Chemical modification of hydroxyl functions: Introduction of hydrolyzable ester function and bactericidal quaternary ammonium groups

作者：F. Baudrion, Alain Perichaud, Serge Coen · 发表于：Journal of Applied Polymer Science · 年份：1998 · DOI：10.1002/(sici)1097-4628(19981226)70:13<2657::aid-app11>3.0.co;2-x · 被引用次数：35 · 研究领域：Antimicrobial agents and applications、Advanced Polymer Synthesis and Characterization、biodegradable polymer synthesis and properties

Polymers carrying a hydrolyzable ester function and bactericidal quaternary ammonium salts were successfully synthesized in 2 steps. The first one was the modification of hydroxyl functions of poly(vinyl alcohol) by chloroacetic anhydride. The structure of synthesized polymers was confirmed by infrared (IR), 1H-, and 13C- nuclear magnetic resonance (NMR). The kinetic results were consistent with a 1-order reaction, and the activation energy in the case of total modification was found to be 16.8 kJ mol−1. The second step was the quaternization of the pendant chlorine atom with a long alkyl chain or aromatic tertiary amines. The percentage of grafting was almost total, except with 3-diethylaminophenol, probably due to steric hindrance. The thermal degradation of polymers was studied. Side chains carrying quaternary ammonium salts begin to degrade at 168°C with the emission of chloride and amine compounds. At about 250°C, acetic and chloroacetic acid are evolved due to acetate and chloroacetate side chains. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 70: 2657–2666, 1998