GB702268A - Polymeric diguanides - Google Patents

Abstract

Polymeric biguanides, which in the form of their free bases are linear polymers having the recurring unit <FORM:0702268/IV(a)/1> wherein x and y are bridging groups having together a total number of carbon atoms directly interposed between adjacent nitrogen atoms greater than 9 and less than 17 are made by reacting (a) a bisdicyandiamide of the formula <FORM:0702268/IV(a)/2> with a diamine of the formula NH2-Y-NH2, or (b) dicyanimide and an equimolar amount of a diamine of the formula NH2-X1-NH2, wherein X1 is a bridging group containing 5 to 8 carbon atoms. In examples, hexamethylene-bis-dicyandiamide is heated with (1) hexamethylenediamine dihydrochloride, (2) decamethylenediamine dihydrochloride, (3) bis-o -aminopropyl ether dihydrochloride, (4) 4:41-diaminodicyclohexylmethane dihydrochloride, (5) 1:4-di-(o -aminopropoxy) benzene di-hydrochloride, (6) N : N1 - di - isobutylaminohexamethylenediamine dihydrochloride; (7) decamethylene-bis-dicyandiamide is heated with trimethylene-diamine dihydrochloride; (8) bis-(1-cyanoguanidino-3-propyl)-ether is heated with bis-(1-amino-3-propyl)-ether dihydrochloride. The polymers are soluble in water in the form of their salts giving nearly neutral solutions, and are characterized by possessing antibacterial and antifungal properties and by giving sparingly soluble copper derivatives. Specifications 522,539, 535,141 and 631,878 are referred to. According to the Provisional Specification, the polymers in the form of their free bases have the recurring unit <FORM:0702268/IV(a)/3> wherein R is hydrogen or an alkyl radical, n and m are integers greater than 2 and smaller than 13, and wherein the polymethylene chains may, if desired, be interrupted, e.g. by oxygen and/or sulphur, and/or may be incorporated wholly or in part into one or more ring systems. In examples, hexamethylene-bis-dicyandiamine is reacted with (2) trimethylenediamine dihydrochloride and (8) 1:3-bis-methylaminoneopentane dihydrochloride; (9) trimethylene-bis-dicyandiamide is reacted with trimethylenediamine dihydrochloride, (10), decamethylene - bis - dicyandiamide is reacted with decamethylenediamine dihydrochloride, and (13) 1:4-di(o -cyanoguanidino-propoxy)-benzene is reacted with 1:4-di-(o -aminopropoxy)-benzene dihydrochloride.ALSO:Hexamethylene-bis-dicyandiamide is made by refluxing a mixture of hexamethylenediamine dihydrochloride and sodium dicyanimide in butanol with subsequent cooling, filtration and crystallisation of the residue from water. It is stated that trimethylene-bis-dicyandiamide, decamethylene-bis-dicyandiamide, bis-(1-cyanoguanidino-3-propyl)-ether and 1:4-di-(o -cyanoguanidino-propoxy)-benzene may be made in a similar manner.