Patent GB-898056-A (GB)
Title: Improvements in or relating to lubricant additives and lubricants containing them
IPC: C07D203/08
Filed: 1959-11-16
Abstract: Lubricating compositions comprise mineral or synthetic lubricating oils and oil-soluble additives prepared by reacting polymerized 1,2-alkylene imines of formula <FORM:0898056/III/1> where R is hydrogen or an alkyl group, with an oil-soluble telomer and/or copolymer derived from at least one olefinically unsaturated monomer (A) which contains an oleophilic group having 8 or more carbon atoms, or from (A) and one or more olefinically unsaturated monomers (B) capable of being copolymerized therewith, which telomer or copolymerized contains at least one polar group derived from the telomerization agent and/or (B). Specified alkylene imines are ethylene imine, propylene imine, butylene imine, C-propyl ethylene imine and C-tetradecyl ethylene imine.  The monomers (A) may be olefins, styrene derivatives, unsaturated ethers, esters of unsaturated alcohols or acids, or amides of unsaturated acids; and the monomers (B) may be olefins, styrene, unsaturated acids, unsaturated alcohols, unsaturated esters and amides, vinyl pyridines and vinyl pyrrolidones, many suitable compounds being listed.  The polyalkylene imines may be reacted with the telomers or copolymers in liquid media; the polyalkylene imines being employed in solution in methanol, ethanol, isopropanol, the butanols, or mixture thereof with water or hydrocarbons; and the telomers or copolymers in solution in benzene, toluene or xylene.  Alternatively the polyalkylene imines may be reacted in situ during the telomerization or copolymerization. In Examples (1) a toluene solution of a stearyl methacrylatemethacrylic acid copolymer is reacted with an aqueous-isopropanol solution of polyethylene imine; (2) a solution of a stearyl methacrylatebetahydroxyethyl methacrylate-methacrylic acid copolymer is reacted with an aqueous-isopropanol solution of polyethylene imine; (3) a toluene solution of a telomer prepared by copolymerizing stearyl methacrylate and betahydroxyethyl methacrylate in the presence of nitrobenzene is reacted with an aqueous isopropanol solution of polyethylene imine; and (4) stearyl methacrylate and beta-hydroxyethyl methacrylate are copolymerized in benzene in the presence of dodecyl mercaptan, azodiisobutyronitrile and a benzene-isopropanol solution of polyethylene imine.  The products of Examples 1, 2 and 3 are added to Venezuelan mineral lubricating oils.  The lubricating compositions may also contain conventional additives such as anti-oxidants, detergent dopes, viscosity-index improvers, corrosion inhibitors, anti-foaming agents, pour point depressants, extreme pressure and oiliness agents. Specification 896,435 is referred to.ALSO:Oil-soluble lubricant additives are prepared by reacting polymerized 1,2-alkylene imines of formula <FORM:0898056/IV (a)/1> where R is hydrogen or an alkyl group, with an oil soluble telomer and/or copolymer derived from at least one olefinically unsaturated monomer (A) which contains an oleophilic group having 8 or more carbon atoms, or from (A) and one or more olefinically unsaturated monomers (B) capable of being copolymerized therewith, which telomer or copolymer contains at least one polar group derived from the telomerization agent and/or (B). Specified alkylene imines are ethylene imine, propylene imine, butylene imine, C-propyl ethylene imine and C-tetradecyl ethylene imine, and the polymers thereof may be prepared by heating the monomers with hydrochloric acid or by the thermal decarboxylation of 2-oxazolidones.  The monomers (A) may be olefins, styrene derivatives, unsaturated ethers, esters of unsaturated alcohols or acids, or amides of unsaturated acids; and the monomers (B) may be olefins, styrene, unsaturated acids, unsaturated alcohols, unsaturated esters and amides, vinyl pyridines and vinyl pyrrolidones, many suitable compounds being listed.  Specified telomerization agents are mercaptans, chloralkanes such as carbon tetrahalides, and aromatic nitro compounds such as nitrobenzene and p-nitrothiophenol.  The polyalkylene imines may be reacted with the telomers or copolymers in liquid media; the imines being employed in solution in methanol, ethanol, isopropanol, the butanols or mixtures thereof with water or hydrocarbons; and the copolymers or telomers in solution in benzene, toluene or xylene. Alternatively the polymerized imines may be reacted in situ during the telomerization and/or copolymerization.  In examples (1) a toluene solution of a stearyl methacrylatemethacrylic acid copolymer is reacted with an aqueous-isopropanol solution of polyethylene imine; (2) a solution of a stearyl methacrylatebetahydroxyethyl methacrylate-methacrylic acid terpolymer in benzene and toluene is reacted with an aqueous-isopropanol solution of polyethylene imine; (3) a toluene solution of a telomer prepared by copolymerizing stearyl methacrylate and beta hydroxyethyl methacrylate in the presence of nitro benzene is reacted with an aqueous isopropanol solution of polyethylene imine; and (4) stearyl methacrylate and betahydroxyethyl methacrylate are copolymerized in benzene in the presence of dodecyl mercaptan, azodiisobutyronitrile and a benzene-isopropanol solution of polyethylene imine.  Specification 896,435 is referred to.