Patent GB-894077-A (GB)
Title: Oil-soluble polymeric compounds, their preparation and hydrocarbon compositions containing them
IPC: C10L1/24
Filed: 1960-11-08
Abstract: As additives to liquid hydrocarbons, especially lubricating oils, these are used oil-soluble polymeric compounds which contain a linear carbon-to-carbon backbone chain having attached thereto a plurality of each of two groups, one being or containing a -COOR group and the other containing a -COOR1-S-R11-Y group, wherein R is an alkyl radical having at least 8 carbon atoms, R1 and R11 are the same or different alkylene radicals and Y is an acidic polar radical, e.g. carboxyl, hydroxyl, mercapto, halogen or cyano, the polymer having a molecular weight of at least 5000.  The examples describe copolymers of: (1) stearyl methacrylate and 5-hydroxy-3-thiaamyl methacrylate, (2) stearyl methacrylate and 6-carboxy-3-thiahexyl methacrylate, (3) lauryl methacrylate and 5-mercapto-3-thiaamyl methacrylate, and (4) stearyl methacrylate lauryl methacrylate and 5-hydroxy-3-thiaamyl methacrylates.  In addition to mineral lubricating oils, the polymers may be added to gasoline jet fuels, transformer oils, turbine oils, hydraulic fluids, metal working fluids and quenching fluids.  For these purposes the polymers may be used in conjunction with other additives such as 2,6-ditert.butyl-4-butyl phenol, 4, 41-methylene (2, 6-ditertbutyl phenol), phenyl-alpha-naphthylamine, alkyl and aryl phosphates, phosphites and phosphonates and thio derivatives thereof, phosphorus pentasulphide-terpene reaction products and alkali metal salts thereof, zinc dialkyl dithiophosphate and zinc dibutyl dithiocarbamate.  Reference has been directed by the Comptroller to Specification 846,856.ALSO:Oil-soluble polymeric compounds are prepared which contain a linear carbon-to-carbon backbone chain having attached thereto a plurality of each of two groups, one being or containing a -COOR group and the other being or containing a -COOR1-S-R11-Y group, wherein R is an alkyl radical having at least 8 carbon atoms, R1 and R11 are the same or different alkylene radicals and Y is an acidic polar radical, e.g. carboxyl, hydroxyl, mercapto, halogen or cyano, the polymer having a molecular weight of at least 5,000.  The polymers are prepared by copolymerizing (A) esters of long chain alkanols and unsaturated acid with (B) esters of omega-acidic polar substituted thia-alkanols.  Monomers (A) specified are nonyl, lauryl and stearyl acrylates and methacrylates, cetyl methacrylate, 2-ethylhexyl methacrylate and tetramethyl-lauryl methacrylate.  Monomers (B) specified are 5-hydroxy-3-thiaamyl, 5-mercapto-3-thiaamyl and 8-hydroxy-4-thiacotyl acrylates and 5-carboxy-4-thiaamyl 6-hydroxy-3-thiahexyl, 7-hydroxy-4-thiaheptyl, 8-carboxy-3-thiaoctyl, 8-mercapto-4-thiaoctyl, 12-mercapto-3-thiadodecyl, 18-mercapto-5-thiastearyl and 6-carboxy-3-thiahexyl methacrylates.  Mixtures of more than two monomers may be used. The copolymers may be prepared by copolymerizing monomer (A) and monomer (B) in a mol ratio of 1:10 to 10:1 in the presence of an initiator, e.g. azodiisobutyronitrile, and a diluent, e.g. benzene, toluene, xylene and mineral oil.  The products are used as additives to hydrocarbons, especially lubricating oils.  Reference has been directed by the Comptroller to Specification 846,856.ALSO:Esters of omega-hydroxy thia-alkanols with acrylic or methacrylic acid are prepared by reacting an acrylyl halide with an omega-hydroxy thia-alkanol in the presence of a suitable base, e.g. pyridine; specified products are 5-hydroxy-3-thia amyl acrylate, 6-hydroxy-3-thia hexyl methacrylate, 8-hydroxy-4-thia octyl acrylate and 7-hydroxy-4-thia heptyl methacrylate. Methacrylate esters of omega-carboxyl thia alkanols are prepared by reacting acetone cyano-hydrin with an omega-carboxylic-thia alkanol in the presence of sulphuric acid; thus, 5-carboxy-4-thia amyl alcohol may be so reacted yielding 5-carboxy-4-thia amyl methacrylate.  The 8-carboxy-3-thia octyl and 6-carboxy-3-thia hexyl methacrylates are also mentioned.  Reference has been directed by the Comptroller to Specification 846,856.