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Thermal Behavior of Bisphenol-A-Based Copolybenzoxazine with a Nitrile Functional Group

니트릴계 비스페놀 A 코폴리벤조옥사진의 열적 거동

  • Han, Ga Yeong (Department of Fiber System Engineering, Dankook University) ;
  • Cho, Kwang Su (Department of Fiber System Engineering, Dankook University) ;
  • Kim, Hodong (Department of Fiber System Engineering, Dankook University)
  • 한가영 (단국대학교 파이버시스템공학과) ;
  • 조광수 (단국대학교 파이버시스템공학과) ;
  • 김호동 (단국대학교 파이버시스템공학과)
  • Received : 2022.07.29
  • Accepted : 2022.08.26
  • Published : 2022.08.31

Abstract

The thermal behavior of copolybenzoxazine with 2,2-bis(3,4-dihydro-3-phenyl-2H-1,3-benzoxazine)propane and 2,2-bis(3,4-dihydro-3-benzonitrile-2H-1,3-benzoxazine)propane was studied. The structure of the two monomers was confirmed by proton nuclear magnetic resonance and Fourier transformed infrared spectroscopies. The thermal polymerization behaviors of the benzoxazine monomers and their blends were studied using differential scanning calorimetry and thermogravimetric analyses. Results indicated that the nitrile functional group in the benzoxazine monomer significantly influences the maximum curing temperature and char yield of the resin. The thermal decomposition behaviors of the polybenzoxazines and copolybenzoxazines were examined at various compositions. The copolybenzoxazines with a nitrile group exhibited excellent thermal stability and a synergy effect on char yield.

