288 Index. as infrared absorbers, 219 CYCOLOR imaging applications, 142 colorants for, 139 comparison with other technologies, 142 process, 135

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1 Index Aflatoxin B 1, 270 Acrylonitrile, 269 Alizarin, 1 Ames test for BONTRON S31, 92 for CI Acid Black 2, 195 for CI Direct Black 19, 193, 195 for CI Direct Black 154, 195 for CI Direct Black 168, 195 for CI Food Black 2, 193, 195 for dye diffusion thermal transfer dyes, 156 for ink-jet dyes, 190, 195 for PVK/TNF, 76 for registration purposes, 257 for SPILON Black TRH, 93 Anthrapyridone for color toners, 101 for ink-jet printing, 201 Anthraquinone carcinogenicity, 259, 266 for color filters, 11 for color toners, 101 for dye diffusion thermal transfer, 159, 164 for ink-jet printing, 201 for liquid crystal displays, 10 natural, 1 for transfer printing toners, 116 Anthrimide, 47 Arsenic triselenide photodischarge sensitivity, 73 spectral sensitivity, 70 Azo carcinogenicity, 260, 264 as charge control agents, 92 for color filters, 17 for dye diffusion thermal transfer, 156, 160, 165 for ink-jet printing, 192 as infrared absorbers, 240 for liquid crystal displays, 9 tautomerism, 198 for thermal wax transfer, 144 for transfer printing toners, 116 Azulenium as infrared absorbers, 222 as organic photoconductors, 82 Bar codes, 250 Basic dyes: see Cationic Benzidine, 255, 260, 264 Benzoquinone infrared absorbers, 236 Benzoyl Leuco Methylene Blue, 55, 130, 140 Binders for dye diffusion thermal transfer, 153 for thermal wax transfer, 146 Bindschleder's Green, 227 Bisphenol A, 126 Black body radiation, 216 Blow-Off test, 90; see also Toners Bond energies, 216 Butter Yellow,

2 286 Index Cadmium sulfide photodischarge sensitivity, 73 spectral sensitivity, 70 Carbinol, 167 Carbon black for bar codes, 249 in thermal wax transfer, 144 Carbostyril, 30 Carcinogens alkylating agents, 267 amines, 259 anthraquinones, 259, 266 azo,264 benzidine, 255, 260, 264 carbonium ions, 267 cationic dyes, 266 classification of, 259 hydrazines, 259 hydroxylamines, 260 Michael acceptors, 269 mode of action, 259, 263, 265, naphthylamine, 255, nitrenium ions, 259, 263 nitro, 259 nitrosamines, 260 polycyclic aromatic hydrocarbons, 268 structure-activity relationships, 261 Carrier, 60, 88; see also Toners Cationic for dye diffusion thermal transfer, 159, 163, 167 mutagenicity of, 266 Charge acceptance, 73 Charge control agents BONTRON E81, 96 BONTRON E82, 92 BONTRON S3l, 92 BONTRON S32, 92 BONTRON S34, 92 cetyl pyridinium chloride, 96 chromium complexes, 92, 96 function, 90 mode of action, 97 negative, 91 nigrosine, 94, 101 noncolored, 95 polymeric, 97 positive, 94 quarternary ammonium, 96 requirements, 93 SPILON Black TRH, 93 toxicology, 98 Charge control agents (Cont.) triboelectric charge, 101 triphenylmethane, 95 Charge coupled devices color filters for, 15 in color copying, 67 Charge generation layer, 77 Charge generation materials; see also Photoconductors azo,78 azulenium, 82 dibromoanthanthrone, 79 perylene, 79 phthalocyanine, 84 polyvinylcarbazole-trinitrofluorenone (PVK-TNF), 76 squarilium, 82 thiapyrylium, 78 Charge transport layer, 77 Charge transport materials; see also Photoconductors arylamines, 85 hydrazones, 78 oxadiazoles, 79 oxazole,84 pyrazolines, 77 stilbenes, 81 leuco-triphenylmethanes, 78 Chlorophyll, 45 Chromium, carcinogenicity of, 270 CI Acid Black 63, 92 CI Acid Black 191, 194 CI Acid Blue 83, 17 CI Acid Green 1,219 CI Acid Red 35, 198 CI Acid Red 249,200 CI Acid Yellow 42, 17 CI Direct Black 19, 192 CI Direct Black 38, 264 CI Direct Black 154, 192 CI Direct Black 168, 194 CI Direct Black 171, 192 CI Direct Blue 86, 17,201 CI Direct Blue 199, 201 CI Direct Yellow 86, 197, 266 CI Disperse Blue 3, 156 CI Disperse Blue 60, 165, 236 CI Disperse Red 60, 156, 159, 201 CI Disperse Violet I, 266 CI Disperse Violet 26, 160 CI Disperse Yellow 3, 157 CI Disperse Yellow 54, 156

