Patent GB-1117643-A (GB)
Title: Imides and related compounds
IPC: C10L1/24
Filed: 1965-10-06
Abstract: Lubricating oil additives are formed by reacting an olefinic succinic anhydride of formula <FORM:1117643/C3/1> with an aminocyclic urea of formula <FORM:1117643/C3/2> where R is an alkenyl radical containing 30 to 200 carbon atoms, X is oxygen or sulphur and A and A1 are alkylene radicals containing 2 or 3 carbon atoms in a chain extending between the nitrogen atoms to which they are attached. Preferably the olefinic succinic anhydride is obtained by polymerizing an olefine containing four carbon atoms and then reacting the polymer produced with maleic anhydride. Aminocyclic ureas mentioned are aminoethylethyleneurea, aminopropylethyleneurea, aminoethylethylenethiourea, aminopropylethylenethiourea, aminoethylhexahydropyrimidinone, aminopropylhexahydropyrimidinone, aminopropylhexahydropyrimidithione, 1-(1-methyl-2-aminoethyl) - 5 - methylethyleneurea and 1-(1 - methyl - 2 - aminoethyl) - 5 - methylhexahydropyrimidinone.  Either a 1:1 or 1:2 ratio of olefinic succinic anhydride to aminocyclic urea may be employed. Cyclic imides and amide acids may be produced using a 1 : 1 ratio, in the former case the water formed is removed.  The amide acids may be reacted with a compound Z-Y-H, followed by reaction with the aminocyclic urea, where Y is oxygen or sulphur and Z is a hydrogen, a C1 to C24 alkyl group, a cycloalkyl group, a phenyl group, a naphthyl group or an alkylphenyl or phenylalkyl group where the alkyl group has 1 to 8 carbon atoms.  The alkyl radicals may contain thio, hydroxy or tertiary amino substituents.ALSO:Lubricating oil and fuel additives of formulae <FORM:1117643/C4-C5/1> are obtained by reacting an olefinic succinic anhydride <FORM:1117643/C4-C5/2> with an aminocyclic urea of formula  <FORM:1117643/C4-C5/3> In the above formulae one R is a hydrogen atom and the other is an alkenyl radical containing 30 to 200 carbon atoms, R1 is an alkenyl radical containing 30 to 200 carbon atoms, A and A1 are alkylene radicals containing 2 or 3 carbon atoms in a chain extending between the nitrogen atoms to which it is attached, X and Y are oxygen or sulphur atoms and Z is a hydrogen atom, a C1-C24 alkyl group, a phenyl group, a cycloalkyl group, a naphthyl group or an alkylphenyl or phenylalkyl group in which the alkyl radical contains 1 to 8 carbon atoms.  The alkyl radicals may be substituted by thio, hydroxy or tertiary amino radicals.  The olefinic succinic anhydride is preferably obtained by reacting a polyolefine with maleic anhydride.  Additives of formula II can be further reacted with a compound 2-y-H, and then with the aminocyclic urea. The lubricating oils may be mineral oils or synthetic lubricants and they may be of naphthenic or paraffinic nature or mixtures thereof, or they may be distillates or mixtures of neutral oils and bright stocks.  The lubricants may be bodied or gelled and used as greases. The oils may vary from spindle oils or hydraulic oils to oils for reciprocating aircraft engines and include oils for sparking combustion and compression ignition engines.  Also hydraulic and automatic transmission fluids.  Synthetic lubricants include esters, polyethers and silicones. When used as hydraulic fluids phosphate esters are added.  Antioxidants, anti-foam agents, anti-rust agents, anti-wear agents, heavy-duty detergents, pour-point depressants, viscosity index improvers, anti-knock agents and ignition control agents may also be present. The fuel include distillate fuels boiling between 75 DEG  and 750 DEG  F., including gasolines, jet and Diesel fuels and furnace oils.