REACTIVE POLYMERS FUNDAMENTALS AND APPLICATIONS

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2 REACTIVE POLYMERS FUNDAMENTALS AND APPLICATIONS A CONCISE GUIDE TO INDUSTRIAL POLYMERS Johannes Karl Fink Montanuniversität Leoben Leoben, Austria

3 Copyright 2005 by William Andrew, Inc. No part of this book may be reproduced or utilized in any form or by any means, electronic or mechanical, including photocopying, recording, or by any information storage and retrieval system, without permission in writing from the Publisher. Cover art 2005 by Brent Beckley / William Andrew, Inc. ISBN: (William Andrew, Inc.) Library or Congress Catalog Card Number: Library of Congress Cataloging-in-Publication Data Fink, Johannes Karl. Reactive polymers : fundamentals and applications : a concise guide to industrial polymers / by Johannes Karl Fink. p. cm. -- (PDL handbook series) Includes bibliographical references and index. ISBN (acid-free paper) 1. Gums and resins, Synthetic. 2. Gums and resins--industrial applications. I. Title. II. Series. TP1185.R46F '.374--dc Printed in the United States of America This book is printed on acid-free paper Published by: William Andrew Publishing 13 Eaton Avenue Norwich, NY NOTICE To the best of our knowledge the information in this publication is accurate; however the Publisher does not assume any responsibility or liability for the accuracy or completeness of, or consequences arising from, such information. This book is intended for informational purposes only. Mention of trade names or commercial products does not constitute endorsement or recommendation for their use by the Publisher. Final determination of the suitability of any information or product for any use, and the manner of that use, is the sole responsibility of the user. Anyone intending to rely upon any recommendation of materials or procedures mentioned in this publication should be independently satisfied as to such suitability, and must meet all applicable safety and health standards.

4 PDL EDITOR S PREFACE The publication of Reactive Polymers Fundamentals and Applications: A Concise Guide to Industrial Polymers in the PDL (Plastics Design Library) series gives me a special pleasure. The author, Dr. Johannes Karl Fink, has brought together an impressive array of information about the reactions polymers undergo, often resulting in cross-linking. The masterful interweaving of the applications of these reactions with the discussion of chemistry has rendered this book easy to read for a variety of scientists and engineers. The reader learns about the incredible penetration of reactive plastics into every day life whether in a dentist s office or an office copier. On the more cutting edge, the book includes information about carborane copolymers, which far exceed the temperature resistance of any existing polymers. Launched in 1990, the Plastics Design Library (PDL) has established itself within the materials engineering community as the "go to" source for information on plastics, elastomers, and adhesives. PDL is a unique series of reference and data books essential to the daily work of practicing engineers and scientists in applied industries. The library encompasses the areas of non-metallic materials with a special emphasis on plastics, elastomers, coatings, and adhesives. Important current and future materials, processing technologies, and applications are emphasized. Future titles are planned in the newer areas of commercial activity such as nanocomposites, bio-based polymers, recycling and mathematical modeling. The breadth of the coverage ranges from the nature and selection of materials to design and fabrication to specification and performance. The uniqueness of PDL is in its balance of practical and theoretical aspects with a clear emphasis of the practical over the theoretical. The encyclopedic format of the books lends itself to easy reading and referral while the theoretical sections provide the curious reader with an opportunity for more in-depth learning. Ample references throughout each book serve as both bibliography and additional learning. Our hope is that this book will meet the needs of people who work with the reactions of polymers for any reason. Sina Ebnesajjad 2005 i

5 ii Sina Ebnesajjad, Editor Plastics Design Library Dr. Sina Ebnesajjad is a senior technical consultant at the DuPont Company, where he has been in a variety of technical assignments since Sina is the author of three handbooks on the science, technology and applications of Fluoroplastics, published by William Andrew, Inc. He is the Series Editor for the Fluorocarbon Handbook Series that includes six handbooks on fluoroplastics, fluoroelastomers, fluorinated coatings and fluoroionomers. He has been the Editor of Plastics Design Library since September 2004.

6 PREFACE Most of the synthetic polymers are produced in chemical plants and delivered to a plastics manufacturer who does the formulating, blending, extruding or molding in order to fabricate articles. The processes required for the final product are purely physical that occur essentially without any chemical reaction of the polymer. Since most of the polymers are immiscible, there is not much room to modify the polymer properties during the plastics manufacturing. The properties of the final product are often modified by the actions of additives. A minor number of polymers, usually called resins, are delivered as precursors by the chemical industry to the manufacturer. Here, the manufacturer gets to the final article by a chemical reaction. There also exists an in-between state where polymers can be modified by reactive extrusion and grafting. The modification of polymers is advantageous if comparatively small changes of certain properties are needed that cannot be achieved in chemical plants. Since many different precursors of the final resin can be combined, the variability of, and thus the ability to modify, the final properties are much more pronounced in comparison to the rest of polymers. This is the topic with which the present book deals, namely, chemical reactions that take place during the final stage of part fabrication from plastics. The text does not deal with the chemical reactions needed to produce resin precursors and the synthesis of polymers. However, chemical topics relevant to the part manufacturer are elaborated here. These range from the manufacture of glass-fiber-reinforced articles such as boats made by the amateur and in a small scale dockyard to what takes place when a dentist is filling teeth. Industrial processes for the plastics batch fabrication are described, in addition to their end uses. The text describes the basic principles of reactive resins as well as the most recent developments. Paints, coatings and adhesives that are constituted from resins are not dealt with here, even when the curing mechanisms are similar. The past art is discussed by reference to monographs, whereas the recent developments are documented by references in the scientific literature and the patent literature after In some topics, e.g., urea-formaldehyde resins, the present research activity is low. In other areas, such as resins used for nanocomposites, there are many recent papers. Even those resins, for which the research activity is rather dormant at the moiii

