Handbook of Natural Colorants: (Wiley Series in Renewable Resource)

Concentration on renewable resources, sustainability and replacement of oil based products are driving forces to reassess the potential of natural resources including natural colorants. The growing consumer interest in purchasing “green” products, which exhibit an improved environmental profile, can be seen as the break-through force needed to reintroduce natural colorants into the modern markets. Written by scientists with specialised knowledge in the field, Handbook of Natural Colorants provides a unique source of information, summarising the present knowledge of natural colorants in depth. Supporting researchers in this emerging field of sustainable chemistry, it provides easy access to the theory and practice of natural colorants from different viewpoints, including agricultural, economic and legislative aspects. Topics covered include: History of coloration technology Present position of natural colorants Regional plant source availability Specific application techniques Chemical properties that professional dyers and chemists have to consider Agricultural sourcing of dyes with an emphasis on renewable resources Discussions on energy and material balance issues arising from the sourcing of  materials Production aspects of colorants, leading on to the key applications Environmental and economic aspects Also included are the pros and cons of natural dyestuffs, presenting some promising results and evaluating the potential use of vegetable dyes as alternatives to chemical-based ones with a focus on green chemistry

Table of Contents:
List of Contributors xv Series Preface xix Preface xxi Part I Historical Aspects 1 1 History of Natural Dyes in the Ancient Mediterranean World 3 Maria J. Melo 1.1 Introduction 3 1.1.1 Ancient Mediterranean World 3 1.1.2 Dyes from Antiquity 4 1.1.3 Unveiling the Secrets of Ancient Dyes with Modern Science 5 1.2 Ancient Reds 6 1.2.1 Anthraquinone Reds 6 1.2.2 Redwoods 8 1.2.3 Flavylium/Anthocyanin Reds 8 1.3 Ancient Blues 10 1.3.1 Indigo Blues 10 1.3.2 Anthocyanin Blues 12 1.4 Ancient Purple (Tyrian Purple) 13 1.5 Ancient Yellows 15 1.5.1 Flavonoid Yellows 15 1.5.2 Carotenoid Yellows 17 1.5.3 Chalcone and Aurone Yellows 17 Acknowledgement 17 References 17 2 Colours in Civilizations of the World and Natural Colorants: History under Tension 21 Dominique Cardon 2.1 Introduction 21 2.2 The Triumph of Mauvein: Synthetic Fulfilment of the Antique Purplemania 22 2.3 Blue: from Kingly Regional to Globally Democratic 23 2.4 Red and Yellow: from Micro to Macro Scales 24 2.5 What Future for Natural Colorants in the Dawning Era of Renewable Resources? 25 Acknowledgement 26 References 26 3 History of Natural Dyes in North Africa ‘Egypt’ 27 Harby Ezzeldeen Ahmed 3.1 Introduction 27 3.2 Natural Dyes in Pharaonic Textiles 28 3.3 Dyeing Techniques 28 3.4 Dye Sources 29 3.4.1 Woad 29 3.4.2 Indigo 30 3.4.3 Red 30 3.4.4 Yellow 30 3.4.5 Black 31 3.4.6 Brown 31 3.4.7 Green 31 3.4.8 Purple 31 3.5 Dyeing in Coptic Textiles 31 3.6 Wool Dyed Fabric with Natural Dye 33 3.7 Dyes in Islamic Textiles 33 3.8 Mordants 34 References 36 Part II Regional Aspects of Availability of Plant Sources 37 4 Dye Plants in Europe 39 Andrea Biertümpfel and Günter Wurl 4.1 Introduction 39 4.2 Potential European Dye Plants 39 4.3 Cultivation of Dye Plants Yesterday and Now 40 4.4 Modern Cultivation Methods for Important European Dye Plants 41 4.4.1 General Facts 41 4.4.2 Blue Dyeing Plants 42 4.4.3 Red Dyeing Plants 43 4.4.4 Yellow Dyeing Plants 44 4.4.5 Brown Dyeing Plants 46 4.5 Production of Dye Extracts 48 4.6 Relevant Examples for the Application 50 4.7 Conclusions, Discussion and Summary 50 References 51 5 Dyes in South