Research Article
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Year 2022, Volume: 9 Issue: 3, 879 - 888, 31.08.2022
https://doi.org/10.18596/jotcsa.1084225

Abstract

Supporting Institution

BİLİMSEL ARAŞTIRMA PROJELERİ KOORDİNATÖRLÜĞÜ (DÜBAP)

Project Number

FEN.19.009

References

  • 1. Xu J, McCarthy SP, Gross RA, Kaplan DL. Chitosan Film Acylation and Effects on Biodegradability. Macromolecules. 1996 Jan 1;29(10):3436–40.
  • 2. Zargar V, Asghari M, Dashti A. A Review on Chitin and Chitosan Polymers: Structure, Chemistry, Solubility, Derivatives, and Applications. ChemBioEng Reviews. 2015 Jun;2(3):204–26.
  • 3. Koc B, Akyuz L, Cakmak YS, Sargin I, Salaberria AM, Labidi J, et al. Production and characterization of chitosan-fungal extract films. Food Bioscience. 2020 Jun;35:100545.
  • 4. Noel SP, Courtney H, Bumgardner JD, Haggard WO. Chitosan Films: A Potential Local Drug Delivery System for Antibiotics. Clinical Orthopaedics & Related Research. 2008 Jun;466(6):1377–82. 5. Kiuchi H, Kai W, Inoue Y. Preparation and characterization of poly(ethylene glycol) crosslinked chitosan films. J Appl Polym Sci. 2008 Mar 15;107(6):3823–30.
  • 6. Patel VF, Liu F, Brown MB. Advances in oral transmucosal drug delivery. Journal of Controlled Release. 2011 Jul;153(2):106–16.
  • 7. Perugini P. Periodontal delivery of ipriflavone: new chitosan/PLGA film delivery system for a lipophilic drug. International Journal of Pharmaceutics. 2003 Feb 18;252(1–2):1–9.
  • 8. Pedro AS, Cabral-Albuquerque E, Ferreira D, Sarmento B. Chitosan: An option for development of essential oil delivery systems for oral cavity care? Carbohydrate Polymers. 2009 May;76(4):501–8.
  • 9. Ahmed M, Harish N, Charyulu R, Prabhu P. Formulation of chitosan-based ciprofloxacin and diclofenac film for periodontitis therapy. Trop J Pharm Res. 2009 Feb 27;8(1):33–41.
  • 10. Hirano S, Yamaguchi R, Matsuda N, Miura O, Kondo Y. Chitosan-aldehyde Gel A Novel Polysaccharide Gel Produced from Chitosan and Aldehydes. Agricultural and Biological Chemistry. 1977 Aug;41(8):1547–8.
  • 11. Sharma S, Jain P, Tiwari S. Dynamic imine bond based chitosan smart hydrogel with magnified mechanical strength for controlled drug delivery. International Journal of Biological Macromolecules. 2020 Oct;160:489–95.
  • 12. Rahnama H, Nouri Khorasani S, Aminoroaya A, Molavian MR, Allafchian A, Khalili S. Facile preparation of chitosan-dopamine-inulin aldehyde hydrogel for drug delivery application. International Journal of Biological Macromolecules. 2021 Aug;185:716–24.
  • 13. Marin L, Stoica I, Mares M, Dinu V, Simionescu BC, Barboiu M. Antifungal vanillin–imino-chitosan biodynameric films. J Mater Chem B. 2013;1(27):3353.
  • 14. Craciun AM, Mititelu Tartau L, Pinteala M, Marin L. Nitrosalicyl-imine-chitosan hydrogels based drug delivery systems for long term sustained release in local therapy. Journal of Colloid and Interface Science. 2019 Feb;536:196–207.
  • 15. Barbosa HFG, Attjioui M, Leitão A, Moerschbacher BM, Cavalheiro ÉTG. Characterization, solubility and biological activity of amphihilic biopolymeric Schiff bases synthesized using chitosans. Carbohydrate Polymers. 2019 Sep;220:1–11.
  • 16. Liu C, Dong C, Liu S, Yang Y, Zhang Z. Multiple chiroptical switches and logic circuit based on salicyl‒ imine‒chitosan hydrogel. Carbohydrate Polymers. 2021 Apr;257:117534.
  • 17. Alkabli J. Progress in preparation of thiolated, crosslinked, and imino-chitosan derivatives targeting specific applications. European Polymer Journal. 2022 Feb;165:110998.
  • 18. Ying G qing, Xiong W yue, Wang H, Sun Y, Liu H zhang. Preparation, water solubility and antioxidant activity of branched-chain chitosan derivatives. Carbohydrate Polymers. 2011 Feb 1;83(4):1787–96.
  • 19. Zidan TA, Abdelhamid AE, Zaki EG. N-Aminorhodanine modified chitosan hydrogel for antibacterial and copper ions removal from aqueous solutions. International Journal of Biological Macromolecules. 2020 Sep;158:32–42.
  • 20. Karakaplan M, Turgut Y, Hoşgören H. A practical synthesis of chiral 3-aryloxy-1,2-propanediols. Journal of Chemical Research. 2005 Jan;2005(1):41–2.
  • 21. Liu J, Meng C guang, Yan Y hua, Shan Y na, Kan J, Jin C hai. Protocatechuic acid grafted onto chitosan: Characterization and antioxidant activity. International Journal of Biological Macromolecules. 2016 Aug;89:518–26.
  • 22. Cardenas G, Miranda SP. Ftir and tga studies of chitosan composite films. J Chil Chem Soc [Internet]. 2004 Dec [cited 2022 Jun 22];49(4).
  • 23. Liu J, Lu J feng, Kan J, Jin C hai. Synthesis of chitosan-gallic acid conjugate: Structure characterization and in vitro anti-diabetic potential. International Journal of Biological Macromolecules. 2013 Nov;62:321–9.
  • 24. Hu Q, Wang T, Zhou M, Xue J, Luo Y. In Vitro Antioxidant-Activity Evaluation of Gallic-Acid-Grafted Chitosan Conjugate Synthesized by Free-Radical-Induced Grafting Method. J Agric Food Chem. 2016 Jul 27;64(29):5893–900.
  • 25. Jiao TF, Zhou J, Zhou J, Gao L, Xing Y, Li X. Synthesis and characterization of chitosan-based Schiff base compounds with aromatic substituent groups. 2011;
  • 26. Cho YW, Jang J, Park CR, Ko SW. Preparation and Solubility in Acid and Water of Partially Deacetylated Chitins. Biomacromolecules. 2000 Dec 1;1(4):609–14.
  • 27. Heras-Mozos R, Hernández R, Gavara R, Hernández-Muñoz P. Dynamic covalent chemistry of imines for the development of stimuli-responsive chitosan films as carriers of sustainable antifungal volatiles. Food Hydrocolloids. 2022 Apr;125:107326.
  • 28. Sun L, Sun J, Chen L, Niu P, Yang X, Guo Y. Preparation and characterization of chitosan film incorporated with thinned young apple polyphenols as an active packaging material. Carbohydrate Polymers. 2017 May;163:81–91.

