Skip to main content
SpringerLink
Log in

Synthesis of cardo poly(arylene ether ketone amide)s by heterogeneous palladium-catalyzed polycondensation of aromatic diiodides, aromatic diamines containing cardo groups and CO

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

New cardo poly(arylene ether ketone amide)s were synthesized by heterogeneous palladium-catalyzed carbonylative polycondensation of aromatic diiodides with ether–ketone linkages, aromatic diamines bearing cardo groups, and carbon monoxide. Polymerizations were conducted in N,N-dimethylacetamide (DMAc) at 120 °C in the presence of a bidentate phosphino-functionalized magnetic nanoparticles-immobilized palladium complex [Fe3O4@SiO2-2P-PdCl2] and 1,8-diazabicyclo[5,4,0]-7-undecene (DBU), yielding a series of cardo poly(arylene ether ketone amide)s with inherent viscosities up to 0.77 dL/g. All the polymers were readily soluble in various dipolar aprotic solvents at room temperature. These polymers showed good thermal stability with the glass transition temperature of 223–289 °C, the temperature at 5% weight loss of 441–464 °C in nitrogen. These cardo poly(arylene ether ketone amide)s could afford transparent, flexible, and strong films by solution-casting with good tensile properties. These polymer films exhibited lower dielectric constants, lower water uptakes, and higher optical transparency. Furthermore, this heterogeneous palladium catalyst can facilely be separated from the reaction mixture by simply applying an external magnet and recycled at least eight times with almost consistent activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Hearle JWS (2001) In high-performance fibers. Woodhead Publishing Limited, Cambridge

    Google Scholar 

  2. Yang HH (1989) Aromatic high-strength fibers. Wiley, New York, pp 66–289

    Google Scholar 

  3. Liou GS, Hsiao SH (2002) Synthesis and properties of new soluble aromatic polyamides and polyimides on the basis of N,N′-bis(3-aminobenzoyl)-N,N′-diphenyl-1,4-phenylenediamine. J Polym Sci Part A Polym Chem 40:2564–2574

    CAS  Google Scholar 

  4. Liaw DJ, Hsu PN, Chen WH, Lin SL (2002) High glass transitions of new polyamides, polyimides, and poly(amide-imide)s containing a triphenylamine group: synthesis and characterization. Macromolecules 35:4669–4675

    CAS  Google Scholar 

  5. 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 Part A Polym Chem 41:1160–1166

    CAS  Google Scholar 

  6. Garcia JM, Garcia FC, Serna F, de laPena JL (2010) High-performance aromatic polyamides. Prog Polym Sci 35:623–686

    CAS  Google Scholar 

  7. Bera D, Padmanabhan V, Banerjee S (2015) Highly gas permeable polyamides based on substituted triphenylamine. Macromolecules 48:4541–4554

    CAS  Google Scholar 

  8. Dewilde S, Hoogerstraete TV, Dehaen W, Binnemans K (2018) Synthesis of poly-p-phenylene terephthalamide (PPTA) in ionic liquid. ACS Sustain Chem Eng 6:1362–1369

    CAS  Google Scholar 

  9. Ankushrao SS, Kadam VN, Patil YS, Ubale VP, Maldar NN, Ghanwat AA (2017) Synthesis and characterization of processable heat resistant co-poly(ester-amide)s containing cyclopentylidene moiety. J Macromol Sci Part A Pure Appl Chem 54:124–132

    CAS  Google Scholar 

  10. Mahindrakar JN, Patil YS, Salunkhe PH, Ankushrao SS, Kadam VN, Ubale VP, Ghanwat AA (2018) Optically transparent, organosoluble poly(ether-amide)s bearing triptycene unit; synthesis and characterization. J Macromol Sci Part A Pure Appl Chem 55:658–667

    CAS  Google Scholar 

  11. Patil YS, Mahindrakar JN, Salunkhe PH, Ubale VP, Ghanwat AA (2018) Synthesis, characterization and structure–property relationships of processable poly(amide-imide)s containing novel tetraphenylthiophene-thiazole diimide-diacid (TPTPThDIDA) moiety. J Macromol Sci Part A Pure Appl Chem 55:572–581

