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Preparation of high-performance polyimide fibers containing benzimidazole and benzoxazole units

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Abstract

A series of aromatic copolyimide (co-PI) fibers containing benzimidazole and benzoxazole were prepared by introducing 5-amino-2-(4-aminobenzene)benzoxazole (BOA) and 2-(4-aminophenyl)-5-aminobenzimidazole (BIA) into the rigid 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA)/p-phenylenediamine (p-PDA) backbone via a typical two-step wet-spinning method. The incorporated BOA and BIA moieties in the polymer chains resulted in significant changes on the comprehensive performances of the resulting PI fibers. The optimum tensile strength was 2.26 GPa with the BIA/BOA molar ratio of 3/1, whereas the optimum initial modulus was 145.0 GPa with the BIA/BOA molar ratio of 1/3. The drastically improved mechanical properties were originated from the hydrogen-bonding intermolecular interactions by BIA moieties and high molecular orientation by BOA moieties. FT-IR results confirmed the presence of hydrogen-bonding interaction in the fibers with high imidization degree. Two-dimensional wide-angle X-ray diffraction (2D WAXD) indicated the existence of highly oriented structures along the fiber axial direction, while this feature varied with different diamine ratios. SEM observations showed that the fibers were obtained with homogeneous and uniform structures at various diamine ratios. Meanwhile, the co-PI fibers exhibited excellent thermal properties with 5 % weight loss temperature ranging from 563 to 570 °C in nitrogen and glass transition temperature ranging from 308 to 321 °C.

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References

  1. Hasegawa M, Horie K (2001) Photophysics, photochemistry, and optical properties of polyimides. Prog Polym Sci 26:259–335

    Article  Google Scholar 

  2. Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS (2012) Advanced polyimide materials: syntheses, physical properties and applications. Prog Polym Sci 37:907–974

    Article  Google Scholar 

  3. Hsiao SH, Chen YJ (2002) Structure–property study of polyimides derived from PMDA and BPDA dianhydrides with structurally different diamines. Eur Polym J 38:815–828

    Article  Google Scholar 

  4. Kaneda T, Katsura T, Nakagawa K, Makino H, Horio M (1986) High-strength–high-modulus polyimide fibers I. One-step synthesis of spinnable polyimides. J Appl Polym Sci 32:3133–3149

    Article  Google Scholar 

  5. Kaneda T, Katsura T, Nakagawa K, Makino H, Horio M (1986) High-strength-high-modulus polyimide fibers II. Spinning and properties of fibers. J Appl Polym Sci 32:3151–3176

    Article  Google Scholar 

  6. Dorogy WE, Clair AKS (1991) Wet spinning of solid polyamic acid fibers. J Appl Polym Sci 43:501–519

    Article  Google Scholar 

  7. Dorogy WE, Clair AKS (1993) Fibers from a soluble, fluorinated polyimide. J Appl Polym Sci 49:501–510

    Article  Google Scholar 

  8. Li WH, Wu ZQ, Jiang H, Eashoo M, Harris FW, Cheng SZD (1996) High-performance aromatic polyimide fibres. J Mater Sci 31:4423–4431. doi:10.1007/BF00356470

    Article  Google Scholar 

  9. Li WH, Wu ZQ, Zhang AQ, Leland ME, Park JY, Harris FW, Cheng SZD (1997) High-performance aromatic polyimide fibers. 6. Structure and morphology changes in compressed BPDA-DMB fibers. J Macromol Sci Part B Phys 36:315–333

    Article  Google Scholar 

  10. Zhang QH, Dai M, Ding MX, Chen DJ, Gao LX (2004) Morphology of polyimide fibers derived from 3, 3′, 4, 4′-biphenyltetracarboxylic dianhydride and 4, 4′-oxydianiline. J Appl Polym Sci 93:669–675

    Article  Google Scholar 

  11. Zhang QH, Luo WQ, Gao LX, Chen DJ, Ding MX (2004) Thermal mechanical and dynamic mechanical property of biphenyl polyimide fibers. J Appl Polym Sci 92:1653–1657

    Article  Google Scholar 

  12. Dong J, Yin CQ, Lin JY, Zhang DB, Zhang QH (2014) Evolution of the microstructure and morphology of polyimide fibers during heat-drawing process. RSC Adv 4:44666–44673

