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Synthesis and characterization of phosphorus containing aromatic poly(amide-imide)s copolymers for high temperature applications

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Abstract

A series of novel thermally stable poly(amide-imide)s (PAIs) based on non-coplaner diimide-diacid (DIDA) monomer is synthesized. These polymers are characterized by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and 31P-NMR spectroscopic techniques and their physical and thermal properties are also studied. Four different dianhydrides pyromellitic anhydride (PMDA)/3,3′,4,4′-benzophenone tetracarboxylic dianhydride (BTDA)/1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA)/4,4′-oxydiphthalic anhydride (ODPA) and amino acid l-tryptophan are used to synthesize DIDA. The polymerization of DIDA with phosphorus containing triamines having phenyl moieties gives poly(amide-imide)s. The synthesized polymers are obtained in high yield and possessed inherent viscosity in the range 0.66–0.98 dL/g. These polymers display higher solubility in polar aprotic solvents, such as DMSO, NMP and DMF. In addition, the absorption edge values (λ o) obtained from their UV curves are determined, and all the resulting poly(amide-imide)s films exhibited high optical transparency. The glass transition temperature (T g) of these polymers is recorded in the range 211–265 °C, initial decomposition temperature in excess of 435 °C and char yield at 800 °C in nitrogen ranged from 52 to 70 %. Wide angle X-ray diffraction showed that all the polymers are almost amorphous.

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References

  1. Behniafar H, Abedini-pozveh A (2011) Flexible, low-colored and transparent thin films prepared from new thermo-stable and organo-soluble poly(amide-imide). Polym Degrad Stab 96:1327–1332

    Article  CAS  Google Scholar 

  2. Babanzadeh S, Mahjoub AR, Mehdipour-Ataei S (2010) Novel soluble thermally stable silane-containing aromatic polyimides with reduced dielectric constant. Polym Degrad Stab 95:2492–2498

    Article  CAS  Google Scholar 

  3. Koytepe S, Adiguzel HI, Seçkin T (2009) Synthesis of nickelocene containing polyimides with low-dielectric constants. J Alloy Compd 470:347–353

    Article  Google Scholar 

  4. Shimamura H, Nakamura T (2010) Investigation of degradation mechanisms in mechanical properties of polyimide films exposed to a low earth environment. Polym Degrad Stab 95:21–30

    Article  CAS  Google Scholar 

  5. Fahim M, Bijwe J, Nalwa HS (2001) Chapter 8—polyimides for microelectronics and tribology applications. Supramol Photosensit Electroact Mater 2001:643–726

    Article  Google Scholar 

  6. Liaw D, Wang K, Huang Y, Lee KR, Lai JY, Ha CS (2012) Advanced polyimides materials: synthesis, physical properties and applications. Prog Polym Sci 37:907–974

    Article  CAS  Google Scholar 

  7. Sasaki T, Moriuchi H, Yano S, Yokota R (2005) High thermal stable thermoplastic-thermosetting polyimide film by use of asymmetric dianhydride (a-BPDA). Polymer 46:6968–6975

    Article  CAS  Google Scholar 

  8. Wang Y, Goh SH, Chung TS, Na P (2009) Polyamide-imide/polyetherimide dual-layer hollow fiber membranes for pervaporation dehydration of C1–C4 alcohols. J Membr Sci 326:222–233

    Article  CAS  Google Scholar 

  9. Zhang Y, Wan R, Yi S, Setiawan L, Hu Fane AG (2011) Novel chemical surface modification to enhance hydrophobicity of polyamide-imide (PAI) hollow fiber membranes. J Membr Sci 380:241–250

    Article  CAS  Google Scholar 

  10. Heo GY, Park SJ (2011) Surface physical and chemical properties of atmospheric pressure plasma-treated polyamideimide fibrous mats using attenuated total reflection Fourier transform infrared imaging. Carbohydr Polym 88:562–567

    Article  Google Scholar 

  11. Kausar A, Zulfiqar S, Ahmad Z, Sarwar MI (2010) Novel processable and heat resistant poly(phenylthiourea azomethine imide)s: synthesis and characterization. Polym Degrad Stab 95:1826–1833

    Article  CAS  Google Scholar 

  12. Mehdipour-Ataei S, Hatami M (2005) Synthesis and characterization of novel heat resistant poly(amide imide)s. Eur Polym J 41:2010–2015

    Article  CAS  Google Scholar 

  13. Rajesh S, Maheswari P, Senthilkumar S, Jayalakshmi A, Mohan D (2011) Preparation and characterization of poly(amide-imide) incorporated cellulose acetate membranes for polymer enhanced ultrafiltration of metal ions. Chem Eng J 171:33–44

    Article  CAS  Google Scholar 

  14. Higashi F, Ogata S-I, Aoki Y (1982) High-molecular-weight poly(p-phenyleneterephthalamide) by the direct polycondensation reaction with triphenyl phosphite. J. Polym Sci A Polym Chem 20:2081–2087

    Article  CAS  Google Scholar 

  15. Banihashemi A, Behniafar H (2003) Synthesis and characterization of novel aromatic poly(amide-imide)s derived from 2,2′-bis(4-trimellitimidophenoxy)biphenyl or 2,2′-bis(4-trimellitimidophenoxy)-1,1′-binaphthyl and various aromatic diamines. Polym Int 52:1136–1144

