EP1828359A1 - Method of friction control - Google Patents
Method of friction controlInfo
- Publication number
- EP1828359A1 EP1828359A1 EP05853776A EP05853776A EP1828359A1 EP 1828359 A1 EP1828359 A1 EP 1828359A1 EP 05853776 A EP05853776 A EP 05853776A EP 05853776 A EP05853776 A EP 05853776A EP 1828359 A1 EP1828359 A1 EP 1828359A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- crankcase
- lubricating composition
- lubricating
- clutch
- 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.)
- Ceased
Links
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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/12—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
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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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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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
- 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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- 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
- 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
- C10M2223/045—Metal containing thio derivatives
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
- C10M2227/062—Cyclic esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/14—Chemical after-treatment of the constituents of the lubricating composition by boron or a compound containing boron
Definitions
- the present invention relates to a method of friction control by lubricating an internal combustion engine comprising a crankcase and at least one of a gear and a wet-clutch with a lubricating composition.
- lubricant universally compatible with two-stroke and/or four-stroke internal combustion engines.
- the lubricants generally contain a number of different performance additives that are not necessarily designed for application in e.g. a four-stroke motorcycle engine where crankcase oil viscosity is required whilst also requiring properties compatible with extreme pressures and temperatures associated with a gearbox, transmission or clutch. Consequently many additives have properties that adversely effect engine performance or fuel economy.
- Kasai et al. 2003 JSAE/SAE International Spring Fuels & Lubricants Meeting, Yokohama, Japan, May 19-22, 2003, Paper title Effect of Engine Oil Additives on Motorcycle Clutch System (SAE2003-01-1956 or JSAE 20030105) discloses borated dispersant in combination with detergents or zinc dithiophosphate as being suitable for friction control.
- Kasai et al. further states that engine oils containing friction modifiers cannot be applied in a 4-stroke motorcycle engine because they decrease clutch capacity.
- US Patent 6,525,004 discloses a composition containing a borated hydrocarbyl succinimide dispersant and a phosphorus compound for use in 2- cycle and small engine four-cycle engines.
- the present invention provides a method of lubricating an internal combustion engine whilst imparting friction control.
- This invention provides a method of lubricating an internal combustion engine comprising a crankcase and at least one of a gear and a wet- clutch, said method comprising supplying to said crankcase and at least one of the gear and wet-clutch a lubricating composition comprising: (a) an oil of lubricating viscosity; (b) a boron containing compound; and (c) a friction modifier.
- This invention provides a method of lubricating an internal combustion engine comprising a crankcase and at least one of a gear and a wet- clutch, said method comprising supplying to said crankcase and at least one of the gear and wet-clutch a lubricating composition comprising: (a) an oil of lubricating viscosity; (b) a boron containing compound; and (c) a friction modifier.
- the internal combustion engine of the invention comprises a crankcase, a gear and a wet-clutch.
- the internal combustion engine further comprises a manual or automatic transmission.
- the gear is from a gearbox.
- wet-clutch is known to a person skilled in the art as meaning one that contains a clutch plate(s) that is bathed or sprayed by a lubricant, e.g., that of the transmission, and the lubricating oil gets between the plate(s).
- the internal combustion engine has a common oil reservoir supplying the same lubricating composition to the crankcase and at least one of a gear and a wet-clutch.
- the lubricating composition is supplied to the crankcase and to the gear (or multiplicity of gears), or to the crankcase and the wet clutch, or to the crankcase and both the gear (or gears) and the wet clutch.
- the internal combustion engine is a 4-stroke engine. In one embodiment the internal combustion engine is also referred to generically as a small engine.
- the small engine in one embodiment has a power output of 2.24 to 18.64 kW (3 to 25 horsepower (hp)), in another embodiment 2.98 to 4.53 kW (4 to 6 hp) and in another embodiment exhibits 100 or 200 cm 3 displacement.
- small engines include those in home/garden tools such as lawnmowers, hedge trimmers, chainsaws, snow blowers or roto-tillers.
