Photoinitiators for polymer synthesis: scope, reactivity and efficiency
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| Main Authors: | , |
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2012
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XXVIII, 476 S. graph. Darst. |
| ISBN: | 3527332103 9783527332106 9783527648245 |
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MARC
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| 020 | |a 9783527648245 |c oBook |9 978-3-527-64824-5 | ||
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| 100 | 1 | |a Fouassier, Jean-Pierre |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Photoinitiators for polymer synthesis |b scope, reactivity and efficiency |c Jean Pierre Fouassier and Jacques Lalevée |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2012 | |
| 300 | |a XXVIII, 476 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Initiator |g Chemie |0 (DE-588)4253893-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Photopolymerisation |0 (DE-588)4174541-3 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Photopolymerisation |0 (DE-588)4174541-3 |D s |
| 689 | 0 | 1 | |a Initiator |g Chemie |0 (DE-588)4253893-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Lalevée, Jacques |e Verfasser |4 aut | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-64826-9 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, MOBI |z 978-3-527-64825-2 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-64827-6 |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025219020&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-025219020 | ||
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| _version_ | 1804149409256046592 |
|---|---|
| adam_text | IMAGE 1
V I I
CONTENTS
ABBREVIATIONS X I X
INTRODUCTION XXV
PART I BASIC PRINCIPLES AND APPLICATIONS O F PHOTOPOLYMERIZATION
REACTIONS 1
1 PHOTOPOLYMERIZATION AND PHOTO-CROSS-LINKING 3
REFERENCES 6
2 LIGHT SOURCES 11
2.1 ELECTROMAGNETIC RADIATION 11
2.2 CHARACTERISTICS O F A LIGHT SOURCE 12
2.3 CONVENTIONAL A N D UNCONVENTIONAL LIGHT SOURCES 13
2.3.1 XENON LAMP 13
2.3.2 MERCURY ARC LAMP 14
2.3.3 DOPED LAMPS 14
2.3.4 MICROWAVE LAMPS 14
2.3.5 EXCIMER LAMPS 14
2.3.6 LIGHT-EMITTING DIODES (LEDS) 16
2.3.7 PULSED LIGHT SOURCES 17
2.3.8 LASER SOURCES 17
2.3.9 SUN 18
2.3.10 HOUSEHOLD LAMPS 18
2.3.11 UV PLASMA SOURCE 19
REFERENCES 2 0
3 EXPERIMENTAL DEVICES AND EXAMPLES O F APPLICATIONS 21
3.1 UV CURING AREA: COATINGS, INKS, VARNISHES, PAINTS, A N D
ADHESIVES 21
3.1.1 EQUIPMENT 21
3.1.2 END USES 21
HTTP://D-NB.INFO/1019094656
IMAGE 2
V I I I I CONTENTS
3.1.3 COATING PROPERTIES 24
3.2 CONVENTIONAL PRINTING PLATES 25
3.3 MANUFACTURE O F OBJECTS A N D COMPOSITES 2 5
3.4 STEREOLITHOGRAPHY 25
3.5 APPLICATIONS IN MICROELECTRONICS 26
3.6 LASER DIRECT IMAGING 26
3.7 COMPUTER-TO-PLATE TECHNOLOGY 27
3.8 HOLOGRAPHY 27
3.9 OPTICS 28
3.10 MEDICAL APPLICATIONS 28
3.11 FABRICATION O F NANO-OBJECTS THROUGH A TWO-PHOTON ABSORPTION
