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E-raamat: Industrial Organic Pigments: Production, Crystal Structures, Properties, Applications

Contributions by (Clariant Deutschland GmbH, Frankfurt), (Johann-Wolfgang-Goethe-Universitat, Fran), Contributions by (Clariant Deutschland GmbH, Frankfurt), (DECERNIS GmbH, Kelkheim, Germany), Contributions by (Clariant Deutschland GmbH, Frankfurt)
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  • Ilmumisaeg: 26-Apr-2019
  • Kirjastus: Blackwell Verlag GmbH
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  • ISBN-13: 9783527648351
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  • Formaat: PDF+DRM
  • Ilmumisaeg: 26-Apr-2019
  • Kirjastus: Blackwell Verlag GmbH
  • Keel: eng
  • ISBN-13: 9783527648351

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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.

This fourth edition 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.





Sets the international standard for information on the synthesis, reaction mechanisms, properties, relevant test methods, and applications of organic pigments Contains all industrially produced pigments of the world market, even those which can no longer be found in producers catalogs are described Standardized methods allow test results to be compared throughout the book The reader is given useful hints as to which pigment is best for a given application Clearly structured and concise text with up-to-date references to the pertinent literature Ecological and toxicological properties of organic pigments are outlined 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

Arvustused

"...eignet sich das Buch zur Einfuhrung in die Thematik, aber auch erfahrene Anwender und Entwickler werden es als wertvolles Nachschlagewerk zu schatzen wissen.... 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 erschließt." Peter Erk, BASF Aktiengesellschaft, Ludwigshafen, Angewandte Chemie, 2004-116/34

List of Contributors
xvii
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(192)
1.1 Definition: Pigments and Dyes
1(2)
1.1.1 Organic and Inorganic Pigments
2(1)
1.2 Historical
3(1)
1.3 Classification of Organic Pigments
4(6)
1.3.1 Hydrazone Pigments (Formerly Called Azo Pigments) (Chapter 2)
4(1)
1.3.1.1 Monohydrazone Yellow and Orange Pigments (Formerly Called Monoazo Yellow and Orange Pigments) (Section 2.3)
5(1)
1.3.1.2 Dihydrazone Pigments (Formerly Called Disazo Pigments) (Section 2.4)
5(1)
1.3.1.3 β-Naphthol Pigments (Section 2.5)
5(1)
1.3.1.4 Naphthol AS Pigments (Section 2.6)
5(1)
1.3.1.5 Hydrazone Pigment Lakes (Formerly Called Azo Pigment Lakes) (Section 2.7)
6(1)
1.3.1.6 Benzimidazolone Pigments (Section 2.8)
6(1)
1.3.1.7 Dihydrazone Condensation Pigments (Formerly Called Disazo Condensation Pigments) (Section 2.9)
7(1)
1.3.2 Polycyclic Pigments (Chapter 3)
7(1)
1.3.2.1 Phthalocyanine Pigments (Section 3.1)
7(1)
1.3.2.2 Quinacridone Pigments (Section 3.2)
