Functional Synthetic Polymers E-Book

Johannes Karl Fink

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 345

Veröffentlichungsjahr: 2019

Beschreibung

The text focuses on the basic issues and also the literature of the past decade. The book provides a broad overview of functional synthetic polymers. Special issues in the text are: Surface functionalization supramolecular polymers, shape memory polymers, foldable polymers, functionalized biopolymers, supercapacitors, photovoltaic issues, lithography, cleaning methods, such as recovery of gold ions olefin/paraffin, separation by polymeric membranes, ultrafiltration membranes, and other related topics.

Leseprobe

Contents

Cover

Preface

Acknowledgements

Chapter 1: Basic Issues of Functionalized Polymers

References

Chapter 2: Methods and Principles of Functionalization

2.1 Analysis and Characterization

2.2 Functional Groups

2.3 Stille Polycondensation

2.4 Light-Mediated Atom Transfer Radical Polymerization

2.5 Catalytic Insertion Polymerization

2.6 C–H Functionalization

2.7 Surface Functionalization

2.8 Compatibilization of Polar Polymers

2.9 Supramolecular Polymers

2.10 Microgels

2.11 Polymers from Sulfur

2.12 Aliphatic Polyesters

2.13 Graphitic Carbon Nitride Polymers

2.14 Functionalized Buckminster[60]fullerene

2.15 Functional Semi-fluorinated Polymers

2.16 Hydroxyl-Terminated Poly(butadiene)

2.17 Poly(carbonate)s

2.18 Poly(styrene)s

2.19 Alkyne-Functional Polymers

2.20 Polymers from Renewable Plant Oils

2.21 Chitin and Chitosan

2.22 Amylose Hybrids

2.23 Poly(acryloyl hydrazide)

2.24 Redox-Active Tetrathiafulvalenes

2.25 Sequence-Controlled Polymers

2.26 Oligomeric Silsesquioxane

2.27 Proteins

2.28 Functional Polymer Microspheres

2.29 Functional Biopolymers

References

Chapter 3: Technical Applications

3.1 Electrical Applications

3.2 Photocatalytic Methods

3.3 Cleaning Methods

3.4 Molecularly Imprinted Polymers

3.5 Metal-Organic Frameworks

3.6 Functional Microcapsules

3.7 Shape-Memory Polymers

3.8 Solder Pastes

3.9 Antimicrobial Food Packaging Films

3.10 Flame Retardants

3.11 Liquid Toner

3.12 Hydroxyl-Functionalized Compositions

3.13 Polymeric Membranes

3.14 Rubber Formulations and Tire Materials

3.15 Polymer Composition for Grease

3.16 Hydrogels

3.17 Coordinating Polymers

3.18 Dye Removal

3.19 Separation Processes

3.20 Nanomaterials

3.21 Sensitive Detection of Explosives

References

Chapter 4: Medical Applications

4.1 Biomedical Applications

4.2 pH-Sensitive Polymers

References

Chapter 5: Pharmaceutical Applications

5.1 Poly(ethylene glycol)

5.2 Poly(hydroxy butyrate)

5.3 Poly(glycerol)

5.4 Poly(carbonate)s

5.5 Poly(ethylene glycol) Derivates

5.6 Nanosized Drug Delivery Systems

5.7 Poly(ethylene imine)s

5.8 Poly(amino acid)s

5.9 Poly(N-acrylamide)s

5.10 Polyphosphates

5.11 Poly(vinyl ether)s

5.12 Poly(N-vinyl amide)s

5.13 Poly(allylamine)

5.14 Poly((meth)acrylate)s

5.15 Poly(acrylonitrile)s

5.16 Antibacterial Agents

5.17 Clenbuterol Analysis

References

Index

Acronyms

Chemicals

General Index

End User License Agreement

Guide

Cover

Table of Contents

Begin Reading

List of Illustrations

Chapter 2

Figure 2.1

2-Trifluoromethyl-2-propanol.

Figure 2.2

Synthesis of azolopyridines and azolopyrimidines (25).

Figure 2.3

Synthesis of salicyloyl-

l

-histidine amide (26).

Figure 2.4

Itaconic acid.

Figure 2.5

Citric acid.

Figure 2.6

Bis[

N,N″′

-(2,4,6-tri(methylphenyl)amido)ethylene diamine...

Figure 2.7

Bis(dimethyldisiloxane)(indene-1-yl)zirconium dichloride.

Figure 2.8

Trithiocyanuric acid.

Figure 2.9

Crosslinking agents.

Figure 2.10

Foam reagents.

Figure 2.11

Poly(sulfur-random-1,3-diisopropenylbenzene) (73).

Figure 2.12

Malide dibenzyl ester.

