Details

Industrial Organic Pigments


Industrial Organic Pigments

Production, Crystal Structures, Properties, Applications
4th Completely Revised Edition

von: Klaus Hunger, Martin U. Schmidt, Thomas Heber, Friedrich Reisinger, Stefan Wannemacher

259,99 €

Verlag: Wiley-VCH
Format: PDF
Veröffentl.: 26.04.2019
ISBN/EAN: 9783527648351
Sprache: englisch
Anzahl Seiten: 804

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Beschreibungen

<p>Revised and updated, this highly acclaimed work, now in its fourth edition, remains the most comprehensive source of information available on organic pigments. It provides up-to-date information on synthesis, reaction mechanism, physical and chemical properties, test methods, and applications of all the industrially produced organic pigments available on the world market.</p> <p>This <i><b>fourth edition</b></i> now includes new chapters on the latest applications and three-dimensional X-ray analysis, while the chapters on legislation, ecology, and toxicology have been rewritten to reflect recent developments.</p> <ul> <li>Sets the international standard for information on the synthesis, reaction mechanisms, properties, relevant test methods, and applications of organic pigments</li> <li>Contains all industrially produced pigments of the world market, even those which can no longer be found in producers’ catalogs are described</li> <li>Standardized methods allow test results to be compared throughout the book</li> <li>The reader is given useful hints as to which pigment is best for a given application</li> <li>Clearly structured and concise text with up-to-date references to the pertinent literature</li> <li>Ecological and toxicological properties of organic pigments are outlined</li> <li>Appendix offers invaluable flow diagrams on the manufacture of numerous pigments, a table of all described pigments with information about their C.I. and CAS registration, and an in-depth subject index</li> </ul>
<p>List of Contributors</p> <p>Preface to the Fourth Edition xix</p> <p>Preface to the Third Edition xxi</p> <p>Preface to the Second Edition xxiii</p> <p>Preface to the First Edition xxv</p> <p>List of Abbreviations xxvii</p> <p><b>1 General 1</b></p> <p>1.1 Definition: Pigments and Dyes 1</p> <p>1.1.1 Organic and Inorganic Pigments 2</p> <p>1.2 Historical 3</p> <p>1.3 Classification of Organic Pigments 4</p> <p>1.3.1 Hydrazone Pigments (Formerly Called Azo Pigments) (Chapter 2) 4</p> <p>1.3.1.1 Monohydrazone Yellow and Orange Pigments (Formerly Called Monoazo Yellow and Orange Pigments) (Section 2.3) 5</p> <p>1.3.1.2 Dihydrazone Pigments (Formerly Called Disazo Pigments) (Section 2.4) 5</p> <p>1.3.1.3 β-Naphthol Pigments (Section 2.5) 5</p> <p>1.3.1.4 Naphthol AS Pigments (Section 2.6) 5</p> <p>1.3.1.5 Hydrazone Pigment Lakes (Formerly Called Azo Pigment Lakes) (Section 2.7) 6</p> <p>1.3.1.6 Benzimidazolone Pigments (Section 2.8) 6</p> <p>1.3.1.7 Dihydrazone Condensation Pigments (Formerly Called Disazo Condensation Pigments) (Section 2.9) 7</p> <p>1.3.2 Polycyclic Pigments (Chapter 3) 