Classifications

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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
  • C10M169/04—Mixtures of base-materials and additives
  • C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
  • C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
  • C10M149/22—Polyamines
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  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
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  • 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
  • C10M141/10—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 phosphorus-containing compound
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
  • C10M169/04—Mixtures of base-materials and additives
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  • 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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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
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  • 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
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
• • C—CHEMISTRY; METALLURGY
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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  • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/223—Five-membered rings containing nitrogen and carbon only
  • C10M2215/224—Imidazoles
• • C—CHEMISTRY; METALLURGY
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  • 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
  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/28—Amides; Imides
• • C—CHEMISTRY; METALLURGY
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/046—Overbased sulfonic acid salts
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
• • 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
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
• • 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
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/106—Thiadiazoles
• • C—CHEMISTRY; METALLURGY
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  • 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
• • 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
  • C10M2223/049—Phosphite
• • 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
• • C—CHEMISTRY; METALLURGY
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  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/08—Resistance to extreme temperature
• • C—CHEMISTRY; METALLURGY
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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  • 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
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
• • 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
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
• • C—CHEMISTRY; METALLURGY
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition

Definitions

• This invention relates to an additive composition useful for providing excellent friction stability to lubricating oils, particularly power transmitting fluids such as automatic transmission fluids (hereinafter referred to as "ATFs”), continuously variable transmission fluids (“CVTFs”), and double clutch transmission fluids (“DCTFs”), and more particularly useful for imparting excellent frictional characteristics to the fluid during high speed clutch engagements.
• ATFs automatic transmission fluids
• CVTFs continuously variable transmission fluids
• DCTFs double clutch transmission fluids
• Further aspects include a method of imparting friction stability to such lubricating oils comprising the use therein of the additive composition, the use of the additive composition in lubricating oil for the purpose of improving friction stability, and other aspects as hereinafter defined.
• the transmissions to which this invention is applicable are those transmissions that contain a lubricated wet clutch that is used under conditions of high energy dissipation.
• These types of applications include the clutches in an automatic transmission used to accomplish ratio or speed changes; wet starting clutches in automatic, continuously variable or double clutch transmissions; or clutches used in torque vectoring or interaxle differential applications.
• These clutches can be characterized as having high differential speed between the two members of the clutch and high energy dissipation in the "engagement" or "lock up" of the clutch.
• one additional aspect of the invention concerns a power transmission apparatus comprising a single or multiple plate clutch device lubricated by the power transmission fluid of the invention, wherein in use the clutch is employed under conditions of high energy, i.e. undergoing engagements at above speeds of about 500 rpm (revolutions per minute), and especially above 500 rpm.
• a common goal of automobile builders is to produce vehicles that are more durable and perform more reliably over their service life.
• One aspect of increased durability and reliability is to produce vehicles that need a minimum of repairs during their service life.
• a second aspect is to have vehicles that perform consistently throughout this "lifetime”.
• In the case of automatic transmissions not only should the transmission not fail during the lifetime of the vehicle, but its shift characteristics should not perceptibly change over this period. Since shift characteristics of automatic transmissions are heavily dependent on the frictional characteristics of the ATF, the fluid needs to have very stable frictional performance with time, and therefore mileage. This aspect of ATF performance is known as friction stability.
• friction stability is known as friction stability.
• many vehicle builders are moving to "fill-for-life" automatic transmission fluids; this trend further increases the need for friction stability of the ATF, since the fluid will no longer be replaced at 15,000 to 50,000 mile service intervals.
• a common method for determining the friction durability of an ATF is through the use of an SAE #2 friction test machine.
• This machine simulates the high speed engagement of a clutch by using the clutch as a brake, thereby absorbing a specified amount of energy.
• the energy of the system is chosen to be equivalent to the energy absorbed by the clutch in completing one shift in the actual vehicle application.
• the machine uses a specified engagement speed, normally 3600 rpm, and a calculated inertia to provide the required amount of energy to the test clutch and fluid.
