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 Sepour/Carraher's

Polymer
Chemistry Sixth Edition
Revised and Expanded

Charles E. Carraher, Jr.

College of Science
Florida Atlantic University
Boca Raton, and
Florida Center for Environmental Studies
Palm Beach Gardens, Florida, U.S.A.

MARCEL DEKKER, INC. NEW YORK • BASEL

This edition published in the Taylor & Francis e-Library, 2005.
“To purchase your own copy of this or any of Taylor & Francis or Routledge’s
collection of thousands of eBooks please go to www.eBookstore.tandf.co.uk.”
Library of Congress Cataloging-in-Publication Data
A catalog record for this book is available from the Library of Congress.

ISBN 0-203-91130-X Master e-book ISBN

ISBN: 0–8247–0806–7 (Print Edition)

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Neither this book nor any part may be reproduced or transmitted in any form or by any means,
electronic or mechanical, including photocopying, microfilming, and recording, or by any informa-
tion storage and retrieval system, without permission in writing from the publisher.
 UNDERGRADUATE CHEMISTRY

A Series of Textbooks

Edited by

J. J. LAGOWSKI
Department of Chemistry
The University of Texas at Austin

1. Modern Inorganic Chemistry, J. J. Lagowski

2. Modern Chemical Analysis and Instrumentation, Harold F. Walton and Jorge
Reyes
3. Problems in Chemistry, Second Edition, Revised and Expanded, Henry O. Daley,
Jr., and Robert F. O'Malley
4 Principles of Colloid and Surface Chemistry, Paul C. Hiemenz
5. Principles of Solution and Solubility, Kozo Shinoda, translated in collaboration with
Paul Becher
6. Physical Chemistry: A Step-by-Step Approach, M. K. Kemp
7. Numerical Methods in Chemistry, K. Jeffrey Johnson
8. Polymer Chemistry An Introduction, Raymond B. Seymour and Charles E.
Carraher, Jr
9. Principles of Colloid and Surface Chemistry, Second Edition, Revised and
Expanded, Paul C. Hiemenz
10. Problems in Chemistry, Second Edition, Revised and Expanded, Henry O. Daley,
Jr, and Robert F. O'Malley
11. Polymer Chemistry: An Introduction, Second Edition, Raymond B. Seymour and
Charles E. Carraher, Jr
12. Polymer Chemistry. An Introduction, Third Edition, Revised and Expanded,
Raymond B. Seymour and Charles E. Carraher, Jr.
13. Seymour/Carraher's Polymer Chemistry: An Introduction, Fourth Edition, Revised
and Expanded, Charles E. Carraher, Jr.
14. Seymour/Carraher's Polymer Chemistry: Fifth Edition, Revised and Expanded,
Charles E. Carraher, Jr.
15. Principles of Thermodynamics, Myron Kaufman
16. Seymour/Carraher's Polymer Chemistry: Sixth Edition, Revised and Expanded,
Charles E Carraher, Jr.

Additional Volumes in Preparation

To Raymond Seymour—educator, scientist,
pioneer, prophet, historian, family man,
and friend—we miss you
Foreword

Polymer science and technology has developed tremendously over the last few decades,
and the production of polymers and plastics products has increased at a remarkable pace.
By the end of 2000, nearly 200 million tons per year of plastic materials were produced
worldwide (about 2% of the wood used, and nearly 5% of the oil harvested) to fulfill the
ever-growing needs of the plastic age; in the industrialized world plastic materials are
used at a rate of nearly 100 kg per person per year. Plastic materials with over $250 billion
dollars per year contribute about 4% to the gross domestic product in the United States.
Plastics have no counterpart in other materials in terms of weight, ease of fabrication,
efficient utilization, and economics.
It is no wonder that the demand and the need for teaching in polymer science and
technology have increased rapidly. To teach polymer science, a readable and up-to-date
introductory textbook is required that covers the entire field of polymer science, engineer-
ing, technology, and the commercial aspect of the field. This goal has been achieved in
Carraher’s textbook. It is eminently useful for teaching polymer science in departments
of chemistry, chemical engineering, and material science, and also for teaching polymer
science and technology in polymer science institutes, which concentrate entirely on the
science and technologies of polymers.
This sixth edition addresses the important subject of polymer science and technology,
with emphasis on making it understandable to students. The book is ideally suited not
only for graduate courses but also for an undergraduate curriculum. It has not become
more voluminous simply by the addition of information—in each edition less important
subjects have been removed and more important issues introduced.
Polymer science and technology is not only a fundamental science but also important
from the industrial and commercial point of view. The author has interwoven discussion
of these subjects with the basics in polymer science and technology. Testimony to the
high acceptance of this book is that early demand required reprinting and updating of each
v
vi Foreword

of the previous editions. We see the result in this new significantly changed and improved
edition.