3 Index 11J7 CI Disperse Yellow 164, 101 CI Food Black 2, 191 CI Pigment Blue 15:1, 46, 100, 144 CI Pigment Blue 16, 105 CI Pigment Red 48:2, 104 CI Pigment Red 51:1, 144 CI Pigment Red 122, 100, 105, 144 CI Pigment Violet 1, 100 CI Pigment Yellow 1, 99 CI Pigment Yellow 12, 99, 144 CI Pigment Yellow 24, 104 CI Pigment Yellow 96, CI Reactive Black 5, 269 CI Reactive Red 120, 17 CI Solvent Black 29, 196 CI Solvent Black 35, 196 CI Solvent Blue 25, 101 CI Solvent Blue 36, 164, 202 CI Solvent Blue 63, 165 CI Solvent Blue 111, 101 CI Solvent Red 49, 101 CI Solvent Red 52, 101, 201 CI Solvent Yellow 16, 100 CI Vat Yellow 2, 104 Color additive primaries, 15,65 space coordinates, 16 subtractive primaries, 15,65 Color copying CYCOLOR process, 135 electrophotographic process, 65 laser process, 67 Color filters applications, 15 color space coordinates, 16, 22 dyes for, 17 pigments for, 20 preparation of, 17, 19 spectra of, 23 Color formers Benzoyl Leuco Methylene Blue, 130 black, 125, 130 blue, 125, 130 Crystal Violet Lactone, 126 for CYCOLOR process, 139 diphenylmethane, 140 encapsulation of, 132 Fuji Green, 130 green, 130 infrared, 134, 225, 249 orange, 125, 131 oxazine, 140 Color formers (ConI.) for pressure-sensitive printing, 130 red, 126, 131 spiropyran, 140 for thermal printing, 125 thiazine, 140 xanthene, 125, 130, 134, 139 Colorants anthrapyridone: see Anthrapyridone anthraquinone: see Anthraquinone azo: see Azo azulenium: see Azulenium carbostyril, 30 for color filters, 17 for color toners, 99 coumarin: see Coumarin cyanine: see Cyanine for CYCOLOR process, 139 for dye diffusion thermal transfer, 157 electrochromic: see Electrochromic for ink-jet, 184; see also Ink-Jet fluorescent: see Fluorescent dyes hazards of, 255 infrared: see Infrared absorbers isoindoline: see Isoindoline for lasers, 27 leuco: see Leuco dyes for liquid crystals, 9 merocyanine: see Merocyanine dyes naphthoquinone: see Naphthoquinone natural, 1 nigrosine: see Nigrosine for nonlinear optics, 36 for optical data storage, 248 for organic photoconductors; 78; see also Charge generation materials oxazine: see Oxazine perylene: see Perylene phosphorescent, 50 phthalocyanine: see Phthalocyanine pyrylium: see Pyrylium quinacridone: see Quinacridone registration of, 256 for solar cells, 46

