Internal catalysis of reactions of activated vinyl compounds via tertiary amino substituents in cotton cellulose

Abstract

AbstractThe tertiary amino groups of 2‐diethylaminoethyl substituents in cotton cellulose have been found to be effective catalysts for reactions of activated vinyl compounds with cellulosic hydroxyl groups. These reactions proceed more slowly and to lesser extents at equilibrium than the corresponding reactions catalyzed by quaternary ammonium substituents. The crosslinking of cotton cellulose with divinyl sulfone is catalyzed by (C2H5)2NCH2CH2 substituents and by (C2H5)2NCH2CH(OH)CH2 substituents, with the development of moderate levels of wrinkle recovery. On the other hand, only the former substituents catalyze the reorganization of the crosslinkages during recure (160°C, 10 min), with substantial increases (40°) in wrinkle recovery angles. These same 2‐diethylaminoethyl substituents are effective in catalyzing the reorganization of crosslinkages from divinyl sulfone which are introduced into the cotton by conventional external catalysis (i.e., NaOH); this effectiveness can be overcome by the introduction of excessive crosslinkages into the cellulosic composition.