Patent GB-953542-A (GB)
Title: Oil-soluble thioether compounds and lubricating oil compositions containing them
IPC: C07F9/40
Filed: 1960-07-01
Abstract: The invention comprises oil-soluble thioether compounds of the formula (Z-(CH2)n-S)n3-(R)-COO-(R11-X) n1-(R1-O)n2-CO.(R) -(S-(CH2)n-Z)n3 wherein R is an aliphatic radical having at least 8 carbon atoms and optionally containing a hydroxyl group, R1 and R11 are C2-8 alkylene radicals, X is oxygen or sulphur, n1, n2 and n3 are integers of at least 1, n is an integer of from 1-4 and Z is -OR111 or -COOR111, R111 being hydrogen or a C1-4 alkyl radical, and in which not more than one -S-(CH2)n-Z group is attached to any carbon atom, and in which there is adjacent to each carbon atom bearing an -S-(CH2)n-Z group a carbon atom bearing at least one hydrogen atom. The thioether derivatives are prepared by the reaction of a di-ester of a long-chain unsaturated fatty acid and a polyoxyalkylene diol or an analogous sulphur containing diol of formula: <FORM:0953542/C2/1> with a mercapto compound of formula: HS(CH2)nZ where R1, R11, X, Z, n, n1 and n2 are as defined above and wherein R1 is an aliphatic radical containing at least 8 carbon atoms and, optionally, a hydroxyl group, at low temperatures in the presence of a free-radical catalyst and a non-reactive solvent.  The diester starting materials of the formula: <FORM:0953542/C2/2> are prepared by conventional esterification of the diol of formula: HO - (R11 - X)n1 - (R1 - O)n2H with an acid R1.COOH, the symbols being as defined above.  Examples are given.  The novel compounds are used as lubricating oil additives (see Division C5).  2-Thia-alkyl-phosphono compounds of the formula: <FORM:0953542/C2/3> wherein R stands for a hydrocarbyl radical having at least 6 carbon atoms, the R1's stand for hydrogen, hydrocarbyl or cationic groups, R2 stands for hydrogen or a C1-4 alkyl radical and the X's stand for oxygen or sulphur, may be prepared by the method of Specification 904,968 and are used as lubricating oil additives (see Division C5).  Examples are given.  Specifications 651,712 and 863,339 also are referred to.ALSO:Lubricating oil compositions comprise synthetic oils or natural hydrocarbon oils and compounds of the formula (Z-CH2)n-S)n3(R)-COO-(R11-X)n1 -(R1-O)n2-CO.(R)-(S-(CH2)n-Z)n3\t wherein R is an aliphatic radical having at least 8 carbon atoms and optionally containing a hydroxyl group, R1 and R11 are C2- 8 alkylene radicals, X is oxygen or sulphur, n1, n2 and n3 are integers of at least 1, n is an integer of from 1-4 and Z is -OR111 or -COOR111, R111 being hydrogen or a C1- 4 alkyl radical, and wherein not more than one -S-(CH2)n-Z group is attached to any carbon atom, and wherein there is adjacent to each carbon atom bearing an -S-(CH2)n-Z group a carbon atom bearing at least one hydrogen atom (see Division C2).  The compositions may additionally contain compounds of the formula <FORM:0953542/C3/1> wherein R stands for a hydrocarbyl radical having at least 6 carbon atoms which may be chlorinated, the R1's stand for hydrogen, hydrocarbyl or cationic (e.g. metal or amine) groups, R2 stands for hydrogen or a C1- 4 alkyl radical and the X's stand for oxygen or sulphur (see Division C2).  The lubricating oil may be any known type of natural hydrocarbon oil, examples being given, or a synthetic oil which may be a polymerized olefin, alkylated aromatic, isomerized wax, a copolymer of alkylene glycol and alkylene oxides, and ethers thereof, organic diesters.  Blends of hydrocarbon oil with castor oil, lard oil, synthetic oils as above, and/or silicone polymers are also mentioned.  Optional additives mentioned include silicone antifoaming agents, phenolic antioxidants, polyacrylate esters and viscosity-index improvers, and lauric or oleic acid as oiliness agents. Specifications 651,712, 863,339, and 904,968 are referred to.