High performance pigments:
Gespeichert in:
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[2009]
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| 245 | 1 | 0 | |a High performance pigments |c edited by Edwin B. Faulkner and Russell J. Schwartz |
| 250 | |a Second, completely revised and extended edition | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2009] | |
| 300 | |a XXII, 516 Seiten |b Illustrationen, Diagramme | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
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| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Faulkner, Edwin B. |d ca. 20./21. Jh. |0 (DE-588)1217605657 |4 edt | |
| 700 | 1 | |a Schwartz, Russell J. |d ca. 20./21. Jh. |e Sonstige |0 (DE-588)1217605754 |4 oth | |
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Datensatz im Suchindex
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Contents
Preface XIX
List of Contributors
XXI
Parti
1
Introduction to Inorganic High Performance Pigments
3
Gunter Buxbaum
1.1
Introduction
3
1.2
Survey of Inorganic Pigments
4
1.3
New Candidates on the Catwalk of Color
5
1.4
Challenges for the Future
6
2
Bismuth Vanadates
7
Hartmut Endriss
2.1
Introduction
7
2.2
Historical Background
7
2.3
Manufacture
8
2.4
Properties and Applications
8
2.4.1
Chemical Properties
8
2.4.2
Physical Properties
9
2.4.3
Coloristic Properties
9
2.4.4
Dispersibility
10
2.4.5
light Fastness and Weather Resistance
10
2.4.6
Chemical and Solvent Resistance
10
2.5
Applications
10
2.5.1
Coatings
10
2.5.2
Plastics
11
2.5.2.1
Properties
11
2.5.2.2
Applications
11
High Performance Pigments. Edited by Edwin B. Faulkner and Russell J. Schwartz
Copyright
© 2009
WILEY-VCH
Verlag
GmbH
&
Co. KGaA,
Weinheim
ISBN:
978-3-527-31405-8
VI
I Contents
2.5.2.3
Conformity of Pigments for Plastics Coloration to Food
and Drug Regulations
11
2.6
Toxicology
12
2.6.1
Acute
Toxicity
12
2.6.2
Chronic
Toxicity
12
2.7
Ecology
12
3
Cadmium Pigments
13
Paul Dunning
3.1
Introduction
13
3.2
Pigment History
13
3.2
Raw Materials
25
3.2.1
Cadmium
15
3.2.2
Selenium
15
3.3
Chemistry of Cadmium, Selenium and Cadmium
Sulfide
16
3.3.1
Cadmium
16
3.3.2
Selenium
Î6
3.3.3
Substitution in the CdS Lattice
17
3.4
Method of Pigment Manufacture
17
3.4.1
General Points
17
3.4.2
Cadmium Oxide Formation
19
3.4.3
Cadmium Metal Dissolution
19
3.4.4
Other Solution Making
20
3.4.5
Precipitation
20
3.4.6
Filtration and Washing
21
3.4.7
Drying
21
3.4.8
Calcination
2
J
3.4.9
Wet Milling
22
3.4.10
Removal of Soluble Cadmium
22
3.4.11
Final Drying and Milling
22
3.5
Physical Properties
22
3.6
Regulatory Issues
24
3.7
Uses
25
4
Cerium Pigments
27
jean-Noel
Berte
4.1
Introduction
27
4.2
Rare Earth
Sulfides
and the Origins of their Color.
28
4.3
Cerium
Sulfide
Pigment: Manufacture
31
4-А
Properties and Applications
34
4.4.1
Coloration of Plastics
34
4.4.2
Paint and Coatings Application
38
4.4.3
Miscellaneous Applications
39
4.5
Toxicology and Environmental Aspects
39
Contents
VII
4.6 Toxicological
and Environmental Concerns during the Manufacturing
Process
40
5
Complex Inorganic Color Pigments: An Overview.
41
James White
5.1
Introduction
41
5.2
Structures of CICPs
42
5.3
Production of CICPs
44
5.4
Titanate Pigments
44
5.4.1
Rutile Titanates
45
5.4.2
Spinel Titanates
46
5.4.3
Other Titanates
47
5.5
Aluminate
Pigments
47
5.6
Cobalt Aluminates
47
5.7
Cobalt Chromium Aluminates
48
5.8
Chromites and
Ferrites
49
5.9
Black CICPs
49
5.10
Brown Pigments
50
5.11
Green Chromites
51
6
Titanate Pigments: Colored
Rutile,
Priderite,
and Pseudobrookite Structured Pigments
53
John Maloney
6.1
Introduction
53
6.2
History
55
6.2.1
Doped-Rutile
(DR)
Pigments
57
6.2.2
Priderite Pigments
58
6.2.3
Pseudobrookite Pigments
58
6.3
Synthesis
58
6.3.1
DR
Pigments
59
6.3.2
Priderite Pigments
61
6.3.3
Pseudobrookite Pigments
62
6.4
Applications
62
6.5
Properties
63
6.5.1
Spectral Properties
63
6.5.1.1
Visible Spectral Characterization
63
6.5.1.2
UVandNIR Spectral Characterization
66
6.5.2
Physical Properties
66
6.5.2.1
Particle Size Distribution
66
6.5.2.2
X-ray Diffraction Characterization
67
6.5.2.3
Specific Gravity
68
6.5.2.4
Oil Absorption and Specific Surface Area
69
6.5.2.5
Powder Flow and Dusting
70
6.5.3
Chemical Properties
70
VIII Contents
6.5.3.1 pH
Measurement
70
6.5.3.2
Weathering
71
6.5.3.3
Particle Chemistry
72
Partii
7
Special Effect Pigments
77
Gerhard Pfaff
7.1
introduction
77
7.2
Pearlescent and Interference Pigments
78
7.2.1
Optical Principles of Pearlescent and Interference Pigments
79
7.2.2
Substrate-Free Pearlescent Pigments
82
7.2.2.1
Natural Pearl Essence
82
7.2.2.2
Basic Lead Carbonate
82
7.2.2.3
Bismuth Oxychloride
82
7.2.2.4
Micaceous Iron Oxide
83
7.2.2.5
Titanium Dioxide Flakes
83
7.2.3
Pigments Formed by Coating of Substrates
84
7.2.3.1
Metal Oxide-Mica Pigments
84
7.2.3.2
Silica Flake Pigments