Figure 2.13

3-[(Benzyloxycarbonyl)-methyl]-1,4-dioxane-2,5-dione.

Figure 2.14

Functional epoxides.

Figure 2.15

β

-Benzyl malolactonate.

Figure 2.16

4-Trifluoroacetyl-7-oxo-1,4-oxazaperhydroepine.

Figure 2.17

Components for a four-membered lactone.

Figure 2.18

Morpholine-2,5-dione.

Figure 2.19

Synthesis of lactide-functionalized polymers (91).

Figure 2.20

Organic ligands (91).

Figure 2.21

Synthesis of mesoporous graphitic C

3

N

4

(93).

Figure 2.22

Organic photoredox catalysts.

Figure 2.23

Glaser coupling.

Figure 2.24

Maltopentaose.

Figure 2.25

1-Butyl-3-methylimidazolium chloride.

Figure 2.26

tert-Butyl-2-acryloylhydrazine-1-carboxylate.

Figure 2.27

2-((Ethylthio)carbonothioyl)thio-2-methylpropanoic acid.

Figure 2.28

4-Imidazolecarboxaldehyde.

Figure 2.29

Tetrathiafulvalene.

Figure 2.30

Tetrathiafulvalene compounds.

Figure 2.31

Compounds for ligands (144).

Figure 2.32

Furan-protected maleimide.

Figure 2.33

1,6-Hexanediol dipropiolate.

Figure 2.34

Materials for thiol-ene and amino-yne click reactions.

Figure 2.35

Octakis(dimethylsiloxy)-T8-silsesquioxane.

Figure 2.36

9-Anthracenylmethyl methacrylate.

Figure 2.37

Monomers for phosphonated peptoid diblock copolymers (171).

Figure 2.38

3,5-Bis(trifluoroacetamido)benzoic acid.

Figure 2.39

Synthesis of 1,3,5-tris(4′-aminophenylcarbamoyl)benzene (177).

Figure 2.40

Acid chlorides.

Figure 2.41

Materials for aramids.

Figure 2.42

Functional monomers.

Figure 2.43

Trypsin.

Figure 2.44

Naphthalen-1-ylboronic acid.

Figure 2.45

5-Hydroxymethylfurfural derivatives.

Figure 2.46

Compounds for syntheses of 5-aminolevulinic acid.

Figure 2.47

Prothrin and Chrysanthemic acid chloride.

Figure 2.48

2-Ethoxy-1,3,2-dioxaphosphinane 2-oxide.

Figure 2.49

Poly(3′,5′-cyclic 3-(3-butenyl) thymidine ethyl phosphate).

Figure 2.50

Synthesis of a phosphoramidite (201).

Figure 2.51

Compounds for the synthesis of phosphoramidite containing an ATRP initiating...

Chapter 3

Figure 3.1

3-Methoxythiophene.

Figure 3.2

p

-Toluenesulfonic acid.

Figure 3.3

Indacenodithiophene.

Figure 3.4

2-(Tributylstannyl)thiophene.

Figure 3.5

Synthesis of a carboxylic acid-directed 3,7-dibromination and cross-coupling (4).

Figure 3.6

Photoisomerization reaction of an azobenzene-functionalized polymer (5).

Figure 3.7

Copolymer with poly disperse orange (5).

Figure 3.8

Terminal alkynes.

Figure 3.9

Materials for grafting.

Figure 3.10

Formaldehyde dimethyl acetal.

Figure 3.11

Synthesis of a hypercrosslinked polymer (21).

Figure 3.12

1,10-Phenanthroline.

Figure 3.13

Monomers for polymeric adsorbents (24).

Figure 3.14

3-Aminopropyl-triethoxysilane.

Figure 3.15

Iminodiacetic acid.

Figure 3.16

Poly(1,4-dioxa-7,12-diazacyclotetradecane-8,11-dione).

Figure 3.17

Naproxen.

Figure 3.18

2-Hydroxy-3-(isopropylamino)propyl methacrylate.

Figure 3.19

Fluorescein.

Figure 3.20

Thiol monomers.

Figure 3.21

Compounds for Michael addition.

Figure 3.22

Compounds for Michael addition.

Figure 3.23

9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.

Figure 3.24

10-(2,5-Dihydroxyl-phenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.

Figure 3.25

3-Aminopropyl-triethoxysilane.

Figure 3.26

Synthesis of

N

-(2-(5,5-dimethyl-l,3,2-dioxaphosphinyl-2-ylamino)...

Figure 3.27

Monomers for poly(hydroxystearic acid) (45).

Figure 3.28

Components for sulfonated poly(ether sulfone).

Figure 3.29

Synthesis of a sulfonated poly(ether sulfone) (51).

