Reactions on Polymers: Proceedings of the NATO Advanced Study Institute held at Rensselaer Polytechnic Institute, Troy, N.Y., U.S.A., July 15–25, 1973 PDF
Preview Reactions on Polymers: Proceedings of the NATO Advanced Study Institute held at Rensselaer Polytechnic Institute, Troy, N.Y., U.S.A., July 15–25, 1973
Reactions on Polymers NATO ADVANCED STUDY INSTITUTES SERIES Proceedings of the Advanced Study Institute Programme, which aims at the dissemination of advanced knowledge and the formation of contacts among scientists from different countries The series is published by an international board of publishers in conjunction with NATO Scientific Affairs Division A Life Sciences Plenum Publishing Corporation B Physics London and New York C Mathematical and D. Reidel Publishing Company Physical Sciences Dordrecht and Boston D Behavioral and Sijthoff International Publishing Company Social Sciences Leiden E Applied Sciences Noordhoff International Publishing Leiden Series C - Mathematical and Physical Sciences Volume 4 - Reactions on Polymers Reactions on Polymers Proceedings of the NATO Advanced Study Institute held at Rensselaer Polytechnic Institute, Troy, N. Y., U.S.A., July 15-25, 1973 edited by J. A. MOORE Rensselaer Polytechnic Institute, Troy, N. Y., U.S.A. D. Reidel Publishing Company Dordrecht-Holland / Boston-U.S.A. Published in cooperation with NATO Scientific Affairs Division First printing: December 1973 Library of Congress Catalog Card Number 73-91207 ISBN-13: 978-94-010-2680-2 e-ISBN-13: 978-94-010-2678-9 DOl: 10.1007/978-94-0 I 0-2678-9 Published by D. Reidel Publishing Company P.O. Box 17, Dordrecht, Holland Sold and distributed in the U.S.A., Canada, and Mexico by D. Reidel Publishing Company, Inc. 306 Dartmouth Street, Boston, Mass. 02116, U.S.A. All Rights Reserved Copyright © 1973 by D. Reidel Publishing Company, Dordrecht Softcover reprint of the hardcover 15t edition 1973 No part of this book may be reproduced in any form, by print, photoprint, microfilm, or any other means, without written permission from the publisher TABLE OF CONTENTS PREFACE vii ACKNOWLEDGEMENT ix ATTENDEES xi CATALYSIS BY POLYMERS C. G. Overberger and T. W. Smith INTERIONIC REACTIONS IN POLYELECTROLYTE SOLUTIONS 27 N. Ise POLYMERS AS CATALYSTS FOR POLYMERIZATION REACTIONS 54 C. H. Bamford THE REACTION OF POLYVINYLAMINE WITH p-NITROPHENYL 61 ACETATE T. St. Pierre, G. Vi gee and A. R. Hughes FUNCTIONALIZATION OF POLYMERS 73 P. Ferruti A KINETIC STUDY OF THE QUATERNIZATION OF TERTIARY 102 AMINE FUNCTIONAL GROUPS IN THE POLY(VINYL PYRIDINE) SERIES WITH ALKYL BROMIDES C. Loucheux INSOLUBLE HALOGENATING AGENTS III C. Yaroslavsky MODIFICATION OF POLYMERS USING IODINE ISOCYANATE. 116 II. IMPROVED METHODS FOR IODINE ISOCYANATE ADDITION TO POLYISOPRENE AND SOME BIOMEDICAL IMPLICATIONS C. G. Gebelein and A. Baytos MODIFICATION OF POLYMERS CONTAINING LEWIS BASE 126 FUNCTIONAL GROUPS VIA CONDENSATION WITH LEWIS ACIDS C. E. Carraher, Jr. SEQUENCE STUDIES DURING REACTIONS ON POLYMERS 137 E. Klesper, D. Strasilla and V. Barth SOME PROBLEMS IN THE REACTIVITY OF MACROMOLECULES 169 N. A. Plate' CHEMICAL REACTIVITY OF COPOLYMERS 188 H. J. Harwood PHOTOCHEMICAL REACTIONS OF POLYMERS IN SOLUTION 230 C. H. Bamford NEW METHODS OF PREPARATION OF TAILOR MADE POLYMER 265 NETWORKS P. Rempp CHEMICAL AND BIOCHEMICAL REACTIONS IN THE GEL PHASE 286 R. Epton SYNTHESIS AND PROPERTIES OF POLYMERS WITH SULFUR- 320 CONTAINING FUNCTIONAL GROUPS E. J. Goethals APPLICATION OF BENDER'S SALTS TO THE SYNTHESIS OF 351 MERCAPTAN-CONTAINING POLYMERS W. H. Daly and C.-D. Lee PARAOXON ANALOGS AS HAPTENS 365 R. Corett, A. Kalir, E. Katz, R. Shahar and M. Torten CHEMICAL REACTIONS OF MACROMOLECULES IN THE SOLID 371 STATE G. Smets CHEMICAL REACTIONS INVOLVING THE BACKBONE CHAIN OF 395 MACROMOLECULAR CR~STALS B. Wunderlich THE CHALLENGE TO POLYMER CHEMISTS IN SOLID PHASE 412 PEPTIDE SYNTHESIS J. M. Stewart SUPPORT-AIDED PEPTIDE SYNTHESIS - REGENERABLE 434 POLYMERIC REAGENTS, RECENT DEVELOPMENTS R. E. Williams AFFINITY CHROMATOGRAPHY 440 I. Parikh and P. Cuatrecasas PREFACE The subject matter of this volume has its roots in the early days of polymer chemistry when gun cotton and Parkesine were first developed. Indeed, its roots can ultimately be traced into anti quity, since, in commerce and daily life, man has always carried out reactions on polymers, e.g. in primitive dyeing and tanning operations. In more modern times Prof. Staudinger is commonly acknowledged as the investigator most responsible for the renais sance of interest in "polymer analogous" reactions. In recent years it has become apparent that the "black art" of conducting chemical reactions on macromolecules is an area which is amenable to basic scientific investigation. Examples of important developments which have come 'about ,in part ,as a result of this realization have been the advances in molecular biology (which may be rightly considered as the biochemistry of