Controlled and living polymerizations: methods and materials
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Wiley-VCH
2009
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| Physical Description: | XXI, 612 S. Ill., graph. Darst. |
| ISBN: | 9783527324927 |
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| 245 | 1 | 0 | |a Controlled and living polymerizations |b methods and materials |c ed. by Axel H. E. Müller ... |
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Titel: Controlled and living polymerizations
Autor: Müller, Axel H. E.
Jahr: 2009
r
Contents
Prefece XV
List of Contributors XIX
1 Anionic Vinyl Polymerization 1
Durairaj Baskaran and Axel H. E. Müller
1.1 Introduction 1
1.1.1 The Discovery of Living Anionic Polymerization 1
1.1.2 Consequences ofTermination-and Transfer-Free Polymerization 2
1.1.3 Suitable Monomers 5
1.2 Structure of Carbanions 6
1.3 Initiation 7
1.3.1 Anionic Initiators 8
1.3.2 Experimental Considerations 11
1.4 Mechanism of Styrene and Diene Polymerization 11
1.4.1 Polymerization of Styrene in Polar Solvents: Ions and Ion Pairs 11
1.4.2 Contact and Solvent-Separated Ion Pairs 13
1.4.3 Polymerization of Styrene in Nonpolar Solvents:
Aggregation Equilibria 15
1.4.3.1 Polymerization in Pure Solvents 15
1.4.3.2 Polymerization in Nonpolar Solvent in the Presence of Ligands 16
IAA Anionic Polymerization ofDienes in Nonpolar Solvent 18
1.4.4.1 Kinetics 18
1.4.4.2 Regiochemistry 19
1.4.5 Architectural Control Using Chain-End Functionalization 20
1.5 Mechanism of Anionic Polymerization ofAcrylic Monomers 20
1.5.1 Side Reactions ofAlkyl (Meth)acrylate Polymerization 22
1.5.2 Alkyl (Meth)acrylate Polymerization in THF 24
1.5.2.1 Propagation by Solvated Ion Pairs 24
1.5.2.2 Association of Enolate Ion Pairs and Their Equilibrium Dynamics 25
1.5.2.3 Effectof Dynamics of the Association Equilibrium on the MWD 27
1.5.3 Modification of Enolate Ion Pairs with Ligands:
Ligated Anionic Polymerization 29
1.5.3.1 Lewis Base ( r-Type) Coordination 29
Controlkd and Living Polymerizations. Edited by Axel H.E. Müller and Krzysztof Matyjaszewski
© 2009 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-32492-7
VI I Contents
1.5.3.2 Lewis Acid (u-Type) Coordination 30
1.5.4 Metal-Free Anionic Polymerization 32
1.5.4.1 Group Transfer Polymerization (GTP) 32
1.5.4.2 Tetraalkylammonium Counterions 35
1.5.4.3 Phosphorous-Containing Counterions 36
1.5.5 Polymerization of Alkyl (Meth)acrylates in Nonpolar Solvents 37
1.5.5.1 H-Type Coordination 38
1.5.5.2 a, (i-Type Coordination 40
1.5.6 Coordinative-Anionic Initiating Systems 40
1.5.6.1 Aluminum Porphyrins 40
1.5.6.2 Metallocenes 41
1.5.7 Polymerization of N,N-Dialkylacrylamides 41
1.6 Some Applications of Anionic Polymerization 43
1.7 Conclusions and Outlook 45
References 46
2 Carbocationic Polymerization 57
Priyadarsi De and Rudolf Faust
2.1 Introduction 57
2.2 Mechanistic and Kinetic Details of Living Cationic Polymerization 58
2.3 Living Cationic Polymerization 60
2.3.1 Monomers and Initiating Systems 61
2.3.2 Additives in Living Cationic Polymerization 61
2.3.3 Living Cationic Polymerization: Isobutylene (IB) 62
2.3.4 /3-Pinene 64
2.3.5 Styrene (St) 64
2.3.6 p-Methylstyrene (p-MeSt) 65
2.3.7 p-Chlorostyrene (p-ClSt) 66
