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Journal of Polymer Research

, 26:34 | Cite as

Synthesis of o-aminophenol-m-phenylenediamine copolymer: an eco-friendly approach

  • M. Sh. ZorombaEmail author
  • M. H. Abdel-AzizEmail author
  • M. Bassyouni
  • E.-S. Z. El-Ashtoukhy
  • S. M. S. Abdel-Hamid
ORIGINAL PAPER
  • 82 Downloads

Abstract

Poly (o-aminophenol-co-m-phenylenediamine) P(oAP-mPDA) as a copolymer is successfully synthesized by mechanochemical solid state polymerization (MCSSP) as a green and simple method. The mechanochemical solid state polymerization is achieved by a developed Mortar Grinder RM200 without using any solvents during the preparation process. The copolymer was also prepared by traditional interfacial polymerization method (IP). A comparison between the resulting copolymers of the two methods is conducted by various analyses including, Fourier transform infrared spectra (FTIR), ultra violet, visible spectra (UV-Vis), X-ray diffraction (XRD), scanning electron microscope (SEM), and thermogravimetric analysis (TGA). The analyses revealed that there is a good agreement between the two copolymers synthesized by MCSSP and IP method. The energy band gap was determined and found to be 2.19 eV and 2.09 eV for the copolymer synthesized by MCSSP method and the IP method, respectively. The investigated copolymers are located in the semiconductor material range and displayed a good thermal stability.

Keywords

Green method Polymers Mechanochemical solid state polymerization Conducting copolymers 

