USRE34459E - Friction modifier - Google Patents
Friction modifier Download PDFInfo
- Publication number
- USRE34459E USRE34459E US07/916,908 US91690892A USRE34459E US RE34459 E USRE34459 E US RE34459E US 91690892 A US91690892 A US 91690892A US RE34459 E USRE34459 E US RE34459E
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- US
- United States
- Prior art keywords
- succinimide
- carbon atoms
- weight
- composition according
- oil
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- 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
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Classifications
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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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
Definitions
- This invention relates to friction modifiers for use in lubricants and lubricant additives.
- Lubricants customarily in use in vehicles driven by internal combustion and other engines include additives designed to reduce engine friction and the fiction between other moving parts.
- One class of such friction reducing additives has been described in European Specification 0020037 in the name of Edwin Cooper Inc.
- the friction reducing additives of this specification comprise a compound having the structure ##STR1## wherein n is an integer from 2 to 4 and wherein Z has the structure R 1 R 2 CH-- wherein .[.R l .]. .Iadd.R 1 .Iaddend.and R 2 are each independently straight or branched chain hydrocarbon groups containing from 1 to 34 carbon atoms such that the total number of carbon atoms in the groups R 1 and R 2 is from 11 to 35.
- the radical Z may be, for example, 1-methylpentadecy, 1-propyltridecenyl, 1-pentyltridecenyl, 1-tridecylpentadecenyl, or 1-tetradecyleicosenyl.
- the above highly preferred additives are made from linear ⁇ -olefins containing from 12 to 36 carbon atoms by isomerizing the ⁇ -olefins to form a mixture of internal olefins and reacting this mixture of internal olefins with maleic acid, anhydride or ester forming an intermediate and reacting the intermediate with ammonia to form amide, imide, or mixtures thereof.
- Additives made from isomerized linear ⁇ -olefins have greatly improved oil solubility compared with additives made with linear ⁇ -olefins.
- Such friction reducing additives are useful in a wide variety of lubricants.
- One class of lubricants in which the above-mentioned friction reducing additives have been used is in lubricating oils for use in wet brake systems.
- Agricultural tractors and similar vehicles, e.g. off-highway vehicles have braking systems which run in the transmission oil of the back axle.
- the oil acts as a heat transfer medium to remove the large amounts of heat generated by braking.
- Such systems are however subject to the problem that the noise generated by braking may have an unacceptably high level.
- there is generally a level of brake pedal pressure above which the noise generated by the braking rapidly rises to an unacceptably high level e.g. over about 100 decibels.
- One function of the friction reducing additives included in the oils used in such braking systems is to maximise the brake pressure which can be used before excessive noise is generated.
- the friction reducing properties of the aforementioned additives may be surprisingly improved by using them in admixture with an oil-soluble saturated or unsaturated acid amide of 1 to 36 preferably 4 to 24 carbon atoms.
- This admixture may be used to enhance the friction reducing properties of lubricants in general, especially in tractor oils. These may be used as lubricants in a wide variety of parts of a tractor e.g. as crankcase lubricant to reduce fuel consumption.
- the admixture finds particular advantage in its use in a wet brake system.
- the present invention accordingly provides a friction reducing additive composition which comprises at least one compound having the structure ##STR2## wherein n and Z are as herein before defined, and, preferably in a ratio of 1:10 to 10:1, at least one oil-soluble acid amide of the formula ##STR3## in which each R, which may be the same or different, is hydrogen or alkyl or alkenyl of 1 to 35 carbon atoms, R 1 and R 2 are each hydrogen or alkyl or alkenyl of 1 to 23 carbon atoms or one of R 1 and .[.R 2 .]. .Iadd.R 2 .Iaddend. is hydrogen and the other is a group RCO-- in which R is as defined above.
- the acid amide is a linear or branched alkyl or alkenyl acid amide of general formula
- R 3 is alkyl or alkenyl of 3 to 23 carbon atoms, or preferably 7 to 21 carbon atoms. More preferably a saturated or unsaturated fatty acid amide of 8 to 20 carbon atoms is used.
- the first type of friction reducing additive is described in European Specification No. 0020037 whose disclosure is incorporated herein by reference.
- the oil-soluble acid amide may be derived from any natural of synthetic acid or mixture of acids although, as indicated above, a fatty acid is preferred.
- the fatty acid should preferably contain at least 8 carbon atoms per molecule, but amides containing more than 20 carbon atoms per molecule are relatively inaccessible and therefore less preferred.