Figure 3.30

Trimesoyl chloride.

Figure 3.31

Allylcyclohexylamine.

Figure 3.32

Monomers (68).

Figure 3.33

1-Butyl-3-methylimidazolium tetrafluoroborate.

Figure 3.34

Glutardialdehyde.

Figure 3.35

β

-Cyclodextrin.

Figure 3.36

Methylene blue.

Figure 3.37

Surface precipitation polymerization materials (81).

Figure 3.38

Tetraacid compounds (82).

Figure 3.39

Tetraamino compounds (82).

Figure 3.40

Tetraamino compounds (82).

Figure 3.41

Thiolene (82).

Figure 3.42

3-(

N

-2-Methacryloyloxyethyl-

N,N

-dimethyl)ammonatobutane-sulfonate.

Figure 3.43

2,2′-Dipyridyl.

Figure 3.44

N,N

-Dimethylaminoethyl methacrylate.

Figure 3.45

Monomers (88).

Figure 3.46

Multifunctional terminators.

Figure 3.47

Tetramethylethylene diamine.

Figure 3.48

Tetraethyl orthosilicate.

Figure 3.49

Diethyl 3,3′-((3-(triethoxysilyl)propyl)azanediyl)dipropionate.

Figure 3.50

Sulfur atom containing cyclic functional initiators (96).

Figure 3.51

Silica coupling agents.

Figure 3.52

1,3-Dimethyl-2-imidazolidinone.

Figure 3.53

Materials for hydrazone compounds (97).

Figure 3.54

Synthesis of Cyclohexanecarboxaldehydepiperidinehydrazone (97).

Figure 3.55

Monomers for a liquid polymer.

Figure 3.56

Vinyl modifiers.

Figure 3.57

Functional initiator precursors (98).

Figure 3.58

Synthesis of a liquid polymer (98).

Figure 3.59

Synthesis of a liquid polymer (98).

Figure 3.60

N-Phenyl-N′-(1,3-Dimethylbutyl)-p-phenylenediamine (98).

Figure 3.61

Accelerators (98).

Figure 3.62

Cyano compounds (99).

Figure 3.63

2-Cyanobenzaldehyde o-methyloxime.

Figure 3.64

Protected amino groups (101).

Figure 3.65

Maleic acid derivatives.

Figure 3.66

Synthesis of the bismalimide pre-product 1,4-diazocane-5,8-dione (147).

Figure 3.67

2,2′:6′,2″-Terpyridine.

Figure 3.68

Merocyanine.

Figure 3.69

Tris(benzyltriazolylmethyl)amine.

Figure 3.70

Dyes.

Figure 3.71

Cationic dyes.

Figure 3.72

Reactive Blue 21.

Figure 3.73

Hemicellulose compounds.

Figure 3.74

2,2′-Azobis(2-methylbutyronitrile).

Figure 3.75

Diamine monomers.

Figure 3.76

1,3,5-Triphenyl-1,5-dichloro-1,4-pentadiene.

Figure 3.77

Picric acid.

Chapter 4

Figure 4.1

Functional fluorophores (18).

Figure 4.2

Azidocoumarin.

Figure 4.3

Isoindoline.

Figure 4.4

Squarylium dye III.

Figure 4.5

Photoclick reaction (18).

Figure 4.6

([2-(2-Methacrylamido)-ethyldithio]-ethylcarbamoyl-methoxy)acetic acid.

Figure 4.7

N,N

′-Methylenebisacrylamide.

Figure 4.8

Materials for blending.

Figure 4.9

Glutathione.

Figure 4.10

Compounds for trigonal glutathione nanospheres.

Figure 4.11

1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene.

Figure 4.12

N-Hydroxysuccinimide.

Figure 4.13

3-Glycidoxypropyl trimethoxysilane.

Figure 4.14

L-Glutamic acid.

Figure 4.15

4-Amino-

N

-[4,6-dimethyl-2-pyrimidinyl]-benzenesulfonamine (sulfomethazine)...

Chapter 5

Figure 5.1

Heptakis(2,6-di-o-methyl)-

β

-cyclodextrin.

Figure 5.2

Compounds for a coupling method (17).

Figure 5.3

Synthesis of pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate.

Figure 5.4

Disulfide chemicals (28).

Figure 5.5

Cytostatic agents.

Figure 5.6

Chlorotriazine.

Figure 5.7

Trifunctional amino acids.

Figure 5.8

N-(2-Hydroxypropyl)methacrylamide.

Figure 5.9

Vinylpyrrolidone derivatives. VPC: 3-Carboxyvinylpyrrolidone, VPS: 3-Sulfoalkylv...

