GB700804A - Lubricating oil compositions - Google Patents

Lubricating oil compositions

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Publication number
GB700804A
GB700804A GB12063/50A GB1206350A GB700804A GB 700804 A GB700804 A GB 700804A GB 12063/50 A GB12063/50 A GB 12063/50A GB 1206350 A GB1206350 A GB 1206350A GB 700804 A GB700804 A GB 700804A
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GB
United Kingdom
Prior art keywords
acids
selenide
selenium
alkyl
metal salts
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
GB12063/50A
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.)
California Research LLC
Original Assignee
California Research LLC
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Filing date
Publication date
Application filed by California Research LLC filed Critical California Research LLC
Publication of GB700804A publication Critical patent/GB700804A/en
Expired legal-status Critical Current

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    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2207/027—Neutral 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
    • 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
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    • 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
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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    • 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
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    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • 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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2209/102—Polyesters
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/044—Polyamides
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/045—Polyureas; Polyurethanes
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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    • 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
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    • 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
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
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    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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    • 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—Semi-solids; greasy
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

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

Abstract

A lubricant (see Group III) comprises an oxidizable synthetic hydrocarbon lubricating oil which may be polymeric and a minor proportion, sufficient to inhibit oxidative deterioration of the oil, of a substance of the general formula R - (X)n - (Y) m - R1 wherein R and R1 are like or unlike organic radicles of which at least one contains not less than 8 carbon atoms, X is selenium or tellurium, Y is oxygen, sulphur selenium or tellurium, m is zero or an integer, n is an integer, and a non-benzenoid carbon atom in each of radicles R and R1 is connected directly to the appropriate X or Y atom of the formula. The lubricating oils mentioned include (a) polyesters such as the linear condensation products of dimers of unsaturated vegetable oil fatty acids with organic dihydroxy compounds, (b) polyamides obtained by condensing dimers of unsaturated vegetable oil fatty acids with diamines or hydroxyamines and (c) polyoxyalkylene glycols or their ester, ether or ester-ether derivatives. The lubricants may contain additional ingredients such as metal salts of organo substituted phosphates, metal salts of phenols, metal salts of organo substituted acids of boron, sulphur and arsenic, metal salts of carboxylic acids and rust inhibitors, especially the higher alkyl acid esters of polybasic aliphatic acids. In the examples, lubricants consist of (i) polymerized propylene oxide lubricating oil and dilauryl selenide, with or without zinc dibutyl dithiocarbonate or zinc dithiocarbonates of reduced cyclic petroleum nitrogen bases, (ii) propylene oxide - isobutylene oxide -1- butylene oxide copolymer lubricating oil and dilauryl selenide and (iii) acetylated polymer of propylene oxide, mineral oil and dilauryl selenide. For comparison purposes, lubricants are described consisting of (iv) propylene oxide polymer and dicetyl sulphide, with or without calcium cetyl phosphate and (v) the copolymer of (ii) and hexadecyl trisulphide. Specification 649,976, [Group III], is referred to.ALSO:Substances of the general formula R-(X)n-(Y)m-R1, wherein R and R1 are like or unlike organic radicles of which at least one contains not less than 8 carbon atoms, X is selenium or tellurium, Y is oxygen, sulphur, selenium or tellurium, m is zero or an integer, n is an integer, and a non-benzenoid carbon atom in each of radicles R and R1 is connected directly to the appropriate X or Y atom of the formula, are employed as lubricant additives (see Group III). Radicles R and R1 may be straight or branched chain alkyl groups, straight or branched chain unsaturated aliphatic groups, or cycloalkyl or other cycloaliphatic groups. Radicles R and R1 may contain aromatic groups, such as phenyl, hydroxyphenyl or aminophenyl groups, and non-hydrocarbon groups or atoms, such as chlorine and bromine atoms, hydroxyl, ether, keto, amino, free carboxyl, metal substituted carboxyl, esterified carboxyl, mercapto, mercaptide and monodi- or