- the internal combustion engine has a capacity of up to 3500 cm 3 displacement, in another embodiment up to 2500 cm 3 displacement and in another embodiment up to 2000 cm 3 displacement. Examples of suitable internal combustion engines with a capacity up to 2500 cm 3 displacement include motorcycles, snowmobiles, jet-skis, quad-bikes, or all- terrain vehicles.
- the internal combustion engine is a tractor or other agricultural vehicle such as a combined harvester.
- the internal combustion engine is not a tractor or other agricultural vehicle.
- the internal combustion engine does not contain a dry-clutch i.e. a system that separates the engine from the transmission such as a transmission on an automotive vehicle.
- the internal combustion engine is not suitable for use with a diesel fuel.
- the internal combustion engine is a 4-stroke engine. In one embodiment the internal combustion engine is suitable for motorcycles for example motorcycles with a 4-stroke internal combustion engine.
- the lubricating composition includes natural or synthetic oils of lubricating viscosity; oil derived from hydrocracking, hydrogenation or hydrofinishing; and unrefined, refined and re-refined oils, and mixtures thereof.
- Natural oils include animal oils, vegetable oils, mineral oils and mixtures thereof.
- Synthetic oils include hydrocarbon oils, silicon-based oils, and liquid esters of phosphorus-containing acids. Synthetic oils may be produced by Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid oils.
- the polymer composition of the present invention is useful when employed in a gas-to-liquid oil. Often Fischer-Tropsch hydrocarbons or waxes may be hydroisomerised.
- the base oil is a polyalphaolefin (PAO) including a PAO-2, PAO-4, PAO-5, PAO-6, PAO-7 or PAO-8 (the numerical value relating to Kinematic Viscosity at 100 0 C).
- PAO polyalphaolefin
- the polyalphaolefin in one embodiment is prepared from dodecene and in another embodiment from decene.
- Oils of lubricating viscosity may also be defined as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
- the oil of lubricating viscosity comprises an API Group I, II,
- oil of lubricating viscosity is a Group III or IV base oil and in another embodiment a Group IV base oil. If the oil of lubricating viscosity is an API Group II, III, IV, V or VI oil there may be up to about 40 wt % and in another embodiment up to a maximum of about 5 wt % of the lubricating oil an API Group I oil present.
- the lubricating composition has a SAE viscosity grade from XW-Y, wherein X is an integer from 0 to 20 and Y is an integer from
- X is an integer chosen from 0, 5, 10, 15 or 20.
- Y is an integer chosen from 20, 25, 30, 35, 40, 45 or 50.
- the oil of lubricating viscosity in one embodiment is present from 40 wt % to 99.98 wt % of the lubricating composition, in another embodiment from
- the boron containing compound of the invention includes a borate ester, a borate alcohol, a borated dispersant or mixtures thereof.
- the boron containing compound in one embodiment is present from
- the boron containing compound is a borate ester or a borate alcohol.
- the borate ester or borate alcohol compounds are substantially the same except the borate alcohol has at least one hydroxyl group that is not esterified.
- borate ester is used to refer to either borate ester or borate alcohol.
- the borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof.
- the alcohols include monohydric alcohols, dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms i.e. vicinal.
- epoxy compounds is used when referring to "at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds and mixtures thereof.”
- Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, HBO 2 , orthoboric acid, H 3 BO 3 , and tetraboric acid, H 2 B 4 O 7 ), boric oxide, boron trioxide and alkyl borates.
- the borate ester may also be prepared from boron halides.
- the borate ester is formed by the reaction of a boron compound with an epoxy compound, dihydric alcohols, trihydric alcohols or higher alcohols.
- the borate ester may be represented by at least one of formulae (D to (VI):
- each R may be hydrogen or hydrocarbyl groups provided that the borate ester is oil soluble.
- At least two of the R groups per the above formulae are hydrocarbyl groups.
