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PhtP Polyimides and other 3 high temPerature K s P .l y o Polymers: synthesis, . n l m t y i h i CharaCterization and t m t a e l ( s id e i aPPliCations d s e s , s .) C a h n a d r a o C t t h e e r r i z h a i t g i h o n t e a m n P d e r a a P t P l u i r C e a t P o i o l n y s m e r s : Edited by K.l. mittal brill.nl/phtp IIIVSPIII IIIVSPIII Polyimides and Other High Temperature Polymers: Synthesis, Characterization and Applications Volume3 TThhiiss ppaaggee iinntteennttiioonnaallllyy lleefftt bbllaannkk POLY IMIDES AND OTHER HIGH TEMPERATURE POLYMERS: SYNTHESIS, CHARACTERIZATION AND APPLICATIONS VoLUME J Editor: K.L. Mittal //IVS Pill UTRECHT • BOSTON 2005 CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2005 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Version Date: 20120727 International Standard Book Number-13: 978-9-04-741514-5 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information stor- age or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copy- right.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that pro- vides licenses and registration for a variety of users. For organizations that have been granted a pho- tocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface IX Part 1. Synthesis, Properties and Bulk Characterization Water as solvent in polyimide synthesis: Thermoset and thermoplastic examples J. Chiefari, B. Dao, A. M. Groth and J. H. Hodgkin 3 Synthesis and properties of polyimides derived from 2-diphenyl methoxy-4,6-diamino-1 ,3,5-triazine and aromatic tetracarboxylic dianhydrides M. Padmanabha Raju, S. Alam and G. N. Mathur 15 New organo-soluble polyimides based on 2,4,6-trinitrotoluene derivatives A. L. Rusanov, L. G. Komarova, M.P. Prigozhina, V. A. Tartakovskiy, S. A. Shevelev, M. D. Dutov, A. Kh. Shakhnes, 0. V. Serushkina, S. S. Vorob'ev, M. ]. M. Abadie and V. Yu. Voitekunas 25 Properties of vapor-deposited polyimides D. R. Harding, F.-Y. Tsai, E. L. Alfonso, S. H. Chen, A. K. Knight and T. N. Blanton 49 Structure/property correlations in new adamantane-based polyimides and copolyimides T. E. Sukhanova, I. V. Gofman, A. I. Grigoriev, M. E. Vylegzhanina, D. V. Novikov, B. S. Orlinson and I. A. Novakov 69 Structure-property relationships as determined in PMDA-ODA polyimide processed by powder metallurgy techniques T. D. Krizan, V. A. Bershtein, T. E. Sukhanova, M. Y. Keating, A. E. Bursian, A. I. Grigoriev, V. M. Egorov, M. E. Vylegzhanina and P. N. Yakushev 89 Porosity and functionality in polyimides: Effects of dendrimer substitution and chemical imidization in a supercritical medium Z. Jia, Y. Gu and M. P. Srinivasan Ill vi Contents Synthesis and characterization of novel bismaleimides S. Anu Abirami, S. Alam and G. N. Mathur 131 Preparation and properties of epoxy/maleimide compounds and their cured resins Y.-L. Liu, Y.-J. Chen, Y.-H. Wang and C.-S. Wu 141 Synthesis and characterization of polybenzimidazopyrrolones based on pyridine-bridged aromatic tetraamines and dianhydrides J.-G. Liu, L.-F. Wang, L. Fan and S.-Y. Yang 155 Synthesis and characterization of novel heterocyclic-ring-based poly(arylene ether)s R. Dubey, S. Alam and G. N. Mathur 175 Cyclic aromatic polyethers H. R. Kricheldorf, M. Garaleh, L. Vakhtangishvili and G. Schwarz 185 Part 2. Hybrids and Composites Fluoro-poly(e ther imide) s and fluoro-poly( ether imide)/ organa-soluble MMT clay nanocomposites: Synthesis, fabrication, characterization and thermal degradation kinetics study of their films R. H. Vora, P. D. Sawant, S. H. Goh and M. Vora 201 Characterization and degradation of acidic fluorinated poly(amide-imide)s and their hybrids with silica T. C. Chang, C. C. Shih and G. P. Wang 267 Poly(amide-imide) nanocomposites for high-temperature wire coatings A. Ranade, N. A. D'Souza and B. Gnade 283 Influence of crystallinity of R-BAPB-type polyimide matrix on thermal and mechanical properties of carbon-fiber-reinforced composites V. E. Yudin, V. M. Svetlichnyi, G. N. Gubanova, A. L. Didenko, E. N. Popova, T. E. Sukhanova, A. I. Grigoriev, T. A. Kostereva, I. Arbel and G. Marom 299 Viscoelastic properties of polyimide--silica ceramers imidized under different curing conditions A. A. M. Ali, F. Al-Sagheer and Z. Ahmad 317 Transport of low-molecular-weight c:ompounds in silicalpolyimide hybrids P. Musto, S. Cotugno, G. Mensitieri and F. Lenzi 333 Contents VII Part 3. Applications and General Papers Peculiarities of segmental dynamics in complex polyimide materials for advanced technologies V. A. Bershtein, L. David, V. M. Ef?orov, P. Pissis, P. Sysel and P. N. Yakushev 353 A new class of photoalignable polyimides with high photosensitivity Z.