US2897152A - Lubricating oils - Google Patents

Lubricating oils Download PDF

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Publication number
US2897152A
US2897152A US643544A US64354457A US2897152A US 2897152 A US2897152 A US 2897152A US 643544 A US643544 A US 643544A US 64354457 A US64354457 A US 64354457A US 2897152 A US2897152 A US 2897152A
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Prior art keywords
butyl
acetate
oil
dithiocarbamyl
additives
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Elliott John Scotchford
Edwards Eric Descamp
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CC Wakefield and Co Ltd
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CC Wakefield and Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/21—Radicals derived from sulfur analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/16—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiourea type, i.e. containing the group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/08—Halogenated waxes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/083—Dibenzyl sulfide
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines

Definitions

  • alubricating composition comprising a mineral lubricating oil base and a minor proportion of a compound having the formulaz' 1 e i 1.
  • R and R are alkyl, aryl, cycloalkyl radicals or where R and R are hydrocarbon radicals, preferably CH and R is an alkyl, aryl or cycloalkyl radical. 7.
  • R R d R it is necessary to select R R d R so thatlthe resulting product is oil-soluble in the proportions in which it is to be employed.
  • R is CH;.;- and R R and R are alkyl radicals, the sum of'the carbon atoms in R R and R being at least six.
  • oils used for turbine lubrication consist of specially selected mineraloil blends stabilised against oxidation by the incorporation of antioxidant additives and containing also additives designed to protect ferrous metal parts against rusting or corrosion by, e.g. sea water.
  • antioxidant additives and containing also additives designed to protect ferrous metal parts against rusting or corrosion by, e.g. sea water.
  • additional additives, incorporated in such oils tor the purpose of enhancing their extreme pressure properties
  • radicals R R or R may contain halogen substituents, but when the additives are to be employed in turbine oils, the presence of halogen is to be avoided.
  • ester groups situated in the alpha position to the dithiocarbamate group exerts an activating influence with the consequent pro-. duction of extreme pressure properties substantially in excess of those obtainable by the use of the simple aliphatic or aromatic dithiocarbamates.
  • suitable compounds falling 'within'i'the above formula include: n-Butyl (dimethyl dithiocarbamyl) acetate, n-Butyl (di-n butyl dithiocarbamyl) acetate, n-Butyl (di isopro'pyl dithiocarbamyl) acetate,
  • CHr-C g C2115 10 percent may be employed, but in general from about 0.5 percent to about 2.0 percent is contemplated, especially for use in turbine oils.
  • smaller proportions of the additives may be employed, e.g. from 0.05 to 0.5.
  • the addi tives may be employed in steam turbine oils, especially in marine turbine oils.
  • the turbine oils to which the additives of the present invention may be added may contain additional antioxidant additives which maybe of the alkylated phenol type, e.g.
  • tertiary butyl cresol 2:4 dimethyl-6-tertiary butyl phenol or 2:6 di-tertiary butyl-p-cresol
  • antirusting additives which may be of various types, one such class of additives being the acid esters of the long chain mono-esters of polyhydric alcohols described in British patent specification No. 643,025. V
  • a copper-staining inhibitor When the lubricants of the present invention are to be employed at relatively high temperatures it is desirable to include therein a copper-staining inhibitor.