7</p> <p>1.3.2.1 Phthalocyanine Pigments (Section 3.1) 7</p> <p>1.3.2.2 Quinacridone Pigments (Section 3.2) 7</p> <p>1.3.2.3 Perylene and Perinone Pigments (Section 3.4) 8</p> <p>1.3.2.4 Diketopyrrolopyrrole (DPP) Pigments (Section 3.5) 8</p> <p>1.3.2.5 Thioindigo Pigments (Section 3.6) 8</p> <p>1.3.2.6 Pigments Derived from Anthraquinone (Section 3.7) 8</p> <p>1.3.2.7 Dioxazine Pigments (Section 3.8) 9</p> <p>1.3.2.8 Quinophthalone Pigments (Section 3.9) 9</p> <p>1.3.2.9 Isoindolinone and Isoindoline Pigments 9</p> <p>1.3.3 Miscellaneous Pigments (Chapter 4) 10</p> <p>1.3.3.1 Triarylcarbonium Pigments (Section 4.1) 10</p> <p>1.3.3.2 Metal Complex Pigments (Section 4.2) 10</p> <p>1.4 Relationship between Chemical Structure and Pigment Properties 10</p> <p>1.4.1 Hue 11</p> <p>1.4.2 Tinctorial Strength 14</p> <p>1.4.3 Lightfastness and Weatherfastness 17</p> <p>1.4.4 Solvent and Migration Fastness 18</p> <p>1.5 Physical Characterization of Pigments 20</p> <p>1.5.1 Specific Surface Area 23</p> <p>1.5.2 Particle Size Distribution 26</p> <p>1.5.2.1 Determination of Particle Size by Ultrasedimentation 27</p> <p>1.5.2.2 Determination by Electron Microscopy 28</p> <p>1.5.2.3 Data Representation 33</p> <p>1.5.3 Crystal Structure and Polymorphism 37</p> <p>1.5.3.1 Effect of the Crystal Structure on the Optical Properties 39</p> <p>1.5.3.2 Polymorphism 41</p> <p>1.5.3.3 Identification of Polymorphic Forms by X-Ray Powder Diffraction 44</p> <p>1.5.3.4 Crystal Structure Determination 44</p> <p>1.5.3.5 Prediction of Crystal Structures; Crystal Engineering 47</p> <p>1.5.4 Crystallinity 48</p> <p>1.6 Important Application Properties and Concepts 51</p> <p>1.6.1 Colouristic Properties (by F. Gläser) 52</p> <p>1.6.1.1 Colour 52</p> <p>1.6.1.2 Colour Depth 55</p> <p>1.6.1.3 Colour Differences 56</p> <p>1.6.1.4 Optical Behaviour of Pigmented Coatings 56</p> <p>1.6.1.5 Tinctorial Strength 58</p> <p>1.6.1.6 Hiding Power 60</p> <p>1.6.1.7 Transparency 61</p> <p>1.6.2 Fastness to Solvents and Special Application Fastness 61</p> <p>1.6.2.1 Organic Solvents 61</p> <p>1.6.2.2 Water, Soap, Alkali and Acids 62</p> <p>1.6.2.3 Pigment Performance in Special Applications 65</p> <p>1.6.2.4 Textile Fastness Properties 66</p> <p>1.6.3 Migration 67</p> <p>1.6.3.1 Blooming 68</p> <p>1.6.3.2 Bleeding/Overspraying Fastness 71</p> <p>1.6.4 Disturbances during the Processing of Pigmented Systems 75</p> <p>1.6.4.1 Plate-Out 75</p> <p>1.6.4.2 Overpigmentation/Chalking 76</p> <p>1.6.4.3 Distortion/Nucleation in Polymers 77</p> <p>1.6.5 Dispersion 78</p> <p>1.6.5.1 General Considerations 78</p> <p>1.6.5.2 Desagglomeration of Pigment Particles 80</p> <p>1.6.5.3 Wetting of Pigment Particle Surfaces 80</p> <p>1.6.5.4 Distribution of the Dispersed Pigment in its Medium 84</p> <p>1.6.5.5 Stabilization 86</p> <p>1.6.5.6 Dispersion and the Critical Pigment Volume Concentration 86</p> <p>1.6.5.7 Test Methods 87</p> <p>1.6.5.8 Flush Pastes 93</p> <p>1.6.5.9 Pigment Preparations 94</p> <p>1.6.6 Lightfastness and Weatherfastness 94</p> <p>1.6.6.1 Definition and General Information 94</p> <p>1.6.6.2 