Synthesis, Characterization, Swelling Behavior and Metal Uptake Studies of Dichloroglyoxime Crosslinked Chitosan Derivative

Abstract

New crosslinked derivative of chitosan was prepared by the condensation reaction of chitosan (CS) and dichloro glyoxime. Structural analysis of chitosan derivative (CSL) was performed by elemental analysis (C, H, N), SEM measurements, FT-IR, solid-state 13C CP/MAS NMR, XRD-powder and TGA. Crosslinking ratio was determined from the elemental analysis by using the C/N and found to be 70%. The swelling behavior of derivative was investigated on pH 3-7 and 10 at 25 and 37°C. Metal ion uptake capacity was studied towards of selected transition metals Cu(II), Ni(II), Co(II), Fe(II) and (Cd(II)  cations in aqueous medium. According to the results of the analyses; water retention capacity and metal uptake capacity of new cross-linked chitosan derivative is higher than chitosan and metal uptake sequence are Cu(II) > Fe(II) >Cd(II) > Co(II) > Ni(II) respectively.

Keywords:

Crosslink; Chitosan; Swelling; Metal-ion uptake.

DOI: 10.17350/HJSE19030000131

Full Text: page_white_acrobat.png

Downloads

Download data is not yet available.

References

1. Peppas NA, Bures P, Leobandung W, Ichikawa H, Modular Hydrogels for Drug Delivery, European Journal of Pharmaceutics and Biopharmaceutics 50 (2000) 27-46.

2. Mogosanu GD, Grumezescu AM, Natural and synthetic polymers for wounds and burns dressing, International Journal of Pharmaceutics 463 (2014) 127-136.

3. Jayakumar R, Prabaharan M, Kumar PTS, Nair SV, Tamura H, Biomaterials based on chitin and chitosan in wound dressing applications, Biotechnology Advances 29 (2011) 322-337.
4. Boonsongrit Y, Mitrevej A, Mueller BW, Chitosan Drug Binding by Ionic Interaction, European Journal of Pharmaceutics and Biopharmaceutic 62 (2006) 267-274.

5. Pillai CKS, Paul W, Sharma CP, Chitin and chitosan polymers: Chemistry, solubility and fiber formation, Progress in Polymer Science 34 (2009) 641-678.

6. Jayakumar R, Prabaharan M, Nair SV, Tokura S, Tamura H, Selvmurugan N, Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications, Progress in Materials Science 55 (2010) 675-709.

7. Muzzarelli RAA, “Chitin”, Pergamon Press, Oxford. 309, 1977.

8. Rinaudo M, Chitin and chitosan: Properties and application, Progress in Polymer Science 31 (2006) 603-632.

9. Rodrigues CA, Laranjeira MCM, De-Fávere VT, Stadler E, Interaction of Cu(II) on N-(2-pyridylmethyl) and N-(4-pyridylmethyl) chitosan, Polymer 39 (1998) 5121-5126.

10. Wan MW, Kan CC, Rogel BD, Dalida MLP, Adsorption of copper(II) and lead(II) ions from aqueous solution on chitosan-coated sand, Carbohydrate Polymers 80 (2010) 891-899.

11. Laftah WA, Hashim S, Ibrahim AN, Polymer hydrogels:A review, Polymer Plastics Technology and Engineering 50 (2011) 1475.

12. Rivas BL, Geckeler KE, Synthesis and metal complexation of poly(ethylenimine) and derivatives, Advances in Polymer Science 102 (1992) 173-183.

13. Rosso F, Barbarıssı A, Barbarıssı M, Petıllo O, Margaruccı S, Calarco A, Peluso G, New polyelectrolyte hydrogels for biomedical applications, Materials Science and Engineering 23 (2003) 371-376.

14. Evmenenko G, Alexev V, Budtova T, Buyanov A, Frenkel S, Swelling-induced changes of polyelectrolyte gels, Polymer 40 (1999) 2975-2979.

15. Dolbow J, Elıot F, Jı H, Chemically induced swelling of hydrogels. Journal of the Mechanics and Physics of Solids 52 (2004) 51-84.

16. Yang Z, Shu J, Zhang L, Wang Y, Preparation and adsorption behavior for metal ions of cyclic polyamine derivative of chitosan, Journal of Applied Polymer Science 100 (2006) 3018-3023.

17. Trimukhe KD, Varma AJ, A morphological study of heavy metal complexes of chitosan and crosslinked chitosans by SEM and WAXRD, Carbohydrate Polymer 71 (2008) 698-702.
18. Lance KA, Goldsby KA, Busch DH, Effective new cobalt(II) dioxygen carriers derived from dimethylglyoxime by the replacement of the linking protons with difluoroboron(1+), Inorganic Chemistry 29 (1990) 4537-4544.