Otto Vogl
Herman F. Mark Professor Emeritus
Department of Polymer Science and Engineering
University of Massachusetts
Amherst, Massachusetts
Preface

An explosive scientific and technological revolution is underway and at its center are
polymers. This revolution is the result of a number of factors that complement one another.
These factors include a better understanding of the science of materials and availability
of new and refined materials, synthetic techniques, and analytical tools. Much of this
revolution is of a fundamental nature and it is explored in the latest edition of this text.
These advances are often based on new and extended understanding and application of
basic principles initially presented in the core chemistry courses (organic, physical, inor-
ganic, analytical, and biological).
Polymer Chemistry complies with the advanced course definition given by the Amer-
ican Chemical Society Committee on Professional Training, building on the foundations
laid in general, organic, physical, analytical/instrumentation, and inorganic chemistry. It
also includes all the major and optional topics recommended in the syllabus adopted by
the joint polymer education committee of the American Chemical Society (Appendix D:
Syllabus). The text integrates and interweaves the important core topic areas. The core
topics are interrelated with information that focuses on polymer topics. This assists students
in integrating their chemical knowledge and illustrates the connection between theoretical
and applied chemical information. Also, industrial practices and testing procedures and
results are integrated with the theoretical treatment of the various topics, allowing the
reader to bridge the gap between industrial practice and the classroom. It is written so
that chapters can be taken out of order and not all the chapters need to be covered to gain
an adequate appreciation of the science of polymers. Many of the chapters begin with
theory, followed by application. Some readers will elect to read the more descriptive
chapters dealing with polymer types before looking at the analytical/analysis/properties
chapters.
This book is user friendly—it is appropriate as an advanced undergraduate text or
an introductory-level graduate-level course text. It can serve as the text for the initial
vii
viii Preface

course in a series taken by a student, or it can be the lone polymer text read by a student
in the study of polymers. Students of chemistry, materials, engineering, medicine, biochem-
istry, physics, and geology will benefit from an understanding of the material found in
this text.
The application and theory of polymers continues to expand. This new edition re-
flects this growth and the continually expanding role of polymers. There is an increased
emphasis on pictorializing, reinforcing, integrating, and interweaving the basic concepts.
The first chapter is shorter in order to allow time for student orientation. However,
the other chapters should not require more than a week’s time each. Each chapter is
essentially self-contained, but each relates to the other chapters. Whenever possible, diffi-
cult concepts are distributed and reinforced over several chapters. A glossary, biography,
suggested questions (and answers), and learning objectives/summary are included at the
end of each chapter.
Application and theory are integrated so that they reinforce one another. This is true
for all the various important and critical types of polymers including synthetic, biological,
organometallic, and inorganic polymers. The principle that the basic concepts that apply
to one grouping of polymers apply to all the other types of polymers is emphasized.
The updating of analytical, physical, and spectral characterization techniques contin-
ues, including expanded coverage of the theory and results arising from atomic force
microscopy and scanning probe microscopy. Special sections dealing with industrially
important polymers are included, and the section dealing with soluble stereoregulating
catalysis has been expanded.
There is still an emphasis on naturally occurring polymers, and discussions of
supercoiling, replication, and compacting are included. As before, the interplay between
natural and synthetic polymers is emphasized.
A number of miscellaneous topics have been drawn together in one chapter, which
includes sections on conductive polymers, smart materials, protomics, human genome,
optical fibers, material selection charts, carbon nanotubes, and liquid crystals.
Emphasis on nanotechnology and nanomaterials remains with added or expanded
sections dealing with zeolites, nanotubes, nanocomposites, molecular wires, dendrites, and
self assembly. The chapter on polymer technology and processing has been rewritten and
expanded. The section listing Web sites has been updated.
The nomenclature section has been enlarged, and a new appendix on the stereoge-
ometry of polymers has been added.
Additional aids and appendixes are included: how to study, nomenclature, over 1500
trade names, about 400 citations to appropriate Journal of Chemical Education and Poly-
mer News articles, Web sites dealing with polymer topics, and over 100 structures of
common polymers.

Charles E. Carraher, Jr.