Evaluation Techniques and Equipment 95</p> <p>1.6.6.3 Factors Determining the Lightfastness 98</p> <p>1.6.7 Thermal Stability 104</p> <p>1.6.8 Flow Properties of Pigmented Systems 110</p> <p>1.6.8.1 Rheological Properties 110</p> <p>1.6.8.2 Viscoelastic Properties 114</p> <p>1.6.8.3 Influence on the Flow Properties 114</p> <p>1.6.8.4 Correlation between Flow Behaviour and Rheological Parameters 115</p> <p>1.6.8.5 Rheological Measurements 116</p> <p>1.7 Particle Size Distribution and Application Properties of Pigmented Media 119</p> <p>1.7.1 Tinctorial Strength 120</p> <p>1.7.2 Hue 122</p> <p>1.7.3 Hiding Power, Transparency 126</p> <p>1.7.4 Lightfastness and Weatherfastness 131</p> <p>1.7.5 Dispersibility 133</p> <p>1.7.6 Gloss 136</p> <p>1.7.7 Solvent and Migration Fastness 139</p> <p>1.7.8 Flow 141</p> <p>1.8 Areas of Application for Organic Pigments 142</p> <p>1.8.1 Printing Inks 144</p> <p>1.8.1.1 Offset Printing 144</p> <p>1.8.1.2 Gravure Printing 149</p> <p>1.8.1.3 Solvent-Based Flexographic Packaging Printing 152</p> <p>1.8.1.4 Non-impact Printing 154</p> <p>1.8.1.5 Security Printing 155</p> <p>1.8.2 Coatings 155</p> <p>1.8.2.1 Oxidatively Drying Paints 156</p> <p>1.8.2.2 Oven Drying Systems 156</p> <p>1.8.2.3 Emulsion Paints 162</p> <p>1.8.3 Plastics 163</p> <p>1.8.3.1 Polyolefins 167</p> <p>1.8.3.2 Poly(vinyl chloride) (PVC) 169</p> <p>1.8.3.3 Polyurethane 174</p> <p>1.8.3.4 Polyamide, Polycarbonate, Polyester, Polyoxymethylene 175</p> <p>1.8.3.5 Polystyrene, Styrene-Copolymers, Poly(methyl methacrylate) 175</p> <p>1.8.3.6 Elastomers 177</p> <p>1.8.3.7 Thermoplastic Elastomers (TPEs) 178</p> <p>1.8.3.8 Thermosets (Thermosetting Plastics) 179</p> <p>1.8.3.9 Spin Dyeing 181</p> <p>1.8.4 Other Areas of Application 183</p> <p>1.8.4.1 Miscellaneous Applications 183</p> <p>1.8.4.2 Colouration of Glass with Organic Pigments 184</p> <p>References for Chapter 1 184</p> <p><b>2 Hydrazone Pigments (Formerly Called Azo Pigments) 193</b></p> <p>2.1 Starting Materials 196</p> <p>2.1.1 Diazo Components 197</p> <p>2.1.1.1 Reduction Methods 199</p> <p>2.1.2 Coupling Compounds 200</p> <p>2.1.2.1 Acetoacetic Anilides 201</p> <p>2.1.2.2 β-Naphthol and its Derivatives 201</p> <p>2.1.2.3 Pyrazolone Derivatives 204</p> <p>2.1.3 Important Intermediates 204</p> <p>2.2 Synthesis of Hydrazone Pigments 205</p> <p>2.2.1 Diazotization 206</p> <p>2.2.1.1 Diazotization Mechanism 207</p> <p>2.2.1.2 Methods of Diazotization 207</p> <p>2.2.2 Coupling 209</p> <p>2.2.2.1 Coupling Techniques 211</p> <p>2.2.3 Finishing 213</p> <p>2.2.4 Filtration, Drying and Milling 214</p> <p>2.2.5 Hydrazone Pigment Synthesis by Continuous Operation 215</p> <p>2.2.5.1 Diazotization by Continuous Technique 216</p> <p>2.2.5.2 Coupling by Continuous Process 218</p> <p>2.2.5.3 Process Control 219</p> <p>2.2.6 Production Units for Hydrazone Pigment Manufacture by Batch Operation 219</p> <p>2.3 Monohydrazone Yellow and Orange Pigments (Formerly Called Monoazo Yellow and Orange Pigments) 221</p> <p>2.3.1 Chemistry, Manufacture and Crystal Structures 223</p> <p>2.3.1.1 Non-laked