US3637500A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

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Publication number
US3637500A
US3637500A US55967A US5596770A US3637500A US 3637500 A US3637500 A US 3637500A US 55967 A US55967 A US 55967A US 5596770 A US5596770 A US 5596770A US 3637500 A US3637500 A US 3637500A
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US
United States
Prior art keywords
disulphide
diester
composition
butyl
diethyl
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 - Lifetime
Application number
US55967A
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English (en)
Inventor
Eric Simon Forbes
Keith George Allum
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BP PLC
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BP PLC
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Publication of US3637500A publication Critical patent/US3637500A/en
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Classifications

    • CCHEMISTRY; METALLURGY
    • 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
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11Complex polyesters
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11Complex polyesters
    • C10M2209/111Complex polyesters having dicarboxylic acid centres
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11Complex polyesters
    • C10M2209/112Complex polyesters having dihydric acid centres
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/083Dibenzyl sulfide
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof

Definitions

  • This invention relates to improvements in lubricating compositions; in particular it relates to lubricating compositions BACKGROUND OF THE INVENTION
  • load-carrying additives may be divided into two classes, namely antiwear and extreme pressure additives.
  • load-carrying additives When two lubricated moving surfaces are lightly loaded against each other, they are separated by an elastohydrodynamic oil film: as the load increases so the oil film thickness decreases.
  • antiwear additives function by improving the oil film strength and thus reducing intermetallic contact.
  • Extreme pressure additives function in this region by reacting with the metal surface to form an inorganic iron compound, such as iron sulphide, which prevents welding of the metal surfaces.
  • This invention therefore, provides an improved lubricating composition based on a mineral base oil and which contains up to 20 percent by weight of an ester and up to 20 percent by weight of a load-carrying additive.
  • the ester is a polyester containing two ester linkages per molecule, i.e., a diester.
  • the most preferred diesters are those which are liquids or low melting solids.
  • Suitable diesters are the compounds of the general formula AOOC-R-COOB Formula I wherein R represents a saturated hydrocarbon, i.e., alkylene, group having from 1 to 25 carbon atoms or a phenylene group and A and B are the sameor different and represent alkyl groups, each group containing from I to 10 carbon atoms, for example, diethyl sebacate. v
  • diesters of Formula I are di-alkyl octadecanl,l8-dioate, di-alkyl-tetracosane-l,24-dioate, di-alkyl phthalate, di-alkyl adipate and di-alkyl sebacate, each of the alkyl groups containing from I to 10 carbon atoms.
  • the load-carrying additive is an organic disulphide
  • the lubricating composition preferably contains 0.l to 10 percent by weight of the ester and 0.1 to 10 percent by weight of the disulphide.
  • E and F are the same or different and represent alkyl, cycloalkyl, aryl, alkaryl or aralkyl groups, each of which may possibly be substituted by ester groups, and wherein at least one of E and F contains up to 20 carbon atoms.
  • E and F are alkyl, cycloalkyl, aryl or alkaryl groups containing up to 10 carbon atoms each.
  • Suitable disulphides include di-n-butyl disulphide, di-cyclohexyl disulphide, 2,2'-(dicarboethoxy)diethyl disulphide, diphenyl disulphide and dibenzyl disulphide.
  • the mineral oil used depends on the use to which it is to be put and any lubricating oil can be used.
  • the lubricating composition according to the invention can also contain, if desired, other additives, for example, dispersants, detergents, viscosity index improvers, oxidation and corrosion inhibitors and pour point depressants.
  • additives for example, dispersants, detergents, viscosity index improvers, oxidation and corrosion inhibitors and pour point depressants.
  • the lubricating compositions according to the invention can be used to lubricate, for example, automotive crankcases and transmission systems.
  • the invention also relates to a method of operating machinery wherein a lubricating composition based on a mineral base oil and which contains up to 20 percent by weight of an ester and up to 20 percent by weight of a load-carrying additive is used as the lubricant.
  • the antiwear test was carried out under a load of l 5 kg; at a running speed of 1,500 revolutions per minute, and wear scars on the balls were measured after 30, 45 and minutes, respectively.
  • compositions Nos. 2-9 of the table composition No. 2 being considerably worse than No. 3 and worse than any of the other results.
  • composition No. 31 it can be seen that the antiwear performance of the ester plus base oil composition at a 10 percent concentration of ester is worse than that of the base oil alone.
  • di-n-butyldisulnearly equal total concentrations of additives are below the levels attained with the corresponding blends containing either component alone.
  • compositions Nos. 40 and 41 the blend of diethyl adipate and base oil has worse antiwear performance than the base oil alone, as has the disulphide alone, compositions Nos. 10-13, yet when they are mixed together, they bring about a marked improvement in wear resistance.
  • a lubricating composition which comprises i. a mineral oil in major amount;
  • compositions Nos. 10-13 leads to conmula siderably worse antiwear performance than the base oil at all AOOCR--COOB 322 2233283252? though it is known to have extreme wherein R is a saturated alkylene group of from 1 to 25 carbon atoms or a phen lene grou and Thus It can be .concluded that composmon for ex- A and B, independently, a re alkyl of from 1 to 10 carbon ample, has an antiwear performance unexpectedly better than atoms and h beStdieter/b2.1se comPgsition. and better than the g iii.
  • organic disulphide load di-n-butyl disulphide COmPOSIIIOIL IIlS unexpected to find th s carrying additive, Said organic disulphide being of the degree of performance because it 18 not possible to obtain general formula such low antiwear results using any amount of diethyl sebacate or di-n-butyl disulphide by themselves.
  • a lubricating composition which comprises i. a mineral oil in major amount;
  • a diester selected from di-alkyloctadecan-l,l 8-dioate, di-alkyl tetracosanel ,24-dioate, di-alkyl phthalate, di-alkyl adipate or di-alkyl sebacate, each of the alkyl groups containing from I to 10.
  • an organic disulphide selected from di-n-butyl disulphide, di-cyclohexyl disulphide, diphenyl disulphide, dibenzyl disulphide or 2,2- (dicarboethoxy)-diethyl disulphide.
  • composition as defined in claim 2 wherein said diester is diethyl sebacate and said disulphide is di-cyclohexyl disulphide.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US55967A 1967-01-31 1970-07-17 Lubricating compositions Expired - Lifetime US3637500A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4581/67A GB1210811A (en) 1967-01-31 1967-01-31 Improvements in lubricating compositions

