Skip to main content
SpringerLink
Log in

Preparation of new enforcement polyamide nanocomposite filled by ternary layer double hydroxide and investigation of electrochemical activity, optical and thermal properties

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

Abstract

Herein, we report synthesis and manipulation of new reinforced polyamide nanocomposites filled by modified ternary (Mg, Zn, Al) layered double hydroxide by a solution intercalation technique. First, a new optically and electrochemically active polyamide 5 containing a new combination of azobenzene unit, imine function, triphenylamine segment and pyridine moiety in the main chain was prepared by reaction of a newly dicarboxylic acid 3 and 2,6-diaminopyridine 4. Then, two resulting nanocomposites containing 3 and 6% of DLDH were prepared and structures, morphology, electrochemical activity, thermal and optically properties of them were investigated. Also, dye-modified ternary layered double hydroxide was obtained by a co-precipitation method. The π–π* transition related to trans azobenzene chromosphere showed a single absorption between 290 and 350 nm. The electrochemically active behavior of resulting films onto glassy carbon exhibited cyclic voltammetry peak at 0.5–0.9 V, which was enhanced by filling polymer matrix with modified DLDH. On the other hand, significant improvements at T5, T10 and char yields of resulting nanocomposites were observed as compared to the polymer.

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
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Ispir E (2009) The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes. Dyes Pigm 82(1):13–19

    Article  CAS  Google Scholar 

  2. Kakanejadifard A, Azarbani F, Zabardasti A, Kakanejadifard S, Ghasemian M, Esna-ashari F, Omidi S, Shirali S, Rafieefar M (2013) The synthesis, structural characterization and antibacterial properties of some 2-((4-amino-1,2,5-oxadiazol-3-ylimino) methyl)-4-(phenyldiazenyl) phenol. Dyes Pigm 97(1):215–221

    Article  CAS  Google Scholar 

  3. Ghasemian M, Kakanejadifard A, Azarbani F, Zabardasti A, Shirali S, Saki Z, Kakanejadifard S (2015) The triazine-based azo-azomethine dyes; synthesis, characterization, spectroscopy, solvatochromism and biological properties of 2,2′-(((6-methoxy-1,3,5-triazine-2,4-diyl) bis (sulfanediyl) bis (2,1-phenylene)) bis (azanylylidene) bis (methanylylidene)) bis (4-(phenyldiazenyl) phenol). Spectrochim Acta Part A Mol Biomol Spectrosc 138:643–647

    Article  CAS  Google Scholar 

  4. Kakanejadifard A, Azarbani F, Saki Z, Kakanejadifard S, Zabardasti A (2014) Synthesis, characterization, solvatochromism and biological properties of 2, 2′-((1E,1′E)-((1,2,5-oxadiazole-3,4-diyl) bis (azanylylidene)) bis (methan-ylylidene)) bis (4-(phenyldiazenyl) phenol). Spectrochim Acta Part A Mol Biomol Spectrosc 132:700–705

    Article  CAS  Google Scholar 

  5. Kakanejadifard A, Azarbani F, Zabardasti A, Rezayat A, Ghasemian M, Kakanejadifard S (2013) Spectroscopic and solvatochromism studies along with antioxidant and antibacterial activities investigation of 2-((2-mercaptophenylimino) methyl)-4-(phenyldiazenyl) phenol. Spectrochim Acta Part A Mol Biomol Spectrosc 114:404–409

    Article  CAS  Google Scholar 

  6. Spiliopoulos IK, Mikroyannidis JA (1996) Soluble, rigid-rod polyamide, polyimides, and polyazomethine with phenyl pendent groups derived from 4,4″-diamino-3,5,3″,5″-tetraphenyl-p-terphenyl. Macromolecules 29(16):5313–5319

    Article  CAS  Google Scholar 

  7. Pfletscher M, Wölper C, Gutmann JS, Mezger M, Giese M (2016) A modular approach towards functional supramolecular aggregates–subtle structural differences inducing liquid crystallinity. Chem Commun 52(55):8549–8552

    Article  CAS  Google Scholar 

  8. Westphal E, Bechtold IH, Gallardo H (2010) Synthesis and optical/thermal behavior of new azo photoisomerizable discotic liquid crystals. Macromolecules 43(3):1319–1328

    Article  CAS  Google Scholar 

  9. Sava I, Burescu A, Stoica I, Musteata V, Cristea M, Mihaila I, Pohoata V, Topala I (2015) Properties of some azo-copolyimide thin films used in the formation of photoinduced surface relief gratings. RSC Adv 5(14):10125–10133