- Amides based on linear saturated or mono-unsaturated fatty acids containing an even number of carbon atoms are easily available and their use is preferred. Specific examples are stearamide, oleylamide, palmitamide, especially oleylamide.
- the combination of friction reducing additives in accordance with the invention may be incorporated directly in a finished lubricant or, more usually, in an additive package including other constituents designed to improve the performance of the lubricant for distribution to manufacturers of the finished oil.
- the package usually contains also 0.5 to 20 wt. percent, preferably 1 to 5 wt. percent of a diluent oil such as a lubricating oil.
- Preferred lubricants in accordance with the invention contain from 0.1% to 2.0% by weight of the long chain succinimide derivative described above and 0.05 to 1% preferably 0.1 to 1% by weight of the long chain fatty acid .[.amide. The.]. .Iadd.amide, the .Iaddend.ratio of the succinimide derivative to the long chain amide being preferably in the range of 5:1 to 1:1 by weight.
- a lubricant composition containing no friction reducing additives was tested in a standard system in which brake pedal pressure is increased until the noise level produced by the brakes begins to rise sharply. If is found in practice that noise level rises only slowly up to a given pedal pressure and then rises steeply. For the oil without friction reducing additives, the pressure above which the noise level began to rise rapidly was only 30 pounds per square inch. If to the same oil is added 1.35% by weight of a succinimide derivative as described above, specifically one in which Z is an alkenyl group containing an average of 22 carbon atoms, the pedal pressure above which noise begins to rise sharply is increased to 70 pounds per square inch.
- a lubricant composition comprising a combination of friction reducing additives also typically comprises one or more, dispersant(s), detergent(s), antioxidant(s) and extreme pressure additives(s). Such additional additives must, of course, be compatible with the friction modifiers mentioned above and with each other.
- the lubricant may also contain as ashless dispersant and an alkaline earth metal salt of a petroleum sulfonic acid or an alkarly sulfonic acid (e.g. alkylbenzene sulfonic acid).
- an alkaline earth metal salt of a petroleum sulfonic acid or an alkarly sulfonic acid e.g. alkylbenzene sulfonic acid.
- the friction-reducing additives can be used in mineral oil or in synthetic oils of a suitable viscosity e.g. viscosity up to about 16 ⁇ 10 -3 m 2 /S (80 SUS) at 100° C. (210° F.).
- a suitable viscosity e.g. viscosity up to about 16 ⁇ 10 -3 m 2 /S (80 SUS) at 100° C. (210° F.).
- Mineral oils include those of suitable viscosity refined from crude oil from all sources including Gulfcoast, midcontienent, Pennsylvania, California, Alaska and the like. Various standard refinery operations can be used in processing the mineral oil.
- Synthetic oil includes both hydrocarbon synthetic oil and synthetic esters.
- Useful synthetic hydrocarbon oils including liquid polymers of ⁇ -olefins having the proper viscosity.
- the hydrogenated liquid oligomers of C 6 -C 12 ⁇ -olefins such as ⁇ -decene trimer.
- alkylbenzenes of proper viscosity can be used, such as didodecylbenzene.
- Useful synthetic esters include the esters of both monocarboxylic acid and polycarboxylic acid as well as monohydroxy alkanols and polyols. Typical examples are didodecyl adipate, trimethylol propane triperlargonate, pentaerythritol tetracaproate, di(2-ethylhexyl)adipate, and dilaurly sebacate.
- Complex esters prepared from mixtures of mono- and dicarboxylic acid and mono- and polyhydroxyl alkanols can also be used.
- Blends of mineral oil with synthetic oil are particularly useful. For example, blends of 5 to 25 weight percent hydrogenerated ⁇ -decene trimer with 75 to 95 weight percent 32 ⁇ 10 -3 m 2 /S(150 SUS 38° C.(100° F.)) mineral oil results in an excellent lubricant. Likewise, blends of about 5 to 25 weight percent di(2-ethylhexyl)adipate with mineral oil of proper viscosity results in a superior lubricating oil. Also blends of synthetic hydrocarbon oil with synthetic esters can be used. Blends of mineral oil with synthetic oil are especially useful when preparing low viscosity oil (e.g. SAE 5W 20) since they permit these low viscosities without contributing excessive volatility.
- low viscosity oil e.g. SAE 5W 20
- the more preferred lubricating oil compositions include zinc dihydrocarbyldithiophosphate (ZDDP) in combination with the present additives.
