WO2022054023A1 - Lubricating oil containing alkyl phosphonic acid - Google Patents

Lubricating oil containing alkyl phosphonic acid Download PDF

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Publication number
WO2022054023A1
WO2022054023A1 PCT/IB2021/058338 IB2021058338W WO2022054023A1 WO 2022054023 A1 WO2022054023 A1 WO 2022054023A1 IB 2021058338 W IB2021058338 W IB 2021058338W WO 2022054023 A1 WO2022054023 A1 WO 2022054023A1
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WO
WIPO (PCT)
Prior art keywords
lubricating oil
oil composition
wear
lubricating
succinimide
Prior art date
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PCT/IB2021/058338
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English (en)
French (fr)
Inventor
Masami Fuchi
Naoya Sasaki
Takahiro Nakagawa
Satoshi Ohta
Naoki Masuda
Koichi Kubo
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Chevron Japan Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Chevron Japan Ltd. filed Critical Chevron Japan Ltd.
Priority to US18/023,945 priority Critical patent/US20240101923A1/en
Priority to EP21783050.4A priority patent/EP4211210A1/en
Priority to AU2021340009A priority patent/AU2021340009A1/en
Priority to JP2023516492A priority patent/JP2023541435A/ja
Priority to CA3193618A priority patent/CA3193618A1/en
Priority to CN202180062873.3A priority patent/CN116323878A/zh
Publication of WO2022054023A1 publication Critical patent/WO2022054023A1/en

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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
    • C10M141/10—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
    • 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
    • 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
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • 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
    • C10N2030/40—Low content or no content compositions
    • 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
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators

Definitions

  • This disclosure relates to lubricating oil additives and lubricating oil compositions containing the same. More specifically, this disclosure describes zinc- free additives that impart anti-wear properties to lubricating oil compositions.
  • Zinc dialkyldithiophosphate has long been used as a wear inhibitor in various lubricating fluids such as automotive engine oil. At least one drawback is that ZnDTP can decompose due to high temperature, oxidative deterioration, or hydrolysis in the presence of water. The result of the decomposition is a sludge that decreases friction coefficient and/or clogs important moving parts.
  • a lubricating oil composition comprising: a major amount of an oil of lubricating viscosity having a kinematic viscosity at 100°C in a range of about 1.5 to about 35 mm 2 /s; and an anti-wear mixture comprising: one or more ashless dispersants and an alkyl phosphonic acid having a structure given by wherein R is a C 3 -C 20 hydrocarbyl group; initial pH of the anti-wear mixture is between 5.0-9.5 as measured by ASTM D664; and wherein the lubricating oil composition is free of zinc.
  • a lubricating oil composition comprising: a major amount of an oil of lubricating viscosity having a kinematic viscosity at 100°C in a range of about 1.5 to about 35 mm 2 /s; and an anti-wear mixture comprising: one or more polyisobutenyl succinimide dispersants and an alkyl phosphonic acid having a structure given by wherein R is a C 3 -C 20 hydrocarbyl group; initial pH of the anti-wear mixture is between 5.0 - 9.5 as measured by ASTM D664; and wherein the lubricating oil composition is free of zinc.
  • a method of reducing wear of a transmission or gear comprising: lubricating the transmission or gear with a lubricating oil composition comprising: a major amount of an oil of lubricating viscosity having a kinematic viscosity at 100°C in a range of about 1.5 to about 35 mm2/s; and an antiwear mixture comprising: one or more ashless dispersants and an alkyl phosphonic acid of the following formula: wherein R is a C 3 -C 20 hydrocarbyl group; wherein the initial pH of the anti-wear mixture is between 5.0 - 9.5 when measured by the ASTM D664 method; and wherein the lubricating oil composition is free of zinc.
  • a lubricating oil composition comprising: a major amount of an oil of lubricating viscosity having a kinematic viscosity at 100°C in a range of about 1.5 to about 35 mm2/s; and an antiwear mixture comprising: one or more ashless dispersants and an
  • succinimide is understood in the art to indude many of the amide, imide, and amidine species which may be formed by the reaction of a succinic anhydride with an amine.
  • Alkenyl or alkyl succinimides are disclosed in numerous references and are well known in the art. Certain fundamental types of succinimides and related materials encompassed by the term of art "succinimide” are taught in U.S. Patent Nos. 2,992,708; 3,018,291; 3,024,237; 3,100,673; 3,219,666; 3,172,892; and 3,272,746.
  • hydrocarbyl refers to a chemical group or moiety derived from hydrocarbons including saturated and unsaturated hydrocarbons.