- the hydrocarbyl groups may be alky or aryl groups or cyclic groups in which two adjacent R groups are connected in a ring.
- R is alkyl
- the group may be saturated or unsaturated.
- the hydrocarbyl group is an unsaturated alkyl.
- the hydrocarbyl group is cyclic.
- the hydrocarbyl groups are mixtures of alkyl and cycloalkyl.
- the number of carbon atoms present in each R may be 1 to 60, 1 to 40 or 1 to 30 carbon atoms, provided the total number of carbon atoms on the R groups in one embodiment is 9 or more, in another embodiment 10 or more, in another embodiment 12 or more and in another embodiment 14 or more.
- all R groups are hydrocarbyl groups containing 1 to 30 carbon atoms, provided the total number of carbon atoms is 9 or more.
- the boron containing compound is represented by formula (I) described above.
- the borate ester represented by formula (I) contains three hydrocarbyl R groups each containing in one embodiment 1 to 8 carbon atoms, in another embodiment 2 to 7 carbon atoms and in another embodiment 3 to 6 carbon atoms, provided the total number of carbon atoms on the R groups is 4 or more, 6 or more, or 8 or more.
- R groups include isopropyl, n-butyl, isobutyl, amyl, 2- pentenyl, 4-methyl-2-pentyl, 2-ethyl-l-hexyl, 2-ethylhexyl, heptyl, isooctyl, nonyl, decyl, undecyl, dodecenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups.
- the epoxy compounds useful for preparing the borate ester of the invention includes materials that may be represented by the formulae (Vila) or (VIIb):
- R in one embodiment is an alkyl chain containing 1 to 4 or 1 to 2 carbon atoms, and in another embodiment hydrogen;
- R 2 is an alkyl chain containing 8 to 30 or 10 to 26 or 12 to 22 carbon atoms
- T is independently hydrogen or a halogen.
- T is a halogen, such as, chlorine, bromine, iodine or fluorine or mixtures thereof and the epoxy compounds are epihalohydrin compounds.
- T is chlorine.
- T is hydrogen.
- the epoxy compounds of the invention include commercial mixtures of Ci 4 -C] 6 epoxides or Ci 4 -Ci 8 epoxides.
- the epoxy compounds of the invention have been purified. Examples of suitable purified epoxy compounds may include 1,2-epoxydecane, 1,2-epoxyundecane,
- purified epoxy compounds include 1,2-epoxytetradecane, 1,2-epoxypentadecane
- purified epoxy compounds include 1,2-epoxyhexadecane.
- the dihydric alcohols, trihydric alcohols or higher alcohols contain 2 to 30, 4 to 26 or 6 to 20 carbon atoms.
- the alcohol compounds may include glycerol compounds, such as, glycerol monooleate.
- the borate ester may be prepared by blending the boron compound and the epoxy compounds or alcohols described above and heating them at a suitable temperature, such as 80 0 C to 25O 0 C, 90 0 C to 240 0 C or 100 0 C to 23O 0 C, until the desired reaction has occurred.
- the molar ratio of the boron compounds to the epoxy compounds is typically 4: 1 to 1:4, 1: 1 to 1 :3, or about 1:2.
- An inert liquid may be used in performing the reaction.
- the liquid may be, for instance, toluene, xylene, chlorobenzene, dimethylformamide and mixtures thereof. Water is typically formed and is distilled off during the reaction. Alkaline reagents may be used to catalyze the reaction.
- suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl borate.
- the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
- the boron containing compound is a borated dispersant typically derived from an N-substituted long chain alkenyl succinimide.
- the N-substituted long chain alkenyl succinimide has a variety of chemical structures and two typical formulae include:
- each R is independently an alkyl group; each R 4 is an alkylene group; and each repeat unit x is an integer from 1 to 20, 1 to 15 or 1 to 10.
- R 3 is a polyisobutyl group with a number average molecular weight of 350 to 5000, or 500 to 3000 or 550 to 1500, such as 550, 750 or 950 to 1000, or alternatively 1500 to 2500.
