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Preparation and characterization of thermally stable poly(amide–ester–imide) nanocomposites based on N,N′-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo [3,4-f]isoindole-2,6-(1H,3H)-diyl)bis-(4-hydroxybenzamide) and surface-coated TiO2 nanoparticles

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Abstract

A thermally stable and optically active poly(amide–ester–imide) (PAEI) was prepared from diol: N,N′-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6-(1H,3H)-diyl)bis-(4-hydroxybenzamide). The structure of the polymer was determined by means of 1H NMR and Fourier transform infrared spectroscopy (FT-IR), elemental analysis; also it was studied with specific rotation technique, X-ray diffraction (XRD), and field emission scanning electron microscopy (FE-SEM). Then, three series of PAEI/modified TiO2 nanocomposites (NC)s with 5, 10, and 15 % of TiO2 nanoparticles (NP)s contents were prepared via ultrasonic irradiation technique. The properties of the synthesized NCs were studied by FT-IR, XRD, FE-SEM, transmission electron microscopy, UV–vis spectroscopy and thermogravimetric analysis methods. It was found that the NCs exhibit enhanced thermal properties compared with the neat PAEI.

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References

  1. Bacosca I, Hamciuc E, Bruma M, Ignat M (2011) Poly(amide imide)s containing functional nitrile groups for high performance materials. React Funct Polym 71:905–915

    Article  CAS  Google Scholar 

  2. Li X-R, Li Y-S (2003) Synthesis and characterization of hyperbranched aromatic poly(ester–imide)s. Polymer 44:3855–3863

    Article  CAS  Google Scholar 

  3. Wu G, Tang Y, Weng R (2010) Dispersion of nano-carbon filled polyimide composites using self-degradated low molecular poly(amic acid) as impurity-free dispersant. Polym Degrad Stab 95:1449–1455

    Article  CAS  Google Scholar 

  4. Shockravi A, Abouzari-Lotf E, Javadi A, Atabaki F (2009) Preparation and properties of new ortho-linked polyamide–imides bearing ether, sulfur, and trifluoromethyl linkages. Eur Polym J 45:1599–1606

    Article  CAS  Google Scholar 

  5. Yang F, Li Y, Bu Q, Zhang S, Ma T, Zhao J (2010) Characterizations and thermal stability of soluble polyimide derived from novel unsymmetrical diamine monomers. Polym Degrad Stab 9:1950–1958

    Article  Google Scholar 

  6. Yu Y-Y, Chien W-C, Tsai T-W (2010) High transparent soluble polyimide/silica hybrid optical thin films. Polym Test 29:33–40

    Article  Google Scholar 

  7. Hsiao S-H, Liou G-S, Kung Y-C, Pan H-Y, Kuo C-H (2009) Electroactive aromatic polyamides and polyimides with adamantylphenoxy-substituted triphenylamine units. Eur Polym J 45:2234–2248

    Article  CAS  Google Scholar 

  8. Hasegawa M, Sakamoto Y, Tanaka Y, Kobayashi Y (2010) Poly(ester imide)s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis(4-aminophenyl)terephthalate and effect of substituents. Eur Polym J 46:151–1524

    Article  Google Scholar 

  9. Nechifor M (2009) Synthesis and properties of some aromatic polyamides with coumarin chromophores. React Funct Polym 69:27–35

    Article  CAS  Google Scholar 

  10. Kim SI, Shin TJ, Ree M, Lee H, Chang T, Lee C, Woo TH, Rhee SB (2000) Structure and properties of various poly(amic diisopropyl ester-alt-imide)s and their alternating copolyimides. Polymer 41:5173–5184

    Article  CAS  Google Scholar 

  11. Mehdipour-Ataei S, Bahri-Laleh N, Amirshaghaghi A (2006) Comparison of one-step and two-step methods of polyimidization and substitution effect in the synthesis of new poly(ester–imide)s with bulky pendent group. Polym Degrad Stab 91:2622–2631

    Article  CAS  Google Scholar 

  12. Zhao JJ, Gong CL, Zhang SJ, Shao Y, Li YF (2010) Synthesis of a new pyridine-containing diamine and related polyimide. Chin Chem Lett 21:277–278

    Article  CAS  Google Scholar 

  13. Mallakpour S, Zadehnazari A (2013) Novel optically active poly(amidethioester–imide)s containing l-a-amino acids and thiadiazol anticorrosion group: production and characterization. High Perform Polym 25:377–386

    Article  Google Scholar 

  14. Abdolmaleki A, Mallakpour S, Borandeh S (2012) Effect of silane-modified ZnO on morphology and properties of bionanocomposites based on poly(ester–amide) containing tyrosine linkages. Polym Bull 69:15–28

