List of Contributors Preface to the Fourth Edition xix Preface to the Third Edition xxi Preface to the Second Edition xxiii Preface to the First Edition xxv List of Abbreviations xxvii 1 General 1 1.1 Definition: Pigments and Dyes 1 1.1.1 Organic and Inorganic Pigments 2 1.2 Historical 3 1.3 Classification of Organic Pigments 4 1.3.1 Hydrazone Pigments (Formerly Called Azo Pigments) (Chapter 2) 4 1.
3.1.1 Monohydrazone Yellow and Orange Pigments (Formerly Called Monoazo Yellow and Orange Pigments) (Section 2.3) 5 1.3.1.2 Dihydrazone Pigments (Formerly Called Disazo Pigments) (Section 2.4) 5 1.
3.1.3 β-Naphthol Pigments (Section 2.5) 5 1.3.1.4 Naphthol AS Pigments (Section 2.6) 5 1.
3.1.5 Hydrazone Pigment Lakes (Formerly Called Azo Pigment Lakes) (Section 2.7) 6 1.3.1.6 Benzimidazolone Pigments (Section 2.8) 6 1.
3.1.7 Dihydrazone Condensation Pigments (Formerly Called Disazo Condensation Pigments) (Section 2.9) 7 1.3.2 Polycyclic Pigments (Chapter 3) 7 1.3.2.
1 Phthalocyanine Pigments (Section 3.1) 7 1.3.2.2 Quinacridone Pigments (Section 3.2) 7 1.3.2.
3 Perylene and Perinone Pigments (Section 3.4) 8 1.3.2.4 Diketopyrrolopyrrole (DPP) Pigments (Section 3.5) 8 1.3.2.
5 Thioindigo Pigments (Section 3.6) 8 1.3.2.6 Pigments Derived from Anthraquinone (Section 3.7) 8 1.3.2.
7 Dioxazine Pigments (Section 3.8) 9 1.3.2.8 Quinophthalone Pigments (Section 3.9) 9 1.3.2.
9 Isoindolinone and Isoindoline Pigments 9 1.3.3 Miscellaneous Pigments (Chapter 4) 10 1.3.3.1 Triarylcarbonium Pigments (Section 4.1) 10 1.3.
3.2 Metal Complex Pigments (Section 4.2) 10 1.4 Relationship between Chemical Structure and Pigment Properties 10 1.4.1 Hue 11 1.4.2 Tinctorial Strength 14 1.
4.3 Lightfastness and Weatherfastness 17 1.4.4 Solvent and Migration Fastness 18 1.5 Physical Characterization of Pigments 20 1.5.1 Specific Surface Area 23 1.5.
2 Particle Size Distribution 26 1.5.2.1 Determination of Particle Size by Ultrasedimentation 27 1.5.2.2 Determination by Electron Microscopy 28 1.5.
2.3 Data Representation 33 1.5.3 Crystal Structure and Polymorphism 37 1.5.3.1 Effect of the Crystal Structure on the Optical Properties 39 1.5.
3.2 Polymorphism 41 1.5.3.3 Identification of Polymorphic Forms by X-Ray Powder Diffraction 44 1.5.3.4 Crystal Structure Determination 44 1.
5.3.5 Prediction of Crystal Structures; Crystal Engineering 47 1.5.4 Crystallinity 48 1.6 Important Application Properties and Concepts 51 1.6.1 Colouristic Properties (by F.
Gläser) 52 1.6.1.1 Colour 52 1.6.1.2 Colour Depth 55 1.6.
1.3 Colour Differences 56 1.6.1.4 Optical Behaviour of Pigmented Coatings 56 1.6.1.5 Tinctorial Strength 58 1.
6.1.6 Hiding Power 60 1.6.1.7 Transparency 61 1.6.2 Fastness to Solvents and Special Application Fastness 61 1.
6.2.1 Organic Solvents 61 1.6.2.2 Water, Soap, Alkali and Acids 62 1.6.2.
3 Pigment Performance in Special Applications 65 1.6.2.4 Textile Fastness Properties 66 1.6.3 Migration 67 1.6.3.
1 Blooming 68 1.6.3.2 Bleeding/Overspraying Fastness 71 1.6.4 Disturbances during the Processing of Pigmented Systems 75 1.6.4.
