[go: up one dir, main page]

GB658183A - Improvements in or relating to lubricating compositions - Google Patents

Improvements in or relating to lubricating compositions

Info

Publication number
GB658183A
GB658183A GB32502/47A GB3250247A GB658183A GB 658183 A GB658183 A GB 658183A GB 32502/47 A GB32502/47 A GB 32502/47A GB 3250247 A GB3250247 A GB 3250247A GB 658183 A GB658183 A GB 658183A
Authority
GB
United Kingdom
Prior art keywords
octyl
cresyl
dithiophosphate
acid
dithiophosphoric acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB32502/47A
Inventor
Elliott Alfred Evans
John Scotchford Elliott
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CC Wakefield and Co Ltd
Original Assignee
CC Wakefield and Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by CC Wakefield and Co Ltd filed Critical CC Wakefield and Co Ltd
Publication of GB658183A publication Critical patent/GB658183A/en
Priority to MY41/54A priority Critical patent/MY5400041A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • 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
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2010/14—Group 7
    • 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
    • C10N2010/16—Groups 8, 9, or 10

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

Tin petroleum sulphonate.-The tin salt of an oil-soluble petroleum sulphonic acid is used as an ingredient of a lubricating composition. In an example, an oil-concentrate containing sodium petroleum sulphonate derived from mahogany acids is dissolved in water. Tin petroleum sulphonate is precipitated from the solution by adding stannous chloride solution. Metal salts of organic dithiophosphoric acids.-Oil-soluble polyvalent metal salts of organic dithiophosphoric acids are used as ingredients of lubricating compositions, (see Group III). The salts may be substances of the general formula <FORM:0658183/IV (b)/1> where n is the valency of the metal M, R1 is any suitable organic radicle and R2 is an alkylated aromatic radicle. R1 may be derived from an aliphatic alcohol such as butyl amyl or lauryl alcohol, a cyclic alcohol such as cyclohexanol or methylcyclohexanol, a phenol such as cresol or octyl cresol or an aromatic alcohol such as benzyl alcohol. The radicle R2 may be derived from p-tert-amyl phenol, p-octyl phenol or octylcresol and preferably contains at least five carbon atoms in the alkyl group. However, the alkyl group of radicle R2 may contain less than five carbon atoms and may even be absent provided R1 is of such a nature as to confer oil-solubility upon the metal salt. The salts may alternatively be substances of the same general formula as that given above but wherein R1 and R2 are alkyl or cyclo-alkyl groups having at least five and preferably not more than ten carbon atoms either in a straight or branched chain or ring. Thus radicles R1 and R2 are preferably similar and may be derived from amyl alcohol, the hexyl alcohols such as n-hexyl alcohol, methyl isobutyl carbinol and 2 ethyl butanol, 2-ethyl hexanol, nonyl alcohol, cyclohexanol or methyl cyclohexanol. Organic dithiophosphoric acids from which the salts may be derived are di-(octyl-cresyl)-dithiophosphoric acid, octyl-cresyl cresyl dithiophosphoric acid, octyl-cresyl 2-ethyl hexyl dithiophosphoric acid, di-(p-octyl phenyl)-dithiophosphoric acid, di - (tert - butyl cresyl) - dithiophosphoric acid, octyl cresyl n-butyl dithiophosphoric acid, octyl cresyl cyclohexyl dithiophosphoric acid, di-(n-hexyl)-dithiophosphoric acid, di-(2-ethyl hexyl)-dithiophosphoric acid, di-(methyl cyclohexyl)-dithiophosphoric acid, diamyl dithiophosphoric acid and di-(a -methyl isoamyl)-dithiophosphoric acid. The octyl cresyl radicle mentioned in some of these acids is that derived from the mixture of octyl cresols obtained by alkylating cresylic acid with diisobutylene. The salts may be salts of chromium, barium, calcium, strontium, magnesium, zinc, aluminium, nickel, cobalt, tin, cadmium or manganese, and they may be derived from a mixture of organic dithiophosphoric acids. The acids may be prepared by reacting the appropriate organic hydroxy compounds with phosphorus pentasulphide. The salts may be prepared from the acids by direct neutralization with metal oxide or hydroxide or by metathesis from the sodium salt. In the examples: (1) chromium di-(octyl-cresyl)-dithiophosphate is prepared by reacting octyl cresol with P2S5, converting the acid obtained to its sodium salt and then precipitating the chromium salt by addition of chrome alum; (2) zinc di-(2-ethyl hexyl)-dithiophosphate is prepared by reacting 2-ethyl hexanol with P2S5 and neutralizing the acid obtained with zinc oxide; (3) tin octylcresyl 2-ethyl hexyl dithiophosphate is prepared by reacting a mixture of octyl cresol and 2-ethyl hexanol with P2S5, converting the acid obtained to its sodium salt, and then precipitating the tin salt with stannous chloride; (4) mixed chromium-zinc salt of di-(2-ethyl hexyl)-dithiophosphoric acid is prepared by reacting 2-ethyl hexanol with P2S5 and neutralizing the acid obtained with chromium hydroxide and zinc oxide; (5) chromium octyl-cresyl cresyl dithiophosphate is prepared by reacting a mixture of octyl cresol and cresylic acid with P2S5 and forming the chromium salt; (6) manganese di - (tert. - butyl cresyl) - dithiophosphate is prepared from a mixture of tert.