macromo lecules) and by such milestone achievements as solid phase pep tide synthesis and affinity chromatography. These few selected examples all have macromolecules (biological and synthetiC) in common. The stimulation to wide areas of scientific endeavor re sulting from these developments would undoubtedly have occurred· sooner, and certainly with much less difficulty, had the various investigators been aware of the problems attending attempts at performing reactions on polymers. The major purposes of this Advanced Studies Institute were threefold: 1. To treat these processes in depth in light of current chem ical knowledge to broaden the backgrounds of specialists in this area, as well as to provide a fUndamental understanding of it for new workers. 2. To aid the dissemination of detailed and current ideas across international boundaries. 3. To aid in the dissemination of information about chemical re action on polymers across interdisciplinary boundries. VIII PREFACE The scientific level of development in this field at the pre sent time is at a stage where accomplishment of these goals will, hopefully, cause the germination of new ideas and new achievments, so that the next giant step to be made in those areas utilizing chemical reactions on macromolecules may be made more rapidly and more efficiently. These goals have, I believe, been accomplished, in part, on a microscale during the time of the Institute. It is our hope that the publication of these proceedings will accomplish them on a macroscale. The lectures and their associated discussions are not necess arily presented in chronological order but in a sequence which I deem most cohesive. The discussions were recorded on tape, transcribed by the respective discussion leaders and edited by me. Regretfully, because of mechanical and electronic difficulties the bulk of the discussion of Prof. Overberger's paper and all of the discussion from Prof. LeChoux's and Dr. Yaroslavsky's papers could not be included in these proceedings. The pressure of keeping the number of pages within a prescribed, manageable limit necessitated the elimination of much of the spontaneous (often somewhat macabre) good humor which characterized all the sessions, from the final draft. Further, three excellent unscheduled presentations by Prof. Smets, Prof. Bamford and Prof. Higgins on photo-conden sation polymerization were eliminated because, despite the fervor of the moment in which they were presented,' they are beyond the scope of these proceedings. The efforts of Mrs. H. Hayes and my wife in typing and re typing portions of the manuscript are thankfully acknowledged. The forbearance of my family during the Institute and the preparation of the final draft of these proceedings was a major component in the ultimate success of the program. James A. Moore Troy, New York September, 1973 ACKNOWLEDGEMENT In Addition to the financial support of the North Atlantic Treaty Organization, the generosity of the following corporations contributed greatly to the completeness and success of the program. Allied Chemical Co. Cabot Corp. Celanese Co. Eastman Kodak Co. Esso Research and Engineering Co. International Telephone and Telegraph, Inc. Johnson and Johnson Associated Industries Lord Corp. Lubrizol Corp. P P G Industries Shell Development Co. ATTENDEES Dr. R. Auerbach Dr. J. Dale Lord Corporation Dynapol 2000 West Grandview Blvd. 1454 Page Mill Rd. Erie, Pa. 16512 Palo Alto, Calif. 94304 Prof. C. H. Bamford Prof. W. H. Daly The University of Liverpool Dept. of Chemistry Dept. of Inorganic, Physical& Louisiana State University/ Industrial Chemistry Baton Rouge Donnan Laboratories Baton Rouge, Louisiana 70803 P.O. Box 147 Liverpool L69 3BX Dr. H. DeLaMare England Shell Development Co. Chemical Research Laboratory Mr. R. Bopp Houston, Texas 77079 Dept of Chemistry Rensselaer Polytechnic Inst. Dr. D. J. Dunn Troy, N.Y. 12181 Dept. of Chemistry University of Keele Prof. C. Carraher Jr. Staffordshire, England Dept of Chemistry University of South Dakota Prof. R. Epton Vermillion, South Dakota 57069 Principal Lecturer in Chemistry The PolytechniC Prof. G. Challa Wo1verhampton, England WV1 1LY The University of Groningen Laboratorium voor Prof. P. Ferruti Polymeerchemie Polytechnic Institute of Milan Zernikelaan, Groningen Piazza Leonardo DaVinci 32 The Netherlands 20133 Milano, Italy Dr. R. Chlanda R. B. Fox Chemical Research Center Organic Polymers Section, Chen. Div. Allied Chemical Corp. Naval Research Laboratory Morristown, N.J. 07960 Washington, D.C. 20390 Dr. 1. Cho Dr. T. Furuyama The Korea Advanced Institut Asahi Chemical Industry America,Inc. of Science 350 Fifth Ave. P. O. Box 150 Chung Ryang Ni New York, N. Y. 10001 Seoul, Korea Dr. R. J. Gander Dr. R. Corett Johnson and Johnson Israel Institute for New Brunswick, N. J. 08903 Biological Research Tel-Aviv University Medical School Ness-Ziona, Israel
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