1 Plate-Out 75 1.6.4.2 Overpigmentation/Chalking 76 1.6.4.3 Distortion/Nucleation in Polymers 77 1.6.
5 Dispersion 78 1.6.5.1 General Considerations 78 1.6.5.2 Desagglomeration of Pigment Particles 80 1.6.
5.3 Wetting of Pigment Particle Surfaces 80 1.6.5.4 Distribution of the Dispersed Pigment in its Medium 84 1.6.5.5 Stabilization 86 1.
6.5.6 Dispersion and the Critical Pigment Volume Concentration 86 1.6.5.7 Test Methods 87 1.6.5.
8 Flush Pastes 93 1.6.5.9 Pigment Preparations 94 1.6.6 Lightfastness and Weatherfastness 94 1.6.6.
1 Definition and General Information 94 1.6.6.2 Evaluation Techniques and Equipment 95 1.6.6.3 Factors Determining the Lightfastness 98 1.6.
7 Thermal Stability 104 1.6.8 Flow Properties of Pigmented Systems 110 1.6.8.1 Rheological Properties 110 1.6.8.
2 Viscoelastic Properties 114 1.6.8.3 Influence on the Flow Properties 114 1.6.8.4 Correlation between Flow Behaviour and Rheological Parameters 115 1.6.
8.5 Rheological Measurements 116 1.7 Particle Size Distribution and Application Properties of Pigmented Media 119 1.7.1 Tinctorial Strength 120 1.7.2 Hue 122 1.7.
3 Hiding Power, Transparency 126 1.7.4 Lightfastness and Weatherfastness 131 1.7.5 Dispersibility 133 1.7.6 Gloss 136 1.7.
7 Solvent and Migration Fastness 139 1.7.8 Flow 141 1.8 Areas of Application for Organic Pigments 142 1.8.1 Printing Inks 144 1.8.1.
1 Offset Printing 144 1.8.1.2 Gravure Printing 149 1.8.1.3 Solvent-Based Flexographic Packaging Printing 152 1.8.
1.4 Non-impact Printing 154 1.8.1.5 Security Printing 155 1.8.2 Coatings 155 1.8.
2.1 Oxidatively Drying Paints 156 1.8.2.2 Oven Drying Systems 156 1.8.2.3 Emulsion Paints 162 1.
8.3 Plastics 163 1.8.3.1 Polyolefins 167 1.8.3.2 Poly(vinyl chloride) (PVC) 169 1.
8.3.3 Polyurethane 174 1.8.3.4 Polyamide, Polycarbonate, Polyester, Polyoxymethylene 175 1.8.3.
5 Polystyrene, Styrene-Copolymers, Poly(methyl methacrylate) 175 1.8.3.6 Elastomers 177 1.8.3.7 Thermoplastic Elastomers (TPEs) 178 1.8.
3.8 Thermosets (Thermosetting Plastics) 179 1.8.3.9 Spin Dyeing 181 1.8.4 Other Areas of Application 183 1.8.
4.1 Miscellaneous Applications 183 1.8.4.2 Colouration of Glass with Organic Pigments 184 References for Chapter 1 184 2 Hydrazone Pigments (Formerly Called Azo Pigments) 193 2.1 Starting Materials 196 2.1.1 Diazo Components 197 2.
1.1.1 Reduction Methods 199 2.1.2 Coupling Compounds 200 2.1.2.1 Acetoacetic Anilides 201 2.
1.2.2 β-Naphthol and its Derivatives 201 2.1.2.3 Pyrazolone Derivatives 204 2.1.3 Important Intermediates 204 2.
