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Industrial Organic Pigments: Production, Properties, Applications, 3rd, Completely Revised Edition

Industrial Organic Pigments: Production, Properties, Applications, 3rd, Completely Revised Edition

Willy Herbst, Klaus Hunger

ISBN: 978-3-527-60406-7 March 2006 678 Pages

 E-Book

$320.99

Description

'Everything there is to know about organic pigments'

Revised and updated, this highly acclaimed work, now in its third edition, remains the most comprehensive source of information available on synthetic organic pigments.
The book provides up-to-date information on synthesis, reaction mechanisms, physical and chemical properties, test methods, and applications of all industrially produced organic pigments of the world market.
Standardized methods have been used to obtain the data thus facilitating comparison between pigments. Chemists, engineers, colorists, and technicians are sure to find this book invaluable.

'Presentation throughout is of the highest quality and the volume must now become the standard reference text in this important area of colouring matters.'
Dyes and Pigments
'This is a very wide-ranging reference work ... it would be difficult to find a topic in this field not covered by this book.'
Ecochem
1 General.

1.1 Definition: Pigments–Dyes.

1.1.1 Organic-Inorganic Pigments.

1.2 Historical.

1.3 Classification of Organic Pigments.

1.3.1 Azo Pigments.

1.3.1.1 Monoazo Yellow and Orange Pigments.

1.3.1.2 Disazo Pigments.

1.3.1.3 β-Naphthol Pigments.