  • hydrocarbyl groups include alkenyl, alkyl, polyalkenyl, polyalkyl, phenyl, and the like.
  • 'oil-soluble' or 'oil-dispersible' do not necessarily indicate that the compounds or additives are soluble, dissolvable, miscible or capable of being suspended in the oil in all proportions. These do mean, however, that they are, for instance, soluble or stably dispersible in oil to an extent sufficient to exert their intended effect in the environment in which the oil is employed. Moreover, the additional incorporation of other additives may also permit incorporation of higher levels of a particular additive, if desired.
  • a dispersant is an essential lubricant additive, particularly in engine oil and automatic transmission fluid, for preventing sludge generation and increasing friction coefficient of wet clutch.
  • dispersants can often reduce the effects of anti-wear agents (e.g., ZnDTP) and extreme pressure (EP) additives particularly in sulfur phosphorus (S-P) type gear oils and automatic transmission fluids.
  • anti-wear agents e.g., ZnDTP
  • EP extreme pressure
  • S-P sulfur phosphorus
  • the present invention describes wear inhibitors (or anti-wear agents) that can impart anti-wear properties to lubricating oil compositions.
  • the present invention describes a wear inhibitor system comprising a succinimide and a phosphonic acid.
  • the wear inhibitor system of the present invention is zinc-free (present in less than about 10 ppm) and therefore avoids at least some of the performance issues associated with conventional zinc anti-wear agents.
  • the wear inhibitor system of the present invention may be added to any compatible lubricating oil such as engine oil, hydraulic fluid, slide way lubricant, automatic transmission fluid (ATF), continuously variable transmission (CVT) fluid, battery electric vehicle (BEV), hybrid electric vehicle (HEV) transmission fluid, and gear oil.
  • ATF automatic transmission fluid
  • CVT continuously variable transmission
  • BEV battery electric vehicle
  • HEV hybrid electric vehicle
  • the succinimide dispersant can be prepared by any known method such as those described in, for example, U.S. Patent Publication No. 20180034635 and U.S. Patent No. 7,091,306, which are hereby incorporated by reference.
  • the succinimide is a hydrocarbyl succinimide obtained as the product of a reaction of alkyl -substituted succinic anhydrides with a polyamine.
  • the succinic anhydrides are typically substituted in alpha position by an alkyl chain such as polyisobutylene (PIBSA) or PIBSA-type moiety.
  • PIBSA polyisobutylene
  • any alkyl group compatible with the present invention may be contemplated.
  • polyalkylene polyamine is commonly used as the polyamine.
  • any polyamine compatible with the present invention may be contemplated.
  • the polyamine can react with the alkyl-substituted succinic anhydride to produce, according to their molar ratio, mono-succinimides, bis-succinimides, trissuccinimides or mixtures of thereof.
  • a hydrocarbyl bis-succinimide can be obtained by reacting a hydrocarbyl-substituted succinic anhydride of structure II
  • R is a hydrocaryl substituent is derived from a polyalkene group having a number average molecular weight of from about 500 to about 3000) with a polyamine.
  • R is a hydrocarbyl substituent is derived from a polyalkene group having a number average molecular weight of from about 1000 to about 2500.
  • R is a polyisobutenyl substituent derived from a polyisobutene having a number average molecular weight of from about 500 to about 3000 (such as from 850 to 1700).
  • R is a polyisobutenyl substituent derived from a polyisobutene having a number average molecular weight of from about 1000 to about 2500.
  • Suitable polyamines can have a straight- or branched-chain structure and may be cyclic, acylic, or combinations thereof.
  • polyalkylene polyamines may be used to prepare the bis-succinimide dispersants.
  • Such polyalkylene polyamines will typically contain about 2 to about 12 nitrogen atoms and about 2 to 24 carbon atoms.
  • Particularly suitable polyalkylene polyamines include those having the formula: H 2 N — (R'NH) x — H wherein R' is a straight- or branched-chain alkylene group having 2 or 3 carbon atoms and x is 1 to 9.
  • suitable polyalkylene polyamines include diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylene hexamine (PEHA), and heavier poly-alkylene-amines (HPA).
  • DETA diethylenetriamine
  • TETA triethylenetetramine
  • TEPA tetraethylenepentamine
  • PEHA pentaethylene hexamine
  • HPA heavier poly-alkylene-amines
  • the polyamine may contain cyclic groups.
  • specific examples include N, N'-bis-(2-aminoethyl)piperazine) (Bis AEP), N-[(2- aminoethyl) 2-aminoethyl]piperazine) (PEEDA), 1-(2-aminoethyl)-4-[(2- aminoethyl)amino]ethyl]- piperazine) (AEPEEDA) and 1 -[2-[[2-[(2-aminoethyl)amino]ethyl]amino]ethyl]- piperazine) (PEDETA).
