Structure, properties and application to water-soluble coatings of complex antimicrobial agent Ag-carboxymethyl chitosan-thiabendazole

Abstract

The structure, properties and application to water-soluble coatings of a new complex antimicrobial agent Ag-carboxylmethyl citosan-thiabendazole (Ag-CMCTS-TBZ) prepared from different materiel ratios were reported. The silver ions were preferably coordinated with the free — NH₂ groups and the — OH groups of secondary alcohol and carboxyl in CMCTS. TBZ preferably bonded to carboxyl group in CMCTS by electrostatic force and hydrogen bonding. Increase in silver ions content in the complex agent improved to some limited extent the antibacterial activity, but enhanced coloring and cost of the complex agent. Increase in TBZ content resulted in increase of antifungal activity, but decrease of water solubility of the complex agent. The antimicrobial MICs of the complex agent to Esherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger, Mucor sp. were 20 – 80, 15 – 60, 20 – 55, 40 – 250, and 400 – 1700 mg/kg, respectively. Addition of 0.1% of this complex agent to acrylic emulsion paint made the paint without substantial change in color, luster, viscosity, odor or pH value, but with an excellent and chronically persisting broad-spectra antimicrobial activity.

Keywords

complex antimicrobial agent / carboxylmethyl chitosan / silver / thiabendazole / water-based acrylic emulsion paint / water-soluble antimicrobial coating

References

[1] XiaJin-lan, WangChun, LiuXin-xing. Antimicrobial agents and antimicrobial mechanisms[J]. Journal of Central South University (Natural Science), 2004, 35(1): 31-38(in Chinese)

[2] BergerT. J., SpadaroJ. A., ChapinS. E., BeckerR. O.. Electrically Generated Silver Ions: Quantitative Effects on Bacterial and Mammalian Cells. Antimicrobial Agents and Chemotherapy, 1976, 9(2): 357-358

[3] BergerT. J., SpadaroJ. A., BiermanR., ChapinS. E., BeckerR. O.. Antifungal Properties of Electrically Generated Metallic Ions. Antimicrobial Agents and Chemotherapy, 1976, 10(5): 856-860

[4] ZHAO Guo-jing, Stevens Jr S E. Multiple parameters for the comprehensive evaluation of the susceptibility of Escherichia coli to the silver ion[J]. BioMetals, 1998, (11): 27–32.

[5] NoH. Antibacterial activity of chitosans and chitosan oligomers with different molecular weights. International Journal of Food Microbiology, 2002, 74(1-2): 65-72

[6] DevlieghereF, VermeulenA, DebevereJ. Chitosan: antimicrobial activity, interactions with food components and applicability as a coating on fruit and vegetables. Food Microbiology, 2004, 21(6): 703-714

[7] GilGabriela, del MónacoSilvana, CerruttiPatricia, GalvagnoMiguel. Selective antimicrobial activity of chitosan on beer spoilage bacteria and brewing yeasts. Biotechnology Letters, 2004, 26(7): 569-574

[8] ChoiBong-Kyu, KimKwang-Yoon, YooYun-Jung, OhSuk-Jung, ChoiJong-Hoon, KimChong-Youl. In vitro antimicrobial activity of a chitooligosaccharide mixture against Actinobacillus actinomycetemcomitans and Streptococcus mutans. International Journal of Antimicrobial Agents, 2001, 18(6): 553-557

[9] RollerS., CovillN.. The antifungal properties of chitosan in laboratory media and apple juice. International Journal of Food Microbiology, 1999, 47(1-2): 67-77

[10] ZhanXue-jun, XiongYuan-zhen, LiuZhe, et al.. Synthesis of silver carboxymethyl chitosan and its experimental study on its bacteriostasis [J]. Chinese Journal of Biochemical Pharmaceutics, 2001, 22(3): 142-144(in Chinese)

[11] ZhaoYu-qing, LiuBao-quan, LiHui, JiangBen-guo. On coordination chitosan with Ag (I) and bacteriostasis of the complexes[J]. Journal of Beihua University (Natural Science), 2000, 1(5): 384-386(in Chinese)

[12] LiKun-ying, LiGui-shen. Analysis of TBZ in DiMei Yan Ji samples by ultraviolet absorption spectrophotometry[J]. Journal of Agricultural University of Hebei, 1997, 20(2): 106-109(in Chinese)

[13] LimSang-Hoon, HudsonSamuel M.. Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group. Carbohydrate Research, 2004, 339(2): 313-319

[14] WANG Xiao-hui, DU Yu-min, LIU Hui. Preparation, characterization and antimicrobial activity of chitosan-Zn complex[J]. Carbohydrate Polymers, 2004, (56): 21–26.

[15] NietoJ.M., Peniche-CovasC., Del BosqueJ.. Preparation and characterization of a chitosan-Fe(III) complex. Carbohydrate Polymers, 1992, 18(3): 221-224

[16] PironE, DomardA. Interaction between chitosan and uranyl ions. Part 2. Mechanism of interaction. International Journal of Biological Macromolecules, 1998, 22(1): 33-40