    CAS  Google Scholar 

  12. Salunkhe PH, Ankushrao SS, Patil YS, Mahindrakar JN, Kadam VN, Ubale VP, Ghanwat AA (2018) Processable heat resistant polyamides containing tetraphenyl thiophene having pendant phenyl moiety with heterocyclic quinoxaline unit: synthesis and characterization. J Macromol Sci Part A Pure Appl Chem 55:377–383

    CAS  Google Scholar 

  13. Patil YS, Salunkhe PH, Mahindrakar JN, Ankushrao SS, Kadam VN, Ubale VP, Ghanwat AA (2018) Synthesis and characterization of aromatic polyimides containing tetraphenylfuranthiazole moiety. J Therm Anal Calorim 134:1–12

    Google Scholar 

  14. Fink JK (2008) High performance polymers. William Andrew, New York

    Google Scholar 

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

    CAS  Google Scholar 

  16. Rao VL (1995) Polyether ketones. J Macromol Sci Rev Macromol Chem Phys C 35:661–712

    Google Scholar 

  17. Kanetaka Y, Yamazaki S, Kimura K (2016) Preparation of poly(ether ketone)s derived from 2,5-furandicarboxylic acid by polymerization in ionic liquid. Macromolecules 49:1252–1258

    CAS  Google Scholar 

  18. Smith KJ, Towle IDH, Moloney MG (2017) Polyaryletherketone polymers and copolymers by a Friedel Crafts dispersion polymerization. Eur Polym J 96:159–175

    CAS  Google Scholar 

  19. Hendrick JL (1991) Poly(aryl ether amides). Macromolecules 24:812–813

    Google Scholar 

  20. Lucas M, Brock P, Hendrick JL (1993) Poly(aryl ether amide)s. J Polym Sci Part A Polym Chem 31:2179–2185

    CAS  Google Scholar 

  21. Wang CY, Li PH, Li G, Jiang JM (2009) High optical transparency and low dielectric constant of novel organosoluble poly(ether ketone amide)s derived from an unsymmetrical diamine containing trifluoromethyl groups. Colloid Polym Sci 287:495–500

    CAS  Google Scholar 

  22. Mercer FW (1993) Synthesis and characterization of aromatic poly(ether ketone amide)s. High Perform Polym 5:187–196

    CAS  Google Scholar 

  23. Cai M, Zhu M, Wang P, Song C (2010) Synthesis and properties of novel poly(aryl ether ketone)s containing both diphenyl moiety and amide linkages in the main chains. Polymer 51:1293–1300

    CAS  Google Scholar 

  24. Cai M, Zhu M, Qian J, Sun Y (2011) Synthesis of aromatic poly(ether amide amide ether ketone ketone)s by electrophilic Friedel–Crafts solution polycondensation. Polym Adv Technol 22:1007–1013

    CAS  Google Scholar 

  25. Huang B, Qian J, Wang G, Cai M (2014) Synthesis and properties of novel copolymers of poly(ether ketone diphenyl ketone ether ketone ketone) and poly(ether amide ether amide ether ketone ketone). Polym Eng Sci 54:1757–1764

    CAS  Google Scholar 

  26. Yoneyama M, Kakimoto M, Imai Y (1988) Novel synthesis of aromatic polyamides by palladium-catalyzed polycondensation of aromatic dibromides, aromatic diamines, and carbon monoxide. Macromolecules 21:1908–1911

    CAS  Google Scholar 

  27. Yoneyama M, Kakimoto M, Imai Y (1989) Synthesis of aliphatic–aromatic polyamides by palladium-catalyzed polycondensation of aliphatic diamines, aromatic dibromides, and carbon monoxide. J Polym Sci Part A Polym Chem 27:1985–1991

    CAS  Google Scholar 

  28. Turner SR, Perry RJ, Blevins RW (1992) High molecular weight aromatic polyamides from aromatic diiodides and diamines. Macromolecules 25:4819–4820

