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Synthesis and characterization of processable aromatic poly(ether ether ketone amide)s modified by phenoxy and 1,3 ketone moiety linkages

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A Correction to this article was published on 24 January 2020

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Abstract

New series of aromatic poly(ether ether ketone amide)s were synthesized by low-temperature solution polymerization of novel aromatic diamine, namely 1,3-bis-4′-(4″-aminophenoxy benzoyl)benzene (XIV), and aromatic diacid chlorides, viz. isophthaloyl chloride (IPC) and terephthaloyl chloride (TPC). Co-poly(ether ether ketone amide)s were also synthesized by employing various mole proportions of IPC and TPC with diamine (XIV). These poly(ether ether ketone amide)s were characterized by FTIR, solubility, inherent viscosity, TGA, DSC, and XRD. Inherent viscosities of these poly(ether ether ketone amide)s were in the range of 0.41–0.52 dL/g in DMAc, indicating the formation of moderate to high molecular weight of polymers. Poly(ether ether ketone amide)s showed good solubility in polar aprotic solvents such as N,N-dimethyl acetamide (DMAc), N-methyl 2-pyrrolidone, N,N-dimethylformamide, and dimethyl sulfoxide. These poly(ether ether ketone amide)s had glass transition temperatures, as determined by DSC, in the range of 252–302 °C. These polymers showed similar decomposition patterns and had no weight loss below 335 °C, and temperatures for 10% weight loss (T10) were in the range of 397–406 °C, indicating that these polymers showed good thermal stability.

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  • 24 January 2020

    The article “Synthesis and characterization of processable aromatic poly(ether ether ketone amide)s

References

  1. Ferreiro JJ, De la Campa JG, Lozano AE, De Abajo J, Preston J (2007) Synthesis and characterization of aromatic polyamides containing alkylphthalimido pendent groups. J Polym Sci A Polym Chem 45:4671

    Article  CAS  Google Scholar 

  2. Liu XL, Wu D, Sun R, Yu LM, Jiang JW, Sheng SR (2013) Synthesis and properties of novel soluble fluorinated polyamides containing pyridine and sulfone moieties. J Fluor Chem 154:16

    Article  CAS  Google Scholar 

  3. Mohanty A, Sen SK, Maji S, Dasgupta B, Chatterjee S, Banerjee S (2010) Synthesis, characterization and comparison of properties of new fluorinated poly(arylene ether)s containing phthalimide moiety in the main chain. J Polym Adv Technol 20:384

    Google Scholar 

  4. Wu SC, Shu CF (2003) Synthesis and properties of soluble aromatic polyamides derived from 2,2-bis(4-carboxyphenoxy)-9,9′-spirobifluorene. J Polym Sci A Polym Chem 41:1160

    Article  CAS  Google Scholar 

  5. Tamboli AB, Bhorkade RG, Kalshetti BS, Ghodake SD, Maldar NN (2019) Soluble aromatic polyamides modified by incorporation of 1,2,4-triazole and pentadecyl units into the backbone of polymer. J Macromol Sci A Pure Appl Chem 160:2475

    Google Scholar 

  6. Tamboli AB, Maldar NN (2019) Soluble aromatic polyamides containing pendant pentadecyl substituted methoxy phenyl unit. J Polym Res 26:139

    Article  Google Scholar 

  7. Matsuo S (1994) Synthesis and properties of poly(arylene ether phenyl -s-triazine)s. J Polym Sci A Polym Chem 32:2093

    Article  CAS  Google Scholar 

  8. Damaceanu MD, Rusa RD, Nicolscu A, Bruma M, Rusnov AL (2011) Organosoluble asymmetric aromatic polyamides bearing pendent phenoxy groups. J Polym Int 60:1248

    Article  CAS  Google Scholar 

  9. Ubale VB, Patil AS, Maldar NN (2007) Polyhydrazide based on 2,5-bis(4-carboxy methylene phenyl)-3,4-diphenyl thiophene. Euro Polym J 43:1038

    Article  CAS  Google Scholar 

  10. Sayyad MM, Maldar NN (2009) Novel poly(arylene ether ether ketone)s containing performed imide unit and pendant long chain alkyl group. J Mater Sci Eng B 10:2016