Acknowledgments

I gratefully acknowledge the contributions of Herman Mark of the Polytechnic Institute

of New York; Charles L. McCormick, University of Southern Mississippi; William Feld,
Wright State University; Eli Pearce, Polytechnic Institute of New York; Fredinard Rodri-
guez, Cornell University; and Otto Vogl, University of Massachusetts, for their reviewing,
advising, and counseling efforts; and Charles Carraher III and Shawn Carraher for their
help in proofing and indexing.
I also thank the following for their special contributions to the book: Charles Gebel-
ein, Les Sperling, Anglo Volpe, Stam Israel, Carl Wooten, Rita Blumstein, Eckhard Hell-
muth, Frank Millich, Norman Miller, Rudy Deanin, Guy Donaruma, Leo Mandelkem, R.
V. Subramanian, Charles Pittman, Brian Currell, C. Bamford, Roger Epton, Paul Flory,
Charles Overberger, William Bailey, Jim O’Donnell, Rob Burford, Edgar Hardy, John H.
Coates, Don Napper, Frank Harris, G. Allan Stahl, John Westerman, William A. Field,
Nan-Loh Yang, Sheldon Clare, E. N. Ipiotis, D. H. Richards, G. Kirshenbaum, A. M.
Sarquis, Lon Mathias, Sukumar Maiti, S. Temin, Yoshinobu Naoshima, Eberhard Neuse,
John Sheats, George Hess, David Emerson, Kenneth Bixgorin, Thomas Miranda, M. B.
Hocking, Marsha Colbert, Joseph Lagowski, Dorothy Sterling, Amanda Murphy, John
Kloss, Qingmao Zhang, Bhoomin Pandya, Ernest Randolph, Alberto Rivalta, and Fengchen
He.
This book could not have been written without the long-time efforts of Professor
Herman Mark, who was one of the fathers of polymer science.
For the fourth edition, a special thanks for the assistance of Colleen Carraher.
I acknowledge the kind permission of Gerry Kirshenbaum and Polymer News for
allowing us to use portions of articles that have appeared in Polymer News.
Finally, I thank Edward S. Wilks for his help with the section on “Chemical Ab-
stracts–Based Polymer Nomenclature.”

ix
Polymer Nomenclature

As with most areas of science, names associated with reactions, particular chemical and
physical tests, etc., were historically derived with few overall guiding principles. Further,
the wide diversity of polymer science permitted a wide diversity in naming polymers.
Even though the International Union of Pure and Applied Chemistry (IUPAC) has a
long-standing commission associated with the nomenclature of polymers [reports include
“Report on nomenclature in the field of macromolecules,” Journal of Polymer Science,
8, 257 (1952); “Report on nomenclature dealing with steric regularity in high polymers,”
Pure and Applied Chemistry, 12, 645 (1966); “Basic definitions of terms relating to poly-
mers,” IUPAC Information Bull. App., 13, 1 (1971); and “Nomenclature of regular single-
strand organic polymers,” Macromolecules, 6(2), 149 (1973)], most of these suggestions
for naming of simple polymers have not yet been accepted by many in the polymer science
community.
Although there is wide diversity in the practice of naming polymers, we will concen-
trate on the most utilized systems.

COMMON NAMES
Little rhyme or reason is associated with the common names of polymers. Some names
are derived from the place of origin of the material, such as Hevea brasiliensis—literally
“rubber from Brazil”—for natural rubber. Other polymers are named after their discoverer,
as is Bakelite, the three-dimensional polymer produced by condensation of phenol and
formaldehyde, which was commercialized by Leo Baekeland in 1905.

Portions adapted from C. Carraher, G. Hess, and L. Sperling, J. Chem. Ed., 64(1), 36 (1987) and L. H. Sperling
W. V. Metanomski, and C. Carraher, Appl Polym Science (C. Craver and C. Carraher, eds.), Elsevier, New
York, 2000.

xi
xii Polymer Nomenclature

For some important groups of polymers, special names and systems of nomenclature
were invented. For example, the nylons were named according to the number of carbons
in the diamine and carboxylic acid reactants (monomers) used in their syntheses. The
nylon produced by the condensation of 1,6-hexanediamine (6 carbons) and sebacic acid
(10 carbons) is called nylon-6,10.

Similarly, the polymer from 1,6-hexanediamine and adipic acid (each with 6 carbons)
is called nylon-6,6 or nylon-66, and the nylon from the single reactant caprolactam (6
carbons) is called nylon-6.

SOURCE-BASED NAMES
Most polymer names used by polymer scientists are source-based; i.e., they are based on
the common name of the reactant monomer, preceded by the prefix “poly.” For example,
polystyrene is the most frequently used name for the polymer derived from the monomer
1-phenylethene, which has the common name styrene.

