The Chemistry and Application of Dyes

It is particularly appropriate that a volume concerned with dye chemistry should be included in the series Topics in Applied Chemistry. The development of the dye industry has been inexorably linked not only with the development of the chemical industry but also with organic chemistry itself since the middle of the last century. The position of dye chemistry at the forefront of chemical 1945 and more markedly so during the last advance has declined somewhat since 15 years, with pharmaceutical and medicinal chemistry assuming an increasingly prominent position. Nevertheless, dye production still accounts for a significant portion of the business of most major chemical companies. The field of dye chemistry has stimulated the publication of many books over the years but surprisingly few have concentrated on or even included the practical aspects of dye synthesis and application. Thus, the present volume is designed to fulfill that need and provide the reader with an account of advances in dye chemistry, concentrating on more recent work and giving, in a single volume, synthetic detail and methods of application of the most important classes, information which will be invaluable to both student and research chemist alike.

1. Introduction: The Evolution of Present-Day Dye Technology.- I. Background.- II. The Historical Development of Synthetic Dyes.- A. The Early History up to 1865.- B. Developments in Dye Chemistry from 1865 to Modern Times.- III. The Development of Color and Constitution Theory.- References.- 2. Classification of Dyes by Chemical Structure.- I. Introduction.- II. Azo Dyes.- A. Basic structure.- B. Synthesis.- C. Tautomerism.- 1. Azo/Hydrazone Tautomerism.- 2. Azo/Imino Tautomerism.- 3. Azonium/Ammonium Tautomerism.- D. Metallized Azo Dyes.- E. Carbocyclic Azo Dyes.- F. Heterocyclic Azo Dyes.- III. Anthraquinone Dyes.- A. Basic structure.- B. Synthesis.- C. Tautomerism/Metal Complexes.- D. Properties.- IV. Benzodifuranone Dyes.- V. Polycyclic Aromatic Carbonyl Dyes.- VI. Indigoid Dyes.- VII. Polymethine and Related Dyes.- A. Azacarbocyanines.- B. Hemicyanines.- C. Diazahemicyanines.- VIII. Styryl Dyes.- IX. Di- and Tri-Aryl Carbonium and Related Dyes :.- X. Phthalocyanines.- XI. Quinophthalones.- XII. Sulfur Dyes.- XIII. Nitro and Nitroso Dyes.- XIV. Miscellaneous Dyes.- XV. Summary.- References.- 3. Dyes for Cellulosic Fibers.- I. Introduction.- II. Fiber Reactive Dyes.- A. Historical Development.- B. Reactive Systems.- C. Chromogens in Reactive Dyes.- 1. Azo Reactive Dyes.- 2. Anthraquinone Reactive Dyes.- 3. Phthalocyanine Reactive Dyes.- 4. Triphenodioxazine and Formazan Reactive Dyes.- III. Direct Dyes.- A. Azo Direct Dyes.- 1. Monoazo Dyes.- 2. Disazo Dyes.- 3. Trisazo Dyes.- 4. Metal Complex Dyes.- 5. Mixed Chromophore Dyes.- B. Aftertreatments.- C. Triphenodioxazine dyes.- IV. Azoic Dyes.- V. Vat Dyes.- A. Anthraquinone Vat Dyes.- B. Fused Ring Polycyclic Vat Dyes.- C. Indigoid Vat Dyes.- VI. Sulfur Dyes.- A. Sulfurized Vat Dyes.- VII. Syntheses of Reactive Dyes.- A. Analysis of Dyes and Intermediates.- B. Methods of Diazotization.- C. Coupling Methods.