  • polyamines suitable for use in the present invention are commercially available and others may be prepared by methods which are well known in the art. For example, methods for preparing amines and their reactions are detailed in Sidgewick's "The Organic Chemistry of Nitrogen", Clarendon Press, Oxford, 1966; Noller's “Chemistry of Organic Compounds”, Saunders, Philadelphia, 2nd Ed., 1957; and Kirk-Othmer's "Encyclopedia of Chemical Technology", 2nd Ed., especially Volume 2, pp. 99 116.
  • the hydrocarbyl-substituted succinic anhydride is reacted with the polyamine at a temperature of about 130°C to 220°C (e.g., 140°C to 200°C, 145°C to 175°C, etc.).
  • the reaction can be carried out under an inert atmosphere, such as nitrogen or argon.
  • a suitable molar charge of polyamine to polyalkenylsubstituted succinic anhydride is from about 0.35:1 to about 1 :1 (e.g., 0.4:1 to 0.75:1).
  • the "molar charge of polyamine to polyalkenyl-substituted succinic anhydride" means the ratio of the number of moles of polyamine to the number of succinic groups in the succinic anhydride reactant.
  • hydrocarbyl succinimides may be represented by the following structure:
  • R and R' are as described herein above and y is 1 to 11.
  • the succinimide dispersant may be post-treated by a reactive boron compound or organic carbonate.
  • Suitable boron compounds that can be used as a source of boron include, for example, boric acid, a boric acid salt, a boric acid ester, and the like.
  • Representative examples of a boric acid include orthoboric acid, metaboric acid, paraboric acid, and the like.
  • Representative examples of a boric acid salt include ammonium borates, such as ammonium metaborate, ammonium tetraborate, ammonium pentaborate, ammonium octaborate, and the like.
  • boric acid ester examples include monomethyl borate, dimethyl borate, trimethyl borate, monoethyl borate, diethyl borate, triethyl borate, monopropyl borate, dipropyl borate, tripropyl borate, monobutyl borate, dibutyl borate, tributyl borate, and the like.
  • Suitable organic carbonates include, for example, cyclic carbonates such as 1,3-dioxolan-2-one (ethylene carbonate); 4-methyl-1,3-dioxolan-2-one(propylene carbonate); 4-ethyl-1,3-dioxolan-2-one(butylene carbonate); 4-hydroxymethyl-1,3- dioxolan-2-one; 4,5-dimethyl-1,3-dioxolan-2-one; 4-ethyl-1,3-dioxolan-2-one; 4,4- dimethyl-1,3-dioxolan-2-one; 4-methyl-5-ethyl-1,3-dioxolan-2-one; 4,5-diethyl-1 ,3- dioxolan-2-one; 4,4-diethyl-1,3-dioxolan-2-one; 1,3-dioxan-2-one; 4,4-dimethyl-1,3- dioxan-2-one; 5,5
  • Suitable cyclic carbonates may be prepared from saccharides such as sorbitol, glucose, fructose, galactose and the like and from vicinal diols prepared from C 1 to C 30 olefins by methods known in the art.
  • Alkyl phosphonic acid may be described as a hydrocarbyl substituted derivative of a phosphonic acid.
  • Phosphonic acids including alkyl phosphonic acids are generally insoluble in base oil due to their diacid structure. This has limited the use of phosphonic acids in lubricating oils.
  • the alkyl phosphonic acid is a monoalkyl phosphonic acid that can be described by the following formula: wherein R is a C 3 -C 20 hydrocarbyl group.
  • R may be saturated or unsaturated.
  • R may be linear, branched, or cyclic.
  • R is aliphatic.
  • R is aromatic.
  • R may be an alkyl, aryl, or alkaryl group.
  • R may include a heteroatom.
  • R may include an ether or thioether moiety.
  • the phosphonic acid may be obtained by any known compatible method.
  • phosphonic acid may be obtained via oxidation of phosphinic acid. Another synthetic pathway involves hydrolysis of dialkyl phosphonate to phosphonic acid under acidic conditions. A more detailed discussion can be found in Beilstein J. Org. Chem. 2017, 13, 2186-2213, which is hereby incorporated by reference.
  • Suitable examples of compatible alkyl phosphonic acids include butyl phosphonic acid, octyl phosphonic acid, decyl phosphonic acid, octadecyl phosphonic acid, and the like.
  • the alkyl phosphonic acid may be pre-mixed with the succinimide dispersant prior to blending with the base oil.
