Patent GB-1424874-A (GB)
Title: Process for the manufacture of low molecular reactive surface- active agents from carbamides
IPC: C09K23/42
Filed: 1973-03-27
Abstract: 1424874 Urea derivatives CIBA-GEIGY AG 27 March 1973 [28 March 1972] 14731/73 Heading C2C [Also in Divisions C3 and D1-D2] Acid-curable low molecular reactive surface active compounds are prepared by (a) reacting a monomethylol derivative of a carbamide, which is optionally etherified with a C 4-7  monohydric alcohol, with a hydrophobic or hydrophilic hydroxy compound, (b) introducing a second methylol group into the resulting monomethylol ether compound by means of formaldehyde or a formaldehyde donor, and (c) etherifying this methylol group with either a hydrophilic or hydrophobic hydroxy compound such that the end product contains at least one hydrophobic and one hydrophilic group. In a modification of the above process a compound of the formula H 2 NCONHCH 2 OR (wherein R denotes C 8-22  alkyl or alkenyl, (C 2-12  alkyl) cyclohexyl, (C 2-12  alkyl) phenyl or cycloalkyl with 8 to 14 ring carbon atoms) is reacted with formaldehyde of a formaldehyde donor and the methylolated product is then further reacted with a polyalkylene glycol having an average molecular weight not exceeding 2,000. Suitable carbamide starting materials are urea, thiourea, alkylureas, arylureas, alkyleneureas, alkylenediureas, dicyandiamide, dicyandiamidine, urones and hexahydropyrimidones. Suitable hydrophobic groups are C 8-22  alkyl or alkenyl, cyclododecyl, paranonylcyclohexyl, hydroabietyl or nonylphenyl. Suitable hydrophilic radicals are derived from polyalkylene glycols having average M.W.s of 106 to 2000, especially polyethylene glycols containing 2 to 35 ethoxy units. In examples (1) monomethylolurea is converted to the n-butyl ether, transetherified with dodecanol, further methylolated to obtain dimethylolurea monododecyl ether and finally etherified with a polyethylene glycol of M.W. 300; (2) dimethylolurea monododecyl ether obtained by (1) is etherified with a polyethylene glycol of M.W. 600; (3) monomethylolurea is etherified with a mixture of C 12-15  alkanols, further methylolated and finally etherified with a polyethylene glycol of M.W. 600; (4) monomethylolurea butyl ether is transetherified with hydroabietyl alcohol, further methylolated and finally etherified with a polyethylene glycol of M.W. 600; (5) monomethylolurea n-butyl ether is transetherified with stearyl alcohol, further methylolated and finally etherified with a polyethylene glycol of M.W. 1540; (6) monomethylolurea oleyl ether is methylolated and further etherified with a polyethylene glycol of M.W. 1000; (7) dimethylolurea monododecyl ether obtained by (1) is further etherified with triethanolamine; and (8) monomethylolurea or its n-butyl ether is etherified or transetherified with a polyethylene glycol of M.W. 300, further methylolated, etherified with n-butanol and finally transetherified with n-dodecanol; Uses.-The products of the above processes are used as detergents, detergent additives, microencapsulating agents, emulsifiers, dispersing agents, hydrophobing agents, carriers and for imparting hydrophilic properties and soft handle.