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The effect of 3-hydroxyphenylboronic acid on thermal characteristics of polybenzoxazine based on phenol and 4-aminomethylbenzoate

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Abstract

In this study, a polybenzoxazine, (PPab) based on phenol and 4-aminomethyl benzoate and its composites containing various amounts of 3-hydroxyphenylboronic acid, (HB) were prepared by stepwise curing. It has been found that thermal properties of composites were improved as the amount of HB introduced was increased. The improvements in thermal characteristics were associated with condensation reactions of hydroxyl groups of polybenzoxazine and ester groups on the aniline linkages yielding a highly cross-linked structure. In addition, application of direct pyrolysis mass spectrometry, DP-MS, technique supplied information pointing out generation of a boroxine network by self-condensation reactions of B-OH groups.

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References

  1. Wang DC, Chang GW, Chen Y (2008) Preparation and thermal stability of boron-containing phenolic resin/clay nanocomposites. Polym Degrad Stab 93:125–133

    Article  CAS  Google Scholar 

  2. Doğan M, Bayramlı E (2011) Synergistic effect of boron containing substances on flame retardancy and thermal stability of clay containing intumescent polypropylene nanoclay composites. Polym Adv Technol 22:1628–1632

    Article  Google Scholar 

  3. Wang J, Jiang N, Jiang H (2010) Micro-structural evolution of phenol-formaldehyde resin modified by boron carbide at elevated temperatures. Mater Chem Phys 120:187–192

    Article  CAS  Google Scholar 

  4. Xu P, Jing X (2010) Pyrolysis of hyperbranched polyborate modified phenolic resin. Polym Eng Sci 50:1382–1388

    Article  CAS  Google Scholar 

  5. Espinosa MA, Galia M (2003) Synthesis and characterization of benzoxazine-based phenolic resins: crosslinking study. J Appl Polym Sci 90:470–481

    Article  CAS  Google Scholar 

  6. Ning X, Ishida H (1994) Phenolic materials via ring- opening polymerization of benzoxazines: effect of molecular structure on mechanical and dynamic mechanical properties. J Polym Sci Part B Polym Phys 32:921–927

    Article  CAS  Google Scholar 

  7. Li H, Yao D, Fu Q, Liu L, Zhang Y, Yao X, Wang Y, Li H (2013) Anti-oxidation and ablation properties of carbon/carbon composites infiltrated by hafnium boride. Carbon 52:418–426

    Article  CAS  Google Scholar 

  8. Wang S, Wang Y, Bian C, Zhong Y, Jing X (2015) The thermal stability and pyrolysis mechanism of boron-containing phenolic resins: the effect of phenyl borates on the char formation. Appl Surf Sci 331:519–529

    Article  CAS  Google Scholar 

  9. Yagci Y, Kiskan B, Ghosh NN (2009) Recent advancement on polybenzoxazine-a newly developed highperformance thermoset. J Polym Sci Polym Chem 47:5565–5576

    Article  CAS  Google Scholar 

  10. Chutayothin P, Ishida H (2010) Cationic ring-opening polymerization of 1,3-benzoxazines: mechanistic study using model compounds. Macromolecules 43:4562–4572

    Article  CAS  Google Scholar 

  11. Jubsilp C, Takeichi T, Rimdusit S (2011) Polymerization kinetics: handbook of benzoxazine resins. Elsevier, New York

    Book  Google Scholar 

  12. He Z, Chen J, Keum JK, Szulczewski G, Li D (2014) Improving performance of TIPS pentacene-based organic thin film transistors with small-molecule additives. Org Electron 15:150–155

    Article  CAS  Google Scholar 

  13. He Z, Asare-Yeboah K, Zhang Z, Bi S (2019) Self-assembly crystal microribbons with nucleation additive for high-performance organic thin film transistors. Jpn J Appl Phys 58:061009

    Article  CAS  Google Scholar 

  14. He Z, Zhang Z, Bi S (2019) Long-range crystal alignment with polymer additive for organic thin film transistors. J Polym Res 26:173–180

    Article  Google Scholar 

  15. He Z, Zhang Z, Bi S, Asare-Yeboah K, Chen J (2020) Ultra-low misorientation angle in small-molecule semiconductor/polyethylene oxide blends for organic thin film transistors. J Polym Res 27:75–81

