Polymères porteurs de dérivés du glycérol, 10. Fixation de l'acide naphtyl‐1 acétique sur le poly(acide méthacrylique)

Abstract

Glycidyl (2,3-epoxypropyl) esters are convenient reagents for the fixation of carboxylic acid moieties on polymeric support of the polyacid type. This way of synthesis was applied to 1-naphthylacetic acid on poly(methacrylic acid). Esterification of 1-naphthylacetyl chloride by glycidol (2,3-epoxy-1-propanol) and addition of 1-naphthylacetic acid on epichlorohydrin (1-chloro-2,3-epoxypropane) with subsequent reformation of the oxirane ring have been used for the synthesis of the glycidyl ester but the reaction of the potassium salt of the acid with epichlorohydrin leads to a better yield. Addition of 1-naphthylacetic acid on glycidyl acetate was studied in N,N-dimethylformamide (DMF) and acetonitrile. The best results were obtained in DMF. The reaction is of first order with respect of epoxide, but 2nd order applies when the solvent is acetonitrile. The same reaction conditions as for glycidyl acetate were used for the chemical modification of poly(methacrylic acid) with glycidyl 1-naphthylacetate except that methanol was used as the solvent.