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Advanced Polymeric Materials Synthesis and Applications RIVER PUBLISHERS SERIES IN POLYMER SCIENCE Series Editors SAJID ALAVI YVES GROHENS Kansas State University University of South Brittany USA France SABU THOMAS Mahatma Gandhi University India Indexing: All books published in this series are submitted to the Web of Science Book Citation Index (BkCI), to CrossRef and to Google Scholar. The “River Publishers Series in Polymer Science” is a series of comprehensive academic and professional books which focus on theory and applications of Polymer Science. Polymer Science, or Macromolecular Science, is a subfield of materials science concerned with polymers, primarily synthetic polymers such as plastics and elastomers. The field of polymer science includes researchers in multiple disciplines including chemistry, physics, and engineering. Books published in the series include research monographs, edited volumes, handbooks and textbooks. The books provide professionals, researchers, educators, and advanced students in the field with an invaluable insight into the latest research and developments. Topics covered in the series include, but are by no means restricted to the following: • Macromolecular Science • Polymer Chemistry • Polymer Physics • Polymer Characterization For a list of other books in this series, visit www.riverpublishers.com The NEC and You Perfect Together: Advanced Polymeric Materials A ComprehensSivyen tShteusdiys oafn tdhAe pplications National Electrical Code Editors Didier Rouxel Gregory P. Bierals Universite´ deLorraine Electrical Design Institute, USA France Sabu Thomas MahatmaGandhiUniversity India Nandakumar Kalarikkal MahatmaGandhiUniversity India Sajith T. Abdulrahman MahatmaGandhiUniversity India River Publishers Published 2018 by River Publishers River Publishers Alsbjergvej 10, 9260 Gistrup, Denmark www.riverpublishers.com Distributed exclusively by Routledge 4 Park Square, Milton Park, Abingdon, Oxon OX14 4RN 605 Third Avenue, New York, NY 10017, USA Advanced Polymeric Materials Synthesis and Applications / by Didier Rouxel, Sabu Thomas, Nandakumar Kalarikkal, Sajith T. Abdulrahman. © 2018 River Publishers. All rights reserved. No part of this publication may be reproduced, stored in a retrieval systems, or transmitted in any form or by any means, mechanical, photocopying, recording or otherwise, without prior written permission of the publishers. Routledge is an imprint of the Taylor & Francis Group, an informa business ISBN 978-87-93609-68-6 (print) While every effort is made to provide dependable information, the publisher, authors, and editors cannot be held responsible for any errors or omissions. DOI: 10.1201/9781003337041 Contents Preface xv List of Contributors xvii List of Figures xxi List of Tables xxvii List of Abbreviations xxix 1 Bisbenzoxazine–Bismaleimide Blends: Thermal Studies 1 S. Shamim Rishwana, M. M. Thahajjathul Kamila and C. T. Vijayakumar 1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.2 Experimental . . . . . . . . . . . . . . . . . . . . . . . . . 13 1.2.1 Materials . . . . . . . . . . . . . . . . . . . . . . . 13 1.2.2 Synthesis of Bis(3,4-Dihydro-2H-3-Phenyl-1, 3-Benzoxazinyl) Isopropane (BAB) . . . . . . . . . 13 1.2.3 Synthesis of 2,2-Bis(4-Nitrophenoxyphenyl) Propane(DN-BPAPCNB) . . . . . . . . . . . . . . 14 1.2.4 Preparation of 2,2-Bis(4-Aminophenoxy Phenyl) Propane(DA-BPAPCNB) . . . . . . . . . . . . . . 14 1.2.5 Preparation of Bisamic Acid (BAX) . . . . . . . . . 15 1.2.6 Preparation of 2,2-Bis[4-(4-Maleimidophenoxy Phenyl)]propane(EXBMI) . . . . . . . . . . . . . . 16 1.2.7 BlendingoftheMaterials. . . . . . . . . . . . . . . 16 1.2.8 Polymerization of the Materials . . . . . . . . . . . 16 1.2.9 FTIRStudies . . . . . . . . . . . . . . . . . . . . . 16 v vi Contents 1.2.10 Differential Scanning Calorimetric (DSC) Studies . . . . . . . . . . . . . . . . . . . . . . . . 17 1.2.11 Thermogravimetric (TG) Studies . . . . . . . . . . 17 1.3 ResultsandDiscussion . . . . . . . . . . . . . . . . . . . . 17 1.3.1 FTIRStudies . . . . . . . . . . . . . . . . . . . . . 