POLYMERIZATION 29
3.12 PHOTOPOLYMERIZATION USING NEAR-FIELD OPTICAL TECHNIQUES 29 3.13
SEARCH FOR NEW PROPERTIES A N D NEW END USES 3 0
3.14 PHOTOPOLYMERIZATION A N D NANOTECHNOLOGY 32 3.15 SEARCH FOR A GREEN
CHEMISTRY 33
REFERENCES 3 4
4 PHOTOPOLYMERIZATION REACTIONS 41
4.1 ENCOUNTERED REACTIONS, MEDIA, AND EXPERIMENTAL CONDITIONS 41
4.2 TYPICAL CHARACTERISTICS O F SELECTED PHOTOPOLYMERIZATION
REACTIONS 45
4.2.1 FILM RADICAL PHOTOPOLYMERIZATION O F ACRYLATES 45 4.2.2 FILM
CATIONIC PHOTOPOLYMERIZATION 4 8
4.2.3 THIOL-ENE PHOTOPOLYMERIZATION 4 9
4.2.4 PHOTOPOLYMERIZATION O F WATER-BORNE LIGHT CURABLE SYSTEMS 52
4.2.5 PHOTOPOLYMERIZATION O F POWDER FORMULATIONS 52 4.2.6
CHARGE-TRANSFER PHOTOPOLYMERIZATION 53 4.2.7 DUAL CURE
PHOTOPOLYMERIZATION 54
4.2.8 HYBRID CURE PHOTOPOLYMERIZATION 55
4.2.9 ANIONIC PHOTOPOLYMERIZATION 55
4.2.10 METATHESIS PHOTOPOLYMERIZATION 56 4.2.11 CONTROLLED
PHOTOPOLYMERIZATION REACTIONS 56 4.2.11.1 RADICAL PHOTOPOLYMERIZATION
REACTIONS 56 4.2.11.2 CATIONIC PHOTOPOLYMERIZATION REACTIONS 5 8
4.2.11.3 ANIONIC PHOTOPOLYMERIZATION REACTIONS 59
4.2.12 HYBRID SOL-GEL PHOTOPOLYMERIZATION 59 4.2.13 PHOTO-CROSS-LINKING
REACTIONS IN THE PRESENCE O F PHOTOBASES OR PHOTOACIDS 59 4.3 TWO-PHOTON
ABSORPTION-INDUCED POLYMERIZATION 60
4.4 REMOTE CURING: PHOTOPOLYMERIZATION WITHOUT LIGHT 60
4.5 PHOTOACTIVATED HYDROSILYLATION REACTIONS 61
REFERENCES 61
IMAGE 3
CONTENTS I I X
5 PHOTOSENSITIVE SYSTEMS 73
5.1 GENERAL PROPERTIES 73
5.2 ABSORPTION O F LIGHT BY A MOLECULE 74
5.2.1 ABSORPTION 74
5.2.2 MOLECULAR ORBITALS AND ENERGY LEVELS 74
5.2.3 ABSORPTION O F LIGHT AND OPTICAL TRANSITIONS 74
5.2.4 RECIPROCITY LAW 76
5.2.5 MULTIPHOTONIC ABSORPTION 77
5.3 JABLONSKI S DIAGRAM 78
5.4 KINETICS O F THE EXCITED STATE PROCESSES 78
5.5 PHOTOINITIATOR A N D PHOTOSENSITIZER 80
5.6 ABSORPTION O F A PHOTOSENSITIVE SYSTEM 81
5.7 INITIATION STEP O F A PHOTOINDUCED POLYMERIZATION 82
5.7.1 PRODUCTION O F INITIATING SPECIES 8 2
5.7.2 COMPETITIVE REACTIONS IN THE EXCITED STATES 83
5.7.3 REACTIVITY IN BULK VERSUS SOLUTION: ROLE O F THE DIFFUSION 84
5.7.4 CAGE EFFECTS 85
5.8 REACTIVITY O F A PHOTOSENSITIVE SYSTEM 86
REFERENCES 8 7
6 APPROACH O F THE PHOTOCHEMICAL AND CHEMICAL REACTIVITY 89
6.1 ANALYSIS O F THE EXCITED-STATE PROCESSES 89
6.1.1 NANOSECOND LASER FLASH PHOTOLYSIS 89
6.1.2 PICOSECOND PUMP-PROBE SPECTROSCOPY 90 6.1.3 PHOTOTHERMAL
TECHNIQUES 90
6.1.4 TIME-RESOLVED FTIR SPECTROSCOPY 91 6.1.5 DIRECT DETECTION O F
RADICALS 92
6.1.6 CIDNP, CIDEP, AND ESR SPECTROSCOPY 92 6.2 Q U A N T U M MECHANICAL
CALCULATIONS 93
6.3 CLEAVAGE PROCESS 94
6.4 HYDROGEN TRANSFER PROCESSES 95
6.5 ENERGY TRANSFER 96
6.6 REACTIVITY O F RADICALS 98
REFERENCES 99
7 EFFICIENCY O F A PHOTOPOLYMERIZATION REACTION 103
7.1 KINETIC LAWS 103
7.1.1 RADICAL PHOTOPOLYMERIZATION 103
7.1.2 CATIONIC PHOTOPOLYMERIZATION 105
7.1.3 DEPENDENCE O F THE PHOTOPOLYMERIZATION RATE 106 7.1.4
LASER-INDUCED PHOTOPOLYMERIZATION 107 7.1.5 KINETICS O F THE