Salicylaldehydediol Grafted onto Chitosan: Characterization and Their Film Properties

Year 2022, Volume: 9 Issue: 3, 879 - 888, 31.08.2022
https://doi.org/10.18596/jotcsa.1084225

Abstract

The concentrations of linker group effect different physicochemical features of the biopolymer, including thermal stability, shape, swelling, and water solubility. Herein, three novel chitosan (CH) based films (CHSD1-3) have been prepared by a facile method for their film characteristics. Thus, amphiphilic salicylaldehydediol (SD) was synthesized from hydrophilic glycidol and salicylaldehyde in high yield and regioselectivity. CHSD1-3 films were prepared by the imine condensation reaction of polymeric chitosan backbone and various ratios of SD linker. The reaction takes place with high conversation and amazingly mechanically resistant thickness films without using any plasticizer that exhibits low water solubility and low swelling ratios at pH > 3, which can be suggested as thin layer protecting systems for medical devices. Chitosan-salicylaldehydediol biopolymer films were characterized by Fourier transform infrared (FT-IR) spectroscopy, differential scanning calorimetry (DSC), and X-ray diffraction (XRD) methods. The FT-IR, DSC, and XRD results show a clear linkage of the SD group to the chitosan backbone, high thermal stability of the films, and a change in the original nature of chitosan, respectively. Scanning Electron Microscopy (SEM) observations have also supported the successful grafting of the SD group onto the chitosan.

