Handbook of Benzoxazine Resins - 1st Edition - ISBN: 9780444537904, 9780444537911

Handbook of Benzoxazine Resins

1st Edition

Editors: Hatsuo Ishida Tarek Agag
Hardcover ISBN: 9780444537904
eBook ISBN: 9780444537911
Imprint: Elsevier
Published Date: 13th July 2011
Page Count: 712
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This handbook provides a wide overview of the field, fundamental understanding of the synthetic methods and structure/property correlation, as well as studies related to applications in a wide range of subjects. The handbook also provides 1H and 13C NMR spectra, FTIR spectra, DSC and TGA thermograms to aid in research activities. Additional tables on key NMR and FTIR frequencies unique to benzoxazine, heat of polymerization, Tg, and char yield will greatly aid in the choice of proper benzoxazine for a specific application.

Key Features

  • Provides thorough coverage of the chemistry and applications of benzoxazine resins with an evidence-based approach to enable chemists, engineers and material scientists to evaluate effectiveness
  • Features spectra, which allow researchers to compare results, avoid repetition and save time as well as tables on key NMR frequency, IR frequency, heat of polymerization, of many benzoxazine resins to aid them in selection of materials
  • Written by the foremost experts in the field


Graduate and post graduate level students and researchers in polymer science, materials science polymer chemistry, chemical/biochemical and biomedical engineering and analytical chemistry

Table of Contents



Chapter 1. Overview and Historical Background of Polybenzoxazine Research

1. Introduction

2. Benzoxazine chemistry

3. Polymerization mechanisms

4. Unique properties of benzoxazines and polybenzoxazines

5. Molecular origin of unusual properties

6. Historical development of monomeric benzoxazines

7. Recent development of high molecular weight benzoxazines

8. Benzoxazines combined with other polymerizing groups

9. Various technologies attractive for applications

10. Characterization of benzoxazines

11. Conclusion

Chapter 2. Benzoxazine Chemistry in Solution and Melt

1. Synthesis of benzoxazine monomers in homogeneous solution

2. Synthesis of benzoxazine monomers in heterogeneous solution

3. Synthesis of benzoxazine monomers by melt or high solid methods

4. Benzoxazine ring formation mechanism

5. Conclusion

Chapter 3. Molecular Modeling

1. Introduction

2. Chemical reaction

3. Structure analysis

4. Structure-property relationship

5. Summary and remarks

Chapter 4. Mono-Substituted Phenol-Based Benzoxazines

1. Chemistry and development of benzoxazines

2. Ring opening reaction of mono-substituted phenol-based benzoxazines: dimerization of benzoxazines and its self-termination

3. Single crystallography of monofunctional benzoxazine dimer

4. Asymmetric reaction of monofunctional benzoxazine dimer

5. Benzoxazine dimer and its metal ion complexation

6. Conclusions

Chapter 5. Using Molecular Simulation to Predict the Physical and Mechanical Properties of Polybenzoxazines

1. Introduction

2. Materials and methods

3. Results and discussion

4. Conclusions

Chapter 6. Chemorheology of Benzoxazine-based Resins

1. Introduction

2. Chemorheology of benzoxazine-based resins

3. Gelation of benzoxazine-based resins investigated by FTMS

4. Conclusion

Chapter 7. Polymerization Kinetics

1. Introduction

2. Kinetic analysis of resin polymerization reaction

3. Conclusions

Chapter 8. Electrochemical Polymerization of Benzoxazines

1. Introduction

2. Experimental

3. Electrochemical polymerization of benzoxazines

4. Conclusions

Chapter 9. Light-Induced Reactions of Benzoxazines and Derivatives

1. Introduction

2. Free radical systems

3. Cationic systems

4. Photodimerization

5. UV stability of benzoxazine resins

6. Conclusion

Chapter 10. Effect of Neighboring Groups on Enhancing Benzoxazine Autocatalytic Polymerization