PHOTOPOLYMERIZATION IN BULK 108 7.2 MONITORING THE PHOTOPOLYMERIZATION
REACTION 109
7.2.1 FTIR ANALYSIS 109
7.2.2 PHOTOCALORIMETRY 110
IMAGE 4
X J CONTENTS
7.2.3
7.2.4
7.3 7.4 7.5
7.6 7.7
8
8 . 1
8 . 1 . 1
8 . 1 . 2
8.1.3
8.1.4 8.1.5 8.1.6 8.1.7
8.1.8 8.1.9
8.1.10 8.1.11 8.2 8 . 2 . 1
8 . 2 . 2
8.2.3
8.2.3.1 8.2.3.2 8.2.4 8.2.5
8 . 2 . 6
8.2.7
8.3 8.4 8.5
8.5.1 8.5.2
8.5.3 8.5.4 8.5.5
OPTICAL PYROMETRY 110 OTHER METHODS 110
EFFICIENCY VERSUS REACTIVITY 111
ABSORPTION O F LIGHT BY A PIGMENT 112
OXYGEN INHIBITION 114
ABSORPTION O F LIGHT STABILIZERS 115
ROLE O F THE ENVIRONMENT 117
REFERENCES 118
PART II RADICAL PHOTOINITIATING SYSTEMS 123
ONE-COMPONENT PHOTOINITIATING SYSTEMS 127
BENZOYL-CHROMOPHORE-BASED PHOTOINITIATORS 127
BENZOIN DERIVATIVES 129
BENZOIN ETHER DERIVATIVES 132 HALOGENATED KETONES 136
DIALKOXYACETOPHENONES AND DIPHENYLACETOPHENONES 136
MORPHOLINO A N D AMINO KETONES 137
HYDROXY ALKYL ACETOPHENONES 137
KETONE SULFONIC ESTERS 140
THIOBENZOATE DERIVATIVES 140
SULFONYL KETONES 144
OXYSULFONYL KETONES 147
OXIME ESTERS 148
SUBSTITUTED BENZOYL-CHROMOPHORE-BASED PHOTOINITIATORS 148
BENZOIN ETHER SERIES 149
MORPHOLINO KETONE A N D AMINO KETONE SERIES 149 HYDROXY ALKYL
ACETOPHENONE SERIES 151
OIL- OR WATER-SOLUBLE COMPOUNDS 151
DIFUNCTIONAL COMPOUNDS 152
MODIFIED SULFONYL KETONES 154
LIMIT O F THE SUBSTITUENT EFFECT 154
MACROPHOTOINITIATORS 156
SUPPORTED CLEAVABLE PHOTOINITIATORS 157
HYDROXY ALKYL HETEROCYCLIC KETONES 157
HYDROXY ALKYL CONJUGATED KETONES 158
BENZOPHENONE- AND THIOXANTHONE-MOIETY-BASED CLEAVABLE
SYSTEMS 158 BENZOPHENONE PHENYL SULFIDES 158
KETOSULFOXIDES 159
BENZOPHENONE THIOBENZOATES 159
BENZOPHENONE-SULFONYL KETONES 159 HALOGENATED DERIVATIVES 160
IMAGE 5
CONTENTS X I
8.5.6 CLEAVABLE BENZOPHENONE, XANTHONE, A N D THIOXANTHONE
DERIVATIVES 160
8.6 BENZOYL PHOSPHINE OXIDE DERIVATIVES 161
8.6.1 COMPOUNDS 161
8.6.2 EXCITED STATE PROCESSES 162
8.6.3 ABSORPTION PROPERTIES A N D PHOTOLYSIS 164
8.6.4 BIS-ACYL PHOSPHINE OXIDE/PHENOLIC COMPOUND INTERACTION 165 8.7
PHOSPHINE OXIDE DERIVATIVES 165
8.8 TRICHLOROMETHYL TRIAZINES 165
8.9 BIRADICAL-GENERATING KETONES 166
8.10 PEROXIDES 166
8.11 DIKETONES 367
8.12 AZIDES A N D AROMATIC BIS-AZIDES 168
8.13 AZO DERIVATIVES 168
8.14 DISULFIDE DERIVATIVES 168
8.15 DISILANE DERIVATIVES 169
8.16 DISELENIDE A N D DIPHENYLDITELLURIDE DERIVATIVES 170
8.17 DIGERMANE A N D DISTANNANE DERIVATIVES 170
8.18 CARBON-GERMANIUM CLEAVABLE-BOND-BASED DERIVATIVES 170 8.19
CARBON-SILICON A N D GERMANIUM-SILICON CLEAVABLE-BOND-BASED
DERIVATIVES 172
8.20 SILICON CHEMISTRY A N D CONVENTIONAL CLEAVABLE PHOTOINITIATORS 172
8.21 SULFUR-CARBON CLEAVABLE-BOND-BASED DERIVATIVES 173 8.22
SULFUR-SILICON CLEAVABLE-BOND-BASED DERIVATIVES 173
8.23 PERESTERS 173
8.24 BARTON S ESTER DERIVATIVES 174
8.25 HYDROXAMIC A N D THIOHYDROXAMIC ACIDS A N D ESTERS 174
8.26 ORGANOBORATES 176
8.27 ORGANOMETALLIC COMPOUNDS 176
8.27.1 TITANOCENES 177
8.27.2 C H R O M I U M COMPLEXES 177
8.27.3 ALUMINATE COMPLEXES 178
