Patent GB-1424872-A (GB)
Title: Aminotriazine-formaldehyde condensation products, their manufacture and use
IPC: C07C275/10
Filed: 1973-03-27
Abstract: 1424872 s-Triazine derivatives CIBA-GEIGY AG 27 March 1973 [28 March 1972 22 Dec 1972] 14729/73 Heading C2C [Also in Divisions C3 C4-C5 and D1-D2] Novel aminotriazine-formaldehyde condensation products possessing at least one hydrophobic radical bonded directed or via an -O- or -N(A)- bridge, wherein A denotes H or C 1-4  alkyl, to a carbon atom of a 1,3,5-triazine ring and at least one monoalkylene or polyalkylene glycol radical as a hydrophilic radical, bonded via a N-methylol-ether bridge, the nitrogen atom of which is bonded to a carbon atom of the 1,3,5-triazine ring, are prepared by reacting an aminotriazine-formaldehyde condensation product which contains at least one hydrophobic radical bonded directly or via an -O- or -N(A)- bridge and at least one free N-methylol group, the nitrogen atom of which is bonded to a carbon atom of the 1,3,5-triazine ring, with either an alkylene glycol in the presence of a weak acid and at a temperature of 80‹ to 120‹ C. and a pressure of 1 to 30 mm. Hg. or an alkylene oxide in the presence of a metal alcoholate of a transition metal of Groups IV, V or VI of the Periodic System and, optionally, in the presence of an alkali metal hydroxide or alcoholate, at a temperature of 10‹ to 160‹ C. and a pressure of 1 to 20 atmospheres gauge. Suitable hydrophobic radicals are C 6-22  alkyl or alkenyl, cycloalkyl with 5 or 6 ring carbon atoms (C 1-12  alkyl) phenyl, phenyl or benzyl. In Examples (1) tetramethylollauroguanamine is tetraetherified with a polyethylene glycol of M.W. 30; (2) dimethyloloctadecylguanamine is prepared by reacting octadecylguanamine with formaldehyde and is subsequently dietherified with a polyethylene glycol of M.W. 600; (3) trimethylollauroylguanamine is prepared by reacting lauroylguanamine with paraformaldehyde and is subsequently etherifced with five units of ethylene oxide; (4) trimethylol-lauroylguanamine is monomethylated and further etherified with 20 units of ethylene oxide; (5) trimethylolcaprinoguanamine is prepared by reacting caprinoguanamine with paraformaldehyde and is subsequently etherified with 5À6 units of ethylene oxide; (6) trimethylolcaprinoguanamine is monomethylated and further etherified with 11À1 units of ethylene oxide; (7) trimethylol-stearylguanamine is prepared by reacting stearylguanamine with paraformaldehyde and is monomethylated and subsequently further etherified with 17À6 units of ethylene oxide; (8) trimethylol-stearylguanamine is etherified with 17À7 units of ethylene oxide; (9) tetramethylol-laurylguanamine is etherified with 6 units of ethylene oxide; (10) a mixture of tetramethylol-oleylguanamine and tetramethylol-stearylguanamine are tetraetherified with a polyethylene glycol of M.W. 600; (11) monostearylmelamine is prepared by reacting melamine with stearylamine at 180‹ C., is trimethylolated and subsequently further etherified with 12 units of ethylene oxide; and (12) distearylaminomonochloro- 1,3,5-triazine is reacted with ammonia solution and the product dimethylolated and subsequently further etherified with 10 units of ethylene oxide. Uses.-The above products are used as detergents, detergent additives, microencapsulating agents, emulsifiers, dipersing agents, hydrophobing agents, carriers and for imparting hydrophilic properties and soft handle.