America 53 Veridiana Vera de Rosso and Adriana Zerlotti Mercadante 5.1 Introduction 53 5.2 Annatto 55 5.3 Turmeric 57 5.4 Marigold 59 5.5 Cochineal and Carmine 60 Acknowledgements 62 References 62 6 Natural Dyes in Eastern Asia (Vietnam and Neighbouring Countries) 65 Hoang Thi Linh 6.1 Introduction 65 6.2 Annatto (Botanical Name Bixa orellana L., Family Bixaceae) 65 6.3 Tea (Botanical Name Camellia sinensis (L.) Kuntze, Family Theaceae) 67 6.4 Umbrella Tree (Botanical Name Terminalia catappa L., Family Combretaceae) 67 6.5 Diospyros mollis – Mackloeur (Botanical Name Diospyros mollis L. Griff, Family Ebenaceae) 68 6.6 Indigo (Botanical Name Indigofera L., Family Fabaceae) 68 6.6.1 Indigofera tinctoria L. 68 6.6.2 Indigofera galegoides DC. 69 6.6.3 Strobilanthes cusia (Baphicacanthus) 69 6.7 Henna (kok khan, or khao youak in Laos) (Botanical Name Lawsonia spinosa L., Family Lythraceae) 69 6.8 Nacre (Botanical Name Khaya senegalensis, Family Meliaceae) 69 6.9 Sappan Wood (Botanical Name Caesalpinia sappan L., Family Fabaceae) 69 6.10 Sophora japonica Flowers (Botanical Name Sophora japonica L., Family Leguminosae) 70 6.11 Turmeric (Botanical Name Curcuma longa L., Family Zingiberaceae) 70 6.12 Sapodilla (Botanical Name Manilkara zapota L. or Achras zapota, Family Sapotaceae) 70 6.13 Betel (Botanical Name Piper betle L., Family Piperaceae) 71 6.14 Eucalyptus (Botanical Name Eucalyptus, Family Myrtaceae) 71 6.15 Caesalpinia Yellow (Botanical Name Caesalpinia pulcherrima L., Family Fabaceae) 71 6.16 Brow-tuber (Botanical Name Dioscorea cirrhosa Lour, Family Dioscoreaceae) 71 Part III Colorant Production and Properties 73 7 Indigo – Agricultural Aspects 75 Philip John and Luciana Gabriella Angelini 7.1 Introduction 75 7.2 Isatis 76 7.2.1 Introduction 76 7.2.2 Agronomy 77 7.3 Persicaria (Polygonum) 92 7.3.1 Introduction 92 7.3.2 Agronomy 93 7.4 Indigofera 101 Acknowledgements 103 References 103 8 Indigo – Extraction 105 Philip John 8.1 Introduction 105 8.2 Methods of Determining Indigo 106 8.3 Precursors in the Plants and Indigo Formation 108 8.4 Extraction Procedures 114 8.4.1 Traditional Process Using Crushed Leaf Material 114 8.4.2 Steeping in Water 117 8.5 Purity of Natural Indigo 126 Acknowledgements 130 References 130 9 Anthocyanins: Nature’s Glamorous Palette 135 Maria J. Melo, Fernando Pina and Claude Andary 9.1 Chemical Basis 135 9.1.1 Chemical Structures 135 9.1.2 Equilibria in Solution 137 9.1.3 Colour and Colour Stability 140 9.1.4 Anthocyanins as Antioxidants 141 9.2 Natural Sources for Anthocyanins 142 9.2.1 Plant Sources, Content, Influencing Parameters 142 9.3 Applications 144 9.3.1 Food Colorants 144 9.3.2 Other Uses 145 9.4 Examples of Commercial Products and Processing 146 References 147 10 Natural Colorants – Quinoid, Naphthoquinoid and Anthraquinoid Dyes 151 Thomas Bechtold 10.1 Introduction 151 10.2 Benzoquinone Dyes 151 10.3 Naphthoquinone Dyes 152 10.3.1 Lawson (2-hydroxy-1,4-naphthoquinone, CI Natural Orange 6) 153 10.3.2 Juglone (5-hydroxy-1,4-naphthoquinone, CI Natural Brown 7) 156 10.4 Anthraquinone Dyes 157 10.4.1 Main Components Emodin and Chrysophanol –Rheum Species and Rumex Species 157 10.4.2 Main Components Alizarin and/or Pseudopurpurin/Purpurin 159 10.5 Other Sources of Anthraquinoid Dyes 171 References 171 11 Dyes from Lichens and Mushrooms 183 Riikka Raisanen 11.1 Use of Lichen and Mushroom Dyes in the Past 183 11.2 Cultivation of Lichens and Mushrooms 184 11.3 Dyestuffs in Lichens and Mushrooms 185 11.3.1 Lichen Dyestuffs: Orchils and Litmus 185 11.3.2 Yellowish, Brownish and Reddish Colorants from Lichen 191 11.3.3 Benzoquinone Derivatives 192 11.3.4 Anthraquinones 192 11.3.5 Other Colorants of Fungi 196 11.4 Colour-fastness of Lichen and