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Chemical modification of hydroxyl functions: Introduction of hydrolyzable ester function and bactericidal quaternary ammonium groups
Author(s) -
Baudrion F.,
Perichaud A.,
Coen S.
Publication year - 1998
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/(sici)1097-4628(19981226)70:13<2657::aid-app11>3.0.co;2-x
Subject(s) - chemistry , chloroacetic acid , polymer chemistry , ammonium , alkyl , chemical modification , organic chemistry
Abstract 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), 1 H‐, and 13 C‐ 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