Contents
Chapter 1 Colour: A Historical Perspective 1
1.1 Introduction 1
1.2 The Early History of Dyes and Pigments 2
1.3 The Era of the Synthetic Dye 6
1.4 Colour Chemistry in the Twentieth Century 13
1.5 Recent and Current Trends in
Colour Chemistry 15
References 19
Chapter 2 The Physical and Chemical Basis of Colour 21
2.1 Introduction 21
2.2 Visible Light 22
2.3 The Eye 25
2.4 The Causes of Colour 27
2.5 The Interaction of Light with Objects 28
2.6 Fluorescence and Phosphorescence 33
2.7 Dyes and Pigments 35
2.8 Classification of Colorants 36
2.9 Colour and Molecular Structure 38
2.9.1 Valence-Bond Approach to Colour/Structure Relationships 40
2.9.2 Molecular Orbital Approach to Colour/Structure Relationships 50
2.9.3 Molecular Mechanics 62
2.9.4 QSAR and QSPR 64
2.10 Colour in Inorganic Compounds 66
2.10.1 Colour in Metal Complexes (Coordination Compounds) 66
2.10.2 Colour from Charge Transfer Transitions in Inorganic Materials 67
2.10.3 Colour in Inorganic Semiconductors 67
References 68
Chapter 3 Azo Dyes and Pigments 72
3.1 Introduction 72
3.2 Isomerism in Azo Dyes and Pigments 73
3.3 Synthesis of Azo Dyes and Pigments 78
3.3.1 Diazotisation 79
3.3.2 Azo Coupling 84
3.4 Strategies for Azo Dye and Pigment Synthesis 87
3.4.1 Synthesis of Monoazo Dyes and Pigments 88
3.4.2 Synthesis of Disazo Dyes and Pigments 88
3.4.3 Synthesis of Dyes and Pigments containing more than two Azo Groups 92
3.5 Metal Complex Azo Dyes and Pigments 93
References 97
Chapter 4 Carbonyl Dyes and Pigments 99
4.1 Introduction 99
4.2 Anthraquinones 100
4.3 Indigoid Dyes and Pigments 105
4.4 Benzodifuranones 110
4.5 Fluorescent Carbonyl Dyes 111
4.6 Carbonyl Pigments 112
4.7 The Quinone–Hydroquinone Redox System 118
4.8 Synthesis of Carbonyl Colorants 119
4.8.1 Synthesis of Anthraquinones 119
4.8.2 Synthesis of Indigoid Colorants 125
4.8.3 Synthesis of Benzodifuranones and Coumarin Dyes 126
4.8.4 Synthesis of Carbonyl Pigments 126
References 131
Chapter 5 Phthalocyanines 133
5.1 Introduction 133
5.2 Structure and Properties of Phthalocyanines 134
5.3 Synthesis of Phthalocyanines 140
References 145
Chapter 6 Miscellaneous Chemical Classes of Organic Dyes and Pigments 147
6.1 Introduction 147
6.2 Polyene and Polymethine Dyes 147
6.3 Arylcarbonium Ion Colorants 155
6.4 Dioxazines 161
6.5 Sulfur Dyes 162
6.6 Nitro Dyes 164
References 166
Chapter 7 Textile Dyes (excluding Reactive Dyes) 168
7.1 Introduction 168
7.2 Dyes for Protein Fibres 172
7.3 Dyes for Cellulosic Fibres 178
7.4 Dyes for Synthetic Fibres 184
References 191
Chapter 8 Reactive Dyes for Textile Fibres 194
8.1 Introduction 194
8.2 Fibre-Reactive Groups 197
8.2.1 Fibre-Reactive Groups Reacting
by Nucleophilic Substitution 197
8.2.2 Fibre-Reactive Groups Reacting
by Nucleophilic Addition 203
8.3 Polyfunctional Reactive Dyes 206
8.4 Chromogenic Groups 207
8.5 Synthesis of Reactive Dyes 209
References 211
Chapter 9 Pigments 212
9.1 Introduction 212
9.2 Inorganic Pigments 217
9.2.1 Titanium Dioxide and other White
Pigments 218
9.2.2 Coloured Oxides and Oxide-hydroxides 221
9.2.3 Cadmium Sulfides, Lead Chromates and
Related Pigments 223
9.2.4 Ultramarines 226
9.2.5 Prussian Blue 227
9.2.6 Carbon Black 227
9.3 Organic Pigments 229
9.3.1 Azo Pigments 230
9.3.2 Copper Phthalocyanines 234
9.3.3 High performance Organic Pigments 235
9.4 Molecular and Crystal Modelling of Pigments 238
9.5 Pigments for Special Effects 244
9.5.1 Metallic Pigments 244
9.5.2 Pearlescent Pigments 245
9.5.3 Optically-Variable Pigments 246
9.5.4 Fluorescent Pigments 246
References 247
Chapter 10 Colour in Cosmetics, with Special Emphasis on Hair
Coloration 250
10.1 Introduction 250
10.2 Colorants for Decorative Cosmetics 251
10.3 Hair Coloration 254
10.3.1 Oxidative Hair Coloration 259
10.3.2 Non-oxidative Hair Dyeing 262
References 265
Chapter 11 Functional or ‘High Technology’ Dyes and
Pigments 267
11.1 Introduction 267
11.2 Electronic Applications of Dyes and
Pigments 269
11.2.1 Colour in Electronic Displays 269
11.2.2 Laser Dyes 280
11.2.3 Dyes in Solar Energy Conversion 282
11.2.4 Dyes in Optical Data Storage 288
11.3 Reprographics Applications of Dyes and
Pigments 291
11.3.1 Electrophotography 291
11.3.2 Inkjet Printing 294
11.3.3 Dye Diffusion Thermal Transfer (D2T2)
Printing 298
11.4 Biomedical Applications of Dyes 299
11.4.1 Biological Stains and Probes 299
11.4.2 Photodynamic Therapy 300
11.5 Chromic Materials 303
11.5.1 Ionochromism 304
11.5.2 Thermochromism 305
11.5.3 Photochromism 309
11.5.4 Electrochromism 312
11.5.5 Miscellaneous Colour Change Phenomena 313
References 314
Chapter 12 Colour and the Environment 318
References 331
Subject Index 333