Monohydrazone Yellow and Orange Pigments 223</p> <p>2.3.1.2 Monohydrazone Yellow Pigment Lakes 227</p> <p>2.3.2 Properties 232</p> <p>2.3.2.1 Non-laked Monohydrazone Yellow and Orange Pigments 232</p> <p>2.3.2.2 Monohydrazone Yellow Pigment Lakes 233</p> <p>2.3.3 Application 233</p> <p>2.3.4 Commercially Available Monohydrazone Yellow and Orange Pigments 235</p> <p>2.3.4.1 General 235</p> <p>2.3.4.2 Individual Non-laked Monohydrazone Yellow and Orange Pigments 235</p> <p>2.3.4.3 Monohydrazone Yellow Pigment Lakes 247</p> <p>2.4 Dihydrazone Pigments (Formerly Called Disazo Pigments) 251</p> <p>2.4.1 Diarylide Yellow Pigments 253</p> <p>2.4.1.1 Chemistry, Manufacture and Crystal Structures 253</p> <p>2.4.1.2 Properties 258</p> <p>2.4.1.3 Application 259</p> <p>2.4.1.4 Commercially Available Diarylide Yellow Pigments 262</p> <p>2.4.2 Bisacetoacetarylide Pigments 278</p> <p>2.4.2.1 Chemistry, Manufacture and Crystal Strctures 278</p> <p>2.4.2.2 Properties and Application 280</p> <p>2.4.2.3 Commercially Available Bisacetoacetarylide Pigments 281</p> <p>2.4.3 Dihydrazonepyrazolone Pigments (Formerly Called Disazopyrazolone Pigments) 284</p> <p>2.4.3.1 Chemistry, Manufacture and Crystal Structures 284</p> <p>2.4.3.2 Properties 285</p> <p>2.4.3.3 Application 285</p> <p>2.4.3.4 Commercially Available Dihydrazonepyrazolone Pigments 285</p> <p>2.5 β-Naphthol Pigments 290</p> <p>2.5.1 Chemistry, Manufacture and Crystal Structures 291</p> <p>2.5.1.1 Crystal Structures 292</p> <p>2.5.2 Properties 293</p> <p>2.5.3 Application 293</p> <p>2.5.4 Commercially Available β-Naphthol Pigments 296</p> <p>2.6 Naphthol AS Pigments 300</p> <p>2.6.1 Chemistry, Manufacture and Crystal Structures 302</p> <p>2.6.1.1 Crystal Structures 303</p> <p>2.6.2 Properties 307</p> <p>2.6.3 Application 309</p> <p>2.6.4 Commercially Available Naphthol AS Pigments 310</p> <p>2.6.4.1 General 310</p> <p>2.6.4.2 Naphthol AS Pigments with Simple Substituents 310</p> <p>2.6.4.3 Naphthol AS Pigments with Sulfonamide or Carbonamide Groups 324</p> <p>2.7 Red Hydrazone Pigment Lakes (Formerly Called Red Azo Pigment Lakes) 337</p> <p>2.7.1 β-Naphthol Pigment Lakes 338</p> <p>2.7.1.1 Chemistry, Manufacture and Crystal Structures 338</p> <p>2.7.1.2 Properties 341</p> <p>2.7.1.3 Application 342</p> <p>2.7.1.4 Commercially Available β-Naphthol Pigment Lakes 342</p> <p>2.7.2 BONA Pigment Lakes 349</p> <p>2.7.2.1 Chemistry, Manufacture and Crystal Structures 349</p> <p>2.7.2.2 Properties 350</p> <p>2.7.2.3 Application 351</p> <p>2.7.2.4 Commercially Available BONA Pigment Lakes 352</p> <p>2.7.3 Naphthol AS Pigment Lakes 362</p> <p>2.7.3.1 Chemistry, Manufacture, Crystal Structures, Properties and Applications 362</p> <p>2.7.3.2 Commercially Available Naphthol AS Pigment Lakes 362</p> <p>2.7.4 Naphthalene Sulfonic Acid Pigment Lakes 366</p> <p>2.7.4.1 Chemistry, Manufacture, Crystal Structures, Properties and Applications 366</p> <p>2.7.4.2 Commercially Available Naphthalene Sulfonic Acid Pigment Lakes 366</p> <p>2.8 Benzimidazolone Pigments 370</p> <p>2.8.1 Chemistry, Manufacture and