- R 3 is further substituted by additional succinimide functionality.
- R 4 is an ethylene (C 2 H 4 ) group.
- the N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, HBO 2 , orthoboric acid, H 3 BO 3 , and tetraboric acid, H 2 B 4 O 7 ), boric oxide, boron trioxide, and alkyl borates described in formulae (I) to (VI) above.
- the borating agent is boric acid which may be used alone or in combination with other borating agents.
- the borated dispersant may be prepared by blending the boron compound and the N-substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 8O 0 C to 250 0 C, 9O 0 C to 23O 0 C or 100 0 C to 21O 0 C, until the desired reaction has occurred.
- the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides in one embodiment is 10: 1 to 1 :4, in another embodiment 4: 1 to 1:3, and in another embodiment 1:2.
- An inert liquid may be used in performing the reaction.
- the liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
- Friction Modifiers [0046]
- the friction modifiers of the invention include a molybdenum dithiocarbamate, a molybdenum ihiophosphate, a long chain fatty acid ester or mixtures thereof.
- the friction modifier is present at 0.01 wt % to 10 wt %, in another embodiment 0.02 wt % to 5 wt % and in another embodiment 0.05 wt % to 3 wt % of the lubricating composition.
- the friction modifier is a long chain fatty acid ester.
- the long chain fatty acid ester is a mono-ester and in another embodiment the long chain fatty acid ester is a (tri)glyceride.
- the long chain fatty acid ester or glyceride in one embodiment is derived from fatty acids, which are a class of compounds containing a long hydrocarbon chain and a terminal carboxylate group and are characterised as unsaturated or saturated.
- the long chain fatty acid ester is derived from the reaction of a long chain fatty acid with an alcohol.
- the long chain fatty acid compounds may be saturated or unsaturated, aliphatic, acyclic or aryl.
- the long chain fatty acid compounds may have a hydrocarbyl group that is linear or branched.
- the hydrocarbyl group is a linear group.
- the long chain fatty acid compounds contain 12 to 24 carbon atoms, for example mixtures of carboxylic acids containing 14 to 20 or 16 to 18 carbon atoms.
- the aliphatic carboxylic acid contains a straight chain hydrocarbyl group. Such acids may be used in combination with acids with more or fewer carbon atoms as well.
- unsaturated long chain fatty acid compounds include carboxylic acids, such as, myristoleic acid, palmitoleic acid, oleic acid or linolenic acid.
- saturated fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid lignoceric acid or mixtures thereof.
- the alcohol is a polyol including diols, triols, and alcohols with higher numbers of alcoholic OH groups (often referred to as polyhydric alcohols).
- Polyhydric alcohols include ethylene glycols, including di-, tri- and tetraethylene glycols; propylene glycols, including di-, tri- and tetrapropylene glycols; glycerol; butane diol; hexane diol; sorbitol; arabitol; mannitol; sucrose; fructose; glucose; cyclohexane diol; erythritol; and pentaerythritols, including di- and tripentaerythritol.
- the polyol includes diethylene glycol, triethylene glycol, glycerol, sorbitol, pentaerythritol or dipentaerythritol.
- the friction modifier is a monoester of a polyol and an aliphatic carboxylic acid.
- the monoester is glycerol monooleate. It is to be understood that glycerol monooleate, as is the case with other such materials, in its commercially available grade, is a mixture which includes such materials as glycerol, oleic acid, other long chain acids, glycerol dioleate, and glycerol trioleate.
- the commercial material is believed to include about 60 + 5 percent by weight of the chemical species "glycerol monooleate,” along with 35 + 5 percent glycerol dioleate, and less than about 5 percent trioleate and oleic acid.
- the amounts of the monoesters, described below, are the amounts of the commercial grade material.