2.3.8 2,4,6-Trimethylstyrene (TMeSt) 66
2.3.9 p-Methoxystyrene (p-MeOSt) 66
2.3.10 a-Methylstyrene (aMeSt) 67
2.3.11 Indene 67
2.3.12 N-Vinylcarbazol 68
2.3.13 Vinyl Ethers 68
2.4 Functional Polymers by Living Cationic Polymerization 69
2.4.1 Functional Initiator Method 69
2.4.2 Functional Terminator Method 71
2.5 Telechelic Polymers 73
2.6 Macromonomers 75
2.6.1 Synthesis Using a Functional Initiator 76
2.6.2 Synthesis Using a Functional Capping Agent 77
2.6.2.1 Chain-End Modification 79
2.6.2.2 Block Copolymers 79
2.7 Linear Diblock Copolymers 80
Contents I VII
2.8 Linear Triblock Copolymers 83
2.8.1 Synthesis Using Difunctional Initiators 83
2.8.2 Synthesis Using Coupling Agents 84
2.9 Block Copolymers with Nonlinear Architecture 85
2.9.1 Synthesis of AnBn Hetero-Arm Star-Block Copolymers 86
2.9.2 Synthesis of AAB, ABB', and ABC Asymmetric Star-Block
Copolymers Using Furan Derivatives 88
2.9.3 Block Copolymers Prepared by the Combination
of Different Polymerization Mechanisms 88
2.9.3.1 Combination of Cationic and Anionic Polymerization 88
2.9.3.2 Combination of Living Cationic and Anionic
Ring-Opening Polymerization 90
2.9.3.3 Combination of Living Cationic and Radical Polymerization 91
2.10 Branched and Hyperbranched Polymers 92
2.11 Surface Initiated Polymerization - Polymer Brushes 93
2.12 Conclusions 94
References 94
3 Radical Polymerization 103
Krzysztof Matyjaszewski
3.1 Introduction 103
3.2 Typical Features of Radical Polymerization 104
3.2.1 Kinetics 104
3.2.2 Copolymerization 107
3.2.3 Monomers 107
3.2.4 Initiators and Additives 107
3.2.5 Typical Conditions 108
3.2.6 Commercially Important Polymers by RP 108
3.3 Controlled Reversible-Deactivation Radical Polymerization 110
3.3.1 General Concepts 110
3.3.2 Similarities and Differences Between RP and CRP 111
3.4 SFRP: NMP and OMRP Systems - Examples
and Peculiarities 112
3.4.1 OMRP Systems 114
3.4.2 Monomers and Initiators 114
3.4.3 General Conditions 114
3.4.4 Controlled Architectures 115
3.5 ATRP - Examples and Peculiarities 115
3.5.1 Basic ATRP Components 117
3.5.1.1 Monomers 117
3.5.1.2 Transition Metal Complexes as ATRP Catalysts 117
3.5.1.3 Initiators 120
3.5.2 Conditions 122
3.5.3 Mechanistic Features 125
3.5.4 Controlled Architectures 125
VIII I Contents
3.6 Degenerative Transfer Processes and RAFT 126
3.5.6.1 Monomers and Initiators 128
3.5.6.2 Transfer Agents 128
3.6.3 Controlled Architectures 129
3.7 Relative Advantages and Limitations of SFRP, ATRP,
and DT Processes 129
3.7.1 Reactivity Orders in Various CRP Systems 131
3.7.2 Interrelation and Overlap Between Various CRP Systems 132
3.8 Controlled Polymer Architectures by CRP: Topology 133
3.8.1 Linear Chains 134
3.8.2 Star-Like Polymers 135
3.8.3 Comb-Like Polymers 137
3.8.4 Branched and Hyperbranched Polymers 138
3.8.5 Dendritic Structures 139
3.8.6 Polymer Networks and Microgels 140
3.8.7 Cyclic Polymers 141
3.9 Chain Composition 141
3.9.1 Statistical Copolymers 141
3.9.2 Segmented Copolymers (Block, Grafts and Multisegmented
Copolymers) 142
3.9.2.1 Block Copolymers by a Single CRP Method 142
3.9.2.2 Block Copolymers by Combination of CRP Methods 142
3.9.2.3 Block Copolymerization by Site Transformation
and Dual Initiators 142