Crystal Structures 372</p> <p>2.8.1.1 Coupling Components for Yellow and Orange Benzimidazolone Pigments 372</p> <p>2.8.1.2 Coupling Components for Red Benzimidazolone Pigments 373</p> <p>2.8.1.3 Pigment Synthesis and Aftertreatment 373</p> <p>2.8.1.4 Crystal Structures 374</p> <p>2.8.2 Properties 380</p> <p>2.8.3 Application 381</p> <p>2.8.4 Commercially Available Benzimidazolone Pigments 382</p> <p>2.8.4.1 The Yellow and Orange Series 382</p> <p>2.8.4.2 The Red and Brown Series 393</p> <p>2.8.5 Quinoxalinedione Pigments 400</p> <p>2.8.5.1 Chemistry, Manufacture and Crystal Structures 400</p> <p>2.8.5.2 Properties and Applications 402</p> <p>2.9 Dihydrazone Condensation Pigments (Formerly Called Disazo Condensation Pigments) 403</p> <p>2.9.1 Chemistry, Manufacture and Crystal Structures 404</p> <p>2.9.2 Properties 407</p> <p>2.9.3 Application 407</p> <p>2.9.4 Commercially Available Dihydrazone Condensation Pigments 409</p> <p>2.9.4.1 General 409</p> <p>2.9.4.2 Yellow Series 409</p> <p>2.9.4.3 Orange, Red and Brown Pigments 414</p> <p>References for Chapter 2 421</p> <p><b>3 Polycyclic Pigments 425</b></p> <p>3.1 Phthalocyanine Pigments 426</p> <p>3.1.1 Starting Materials 427</p> <p>3.1.1.1 Phthalic Anhydride 428</p> <p>3.1.1.2 Phthalonitrile 428</p> <p>3.1.2 Manufacture 428</p> <p>3.1.2.1 Phthalonitrile Process 429</p> <p>3.1.2.2 Phthalic Anhydride/Urea Process 432</p> <p>3.1.2.3 Manufacturing the Different Crystal Modifications 435</p> <p>3.1.2.4 Phase- and Flocculation-Stabilized Copper Phthalocyanine Blue Pigments 437</p> <p>3.1.2.5 Manufacture of Green Types 438</p> <p>3.1.2.6 Metal-Free Phthalocyanine Blue 439</p> <p>3.1.3 Crystal Structures and Properties 440</p> <p>3.1.4 Application 445</p> <p>3.1.5 Commercially Available Phthalocyanine Pigments 447</p> <p>3.2 Quinacridone Pigments 460</p> <p>3.2.1 Starting Materials, Manufacture and Crystal Structures 461</p> <p>3.2.1.1 Thermal Ring Closure 461</p> <p>3.2.1.2 Acidic Ring Closure 463</p> <p>3.2.1.3 Dihalo-terephthalic Acid Process 463</p> <p>3.2.1.4 Hydroquinone Process 464</p> <p>3.2.1.5 Substituted Quinacridones 465</p> <p>3.2.1.6 Quinacridone Quinone 466</p> <p>3.2.1.7 Polymorphism 466</p> <p>3.2.1.8 Crystal Structures 468</p> <p>3.2.1.9 Solid Solutions 475</p> <p>3.2.2 Properties 477</p> <p>3.2.3 Application 477</p> <p>3.2.4 Commercially Available Quinacridone Pigments 477</p> <p>3.3 Vat Dyes Prepared as Pigments 487</p> <p>3.4 Perylene and Perinone Pigments 488</p> <p>3.4.1 Perylene Pigments 488</p> <p>3.4.1.1 Preparation of the Starting Materials 489</p> <p>3.4.1.2 Chemistry, Manufacture 489</p> <p>3.4.1.3 Crystal Structures and Properties 491</p> <p>3.4.1.4 Application 498</p> <p>3.4.1.5 Commercially Available Perylene Pigments 498</p> <p>3.4.2 Perinone Pigments 504</p> <p>3.4.2.1 Preparation of the Starting Materials 504</p> <p>3.4.2.2 Chemistry, Manufacture and Crystal Structures 505</p> <p>3.4.2.3 Properties 510</p> <p>3.4.2.4 Commercially Available Perinone Pigments and Their Application 510</p> <p>3.4.3 Semiperinone Pigments and Similar Pigments 513</p> <p>3.5 