GB798635A - Lubricating oil compositions - Google Patents

Lubricating oil compositions

Info

Publication number
GB798635A
GB798635A GB18809/56A GB1880956A GB798635A GB 798635 A GB798635 A GB 798635A GB 18809/56 A GB18809/56 A GB 18809/56A GB 1880956 A GB1880956 A GB 1880956A GB 798635 A GB798635 A GB 798635A
Authority
GB
United Kingdom
Prior art keywords
amine
acids
acid
carbon atoms
phosphonic
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
GB18809/56A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB798635A publication Critical patent/GB798635A/en
Expired legal-status Critical Current

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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06Well-defined aromatic compounds
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14Synthetic waxes, e.g. polythene waxes
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/17Fisher Tropsch reaction products
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    • C10M2207/02Hydroxy compounds
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    • C10M2207/02Hydroxy compounds
    • C10M2207/021Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/082Macromolecular 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 monocarboxylic
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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  • Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

Partial or full salts of branched chain primary or secondary aliphatic or cycloaliphatic amines having at least 8 carbon atoms and organic phosphorus acids of general formula: <FORM:0798635/IV (b)/1> where R is a hydrocarbon or halohydrocarbon radical, X is a non-metallic element of Group VIb of the Periodic Table, and y is H, XH, or R are referred to for use as lubricant additives (see Group III). C8-36 amines are preferred, extensive lists being given including 1,1,3,3-tetramethyl butyl amine, isoheptyl diethyl carbinylamine, di-(2-ethyl hexyl) amine, dibromo-dioctadecylamine, butyl ricinoleylamine, dicyclopentylamine, benzyl 2-ethyl hexyl amine, allyl octyl amine, N-n-dodecyl diethylene triamine, N-2-ethyl hexyl N-hexadecyl triethylene tetramine, and N,N1-diallyl trimethylene diamine. Many examples are given of paraffinic and alicyclic hydrocarbon-, chlorohydrocarbon-, bromohydrocarbon-, and chlorobromohydrocarbon - substituted phosphinic, thiophosphinic, phosphonic, thiophosphonic, and selenophosphonic acids which may be used to form the amine salts. The salts have the general formul : <FORM:0798635/IV (b)/2> where A is the amine and R1 is R or H. They may be prepared by reacting the selected amine and acid in a solvent or in the presence of water under suitable conditions such as mixing at room temperature, stirring or heating. They may be purified by recrystallization. A long list of preferred salts includes salts of trifluoromethane phosphonic acid and trichloromethane dithiophosphonic acid. The preparation is described of compounds of the formula: <FORM:0798635/IV (b)/3> by the reaction at 50 DEG C. of 1 mol. of trichloromethane phosphonic acid and 2 mols. of A3, 1 mol. of A3 and 2 mols. of A1 respectively. A3 is a mixture of t-alkyl (C18-24) primary amines and A1 a mixture of t-alkyl (C12-15) primary amines. In examples the above amines are incorporated in lubricating oil compositions, the amine and acid being added to the oil separately. Specifications 505,016, [Group IV], 634,720, 637,389 and 689,872 are referred to.ALSO:A lubricating oil composition comprises a major proportion of a lubricating oil and minor proportions of (a) salt of a branched-chain primary or secondary aliphatic or cycloaliphatic amine having at least 8 carbon atoms and an organic phosphorus acid of the general formula <FORM:0798635/III/1> where R is a hydrocarbon or halohydrocarbon radical, X is a non-metallic element of Group VI (b) of the Periodic Table and Y is H, XH, or R; and (b) a partial ester of a polyhydric alcohol and an organic carboxylic or sulphonic acid. The lubricating oil is preferably a mineral or sulphurized mineral oil but synthetic oils may also be used, e.g. polymerized olefins, alkylated aromatics, polyalkyl silicone polymers, hydrogen sulphide adducts of unsaturated ethers and thioethers and esters such as di-(2-ethyl hexyl) sebacate. The amine used in component (a) preferably contains from 8 to 36 carbon atoms, extensive lists of branchedchain primary and secondary amines being given, including dibromodioctadecyl amine and diricinoleyl amine. Many examples are given of hydrocarbon, chloro-hydrocarbon and bromohydrocarbon substituted phosphinic, thiophosphinic, phosphonic, thio-phosphonic and seleno-phosphonic acids which may be used to form the amine salts which have the general formul <FORM:0798635/III/2> where A is the amine and R1 is R or H. A solubilizing agent may be associated with the amine salt, examples being oil-soluble aliphatic alcohols and/or thiols which may be straight or branched chain, saturated or unsaturated, and which contain at least 6 carbon atoms and the fatty alcohols and their thiol analogues. The polyhydric alcohols used to form the esters of (b) may be water-soluble alkane polyols of from 2 to 6 carbon atoms, e.g. propylene glycol and mannitol; ether alcohols, e.g. triethylene glycol and hexitans such as mannitans which may be etherified with alkylene oxides or glycols; or sugars. The acids used to form the esters include saturated or unsaturated aliphatic mono- or polycarboxylic acids, cycloaliphatic carboxylic acids, aromatic carboxylic acids, aromatic sulphonic acids and higher alkane sulphonic acids. Optional ingredients mentioned are fatty acids of at least 12 carbon atoms, esters of these acids and waxes, and derivatives obtained from them by sulphurization, halogenation and/or polymerization, e.g. sulphurized and sulphochlorinated fats and fatty oils; anti-oxidants, e.g. alkyl phenols; corrosion inhibitors, e.g. mercaptobenzothiazole, nitrites, and 9 to 11 carbon fatty acids; and anti-form agents, e.g. silicone polymers, organic phosphates and aliphatic alcohols. A composition typical of several examples comprises: sulphurized oleic acid, glycerol mono-oleate, trichloromethane phosphonic acid, a commercial mixture of 12-15 carbon branchedchain primary amines and SAE 90 mineral oil. Specifications 505,016 [Group IV], 634,720, 637,389 and 689,872, [Group IV (b)], are referred to.
GB18809/56A 1955-06-20 1956-06-18 Lubricating oil compositions Expired GB798635A (en)

