US3637500A - Lubricating compositions - Google Patents
Lubricating compositions Download PDFInfo
- 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
- Authority
- 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
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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/30—Complex 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
-
- 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
- C10M2207/28—Esters
- C10M2207/30—Complex 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
- C10M2207/302—Complex 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
-
- 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
- C10M2207/28—Esters
- C10M2207/30—Complex 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
- C10M2207/304—Complex 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
-
- 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid 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
- 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
- C10M2209/11—Complex polyesters
-
- 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
- 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
- C10M2209/11—Complex polyesters
- C10M2209/111—Complex polyesters having dicarboxylic acid centres
-
- 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
- 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
- C10M2209/11—Complex polyesters
- C10M2209/112—Complex polyesters having dihydric acid centres
-
- 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
-
- 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
- C10M2219/083—Dibenzyl sulfide
-
- 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
- C10M2219/085—Thiols; 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.
Landscapes
- 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)
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 |
Family
ID=9779865
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US55967A Expired - Lifetime US3637500A (en) | 1967-01-31 | 1970-07-17 | Lubricating compositions |
Country Status (6)
Country | Link |
---|---|
US (1) | US3637500A (fr) |
BE (1) | BE710139A (fr) |
DE (1) | DE1644868A1 (fr) |
FR (1) | FR1551748A (fr) |
GB (1) | GB1210811A (fr) |
NL (1) | NL6801192A (fr) |
Cited By (5)
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 (fr) * | 1994-05-24 | 1997-03-19 | Idemitsu Kosan Company Limited | Huile de coupe et de meulage |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1047493A (fr) * | 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 |
-
1967
- 1967-01-31 GB GB4581/67A patent/GB1210811A/en not_active Expired
-
1968
- 1968-01-23 FR FR1551748D patent/FR1551748A/fr not_active Expired
- 1968-01-24 DE DE19681644868 patent/DE1644868A1/de active Pending
- 1968-01-26 NL NL6801192A patent/NL6801192A/xx unknown
- 1968-01-31 BE BE710139A patent/BE710139A/xx unknown
-
1970
- 1970-07-17 US US55967A patent/US3637500A/en not_active Expired - Lifetime
Patent Citations (4)
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 (fr) * | 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)
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 (fr) * | 1994-05-24 | 1997-03-19 | Idemitsu Kosan Company Limited | Huile de coupe et de meulage |
EP0763590A4 (fr) * | 1994-05-24 | 1999-04-21 | Idemitsu Kosan Co | Huile de coupe et de meulage |
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 (fr) | 1968-07-31 |
GB1210811A (en) | 1970-11-04 |
DE1644868A1 (de) | 1971-04-29 |
NL6801192A (fr) | 1968-08-01 |
FR1551748A (fr) | 1968-12-27 |
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