• the clutch is lubricated by the fluid being evaluated, and each deceleration (i.e., braking) of the system is termed one cycle. To evaluate friction stability many cycles are run consecutively.
• Friction control in a power transmission fluid such as an ATF, CVTF or DCTF is primarily the function of the friction modifiers in the fluid.
• the thermal and oxidative stresses under which such fluids are used in the transmissions lead to additive degradation and thereby changes in fluid properties. Oxidation or thermal destruction of the friction modifiers is often first seen in the fluid as rising static friction. Rising static friction causes abrupt shifts which vehicle occupants can feel as a jerk or lurch as the shift completes. Rising static friction is a common mode of failure of power transmission fluids. In some circumstances, however, oxidation of friction modifiers can transform them into more active species. In these situations static friction can actually decrease during service.
• U.S patents 5,750,476 and 5,840,662 report that a combination of antioxidants, oil soluble phosphorus compounds, and specific low potency friction modifiers can confer outstanding friction durability to ATFs. These low potency friction modifiers are characterized by the fact that once a saturation concentration of the friction modifier is reached in the fluid, increasing the concentration causes no further reduction in the measured friction levels. Fluids can thus be treated with very high concentrations of these low potency friction modifiers to create a larger reservoir of additive in the oil and still exhibit satisfactory levels of friction. It is believed that as the low potency friction modifier molecules are consumed, through shearing or oxidation, there is always an ample concentration available to take their place on the friction surfaces. An oil-soluble phosphorus-containing compound must also be present to protect the system from wear.
• Such friction modifiers show improved properties over existing solutions and provide a more cost-effective solution to the problem of friction durability in oils, especially in power transmission fluids.
• this invention relates to lubricating oil (and particularly to power transmission fluid) compositions comprising an oil soluble phosphorus containing compound and a polyalkylene polyamine-based friction modifier carrying at least one hydrocarbyl substituent, the or each hydrocarbyl substituent comprising between 6 and 30 carbon atoms, wherein at least one secondary amino group in the polyamine chain of the friction modifier has been acylated to the corresponding amide group.
• this invention relates to lubricating oil (and particularly to power transmission fluid) compositions comprising:
• R 3 is preferably a C 1 to C 20 hydrocarbyl substituent, more preferably being an alkyl or aryl group or one of their hetero atom-containing analogs. Even more preferably R 3 is a C 1 to C 10 alkyl or aryl group and most preferably R 3 is a C 1 to C 6 alkyl or aryl group, especially methyl, ethyl, propyl or butyl.
• aspects of the invention include the polyalkylene polyamine-based friction modifier (b) (i) per se as defined above; an additive composition comprising the friction modifier defined above in combination with an oil soluble phosphorus containing compound; a method of imparting friction stability to lubricating oils, comprising the use therein of a friction stability improving effective amount of the additive combination defined above; and the use, in lubricating oil, of the additive composition defined above, in an amount effective to improve the friction stability thereof.
• This invention concerns a method for improving the friction stability of lubricating oils, without disadvantageously lowering the coefficients of friction. It comprises the combined use in the oil of a friction modifier derived from a defined polyalkylene polyamine and an oil-soluble source of phosphorus. This combination of additives provides outstanding friction stability to lubricating oils, especially transmission fluids.
• While the benefits of this invention are contemplated to be applicable to a wide variety of lubricating oils wherein friction modifiers are usefully employed (e.g., crankcase engine oils, etc.), particularly preferred compositions are power transmitting fluids, especially automatic transmission fluids (ATFs), continuously variable transmission fluids (CVTFs) and double clutch transmission fluids (DCTFs).
• ATFs automatic transmission fluids
• CVTFs continuously variable transmission fluids
• DCTFs double clutch transmission fluids
• Examples of other, less preferred types of power transmitting fluids included within the scope of this invention are gear oils, hydraulic fluids, tractor fluids, universal tractor fluids and the like. These power transmitting fluids can be formulated with a variety of additional performance additives and in a variety of base oils.