Diketopyrrolopyrrole (DPP) Pigments 514</p> <p>3.5.1 Chemistry, Manufacture and Crystal Structures 514</p> <p>3.5.2 Properties and Application 520</p> <p>3.5.3 Commercially Available DPP Pigments 520</p> <p>3.6 Indigo, Thioindigo and Thiazine Indigo Pigments 525</p> <p>3.6.1 Indigo 525</p> <p>3.6.1.1 Crystal Structure 525</p> <p>3.6.1.2 Properties and Application 525</p> <p>3.6.2 Thioindigo Pigments 526</p> <p>3.6.2.1 Chemistry, Manufacture and Crystal Structures 526</p> <p>3.6.2.2 Properties and Application 528</p> <p>3.6.2.3 Commercially Available Thioindigo Pigments and Their Application 529</p> <p>3.6.3 Thiazine Indigo Pigments 532</p> <p>3.6.3.1 Chemistry, Manufacture and Crystal Structures 532</p> <p>3.6.3.2 Properties 534</p> <p>3.6.3.3 Commercially Available Thiazine Indigo Pigments and Their Application 534</p> <p>3.7 Various Polycyclic Pigments Derived from Anthraquinone 534</p> <p>3.7.1 Aminoanthraquinone Pigments 535</p> <p>3.7.1.1 Synthesis of 1-Aminoanthraquinone 535</p> <p>3.7.1.2 Anthraquinone-Hydrazone Pigments 536</p> <p>3.7.1.3 Other Aminoanthraquinone Pigments 538</p> <p>3.7.1.4 Commercially Available Aminoanthraquinone Pigments 542</p> <p>3.7.2 Hydroxyanthraquinone Pigments 544</p> <p>3.7.2.1 Commercially Available Hydroxyanthraquinone Pigments 546</p> <p>3.7.3 Heterocyclic Anthraquinone Pigments 546</p> <p>3.7.3.1 Anthrapyrimidine Pigments 546</p> <p>3.7.3.2 Indanthrone and Flavanthrone Pigments 548</p> <p>3.7.4 Polycarbocyclic Anthraquinone Pigments 557</p> <p>3.7.4.1 Pyranthrone Pigments 557</p> <p>3.7.4.2 Anthanthrone Pigments 561</p> <p>3.7.4.3 Isoviolanthrone Pigments 565</p> <p>3.7.4.4 Violanthrone Pigments 567</p> <p>3.8 Dioxazine Pigments 569</p> <p>3.8.1 Preparation of the Starting Materials 570</p> <p>3.8.2 Chemistry, Manufacture and Crystal Structures 570</p> <p>3.8.2.1 Crystal Structures 574</p> <p>3.8.3 Properties 574</p> <p>3.8.4 Commercially Available Dioxazine Pigments and Their Application 577</p> <p>3.9 Quinophthalone Pigments 581</p> <p>3.9.1 Chemistry, Manufacture and Crystal Structures 581</p> <p>3.9.2 Properties and Application 585</p> <p>3.9.3 Commercially Available Quinophthalone Pigments 585</p> <p>3.9.3.1 Pigment Yellow 138 585</p> <p>3.10 Isoindolinone and Isoindoline Pigments 586</p> <p>3.10.1 General 586</p> <p>3.10.1.1 Isoindolinone Pigments 586</p> <p>3.10.1.2 Isoindoline Pigments 587</p> <p>3.10.2 Chemistry, Manufacture and Crystal Structures 588</p> <p>3.10.2.1 Isoindolinone Pigments 588</p> <p>3.10.2.2 Isoindoline Pigments 591</p> <p>3.10.3 Properties 597</p> <p>3.10.3.1 Isoindolinone Pigments 597</p> <p>3.10.3.2 Isoindoline Pigments 597</p> <p>3.10.4 Application 597</p> <p>3.10.5 Commercially Available Isoindolinone and Isoindoline Pigments 597</p> <p>References for Chapter 3 606</p> <p><b>4 Miscellaneous Pigments 613</b></p> <p>4.1 Triarylcarbonium Pigments 613</p> <p>4.1.1 Inner Salts of Sulfonic Acids (Alkali Blue Types) 614</p> <p>4.1.1.1 Chemistry, Manufacture 615</p> <p>4.1.1.2 Properties and Application 619</p> <p>4.1.1.3 Commercially Available Alkali Blue Pigments 