Patent GB-879991-A (GB)
Title: Metal-organic salt-amine complexes and their use in hydrocarbon oil compositions
Inventor: BURNOP VICTOR CHARLES ERNEST
IPC: C07F15/06
Filed: 1958-04-28
Abstract: A process for preparing hydrocarbon oil soluble complex metal salts of a fatty acid, chlorinated fatty acid or salicylic acid comprises forming a complex of a metal salt of the said organic acid with a branched chain aliphatic primary amine by (a) mixing the metal salt of the said organic acid with the amine at room temperature or at a temperature below the boiling point of the amine or below 200 DEG C. which ever temperature is the lower or (b) neutralizing the amine with the said organic acid and then dissolving an oxide or base of the metal in the salt so formed. Amines which may be employed in the preparation of the complexes include secondary and tertiary alkyl primary amines which may be prepared from polymers of propylene and isobutene, copolymers of propylene and isobutene and of isobutene and other butenes and pentenes e.g. C12-C15 amines and C19-C24 amines prepared from triisobutene and hexapropylene respectively and C18-C24 amines obtained by reacting tetrapropylene and other polymerized olefines with ammonia.  Other amines mentioned include 3-amino-3,5,8-trimethylnonane, 5-amino-5,13-dimethyl hexadecane, 3 - amino - 3,5,7,9,12 - pentamethyltridecane, 4 - amino - 2,4,6,8,10 - pentamethyltridecane, 2 - amino - 2,4,4,6,6,8,8 - heptamethylnonane and 6-amino-2,2,4,4,6,8,8-heptamethylnonane. Organic acids which may be employed in preparing the complexes include C1 to C25 fatty acids or chlorinated fatty acids e.g. acetic and chloracetic acid especially monoand dichlorinated fatty acids containing from 2 to 6 carbon atoms. Metals which may be present in the complexes include cadmium, cobalt, copper, silver and zinc.  Complexes are prepared in examples from copper stearate and "Primene" (Registered Trade Mark) J.M.T., a mixture of C18-C24 alkyl branched chain primary amines, (1); zinc oxide, acetic or chloracetic acid and "Primene" J.M.T. (2, 3); cobalt stearate, copper octoate, acetate, stearate and propionate, silver acetate, zinc octoate, acetate, caproate, propionate, stearate salicylate and cadmium stearate and "Primene" 81-R a mixture of C12 alkyl branched chain primary amines (4). Complexes prepared from zinc diethyldithiocarbamate and "Primenes" J.M.T and 81-R, zinc stearate and 2 ethylhexylamine, 2-dimethyl(amino)ethanol and a C12 amine mixture obtained by reacting tetra propylene with ammonia are also mentioned.ALSO:Lubricating and fuel oil compositions comprise an oil-soluble complex formed by reacting a metal salt of a fatty acid, chlorinated fatty acid or salicylic acid with a branched chain aliphatic primary amine or by reacting a salt of such amine with a fatty acid, chlorinated fatty acid or salicylic acid and a metallic oxide or base (see Group IV(b)).  The lubricating oils may be hydrocarbon or ester or polyalkylene ether and ester oils. Amines which may be employed in the preparation of the complexes include secondary and tertiary alkyl primary amines prepared from polymers of propylene and isobutene, copolymers of propylene and isobutene and of isobutene and other butenes or pentenes, e.g. C12-C15 amines and C19-C24 amines prepared from triisobutene and hexapropylene respectively and C18-C24 amines obtained by reacting tetrapropylene with ammonia.  Other amines mentioned include 3-amino-3,5,8-trimethylnonone, 5-amino-5,13-dimethyl hexadecane, 3-amino-3,5,7,9,12-pentamethyltridecane, 2-amino-2,4,4,6,6,8,8-heptamethylnonane and 6-amino-2,2,4,6,8,8-heptamethylnonane.  Organic acids which may be employed in preparing the complexes include C1 to C25 fatty acids optionally chlorinated, e.g. acetic and chloracetic acid and salicylic acid.  Metals which may be present in the complexes include cadmium, cobalt, copper, silver and zinc. Specific compositions described include while oil solutions of complexes of copper stearate with "Primene" (Registered Trade Mark) VMT, a mixture of C18-C24 alkyl branched chain primary amines, complexes of cobalt stearate, copper octoate, acetate, stearate, propionate, silver stearate, zinc octoate, acetate, coprate, propionate, stearate, salicylate and cadmium stearate with "Primene" 81R, a mixture of C12 alkyl branched chain primary amines.  Other oil soluble complexes described include those formed from zinc chloracetate and a C12 amine obtained by reacting tetrapropylene with ammonia and zinc diethyldithio carbonate with "Primenes" VMT and 81-R. Other lubricating compositions described comprise in addition to the complexes of the invention a dialkyl dithiophosphate, e.g. a zinc dialkyldithiophosphate, the alkyl groups in which are preferably derived from mixtures of methyl isobutyl carbinol and isopropanol or primary C4 and C5 oxo alcohols. Examples are furnished of lubricating compositions comprising mineral oil, and "Primene" VMT complexes with zinc acetate and chloracetate with and without dialkyldithiophosphates of the kind defined above. Further compositions are described comprising mineral lubricating oil and zinc propionate, coprate, and salicylate complexes with "Primene" 81-R.  Further additives mentioned include mixtures of calcium or barium sulphonate or barium phenate and phosphosulphurized polybutene. ALSO:Fungicidal compositions comprise as active ingredient a complex of a copper salt of an organic acid with a branched chain aliphatic primary amine (see Group IV (b)).  In Example (1) a white oil solution of a complex of copper stearate and a mixture of C18-24 alkyl branched chain primary amines is prepared. Other copper complexes soluble in white oil are prepared from copper octoate, acetate and propionate and a mixture of C12 alkyl branched chain primary amines.