit when extraction is conducted for 2 h at 70°C; the pigment must, however, be pre-inspected for primary aromatic amine release because trace impurities arising from the synthetic route can occasionally exceed the 0.01 mg/kg detection threshold if the crude presscake is not washed to a conductivity below 50 µS/cm.When low-density polyethylene squeeze tubes are pigmented to an opaque orange finish for sun-care packaging, the migration kinetic profile of the diketopyrrolopyrrole colourant becomes the dominant stability constraint. The compound 3,6-bis[4-(1,1-dimethylethyl)phenyl]-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione exhibits an octanol-water partition coefficient (log P) calculated to be above 6.5, which practically eliminates spontaneous leaching from the polyolefin matrix, yet diffusion coefficients measured through Franz-cell permeation tests across 2 mm sheets of LDPE (density 0.918–0.922 g/cm³) indicate a lag time exceeding 400 hours at 40°C before quantifiable penetration into 50% v/v ethanol food simulant. Tube-wall formulations therefore routinely incorporate 0.15–0.30 wt% of the neat powder, pre-dispersed as a 50% masterbatch in a metallocene LLDPE base, and co-extruded as a thin outer skin layer so that the colourant never directly contacts the product. Pin-hole failures during extrusion are avoided by pre-drying the masterbatch at 80°C for 4 hours in a desiccant-bed dryer with a dew point below −40°C; moisture levels above 0.03% generate steam bubbles that manifest as surface craters visible under 20× magnification. Ultraviolet screening efficacy tested per ASTM D4329-21 cycle A (UVA-340 lamps, 0.89 W/m²·nm at 340 nm) for 1500 hours confirms that the pigment’s intrinsic photostability allows less than DE*ab 1.0 colour drift, provided the tube wall contains 0.5% of a benzotriazole-type UV absorber to scavenge radical species generated in the amorphous phase of the polymer.A nanocolloidal disperse form of the same diketopyrrolopyrrole is essential for high-speed digital textile printers relying on piezo-electric drop-on-demand printheads. Extensive bench optimisation on a 10 L closed-circuit horizontal bead mill charged with 0.3 mm yttria-stabilised zirconia beads demonstrates that a grinding residence time of 45–60 minutes reduces the 50th-percentile volume diameter (d50) to 95–115 nm as verified by laser diffraction (ISO 13320:2020, Mie optical model). The aqueous dispersion is stabilised with 3.5–4.5 wt% of a styrene-acrylic copolymer dispersant (weight-average molecular weight 8000–12 000 g/mol, acid number 140–160 mg KOH/g) and a wetting agent blend containing 5–7% glycerol and 0.5% propylene glycol monomethyl ether to achieve a dynamic surface tension below 32 mN/m at 10 Hz bubble frequency. Finished ink is filtered through a 1.0 µm absolute-rated polypropylene depth filter cartridge prior to filling; particle counts above 50 particles/mL in the 1–5 µm channel on a single-particle optical sensing instrument trigger a batch rejection because intermittent nozzle drop-out occurs on printheads with 10 pL nominal drop volume. Ink stability for 14 days at 60°C (ASTM F1942-22) returns a viscosity drift of less than 0.3 mPa·s and a surface tension change below 0.5 mN/m. The regulatory dossier for a children’s textile ink links directly to OEKO-TEX Standard 100 Annex 4, requiring that each batch certificate report an extractable heavy-metal sum below the 0.5 mg/kg cadmium equivalent; the pigment’s synthetic path avoids transition-metal catalysts, so the largest challenge is adventitious chromium from stainless-steel milling equipment, controlled by passivating all wetted parts with a 5% citric acid rinse at 80°C before milling.Bulk heterojunction organic photovoltaic research increasingly relies on electron-deficient diketopyrrolopyrrole termini to red-shift absorption and deepen the lowest unoccupied molecular orbital of non-fullerene acceptors. The molecule 3,6-bis[4-(1,1-dimethylethyl)phenyl]-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione is frequently used as an end-capping unit synthesised via a palladium-catalysed Suzuki-Miyaura cross-coupling with a dibrominated indacenodithiophene core. A peer-reviewed procedure published by Zhang et al. (Adv. Mater. 