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US516784A US2882228A (en) 1955-06-20 1955-06-20 Metal working lubricants

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GB798635A true GB798635A (en) 1958-07-23

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US (1) US2882228A (en)
BE (1) BE548812A (en)
DE (1) DE1015169B (en)
FR (1) FR1154532A (en)
GB (1) GB798635A (en)
NL (2) NL102996C (en)

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Publication number Priority date Publication date Assignee Title
NL243555A (en) * 1958-09-22
DE1160967B (en) * 1960-06-15 1964-01-09 Shell Int Research lubricant
US3185728A (en) * 1960-06-20 1965-05-25 Texaco Inc Ethylene diamine salts of thiophosphonic acids
US3143506A (en) * 1960-06-20 1964-08-04 Texaco Inc Lubricants containing amine salts
US3243452A (en) * 1962-06-28 1966-03-29 Olin Mathieson Bis (hydroxydiarylphosphine) decaboranes
US3499923A (en) * 1965-09-07 1970-03-10 Universal Oil Prod Co Polychloroalkylphosphonic acid salts
US3635823A (en) * 1966-11-04 1972-01-18 Universal Oil Prod Co Synergistic composition and use thereof
US3793199A (en) * 1970-06-08 1974-02-19 Texaco Inc Friction reducing agent for lubricants
US3984599A (en) * 1973-10-30 1976-10-05 Exxon Research And Engineering Company Lubricant coating compositions for use in metal drawing operations
US4252660A (en) * 1979-11-23 1981-02-24 Mobil Oil Corporation Reaction products of organophosphorus halides with inorganic thiocyanates as load-carrying additives in lubricating oil compositions
US4615818A (en) * 1985-03-15 1986-10-07 The Lubrizol Corporation Hydrogen sulfide stabilized oil-soluble sulfurized organic compositions
US5092908A (en) * 1990-06-28 1992-03-03 Exxon Research And Engineering Company Composition for improving cold flow properties of middle distillates (OP-3571)
JPH08209172A (en) * 1994-11-15 1996-08-13 Lubrizol Corp:The Lubricant and fluid containing thiocarbomate and phosphonate
CA2195702C (en) * 1996-01-31 2005-11-22 Sumanth Addagarla Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke cycle engines
AU2002367816A1 (en) * 2001-08-14 2003-10-08 United Soy Bean Board Soy-based methyl ester high performance metal working fluids
US7439212B2 (en) 2001-09-05 2008-10-21 United Soybean Board Soybean oil based metalworking fluids

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CA471213A (en) * 1951-01-30 F. Schiermeier Knapel Corrosion inhibiting compositions
US1463092A (en) * 1921-07-07 1923-07-24 Technical Res Works Ltd Lubricant and process of preparing same
US2249800A (en) * 1936-04-24 1941-07-22 Du Pont Hydraulic fluid
US2531801A (en) * 1946-06-21 1950-11-28 Monsanto Chemicals Lubricating oil composition
US2515115A (en) * 1947-10-29 1950-07-11 Standard Oil Dev Co Nonfoaming compositions
US2479424A (en) * 1947-12-03 1949-08-16 Standard Oil Dev Co Rust inhibiting lubricants
US2587545A (en) * 1949-04-14 1952-02-26 Standard Oil Dev Co Rust-preventing lubricant
GB709903A (en) * 1950-04-06 1954-06-02 Standard Oil Dev Co Lubricating oil composition
US2683691A (en) * 1951-08-18 1954-07-13 Shell Dev Extreme pressure lubricants

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DE1015169B (en) 1957-09-05

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