- D. Synthetic Examples of Reactive Dyes.- VIII. Synthesis of Direct Dyes.- A. Synthetic Examples of Direct Dyes.- IX. Synthesis of Vat Dyes.- A. Synthetic Examples of Vat Dyes.- X. Synthesis of Sulfur Dyes.- A. Synthetic Examples of Sulfur Dyes.- Acknowledgments.- References.- 4. Dyes for Polyester Fibers.- I. Introduction.- II. Anthraquinone Dyes.- A. Preparative Index.- B. Discussion.- III. Methine Dyes.- A. Preparative Index.- B. Discussion.- IV. Nitrodiphenylamine Dyes.- A. Preparative Index.- B. Discussion.- V. Azo Dyes.- A. Preparative Index.- B. Discussion.- 1. Diazonium Components.- 2. Coupling Components.- 3. Dyes.- VI. Miscellaneous Classes.- A. Preparative Index.- B. Discussion.- References.- 5. Dyes for Polyacrylonitrile.- I. Introduction.- II. Pendant Cationic Dyes.- A. Yellow dyes.- 1. Miscellaneous Chromogens.- 2. Azopyridone Dyes.- B. Red Dyes.- C. Blue Dyes.- 1. AzoDyes.- 2. Anthraquinone Dyes.- D. Miscellaneous Cationic Groups.- III. Delocalized Cationic Dyes.- A. Comparison with Pendant Dyes.- B. Protonated Azo Dyes.- C. Yellow Dyes.- 1. Azacarbocyanines.- 2. Diazacarbocyanines.- 3. Triazacarbocyanines.- D. Red Dyes.- 1. Hemicyanines.- 2. Diazahemicyanines.- E. Blue Dyes.- 1. Oxazines.- 2. Thiazines.- 3. Triphenylmethanes.- 4. Naphtholactams.- 5. Diazahemicyanines.- IV. Synthesis.- A. Pendant Cationic Dyes.- 1. Azopyridone Yellow.- 2. Azobenzene Red.- 3. Anthraquinone Blue.- B. Delocalized Cationic Dyes.- 1. Azacarbocyanine Yellow.- 2. Diazacarbocyanine Yellow.- 3. Triazacarbocyanine Yellow.- 4. Hemicyanine Red.- 5. Diazahemicyanine Red.- 6. Oxazine Blue.- 7. Triphenylmethane Green.- 8. Naphtholactam Blue.- 9. Diazahemicyanine Blue.- V. Summary.- References.- 6. Dyes for Polyamide Fibers.- I. Introduction.- II. Dyes for Wool and Other Animal Fibers.- A. Historical.- B. Acid Dyes.- 1. Azo Dyes.- 2. Chrome Mordant Dyes.- 3. Metallized Dyes.- a. 1:1 Complexes.- b. 2:1 Complexes.- 4. Anthraquinone Acid Dyes.- 5. Miscellaneous Dyes.- a. Vat Dyes.- b. Xanthene Dyes.- c. Triphenylmethane Dyes.- d. Nitro Dyes.- e. Reactive Dyes.- f. Phthalocyanine Dyes.- III. Dyes for Nylon.- IV. Synthesis of Dyes.- A. CI Acid Yellow 19.- B. CI Acid Red 57.- C. CI Acid Orange 67.- D. CI Acid Yellow 76.- E. CI Acid Orange 3.- F. CI Mordant Yellow 8.- G. CI Mordant Red 7.- H. CI Mordant Orange 6.- I. CI Acid Red 249.- J. CI Acid Black 60.- K. CI Acid Blue 129.- L. CI Acid Green 25.- M. Coumarin Acid Dye.- N. Phthalocyanine Acid Dye.- References.- 7. Application of Dyes.- I. Introduction.- A. Classification of Dyes and Pigments.- B. Textile Fibers.- 1. Mass Pigmentation.- 2. Gel Dyeing.- 3. Loose State Dyeing.- 4. Yarn Dyeing.- 5. Fabric Dyeing.- 6. Garment Dyeing.- C. Dyeing Methods.- 1. Immersion (Exhaustion) Methods.- 2. Impregnation-Fixation Methods.- D. Fastness of Dyed Textiles.- II. Dyeing of Wool.- A. Nonmetallized Acid Dyes.- 1. Azo.- 2. Anthraquinoid.- 3. Triphenylmethane.- 4. Dissolving the Dyes.- 5. Dyeing Behavior.- B. Mordant Dyes.- 1. Anthraquinone.- 2. Azo.- 3. Triphenylmethane.- 4. Xanthene.- 5. Dissolving the Dyes.- 6. Dyeing Behavior.- C. Metal-Complex or Premetallized Dyes.- 1. Dissolving the Dyes.