-butyl cresols derived from cresylic acid, and (7) zinc di-(methyl cyclohexyl)-dithiophosphate is prepared from a mixture of methyl cyclohexanols obtained by the hydrogenation of cresylic acid. Reference has been directed by the Comptroller to Specifications 623,591 and 658,243.ALSO:A mineral lubricating oil composition suitable for use as the lubricant in petrol- or oil-operated internal-combustion engines comprises minor proportions of (a) the tin salt of an oil-soluble petroleum sulphonic acid and (b) an oil-soluble polyvalent metal salt of an organic dithiophosphoric acid. The composition possesses detergent properties and any tendency of the mineral oil to form deleterious oxidation products, particularly products corrosive to metals, is inhibited. The composition is particularly suitable for use as a heavy-duty lubricant in Diesel and other oil-operated engines. Ingredient (b) may be a substance of the general formula <FORM:0658183/III/1> where n is the valency of a metal M, R1 is any suitable organic radicle and R2 is an alkylated aromatic radicle. R1 may be derived from an aliphatic alcohol such as butyl, amyl or lauryl alcohol, a cyclic alcohol such as cyclohexanol or methyl cyclohexanol, a phenol such as cresol or octyl cresol or an aromatic alcohol such as benzyl alcohol. The radicle R2 may be derived from p-tert.-amyl phenol, p-octyl phenol or octyl cresol and preferably contains at least five carbon atoms in the alkyl group. However, the alkyl group of radicle R2 may contain less than five carbon atoms and may even be absent provided R1 is of such a nature as to confer oil-solubility upon the metal salt. Ingredient (b) may alternatively be a substance of the same general formula as that given above but wherein R1 and R2 are alkyl or cyclo-alkyl groups having at least five and preferably not more than ten carbon atoms either in a straight or branched chain or ring. Thus radicles R1 and R2 are preferably similar and may be derived from amyl alcohol, the hexyl alcohols such as n-hexyl alcohol, methyl isobutyl carbinol and 2-ethyl butanol, 2-ethyl hexanol, nonyl alcohol, cyclohexanol or methyl cyclohexanol. Organic dithiophosphoric acids from which ingredient (b) may be derived are di-(octyl-cresyl) dithiophosphoric acid, octyl-cresyl cresyl dithiophosphoric acid, octyl-cresyl 2-ethyl hexyl dithiophosphoric acid, di-(p-octyl phenyl) dithiophosphoric acid, di-(tert.-butyl cresyl) dithiophosphoric acid, octyl cresyl n-butyl dithiophosphoric acid, octyl cresyl cyclohexyl dithiophosphoric acid, di-(n-hexyl) dithiophosphoric acid, di-(2-ethyl hexyl) dithiophosphoric acid, di-(methyl cyclohexyl) dithiophosphoric acid, diamyl dithiophosphoric acid and di-(a -methyl isoamyl) dithiophosphoric acid. The octyl cresyl radicle mentioned in some of these acids is that derived from the mixture of octyl cresols obtained by alkylating cresylic acid with di-isobutylene. Ingredient (b) may be a salt of chromium, barium, calcium, strontium, magnesium, zinc, aluminium, nickel, cobalt, tin, cadmium or manganese and it may be derived from a mixture of organic dithiophosphoric acids. Since ingredient (b) may be prepared from the free organic dithiophosphoric acid and since this may first be converted to the sodium salt and then the desired metal salt obtained by metathesis, ingredient (b) may be contaminated with free organic dithiophosphoric acids or their sodium salts. The mineral lubricating oil composition may also contain as a third ingredient one or more of (1) a hydroxy-substituted aromatic thio-ether and/or di- or poly-sulphide, particularly di - (3 - carbomethoxy - 4 - hydroxyphenyl) thioether, disulphide or polysulphides; (2) an aromatic phosphite or thiophosphite ester derived from substance (1), particularly di-(3-carbomethoxy - 4 - hydroxyphenyl) thioether cresyl phosphite, and (3) a tri-aryl phosphite, particularly triphenyl phosphite or tri-(p-tert.-amyl phenyl) phosphite. In the examples there are described mineral lubricating cil compositions containing tin mahogany sulphonate and one of the following metal salts of organic dithiophosphoric acids: zinc di-(a -methyl isoamyl) dithiophosphate, chromium or zinc di-(octyl cresyl) dithiophosphate, chromium or magnesium di-(2-ethyl hexyl) dithiophosphate, cobalt octyl cresyl n-butyl dithiophosphate, chromium di-(p-octyl phenyl) dithiophosphate, cadmium octyl-cresyl cyclohexyl dithiophosphate, nickel di-(methyl cyclohexyl) dithiophosphate, manganese di-(tert.-butyl cresyl) dithiophosphate, chromium, zinc or tin octyl cresyl 2-ethyl hexyl dithiophosphate, zinc di-(a -methyl isoamyl) dithiophosphate. Other examples describe mineral lubricating oil compositions containing tin mahogany sulphonate and (i) zinc di-n-hexyl dithiophosphate and chromium octyl cresyl cresyl dithiophosphate; (ii) zinc di-(2-ethyl hexyl) dithiophosphate and tri-(p-tert.-amyl phenyl) phosphite; (iii) zinc di-(methyl cyclohexyl) dithiophosphate and octyl cresol thioether; (iv) zinc di-(a -methyl isoamyl) dithiophosphate and chromium di-(octyl cresyl) dithiophosphate with or without di-(3-carbomethoxy-4-hydroxy phenyl) thioether or di-(3-carbomethoxy-4-hydroxy phenyl) thioether cresyl phosphite; or (v) chromium di-(octyl cresyl) dithiophosphate with either di-(3-carbomethoxy-4-hydroxy phenyl) thioether cresyl phosphite or di-(3-carbomethoxy-4-hydroxy phenyl) polysulphide. For comparison purposes mineral lubricating oil compositions are described which contain (1) tin mahogany sulphonate; (2) zinc di-(a -methyl isoamyl) dithiophosphate; or (3) chromium di-(octyl cresyl) dithiophosphate with or without sodium or calcium mahogany sulphonate. Specifications 561,898, 567,939, 574,445, 594,960, 658,182 and U.S.A. Specification 2,125,936 are referred to. In the Provisional Specifications, Specifications 43
GB32502/47A 1947-12-09 1947-12-09 Improvements in or relating to lubricating compositions Expired GB658183A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
MY41/54A MY5400041A (en) 1947-12-09 1954-12-30 Improvements in or relating to lubricating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB277989X 1947-12-09
GB41148X 1948-11-04