1. Introduction

2. Polymerization mechanism of benzoxazine monomers

3. Substituted benzoxazine monomers

4. Carboxylic acid functional benzoxazine monomers

5. Hydroxyl-functional benzoxazine monomers

6. Conclusion

Chapter 11. Catalytic Opening of Lateral Benzoxazine Rings by Thiols

1. Introduction

2. Experimental

3. Results and discussion

4. Proposed colbert reaction mechanism

5. Linear aromatic polymers

6. Conclusion

Chapter 12. Hydrogen Bonding of Polybenzoxazines

1. Introduction

2. Structure of hydrogen bonding

3. Conclusion

Chapter 13. Thermal Properties Enhancement of Polybenzoxazines

1. Introduction

2. Polymerization of benzoxazine monomers

3. Polybenzoxazine thermal stability

4. Additional cross-linking sites in benzoxazine structure

5. Alkyne functional benzoxazine

6. Alkene-functional benzoxazine

7. Nitrile-functional benzoxazine monomers

8. Maleimide-functional benzoxazine monomers

9. Epoxy functional benzoxazine

10. Methacrylate-functional benzoxazine

11. Conclusion

Chapter 14. Thermal Degradation Mechanisms of Polybenzoxazines

1. Introduction

2. Thermal characteristics of polybenzoxazines

3. Conclusions

Chapter 15. Various Approaches for Main-Chain Type Benzoxazine Polymers

1. Introduction

2. Polymeric mannich base condensation

3. Polymers with mannich condensation of ab-type

4. Chain extension through reactive benzoxazine monomers

5. Conclusion

Chapter 16. Side- and End-Chain Benzoxazine Functional Polymers

1. Introduction

2. Side-chain benzoxazine functional polymers

3. Benzoxazine telechelics

4. Conclusions

Chapter 17. Supramolecular Chemistry of Benzoxazines

1. Concept of supramolecules

2. Resembled structure of benzoxazine and calixarenes

3. Supramolecular structures of benzoxazine dimers

4. Molecular designs and syntheses of benzoxazine dimer-based macrocycles

5. Benzoxazine dimer-based macrocycles

6. Inclusion phenomena of macrocyclic compounds

7. Conclusions

Chapter 18. Main-Chain Type Benzoxazine Oligomers

1. Introduction

2. Synthesis of bisphenol F-Based MCBOs

3. Polymerization behavior of MCBOs

4. Thermal stability of cross-linked MCBOs

5. Viscoelastic properties of MCBOs

6. Viscosity study of MCBOs

7. Conclusions

Chapter 19. Study of a Cardanol-Based Benzoxazine as Reactive Diluent and Toughening Agent of Conventional Benzoxazines

1. Introduction

2. Experimental

3. Results and discussion

4. Conclusion

Chapter 20. Polybenzoxazine/Polyimide Alloys

1. Introduction

2. Polybenzoxazine/pi alloy

3. Effect of preparation method on the properties of poly(ba-a)/pi alloy [17]

4. Polybenzoxazine-poly(imide-siloxane) alloys [19]

5. Conclusions

Chapter 21. Polybenzoxazine/Polyurethane Alloys

1. Introduction

2. Different approaches for the preparation of polybenzoxazine/Polyurethane alloys

3. Conclusion

Chapter 22. The Blends of a Silicon-Containing Arylacetylene Resin and an Acetylene-Functional Benzoxazine

1. Introduction

2. Experimental

3. Properties of blend resins

4. Properties of fiber-reinforced blend resin composites

5. Conclusion

Chapter 23. Polybenzoxazine/Polysiloxane Hybrids

1. Introduction

2. Polybenzoxazine-PDMS hybrid [22]

3. Hybridization with polysiloxanes having a phenyl group as the pendant [23]

4. Polybenzoxazine-poly(dimethylsiloxane-co-diphenylsiloxane) hybrids [24]

5. High-molecular-weight polybenzoxazine prepolymers containing polysiloxane

6. Conclusions

Chapter 24. Poly(Benzoxazine/Bisoxazoline)