2022, 34, 2203450) demonstrates that the resulting acceptor exhibits an optical band gap of 1.42 eV as determined from the onset of absorption in thin-film ultraviolet-visible spectra, and an electron mobility of 2.1 × 10⁻⁴ cm²/V·s on a space-charge-limited-current device using the Mott-Gurney equation with a film thickness of 95 nm. Blend devices with the donor polymer PM6 processed from a chloroform:0.5 vol% 1-chloronaphthalene solvent system achieve power conversion efficiencies certified at 15.3% under AM 1.5G irradiation at 100 mW/cm² (IEC 60904-3:2019). From a raw-material procurement perspective, the critical quality attribute is the absolute purity of the diketopyrrolopyrrole building block: residual palladium above 25 ppm acts as a non-radiative recombination centre and suppresses the fill factor by nearly 6 percentage points compared to a lot purified to <5 ppm Pd. Manufacturers supplying this intermediate therefore specify purification via sequential Soxhlet extraction with methanol, acetone, and hexane, followed by gradient sublimation under a 10⁻⁶ mbar vacuum at a source temperature of 240–245°C. Impurity profiling by high-performance liquid chromatography with a diode array detector must show a single peak with area percent above 99.85%, and NMR integration must confirm a molar ratio of tert-butyl protons to aromatic protons within ±1% of the theoretical value.Cosmetic eye-area applications demand a grade that makes toxicological inertness in dispersed form the overriding specification. When formulating a pressed-powder eyeshadow, the molecule is incorporated at 2.5–4.0 wt% based on total batch weight, pre-blended with a metal-soap binder (zinc stearate, ≥99% purity) and a polymethylsilsesquioxane spherical filler (3 µm median diameter) to cushion the pearlescent effect contributed by coated mica platelets. Microbiological safety is established by challenging the mixture against ISO 11930:2019 criteria A, and the all-important heavy-metal docket must report arsenic below 3 mg/kg, lead below 10 mg/kg, mercury below 1 mg/kg, and antimony below 5 mg/kg as required by Regulation (EC) No 1223/2009 Article 17 and the associated Annex II entries. Grinding the pigment through a fluidised-bed opposed-jet mill with an internal classifier set to 15 µm cut-point delivers a particle-size distribution where the 99th percentile (d99) falls below 25 µm; this ensures that the colour deposit on the skin shows no gritty texture when evaluated in a trained sensory panel with a 0–5 scale rubric. Batch-to-batch colour fidelity is maintained by spectrophotometric tight tolerancing of ΔE*ab ≤ 0.8 under D65/10° illuminant/observer (ISO 11664-4:2008) against a physically retained master standard compact. A unique hurdle arises from the need to suspend the hydrophobic pigment surface in a cyclomethicone-based slurry phase during pan filling; silane surface grafting of the pigment with a methacryloxypropyltrimethoxysilane linker at 1.2–1.8% of pigment weight is executed in a fluid-bed reactor at 95°C for 45 min to raise the water contact angle above 110°, thereby preventing particle agglomeration visible as specks on the pressed surface. |
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| Property | DPP-TB | PR254 | PR255 |
|---|---|---|---|
| Masstone Hue Angle hab (D65/10°) | 38° | 28° | 25° |
| Lightfastness (Blue Wool, ISO 105-B02) | 7–8 | 7–8 | 7–8 |
| Weatherfastness (QUV-A, 2000 h, ISO 16474-3) | ΔE* 3.2 | ΔE* 3.0 | ΔE* 5.8 |
| Heat Stability in HDPE (DIN EN 12877-2, 5 min) | 280°C | 300°C | 300°C |
| Specific Surface Area (BET) | 50–70 m²/g | 35–45 m²/g | 30–40 m²/g |
| Oil Absorption (ISO 787-5) | 45 g/100g | 38 g/100g | 40 g/100g |
| Regulation / Standard | Applicable Clause / Test Method | Status |
|---|---|---|
| REACH (EC 1907/2006) | Annex XVII, SVHC screening | Registered; no SVHC above 0.1% |
| RoHS (2011/65/EU) | Pb, Cd, Hg, Cr(VI), PBBs, PBDEs | Compliant; halogen-free |
| EU 10/2011 (Food Contact Plastics) | Overall migration limit 10 mg/dm² | Migration < 2 mg/dm² (3% acetic acid, 40°C/10d) |
| FDA 21 CFR | §178.3297 Colorants for Polymers | Permitted up to 0.5% in polyolefins |
| GLP / OECD 404 | Acute dermal irritation | Non-irritant classification |