90
7.2.3.3
Alumina Flake Pigments
94
7.2.3.4
Borosilicate-based Pigments
96
7.3
Effect Pigments Formed by Coating of Metal Flakes
96
7.4
Pigments Formed by Grinding a Film
97
7.5
Pigments Based on Liquid Crystal Polymers
98
7.6.1
Diffractive Pigments
101
7.6.2
Pigments Based on Holography and Gratings
102
Acknowledgments
103
&
Crystal Design of High Performance Pigments
105
Martin Schmidt
8.1
Introduction
105
8.2
Crystal Engineering of Organic Pigments
106
8.2.1
Close Packing
106
8.2.2
Crystal Energy
108
8.2.3
Specific Interactions
109
8.3
Crystal Structure Determination
113
8.4
Crystal Structure Calculation
115
8.4.1
Genera) Methods
115
8.4.2
Crystal Structure Calculations of Pigments
116
8.4.3
Crystallochromy
118
8.4.4
Morphology Calculation
119
Contents
IX
8.4.5 Pigment
Morphologies
121
8.5
Control
of
Interfacial
Properties Through Tailor-Made Additives
122
Part III
129
9
The Global Market for Organic High Performance Pigments
13 1
Fritz Brenzikofer
9.1
Introduction
131
9.2
The
1999
Market for Organic High Performance Pigments
¡32
9.3
The Producers of High Performance Pigments
133
9.4
The Demand for
HPP
by Consumer Market Segments
133
9.4.1
The Demand by Regions
Ì34
9.4.2
The Trade Balance of HPP among these Regions
134
9.5
Demand Factors for
H
PPs
137
9.5.1
Market Requirements and Trends
138
9.5.1.1
Industrial/Decorative Paints
138
9.5.1.2
Plastics
Ì38
9.5.1.3
New Markets
138
9.5.2
Marketing Strategies of Main HPP Producers
138
9.5.3
Globalization Prozess
UH
9.6
Conclusions/Outlook
138
10
Benzimidazolone Pigments and Related Structures
139
Hans-Joachim Metz
and Frank
Morgenroth
10.1
Introduction
139
10.2
Historical Background
143
10.3
Method of Manufacture
145
10.4
Typical Properties and Major Reasons for Use
146
10.5
Pigment Grades, Discussion of Individual Pigments
154
10.6
Pigment Manufacturers, Economics
158
10.7
Safety, Health and Environmental Aspects
164
Π
Diketopyrrolopyrrole (DPP) Pigments
/65
OlofWallquist and Roman
Lenz
11.1
Introduction
/65
History
165
11.2
Syntheses
166
11.2.1
Reformatsky Route
166
11.2.2
Succinic Ester Route
168
11.2.3
Succinic Amide Route
/69
11.2.4
Miscellaneous Routes
/69
11.3
Molecular Structure and Properties
170
11.3.1
Spectral Properties
170
Χ Ι
Contents
11.3.2
Spectral Properties
-
Fluorescence
172
11.3.3
Single X-ray Structure Analysis
174
11.4
Chemical Properties
176
11.4.1
Electrophilic Aromatic Substitution
177
11.4.2
Nucleophilic Aromatic Substitution
177
11.4.3
N-Alkylation
178
11.4.4
Transformations on the Carbonyl Group
179
11.5
Solid-State Properties
180
11.5.1
General Properties
180
11.5.2
Particle Size Control ISO
11.5.3
Polymorphism
182
11.5.4
Solid Solutions
182
11.5.5
Surface Modifications
184
11.6
Conventional Applications
185
11.7
Nonconventional Applications
190
12
Dioxazine Violet Pigments
195
Terence Chamberlain
12.1
Introduction
195
12.1.1
The Chemistry of Dioxazine Pigments
195
12.2
Synthesis
196
12.2.1
Dianil Formation
197
12.2.2
Cyclization of the Dianil
197
12.3
Pigmentation and Properties
202
12.3.1
Pigment Violet
23 202
12.3.2
Pigment Violet
37 203
12.4
Recent Developments
203
12.4.1
Preparation/Production Methods
203
12.4.2
New Products
204
13
Disazocondensation Pigments
205
Fritz
Herren
13.1
Introduction
205
13.2
Historical Background
205
13.3
Chemistry
206
13.3.1
Commercialized Pigments (Past and Present
[4]) 207
13.3.2
Recent Developments
212
13.4
Synthesis and Manufacture
224
13.5
Characterization, Properties, Application
226
13.5.1
Physical Characterization
226
13.5.2
Available Grades
216
13.5.3
Properties and Applications
227
Contents
XI
14 Isoindoline Pigments 221
Volker Radtke, Peter Erk, and Benno
Sens
14.1
Introduction
221
14.2
Historical Background
224
14.3
Methods of Manufacture
226
14.4
Typical Properties and Major Reasons for Use
229
14.5
Crystal Structures of Isoindoline Pigments
229
14.5.1
Structure Determination
229
14.5.2
Discussion
232
14.5.3 ESA Data 233
14.5
Pigment Grades; Discussion of Individual Pigments
236
14.6
Pigment Manufacturers; Economics
239
14.7
Toxicology and Ecology
240
15
Isoindolinone Pigments
243
Abul Iqbal, Fritz
Herren,
and OlofWallquist
15.1
Introduction
243
15.2
Chemistry
244
15.2.1
Azomethine-Type Isoindolinones
244
15.2.2
Methine-Type Isoindolinones
252
15.2.3
Metal Complexes Based on Isoindolinones
253
15.3
Physicochemical Properties
254
15.4
Commercial Products and Applications
257
16
Pery
lene
Pigments
261
Brian Thompson
16.1
Definition of
Perviene
Pigments
261
16.1.1
History
263
16.1.2
Color Index and Identity
263
16.2
Synthesis of Perylenes
263
16.2.1
Conversion of Perylenes: Acenaphthene to Perylene Tetracarboxylic Acid
Diimide (PTCI, Pigment Violet
29) 263
16.2.2
Synthesis of Perylene Tetracarboxylic Acid
Dianhydride (PTCA)
by
Hydrolysis of PTCI to PTCA, and PTCA as a Pigment (Pigment Red
224) 265
16.2.3