    Article  CAS  Google Scholar 

  15. Honkhambe PN, Bhairamadgi NS, Biyani MV, Wadgaonkar PP, Salunkhe MM (2010) Synthesis and characterization of new aromatic polyesters containing cardo decahydronaphthalene groups. Eur Polym J 46:709–718

    Article  CAS  Google Scholar 

  16. Banu P, Sundar S, Dhathathreyan A, Radhakrishnan G (2004) Synthesis and surface properties of aqueous dispersions of poly(ester–imide) prepared from anhydride terminated polyester prepolymer and diisocyanate. J Colloid Interface Sci 277:304–308

    Article  CAS  Google Scholar 

  17. Li H, Wang D, Fan L, Yang S (2006) Preparation and characterization of a novel thermally stable unsaturated poly(ester–imide) based on 1,4-bis[2′-trifluoromethyl-4′-(4″-carboxylic acid) trimellitimido phenoxy]benzene. Eur Polym J 42:534–543

    Article  CAS  Google Scholar 

  18. Shang Z, Lu C, Lu X, Gao L (2007) Studies on syntheses and properties of novel CeO2/polyimide nanocomposite films from Ce(Phen)3 complex. Polymer 48:4041–4046

    Article  CAS  Google Scholar 

  19. Chan KL, Mariatti M, Lockman Z, Sim LC (2010) Effect of ultrasonication medium on the properties of copper nanoparticle-filled epoxy composite for electrical conductive adhesive (ECA) application. J Mater Sci Mater Electron 21:772–778

    Article  CAS  Google Scholar 

  20. Veres A, Ménesi J, Juhász A, Berkesi O, Ábrahám N, Bohus G, Oszkó A, Pótári G, Buzás N, Janovák L, Dékány I (2014) Photocatalytic performance of silver-modified TiO2 embedded in poly(ethyl-acrylate-co-methyl metacrylate) matrix. Colloid Polym Sci 292:207–217

    Article  CAS  Google Scholar 

  21. Nakayama N, Hayashi T (2008) Preparation of TiO2 nanoparticles surface-modified by both carboxylic acid and amine: dispersibility and stabilization in organic solvents. Colloid Surf A Physicochem Eng Asp 317:543–550

    Article  CAS  Google Scholar 

  22. Mallakpour S, Shahmohammadi MH (2004) Microwave-promoted rapid synthesis of new optically active poly(amide–imide)s derived from N,N′-(Pyromellitoyl)-bis-l-isoleucine diacid chloride and aromatic diamines. J Appl Polym Sci 92:951–959

    Article  CAS  Google Scholar 

  23. Mallakpour S, Khani M (2013) Investigating thermophysical properties of novel chiral nanostructured poly(amide–ester–imide)s containing different amino acids based on biological active N,N′-(Pyromellitoyl)-bis-l-amino acids and diol. High Perform Polym 25:723–732

    Article  Google Scholar 

  24. Mallakpour S, Aalizadeh R (2013) A simple and convenient method for the surface coating of TiO2 nanoparticles with bioactive chiral diacids containing different amino acids as the coupling agent. Prog Org Coat 76:648–653

    Article  CAS  Google Scholar 

  25. Higashi F, Tobe A (2001) A new polycondensation involving dicarboxylic acids with differently activated carboxyl groups by TsCl/DMF/Py. Macromol Chem Phys 202:745–749

    Article  CAS  Google Scholar 

  26. Abdolmaleki A, Mallakpour S, Borandeh S (2011) Preparation, characterization and surface morphology of novel optically active poly(ester–amide)/functionalized ZnO bionanocomposites via ultrasonication assisted process. Appl Surf Sci 257:6725–6733

    Article  CAS  Google Scholar 

  27. Nakayama N, Hayashi T (2007) Preparation and characterization of poly(l-lactic acid)/TiO2 nanoparticle nanocomposite films with high transparency and efficient photodegradability. Polym Degrad Stab 92:1255–1264

    Article  CAS  Google Scholar 

  28. Van Krevelen DW, Hoftyzer PJ (1976) Properties of polymers, 3rd edn. Elsevier, New York

    Google Scholar 

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Acknowledgments

The authors thank the Research Affairs Division Isfahan University of Technology (IUT), Isfahan, for partial financial support. Further financial support from Iran Nanotechnology Initiative Council (INIC), National Elite Foundation (NEF) and Center of Excellence in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged. We also thank Miss. M. Khani and Miss. M. Madani for their helpful assistance.

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Mallakpour, S., Aalizadeh, R. Preparation and characterization of thermally stable poly(amide–ester–imide) nanocomposites based on N,N′-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo [3,4-f]isoindole-2,6-(1H,3H)-diyl)bis-(4-hydroxybenzamide) and surface-coated TiO2 nanoparticles. Polym. Bull. 73, 3019–3032 (2016). https://doi.org/10.1007/s00289-016-1638-y

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  • DOI: https://doi.org/10.1007/s00289-016-1638-y

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