Skip to main content
SpringerLink
Log in

Synthesis and characterization of new poly(ether–ester–imide)s as a generation of soluble and thermally stable polymers

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

Abstract

A new-type of dicarboxylic acid 6 was synthesized from the reaction of 1,4-bis[4-aminophenoxy]butane 4 with trimellitic anhydride 5 in a solution of glacial acetic acid/pyridine (Py) at refluxing temperature. 1,4-Bis[4-nitrophenoxy]butane 3 was prepared by reaction of 4-nitrophenol 1 with 1,4-dibromo butane 2 in N,N-dimethylformamide (DMF) solution. Then dinitro 3 was reduced to 1,4-bis[4-aminophenoxy]butane 4 by using 10% Pd–C, ethanol, and hydrazine monohydrate. So six new thermally stable and organosoluble poly(ether–ester–imide)s (PEEIs) 8a–f with good inherent viscosities were synthesized by the direct polycondensation reaction of new 1,4-bis[4-(trimellitimido)phenoxy]butane 6 with several aromatic diols 7a–f through direct polycondensation using tosyl chloride (TsCl)/pyridine (Py)/DMF system as condensing agent. The resulted polymers were fully characterized by means of FTIR and 1H NMR spectroscopy, elemental analyses, inherent viscosity, solubility tests, differential scanning calorimeter (DSC), thermogravimetric analysis (TGA), and derivative of thermogravimetric (DTG).

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

Similar content being viewed by others

References

  1. Wilson D, Stenzenberger HD, Hergenrother PM (1990) Polyimide. Chapman & Hall, New York

    Google Scholar 

  2. Ghosh MK, Mittal KL (1996) Polyimides: fundamentals and applications. Marcel Dekker, New York

    Google Scholar 

  3. Cassidy PE (1980) Thermally stable polymers. Marcel Dekker, New York

    Google Scholar 

  4. Saxena A, Rao VL, Prabhakaran PV, Ninan KN (2003) Synthesis and characterization of polyamides and poly(amide–imide)s derived from 2,2-bis(4-aminophenoxy)benzonitrile. Eur Polym J 39:401–405

    Article  CAS  Google Scholar 

  5. Liaw DJ, Liaw BY, Hsu PN, Hwang CY (2001) Synthesis and characterization of new highly organosoluble poly(ether–imide)s bearing a noncoplanar 2,2′-dimethyl-4,4′-biphenyl unit and kink diphenylmethylene linkage. Chem Mater 13:1811–1816

    Article  CAS  Google Scholar 

  6. Mallakpour S, Kowsari E (2006) Preparation and characterization of new thermally stable and optically active poly(ester–imide)s by direct polycondensation with thionyl chloride in pyridine. Polym Adv Technol 17:174–179

    Article  CAS  Google Scholar 

  7. Faghihi Kh, Hajibeygi M, Shabanian M (2010) Synthesis and properties of new photosensitive and chiral poly(amide–imide)s based on bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide and dibenzalacetone moieties in the main chain. Polym Int 59:218–226

    CAS  Google Scholar 

  8. Faghihi Kh, Hajibeygi M, Shabanian M (2009) Synthesis and properties of novel flame-retardant and thermally stable poly(amide–imide)s from N,N′-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-l-amino acids and phosphine oxide moiety by two different methods. Macromol Res 17:739–745

    CAS  Google Scholar 

  9. Faghihi Kh, Shabanian M, Hajibeygi M (2009) Optically active and organosoluble poly(amide–imide)s derived from N,N′-(pyromellitoyl)bis-l-histidine and various diamines: synthesis and characterization. Macromol Res 17:912–918

    CAS  Google Scholar 

  10. Hale WF, Farnham AG, Johnson RN, Clendinning RA (1967) Poly(aryl–ethers) by nucleophilic aromatic substitution. II. Thermal stability. J Polym Sci A 5:2399–2414

    Article  CAS  Google Scholar 

  11. Johnson RN, Farnham AG, Clendinning RA, Hale WF, Merriman CN (1967) Poly(aryl–ethers) by nucleophilic aromatic substitution. I. Synthesis and properties. J Polym Sci A 5:2375–2398

    Article  CAS  Google Scholar 

  12. Bottino FA, Pasquale GD, Scalia L, Pollicino A (2001) Synthesis and characterisation of new polyamides containing 6,6′-oxy or 6,6′-carbonyldiquinoline units. Polymer 42:3323–3332

    Article  CAS  Google Scholar 

  13. Gutch PK, Banerjee S, Jaiswal DK (2003) Synthesis and properties of novel aromatic polyamides derived from 2,2-bis[4-(4-amino-2-fluorophenoxy)phenyl]hexafluoropropane and aromatic dicarboxylic acids. J Appl Polym Sci 89:691–696

    Article  CAS  Google Scholar 

  14. Mallakpour S, Kowsari E (2006) Synthesis of novel optically active poly(ester–imide)s by direct polycondensation reaction promoted by tosyl chloride in pyridine in the presence of N,N-dimethyformamide. J Appl Polym Sci 101:455–460

    Article  CAS  Google Scholar 

  15. Van Krevelen DW, Hoftyzer PJ (1976) Properties of polymers. Elsevier, New York

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, 38158-879, Arak, Iran

    Khalil Faghihi, Meisam Shabanian, Mohsen Hajibeygi & Yasser Mohammadi

Authors
  1. Khalil Faghihi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Meisam Shabanian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohsen Hajibeygi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yasser Mohammadi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Khalil Faghihi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Faghihi, K., Shabanian, M., Hajibeygi, M. et al. Synthesis and characterization of new poly(ether–ester–imide)s as a generation of soluble and thermally stable polymers. Polym. Bull. 66, 37–49 (2011). https://doi.org/10.1007/s00289-010-0256-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-010-0256-3

Keywords

Search

Navigation