The Chemistry and Applications of Benzoxazines

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Presentation transcript:

The Chemistry and Applications of Benzoxazines Reporter: Meng Wei Wang Advising Prof: Ru Jong Jeng 5.6.8.14.17-20.22.24.25.27-31.36.38 Hatsuo Ishida and Tarek Agag, Handbook of Benzoxazine Resins

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

Benzoxazine (Bz) resins Benzene Polybenzoxazine themosets. 1. Low cost of raw materials 5. 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 curing 8. Considerable flexibility in the molecular design. 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.

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

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

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

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

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

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

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.

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.

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

Monomeric benzoxazines (I) Bisphenol type Diamine type Sample Tg (oC) Td (oC) Char yield (%) P(13) 208 425 52 P(F-a) 155 314 49 Poor mechanical property Lin. C.H., et al ,Polymer 2008, 49, 1220

Monomeric benzoxazines (II) Takeichi, T., et al, Macromolecules 2001, 34, 7257. Sample Tg (oC) PPa 161 PP-appe 251 PBa 171 PB-appe 318 Curing Lin, C. H., et al, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 4555.

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

Side chain type polybenzoxazine precursors Kimura. H., et al , J. Appl. Polym. Sci. 2001, 79, 555 Sample Tg (oC) Va/DGEBA 174 VBa/DGEBA 143 Endo. T., et al , J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 3174

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

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.

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

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

Thanks for your attention.