Paul Rempp and Edward W. Merrill. Polymer Synthesis. 2nd, revised Edition. Hüthig & Wepf Verlag Basel Heidelberg New York

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1 Paul Rempp and Edward W. Merrill Polymer Synthesis 2nd, revised Edition Hüthig & Wepf Verlag Basel Heidelberg New York

2 Table of Contents Part I: Polymerization Reactions Chapter 1: General Considerations about Polymers and Polymer Synthesis 1.1 Introduction Polymerization Reactions Step Growth Polymerizations Chain Growth Polymerizations Thermodynamics Structural Characteristics of Polymers: Shape and Size Placement of the Monomer Units and Stereoregularity Tacticity of Vinyl Polymers Stereoregularity of Diene Polymers Stereoregularity of Polymers Resulting from Ring Opening Polymerization Homopolymers and Copolymers Molecular Weight Distribution and Molecular Weight Averages Chapter 2: Step-Growth Polymerization (Polycondensation) 2.1 Introduction Calculation of Molecular Weights and Molecular Weight Distributions of Polycondensates Molecular Weight Averages Molecular Weight Distributions Polycondensates Obtained from ab Type Base Molecules aa + bb Type Polycondensates Kinetics of Step-Growth Polymerization in Homogeneous Systems Network Formation by Step-Growth Polymerization Examples of Step-Growth Polymerization Reactions Polyesters Polyamides Polyurethanes Polycarbonates Polybenzimidazoles and Aromatic Polyimides Crosslinked Polycondensates Special Cases of Polycondensation Reactions Branched Uncrosslinked Polycondensates Chain Extension Reactions Polyrecombination Reactions Ionenes Polyphenylene Oxides 60

3 10 Table of Contents Chapter 3: free Radical Chain Polymerization 3.1 Introduction Initiators and Monomers Fitted for Free Radical Polymerization Initiators and Initiation Processes Monomers Mechanism of Free Radical Polymerization Initiation Propagation Termination Transfer Reactions Remarks Kinetics of Free Radical Polymerization Kinetic Chain Length, Average Degree of Polymerization and Molecular Weight Distribution Influence of Transfer Reactions on the Degree of Polymerization Determination of Rate Constants in Homogeneous Free Radical Polymerization Temperature Dependence of Rate Constants and of Degrees of Polymerization Trommsdorff Effect Telomerization "Living" Free Radical Polymerizations 86 Chapter 4: Free Radical Copolymerization 4.1 Introduction Copolymerization and Compositional Heterogeneity Plots of the Instantaneous Copolymer Composition Variation of Copolymer Composition versus Conversion Determination of the Radical Reactivity Ratios Methods Experimental Procedures Factors Affecting the Copolymerization Reactivity Q-e-Scheme Kinetics of Radical Copolymerization Sequence Distributions in Radical Copolymerization Penultimate Effects Crosslinking Free Radical Copolymerization Ill 4.10 Some Specific Cases Polyalkylene Sulfones Cyclopolymerization 112 Chapter 5: Anionic Polymerizations 5.1 Introduction Anionic Polymerizations Carried out in Protic Media 117

4 Table of Contents Reaction Scheme Kinetics Molecular Weight Distribution of Polymers Obtained by Anionic Polymerization in Protic Media Ring Opening Polymerization in Protic Media Anionic Polymerization in Aprotic Media: "Living" Polymers Reaction Scheme Kinetics and Molecular Weight Distribution of "Living" Polymers Monomers, Initiators and Solvents in Living Anionic Polymerizations Monomers Initiators: Metal Organic and Radical Anionic Solvents Specific Features of Anionic Polymerizations in Apolar Solvents Specific Features of Anionic Polymerizations Carried out in Polar Solvents Ions and Ion Pairs Contact and Solvent Separated Ion Pairs Applications of Anionic "Living" Polymerizations Protonation ю-functional and aca-difunctional Polymers Block Copolymers Graft Copolymers Networks Stereoelective Polymerizations 139 Chapter 6: Cationic Polymerizations 6.1 Introduction Cationic Polymerization of Vinylic Monomers Initiators and Initiating Reactions Propagation Reaction Transfer and Termination Reactions Kinetic Expressions for Cationic Polymerizations Polyisobutene and Butyl Rubber Inifer Processes Cationic Polymerization of Heterocycles Initiation Propagation Transfer and Termination "Living" Cationic Ring Opening Polymerizations Some Specific Cases Other Ring Opening Polymerizations Polyphosphonitrilic Chloride (Polyphosphazenes) Polydimethylsiloxanes 160

