Phosphorus-based Polymers From Synthesis to Applications

334 Pages·2014·6.64 MB·English

by  Monge, Sophie, David, Ghislain

Phosphorus-Based Polymers
From Synthesis to Applications
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RSC Polymer Chemistry Series
Series Editors:
Professor Ben Zhong Tang (Editor-in-Chief), The Hong Kong University of
Science and Technology, Hong Kong, China
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0 Professor Alaa S. Abd-El-Aziz, University of Prince Edward Island, Canada
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F Professor Stephen L. Craig, Duke University, USA
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2 ProfessorJianhuaDong,NationalNaturalScienceFoundationofChina,China
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2 Professor Toshio Masuda, Fukui University of Technology, Japan
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8 Professor Christoph Weder, University of Fribourg, Switzerland
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9/9 Titles in the Series:
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10 1: Renewable Resources for Functional Polymers and Biomaterials
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1 2: Molecular Design and Applications of Photofunctional Polymers and
doi: Materials
org | 3: Functional Polymers for Nanomedicine
c. 4: Fundamentals of Controlled/Living Radical Polymerization
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bs.r 5: Healable Polymer Systems
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p://p 6: Thiol-X Chemistries in Polymer and Materials Science
htt 7: Natural Rubber Materials: Volume 1: Blends and IPNs
n 8: Natural Rubber Materials: Volume 2: Composites and Nanocomposites
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14 9: Conjugated Polymers: A Practical Guide to Synthesis
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Phosphorus-Based Polymers
From Synthesis to Applications
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2 University of Montpellier 2, Institut Charles Gerhardt de
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F Preface
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1 Phosphorus-BasedPolymers:FromSynthesistoApplicationsaimsatprovidinga
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oi:1 broad overview of recent developments in the synthesis and applications of
g | d phosphorus-containing polymers. Over the last few years, more and more
or research papers have been published on this field. Polymerization of dif-
c.
s.rs ferent kinds of phosphorus-based monomers using various methods has
ub beencarriedout:(meth)acrylates,(meth)acrylamides,vinylphosphonicacid,
p
p:// styrenic, and allylic monomers. The resulting phosphorus-based materials
htt have found applications in different domains: biomedical, complexation
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o with metals, fire retardant additives, fuel cell membranes, etc.
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01 Each chapter of this book provides precise and complete information on
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y the state of current knowledge in the field of phosphorus materials. Con-
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7 tributions were written by experts that we deeply acknowledge for sharing
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. n theirexpertiseandknowledge,makingthisbookunderstandableforabroad
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d readership. Chapters 1 to 7 are devoted to the polymerization of various
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ThebookbeginswithChapter1byRobinandco-workers,whichdescribes
the synthesis and polymerization of phosphorus-containing (meth)acrylate
monomers. This class of polymers is probably the most studied in the field
of phosphorus-containing polymers, since the corresponding polymers
may contain phosphonated ester, phosphonic acid, or phosphoric ester
functions.Thischapterstartswithathoroughdescriptionofthewiderange
of (meth)acrylate monomers carrying different types of phosphorus groups,
i.e. phosphonate, aminobisphosphonate, etc. Then, both conventional and
controlledradicalpolymerization(mainlyreversibleaddition–fragmentation
chain transfer) are discussed in the following sections, as well as the pho-
topolymerization of these monomers for use as dental applications.
RSCPolymerChemistrySeriesNo.11
Phosphorus-BasedPolymers:FromSynthesistoApplications
EditedbySophieMongeandGhislainDavid
rTheRoyalSocietyofChemistry2014
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
v
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vi Preface
Chapter 2 by Monge et al. details the synthesis and polymerization of
phosphorus-containing (meth)acrylamide monomers. Compared to their
(meth)acrylate homologues, this class of monomer is more hydrolytically
stable and thus more interesting for a large variety of applications. Never-
theless, these monomers are less studied and most of the results mainly
05 report their photopolymerization in order to develop stable self-etching
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23- monomersisalsodiscussedinthischapterandspecificallythesynthesisof
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24 block copolymers by controlled radical polymerization is investigated.
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82 Chapter 3 by David and Negrell-Guirao reviews phosphorus-containing
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81 allylandvinylmonomers.Thesyntheticstrategiestoobtainsuchmonomers
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9/9 are described, covering Arbuzov reactions, transetherification, etc. The
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0 radical copolymerization of these monomers in the presence of electron-
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10. donating monomers is thoroughly discussed, as well as chain transfer
oi: reactions leading to chain scission. The use of the resulting copolymers in
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c. Chapter 4 by Macarie and Ilia aims at discussing the synthesis and poly-
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s.r merization of vinylphosphonic acid (VPA), as well as the properties of the
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http:// VPA is based on 2-chloroethylphosphonic acid, a plant growth regulator ob-
n tained on an industrial scale. According to its poor reactivity in radical poly-
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4 merization, its polymerization is very challenging. Furthermore, the authors
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2 affordadeepinsightintothestructureofpoly(vinylphosphonicacid),whichis
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07 well as the thermal and mechanical properties of poly(VPA) are detailed.
. on Chapter 5 by Ishihara and Fukazawa focuses on polymers obtained from
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he 2-methacryloyloxyethyl phosphorylcholine (MPC) monomer. Indeed, the
