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Type: Artigo de periódico
Title: Reaction of Glycidyl Methacrylate at the Hydroxyl and Carboxylic Groups of Poly(vinyl alcohol) and Poly(acrylic acid): Is This Reaction Mechanism Still Unclear?
Author: Reis, AV
Fajardo, AR
Schuquel, ITA
Guilherme, MR
Vidotti, GJ
Rubira, AF
Muniz, EC
Abstract: Transesterification and epoxide ring-opening reactions are two mechanism routes that explain chemical modifications of macromolecules by glycidyl methacrylate (GMA). Although the coupling reaction of the GMA with macromolecules has widely been investigated, there are still mechanisms that remain to be explained when GMA is processed in an aqueous solution at different pH conditions. To this end, reaction mechanisms of poly(vinyl alcohol) (PVA) and poly(acrylic acid) (PAAc) by GMA in water in acidic and basic conditions were investigated thoroughly. The presence of hydroxyl groups in PVA and carboxyl groups in PAAc allowed for a better evaluation of the reaction mechanisms. The analysis of the (1)H and (13)C NMR spectra clearly demonstrated that the chemical reactions of GMA with carboxyl groups and alcohols of the macromolecules in an aqueous solution are dependent on pH conditions. At pH 3.5, the GMA reacts with both the carboxylic and the hydroxyl groups through an epoxide ring-opening mechanism. At pH 10.5, the GMA undergoes a hydrolysis process and reacts with hydroxyl groups by way of both the transesterification and the epoxide ring-opening mechanisms, whereas the ring-opening reaction is the preferential pathway.
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 74, n. 10, n. 3750, n. 3757, 2009.
Rights: fechado
Identifier DOI: 10.1021/jo900033c
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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