Phosphorus-Based Polymers: From Synthesis to Applications (RSC Polymer Chemistry Series)

[BOOK DESCRIPTION]

Phosphorus-containing (co)polymers are gaining wide appeal for many uses, from healthcare and medicine to energy and environmental applications. Phosphorus-Based Polymers is the first book dedicated to this topic and provides a comprehensive overview of the different polymers and their uses. The first part of the book covers the synthesis and polymerisation of different phosphorus containing systems including phosphorus containing (meth)acrylate, (meth)acrylamide and viny or allyl monomers, as well as vinyl phosphonic acid, 2-methacryloyloxyethyl phosphorylcholine, poly(phosphoesters)and polyphosphazenes. The second part of the book contains specific chapters detailing different applications such as biomedical applications in dental materials, tissue engineering and drug delivery, metal complexation for anti-corrosion and wastewater purification materials, fire retardant additives and fuel cell membranes. Written by expert researchers in the chemistry of phosphorus-containing polymers, this book is suitable for academic and industrial researchers interested in polymer and materials synthesis as well as their applications.

[TABLE OF CONTENTS]

Chapter 1 Polymerization of                    1  (18)
    Phosphorus-Containing (Meth)acrylate
    Monomers
          Sophie Monge
          Benjamin Canniccioni
          Ghislain David
          Jean-Jacques Robin
      1.1 Introduction                             1  (2)
      1.2 Synthesis by Free or Controlled          3  (2)
      Radical Polymerization of
      Phosphorus-Based Poly(meth)acrylates as
      Adhesion Promoters
      1.3 Synthesis by Radical Polymerization      5  (2)
      of Phosphorus-Based Poly(meth)acrylates
      for Flame Retardancy
      1.4 Synthesis by Free and Controlled         7  (2)
      Radical Polymerization of
      Phosphorus-Based Poly(meth)acrylates for
      Tissue Engineering
      1.5 Synthesis by Photopolymerization of      9  (4)
      Phosphorus-Based Poly(meth)acrylates for
      Dental Applications
      1.6 Living Radical Polymerization of         13 (1)
      Phosphonated Methacrylate
      1.7 Conclusion                               14 (5)
        References                                 15 (4)
    Chapter 2 Polymerization of                    19 (16)
    Phosphorus-Containing (meth)acrylamide
    Monomers
          Sophie Monge
          Alain Graillot
          Jean-Jacques Robin
      2.1 Introduction                             19 (1)
      2.2 Photopolymerization                      20 (4)
      2.3 Free Radical Polymerization              24 (2)
      2.4 Controlled Radical Polymerization        26 (6)
      2.5 Conclusion and Perspectives              32 (3)
        References                                 33 (2)
    Chapter 3 Phosphorus-Containing Vinyl or       35 (16)
    Allyl Monomers
          Ghislain David
          Claire Negrell-Guirao
      3.1 Introduction                             35 (1)
      3.2 Phosphorus-Containing Vinyl Monomers     36 (7)
        3.2.1 Dialkyl Phosphonate-Containing       36 (2)
        Vinyl Monomers
        3.2.2 Dialkyl Phosphonate-Containing       38 (5)
        Vinyl Ether Monomers
      3.3 Phosphorus-Containing Allyl Monomers     43 (4)
        3.3.1 Radical Homopolymerization           43 (2)
        3.3.2 Radical Copolymerization             45 (2)
      3.4 Conclusions                              47 (4)
        References                                 48 (3)
    Chapter 4 Synthesis and Polymerization of      51 (17)
    Vinylphosphonic Acid
          Lavinia Macarie
          Gheorghe Ilia
      4.1 Introduction                             51 (1)
      4.2 Synthesis of Vinylphosphonic Acid        52 (3)
      4.3 Synthesis of Poly(vinylphosphonic        55 (8)
      acid)
        4.3.1 Synthesis of Poly(Vinylphosphonic    56 (5)
        Acid) from Vinylphosphonic Acid