The vast majority of polymers based on the vinyl group (CH2BCHX) or the vinyli-
dene group (CH2BCX2) as the repeat unit are known by their source-based names. For
example, polyethylene is derived from the monomer ethylene, poly(vinyl chloride) from
the monomer vinyl chloride, and poly(methyl methacrylate) from methyl methacrylate:

Many condensation polymers are also named in this manner. In the case of poly(eth-
ylene terephthalate), the glycol portion of the name of the monomer, ethylene glycol, is
used in constructing the polymer name, so that the name is actually a hybrid of a source-
based and a structure-based name.
Polymer Nomenclature xiii

This polymer is well known by trade names, such as Dacron, or its common grouping,
polyester.
Although it is often suggested that parentheses be used in naming polymers of more
than one word [like poly(vinylidene chloride)] but not for single-word polymers (like
polyethylene), many authors omit entirely the use of parentheses for either case (like
polyvinylidene chloride). Thus there exists a variety of practices with respect to even
source-based names.
Copolymers are composed of two or more monomer units. Source-based names are
conveniently used to describe copolymers by using an appropriate term between the names
of the monomers. Any of a half dozen or so connecting terms may be used, depending
on what is known about the structure of the copolymer. When no information is specified
about the sequence of monomer units in the copolymer, the connective term co is used
in the general format poly(A-co-B), where A and B are the names of the two monomers.
An unspecified copolymer of styrene and methyl methacrylate would be called poly[sty-
rene-co-(methyl methacrylate)].
Kraton, the yellow rubber-like material on the bottom of many running shoes, is an
example of a copolymer about which structural information is available. It is formed from
a group of styrene units, i.e., a “block” of polystyrene, attached to a group of butadiene
units, or a block of polybutadiene, which is attached to another block of polystyrene
forming a triblock copolymer. The general representation of such a block copolymer is
—AAAAABBBBBAAAAA—, where each A or B represents an individual monomer
unit. The proper source-based name for Kraton is polystyrene-block-polybutadiene-block-
polystyrene, with the prefix “poly” being retained for each block.

STRUCTURE-BASED NAMES
Although source-based names are generally employed for simple polymers, the interna-
tional body responsible for systematic nomenclature of chemicals, IUPAC, has published
a number of reports for the naming of polymers, now being accepted for more complex
polymers. The IUPAC system names the components of the repeat unit, arranged in a
prescribed order. The rules for selecting the order of the components to be used as the
repeat unit are found elsewhere [Macromolecules, 6(2), 149 (1973); Pure and Applied
Chemistry, 48, 373 (1976), 57, 149 (1985), and 57, 1427 (1985)]. However, once the order
is selected, the naming is straightforward for simple linear molecules, as indicated in the
following examples:

A listing of source- and structure-based names for some common polymers is given
in Table 1.

LINKAGE-BASED NAMES
Many polymer “families” are referred to by the name of the particular linkage that connects
the polymers (Table 2). The family name is “poly” followed by the linkage name. Thus,
xiv Polymer Nomenclature

Table 1 Source- and Structure-Based Names

Table 2 Linkage-Based Names

Polymer Nomenclature xv

those polymers that contain the carbonate linkage are known as polycarbonates; those
containing the ether linkage are called polyethers, etc.

CHEMICAL ABSTRACTS–BASED POLYMER NOMENCLATURE

The most complete indexing of any scientific discipline is done in chemistry and is pro-
vided by Chemical Abstracts (CA). Almost all of the modern searching tools for chemicals
and chemical information depend on CA for at least some of their information base. It is
critical for polymer chemists to have some grasp of how CA names chemical compounds.
The full description of the guidelines governing the naming of chemical compounds and
related properties is given in Appendix IV at the end of the CA Index Guide. This descrip-
tion is about 200 pages. While small changes are made with each new edition, the main
part has remained largely unchanged since 1972.
CA organizes the naming of materials into twelve major arrangements that tie to-
gether about 200 subtopics. These main topic headings are
A. Nomenclature systems and general principles
B. Molecular skeletons
C. Principal chemical groups
D. Compound classes
E. Stereochemistry and stereoparents
F. Specialized substances
G. Chemical substance names for retrospective searches
H. Illustrative list of substituent prefixes
J. Selective bibliography of nomenclature of chemical substances
K. Chemical prefixes
L. Chemical structural diagrams from CA Index Names
M. Index

The section dealing with polymers is subtopic 222: Polymers. The subsection on
polymers builds on the foundations given before. Some of the guidelines appear to be
confusing and counterproductive to the naming of polymers, but the rules were developed
for the naming of small molecules. Following is a description of the guidelines that are
most important to polymer chemists. Additional descriptions are found in the CA Appendix
IV itself and in articles listed in the readings. Appendix IV concentrates on linear polymers.
A discussion of other more complex polymeric materials is also found in articles cited in
the readings section.

