Skip to main content
SpringerLink
Log in

Synthesis, thermal and antimicrobial studies of some Schiff bases of chitosan

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

The Schiff bases of chitosan are synthesized by the reaction of chitosan with different aromatic aldehydes. The structures of the biopolymeric Schiff bases are characterized by Fourier transform infrared spectroscopy, 1H-NMR spectroscopy and elemental analysis (C, H, N). The 1H NMR spectroscopy is used to determine degree of deacetylation of chitosan and degree of substitution of Schiff bases. The Schiff base polymers have greater degrees of substitution varying from 65 to 88.5 %. Thermogravimetry of Schiff base polymers shows that they have nearly the same decomposition temperature as the chitosan, indicating that Schiff bases are thermally stable. The antimicrobial activities of chitosan and its Schiff bases are tested against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Aspergillus niger and found that the antimicrobial activities of the Schiff bases of chitosan were stronger than those of chitosan.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Kurita K. Chemistry and application of chitin and chitosan. Polym Degrad Stab. 1998;59:117–20.

    Article  CAS  Google Scholar 

  2. Prashanth KVH, Tharanathan RN. Chitin/chitosan: modifications and their unlimited application potential an overview. Trends Food Sci Technol. 2007;18:117–31.

    Article  CAS  Google Scholar 

  3. Honarkar H, Barikani M. Applications of biopolymers I: chitosan. Monatsh Chem. 2009;140:1403–20.

    Article  CAS  Google Scholar 

  4. Ravi Kumar MNV. A review of chitin and chitosan applications. React Funct Polym. 2000;46:1–27.

    Article  Google Scholar 

  5. Rinaudo M, Pavlov G, Desbrieres P. Influence of acetic acid concentration on the solubilization of chitosan. Polymer. 1999;40:7029–32.

    Article  CAS  Google Scholar 

  6. Yin X, Chen J, Yuan W, Lin Q, Ji L, Liu F. Preparation and antibacterial activity of Schiff bases from O-carboxymethyl chitosan and para-substituted benzaldehydes. Polym Bull. 2012;68:1215–26.

    Article  CAS  Google Scholar 

  7. Tirkistani FAA. Thermal analysis of some chitosan Schiff bases. Polym Degrad Stab. 1998;60:67–70.

    Article  CAS  Google Scholar 

  8. Dos Santos JE, Dockal ER, Cavalheiro ETG. Synthesis and characterization of Schiff bases from chitosan. Carbohydr Polym. 2005;60:277–82.

    Article  Google Scholar 

  9. Pereira FS, Agostini DLS, Job AE, GonzálezJiao ERP. Thermal studies of chitin–chitosan derivatives. J Therm Anal Calorim. 2013;114:321–7.

    Article  CAS  Google Scholar 

  10. Cimerman Z, Galic N, Bosner B. The Schiff bases of salicylaldehyde and aminopyridines as highly sensitive analytical reagents. Anal Chim Acta. 1997;343:145–53.

    Article  CAS  Google Scholar 

  11. Dos Santos JE, Dockal ER, Cavalheiro ETG. Thermal behavior of Schiff base from chitosan. J Therm Anal Calorim. 2005;79:243–8.

    Article  Google Scholar 

  12. Kurita K, Mori S, Nishiyama Y, Harata M. N-alkylation of chitin and some characteristics of the novel derivatives. Polym Bull. 2002;48:159–66.

    Article  CAS  Google Scholar 

  13. Arora S, Lal S, Kumar S, Kumar M, Kumar M. Comparative degradation kinetic studies of three biopolymers: chitin, chitosan and cellulose. Arch Appl Sci Res. 2011;3(3):188–201.

    CAS  Google Scholar 

  14. Aneja KR, Sharma C, Joshi R. Fungal infection of ear: a common problem in north eastern part of Haryana. Inter J Otorhinolaryngol. 2010;74:604–7.

    Article  CAS  Google Scholar 

  15. Ahmad I, Beg AJ. Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multidrug resistant human pathogens. J Ethnopharmacol. 2001;74:113–23.

    Article  CAS  Google Scholar 

  16. Andrews JM. Determination of minimum inhibitory concentrations. J Antimicrob Chemother. 2001;48:5–16.

    Article  CAS  Google Scholar 

  17. Al-Burtamani SKS, Fatope MO, Marwah RG, Onifade AK, Al-Saidi SH. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. J Ethnopharmocol. 2005;96:107–12.

    Article  CAS  Google Scholar 

  18. Jin X, Wang J, Bai J. Synthesis and antimicrobial activity of the Schiff base from chitosan and citral. Carbohyd Res. 2009;344:825–9.

    Article  CAS  Google Scholar 

  19. Colthup NB, Daly LH, Wiberley SE. Introduction to infrared and Raman spectroscopy. 3rd ed. San Diego: Academic Press; 1990.

    Google Scholar 

  20. Silverstein RM, Bassler GC, Morrill TC. Spectrometric identification of organic compounds. 5th ed. New York: Wiley; 1991.

    Google Scholar 

  21. Pawlak A, Mucha M. Thermogravimetric and FTIR studies of chitosan blends. Thermochim Acta. 2003;396:153–66.

    Article  CAS  Google Scholar 

  22. Tsai GJ, Su WH. Antibacterial activity of shrimp chitosan against Escherichia coli. J Food Prot. 1999;62:239–43.

    CAS  Google Scholar 

  23. Hwang JK, Kim HJ, Yoon SJ, Pyun YR. Bactericidal activity of chitosan on E. coli. In: Chen RH, Chen HC, editors. Advances in chitin science, vol. III. Taiwan: Rita Advertising; 1998. p. 340–4.

    Google Scholar 

Download references

Acknowledgements

One of the authors, Sohan Lal, is extremely thankful to the Council of Scientific and Industrial Research and University Grant Commission, New Delhi, India, for providing the research grant.

Author information

Authors and Affiliations

  1. Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, India

    Sohan Lal & Sanjiv Arora

  2. Department of Microbiology, M. M. University, Mullana, Ambala, Haryana, India

    Chetan Sharma

Authors
  1. Sohan Lal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sanjiv Arora
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chetan Sharma
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sohan Lal.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lal, S., Arora, S. & Sharma, C. Synthesis, thermal and antimicrobial studies of some Schiff bases of chitosan. J Therm Anal Calorim 124, 909–916 (2016). https://doi.org/10.1007/s10973-015-5227-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-015-5227-3

Keywords

Search

Navigation