-X. Zhong, X. Li, S. H. Lee and M.-H. Lee 401 Enhancing the photoconductivity of polyimides by incorporating intrinsic chromophore units B.-K. Zhu, Y.-Y. Xu and Z.-K. Xu 423 Polyimide as a tunneling barrier in single-electron tunneling junctions Y. Noguchi, T. Manaka and M. Iwamoto 439 Preparation and performance of ultrafiltration membranes from polyetherimide and its sulfonated derivatives Z.-K. Xu, L.-S. Wan and Q. Yang 453 Design and properties of polymer materials with high glass-transition temperatures for nonlinear optical applications C. Samyn, G. Koeckelherghs, T. Verhiest and A. Persoons 499 Alignment of SWNTs in lyotropic rigid-rod polymer compositions T. D. Dang, S. Kumar, T. Uchida, K. L. Strong and N. Venkatasuhramanian 517 Adhesion of copper to UV photo-oxidized polyimide (PMDA-ODA) surfaces U. Sener, A. Entenherg, B. Kahn, F. D. Egitto, L. J. Matienzo, T. Dehies and G. A. Takacs 535 Polyimide erosion in a low Earth orbit space environment simulated by a laser detonation atomic oxygen beam facility M. Tagawa and K. Yokota 553 TThhiiss ppaaggee iinntteennttiioonnaallllyy lleefftt bbllaannkk Polyimides and Other High Temperature Polymers, Vol. 3, pp. ix-x Ed. K.L. Mittal ©VSP2005 Preface This volume chronicles the proceedings of the Third International Symposium on Polyimides and Other High Temperature Polymers: Synthesis, Characterization and Applications held under the aegis of MST Conferences in Orlando, FL, De cember 17-19, 2003. The first and second symposia in this series were held in 1999 and 2001, respectively, the proceedings of which were properly documented in hard-bound books [1, 2]. As these symposia have elicited much interest from the R&D community in this arena, so the next symposium on this topic is planned some time in December 2005. Because of their unique and highly desirable properties, polyimides have found a legion of applications ranging from aerospace to microelectronics to optics to membranes to composites. Even a cursory look at the literature will evince that currently there is tremendous R&D activity in the realm of polyimides and other high temperature polymers, and all signals indicate that this high tempo will con tinue unabated. Moreover, as new and improved variants of these materials be come available, new applications will emerge. The technical program for this symposium comprised 34 papers covering many ramifications of these materials. There were lively (not exothermic) discussions throughout the symposium, both formally and informally. If comments from the attendees is a barometer then this symposium was a huge success. As for this volume, it contains a total of 27 papers (others are not included for a variety of reasons) addressing the latest developments, ranging from synthesis to applications, relative to polyimides and other high temperature polymers. As re corded in the Prefaces to previous volumes, it must again be underscored that all manuscripts for this volume were rigorously peer reviewed, appropriately revised (some twice or thrice), and meticulously edited before inclusion in this volume. So this volume is not a mere collection of unreviewed papers - which generally is the case with many, if not all, so-called proceedings volumes -but reflects the highest standard of publication. This volume is divided into three parts. Part 1 "Synthesis, Properties and Bulk Characterization"; Part 2 "Hybrids and Composites"; and Part 3 "Applications and General Papers". The topics covered include: Synthesis, characterization and processing (including some novel approaches) of a variety of polyimides and other high temperature polymers; structure-property relationships; hybrids and nanocomposites using these materials and their characterization, properties and applications; segmental dynamics in polyimide materials; photoalignable polyim ides; photoconductivity and photosensitivity of polyimides; ultrafiltration mem-

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