    Article  CAS  Google Scholar 

  16. Mallakpour S, Kolahdoozan M (2008) Synthesis and properties of novel soluble aromatic polyamides derived from 5-(2-phthalimidyl-3-methyl butanoylamino)isophthalic acid and aromatic diamines. React Fundam Polym 68:91–96

    Article  CAS  Google Scholar 

  17. Liaw D, Chen W (2006) High glass transitions of novel organosoluble polyamide-imides based on noncoplaner and rigid diimide-dicarboxylic acid. Polym Degrad Stab 91:1731–1739

    Article  CAS  Google Scholar 

  18. Faghihi K, Hajibeygi M, Shabanian M (2009) Novel flame-retardant and thermally stable poly(amide-imide)s based on bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide and phosphine oxide in the main chain: synthesis and characterization. J Chin Chem Soc 56:609–618

    CAS  Google Scholar 

  19. Faghihi K, Hagibeygi M (2007) New aromatic polyamide with azo and phosphine oxide groups in the main chain. Turk J Chem 31:65–73

    CAS  Google Scholar 

  20. Chen X, Zhang M, Tang X (2008) Synthesis and properties of soluble aromatic copolyamides containing phosphine oxide moiety. Chin J Polym Sci 26:793–797

    Article  CAS  Google Scholar 

  21. Wang L, Kang H, Wang S, Liu W, Wang R (2007) Solubilities, thermostabilities and flame retardance behaviour of phosphorus-containing flame retardants and copolymers. Fluid Phase Equilib 258:99–107

    Article  CAS  Google Scholar 

  22. Vlad-Bubulac T, Hamciuc C (2009) Aliphatic-aromatic copolyesters containing phosphorus cyclic bulky groups. Polymer 50:2220–2227

    Article  CAS  Google Scholar 

  23. Chen H, Zhou Q, Dong X, Zhang Y, Chen L, Wang Y (2012) Pyrolysis study of poly(trimethylene terephthalate) and its phosphorus-containing copolyesters. Polym Degrad Stab 97:905–913

    Article  CAS  Google Scholar 

  24. Chen H, Zhang K, Xu J (2011) Synthesis and characterization of novel phosphorus-nitrogen containing poly(ether sulphone)s. Polym Degrad Stab 96:197–203

    Article  CAS  Google Scholar 

  25. Mallakpour S, Hatami M (2012) Production and evaluation of the surface properties of chiral poly(amide-imide)/TiO2 nanocomposites containing l-phenylalanine unites. Prog Polym Coat 74:564–571

    Article  CAS  Google Scholar 

  26. Zahmatkesh S, Alborzi AR, Sadeghi J, Zare K (2011) Interfacial synthesis and properties of l-lysine-derived optically active poly(ester-imide)s. Chin Chem Lett 22:607–610

    Article  CAS  Google Scholar 

  27. Marcos-Fernández A, Abraham GA, Valentín JL, Román JS (2006) Synthesis and characterization of biodegradable non-toxic poly(ester-urethane-urea)s based on poly(ε-caprolactone) and amino acid derivatives. Polymer 47:785–798

    Article  Google Scholar 

  28. Pang X, Chu C–C (2010) Synthesis, characterization and biodegradation of functionalized amino acid-based poly(ester amide)s. Biomaterials 31:3745–3754

    Article  CAS  Google Scholar 

  29. Sanda F, Endo T (1999) Synthesis and functions of polymers based on amino acids. Macromol Chem Phys 200:2651–2661

    Article  CAS  Google Scholar 

  30. Khurana P, Aggarwal S, Narula AK, Choudhary V (2003) Curing and thermal behaviour of epoxy resin in the presence of silicon-containing amide amines. J Appl Polym Sci 87:1345–1353

    Article  CAS  Google Scholar 

  31. Liu C, Li X, Xu J, Jian X (2011) Synthesis and characterization of novel polybenzimidazoles containing 4-phenyl phthalazinone moiety. Eur Polym J 47:1852–1860

    Article  CAS  Google Scholar 

  32. Jeong KU, Kim J–J, Yoon T-H (2001) Synthesis and characterization of novel polyimides containing fluorine and phosphine oxide moieties. Polymer 42:6019–6030

    Article  CAS  Google Scholar 

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Acknowledgments

The author (S. Agrawal) wishes to express the gratitude to Guru Gobind Singh Indraprastha University, New Delhi for providing financial support in the form of IPRF.

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  1. GGS Indraprastha University, Sector-16C, Dwarka, New Delhi, 110078, India

    Seema Agrawal & Anudeep Kumar Narula

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  1. Seema Agrawal
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  2. Anudeep Kumar Narula
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Correspondence to Anudeep Kumar Narula.

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Agrawal, S., Narula, A.K. Synthesis and characterization of phosphorus containing aromatic poly(amide-imide)s copolymers for high temperature applications. Polym. Bull. 70, 3241–3260 (2013). https://doi.org/10.1007/s00289-013-1021-1

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  • DOI: https://doi.org/10.1007/s00289-013-1021-1

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