  • a copper-staining inhibitor there may be included in the lubricant a minor proportion of a mercapto-arylene-thiazole or a derivative thereof, or an alkyl thiuram disulphide, or an additive or combination of additives of the type disclosed in United States patent application Serial No. 507,147, now US. Patent No. 2,836,561.
  • the copper-staining inhibitor is a cyclic compound capable of homolytic dissociation into free radicals
  • a preferred subclass of inhibitors of this type are 2-mercaptobenzothiazole and its derivatives such as benzothiazole disulphide, hydroxy methyl thiobenzothiazole .and triphenyl methyl thiobenzothiazole, but the corresponding derivatives of other Z-mercaptothiazoles may be employed, all as disclosed in my aforementioned application Serial No. 507,147.
  • the additives of the present invention may, if desired, be employed in conjunction with organic halogenated compounds in mineral lubricating oils to provide, for example, extreme pressure lubricants for hypoid gears.
  • organic halogenated compound is chlorinated parafiin wax which may be employed in an amount from 1 to 15% by Weight. Oils containing such combinations of additives are capable of withstanding higher loads than oils which contain only the sulphur compound. As already stated, however, the presence of halogen compounds in turbine oils is undesirable.
  • Oil B which consisted of 80% of a solvent-re- 0 r0 dimeth 1 dithiocarbaml acetate solid er- I Is g 2(86; thegretical, 28.9% n (p 5 guild mniieral oil havmg a viscosity of about 150 seconds Isobu 1 dm eth l dithiocarbam l acetate .0 stalline 6 9 140 i of solvent'refined g y y) I W eral 011 having a viscosity of about seconds Redwood 140 F.
  • Oil B which consisted of 80% of a solvent-re- 0 r0 dimeth 1 dithiocarbaml acetate solid er- I Is g 2(86; thegretical, 28.9% n (p 5 guild mniieral oil havmg a viscosity of about 150 seconds Isobu 1 dm eth l dithiocarb
  • Tests were normally run for one minute at a series of difierent loads, but in certain cases supplementary tests were carried out for a duration of ten seconds, the Mean Hertz Load" being calculated by the standard procedure described in U.S. Federal Specification VV-L-79ld Method 650.3 (1950).
  • tests '2 to 10 summarize the load-carrying properties of a vairety of lubricating oils prepared in ac cordance with the present invention, from which it will be seen that in all cases the load-carrying'capacity of the base oil (test 1) 'is greatly increased by the presence of organic dithiocarbamyl acetates.
  • Tests 11 and, 12 give comparative figures obtained with a simple conventional organic dithioca-rbamate, while test 13 quotes similar figures for dibenzyl disulphide, a well known extreme pressure additive known to be among the most efiective of the simple organic disulphides.
  • test 11 By comparing test 11 with tests 4 to 10 (all about .40% added S) it will again be seen that the simple thiocarbamate ester was inferior to the compounds of the present invention.
  • the organic dithiocarbamyl acetates When used in turbine oils, the organic dithiocarbamyl acetates not only do not adversely affect the properties of such oils but confer valuable'antioxidant' and antifoaming properties, thus rendering unnecessary the addition of specific antioxidant and antifoaming additives. If special load-carrying properties are not required, quite small amounts of the dithiocarbamyl acetates are sulficient to confer a degree of oxidation, and foaming sta:
  • B 0.11 630 do Nil N 17 n-Butyl (dimethyldithiocarbamyl) acetate (0.1%)
  • 18 n-Bntyl (di-n-butyl dithiocarbamyl) acetate (2.0%).
  • Table 2 illustrates the effect of the additives on typ1- temperatures, a selection of the results belng given in cal turbine oils containing rust inhibitors which, with the 20 Table 3.
  • test 17 the foaming test was carried out using as base oil the higher viscosity component of oil A without rust inhibitors.
  • test 15 to 17 and 19 By comparing tests 15 to 17 and 19 with test 14, it will be seen that they also function effectively as inhibitors of foaming. In test 20, the presence of zinc di-n-butyl dithiocarbamate evidently interfered with this eifect.