Alkylation of PTCI to Pigment Red
179
and other Perylene Pig¬
ments
265
16.2.4
Synthesis of Perylene Pigments and Mixed Crystals by Condensation of
PTCA with Amines
266
16.2.5
Halflmide, Half Anhydrides of PTCA
(10) 266
16.2.6
Derivatives of Perylene as Performance Enhancers
267
16.3
The Conditioning of Perylene Diimide Pigments
267
16.4
Mixed Crystals and Solid Solutions of Perylene Diimide Pigments
268
XI
Ρ Ι
Contents
16.5
Drying of Perylene Pigments
268
16.6
Physical Chemistry and Color Physics of Perylene Pigments
269
16.7
Perylene Pigments and their Applications
270
16.8
Perylenes as Functional Colorants
271
16.9
Current Producers
271
16.10
Pricing Trends and Economics of Use
272
16.11
Health, Safety, and Environmental Considerations
272
17
Phthalocyanines
-
High Performance Pigments
and Their Applications
275
Masao
Janáka
17.1
Introduction
27
S
17.2
Application of Optical Properties
276
17.2.1
Color Filters for Liquid Crystal Display Devices
276
17.2.2
Ink Jet Inks
277
17.2.3
Infrared Ray Absorbents
279
17.2.4
CD-R
281
17.3
Application of Optoelectronic Properties
282
173
Λ
Electrophotographic Photoreceptor
282
17.3.2
Nonlinear Optical Devices
286
17.4
Application of Catalysis
287
17.4.1
Deodorizers
287
17.4.2
Photodynamic Therapy
288
17.5
Conclusion
289
18
Quinacridone Pigments
293
Terence R. Chamberlain (modification of original chapter by Edward E.Jaffe)
18.1
Introduction
293
18.2
Historical Background
293
18.3
Quinacridone Syntheses
295
18.3.1
The Synthesis of DMSS from Dimethyl Succinate
295
18.3.1.1
By-Products Produced During the Synthesis and Isolation of DMSS
295
18.3.2
Synthesis of DMSS from Diketene (Methyl 4-Chloroacetoacetate)
297
18.3.3
Synthesis of Quinacridones by the Thermal Process
298
18.3.4
Synthesis of Quinacridones by the PPA Process
300
18.3.5
Synthesis of Quinacridones by Application of the Ullmann
Reaction
303
18.4
Recently Introduced Quinacridone Products
304
18.5
Structural Data and Spectra
305
18.6
Polymorphism
308
18.7
Substituted Quinacridones
311
18.8
Photostability and a Suggested Mechanism
313
18.9
Quinacridonequinone
315
18.10
Other
6,
13-Disubstituted Quinacridones
317
Contents XIII
18.11 Solid Solutions 318
18.12
Conditioning and Surface Treatment of Quinacridones
323
18.13
Applications
325
18.14
Health and Safety Factors
326
18.15
Business Aspects
326
19
Quinophthalone Pigments
331
Volker Radtke
19.1
Introduction
331
19.2
Historical Background
333
19.3
Methods of Manufacture
334
19.4
Typical Properties and Major Reasons for Use
335
19.5
Pigment Grades and Discussion of Individual Pigments
336
19.5.1
Discussion of Individual Pigments
338
19.6
Pigment Manufacturers: Economics
339
19.7
Toxicology and Ecology
340
20
Imidazolone-Annellated Triphenedioxazine Pigments
341
Martin U. Schmidt
20.1
Introduction
341
20.2
On the Structure of Pigment Violet
23 342
20.3
Imidazolone-Annellated Triphenedioxazine Pigments
344
20.3.1
Syntheses
345
20.3.2
Properties
346
20.3.2.1
Pigment Blue
80 346
20.3.2.2
Other Imidazolone-Annellated Triphenedioxazine Pigments
347
20.3.3
Crystal Engineering on Imidazolone-Annellated Triphenedioxazine
Pigments
347
20.3.3.1
Structure Determination from
Х
-Ray Powder Data
348
20.3.3.2
Crystal Structures of Pigment Blue
80
and the Dimethyl Derivative
(4b)
349
20.3.3.3
Crystal Engineering: Pigment Violet
57 351
Part IV
355
21
Chemical and Physical Characterization of High Performance
Organic Pigments
357
Constantinos Nicolaou
21.1
Introduction
357
21.2
Visible Spectrophotometry
359
21.2.1
Introduction
359
21.2.2
Applications of Visible Spectroscopy
362
21.2.2.1
Copper Phthalocyanines
362
XIV Contents
21.2.2.2
Visible
Spectra of Quinacridone
Pigments
364
21.2.2.3
Visible Spectra of Other Pigments
366
21.3
Applications of FT-IR Spectroscopy
368
21.3.1
Introduction
368
21.3.2
Applications of Infrared Spectroscopy
370
21.4
Mass Spectrometry Techniques
373
21.4.1
Introduction
373
21.5
High-Performance Liquid Chromatography
378
21.5.1
Introduction
378
21.5.2
Η Ρ
LC Applications
378
21.6
Powder X-ray Diffraction
380
21.6.1
Introduction
380
21.6.2
XRD Sample Preparation
382
21.6.3
Applications of XRD
382
21.7
Particle Sizing Techniques
390
21.7.1
Introduction
390
21.7.2
Transmission Electron Microscopy
393
21.7.2.2
Sample Preparation for
ТЕМ
Analysis
393
21.7.2.3
Applications of
ТЕМ
394
21.7.3
Optical Microscopy
396
21.7.3.1
Introduction
396
21.7.3.2
Applications of Optical Microscopy
397
21.7.4
Particle Size by
Ultracentrifugai
Sedimentation and Comparison to
ТЕМ
398
21.7.4.1
Introduction
398
21.7.4.2
Applications of Particle Sizing by Ultracentrifugation
399
21.8
Thermal Analysis and Decomposition Temperatures of HPOPs
404
21.9
Product Safety and Environmental Testing of HPOPs
407
22
Regulatory Affairs for High Performance Pigments: North America
409
Harold F. Fitzpatrick, Esq. and Glenn
С
Merritt, Esq.
