Diazonium derivatives of cellulose as initiators of graft polymerization

Cellulose p ‐aminophenacyl ether (I) has been prepared from cotton and the partial p ‐aminophenacyl ester of carboxymethyl cellulose (III) has also been prepared. Derivatives (I) and (III) have been diazotized and then used to initiate polymerization of acrylonitrile. In the presence of ferrous sulfate the polymerization proceeds to formation of a graft copolymer and no polyacrylonitrile homopolymer was detected. Attempts to graft styrene and vinyl acetate on the same derivatives were not successful. Thermal degradation of the diazonium derivatives leads to insolubilization, probably due to crosslinking by combination of free radicals. Attempts to prepare cellulose p ‐aminobenzoate by reaction of cellulose derivatives with p ‐aminobenzoyl chloride (IV) in the presence of a basic catalyst led to polymerization of (IV) and to the formation of a supposed cellulose–poly‐ p ‐benzamide graft copolymer.