17 1.3.2 DSCStudies . . . . . . . . . . . . . . . . . . . . . 20 1.3.3 TGandDTGStudies . . . . . . . . . . . . . . . . . 22 1.4 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . 23 Acknowledgements . . . . . . . . . . . . . . . . . . . . . . 24 References . . . . . . . . . . . . . . . . . . . . . . . . . . 24 2 Studies on Thermosetting Resin Blends: Bispropargyl Ether-Bismaleimide 27 J. Dhanalakshmi, K. G. Sudhamani and C. T. Vijayakumar 2.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 27 2.1.1 ThermosettingResins . . . . . . . . . . . . . . . . 27 2.1.2 High Performance Thermosets . . . . . . . . . . . . 28 2.1.3 Bismaleimide . . . . . . . . . . . . . . . . . . . . . 29 2.1.4 Acetylene-terminated Resins (ATRs) . . . . . . . . 31 2.1.5 Propargyl-terminated Resins (PTRs) . . . . . . . . . 32 2.1.6 Property Enhancement in PT Resins . . . . . . . . . 34 2.1.7 Literature . . . . . . . . . . . . . . . . . . . . . . . 35 2.2 Experimental . . . . . . . . . . . . . . . . . . . . . . . . . 46 2.2.1 Preparation of BPEBPA, BMIM, and BMIE . . . . . 46 2.2.2 Blending of Bispropargyl Ether of Bisphenol-A with BMIMandBMIE . . . . . . . . . . . . . . . . . . . 47 2.2.3 Thermal Curing of the Materials . . . . . . . . . . . 47 2.2.4 Methods . . . . . . . . . . . . . . . . . . . . . . . 47 2.2.4.1 FTIRanalysis . . . . . . . . . . . . . . . 47 2.2.4.2 DSCanalysis . . . . . . . . . . . . . . . 48 2.2.4.3 TGanalysis . . . . . . . . . . . . . . . . 48 2.3 ResultsandDiscussion . . . . . . . . . . . . . . . . . . . . 48 2.3.1 FTIRStudies . . . . . . . . . . . . . . . . . . . . . 48 2.3.2 DSCStudies . . . . . . . . . . . . . . . . . . . . . 49 2.3.3 TGandDTGStudies . . . . . . . . . . . . . . . . . 52 2.4 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . 55 Acknowledgements . . . . . . . . . . . . . . . . . . . . . . 56 References . . . . . . . . . . . . . . . . . . . . . . . . . . 56 Contents vii 3 Synthesis, Characterization, Magnetic, Thermal and Electrochemical Studies of Oxovanadium(IV) Complex of 2-thiophenecarba Benzhydrazone 59 Jyothy G. Vijayan 3.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 60 3.2 Experimental . . . . . . . . . . . . . . . . . . . . . . . . . 60 3.2.1 PhysicalMeasurements . . . . . . . . . . . . . . . . 60 3.2.2 Materials . . . . . . . . . . . . . . . . . . . . . . . 61 3.2.3 SynthesisofLigand. . . . . . . . . . . . . . . . . . 61 3.2.3.1 Synthesis of 2-thiophenecarba benzhydrazone . . . . . . . . . . . . . . . 61 3.2.4 SynthesisofComplex . . . . . . . . . . . . . . . . 61 3.2.4.1 Preparation of 2-thiophenecarba benzhydrazonato oxovanadium(IV) . . . . 61 3.3 ResultsandDiscussion . . . . . . . . . . . . . . . . . . . . 62 3.3.1 Characterization of the Ligand (2-Thiophenecarba Benzhydrazone) . . . . . . . . . . . . . . . . . . . 62 3.3.2 Characterization of the Complex . . . . . . . . . . . 63 3.3.3 Proposed Structure of the Complex . . . . . . . . . 69 3.4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . 69 Acknowledgements . . . . . . . . . . . . . . . . . . . . . . 70 References . . . . . . . . . . . . . . . . . . . . . . . . . . 70 4 Sorption and Desorption Analyses of Sorbents for Oil-spill Control 73 Neha Bhardwaj and Ashok N. Bhaskarwar 4.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 74 4.1.1 Pollution-prevention Application of Polymers . . . . 75 4.1.2 ProblemofOilSpill . . . . . . . . . . . . . . . . . 76 4.2 Factors Affecting the Performance of Sorbents . . . . . . . 81 4.3 SorptionandDesorptionKinetics . . . . . . . . . . . . . . 83 4.3.1 SorptionKinetics . . . . . . . . . . . . . . . . . . . 83 4.3.2 DesorptionModels . . . . . . . . . . . . . . . . . . 86 4.3.3 Sorption-desorption Analysis of PolyurethaneFoam . . . . . . . . . . . . . . . . . . 89 4.4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . 95 References . . . . . . . . . . . . . . . . . . . . . . . . . . 95 viii Contents 5 Polyhexahydrotriazines: Synthesis and Thermal Studies 101 Nitish Paul Tharakan, J. Dhanalakshmi, and C. T. Vijayakumar 5.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 101 5.1.1 Polymer . . . . . . . . . . . . . . . . . . . . . . . . 