• the preferred friction modifiers of the present invention are either produced from succinimides carrying at least one hydrocarbyl substituent wherein the or each hydrocarbyl substituent comprises between 6 and 30 carbon atoms and is preferably an alkenyl group or the fully saturated alkyl analog; or are produced from carboxylic amides having at least one alkenyl or alkyl chain comprising between 6 and 30 carbon atoms and being one or more structures formed from the reaction of the corresponding alkenyl or alkyl carboxylic acids and polyalkylene polyamines.
• the most preferred type of friction modifier is produced firstly by reaction of alkyl or alkenyl succinic anhydrides, the akyl or alkenyl substituents thereon being isomerized chains, with one or more polyalkylene polyamines, preferably one or more polyethylene polyamines.
• the isomerised chain is bonded to an ⁇ -carbon atom of the succinimide ring, giving rise to a two-branched substituent attached to the ring ⁇ -carbon atom via a tertiary carbon atom, as exemplified in the structure below for the alkenyl-substituted structure reacted with polyethylene polyamine: wherein x and y are independent integers whose sum is from 1 to 25, and z is an integer from 1 to 10.
• isomerized alkenyl succinic anhydrides is well known and is described in, for example, U.S. 3,382,172 .
• these materials are prepared by heating alpha-olefins with acidic catalysts to migrate the double bond to an internal position. This mixture of olefins (2-enes, 3-enes, etc.) is then thermally reacted with maleic anhydride. Typically olefins from C 6 (1-hexene) to C 30 (1-triacontene) are used.
• Preferred materials are iso-hexadecylsuccinic anhydride and iso-octadecylsuccinic anhydride, for which especially good performance is seen.
• the materials produced by this process contain one double bond (alkenyl group) in the alkyl chain.
• the alkenyl substituted succinic anhydrides may be easily converted to their saturated alkyl analogs by hydrogenation.
• the isomerized-alkenyl or -alkyl substituted succinic anhydrides can thereafter be reacted with suitable amines to produce friction modifiers of the types shown in structure (I), from which the friction modifiers (b) (i) of the invention are thereafter formed by acylation with R 3 COX.
• carboxylic acids possessing at least one alkenyl or alkyl chain comprising between 6 and 30 carbon atoms may be reacted with suitable amines to produce friction modifiers of the types shown in structures (II) and (III).
• Such acids are preferably alkyl or alkenyl acids comprising between 12 and 22 carbon atoms, and especially between 16 and 20 carbon atoms.
• the friction modifiers of the invention are thereafter formed by acylation with R 3 COX.
• Suitable amines useful to produce the friction modifier of structures (I), (II) and (III) are represented by structure (XI): wherein n and m are each independently integers from 1 to 6 and R 2 is as previously defined.
• the amines of the structure XI may in turn be produced from the reaction of primary polyamines.
• a particularly useful class of such amines is the polyalkylene polyamines of the general formula (XII), where (XII) is: wherein a is an integer from 1 to 5, preferably 2 to 4; and each n is independently an integer from 1 to 6, preferably from 1 to 4.
• Non-limiting examples of suitable polyamine compounds include: diethylene triamine, triethylene tetramine, tetraethylene pentamine and pentaethylene hexamine. Low cost mixtures of polyamines having from 5 to 7 nitrogen atoms per molecule are available from Dow Chemical Co. as Polyamine H, Polyamine 400 and Polyamine E-300.
• Such polyamines may be reacted with the above-described succinic anhydrides substituted with alkenyl groups or their fully saturated alkyl analogs to form the structure I; or the above-described alkenyl or alkyl carboxylic acids to form structures or III, .
• the preferred friction modifiers of this invention are normally prepared by heating the isomerized alkenyl succinic anhydride described above (or its saturated-alkyl analog) with the above polyamine and removing the water formed.
• the ratio of primary amine groups to succinic anhydride groups is usually 1 to 1.
• the acylating agents of the present invention are those materials capable of converting a secondary amine to an amide. Such materials are of the formula R 3 COX wherein R 3 is a hydrocarbyl group and X is a leaving group, which leaving group may also be connected to the R 3 group of the acylating agent so as to form a ring structure.
