Industrial Organic Pigments

Hunger, Klaus; Schmidt, Martin

doi:10.1002/9783527648320

Cited by 44 publications

(27 citation statements)

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“…The Cl deficiency does not change the crystal structure. Organic pigments are known to easily form mixed crystals (solid solution) (Schmidt et al, 2006(Schmidt et al, , 2007Paulus et al, 2007;Hunger & Schmidt, 2018;Schlesinger et al, 2020). Correspondingly, the mixture with 14-15 Cl atoms will surely form a solid solution having the same crystal structure as CuPcCl 16 .…”

Section: Figurementioning

confidence: 99%

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Crystal structure of copper perchlorophthalocyanine analysed by 3D electron diffraction

Gorelik

Habermehl

Shubin

et al. 2021

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Copper perchlorophthalocyanine (CuPcCl16, CuC32N8Cl16, Pigment Green 7) is one of the commercially most important green pigments. The compound is a nanocrystalline fully insoluble powder. Its crystal structure was first addressed by electron diffraction in 1972 [Uyeda et al. (1972). J. Appl. Phys. 43, 5181–5189]. Despite the commercial importance of the compound, the crystal structure remained undetermined until now. Using a special vacuum sublimation technique, micron-sized crystals could be obtained. Three-dimensional electron diffraction (3D ED) data were collected in two ways: (i) in static geometry using a combined stage-tilt/beam-tilt collection scheme and (ii) in continuous rotation mode. Both types of data allowed the crystal structure to be solved by direct methods. The structure was refined kinematically with anisotropic displacement parameters for all atoms. Due to the pronounced crystal mosaicity, a dynamic refinement was not feasible. The unit-cell parameters were verified by Rietveld refinement from powder X-ray diffraction data. The crystal structure was validated by many-body dispersion density functional theory (DFT) calculations. CuPcCl16 crystallizes in the space group C2/m (Z = 2), with the molecules arranged in layers. The structure agrees with that proposed in 1972.

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Section: Figurementioning

confidence: 99%

“…Copper phthalocyanine (CuPc, Scheme 1) is the most important blue pigment used today (Hunger & Schmidt, 2018).…”

Section: Introductionmentioning

confidence: 99%

Crystal structure of copper perchlorophthalocyanine analysed by 3D electron diffraction

Gorelik

Habermehl

Shubin

et al. 2021

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…This is not only true for NaOEt, but also for other alkoxides. For example, sodium tert-amylate (sodium 2-methyl-2-butoxide, NaO t Am) is used industrially on a multi-ton scale in the synthesis of diketopyrrolopyrrole pigments, which today are the most commonly used pigments for red car coatings (Hunger & Schmidt, 2018).…”

Section: Generalmentioning

confidence: 99%

Disordered sodium alkoxides from powder data: crystal structures of sodium ethoxide, propoxide, butoxide and pentoxide, and some of their solvates

Beske

Cronje

Schmidt

et al. 2021

Acta Crystallogr B Struct Sci Cryst Eng Mater

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The crystal structures of sodium ethoxide (sodium ethanolate, NaOEt), sodium n-propoxide (sodium n-propanolate, NaO n Pr), sodium n-butoxide (sodium n-butanolate, NaO n Bu) and sodium n-pentoxide (sodium n-amylate, NaO n Am) were determined from powder X-ray diffraction data. NaOEt crystallizes in space group P 421 m, with Z = 2, and the other alkoxides crystallize in P4/nmm, with Z = 2. To resolve space-group ambiguities, a Bärnighausen tree was set up, and Rietveld refinements were performed with different models. In all structures, the Na and O atoms form a quadratic net, with the alkyl groups pointing outwards on both sides (anti-PbO type). The alkyl groups are disordered. The disorder becomes even more pronounced with increasing chain length. Recrystallization from the corresponding alcohols yielded four sodium alkoxide solvates: sodium ethoxide ethanol disolvate (NaOEt·2EtOH), sodium n-propoxide n-propanol disolvate (NaO n Pr·2 n PrOH), sodium isopropoxide isopropanol pentasolvate (NaO i Pr·5 i PrOH) and sodium tert-amylate tert-amyl alcohol monosolvate (NaO t Am· t AmOH, t Am = 2-methyl-2-butyl). Their crystal structures were determined by single-crystal X-ray diffraction. All these solvates form chain structures consisting of Na+, –O− and –OH groups, encased by alkyl groups. The hydrogen-bond networks diverge widely among the solvate structures. The hydrogen-bond topology of the i PrOH network in NaO i Pr·5 i PrOH shows branched hydrogen bonds and differs considerably from the networks in pure crystalline i PrOH.

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“…These linkages are found in pigment classes including β-naphthols, arylide (Hansa) yellows, Naphthol AS, diarylide yellow and oranges, BONA pigments, benzimidazolones, and disazo condensation pigments. More recently, polycyclic pigments such as quinacridones, phthalocyanines, perinones, perylenes and diketopyrrolopyrrole have been introduced [1].…”

Section: Introductionmentioning

confidence: 99%

The synthesis characterization of historical novel azo pigments: implications for conservation science

Lomax

2019

Herit Sci

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Industrial Organic Pigments

Cited by 44 publications

References 0 publications

Crystal structure of copper perchlorophthalocyanine analysed by 3D electron diffraction

Crystal structure of copper perchlorophthalocyanine analysed by 3D electron diffraction

Disordered sodium alkoxides from powder data: crystal structures of sodium ethoxide, propoxide, butoxide and pentoxide, and some of their solvates

The synthesis characterization of historical novel azo pigments: implications for conservation science

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