8.28 METAL SALTS AND METALLIC SALT COMPLEXES 178
8.29 METAL-RELEASING COMPOUND 178
8.30 CLEAVABLE PHOTOINITIATORS IN LIVING POLYMERIZATION 179 8.30.1
CLEAVABLE C-S- OR S-S-BOND-BASED PHOTOINIFERTERS 179
8.30.2 TEMPO-BASED ALKOXYAMINES 182 8.31 OXYAMINES 183
8.31.1 ALKOXYAMINES 183
8.31.2 SILYLOXYAMINES 184
8.32 CLEAVABLE PHOTOINITIATORS FOR TWO-PHOTON ABSORPTION 184 8.33
NANOPARTICLE-FORMATION-MEDIATED CLEAVABLE PHOTOINITIATORS 185
8.34 MISCELLANEOUS SYSTEMS 185
8.35 TENTATIVELY EXPLORED UV-LIGHT-CLEAVABLE BONDS 185 REFERENCES 187
IMAGE 6
X I I | CONTENTS
9 TWO-COMPONENT PHOTOINITIATING SYSTEMS 199
9.1 KETONE-/HYDROGEN-DONOR-BASED SYSTEMS 199
9..1.1 BASIC MECHANISMS 199
9.1.2 HYDROGEN DONORS 201
9.1.2.1 AMINES 201
9.1.2.2 THIO DERIVATIVES 203
9.1.2.3 BENZOXAZINES 204
9.1.2.4 ALDEHYDES 204
9.1.2.5 ACETALS 204
9.1.2.6 HYDROPEROXIDES 205
9.1.2.7 SILANES 205
9.1.2.8 SILYLAMINES 207
9.1.2.9 METAL-(IV) AND AMINE-CONTAINING STRUCTURES 208 9.1.2.10
SILYLOXYAMINES 2 1 0
9.1.2.11 GERMANES A N D STANNANES 210
9.1.2.12 PHOSPHORUS-CONTAINING COMPOUNDS 211
9.1.2.13 BORANE COMPLEXES 211
9.1.2.14 ALKOXYAMINES 212
9.1.2.15 MONOMERS 213
9.1.2.16 PHOTOINITIATOR ITSELF 214
9.1.2.17 ALCOHOLS AND T H F 214
9.1.2.18 POLYMER SUBSTRATE 214
9.1.2.19 SILICON-HYDRIDE-TERMINATED SURFACE 214
9.1.3 BENZOPHENONE DERIVATIVES 215
9.1.3.1 BENZOPHENONE 215
9.1.3.2 AMINOBENZOPHENONES 218
9.1.3.3 OTHER BENZOPHENONES 218
9.1.3.4 PHOTOPOLYMERIZATION ACTIVITY 219
9.1.4 THIOXANTHONE DERIVATIVES 219
9.1.4.1 THIOXANTHONE 219
9.1.4.2 SUBSTITUTED THIOXANTHONES 2 2 0 9.1.5 DIKETONES 223
9.1.5.1 AROMATIC DIKETONES 223
9.1.5.2 CAMPHORQUINONE 224
9.1.6 KETOCOUMARINS 225
9.1.7 COUMARINS 225
9.1.8 ALKYLPHENYLGLYOXYLATES 225
9.1.9 OTHER TYPE II KETONE SKELETONS 228
9.1.9.1 ANTHRAQUINONES 228
9.1.9.2 FLUORENONES 229
9.1.10 ALDEHYDES 229
9.1.11 ALIPHATIC KETONES 229
9.1.12 CLEAVABLE KETONES AS TYPE II PHOTOINITIATORS 229
9.1.13 TAILOR-MADE TYPE II KETONES 229
IMAGE 7
CONTENTS X I I I
9.1.13.1 LOW- AND HIGH-MOLECULAR-WEIGHT COMPOUNDS A N D
MACROPHOTOINITIATORS 229 9.1.13.2 WATER-SOLUBLE COMPOUNDS 233 9.1.13.3
TWO-PHOTON ABSORPTION PHOTOINITIATORS 235 9.1.13.4 PHOTOMASKED
PHOTOINITIATOR 235
9.1.13.5 OXYGEN SELF-CONSUMING THIOXANTHONE DERIVATIVES 236 9.1.13.6
LOW-MOLECULAR-WEIGHT ONE-COMPONENT SYSTEMS 236 9.2 DYE-BASED SYSTEMS 238
9.2.1 DYE/AMINE SYSTEMS 238
9.2.2 DYE/COINITIATOR SYSTEMS 239
9.2.3 IMPROVEMENT O F DYE/AMINE SYSTEMS 2 4 0
9.2.4 DYE/AMINE WATER-SOLUBLE SYSTEMS 241 9.2.5 KINETIC DATA 241
9.3 OTHER TYPE II PHOTOINITIATING SYSTEMS 241
9.3.1 - MALEIMIDE/AMINE A N D PHOTOINITIATOR/MALEIMIDE 241 9.3.2
DONOR/ACCEPTOR SYSTEMS 243
9.3.3 BISARYLIMIDAZOLE DERIVATIVE/ADDITIVE 2 4 4 9.3.4 PYRYLIUM AND
THIOPYRYLIUM SALTS/ADDITIVE 245 9.3.5 KETONE/KETONE-BASED SYSTEMS 246
9.3.6 ORGANOMETALLIC COMPOUND/KETONE-BASED SYSTEMS 247 9.3.7
ORGANOMETALLIC COMPLEX/ADDITIVE 248 9.3.7.1 ORGANOMETALLIC DERIVATIVES
248 9.3.7.2 FERROCENIUM SALTS 248
9.3.8 METAL CARBONYL/SILANE 250