22.1
Introduction
409
22.2
Toxic Substances Control Act
409
22.3
Canada
411
22.3.1
Assessment of the Canadian DSL
412
22
A Mexico
413
22.5
Toxic Release Inventory Reporting
414
22.6
Regulation of
de minimis
Levels
414
22.7
Food and Drug Administration
415
22.8
Color Pigments in General
415
22.9
PBT-TRI Rules
418
22.10
Nanotechnology and Regulation
420
22.11
High Production Volume (HPV) Substances
423
22.12
Phthalocyanine Pigments
424
Contents
XV
22.13 Quinacridone Pigments 424
22.14 Carbazole
Violet
Pigments 425
22.15 Perylene Pigments 426
22.16
Inorganic
Pigments 426
22.16.1
Complex Inorganic Color
Pigments 426
22.16.2
Cadmium
Pigments 427
22.17
Conclusion
428
23
Regulatory and Legislative Aspects of Relevance to High Performance
Pigments: Europe
431
Eric Clarke and Herbert Motschi
23.1
Introduction
431
23.2
The European Union and its Institutions
431
23.2.1
European Commission
432
23.2.2
European Parliament (E.P.)
433
23.2.3
The Council of the European Union and other Institutions
434
23.2.4
Legal Instruments
434
23.3
The Major
EU
Directives Governing Chemical Control
435
23.3.1
Dangerous Substances (Commission Directive 67/548/EEC)
436
23.3.1.1
Some Differences between
EU
and US Requirements
437
23.3.1.2
Notification
438
23.3.1.3
Classification and Labeling
440
23.3.2
Dangerous Preparations (E.P. and Council Directive 1999/45/EEC)
444
23.3.3
Safety Data Sheets (Commission Directive 2001/58/EC)
444
23.3.4
Existing Substances, Priority Lists, Risk Assessment (Council Regulation
EEC
793/93) 444
23.3.5
Restrictions of Marketing and Use
445
23.3.6
REACH
447
23.3.7
Pollution Control
448
23.3.8
Packaging and Packaging Waste (E.P. and Council Directive
94/62/EC)
448
23.3.9
Eco-Labels
448
23.3.10
Food Packaging Legislation
449
23.3.11
Technical Barriers to Trade
452
2ЪЛ
National Regulations
452
23.4.1
Germany
453
23.4.1.2 Wassergefährdungsklassen
(Water-Hazard Classes)
453
23.4.1.3 Dioxin
Limits
454
23.4.2
France
455
23.4.3
Switzerland
457
23.5
Future Enlargement of the
EU (PHARE
and similar programs)
458
23.6
Nonregulatory Initiatives
460
23.6.1
High Production Volume (HPV) Chemicals Testing Initiative
460
23.6.2
Precautionary Principle
460
XVI Contents
23.6.3
Black-listing
461
23.7
Confidentiality
462
23.8
Availability of Information on Current Regulations
462
23.9
Future Outlook
463
24
Infrared Reflecting Complex Inorganic Colored Pigments
467
Terry Detrie and Dan Swiier
24.1
Introduction
467
24.2
Background/Physics
468
24.2.1
Source of Infrared Light
468
24.2.2
Heating Mechanisms
469
24.2.3
Cooling Mechanisms
470
24.3
Measurement
471
24.3.1
ASTM E903:
Integrating Sphere Spectrophotometer
[3] 472
24.3.2
ASTM
C1549: Portable Solar Reflectometer
[4] 472
24.3.3
ASTM
£1918:
Pyranometer
[5] 472
243A
ASTM D4803:
Heat Buildup
[6] 472
24.4
Pigments
473
24.4.1
Introduction
473
24.4.2
Doped
Rutile Titanate
Yellows and Tans
473
24.4.3
CICP Tans and Browns
475
24.4.4
CrFe and Other CICP
IR
Blacks
476
24.4.5
New Inorganic
IR
Black Pigments
479
24.4.6
Blue Pigments
480
24.4.7
Green CICP Pigments
482
24.5
Formulation with
IR
Pigments
482
24.5.1
Opacity
483
24.5.2
Absorptions
484
24.6
Market Driving Forces
485
24.6.1
Studies
485
24.6.2
Specifications on "Cool Roof'
486
24.6.3
Rebate Programs
486
24.7
Conclusions
487
25
Toxicology and Ecotoxicology Issues with High Performance
Pigments
489
Robert
Mott
(revision of original chapter by Hugh M. Smith)
25.1
Introduction
489
25.2
Recent Toxicological Testing of High Performance Pigments
489
25.3
Past Confusion in Assessment of HPPs
490
25.3.1
Confusion between Water Soluble Salts of Inorganic Metals and Related
but Insoluble Pigments
490
25.3.2
Confusion bBetween Pigments and their Associated Impurities
492
25.3.3
False Positives in Genotoxicity Testing of Organic HPPs
492
Contents XVII
25.3.3
Over-Reliance on Structure Activity Relationship
(SAR)
Assessment of
HPPs
491
25.3.4
Confusion over Inaccurate "PBT" Classifications of HPPs
492
25.3.4
Inadequacy of Recent Computer-Driven Models for Substance
Profiling
492
25.3.5
Inadequacy of Partition Coefficient Calculations in Evaluating
Bioaccumulation
492
25.3.6
Continued Polarization Between Environmental
NGOs
and Industry
Groups
493
25.4
Current Programs for Toxicological and Ecotoxicological Assessment of
HPPs
493
25.5
The Way Ahead
494
25.5.1
Future Protocols for HPPs
494
25.5.2
Implementation of the Prior Informed Consent (PIC) Treaty
494
Appendix
497
Index
503 |
| adam_txt |
Contents
Preface XIX
List of Contributors
XXI
Parti
1
Introduction to Inorganic High Performance Pigments
3
Gunter Buxbaum
1.1
Introduction
3
1.2
Survey of Inorganic Pigments
4
1.3
New Candidates on the Catwalk of Color
5
1.4
Challenges for the Future
6
2
Bismuth Vanadates
7
Hartmut Endriss
2.1