Mushroom Dyes 197 11.5 New Approaches to Lichen and Fungal Natural Dyes 198 References 198 12 Tannins and Tannin Agents 201 Riitta Julkunen-Tiitto and Hely Haggman 12.1 Introduction 201 12.2 Chemical Structure, Biosynthesis and Degradation 203 12.3 Properties of Tannins 207 12.4 Chemical Activities of Tannins 208 12.5 Analysis of Tannins 209 12.5.1 Sample Preservation 209 12.5.2 Extraction and Purification 209 12.5.3 Quantification of Tannins 210 12.6 Use, Toxicology and Safety Aspects of Tannins 212 References 214 13 Carotenoid Dyes – Properties 221 U. Gamage Chandrika 13.1 Introduction 221 13.1.1 Occurrence of Carotenoids 221 13.1.2 Chemistry of Carotenoids 221 13.1.3 Chemical Characteristics of Natural Carotenoids 222 13.2 Properties and Functions of Carotenoids 225 13.2.1 Carotenoids Role as Pro-vitamin A 225 13.2.2 Use of Carotenoids as Markers of Dietary Practices 227 13.2.3 Carotenoids as Antioxidants 227 13.2.4 Carotenoids in the Macular Region of the Retina 227 13.2.5 Carotenoids as Anticancer Agent 228 13.2.6 Carotenoids as a Natural Colorant 228 13.3 General Procedure for Carotenoid Analysis 228 13.3.1 Sampling 228 13.3.2 Extraction 230 13.3.3 Saponification of Carotenoids 230 13.3.4 Chromatographic Separation 230 13.3.5 Chemical Tests 231 13.3.6 Detection and Identification of Carotenoids 231 13.3.7 Quantification of Carotenoids 233 13.4 Problems in Carotenoid Analysis 233 References 234 14 Carotenoid Dyes – Production 237 U. Gamage Chandrika 14.1 Factors Influencing Carotenoid Composition in Plant Sources 237 14.1.1 Stage of Maturity 237 14.1.2 Cultivar or Varietal Differences 238 14.1.3 Climatic or Geographic Effects 238 14.1.4 Post-harvest Storage and Packing 239 14.1.5 Changes in Processing/Cooking 239 14.1.6 Effect of Agrochemicals 241 References 241 15 Chlorophylls 243 Ursula Maria Lanfer Marquez and Daniela Borrmann 15.1 Introduction 243 15.2 Chlorophylls as Colorants 244 15.3 Other Applications of Chlorophylls and their Derivatives 247 15.4 Chemical Structures and Physicochemical Properties 247 15.5 Stability and Analysis 250 15.6 Sources, Storage and Handling 250 15.7 Purity, Standardization and Quality Control 251 15.8 Toxicological and Safety Aspects 252 References 253 Part IV Application in Technical Use and Consumer Products 255 16 Flavonoids as Natural Pigments 257 M. Monica Giusti and Taylor C. Wallace 16.1 Introduction 257 16.2 Role of Localized Flavonoids in the Plant 258 16.3 General Flavonoid Chemical Structure 258 16.4 Biosynthesis of Flavonoids 259 16.5 Anthocyanins as Natural Colorants 261 16.5.1 Color Stability 261 16.5.2 Structure 261 16.5.3 Structural Transformation and pH 263 16.5.4 Temperature 264 16.5.5 Oxygen and Ascorbic Acid 264 16.5.6 Light 265 16.5.7 Enzymes and Sugars 265 16.5.8 Sulfur Dioxide 266 16.5.9 Co-pigmentation and Metal Complexation 267 16.6 Other Flavonoids as Natural Colorants 268 16.6.1 Yellow Flavonoid Pigments 268 16.6.2 Tannins 269 16.7 Therapeutic Effects of Flavonoids in the Diet 270 16.8 Regulations on the Use of Flavonoid Colorants 271 References 272 17 Application of Natural Dyes in the Coloration of Wood 277 Martin Weigl, Andreas Kandelbauer, Christian Hansmann, Johannes Pöckl, Ulrich Müller and Michael Grabner 17.1 Introduction 277 17.1.1 General Basics 278 17.1.2 Color Measurement 282 17.1.3 Color Stability 283 17.2 Coatings 283 17.3 Dyes 285 17.3.1 Dyeing for Analytical Purposes 285 17.3.2 Impregnation 286 17.4 Color Modification 290 17.4.1 Drying 291 17.4.2 Steaming 295 17.4.3 Thermal Treatment 297 17.4.4 Ammoniation 298 17.4.5 Bleaching 301 17.4.6 Enzymatic Treatment 303 17.4.7 Radiation 305 17.5 Outlook 308 References 308 18 Natural Colorants in Textile Dyeing 315 Rita A. M. Mussak and Thomas Bechtold 18.1 