9.3.9 PHOTOSENSITIZER-LINKED PHOTOINITIATOR OR COINITIATOR-BASED SYSTEMS
2 5 0
9.3.10 PHOTOINITIATOR/PEROXIDE-OR HYDROPEROXIDE-BASED SYSTEMS 251 9.3.11
PHOTOINITIATOR/DISULFIDE OR GROUP 4B DIMETAL DERIVATIVES 252 9.3.12
PHOTOINITIATOR/PHOSPHORUS-CONTAINING COMPOUNDS 253 9.3.13
PHOTOINITIATOR/ONIUM SALTS 254
9.3.14 PHOTOSENSITIZER/TITANOCENES 254 9.3.15 TYPE I
PHOTOINITIATOR/ADDITIVE: SEARCH FOR NEW PROPERTIES 255 9.3.16
NANOPARTICLE-FORMATION-MEDIATED TYPE II PHOTOINITIATORS 256 9.3.17
MISCELLANEOUS TWO-COMPONENT SYSTEMS 257 9.3.17.1 LIGHT ABSORBING
AMINE/MONOMER 2 5 7 9.3.17.2 NITRO COMPOUND/AMINE 257 9.3.17.3
HYDROCARBON/AMINE 257 9.3.17.4 PHOTOSENSITIZER/TRIAZINE DERIVATIVE 257
9.3.17.5 OTHER SYSTEMS 258
REFERENCES 258
10 MULTICOMPONENT PHOTOINITIATING SYSTEMS 269
10.1 GENERALLY ENCOUNTERED MECHANISM 269
10.1.1 KETONE/AMINE/ONIUM SALT OR BROMO COMPOUND 269 10.1.2
DYE/AMINE/ONIUM SALT OR BROMO COMPOUND 270
IMAGE 8
X I V CONTENTS
10.1.3 KETONE/AMINE/IMIDE DERIVATIVES 270
10.1.4 KETONE/KETONE/AMINE 271
10.1.5 DYE/ARNINE/TRIAZINE DERIVATIVE 271 10.2 OTHER MECHANISMS 271
10.2.1 TRIAZINE-DERIVATIVE-CONTAINING THREE-COMPONENT SYSTEMS 272 10.2.2
DYE/KETONE/AMINE 272
10.2.3 DYE/AMINE/METAL SALT 272
10.2.4 DYE/BORATE/ADDITIVE 273
10.2.5 PHOTOSENSITIZER/CL-HABI/ADDITIVE 273 10.2.6 METAL CARBONYL
COMPOUND/SILANE/HYDROPEROXIDE 275 10.2.7 PHOTOSENSITIZER/AMINE/HABI
DERIVATIVES/ONIUM SALT 276 10.2.8 DYE/FERROCENIUM SALT/HYDROPEROXIDE 277
10.2.9 COUMARIN/AMINE/FERROCENIUM SALT 277 10.2.10 DYE/FERROCENIUM
SALT/AMINE/HYDROPEROXIDE 278 10.2.11 ORGANOMETALLIC
COMPOUND/SILANE/IODONIUM SALT 279 10.3 TYPE II PHOTOINITIATOR/SILANE:
SEARCH FOR NEW PROPERTIES 279 10.4 MISCELLANEOUS MULTICOMPONENT SYSTEMS
281
REFERENCES 281
11 OTHER PHOTOINITIATING SYSTEMS 283
11.1 PHOTOINITIATOR-FREE SYSTEMS OR SELF-INITIATING MONOMERS 283 11.2
SEMICONDUCTOR NANOPARTICLES 284
11.3 SELF-ASSEMBLED PHOTOINITIATOR MONOLAYERS 284 REFERENCES 285
PART III NONRADICAL PHOTOINITIATING SYSTEMS 287
12 CATIONIC PHOTOINITIATING SYSTEMS 289
12.1 DIAZONIUM SALTS 289
12.2 O N I U M SALTS 289
12.2.1 IODONIUM AND SULFONIUM SALTS 289
12.2.1.1 COMPOUNDS 289
12.2.1.2 PHOTOPOLYMERIZATION REACTION 290 12.2.1.3 ROLE O F THE ANION
292
12.2.1.4 ABSORPTION PROPERTIES 293 12.2.1.5 DECOMPOSITION PROCESSES O F
IODONIUM SALTS 294 12.2.1.6 DECOMPOSITION PROCESSES O F SULFONIUM SALTS
299 12.2.1.7 ACYLSULFONIUM SALTS 301 12.2.1.8 SUBSTITUTED IODONIUM AND
SULFONIUM SALT DERIVATIVES 301 12.2.2 OTHER O N I U M SALTS 303
12.2.3 SEARCH FOR NEW PROPERTIES 3 0 4
12.2.3.1 ABSORPTION 304
12.2.3.2 SOLUBILITY 305
12.2.3.3 STABILITY 305
12.2.3.4 BENZENE RELEASE 307
IMAGE 9
CONTENTS X V
12.2.3.5 ODOR 307
12.2.3.6 TOXICITY 3 0 7
12.2.3.7 AMPHIFUNCTIONALITY 308 12.3 ORGANOMETALLIC DERIVATIVES 308
12.3.1 TRANSITION ORGANOMETALLIC COMPLEXES 308 12.3.2 INORGANIC
TRANSITION METAL COMPLEXES 3 1 0 12.3.3 NON-TRANSITION-METAL COMPLEXES 3
1 0 12.4 O N I U M SALT/PHOTOSENSITIZER SYSTEMS 311
