Polymer Bulletin

, Volume 76, Issue 1, pp 53–72 | Cite as

Investigation of morphological aspects and thermal properties of ZnO/poly(amide–imide) nanocomposites based on levodopa-mediated diacid monomer

  • Mehdi Ahmadi
  • Kurosh Rad-MoghadamEmail author
  • Mehdi HatamiEmail author
Original Paper


Hybrid nanocomposites (NCs) manufactured by distribution of zinc oxide (ZnO) nanoparticles (NPs) in poly[hydroxy(amide–imide)] (PHAI) are considered and produced by using an ultrasonic-assisted method. A novel monomer namely N,N′-pyromellitoyl-bis-l-(3,4-dihydroxyphenyl)alanine (NPDA) was synthesized by using levodopa as a starting material. The monomer structure was characterized by FT-IR and NMR spectroscopy. Reaction of the monomer containing pendent catechol moieties by a diamine by Yamazaki method provided the thermally stable PHAI matrix with well-designed units. FT-IR and 1H-NMR spectra confirmed the accomplishment of preparation step for the PHAI. The surface of ZnO NPs was functionalized with 3-aminopropyltriethoxysilane (KH550) coupling agent and donated a better dispersion and ornamental interactions with catechol functional units of PHAI matrix by hydrogen bonds. Provided NCs were characterized by FT-IR, X-ray powder diffraction (XRD), atomic force microscopy (AFM), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM) and thermogravimetric analysis. The FE-SEM and TEM pictures confirm the coral-like structures for NCs. The FE-SEM and AFM analyses show the good dispersion of ZnO nanostructure in the PHAI matrix. The XRD patterns of NCs show the presence of crystalline ZnO NPs in amorphous PHAI matrix.


Nanocomposites Levodopa Poly(amide–imide) ZnO 



The authors are grateful to research council of University of Guilan for the supports of this work. Further financial supports from research council of University of Bonab are appreciatively acknowledged.