  • oils such as acidity, demulsification value and salt-water corrosion resistance were unafi'ected by the addition of the dithiocarbamylacetates.
  • a turbine oil complying with British Admiralty Specification O.M. 100 and consisting of base oil B containing 1.0% n-butyl (dimethyl dithiocarbamyl) acetate together with rust inhibitors as in Example 1 and copper deactivators as in Example 4 was subjected to a test on the well known Institution of Automobile Engineers (I.A.E.) 3 A" Centres Gear Machine described by Mansion in the Journal of the Institute of Petroleum, volume 38, page 633 (1952). This machine was operated at 4000 rpm. using En. 34 gears, with an oil temperature of 70 C. The average failure load was 93 lbs, a typical 0.M. 100 turbine oil without load-carrying additive failing at 29 lbs.
  • Example 3 To,illustrate the use of dithiocanbamyl acetates in extreme pressure lubricants suitable for hypoid gears, the composition of Example 3 was tested on the four ball machine (standard one minute run), the weld point being 490-500 kg. and the mean wear scar diameter at 100, 200, 300 and 400 kg. load being respectively 0.5, 1.2, 1.7 and 2.3 mms.
  • a commercially available hypoid gear oil having approximately the same viscosity and complyingwith US. Army Specification MILL2105 welded at 400 kg, the mean Wear scar diameter at 100, 200 and 300 kg. load being respectively 0.4, 1.5 and 2.0 ms.
  • a lubricating composition consisting essentially of a mineral lubricating oil base containing 'from"0;05
  • X is selected from the group consisting of R1 and R2 hydrocarbon chain of nitrogen atom so as to form a ring structure, from the group consisting of -CH being lower alkyl radicals, and an aliphatic five carbon atoms attached to the R is selected 8 XNJL-S-RCOOR:
  • R is selected from the group consisting of 'CH2,
  • R; and R are lower alkyl radicals, and R is selected from the group consisting of a phenyl radical and an alkyl radical containing no more than eight carbon atoms.
  • a lubricating composition consisting essentially of a mineral lubricating oil base containing from 0.05 percent up to 2 percent by weight of n-butyl (dimethyl dithiocarbamyl) acetate.
  • a lubricating composition consisting essentially of "10 a mineral lubricating oil base containing from 0.0519 0.5 percent by weight of a compound having the formula: a. s
  • R where R and R are lower alkyl radicals and R is'au alkyl radical containing not more than eight carbon atoms.
  • a steam turbine oil' consisting essentially of a mineral lubricating oil base containing from 0.5 to 2 percent by weight of a compound having the formula:
  • R is selected from the group consisting of R.
  • R and R being lower alkyl radicals, and an aliphatic hydrocarbon chain of five carbon atoms attached to the nitrogen atom so as to form a ring structure
  • R is selected from the group consisting of CH where R; and R are lower alkyl radicals, and R is selected from the group consisting of a phenyl radical and an alkyl radical containing no more than eight carbon atoms.
  • a steam turbine oil consisting essentially of a mineral lubricating oil base containing from 0.5 to 2 percent by weight of a compound having the formula:
  • R and R are lower alkyl radicals and R is an alkyl radical containing no more than eight carbon atoms.
  • a lubricating composition consisting essentially of a mineral lubricating oil base containing from 0.05 percent up to 10 percent by weight of a compound having the formula:
  • X is selected from the group consisting of Elli 12 R and R being lower alkyl radicals, and an aliphatic Where R and R 'are lower alkyl radicals, and R is hydrocarbon chain of five carbon atoms attached to selected from the group consisting of a phenyl radical the nitrogen atom so as to form a ring structure, R is and an alkyl radical containing no more than eight selected from the group consisting of -CH carbon atoms, and from 1 to 15 percent by weight of '5 a chlorinated paraflin wax.