12.4.1 PHOTOSENSITIZATION THROUGH ENERGY TRANSFER 312 12.4.2
PHOTOSENSITIZATION THROUGH ELECTRON TRANSFER 312 12.4.2.1
PHOTOSENSITIZERS 312
12.4.2.2 PHOTOINITIATION STEP 3 1 7 12.5 FREE-RADICAL-PROMOTED CATIONIC
PHOTOPOLYMERIZATION 318 12.5.1 RADICAL/ONIUM SALT INTERACTION 318 12.5.2
RADICAL SOURCE/ONIUM SALT BASED SYSTEMS 318
12.5.2.1 RADICAL SOURCE/IODONIUM SALT TWO-COMPONENT SYSTEMS 318 12.5.2.2
RADICAL SOURCE/IODONIUM SALT THREE-COMPONENT SYSTEMS 3 2 0 12.5.2.3 ROLE
O F THE O N I U M SALT 329
12.5.2.4 ONE-COMPONENT RADICAL SOURCE-ONIUM SALT SYSTEM 3 3 0 12.5.2.5
PHOTOINITIATION STEP 3 3 0 12.5.2.6 RECENT APPLICATIONS 331 12.5.3
RADICAL/METAL-SALT-BASED SYSTEMS 331
12.5.4 ADDITION/FRAGMENTATION REACTION 331 12.6 MISCELLANEOUS SYSTEMS
332
12.7 PHOTOSENSITIVE SYSTEMS FOR LIVING CATIONIC POLYMERIZATION 3 3 2
12.8 PHOTOSENSITIVE SYSTEMS FOR HYBRID CURE 333
REFERENCES 333
13 ANIONIC PHOTOINITIATORS 343
13.1 INORGANIC COMPLEXES 343
13.2 ORGANOMETALLIC COMPLEXES 343
13.3 CYANO DERIVATIVE/AMINE SYSTEM 344
13.4 PHOTOSENSITIVE SYSTEMS FOR LIVING ANIONIC POLYMERIZATION 344
REFERENCES 345
14 PHOTOACID GENERATORS (PAG) SYSTEMS 347
14.1 IMINOSULFONATES A N D OXIMESULFONATES 3 4 7
14.2 NAPHTHALIMIDES 348
14.3 PHOTOACIDS A N D CHEMICAL AMPLIFICATION 349
REFERENCES 349
15 PHOTOBASE GENERATORS (PBG) SYSTEMS 351
15.1 OXIME ESTERS 351
15.2 CARBAMATES 351
15.3 A M M O N I U M TETRAORGANYL BORATE SALTS 351
IMAGE 10
X V I CONTENTS
15.4 N-BENZYLATED-STRUCTURE-BASED PHOTOBASES 352
15.5 OTHER MISCELLANEOUS SYSTEMS 353
15.6 PHOTOBASES A N D BASE PROLIFERATION PROCESSES 354
REFERENCES 354
PART IV REACTIVITY O F THE PHOTOINITIATING SYSTEM 357
16 ROLE O F T H E EXPERIMENTAL CONDITIONS IN T H E PERFORMANCE O F A
RADICAL PHOTOINITIATOR 359
16.1 ROLE O F VISCOSITY 360
16.2 ROLE O F THE SURROUNDING ATMOSPHERE 361
16.3 ROLE O F THE LIGHT INTENSITY 363
REFERENCES 364
17 REACTIVITY AND EFFICIENCY O F RADICAL PHOTOINITIATORS 367 17.1
RELATIVE EFFICIENCY O F PHOTOINITIATORS 367
17.1.1 PHOTOPOLYMERIZATION O F MMA I N ORGANIC SOLVENTS 367 17.1.2
PHOTOPOLYMERIZATION O F VARIOUS MONOMERS I N ORGANIC SOLVENTS AND BULK
MEDIA 367 17.1.3 PHOTOPOLYMERIZATION O F TMPTA I N FILM 371
17.1.4 PHOTOPOLYMERIZATION O F MONOMER/OLIGOMER FILM 373
17.1.5 PHOTOPOLYMERIZATION O F ACRYLAMIDE IN WATER 376 17.1.6
PHOTOPOLYMERIZATION O F OIL-SOLUBLE MONOMERS IN DIRECT MICELLES 376
17.1.7 PHOTOPOLYMERIZATION O F WATER-SOLUBLE MONOMERS I N REVERSE
MICELLES 377
17.2 ROLE O F THE EXCITED-STATE REACTIVITY 377
17.2.1 GENERATION O F RADICALS 377
17.2.2 ROLE O F MONOMER QUENCHING 378
17.3 ROLE O F THE MEDIUM O N THE PHOTOINITIATOR REACTIVITY 381
17.3.1 REACTIVITY IN SOLUTION 381
17.3.2 REACTIVITY IN MICROHETEROGENEOUS SOLUTION 383
17.3.3 REACTIVITY IN BULK 386
17.4 STRUCTURE/PROPERTY RELATIONSHIPS IN PHOTOINITIATING SYSTEMS 388
17.4.1 ROLE O F THE BOND DISSOCIATION ENERGY IN CLEAVABLE SYSTEMS 388
17.4.2 ROLE O F THE BOND DISSOCIATION ENERGY IN NONCLEAVABLE SYSTEMS 389