4 288 Index Colorants (Cont.) spiropyran: see Spiropyran squarilium: see Squarlium for thermal paper, 125 for thermal wax transfer, 144 thiazine: see Thiazine thiapyrylium: see Thiapyrylium for toners, 99, 116 toxicology of, 264 triboelectric charge of, 10 1 tricyanovinyl, 162 triphenylmethanes: see Triphenylmethane viologens, 53 xanthene: see Xanthene Coumarin for lasers, 30 for solar cells, 47 Croconium infrared absorbers, 227 Crystal Violet Lactone, 126, 130 Cyanine for lasers, 30 as infrared absorbers, 219 CYCOLOR imaging applications, 142 for, 139 comparison with other technologies, 142 process, 135 Dark decay, 73 Developers for toners, for thermal printing, 126 for pressure sensitive printing, 132 Dibromoanthanthrone for organic photoconductors, 79 DNA, 258, 266 Dye diffusion thermal transfer (D2T2) advantages, 149 cyan dyes, 163 dyesheet, 153 for electronic photography, 149 history, 151 magenta dyes, 159 process, 152, 156 receiver sheet, 168 sublimation transfer, 151 yellow dyes, 157 ECOIN,256 EINECS, 256 Electrochrornic displays, 53 Electrochrornic dyes, 53 Electrochrornic printing, 54 Electrographic printing, 207 Electronics future trends, 273 technologies, 5 Electronic transitions, 217 Electronic photography, 149 Eiectrophotography; see also Photoconductors; Toners future trends, 278 processes, 59 Electrothermal printing, 147 Encapsulation coacervation, 132 interfacial polycondensation, 133 Fluoran : see Xanthene Fluorescein, 48 Fluorescent dyes in infrared, 251 for lasers, 29 for liquid crystals, 11 mutagenic, 266 for nonphotocopiable documents, 113 for solar cells, 48 Fuji Green, 130 Gamma acid, 198 H-acid, 198, 264 Hydrazines, 262 Hydroxylamines, 262 Ion deposition printing: see Ionography Ionography dielectric drum, 209 durability, 211 process, 209 Indanthrone, 243 Indoaniline dyes, 166 Infrared absorbers aniline black, 243 anthraquinone, 235, 248, 251 applications, 218, 243 in automatic identification, 248 in bar codes, 250 flash fusion of toners, 245 laser imaging, 243

5 Index 289 Infrared absorbers (Cont.) applications (Cont.) in nonphotocopiable paper, 113 for optical data storage, 247 as organic photoconductors, 246 in pressure sensitive printing, 134 for solar heating, 245 in thermal imaging, 244 azo,24o benzoquinone, 236 Bindschleder's Green, 227 carbon black, 248 classification, 218 color formers, 225, 249 colorless, 251 cyanine, 219, 224, 248, 251 donor-acceptor, 243 effects, 218 energy conversion, 243 heat ray blocking, 243 fluorescent, 251 imminium, 227 indanthrone, 243 indoaniline, 242 for liquid crystals, 11 naphthoquinone, 235, 248 nickel dithiolene, 230, 248 nigrosine, 225 nitroso, 219, 224 phthalocyanine, 236, 248 quinone, 235, 248 squarilium, 229, 248 sulfur dyes, 243 triphenylmethane, 225 Infrared radiation, 215 Ink-jet Ames test, 190, 193, 195 anthrapyridone, 201 anthraquinone, 201 azo, 190, 192, 197 black, water soluble, 192 black, solvent soluble, 196 color requirements, 184, 189, 196 color strength, 185 cyan, 201 differential solubility, 188 impurities electrolytes, 187 insolubles, 187 kogation, 190 lightfastness, 188, 195, 198, 200 magenta, water soluble, 197 Ink-jet (Cont.) magenta, solvent soluble, 201 metals, 187 phthalocyanine, 201 properties, 184 smear fastness, 189 solubility, 186, 195 tautomerism, 198 thermal stability, 190 toxicology, 190 triphenylmethane, 188 water fastness, 188, 195 yellow, 197 Ink-jet printing applications, 202 bubble-jet, 175, 179 continuous, 177 drop-on-demand, 179 future trends, 281 history, 176 hot melt, 179 industrial, 202 ink-paper interactions, 182 inks general features, 180 hot melt, 182 solvent based, 182 water based, 181 office, 179 patent activity, 176 piezo, 175, 179 technologies, 175 thermal, 175, 179 Intercalation, 266 Isoindoline for color filters, 22 Kogation, 190 Landa technology, 90, 116 Laser dyes lasing wavelengths, 30 theory of, 28 Laser printers, 64 Laser printing process, 63 Lasers for automatic identification, 249 in direct thermal printing, 128, 243 emission wavelenghts, 27, 69, 216 in thermal transfer printing, 149, 244

