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Phenolic Resins Chemistry, Applications.Pdf Phenolic Resins Springer-Verlag Berlin Heidelberg GmbH A. Gardziella · L. A. Pilato · A. Knop Phenolic Resins Chemistry, Applications, Standardization, Safety and Ecology 2nd completely revised edition With 309 Figures and 166 Tables i Springer Dr. Arno Gardziella (ehern. Bakelite AG) Rüdinghausener Berg 4 D-58454 Witten Germany Dr. Louis A. Pilato Phenolic Resin Technology Advanced Composite Systems 598 Watchung Road Bound Brook, NJ 08805 USA Dr. Andre Knop Schillerstraße 31 D-61350 Bad Hornburg Germany ISBN 978-3-642-08484-3 Cataloging-in-Publication Data applied for Die Deutsche Bibliothek- CIP-Einheitsaufnahme Gardziella, Arno: Phenolic resins ; chemistry, applications, standardization, safety and ecology ; with 166 tables I A. Gardziella; L.A. Pilato; A. Knop.- 2., completely rev. ed. 1. Aufl. u. d. T.: Knop, Andre: Phenoloc resins ISBN 978-3-642-08484-3 ISBN 978-3-662-04101-7 (eBook) DOI 10.1007/978-3-662-04101-7 This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other way, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer-Verlag Berlin Heidelberg GmbH . Violations are liable for Prosecution under the German Copyright Law. ©Springer-Verlag Berlin Heidelberg 2000 Originally published by Springer-V erlag Berlin Heidelberg N ew Y ork in 2000 Softcover reprint of the hardcover 2nd edition 2000 The use of generat descriptive names, registered names, etc. in this publication does not imply, even in the absence of a specific Statement, that such names are exempt from the relevant protec­ tive laws and regulations and free for generat use. Product liability: The publisher cannot guarantee the accuracy of any information about dosage and application contained in this book. In every individual case the user must check such information by consulting the relevant literature. Production Editor: Christiaue Messerschmidt, Rheinau Typesetting: Fotosatz-Service Köhler GmbH, Würzburg Coverdesign: Design & Production, Beideiberg SPIN: 10489866 2/3020-5 4 3 2 1 0- printed on acid-free paper Preface A backward glance of the many new industries that emerged in the 20th century would surely recognize communications, automobile, aircraft, computer and several others that have had a global impact on world economy. Yet another industry, and an often neglected industry, made its debut early in the 20th century - the Plastics Industry. The Plastics Industry owes its identity to the brilliance of Dr. Leo Hendrik Baekeland (1863 -1944). He discovered the technique, currently in use to this day, to manu­ facture highly crosslinked plastics by transforming monomerk and/or oligomeric phenolic materials into attractive phenolic products. Today phenolics represent one of the many different types of com­ mercially available plastics (thermoset and thermoplastic). Phenolics are distinguished by a broad array of application areas that utilize phenolics as compared to other thermoset or thermoplastic resins. Thermoplastic resins transformed into molded products, films or synthetic fibers (polypropylene as an example) are rapidly recognized as "plastics" whereas the phenolic resin is a component in a material system and the identity of the phenolic resin within the system is not easily identified as "plastic". These systems consist of fiber reinforced composites, honeycomb paneling, electrical Iaminates, acid resistant coatings, wood panels, glass fiber or rock wool insulation. Phenolic resin identity is hidden and has little consumer recognition or identity. The apparent hidden but security/comfort aspect of phenolic resins is best illustrated by considering the use of phenolic resin as hinder in friction linings or automobile brakes. Although there are as many as 30 components including phenolic resin hinder in the brake formulation, phenolic resin is the preferred bin der in this "life or death'' application. During the braking operation, the kinetic energy of the vehicle is largely converted into heat; peak temperatures of greater that 800 oc occur at the surface of the brake lining, depending on the stress and type of vehicle. Through the analyses of various bonding functions (temporary, complementary, carbon forming and chemically reactive) the perfor­ mance of phenolic resin as the preeminent hinder for the automobile brake is best described. lt maintains the integrity of the brake system. The main objective of this publication is to familiarize the reader with phenolic resins by describing in more detail the subject of VI Preface phenolic resins than the previous publications: A. Knop and Scheib, "Chemistry and