Publications (1)

Publication Number Publication Date
US3637500A true US3637500A (en) 1972-01-25

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US55967A Expired - Lifetime US3637500A (en) 1967-01-31 1970-07-17 Lubricating compositions

Country Status (6)

Country Link
US (1) US3637500A (es)
BE (1) BE710139A (es)
DE (1) DE1644868A1 (es)
FR (1) FR1551748A (es)
GB (1) GB1210811A (es)
NL (1) NL6801192A (es)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4218331A (en) * 1978-07-24 1980-08-19 Gulf Research & Development Company Extreme pressure lubricating compositions
US4902438A (en) * 1987-05-12 1990-02-20 Bp Chemicals Limited Lubricating oil compositions containing anti-wear/extreme pressure additives
EP0763590A1 (en) * 1994-05-24 1997-03-19 Idemitsu Kosan Company Limited Cutting or grinding fluid composition
US6599868B2 (en) * 2000-10-13 2003-07-29 Infineum International Ltd. Lubricating oil compositions
US6649576B2 (en) * 2001-06-15 2003-11-18 Infineum International Inc. Lubricating oil compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1047493A (es) * 1963-01-30
US2110281A (en) * 1934-03-31 1938-03-08 Standard Oil Co Pure compounds as extreme-pressure lubricants
US2744070A (en) * 1952-12-22 1956-05-01 Continental Oil Co Soluble cutting oil
US3337457A (en) * 1964-02-11 1967-08-22 Exxon Research Engineering Co Crankcase lubricants comprising a mineral and synthetic ester oil blend

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2110281A (en) * 1934-03-31 1938-03-08 Standard Oil Co Pure compounds as extreme-pressure lubricants
US2744070A (en) * 1952-12-22 1956-05-01 Continental Oil Co Soluble cutting oil
GB1047493A (es) * 1963-01-30
US3337457A (en) * 1964-02-11 1967-08-22 Exxon Research Engineering Co Crankcase lubricants comprising a mineral and synthetic ester oil blend

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4218331A (en) * 1978-07-24 1980-08-19 Gulf Research & Development Company Extreme pressure lubricating compositions
US4902438A (en) * 1987-05-12 1990-02-20 Bp Chemicals Limited Lubricating oil compositions containing anti-wear/extreme pressure additives
EP0763590A1 (en) * 1994-05-24 1997-03-19 Idemitsu Kosan Company Limited Cutting or grinding fluid composition
EP0763590A4 (en) * 1994-05-24 1999-04-21 Idemitsu Kosan Co CUTTING OR GRINDING COMPOSITION
US6599868B2 (en) * 2000-10-13 2003-07-29 Infineum International Ltd. Lubricating oil compositions
US6649576B2 (en) * 2001-06-15 2003-11-18 Infineum International Inc. Lubricating oil compositions

Also Published As

Publication number Publication date
BE710139A (es) 1968-07-31
NL6801192A (es) 1968-08-01
GB1210811A (en) 1970-11-04
FR1551748A (es) 1968-12-27
DE1644868A1 (de) 1971-04-29

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