Introduction
7
2.2
Historical Background
7
2.3
Manufacture
8
2.4
Properties and Applications
8
2.4.1
Chemical Properties
8
2.4.2
Physical Properties
9
2.4.3
Coloristic Properties
9
2.4.4
Dispersibility
10
2.4.5
light Fastness and Weather Resistance
10
2.4.6
Chemical and Solvent Resistance
10
2.5
Applications
10
2.5.1
Coatings
10
2.5.2
Plastics
11
2.5.2.1
Properties
11
2.5.2.2
Applications
11
High Performance Pigments. Edited by Edwin B. Faulkner and Russell J. Schwartz
Copyright
© 2009
WILEY-VCH
Verlag
GmbH
&
Co. KGaA,
Weinheim
ISBN:
978-3-527-31405-8
VI
I Contents
2.5.2.3
Conformity of Pigments for Plastics Coloration to Food
and Drug Regulations
11
2.6
Toxicology
12
2.6.1
Acute
Toxicity
12
2.6.2
Chronic
Toxicity
12
2.7
Ecology
12
3
Cadmium Pigments
13
Paul Dunning
3.1
Introduction
13
3.2
Pigment History
13
3.2
Raw Materials
25
3.2.1
Cadmium
15
3.2.2
Selenium
15
3.3
Chemistry of Cadmium, Selenium and Cadmium
Sulfide
16
3.3.1
Cadmium
16
3.3.2
Selenium
Î6
3.3.3
Substitution in the CdS Lattice
17
3.4
Method of Pigment Manufacture
17
3.4.1
General Points
17
3.4.2
Cadmium Oxide Formation
19
3.4.3
Cadmium Metal Dissolution
19
3.4.4
Other Solution Making
20
3.4.5
Precipitation
20
3.4.6
Filtration and Washing
21
3.4.7
Drying
21
3.4.8
Calcination
2
J
3.4.9
Wet Milling
22
3.4.10
Removal of Soluble Cadmium
22
3.4.11
Final Drying and Milling
22
3.5
Physical Properties
22
3.6
Regulatory Issues
24
3.7
Uses
25
4
Cerium Pigments
27
jean-Noel
Berte
4.1
Introduction
27
4.2
Rare Earth
Sulfides
and the Origins of their Color.
28
4.3
Cerium
Sulfide
Pigment: Manufacture
31
4-А
Properties and Applications
34
4.4.1
Coloration of Plastics
34
4.4.2
Paint and Coatings Application
38
4.4.3
Miscellaneous Applications
39
4.5
Toxicology and Environmental Aspects
39
Contents
VII
4.6 Toxicological
and Environmental Concerns during the Manufacturing
Process
40
5
Complex Inorganic Color Pigments: An Overview.
41
James White
5.1
Introduction
41
5.2
Structures of CICPs
42
5.3
Production of CICPs
44
5.4
Titanate Pigments
44
5.4.1
Rutile Titanates
45
5.4.2
Spinel Titanates
46
5.4.3
Other Titanates
47
5.5
Aluminate
Pigments
47
5.6
Cobalt Aluminates
47
5.7
Cobalt Chromium Aluminates
48
5.8
Chromites and
Ferrites
49
5.9
Black CICPs
49
5.10
Brown Pigments
50
5.11
Green Chromites
51
6
Titanate Pigments: Colored
Rutile,
Priderite,
and Pseudobrookite Structured Pigments
53
John Maloney
6.1
Introduction
53
6.2
History
55
6.2.1
Doped-Rutile
(DR)
Pigments
57
6.2.2
Priderite Pigments
58
6.2.3
Pseudobrookite Pigments
58
6.3
Synthesis
58
6.3.1
DR
Pigments
59
6.3.2
Priderite Pigments
61
6.3.3
Pseudobrookite Pigments
62
6.4
Applications
62
6.5
Properties
63
6.5.1
Spectral Properties
63
6.5.1.1
Visible Spectral Characterization
63
6.5.1.2
UVandNIR Spectral Characterization
66
6.5.2
Physical Properties
66
6.5.2.1
Particle Size Distribution
66
6.5.2.2
X-ray Diffraction Characterization
67
6.5.2.3
Specific Gravity
68
6.5.2.4
Oil Absorption and Specific Surface Area
69
6.5.2.5
Powder Flow and Dusting
70
6.5.3
Chemical Properties
70
VIII Contents
6.5.3.1 pH
Measurement
70
6.5.3.2
Weathering
71
6.5.3.3
Particle Chemistry
72
Partii
7
Special Effect Pigments
77
Gerhard Pfaff
7.1
introduction
77
7.2
Pearlescent and Interference Pigments
78
7.2.1
Optical Principles of Pearlescent and Interference Pigments
79
7.2.2
Substrate-Free Pearlescent Pigments
82
7.2.2.1
Natural Pearl Essence
82
7.2.2.2
Basic Lead Carbonate
82
7.2.2.3
Bismuth Oxychloride
82
7.2.2.4
Micaceous Iron Oxide
83
7.2.2.5
Titanium Dioxide Flakes
83
7.2.3
Pigments Formed by Coating of Substrates
84
7.2.3.1
Metal Oxide-Mica Pigments
84
7.2.3.2
Silica Flake Pigments
90
7.2.3.3
Alumina Flake Pigments
94
7.2.3.4
Borosilicate-based Pigments
96
7.3
Effect Pigments Formed by Coating of Metal Flakes
96
7.4
Pigments Formed by Grinding a Film
97
7.5
Pigments Based on Liquid Crystal Polymers
98
7.6.1
Diffractive Pigments
101
7.6.2
Pigments Based on Holography and Gratings
102
Acknowledgments
103
&
Crystal Design of High Performance Pigments
105
Martin Schmidt
8.1
Introduction
105
8.2
Crystal Engineering of Organic Pigments
106
8.2.1
Close Packing
106
8.2.2
Crystal Energy
108
8.2.3
Specific Interactions
109
8.3
Crystal Structure Determination
113
8.4
Crystal Structure Calculation
115
8.4.1
Genera) Methods
115
8.4.2
Crystal Structure Calculations of Pigments
116
8.4.3
Crystallochromy
118
8.4.4
Morphology Calculation
119
Contents
IX
8.4.5 Pigment
Morphologies
121
8.5
Control
of
Interfacial
Properties Through Tailor-Made Additives
122
Part III
129
9
The Global Market for Organic High Performance Pigments
13 1
Fritz Brenzikofer
9.1
Introduction
131
9.2
The
1999
Market for Organic High Performance Pigments
¡32
9.3
The Producers of High Performance Pigments
133
9.4
