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SYNTHETIC DYES, PIGMENTS & INTERMEDIATES

Written By :

TECHNOLOGY OF

EIRI Consultants and Engineers

Copy Reserved by Sudhir Gupta, Delhi

ISBN : 978-81-86732-51-9

4449, Nai Sarak, Main Road, Delhi-110 006 (India) E-Mail : eiribooks@yahoo.com

Preface
The book Technology of Synthetic Dyes, Pigments and Intermediates covers almost all the basic and advanced details of setup own Dyes Processing Industry. The new edition of the book is covering latest technology including Dyes, Azo Dyes, Azoic Dyes, Acid Dyes, Basic Dyes, Disperse Dyes, Vat Dyes, Anthrimides and Carbazoles, Vat Dyes and Vat Pastes, Indigoid and Thioindigoid Dyes, Indigosol, Flourination of Dyes, Sulphur Dyes,, Reactive Dyes, Intermediates for Dyes and Pigments, Flouroscent Brightesns and Optical Whtiening Agents, Typcial Commercial Brands, Names of Textiles, Colouratns Accessories Products etc. Classification of Pigments and Extenders, Inorganic Pigments, Azo pigments, highgrade organic pigments, phthalocyanines, fluorscent pigments quality control and evaluation of pigments, pigments for textiles, pigments for paints pigments for printinginks, pigments for plastics, rubber and cosmetics, chemical plants daa for dyes and pigments, plant economics of dyes and dye intermediates, plant economics of methyle blues, plant economics of acid block dye, plant economics of green oxide and blue oxide, plant economics of Azo Dyes, Plant Economics of Dyes, Suppliers of Plants Machineries and Equipements.
Director
Nai Sarak, Main Road, Delhi-110 006 (India) E-mail : eiribooks@yahoo.com

CONTENTS-CUM-SUBJECT INDEX
1 Dyes 1-35 Requisites of a True Dye 1 Types of Fibres 2 Dyeing 6 Various methods of dyeing 11 Fastness properties 15 Historical development from natural to synthetic dyes 16 Nomenclature of dyes intermediates 19 Nomenclature of dyes 20 Historical Development of Dyes 24 Natural dyes 24 Limitations of Natural Dyes 26 Synthetic Dyes 27 Important dyestuff intermediates 28 Disperse azo dye 34 2 Azo Dyes 36-69 The Azo coupling reactions 37 Congo Red 51 Diazotization 51 Coupling 51 Isolation 52 Direct Black E 52 Diazotization of Benzidine 53 First Coupling 53 Second Coupling 53 Third Coupling 53 Isolation 54 Direct Blue 2B 54 Diazotization 54 Coupling 55 Isolation 55 Violet N 55 Diazotization of Benzidine Coupling Isolation Sky-Blue FF Diazotization of Dianisidine Coupling Yield Ethylation Direct Light Fast Blue 4GH Plant for Azo Dyes Important notes for diazotization and coupling 55 56 56 56 56 57 57 58 58 59 60

3 Azoic Dyes 70-98 Azo Coupling Components 70 Bases 70 Rapid Fast Colours 84 Rapidogens 85 m-Nitro Aniline (Fast orange R) 85 Properties 88 Solubility 88 O-Chloroaniline (Fast Yellow G, Gc) 88 O-Anisidine (Fast Red BB) 89 Solvolysis 89 Reduction 90 Properties 90 2-Nitro-p-Anisidine (Fast Bordeaux G P) 90 Purification 91 Nitration 91 Hydrolysis 91 Purification 91 Naphthol AS 92 Properties of finished product 92 Naphthol AS-BS 93

Properties of finished product Physical Properties of Naphthol AS-OL Naphthol AS-G 4 Acid Dyes Simple Acid Dyes Mordant Acid Dyes Premetallized Acid Dyes Manufacturing Processes Acid Orange II Acid Flourescein Acid Light Fast Yellow G Acid Fast Red A Metanil Yellow Acid Black 10 BX