17.4.3 ROLE O F THE INITIATING RADICAL IN THE INITIATION STEP 391
17.4.3.1 GENERATION O F THE FIRST MONOMER RADICAL 391
17.4.3.2 ADDITION RATE CONSTANTS TO MONOMER 392
17.4.3.3 DESCRIPTION O F THE RADICAL/MONOMER REACTIVITY 392 REFERENCES
394
IMAGE 11
CONTENTS | X V I I
18 REACTIVITY O F RADICALS TOWARD OXYGEN, HYDROGEN DONORS, MONOMERS,
AND ADDITIVES: UNDERSTANDING AND DISCUSSION 399 18.1 ALKYL AND RELATED
CARBON-CENTERED RADICALS 399 18.2 ARYL RADICALS 401
18.3 BENZOYL RADICALS 402
18.4 ACRYLATE A N D METHACRYLATE RADICALS 403
18.5 AMINOALKYL RADICALS 404
18.5.1 REACTIVITY 404
18.5.2 ROLE O F THE CLASS O F THE AMINE 408
18.5.3 N-PHENYL GLYCINE DERIVATIVES 408 18.5.4 CHAIN LENGTH EFFECT 409
18.5.5 REGIOSELECTIVITY O F THE HYDROGEN ABSTRACTION REACTION 4 0 9
18.5.6 AMINOALKYL RADICALS A N D THE HALOGEN ABSTRACTION REACTION 4 1 0
18.5.7 REACTIVITY U N D E R AIR 411
18.6 PHOSPHORUS-CENTERED RADICALS 412
18.7 THIYL RADICALS 413
18.8 SULFONYL AND SULFONYLOXY RADICALS 4 1 7
18.9 SILYL RADICALS 418
18.9.1 THE PARTICULAR BEHAVIOR O F THE TRIS(TRIMETHYLSILYL)SILYL RADICAL
421 18.9.2 REACTIVITY AND PHOTOINITIATION U N D E R AIR 422 18.9.3 OTHER
SOURCES O F SILYL RADICALS 4 2 4
18.10 OXYL RADICALS 425
18.11 PEROXYL RADICALS 426
18.11.1 INTERACTION WITH H-DONORS 428 18.11.2 INTERACTION WITH MONOMERS
430 18.11.3 INTERACTION WITH TRIPHENYLPHOSPHINE 4 3 0 18.11.4 SH2
SUBSTITUTION 4 3 0
18.11.5 OTHER OXYLS A N D PEROXYLS 431 18.12 AMINYL RADICALS 431
18.13 GERMYL A N D STANNYL RADICALS 432
18.13.1 REACTIVITY 433
18.13.2 REACTIVITY U N D E R AIR 434
18.13.3 REACTIVITY AND STRUCTURE O F (TMS) 3GE* VERSUS (TMS^SI* 434
18.14 BORYL RADICALS 435
18.14.1 REACTIVITY 436
18.14.2 REACTIVITY U N D E R AIR 438
18.14.3 PHOTOINITIATION U N D E R AIR 438 18.15 LOPHYL RADICALS 439
18.16 IMINYL RADICALS 439
18.17 METAL-CENTERED RADICALS 4 4 0
18.18 PROPAGATING RADICALS 442
18.19 RADICALS I N CONTROLLED PHOTOPOLYMERIZATION REACTIONS 443 18.19.1
PHOTOINIFERTERS AND DITHIOCARBAMYL RADICALS 443 18.19.2 LIGHT-SENSITIVE
ALKOXYAMINES A N D GENERATION O F NITROXIDES 445
IMAGE 12
X V I I I | CONTENTS
18.20 RADICALS IN HYDROSILYLATION REACTIONS 446
REFERENCES 447
19 REACTIVITY O F RADICALS: TOWARDS THE OXIDATION PROCESS 455 19.1
REACTIVITY O F RADICALS TOWARD METAL SALTS 455
19.2 RADICAL/ONIUM SALT REACTIVITY I N FREE-RADICAL-PROMOTED CATIONIC
PHOTOPOLYMERIZATION 456 REFERENCES 459
CONCLUSION 461
INDEX 465
|
| any_adam_object | 1 |
| author | Fouassier, Jean-Pierre Lalevée, Jacques |
| author_facet | Fouassier, Jean-Pierre Lalevée, Jacques |
| author_role | aut aut |
| author_sort | Fouassier, Jean-Pierre |
| author_variant | j p f jpf j l jl |
| building | Verbundindex |
| bvnumber | BV040365283 |
| classification_rvk | VK 8000 |
| classification_tum | CHE 725f CHE 189f |
| ctrlnum | (OCoLC)809371230 (DE-599)DNB1019094656 |
| dewey-full | 547.28 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.28 |
| dewey-search | 547.28 |