    Google Scholar 

  11. Feihua Z, Huan W, Tao Y, Mingzhong C (2016) Synthesis and properties of novel soluble aromatic polyamides containing 4-aryl-2,6-diphenylpyridine moieties and pendant fluorinated phenoxy group. J Polym Res 23:225

    Article  Google Scholar 

  12. Yamazaki N, Higashi F, Kawataba J (1974) Studies on reactions of the N-phosphonium salts of pyridines. XI. Preparation of polypeptides and polyamides by means of triarylphosphites in pyridine. J Polym Sci A Polym Chem 12:2149

    Article  CAS  Google Scholar 

  13. Debaditya B, Venkat P, Banerjee S (2015) Highly gas permeable polyamides based on substituted Triphenylamine. J Macromolecules 48:4541

    Article  Google Scholar 

  14. Lu J, Yan G, Zhang G, Yang J (2017) Synthesis and property investigation of poly(arylene ethers) with pendant cyclohexyl units. J Polym Res 24:152

    Article  Google Scholar 

  15. Labadie JW, Hedrick JL, Ueda M (1996) Poly(aryl ether) synthesis. ACS Symp 624:210–225

    Article  CAS  Google Scholar 

  16. Rose JB (1997) Preparation and properties of poly(arylene ether sulfone). J Polym 15:456

    Article  Google Scholar 

  17. Attwood TE, Dawson PC, Freeman J, Hoy LR, Rose JB, Staniland PA (1981) Synthesis and properties of poly (aryl ether ketone). J Polym 22:1096

    Article  CAS  Google Scholar 

  18. Shukla D, Negi YS, Upadhyaya TS, Kumar V (2012) Synthesis and modification of poly(ether ether ketone) and their properties; a review. J Polym Rev 52:189

    Article  CAS  Google Scholar 

  19. Tawade BV, Valsange NG, Wadgaonkar PP (2016) Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains. High Perform Polym. https://doi.org/10.1177/0954008316660368

    Article  Google Scholar 

  20. Hamciuc C, Hamciuc E, Bruma M, Klapper M, Pakula T (2001) Poly(ether-imide) and poly(ether-imide)-polydimethyl-siloxane containing isopropylidene groups. Polym Bull 47:1

    Article  CAS  Google Scholar 

  21. Dinari M, Haghighi A (2017) Synthesis and characterization of new heat-resistant polyamides bearing an s-triazine under green condition. J Polym Res 24:29

    Article  Google Scholar 

  22. Morgan PW (1963) Low temperature solution polycondensation. J Polym Sci C 4:1075

    Article  Google Scholar 

  23. Sagar AD, Shingte RD, Wadgaonkar PP, Salunkhe MM (2001) Polyamides containing s-triazine ring and fluorene cardo group: synthesis and characterization. Eur Polym J 37:1493

    Article  CAS  Google Scholar 

  24. Mathew JS (2001) Ph.D. Thesis submitted to university Pune (India). Novel thermally stable polymers from renewable resources (cashew nut shell liquid) synthesis, characterization and application

  25. Hsiao SH, Chang YH (2004) New soluble aromatic polyamides containing ether linkages and laterally attached p-terphenyls. Eur Polym J 40:1749

    Article  CAS  Google Scholar 

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Acknowledgements

Dr. A.B.Tamboli is thankful to University Grants Commission (UGC) (Grant No. 17.145-2013-14(SA-1)) for providing Research fellowship JRF and SRF as financial assistance.

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  1. Santosh Bhimrao Patil College of Arts, Commerce and Science, Mandrup, Maharashtra, 413221, India

    A. B. Tamboli & N. N. Maldar

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  1. A. B. Tamboli
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  2. N. N. Maldar
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Tamboli, A.B., Maldar, N.N. Synthesis and characterization of processable aromatic poly(ether ether ketone amide)s modified by phenoxy and 1,3 ketone moiety linkages. Polym. Bull. 77, 6591–6605 (2020). https://doi.org/10.1007/s00289-019-03093-3

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