    Article  CAS  Google Scholar 

  10. Schab-Balcerzak E, Flakus H, Jarczyk-Jedryka A, Konieczkowska J, Siwy M, Bijak K, Sobolewska A, Stumpe J (2015) Photochromic supramolecular azopolyimides based on hydrogen bonds. Opt Mater 47:501–511

    Article  CAS  Google Scholar 

  11. Devi S, Bala I, Gupta SP, Kumar P, Pal SK, Venkataramani S (2019) Reversibly photoswitchable alkoxy azobenzenes connected benzenetricarboxamide discotic liquid crystals with perpetual long range columnar assembly. Org Biomol Chem 17(7):1947–1954

    Article  CAS  PubMed  Google Scholar 

  12. Faghihi K, Shabanian M (2010) Novel poly (ether-amide) s derived from 1,4-(4-carboxy phenoxy) butane and ethereal diamines: synthesis and properties. Macromol Res 18(12):1148–1153

    Article  CAS  Google Scholar 

  13. Shabanian M, Basaki N (2013) New photosensitive semi aramid/organoclay nanocomposite containing cinnamoyl groups: synthesis and characterization. Compos B Eng 52:224–232

    Article  CAS  Google Scholar 

  14. Shabanian M, Faghihi K, Shabani F (2012) Clay-reinforced semi-aromatic polyether-amide nanocomposites containing phosphine oxide moieties: synthesis and characterization. Polym Bull 68(2):375–390

    Article  CAS  Google Scholar 

  15. Shabanian M, Ardeshir H, Haji-Ali S, Moghanian H, Hajibeygi M, Faghihi K, Khonakdar HA, Salimi H (2016) Efficient poly (methyl-ether-imide)/LDH nanocomposite derived from a methyl rich bisphenol: from synthesis to properties. Appl Clay Sci 123:285–291

    Article  CAS  Google Scholar 

  16. Shabanian M, Basaki N, Khonakdar HA, Jafari SH, Hedayati K, Wagenknecht U (2014) Novel nanocomposites consisting of a semi-crystalline polyamide and Mg–Al LDH: morphology, thermal properties and flame retardancy. Appl Clay Sci 90:101–108

    Article  CAS  Google Scholar 

  17. 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(8):2234–2248

    Article  CAS  Google Scholar 

  18. Mao H, Zhang S (2014) Synthesis, characterization and gas transport properties of novel poly(amine-imide) s containing tetraphenylmethane pendant groups. J Mater Chem A 2(25):9835–9843

    Article  CAS  Google Scholar 

  19. Hsiao SH, Chang YM, Chen HW, Liou GS (2006) Novel aromatic polyamides and polyimides functionalized with 4-tert-butyltriphenylamine groups. J Polym Sci Part A Polym Chem 44(15):4579–4592

    Article  CAS  Google Scholar 

  20. Liou G-S, Chang C-W (2008) Highly stable anodic electrochromic aromatic polyamides containing N,N,N′,N′-tetraphenyl-p-phenylenediamine moieties: synthesis, electrochemical, and electrochromic properties. Macromolecules 41(5):1667–1674

    Article  CAS  Google Scholar 

  21. Hajibeygi M, Shabanian M, Omidi-Ghallemohamadi M, Khonakdar HA (2017) Optical, thermal and combustion properties of self-colored polyamide nanocomposites reinforced with azo dye surface modified ZnO nanoparticles. Appl Surf Sci 416:628–638

    Article  CAS  Google Scholar 

  22. Hajibeygi M, Shafiei-Navid S, Shabanian M, Vahabi H (2018) Novel poly(amide-azomethine) nanocomposites reinforced with polyacrylic acid-co-2-acrylamido-2-methylpropanesulfonic acid modified LDH: synthesis and properties. Appl Clay Sci 157:165–176

    Article  CAS  Google Scholar 

  23. Coluccini C, Sporer I, Leuteritz A, Kuehnert I, Wang D-Y (2014) Layered double hydroxide: a new promising nanomaterial in energy application. Nanomater Energy 3(5):177–191

    Article  Google Scholar 

  24. Goh K-H, Lim T-T, Dong Z (2008) Application of layered double hydroxides for removal of oxyanions: a review. Water Res 42(6–7):1343–1368