7(1)
1.3.2.3 Perylene and Perinone Pigments (Section 3.4)
8(1)
1.3.2.4 Diketopyrrolopyrrole (DPP) Pigments (Section 3.5)
8(1)
1.3.2.5 Thioindigo Pigments (Section 3.6)
8(1)
1.3.2.6 Pigments Derived from Anthraquinone (Section 3.7)
8(1)
1.3.2.7 Dioxazine Pigments (Section 3.8)
9(1)
1.3.2.8 Quinophthalone Pigments (Section 3.9)
9(1)
1.3.2.9 Isoindolinone and Isoindoline Pigments
9(1)
1.3.3 Miscellaneous Pigments (Chapter 4)
10(1)
1.3.3.1 Triarylcarbonium Pigments (Section 4.1)
10(1)
1.3.3.2 Metal Complex Pigments (Section 4.2)
10(1)
1.4 Relationship between Chemical Structure and Pigment Properties
10(10)
1.4.1 Hue
11(3)
1.4.2 Tinctorial Strength
14(3)
1.4.3 Lightfastness and Weatherfastness
17(1)
1.4.4 Solvent and Migration Fastness
18(2)
1.5 Physical Characterization of Pigments
20(31)
1.5.1 Specific Surface Area
23(3)
1.5.2 Particle Size Distribution
26(1)
1.5.2.1 Determination of Particle Size by Ultrasedimentation
27(1)
1.5.2.2 Determination by Electron Microscopy
28(5)
1.5.2.3 Data Representation
33(4)
1.5.3 Crystal Structure and Polymorphism
37(2)
1.5.3.1 Effect of the Crystal Structure on the Optical Properties
39(2)
1.5.3.2 Polymorphism
41(3)
1.5.3.3 Identification of Polymorphic Forms by X-Ray Powder Diffraction
44(1)
1.5.3.4 Crystal Structure Determination
44(3)
1.5.3.5 Prediction of Crystal Structures; Crystal Engineering
47(1)
1.5.4 Crystallinity
48(3)
1.6 Important Application Properties and Concepts
51(68)
1.6.1 Colouristic Properties (by F. Glaser)
52(1)
1.6.1.1 Colour
52(3)
1.6.1.2 Colour Depth
55(1)
1.6.1.3 Colour Differences
56(1)
1.6.1.4 Optical Behaviour of Pigmented Coatings
56(2)
1.6.1.5 Tinctorial Strength
58(2)
1.6.1.6 Hiding Power
60(1)
1.6.1.7 Transparency
61(1)
1.6.2 Fastness to Solvents and Special Application Fastness
61(1)
1.6.2.1 Organic Solvents
61(1)
1.6.2.2 Water, Soap, Alkali and Acids
62(3)
1.6.2.3 Pigment Performance in Special Applications
65(1)
1.6.2.4 Textile Fastness Properties
66(1)
1.6.3 Migration
67(1)
1.6.3.1 Blooming
68(3)
1.6.3.2 Bleeding/Overspraying Fastness
71(4)
1.6.4 Disturbances during the Processing of Pigmented Systems
75(1)
1.6.4.1 Plate-Out
75(1)
1.6.4.2 Overpigmentation/Chalking
76(1)
1.6.4.3 Distortion/Nucleation in Polymers
77(1)
1.6.5 Dispersion
78(1)
1.6.5.1 General Considerations
78(2)
1.6.5.2 Desagglomeration of Pigment Particles
80(1)
1.6.5.3 Wetting of Pigment Particle Surfaces
80(4)
1.6.5.4 Distribution of the Dispersed Pigment in its Medium
84(2)
1.6.5.5 Stabilization
86(1)
1.6.5.6 Dispersion and the Critical Pigment Volume Concentration
86(1)
1.6.5.7 Test Methods
87(6)
1.6.5.8 Flush Pastes
93(1)
1.6.5.9 Pigment Preparations
94(1)
1.6.6 Lightfastness and Weatherfastness
94(1)
1.6.6.1 Definition and General Information
94(1)
1.6.6.2 Evaluation Techniques and Equipment
95(3)
1.6.6.3 Factors Determining the Lightfastness
98(6)
1.6.7 Thermal Stability
104(6)
1.6.8 Flow Properties of Pigmented Systems
110(1)