• R 3 is preferably a C 1 to C 20 hydrocarbyl substituent, preferably being an alkyl or aryl group or one of their hetero atom-containing analogs. More preferably R 3 is a C 1 to C 10 alkyl or aryl group and most preferably R 3 is a C 1 to C 6 alkyl or aryl group. Most preferably alkyl such as methyl, ethyl, propyl or butyl.
• acylating agents preferred for use are, in particular, acetic anhydride, propionic anhydride, butyric anhydride, trifluoroacetic anhydride, acetyl chloride, propionyl chloride, butyryl bromide, butyrolactone, caprolactone, methyl acetate, ethyl acetate, butyl acetate, butyl propionate and butyl butrate.
• Acetic anhydride is most preferred.
• the preferred friction reducers of this invention are those produced by firstly reacting alkenyl succinic anhydrides with those polyamines (XI), and thereafter with acetic anhydride.
• the most preferred products of this invention are those produced from reaction of the isomerized-alkenyl succinic anhydrides with polyamines (XII) which are then reacted with acetic anhydride.
• the most preferred friction modifier (b)(i) of the invention has the structure : which may suitably by formed by the acetylation of the reaction product of diethylene triamine and the requisite isomerised octadecenyl succinic anhydride. This material has been found to give especially good performance in the present invention. Both the friction modifer additive comprising this compound, and this compound per se, represent further aspects of the present invention.
• the treat rates of the friction modifiers are usually from about 0.1 to about 10, preferably 0.5 to 7, and most preferably from 1.0 to 5.0 weight percent in the lubricating composition.
• Example A (Preparation of the isomerised succinimide) - Into a one liter round bottomed flask fitted with a mechanical stirrer, nitrogen sweep, Dean Starke trap and condenser was placed 352 gm (1.00 mole) of iso-octadecenylsuccinic anhydride (ODSA from Dixie Chemical Co.). A slow nitrogen sweep was begun, the stirrer started and the material heated to 130°C. Immediately thereafter, 95 gm (0.50 moles) of commercial tetraethylene pentamine was added slowly via an addition funnel to the hot stirred iso-octadecenylsuccinic anhydride. The temperature of the mixture was increased to 150°C where it was held for two hours. During this heating period 10 ml. of water ( ⁇ 50% of theoretical yield) were collected in the Dean Starke trap. The flask was cooled to yield the product. Yield: 435 gm. Percent nitrogen: 8.1.
• Example B (Preparation of the isomerised succinimide) - The same procedure was followed as in Example A, except that the following amounts were used: iso-octadecenylsuccinic anhydride, 700 gm (2.0 moles), and diethylenetriamine, 103 gm (1.0 mole). The water recovered was 32 ml. Yield: 765 gm. Percent nitrogen: 5.5.
• Example C (Preparation of the acylated isomerised succinimide of the invention) - Into a one liter round bottomed flask fitted with a mechanical stirrer, nitrogen sweep, Dean Starke trap and condenser was placed 765 gm (1.0 mole) of the product of Example B. A slow nitrogen sweep was begun, the stirrer started and the material heated to 90°C. Acetic anhydride, 102 gm (1.0 mole) was added drop wise through an addition funnel. Once the addition was complete the temperature was raised to 140°C and held for 3 hours. Residual acetic acid was removed by distillation at 150°C at 50 mm Hg. Yield: 805 gm. Percent nitrogen: 5.2.
• Example D (Preparation of the acylated isomerised succinimide of the invention) - The same procedure was followed as in Example C, except that the following amounts were used: Product of Example B, 765 gm (1.0 mole); caprolactone 131 gm (1.15 moles). The mixture was heated at 170°C for 6 hours followed by the addition of 2 mls of stannous octanoate. After addition of the octanoate the temperature was increased to 180°C for an additional 4 hours. Yield: 895 gm.