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Cited By (37)

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US3376224A (en) * 1963-05-24 1968-04-02 Castrol Ltd Lubricating compositions and antioxidants therefor
US3833496A (en) * 1973-04-06 1974-09-03 Ethyl Corp Oil composition
US4076639A (en) * 1976-08-30 1978-02-28 Mobil Oil Corporation Lubricant compositions
EP0125592A1 (de) * 1983-05-13 1984-11-21 BASF Aktiengesellschaft Verwendung von Tri- und Tetrachlorbutanolderivaten als Schmiermittelzusatz sowie Schmiermittel, enthaltend solche Zusätze
WO1987005622A1 (en) * 1986-03-18 1987-09-24 The Lubrizol Corporation Carbamate additive for low phosphorus or phosphorus free lubricating compositions
US5391310A (en) * 1993-11-23 1995-02-21 Cincinnati Milacron Inc. Sulfurized aqueous machining fluid composition
EP0712923A1 (en) 1994-11-15 1996-05-22 The Lubrizol Corporation Lubricants and fluids containing thiocarbamates and phosphorus esters
EP0769546A2 (en) 1995-10-18 1997-04-23 The Lubrizol Corporation Antiwear enhancing composition for lubricants and functional fluids
US5902776A (en) * 1995-09-19 1999-05-11 The Lubrizol Corporation Additive compositions for lubricants and functional fluids
US6228818B1 (en) 1991-12-06 2001-05-08 The Lubrizol Corporation Organophosphoryl borates and lubricants and aqueous fluids containing the same
US6599865B1 (en) 2002-07-12 2003-07-29 Ethyl Corporation Effective antioxidant combination for oxidation and deposit control in crankcase lubricants
US20060205615A1 (en) * 2005-03-14 2006-09-14 Esche Carl K Jr Additives and lubricant formulations for improved antioxidant properties
US20070111907A1 (en) * 2005-11-16 2007-05-17 Esche Carl K Jr Additives and lubricant formulations for providing friction modification
US20070135317A1 (en) * 2005-12-12 2007-06-14 Tze-Chi Jao Nanosphere additives and lubricant formulations containing the nanosphere additives
US20070132274A1 (en) * 2005-12-09 2007-06-14 Lam William Y Titanium-containing lubricating oil composition
US20070149418A1 (en) * 2005-12-22 2007-06-28 Esche Carl K Jr Additives and lubricant formulations having improved antiwear properties
US20070254820A1 (en) * 2006-04-28 2007-11-01 Tze-Chi Jao Diblock monopolymers as lubricant additives and lubricant formulations containing same
US20080132432A1 (en) * 2006-12-01 2008-06-05 Mathur Naresh C Additives and lubricant formulations for providing friction modification
US20080161213A1 (en) * 2007-01-03 2008-07-03 Tze-Chi Jao Nanoparticle additives and lubricant formulations containing the nanoparticle additives
US20080277203A1 (en) * 2007-05-08 2008-11-13 Guinther Gregory H Additives and lubricant formulations for improved phosphorus retention properties
US20080280796A1 (en) * 2007-05-08 2008-11-13 Guinther Gregory H Additives and lubricant formulations for improved catalyst performance
US20090069205A1 (en) * 2007-09-10 2009-03-12 Devlin Mark T Additives and lubricant formulations having improved antiwear properties
US20090111722A1 (en) * 2007-10-25 2009-04-30 Guinther Gregory H Engine wear protection in engines operated using ethanol-based fuel
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
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US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
US20100144563A1 (en) * 2008-12-09 2010-06-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
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US20100292112A1 (en) * 2009-05-14 2010-11-18 Afton Chemical Corporation Extended drain diesel lubricant formulations
EP2261311A1 (en) 2009-06-10 2010-12-15 Afton Chemical Corporation Lubricating method and composition for reducing engine deposits
WO2011119918A1 (en) 2010-03-25 2011-09-29 R.T. Vanderbilt Company, Inc. Ultra low phosphorus lubricant compositions
EP2489637A1 (en) 2011-02-17 2012-08-22 Afton Chemical Corporation Cerium oxide nanoparticle additives and lubricant formulations containing the nanoparticle additives
WO2012122202A1 (en) * 2011-03-10 2012-09-13 The Lubrizol Corporation Lubricating composition containing a thiocarbamate compound
US8377856B2 (en) 2009-05-14 2013-02-19 Afton Chemical Corporation Extended drain diesel lubricant formulations
WO2013182581A1 (en) 2012-06-06 2013-12-12 Evonik Oil Additives Gmbh Fuel efficient lubricating oils
EP4202023A1 (en) 2021-12-21 2023-06-28 Afton Chemical Corporation Mixed fleet capable lubricating compositions

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US2160851A (en) * 1937-04-02 1939-06-06 Sonneborn Sons Inc L Stabilized petroleum oil distillates

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Cited By (64)

