US2689220A - Lubricating oil compositions of mixed diester dithiophosphates - Google Patents

Lubricating oil compositions of mixed diester dithiophosphates Download PDF

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Publication number
US2689220A
US2689220A US218282A US21828251A US2689220A US 2689220 A US2689220 A US 2689220A US 218282 A US218282 A US 218282A US 21828251 A US21828251 A US 21828251A US 2689220 A US2689220 A US 2689220A
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alcohols
oil
zinc
alcohol
zinc salts
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US218282A
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Paul K Mulvany
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California Research LLC
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California Research LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
    • C10M2207/027—Neutral salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/08—Halogenated waxes
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention pertains to a new composition of matter; that is, a lubricating oil composition comprising an oil of lubricating viscosity and zinc salts of mixed diesters of dithiophosphoric acids (i. e., wherein the organic portions of the acids are derived from two different alcohols e. g., butyl alcohol and hexyl alcohol).
  • this invention pertains to lubricants containing zinc salts of mixed diesters of dithiophosphoric acids wherein the alcohols used in the preparation of the dithiophosphoric acids are of low molecular weight.
  • zinc salts of dialkyldithiophosphoric acids inhibit oxidation of lubricating oil compositions.
  • the alkyl groups of these zinc dialkyldithiophosphates may be of high molecular weight or low molecular weight.
  • the lubricants considered herein comprise, in particular, oils of lubricating viscosity and zinc salts of mixed esters of dithiophosphoric acids.
  • the zinc salts of mixed esters of diothiophosphoric acids incorporated in the lubricating compositions of this invention are zinc salts of products obtained by reacting phosphorus pentasulfide with two different alcohols.
  • One of the alcohols used in preparing the mixed ester of dithiophosphoric acids contains not more than 4 carbon atoms; for example, methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol, sec-butyl alcohol and tertiary butyl alcohol.
  • this group of alcohols will hereinafter be called the R1 alcohols.
  • the other alcohols used in the preparation of mixed esters of dithiophosphoric acids contain from 6 to 18 carbon atoms. These include the following alcohols: hexyl, methylisobutylcarbinol, ethylisopropylcarbinol, heptyl, isoheptyl, 2-ethyl amyl, octyl, isooctyl, 3-ethyl hexyl, 2- propyl amyl, decyl, undecyl, dodecyl, hexadecyl, octadecyl, etc.
  • this group of alcohols will hereinafter be known as the R2 alcohols.
  • the R1 and R2 alcohols need not be present in the reaction mixture in equal molar amounts.
  • the mole ratio of R1 alcohols to R2 alcohols be from 1 to 5. It is particularly preferred to use a mole ratio of R1 alcohols to R2 alcohols from 2 to 4.
  • Suitable oils of lubricating viscosity include a wide variety of lubricating oils such as naphthenic base, parailin base, and mixed base mineral oils, other hydrocarbon lubricants, e. g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof), alkylene oxide type polymers, dicarboxylic acid esters and liquid esters of acids of phosphorus.
  • Synthetic oils of the alkylene oxide type polymer which may be used include those exemplified by alkylene oxide polymers (e. g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxides (e.
  • propylene oxide in the presence of water or alcohols, e. g., ethyl alcohol, and esters of alkylene oxide-type olymers, e. g., acetylated propylene oxide polymers prepared by acetylating the propylene oxide polymers containing hydroxyl groups.
  • alcohols e. g., ethyl alcohol
  • esters of alkylene oxide-type olymers e. g., acetylated propylene oxide polymers prepared by acetylating the propylene oxide polymers containing hydroxyl groups.
  • Synthetic oils of the dicarboxylic acid ester type include those which are prepared by esterifying such 'di'carboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alxenyl succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, etc.
  • Examples of dicarboxylic acid ester synthetic oils include dibutyl adipate, dihexyl adipate, di-2-ethylhexyl sebacat'e, di-n-hexyl fumarate polymer, etc.
  • Synthetic oils of the type of liquid esters of acids of phopshorus include the esters of phosphoric acid, e. g., tricresyl phosphate; the esters of phosphonic acid, e. g., diethyl ester of decane phosphonic acid, or other such esters as obtained by reacting alkyl phosphonyl chlorides with hydroxyl-containing compounds, such as phenols and aliphatic alcohols, and with olefin oxides such as propylene oxide, as described in Jensen et al., U. S. application Serial No. 86,856, filed April 11, 19 9, now abandoned.
  • the zinc salts of this invention that is, the zinc salts of mixed esters of dithiophosphoric acids are normally used in lubricating oil compositions in amounts su'fiicient to inhibit oxida tion of the base oil. Although it is preferred to use from 0.05% to 2.0% by weight, based on the final oil composition, lubricating oil concentrates containing as much as 50% or more by weight may be prepared.