1.6.8.1 Rheological Properties
110(4)
1.6.8.2 Viscoelastic Properties
114(1)
1.6.8.3 Influence on the Flow Properties
114(1)
1.6.8.4 Correlation between Flow Behaviour and Rheological Parameters
115(1)
1.6.8.5 Rheological Measurements
116(3)
1.7 Particle Size Distribution and Application Properties of Pigmented Media
119(12)
1.7.1 Tinctorial Strength
120(2)
1.7.2 Hue
122(4)
1.7.3 Hiding Power, Transparency
126(5)
1.7 A Lightfastness and Weatherfastness
131(11)
1.7.5 Dispersibility
133(3)
1.7.6 Gloss
136(3)
1.7.7 Solvent and Migration Fastness
139(2)
1.7.8 Flow
141(1)
1.8 Areas of Application for Organic Pigments
142(42)
1.8.1 Printing Inks
144(1)
1.8.1.1 Offset Printing
144(5)
1.8.1.2 Gravure Printing
149(3)
1.8.1.3 Solvent-Based Flexographic Packaging Printing
152(2)
1.8.1.4 Non-impact Printing
154(1)
1.8.1.5 Security Printing
155(1)
1.8.2 Coatings
155(1)
1.8.2.1 Oxidatively Drying Paints
156(1)
1.8.2.2 Oven Drying Systems
156(6)
1.8.2.3 Emulsion Paints
162(1)
1.8.3 Plastics
163(4)
1.8.3.1 Polyolefins
167(2)
1.8.3.2 Poly(vinyl chloride) (PVC)
169(5)
1.8.3.3 Polyurethane
174(1)
1.8.3.4 Polyamide, Polycarbonate, Polyester, Polyoxymethylene
175(1)
1.8.3.5 Polystyrene, Styrene-Copolymers, Poly(methyl methacrylate)
175(2)
1.8.3.6 Elastomers
177(1)
1.8.3.7 Thermoplastic Elastomers (TPEs)
178(1)
1.8.3.8 Thermosets (Thermosetting Plastics)
179(2)
1.8.3.9 Spin Dyeing
181(2)
1.8.4 Other Areas of Application
183(1)
1.8.4.1 Miscellaneous Applications
183(1)
1.8.4.2 Colouration of Glass with Organic Pigments
184(1)
References for
Chapter 1
184(9)
2 Hydrazone Pigments (Formerly Called Azo Pigments)
193(232)
2.1 Starting Materials
196(9)
2.1.1 Diazo Components
197(2)
2.1.1.1 Reduction Methods
199(1)
2.1.2 Coupling Compounds
200(1)
2.1.2.1 Acetoacetic Anilides
201(1)
2.1.2.2 β-Naphthol and its Derivatives
201(3)
2.1.2.3 Pyrazolone Derivatives
204(1)
2.1.3 Important Intermediates
204(1)
2.2 Synthesis of Hydrazone Pigments
205(16)
2.2.1 Diazotization
206(1)
2.2.1.1 Diazotization Mechanism
207(1)
2.2.1.2 Methods of Diazotization
207(2)
2.2.2 Coupling
209(2)
2.2.2.1 Coupling Techniques
211(2)
2.2.3 Finishing
213(1)
2.2.4 Filtration, Drying and Milling
214(1)
2.2.5 Hydrazone Pigment Synthesis by Continuous Operation
215(1)
2.2.5.1 Diazotization by Continuous Technique
216(2)
2.2.5.2 Coupling by Continuous Process
218(1)
2.2.5.3 Process Control
219(1)
2.2.6 Production Units for Hydrazone Pigment Manufacture by Batch Operation
219(2)
2.3 Monohydrazone Yellow and Orange Pigments (Formerly Called Monoazo Yellow and Orange Pigments)
221(30)
2.3.1 Chemistry, Manufacture and Crystal Structures
223(1)
2.3.1.1 Non-laked Monohydrazone Yellow and Orange Pigments
223(4)
2.3.1.2 Monohydrazone Yellow Pigment Lakes
227(5)
2.3.2 Properties
232(1)
2.3.2.1 Non-laked Monohydrazone Yellow and Orange Pigments
232(1)
2.3.2.2 Monohydrazone Yellow Pigment Lakes
233(1)
2.3.3 Application
233(2)
2.3.4 Commercially Available Monohydrazone Yellow and Orange Pigments