The Demand for
HPP
by Consumer Market Segments
133
9.4.1
The Demand by Regions
Ì34
9.4.2
The Trade Balance of HPP among these Regions
134
9.5
Demand Factors for
H
PPs
137
9.5.1
Market Requirements and Trends
138
9.5.1.1
Industrial/Decorative Paints
138
9.5.1.2
Plastics
Ì38
9.5.1.3
New Markets
138
9.5.2
Marketing Strategies of Main HPP Producers
138
9.5.3
Globalization Prozess
UH
9.6
Conclusions/Outlook
138
10
Benzimidazolone Pigments and Related Structures
139
Hans-Joachim Metz
and Frank
Morgenroth
10.1
Introduction
139
10.2
Historical Background
143
10.3
Method of Manufacture
145
10.4
Typical Properties and Major Reasons for Use
146
10.5
Pigment Grades, Discussion of Individual Pigments
154
10.6
Pigment Manufacturers, Economics
158
10.7
Safety, Health and Environmental Aspects
164
Π
Diketopyrrolopyrrole (DPP) Pigments
/65
OlofWallquist and Roman
Lenz
11.1
Introduction
/65
History
165
11.2
Syntheses
166
11.2.1
Reformatsky Route
166
11.2.2
Succinic Ester Route
168
11.2.3
Succinic Amide Route
/69
11.2.4
Miscellaneous Routes
/69
11.3
Molecular Structure and Properties
170
11.3.1
Spectral Properties
170
Χ Ι
Contents
11.3.2
Spectral Properties
-
Fluorescence
172
11.3.3
Single X-ray Structure Analysis
174
11.4
Chemical Properties
176
11.4.1
Electrophilic Aromatic Substitution
177
11.4.2
Nucleophilic Aromatic Substitution
177
11.4.3
N-Alkylation
178
11.4.4
Transformations on the Carbonyl Group
179
11.5
Solid-State Properties
180
11.5.1
General Properties
180
11.5.2
Particle Size Control ISO
11.5.3
Polymorphism
182
11.5.4
Solid Solutions
182
11.5.5
Surface Modifications
184
11.6
Conventional Applications
185
11.7
Nonconventional Applications
190
12
Dioxazine Violet Pigments
195
Terence Chamberlain
12.1
Introduction
195
12.1.1
The Chemistry of Dioxazine Pigments
195
12.2
Synthesis
196
12.2.1
Dianil Formation
197
12.2.2
Cyclization of the Dianil
197
12.3
Pigmentation and Properties
202
12.3.1
Pigment Violet
23 202
12.3.2
Pigment Violet
37 203
12.4
Recent Developments
203
12.4.1
Preparation/Production Methods
203
12.4.2
New Products
204
13
Disazocondensation Pigments
205
Fritz
Herren
13.1
Introduction
205
13.2
Historical Background
205
13.3
Chemistry
206
13.3.1
Commercialized Pigments (Past and Present
[4]) 207
13.3.2
Recent Developments
212
13.4
Synthesis and Manufacture
224
13.5
Characterization, Properties, Application
226
13.5.1
Physical Characterization
226
13.5.2
Available Grades
216
13.5.3
Properties and Applications
227
Contents
XI
14 Isoindoline Pigments 221
Volker Radtke, Peter Erk, and Benno
Sens
14.1
Introduction
221
14.2
Historical Background
224
14.3
Methods of Manufacture
226
14.4
Typical Properties and Major Reasons for Use
229
14.5
Crystal Structures of Isoindoline Pigments
229
14.5.1
Structure Determination
229
14.5.2
Discussion
232
14.5.3 ESA Data 233
14.5
Pigment Grades; Discussion of Individual Pigments
236
14.6
Pigment Manufacturers; Economics
239
14.7
Toxicology and Ecology
240
15
Isoindolinone Pigments
243
Abul Iqbal, Fritz
Herren,
and OlofWallquist
15.1
Introduction
243
15.2
Chemistry
244
15.2.1
Azomethine-Type Isoindolinones
244
15.2.2
Methine-Type Isoindolinones
252
15.2.3
Metal Complexes Based on Isoindolinones
253
15.3
Physicochemical Properties
254
15.4
Commercial Products and Applications
257
16
Pery
lene
Pigments
261
Brian Thompson
16.1
Definition of
Perviene
Pigments
261
16.1.1
History
263
16.1.2
Color Index and Identity
263
16.2
Synthesis of Perylenes
263
16.2.1
Conversion of Perylenes: Acenaphthene to Perylene Tetracarboxylic Acid
Diimide (PTCI, Pigment Violet
29) 263
16.2.2
Synthesis of Perylene Tetracarboxylic Acid
Dianhydride (PTCA)
by
Hydrolysis of PTCI to PTCA, and PTCA as a Pigment (Pigment Red
224) 265
16.2.3
Alkylation of PTCI to Pigment Red
179
and other Perylene Pig¬
ments
265
16.2.4
Synthesis of Perylene Pigments and Mixed Crystals by Condensation of
PTCA with Amines
266
16.2.5
Halflmide, Half Anhydrides of PTCA
(10) 266
16.2.6
Derivatives of Perylene as Performance Enhancers
267
16.3
The Conditioning of Perylene Diimide Pigments
267
16.4
Mixed Crystals and Solid Solutions of Perylene Diimide Pigments
268
XI
Ρ Ι
Contents
16.5
Drying of Perylene Pigments
268
16.6
Physical Chemistry and Color Physics of Perylene Pigments
269
16.7
Perylene Pigments and their Applications
270
16.8
Perylenes as Functional Colorants
271
16.9
Current Producers
271
16.10
Pricing Trends and Economics of Use
272
16.11
Health, Safety, and Environmental Considerations
272
17
Phthalocyanines
-
High Performance Pigments
and Their Applications
275
Masao
Janáka
17.1
Introduction
27
S
17.2
Application of Optical Properties
276
17.2.1
Color Filters for Liquid Crystal Display Devices
276
17.2.2
Ink Jet Inks
277
17.2.3
Infrared Ray Absorbents
279
17.2.4