Keywords

References

  1. C. P. R. Nair, "Advances in Addition-cure Phenolic Resins", Prog. Polym. Sci., 2004, 29, 401-498. https://doi.org/10.1016/j.progpolymsci.2004.01.004
  2. N. N. Ghosh, B. Kiskan, and Y. Yagci, "Polybenzoxazines - New High Performance Thermosetting Resins: Synthesis and Properties", Prog. Polym. Sci., 2007, 32, 1344-1391. https://doi.org/10.1016/j.progpolymsci.2007.07.002
  3. H. Ishida and T. Agag (Ed.), "Handbook of Benzoxazine Resins", Elsevier, Burlington, 2011, pp.3-81.
  4. B. Kiskan, B. Koz, and Y. Yagci, "Synthesis and Characterization of Fluid 1,3-benzoxazine Monomers and Their Thermally Activated Curing", J. Polym. Sci. A: Polym. Chem., 2009, 47, 6955-6961. https://doi.org/10.1002/pola.23735
  5. B. Koz, B. Kiskan, and Y. Yagci, "A Novel Benzoxazine Monomer with Methacrylate Functionality and Its Thermally Curable (Co)polymers", Polym. Bull., 2011, 66, 165-174. https://doi.org/10.1007/s00289-010-0261-6
  6. Y. L. Liu, C. Y. Chang, C. Y. Hsu, M. C. Tseng, and I. C. Chou, "Preparation, Characterization, and Properties of Fluorenecontaining Benzoxazine and Its Corresponding Cross-linked Polymer", J. Polym. Sci. A: Polym. Chem., 2010, 48, 4020-4026. https://doi.org/10.1002/pola.24187
  7. C. H. Lin, S. L. Chang, H. H. Lee, H. C. Chang, K. Y. Hwang, A. P. Tu, and W. C. Su, "Fluorinated Benzoxazines and The Structure-property Relationship of Resulting Polybenzoxazines", J. Polym. Sci. A: Polym. Chem., 2008, 46, 4970-4983. https://doi.org/10.1002/pola.22823
  8. Y. L. Liu, J. M. Yu, and C. I. Chou, "Preparation and Properties of Novel Benzoxazine and Polybenzoxazine with Maleimide Groups", J. Polym. Sci. A: Polym. Chem., 2004, 42, 5954-5963. https://doi.org/10.1002/pola.20428
  9. T. Agag and T. Takeichi, "Synthesis and Characterization of Novel Benzoxazine Monomers Containing Allyl Groups and their High Performance Thermosets", Macromolecules, 2003, 36, 6010-6017. https://doi.org/10.1021/ma021775q
  10. Z. Brunovska, R. Lyon, and H. Ishida, "Thermal Properties of Phthalonitrile Functional Polybenzoxazines", Thermochim. Acta, 2000, 357-358, 195-203. https://doi.org/10.1016/S0040-6031(00)00388-9
  11. H. Kimura, Y. Murata, A. Matsumoto, K. Hasegawa, K. Ohtsuka, and A. Fukuda, "New Thermosetting Resin from Terpenediphenol-based Benzoxazine and Epoxy Resin", J. Appl. Polym. Sci., 1999, 74, 2266-2273. https://doi.org/10.1002/(SICI)1097-4628(19991128)74:9<2266::AID-APP16>3.0.CO;2-5
  12. H. J. Kim, Z. Brunovska, and H. Ishida, "Molecular Characterization of the Polymerization of Acetylene-functional Benzoxazine Resins", Polymer, 1999, 40, 1815-1822. https://doi.org/10.1016/S0032-3861(98)00393-0
  13. D. F. Pei, Y. Gu, and X. X. Cai, "Structure and Curing Behavior of a New Dibenzoxazine Precursor Containing Allyl Group", Acta. Polym. Sin., 1998, 5, 595-598.
  14. R. Andreu, J. A. Reina, and J. C. Ronda, "Studies on the Thermal Polymerization of Substituted Benzoxazine Monomers: Electronic Effects", J. Polym. Sci: A. Polym. Chem., 2008, 46, 3353-3366. https://doi.org/10.1002/pola.22677
  15. Y. Yagci, B. Kiskan, and N. N. Ghosh, "Recent Advancement on Polybenzoxazine - a Newly Developed High Performance Thermoset", J. Polym. Sci. A: Polym. Chem., 2009, 47, 5565-5576. https://doi.org/10.1002/pola.23597
  16. B. Kiskan, B. Aydogan, and Y. Yagci, "Synthesis, Characterization, and Thermally Activated Curing of Oligosiloxanes Containing Benzoxazine Moieties in the Main Chain", J. Polym. Sci. A: Polym. Chem., 2009, 47, 804-811. https://doi.org/10.1002/pola.23197
  17. B. Kiskan, Y. Yagci, and H. Ishida, "Synthesis, Characterization, and Properties of New Thermally Curable Polyetheresters Containing Benzoxazine Moieties in the Main Chain", J. Polym. Sci. A: Polym. Chem., 2008, 46, 414-420. https://doi.org/10.1002/pola.22392
  18. M. Ergin, B. Kiskan, B. Gacal, and Y. Yagci, "Thermally Curable Polystyrene via Click Chemistry", Macromolecules, 2007, 40, 4724-4727. https://doi.org/10.1021/ma070549j