- ZDDP zinc dihydrocarbyldithiophosphate
- Both zinc dialkydithiophosphates and zinc dialkaryldithiophosphates as well as mixed alkyl-aryl dithiophosphates can be used.
- alkyl-type ZDDP are those in which the hydrocarbyl groups are a mixture of isobutyl and isoamyl alkyl groups.
- Zinc di(nonylphenyl)-dithiophosphate is an example of an aryl-type ZDDP.
- Good results are achieved using sufficient zinc dihydrocarbyldithiophosphate to provide about 0.01 to 0.5 weight percent zinc.
- a preferred concentration supplies about 0.05 to 0.3 weight percent zinc.
- Another additive which may be used in the oil composition is an alkaline earth metal petroleum sulfonate or alkaline earth metal alkaryl aulfonate.
- alkaline earth metal petroleum sulfonate or alkaline earth metal alkaryl aulfonate examples are calcium petroleum sulfonates, magnesium petroleum sulfonates, barium alkarly sufonates, calcium alkaryl sulfonates or magnesium alkarly sulfonates.
- Both the neutral and the overbased sulfonates having base numbers of up to about 400 can be beneficially used. These are used in an amount to provide about 0.05 to 1.5 weight percent alkaline earth metal and more preferably about 0.1 to 1.0 weight percent.
- crankcase oils also contain an ashless dispersant such as a polyolefin succinamide or succinimide of a polyethylene polyamine such as tetraethylenepentamine.
- the polyolefin succinic substituent is preferably a polyisobutene group having a molecular weight of from about 800 to 5,000.
- Such ashless dispersants are more fully described in U.S. Pat. Nos. 3,172,892 and 3,219,666.
- ashles dispersants include the Mannich condensation products of polyolefine substituted phenols, formaldehyde and polyethylene polyamine.
- the polyolefin phenol is a polyisobutylene-substituted phenol in which the polyisobutylene group has a molecular weight of from about 800 to 5,000.
- the preferred polyethylene polyamine is tetracethylene pentamine.
- antioxidants such as alkyl phenols, sulphurised alkyl phenols and alkyl aromatic amines, particularly hindered alkyl phenols.
- Viscosity index improvers, pour point depressants and antifoamants are examples of other additives which may also be present.
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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
Description
R.sup.3 --CO--NH.sub.2
Claims (9)
R.sup.3 --CO--NH.sub.2
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/916,908 USRE34459E (en) | 1989-03-20 | 1992-07-20 | Friction modifier |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8906345 | 1989-03-20 | ||
GB898906345A GB8906345D0 (en) | 1989-03-20 | 1989-03-20 | Friction modifier |
US07/487,779 US5021176A (en) | 1989-03-20 | 1990-03-05 | Friction modifier |
US07/916,908 USRE34459E (en) | 1989-03-20 | 1992-07-20 | Friction modifier |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/487,779 Reissue US5021176A (en) | 1989-03-20 | 1990-03-05 | Friction modifier |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE34459E true USRE34459E (en) | 1993-11-30 |
Family
ID=27264374
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/916,908 Expired - Lifetime USRE34459E (en) | 1989-03-20 | 1992-07-20 | Friction modifier |
Country Status (1)
Country | Link |
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US (1) | USRE34459E (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5767045A (en) * | 1995-12-01 | 1998-06-16 | Ethyl Petroleum Additives Limited | Hydraulic fluids |
US6165952A (en) | 1999-04-05 | 2000-12-26 | King Industries, Inc. | Ashless rust inhibitor lubricant compositions |
US6588393B2 (en) | 2000-09-19 | 2003-07-08 | The Lubrizol Corporation | Low-sulfur consumable lubricating oil composition and a method of operating an internal combustion engine using the same |
US20060264340A1 (en) * | 2005-05-20 | 2006-11-23 | Iyer Ramnath N | Fluid compositions for dual clutch transmissions |
US20090005275A1 (en) * | 2007-06-28 | 2009-01-01 | Chevron U.S.A. Inc. | Power steering fluid |
US8557752B2 (en) | 2005-03-23 | 2013-10-15 | Afton Chemical Corporation | Lubricating compositions |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3764536A (en) * | 1971-10-14 | 1973-10-09 | Texaco Inc | Overbased calcium salts of alkenylsuccinimide |
US3894958A (en) * | 1973-11-05 | 1975-07-15 | Texaco Inc | Mixed secondary alkyl amide synthetic lubricant compositions |