Publications (1)

Publication Number Publication Date
GB658183A true GB658183A (en) 1951-10-03

Family

ID=26238882

Family Applications (2)

Application Number Title Priority Date Filing Date
GB32502/47A Expired GB658183A (en) 1947-12-09 1947-12-09 Improvements in or relating to lubricating compositions
GB32434/47A Expired GB658182A (en) 1947-12-09 1947-12-09 Improvements in or relating to lubricating compositions and the preparation of additives therefor

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB32434/47A Expired GB658182A (en) 1947-12-09 1947-12-09 Improvements in or relating to lubricating compositions and the preparation of additives therefor

Country Status (6)

Country Link
US (2) US2579037A (en)
CH (1) CH277989A (en)
DE (1) DE832030C (en)
FR (2) FR976343A (en)
GB (2) GB658183A (en)
NL (2) NL69724C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1042807B (en) * 1955-01-27 1958-11-06 Lubrizol Corp Liquid lubricant additive containing dithiophosphoric acid derivatives and organic polysulphides
DE1090361B (en) * 1957-01-22 1960-10-06 Lubrizol Corp Lubricant additives for internal combustion engines

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL76200C (en) * 1950-05-12
NL85589C (en) * 1951-03-29
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US2905683A (en) * 1952-12-17 1959-09-22 Lubrizol Corp Ether containing esters of dithiophosphoric acid and salts thereof
DE961484C (en) * 1952-12-18 1957-04-04 Exxon Research Engineering Co Process for increasing the viscosity index of lubricating oils
US2824063A (en) * 1956-05-11 1958-02-18 Sinclair Refining Co Lubricating oils containing a zinc dithiophosphate and nickel mahogany sulfonate
US2916448A (en) * 1957-05-31 1959-12-08 Sinclair Refining Co Oxidation inhibitor-detergent material
US3070546A (en) * 1959-01-16 1962-12-25 Lubrizol Corp Nitrogen-, phosphorus- and sulfurcontaining lubricants
DE1245013B (en) * 1960-05-12 1967-07-20 Sineclair Refining Company Mineral lubricating oil
US3243482A (en) * 1962-01-10 1966-03-29 Gen Aniline & Film Corp Surface-active thiophosphoric acid esters of polyglycol ethers
US3909447A (en) * 1972-07-17 1975-09-30 Petrolite Corp Mixtures of thiophosphates, oxygen phosphates and pyrophosphates
US4042323A (en) * 1972-07-17 1977-08-16 Petrolite Corporation Process of inhibiting corrosion of metal in an aqueous environment with mixtures of thio-, oxygen and thio- oxygen phosphates and pyrophosphates
US5919740A (en) * 1998-05-29 1999-07-06 Exxon Chemical Patents Inc Alkylthiophosphate salts for lubricating oils
CN113680535B (en) * 2021-08-24 2023-03-21 中南大学 Alkyl ether group dithiophosphate collecting agent and preparation method and application thereof

