Skip to main content
Log in

Cyclocopolymerization of N,N-Diallylammonium and N,N-Diallylguanidinium Acetate with Acrylonitrile Characterization, Thermal and Morphological Properties

  • Research Article - Chemistry
  • Published:
Arabian Journal for Science and Engineering Aims and scope Submit manuscript

Abstract

Two diallylamine salts, diallylammonium acetate (DAA acetate) and diallylguanidinium acetate (DAGA) were cyclocopolymerized in water with acrylonitrile (AN) using power ultrasound in order to prepare acrylonitrile copolymers involving thermally stable heterocyclic rings in their polymeric matrix. The structural characterization of the copolymers was performed using FTIR, \(^{13}\)C NMR, UV/Vis spectroscopy and elemental analysis. The results revealed that the diallyl amine salts cyclopolymerized to form pyrrolidine and not piperidine rings throughout the polymeric chains. The thermal behavior of the copolymers prepared under nitrogen atmosphere was investigated using thermogravimetry, differential thermal analysis (TGA/DTA) and differential scanning calorimetry. The morphological property was also discussed using scanning electron microscopy (ESEM). The results revealed that the thermal stability of the copolymers was improved by the increase in the content of N,N-diallylammonium and N,N-diallylguanidinium acetate. The power of ultrasonic waves enhanced the homogeneity of the copolymers blend films irrespective of the copolymer compositions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Abdel-Naby, A.: Copolymerization of acrylonitrile with N(substituted phenyl) itaconimide. J. Appl. Polym. Sci. 121, 169–175 (2011)

    Article  Google Scholar 

  2. Korobeinyk, A.; Whitby, R.; Mikhalovsky, S.: High temperature oxidative resistance of polyacrylonitrile-methylmethacrylate copolymer powder converting to a carbonized monolith. Eur. Polym. J. 48, 97–104 (2012)

    Article  Google Scholar 

  3. Tan, J.; Wang, X.; Tai, J.; Luo, Y.; Jia, D.: Novel blends of acrylonitrile butadiene rubber and polyurethane-silica hybrid networks. Expr. Polym. Lett. 6, 588–600 (2012)

    Article  Google Scholar 

  4. Bajaj, P.; Sreekumar, T.; Sen, K.: Thermal behaviour of acrylonitrile copolymers having methacrylic and itaconic acid comonomers. Polymer 24, 1707–1718 (2001)

    Article  Google Scholar 

  5. Sabaa, M.; Mikhael, M.; Yassin, A.; Elsabeè, M.: Copolymerization of acrylonitrile with N-substituted maleimides. Die. Angew. Makromol. Chem. 139, 95–112 (1986)

    Article  Google Scholar 

  6. Abdel-Naby, A.: Ultrasound assisted copolymerization of acrylonitrile with N-amino phenyl maleimides and N-amino phenyl 2,3 dimethyl maleimides. Ultrason. Sonochem. 19, 1180–1185 (2012)

    Article  Google Scholar 

  7. Butler, G.B.; Ingley, F.: Preparation and polymerization of unsaturated quaternary ammonium compounds. II. Halogenated allyl derivatives\(^{1,2}\). J. Am. Chem. Soc. 73, 895–896 (1951)

    Article  Google Scholar 

  8. Kadem, K.: Cyclopolymerization of diallyamine and its condensation with carboxylic drugs. Int. J. Chem. Sci. 13(2), 725–736 (2015)

    Google Scholar 

  9. Ali, Sh; Goni, L.; Mazumder, M.: Butler’s cyclopolymerizaton protocol in the synthesis of diallylamine salts/sulfur dioxide alternate polymers containing amino acid residues. J. Polym. Res. 24(184), 1–12 (2017)

    Google Scholar 

  10. Ali, Sh; Al-Hamouz, O.: Synthesis and cyclopolymerization of diallylammoniomethanesulfonate. Polym. Eng. Sci. 53, 2378–2388 (2013)

    Article  Google Scholar 

  11. Zaikov, G.; Malkanduev, Y.U.; Khashirova, S.; Esmurziev, A.; Mortynenko, A.; Sivova, L.; Sivov, N.: Synthesis and potential radical copolymerization of new monomers based on diallylamine. J. Appl. Sci. 91, 439–444 (2001)

    Article  Google Scholar 

  12. Vivekanandam, T.; Gopalan, A.; Vasudevan, T.; Umapathy, S.: Sonochemical cyclopolymerization of diallylamine in the presence of peroxomonosulfate. J. Appl. Polym. Sci. 98, 1548–1553 (2005)

    Article  Google Scholar 

  13. Kamel, M.; Helmy, H.; Mashaly, H.; Kafafy, H.: Ultrasonic assisted dyeing: dyeing of acrylic fabrics C.I. Astrazon basic red 5BL 200%. Ultrason Sonochem. 17, 92–97 (2010)

    Article  Google Scholar 

  14. Abdel-Naby, A.; Al-Harthi, S.: Dyeability and mechanical properties of acrylonitrile–diallylamine salts copolymers. Am. J. Appl. Sci. 10, 525–532 (2013)

    Article  Google Scholar 

  15. Sivov, N.; Martynenko, A.; Bondarenko, G.; Filatova, M.; Kabanova, E.; Popova, N.; Sivo, A.; Kruts’ko, E.: Structure and composition of guanidine acrylate, guanidine methacrylate, their homopolymers, and copolymers with diallyldimethylammonium chloride. Pet. Chem. 46, 41–59 (2006)

    Article  Google Scholar 

  16. Beevers, R.; White, E.: A note on the glass-transition temperatures of acrylonitrile + styrene copolymers. Polym. Lett. 1, 171–176 (1963)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Abir S. Abdel-Naby.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Al-Ghamdi, A.A., Al-Harthi, S.N., EL-Sharif, A.M. et al. Cyclocopolymerization of N,N-Diallylammonium and N,N-Diallylguanidinium Acetate with Acrylonitrile Characterization, Thermal and Morphological Properties. Arab J Sci Eng 44, 6303–6311 (2019). https://doi.org/10.1007/s13369-019-03734-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13369-019-03734-9

Keywords

Navigation