94 94 95 99-122 99 99 100 116 116 116 117 118 118 119

Cooking Isolation Rhodamine B Reaction Process

140 141 141 141 141

5 Basic Dyes 122-142 Diphenyl methane 126 Triphenyl methane dyes 126 Thiazines 127 Oxazine Dyes 128 Xanthene Dyes 128 Manufacturing Process 129 Auramine O 129 Reaction 130 Process 130 Malachite Green 131 Reaction 132 Process 133 Leuco Malachite Green 133 New Magenta 134 Process 135 Process 136 Safranine T 136 Process 136 Aminoazotoluene Preparation 136 Reduction 137 Oxidation 137 Methylene Blue 138 Nitrosoation 139 Reduction 139 Acid Formation 139 Indamine Formation 140

6 Disperse Dyes 143-175 Dispersion 144 Effect of Dispersing Agents 144 Levelling Agents 145 Classification 145 Disperse dyes in the dye bath 147 Disperse dyes in the fibre 147 Sensitivity to metal 147 Solacet Dyes (Water Soluble) 148 Light 148 Gas Fumes 148 Sublimation 149 Wash fastness 149 Current Research Work 149 Disperse Yellow 1 161 Reaction 162 Disperse Yellow 13 163 Acid Pasting 163 Dispersion 163 Disperse Yellow 42 163 Reaction 164 Stage I 164 Stage II 164 Disperse Orange 1 165 Procedure 165 Emulsion of Diphenylamine 165 Test 165 Coupling 166 Disperse Orange 13 166 Diazotisation of Aniline 166 Coupling Solution 167 Coupling 167 Stage II Diazotization of aniline azo dye 167 Coupling Solution 167 Coupling 167 Dispersion 167 Disperse Red 4 168 Acid pasting and Dispersion 168 Dispersion 168

Test Disperse Red 9 Treatment with hydrochloric acid Disperse Blue 1 Reactions Stage II Reduction Stage III Acetylation of 1 : 5 and 1:8 diamino anthraquinone Stage IV Nitration and Reduction Reduction Stage V Hydrolysis Disperse Blue 3 Reaction Test I Test II Disperse Black 1 Coupling Test Disperse Violet 8 Reaction Sulfonation Nitration Hydrolysis Dispersion 7

168 168 169 169 169 170

Fused Ring System Dyes containing larger ring systems

188 191

171 171 171 171 171 172 172 172 173 173 173 173 174 174 174 174 174

8 Anthrimides and Carbazoles 193-209 Anthraquinone-carbazoles 195 Ring closure with aluminium chloride 196 Ring Closure with Titanium Tetrachloride 198 Ring closure with sulphuric acid 199 Ring closure with Potassium Hydroxide 202 Oxidation 202 Characterisation of Anthrimides and Anthraquinone Carbazoles 204 Spectral Differentiation 206 Ultraviolet and Visible Spectra 206 Infrared 208 C=O Stretching and NH deformation vibrations 208 9 Vat Dyes & Vat Pastes 210-230 Vat Paste 211 Manufacturing of Vat Pastes 211 Vat Orange RF Paste 211 Golden Yellow G.O.K. Paste 211 Magenta B Paste 211 Vat Blue 4G Paste 212 Vat Pink R Paste 212 Vat Blue 4B Paste 212 Vat Black BB Paste 212 Vat Green FB Paste 213 Vat Brown RRO Paste Special 213 Vat Violet 2R Paste 213 Vat Violet GCN Paste 213 Vat Scarlet GGN Paste 214 Vat Grey 3B Paste 214 Manufacturing Process 214 Indanthrene Rubine R 214

Vat Dyes 176-192 Five Membered Rings 176 One Heteroatom 176 Two Heteroatoms 178 Attachment at 2-position 178 Attachment at 1, 2-position 178 Attachment at 2,3-position 180 Attachment at 1,9-positions 181 Vat Dyes Containing Six Membered Rings 181 Attachment at 1,2-positions 181 Attachment at 1,9-positions 182 Attachment at 3,4-position of benzanthrone 184 Attachment at 1-position 186 Attachment at 1,2-positions 186 Attachment at 2,3-position 187 Attachment at 1,9-position 188