- the monoester of a polyol and an aliphatic carboxylic acid is in the form of a mixture with a sunflower oil or the like, which in one embodiment is present in the friction modifier mixture from 5 to 95 wt %, in another embodiment from 10 to 90 wt %, n another embodiment from 20 to 85 wt % and n another embodiment from 20 to 80 wt % of said mixture.
- the long chain fatty acid ester is beef tallow oil, lard oil, palm oil, castor oil, cottonseed oil, corn oil, peanut oil, soybean oil, sunflower oil, olive oil, whale oil, menhaden oil, sardine oil, coconut oil, palm kernel oil, babassu oil, rape oil, soya oil or linseed oil.
- Molybdenum Dithiocarbamate is beef tallow oil, lard oil, palm oil, castor oil, cottonseed oil, corn oil, peanut oil, soybean oil, sunflower oil, olive oil, whale oil, menhaden oil, sardine oil, coconut oil, palm kernel oil, babassu oil, rape oil, soya oil or linseed oil.
- the friction modifier is a molybdenum dithiocarbamate (MoDTC).
- MoDTCs include commercial materials such as VanlubeTM 822 and MolyvanTM A from R. T. Vanderbilt Co., Ltd., and Adeka Sakura-LubeTM S-100, S-165 and S-600 from Asahi Denka Kogyo K. K.
- Other molybdenum dithiocarbamates are described by Ward in US Patent 4,846,983; by de Vries et al. in US Patent 4,265,773 and by Inoue et al. in US Patent 4,529,536. Additional Performance Additives
- the method optionally includes at least one additional performance additive.
- the additional performance additive includes at least one of metal deactivators, detergents, dispersants, viscosity modifiers, dispersant viscosity modifiers, extreme pressure agents, antiwear agents, antioxidants, corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents and mixtures thereof.
- the additional performance additives may be used alone or in combination.
- the total combined amount of the other performance additive compounds present ranges from 0 wt % to 30 wt %, in another embodiment from 0.01 wt % to 25 wt % and in another embodiment 0.1 wt % to 20 wt % of the lubricating composition. Although one or more of the other performance additives may be present, it is common for the other additional performance additives to be present in different amounts relative to each other.
- the present invention is in the form of a concentrate (which may be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the various additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 80:20 to 10:90 by weight.
- Antioxidants include sulphurised olefins, hindered phenols, diphenylamines; detergents include neutral or overbased, Newtonian or non- Newtonian, basic salts of alkali, alkaline earth and transition metals with one or more of a phenate, a sulphurised phenate, a sulphonate, a carboxylic acid, a phosphorus acid, a mono- and/or a di- thiophosphoric acid, a saligenin, an alkylsalicylate, a salixarate; and dispersants include N-substituted long chain alkenyl succinimide as well as post treated version thereof (excluding post treating with boron compounds).
- Post-treated dispersants include those further treated by reaction with materials such as urea, thiourea, dimercaptothiadiazoles, carbon disulphide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted succinic anhydrides, nitriles, epoxides and phosphorus compounds.
- Antiwear agents include compounds such as metal thiophosphates, especially zinc dialkyldithiophosphates; phosphoric acid esters or salt thereof; phosphites; and phosphorus-containing carboxylic esters, ethers, and amides; antiscuffing agents including organic sulphides and polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, di- tertiary butyl polysulphide, di-tert-butylsulphide, sulphurised Diels-Alder adducts or alkyl sulphenyl N'N-dialkyl dithiocarbamates.
- metal thiophosphates especially zinc dialkyldithiophosphates
- phosphoric acid esters or salt thereof phosphites
- antiscuffing agents including
- EP agents including chlorinated wax, organic sulphides and polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, sulphurised methyl ester of oleic acid, sulphurised alkylphenol, sulphurised dipentene, sulphurised terpene, and sulphurised Diels-Alder adducts; phosphosulphurised hydrocarbons, metal thiocarbamates, such as zinc dioctyldithiocarbamate and barium heptylphenol diacid; may also be used in the composition of the invention.