    Article  CAS  Google Scholar 

  16. Chozhan C, Alagar M (2009) Gnanasundaram P synthesis and characterization of 1,1-bis(3-methyl-4-hydroxy phenyl)cyclohexane polybenzoxazine–organoclay hybrid nanocomposites. Acta Mater 57:782–794

    Article  CAS  Google Scholar 

  17. Ishida H, Low HY (1998) Synthesis of benzoxazine functional silane and adhesion properties of glass-fiber-reinforced polybenzoxazine composites. J Appl Polym Sci 69:2559–2567

    Article  CAS  Google Scholar 

  18. Low HY, Ishida H (1999) An investigation of the thermal and thermo-oxidative degradation of polybenzoxazines with a reactive functional group. J Polym Sci B Polym Phys 37:647–659

    Article  CAS  Google Scholar 

  19. Huang MT, Ishida H (1999) Investigation of the boron nitride/polybenzoxazine interphase. J Polym Sci B Polym Phys 37:2360–2372

    Article  CAS  Google Scholar 

  20. Zhang R, Lu X, Lou C, Zhou C, Xin Z (2019) Preparation of diamine-based polybenzoxazine coating for corrosion protection on mild steel. J Polym Res 26:29–36

    Article  Google Scholar 

  21. Yu X, Zhang K (2020) Studies on the isomeric effect of nitrile functionality on the polymerization and thermal properties of ortho-norbornene-based benzoxazine resins. J Polym Res 27:130–137

    Article  CAS  Google Scholar 

  22. Wang S, Jing X, Wang Y, Si J (2014) Synthesis and characterization of novel phenolic resins containing aryl-boron backbone and their utilization in polymeric composites with improved thermal and mechanical properties. Polym Adv Technol 25:152–159

    Article  CAS  Google Scholar 

  23. Si J, Xu P, He W, Wang S, Jing X (2012) Bis-benzoxazine resins with high char yield and toughness modified by hyperbranched poly(resorcinol borate). Composites A: Appl Sci Man 43:2249–2255

    Article  CAS  Google Scholar 

  24. Ramdani N, Derradji M, Wang J, Mokhnache EIQ, Liu WB (2016) Improvements of thermal, mechanical and water-resistance properties of polybenzoxazine/boron carbide nanocomposites. JOM 68:2533–2542

    Article  CAS  Google Scholar 

  25. Liu Y, Zhang X, Yang X (2013) A novel hyperbranched polyborazine and its reactive blend with benzoxazine thermosets. Polym Eng Sci 53:507–515

    Article  CAS  Google Scholar 

  26. Wang S, Jia Q, Liu Y, Jing X (2015) An investigation on the effect of phenylboronic acid on the processabilities and thermal properties of bis-benzoxazine resins. React Funct Polym 93:111–119

    Article  CAS  Google Scholar 

  27. Telli AH, Hacaloglu J (2018) Effects of aromatic diboronic acid on thermal charateristics of polybenzoxazines based on phenol and aniline. Europ Polym J 108:182–190

    Article  CAS  Google Scholar 

  28. Ipek H, Hacaloglu J (2018) The effect of aromatic diboronic acid on characteristics of polybenzoxazine based on phenol and 4-aminomethylbenzoate. J Polym Res 25:263–269

    Article  Google Scholar 

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Authors and Affiliations

  1. The Scientific and Technological Research Council of Turkey, Defense Industries Research and Development Institute, TR-06800, Ankara, Turkey

    Halil Ipek

  2. Department of Chemistry, Middle East Technical University, TR-06800, Ankara, Turkey

    Jale Hacaloglu

  3. Department of Polymer Science & Technology, Middle East Technical University, TR-06800, Ankara, Turkey

    Jale Hacaloglu

Authors
  1. Halil Ipek
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  2. Jale Hacaloglu
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Correspondence to Halil Ipek or Jale Hacaloglu.

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Highlights

• Polybenzoxazine composites were prepared by using aromatic boronic acid.

• Improvement in thermal characteristics of polybenzoxazine was detected.

• Interactions between functional groups of benzoxazine and boronic acid were detected.

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Ipek, H., Hacaloglu, J. The effect of 3-hydroxyphenylboronic acid on thermal characteristics of polybenzoxazine based on phenol and 4-aminomethylbenzoate. J Polym Res 27, 245 (2020). https://doi.org/10.1007/s10965-020-02221-2

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  • DOI: https://doi.org/10.1007/s10965-020-02221-2

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