Introduction 315 18.2 Reasons for Natural Coloration 316 18.3 Analysis of a Dyeing Process 317 18.3.1 Water 318 18.3.2 Energy 318 18.3.3 Dyestuff and Chemicals (Mordants and Auxiliaries) 319 18.3.4 Machinery 321 18.4 Basics of Natural Dyeings 321 18.4.1 Requirements of the Dyestuff 321 18.4.2 Dye-ability of Substrates 321 18.4.3 Standardization of the Dyestuff 326 18.4.4 Ecological Aspects 327 18.4.5 Aspects of Application 328 18.4.6 Dyeing Technology 329 18.4.7 Mordanting 330 18.4.8 Standardization of the Coloration Process 331 18.4.9 Mixtures of Plant Material 331 18.5 Natural Dyes on an Industrial Scale 332 18.5.1 Hank Dyeing of Woolen Yarn and Production of Woolen Caps 332 18.5.2 Dyeing of Cones in a Yarn Dyeing Machine 333 18.5.3 Dyeing of Cotton Fabric on a Jet Dyeing Machine 333 18.5.4 Dyeing of Cotton Fabric on a Jig Dyeing Machine 333 18.5.5 Fabric Dyeing on a Garment Dyeing Machine 333 18.5.6 Dyeing of Polyamide Tights in a Paddle Dyeing Machine 334 18.6 Conclusion 334 Acknowledgment 334 References 335 19 Natural Colorants in Hair Dyeing 339 Thomas Bechtold 19.1 Introduction 339 19.2 Human Hair 340 19.3 General Requirements on Hair Dyeing Concepts 340 19.4 Chemical Principles of Dyestuff Binding 341 19.5 Relevant Natural Dyes for Hair Dyeing 342 19.5.1 Naphthoquinone Dyes – Henna and Walnut 342 19.5.2 Indigo 343 19.5.3 Metal Complexes 345 19.5.4 Metal Reaction Dyes 346 19.5.5 Anthraquinoid Dyes 347 19.6 Specialities 347 19.7 Regulations 347 References 347 Part V Environmental 351 20 Environmental Aspects and Sustainability 353 Erika Ganglberger 20.1 Introduction 353 20.2 Supply of Plant Material 354 20.2.1 Cultivation of Dye Plants 354 20.2.2 Residual Materials and By-products 355 20.2.3 Selection Process for a Sustainable Supply of Plant Material 356 20.3 Processing to Dyestuff 357 20.3.1 Energy Consumption 358 20.3.2 Water Consumption 359 20.4 Application of Colouring Matter 360 20.4.1 Dyeing Procedure 361 20.5 Considerations Concerning the Life Cycle 361 20.5.1 Raw Material 361 20.5.2 Processing of Raw Material 362 20.5.3 Extraction of Dyestuff 362 20.5.4 Dyeing Procedure 363 20.5.5 Transport 363 20.6 Conclusion 364 20.6.1 Dealing with Sustainability 364 References 365 21 Economic Aspects of Natural Dyes 367 Susanne Geissler 21.1 Introduction 367 21.2 Basic Requirements for the Industrial Use of Natural Colorants 368 21.3 Challenges for the Industrial Use of Natural Colorants 370 21.3.1 Quality of Raw Material and Reproducibility of Colours 370 21.3.2 Range of Available Colours 370 21.4 Consumer Expectations 371 21.4.1 Market Research for Naturally Dyed Products 372 21.5 Production Costs of Natural Colorant Products 375 21.5.1 Cost Categories 375 21.5.2 Aspects Influencing Production Costs 376 21.5.3 Prices of Synthetic Dyes – How Much Are Textile Companies Prepared to Pay for Dyes? 378 21.5.4 Acceptable Production Costs through a Mixed Portfolio (Agricultural Primary Production and Residues from Other Production Processes) 379 21.6 Closed-Loop Economy: Towards a Zero-Emission and Zero-Waste Society 381 21.7 Conclusion: Aspects Influencing Market Development for Natural Colorants 382 References 383 Index 385

About the Author :
Dr Thomas Bechtold is Head of the Institute for Textile Chemistry and Textile Physics at the Leopold-Franzens University of Innsbruck, Austria. His key research interests are: dyeing with vat, indigo and sulfur dyes; electrochemistry in textile processes; formulation of special detergents. He has published over 70 papers in this research field in the last 20 years. Dr Rita Mussak is based in the Department of Theoretical Chemistry at the Leopold-Franzens University of Innsbruck, Austria.

Review :
Review copy sent 02/11/10: Chimie Nouvelle