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2125936A (en) * 1936-03-03 1938-08-09 Sonneborn Sons Inc L Lubricating oil
US2228659A (en) * 1938-11-21 1941-01-14 Standard Oil Co Compounded mineral oil
US2241243A (en) * 1939-03-25 1941-05-06 Texas Co Lubricating oil
USRE22829E (en) * 1939-05-06 1947-01-14 Compounded hydrocarbon oil
US2322307A (en) * 1939-06-20 1943-06-22 Standard Oil Co California Compounded oil
US2372244A (en) * 1941-09-24 1945-03-27 Standard Oil Co Esters of acids of phosphorus
US2344392A (en) * 1941-11-08 1944-03-14 American Cyanamid Co Crankcase lubricant and chemical compound therefor
US2369632A (en) * 1941-11-13 1945-02-13 American Cyanamid Co Lubricating oils
US2382775A (en) * 1942-06-16 1945-08-14 American Cyanamid Co Dithiophosphoric acids and salts thereof
US2344395A (en) * 1942-06-16 1944-03-14 American Cyanamid Co Lubricating oil
US2383917A (en) * 1942-07-09 1945-08-28 Cities Service Oil Co Lubricant
GB561941A (en) * 1942-07-29 1944-06-12 Elliott Alfred Evans Improvements in or relating to lubricating oils
US2417876A (en) * 1944-08-16 1947-03-25 Tide Water Associated Oil Comp Inhibited oil
US2418422A (en) * 1944-12-11 1947-04-01 Sinclair Refining Co Lubricant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1042807B (en) * 1955-01-27 1958-11-06 Lubrizol Corp Liquid lubricant additive containing dithiophosphoric acid derivatives and organic polysulphides
DE1090361B (en) * 1957-01-22 1960-10-06 Lubrizol Corp Lubricant additives for internal combustion engines

Also Published As

Publication number Publication date
DE832030C (en) 1952-02-21
US2579038A (en) 1951-12-18
NL70344C (en)
NL69724C (en)
GB658182A (en) 1951-10-03
CH277989A (en) 1951-09-30
US2579037A (en) 1951-12-18
FR976342A (en) 1951-03-16
FR976343A (en) 1951-03-16

Similar Documents

Publication Publication Date Title
US2369632A (en) Lubricating oils
GB658183A (en) Improvements in or relating to lubricating compositions
US3376222A (en) Process for preparing lubricating grease
GB670077A (en) Improved oxidation resisting compositions comprising mineral lubricating oils, and hydrocarbon polymers, synthetic rubbers and waxes
US2767164A (en) Complexes containing phosporus and sulphur and methods of making same
US3595790A (en) Oil soluble highly basic metal salts of organic acids
US2645657A (en) Thiophosphate esters
GB603238A (en) An improved lubricant, and manufacture of addition agents therefor
US3259579A (en) Esters of dithiophosphoric acids and lubricating oil compositions containing same
US2758971A (en) Blending agents for mineral oils
US2655544A (en) Alkylation of phenols with polypropylene
US2368000A (en) Lubricating compositions
GB968801A (en) Improvements in or relating to the preparation of metal dialkyl dithiophosphates
US2734865A (en) Stabilized lubricating compositions
US3376221A (en) Metal salts of mixed phosphorothioic and phosphinothioic acids
US2358305A (en) Lubricating composition
US2329436A (en) Lubricating oil composition
GB696064A (en) Lubricating compositions
US2420068A (en) Lubricant
US2966460A (en) Lubricating oil composition
GB1047098A (en) Lubricant-fuel mixture for two-stroke internal combustion engines
US2659705A (en) Corrosion preventing agent
US2605278A (en) Salt of a thiuronium base and an acid of phosphorus
US2824063A (en) Lubricating oils containing a zinc dithiophosphate and nickel mahogany sulfonate
US2528257A (en) Lubricating composition