1.3.1.4 Naphthol AS Pigments (Naphthol Reds).

1.3.1.5 Azo Pigment Lakes (Salt Type Pigments).

1.3.1.6 Benzimidazolone Pigments.

1.3.1.7 Disazo Condensation Pigments.

1.3.1.8 Metal Complex Pigments.

1.3.1.9 Isoindolinone and Isoindoline Pigments.

1.3.2 Polycyclic Pigments.

1.3.2.1 Phthalocyanine Pigments.

1.3.2.2 Quinacridone Pigments.

1.3.2.3 Perylene and Perinone Pigments.

1.3.2.4 Diketopyrrolo–Pyrrole (DPP) Pigments.

1.3.2.5 Thioindigo Pigments.

1.3.3 Anthraquinone Pigments.

1.3.3.1 Anthrapyrimidine Pigments.

1.3.3.2 Flavanthrone Pigments.

1.3.3.3 Pyranthrone Pigments.

1.3.3.4 Anthanthrone Pigments.

1.3.4 Dioxazine Pigments.

1.3.5 Triarylcarbonium Pigments.

1.3.6 Quinophthalone Pigments.

1.4 Chemical Characterization of Pigments.

1.4.1 Hue.

1.4.1.1 Crystal Modification and Crystal Structure.

1.4.2 Tinctorial Strength.

1.4.3 Lightfastness and Weatherfastness.

1.4.4 Solvent and Migration Fastness.

1.5 Physical Characterization of Pigments.

1.5.1 Specific Surface Area.

1.5.2 Particle Size Distribution.

1.5.2.1 Determination of Particle Size by Ultrasedimentation.

1.5.2.2 Determination by Electron Microscopy.

1.5.2.3 Data Representation.

1.5.3 Polymorphism.

1.5.4 Crystallinity.

1.6 Important Application Properties and Concepts.

1.6.1 Coloristic Properties (by F. Gläser).

1.6.1.1 Color.

1.6.1.2 Color Depth.

1.6.1.3 Color Differences.

1.6.1.4 Optical Behaviour of Pigmented Coatings.

1.6.1.5 Tinctorial Strength.

1.6.1.6 Hiding Power.

1.6.1.7 Transparency.

1.6.2 Fastness to Solvents and Special Application Fastness.56

1.6.2.1 Organic Solvents.

1.6.2.2 Water, Soap, Alkali, and Acids.

1.6.2.3 Pigment Performance in Special Applications.

1.6.2.4 Textile Fastness Properties.

1.6.3 Migration.

1.6.3.1 Blooming.

1.6.3.2 Bleeding/Overspraying Fastness.

1.6.4 Disturbances During the Processing of Pigmented Systems.

1.6.4.1 Plate-Out.

1.6.4.2 Overpigmentation/Chalking.

1.6.4.3 Distortion/Nucleation in Polymers.

1.6.5 Dispersion.

1.6.5.1 General Considerations.

1.6.5.2 Desagglomeration of Pigment Particles.

1.6.5.3 Wetting of Pigment Particle Surfaces.

1.6.5.4 Distribution of the Dispersed Pigment in its Medium.

1.6.5.5 Stabilization.

1.6.5.6 Dispersion and the Critical Pigment Volume Concentration.

1.6.5.7 Test Methods.

1.6.5.8 Flush Pastes.

1.6.5.9 Pigment Preparations.87

1.6.6 Lightfastness and Weatherfastness.

1.6.6.1 Definition and General Information.

1.6.6.2 Evaluation Techniques and Equipment.

1.6.6.3 Factors Determining the Lightfastness.

1.6.7 Thermal Stability.

1.6.8 Flow Properties of Pigmented Systems.

1.6.8.1 Rheological Properties.

1.6.8.2 Viscoelastic Properties.

1.6.8.3 Influence on the Flow Properties.

1.6.8.4 Correlation between Flow Behavior and Rheological Parameters.

1.6.8.5 Rheological Measurements.

1.7 Particle Size Distribution and Application Properties of Pigmented Media.

1.7.1 Tinctorial Strength.

1.7.2 Hue.

1.7.3 Hiding Power, Transparency.

1.7.4 Lightfastness and Weatherfastness.

1.7.5 Dispersibility.

1.7.6 Gloss.

1.7.7 Solvent and Migration Fastness.

1.7.8 Flow.

1.8 Areas of Application for Organic Pigments.

1.8.1 Printing Inks.

1.8.1.1 Offset/Letterpress Printing.

1.8.1.2 Gravure Printing.

1.8.1.3 Flexo and Screen Printing and Other Printing Processes.

1.8.1.4 Security Printing.

1.8.2 Coatings.

1.8.2.1 Oxidatively Drying Paints.

1.8.2.2 Oven Drying Systems.

1.8.2.3 Emulsion Paints.

1.8.3 Plastics.

1.8.3.1 Polyolefins.

1.8.3.2 Polyvinyl Chloride (PVC).

1.8.3.3 Polyurethane.

1.8.3.4 Polyamide, Polycarbonate, Polyester, Polyoxymethylene.

1.8.3.5 Polystyrene, Styrene-Copolymers, Poly(Methyl Methacrylate).

1.8.3.6 Elastomers.

1.8.3.7 Thermosets (Thermosetting Plastics).

1.8.3.8 Spin Dyeing.

1.8.4 Other Areas of Application.

2 Azo Pigments.

2.1 Starting Materials, Synthesis.

2.1.1 Diazo Components.

2.1.2 Coupling Compounds.

2.1.3 Important Intermediates.

2.2 Synthesis of Azo Pigments.

2.2.1 Diazotization.

2.2.1.1 Diazotization Mechanism.

2.2.1.2 Methods of Diazotization.

2.2.2 Coupling.

2.2.2.1 Coupling Techniques.

2.2.3 Finishing.

2.2.4 Filtration, Drying, Milling.

2.2.5 Azo Pigment Synthesis by Continuous Operation.

2.2.6 Production Units for Azo Pigment Manufacture by Batch Operation.

2.3 Monoazo Yellow and Orange Pigments.

2.3.1 Chemistry, Manufacture.

2.3.1.1 Non-laked Monoazo Yellow and Orange Pigments.

2.3.1.2 Monoazo Yellow Pigment Lakes.

2.3.2 Properties.

2.3.2.1 Non-laked Monoazo Yellow and Orange Pigments.

2.3.2.2 Monoazo Yellow Pigment Lakes.

2.3.3 Application.

2.3.4 Commercially Available Monoazo Yellow and Orange Pigments.

2.4 Disazo Pigments.

2.4.1 Diarylide Yellow Pigments.

2.4.1.1 Chemistry, Manufacture.

2.4.1.2 Properties.

2.4.1.3 Application.

2.4.1.4 Commercially Available Diarylide Yellow and Orange Pigments.

2.4.2 Bisacetoacetarylide Pigments.

2.4.2.1 Commercially Available Bisacetoacetarylide Pigments and Their Properties.

2.4.3 Disazopyrazolone Pigments.

2.4.3.1 Chemistry, Manufacture.

2.4.3.2 Properties.

2.4.3.3 Application.

2.4.3.4 Commercially Available Pigments.

2.5 β-Naphthol Pigments.

2.5.1 Chemistry, Manufacture.

2.5.2 Properties.

2.5.3 Application.

2.5.4 Commercially Available β-Naphthol Pigments.

2.6 Naphthol AS Pigments.

2.6.1 Chemistry, Manufacture.

2.6.2 Properties.

2.6.3 Application.

2.6.4 Commercially Available Naphthol AS Pigments.

2.7 Red Azo Pigment Lakes.

2.7.1 _-Naphthol Pigment Lakes.