101 5.1.2 Classification based on Thermal Behavior . . . . . . 102 5.1.3 ThermosettingPolymer . . . . . . . . . . . . . . . . 102 5.1.4 ThermosetMaterials . . . . . . . . . . . . . . . . . 104 5.1.4.1 Phenol formaldehyde . . . . . . . . . . . 104 5.1.4.1.1 Novolacs . . . . . . . . . . . . . 104 5.1.4.1.2 Resoles . . . . . . . . . . . . . 104 5.1.4.2 Urea–formaldehyde resin . . . . . . . . . 105 5.1.4.3 Melamine formaldehyde resin . . . . . . . 106 5.1.4.4 Unsaturated polyester resin . . . . . . . . 106 5.1.4.5 Epoxyresins . . . . . . . . . . . . . . . . 107 5.1.4.6 Bismaleimides . . . . . . . . . . . . . . . 107 5.1.4.7 Bispropargyl ethers . . . . . . . . . . . . 108 5.1.4.8 Cyanateester . . . . . . . . . . . . . . . 109 5.1.4.9 Triazines . . . . . . . . . . . . . . . . . . 110 5.1.4.10 Polyhexahydrotriazine . . . . . . . . . . . 110 5.2 Experimental . . . . . . . . . . . . . . . . . . . . . . . . . 111 5.2.1 Preparation of Hemiaminal Using 4,4’-Methylenedianiline (HA-MDA) . . . . . . . . . 111 5.2.2 ThermalCuring . . . . . . . . . . . . . . . . . . . 113 5.2.3 Methods . . . . . . . . . . . . . . . . . . . . . . . 113 5.3 ResultsandDiscussion . . . . . . . . . . . . . . . . . . . . 113 5.3.1 FTIRStudies . . . . . . . . . . . . . . . . . . . . . 113 5.3.2 ThermalStudies . . . . . . . . . . . . . . . . . . . 115 5.4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . 118 Acknowledgements . . . . . . . . . . . . . . . . . . . . . . 118 References . . . . . . . . . . . . . . . . . . . . . . . . . . 119 6 Influence of Cement Behavior with and without Polymer Nano Composites 121 Mainak Ghosal and Arun Kumar Chakraborty 6.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 122 6.2 ExperimentalProgram . . . . . . . . . . . . . . . . . . . . 131 6.2.1 TestsonCementMortar . . . . . . . . . . . . . . . 132 6.3 Results . . . . . . . . . . . . . . . . . . . . . . . . . . . . 134 Contents ix 6.4 DiscussionsofTestResults . . . . . . . . . . . . . . . . . . 134 6.4.1 PhysicalCharacteristics . . . . . . . . . . . . . . . 136 6.4.2 DispersionMechanism . . . . . . . . . . . . . . . . 137 6.4.3 CompressiveStrength . . . . . . . . . . . . . . . . 139 6.5 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . 139 References . . . . . . . . . . . . . . . . . . . . . . . . . . 139 7 Effect of Structure of Diphenol on Polymerization of Bis(isoimide) 143 V. Sarannya, R. Surender, S. Shamim Rishwana, R. Mahalakshmy, and C. T. Vijayakumar 7.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 143 7.1.1 High-performance Thermosetting Resin . . . . . . . 143 7.1.2 AlkydResins . . . . . . . . . . . . . . . . . . . . . 144 7.1.3 AminoResins . . . . . . . . . . . . . . . . . . . . . 145 7.1.4 Unsaturated Polyester Resins . . . . . . . . . . . . . 145 7.1.5 AllylResins . . . . . . . . . . . . . . . . . . . . . . 145 7.1.6 EpoxyResins . . . . . . . . . . . . . . . . . . . . . 146 7.1.7 Polyurethanes . . . . . . . . . . . . . . . . . . . . . 146 7.1.8 SiliconeResins . . . . . . . . . . . . . . . . . . . . 146 7.1.9 CyanateEsterResins . . . . . . . . . . . . . . . . . 147 7.1.10 PhenolicResins . . . . . . . . . . . . . . . . . . . . 147 7.1.10.1 Allyl functional phenols . . . . . . . . . . 148 7.1.10.2 Bisoxazoline phenols . . . . . . . . . . . 148 7.1.10.3 Phenolic resins epoxy systems . . . . . . 149 7.1.11 Polyimide . . . . . . . . . . . . . . . . . . . . . . . 149 7.1.11.1 Classification of polyimides . . . . . . . . 150 7.1.11.2 Properties of polyimide . . . . . . . . . . 150 7.1.12 Bismaleimides(BMIs) . . . . . . . . . . . . . . . . 151 7.1.13 Isoimides . . . . . . . . . . . . . . . . . . . . . . . 153 7.1.14 Polyisoimide . . . . . . . . . . . . . . . . . . . . . 155 7.1.15 Bis(isoimides) . . . . . . . . . . . . . . . . . . . . 155 7.1.16 Maleimide and Isomaleimide . . . . . . . . . . . . . 156 7.2 Experimental . . . . . . . . . . . . . . . . . . . . . . . . . 160 7.2.1 Materials . . . . . . . . . . . . . . . . . . . . . . . 160 7.2.2 Preparation of Bis(isoimide) of 4,4’-Methylene Dianiline . . . . . . . . . . . . . . . . . . . . . . . 160 7.2.3 Blending of Bisphenols with Bis(isoimide) (VS) . . 160