6 290 Index Leuco dyes in dye diffusion thermal transfer, 159 for electrochromic printing, 55 Light emitting diodes (LEDs) for automatic identification, 249 emission wavelengths, 69 printing process, 63 Liquid crystal displays, 7 Liquid crystal dyes, 7 Lightfastness azo dyes in dye diffusion thermal transfer, 155 azo dyes in ink-jet printing, 195, 198 improvers, 128, 169 triphenylmethane dyes, 188 Madder, 1 Magnetography, 211 Mauveine,2 Merocyanine dyes for nonlinear optics, 39 for solar cells, 46 Metals, carcinogenicity of, 270 Methine dyes,158 Methylene Blue, 55, 130, 140 MITI,256 MOBA Y Black SP Liquid, 203 Molecular orbital calculations, 269 Naphthoquinone for dye diffusion thermal transfer, 166 as infrared absorbers, Naphthylamine, 255, 260, 266 Nigrosine as charge control agents, 94 as infrared absorbers, 225 Nitroso, 219 Nonlinear optics applications general,33 for optical data storage, 35 for telecommunications, 34 beta values, 36 effects, 34 frequency doubling, 34 hyperpolarizability, 35 molecular alignment, 40 molecules for, 36 noncentrosymmetric effects, 37 relative harmonic intensity, 41 Nonphotocopiable documents infrared absorbers for, 113 fluorescent dyes for, 113 principle of, 111 Optical data storage infrared absorbers for, 248 principle of, 247 Optical density formula, 186 of ink -jet blacks, 194 Organic photoconductors: see Photoconductors, organic Order parameter, 7 Oxazine for CYCOLOR process, 140 for D2T2, 167 for electrochromic printing, 55 PARAQUAT,53 Patent Blue A, 188 Perkin, 2 Perylene for color filters, 20 for liquid crystals, 11 for solar cells, 47 Phenalenes, 47 Phosphorescent dyes, 50 Photoactive pigment electrophoresis for, 104 correlation with organic photoconductors, problems of, 107 process, 103 Photoconductors charge acceptance, 73 charge generation: see Charge generation materials charge generation layer, 77 charge transport: see Charge transport materials charge transport layer, 77 dark decay, 73 durability, 87 inorganic amorphous silicon (a-si), 70, 75 arsenic triselenide, 70, 74 cadmium sulfide, 70, 74