3.9.2.4 Multisegmented Block Copolymers 144
3.9.2.5 Stereoblock Copolymers 145
3.9.3 Graft Copolymers 145
3.9.4 Periodic Copolymers 147
3.9.5 Gradient Copolymers 147
3.9.6 Molecular Hybrids 148
3.9.7 Templated Systems 148
3.10 Functional Polymers 149
3.10.1 Polymers with Side Functional Groups 150
3.10.2 End Group Functionality: Initiators 150
3.10.3 End Group Functionality through Conversion
of Dormant Chain End 151
3.11 Applications of Materials Prepared by CRP 152
3.11.1 Polymers with Controlled Compositions 152
3.11.2 Polymers with Controlled Topology 152
3.11.3 Polymers with Controlled Functionality 153
3.11.4 Hybrids 153
3.12 Outlook 153
3.12.1 Mechanisms 154
3.12.2 Molecular Architecture 154
3.12.3 Structure-Property Relationship 155
Contents I IX
Acknowledgments 156
References 156
4 Living Transition Metal-Catalyzed Alkene Polymerization:
Polyolefin Synthesis and New Polymer Architectures 167
Joseph B. Edson, GregoryJ. Domski, Jeffrey M. Rose, Andrew D. Bolig,
Maurice Brookhart, and Geoffrey W. Coates
4.1 Introduction 167
4.2 Living a-Olefin Polymerization 169
4.2.1 Metallocene-Based Catalysts 170
4.2.2 Catalysts Bearing Diamido Ligands 171
4.2.3 Catalysts Bearing Diamido Ligands with Neutral Donors 171
4.2.4 Amine-Phenolate and Amine-Diol Titanium
and Zirconium Catalysts 173
4.2.5 Monocyclopentadienylzirconium Amidinate Catalysts 176
4.2.6 Pyridylamidohafnium Catalysts 177
4.2.7 Titanium Catalysts for Styrene Homo-and Copolymerization 178
4.2.8 Tripodal Trisoxazoline Scandium Catalysts 179
4.2.9 Late Transition Metal Catalysts 179
4.3 Living Propylene Polymerization 182
4.3.1 Vanadium Acetylacetonoate Catalysts 183
4.3.2 Metallocene-Based Catalysts 185
4.3.3 Catalysts Bearing Diamido Ligands 186
4.3.4 Bis(phenoxyimine)titanium Catalysts 187
4.3.5 Bis(phenoxyketimine)titanium Catalysts 190
4.3.6 Amine Bisphenolate Zirconium Catalysts 191
4.3.7 Monocyclopentadienylzirconium Amidinate Catalysts 192
4.3.8 Pyridylamidohafnium Catalysts 194
4.3.9 Late Transition Metal Catalysts 195
4.4 Living Polymerization of Ethylene 196
4.4.1 Non-Group 4 Early Metal Polymerization Catalysts 197
4.4.2 Bis(phenoxyimine)titanium Catalysts 199
4.4.3 Bis(phenoxyketimine)titanium Catalysts 201
4.4.4 Titanium Indolide-Imine Catalysts 201
4.4.5 Bis(enaminoketonato)titanium Catalysts 202
4.4.6 Aminopyridinatozirconium Catalysts 202
4.4.7 Tris(pyrazolyl)borate Catalysts 203
4.4.8 Late Transition Metal Catalysts 203
4.5 Living Nonconjugated Diene Polymerization 206
4.5.1 Vanadium Acetylacetonoate Catalysts 207
4.5.2 Bis(phenoxyimine)titanium Catalysts 207
4.5.3 Cyclopentadienyl Acetamidinate Zirconium Catalysts 208
4.5.4 Late Transition Metal Catalysts 208
4.6 Living Homo- and Copolymerizations of Cyclic Olefins 209
4.6.1 Norbornene Homopolymerization 209
X Contents
4.6.2 Copolymers of Norbornene/Ethylene and Cyclopentene/Ethylene 210
4.6.2.1 Non-Group 4 Early Transition Metal Catalysts 210
4.6.2.2 Group 4 Metallocene-Based Catalysts 210
4.6.2.3 Titanium Catalysts for Living Ethylene-Cyclic
Olefin Copolymerization 211
4.6.2.4 Palladium a-Diimine Catalysts 212
4.7 Random Copolymers 212
4.7.1 Random Copolymers Incorporating Polar Monomers 212
4.8 Block Copolymers 213
4.8.1 Block Copolymers Containing Poly(a-olefin) Blocks 213
