Patent GB-681554-A (GB)
Title: Improvements in or relating to the preservation of bearing surfaces
IPC: C10M133/16
Filed: 1949-09-14
Abstract: Hydroxy-amine reaction products.-Reaction products, which may be esters, amides, oxazolines, ester-amides or ester-oxazolines or mixtures thereof, are formed by reacting an aliphatic or cycloaliphatic acid containing 6-24 carbon atoms, or an acid anhydride or acid halide derived therefrom, with a hydroxyaliphatic amine.  The amine has the formula <FORM:0681554/IV (b)/1> where at least 2 of the radicals R, R1 and R11 are of the type <FORM:0681554/IV (b)/2> where each R111 is hydrogen or an aliphatic hydrocarbon radical containing 1-12 carbon atoms, and any remaining radical R, R1 or R11 is hydrogen or an aliphatic hydrocarbon radical containing 1-8 carbon atoms.  From 1-2 acid radicals are provided for each molecule of amine, and the reaction is conducted so that at least one molecular proportion of water or halogen halide is formed, for example by heating to 160-190 DEG  C., but so that at least one free hydroxyl group is left unreacted, Acids specified are lauric, palmitic, stearic, oleic, linoleic, ricinoleic, eleomargaric, erucic, behenic, arachidic and lignoceric acids, naphthenic acids, acids derived by the oxidation of petroleum products or by the oxidation of "Oxo" products produced by the reaction of carbon monoxide and hydrogen upon an olefin, and fatty acids derived from tall oil, castor, soybean, linseed, olive, tung, rapeseed and menhaden oils. In one example, trimethylol amino methane and pyridine are heated to 50-70 DEG  C. in a flask in which an atmosphere of nitrogen is maintained, and oleyl chloride is added, equimolecular proportions of the hydroxy amine and acid chloride being used.  The pyridine is removed by heating under reduced pressure and the reaction product is dissolved in toluene.  The toluene solution of the reaction product is washed and the toluene removed by distillation.  In other examples equimolecular proportions of dimethylol-methyl amino methane and oleic acid, and 1 molecular proportion of trimethylol amino methane to 2 molecular proportions of oleic acid, are reacted. Hydroxyaliphatic amines.-Hydroxyaliphatic amines of the type defined above are prepared by reacting a nitroparaffin with an aliphatic aldehyde in the presence of an alkali catalyst, and reducing the nitro-alcohol so formed.  A nitroparaffin having a hydrogen atom attached to the carbon atom adjacent to the nitro group is employed. Aldehydes having one or more hydroxy groups attached to the hydrocarbon chain, such as those formed in the aldol reaction, may be used.  Specifications 613,835, 681,555, and U.S.A. Specification 2,388,281 are referred to.ALSO:Bearing surfaces, for example of an internal combustion engine, are preserved from rusting by lubrication with a composition comprising a hydrocarbon lubricating oil containing a minor proportion of a product formed by reacting an aliphatic or cycloaliphatic acid containing 6-24 carbon atoms, or an acid anhydride or acid halide derived therefrom, with a hydroxy-aliphatic amine of the formula:-  <FORM:0681554/III/1> where at least 2 of the radicals R, R1 and R11 are of the type:- <FORM:0681554/III/2> where each R111 is hydrogen or an aliphatic hydrocarbon radical containing 1-12 carbon atoms, and any remaining radical R, R1 or R11 is hydrogen or an aliphatic hydrocarbon radical containing 1-8 carbon atoms.  From 1-2 acid radicals are provided for each moelcule of amine, and the reaction is conducted so that at least one molecular proportion of water or halogen halide is formed, but so that at least one free hydroxyl group is left unreacted.  The products may be esters, amides, oxazolines, ester-amides, ester-oxazolines, or mixtures thereof.  Acids specified are lauric, palmitic, stearic, oleic, linoleic, ricinoleic, eleomargarkic, erucic, behenic, arachidic and lignoceric acids, naphthenic acids, acids derived by the oxidation of petroleum products or by the oxidation of "Oxo" products produced by the reaction of carbon monoxide and hydrogen upon an olefin, and fatty acids derived from tall oil, castor, soyabean, linseed, olive, tung, rapeseed and menhaden oils.  Reaction products of oleic acid or oleyl chloride with dimethylol methyl amino methane and trimethylol amino methane are particularly mentioned.  From 0.01-10 per cent of the products is preferably used.  Hydrocarbon oils referred to are petroleum oils and synthetic oils such as those obtained by the polymerization of olefins or by the hydrogenation of coal.  Mixtures of naphtha and a hydrocarbon lubricating oil, with or without small amounts of petrolatum or degras may also be used.  Specifications 613,835, and 681,555, and U.S.A. Specification 2,388,281, are referred to.