    Article  CAS  PubMed  Google Scholar 

  25. Xu ZP, Zhang J, Adebajo MO, Zhang H, Zhou C (2011) Catalytic applications of layered double hydroxides and derivatives. Appl Clay Sci 53(2):139–150

    Article  CAS  Google Scholar 

  26. Alcantara A, Aranda P, Darder M, Ruiz-Hitzky E (2010) Bionanocomposites based on alginate–zein/layered double hydroxide materials as drug delivery systems. J Mater Chem 20(42):9495–9504

    Article  CAS  Google Scholar 

  27. Wang X, Lin Y, Su Y, Zhang B, Li C, Wang H, Wang L (2017) Design and synthesis of ternary-component layered double hydroxides for high-performance supercapacitors: understanding the role of trivalent metal ions. Electrochim Acta 225:263–271

    Article  CAS  Google Scholar 

  28. Li J, Fan Q, Wu Y, Wang X, Chen C, Tang Z, Wang X (2016) Magnetic polydopamine decorated with Mg–Al LDH nanoflakes as a novel bio-based adsorbent for simultaneous removal of potentially toxic metals and anionic dyes. J Mater Chem A 4(5):1737–1746

    Article  CAS  Google Scholar 

  29. Shabanian M, Kang N-J, Wang D-Y, Wagenknecht U, Heinrich G (2013) Synthesis of aromatic–aliphatic polyamide acting as adjuvant in polylactic acid (PLA)/ammonium polyphosphate (APP) system. Polym Degrad Stab 98(5):1036–1042

    Article  CAS  Google Scholar 

  30. Tsai T-Y, Naveen B, Shiu W-C, Lu S-W (2014) An advanced preparation and characterization of the PET/MgAl-LDH nanocomposites. Rsc Adv 4(49):25683–25691

    Article  CAS  Google Scholar 

  31. Iyi N, Ebina Y, Sasaki T (2011) Synthesis and characterization of water-swellable LDH (layered double hydroxide) hybrids containing sulfonate-type intercalant. J Mater Chem 21(22):8085–8095

    Article  CAS  Google Scholar 

  32. Nhlapo N, Motumi T, Landman E, Verryn SM, Focke WW (2008) Surfactant-assisted fatty acid intercalation of layered double hydroxides. J Mater Sci 43(3):1033–1043

    Article  CAS  Google Scholar 

  33. Woo MA, Kim TW, Paek M-J, Ha H-W, Choy J-H, Hwang S-J (2011) Phosphate-intercalated Ca–Fe-layered double hydroxides: crystal structure, bonding character, and release kinetics of phosphate. J Solid State Chem 184(1):171–176

    Article  CAS  Google Scholar 

  34. Kaul PK, Samson AJ, Selvan GT, Enoch I, Selvakumar PM (2017) Synergistic effect of LDH in the presence of organophosphate on thermal and flammable properties of an epoxy nanocomposite. Appl Clay Sci 135:234–243

    Article  CAS  Google Scholar 

  35. Kakanejadifard A, Esna-ashari F, Hashemi P, Zabardasti A (2013) Synthesis and characterization of an azo dibenzoic acid Schiff base and its Ni(II), Pb(II), Zn(II) and Cd(II) complexes. Spectrochim Acta Part A Mol Biomol Spectrosc 106:80–85

    Article  CAS  Google Scholar 

  36. Basaki N, Kakanejadifard A, Faghihi K (2020) New electroactive and photosensitive polyamide/ternary LDH nanocomposite containing triphenylamine moieties in its backbone: synthesis and characterization. Iran Polym J 29(1):57–66

    Article  CAS  Google Scholar 

  37. Basaki N, Kakanejadifard A, Shabanian M, Faghihi K (2019) Synthesis and characterization of a new photosensitive and electroactive polyamide/LDH nanocomposite containing azo groups. Polym Bull 2019:1–16

    Google Scholar 

  38. Ghasemian M, Kakanejadifard A, Karami T (2016) Synthesis, structural characterization, antimicrobial activities and theoretical investigations of some 4-(4-aminophenylsulfonyl) phenylimino) methyl)-4-(aryldiazenyl) phenol. Spectrochim Acta Part A Mol Biomol Spectrosc 168:190–198

    Article  CAS  Google Scholar 

  39. Wang X, Spörer Y, Leuteritz A, Kuehnert I, Wagenknecht U, Heinrich G, Wang D-Y (2015) Comparative study of the synergistic effect of binary and ternary LDH with intumescent flame retardant on the properties of polypropylene composites. RSC Adv 5(96):78979–78985