4.8.2 Block Copolymers Containing Polypropylene Blocks 216
4.8.2.1 Isotactic Polypropylene-Containing Block Copolymers 216
4.8.2.2 Syndiotactic Polypropylene-Containing Block Copolymers 218
4.8.2.3 Atactic Polypropylene-Containing Block Copolymers 220
4.8.3 Polyethylene-Containing Block Copolymers 221
4.8.4 Norbornene- and Cyclopentene-Containing Block Copolymers 222
4.8.5 Block Copolymers Containing Blocks Derived
from 1,5-Hexadiene Polymerization 224
4.8.6 Block Copolymers Containing Blocks Derived
from Polar Monomers 226
4.9 Outlook and Summary 231
References 232
5 Living Ring-Opening Polymerization of Heterocyclic Monomers 241
Stanislaw Penczek, Marek Cypryk, Andrzej Duda, Przemyslaw Kubisa,
and Stanislaw Sfomkowski
5.1 Introduction 241
5.2 Anionic and Coordination Living Ring-Opening
Polymerization (LROP) 246
5.2.1 Initiation in the Anionic LROP 248
5.2.2 Propagation in the Anionic LROP 249
5.2.2.1 Polymerization of O- and S-Heterocyclic Monomers 249
5.2.2.2 Polymerization of Si-, N-, and P-Heterocyclic Monomers 253
5.2.3 Coordination Polymerization 259
5.2.4 Organocatalytic ROP of Cyclic Esters 265
5.2.5 Transfer Processes in the LROP 267
5.2.6 Departures from the Livingness 273
5.3 Cationic CROP and LROP 274
5.3.1 Cationic ROP of Tetrahydrofuran (THF) 274
5.3.2 Propagation in the Cationic ROP 276
5.3.3 Macroion-Macroester Interconversions in the Cationic ROP 278
5.3.4 Cationic ROP of Cyclic Imino Ethers (Oxazolines)
and Cyclic Thioesters 280
5.3.5 Cationic ROP of Cyclosiloxanes 282
5.3.6 Activated Monomer Cationic ROP of Cyclic Monomers 283
Contents I XI
5.4 CROP and LROP Conducted in Dispersions 287
5.5 Conclusion 289
References 289
6 Living Ring-Opening Metathesis Polymerization 297
Christopher W. Bielawski and Robert H. Crubbs
6.1 Overview of Ring-Opening Metathesis Polymerization (ROMP) 297
6.1.1 Introduction 297
6.1.2 ROMP Essentials: Mechanism and Thermodynamics 297
6.1.3 Living Ring-Opening Metathesis Polymerization 300
6.2 Initiators for Living ROMP 302
6.2.1 Historical Aspects 302
6.2.2 Ill-Defined Initiators 302
6.2.3 Titanium 304
6.2.4 Tantalum 307
6.2.5 Tungsten 309
6.2.6 Molybdenum 313
6.2.7 Ruthenium 318
6.3 Applications of Polymers Synthesized Using ROMP:
From Novel Materials to Commercial Products 326
6.3.1 Selected Applications for Polymers Synthesized Using ROMP 327
6.3.2 Commercial Polymers Synthesized Using ROMP 331
6.4 Challenges and Perspectives for the Future 333
6.4.1 Development of New Initiators 333
6.4.2 Polymerization of "New" and "Old" Monomers 334
6.5 Conclusion 335
Acknowledgments 336
References 336
7 Macromolecular Architectures by Living and Controlled/
Living Polymerizations 343
Nikos Hadjichristidis, Marinos Pitsikalis, Hermis latrou, and Ceorgios Sakellariou
7.1 Introduction 343
7.2 Star Polymers 344
7.2.1 Symmetric Stars 344
7.2.1.1 Multifunctional Initiators (MFIs) 344
7.2.1.2 Multifunctional Linking Agents (MFLAs) 350
7.2.13 Difunctional Monomers (DFMs) 355
7.2.2 Star-Block Copolymers 359
7.2.3 Asymmetric Stars 362
7.2.3.1 Molecular Weight Asymmetry 363
7.2.3.2 Topological Asymmetry 369
7.2.4 Miktoarm Star Polymers 370
7.3 Comb Polymers 379
7.3.1 "Grafting Onto" Methods 381
XII I Contents
7.3.2 "Grafting from" Methods 382