Formula Stage I Stage II Ethylation of Anthrapyrazole yellow Stage III Acid pasting Anthrapyrazole Stage I Stage II Stage III IndanthrenE Grey M Stage III Cyclisation of anthrimide to carbazoles. Vat Red Stage I Oxidation of 1-Nitro2-methyl anthraquinone. Stage II Microscopic Test Purification Vat Black Reduction Introduction Procedure Indanthrene Dark Blue Boa (Violanthrone) Indanthrene Golden Orange 3-G I. Anthrimide Formation II. Indanthrene Golden Orange 3G (carbazol) Indanthrene Brilliant Green Feb 2:2 Dibenzanthroanl Dihydroxy dibenzanthrone Indanthrene Brilliant Green FFB Crude Standardisation of Vat Dyestuffs The spray drying method The W & P Mixer Method Indentification of Vat Dyes Procedure Sulphuric Acid or Nitric Acid Test Alkaline Hydrosulphite Test Acid Hydrosulphite Test

214 214 215 215 215 215 216 216 217 218 218 219 219 219 219 220 220 220 221 221 222 223 223 223 223 226 226 227 228 228 229 229 229 230 230

10 Indigoid and Thioindigoid Dyes 231-241 Technical Synthesis of Indigo 232 Thioindigoid dyes 234 Indigo 237 Stage 1 237 Stage 2 237 Brilliant Indigo-G 239 Thioindigo Red B 239 Procedure 239 Algol Orange-RF 240 Standardisation 240 Vat Printing Brown-G 240 11 Indigosol 242-249 Anthrasol Brilliant Orange IRK 246 Anthrasol Blue IBC 247 Oxidation to tetraester 248 Identification of Leuco Ester Vat Dyes 249 12 Fluorination of Dyes 250-256 Hydorofluric Acid 250 Material of Construction 251 Fluorine 251 Material of Construction 251 Indanthrene Brilliant 253 Violet F3RK (C.I. 63350) Indanthrene Printing Blue HFG 254 Nuclear Fluorination 254 13 Sulphur Dyes 257-265 Thionation 259 Types of Sulphur Dyes 260 Properties of Sulphur Dyes 261 Manufacturing Process 262 Sulphur Black T 262 Hydrolysis 262 Oxidation 262 Grain Standardisation 263

Immedial Orange C Sulphur Orange 1 Property Hydron Blue R Powder R Base Hydron Blue R powder Procedure

264 264 264 264 264 265 265

14 Reactive Dyes 266-297 Classification of Reactive Dyes 266 Reactive dyes containing a cyanuric chloride nucleus 266 Reactive dyes containing a chloro pyrimidine nucleus 267 The vinyl sulfone reactive type 267 Reactive dye containing an epoxy group 267 Pyridazone 268 Dichloroquinoxaline 268 Acrylamide 268 Methylolated Nitrogen 268 Reactive dyes containing a Cyanuric Chloride nucleus 269 Vinyl Sulfone Reactive Dyes 274 Chemistry of tetrachloropyrimidines 274 Reactive Dyes based on Epoxides 278 Other types of Reactive Dyes 278 Reactivity of different types of Reactive Dyes 279 Application 279 Purification of Reactive Dyes 280 Advantage and Limitations of Reactive Dyes 280 Fabric Preparation 281 Washing Off 281 New Developments of Reactive Dyes 281 Kayacelon Reaction Dyes 282 Cibacron C Dyes 282

Procion Supra Dyes of (I.C.I.) Procion HEXL Dyes Prociline N Dyes Reactive Red Reactive Rose Red Reactive Violet Reactive Orange Reactive Yellow Reactive Red M8B Acetylation of H Acid Diazotisation of Tobias Acid Reactive Dyes with Trichloropyrimidine As Reactive Group Preparation Reactive Dyes with 2,3-Dichloroquinoxaline6-Carbonyl Chloride as Reactive Group Preparation Reactive Dyes with Chloroacetyl As Reactive Group Reactive Dyes with 6Amino-2-Chlorobenzothiazole-5-Sulphonic Acid As Reactive Group Preparations Properties of Cyanuric Chloride Chlorosulfonic Acid Identification of Reactive Dyes Procedure