5 12 Table of Contents Chapter 7: Special Features of Ionic and Pseudo-Ionic Polymerizations 7.1 Propagation-Depropagation Equilibria General Kinetics and Thermodynamics of Reversible Propagation Influence of the Reversibility of Chain Growth on the Molecular Weight Distribution Consequences of the Reversibility of the Propagation Step Polymerization Processes Involving Dipole-Dipole Interactions "Living" Cationic Polymerization of Vinylic or Vinylenic Monomers Group Transfer Polymerization Activated Monomer Polymerizations Anionic "Activated Monomer" Polymerizations Cationic "Activated Monomer" Polymerizations Rationalization of Polymerization Processes Involving Ions or Dipoles 178 Chapter 8: Polymerizations Involving Stereoregulation 8.1 Introduction Ziegler-Natta Polymerizations Mechanisms Involved in Ziegler-Natta Polymerizations Kinetics of Ziegler-Natta Polymerizations Ziegler-Natta Ring Opening Polymerizations Ziegler-Natta Copolymerization Reactions Applications of Ziegler-Natta Polymerizations Other Stereoregulating Catalyst Systems Metathesis Polymerizations 195 Chapter 9: Chemical Reactions on Polymers 9.1 Introduction Chemical Reactions Involving the Backbone Chain Oxydative Degradation Chain Unzipping Cleavage by Ozone Periodic Acid Cleavage Free Radical Crosslinking Vulcanization of Elastomers Chemical Reactions Involving the Functions Kinetic Aspects of the Chemical Modification of Polymers Cyclization Reactions Examples of Chemical Reactions Affecting the Substituents of a Polymer Chain Addition Reactions Elimination Reactions Substitution Reactions 210

6 Table of Contents 13 Chapter 10: Functional Polymers, Block and Graft Copolymers, Model Networks 10.1 Introduction Functional Polymers Functionalization by Step Growth Polymerization Functionalization by Free Radical Polymerization Functional Initiators Functionalization by Transfer Processes Telomerizations Functionalization by Anionic Polymerization Functionalization by Cationic Polymerization Block Copolymers Block Copolymers by Free Radical Copolymerization Techniques Block Copolymers by Anionic Living Polymerization Techniques Other Techniques to Synthesize Block Copolymers Cationic Polymerization Site Transformation Tfechniques Coupling between Preformed Functional Blocks Graft Copolymer Synthesis "Grafting from" Methods "Grafting onto" Methods Graft Copolymer Synthesis via Macromonomers Network Formation General Methods - Random Crosslinking End-Linking Methods 234 Part- II: Reactors and Processes for Manufacturing Polymers Chapter 11: Interrelationships of Polymer Structure, Chemistry of Synthesis, and Process Engineering 11.1 Product Definition: Choice of Chemical Route: Engineering Decisions Physical Properties: Variation as Monomer is Converted to Polymer Engineering Decisions Regarding Process and Reactor 242 Chapter 12: Emulsion and Suspension Polymerization 12.1 Emulsion Polymerization Introduction Advantages and Disadvantages Initiators Smith-Ewart Kinetic Scheme Rate of Conversion According to Stage Multiple Radical Effects in Emulsion Polymerization Emulsion Copolymerization 259

7 14 Table of Contents Anomalous Emulsion Polymerization Suspension Polymerization Introduction Problems of Fluid Mechanics Preferred Sequence of Operations Special Bead Polymerized Materials 263 Chapter 13: Heterogeneous Polymerizations and Interfacial Reactions 13.1 Introduction Polymerization of Monomer without Solvent Resulting in a "Precipitated" Polymer Polymerization of Monomer in a Solvent which Causes "Precipitation" of the Polymer Polymerizations with Particulate Stereoregulating Catalysts Introduction Micromolecules, Macromolecules and Heterogeneous Catalysts Polymerizations by Heterogeneous Catalysts with Continuous Liquid Phase Polymerization by Heterogeneous Catalysts in a Gas Fluidized Bed Interfacial Polymerization and Interfacial Reactions Introduction Polymer Formation at an Interfacial Zone Between Two Immiscible Phases Each Containing a Reagent Monomer Reactions on Polymers at Interfacial Zones Hydrolysis of Xanthate Cellulose Hydrolysis of Poly(methyl acrylate) Presented as Cross-Linked Beads 284 Appendices: Examples of Polymerization or Cross-Linking Processes in Reactors which Impart Special Shape A.l Soft Contact Lens: Hydroxyethylmethacrylate 288 A.2 Unsaturated Polyester-Styrene Reinforced with Glass Fiber 289 A.3 Laminates from Epoxy Resins Reinforced with Fabrics 290 A.4 Reaction Injection Molding of Polyurethanes 292 A.5 Reaction Injection Molding of Nylon A.6 Polymethacrylate Formed into Tube, Rod, Sheet 294 В High Pressure Radical Polymerization of Ethylene 295 Solutions of the Problems 298 Bibliography 334

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