Project Number

FEN.19.009

References

  • 1. Xu J, McCarthy SP, Gross RA, Kaplan DL. Chitosan Film Acylation and Effects on Biodegradability. Macromolecules. 1996 Jan 1;29(10):3436–40.
  • 2. Zargar V, Asghari M, Dashti A. A Review on Chitin and Chitosan Polymers: Structure, Chemistry, Solubility, Derivatives, and Applications. ChemBioEng Reviews. 2015 Jun;2(3):204–26.
  • 3. Koc B, Akyuz L, Cakmak YS, Sargin I, Salaberria AM, Labidi J, et al. Production and characterization of chitosan-fungal extract films. Food Bioscience. 2020 Jun;35:100545.
  • 4. Noel SP, Courtney H, Bumgardner JD, Haggard WO. Chitosan Films: A Potential Local Drug Delivery System for Antibiotics. Clinical Orthopaedics & Related Research. 2008 Jun;466(6):1377–82. 5. Kiuchi H, Kai W, Inoue Y. Preparation and characterization of poly(ethylene glycol) crosslinked chitosan films. J Appl Polym Sci. 2008 Mar 15;107(6):3823–30.
  • 6. Patel VF, Liu F, Brown MB. Advances in oral transmucosal drug delivery. Journal of Controlled Release. 2011 Jul;153(2):106–16.
  • 7. Perugini P. Periodontal delivery of ipriflavone: new chitosan/PLGA film delivery system for a lipophilic drug. International Journal of Pharmaceutics. 2003 Feb 18;252(1–2):1–9.
  • 8. Pedro AS, Cabral-Albuquerque E, Ferreira D, Sarmento B. Chitosan: An option for development of essential oil delivery systems for oral cavity care? Carbohydrate Polymers. 2009 May;76(4):501–8.
  • 9. Ahmed M, Harish N, Charyulu R, Prabhu P. Formulation of chitosan-based ciprofloxacin and diclofenac film for periodontitis therapy. Trop J Pharm Res. 2009 Feb 27;8(1):33–41.
  • 10. Hirano S, Yamaguchi R, Matsuda N, Miura O, Kondo Y. Chitosan-aldehyde Gel A Novel Polysaccharide Gel Produced from Chitosan and Aldehydes. Agricultural and Biological Chemistry. 1977 Aug;41(8):1547–8.
  • 11. Sharma S, Jain P, Tiwari S. Dynamic imine bond based chitosan smart hydrogel with magnified mechanical strength for controlled drug delivery. International Journal of Biological Macromolecules. 2020 Oct;160:489–95.
  • 12. Rahnama H, Nouri Khorasani S, Aminoroaya A, Molavian MR, Allafchian A, Khalili S. Facile preparation of chitosan-dopamine-inulin aldehyde hydrogel for drug delivery application. International Journal of Biological Macromolecules. 2021 Aug;185:716–24.
  • 13. Marin L, Stoica I, Mares M, Dinu V, Simionescu BC, Barboiu M. Antifungal vanillin–imino-chitosan biodynameric films. J Mater Chem B. 2013;1(27):3353.
  • 14. Craciun AM, Mititelu Tartau L, Pinteala M, Marin L. Nitrosalicyl-imine-chitosan hydrogels based drug delivery systems for long term sustained release in local therapy. Journal of Colloid and Interface Science. 2019 Feb;536:196–207.
  • 15. Barbosa HFG, Attjioui M, Leitão A, Moerschbacher BM, Cavalheiro ÉTG. Characterization, solubility and biological activity of amphihilic biopolymeric Schiff bases synthesized using chitosans. Carbohydrate Polymers. 2019 Sep;220:1–11.