235(1)
2.3.4.1 General
235(1)
2.3.4.2 Individual Non-laked Monohydrazone Yellow and Orange Pigments
235(12)
2.3.4.3 Monohydrazone Yellow Pigment Lakes
247(4)
2.4 Dihydrazone Pigments (Formerly Called Disazo Pigments)
251(39)
2.4.1 Diarylide Yellow Pigments
253(1)
2.4.1.1 Chemistry, Manufacture and Crystal Structures
253(5)
2.4.1.2 Properties
258(1)
2.4.1.3 Application
259(3)
2.4.1.4 Commercially Available Diarylide Yellow Pigments
262(16)
2.4.2 Bisacetoacetarylide Pigments
278(1)
2.4.2.1 Chemistry, Manufacture and Crystal Strctures
278(2)
2.4.2.2 Properties and Application
280(1)
2.4.2.3 Commercially Available Bisacetoacetarylide Pigments
281(3)
2.4.3 Dihydrazonepyrazolone Pigments (Formerly Called Disazopyrazolone Pigments)
284(1)
2.4.3.1 Chemistry, Manufacture and Crystal Structures
284(1)
2.4.3.2 Properties
285(1)
2.4.3.3 Application
285(1)
2.4.3.4 Commercially Available Dihydrazonepyrazolone Pigments
285(5)
2.5 β-Naphthol Pigments
290(10)
2.5.1 Chemistry, Manufacture and Crystal Structures
291(1)
2.5.1.1 Crystal Structures
292(1)
2.5.2 Properties
293(1)
2.5.3 Application
293(3)
2.5.4 Commercially Available β-Naphthol Pigments
296(4)
2.6 Naphthol AS Pigments
300(37)
2.6.1 Chemistry, Manufacture and Crystal Structures
302(1)
2.6.1.1 Crystal Structures
303(4)
2.6.2 Properties
307(2)
2.6.3 Application
309(1)
2.6.4 Commercially Available Naphthol AS Pigments
310(1)
2.6.4.1 General
310(1)
2.6.4.2 Naphthol AS Pigments with Simple Substituents
310(14)
2.6.4.3 Naphthol AS Pigments with Sulfonamide or Carbonamide Groups
324(13)
2.7 Red Hydrazone Pigment Lakes (Formerly Called Red Azo Pigment Lakes)
337(33)
2.7.1 β-Naphthol Pigment Lakes
338(1)
2.7.1.1 Chemistry, Manufacture and Crystal Structures
338(3)
2.7.1.2 Properties
341(1)
2.7.1.3 Application
342(1)
2.7.1.4 Commercially Available β-Naphthol Pigment Lakes
342(7)
2.7.2 BONA Pigment Lakes
349(1)
2.7.2.1 Chemistry, Manufacture and Crystal Structures
349(1)
2.7.2.2 Properties
350(1)
2.7.2.3 Application
351(1)
2.7.2.4 Commercially Available BONA Pigment Lakes
352(10)
2.7.3 Naphthol AS Pigment Lakes
362(1)
2.7.3.1 Chemistry, Manufacture, Crystal Structures, Properties and Applications
362(1)
2.7.3.2 Commercially Available Naphthol AS Pigment Lakes
362(4)
2.7.4 Naphthalene Sulfonic Acid Pigment Lakes
366(1)
2.7.4.1 Chemistry, Manufacture, Crystal Structures, Properties and Applications
366(1)
2.7.4.2 Commercially Available Naphthalene Sulfonic Acid Pigment Lakes
366(4)
2.8 Benzimidazolone Pigments
370(33)
2.8.1 Chemistry, Manufacture and Crystal Structures
372(1)
2.8.1.1 Coupling Components for Yellow and Orange Benzimidazolone Pigments
372(1)
2.8.1.2 Coupling Components for Red Benzimidazolone Pigments
373(1)
2.8.1.3 Pigment Synthesis and Aftertreatment
373(1)
2.8.1.4 Crystal Structures
374(6)
2.8.2 Properties
380(1)
2.8.3 Application
381(1)
2.8.4 Commercially Available Benzimidazolone Pigments
382(1)
2.8.4.1 The Yellow and Orange Series