282 285 285 285 286 287 287 288 288 289 289

290 290

291 291

292

292 293 294 295 296 296

15 Intermediates for Dyes and Pigments 298-344 Electrophilic 298 Nucleophilic substitution 298 Free radical 298 Sulphanilic Acid 299 Metanilic Acid 324 p-Aminophenol 325 Reduction 326 o-Phenylene Diamine 326

Property o-And-p-Nitrochlorobenzene p-Phenylenediamine Reduction Control Test 1-Phenyl 3-Methyl 5Pyrazolone Quality of phenyl methyl pyrazolone Tobias Acid Quality H-Acid 1-amino-2-Naphthol-4Sulphonic Acid Schaeffers Acid J-Acid Alkali Fusion of Amino J-acid N-Phenyl J-Acid Anthraquinone 2-chloroAnthraquinone 2-Amino Anthraquinone 1 Hydroxy Anthraquinone Anthraquinone 1-sufonate potassium salt 1-Hydroxy Anthraquinone 1:4 Dihydroxy Anthraquinone-(quinizarine) Purification 1:4 Diaminoanthraquinone Test for completion Oxidation 1-Amino-2-MethylAnthraquinone 2 Methyl Anthraquinone 1-Nitro-2-methylanthraquinone Purification of crude product 1-Amino-2-methylanthra quinone Benzanthrone

326 326 327 327 327 328 328 329 329 330 331 333 333 334 334 335 336 337 338 338 339 339 340 340 340 340 341 341 341 342 342 342

16 Fluorescent Brightners and Optical Whitening Agents 345-365 Chemical Constitution 346 Stilbene derivatives 346 Derivatives of dibenzothiophene-5, 5-dioxide 352 Azoles 353 Monoazoles 353 Bisazoles 353 Coumarian Derivatives 353 Derivaties of 6-membered ring heterocycles 355 Derivative of pyrazoline 355 Finishing of Commercial Optical Brightners 356 Pastes 356 Powder 356 Instant finish (easily water soluble) 356 Liquid forms 357 Stable Dispersions 358 Evaluation and testing 358 Active strength of fluorescent brightners 359 Uses 359 Detergent Brightners 360 Brightners for the textile industry 360 Natural Fibres 360 Brightner for cellulose 361 Brightners for wool 361 Brightners for synthetic fibres 361 Brightners for Cellulose Acetate 362 Brightners for Polyamide fibres 362 Brightners for polyester fibres 362 Brightners for Acrylic fibres 363 Brightners for Polyacrylonitrile fibres 364

Multi-fibre brightening Paper Brightners Brightners for plastics Brightners for Cosmetic Preparations Brightners for Miscellaneous Application Biological aspects

363 364 364 364 365 365

(Synthetics) Barytes Barium Sulphate Silicates China Clay (Kaolin) Silica (Silicon Dioxide)

384 384 384 384 385 385

17 Typical Commercial Brand Names of Textile Colorants, Accessory Products etc. 366-377 18 Classification of Pigments and Extendres 378-386 Inorganic Pigment 378 Organic Pigment 378 Difference between Organic and Inorganic Pigments 378 Difference between Pigments & Dyes 379 Classification of Pigments 379 Inorganics 379 White 380 Black 380 Red Brown 380 Yellow Orange 380 Green 380 Blue Purple 381 Metallic Powder 381 Organic Pigments 381 Lakes 381 Metal Toners 382 Azo Pigment 382 Yellow Pigments 383 Vat Pigment and Polycyclic Pigments 382 Phthalocyanines Blue, Green 382 Extenders 382 Types of Extenders Pigment 383 WhitingCalcium Carbonate (Natural) 383 Calcium Carbonate