• Example E (Preparation of the acylated isomerised succinimide of the invention) - Into a one liter round bottomed flask fitted with a mechanical stirrer, nitrogen sweep, Dean Starke trap and condenser was placed 429 gm (0.50 moles) of the product of Example A. A slow nitrogen sweep was begun, the stirrer started and the material heated to 90°C. Acetic anhydride, 61 gm (0.5 moles) was added drop wise through an addition funnel. Once the addition was complete the temperature was raised to 140°C and held for 3 hours. Residual acetic acid was removed by distillation at 150°C at 50 mm Hg. Yield: 485 gm. Percent nitrogen: 7.1.
• Example F (Preparation of the acylated product of isostearic acid-TEPA) - Into a one liter round bottomed flask fitted with a mechanical stirrer, nitrogen sweep, Dean Starke trap and condenser was placed 402 gm (1.37 mole) of iso-stearic acid. A slow nitrogen sweep was begun, the stirrer started and the material heated to 100°C. Tetraethylene pentamine (TEPA), 130 gm (0.69 moles) was added drop wise through a dropping funnel over one hour. Once addition was complete the mixture was heated to 160°C for 6 hours, during which time 24 gm of water were recovered (98% of theory).
• TEPA Tetraethylene pentamine
• the oil-soluble phosphorus-containing compounds useful in this invention may vary widely and are not limited by chemical type. The only limitation is that the material be oil soluble so as to permit the dispersion and transport of phosphorus-containing compound within the lubricating oil system to its site of action.
• suitable phosphorus compounds are: phosphites and thiophosphites (mono-alkyl, di-alkyl, tri-alkyl and partially hydrolyzed analogs thereof); phosphates and thiophosphates; amines treated with inorganic phosphorus such as phosphorous acid, phosphoric acid or their thio analogs; zinc dithiodiphosphates; amine phosphates.
• phosphorus compounds include: mono-n-butyl-hydrogen-acid-phosphite; di-n-butyl-hydrogen phosphite; triphenyl phosphite; triphenyl thiophosphite; tri-n-butylphosphate; dimethyl octadecenyl phosphonate, 900MW polyisobutenyl succinic anhydride (PIBSA) polyamine dispersant post treated with H 3 PO 3 and H 3 BO 3 (see e.g., U.S. 4,857,214 ); zinc (di-2-ethylhexyldithiophosphate).
• PIBSA polyisobutenyl succinic anhydride
• the preferred oil soluble phosphorus compounds are the esters of phosphoric and phosphorous acid. These materials would include the di-alkyl, tri-alkyl and tri-aryl phosphites and phosphates.
• a preferred oil soluble phosphorus compound is the mixed thioalkyl phosphite esters, for example as produced in U.S. 5,314,633 , incorporated herein by reference.
• the most preferred phosphorus compounds are thioalkyl phosphites, for example as illustrated by Example G below.
• the phosphorus compounds of the invention can be used in the oil in any effective amount. However, a typical effective concentration of such compounds would be that delivering from about 5 to about 5000 ppm phosphorus into the oil. A preferred concentration range is from about 10 to about 1000 ppm of phosphorus in the finished oil and the most preferred concentration range is from about 50 to about 500 ppm.
• EXAMPLE G An alkyl phosphite mixture was prepared by placing in a round bottom 4-neck flask equipped with a reflux condenser, a stirrer and a nitrogen bubbler, 194 grams (1.0 mole) of dibutyl hydrogen phosphite. The flask was flushed with nitrogen, sealed and the stirrer started. The dibutyl hydrogen phosphite was heated to 150°C under vacuum (-90 kPa) and 190 grams (1 mole) of hydroxylethyl-n-octyl sulfide was added through a dropping funnel over about one hour. During the addition approximately 35 ml of butanol was recovered in a chilled trap.
• additives known in the art may be added to the lubricating oil of the invention, or included in the additive composition of the invention.
• additives include dispersants, antiwear agents, corrosion inhibitors, detergents, extreme pressure additives, and the like. They are typically disclosed in, for example, " Lubricant Additives” by C. V. Smallheer and R. Kennedy Smith, 1967, pp. 1-11 and U.S. Patent 4,105,571 .