- organic sulphides and polysulphides such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, sulphurised methyl ester of oleic acid, sulphurised alkylphenol,
- the viscosity modifiers include hydrogenated copolymers of styrene- butadiene, ethylene-propylene polymers, polyisobutenes, hydrogenated styrene- isoprene polymers, hydrogenated isoprene polymers, polymethacrylate acid esters, polyacrylate acid esters, polyalkyl styrenes, alkenyl aryl conjugated diene copolymers, polyolefins, polyalkylmethacrylates and esters of maleic anhydride- styrene copolymers.
- Dispersant viscosity modifiers include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, polymethacrylates functionalised with an amine (e.g., from incorporation of a nitrogen-containing comonomer), or styrene-maleic anhydride copolymers reacted with an amine.
- functionalised polyolefins for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, polymethacrylates functionalised with an amine (e.g., from incorporation of a nitrogen-containing comonomer), or styrene-maleic anhydride copolymers reacted with an amine.
- Additional performance additives such as corrosion inhibitors include octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and a fatty acid such as oleic acid with a polyamine; metal deactivators including derivatives of benzotriazoles, 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles; foam inhibitors including copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally vinyl acetate; demulsifiers including polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide-propylene oxide) polymers; pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides; and seal swell agents including Exxon Necton-37TM (FN 1380) and Exxon Ne
- a composition is prepared by blending additives as shown in Table 1 into a 10W-40 lubricant.
- the amounts in Table 1 are presented inclusive of diluent oil and for glycerol monooleate the other components in the commercial grade material.
- a friction test is carried out employing a commercially available Variable Speed Friction Test instrument.
- the instrument employed in the test is modified by replacing the standard lower plate with a 1998 Hyundai YZFlOOO Rl motorcycle clutch plate sections.
- the instrument upper plate is also modified with a small diameter track to fit a shallow C shape (a 30° segment) clutch plate section of the following dimensions: 13mm wide, the long 'side' of the C is 38mm, the short side is 32mm.
- the instrument is operated at 100°C, with a linear slip velocity of 0.2 m/s and a load of 59 N (or 6 kgf). Before measuring friction of co-efficient, the instrument is allowed to equilibrate under the conditions mentioned above. The instrument is then run on the samples for 60 minutes. The results obtained for Examples 1-2 and Reference Examples 1-2 are shown in Table 2.
- hydrocarbyl substituent or “hydrocarbyl group,” as used herein are used in its ordinary sense, which is well- known to those skilled in the art. Specifically, it refers to a group primarily composed of carbon and hydrogen atoms and attached to the remainder of the molecule through a carbon atom and which does not exclude the presence of other atoms or groups in a proportion insufficient to detract from the molecule having a predominantly hydrocarbon character.
Abstract
Description
Claims
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US63861804P | 2004-12-22 | 2004-12-22 | |
PCT/US2005/044936 WO2006068868A1 (en) | 2004-12-22 | 2005-12-13 | Method of friction control |
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EP1828359A1 true EP1828359A1 (en) | 2007-09-05 |
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ID=36129882
Family Applications (1)
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EP05853776A Ceased EP1828359A1 (en) | 2004-12-22 | 2005-12-13 | Method of friction control |