  • 16. Liu C, Dong C, Liu S, Yang Y, Zhang Z. Multiple chiroptical switches and logic circuit based on salicyl‒ imine‒chitosan hydrogel. Carbohydrate Polymers. 2021 Apr;257:117534.
  • 17. Alkabli J. Progress in preparation of thiolated, crosslinked, and imino-chitosan derivatives targeting specific applications. European Polymer Journal. 2022 Feb;165:110998.
  • 18. Ying G qing, Xiong W yue, Wang H, Sun Y, Liu H zhang. Preparation, water solubility and antioxidant activity of branched-chain chitosan derivatives. Carbohydrate Polymers. 2011 Feb 1;83(4):1787–96.
  • 19. Zidan TA, Abdelhamid AE, Zaki EG. N-Aminorhodanine modified chitosan hydrogel for antibacterial and copper ions removal from aqueous solutions. International Journal of Biological Macromolecules. 2020 Sep;158:32–42.
  • 20. Karakaplan M, Turgut Y, Hoşgören H. A practical synthesis of chiral 3-aryloxy-1,2-propanediols. Journal of Chemical Research. 2005 Jan;2005(1):41–2.
  • 21. Liu J, Meng C guang, Yan Y hua, Shan Y na, Kan J, Jin C hai. Protocatechuic acid grafted onto chitosan: Characterization and antioxidant activity. International Journal of Biological Macromolecules. 2016 Aug;89:518–26.
  • 22. Cardenas G, Miranda SP. Ftir and tga studies of chitosan composite films. J Chil Chem Soc [Internet]. 2004 Dec [cited 2022 Jun 22];49(4).
  • 23. Liu J, Lu J feng, Kan J, Jin C hai. Synthesis of chitosan-gallic acid conjugate: Structure characterization and in vitro anti-diabetic potential. International Journal of Biological Macromolecules. 2013 Nov;62:321–9.
  • 24. Hu Q, Wang T, Zhou M, Xue J, Luo Y. In Vitro Antioxidant-Activity Evaluation of Gallic-Acid-Grafted Chitosan Conjugate Synthesized by Free-Radical-Induced Grafting Method. J Agric Food Chem. 2016 Jul 27;64(29):5893–900.
  • 25. Jiao TF, Zhou J, Zhou J, Gao L, Xing Y, Li X. Synthesis and characterization of chitosan-based Schiff base compounds with aromatic substituent groups. 2011;
  • 26. Cho YW, Jang J, Park CR, Ko SW. Preparation and Solubility in Acid and Water of Partially Deacetylated Chitins. Biomacromolecules. 2000 Dec 1;1(4):609–14.
  • 27. Heras-Mozos R, Hernández R, Gavara R, Hernández-Muñoz P. Dynamic covalent chemistry of imines for the development of stimuli-responsive chitosan films as carriers of sustainable antifungal volatiles. Food Hydrocolloids. 2022 Apr;125:107326.
  • 28. Sun L, Sun J, Chen L, Niu P, Yang X, Guo Y. Preparation and characterization of chitosan film incorporated with thinned young apple polyphenols as an active packaging material. Carbohydrate Polymers. 2017 May;163:81–91.
There are 27 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Murat Evcil 0000-0002-4646-8042

Mehmet Karakaplan 0000-0002-9833-3633

Project Number FEN.19.009
Publication Date August 31, 2022
Submission Date March 7, 2022
Acceptance Date June 1, 2022
Published in Issue Year 2022 Volume: 9 Issue: 3

Cite

Vancouver Evcil M, Karakaplan M. Salicylaldehydediol Grafted onto Chitosan: Characterization and Their Film Properties. JOTCSA. 2022;9(3):879-88.