7 iv Reactive Polymers Fundamentals and Applications ment, find widespread use and well established applications. They are not covered here because they are presented in general reviews cited at the beginning of the respective chapters. Newer applications of these resins are discussed in detail. The text originates from a lecture manuscript developed by the author that has been expanded into a monograph. The original literature presented here covers the period until July The text is at a level that a chemist with a general eduction in polymer chemistry should understand. Further, the text is addressed to the advanced student of plastics engineering and the practicing engineer. HOW TO USE THIS BOOK Utmost care has been taken to present reliable data. Because of the vast variety of material presented here, however, it cannot be complete in all relevant aspects, and it is recommended that the reader study the original literature for complete information. Therefore, the author cannot assume responsibility for the completeness and validity of, nor for the consequences of, the use of the material presented here. Every attempt was made to identify trademarked products in this volume; however, there were some that the author was unable to locate, and we apologize for any inadvertent omission. Index There are three indices: an index of acronyms, an index of chemicals, and a general index. Unfortunately the acronyms presented in the literature are not always consistent. This means that in a few cases the same acronym stands for different terms. Further, in the literature the acronyms are sometimes expanded in a different way, in particular for chemical names. The author has not unified the system of chemical names, even when the same compound appears with different names, because otherwise back tracing in the original literature would be difficult. I apologize here for this somewhat unsatisfactory situation. In the index of chemicals, compounds that occur extensively, e.g., styrene, are not included at every occurrence, but rather when they appear in an important context.

8 Preface v ACKNOWLEDGEMENTS I am indebted to our local library, Dr. Lieselotte Jontes, Dr. Johann Delanoy, Franz Jurek, Friedrich Scheer, and Christian Slamenik for support in literature acquisition. I express my gratitude to all the scientists who have carefully published their results concerning the topics dealt with here. The book could not have been compiled otherwise. I would like to thank Dr. Sina Ebnesajjad, Editor of Plastics Design Library (PDL) for his review and comments on the manuscript. The Editorial Staff of William Andrew, Inc. have been most supportive of this project, especially Ms. Millicent Treloar, Senior Acquisitions Editor, who has been tireless in her efforts. Thank you Ms. Joan Bally for copy editing the manuscript. J. K. F.

9 Plastics Design Library PDL Editor: Sina Ebnesajjad Founding Editor: William A. Woishnis Fluoroelastomers Applications in Chemical Processing Industries ISBN: Khaladkar, P. R., Ebnesajjad, S., Pub. Date: 2005, 592 Pages The Effect of Sterilization Methods on Plastics and Elastomers, 2 nd Ed. ISBN: Massey, L. K., Pub. Date: 2005, 408 Pages Extrusion: The Definitive Processing Guide and Handbook ISBN: Giles, H. F., Jr., Wagner,J. R., Jr., Mount, E. M., III, Pub. Date: 2005, 572 Pages Film Properties of Plastics and Elastomers, 2 nd Ed. ISBN Massey, L. K., Pub. Date: 2004, 250 Pages Handbook of Molded Part Shrinkage and Warpage ISBN Fischer, J., Pub. Date: 2003, 244 Pages Fluoroplastics, Volume 2: Melt-Processible Fluoroplastics ISBN Ebnesajjad, S., Pub. Date: 2002, 448 Pages Permeability Properties of Plastics and Elastomers, 2 nd Ed. ISBN Massey, L. K., Pub. Date: 2002, 550 Pages Rotational Molding Technology ISBN Crawford, R. J., and Throne, J. L., Pub. Date: 2002, 450 Pages Specialized Molding Techniques & Application, Design, Materials and Processing ISBN X Heim, H. P., and Potente, H., Pub. Date: 2002, 350 Pages

10 Chemical Resistance CD-ROM (3 rd Ed.) ISBN Plastics Design Library Staff, Pub. Date: 2001, CD-rom Plastics Failure Analysis and Prevention ISBN Moalli, J., Pub. Date: 2001, 400 Pages Fluoroplastics, Volume 1: Non-Melt Processible Fluoroplastics ISBN Ebnesajjad, S., Pub. Date: 2000, 365 Pages Coloring Technology for Plastics ISBN Harris, R. M., Pub. Date: 1999, 333 Pages Conductive Polymers and Plastics in Industrial Applications ISBN Rupprecht, L. M., Pub. Date: 1999, 302 Pages Imaging and Image Analysis Applications for Plastics ISBN Pourdeyhimi, B., Pub. Date: 1999, 398 Pages Metallocene Technology in Commercial Applications ISBN Benedikt, G. M., Pub. Date: 1999, 325 Pages Weathering of Plastics ISBN Wypych, G., Pub. Date: 1999, 325 Pages Dynamic Mechanical Analysis for Plastics Engineering ISBN Sepe, M.. Pub. Date: 1998, 230 Pages Medical Plastics: Degradation Resistance and Failure Analysis ISBN X Portnoy, R. C., Pub. Date: 1998, 215 Pages