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bli moleculardesignofMPCpolymerswithsignificantfunctionsforbiomedical
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some MPC polymers can provide artificial cell membrane-like structures at
the surface as excellent interfaces between artificial systems and biological
systems. In the clinical medicine field, MPC polymers have been used for
surface modification of medical devices, including long-term implantable
artificialorganstoimprovebiocompatibility.ThussomeMPCpolymershave
been provided commercially for these applications.
Montembault and Fontaine highlight the synthesis and development of
polyphosphoestersinChapter6.Thesyntheticstrategiesthatcanbeusedfor
polyphosphoesters synthesis, including poly(alkylene H-phosphonate)s,
poly(alkylene phosphate)s, poly(alkylene phosphoramidate)s, and poly-
(alkylenephosphonate)s,arereviewed.Thischapteralsosummarizesrecent
developments employing new and efficient chemistries, such as organo-
catalyzed ring-opening polymerization and ‘‘click’’ chemistry, to prepare
complex polyphosphoester-based macromoleculararchitectures (block,graft,
andhyperbranchedcopolymers).Thesephosphorus-containingmaterialsare
veryuseful, especially for biomedicalapplications suchastissueengineering
or drug delivery.
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Preface vii
Chapter 7 by Allcock and Pugh describes the family of polyphosphazene
polymers that have a structure based on a backbone of alternating phos-
phorus and nitrogen atoms, and with two organic side groups attached to
each phosphorus. The authors of this chapter show that polyphosphazenes
aremostlysynthesizedbyamacromolecularsubstitutionmethodinwhicha
05 reactive intermediate, polydichlorophosphazene, is used as a substrate for
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23- tial uses for these polymers are in the field of aerospace, fire resistant
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24 polymers, fuel cells, and also for biomedical applications.
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82 The following chapters are devoted to applications of phosphorus-based
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81 materials. Thus Chapter 8 by Mozsner and Catel deals with the use of
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9/9 polymerizable phosphonic acids (PAs) and dihydrogen phosphates (DHPs)
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0 for dental applications. Several PAs and DHPs were synthesized to notably
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10. improve the shear bond strength to dentin and enamel, the stability of the
oi: adhesive formulation, and the chemical adhesion to tooth tissues. Some of
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g | these monomers are nowadays included in commercial dental adhesives.
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c. Chapter9byWentrup-Byrneetal.reportsonthebiomedicalapplications
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s.r of phosphorus-containing polymers such as poly[2-(acryloyloxy)ethyl phos-
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p phate], poly[2-(methacryloyloxy)ethyl phosphate], and polyphosphoesters,
http:// especially tissue repair and regeneration, medical device development, and
n tissueengineering.Abroadoverviewisachieved,asapplicationsconsidered
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4 includecardiovascular,ophthalmological,drugandgenedelivery,aswellas
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2 orthopedics and bone-interface repair, their surface chemistry, and the
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07 AnticorrosionpropertiesarehighlightedintheChapter10byDavidetal.
. on Recent trends concern the development of organic coatings containing
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Chapter11byPopaetal.isdevotedtotheuseofchelatingresinsobtained
by the chemical modification of their surface with different phosphorus
pendant groups for the removal of heavy metals from various industrial
waste effluents. It is shown that modification of the polymeric matrix
through phosphorylation of its surface with different phosphorus pendant
groupsleadstoanincreaseintheadsorptionefficiencyofthepolymerinthe
removal of metal ions from various aqueous solutions.
Theinfluenceofphosphorusincorporatedthroughareactiveapproachon
theflameretardancyofpolymersisreviewedinChapter12bySonnieretal.
It is notably demonstrated that phosphorus has an influence on the deg-
radation pathway of the polymer and hence its thermal stability and
charring.
Finally,Chapter13byJannaschandBingo¨ldealswithproton conducting
phosphonated polymers and membranes for fuel cells. Polymers functio-
nalized with phosphonic acids enable both intrinsic and water-assisted
protonconductivityandarethusattractiveforuseaselectrolytematerialsin
electrochemical devices.
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viii Preface
We expect that both specialist and non-specialist readers will find
Phosphorus-Based Polymers: From Synthesis to Applications very valuable
to update or discover the newest trends in phosphorus-containing
materials.
Sophie Monge
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9/ Chapter1 PolymerizationofPhosphorus-Containing(Meth)acrylate
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10 Monomers 1
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1 Sophie Monge, Benjamin Canniccioni, Ghislain David and
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bs.r 1.2 Synthesis by Free or Controlled Radical
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htt Poly(meth)acrylates as Adhesion Promoters 3
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Dental Applications 9
1.6 Living Radical Polymerization of Phosphonated
Methacrylate 13
1.7 Conclusion 14
References 15
Chapter 2 Polymerization of Phosphorus-Containing
(meth)acrylamide Monomers 19
Sophie Monge, Alain Graillot and Jean-Jacques Robin
2.1 Introduction 19
2.2 Photopolymerization 20
RSCPolymerChemistrySeriesNo.11
Phosphorus-BasedPolymers:FromSynthesistoApplications
EditedbySophieMongeandGhislainDavid
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x Contents
2.3 Free Radical Polymerization 24
2.4 Controlled Radical Polymerization 26
2.5 Conclusion and Perspectives 32
References 33
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org | 3.3.1 Radical Homopolymerization 43
sc. 3.3.2 Radical Copolymerization 45
bs.r 3.4 Conclusions 47
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4.3.2 SynthesisofPoly(vinylphosphonicacid)from
Vinylphosphonic Acid Derivatives 61
4.4 Properties of Poly(vinylphosphonic acid) 63
4.5 Conclusions 64
References 65
Chapter 5 2-Methacryloyloxyethyl Phosphorylcholine Polymers 68
Kazuhiko Ishihara and Kyoko Fukazawa
5.1 Molecular Design of 2-Methacryloyloxyethyl
Phosphorylcholine Polymers 68
5.1.1 Molecular Design Concept for
2-Methacryloyloxyethyl Phosphorylcholine
Polymers 68
5.1.2 Synthesis of MPC 70
5.1.3 Parameters for the Polymerization of MPC 72
5.2 Variations in MPC Polymers 73