    Article  Google Scholar 

  13. Yin CQ, Dong J, Zhang ZX, Zhang QH, Lin JY (2015) Structure and properties of polyimide fibers containing benzimidazole and Amide Units. J Polym Sci, Part B 53:183–191

    Article  Google Scholar 

  14. Yin CQ, Dong J, Tan WJ, Lin JY, Chen DJ, Zhang QH (2015) Strain-induced crystallization of polyimide fibers containing 2-(4-aminophenyl)-5-aminobenzimidazole moiety. Polymer 75:178–186

    Article  Google Scholar 

  15. Zhang MY, Niu HQ, Chang JJ, Ge QY, Cao L, Wu DZ (2015) High-performance fibers based on copolyimides containing benzimidazole and ether moieties: molecular packing, morphology, hydrogen-bonding interactions and properties. Polym Eng Sci 55:2615–2625

    Article  Google Scholar 

  16. Liu XY, Gao GQ, Dong L, Ye GD, Gu Y (2009) Correlation between hydrogen-bonding interaction and mechanical properties of polyimide fibers. Polym Adv Technol 20:362–366

    Article  Google Scholar 

  17. Zhang QH, Dai M, Ding MX, Chen DJ, Gao LX (2004) Mechanical properties of BPDA–ODA polyimide fibers. Eur Polym J 40:2487–2493

    Article  Google Scholar 

  18. Eashoo M, Shen DX, Wu ZQ, Lee CJ, Harris FW, Cheng SZD (1993) High-performance aromatic polyimide fibres: 2. Thermal mechanical and dynamic properties. Polymer 34:3209–3215

    Article  Google Scholar 

  19. Chang JJ, Niu HQ, Zhang MY, Ge QY, Li Y, Wu DZ (2015) Structures and properties of polyimide fibers containing ether units. J Mater Sci 50:4104–4114. doi:10.1007/s10853-015-8966-4

    Article  Google Scholar 

  20. Cheng SZD, Wu ZQ, Mark E (1991) A high-performance aromatic polyimide fibre: 1. Structure, properties and mechanical-history dependence. Polymer 32:1803–1810

    Article  Google Scholar 

  21. Eashoo M, Wu ZQ, Zhang AQ, Shen DX, Tse C, Harris FW, Cheng SZD, Gardner KH, Hsiao BS (1994) High performance aromatic polyimide fibers, 3. A polyimide synthesized from 3, 3′, 4, 4′-biphenyltetracarboxylic dianhydride and 2, 2′-dimethyl-4, 4′-diaminobiphenyl. Macromol Chem Phys 195:2207–2225

    Article  Google Scholar 

  22. Dong J, Yin CQ, Luo WQ, Zhang QH (2013) Synthesis of organ-soluble copolyimides by one-step polymerization and fabrication of high performance fibers. J Mater Sci 48:7594–7602. doi:10.1007/s10853-013-7576-2

    Article  Google Scholar 

  23. Niu HQ, Qi SL, Han EL, Tian GF, Wang XD, Wu DZ (2012) Fabrication of high-performance copolyimide fibers from 3, 3′, 4, 4′-biphenyltetracarboxylic dianhydride, p-phenylenediamine and 2-(4-aminophenyl)-6-amino-4 (3H)-quinazolinone. Mater Lett 89:63–65

    Article  Google Scholar 

  24. Chang JJ, Niu HQ, He M, Sun M, Wu DZ (2015) Structure–property relationship of polyimide fibers containing ether groups. J Appl Polym Sci 132:42474

    Google Scholar 

  25. Chang JJ, Ge QY, Zhang MY, Liu WW, Cao L, Niu HQ, Sui G, Wu DZ (2015) Effect of pre-imidization on the structures and properties of polyimide fibers. RSC Adv 5:69555–69566

    Article  Google Scholar 

  26. Zhang MY, Niu HQ, Lin ZW, Qi SL, Chang JJ, Ge QY, Wu DZ (2015) Preparation of high performance copolyimide fibers via increasing draw ratios. Macromol Mater Eng 300:1096–1107

    Article  Google Scholar 

  27. Eashoo M, Buckley LJ, Clair AKS (1997) Fibers from a low dielectric constant fluorinated polyimide: solution spinning and morphology control. J Polym Sci 35:173–185

    Article  Google Scholar 

  28. Chang JJ, Liu WW, Zhang MY, Cao L, Ge QY, Niu HQ, Sui G, Wu DZ (2015) Structures and properties of polyimide fibers containing fluorine groups. RSC Adv 5:71425–71432