619</p> <p>4.1.2 Dye Salts with Complex Anions 622</p> <p>4.1.2.1 Chemistry, Manufacture and Crystal Structures 623</p> <p>4.1.2.2 Properties 629</p> <p>4.1.2.3 Application 630</p> <p>4.1.2.4 Commercially Available Dye Salts with Complex Anions 630</p> <p>4.1.3 Aluminium Pigment Lakes 638</p> <p>4.2 Metal Complex Pigments 640</p> <p>4.2.1 Chemistry, Synthesis and Crystal Structures 641</p> <p>4.2.1.1 Azo Metal Complexes 642</p> <p>4.2.1.2 Azomethine Metal Complexes 643</p> <p>4.2.2 Properties 647</p> <p>4.2.3 Application 647</p> <p>4.2.4 Commercially Available Metal Complex Pigments 647</p> <p>4.3 Pigments with Known Chemical Structure Which Cannot be Assigned to Other Chapters 655</p> <p>4.3.1 Pigment Yellow 101 655</p> <p>4.3.2 Pigment Yellow 148 657</p> <p>4.3.3 Pigment Yellow 182 657</p> <p>4.3.4 Pigment Yellow 201 659</p> <p>4.3.5 Quinolonoquinolone Pigments (P.Y.218, P.Y.220, P.Y.221) 659</p> <p>4.3.6 Pigment Orange 64 661</p> <p>4.3.7 Pigment Orange 67 661</p> <p>4.3.8 Pigment Red 90 662</p> <p>4.3.9 Pigment Red 252 664</p> <p>4.3.10 Pigment Blue 63 664</p> <p>4.3.11 Pigment Brown 22 665</p> <p>4.3.12 Pigment Black 1 665</p> <p>4.4 Pigments with Hitherto Unpublished Chemical Structures 666</p> <p>4.4.1 Pigment Yellow 99 666</p> <p>4.4.2 Pigment Yellow 187 667</p> <p>4.4.3 Pigment Yellow 214 667</p> <p>4.4.4 Pigment Orange 83 667</p> <p>4.4.5 Pigment Red 204 667</p> <p>4.4.6 Pigment Red 278 668</p> <p>4.4.7 Pigment Red 285 668</p> <p>4.4.8 Pigment Red 293 668</p> <p>4.4.9 Pigment Violet 51 669</p> <p>4.4.10 Pigment Black 20 669</p> <p>4.5 Organic/Inorganic Hybrid Pigments 669</p> <p>References for Chapter 4 673</p> <p><b>5 Legislation, Ecology, Toxicology 675</b></p> <p>5.1 Introduction 675</p> <p>5.2 Chemicals Legislation 676</p> <p>5.2.1 General 676</p> <p>5.2.1.1 Chemical Inventories 676</p> <p>5.2.1.2 GHS – Globally Harmonized System 677</p> <p>5.2.1.3 REACH (European Union) 679</p> <p>5.2.1.4 REACH Restricted Substances List 679</p> <p>5.2.2 Legislation Concerning Organic Pigments 681</p> <p>5.2.2.1 Food Packaging/Food Contact 683</p> <p>5.2.2.2 Purity Criteria 685</p> <p>5.2.2.3 Toys 687</p> <p>5.2.2.4 Consumer Goods 688</p> <p>5.3 Ecology 691</p> <p>5.4 Toxicology 692</p> <p>5.4.1 Acute Toxicity 693</p> <p>5.4.2 Irritation of Skin and Mucous Membrane 693</p> <p>5.4.3 Toxicity after Repeated Application 694</p> <p>5.4.4 Mutagenicity 694</p> <p>5.4.5 Chronic Toxicity – Carcinogenicity 694</p> <p>References for Chapter 5 696</p> <p><b>Reaction Schemes 699</b></p> <p>A1 Starting Materials (Section 2.1) 699</p> <p>A2 Synthesis of Hydrazone Pigments (Section 2.2) 700</p> <p>A3 Monohydrazone Yellow and Monohydrazone Orange Pigments (Section 2.3) 702</p> <p>A4 Dihydrazone Pigments (Section 2.4) 704</p> <p>A5 ß-Naphthol Pigments (Section 2.5) 705</p> <p>A6 Naphthol AS Pigments (Section 2.6) 706</p> <p>A7 Red Hydrazone Pigment Lakes (Section 2.7) 706</p> <p>A8 Benzimidazolone Pigments (Section 2.8) 709</p> <p>A9 Dihydrazone Condensation Pigments (Section 2.9) 710</p> <p>A10 Phthalocyanine Pigments (Section 3.1) 713</p> <p>A11 