General Rules
In the chemical literature—in particular, systems based on Chemical Abstracts—searches
for particular polymers can be conducted using the Chemical Abstracts Service number,
(CAS
) (where known) or the repeat unit. The International Union of Pure and Applied
Chemistry (IUPAC) and CAS have agreed on a set of guidelines for the identification,
orientation, and naming of polymers based on the structural repeat unit (SRU). IUPAC
refers to polymers as “poly(constitutional repeat unit)” while CAS utilizes a “poly(struct-
ural repeating unit).” These two approaches typically give similar results.
Here we will practice using the sequence “identification, orientation, and naming,”
first by giving some general principles and finally by using specific examples.
xvi Polymer Nomenclature

In the identification step, the structure is drawn, usually employing at least two
repeat units. Next, in the orientation step, the guidelines are applied. Here we concentrate
on basic guidelines. Within these guidelines are subsets of guidelines that are beyond our
scope.
Structures will generally be drawn in the order, from left to right, in which they are
to be named.

Seniority
The starting point for the naming of a polymer unit involves determining seniority among
the subunits.
A. This order is
Heterocyclic rings⬎
Greatest number of most preferred acyclic heteroatoms⬎
Carbocyclic rings⬎
Greatest number of multiple bonds⬎
Shortest path or route (or lowest locant) to these substituents
Chains containing only carbon atoms.
with the symbol “⬎” indicating “is senior to.”
This is illustrated below.
Heterocyclic ring ⬎ Acyclic hetero atoms ⬎ Carbocyclic rings

⬎ MOMCH2M ⬎

⬎ Multiple bonds ⬎ Lowest locant ⬎ Only carbon chains

⬎ MCHBCHM ⬎ MCF2MCHF ⬎ MCHFMCF2M ⬎ MCH2MCH2M
This order is partially derived from guidelines found in other sections such as Section
133, Compound Radicals, where the ordering is given as
Greatest number of acyclic hetero atoms⬎
Greatest number of skeletal atoms⬎
Greatest number of most preferred acyclic hetero atoms⬎
Greatest number of multiple bonds⬎
Lowest locants or shortest distance to nonsaturated carbons.
The lowest locant or shortest distance refers to the number of atoms from one senior
subunit to the next most senior subunit when there is only one occurrence of the senior
subunit.
This order refers to the backbone and not substitutions. Thus, polystyrene and poly(-
vinyl chloride) are contained within the “chains containing only carbon atoms” grouping.
B. For ring systems the overall seniority is
Heterocyclic⬎
Carbocyclic
but within the rings there is also an ordering (Section 138) that is
Polymer Nomenclature xvii

Nitrogenous heterocyclic⬎
Heterocyclic⬎
Largest number of rings⬎
Cyclic system occurring earliest in the following list of systems
spiro, bridged fused,
bridges nonfused, fused⬎
Largest individual ring (applies to fused carbocyclic systems)⬎
Greatest number of ring atoms

For example,

and

and

C. For hetero-atomed linear chains or cyclic rings, the order of seniority is O ⬎ S ⬎

Se ⬎ Te ⬎ N ⬎ P ⬎ As ⬎ Sb ⬎ Bi ⬎ Si ⬎ Ge ⬎ Sn ⬎ Pb ⬎ B ⬎ Hg.
Thus, because MOM CH2 —is senior to MSMCH2M, it would be named first in a
polymer that contained both MOMCH2M and MSMCH2 Msegments. Further, a polymer
containing these alternating units would not be poly(thiomethyleneoxymethylene) but
would be named poly(oxymethylenethiomethylene).
Another example,

O

M(MOMCMCH2M)nM

is named poly[oxy(1-oxy-1,2-ethanediyl)] or less preferred poly[oxy(1-oxoethylene)] but

not poly[(2-oxo-1,2-ethanediyl)oxy] or poly[(2-oxoethylene)oxy].
D. In rings, unsaturation is senior to saturation. The more unsaturated, the more senior
with all other items being equal. Thus 1,4-phenylene is senior to 2,5-cyclohexadiene-1,4-
diyl, which in turn is senior to 2-cyclohexene-1,4-diyl, which is senior to 1,4-cyclohexaned-
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