• Suitable dispersants include long chain (i.e. greater than forty carbon atoms) substituted hydrocarbyl succinimides and hydrocarbyl succinamides, mixed ester/amides of long chain (i.e. greater than forty carbon atoms) hydrocarbyl-substituted succinic acid, hydroxyesters of such hydrocarbyl-substituted succinic acid, and Mannich condensation products of long chain (i.e. greater than forty carbon atoms) hydrocarbyl-substituted phenols, formaldehyde and polyamines. Mixtures of such dispersants can also be used.
• the preferred dispersants are the long chain alkenyl succinimides. These include acyclic hydrocarbyl substituted succinimides formed with various amines or amine derivatives such as are widely disclosed in the patent literature. Use of alkenyl succinimides which have been treated with an inorganic acid of phosphorus (or an anhydride thereof) and a boronating agent are also suitable for use in the compositions of this invention as they are much more compatible with elastomeric seals made from such substances as fluoro-elastomers and silicon-containing elastomers.
• Polyisobutenyl succinimides formed from polyisobutenyl succinic anhydride and an alkylene polyamine such as triethylene tetramine or tetraethylene pentamine wherein the polyisobutenyl substituent is derived from polyisobutene having a number average molecular weight in the range of 500 to 5000 (preferably 800 to 2500) are particularly suitable.
• Dispersants may be post-treated with many reagents known to those skilled in the art. (see, e.g., U.S. Pat. Nos. 3,254,025 , 3,502,677 and 4,857,214 ).
• the additive combinations of this invention may be combined with other desired lubricating oil additives to form a concentrate.
• the active ingredient (a.i.) level of the concentrate will range from 20 to 90%, preferably from 25 to 80%, most preferably from 35 to 75 weight percent of the concentrate.
• the balance of the concentrate is a diluent typically comprised of a lubricating oil or solvent.
• Lubricating oils useful in this invention are derived from natural lubricating oils, synthetic lubricating oils, and mixtures thereof. In general, both the natural and synthetic lubricating oil will each have a kinematic viscosity ranging from about 1 to about 100 mm 2 /s (cSt) at 100°C, although typical applications will require each oil to have a viscosity ranging from about 2 to about 8 mm 2 /s (cSt) at 100°C.
• Natural lubricating oils include animal oils, vegetable oils (e.g., castor oil and lard oil), petroleum oils, mineral oils, and oils derived from coal or shale.
• the preferred natural lubricating oil is mineral oil.
• Suitable mineral oils include all common mineral oil basestocks. This includes oils that are naphthenic or paraffinic in chemical structure. Oils that are refined by conventional methodology using acid, alkali, and clay or other agents such as aluminum chloride, or they may be extracted oils produced, for example, by solvent extraction with solvents such as phenol, sulfur dioxide, furfural, dichlordiethyl ether, etc. They may be hydrotreated or hydrofined, dewaxed by chilling or catalytic dewaxing processes, or hydrocracked. The mineral oil may be produced from natural crude sources or be composed of isomerized wax materials or residues of other refining processes.
• the mineral oils will have kinematic viscosities of from 2.0 mm 2 /s (cSt) to 8.0 mm 2 /s (cSt) at 100°C.
• the preferred mineral oils have kinematic viscosities of from 2 to 6 mm 2 /s (cSt), and most preferred are those mineral oils with viscosities of 3 to 5 mm 2 /s (cSt) at 100°C.
• Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as oligomerized, polymerized, and interpolymerized olefins [e.g., polybutylenes, polypropylenes, propylene, isobutylene copolymers, chlorinated polylactenes, poly(1-hexenes), poly(1-octenes), poly-(1-decenes), etc., and mixtures thereof]; alkylbenzenes [e.g., dodecyl-benzenes, tetradecylbenzenes, dinonyl-benzenes, di(2-ethylhexyl)benzene, etc.]; polyphenyls [e.g., biphenyls, terphenyls, alkylated polyphenyls, etc.]; and alkylated diphenyl ethers, alkylated diphenyl sulf
• Synthetic lubricating oils also include alkylene oxide polymers, interpolymers, copolymers, and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc.