Figure 5.10

2-Dimethylaminoethyl methacrylate.

Figure 5.11

Glycidyl methacrylate.

Figure 5.12

Clenbuterol and the structural analogues.

List of Tables

Chapter 1

Table 1.1

Uses of functional polymers (5).

Table 1.2

Standards in the context of functional polymers.

Chapter 2

Table 2.1

Catalysts (43).

Table 2.2

Shuttling agents (43).

Table 2.3

Crosslinking agents for inverse vulcanization (50).

Table 2.4

Complexation effects (115,116).

Table 2.5

Tetrathiafulvalene derivates (138).

Table 2.6

Nitroxide-mediated polymerization initiators (201).

Chapter 3

Table 3.1

Designs of the compositions (37).

Table 3.2

Monomers (88).

Table 3.3

Multifunctional terminators (88).

Table 3.4

Metal ester compounds (93).

Table 3.5

Organolithium initiators (94).

Table 3.6

Silica coupling agents (94).

Table 3.7

Materials for hydrazone compounds (97).

Table 3.8

Monomers for a liquid polymer (98).

Table 3.9

Anionic initiators (98).

Table 3.10

Vinyl modifiers (98).

Table 3.11

Functional initiator precursors (98).

Table 3.12

Formulation (98).

Table 3.13

Cyano compounds for modification (99).

Table 3.14

Applications of polymer hydrogels (107).

Table 3.15

Kinetic model analysis of maleic acid-ethylene diamine hydrogel adsorption behavior...

Table 3.16

Maximum adsorption capacities (159).

Table 3.17

Primary amine-functionalized polymers (160).

Chapter 4

Table 4.1

Functional fluorophores (18).

Chapter 5

Table 5.1

Polymer classes used for pharmaceutical applications (1).

Table 5.2

Poly(ethylene glycol) derivatives (1).

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Scrivener Publishing100 Cummings Center, Suite 541JBeverly, MA 01915-6106

Publishers at ScrivenerMartin Scrivener ([email protected])Phillip Carmical ([email protected])

Functional Synthetic Polymers

Johannes Karl Fink

This edition first published 2019 by John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, USA and Scrivener Publishing LLC, 100 Cummings Center, Suite 541J, Beverly, MA 01915, USA © 2019 Scrivener Publishing LLC For more information about Scrivener publications please visit www.scrivenerpublishing.com.

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Library of Congress Cataloging-in-Publication Data ISBN 978-1-119-59202-0

Preface

The scientific literature with respect to functional synthetic polymers is collected in this monograph. The text focuses on the basic issues and also the literature of the past decades. The book provides a broad overview of the synthesis procedures for functional synthetic polymers and the materials used therein.

In addition to basic issues concerning functionalized polymers, particular emphasis is given to the principles of functionalization, basic functional groups, and surface functionalization. Also, fields of special application, such as electrical applications, water cleaning methods, and medical and pharmaceutical applications, are reviewed.

Beyond educating students of polymer chemistry, this book will be of importance to chemists and other scientists in specialty fields, such as electronics, medicine and pharmacology, interested in expanding their knowledge about topics concerning the issues in this field.

Among the special issues addressed in the text are: Surface functionalization supramolecular polymers, shape-memory polymers, foldable polymers, functionalized biopolymers, supercapacitors, photovoltaics, lithography, cleaning methods, such as recovery of gold ions olefin/paraffin, separation by polymeric membranes, ultrafiltration membranes, and other related topics.

How to Use This Book

Utmost care has been taken to present reliable data. However, because of the vast variety of material presented herein, it is not possible to include detailed information on all aspects of the topic, and it is recommended that the reader study the original literature for more complete information.

Index

There are three indices: an index of acronyms, an index of chemicals, and a general index. In the index of chemicals, compounds that occur extensively are not included at every occurrence, but rather when they appear in an important context. When a compound is found in a figure, the entry is marked in boldface letters in the chemical index.

Acknowledgements

I am indebted to our university librarians, Dr. Christian Hasenhüttl, Dr. Johann Delanoy, Gerlinde Iby, Franz Jurek, Margit Keshmiri, Friedrich Scheer, Christian Slamenik, Renate Tschabuschnig, and Elisabeth Groß for their support in literature acquisition. In addition, many thanks to the head of my department, Professor Wolfgang Kern, for his interest and permission to prepare this text.

I also want to express my gratitude to all the scientists who have carefully published their results concerning the topics dealt with herein. This book could not have been otherwise compiled.

Last, but not least, I want to thank the publisher, Martin Scrivener, for his abiding interest and help in the preparation of the text. In addition, my thanks go to Jean Markovic, who made the final copyedit with utmost care.

Johannes Fink

Leoben, 7th February 2019