Kinetic study of cyanoguanidine resin formation: acid hydrolysis of hydroxymethyl and methoxymethyl cyanoguanidine

The hydrolysis of hydroxymethyl cyanoguanidine and methoxymethyl cyanoguianidine in acidic aqueous media were studied by analyzing the eluted formaldehyde and the reaction products. Dihydroxymethyl cyanoguanidine released two formaldehydes with different rates because one of the two hydroxymethyl groups is intramolecularly interactive through the hydrogen bond. Methanol dissociation from methoxymethyl cyanoguanidine was seven to eight times faster than the dissociation of hydroxymethyl group, and the overall hydrolysis kinetics were similar to those of hydroxymethyl cyanoguanidine.