- 2. 1:1 Metal-Complex (Acid Dyeing Premetallized) Dyes.- 3. 2:1 Metal-Complex (Neutral Dyeing Premetallized) Dyes.- D. Reactive Dyes.- 1. Dissolving the Dyes.- 2. Dyeing Behavior.- E. Dyeing Shrink-Resist Treated Wool.- 1. Reactive Dyes.- 2. Mordant Dyes.- 3. 2:1 Premetallized Dyes.- III. Dyeing of Cellulosic Fibers.- A. Direct Dyes.- 1. Azo.- 2. Stilbene.- 3. Phthalocyanine.- 4. Dioxazine.- 5. Miscellaneous Dyes.- 6. Dissolving the Dyes.- 7. Dyeing Behavior.- 8. Aftertreatments.- B. Vat Dyes.- 1. Indigoid and Thioindigoid.- 2. Anthraquinone.- 3. Dyeing Behavior.- 4. Dyeing Auxiliaries.- 5. Oxidation.- 6. Soaping.- 7. Acidification.- 8. Dispersing the Dyes.- 9. Leuco Dyeing.- 10. Pigmentation Processes.- 11. Solubilized Vat Dyes.- 12. Sulfurized Vat Dyes.- 13. Dyeing with Indigo.- C. Sulfur Dyes.- 1. CI Sulfur Dyes.- 2. CI Leuco Sulfur Dyes.- 3. CI Solubilized Sulfur Dyes.- 4. CI Condense Sulfur Dyes.- 5. Dyeing Behavior.- 6. Batchwise Dyeing Processes.- 7. Semicontinuous Processes.- 8. Continuous Processes.- D. Azoic Colorants.- 1. Coupling Components.- 2. Diazo Components.- 3. Azoic Compositions.- 4. Dyeing Behavior.- 5. Application of Coupling Components.- 6. Removal of Surplus Coupling Component.- 7. Development.- 8. Aftertreatment.- E. Reactive Dyes.- 1. Dissolving the Dyes.- 2. Dyeing Behavior.- 3. Aftertreatment.- IV. Dyeing of Secondary Acetate and Triacetate Fibers.- A. Disperse Dyes.- 1. Azo.- 2. Anthraquinone.- 3. Nitrodiphenylamine.- 4. Styryl.- 5. Dispersing the Dyes.- 6. Dyeing Behavior.- 7. High-Temperature Dyeing.- 8. Carrier Dyeing.- 9. Barré Effects.- 10. Dyeing Auxiliaries.- 11. Aftertreatment.- 12. Dyeing Processes.- B. Azoic Colorants.- C. Vat Dyes.- D. Other Dyes.- V. Dyeing of Polyester Fibers.- A. Disperse Dyes.- 1. Dispersing the Dyes.- 2. Dyeing Behavior.- 3. Barré Effects.- 4. Oligomers.- 5. Dyeing Auxiliaries.- 6. Aftertreatment.- 7. Batchwise Dyeing.- 8. Semicontinuous Dyeing.- 9. Continuous Dyeing.- B. Azoic Colorants.- C. Vat Dyes.- D. Dyeing of Modified Polyester Fibers.- 1. Dyeing of Deep-Dyeing Polyester Fibers.- 2. Dyeing of Noncarrier Dyeing Polyester Fibers.- 3. Dyeing of Anionic-Modified PET Fibers.- 4. Dyeing of Differential-Dyeing PET Fibers.- VI. Dyeing of Polyamide Fibers.- A. Nonmetallized Acid Dyes.- 1. Dissolving the Dyes.- 2. Dyeing Behavior.- 3. Aftertreatment.- B. Disperse Dyes.- C. Mordant Dyes.- D. Premetallized Acid Dyes.- 1. 1:1 Metal-Complex Dyes.- 2. 2:1 Metal-Complex Dyes.- E. Direct Dyes.- F. Reactive Dyes.- G. Dyeing of Modified Nylons.- VII. Dyeing of Acrylic Fibers.- A. Basic Dyes.- 1. Positive Charge Delocalized over the Dye Cation.- 2. Positive Charge Localized on an Ammonium Group.- 3. Dissolving the Dyes.- 4. Dyeing Behavior.- 5. Aftertreatment.- 6. Cooling of the Dyebath.- 7. Exhaustion Dyeing.- 8. Continuous Dyeing.- 9. Migrating Cationic Dyes.- B. Disperse Dyes.- C. Dyeing Modacrylic Fibers.- References.- 8. Nontextile Applications of Dyes.- I. Introduction.- II. Dyes for Displays.- III. Laser Dyes.- IV. Dyes for Optical Data Storage.- V. Organic Photoconductors.- VI. Nonlinear Optics.- VII. Conclusion.- References.- Index of Dyes.