2.7.1.1 Chemistry, Manufacture.

2.7.1.2 Properties.

2.7.1.3 Application.

2.7.1.4 Commercially Available Pigments.

2.7.2 BONA Pigment Lakes.

2.7.2.1 Chemistry, Manufacture.

2.7.2.2 Properties.

2.7.2.3 Application.

2.7.2.4 Commercially Available BONA Pigment Lakes.

2.7.3 Naphthol AS Pigment Lakes.

2.7.3.1 Chemistry, Manufacture, and Properties.

2.7.3.2 Commercially Available Naphthol AS Pigment Lakes.

2.7.4 Naphthalene Sulfonic Acid Pigment Lakes.

2.7.4.1 Chemistry, Manufacture, and Properties.

2.7.4.2 Commercially Available Pigments.

2.8 Benzimidazolone Pigments.

2.8.1 Chemistry, Manufacture.

2.8.1.1 Yellow and Orange Benzimidazolone Pigments – Coupling Component.

2.8.1.2 Red Benzimidazolone Pigments – Coupling Component.

2.8.1.3 Pigment Synthesis and Aftertreatment.

2.8.1.4 Results of Crystal Structure Analyses.

2.8.2 Properties.

2.8.3 Application.

2.8.4 Commercially Available Benzimidazolone Pigments.

2.9 Disazo Condensation Pigments.

2.9.1 Chemistry, Manufacture.

2.9.2 Properties.

2.9.3 Application.

2.9.4 Commercially Available Pigments.

2.10 Metal Complex Pigments.

2.10.1 Chemistry, Synthesis.

2.10.1.1 Azo Metal Complexes.

2.10.1.2 Azomethine Metal Complexes.

2.10.2 Properties.

2.10.3 Application.

2.10.4 Commercially Available Pigments.

2.11 Isoindolinone and Isoindoline Pigments.

2.11.1 Chemistry, Synthesis, Starting Materials.

2.11.1.1 Azomethine Type: Tetrachloroisoindolinone Pigments.

2.11.1.2 Methine Type: Isoindoline Pigments.

2.11.2 Properties.

2.11.3 Application.

2.11.4 Commercially Available Isoindolinone and Isoindoline Pigments.

3 Polycyclic Pigments.

3.1 Phthalocyanine Pigments.

3.1.1 Starting Materials.

3.1.2 Manufacture.

3.1.2.1 Phthalonitrile Process.

3.1.2.2 Phthalic Anhydride/Urea Process.

3.1.2.3 Manufacturing the Different Crystal Modifications.

3.1.2.4 Phase- and Flocculation-Stabilized Copper Phthalocyanine Blue Pigments.

3.1.2.5 Manufacture of Green Types.

3.1.2.6 Metal-free Phthalocyanine Blue.

3.1.3 Properties.

3.1.4 Application.

3.1.5 Commercially Available Pigments.

3.2 Quinacridone Pigments.

3.2.1 Manufacture, Starting Materials.

3.2.1.1 Thermal Ring Closure.

3.2.1.2 Acidic Ring Closure.

3.2.1.3 Dihalo Terephthalic Acid Process.

3.2.1.4 Hydroquinone Process.

3.2.1.5 Substituted Quinacridones.

3.2.1.6 Quinacridone Quinone.

3.2.1.7 Polymorphism.

3.2.2 Properties.

3.2.3 Application.

3.2.4 Commercially Available Quinacridone Pigments.

3.3 Vat Dyes Prepared as Pigments.

3.4 Perylene and Perinone Pigments.

3.4.1 Perylene Pigments.

3.4.1.1 Preparation of the Starting Materials.

3.4.1.2 Chemistry, Manufacture.

3.4.1.3 Properties.

3.4.1.4 Application.

3.4.1.5 Commercially Available Perylene Pigments.

3.4.1.6 Various Other Perylene Tetracarboxylic Acid Pigments.

3.4.2 Perinone Pigments.

3.4.2.1 Preparation of the Starting Materials.

3.4.2.2 Chemistry, Manufacture.

3.4.2.3 Properties.

3.4.2.4 Commercially Available Perinone Pigments and Their Application.

3.5 Diketopyrrolo-Pyrrole (DPP) Pigments.

3.5.1 Chemistry, Manufacture.

3.5.2 Properties and Application.

3.5.3 Commercially Available DPP Pigments.

3.6 Thioindigo Pigments.

3.6.1 Chemistry, Manufacture.

3.6.2 Properties.

3.6.3 Commercially Available Types and Their Application.

3.7 Various Polycyclic Pigments.

3.7.1 Aminoanthraquinone Pigments.

3.7.1.1 Anthraquinone-Azo Pigments.

3.7.1.2 Other Aminoanthraquinone Pigments.

3.7.1.3 Properties and Application.

3.7.2 Hydroxyanthraquinone Pigments.

3.7.2.1 Properties and Application.

3.7.3 Heterocyclic Anthraquinone Pigments.

3.7.3.1 Anthrapyrimidine Pigments.

3.7.3.2 Indanthrone and Flavanthrone Pigments.

3.7.4 Polycarbocyclic Anthraquinone Pigments.

3.7.4.1 Pyranthrone Pigments.

3.7.4.2 Anthanthrone Pigments.

3.7.4.3 Isoviolanthrone Pigments.

3.8 Dioxazine Pigments.

3.8.1 Preparation of the Starting Materials.

3.8.2 Chemistry, Manufacture.