2 Synthesis of Hydrazone Pigments 205 2.2.1 Diazotization 206 2.2.1.1 Diazotization Mechanism 207 2.2.1.
2 Methods of Diazotization 207 2.2.2 Coupling 209 2.2.2.1 Coupling Techniques 211 2.2.3 Finishing 213 2.
2.4 Filtration, Drying and Milling 214 2.2.5 Hydrazone Pigment Synthesis by Continuous Operation 215 2.2.5.1 Diazotization by Continuous Technique 216 2.2.
5.2 Coupling by Continuous Process 218 2.2.5.3 Process Control 219 2.2.6 Production Units for Hydrazone Pigment Manufacture by Batch Operation 219 2.3 Monohydrazone Yellow and Orange Pigments (Formerly Called Monoazo Yellow and Orange Pigments) 221 2.
3.1 Chemistry, Manufacture and Crystal Structures 223 2.3.1.1 Non-laked Monohydrazone Yellow and Orange Pigments 223 2.3.1.2 Monohydrazone Yellow Pigment Lakes 227 2.
3.2 Properties 232 2.3.2.1 Non-laked Monohydrazone Yellow and Orange Pigments 232 2.3.2.2 Monohydrazone Yellow Pigment Lakes 233 2.
3.3 Application 233 2.3.4 Commercially Available Monohydrazone Yellow and Orange Pigments 235 2.3.4.1 General 235 2.3.
4.2 Individual Non-laked Monohydrazone Yellow and Orange Pigments 235 2.3.4.3 Monohydrazone Yellow Pigment Lakes 247 2.4 Dihydrazone Pigments (Formerly Called Disazo Pigments) 251 2.4.1 Diarylide Yellow Pigments 253 2.
4.1.1 Chemistry, Manufacture and Crystal Structures 253 2.4.1.2 Properties 258 2.4.1.
3 Application 259 2.4.1.4 Commercially Available Diarylide Yellow Pigments 262 2.4.2 Bisacetoacetarylide Pigments 278 2.4.2.
1 Chemistry, Manufacture and Crystal Strctures 278 2.4.2.2 Properties and Application 280 2.4.2.3 Commercially Available Bisacetoacetarylide Pigments 281 2.4.
3 Dihydrazonepyrazolone Pigments (Formerly Called Disazopyrazolone Pigments) 284 2.4.3.1 Chemistry, Manufacture and Crystal Structures 284 2.4.3.2 Properties 285 2.4.
3.3 Application 285 2.4.3.4 Commercially Available Dihydrazonepyrazolone Pigments 285 2.5 β-Naphthol Pigments 290 2.5.1 Chemistry, Manufacture and Crystal Structures 291 2.
5.1.1 Crystal Structures 292 2.5.2 Properties 293 2.5.3 Application 293 2.5.
4 Commercially Available β-Naphthol Pigments 296 2.6 Naphthol AS Pigments 300 2.6.1 Chemistry, Manufacture and Crystal Structures 302 2.6.1.1 Crystal Structures 303 2.6.
2 Properties 307 2.6.3 Application 309 2.6.4 Commercially Available Naphthol AS Pigments 310 2.6.4.1 General 310 2.
6.4.2 Naphthol AS Pigments with Simple Substituents 310 2.6.4.3 Naphthol AS Pigments with Sulfonamide or Carbonamide Groups 324 2.7 Red Hydrazone Pigment Lakes (Formerly Called Red Azo Pigment Lakes) 337 2.7.
1 β-Naphthol Pigment Lakes 338 2.7.1.1 Chemistry, Manufacture and Crystal Structures 338 2.7.1.2 Properties 341 2.7.
1.3 Application 342 2.7.1.4 Commercially Available β-Naphthol Pigment Lakes 342 2.7.2 BONA Pigment Lakes 349 2.7.
2.1 Chemistry, Manufacture and Crystal Structures 349 2.7.2.2 Properties 350 2.7.2.3 Application 351 2.
7.2.4 Commercially Available BONA Pigment Lakes 352 2.7.3 Naphthol AS Pigment Lakes 362 2.7.3.1 Chemistry, Manufacture, Crystal Structures, Properties a.