Patent GB-768067-A (GB)
Title: Improvements in or relating to isothiouronium compounds
IPC: B03D1/012
Filed: 1955-03-15
Abstract: The invention comprises isothiouronium salts of the formula <FORM:0768067/IV(b)/1> where X is halogen or R1SO4, R1 is an aliphatic radical of 1-5 carbon atoms and R is an aliphatic hydrocarbon radical of 8-22 carbon atoms or a radical of the formula -[-(CH2)n-N(CH3)R1R11]+X-, R11 being an aliphatic hydrocarbon radical of 8-22 carbon atoms and n being 2-10.  The compounds of the first type are prepared by reacting RNH2 with CS2 to give an N : N1-disubstituted thiourea and treating the product with a compound R1X such as an alkyl chloride, dialkyl sulphate or alkylene chlorhydrin.  The residue R may be saturated or unsaturated and may be derived from the fatty acids of tallow, soybean oil, coconut oil or tall oil.  The compounds of the second type are prepared from RNH2 by reaction with an unsaturated nitrile to give R-NH-(CH2)n-1 CN, N-methylation of the latter (with formaldehyde and formic acid), catalytic hydrogenation to the diamine R(CH3)N-(CH2)n-NH2, conversion to thiourea as above and reaction with 3 mols. of R1X to alkylate the S atom and quaternize the two N atoms.  Examples are given of the preparation of compounds (1) R = octadecyl, R1 = methyl; (2) R = dodecyl, R1 = methyl, (3) R = dodecyl, R1 = b -hydroxyethyl and (4) R = methochloride of g  - (dodecylmethylamino)-propyl, R1 = methyl, X being chloride throughout.  In the last case the product is mixed with the corresponding compound quaternated on one N atom only and with the thiourea without the S-methyl substituent.  Intermediates described are N : N1-didodecyl-thiourea, b -(dodecylamino) - propionitrile, b  - (dodecylmethylamino)-propionitrile, g  - (dodecylmethylamino) - propylamine and N : N1 - di - [g  - (dodecylmethyl - amino)-propyl]-thiourea.ALSO:Metallic surfaces are protected from corrosion by acidic substances by applying thereto (e.g. in organic solvent solution) a compound of the formula <FORM:0768067/III/1> where X is halogen or R1SO4, R1 is an aliphatic radical of 1-5 carbon atoms and R is an aliphatic hydrocarbon radical of 8-22 carbon atoms or a radical of the formula -[(CH2)n-N(CH3)R1R11]\sWX-, R11 being an aliphatic hydrocarbon radical of 8-22 carbon atoms and n being 2-10.  The compound is preferably used in a concentration range of 10 to 50,000 parts per million.ALSO:Mineral ores are separated by employing as flotation agent a compound of the formula <FORM:0768067/II/1> where X is halogen or R1SO4, R1 is an aliphatic radical of 1-5 carbon atoms and R is an aliphatic hydrocarbon radical of 8-22 carbon atoms or a radical of the formula:- [(CH2)n-N(CH3) R1R11]\sW-R11 being an aliphatic hydrocarbon radical of 8-22 carbon atoms and n being 2-10. The compound may be used in amounts of 0.03-0.05 lb. per ton of ore processed.ALSO:Insecticidal compositions (e.g. solutions in organic solvents or emulsions) contain as active ingredient a compound of the formula <FORM:0768067/VI/1> where X is halogen or R1SO4, R1 is an aliphatic radical of 1-5 carbon atoms and R is an aliphatic hydrocarbon radical of 8-22 carbon atoms or a radical of the formula [(CH2)n-N(CH3) R1R11]+X-R11 being an aliphatic hydrocarbon radical of 8-22 carbon atoms and n being 2-10.  The active ingredient can be employed in a concentration range of 3-10 per cent of the inert carrier.