  1. 1.
    Cassidy PE (1980) Thermally stable polymers. Marcel Dekker, New YorkGoogle Scholar
  2. 2.
    Wilson D, Stenzenberger HD, Hergenrother PM (1990) Polyimides. Blackie, LondonGoogle Scholar
  3. 3.
    Mehdipour-Ataei S, Sarrafi Y, Hatami M (2004) Novel thermally stable polyimides based on flexible diamine: synthesis, characterization, and properties. Eur Polym J 40:2009–2015Google Scholar
  4. 4.
    Mehdipour-Ataei S, Hatami M (2007) Aromatic poly (sulfone sulfide amide imide) s as new types of soluble thermally stable polymers. Polym Adv Technol 18:292–298Google Scholar
  5. 5.
    Fang Q, Wang J, Gu S, Kaspar RB, Zhuang Z, Zheng J, Guo H, Qiu S, Yan Y (2015) 3D porous crystalline polyimide covalent organic frameworks for Ddrug delivery. J Am Chem Soc 137:8352–8355Google Scholar
  6. 6.
    Aksoy B, Gungor O, Koytepe S, Seckin T (2016) Preparation of novel sensors based on polyimide membrane for sensitive and selective determination of dopamine. Polym Plast Technol Eng 55:119–128Google Scholar
  7. 7.
    Hatami M (2017) Production and morphological characterization of low resistance polyimide/silver nanowire nanocomposites: potential application in nanoconductive adhesives. J Mater Sci Mater Electron 28:3897–3908Google Scholar
  8. 8.
    Hu X, Mu H, Wang Y, Wang Z, Yan J (2018) Colorless polyimides derived from isomeric dicyclohexyl-tetracarboxylic dianhydrides for optoelectronic applications. Polymer 134:8–19Google Scholar
  9. 9.
    Singto S, Tantayanon S, Zoto CA, Connors RE (2018) Syntheses and photophysical properties of diaminotetraphenylporphyrins and their corresponding polyimides. J Mol Struct 1154:114–130Google Scholar
  10. 10.
    Yang SY (2018) Advanced polyimide materials. Elsevier, AmsterdamGoogle Scholar
  11. 11.
    You H, Hossain I, Kim T-H (2018) Piperazinium-mediated crosslinked polyimide-polydimethylsiloxane (PI-PDMS) copolymer membranes: the effect of PDMS content on CO2 separation. RSC Adv 8:1328–1336Google Scholar
  12. 12.
    Huang H, Yu J, Guo H, Shen Y, Yang F, Wang H, Liu R, Liu Y (2018) Improved antifouling performance of ultrafiltration membrane via preparing novel zwitterionic polyimide. Appl Surf Sci 427:38–47Google Scholar
  13. 13.
    Govindaraj B, Sarojadevi M (2016) Microwave-assisted synthesis and characterization of polyimide/functionalized MWCNT nanocomposites containing quinolyl moiety. Polym Compos 37:2417–2424Google Scholar
  14. 14.
    Yi L, Huang W, Yan D (2017) Polyimides with side groups: synthesis and effects of side groups on their properties. J Polym Sci A 1(55):533–559Google Scholar
  15. 15.
    Mehdipour-Ataei S, Sarrai Y, Hatami M (2005) Naphthalene-ring containing diamine and resulting thermally stable polyamides. Eur Polym J 41:2887–2892Google Scholar
  16. 16.
    Hatami M, Azarkar BF, Qandalee M, Hasanabadi H (2015) Morphological investigation of synthetic poly (amic acid)/cerium oxide nanostructures. Polym Eng Sci 55:2339–2348Google Scholar
  17. 17.
    Guan Q, Norder B, Dingemans TJ (2017) Flexible all-aromatic polyesterimide films with high glass transition temperatures. J Appl Polym Sci 133:44774–44788Google Scholar
  18. 18.
    Mallakpour S, Hatami M (2012) Production and evaluation of the surface properties of chiral poly (amide–imide)/TiO2 nanocomposites containing l-phenylalanine units. Prog Org Coat 74:564–571Google Scholar
  19. 19.
    Mehdipour-Ataei S, Hatami M (2009) Organosoluble, thermally stable polyamides containing sulfone and sulfide units. Chin J Polym Sci 27:781787Google Scholar
  20. 20.
    Selegny E (1979) Optically active polymers. Springer, DordrechtGoogle Scholar
  21. 21.
    Sadhasivam B, Rigana MF, Rukmanikrishnan B, Muthusamy S (2018) Chiral polyimide and its nanocomposites with graphene oxide using l-phenylalanine-based diamine. Polym Bull 75:829–849Google Scholar
  22. 22.
    Garreau A, Duvail JL (2014) Recent advances in optically active polymer-based nanowires and nanotubes. Adv Opt Mater 2:1122–1140Google Scholar
  23. 23.
    Miyagi Y, Otaki Y, Takahashi Y, Sanda F (2017) Synthesis of novel optically active poly(thiophenyleneethynylenephenylene)s. Effects of chirality competition and cooperation at the side chains on higher order structures. Polymer 130:250–257Google Scholar