Quinacridone Pigments (Section 3.2) 715</p> <p>A12 Perylene and Perinone Pigments (Section 3.4) 721</p> <p>A13 Diketopyrrolopyrrole (DPP) Pigments (Section 3.5) 722</p> <p>A14 Indigo, Thioindigo and Thiazine Indigo Pigments (Section 3.6) 723</p> <p>A15 Various Polycyclic Pigments Derived from Anthraquinone (Section 3.7) 725</p> <p>A16 Dioxazine Pigments (Section 3.8) 729</p> <p>A17 Quinophthalone Pigments (Section 3.9) 730</p> <p>A18 Isoindolinone and Isoindoline Pigments (Section 3.10) 731</p> <p>A19 Triarylcarbonium Pigments (Section 4.1) 733</p> <p>A20 Metal Complex Pigments (Section 4.2) 736</p> <p>List of Commercially Available Pigments 739</p> <p>Index 755</p>
"...eignet sich das Buch zur Einfuhrung in die Thematik, aber auch erfahrene Anwender und Entwickler werden es als wertvolles Nachschlagewerk zu schatzen wissen...<br /> Der "Herbst/Hunger" ist auch in der dritten Auflage seinem Genre zwischen Lehrbuch und Nachschlagewerk treu geblieben. Es gibt kein vergleichbares Buch, das einem die physikalischen Grundlagen, die Chemie und die Anwendungseigenschaften organischer Buntpigmente so umfassend, kompakt und eingangig erschlie?t."<br /> <br /> Peter Erk, BASF Aktiengesellschaft, Ludwigshafen<br /> Angewandte Chemie 2004-116/34
<p><b>Klaus Hunger</b> (Dr. rer. nat., TU München) was the research director of the hydrazone pigments unit at Hoechst AG. Today, he is the Managing Director of Decernis GmbH.</p> <p><b>Martin U. Schmidt</b> (Dr. rer. nat., Aachen) was employed at Hoechst AG, later Clariant, in the pigment research group. Today, he is a professor at the Goethe University in Frankfurt. His main research interest is the determination of crystal structures of industrial organic pigments and pharmaceuticals.</p>
Revised and updated, this highly acclaimed work, now in its fourth edition, remains the most comprehensive source of information available on organic pigments. It provides up-to-date information on syntheses, structures, physical and chemical properties, test methods, and applications of all industrially produced organic pigments available on the world market.<br> The fourth edition has been completely revised and extended. The chapter on the product safety and the legislation of organic pigments has been rewritten to reflect recent developments.<br> Today it is known that all industrial "azo pigments" actually adopt the hydrazone-tautomeric form in the solid state. Correspondingly, for the first time all structural formulae now show the correct tautomer and the name "hydrazone pigments" is used throughout. Since the pigments' properties strongly depend on their crystal structures, for the first time all available information on the crystal structures of all industrial organic pigments has been compiled, including unpublished data from the authors' own work.<br> With its comprehensive survey of organic pigments and their industrial applications, this is the standard reference for everyone working with pigments, plastics, printing inks, paints and coatings.

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