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Synthesis and properties of novel poly(aryl ether ketone)s containing imide linkages in the main chains

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Abstract

A new monomer containing imide linkages, bis[4-(p-phenoxybenzoyl)-1,2-benzenedioyl]-N,N,N′,N′-4,4′-diaminodiphenyl ether (BPBDADPE), was prepared by the Friedel–Crafts reaction of bis(4-chloroformyl-1,2-benzenedioyl)-N,N,N′,N′-4,4′-diaminodiphenyl ether (BCBDADPE) with diphenyl ether (DPE). Novel poly(aryl ether ketone)s containing imide linkages in the main chains (PEK-I) were synthesized by electrophilic Friedel–Crafts solution copolycondensation of terephthaloyl chloride (TPC) with a mixture of DPE and BPBDADPE. The polymers were characterized by different physico-chemical techniques. The polymers with 10–40 mol% BPBDADPE are semicrystalline and had increased T gs over commercially available poly(ether ether ketone) (PEEK) and poly(ether ketone ketone) (PEKK) (70/30) due to the incorporation of imide linkages in the main chains. The polymers IV and V with 30–40 mol% BPBDADPE had not only high T gs of 182–183 °C, but also moderate T ms of 341–343 °C, having good potential for melt processing and exhibited high thermal stability and good resistance to common organic solvents.

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References

  1. Rose JB (1974) Preparation and properties of poly(arylene ether sulphones). Polymer 15:456–465

    Article  CAS  Google Scholar 

  2. Ohno M, Takata T, Endo T (1995) Synthesis of a novel naphthalene-based poly(arylene ether-ketone) by polycondensation of 1,5-bis(4-fluorobenzoyl)-2,6-dimethylnaphthalene with bisphenol. J Polym Sci Polym Chem Ed 33:2647–2655

    Article  CAS  Google Scholar 

  3. Ji XL, Yu DH, Zhang WJ, Wu ZW (1997) The multiple melting behavior of immiscible poly(ether ether ketone)/poly(ether diphenyl ether ketone) blend. Polymer 38:3501–3504

    Article  CAS  Google Scholar 

  4. Rose JB (1986) In: Seymour RB, Kirshenbaum GS (eds) High performance polymers: their origin and development. Elsevier, New York, p 187

  5. Mullins MJ, Woo EP (1987) The synthesis and properties of poly(aromatic ketones). J Macromol Sci Rev Macromol Chem Phys C27:313–341

    CAS  Google Scholar 

  6. Staniland PA (1989) In: Allen G, Bevington JC (eds) Comprehensive polymer science, vol 5. Pergamon Press, Oxford, p 483

  7. Clendinning RA, Kelsey DR, Botkin JH, Winslow PA, Youssefi M, Cotter RJ, Matzner M, Kwiatkowski GT (1993) Poly(aryl ether ketone) block and chain-extended copolymers. 1. Preparation and characterization of a new class of functional poly(aryl ether ketone) oligomers. Macromolecules 26:2361–2365

    Article  CAS  Google Scholar 

  8. Chan KP, Wang Y, Hay AS (1995) Convenient synthesis and facile polymerization of cyclic aryl ether ketones containing the 1,2-dibenzoylbenzene moiety. Macromolecules 28:653–655

    Article  CAS  Google Scholar 

  9. Colquhoun HM, Sestiaa LG, Zolotukhin MG (2000) Macrocyclic ring-chain poly(ether ketone)s. Macromolecules 33:8907–8909

    Article  CAS  Google Scholar 

  10. Ben-Haida A, Colquhoun HM, Hodge P, Williams DJ (2006) Synthesis of a catechol-based poly(ether ether ketone) (“o-PEEK”) by classical step-growth polymerization and by entropically driven ring-opening polymerization of macrocyclic oligommers. Macromolecules 39:6467–6472

    Article  CAS  Google Scholar 

  11. Wang J, Gao Y, Hlil AR, Hay AS (2008) Synthesis of high molecular weight poly(phthalazinone ether)s by Ullmann C–N and C–O condensation reactions. Macromolecules 41:298–300

    Article  CAS  Google Scholar 

  12. Sakaguchi Y, Tokai M, Kato Y (1993) Synthesis of poly(ether ketone) by Friedel-Crafts acylation: effects of reaction conditions. Polymer 34:1512–1515

    Article  CAS  Google Scholar 

  13. Zolotukhin MG, Dosieret M, Fougnies C, Villers D, Gileva NG, Fatykhov AA (1995) Aromatic homopolymers obtained by precipitation polycondensation: 1. Synthesis of naphthalene-containing polyketones. Polymer 36:3575–3583