CD-R
281
17.3
Application of Optoelectronic Properties
282
173
Λ
Electrophotographic Photoreceptor
282
17.3.2
Nonlinear Optical Devices
286
17.4
Application of Catalysis
287
17.4.1
Deodorizers
287
17.4.2
Photodynamic Therapy
288
17.5
Conclusion
289
18
Quinacridone Pigments
293
Terence R. Chamberlain (modification of original chapter by Edward E.Jaffe)
18.1
Introduction
293
18.2
Historical Background
293
18.3
Quinacridone Syntheses
295
18.3.1
The Synthesis of DMSS from Dimethyl Succinate
295
18.3.1.1
By-Products Produced During the Synthesis and Isolation of DMSS
295
18.3.2
Synthesis of DMSS from Diketene (Methyl 4-Chloroacetoacetate)
297
18.3.3
Synthesis of Quinacridones by the Thermal Process
298
18.3.4
Synthesis of Quinacridones by the PPA Process
300
18.3.5
Synthesis of Quinacridones by Application of the Ullmann
Reaction
303
18.4
Recently Introduced Quinacridone Products
304
18.5
Structural Data and Spectra
305
18.6
Polymorphism
308
18.7
Substituted Quinacridones
311
18.8
Photostability and a Suggested Mechanism
313
18.9
Quinacridonequinone
315
18.10
Other
6,
13-Disubstituted Quinacridones
317
Contents XIII
18.11 Solid Solutions 318
18.12
Conditioning and Surface Treatment of Quinacridones
323
18.13
Applications
325
18.14
Health and Safety Factors
326
18.15
Business Aspects
326
19
Quinophthalone Pigments
331
Volker Radtke
19.1
Introduction
331
19.2
Historical Background
333
19.3
Methods of Manufacture
334
19.4
Typical Properties and Major Reasons for Use
335
19.5
Pigment Grades and Discussion of Individual Pigments
336
19.5.1
Discussion of Individual Pigments
338
19.6
Pigment Manufacturers: Economics
339
19.7
Toxicology and Ecology
340
20
Imidazolone-Annellated Triphenedioxazine Pigments
341
Martin U. Schmidt
20.1
Introduction
341
20.2
On the Structure of Pigment Violet
23 342
20.3
Imidazolone-Annellated Triphenedioxazine Pigments
344
20.3.1
Syntheses
345
20.3.2
Properties
346
20.3.2.1
Pigment Blue
80 346
20.3.2.2
Other Imidazolone-Annellated Triphenedioxazine Pigments
347
20.3.3
Crystal Engineering on Imidazolone-Annellated Triphenedioxazine
Pigments
347
20.3.3.1
Structure Determination from
Х
-Ray Powder Data
348
20.3.3.2
Crystal Structures of Pigment Blue
80
and the Dimethyl Derivative
(4b)
349
20.3.3.3
Crystal Engineering: Pigment Violet
57 351
Part IV
355
21
Chemical and Physical Characterization of High Performance
Organic Pigments
357
Constantinos Nicolaou
21.1
Introduction
357
21.2
Visible Spectrophotometry
359
21.2.1
Introduction
359
21.2.2
Applications of Visible Spectroscopy
362
21.2.2.1
Copper Phthalocyanines
362
XIV Contents
21.2.2.2
Visible
Spectra of Quinacridone
Pigments
364
21.2.2.3
Visible Spectra of Other Pigments
366
21.3
Applications of FT-IR Spectroscopy
368
21.3.1
Introduction
368
21.3.2
Applications of Infrared Spectroscopy
370
21.4
Mass Spectrometry Techniques
373
21.4.1
Introduction
373
21.5
High-Performance Liquid Chromatography
378
21.5.1
Introduction
378
21.5.2
Η Ρ
LC Applications
378
21.6
Powder X-ray Diffraction
380
21.6.1
Introduction
380
21.6.2
XRD Sample Preparation
382
21.6.3
Applications of XRD
382
21.7
Particle Sizing Techniques
390
21.7.1
Introduction
390
21.7.2
Transmission Electron Microscopy
393
21.7.2.2
Sample Preparation for
ТЕМ
Analysis
393
21.7.2.3
Applications of
ТЕМ
394
21.7.3
Optical Microscopy
396
21.7.3.1
Introduction
396
21.7.3.2
Applications of Optical Microscopy
397
21.7.4
Particle Size by
Ultracentrifugai
Sedimentation and Comparison to
ТЕМ
398
21.7.4.1
Introduction
398
21.7.4.2
Applications of Particle Sizing by Ultracentrifugation
399
21.8
Thermal Analysis and Decomposition Temperatures of HPOPs
404
21.9
Product Safety and Environmental Testing of HPOPs
407
22
Regulatory Affairs for High Performance Pigments: North America
409
Harold F. Fitzpatrick, Esq. and Glenn
С
Merritt, Esq.
22.1
Introduction
409
22.2
Toxic Substances Control Act
409
22.3
Canada
411
22.3.1
Assessment of the Canadian DSL
412
22
A Mexico
413
22.5
Toxic Release Inventory Reporting
414
22.6
Regulation of
de minimis
Levels
414
22.7
Food and Drug Administration
415
22.8
Color Pigments in General
415
22.9
PBT-TRI Rules
418
22.10
Nanotechnology and Regulation
420
22.11
High Production Volume (HPV) Substances
423
22.12
Phthalocyanine Pigments
424
Contents
XV
22.13 Quinacridone Pigments 424
22.14 Carbazole
Violet
Pigments 425
22.15 Perylene Pigments 426
22.16
Inorganic
Pigments 426
22.16.1
Complex Inorganic Color
Pigments 426
22.16.2
Cadmium
Pigments 427
22.17
Conclusion
428
23
Regulatory and Legislative Aspects of Relevance to High Performance
Pigments: Europe
431
Eric Clarke and Herbert Motschi
23.1
Introduction
431
23.2
The European Union and its Institutions
431
23.2.1
European Commission
432
23.2.2
European Parliament (E.P.)