| dewey-sort | 3547.28 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Physik Chemie |
| format | Book |
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| id | DE-604.BV040365283 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T00:22:34Z |
| institution | BVB |
| isbn | 3527332103 9783527332106 9783527648245 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-025219020 |
| oclc_num | 809371230 |
| open_access_boolean | |
| owner | DE-11 DE-703 DE-91G DE-BY-TUM |
| owner_facet | DE-11 DE-703 DE-91G DE-BY-TUM |
| physical | XXVIII, 476 S. graph. Darst. |
| publishDate | 2012 |
| publishDateSearch | 2012 |
| publishDateSort | 2012 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Fouassier, Jean-Pierre Verfasser aut Photoinitiators for polymer synthesis scope, reactivity and efficiency Jean Pierre Fouassier and Jacques Lalevée Weinheim Wiley-VCH 2012 XXVIII, 476 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Initiator Chemie (DE-588)4253893-2 gnd rswk-swf Photopolymerisation (DE-588)4174541-3 gnd rswk-swf Photopolymerisation (DE-588)4174541-3 s Initiator Chemie (DE-588)4253893-2 s DE-604 Lalevée, Jacques Verfasser aut Erscheint auch als Online-Ausgabe, EPUB 978-3-527-64826-9 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-64825-2 Erscheint auch als Online-Ausgabe, PDF 978-3-527-64827-6 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025219020&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Fouassier, Jean-Pierre Lalevée, Jacques Photoinitiators for polymer synthesis scope, reactivity and efficiency Initiator Chemie (DE-588)4253893-2 gnd Photopolymerisation (DE-588)4174541-3 gnd |
| subject_GND | (DE-588)4253893-2 (DE-588)4174541-3 |
| title | Photoinitiators for polymer synthesis scope, reactivity and efficiency |
| title_auth | Photoinitiators for polymer synthesis scope, reactivity and efficiency |
| title_exact_search | Photoinitiators for polymer synthesis scope, reactivity and efficiency |
| title_full | Photoinitiators for polymer synthesis scope, reactivity and efficiency Jean Pierre Fouassier and Jacques Lalevée |
| title_fullStr | Photoinitiators for polymer synthesis scope, reactivity and efficiency Jean Pierre Fouassier and Jacques Lalevée |
| title_full_unstemmed | Photoinitiators for polymer synthesis scope, reactivity and efficiency Jean Pierre Fouassier and Jacques Lalevée |
| title_short | Photoinitiators for polymer synthesis |
| title_sort | photoinitiators for polymer synthesis scope reactivity and efficiency |
| title_sub | scope, reactivity and efficiency |
| topic | Initiator Chemie (DE-588)4253893-2 gnd Photopolymerisation (DE-588)4174541-3 gnd |
| topic_facet | Initiator Chemie Photopolymerisation |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025219020&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT fouassierjeanpierre photoinitiatorsforpolymersynthesisscopereactivityandefficiency AT laleveejacques photoinitiatorsforpolymersynthesisscopereactivityandefficiency |