    CAS  Google Scholar 

  29. Perry RJ, Turner SR, Blevins RW (1993) Synthesis of linear, high molecular weight aromatic polyamides by the palladium-catalyzed carbonylation and condensation of aromatic diiodides, diamines, and carbon monoxide. Macromolecules 26:1509–1513

    CAS  Google Scholar 

  30. Perry RJ, Turner SR, Blevins RW (1994) Palladium-catalyzed formation of poly(imide-amides). 1. Reactions with diiodides and diamines. Macromolecules 27:4058–4082

    CAS  Google Scholar 

  31. Ueda M, Yokoo T (1994) Synthesis of poly(ether-ketone-amide)s by palladium-catalyzed polycondensation of aromatic dibromides containing ether ketone structure, aromatic diamines, and carbon monoxide. J Polym Sci Part A Polym Chem 32:2065–2071

    CAS  Google Scholar 

  32. Ueda M, Yokoo T, Nakamura T (1994) Synthesis of poly(ether-sulfone-amide)s by palladium-catalyzed polycondensation of aromatic dibromides containing ether sulfone structure, aromatic diamines, and carbon monoxide. J Polym Sci Part A Polym Chem 32:2989–2995

    CAS  Google Scholar 

  33. Perry RJ, Turner SR, Blevins RW (1995) Palladium-catalyzed formation of poly(imide-amides). 2. Reactions with chloroiodophthalimides and diamines. Macromolecules 28:2607–2610

    CAS  Google Scholar 

  34. Rabani G, Kraft A (2002) Synthesis of poly(ether-esteramide) elastomers by a palladium-catalyzed polycondensation of aromatic diiodides with telechelic diamines and carbon monoxide. Macromol Rapid Commun 23:375–379

    CAS  Google Scholar 

  35. Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J-M (2011) Magnetically recoverable nanocatalysts. Chem Rev 111:3036–3075

    CAS  PubMed  Google Scholar 

  36. Nasir Baig RB, Varma RS (2013) Magnetically retrievable catalysts for organic synthesis. Chem Commun 49:752–770

    Google Scholar 

  37. Wang D, Astruc D (2014) Fast-growing field of magnetically recyclable nanocatalysts. Chem Rev 114:6949–6985

    CAS  PubMed  Google Scholar 

  38. Stevens PD, Li G, Fan J, Yen M, Gao Y (2005) Recycling of homogeneous Pd catalysts using superparamagnetic nanoparticles as novel soluble supports for Suzuki, Heck, and Sonogashira cross-coupling reactions. Chem Commun 35:4435–4437

    Google Scholar 

  39. Liu J, Peng X, Sun W, Zhao Y, Xia C (2008) Magnetically separable Pd catalyst for carbonylative Sonogashira coupling reactions for the synthesis of α, β-alkynyl ketones. Org Lett 10:3933–3936

    CAS  PubMed  Google Scholar 

  40. Baruwati B, Guin D, Manorama SV (2007) Pd on surface-modified NiFe2O4 nanoparticles: a magnetically recoverable catalyst for Suzuki and Heck reaction. Org Lett 9:5377–5380

    CAS  PubMed  Google Scholar 

  41. Jin M-J, Lee D-H (2010) A practical heterogeneous catalyst for the Suzuki, Sonogashira, and Stille coupling reactions of unreactive aryl chlorides. Angew Chem Int Ed 49:1119–1122

    CAS  Google Scholar 

  42. Shylesh S, Wang L, Thiel WR (2010) Palladium(II)-phosphine complexes supported on magnetic nanoparticles: filtration-free, recyclable catalysts for Suzuki–Miyaura coupling reactions. Adv Synth Catal 352:425–432

    CAS  Google Scholar 

  43. Li P, Wang L, Zhang L, Wang G-W (2012) Magnetic nanoparticles-supported palladium: a highly efficient and reusable catalyst for the Suzuki, Sonogashira, and Heck reactions. Adv Synth Catal 354:1307–1318

    CAS  Google Scholar 

  44. Zhang L, Li P, Liu C, Yang J, Wang M, Wang L (2014) A highly efficient and recyclable Fe3O4 magnetic nanoparticle immobilized palladium catalyst for the direct C-2 arylation of indoles with arylboronic acids. Catal Sci Technol 4:1979–1988