  • the zinc salts of this invention are formed from mixed esters of dithiophospho'ric acids prepared by reacting phosphorus pentasulfide (P285) with a mixture of two different alcohols at temperatures ranging from about 120 F. to 200 F.
  • P285 phosphorus pentasulfide
  • 4 moles of the desired alcohols e. g., 3 moles of methyl alcohol and 1 mole of hexyl alcohol, wherein the mol ratio of methyl alcohol to hexyl alcohol is 3:1
  • PzSs e. g., 3 moles of methyl alcohol and 1 mole of hexyl alcohol, wherein the mol ratio of methyl alcohol to hexyl alcohol is 3:1
  • the mixed dialkyldithiophosphoric acids e. g., zinc methyl hexyl dithiophosphate
  • the mixed dialkyldithiophoshphoric acids are reacted with zinc oxide at temperatures ranging from 70 F. to 170 F.
  • Example 1 Zinc salt of reactionproduct of isopropyl alcohol, methylisobutylcarbinol and P285
  • a mixture of 252 parts by weight (67 mole per cent) of isopropyl alcohol and 206 parts by weight (33 mole per cent) of methylisobutylcarbinol was placed in a glass reaction vessel.
  • To this mixture was added 333 partsby weight of P265.
  • the whole mixture was heated at 170 F. for 2 hours, after which the reaction mixture was cooled, and the product filtered to remove a small amount of unreacted P2S5.
  • Example 2 --Zinc salt of reaction product of butyl alcohol, methylisobutylcarbinol and PzSs
  • a mixture of 237 parts by weight (77 mol per cent) of sec-butyl alcohol, 98 parts by weight (23 mole per cent) of methylisobutylcarbinol and 222 parts by weight of P285 was charged to a reaction vessel and agitated at F. for a period of 2 hours.
  • the reaction mixture was cooled and filtered to remove a small amount of unreacted P285.
  • the resulting butylmethylisobutylcarbinol dithiophosphate was a dark red green liquid having a neutralization number of 193 (mgs. KOH/gram) a viscosity of 35.7 SSU at 100 F., a specific gravity of 1.04 (60/60), and contained 24.0% sulfur and 11.9% phosphorus.
  • the oil solubility of mixed diester dithiophosphoric acids is considerably greater than the same mole ratio of a mixture of two diester dithiophosphoric acids (wherein the ester groups in each acid are the same; that is, each acid contains only one of the ester radicals of the above mixed diester dithiophosphoric acid).
  • a 35% petroleum oil solution of a mixture of zinc di(sec-butyl) dithiophosphate and zinc di(methylisobutylcarbinol) dithiophosphate (mole ratio of 3.35:1) began to crystallize from solution within a period of 2 days at -20 F.
  • the table below presents data concerning the effectiveness of zinc salts of mixed esters of dithiophosphoric acids in reducing corrosion of metal parts due to oxidation of lubricating oils during operation of internal combustion engines.
  • a stock Chevrolet engine was used. Instead of the normal babbitt bearings of the Chevrolet engine, two of the connecting rods were modified to accommodate copper-lead bearing inserts, Which were weighed before being assembled in the engine.
  • the Chevro et engine was operated at 3150 R. P. M., the engine jacket temperature was maintained at 200 F., the crankcase oil temperature was maintained at 280 F., and the engine was operated for a period of 36 hours before being disassembled and the bearing inserts weighed. Before weighing, the bearing inserts were carefully washed with solvents to remove the oil therefrom.
  • This reference 011 was a Mid-Continent SAE 30 oil.
  • Tests were also run to determine the effectiveness of the zinc salts of mixed diesters of dithiophosphoric acids for increasing the inhibition period of lubricating oils.
  • a medicinal white oil was the base oil.
  • the inhibition period (the time in hours before 100 grams of oil sample utilizes 1000 cubic centimeters of oxygen at 340 F.) of medicinal white oil was zero hours.
  • the inhibition period of the same base oil containing 0.19% of the zinc salt of Example 2 above was 4.2 hours.
  • zinc salts of mixed esters of this invention also include phenates (e. g'., calcium cetyl phenate), sulfonates (e. g., calcium petroleum sulfonate), phenols (e. g., 2,6-di-tertiary butyl-4-methyl phenol), phosphonates (e. g., calcium white oil phosphonate), thiophosphonates (e. g., calcium cetyl thiophosphonate), sulfur-containing parafiins (e. g., sulfurized diparaffin sulfide), etc.
  • phenates e. g'., calcium cetyl phenate
  • sulfonates e. g., calcium petroleum sulfonate
  • phenols e. g., 2,6-di-tertiary butyl-4-methyl phenol
  • phosphonates e. g., calcium white oil phosphonate
  • thiophosphonates
  • a lubricant consisting essentially of a major proportion of an oil of lubricating viscosity and from 0.05% to 2.0% of zinc salts of mixed esters of dithiophosphoric acids produced by reacting phosphorus pentasulfide with a blend of 2 aliphatic monohydric alcohols at temperatures from F. to 200 F., one of said alcohols containing not more than 4 carbon atoms, the other of said alcohols containing from 6 to 18 carbon atoms, the ratio of the lower molecular weight alcohol to the higher molecular weight alcohol being from 1.0 to 5.0.
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.05% to 2.0% of zinc salts of mixed esters of dithiophosphoric acids produced by reacting phosphorus pentasulfide with a blend of 2 aliphatic monohydric alcohols at temperatures from 120 F. to 200 F., one of said alcohols containing not more than 4 carbon atoms, the other of said alcohols containing from 6 to 10 carbon atoms, the ratio of the lower molecular weight alcohol to the higher molecular weight of alcohol being from 1.0 to 5.0.