382(11)
2.8.4.2 The Red and Brown Series
393(7)
2.8.5 Quinoxalinedione Pigments
400(1)
2.8.5.1 Chemistry, Manufacture and Crystal Structures
400(2)
2.8.5.2 Properties and Applications
402(1)
2.9 Dihydrazone Condensation Pigments (Formerly Called Disazo Condensation Pigments)
403(18)
2.9.1 Chemistry, Manufacture and Crystal Structures
404(3)
2.9.2 Properties
407(1)
2.9.3 Application
407(2)
2.9.4 Commercially Available Dihydrazone Condensation Pigments
409(1)
2.9.4.1 General
409(1)
2.9.4.2 Yellow Series
409(5)
2.9.4.3 Orange, Red and Brown Pigments
414(7)
References for
Chapter 2
421(4)
3 Polycyclic Pigments
425(188)
3.1 Phthalocyanine Pigments
426(34)
3.1.1 Starting Materials
427(1)
3.1.1.1 Phthalic Anhydride
428(1)
3.1.1.2 Phthalonitrile
428(1)
3.1.2 Manufacture
428(1)
3.1.2.1 Phthalonitrile Process
429(3)
3.1.2.2 Phthalic Anhydride/Urea Process
432(3)
3.1.2.3 Manufacturing the Different Crystal Modifications
435(2)
3.1.2.4 Phase- and Flocculation-Stabilized Copper Phthalocyanine Blue Pigments
437(1)
3.1.2.5 Manufacture of Green Types
438(1)
3.1.2.6 Metal-Free Phthalocyanine Blue
439(1)
3.1.3 Crystal Structures and Properties
440(5)
3.1.4 Application
445(2)
3.1.5 Commercially Available Phthalocyanine Pigments
447(13)
3.2 Quinacridone Pigments
460(27)
3.2.1 Starting Materials, Manufacture and Crystal Structures
461(1)
3.2.1.1 Thermal Ring Closure
461(2)
3.2.1.2 Acidic Ring Closure
463(1)
3.2.1.3 Dihalo-terephthalic Acid Process
463(1)
3.2.1.4 Hydroquinone Process
464(1)
3.2.1.5 Substituted Quinacridones
465(1)
3.2.1.6 Quinacridone Quinone
466(1)
3.2.1.7 Polymorphism
466(2)
3.2.1.8 Crystal Structures
468(7)
3.2.1.9 Solid Solutions
475(2)
3.2.2 Properties
477(1)
3.2.3 Application
477(1)
3.2.4 Commercially Available Quinacridone Pigments
477(10)
3.3 Vat Dyes Prepared as Pigments
487(1)
3.4 Perylene and Perinone Pigments
488(26)
3.4.1 Perylene Pigments
488(1)
3.4.1.1 Preparation of the Starting Materials
489(1)
3.4.1.2 Chemistry, Manufacture
489(2)
3.4.1.3 Crystal Structures and Properties
491(7)
3.4.1.4 Application
498(1)
3.4.1.5 Commercially Available Perylene Pigments
498(6)
3.4.2 Perinone Pigments
504(1)
3.4.2.1 Preparation of the Starting Materials
504(1)
3.4.2.2 Chemistry, Manufacture and Crystal Structures
505(5)
3.4.2.3 Properties
510(1)
3.4.2.4 Commercially Available Perinone Pigments and Their Application
510(3)
3.4.3 Semiperinone Pigments and Similar Pigments
513(1)
3.5 Diketopyrrolopyrrole (DPP) Pigments
514(11)
3.5.1 Chemistry, Manufacture and Crystal Structures
514(6)
3.5.2 Properties and Application
520(1)
3.5.3 Commercially Available DPP Pigments
520(5)
3.6 Indigo, Thioindigo and Thiazine Indigo Pigments
525(9)
3.6.1 Indigo
525(1)
3.6.1.1 Crystal Structure
525(1)
3.6.1.2 Properties and Application
525(1)
3.6.2 Thioindigo Pigments
526(1)
3.6.2.1 Chemistry, Manufacture and Crystal Structures
526(2)
3.6.2.2 Properties and Application
528(1)