433
23.2.3
The Council of the European Union and other Institutions
434
23.2.4
Legal Instruments
434
23.3
The Major
EU
Directives Governing Chemical Control
435
23.3.1
Dangerous Substances (Commission Directive 67/548/EEC)
436
23.3.1.1
Some Differences between
EU
and US Requirements
437
23.3.1.2
Notification
438
23.3.1.3
Classification and Labeling
440
23.3.2
Dangerous Preparations (E.P. and Council Directive 1999/45/EEC)
444
23.3.3
Safety Data Sheets (Commission Directive 2001/58/EC)
444
23.3.4
Existing Substances, Priority Lists, Risk Assessment (Council Regulation
EEC
793/93) 444
23.3.5
Restrictions of Marketing and Use
445
23.3.6
REACH
447
23.3.7
Pollution Control
448
23.3.8
Packaging and Packaging Waste (E.P. and Council Directive
94/62/EC)
448
23.3.9
Eco-Labels
448
23.3.10
Food Packaging Legislation
449
23.3.11
Technical Barriers to Trade
452
2ЪЛ
National Regulations
452
23.4.1
Germany
453
23.4.1.2 Wassergefährdungsklassen
(Water-Hazard Classes)
453
23.4.1.3 Dioxin
Limits
454
23.4.2
France
455
23.4.3
Switzerland
457
23.5
Future Enlargement of the
EU (PHARE
and similar programs)
458
23.6
Nonregulatory Initiatives
460
23.6.1
High Production Volume (HPV) Chemicals Testing Initiative
460
23.6.2
Precautionary Principle
460
XVI Contents
23.6.3
Black-listing
461
23.7
Confidentiality
462
23.8
Availability of Information on Current Regulations
462
23.9
Future Outlook
463
24
Infrared Reflecting Complex Inorganic Colored Pigments
467
Terry Detrie and Dan Swiier
24.1
Introduction
467
24.2
Background/Physics
468
24.2.1
Source of Infrared Light
468
24.2.2
Heating Mechanisms
469
24.2.3
Cooling Mechanisms
470
24.3
Measurement
471
24.3.1
ASTM E903:
Integrating Sphere Spectrophotometer
[3] 472
24.3.2
ASTM
C1549: Portable Solar Reflectometer
[4] 472
24.3.3
ASTM
£1918:
Pyranometer
[5] 472
243A
ASTM D4803:
Heat Buildup
[6] 472
24.4
Pigments
473
24.4.1
Introduction
473
24.4.2
Doped
Rutile Titanate
Yellows and Tans
473
24.4.3
CICP Tans and Browns
475
24.4.4
CrFe and Other CICP
IR
Blacks
476
24.4.5
New Inorganic
IR
Black Pigments
479
24.4.6
Blue Pigments
480
24.4.7
Green CICP Pigments
482
24.5
Formulation with
IR
Pigments
482
24.5.1
Opacity
483
24.5.2
Absorptions
484
24.6
Market Driving Forces
485
24.6.1
Studies
485
24.6.2
Specifications on "Cool Roof'
486
24.6.3
Rebate Programs
486
24.7
Conclusions
487
25
Toxicology and Ecotoxicology Issues with High Performance
Pigments
489
Robert
Mott
(revision of original chapter by Hugh M. Smith)
25.1
Introduction
489
25.2
Recent Toxicological Testing of High Performance Pigments
489
25.3
Past Confusion in Assessment of HPPs
490
25.3.1
Confusion between Water Soluble Salts of Inorganic Metals and Related
but Insoluble Pigments
490
25.3.2
Confusion bBetween Pigments and their Associated Impurities
492
25.3.3
False Positives in Genotoxicity Testing of Organic HPPs
492
Contents XVII
25.3.3
Over-Reliance on Structure Activity Relationship
(SAR)
Assessment of
HPPs
491
25.3.4
Confusion over Inaccurate "PBT" Classifications of HPPs
492
25.3.4
Inadequacy of Recent Computer-Driven Models for Substance
Profiling
492
25.3.5
Inadequacy of Partition Coefficient Calculations in Evaluating
Bioaccumulation
492
25.3.6
Continued Polarization Between Environmental
NGOs
and Industry
Groups
493
25.4
Current Programs for Toxicological and Ecotoxicological Assessment of
HPPs
493
25.5
The Way Ahead
494
25.5.1
Future Protocols for HPPs
494
25.5.2
Implementation of the Prior Informed Consent (PIC) Treaty
494
Appendix
497
Index
503 |
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| illustrated | Illustrated |
| index_date | 2024-07-02T21:25:49Z |
| indexdate | 2024-07-20T09:45:29Z |
| institution | BVB |
| isbn | 9783527314058 3527314059 |
| language | English |
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| physical | XXII, 516 Seiten Illustrationen, Diagramme |
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| publishDateSort | 2009 |
| publisher | Wiley-VCH |
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| spelling | High performance pigments edited by Edwin B. Faulkner and Russell J. Schwartz Second, completely revised and extended edition Weinheim Wiley-VCH [2009] XXII, 516 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Früher mit der Nummer 9783527302048 Pigment (DE-588)4132245-9 gnd rswk-swf Hochleistungswerkstoff (DE-588)4312250-4 gnd rswk-swf Pigment (DE-588)4132245-9 s Hochleistungswerkstoff (DE-588)4312250-4 s DE-604 Faulkner, Edwin B. ca. 20./21. Jh. (DE-588)1217605657 edt Schwartz, Russell J. ca. 20./21. Jh. Sonstige (DE-588)1217605754 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3060775&prov=M&dok_var=1&dok_ext=htm Inhaltstext Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016589311&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | High performance pigments Pigment (DE-588)4132245-9 gnd Hochleistungswerkstoff (DE-588)4312250-4 gnd |
| subject_GND | (DE-588)4132245-9 (DE-588)4312250-4 |
| title | High performance pigments |
| title_auth | High performance pigments |
| title_exact_search | High performance pigments |
| title_exact_search_txtP | High performance pigments |
| title_full | High performance pigments edited by Edwin B. Faulkner and Russell J. Schwartz |
| title_fullStr | High performance pigments edited by Edwin B. Faulkner and Russell J. Schwartz |
| title_full_unstemmed | High performance pigments edited by Edwin B. Faulkner and Russell J. Schwartz |
| title_short | High performance pigments |
| title_sort | high performance pigments |
| topic | Pigment (DE-588)4132245-9 gnd Hochleistungswerkstoff (DE-588)4312250-4 gnd |
| topic_facet | Pigment Hochleistungswerkstoff |
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