        4.3.2 Synthesis of Poly(vinylphosphonic    61 (2)
        acid) from Vinylphosphonic Acid
        Derivatives
      4.4 Properties of Poly(vinylphosphonic       63 (1)
      acid)
      4.5 Conclusions                              64 (4)
        References                                 65 (3)
    Chapter 5 2-Methacryloyloxyethyl               68 (29)
    Phosphorylcholine Polymers
          Kazuhiko Ishihara
          Kyoko Fukazawa
      5.1 Molecular Design of                      68 (5)
      2-Methacryloyloxyethyl Phosphorylcholine
      Polymers
        5.1.1 Molecular Design Concept for         68 (2)
        2-Methacryloyloxyethyl
        Phosphorylcholine Polymers
        5.1.2 Synthesis of MPC                     70 (2)
        5.1.3 Parameters for the Polymerization    72 (1)
        of MPC
      5.2 Variations in MPC Polymers               73 (8)
        5.2.1 Control of Chemical Structure        73 (5)
        5.2.2 Surface Characteristics of MPC       78 (2)
        Polymers
        5.2.3 Protein Adsorption Resistance on     80 (1)
        MPC Polymers
      5.3 Functionalization of MPC Polymers        81 (5)
        5.3.1 MPC Polymers for Bioconjugation      81 (2)
        5.3.2 Surface Reactive MPC Polymers for    83 (2)
        Formation of a Durable Polymer Layer
        5.3.3 Photoreactive MPC Polymers for       85 (1)
        Simple Substrate Modification
      5.4 Biomedical Applications of MPC           86 (4)
      Polymers
        5.4.1 Antithrombogenic Surface Coatings    86 (2)
        on Implantable Artificial Organs
        5.4.2 Prevention of Bioresponses at the    88 (1)
        Interface of Biomedical Devices
        5.4.3 Highly Lubricated Surfaces for       88 (2)
        Orthopedic Devices
      5.5 Concluding Remarks                       90 (7)
        Acknowledgements                           90 (1)
        References                                 91 (6)
    Chapter 6 Polyphosphoesters                    97 (28)
          Veronique Montembault
          Laurent Fontaine
      6.1 Introduction                             97 (2)
      6.2 Synthesis by Polycondensation            99 (1)
      6.3 Synthesis by Ring-Opening                100(6)
      Polymerization
        6.3.1 Monomer Synthesis                    101(1)
        6.3.2 ROP of Cyclic Alkylene Phosphates    101(4)
        6.3.3 ROP of Cyclic Alkylene               105(1)
        Phosphonates
        6.3.4 Block, Graft, and Hyperbranched      105(1)
        Copolymers via ROP
      6.4 Synthesis by Post-Polymerization         106(10)
      Functionalization
        6.4.1 Polyphosphates                       108(4)
        6.4.2 Polyphosphoramidates                 112(3)
        6.4.3 Complex Macromolecular               115(1)
        Architectures From Poly(alkylene
        H-Phosphonate)s
      6.5 Conclusion                               116(9)
        References                                 116(9)
    Chapter 7 Phosphazene High Polymers            125(26)
          Harry R. Allcock
      7.1 Introduction                             125(1)
      7.2 Synthesis                                126(3)
        7.2.1 Ring-Opening Polymerization of a     126(2)
        Small-Molecule Cyclic Chlorophosphazene
        such as (NPCl2)3, followed by
        Replacement of the Chlorine Atoms in
        the Resultant Chlorophosphazene High
        Polymer by Organic Groups
        7.2.2 Living Cationic Condensation         128(1)
        Polymerization of a
        Chlorophosphoranimine
        7.2.3 Production of                        128(1)
        Poly(dichlorophosphazene) via the
        Solution Phase Thermal Condensation
        Polymerization of Cl3P=N--POCl2, itself
        Obtained by Reaction of PCl5 and an
        Ammonium Salt
        7.2.4 Polymerization of                    128(1)
        Organophosphoranimines
      7.3 Properties Generated by the              129(1)
      Phosphazene Skeleton
