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The Chemistry and Applications of Benzoxazines

The Chemistry and Applications of Benzoxazines. Reporter: Meng Wei Wang Advising Prof: Ru Jong Jeng. Hatsuo Ishida and Tarek Agag, Handbook of Benzoxazine Resins. Outline. Chemistry of benzoxazines Synthesis Ring-opening mechanisms Recent development of benzoxazines

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The Chemistry and Applications of Benzoxazines

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  1. The Chemistry and Applications of Benzoxazines Reporter: Meng Wei Wang Advising Prof: Ru Jong Jeng Hatsuo Ishida and Tarek Agag, Handbook of Benzoxazine Resins

  2. Outline • Chemistry of benzoxazines • Synthesis • Ring-opening mechanisms • Recent development of benzoxazines • Monomeric benzoxazines • Main chain type • Side chain type • Another applications for benzoxazine resins • Conclusions

  3. Benzoxazine (Bz) resins 1. Low cost of raw materials5. Low water absorption 2. No need for harsh catalysts 6. Low surface energy 3. No by-product 7. Superior electrical properties 4. Small shrinkage in curing8.Considerable flexibility in the molecular design. Oxazine Benzene Polybenzoxazine themosets. How to synthesize benzoxazines? 5,6Wang, C.-F., et al ,Angew. Chem. Int. Ed. 2006, 45, 2248. 7Ishida, H., et al ,J. Polym. Sci. Part A: Polym. Chem. 1994, 32, 1121.

  4. One-potprocedure(Traditional procedure) Brunovska, Z.; Liu, J.-P.; Ishida, H. Macromol. Chem. Phys.1999, 200, 1745.

  5. Two-pot procedure Lin. C.H., et al ,Polymer 2008, 49, 1220

  6. Ring-opening mechanism of benzoxazines What is the mechanism of polymerization?

  7. Type I - Phenoxy structure Ishida, H., et al , Macromolecules 2000, 33, 2839.

  8. Type II – Phenolic structure Ishida, H., et al , Macromolecules 2000, 33, 2839.

  9. Main chain rearrangement Endo, T., et al , Macromolecules 2008, 41, 9030.

  10. The acceleration of benzoxazine polymerization (I) Andreu, R. et al., J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3353. When R1 is electron-withdrawing group → Decrease in the polymerization temp. When R2 is electron-withdrawing group → Increase in the polymerization temp. Gu, Y. et al., J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 1443.

  11. The acceleration of benzoxazine polymerization (II) Ronda, J. C., et al., J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3353. Endo, T., Macromolecules 2010, 43, 1185. Ishida, H., Macromolecules 2012, 45, 8119.

  12. Outline • Chemistry of benzoxazines • Synthesis • Ring-opening mechanisms • Recent development of benzoxazines • Monomeric benzoxazines • Main chain type • Side chain type • Another applications for benzoxazine resins • Conclusions

  13. Monomericbenzoxazines (I) Bisphenol type Diamine type Poor mechanical property Lin. C.H., et al ,Polymer 2008, 49, 1220

  14. Monomericbenzoxazines (II) Takeichi, T., et al, Macromolecules 2001, 34, 7257. Curing Lin, C. H., et al, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 4555.

  15. Main chain type polybenzoxazine precursors Takeichi, T., et al, Polymer 2005, 46, 12172. Lin. C.H., et al ,Polym. Chem. 2012, 3, 935

  16. Side chain type polybenzoxazine precursors Kimura. H., et al , J. Appl. Polym. Sci. 2001, 79, 555 Endo. T., et al , J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 3174

  17. Outline • Chemistry of benzoxazines • Synthesis • Ring-opening mechanisms • Recent development of benzoxazines • Monomeric benzoxazines • Main chain type • Side chain type • Another applications for benzoxazine resins • Conclusions

  18. Another applications for benzoxazine resins (I) Ishida, H., et al., Polym. Chem. 2011, 49, 4335. Takeichi, T., et al, Polymer 2008, 49, 1173. Takeichi, T., et al, J. Polym. Sci. Part A: Polym. Chem.2001, 39, 2633.

  19. Another applications for benzoxazine resins (II) Ishida, H., et al., Macromolecules 2012, 45, 8991. Endo, T., et al .ACS Macro Lett. 2013, 2, 1.

  20. Conclusions • Considerable flexibility in the molecule-design • Crosslink • No by-product Future work • More functionality • Brittle • Ring-open temperature

  21. Thanks for your attention.

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