Notes

References

  1. 1.
    Salunkhe PH, Patil YS, Patil VB, Navale YH, Dhole IA, Ubale VP, Maldar NN, Ghanwat AA (2018) Synthesis and characterization of conjugated porous polyazomethines with excellent electrochemical energy storage performance. J Polym Res 25:147CrossRefGoogle Scholar
  2. 2.
    Zoromba MS, Alghool S, Abdel-Hamid SMS, Bassyouni M, Abdel-Aziz MH (2017) Polymerization of aniline derivatives by K2Cr2O7 and production of Cr2O3 nanoparticles. Polym Adv Technol 28:842–848CrossRefGoogle Scholar
  3. 3.
    Slimane AB, Al-Hossainy AF, Zoromba MS (2018) Synthesis and optoelectronic properties of conductive nanostructured poly (aniline-co-o-aminophenol) thin film. J Mater Sci Mater Electron 29:8431–8445CrossRefGoogle Scholar
  4. 4.
    Hosny NM, Zoromba MS, Samir G, Alghool S (2016) Synthesis, structural and optical properties of nanoparticles derived from Cr doped polyanthranilic acid (CrPANA). J Mol Struct 1122:117–122CrossRefGoogle Scholar
  5. 5.
    Li C, Li Y, Wang X, Zhang B, Chen Y (2015) Synthesis and photovoltaic properties of conjugated copolymers containing cyclopentadithiophene and two different electron-deficient moieties in the polymer backbone. J Polym Res 22:96CrossRefGoogle Scholar
  6. 6.
    Zhang Z, Deng J, Wan M (2009) Highly crystalline and thin polyaniline nanofibers oxidized by ferric chloride. Mater Chem Phys 115:275–279CrossRefGoogle Scholar
  7. 7.
    Chen CH, Ko CJ, Chuang CH, Mao CF, Liao WT, Hsieh CD (2017) Synthesis and characterization of polyaniline co-doped with nitric acid and dodecyl benzene sulfonic acid. J Polym Res 24:10CrossRefGoogle Scholar
  8. 8.
    Jafari Y, Ghoreishi SM, Shabani-Nooshabadi M (2016) Electrochemical deposition and characterization of polyaniline-graphene nanocomposite films and its corrosion protection properties. J Polym Res 23:91CrossRefGoogle Scholar
  9. 9.
    Pinto NJ, Ramos I, Rojas R, Wang PC, Johnson Jr AT (2008) Electric response of isolated electrospun polyaniline nanofibers to vapors of aliphatic alcohols. Sensors Actuators B Chem 129:621–627CrossRefGoogle Scholar
  10. 10.
    Zoromba MS, Ismail MIM, Bassyouni M, Abdel-Aziz MH, Salah N, Alshahrie A, Memic A (2017) Fabrication and characterization of poly (aniline-co-o- anthranilic acid)/ magnetite nanocomposites and their application in wastewater treatment. Colloid Surface A: Physicochem Eng Aspects 520:121–130CrossRefGoogle Scholar
  11. 11.
    Zhou CF, Du XS, Liu Z, Ringer SP, Mai YW (2009) Solid phase mechanochemical synthesis of polyaniline branched nanofibers. Synth Met 159:1302–1307CrossRefGoogle Scholar
  12. 12.
    Hosny NM, Nowesser N, Al-Hussaini AS, Zoromba MS (2016) Doped copolymer of polyanthranilic acid and o-aminophenol (AA-co-OAP): synthesis, spectral characterization and the use of the doped copolymer as precursor of α-Fe2O3 nanoparticles. J Mol Struct 1106:479–484CrossRefGoogle Scholar
  13. 13.
    Somboonsub B, Srisuwan S, Invernale MA, Thongyai S, Praserthdam P, Scola DA, Sotzing GA (2010) Comparison of the thermally stable conducting polymers PEDOT, PANi, and PPy using sulfonated poly (imide) templates. Polymer 51:4472–4476CrossRefGoogle Scholar
  14. 14.
    Abdiryim T, Xiao-Gang Z, Jamal R (2005) Comparative studies of solid-state synthesized polyaniline doped with inorganic acid. Mater Chem Phys 15:367–372CrossRefGoogle Scholar
  15. 15.
    Meng H, Perepichka DF, Bendikov M, Wudl F, Pan GZ, Yu W, Dong W, Brown S (2003) Solid-state synthesis of a conducting polythiophene via an unprecedented heterocyclic coupling reaction. J Am Chem Soc 125:15151–15162CrossRefGoogle Scholar
  16. 16.
    Zoromba MS, Abdel-Aziz MH (2017) Ecofriendly method to synthesize poly (o-aminophenol) based on solid state polymerization and fabrication of nanostructured semiconductor thin film. Polymer 120:20–29CrossRefGoogle Scholar
  17. 17.
    Basavaraja C, Veeranagouda Y, Lee K, Vishnuvardhan TK, Pierson R (2010) Synthesis and characterization of conducting polypyrrole-polymannuronate nanocomposites. J Polym Res 17:233–239CrossRefGoogle Scholar
  18. 18.
    Mahmood WA, Azarian MH (2016) Sol-gel synthesis of polyaniline/zirconia composite conducting materials. J Polym Res 23:88CrossRefGoogle Scholar
  19. 19.
    Li XG, Huang MR, Hua YM (2005) Facile synthesis of processible aminoquinoline/phenetidine copolymers and their pure semiconducting nanoparticles. Macromolecules 38:4211–4219CrossRefGoogle Scholar
  20. 20.
    Li XG, Huang MR, Duan W, Yang YL (2002) Novel multifunctional polymers from aromatic diamines by oxidative polymerizations. Chem Rev 102:2925–3030CrossRefGoogle Scholar
  21. 21.
    Gupta B, Prakash R (2012) Interfacial polymerization of polyanthranilic acid: morphology controlled synthesis. Macromol Chem Phys 213:1457–1464CrossRefGoogle Scholar
  22. 22.
    Tauc J, Grigorovici R, Vancu A (1966) Optical properties and electronic structure of amorphous germanium. Ge and Si, Mater Res Phys Status Solidi B 15:627–637CrossRefGoogle Scholar
  23. 23.