poly-sulphide groups. Substances specified may be classified as normal or branched chain alkyl monoselenides, alkyl monoselenides bearing non-hydrocarbon substituents in the alkyl groups (e.g. bis (b -chlorocetyl) selenide and bis (b -hydroxy cetyl) selenide), alkyl diselenides, alkyl mono- and di-tellurides, the various mono- and polyselenides and mono- and poly-tellurides prepared by reacting sodium or other alkali metal mono- or poly-selenides or mono- or poly-tellurides with halogenated hydrocarbons such as alkyl chlorides, chlorinated hydrocarbon lubricating oil and chlorinated hydrocarbon wax, diparaffin sulphoselenide prepared by condensing chlorinated paraffin wax with the product of dissolving selenium in aqueous or alcoholic sodium sulphide or polysulphide, dilauryl selenoxide. Suitable methods of preparing these selenides and tellurides are as follows:-(1) by condensation of aliphatic halides with metal selenides, tellurides, polyselenides or polytellurides, (2) by condensation of metal selenomercaptides or telluromercaptides with halogenated hydrocarbons, (3) by oxidation of selenomercaptans, (4) by action of caustic alkali on aliphatic selenocyanates and (5) by heating aliphatic or aryl-substituted aliphatic monoselenides with selenium. In examples, (a) dicetyl selenide is prepared by condensing normal cetyl chloride with sodium selenide in ethyl alcohol solution, (b) dicetyl telluride is prepared by condensing normal cetyl chloride with sodium telluride in ethyl alcohol solution, (c) dilauryl diselenide is prepared by the action of caustic soda on lauryl selenocyanate and (d) dioctadecyl diselenide is prepared by condensing sodium diselenide with octadecyl chloride. Specification 649,976 is referred to.ALSO:A lubricant comprises an oxidizable synthetic non-hydrocarbon lubricating oil and a minor proportion, sufficient to inhibit oxidative deterioration of the oil, of a substance of the general formula R-(X)n-(Y)m-R4, wherein R and R1 are like or unlike organic radicles of which at least one contains not less than 8 carbon atoms, X is selenium or tellurium, Y is oxygen, sulphur, selenium or tellurium, m is zero of an integer, n is an integer, and a non-benzenoid carbon atom in each of radicles R and R1 is connected directly to the appropriate X or Y atom of the formula. The preparation of such substances is described (see Group IV(b)). The lubricating oils may be polymeric (see Group IV(a)) and oils mentioned are (a) polyesters such as the linear condensation products of dimers of unsaturated vegetable oil fatty acids with organic dihydroxy compounds and the polymers of esterfied unsaturated dicarboxylic acids, (b) polyamides obtained by condensing dimers of unsaturated vegetable oil fatty acids with diamines or hydroxyamines, (c) polyoxyalkylene glycols or their ester, ether or ester-ether derivatives, (d) alkyl diesters of dicarboxylic acids and (e) thioethers such as bis (gamma-2-ethyl-hexyl-oxypropyl) sulphide. The lubricants may contain additional ingredients such as metal salts of organo substituted phosphates, metal salts of phenols (especially polyvalent metal salts of higher alkyl phenols), metal salts of organo substituted acids of boron, sulphur and arsenic (particularly calcium, magnesium, zinc, cadmium or aluminium salts of aryl sulphonic acids or petroleum sulphonic acids), metal salts of carboxylic acids (such as salts of aryl carboxylic acids, fatty acids and substituted aliphatic mono- and polycarboxylic acids containing nonhydrocarbon substituents; specific salts mentioned are calcium cetyl oxalate, calcium cetyl citrate, magnesium alpha hydroxy stearate and magnesium tartrate), rust inhibitors (especially the higher alkyl acid esters of polybasic aliphatic acids such as lauryl acid maleate and mono-or dicetyl citrate). The lubricants may be crankcase oils, especially for use under heavy load, turbine oils or cutting oils. In the examples, lubricants consist of (i) polymerized propylene oxide lubricating oil and dilauryl selenide, with or without zinc dibutyl dithiocarbamate or zinc dithiocarbamates of reduced cyclic petroleum nitrogen bases, (ii) propylene oxide-isobutylene oxide- 1-butylene oxide copolymer lubricating oil and dilauryl selenide and (iii) acetylated polymer of propylene oxide, mineral oil and dilauryl selenide. For comparison purposes, lubricants are described consisting of (iv) propylene oxide polymer and dicetyl sulphide, with or without calcium cetyl phosphate and (v) the copolymer of (ii) and hexadecyl trisulphide. Specification 649,976 is referred to.
GB12063/50A 1949-06-18 1950-05-15 Lubricating oil compositions Expired GB700804A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1003901B (en) * 1955-04-25 1957-03-07 Bataafsche Petroleum Grease
DE1054196B (en) * 1955-05-18 1959-04-02 Bayer Ag Additives to lubricants and metalworking agents
DE1063739B (en) * 1956-05-14 1959-08-20 Wakefield & Co Ltd C C Neutral ester based lubricants
DE1234348B (en) * 1954-02-09 1967-02-16 Douglas Aircraft Co Inc lubricant

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1234348B (en) * 1954-02-09 1967-02-16 Douglas Aircraft Co Inc lubricant
DE1003901B (en) * 1955-04-25 1957-03-07 Bataafsche Petroleum Grease
DE1054196B (en) * 1955-05-18 1959-04-02 Bayer Ag Additives to lubricants and metalworking agents
DE1063739B (en) * 1956-05-14 1959-08-20 Wakefield & Co Ltd C C Neutral ester based lubricants

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