Patent GB-826171-A (GB)
Title: Process for the preparation of surface-active substances
IPC: C08G18/38
Filed: 1957-02-01
Abstract: A washing composition comprises a 1% aqueous solution of the following mixture, percentages being by weight; the reaction product of hexamethylene di-isocyanate and stearic acid diethanolamide, which is then reacted with a polyethylene glycol ether of molecular weight about 1000 (25%); sodium tripolyphosphate (30%); sodium pyrophosphate (15%); sodium sulphate (15%); waterglass (6%); cellulose glycolate (0.2%); optical brightener (0.1%) and water to 100%.ALSO:Surface active substances are obtained by reacting one mol. of an acid dialkanolamide with two mols. of a di-isocyanate and reacting the product with a polyglycol ether.  Suitable dialkanolamides preferably contain at least 10 carbon atoms, and include dialkanolamides of aliphatic, aromatic and heterocyclic monocarboxylic acids, whose aliphatic chains may be interrupted by nitrogen, oxygen or sulphur atoms.  Diethanolamides and di-isopropanolamides are preferred, especially of higher fatty acids such as lauric, myristic, palmitic, stearic, arachidic and behenic acids (the dialkanolamides containing at least 8 carbon atoms), and of N-lauroyl-aminocaproic acid and abietic acid. Suitable di-isocyanates include 1,6-hexamethylene -, tolylene -, 1,5 - naphthalene -, 1,4-phenylene -, methylphenylene -, 4,41 - diphenyl -, 4,41 - diphenylmethane - and other di-isocyanates, e.g. such as are mentioned in Liebigs Annalen, Vol. 562, pages 122-134.  The  polyglycol ethers may be those formed by polymerization of ethylene oxide, or by the action of ethylene oxide on bi-functional compounds having reactive hydrogen, e.g. diols, dimercaptans, secondary diamines or monoglycerides.  Polyglycol ethers having a molecular weight of 200-4000 are suitable, preferably with a molecular weight of 400-1600.  The reactions may be carried out in the absence or, preferably, in the presence of an inert solvent at a temperature of 15-150 DEG  C.  Suitable solvents include benzene, toluene, dioxan, chlorobenzene and carbon tetrachloride. The amount of solvent is 2-30 parts by weight per part by weight of intermediate product.  It is advantageous to work in an inert atmosphere.  Basic catalysts, such as tertiary nitrogen bases, may be added.  In examples: (1) hexamethylene diisocyanate is reacted with palmitic acid diethanolamide and the product reacted with a polyglycol ether of M.W. 4000; (2) the first reaction product of (1) is reacted with a polyethylene glycol of M.W. about 1550; (3) the reaction product of hexamethylene diisocyanate and stearic acid diethanolamide is reacted with a polyglycol ethylene ether of M.W. about 1000; (4) the reaction product of tolylene-diisocyanate and stearic acid diethanolamide is reacted with a polyglycol ethylene ether of M.W. about 600; (5) the reaction product of 1,5 - naphthalene - diisocyanate and N - lauroyl-e -aminocaproic acid diisopropanolamide is reacted with a polyglycol ethylene ether of M.W. about 400; and (6) the reaction product of 4,41-diphenyl-diisocyanate and abietic acid diethanolamide is further reacted with a polyglycol ethylene ether of M.W. about 600.ALSO:Surface-active substances are obtained by reacting one mol. of an acid dialkanolamide with two mols. of a di-isocyanate (to form the bis-isocyanate N,N-dicarbamic ester of the dialkanolamide) and reacting the product with a polyglycol ether.  Suitable dialkanolamides preferably contain at least 10 carbon atoms, and include dialkanolamides of aliphatic, aromatic and heterocyclic monocarboxylic acids, whose aliphatic chains may be interrupted by nitrogen, oxygen or sulphur atoms.  Diethanolamides and di-isopropanolamides are preferred, especially of higher fatty acids such as lauric, myristic, palmitic, stearic, arachidic and behenic acids (the dialkanolamides containing at least 8 carbon atoms), and of N-lauroyl-aminocaproic acid and abietic acid. Suitable di-isocyanates include 1,6-hexamethylene -, tolylene -, 1,5 - naphthalene-, 1,4 - phenylene -, methylphenylene -, 4,41 - diphenyl -, 4,41 - diphenylmethane - and other di-isocyanates, e.g. such as are mentioned in Liebigs Annalen, Vol. 562, pages 122-134.  The polyglycol ethers may be those formed by polymerization of ethylene oxide, or by the action of ethylene oxide on bi-functional compounds having reactive hydrogen, e.g. diols, dimercaptans, secondary diamines or monoglycerides.  Polyglycol ethers having a molecular weight of 200-4000 are suitable, preferably with a molecular weight of 400-1600.  The reactions may be carried out in the absence or, preferably, in the presence of an inert solvent at a temperature of 15-150 DEG  C.  Suitable solvents include benzene, toluene, dioxan, chlorobenzene and carbon tetrachloride.  The amount of solvent is 2-30 parts by weight per part by weight of intermediate product.  It is advantageous to work in an inert atmosphere.  Basic catalysts, such as tertiary nitrogen bases, may be added.  In examples: (1) hexamethylene diisocyanate is reacted with palmitic acid diethanolamide, and the product reacted with a polyglycol ether of M.W. 4000; (2) the first reaction product of (1) is reacted with a polyethylene glycol of M.W. about 1550; (3) the reaction product of hexamethylene diisocyanate and stearic acid diethanolamide is reacted with a polyglycol ethylene ether of M.W. about 1000; (4) the reaction product of tolylene-diisocyanate and stearic acid diethanolamide is reacted with a polyglycol ethylene ether of M.W. about 600; (5) the reaction product of 1,5-naphthalene-diisocyanate and N-lauroyl-e -aminocaproic acid diisopropanolamide is reacted with a polyglycol ethylene ether of M.W. about 400; and (6) the reaction product of 4,41-diphenyl-diisocyanate and abietic acid diethanolamide is further reacted with a polyglycol ethylene ether of M.W. about 600.