    CAS  Google Scholar 

  45. Tang H, Huang B, Zhu X, Cai M (2018) Synthesis of poly(ether ketone amide)s containing 4-aryl-2,6-diphenylpyridine moieties by a heterogeneous palladium-catalyzed polycondensation of aromatic diiodides, aromatic diamines, and carbon monoxide. Polym Adv Technol 29:2204–2215

    CAS  Google Scholar 

  46. Hu Z, Li S, Zhang C (2007) Synthesis and properties of polyamide-imides containing fluorenyl cardo structure. J Appl Polym Sci 106:2494–2501

    CAS  Google Scholar 

  47. Yang CP, Su YY, Hsu MY (2006) Synthesis and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]fluorene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides. Colloid Polym Sci 284:990–1000

    CAS  Google Scholar 

  48. Sheng S, Li T, Jiang J, He W, Song C (2010) Synthesis and properties of novel polyamides containing sulfone-ether linkages and xanthene cardo groups. Polym Int 59:1014–1020

    CAS  Google Scholar 

  49. Sheng S-R, Ma C-X, Jiang J-W, Li Q, Song C-S (2011) Optically high transparency and light color of organosoluble fluorinated polyamides with bulky xanthene pendent groups. Polym Adv Technol 22:2523–2532

    CAS  Google Scholar 

  50. Yang CP, Lin JH (1993) Syntheses and properties of aromatic polyamides and polyimides derived from 9,9-bis[4-(p-aminophenoxy)phenyl]fluorine. J Polym Sci Part A Polym Chem 31:2153–2163

    CAS  Google Scholar 

  51. Hsiao SH, Yang CP, Lin WL (1999) Synthesis and characterization of new diphenylfluorene-based aromatic polyamides derived from 9,9-bis[4-(4-carboxyphenoxy)phenyl]fluorine. Macromol Chem Phys 200:1428–1433

    CAS  Google Scholar 

  52. Yang CP, Lin JH (1995) Syntheses and properties of aromatic polyamides and polyimides based on 3,3-bis[4-(4-aminophenoxy)phenyl]phthalimidine. Polymer 36:2607–2614

    CAS  Google Scholar 

  53. Liaw DJ, Liaw BY (1999) Synthesis and characterization of norbornane-containing cardo polyamides. J Polym Sci Part A Polym Chem 37:2791–2794

    CAS  Google Scholar 

  54. Liaw DJ, Liaw BY, Chung CY (2000) Synthesis and characterization of new cardo polyamides and polyimides containing tert-butylcyclohexylidene units. Macromol Chem Phys 201:1887–1893

    CAS  Google Scholar 

  55. Ge Z, Yang S, Tao Z, Liu J, Fan L (2004) Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines. Polymer 45:3627–3635

    CAS  Google Scholar 

  56. Hougham G, Tesoro G, Viehbeck A (1996) Influence of free volume change on the relative permittivity and refractive index in fluoropolyimides. Macromolecules 29:3453–3456

    CAS  Google Scholar 

Download references

Acknowledgements

We thank the National Natural Science Foundation of China (Project 21664008), the Natural Science Foundation of Jiangxi Province of China (Project 20181BAB203011), and Key Laboratory of Functional Small Organic Molecule, Ministry of Education (No. KLFS-KF-201704) for financial support.

Author information

Authors and Affiliations

  1. Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, China

    Feihua Zou, Bin Huang, Limin Liu & Mingzhong Cai

Authors
  1. Feihua Zou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bin Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Limin Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mingzhong Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mingzhong Cai.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 3830 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zou, F., Huang, B., Liu, L. et al. Synthesis of cardo poly(arylene ether ketone amide)s by heterogeneous palladium-catalyzed polycondensation of aromatic diiodides, aromatic diamines containing cardo groups and CO. Polym. Bull. 77, 1983–2001 (2020). https://doi.org/10.1007/s00289-019-02844-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-019-02844-6

Keywords

Search

Navigation