3.8.3 Properties.

3.8.4 Commercially Available Dioxazine Pigments and Their Application.

3.9 Quinophthalone Pigments.

3.9.1 Chemistry, Manufacture.

3.9.2 Properties and Application.

3.10 Triarylcarbonium Pigments.

3.10.1 Inner Salts of Sulfonic Acids (Alkali Blue Types).

3.10.1.1 Chemistry, Manufacture.

3.10.1.2 Properties.

3.10.1.3 Commercially Available Types and Their Application.

3.10.2 Dye Salts with Complex Anions.

3.10.2.1 Chemistry, Manufacture.

3.10.2.2 Properties.

3.10.2.3 Application.

3.10.2.4 Important Representatives.

4 Miscellaneous Pigments.

4.1 Aluminum Pigment Lakes.

4.2 Pigments with Known Chemical Structure Which Cannot be Assigned to Other Chapters.

4.3 Pigments with Hitherto Unknown Chemical Structure.

5 Legislation, Ecology, Toxicology.

5.1 Introduction.

5.2 Legislation.

5.2.1 General.

5.2.2 Legislation Concerning Organic Pigments.

5.2.2.1 Food Packaging.

5.2.2.2 Toys.

5.2.2.3 Consumer Goods.

5.3 Ecology.

5.4 Toxicology.

5.4.1 Acute Toxicity.

5.4.2 Irritation of Skin and Mucous Membrane.595

5.4.3 Toxicity After Repeated Application.

5.4.4 Mutagenicity.

5.4.5 Chronic Toxicity – Carcinogenicity.

Review of Chemical Structures and Chemical Reactions.

List of Commercially Available Pigments.

Subject Index.

"…a valuable source of information on synthesis and properties of organic pigments." (E-STREAMS, December 2004)

"...This volume can be recommended unreservedly to industrial and academic practitioners concerned in any way with the technological aspects of organic pigments..." (Dyes and Pigments)

"...The authors have succeeded to present an excellent and critical review on the state of the art of organic pigments.... This book has already become a standard in the field of organic coatings science..." (Progress in Organic Coatings)

"...This book is a very wide-ranging reference work...it would be difficult to find a topic in this field that is not covered." (Ecochem)

"...This present volume is an especially welcome addition to the current texts on colouring matters.... The volume can be recommended unreservedly to industrial and academic practitioners. Presentation throughout is of highest quality and the volume must now become the standard reference text in this important area of colouring matters." (Dyes and Pigments)

"A complete presentation of organic pigments in the context of their industrial importance, without competition as fa r as presentation and content are concerned.... An outstanding performance by the two authors, who have probably created a future standard reference work." (Einkaufszentrale für öffentliche Bibliotheken)

"...The book shows masterly treatment of the subject with high-quality presentation..." (Chemical Engineering World)

"...The eclecticism of the present work is a tribute to the authors in having succeeded, so very eminently, in providing us with such a highly and commendably useful work in an area where many other authors have failed. In other words, a book that can be profitably lined up on any technological bookshelf in the English-speaking world, as being a paradigm of technological publishing excellence in the field of industrial organic pigments." (Paint India)

"...This book definitely fills a gap in the literature of pigment application properties and can be recommended to every technologist working in this subject area." (Nachrichten aus Chemie, Technik und Laboratorium)

"...a comparable work does not exist..." (Kunststoffe)

"...the strength of this work lies in the logic and consequence of its structure. Thanks to its clarity, the numerous tables and the index, one can quickly find a comprehensive answer to almost every question in the subject area of organic pigments.... This versatile reference work can be warmly recommended to every specialist in the paints and coatings, printing inks, and pigment production industry." (farbe und lack)