Antimicrobial copolymers bearing quaternary ammonium and phosphonium salts based on a copolymer of glycidyl methacrylate and 2‐hydroxyethyl methacrylate were synthesized. Poly(glycidyl methacrylate‐co‐2‐hydroxyethyl methacrylate) was modified for the introduction of chloromethyl groups by its reaction with chloroacetyl chloride. The chloroacetylated copolymer was modified for the production of quaternary ammonium or phosphonium salts. The antimicrobial activity of the obtained copolymers was studied against gram‐negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Shigella sp., and Salmonella typhae), gram‐positive bacteria (Bacillus subtilus and B. cereus), and the fungus Trichophyton rubrum by the cut‐plug method. The results showed that the three copolymers had high antimicrobial activity. A control experiment was carried out on the main polymer without ammonium or phosphonium groups. The copolymer bearing quaternary salt made from tributyl phosphine was the most effective copolymer against both gram‐negative and gram‐positive bacteria and the fungus T. rubrum. The diameters of the inhibition zones ranged between 20 and 60 mm after 24 h. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 2384–2393, 2002

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The principal derivative of chitin is chitosan, which is obtained by deacetylation of chitin. Chemical modification of synthetic and natural polymers is a convenient way to obtain materials with unique chemical and physical properties. Chitosan has an amino group at C-2 which is important because amino groups are nucleophilic and readily react with electrophilic reagents. Chitosan modified under mild conditions often results in regioselectivity for the C-2 amino group. In the present work, this reactivity was exploited to attach biologically active moieties into the amino groups of chitosan to yield anti-microbial chitosans. Specifically, vanillin, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, anisaldehyde, methyl 4-hydroxybenzoate, methyl 2,4-dihydroxybenzoate, propyl 3,4,5-trihydroxybenzoate and 2-hydroxymethylbenzoate were attached. The anti-microbial activity of these modified chitosans was explored against fungi such as Candida albicans SC5314, Aspergillus flavus and Fusarium oxysporium. Also, they were tested against bacteria such as Bacillus subtilis, Escherichia coli and Staphylococcus aureus. These modified chitosans were found to be highly active toward fungi species more than bacterial species.