1. Introduction

2. Experimental

3. Results and discussion

4. Conclusion

Chapter 25. Morphology and Properties of Polybenzoxazine Blends

1. Introduction

2. Miscibility of polybenzoxazine blends

3. Morphology and properties of polybenzoxazine blends

4. Conclusion

Chapter 26. Porous Materials from Polybenzoxazine

1. Introduction

2. Traditional phenolic-based porous carbon via sol-gel process

3. Porous materials and porous carbon from polybenzoxazine

4. Summary

Chapter 27. Spherical Polybenzoxazine Resin

1. Introduction

2. Experimental

3. Results and discussion

4. Conclusion

Chapter 28. Polybenzoxazine/Fiber Composites

1. Introduction

2. Processing of polybenzoxazine/fiber composites

3. Interface modification of polybenzoxazine/fiber composites

4. Properties and application of polybenzoxazine/fiber composites

Chapter 29. Polybenzoxazine-Clay Nanocomposites

1. Introduction

2. Polybenzoxazines

3. Polybenzoxazine nanocomposites

4. Montmorillonite

5. Synthesis of polybenzoxazine-clay nanocomposites

6. Polymerization behavior of benzoxazines

7. Structure characterization

8. Surface energy properties

9. Viscoelastic properties

10. Thermal stability

11. Conclusions

Chapter 30. Polybenzoxazine-POSS Nanocomposites

1. Introduction

2. Preparation of PBZ-POSS nanocomposties

3. Properties of PBZ-POSS nanocomposites

4. Conclusions and future directions

Chapter 31. Polybenzoxazine-CNT Nanocomposites

1. Introduction

2. Characterization of modified MWNT

3. The preparation of polybenzoxazine-CNT nanocomposites

4. Properties of polybenzoxazine-CNT nanocomposites

5. Conclusion

Chapter 32. Polybenzoxazines with Enhanced Flame Retardancy

1. Introduction

2. Flame retardants: mechanism and environmental concerns

3. Heteroelement-containing polybenzoxazines

4. Conclusion

Chapter 33. Surface Properties of Polybenzoxazines

1. Introduction

2. Surface properties of polybenzoxazines

3. Conclusions

Chapter 34. Advanced Benzoxazine Chemistries Provide Improved Performance in a Broad Range of Applications*

1. Introduction

2. Benzoxazine chemistry

3. Cured characteristics

4. Applications

5. Conclusion

Chapter 35. Benzoxazines for Industrial Applications Comparison with Other Resins, Formulation and Toughening Know-How, and Water-Based Dispersion Technology

1. Introduction and comparison with other resins

2. Chemistry variations, chemical engineering, and tailoring of desired properties

3. Benzoxazine resins in fiber reinforced plastics and water-based dispersions

4. Conclusions

Chapter 36. Polybenzoxazine-Based Composites for Increased Dielectric Constant

1. Polybenzoxazines and their composites

2. Performances of polybenzoxazines and their dielectric properties

3. Dielectric properties in solid materials

4. Dielectric properties of polymer-ceramic composites

5. Dielectric properties of polybenzoxazine-ceramic composites

6. Enhancement of dielectric properties by surface modification of ceramic fillers in composites

7. Conclusion

Chapter 37. Preparation of Polybenzoxazine-Ni-Zn Ferrite Nanocomposites and Their Magnetic Property

1. Introduction

2. Experimental methods

3. Results and discussion

4. Conclusion and future direction

Chapter 38. 1H-NMR Spectra

Chapter 39. IR Spectra

Chapter 40. Raman Spectra

Chapter 41. DSC Thermograms

Chapter 42. TGA Thermograms

Chapter 43. DMA Spectra



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About the Editor

Hatsuo Ishida

Professor Ishida has been a pioneer in the molecular characterization of composite interfaces. His activity extends to synthesis, surface vibrational spectroscopy, and rheology and processing of composite materials. He has also pioneered the development of new, very versatile polymers called polybenzoxazines. Professor Ishida received the following awards among others: The Global Salute to Polymers Award (The American Chemical Society); The Alexander von Humboldt Award for Senior Scientist, Humboldt Foundation, Germany, Oct. (1999); Eminent Scientist, Institute for Physical and Chemical Sciences (RIKEN:Japan); Award for Excellence in Adhesion Research, The Society of Adhesion; and The International Research Award, Society of Plastic Engineers (SPE). He is both SAMPE Fellow and SPE Fellow. He has been the coordinator for establishing a graduate college in polymers and petrochemistry at Chulalongkorn University, Bangkok, Thailand, in the past 20 years. He has 11 edited and translated books, 40 disclosures and patents, and over 440 papers to his credit. His H-index is 63 with total citations of more than 13,000 (as of 09/18/2014). He is a member of the editorial board of “The Journal of Adhesion,” “Journal of Nanostructured Polymers and Nanocomposites,” “Polymers,” “Journal of Materials,” “International Research Journal of Pure and Applied Chemistry,” “Austin Journal of Nanomedicine & Nanotechnology,” “International Journal of Nano Studies & Technology,” “International Research Journal of Pure and Applied Chemistry,” and “Recent Patents on Materials Science,” and Editor-in-Chief of "Composite Interfaces," and Associate Editor of “Polymers and Polymer Composites” as well as “Frontiers: Composite Materials.”

Affiliations and Expertise

Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio, USA

Tarek Agag

Affiliations and Expertise

Elastomer Adhesives & Coatings Technologies (EACT), LORD Corporation, Erie, PA, USA