19 Inorganic Pigments 387-419 Titanium Dioxide 388 Manufacture 391 Sulphate process 391 Wet treatment 393 The chloride process 393 Application of Titanium pigments 393 Paper 395 Textile 395 Plastics 396 Ceramics 396 Rubber 396 Plastics 396 Ceramics 396 Rubber 396 Miscellaneous 396 Iron Oxides 397 Manufacture 398 Uses 402 Synthetic Iron Oxide 403 Manufacture 405 Calcined Copperas Red 405 Ferrite Red 405 Precipitated Synthetic Red Iron Oxide 405 Calcined Black (Red) Iron Oxide 405 Uses 405 Chromates 406 Zinc Chromate 406+ Lead Chromate 406 Primrose Yellow 406 Light or Lemon Yellow 406 Medium Yellow 407 Chrome Orange 407 Manufacture 409 Chromium oxide green 409 Cadmium Pigments 411 Manufacture 412

Zinc Oxide From Zinc Metal (French or Indirected Process) From Zinc Oxide Ores (American or Direct process) From Zinc Sulphide Ore Zinc Sulphide Lithopone Zinc Phosphate Metallic Pigments Copper and Copper Alloy Flake Powders Zinc Pigment Stainless Steel Flake Pigment Carbon Blacks Uses Ultramarine Pigments Prussian Blue

413 415

415 415 415 415 415 415 419 419 420 421 423 427 428

21 High Grade Organic Pigments 450-467 Azo condensation 450 Vat Pigments and Related Compounds 450 Anthraquinone pigments 451 Thioindigo Pigments 455 Dioxazine 457 Quinacridone 457 Toning White Enamels 464 Isoindolinone 464 Applications 464 Phthalocyanine 465 22 Phthalocyanines 468-4823 Manufacturedine 469 Methods for formation of pigments from crude 472 Acid pasting 472 Acid slurry 472 Concentration of the sulfuric acid 474 Amounts of the sulfuric acid 474 Slurrying time 474 Temperature of the slurry 474 Production of b-form pigment by salt grinding 474 Manufacture of metal free phthalocyanine 474 Manufacture of phthalocyanine green 474 Properties Phthalocyanines 478 Flocculation, flotation and flooding 480 Control of flocculation 480 Flotation 481 Flooding 481 Application of phthalocyanine pigments 481 Phthalocyanine dyes of Textile materials 482 Phthalocyanine formation in the fibre 483

20 Azo Pigments 430-449 Red Pigments 431 Permanent Reds 433 The Pyrazolone Red 433 Yellow Pigments 433 Manufacture of azo pigments 439 Pigment Yellow G 440 Procedure 440 Diazotization 440 Coupling Component 440 Pigment Yellow 10G 440 Procedure 447 Diazotization 447 Coupling preparation 447 Coupling 447 Benzidine Yellow 447 Diazotization 447 Coupling Preparations 448 Coupling 448 Benzidine Orange 448 Diazotization 448 Preparation of Coup ling component 449 Coupling 449

23 Fluorescent Pigments 484-491 Photostability of Fluorescent Pigments 485 Fluorescent Application 486 Phosphorescent Luminous Pigments 488 Properties and Characteristics 488 Uses 489 Use in Plastic 489 Pearl Luster Pigments 490 24 Quality Control and Evaluation of Pigments 492-502 Quality Control 492 Evaluation of Pigments 494 Physical Properties of Pigment 494 Moisture Content 494 Bulking Volume 495 Mesh Residue 495 Particle Size 495 Procedure 495 IS Specification 496 Solvent Stability 496 Aim 496 Importance of the test 496 Procedure 496 IS Value 496 Water Soluble Matter 496 pH of the Pigments 497 Oil Absorption 497 Raw Materials required 497 Procedure 497 Defination of Oil Absorption 497 Opacity 497 Colour 497 By Automatic Muller 498 Mass Tone 498 Apparatus required 498 Reduction Tone 498 Raw Materials Used 498 Other materials required 498 Procedure 498 Raw Material required 499

Dispersibility, Texture and Rheology Stability and Fastness Other Properties To determine the Sp. Gravity of Pigment To determine percentage purity of crude phthalocyanine Volumetric Method for the determination of Copper in Cuprous Chloride Estimation of Organically Bound hlorine

