Cyclopolymerization and Polymers with Chain-Ring Structures

448 Pages·1982·6.9 MB·English

by  George B. Butler and Jiri E. Kresta (Eds.)

Cyclopolymerization
and
Polymers with
Chain-Ring Structures
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
Cyclopolymerization
and
Polymers with
Chain-Ring Structures
George B. Butler,
EDITOR
University
Jiri E. Kresta, EDITOR
University of Detroit
Based on a symposium
cosponsored by the Divisions of
Polymer Chemistry and
Organic Coatings and
Plastics Chemistry
at the 181st ACS National Meeting,
Atlanta, Georgia,
March 30-April 1, 1981.
ACS S Y M P O S I U M SERIES 195
AMERICAN CHEMICAL SOCIETY
WASHINGTON, D. C. 1982
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
Library of Congress Cataloging in Publication Data
Cyclopolymerization and polymers with chain-ring
structures.
(ACS symposium series, ISSN 0097-6156; 195)
Includes bibliographies and index
1. Polymers and polymerization—Congresses
Cyclic compounds—Congresses
I. Butler, George B., 1916 . II. Kresta, Jiri E.,
1934- . III. American Chemical Society. Division
of Polymer Chemistry. IV. American Chemical Society.
Division of Organic Coatings and Plastics Chemistry.
V. Series.
QD380.C9 1982 547.7 82-11331
ISBN 0-8412-0731-3 ACSMC8 195 1-459
1982
Copyright © 1982
American Chemical Society
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PRINTED IN THE UNITED STATES OF AMERICA
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
ACS Symposium Series
Μ. Joa
Advisory Board
David L. Allara Marvin Margoshes
Robert Baker Robert Ory
Donald D. Dollberg Leon Petrakis
Robert E. Feeney Theodore Provder
Brian M. Harney Charles N. Satterfield
W. Jeffrey Howe Dennis Schuetzle
James D. Idol, Jr. Davis L. Temple, Jr.
Herbert D. Kaesz Gunter Zweig
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
FOREWORD
The ACS SYMPOSIUM SERIES was founded in 1974 to provide
a medium for publishing symposia quickly in book form. The
format of the Series parallels that of the continuing ADVANCES
IN CHEMISTRY SERIES except that in order to save time the
papers are not typeset but are reproduced as they are sub
mitted by the authors in camera-ready form. Papers are re
viewed under the supervision of the Editors with the assistance
of the Series Advisory Board and are selected to maintain the
integrity of the symposia; however, verbatim reproductions of
previously published papers are not accepted. Both reviews
and reports of research are acceptable since symposia may
embrace both types of presentation.
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
This book is dedicate
a pioneer of cyclopolymerization chemistry,
on the anniversary of his 65th birthday.
vii
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
viii
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
GEORGE BERGEN BUTLER was born in Liberty, Mississippi, in April
1916. He studied at Mississippi College, Mississippi (B.A. 1938), and
at the University of North Carolina at Chapel Hill (Ph.D. 1942). In
1946, after working briefly at the Rohm and Haas Co., he joined the
faculty of the Chemistry Department at the University of Florida as an
instructor. He was promote
professor in 1951 and t
career, over 80 students have obtained advanced degrees under his guid
ance, and he has published hundreds of scientific papers.
His research contributions to polymer chemistry span many areas,
from studies of alternating copolymers of maleic anhydride and vinyl ether
("pyran copolymer") having interferon inducing capability and antitumor
activity, to polymerization of triazoline diones and synthesis of the anti-
aromatic 3,3-dimethoxycyclopropene.
His best known contribution to polymer science is the discovery of
the cyclopolymerization reaction in 1956, during the study of free radical
polymerization of divinyl monomers. For this pioneering work he was
awarded the 1980 American Chemical Society Witco Award for Polymer
Chemistry. Among other awards, he also received the Florida Section
ACS Award in 1963, and the Herty Award from the Georgia Section of
the ACS in 1978.
Besides his research work, he is an organizer and co-editor of Re
views in Macromolecular Chemistry and the Journal of Macromolecular
Science—Reviews. He also serves on the editorial boards of the Journal
of Macromolecular Science—Chemistry, Macromolecules, the Journal of
Polymer Science, and Macromolecular Synthesis.
On the occasion of his 65th birthday, the contributors to this book
wish Professor Butler many productive years in his future research activities
in polymer chemistry.
ix
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.
PREFACE
C^YCLOPOLYMERIZATION HAS BEEN DEFINED as a chain-growth polymeri
zation reaction of l,X-bis-(multiple bonded) monomers which introduces
cyclic structures into the main chain of the resulting polymers. However,
polymers containing cyclic units in the main chain can be synthesized by
a wide variety of methods
upon which this book is based decided to broaden its scope to include
both polymers formed by cyclopolymerization and polymers containing
chain-ring structures.
Although cyclopolymerization has been extensively investigated, be
cause of its complexity and the variety of monomers capable of partici
pating in this mode of chain propagation, considerable research emphasis
continues in this area. The microstructure of cyclopolymers studied by
modern spectroscopic techniques, particularly 13C NMR, has yielded sig
nificant results. Aspects not totally understood and which continue to be
investigated include ring size, theoretical interpretations of the driving
force for control of ring size, the relative importance of kinetic versus
thermodynamic control, electronic interactions, steric effects, macrocyclic
polymers, and charge-transfer complexes in cyclocopolymerization. This
volume includes 16 papers dealing with the various aspects of cyclo
polymers and cyclopolymerization.
Sixteen papers dealing with polymers containing chain-ring struc
tures are also included. During an extended period in which considerable
emphasis was placed on development of thermally stable polymers, a
wide variety of synthetic methods have been developed, and numerous
polymers having interesting and occasionally superior properties have
been reported. Among these reactions are the novel cross-linking or chain
extension trimerization reactions of various end groups, and a variety of
condensation reactions leading to heterocyclic structures in the main
polymer chain.
xv
In Cyclopolymerization and Polymers with Chain-Ring Structures; Butler, G., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1982.