    Article  CAS  Google Scholar 

  40. Chiang M-F, Chen E-C, Wu T-M (2012) Preparation, mechanical properties and thermal stability of poly (l-lactide)/γ-polyglutamate-modified layered double hydroxide nanocomposites. Polym Degrad Stab 97(6):995–1001

    Article  CAS  Google Scholar 

  41. Kang N-J, Wang D-Y, Kutlu B, Zhao P-C, Leuteritz A, Wagenknecht U, Heinrich G (2013) A new approach to reducing the flammability of layered double hydroxide (LDH)-based polymer composites: preparation and characterization of dye structure-intercalated LDH and its effect on the flammability of polypropylene-grafted maleic anhydride/d-LDH composites. ACS Appl Mater Interfaces 5(18):8991–8997

    Article  CAS  PubMed  Google Scholar 

  42. Kozanecka-Szmigiel A, Konieczkowska J, Switkowski K, Antonowicz J, Trzebicka B, Szmigiel D, Schab-Balcerzak E (2016) Influence of supramolecular interactions on photoresponsive behavior of azobenzene poly (amide imide) s. J Photochem Photobiol A 318:114–123

    Article  CAS  Google Scholar 

  43. Han Y-U, Lee W-S, Lee C-G, Park S-J, Kim K-W, Kim S-B (2011) Entrapment of Mg–Al layered double hydroxide in calcium alginate beads for phosphate removal from aqueous solution. Desalinat Water Treatment 36(1–3):178–186

    Article  CAS  Google Scholar 

  44. Iwan A, Schab-Balcerzak E, Grucela-Zajac M, Skorka L (2014) Optical properties of unsymmetrical azomethines with one imine bonds. Spectrochim Acta Part A Mol Biomol Spectrosc 117:152–157

    Article  CAS  Google Scholar 

  45. Ghasemian M, Kakanejadifard A, Azarbani F, Zabardasti A, Kakanejadifard S (2014) Spectroscopy and solvatochromism studies along with antioxidant and antibacterial activities investigation of azo–azomethine compounds 2-(2-hydroxyphenylimino) methyl)-4-phenyldiazenyl) phenol. Spectrochim Acta Part A Mol Biomol Spectrosc 124:153–158

    Article  CAS  Google Scholar 

  46. Khanmohammadi H, Abdollahi A (2012) New diaminomaleonitrile-based azo-azomethine dyes; synthesis, characterization and spectral properties. Dyes Pigm 94(1):163–168

    Article  CAS  Google Scholar 

  47. Sahoo M, Sinha B, Marbaniang M, Naik D (2011) Degradation and mineralization of Calcon using UV365/H2O2 technique: influence of pH. Desalination 280(1–3):266–272

    Article  CAS  Google Scholar 

  48. Chang C-W, Chung C-H, Liou G-S (2008) Novel anodic polyelectrochromic aromatic polyamides containing pendent dimethyltriphenylamine moieties. Macromolecules 41(22):8441–8451

    Article  CAS  Google Scholar 

  49. Hsiao S-H, Liou G-S, Kung Y-C, Lee Y-J (2010) Synthesis and characterization of electrochromic poly (amide–imide) s based on the diimide-diacid from 4, 4′-diamino-4″-methoxytriphenylamine and trimellitic anhydride. Eur Polymer J 46(6):1355–1366

    Article  CAS  Google Scholar 

  50. Zhan T, Song Y, Tan Z, Hou W (2017) Electrochemical bisphenol A sensor based on exfoliated Ni2Al-layered double hydroxide nanosheets modified electrode. Sensors Actuators B Chem 238:962–971

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran

    Nematollah Basaki & Ali Kakanejadifard

  2. Department of Chemistry, Faculty of Science, Arak University, Arāk, 38156-8-8349, Iran

    Khalil Faghihi

Authors
  1. Nematollah Basaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ali Kakanejadifard
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Khalil Faghihi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ali Kakanejadifard.

Additional information

Publisher's Note

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

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Basaki, N., Kakanejadifard, A. & Faghihi, K. Preparation of new enforcement polyamide nanocomposite filled by ternary layer double hydroxide and investigation of electrochemical activity, optical and thermal properties. Polym. Bull. 78, 6723–6741 (2021). https://doi.org/10.1007/s00289-020-03508-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-020-03508-6

Keywords

Search

Navigation