        7.3.1 Vital Reactivity of the P--Cl Bond   129(1)
        7.3.2 Unusual Characteristics of the       129(1)
        P--N Bond
        7.3.3 Hydrolytic Sensitivity on Demand     130(1)
        7.3.4 Radiation Stability                  130(1)
      7.4 Influence by the Side Groups             130(5)
        7.4.1 Fluorinated Side Groups              131(1)
        7.4.2 Aryloxy Side Groups                  132(1)
        7.4.3 Alkylamino and Arylamino Side        132(1)
        Groups
        7.4.4 Amino Acid Ester Side Groups         133(1)
        7.4.5 Inorganic and Organometallic Side    133(2)
        Groups
      7.5 Different Architectures: Block           135(3)
      Copolymers, Combs, Grafts, Stars, and
      Dendrimers
        7.5.1 Block Copolymers                     135(2)
        7.5.2 Grafts, Combs, Stars, and            137(1)
        Dendrimers
        7.5.3 Polymers with Pendent                137(1)
        Cyclotriphosphazene Rings
      7.6 Polyphosphazenes with Other Elements     138(1)
      in the Main Chain
      7.7 Actual and Potential Uses of             139(4)
      Polyphosphazenes
        7.7.1 Fluoroalkoxyphosphazene Polymers     139(1)
        7.7.2 Polyphosphazenes with                139(2)
        Oligoethylenoxy Side Chains
        7.7.3 Poly(p-carboxyphenoxyphosphazene)    141(1)
        7.7.4 Fire-Resistant Polymers              141(1)
        7.7.5 Optical Materials                    142(1)
        7.7.6 Ion Conducting Membranes             143(1)
        7.7.7 Films, Fibers, and Nanofibers        143(1)
      7.8 Future Challenges                        143(8)
        References                                 144(7)
    Chapter 8 Phosphorus-Based Monomers Used       151(16)
    for Dental Application
          Norbert Moszner
          Yohann Catel
      8.1 Introduction to Dental Materials         151(1)
      8.2 Enamel/Dentin Adhesives                  152(2)
        8.2.1 Dental Adhesive Systems              152(1)
        8.2.2 Composition of Self-Etch Adhesives   153(1)
      8.3 Polymerizable Phosphonic Acids           154(5)
        8.3.1 Methacrylates and                    155(2)
        α-Substituted Acrylates
        8.3.2 Hydrolytically Stable Monomers       157(2)
      8.4 Polymerizable Dihydrogen Phosphates      159(4)
        8.4.1 (Meth)acrylates                      159(2)
        8.4.2 Hydrolytically Stable Monomers       161(2)
      8.5 Conclusions                              163(4)
        References                                 163(4)
    Chapter 9 Biomedical Applications of           167(43)
    Phosphorus-Containing Polymers
          Edeline Wentrup-Byrne
          Shuko Suzuki
          Lisbeth Grøndahl
      9.1 Introduction                             167(6)
      9.2 Non-Fouling Applications                 173(4)
      9.3 Cardiovascular Applications              177(4)
        9.3.1 Introduction                         177(1)
        9.3.2 Coronary Stents                      178(1)
        9.3.3 Prosthetic Vascular Grafts           179(1)
        9.3.4 Other Blood-Contacting Devices       180(1)
      9.4 Orthopedics                              181(1)
        9.4.1 Introduction                         181(1)
        9.4.2 Polyethylene Non-Frictional          181(1)
        Applications
        9.4.3 Cobalt--Chromium--Molybdenum         182(1)
        Non-Frictional Applications
      9.5 Bone and Bone-Interfacing Biomaterials   182(6)
        9.5.1 Introduction                         182(1)
        9.5.2 Hydrogels                            183(1)
        9.5.3 Grafted Systems                      184(4)
      9.6 Ophthalmological Applications            188(1)
      9.7 Applications in Drug and Gene Delivery   189(8)
        9.7.1 Introduction                         189(1)
        9.7.2 Poly[2-(methacryloyloxy)ethyl        190(1)
        phosphate] (PMOEP)
        9.7.3 Poly[2-(methacryloyloxy)ethyl        191(3)
