Patent GB-1021182-A (GB)
Title: Oil-soluble nitrogen containing products and process for preparing same
IPC: C10N30/04
Filed: 1962-08-15
Abstract: A lubricating composition comprises a major portion of a lubricating oil and a minor proportion of a nitrogen and boron-containing composition made by treating an acylated nitrogen composition having within its structure (A) a substantially hydrocarbon substituted succinoyl, succinimidoyl, or succinoyloxy radical wherein the substantially hydrocarbon substituent contains at least 50 aliphatic carbon atoms and (B) a nitrogen containing group having a nitrogen atom attached directly to said succinoyl, succinimidoyl or succinoyloxy radical, with a boron oxide, a boron halide, a boron acid or an ester of a boron acid in such an amount as to provide from 0.1 atomic proportions of boron for each mole of said acylated nitrogen composition to 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen composition. The lubricating oils may be mineral, animal or vegetable or synthetic oils such as didodecyl adipate and di-2-ethylhexyl sebacate.  The lubricating composition may also contain oil-soluble neutral or basic salts of alkali or alkaline earth metals with sulphonic acids, carboxylic or organic phosphorus acids; metal dithiocarbamates, xanthates, the Group II metal phosphorodithioates and their epoxide adducts, hindered phenols, sulphurized cycloalkanes, dialkyl polysulphides, sulphurized fatty esters, phosphosulphurized fatty esters, alkaline earth metal salts of alkylated phenols, dialkyl phosphites, triaryl phosphites, and esters of phosphorodithioic acids. The compositions may also contain poly(alkyl-methacrylates), polybutenes, and poly(alkyl siloxanes).ALSO:Oil-soluble nitrogen and boron-containing compounds are made by treating an acylated nitrogen compound having within its structure (A) a substantially hydrocarbon substituted succinoyl, succinimidoyl, or succinoyloxy radical wherein the substantially hydrocarbon substituent contains at least about 50 aliphatic carbon atoms and (B) a nitrogen-containing group having a nitrogen atom directly attached to said succinoyl, succinimidoyl or succinoyloxy radical, with a boron oxide, a boron halide or complex thereof, a boron acid/including alkyl- or aryl-boronic acids, tetraboric and metaboric acids, as well as orthoboric acid) or an ester of a boron acid in such an amount as to provide from 0.1 to 10 atomic proportions of boron for each mole of said acylated nitrogen compound. The substantially hydrocarbon substituent may be derived from substantially saturated olefin polymers, particularly polymers or copolymers of mono-olefins having from 2 to 30 carbon atoms, having a molecular weight of 700-5000. The nitrogen-containing group may be derived from ammonia; or aliphatic, aromatic, carbocyclic or heterocyclic amines which may be primary or secondary, mono- or polyamines; hydroxyalkyl - substituted alkylene amines; ureas, thioureas, hydrazines, guanidines, amidines, amides, thioamides and cyanamides. The acylated nitrogen compounds are made by reacting the appropriate high molecular weight succinic acid, halide, ester or anhydride with at least one half of an equivalent amount of the nitrogen-containing compound, at a temperature above 80 DEG  C., preferably in the range 100 DEG  to 250 DEG  C.  Detailed examples utilize polyisobutenyl or polyisopropenyl succinic anhydride or a substituted succinic anhydride prepared from maleic anhydride and a chlorinated copolymer of isobutylene and styrene or isoprene.ALSO:Oil-soluble nitrogen and boron-containing compounds are made by treating an acylated nitrogen compound having within its structure (A) a substantially hydrocarbon substituted succinoyl, succinimidoyl, or succinoyloxy radical wherein the substantially hydrocarbon substituent contains at least about 50 aliphatic carbon atoms and (B) a nitrogen-containing group having a nitrogen atom attached directly to said succinoyl, succinimidoyl or succinoyloxy radical, with a boron oxide, a boron halide or complex thereof, a boron acid (including alkylor aryl-boronic acids, tetraboric and metaboric acids, as well as orthoboric acid) or an ester of a boron acid in such an amount as to provide from 0.1 to 10 atomic proportion of boron for each mole of said acylated nitrogen compound. The reaction preferably takes place between 50 DEG  and 250 DEG  C. for 1/2 to 6 hours.  The substantially hydrocarbon substituent may be derived from high molecular weight substantially saturated petroleum fractions, such as highly refined white oils, or synthetic alkanes obtained by hydrogenation of olefin polymer.  The nitrogen-containing group may be derived from ammonia; or aliphatic, aromatic, carbocyclic or heterocyclic amines which may be primary or secondary, mono- or polyamines; hydroxyalkyl-substituted alkylene amines; ureas, thioureas, hydrazines, guanidines, amidines, amides, thioamides and cyanamides.  Examples also describe the production of (a) a cyanoethyl-substituted ethylene amine by heating acrylonitrile with a mixture of triethylene tetramine and diethylene tetramine; (b) a diisobutenyl-substituted ethylene amine from diisobutenyl chloride and a mixture of triethylene tetramine and diethylene tetramine.