    Barbero C, Silber JJ, Sereno L (1989) Formation of a novel electroactive film by electropolymerization of ortho-aminophenol: study of its chemical structure and formation mechanism. Electropolymerization of analogous compounds. J Electroanal Chem 263:333–352CrossRefGoogle Scholar
  24. 24.
    Tucceri R, Arnal PM, Scian AN (2012) Spectroscopic characterization of poly (ortho-aminophenol) film electrodes: a review article. J Spectroscopy 2013:1–26CrossRefGoogle Scholar
  25. 25.
    Yu S, Xi M, Han K, Wang Z, Yang W, Zhu H (2010) Preparation and photoelectrocatalytic properties of polyaniline/layered manganese oxide self-assembled film. Thin Solid Films 519:357–361CrossRefGoogle Scholar
  26. 26.
    Li J, Zhu L, Wu Y, Harima Y, Zhang A, Tang H (2006) Hybrid composites of conductive polyaniline and nanocrystalline titanium oxide prepared via self-assembling and graft polymerization. Polymer 47:7361–7367CrossRefGoogle Scholar
  27. 27.
    Olgun U, Gülfen M (2014) Doping of poly (o-phenylenediamine): spectroscopy, voltammetry, conductivity and band gap energy. React Funct Polym 77:23–29CrossRefGoogle Scholar
  28. 28.
    Thenmozhi G, Arockiasamy P, Santhi RJ (2014) Isomers of poly aminophenol: chemical synthesis, characterization, and its corrosion protection aspect on mild steel in 1 M HCl. Int J Electrochem 2014:1–11CrossRefGoogle Scholar
  29. 29.
    Sayyah SM, El-Rabiey MM, El-Rehim SS, Azooz RE (2006) Electropolymerization kinetics of o-aminophenol and characterization of the obtained polymer films. J Appl Polym Sci 99:3093–3109CrossRefGoogle Scholar
  30. 30.
    Dirlam PT, Glass RS, Char K, Pyun J (2017) The use of polymers in Li-S batteries: a review. J Polym Sci Part A: Polym Chem 55:1635–1668CrossRefGoogle Scholar
  31. 31.
    Mobarak Y, Bassyouni M, Almutawa M (2013) Materials selection, synthesis, and dielectrical properties of PVC nanocomposites. Adv Mater Sci Eng 2013:1–6CrossRefGoogle Scholar
  32. 32.
    Zoromba MS, Abdel-Aziz MH, Bassyouni M, Bahaitham H, Al-Hossainy AF (2018) Poly (o-phenylenediamine) thin film for organic solar cell applications. J Solid State Electrochem 22:3673–3687CrossRefGoogle Scholar
  33. 33.
    Al-Hossainy AF, Thabet HK, Zoromba MS, Ibrahim A (2018) Facile synthesis and fabrication of a poly (ortho-anthranilic acid) emeraldine salt thin film for solar cell applications. New J Chem 42:10386–10395CrossRefGoogle Scholar
  34. 34.
    Zoromba MS (2017) Novel and economic Acid-Base Indicator based on (p-toluidine) oligomer: synthesis; characterization; photoluminescence and Solvatochromism applications. Spectrochim Acta A: Mol Biomol Spectroscopy 187:61–67CrossRefGoogle Scholar
  35. 35.
    Zoromba MS, Abdel-Aziz MH, Bassyouni M (2017) New microstructured chromium doped poly (p-toluidine) as a new acid–base indicator and precursor for chromic oxide nanostructured. Polym Adv Technol 28:1743–1749CrossRefGoogle Scholar
  36. 36.
    Naveen MH, Gurudatt NG, Shim YB (2017) Applications of conducting polymer composites to electrochemical sensors: a review. Appl Mater Today 9:419–433CrossRefGoogle Scholar
  37. 37.
    El-Ashtoukhy ESZ, Abdel-Aziz MH (2013) Removal of copper from aqueous solutions by cementation in a bubble column reactor fitted with horizontal screens. Int J Miner Process 121:65–69CrossRefGoogle Scholar
  38. 38.
    Zoromba MS, Abdel-Aziz MH, Bassyouni M, Gutub S, Demko D, Abdelkader A (2017) Electrochemical activation of graphene at low temperature: the synthesis of three-dimensional nanoarchitectures for high performance supercapacitors and capacitive deionization. ACS Sustain Chem Eng 5:4573–4581CrossRefGoogle Scholar
  39. 39.
    Wang H, Barrett M, Duane B, Gu J, Zenhausern F (2018) Materials and processing of polymer-based electrochromic devices. Mater Sci Eng B 228:167–174CrossRefGoogle Scholar
  40. 40.
    Ravichandran R, Sundarrajan S, Venugopal JR, Mukherjee S, Ramakrishna S (2010) Applications of conducting polymers and their issues in biomedical engineering. J Royal Soc Interface 7:S559–S579CrossRefGoogle Scholar
  41. 41.
    Xia H, Wang Q (2002) Ultrasonic irradiation: a novel approach to prepare conductive polyaniline/nanocrystalline titanium oxide composites. Chem Mater 14:2158–2165CrossRefGoogle Scholar
  42. 42.
    Saravanan C, Palaniappan S, Chandezon F (2008) Synthesis of nanoporous conducting polyaniline using ternary surfactant. Mater Lett 62:882–885CrossRefGoogle Scholar

Copyright information

© The Polymer Society, Taipei 2019

Authors and Affiliations

  1. 1.Department of Chemical and Materials EngineeringKing Abdulaziz UniversityRabighSaudi Arabia
  2. 2.Chemistry Department, Faculty of SciencePort Said UniversityPort-SaidEgypt
  3. 3.Chemical Engineering Department, Faculty of EngineeringAlexandria UniversityAlexandriaEgypt
  4. 4.Department of Chemical EngineeringFaculty of Engineering Port Said UniversityPort SaidEgypt
  5. 5.Department of Chemical EngineeringThe Egyptian Academy for Engineering and Advanced Technology, Ministry of Military ProductionCairoEgypt

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