7 Index 291 Photoconductors (Cont.) inorganic (Cont.) selenium, 70, 73 selenium/tellurium, 70, 73, 75 zinc oxide, 70, 75 for laser printers, 84 mode of action, 86 organic, 62, 75, 246; see also Charge generation materials; Charge transport materials for photocopiers, 78 photodischarge sensitivity, 73 residual potential, 73 spectral sensitivity, 69 testing of, 72 toxicity of, 75, 76 trends in, 76 wastage of, 75 Photocopying process, 60 Photoinitiators, 139 Photomicrolithography organic photoconductors for, 113 process, 113 toners for, 113 Photopolymerization, 136 Photosynthesis mimics, 45 Phthalides: see Xanthenes Phthalocyanine for color filters, 17 for ink -jet printing, 20 I as infrared absorbers, 236 for solar cells, 46 for thermal wax transfer, 144 Planck's equation, 215 Polycarbonate for dye diffusion thermal transfer, 168 Polyester, 168 Polymorphism, 236 Porphyrins, 46 Prepress proofing, 114 Pressure sensitive printing carbonless paper construction of, 130 market for, 133 Pressure sensitive printing (Cont.) color formers for, 130 encapsulation of, 132 developers for, 132 process, 129 Print contrast ratio, 250 Pyronine B, 266 Pyrylium as infrared absorbers, 222 as organic photoconductors, 77 Quinacridone for thermal wax transfer, 144 Quinophthalones, 157 Reactive dyes, 17, 167,269 Receiver sheet, 168 Registration of chemicals, 256 Reprographics definition, 57 future trends, 274 market data, 275, 278 technologies, 58 Residual potential, 75 Risk assessment, 271 Rhodamine 6GP, 48 Rhodamine dyes: see Xanthene Rotational transitions, 217 Ruthenium bipyridyl complex, 50 Selenium: see Photoconductors, inorganic Selenium/tellurium: see Photoconductors, inorganic Sensitizers, 127 Sensitivity of photoconductors, 69, 73 of thermal paper, 127 a-silicon (amorphous silicon), 70, 75 Silicon detectors, 216, 249 Solar cells for, 46 luminescent, 47 Solar heating, 245 Solar spectrum, 48, 216 Spiropyran for CYCOLOR process, 140 for dye diffusion thermal transfer, 163 Squarilium as infrared absorbers, 227 Stokes shift, 48

8 292 Index Television for electronic photography, 150 flat screen, 16 Thermal paper additives, 127 for, 125 construction, 124 manufacturers, 128 production, 128 requirements, 127 sensitivity, 127 uses, 128 Thermal printing direct, 124 dye diffusion thermal transfer, 148 future trends, 279 history, 123 laser driven, 128, 148 wax transfer, 143; see also Thermal wax transfer Thermal wax transfer additives, 146 binders, 146 color sheet, 144 for, 144 patent activity, 147 process, 143 receiver sheet, 147 requirements, 147 waxes, 147 Thiapyrylium as infrared absorbers, 222 Thiazine, 55 ortho-tolidine, 255, 261 Toners additives, 88 Blow-Off test, 90 carrier, 60, 88 charge control additives, 90; see also Charge control agents for color copying, 66 for, 99, 116 composition of, 88 developers, 90 dry, 88 in electrography, 207 flash fusion of, 245 in ionography, 211 in laser printing, 63 liquid, 90, 106, 207 Toners (Cant.) magnetic, 88, 211 in magnetography, 211 manufacture, 89 monocomponent, 88 in photocopying, 61 resins, 88 for transfer printing, 116 triboelectric charge, 90, 101 two-component, 89 TOSCA,256 Toxicology acute tests, 256 alkylating agents, 267 Ames test, 76, 92, 93, 156, 190, 193, 195, 257 amines, 259 anthraquinones, 259, 266 azo, 264 carbonium ions, 267 of charge control agents, 92 of dye diffusion thermal transfer, 156 and DNA, 258, 266 ecotoxicological tests, 257 hydrazines, 262 hydroxylamines, 262 of impurities, 270 of ink-jet, 190 Michael acceptors, 269 mutagenicity tests, 257 nitrenium ions, 259 nitro, 259 nitrosamines, 260 and physical properties, 258 polycyclic aromatic hydrocarbons, 268 registration, 256 risk assessment, 271 structure-carcinogenicity guidelines, 258 Triboelectric charge measurement, 90 of, 101 Tricyanovinyl, 162 Triphenylmethane as charge control agents, 94 in color filters, 18 as infrared absorbers, 225 Tyrian Purple, 1

9 Index 293 Vibrational transitions, 217 Viologens, 53 Xanthene for CYCOLOR process, 139 for lasers, 30 for pressure sensitive printing, 130 Xanthene (Cont.) for thermal printing, 125 Xenon flash spectrum, 246 Zinc oxide photodischarge sensitivity, 73 spectral sensitivity, 70

High-Technology Applications of Organic Colorants

High-Technology Applications of Organic Colorants Peter Gregory Specialties Research Centre ICI Specialties Imperial Chemical Industries PLC Blackley, Manchester, England Plenum Press New York and London