3.6.2.3 Commercially Available Thioindigo Pigments and Their Application
529(3)
3.6.3 Thiazine Indigo Pigments
532(1)
3.6.3.1 Chemistry, Manufacture and Crystal Structures
532(2)
3.6.3.2 Properties
534(1)
3.6.3.3 Commercially Available Thiazine Indigo Pigments and Their Application
534(1)
3.7 Various Polycyclic Pigments Derived from Anthraquinone
534(35)
3.7.1 Aminoanthraquinone Pigments
535(1)
3.7.1.1 Synthesis of 1-Aminoanthraquinone
535(1)
3.7.1.2 Anthraquinone-Hydrazone Pigments
536(2)
3.7.1.3 Other Aminoanthraquinone Pigments
538(4)
3.7.1.4 Commercially Available Aminoanthraquinone Pigments
542(2)
3.7.2 Hydroxyanthraquinone Pigments
544(2)
3.7.2.1 Commercially Available Hydroxyanthraquinone Pigments
546(1)
3.7.3 Heterocyclic Anthraquinone Pigments
546(1)
3.7.3.1 Anthrapyrimidine Pigments
546(2)
3.7.3.2 Indanthrone and Flavanthrone Pigments
548(9)
3.7.4 Polycarbocyclic Anthraquinone Pigments
557(1)
3.7.4.1 Pyranthrone Pigments
557(4)
3.7.4.2 Anthanthrone Pigments
561(4)
3.7.4.3 Isoviolanthrone Pigments
565(2)
3.7.4.4 Violanthrone Pigments
567(2)
3.8 Dioxazine Pigments
569(12)
3.8.1 Preparation of the Starting Materials
570(1)
3.8.2 Chemistry, Manufacture and Crystal Structures
570(4)
3.8.2.1 Crystal Structures
574(1)
3.8.3 Properties
574(3)
3.8.4 Commercially Available Dioxazine Pigments and Their Application
577(4)
3.9 Quinophthalone Pigments
581(5)
3.9.1 Chemistry, Manufacture and Crystal Structures
582(3)
3.9.2 Properties and Application
585(1)
3.9.3 Commercially Available Quinophthalone Pigments
585(1)
3.9.3.1 Pigment Yellow 138
585(1)
3.10 Isoindolinone and Isoindoline Pigments
586(20)
3.10.1 General
586(1)
3.10.1.1 Isoindolinone Pigments
586(1)
3.10.1.2 Isoindoline Pigments
587(1)
3.10.2 Chemistry, Manufacture and Crystal Structures
588(1)
3.10.2.1 Isoindolinone Pigments
588(3)
3.10.2.2 Isoindoline Pigments
591(6)
3.10.3 Properties
597(1)
3.10.3.1 Isoindolinone Pigments
597(1)
3.10.3.2 Isoindoline Pigments
597(1)
3.10.4 Application
597(1)
3.10.5 Commercially Available Isoindolinone and Isoindoline Pigments
597(9)
References for
Chapter 3
606(7)
4 Miscellaneous Pigments
613(62)
4.1 Triarylcarbonium Pigments
613(27)
4.1.1 Inner Salts of Sulfonic Acids (Alkali Blue Types)
614(1)
4.1.1.1 Chemistry, Manufacture
615(4)
4.1.1.2 Properties and Application
619(1)
4.1.1.3 Commercially Available Alkali Blue Pigments
619(3)
4.1.2 Dye Salts with Complex Anions
622(1)
4.1.2.1 Chemistry, Manufacture and Crystal Structures
623(6)
4.1.2.2 Properties
629(1)
4.1.2.3 Application
630(1)
4.1.2.4 Commercially Available Dye Salts with Complex Anions
630(8)
4.1.3 Aluminium Pigment Lakes
638(2)
4.2 Metal Complex Pigments
640(15)
4.2.1 Chemistry, Synthesis and Crystal Structures
641(1)
4.2.1.1 Azo Metal Complexes
642(1)
4.2.1.2 Azomethine Metal Complexes
643(4)
4.2.2 Properties
647(1)
4.2.3 Application
647(1)
4.2.4 Commercially Available Metal Complex Pigments
647(8)
4.3 Pigments with Known Chemical Structure Which Cannot be Assigned to Other