    Article  CAS  Google Scholar 

  14. Krishnaswamy RK, Kalika DS (1996) Glass transition characteristics of poly(aryl ether ketone ketone) and its copolymers. Polymer 37:1915–1923

    Article  CAS  Google Scholar 

  15. Zolotukhin MG, Rueda DR, Balta Calleja FJ, Cagiao ME, Sedova EA, Gileva NG (1997) Aromatic polymers obtained by precipitation polycondensation: 4*. Synthesis of poly(ether ketone ketone)s. Polymer 38:1471–1476

    Article  CAS  Google Scholar 

  16. Rueda DR, Zolotukhin MG, Cagiao ME, Balta Calleja FJ, Villers D, Dosiere M (1996) Aromatic polymers obtained by precipitation polycondensation. 3. Thermal behavior and microstructure of PEKEKK particles. Macromolecules 29:7016–7021

    Article  CAS  Google Scholar 

  17. Zolotukhin MG, Colquhoun HM, Sestiaa LG, Rueda DR, Flot D (2003) One-pot synthesis and characterization of soluble poly(aryl ether-ketone)s having pendant carboxyl groups. Macromolecules 36:4766–4771

    Article  CAS  Google Scholar 

  18. Ritter H, Thorwirth R, Muller G (1993) Comb-like poly(aryl-ether-ketones) containing naphthalene moieties in the main chain. Makromol Chem 194:1469–1481

    Article  CAS  Google Scholar 

  19. Ohno M, Takata T, Endo T (1994) Synthesis of a novel naphthalene-based poly(arylene ether ketone) with high solubility and thermal stability. Macromolecules 27:3447–3448

    Article  CAS  Google Scholar 

  20. Liu B, Wang G, Hu W, Jin Y, Chen C, Jiang Z, Zhang W, Wu Z, Wei Y (2002) Poly(aryl ether ketone)s with (3-methyl)phenyl and (3-trifluoromethyl)phenyl side groups. J Polym Sci Polym Chem Ed 40:3392–3398

    Article  CAS  Google Scholar 

  21. Zhang Y, Sun X, Xu R, Niu Y, Wang G, Jiang Z (2006) Synthesis and characterization of novel fluorine-containing poly(aryl ether ketone)s containing 1,4-naphthalene units. Mater Chem Phys 99:465–469

    Article  CAS  Google Scholar 

  22. Liu B, Hu W, Chen C, Jiang Z, Zhang W, Wu Z, Matsumoto T (2004) Soluble aromatic poly(ether ketone)s with a pendant 3,5-ditrifluoromethylphenyl group. Polymer 45:3241–3247

    Article  CAS  Google Scholar 

  23. Liu B, Robertson GP, Kim DS, Guiver MD, Hu W, Jiang Z (2007) Aromatic poly(ether ketone)s with pendant sulfonic acid phenyl groups prepared by a mild sulfonation method for proton exchange membranes. Macromolecules 40:1934–1944

    Article  CAS  Google Scholar 

  24. Shibata M, Cao J, Yosomiya R (1997) Synthesis and properties of the block copolymers of poly(ether ether ketone) and the poly(aryl ether sulfone) containing biphenylene moiety. Polymer 38:3103–3108

    Article  CAS  Google Scholar 

  25. Faghihi K, Haijibeygi M (2004) Synthesis and properties of new poly(amide imide)s containing trimellitic rings and hydantoin moieties in the main chain under microwave irradiation. J Appl Polym Sci 92:3447–3453

    Article  CAS  Google Scholar 

  26. Janson V, Gors HC (1984) Preparation of aromatic polymer. WO 8403891

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Acknowledgment

The authors thank the National Natural Science Foundation of China (Project 20764001) for financial support.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Guangzhou, 510006, People’s Republic of China

    Hong Zhao & Qin Xi

  2. Department of Chemistry, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Mingzhong Cai

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  1. Hong Zhao
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  2. Qin Xi
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  3. Mingzhong Cai
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Correspondence to Mingzhong Cai.

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Zhao, H., Xi, Q. & Cai, M. Synthesis and properties of novel poly(aryl ether ketone)s containing imide linkages in the main chains. Polym. Bull. 67, 1139–1152 (2011). https://doi.org/10.1007/s00289-010-0443-2

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  • DOI: https://doi.org/10.1007/s00289-010-0443-2

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