• This class of synthetic oils is exemplified by: polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide; the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl-polyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of polypropylene glycol having a molecular weight of 1000 - 1500); and mono- and poly-carboxylic esters thereof (e.g., the acetic acid esters, mixed C 3 -C 8 fatty acid esters, and C 12 oxo acid diester of tetraethylene glycol).
• Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids, alkenyl malonic acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoethers, propylene glycol, etc.).
• dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic
• esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebasic acid with two moles of tetraethylene glycol and two moles of 2-ethyl-hexanoic acid, and the like.
• a preferred type of oil from this class of synthetic oils is adipates of C 4 to C 12 alcohols.
• Esters useful as synthetic lubricating oils also include those made from C 5 to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane pentaerythritol, dipentaerythritol, tripentaerythritol, and the like.
• Silicon-based oils (such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils) comprise another useful class of synthetic lubricating oils. These oils include tetra-ethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl-2-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, hexa-(4-methyl-2-pentoxy)-disiloxane, poly(methyl)-siloxanes and poly(methylphenyl) siloxanes, and the like.
• oils include tetra-ethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl-2-eth
• Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, and diethyl ester of decylphosphonic acid), polymeric tetra-hydrofurans, poly- ⁇ -olefins, and the like.
• liquid esters of phosphorus-containing acids e.g., tricresyl phosphate, trioctyl phosphate, and diethyl ester of decylphosphonic acid
• polymeric tetra-hydrofurans e.g., polymeric tetra-hydrofurans, poly- ⁇ -olefins, and the like.
• the lubricating oils may be derived from refined, rerefined oils, or mixtures thereof.
• Unrefined oils are obtained directly from a natural source or synthetic source (e.g., coal, shale, or tar sands bitumen) without further purification or treatment.
• Examples of unrefined oils include a shale oil obtained directly from a retorting operation, a petroleum oil obtained directly from distillation, or an ester oil obtained directly from an esterification process, each of which is then used without further treatment.
• Refined oils are similar to the unrefined oils except that refined oils have been treated in one or more purification steps to improve one or more properties.
• Suitable purification techniques include distillation, hydrotreating, dewaxing, solvent extraction, acid or base extraction, filtration, and percolation, all of which are known to those skilled in the art.
• Rerefined oils are obtained by treating used oils in processes similar to those used to obtain the refined oils. These rerefined oils are also known as reclaimed or reprocessed oils and are often additionally processed by techniques for removal of spent additives and oil breakdown products.
• Suitable lubricating oils are those basestocks produced from oligomerization of natural gas feed stocks or isomerization of waxes. These basestocks can be referred to in any number of ways but commonly they are known as Gas-to-Liquid (GTL) or Fischer-Tropsch base stocks.
• GTL Gas-to-Liquid
• Fischer-Tropsch base stocks Fischer-Tropsch base stocks
• the lubricating oil is a mixture of natural and synthetic lubricating oils (i.e., partially synthetic)
• the choice of the partial synthetic oil components may widely vary, however, particularly useful combinations are comprised of mineral oils and poly- ⁇ -olefins (PAO), particularly oligomers of 1-decene.
• PAO poly- ⁇ -olefins
• test fluids were blended using exactly the same base lubricating oils, dispersants, anti-oxidants, and viscosity modifiers.
• the test blends contained the most preferred source of oil soluble phosphorus (Example G above), prepared as described in U.S. 5,314, 633 .
• Into each fluid was added 3.0 mass percent of the friction modifier as follows:
• compositions of the test fluids and a summary of the test results are given in Table 1 below.
• Example B Flud A
• Example C has a decrease in static friction of 0.013 over the period of 500 to 10,000 cycles.
• the fluids containing the products of the invention, the products of Examples C and D exhibit lower changes in static friction : for Fluid B, a decrease of 0.002 and for Fluid C, a decrease of 0.003.

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