7.3.3 "Grafting Through" or Macromonomer Method 384
7.4 Cyclic Polymers 393
7 A.I Cyclic Polymers from Precursors with Homodifunctional Groups 395
7.4.2 Cyclic Homopolymers 395
7.43 Cyclic Block Copolymers 399
7.5 Dendritic Polymers 400
7.5.1 Dendrimers 401
7.5.2 Dendritic Polymers 408
7.6 Complex Macromolecular Architectures 416
7.6.1 ^-Branched Polymers 416
7.6.2 a,w-Branched Polymers 417
7.6.3 Hyperbranched and Dendrigraft Polymers 420
7.6 A Other Complex Architectures 426
7.7 Applications 431
7.8 Conclusions 436
References 438
8 Synthesis of Block and Craft Copolymers 445
Constantinos Tsitsilianis
8.1 Introduction 445
8.2 Principles of Block Copolymerization 446
8.2.1 AB by Anionic Polymerization 447
8.2.2 AB by Cationic Polymerization 448
8.2.3 AB by Controlled Radical Polymerization 450
8.2.3.1 ABbyATRP 450
8.2.3.2 AB by NMP 451
8.2.3.3 AB by RAFT 451
8.2.4 AB by Combination of Methods 452
8.2.4.1 Site-Transformation Reactions 452
8.2.4.2 By Using Dual Initiator 454
8.2.5 AB by Coupling Reactions 455
8.3 ABA Triblock Copolymers 457
8.3.1 Synthetic Strategies 457
8.3.2 ABA by Anionic Polymerization 459
8.3.3 ABAbyGTP 461
8.3.4 ABA by Cationic Polymerization 462
8.3.5 ABA by Controlled Radical Polymerization 463
8.3.6 ABA by Combination of Methods 465
8.4 (AB)n Linear Multiblock Copolymers 466
8.5 ABC Triblock Terpolymers 466
8.5.1 Synthetic Strategies 467
8.5.2 ABC by Anionic Polymerization 468
8.5.3 ABC by GTP 471
Contents I XIII
8.5.4 ABC by Cationic Polymerization 472
8.5.5 ABC by Controlled Radical Polymerization 472
8.5.6 ABC by Combination of Methods 473
8.6 Synthesis of ABCA Tetra- and ABCBA Pentablock Terpolymers 474
8.7 Synthesis of ABCD Quaterpolymers 475
8.8 Graft Copolymers 476
8.8.1 Synthetic Strategies 477
8.8.2 A-g-B Graft Copolymers 478
8.8.3 Model Graft-Like Architectures 483
8.9 Applications 486
8.10 Concluding Remarks 488
References 488
9 Morphologies in Block Copolymers 493
Volker Abetz, Adriana Boschetti-de-Fierro, andJean-Franqois Cony
9.1 Introduction 493
9.2 Block Copolymers in Bulk State 494
9.2.1 Theoretical Descriptions of Block Copolymer Morphologies
in the Bulk State 495
9.2.2 Experimental Results on the Morphological Properties
of Block Copolymers in the Bulk State 500
9.3 Block Copolymer Thin Films 505
9.3.1 General Concepts of Block Copolymer Thin Films 505
9.3.2 Controlled Self-Assembly in Block Copolymer Thin Films 507
9.3.2.1 Interactions with Air and Substrate Interfaces 507
9.3.2.2 Alignment by External Fields 511
9.3.2.3 Crystallization 513
9.4 Block Copolymer Micelles 516
9.4.1 General Concepts of Block Copolymer Micelles 516
9.4.2 Block Copolymer Micelles Containing Metal-Ligand Complexes 520
9.4.3 Multicompartment Micelles Made from ABC
Triblock Terpolymers 530
9.4.3.1 Micelles with a Compartmentalized Core 530
9.4.3.2 Micelles with a Compartmentalized Corona 536
9.5 Applications 539
9.6 Summary and Outlook 542
References 544
10 Industrial Applications 555
Dale L Handl'm,Jr., David R. Hansen, KathrynJ. Wright, and Scott R. Trenor
10.1 Introduction 555
10.2 Synthesis of Anionic Styrenic Block Copolymers 561
10.3 Adhesives and Sealants 564
10.4 Compounding Applications 568
10.4.1 Raw Material Selection 568
XIV I Contents
10.4.2 Processing and Forming 573