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US (2) | US20080096776A1 (en) |
EP (1) | EP1828359A1 (en) |
JP (2) | JP2008525584A (en) |
CN (1) | CN101124306A (en) |
WO (1) | WO2006068868A1 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5941342B2 (en) * | 2012-06-05 | 2016-06-29 | Jxエネルギー株式会社 | Lubricating oil composition |
JP5973311B2 (en) * | 2012-10-12 | 2016-08-23 | Jxエネルギー株式会社 | Lubricating oil composition |
CN103160364B (en) * | 2013-03-27 | 2015-10-28 | 中国人民解放军后勤工程学院 | Energy-conservation antifriction diesel engine oil |
WO2015048719A1 (en) * | 2013-09-30 | 2015-04-02 | The Lubrizol Corporation | Method of friction control |
JP2015203052A (en) * | 2014-04-11 | 2015-11-16 | Jx日鉱日石エネルギー株式会社 | Lubricant composition for internal combustion engine |
WO2015156393A1 (en) * | 2014-04-11 | 2015-10-15 | Jx日鉱日石エネルギー株式会社 | Lubricant composition |
EP3158032B1 (en) * | 2014-06-18 | 2022-09-14 | The Lubrizol Corporation | Motorcycle engine lubricant |
US9951290B2 (en) | 2016-03-31 | 2018-04-24 | Exxonmobil Research And Engineering Company | Lubricant compositions |
US20190024007A1 (en) * | 2017-07-24 | 2019-01-24 | Infineum International Limited | Motorcycle Lubricant |
US20200369978A1 (en) * | 2018-01-04 | 2020-11-26 | The Lubrizol Corporation | Boron containing automotive gear oil |
JP2022090378A (en) * | 2020-12-07 | 2022-06-17 | Eneos株式会社 | Lubricating oil composition |
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US4265773A (en) * | 1979-06-28 | 1981-05-05 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
JPS58118481A (en) * | 1982-01-09 | 1983-07-14 | 本田技研工業株式会社 | Swing type power unit for motorcycle |
JPS59122597A (en) * | 1982-11-30 | 1984-07-16 | Honda Motor Co Ltd | Lubricating oil composition |
US4664822A (en) * | 1985-12-02 | 1987-05-12 | Amoco Corporation | Metal-containing lubricant compositions |
US4846983A (en) * | 1986-02-21 | 1989-07-11 | The Lubrizol Corp. | Novel carbamate additives for functional fluids |
AU710294B2 (en) * | 1995-09-12 | 1999-09-16 | Lubrizol Corporation, The | Lubrication fluids for reduced air entrainment and improved gear protection |
US7214648B2 (en) * | 1997-08-27 | 2007-05-08 | Ashland Licensing And Intellectual Property, Llc | Lubricant and additive formulation |
JP4076634B2 (en) * | 1998-09-09 | 2008-04-16 | 新日本石油株式会社 | 4-cycle engine oil composition for motorcycles |
JP4015355B2 (en) * | 2000-09-29 | 2007-11-28 | 新日本石油株式会社 | Lubricating oil composition |
JP4278292B2 (en) * | 2000-10-13 | 2009-06-10 | 本田技研工業株式会社 | Valve operating apparatus for vehicle-mounted internal combustion engine |
US6525004B1 (en) * | 2001-05-01 | 2003-02-25 | Infineum International Inc. | Combustion improving additive for small engine lubricating oils |
US6583092B1 (en) * | 2001-09-12 | 2003-06-24 | The Lubrizol Corporation | Lubricating oil composition |
EP1298189A1 (en) * | 2001-09-28 | 2003-04-02 | Infineum International Limited | Lubricating oil compositions for marine diesel engines |
-
2005
- 2005-12-13 JP JP2007548279A patent/JP2008525584A/en active Pending
- 2005-12-13 US US11/722,373 patent/US20080096776A1/en not_active Abandoned
- 2005-12-13 EP EP05853776A patent/EP1828359A1/en not_active Ceased
- 2005-12-13 WO PCT/US2005/044936 patent/WO2006068868A1/en active Application Filing
- 2005-12-13 CN CNA200580048504XA patent/CN101124306A/en active Pending
-
2010
- 2010-01-06 US US12/652,859 patent/US20100101519A1/en not_active Abandoned
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2012
- 2012-09-14 JP JP2012203136A patent/JP2012246500A/en active Pending
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US20080096776A1 (en) | 2008-04-24 |
JP2012246500A (en) | 2012-12-13 |
US20100101519A1 (en) | 2010-04-29 |
JP2008525584A (en) | 2008-07-17 |
CN101124306A (en) | 2008-02-13 |
WO2006068868A1 (en) | 2006-06-29 |
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