        phosphorylcholine] (PMPC)
        9.7.4 Polyphosphoester (PPE)               194(3)
      9.8 Tissue Engineering and Other             197(3)
      Miscellaneous Applications
        9.8.1 Nerve Regeneration                   197(1)
        9.8.2 Nanocomposites                       197(1)
        9.8.3 Biomimetics                          197(1)
        9.8.4 Hydrogels                            198(1)
        9.8.5 Pancreas                             199(1)
      9.9 Summary and Future Directions            200(10)
        Acknowledgements                           200(1)
        References                                 200(10)
    Chapter 10 Complexation with Metals:           210(15)
    Anticorrosion Phosphorus-Containing Polymer
    Coatings
          Ghislain David
          Claire Negrell-Guirao
      10.1 Introduction                            210(1)
      10.2 Coatings Made from Blend Polymers       211(4)
      10.3 Phosphorus-Containing UV Polymer        215(5)
      Coatings
      10.4 Phosphonation of Pre-Made Polymers      220(1)
      10.5 Conclusions                             221(4)
        References                                 222(3)
    Chapter 11 Use of Phosphorus-Containing        225(27)
    Polymers for the Removal of Metal Ions from
    Wastewater
          Lavinia Lupa
          Adriana Popa
          Gheorghe Ilia
      11.1 Introduction                            225(2)
      11.2 Natural Polymers                        227(7)
        11.2.1 Cellulose                           227(3)
        11.2.2 Chitin and Chitosan                 230(4)
      11.3 Synthetic Polymers                      234(14)
        11.3.1 Styrene--Divinylbenzene Copolymer   234(12)
        11.3.2 Other Types of Polymers             246(2)
      11.4 Conclusions                             248(4)
        References                                 248(4)
    Chapter 12 Flame Retardancy of                 252(19)
    Phosphorus-Containing Polymers
          Rodolphe Sonnier
          Laurent Ferry
          Jose-Marie Lopez-Cuesta
      12.1 Introduction                            252(1)
      12.2 Thermal Stability and Charring          253(1)
      Promotion
      12.3 Combustion                              253(5)
      12.4 Calculation of the Phosphorus           258(2)
      Contribution to Flammability
      12.5 Limiting Oxygen Index                   260(1)
      12.6 Chemical Environment of Phosphorus      261(6)
        12.6.1 Aromatic Rings                      262(1)
        12.6.2 Oxidation State of Phosphorus       262(1)
        12.6.3 DOPO                                263(1)
        12.6.4 Additive versus Reactive            264(1)
        Approaches
        12.6.5 Polymeric Additives                 265(1)
        12.6.6 Synergism with Nitrogen             266(1)
      12.7 Conclusion                              267(4)
        References                                 268(3)
    Chapter 13 Proton Conducting Phosphonated      271(23)
    Polymers and Membranes for Fuel Cells
          Bahar Bingol
          Patric Jannasch
      13.1 Introduction                            271(2)
      13.2 Molecular Design of Phosphonated        273(3)
      Polymers for Proton Conducting Membranes
      13.3 Phosphonated Non-Aromatic               276(4)
      Hydrocarbon Polymers
      13.4 Phosphonated Aromatic Backbone          280(3)
      Polymers
        13.4.1 Aromatic Polymers Directly          280(2)
        Phosphonated on the Main Chain
        13.4.2 Aromatic Polymers with              282(1)
        Phosphonated Side Chains
      13.5 Phosphonated Fluoropolymers             283(2)
      13.6 Phosphonated Block and Graft            285(3)
      Copolymers
      13.7 Phosphonated Inorganic--Organic         288(1)
      Membranes
      13.8 Possible Future Directions              289(5)
        References                                 290(4)
Subject Index                                      294