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US218282A 1951-03-29 1951-03-29 Lubricating oil compositions of mixed diester dithiophosphates Expired - Lifetime US2689220A (en)

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2837549A (en) * 1955-05-12 1958-06-03 American Cyanamid Co Zinc dialkyl dithiophosphates
DE1042807B (de) * 1955-01-27 1958-11-06 Lubrizol Corp Dithiophosphorsaeurederivate und organische Polysulfide enthaltender fluessiger Schmiermittelzusatz
DE1112067B (de) * 1957-04-18 1961-08-03 American Cyanamid Co Verfahren zur Herstellung von Zinksalzen gemischter Dithiophosphorsaeuredialkylester
US3000822A (en) * 1957-01-22 1961-09-19 Lubrizol Corp Phosphorodithioate inhibitors
US3013971A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3013970A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3013969A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
DE1119854B (de) * 1958-01-07 1961-12-21 Exxon Research Engineering Co Verfahren zur Herstellung von Metallsalzen von O, O-Dialkyldithio-phosphorsaeuren von verbesserter Bestaendigkeit
US3018247A (en) * 1960-03-15 1962-01-23 California Research Corp Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
US3073781A (en) * 1960-07-07 1963-01-15 Standard Oil Co Demulsifiable lubricant compositions
US3074990A (en) * 1958-12-29 1963-01-22 Universal Oil Prod Co Alkylthiophosphoric acid salt of polymeric condensation product and use thereof
US3087950A (en) * 1959-01-22 1963-04-30 Exxon Research Engineering Co Extreme pressure lubricant additive
US3112271A (en) * 1959-04-13 1963-11-26 Shell Oil Co Liquid hydrocarbon composition
US3293181A (en) * 1965-10-15 1966-12-20 Chevron Res Dialkyl dithiophosphates and lubricants containing them
US3318808A (en) * 1963-10-15 1967-05-09 Standard Oil Co Extreme pressure lubricants
US3390082A (en) * 1967-09-19 1968-06-25 Lubrizol Corp Lubricants containing metal-free dispersants and inhibitors
US3442804A (en) * 1967-01-19 1969-05-06 Lubrizol Corp Lubricating composition containing a phosphorodithioate inhibitor
US3511780A (en) * 1966-02-09 1970-05-12 Exxon Research Engineering Co Oil-soluble ashless dispersant-detergent-inhibitors
US4092341A (en) * 1976-02-27 1978-05-30 Edwin Cooper And Company Limited Process of making an oil solution of zinc dihydrocarbyldithiophosphates
US4377527A (en) * 1981-03-09 1983-03-22 Standard Oil Company (Indiana) Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US3341633A (en) * 1955-01-27 1967-09-12 Lubrizol Corp Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides
US2925398A (en) * 1957-02-11 1960-02-16 Monsanto Chemicals Composition comprising solid polyolefin and a hydrogenated polyphenyl
US2932614A (en) * 1958-01-07 1960-04-12 Exxon Research Engineering Co Manufacture of metal salts of dialkyl dithiophosphoric acids and concentrate in oil solution
GB1565961A (en) * 1976-02-25 1980-04-23 Orobis Ltd Composition comprising a mixture of the zinc salts of o,o'-dialkyl dithiophosphoric acids
DE3048087A1 (de) * 1980-12-19 1982-07-15 Bayer Ag, 5090 Leverkusen Zinkkomplexe, ein verfahren zu ihrer herstellung und ihre verwendung als verschleissschutz-additive
US4577037A (en) * 1984-02-10 1986-03-18 Chevron Research Methods for preventing the precipitation of mixed zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group
US4495075A (en) * 1984-05-15 1985-01-22 Chevron Research Company Methods and compositions for preventing the precipitation of zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group
GB8729963D0 (en) * 1987-12-23 1988-02-03 Exxon Chemical Patents Inc Dithiophosphates
US6884855B2 (en) 2003-01-30 2005-04-26 Chevron Oronite Company Llc Sulfurized polyisobutylene based wear and oxidation inhibitors
US7368596B2 (en) * 2003-11-06 2008-05-06 Afton Chemical Corporation Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US8211840B2 (en) * 2008-12-09 2012-07-03 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2334393A (en) * 1940-02-26 1943-11-16 Union Oil Co Determination of magnetic and electrical anisotropy of formation core samples
US2342432A (en) * 1941-12-22 1944-02-22 Gulf Oil Corp Mineral oil lubricating composition and an improvement agent therefor and its methodof preparation
US2368000A (en) * 1941-12-04 1945-01-23 American Cyanamid Co Lubricating compositions