19. Sankararamakrishnan N, Sanghi R, Preparation and characterization of a novel xanthated chitosan, Carbohydrate Polymers 66 (2006) 2, 160-167.

20. Sheldrick GM, SHELX 97 Programs for the refinement of Crystal Structures, University of Göttingen: Germany 1997.

21. Taner B, Deveci P, Bereket S Solak AO, Ozcan E, The first example of calix[4] pyrrole functionalized vic-dioximeligand: synthesis, characterization, spectroscopic studies andredox properties of the mononuclear transition metal complexes, Inorgic Chimica Acta 363 (2010) 4017-4023.

22. Coşkun A, Yılmaz F, Akgemici EG, Synthesis, characterization and electrochemical investigation of a novel vic-dioximeligand and its some transition metal complexes, Journal of Inclusion Phenomena and Macrocyclic Chemistry 60 (2008) 393–400.
23. Brugnerotto J, Lizardi J, Goycoolea FM, Arguelles-Monal W, Desbrieres J, Rinaudo M, An infrared investigation in relation with chitin and chitosan characterization, Polymer 42 (2001) 3569-3580.

24. Kasaai MR, A review of several reported procedures to determine the degree of N-acetylation for chitin and chitosan using infrared spectroscopy, Carbohydrate. Polymers 71(2008) 497-508.

25. Baran T, Açıksöz E, Menteş A, Highly efficient, quick and green synthesis of biarlys with chitosan supported catalyst using microwave irradiation in the absence of solvent, Carbohydrate Polymers 142 (2016) 189–198.

26. Wang X, Du Y, Fan L, Liu H, Hu Y, Chitosan- metal complexes as antimicrobial agent: synthesis, characterization and Structure-activity study, Polymer Bulletin 55 (2005) 105–113.

27. Franca EF, Lins RD, Freitas LCG, Straatsma TP, Characterization of chitin and chitosan molecular structure in aqueous solution, Journal of Chemical Theory and Computation 4(12) (2008) 2141–2149.

28. Wan Y, Creber KAM, Peppley B, Bui VT, Ionic conductivity and tensile properties of hydroxyethyl and hydroxypropyl chitosan membranes, Polymer Physics 42(8) (2004) 1379–1397.

29. Jothimani B, Sureshkumar S, Venkatachalapathy B, Hydrophobic structural modification of chitosan and its impact on nanoparticle synthesis–A physicochemical study, Carbohydrate Polymers 173 (2017) 714-720.

30. Serin S, New vic-dioxime transition metal complexes, Transition Metal Chemistry 26(3) (2001) 300–306.
31. Voloshin YZ, Kostromina NN, Roland K, Clathrochelates synthesis, structure and properties, Elsevier, Amsterdam, Netherlands, 2002.

32. Demetgül C, Serin S, Synthesis and Characterization of a New vic-dioxime of Chitosan Derivative ant Its Transition Metal Complexes, Carbohydrate Poylmers 72(3) (2008) 506-512.

33. Sharma AL, Saxena V, Annapoorni S, Malhotra BD, Synthesis and characterization of a copolymer: Poly(aniline-co-fluoroaniline), Journal of Applied Polymer Science, 81(6) (2001) 1460-1466.

34. Üzüm ÖB, Karadağ E, Dye sorption and water uptake properties of crosslinked acrylamide/sodium methacrylate copolymers and semi-interpenetrating polymer networks composed of PEG, Seperation Science and Technology, 46(2011) 489-499.
35. Duman SS, Şenel S, Kitosan ve Veteriner Alandaki Uygulamaları, Veteriner Cerrahi Dergisi 10(3-4) (2004) 62-72.

36. Saraydın D, Karadag E, Isıkver Y, Sahiner N, Güven O, The influence of preparation methods on the swelling and network properties of acrylamide hydrogels with crosslinkers, Journal of Macromolecular Science Part; A_Pure and Applied Chemistry A41(4) (2004) 421-433.

37. Karadag E, Saraydın D, Swelling of Superabsorbent Acrylamide/Sodium Acrylate Hydrogels Prepared by Using Multi-Functional Cross-Linkers, Turkish Journal Of Chemistry 26 (2002) 863-875.
Published
2019-01-31
How to Cite
Timur, M. (2019). Synthesis, Characterization, Swelling Behavior and Metal Uptake Studies of Dichloroglyoxime Crosslinked Chitosan Derivative. Hittite Journal of Science & Engineering, 6(1), 37-44. Retrieved from https://www.hjse.hitit.edu.tr/hjse/index.php/HJSE/article/view/HJSE19030000131
Section
SCIENCE