Application of Phenolic Resins" (1979); and A. Knop and L.A. Pilato, "Phenolic Resins, Chemistry,Applications and Perfor­ mance - Future Directions" (1985). The title of this current publica­ tion is deliberately long and is due to the authors' attempt to broaden the scope of phenolics beyond the achievements of the earlier books. For those acquainted with phenolic resins, they will appreciate the novel approach to identify the role of phenolic resins as adhesives by considering SIX functions to illustrate the binding versatility of phenolic resins. For those less familiar readers, their introduction to phenolic resins will be rewarding since they will encounter raw materials, chemistry, reactions, mechanisms and resin production in the beginning of the book. The chemical portion is based on current scientific publications. The applications areas and the phenolic resins used in these market areas are extensively illustrated and described. Once both neophyte and veteran complete the chemistry and six bonding functions segments, comparison of phenolic resins with other thermosetting resins as well as thermoplastic resins are des­ cribed in which both filled and unfilled resin systems are compared. These camparisans provide ample evidence for the superiority of phenolic resins with many of the competitive thermosetting and thermoplastic resins. Prominent features of phenolic resins are: 1. Excellent thermal behavior 2. High strength level 3. Long term thermal and mechanical stability 4. Excellent fire, smoke, and low toxicity characteristics 5. Excellent electrical and thermal insulating capabilities 6. Excellent cost performance characteristics These criteria provide an entry into many application areas which utilize phenolic resins along with the appropriate bonding function. In each application area the final product which combines phenolic resin with other components exhibits the necessary performance characte­ ristics of the intended application. By considering the type ofbonding function (permanent, temporary, complementary, etc.) and the role of the phenolic resin in the commercial product, it allows one to examine critically the fundamental aspects that are responsible in the success­ ful design and performance of the resulting product. It is possible that the bonding function(s) coupled to new phenolic resin mechanistic perceptions and new analytical techniques may stimulate or challenge the reader to develop improved products/processes. The timing of the section related to standardization and certifica­ tion is opportune. Currently standardization of phenolic based electrical Iaminates and molding compounds is encountering con­ siderable change and is becoming even more international or global in nature. An extensive ISO and CEN system of test methods for phenolic resins now exists and of great importance for purposes of Preface VII ISO 9001 ff certification, European standardization and globalization of plastics production and application. It is discussed in detail. The chemical industry and resin manufacturers remain vigilant in their endeavors to provide environmental and worker safety. Enhance­ ment of worker safety and related environment is a continuing activity of both resin manufacturer and resin processor. Continued reduction of residual monomers to very low levels, accelerated changes of solvent based systems to aqueous types, environmentally friendly resins, melt processing... are evergreen activities ensuring collaborative efforts between resin manufacturer and resin processor. Recycling, renewable raw materials, and future development guidelines for phenolic resins are discussed. With technical advice, brochures, photos and drawings, numerous experts and business associates in the USA and FRG have greatly aided us in expanding our level of knowledge. Corporate management of Bakelite AG, Iserlohn, and company employees in the development and application research, analytical and environmental technology departments as well as in the business areas of phenolic resins and molding compounds have joined in the development of this new reference work with many comments and suggestions. We would like to extend our warmest thanks to all of them. August 1999 Arno Gardziella, Louis A. Pilato, Andre Knop Table of Contents Abbreviations . XXI Conversion Factors . XXV PartA Chemistry/Production . 1 Chapter 1 Raw Materials . 3 1.1 Phenols ......................... 3 1.1.1 Physical Properties of Phenol . 4 1.1.2 Supply and Use of Phenol . 4 1.1.3 Phenol Production Processes . 5 1.1.3.1 Cumene Oxidation (Hock Process) ......... 5 1.1.3.2 Toluene
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