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1939951A (en) * 1929-06-26 1933-12-19 American Cyanamid Co Seed disinfection
US2063629A (en) * 1935-02-19 1936-12-08 Du Pont Esters of the thio acids of phosphorus
USRE22829E (en) * 1939-05-06 1947-01-14 Compounded hydrocarbon oil
US2261047A (en) * 1941-07-28 1941-10-28 Lubri Zol Corp Lubricant
US2343213A (en) * 1942-04-10 1944-02-29 American Cyanamid Co Preparation of barium salts of dithiophosphoric acid esters
US2361746A (en) * 1943-04-12 1944-10-31 American Cyanamid Co Crankcase lubricating oil composition
US2466408A (en) * 1946-01-26 1949-04-05 American Cyanamid Co Lubricating composition
US2540084A (en) * 1947-05-14 1951-02-06 Lubrizol Corp Metallic salt of reaction product of phosphorus sulfide and alkylated cycloaliphatic alcohol
GB626251A (en) * 1947-06-30 1949-07-12 Shell Refining & Marketing Co Improvements in or relating to mineral lubricating oil compositions
NL69724C (Home) * 1947-12-09

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2334393A (en) * 1940-02-26 1943-11-16 Union Oil Co Determination of magnetic and electrical anisotropy of formation core samples
US2368000A (en) * 1941-12-04 1945-01-23 American Cyanamid Co Lubricating compositions
US2342432A (en) * 1941-12-22 1944-02-22 Gulf Oil Corp Mineral oil lubricating composition and an improvement agent therefor and its methodof preparation

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1042807B (de) * 1955-01-27 1958-11-06 Lubrizol Corp Dithiophosphorsaeurederivate und organische Polysulfide enthaltender fluessiger Schmiermittelzusatz
US3013971A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3013970A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3013969A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US2837549A (en) * 1955-05-12 1958-06-03 American Cyanamid Co Zinc dialkyl dithiophosphates
US3000822A (en) * 1957-01-22 1961-09-19 Lubrizol Corp Phosphorodithioate inhibitors
DE1112067B (de) * 1957-04-18 1961-08-03 American Cyanamid Co Verfahren zur Herstellung von Zinksalzen gemischter Dithiophosphorsaeuredialkylester
DE1119854B (de) * 1958-01-07 1961-12-21 Exxon Research Engineering Co Verfahren zur Herstellung von Metallsalzen von O, O-Dialkyldithio-phosphorsaeuren von verbesserter Bestaendigkeit
US3074990A (en) * 1958-12-29 1963-01-22 Universal Oil Prod Co Alkylthiophosphoric acid salt of polymeric condensation product and use thereof
US3087950A (en) * 1959-01-22 1963-04-30 Exxon Research Engineering Co Extreme pressure lubricant additive
US3112271A (en) * 1959-04-13 1963-11-26 Shell Oil Co Liquid hydrocarbon composition
US3018247A (en) * 1960-03-15 1962-01-23 California Research Corp Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
US3073781A (en) * 1960-07-07 1963-01-15 Standard Oil Co Demulsifiable lubricant compositions
US3318808A (en) * 1963-10-15 1967-05-09 Standard Oil Co Extreme pressure lubricants
US3293181A (en) * 1965-10-15 1966-12-20 Chevron Res Dialkyl dithiophosphates and lubricants containing them
US3511780A (en) * 1966-02-09 1970-05-12 Exxon Research Engineering Co Oil-soluble ashless dispersant-detergent-inhibitors
US3442804A (en) * 1967-01-19 1969-05-06 Lubrizol Corp Lubricating composition containing a phosphorodithioate inhibitor
US3390082A (en) * 1967-09-19 1968-06-25 Lubrizol Corp Lubricants containing metal-free dispersants and inhibitors
US4092341A (en) * 1976-02-27 1978-05-30 Edwin Cooper And Company Limited Process of making an oil solution of zinc dihydrocarbyldithiophosphates
US4377527A (en) * 1981-03-09 1983-03-22 Standard Oil Company (Indiana) Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates

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DE1097606B (de) 1961-01-19
US2680123A (en) 1954-06-01

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