  24. 24.
    Thakur VK, Thakur MK, Pappu A (2017) Hybrid polymer composite materials. Elsevier, AmsterdamGoogle Scholar
  25. 25.
    Xu K, Nakazono K, Takata T (2016) Diastereoselective synthesis of optically active rotaxane amine N-oxides via through-space chirality transfer. Tetrahedron Lett 57:4356–4359Google Scholar
  26. 26.
    Eiden LE (2013) A new era of catecholamines in the laboratory and clinic. Elsevier, AmsterdamGoogle Scholar
  27. 27.
    Silverman RB, Holladay MW (2014) The organic chemistry of drug design and drug action. Elsevier, WalthamGoogle Scholar
  28. 28.
    Dastan D, Banpurkar AG (2016) Solution processable sol–gel derived titania gate dielectric for organic field effect transistors. J Mater Sci Mater Electron 28:3851–3859Google Scholar
  29. 29.
    Hatami M, Ahmadipour M, Asghari S (2017) Heterocyclic grafting functionalization of silica nanoparticles: fabrication, morphological investigation and application for PVA nanocomposites. J Inorg Organomet Polym 27:1072–1083Google Scholar
  30. 30.
    Mallakpour S, Hatami M (2011) Bionanocomposites preparation and characterization: dispersion of surface-modified ZnO nanoparticles in optically active poly(amide–imide) derived from 3,5-diamino-N-(4-hydroxyphenyl)benzamide and amino acid. Des Monomers Polym 14:461–473Google Scholar
  31. 31.
    Mallakpour S, Zadehnazari A (2013) The production of functionalized multiwall carbon nanotube/amino acid-based poly(amide–imide) composites containing a pendant dopamine moiety. Carbon 56:27–37Google Scholar
  32. 32.
    Hu G, Liang G, Zhang W, Jin W, Zhang Y, Chen Q, Cai Y, Zhang W (2018) Silver nanoparticles with low cytotoxicity: controlled synthesis and surface modification with histidine. J Mater Sci 53:4768–4780Google Scholar
  33. 33.
    Mallakpour S, Motirasoul F (2017) Bio-functionalizing of α-MnO2 nanorods with natural l-amino acids: a favorable adsorbent for the removal of Cd(II) ions. Mater Chem Phys 191:188–196Google Scholar
  34. 34.
    Cai H, Yao P (2014) Gold nanoparticles with different amino acid surfaces: serum albumin adsorption, intracellular uptake and cytotoxicity. Colloid Surf B 123:900–906Google Scholar
  35. 35.
    Faridi S, Moghanian H, Shabanian M (2018) Novel heat-resistant and soluble poly(amide–ether)/zinc oxide nanocomposites: synthesis, characterization and computational study. Polym Bull. Google Scholar
  36. 36.
    Naganathan D, Thangamani P, Selvam T, Narayanasamy T (2018) Ce doped ZnO/f-MWCNT moss ball like nanocomposite: a strategy for high responsive current detection of l-tryptophan. Microchim Acta 185:96–105Google Scholar
  37. 37.
    Wang C, Fan H, Ren X, Fang J (2018) Room temperature synthesis and enhanced photocatalytic property of CeO2/ZnO heterostructures. Appl Phys A 124:99–111Google Scholar
  38. 38.
    Martin M, Prasad N, Sivalingam MM, Sastikumar D, Karthikeyan B (2018) Optical, phonon properties of ZnO–PVA, ZnO–GO–PVA nanocomposite free standing polymer films for UV sensing. J Mater Sci Mater Electron 29:365–373Google Scholar
  39. 39.
    Mujeeb Rahman P, Abdul Mujeeb VM, Muraleedharan K, Thomas SK (2018) Chitosan/nano ZnO composite films: enhanced mechanical, antimicrobial and dielectric properties. Arab J Chem 11:120–127Google Scholar
  40. 40.
    Mallakpour S, Hatami M (2013) Study on constructional design and structural analysis of poly (amide–imide)/ZnO nanocomposites containing pyromellitoyl-bis-l-isoleucine moieties. High Perform Polym 25:436–444Google Scholar
  41. 41.
    Hatami M, Yazdan Panah M (2017) Ultrasonic assisted synthesis of nanocomposite materials based on resole resin and surface modified nano CeO2: chemical and morphological aspects. Ultrason Sonochem 39:160–173Google Scholar
  42. 42.
    Van Krevelen DW, Hoftyzer PJ (1976) Properties of polymers, 3rd edn. Elsevier, AmsterdamGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of GuilanRashtIran
  2. 2.Polymer Research Laboratory, Department of Polymer Science and EngineeringUniversity of BonabBonabIran

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