499 499 500 500

500

501 501

25 Pigments for Textiles 503-513 Viscosity of Batch 504 Amount of Grinding Media 505 Amount of Material to be Ground 505 Handy Hints for Milling 505 Anionic surfactants 505 Non-ionic surfactants 505 Auxilliary or water retaining agents in pigmentemulsion 506 Mill Cleaning Methods 506 Formulations of different pigment Emulsions 507 Binder 511 Thickners 511 Water-Retaining agents 512 Catalysts 512 Preparation of 10% Binder Reduction Thickening 512 Recipe for printing paste 512 After treatments 513 26 Pigments for Paints 514-540 Mass Tone Colour 516 Under Tone Colour 516 Particle Shape 516 Particle Size Distribution 516 DispersIbility 516

Effect on Vehicle Viscosity Weathering Parameters of pigment performance in paint industry Dispersion Surface Treatment Particle Size Surface area and characteristics Mechanical Properties Paint Drying Flushed pigments Fluorescent pigments Pigments Fastness Properties Light Fastness Fastness to solvents Heat Fastness Chemical Fastness General Paint Pigment tailored to suit many specific uses are now available Characteristics and fastness properties of the various classes of pigment Dinitroaniline Orange Toluidine Reds Hansa Yellow Pigments (pigment yellows) Polycyclic Pigments Manufacture of Paint Suitability of different pigments for use in various paints systems Catalysed Paints Unsaturated polyester paints Acid-curing paints Polyurethane paints Cold-curing epoxy paints Epoxy stoving enamels Metallic finishes Colouration of Aqueous Paint Systems, Particularly of

516 516

517 517 517 517 517 517 517 518 518 518 518 518 519 519 519 519 519

Emulsion Binders Pigment paste from pigment powders Detail Formulation of Different Pigment Paste Separation and identification of pigments from synthetic enamel

527 528 528

531

27 Pigments for Printing Inks 541--549 Fastness to Light 542 Fastness to alkali 542 Fastness to acid 542 Transparency 543 Dispersion 544 Organic pigment for printing ink should offer 543 28 Pigments for Plastics, Rubber and Cosmetics 550-558 Selection of pigment 551 Colouring Techniques 553 Colouring plastic materials for injection moulding 553 Colouration of moulding compounds 554 Phenoplasts 554 Colouring Thermoplasticslastics 554 Plasticised polyviynl chloride 554 Rigid PVC 554 Polyethylene 554 Polypropylene 555 Polystyrene 555 Polyurethane foams 555 Pigments for Rubber 555 Vulcan Fast and Vulcan Pigments 556 Colourant For Cosmeticsmetics 557 Miscellaneous applications 558

520

520 521 521 522 523 523

524 526 526 526 526 526 526 527

29 Chemical Plant Data for Dyes and Pigments 559-579 Plant Layout 560 Typical weaknesses in a poor plant layout 561 Materials Handling 562 Reduction in time 562 Reduction in handling 563 Equipment design 563 Summary 563 Material of construction 564 Metals 564 Cast Iron 564 White Cast Iron 565 Plain Carbon Steel 565 Low carbon steel or Mild steel 565 Medium carbon steel 565 High carbon steel 565 Alloy Steel 567 Low alloy steel 567 High alloy steel (Stainless steel) 567 Non Metals 567 Cement and Stoneware Products 567 Glass 567 Rubber 568 Plastics 568 Other Materials 568 Wood 568 Linings for Chemical Plants Plants and Equipment 568 Important Equipments for Dyes, Pigments and Chemical Plant 569 Autoclaves or Pressure Vessels 569 Reaction kettle or Reactor 570 Materials of Construction 570 Type and shape of reactor 570 Agitation 570

Jacket Design Glass Line Reactor Mechanical Resistance Thermal Resistance Testing Vacuum Distillation Plant Filter Presses Filtrate discharge Dryers Spray dryers Advantage of Micropulverizer Research and Development 30 Plant Economics of Dye & Dye Intermediate 31 Plant Economics of Methyle Blue 32 Plant Economics of Acid Block Dye 33 Plant Economics of Green oxide and Blue Oxide 34 Plant Economics of Azo Dye (Rhodamine-B) 35 Plant Economics of Dyes (Anthraquinone, B-Naphthol etc.) 36 Suppliers of Plants, Machinery and Equipments

571 571 571 571 571 573 576 577 577 577 578 579

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