Handbook of Maleic Anhydride Based Materials
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Osama M. Musa Editor Handbook of Maleic Anhydride Based Materials Syntheses, Properties and Applications
Editor Osama M. Musa Ashland Inc. Bridgewater, New Jersey USA ISBN 978-3-319-29453-7 ISBN 978-3-319-29454-4 (ebook) DOI 10.1007/978-3-319-29454-4 Library of Congress Control Number: 2016952878 Springer International Publishing Switzerland 2016 This work is subject to copyright. All rights are reserved by the Publisher, 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 physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. Printed on acid-free paper This Springer imprint is published by Springer Nature The registered company is Springer International Publishing AG Switzerland
Preface Within the chemical industry, the chemical compound known as maleic anhydride is a critical material that is globally produced at significant and increasing volumes. The wide availability of this compound is due to a precious coupling of low cost and high functionality. This functionality easily bridges the domains of chemical synthesis and transformation to extreme market application and diversification. This functionality is further reflected in the tens of thousands of peer-reviewed journal articles and granted patents that highlight some form of maleic anhydride utility. This book is written from the perspective of an industrial scientist. By bridging the science and technology found in both academia and industry, a comprehensive and contemporary picture of maleic anhydride s impact on the world today, as well as tomorrow, emerges. Perhaps the most unique aspect of this work is the group of scientists that prepared and contributed to this manuscript. They are all members of the Research and Development community at Ashland, Inc., where maleic anhydride is a core technology. This team closely collaborated and debated the most relevant technical topics, which should be of great benefit to the reader. Remembering that in 1982, B.C. Trivedi and B.M. Culbertson coauthored the seminal book entitled Maleic Anhydride, covering topics such as its production, chemical reactions, and polymerizations. This comprehensive treatise was a truly ambitious achievement. Our book seeks to build upon this foundation, built 34 years ago, by focusing on many of the key technical insights and commercial developments since 1982. It is my hope that the reader will obtain a deeper and more comprehensive understanding of the beauty, nuances, and complexities of maleic anhydride through our exploration of production, synthesis and transformation, and diverse application topics that are incorporated into these ten chapters. Chapter 1 reviews the main production processes, analyzes the current understanding of catalyst structure/function in the butane oxidation process, and reviews a variety of contemporary research topics such as catalyst additives that improve yield and purity, catalyst dimensional strength, morphology, porosity, shape, regeneration, reactor designs, and improvements in product quality and safety. v
vi Preface Chapter 2 reviews virtually all maleic anhydride chemical reactions, including its acid form, in the context of the influence the parent structure imparts on the molecule s final behavior and properties. Chapter 3 reviews small molecule chemistry and applications such as maleatedvegetable oil derivatives and its oligomeric products. Modern topics such as maleimide-based compounds are also detailed in elegant fashion. Chapter 4 is a detailed review of the maleic anhydride-co-alkyl vinyl ether copolymer family of materials discussing polymerization, architecture, physical properties, and attributes. Chapter 5 reviews other industrially significant polymers, ranging from unsaturated polyester and alkyd resins to styrenic, acrylic, and N-vinyl amide copolymers. Incorporated into this overview are recent advances in controlled free radical polymerization materials. Chapter 6 highlights higher molecular weight maleic anhydride-derived polymers. Polymerization processes, including alternating copolymers by conventional free-radical methods, as well as newer approaches such as ROMP methodologies are discussed. Chapter 7 discusses the colloidal and physicochemical properties for maleic anhydride-based polymers in addition to providing insight into how such material features can relate to application performance. Chapter 8 provides an in depth discussion of key Personal Care applications of maleic anhydride in markets ranging from Hair Care and Skin Care to Transdermal Delivery and Oral Care. Maleic anhydride chemistry is paramount in many commercially available consumer products in this arena and where it has become an essential key ingredient. Chapter 9 reviews the