26 Diketopyrrolopyrrole (DPP) pigments
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Robert Christie
Abstract
Since their industrial introduction in the 1980s, DPP pigments now constitute a highly important group of high-performance carbonyl pigments. The DPP system was first discovered by accident in 1974, and was subsequently re-investigated by Ciba Geigy who recognized its potential to provide commercial organic pigments. DPP pigments exhibit strong similarities compared with quinacridone pigments, in terms of their molecular and crystal structures and their properties, including low solubility and excellent fastness properties. X-ray crystal structural analysis has demonstrated that their technical performance is the result of intermolecular hydrogen bonding and π-π stacking interactions in the crystal lattice structure. Based on a simple retrosynthetic analysis, an efficient synthetic process was developed by Ciba Geigy for their large-scale manufacture. DPP pigments currently provide orange through to reddish violet shades and have become of special importance in providing brilliant saturated red shades with the outstanding durability required for applications such as automotive paints.
Abstract
Since their industrial introduction in the 1980s, DPP pigments now constitute a highly important group of high-performance carbonyl pigments. The DPP system was first discovered by accident in 1974, and was subsequently re-investigated by Ciba Geigy who recognized its potential to provide commercial organic pigments. DPP pigments exhibit strong similarities compared with quinacridone pigments, in terms of their molecular and crystal structures and their properties, including low solubility and excellent fastness properties. X-ray crystal structural analysis has demonstrated that their technical performance is the result of intermolecular hydrogen bonding and π-π stacking interactions in the crystal lattice structure. Based on a simple retrosynthetic analysis, an efficient synthetic process was developed by Ciba Geigy for their large-scale manufacture. DPP pigments currently provide orange through to reddish violet shades and have become of special importance in providing brilliant saturated red shades with the outstanding durability required for applications such as automotive paints.
Kapitel in diesem Buch
- Frontmatter I
- Preface V
- Contents VII
- List of contributors XV
- 23 Color measurement 407
- 24 Cyanine dyes 465
- 25 Diarylethene dyes 503
- 26 Diketopyrrolopyrrole (DPP) pigments 525
- 27 Dioxazine pigments 535
- 28 Disazo (Bishydrazone) condensation pigments 543
- 29 Disazo (Bishydrazone) pigments based on acetoacetanilides 555
- 30 Disazo (Bishydrazone) pigments based on pyrazolones 571
- 31 Dyes: quantum chemical calculation of electronic spectra 577
- 32 Effect pigments 605
- 33 Fluorescence and fluorescent dyes 611
- 34 Fulgide dyes 651
- 35 Hemicyanine dyes 671
- 36 Hemioxonol dyes 685
- 37 Historical pigments, dyes and binders 691
- 38 Indophenol and related dyes 749
- 39 Inorganic luminescent pigments 765
- 40 Iron blue pigments 777
- 41 Iron oxide pigments 783
- 42 Merocyanine dyes 799
- 43 Metal complex pigments 815
- 44 Metal effect pigments 829
- Index 849
Kapitel in diesem Buch
- Frontmatter I
- Preface V
- Contents VII
- List of contributors XV
- 23 Color measurement 407
- 24 Cyanine dyes 465
- 25 Diarylethene dyes 503
- 26 Diketopyrrolopyrrole (DPP) pigments 525
- 27 Dioxazine pigments 535
- 28 Disazo (Bishydrazone) condensation pigments 543
- 29 Disazo (Bishydrazone) pigments based on acetoacetanilides 555
- 30 Disazo (Bishydrazone) pigments based on pyrazolones 571
- 31 Dyes: quantum chemical calculation of electronic spectra 577
- 32 Effect pigments 605
- 33 Fluorescence and fluorescent dyes 611
- 34 Fulgide dyes 651
- 35 Hemicyanine dyes 671
- 36 Hemioxonol dyes 685
- 37 Historical pigments, dyes and binders 691
- 38 Indophenol and related dyes 749
- 39 Inorganic luminescent pigments 765
- 40 Iron blue pigments 777
- 41 Iron oxide pigments 783
- 42 Merocyanine dyes 799
- 43 Metal complex pigments 815
- 44 Metal effect pigments 829
- Index 849
