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Synthesis and properties of novel copolymers of poly(ether ketone biphenyl ketone ether ketone ketone) and poly(ether ketone sulfone amide)

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Abstract

The monomer containing sulfone and amide linkages, namely N,N'-bis(4-phenoxybenzoyl)-4,4'-diaminodiphenyl sulfone (BPBDAS), was conveniently prepared by the condensation of 4,4′-diaminodiphenyl sulfone with 4-phenoxybenzoyl chloride in N,N-dimethylacetamide (DMAc). Novel copolymers of poly (ether ketone biphenyl ketone ether ketone ketone) and poly (ether ketone sulfone amide) were synthesized by the modified Friedel-Crafts acylation solution copolycondensation of isophthaloyl chloride (IPC) with a mixture of 4,4′-bis (4-phenoxybenzoyl) biphenyl (BPOBBP) and BPBDAS. The copolymers obtained were characterized by different physico-chemical techniques. The copolymers with 10–25 mol% BPBDAS are semicrystalline and had increased T gs over the conventional PEEK and PEKK due to the incorporation of rigid biphenylene moieties, sulfone and amide linkages in the main chains. The copolymers III and IV with 20–25 mol% BPBDAS had not only high T gs of 182–185 °C, but also moderate T ms of 337–339 °C, having good potential for the melt processing. The copolymers III and IV had tensile strengths of 102.2–103.5 MPa, Young’s moduli of 2.65–2.76 GPa, and elongations at break of 17.5–18.9 % and exhibited high thermal stability and excellent resistance to organic solvents.

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References

  1. Rose JB (1974) Polymer 15:456–465

  2. Ohno M, Takata T, Endo T (1995) J Polym Sci A Polym Chem 33:2647–2655

    CAS  Google Scholar 

  3. Ji XL, Yu DH, Zhang WJ, Wu ZW (1997) Polymer 38:3501–3504

    Article  CAS  Google Scholar 

  4. Horner PJ, Whiteley RH (1991) J Mater Chem 1:271–280

    CAS  Google Scholar 

  5. He L, Chao D, Wang X, Jia X, Wang C, Liu X (2012) J Polym Res 19:9999–10006

    Article  Google Scholar 

  6. Rose JB (1986) In High Performance Polymers: Their Origin and Development; Seymour RB, Kirshenbaum GS, Eds; Elsevier: New York, p187.

  7. Mullins MJ, Woo EP (1987) J Macromol Sci Rev Macromol Chem Phys C 27:313–341

    Article  Google Scholar 

  8. Staniland PA (1989) In Comprehensive Polymer Science; Allen G, Bevington JC, Eds; Pergamon Press: Oxford, Vol.5, p483

  9. Cotter RJ (1995) Engineering Plastics: A Handbook of Polyarylethers. Gordon and Breach Science Publishers, Basel, Switzerland

    Google Scholar 

  10. Yonezawa N, Okamoto A (2009) Polym J 41:899–928

    Article  CAS  Google Scholar 

  11. Clendinning RA, Kelsey DR, Botkin JH, Winslow PA, Youssefi M, Cotter RJ, Matzner M, Kwiatkowski GT (1993) Macromolecules 26:2361–2365