US4048080A (en) * | 1976-06-07 | 1977-09-13 | Texaco Inc. | Lubricating oil composition |
US4151101A (en) * | 1977-12-23 | 1979-04-24 | Stauffer Chemical Company | Method and composition for controlling foam in non-aqueous fluid systems |
US4204970A (en) * | 1978-12-07 | 1980-05-27 | Standard Oil Company (Indiana) | Lubricant compositions containing alkylated aromatic amino acid antioxidants |
US4303535A (en) * | 1980-05-12 | 1981-12-01 | Texaco Inc. | Hydrocarbyl carbamidopropanamide, its method of preparation and lubricating oil composition containing same |
US4371446A (en) * | 1979-11-15 | 1983-02-01 | Hirotsugu Kinoshita | Lubricant |
EP0020037B1 (en) * | 1979-05-18 | 1984-08-15 | Edwin Cooper Inc. | Oil-soluble friction-reducing additive, process for the preparation thereof, and lubricating oil or fuel composition containing the additive |
US4482464A (en) * | 1983-02-14 | 1984-11-13 | Texaco Inc. | Hydrocarbyl-substituted mono- and bis-succinimide having polyamine chain linked hydroxyacyl radicals and mineral oil compositions containing same |
US4521318A (en) * | 1983-11-14 | 1985-06-04 | Texaco Inc. | Lubricant compositions containing both hydrocarbyl substituted mono and bissuccinimide having polyamine chain linked hydroxacyl radicals, and neopentyl derivative |
US4839073A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate and substituted acetate adducts as compatibilizer additives in lubricating oil compositions |
US4839071A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions |
US4839072A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts |
-
1992
- 1992-07-20 US US07/916,908 patent/USRE34459E/en not_active Expired - Lifetime
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3764536A (en) * | 1971-10-14 | 1973-10-09 | Texaco Inc | Overbased calcium salts of alkenylsuccinimide |
US3894958A (en) * | 1973-11-05 | 1975-07-15 | Texaco Inc | Mixed secondary alkyl amide synthetic lubricant compositions |
US4048080A (en) * | 1976-06-07 | 1977-09-13 | Texaco Inc. | Lubricating oil composition |
US4151101A (en) * | 1977-12-23 | 1979-04-24 | Stauffer Chemical Company | Method and composition for controlling foam in non-aqueous fluid systems |
US4204970A (en) * | 1978-12-07 | 1980-05-27 | Standard Oil Company (Indiana) | Lubricant compositions containing alkylated aromatic amino acid antioxidants |
EP0020037B1 (en) * | 1979-05-18 | 1984-08-15 | Edwin Cooper Inc. | Oil-soluble friction-reducing additive, process for the preparation thereof, and lubricating oil or fuel composition containing the additive |
US4371446A (en) * | 1979-11-15 | 1983-02-01 | Hirotsugu Kinoshita | Lubricant |
US4303535A (en) * | 1980-05-12 | 1981-12-01 | Texaco Inc. | Hydrocarbyl carbamidopropanamide, its method of preparation and lubricating oil composition containing same |
US4482464A (en) * | 1983-02-14 | 1984-11-13 | Texaco Inc. | Hydrocarbyl-substituted mono- and bis-succinimide having polyamine chain linked hydroxyacyl radicals and mineral oil compositions containing same |
US4521318A (en) * | 1983-11-14 | 1985-06-04 | Texaco Inc. | Lubricant compositions containing both hydrocarbyl substituted mono and bissuccinimide having polyamine chain linked hydroxacyl radicals, and neopentyl derivative |
US4839073A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate and substituted acetate adducts as compatibilizer additives in lubricating oil compositions |
US4839071A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions |
US4839072A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5767045A (en) * | 1995-12-01 | 1998-06-16 | Ethyl Petroleum Additives Limited | Hydraulic fluids |
US6165952A (en) | 1999-04-05 | 2000-12-26 | King Industries, Inc. | Ashless rust inhibitor lubricant compositions |
US6588393B2 (en) | 2000-09-19 | 2003-07-08 | The Lubrizol Corporation | Low-sulfur consumable lubricating oil composition and a method of operating an internal combustion engine using the same |
US8557752B2 (en) | 2005-03-23 | 2013-10-15 | Afton Chemical Corporation | Lubricating compositions |
US20060264340A1 (en) * | 2005-05-20 | 2006-11-23 | Iyer Ramnath N | Fluid compositions for dual clutch transmissions |
US20090005275A1 (en) * | 2007-06-28 | 2009-01-01 | Chevron U.S.A. Inc. | Power steering fluid |
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