  19. A. Yildirim, B. Kiskan, A. L. Demirel, and Y. Yagci, "Synthesis, Characterization and Properties of Naphthoxazine-functional Poly(Propyleneoxide)s", Eur. Polym. J., 2006, 42, 3006-3014. https://doi.org/10.1016/j.eurpolymj.2006.07.019
  20. M. A. Tasdelen, B. Kiskan, and Y. Yagci, "Photoinitiated Free Radical Polymerization Using Benzoxazines as Hydrogen Donors", Macromol. Rapid. Commun., 2006, 27, 1539-1544. https://doi.org/10.1002/marc.200600424
  21. B. Kiskan, D. Colak, A. E. Muftuoglu, I. Cianga, and Y. Yagci, "Synthesis and Characterization of Thermally Curable Benzoxazine-functionalized Polystyrene Macromonomers", Macromol. Rapid. Commun., 2005, 26, 819-824. https://doi.org/10.1002/marc.200500079
  22. M. Nakamura and H. Ishida, "Synthesis and Properties of New Crosslinkable Telechelics with Benzoxazine Moiety at the Chain End", Polymer, 2009, 50, 2688-2695. https://doi.org/10.1016/j.polymer.2009.03.053
  23. A. Chernykh, T. Agag, and H. Ishida, "Synthesis of Linear Polymers Containing Benzoxazine Moieties in the Main Chain with High Molecular Design Versatility via Click Reaction", Polymer, 2009, 50, 382-390. https://doi.org/10.1016/j.polymer.2008.11.017
  24. T. Agag and T. Takeichi, "High-molecular- Weight AB-type Benzoxazines as New Precursors for High-performance Thermosets", J. Polym. Sci. A: Polym. Chem., 2007, 45, 1878-1888. https://doi.org/10.1002/pola.21953
  25. T. Takeichi, T. Kano, and T. Agag, "Synthesis and Thermal Cure of High Molecular Weight Polybenzoxazine Precursors and the Properties of the Thermosets", Polymer, 2005, 46, 12172-12180. https://doi.org/10.1016/j.polymer.2005.10.088
  26. L. Wang and S. Zheng, "Morphology and Thermomechanical Properties of Main-chain Polybenzoxazine-block-polydimethylsiloxane Multiblock Copolymers", Polymer, 2010, 51, 1124-1132. https://doi.org/10.1016/j.polymer.2010.01.008
  27. I. Nam and H. D. Kim, "Preparation of High Performance Thermoset Fiber Using Polybenzoxazine and Polyacrylonitrile", Text. Sci. Eng., 2008, 45, 166-172.
  28. Z. Brunovska and H. Ishida, "Thermal Study on the Copolymers of Phthalonitrile and Phenylnitrile-functional Benzoxazines", J. Appl. Polym. Sci., 1999, 73, 2937-2949. https://doi.org/10.1002/(SICI)1097-4628(19990929)73:14<2937::AID-APP18>3.0.CO;2-E
  29. H. J. Kim, Z. Brunovska, and H. Ishida, "Synthesis and Thermal Characterization of Polybenzoxazines Based on Acetylene-functional Monomers", Polymer, 1999, 40, 6565-6573. https://doi.org/10.1016/S0032-3861(99)00046-4
  30. T. Takeichi, Y. Guo, and S. Rimdusit, "Performance Improvement of Polybenzoxazine by Alloying with Polyimide: Effect of Preparation Method on the Properties", Polymer, 2005, 46, 4909-4916. https://doi.org/10.1016/j.polymer.2005.03.096
  31. I. Dueramae, C. Jubsilp, T. Takeichi, and S. Rimdusit, "High Thermal and Mechanical Properties Enhancement Obtained in Highly Filled Polybenzoxazine Nanocomposites with Fumed Silica", Compos. B: Eng., 2014, 56, 197-206. https://doi.org/10.1016/j.compositesb.2013.08.027
  32. A. P. Kumar and G. R. Rao, "Vibrational Analysis of Substituted Benzonitriles. I. Vibrational Spectra, Normal Coordinate Analysis and Transfer- Ability of Force Constants of Monohalogenated Benzonitriles", Spectrochim. Acta. A: Mol. Biomol. Spectrosc., 1997, 53, 2023-2032. https://doi.org/10.1016/S1386-1425(97)00131-5
  33. A. F. McDonagh and H. E. Smith, "Ring-chain Tautomerism of Derivatives of o-hydroxybenzylamine with Aldehydes and Ketones", J. Org. Chem., 1968, 33, 1-8. https://doi.org/10.1021/jo01265a001
  34. A. F. McDonagh and H. E. Smith, "Ring-chain Tautomerism of Derivatives of o-hydroxybenzylamine with Aldehydes and Ketones: The Nuclear Magnetic Resonance Spectra of Immonium Ions", J. Org. Chem., 1968, 33, 8-12. https://doi.org/10.1021/jo01265a002
  35. L. Chen, D. Ren, S. Chen, K. Li, M. Xu, and X. Liu, "Improved Thermal Stability and Mechanical Properties of Benzoxazinebased Composites with the Enchantment of Nitrile", Polym. Test., 2019, 74, 127-137. https://doi.org/10.1016/j.polymertesting.2018.11.032