utility of maleic anhydride in industrial adhesive and coating applications in markets ranging from coatings, boats, and electronics through the exploitation of materials including alkyd resins, reactive polymeric surfactant, unsaturated polyester resins, bismaleimides, and epoxy resins. Insights into printing and imaging materials are also incorporated into this discussion. Chapter 10 is a continuation of Chap. 9, where the variety of different application areas of maleic anhydride chemistry is expanded into lubricants, fuels, and biologically active compounds as well as pharmaceutical compositions, microencapsulation, thermoplastics, films, and water treatment materials. This book provides the reader with a broad and in-depth resource on maleic anhydride and its derivatives, enabling a more complete understanding of the science and technology of maleic anhydride. Bridgewater, NJ Osama M. Musa
Acknowledgements I would like to gratefully acknowledge the authors and their families, who sacrificed significant time and effort to make this text possible. I would also like to thank my family for their tremendous patience and encouragement. Finally, on behalf of the authors, I would like to thank the management of Ashland Inc. for their support in bringing this manuscript to fruition. vii
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Contents Part I Introduction 1 Progress in Maleic Anhydride Production... 3 David K. Hood and Osama M. Musa Part II Reactions and Derivatives 2 Reactions Involving Maleic Anhydride... 59 Michael A. Tallon 3 Vegetable Oil Maleic Anhydride and Maleimide Derivatives: Syntheses and Properties... 151 Fan Wu and Osama M. Musa Part III Maleic Anydride-Derived Polymers 4 The Quintessential Alternating Copolymer Family: Alkyl Vinyl Ether co-maleic Anhydride Copolymers... 211 Krystyna Plochocka, Xuejun (Jay) Liu, Michael A. Tallon, and Osama M. Musa 5 Industrially Significant Copolymers Containing Maleic Anhydride... 251 Michael A. Tallon and Xuejun (Jay) Liu 6 Ring-Opening Metathesis Polymerization (ROMP) Using Maleic Anhydride-Based Monomers... 311 Michael A. Tallon 7 Colloidal and Physicochemical Properties of Maleic Anhydride Polymers... 399 Roger L. McMullen ix
x Contents Part IV Applications 8 Maleic Anhydride Applications in Personal Care... 441 Roger L. McMullen 9 Application of Maleic Anhydride in Coatings, Adhesives and Printing... 509 David K. Hood and Osama M. Musa 10 Application of Maleic Anhydride-Based Materials... 577 David K. Hood and Osama M. Musa Index... 629
Biography Osama M. Musa Ph.D. Dr. Osama M. Musa is currently Vice President and Chief Technology Officer for Ashland Inc. (NYSE: ASH). He leads Ashland s Global Research and Development focusing on consumer and industrial markets including pharmaceutical, personal care, beverage, nutrition, agricultural, coatings, adhesives, and energy applications. Dr. Musa has overall responsibility for the global technology platforms including Molecular Science, Measurement Science, Process Research, Biofunctionals, Acrylates & Microencapsulation, Preservatives & Microbial Technology, as well as the R&D Stage-Gate development process. He also leads the R&D Council and Multifunctional Innovation Engagement Team, which are charged with managing and enhancing new product development processes. In addition to these technical roles, he has the commercial and technical responsibility for Ashland s Advanced Materials business. Dr. Musa is a strategic R&D leader with broad experience in the specialty chemicals business sector. He utilizes a wide-ranging network, cooperating with partners both in the industry and in academia. Dr. Musa joined Ashland in 2011 following the company s acquisition of International Specialty Products (ISP) Incorporated. Previously, he held technical and leadership positions with the National Starch and Chemical Company. As a passionate leader, Dr. Musa is committed to addressing customer needs through the application of innovative chemistry. He holds more than 50 issued U.S. patents and has authored numerous technical publications. From Ashland s Open Innovation platform, he cultivates student scholarship through numerous collaborations with universities, providing encouragement and motivational mentoring to the next generation of young, promising scientists. He serves as a xi
xii Biography member of the Board of Advisors at Manhattan College s Department of Electrical and Computer Engineering. Dr. Musa earned a Ph.D. in organic chemistry from Wayne State University, where he also completed a postdoctoral fellowship. In addition, he received an M.S. in macromolecular chemistry from the University of Detroit Mercy, an M.S. degree in heterocyclic organic chemistry from the University of Jordan, and a B.S. in chemistry from Yarmouk University.