10.4.3 Automotive 575
10.4.4 Wire and Cable 577
10.4.5 Medical 578
10.4.6 Soft-Touch Overmolding 578
10.4.7 Ultrasoft Compounds 579
10.4.8 Elastic Films and Fibers 579
10.5 Polymer Modification 580
10.6 Cross-Linked Systems 582
10.6.1 SBC-Based Dynamic Vulcanizates 582
10.6.2 Flexographic Printing Plates 583
10.7 Bitumen Modification 584
10.7.1 Paving 584
10.7.2 Road Marking 587
10.7.3 Roofing 588
10.8 Footwear 589
10.9 Viscosity Modification and Other Highly Diluted
SBC Applications 590
10.9.1 Viscosity Index Improvers 590
10.9.2 Oil Gels 591
10.10 Emerging Technology in Block Copolymers 591
10.10.1 Recycling Compatibilization 591
10.10.2 PVC and Silicone Replacement 592
10.10.3 Sulfonated Block Copolymers 592
10.10.4 Methacrylate and Acrylate Block Copolymers
by Anionic Polymerization 593
10.10.5 Styrene-Isobutylene-Styrene (SiBS) via Cationic Polymerization 596
10.10.6 Commercial Uses of Other Controlled Polymerized Polymers 596
References 599
Index 605 |
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| discipline | Chemie / Pharmazie Physik |
| format | Book |
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| id | DE-604.BV035675941 |
| illustrated | Illustrated |
| indexdate | 2024-07-20T10:16:44Z |
| institution | BVB |
| isbn | 9783527324927 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-017730280 |
| oclc_num | 436261810 |
| open_access_boolean | |
| owner | DE-703 DE-83 DE-19 DE-BY-UBM DE-11 |
| owner_facet | DE-703 DE-83 DE-19 DE-BY-UBM DE-11 |
| physical | XXI, 612 S. Ill., graph. Darst. |
| publishDate | 2009 |
| publishDateSearch | 2009 |
| publishDateSort | 2009 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Controlled and living polymerizations methods and materials ed. by Axel H. E. Müller ... Weinheim Wiley-VCH 2009 XXI, 612 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Polymerization Polymerisation (DE-588)4046704-1 gnd rswk-swf Polymerisation (DE-588)4046704-1 s DE-604 Müller, Axel H. E. 1947- Sonstige (DE-588)133840123 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3294502&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017730280&sequence=000004&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Controlled and living polymerizations methods and materials Polymerization Polymerisation (DE-588)4046704-1 gnd |
| subject_GND | (DE-588)4046704-1 |
| title | Controlled and living polymerizations methods and materials |
| title_auth | Controlled and living polymerizations methods and materials |
| title_exact_search | Controlled and living polymerizations methods and materials |
| title_full | Controlled and living polymerizations methods and materials ed. by Axel H. E. Müller ... |
| title_fullStr | Controlled and living polymerizations methods and materials ed. by Axel H. E. Müller ... |
| title_full_unstemmed | Controlled and living polymerizations methods and materials ed. by Axel H. E. Müller ... |
| title_short | Controlled and living polymerizations |
| title_sort | controlled and living polymerizations methods and materials |
| title_sub | methods and materials |
| topic | Polymerization Polymerisation (DE-588)4046704-1 gnd |
| topic_facet | Polymerization Polymerisation |
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