Chapters
655(11)
4.3.1 Pigment Yellow 101
655(2)
4.3.2 Pigment Yellow 148
657(1)
4.3.3 Pigment Yellow 182
657(2)
4.3.4 Pigment Yellow 201
659(1)
4.3.5 Quinolonoquinolone Pigments (P.Y.218, P.Y.220, P.Y.221)
659(2)
4.3.6 Pigment Orange 64
661(1)
4.3.7 Pigment Orange 67
661(1)
4.3.8 Pigment Red 90
662(2)
4.3.9 Pigment Red 252
664(1)
4.3.10 Pigment Blue 63
664(1)
4.3.11 Pigment Brown 22
665(1)
4.3.12 Pigment Black 1
665(1)
4.4 Pigments with Hitherto Unpublished Chemical Structures
666(3)
4.4.1 Pigment Yellow 99
666(1)
4.4.2 Pigment Yellow 187
667(1)
4.4.3 Pigment Yellow 214
667(1)
4.4.4 Pigment Orange 83
667(1)
4.4.5 Pigment Red 204
667(1)
4.4.6 Pigment Red 278
668(1)
4.4.7 Pigment Red 285
668(1)
4.4.8 Pigment Red 293
668(1)
4.4.9 Pigment Violet 51
669(1)
4.4.10 Pigment Black 20
669(1)
4.5 Organic/Inorganic Hybrid Pigments
669(4)
References for
Chapter 4
673(2)
5 Legislation, Ecology, Toxicology
675(24)
5.1 Introduction
675(1)
5.2 Chemicals Legislation
676(15)
5.2.1 General
676(1)
5.2.1.1 Chemical Inventories
676(1)
5.2.1.2 GHS - Globally Harmonized System
677(2)
5.2.1.3 REACH (European Union)
679(1)
5.2.1.4 REACH Restricted Substances List
679(2)
5.2.2 Legislation Concerning Organic Pigments
681(2)
5.2.2.1 Food Packaging/Food Contact
683(2)
5.2.2.2 Purity Criteria
685(2)
5.2.2.3 Toys
687(1)
5.2.2.4 Consumer Goods
688(3)
5.3 Ecology
691(1)
5.4 Toxicology
692(4)
5.4.1 Acute Toxicity
693(1)
5.4.2 Irritation of Skin and Mucous Membrane
693(1)
5.4.3 Toxicity after Repeated Application
694(1)
5.4.4 Mutagenicity
694(1)
5.4.5 Chronic Toxicity - Carcinogenicity
694(2)
References for
Chapter 5
696(3)
Reaction Schemes
699(40)
A1 Starting Materials (Section 2.1)
699(1)
A2 Synthesis of Hydrazone Pigments (Section 2.2)
700(2)
A3 Monohydrazone Yellow and Monohydrazone Orange Pigments (Section 2.3)
702(2)
A4 Dihydrazone Pigments (Section 2.4)
704(1)
A5 β-Naphthol Pigments (Section 2.5)
705(1)
A6 Naphthol AS Pigments (Section 2.6)
706(1)
A7 Red Hydrazone Pigment Lakes (Section 2.7)
706(3)
A8 Benzimidazolone Pigments (Section 2.8)
709(1)
A9 Dihydrazone Condensation Pigments (Section 2.9)
710(3)
A10 Phthalocyanine Pigments (Section 3.1)
713(2)
A11 Quinacridone Pigments (Section 3.2)
715(6)
A12 Perylene and Perinone Pigments (Section 3.4)
721(1)
A13 Diketopyrrolopyrrole (DPP) Pigments (Section 3.5)
722(1)
A14 Indigo, Thioindigo and Thiazine Indigo Pigments (Section 3.6)
723(2)
A15 Various Polycyclic Pigments Derived from Anthraquinone (Section 3.7)
725(4)
A16 Dioxazine Pigments (Section 3.8)
729(1)
A17 Quinophthalone Pigments (Section 3.9)
730(1)
A18 Isoindolinone and Isoindoline Pigments (Section 3.10)
731(2)
A19 Triarylcarbonium Pigments (Section 4.1)
733(3)
A20 Metal Complex Pigments (Section 4.2)
736(3)
List of Commercially Available Pigments 739(16)
Index 755
Klaus Hunger (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.

Martin U. Schmidt (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.