    Article  Google Scholar 

  29. Huang SB, Jiang ZY, Ma XY, Qiu XP, Men YF, Gao LX, Ding MX (2013) Properties, morphology and structure of BPDA/PPD/ODA polyimide fibres. Plast, Rubber Compos 42:407–415

    Article  Google Scholar 

  30. Luo LB, Yao J, Wang X, Li K, Huang JY, Li BY, Wang HN, Liu XY (2014) The evolution of macromolecular packing and sudden crystallization in rigid-rod polyimide via effect of multiple H-bonding on charge transfer (CT) interactions. Polymer 55:4258–4269

    Article  Google Scholar 

  31. Gao GQ, Dong L, Liu XY, Ye GD, Gu Y (2008) Structure and properties of novel PMDA/ODA/PABZ polyimide fibers. Polym Eng Sci 48:912–917

    Article  Google Scholar 

  32. Dong J, Yin CQ, Zhang ZX, Wang XY, Li HB, Zhang QH (2014) Hydrogen-bonding interactions and molecular packing in polyimide fibers containing benzimidazole units. Macromol Mater Eng 299:1170–1179

    Article  Google Scholar 

  33. Zhuang YB, Liu XY, Gu Y (2012) Molecular packing and properties of poly (benzoxazole-benzimidazole-imide) copolymers. Polym Chem 3:1517–1525

    Article  Google Scholar 

  34. Yin CQ, Dong J, Zhang DB, Lin JY, Zhang QH (2015) Enhanced mechanical and hydrophobic properties of polyimide fibers containing benzimidazole and benzoxazole units. Eur Polym J 67:88–98

    Article  Google Scholar 

  35. Luo LB, Zheng YX, Huang JY, Li K, Wang HN, Feng Y, Wang X, Liu XY (2015) High-performance copoly (benzimidazole-benzoxazole-imide) fibers: fabrication, structure, and properties. J Appl Polym Sci 132:42001

    Google Scholar 

  36. Liu XY, Guo LH, Gu Y (2005) A novel aromatic polyimide with rigid biphenyl side-groups: formation and evolution of structures in thermoreversible gel. Polymer 46:11949–11957

    Article  Google Scholar 

  37. Luo LB, Pang YW, Jiang X, Wang X, Zhang P, Chen Y, Peng CR, Liu XY (2012) Preparation and characterization of novel polyimide films containing amide groups. J Polym Res 19:1–7

    Article  Google Scholar 

  38. Wu TM, Chvalun SN, Blackwell J, Cheng SZD, Wu Z, Harris FW (1995) Effect of draw ratio on the structure of aromatic copolyimide fibers of random monomer sequence. Acta Polym 46:261–266

    Article  Google Scholar 

  39. Niu HQ, Huang MJ, Qi SL, Han EL, Tian GF, Wang XD, Wu DZ (2013) High-performance copolyimide fibers containing quinazolinone moiety: preparation, structure and properties. Polymer 54:1700–1708

    Article  Google Scholar 

  40. Goel RN, Hepworth A, Deopura BL, Varma IK, Varma DS (1979) Polyimide fibers: structure and morphology. J Appl Polym Sci 23:3541–3552

    Article  Google Scholar 

Download references

Acknowledgement

The authors greatly thank the financial support from the National Natural Science Foundation of China (NSFC, Project No. 51373008), National Key Basic Research Program of China (973 Program, No. 2014CB643606), and Beijing Key New Materials Research and Application Project (No. Z141100004214005).

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Authors and Affiliations

  1. State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029, China

    Meng Sun, Jingjing Chang, Guofeng Tian & Dezhen Wu

  2. Key Laboratory of Carbon Fiber and Functional Polymers, Ministry of Education, Beijing University of Chemical Technology, Beijing, 100029, China

    Hongqing Niu

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  1. Meng Sun
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  2. Jingjing Chang
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  3. Guofeng Tian
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  4. Hongqing Niu
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Correspondence to Hongqing Niu or Dezhen Wu.

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Sun, M., Chang, J., Tian, G. et al. Preparation of high-performance polyimide fibers containing benzimidazole and benzoxazole units. J Mater Sci 51, 2830–2840 (2016). https://doi.org/10.1007/s10853-015-9591-y

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