    Article  CAS  Google Scholar 

  12. Chan KP, Wang Y, Hay AS (1995) Macromolecules 28:653–655

    Article  CAS  Google Scholar 

  13. Colquhoun HM, Sestiaa LG, Zolotukhin MG (2000) Macromolecules 33:8907–8909

    Article  CAS  Google Scholar 

  14. Ben-Haida A, Colquhoun HM, Hodge P, Williams DJ (2006) Macromolecules 39:6467–6472

    Article  CAS  Google Scholar 

  15. Wang J, Gao Y, Hlil AR, Hay AS (2008) Macromolecules 41:298–300

    Article  CAS  Google Scholar 

  16. Sakaguchi Y, Tokai M, Kato Y (1993) Polymer 34:1512–1515

    Article  CAS  Google Scholar 

  17. Zolotukhin MG, Dosieret M, Fougnies C, Villers D, Gileva NG, Fatykhov AA (1995) Polymer 36:3575–3583

    Article  CAS  Google Scholar 

  18. Krishnaswamy RK, Kalika DS (1996) Polymer 37:1915–1923

    Article  CAS  Google Scholar 

  19. Zolotukhin MG, Rueda DR, Balta Calleja FJ, Cagiao ME, Sedova EA, Gileva NG (1997) Polymer 38:1471–1476

    Article  CAS  Google Scholar 

  20. Rueda DR, Zolotukhin MG, Cagiao ME, Balta Calleja FJ, Villers D, Dosiere M (1996) Macromolecules 29:7016–7021

    Article  CAS  Google Scholar 

  21. Zolotukhin MG, Colquhoun HM, Sestiaa LG, Rueda DR, Flot D (2003) Macromolecules 36:4766–4771

    Article  CAS  Google Scholar 

  22. Ritter H, Thorwirth R, Muller G (1993) Makromol Chem 194:1469–1481

    Article  CAS  Google Scholar 

  23. Ohno M, Takata T, Endo T (1994) Macromolecules 27:3447–3448

    Article  CAS  Google Scholar 

  24. Liu B, Wang G, Hu W, Jin Y, Chen C, Jiang Z, Zhang W, Wu Z, Wei Y (2002) J Polym Sci Polym Chem Ed 40:3392–3398

    CAS  Google Scholar 

  25. Zhang Y, Sun X, Xu R, Niu Y, Wang G, Jiang Z (2006) Mater Chem Phys 99:465–469

    CAS  Google Scholar 

  26. Liu B, Hu W, Chen C, Jiang Z, Zhang W, Wu Z, Matsumoto T (2004) Polymer 45:3241–3247

    Article  CAS  Google Scholar 

  27. Cao J, Su W, Wu Z, Kitayama T, Hatada K (1994) Polymer 35:3549–3556

    Article  CAS  Google Scholar 

  28. Wu Z, Zheng Y, Yan H, Nakamura T, Nozawa T, Yosomiya R (1989) Angew Makromol Chem 173:163–181

    Article  CAS  Google Scholar 

  29. Yu X, Zheng Y, Wu Z, Tang X (1990) J Appl Polym Sci 41:2649–2654

    Article  CAS  Google Scholar 

  30. Shibata M, Cao J, Yosomiya R (1997) Polymer 38:3103–3108

    Article  CAS  Google Scholar 

  31. Kruger KN, Zachmann HG (1993) Macromolecules 26:5202–5208

    Article  Google Scholar 

  32. Yu Y, Xiao F, Cai M (2007) J Appl Polym Sci 104:3601–3606

    Article  CAS  Google Scholar 

  33. Cai M, Xiao F, Ding N, Song C (2009) Polym Adv Technol 20:981–986

    Article  CAS  Google Scholar 

  34. Yan T, Chen M, Xu Q, Cai M (2013) J Polym Res 21:336–343

    Article  Google Scholar 

  35. Huang B, Sun Y, Wang G, Cai M (2013) J Polym Res 20:81–88

    Article  Google Scholar 

  36. Janson V, Gors HC (1984) Preparation of aromatic polymer. PCT Int WO 8:403,891

    Google Scholar 

  37. Bonner WH (1962) Aromatic polyketones and preparation. US Patent 3065205

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Acknowledgments

The authors thank the National Natural Science Foundation of China (Project 21,264,010) and the Natural Science Foundation of Jiangxi Province of China (Project 20132BAB203015) for financial support.

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Authors and Affiliations

  1. Analytical & Testing Centre and Department of Chemistry, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Yu Wang, Qiang Xu, Tao Yan & Mingzhong Cai

  2. Department of Chemistry, Jiujiang University, Jiujiang, 332000, People’s Republic of China

    Pingping Wang

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  1. Yu Wang
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  2. Pingping Wang
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  3. Qiang Xu
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  4. Tao Yan
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  5. Mingzhong Cai
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Correspondence to Mingzhong Cai.

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Wang, Y., Wang, P., Xu, Q. et al. Synthesis and properties of novel copolymers of poly(ether ketone biphenyl ketone ether ketone ketone) and poly(ether ketone sulfone amide). J Polym Res 21, 533 (2014). https://doi.org/10.1007/s10965-014-0533-1

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  • DOI: https://doi.org/10.1007/s10965-014-0533-1

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