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Publication number Priority date Publication date Assignee Title
US3376224A (en) * 1963-05-24 1968-04-02 Castrol Ltd Lubricating compositions and antioxidants therefor
US3833496A (en) * 1973-04-06 1974-09-03 Ethyl Corp Oil composition
US4076639A (en) * 1976-08-30 1978-02-28 Mobil Oil Corporation Lubricant compositions
EP0125592A1 (de) * 1983-05-13 1984-11-21 BASF Aktiengesellschaft Verwendung von Tri- und Tetrachlorbutanolderivaten als Schmiermittelzusatz sowie Schmiermittel, enthaltend solche Zusätze
JPS63502905A (ja) * 1986-03-18 1988-10-27 ザ　ルブリゾル　コ−ポレ−ション 低リン潤滑組成物または無リン潤滑組成物のためのカルバメ−ト添加剤
US4758362A (en) * 1986-03-18 1988-07-19 The Lubrizol Corporation Carbamate additives for low phosphorus or phosphorus free lubricating compositions
AU599371B2 (en) * 1986-03-18 1990-07-19 Lubrizol Corporation, The Thio carbamate additives in low phosphorus lubricating compositions
WO1987005622A1 (en) * 1986-03-18 1987-09-24 The Lubrizol Corporation Carbamate additive for low phosphorus or phosphorus free lubricating compositions
US6228818B1 (en) 1991-12-06 2001-05-08 The Lubrizol Corporation Organophosphoryl borates and lubricants and aqueous fluids containing the same
US5391310A (en) * 1993-11-23 1995-02-21 Cincinnati Milacron Inc. Sulfurized aqueous machining fluid composition
EP0712923A1 (en) 1994-11-15 1996-05-22 The Lubrizol Corporation Lubricants and fluids containing thiocarbamates and phosphorus esters
US5902776A (en) * 1995-09-19 1999-05-11 The Lubrizol Corporation Additive compositions for lubricants and functional fluids
EP0769546A2 (en) 1995-10-18 1997-04-23 The Lubrizol Corporation Antiwear enhancing composition for lubricants and functional fluids
US6599865B1 (en) 2002-07-12 2003-07-29 Ethyl Corporation Effective antioxidant combination for oxidation and deposit control in crankcase lubricants
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US7615520B2 (en) 2005-03-14 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US20060205615A1 (en) * 2005-03-14 2006-09-14 Esche Carl K Jr Additives and lubricant formulations for improved antioxidant properties
US20070111907A1 (en) * 2005-11-16 2007-05-17 Esche Carl K Jr Additives and lubricant formulations for providing friction modification
US7709423B2 (en) 2005-11-16 2010-05-04 Afton Chemical Corporation Additives and lubricant formulations for providing friction modification
US7776800B2 (en) 2005-12-09 2010-08-17 Afton Chemical Corporation Titanium-containing lubricating oil composition
US20070132274A1 (en) * 2005-12-09 2007-06-14 Lam William Y Titanium-containing lubricating oil composition
US7632788B2 (en) 2005-12-12 2009-12-15 Afton Chemical Corporation Nanosphere additives and lubricant formulations containing the nanosphere additives
US20070135317A1 (en) * 2005-12-12 2007-06-14 Tze-Chi Jao Nanosphere additives and lubricant formulations containing the nanosphere additives
US20070149418A1 (en) * 2005-12-22 2007-06-28 Esche Carl K Jr Additives and lubricant formulations having improved antiwear properties
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
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US20080132432A1 (en) * 2006-12-01 2008-06-05 Mathur Naresh C Additives and lubricant formulations for providing friction modification
DE102007023939A1 (de) 2007-01-03 2008-07-10 Afton Chemical Corp. Nanoteilchenadditive und Schmiermittelformulierungen, die die Nanoteilchenadditive enthalten
US20080161213A1 (en) * 2007-01-03 2008-07-03 Tze-Chi Jao Nanoparticle additives and lubricant formulations containing the nanoparticle additives
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US20080280796A1 (en) * 2007-05-08 2008-11-13 Guinther Gregory H Additives and lubricant formulations for improved catalyst performance
DE102008009042A1 (de) 2007-05-08 2008-11-13 Afton Chemical Corp. Additive und Schmiermittelformulierungen für verbesserte Phosphor-Retentionseigenschaften
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