  • the initial pH of such a mixture is between about 5.0 to about 9.5 as measured by ASTM D664. In other embodiments, no pre-mixing is required.
  • the succinimide is usually present in the lubricating oil composition in concentrations ranging from about 0.001 to about 20 wt. % (including, but not limited to, 0.01 to 5 wt. %, 0.2 to 4 wt. %, 0.5 to 3 wt. %, 1 to 2 wt. %, and so forth), based on the total weight of the lubricating oil composition.
  • the phosphonic acid may be present in concentrations ranging from about 0.001 to about 20 wt. % (including, but not limited to, 0.01 to 5 wt. %, 0.02 to 4 wt. %, 0.05 to 3 wt. %, 0.1 to 2 wt. %, and so forth), based on the total weight of the lubricating oil composition.
  • Oils used as the base oil will be selected or blended depending on the desired end use and the additives in the finished oil to give the desired grade of engine oil, e.g. a lubricating oil composition having an Society of Automotive Engineers (SAE) Viscosity Grade of 0W, 0W-8, 0W-16, 0W-20, 0W-30, 0W-40, 0W-50, 0W-60, 5W, 5W- 20, 5W-30, 5W-40, 5W-50, 5W-60, 10W, 10W-20, 10W-30, 10W-40, 10W-50, 15W, 15W-20, 15W-30, or 15W-40.
  • SAE Society of Automotive Engineers
  • the oil of lubricating viscosity (sometimes referred to as “base stock” or “base oil”) is the primary liquid constituent of a lubricant, into which additives and possibly other oils are blended, for example to produce a final lubricant (or lubricant composition).
  • a base oil which is useful for making concentrates as well as for making lubricating oil compositions therefrom, may be selected from natural (vegetable, animal or mineral) and synthetic lubricating oils and mixtures thereof.
  • base stocks and base oils in this disclosure are the same as those found in American Petroleum Institute (API) Publication 1509 Annex E ("API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils," December 2016).
  • Group I base stocks contain less than 90% saturates and/or greater than 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • Group II base stocks contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • Group III base stocks contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 120 using the test methods specified in Table E-1.
  • Group IV base stocks are polyalphaolefins (PAO).
  • Group V base stocks include all other base stocks not included in Group I, II, III, or IV.
  • Natural oils include animal oils, vegetable oils (e.g., castor oil and lard oil), and mineral oils. Animal and vegetable oils possessing favorable thermal oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely as to their crude source, for example, as to whether they are paraffinic, naphthenic, or mixed paraffinic-naphthenic. Oils derived from coal or shale are also useful. Natural oils vary also as to the method used for their production and purification, for example, their distillation range and whether they are straight run or cracked, hydrorefined, or solvent extracted.
  • Synthetic oils include hydrocarbon oil.
  • Hydrocarbon oils include oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylenealphaolefin copolymers).
  • Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oil.
  • PAOs derived from C 8 to C 14 olefins e.g., C 8 , C 10 , C 12 , C 14 olefins or mixtures thereof, may be utilized.
  • base oils include non-conventional or unconventional base stocks that have been processed, preferably catalytically, or synthesized to provide high performance characteristics.
  • Non-conventional or unconventional base stocks/base oils include one or more of a mixture of base stock(s) derived from one or more Gas-to-Liquids (GTL) materials, as well as isomerate/isodewaxate base stock(s) derived from natural wax or waxy feeds, mineral and or non-mineral oil waxy feed stocks such as slack waxes, natural waxes, and waxy stocks such as gas oils, waxy fuels hydrocracker bottoms, waxy raffinate, hydrocrackate, thermal crackates, or other mineral, mineral oil, or even nonpetroleum oil derived waxy materials such as waxy materials received from coal liquefaction or shale oil, and mixtures of such base stocks.
  • Other base oils include Coal to liquid (CTL) products and alkyl-naphthalene.
  • Base oils for use in the lubricating oil compositions of present disclosure are any of the variety of oils corresponding to API Group I, Group II, Group III, Group IV, and Group V oils, and mixtures thereof, preferably API Group II, Group III, Group IV, and Group V oils, and mixtures thereof, more preferably the Group III to Group V base oils due to their exceptional volatility, stability, viscometric and cleanliness features.
  • the base oil will have a kinematic viscosity at 100°C (ASTM D445) in a range of 1.5 to 35 mm 2 /s (e.g., 1.5 to 25 mm 2 /s, 2.0 to 20 mm 2 /s, or 2.0 to 15 mm 2 /s).
  • the present lubricating oil compositions may also contain conventional lubricant additives for imparting auxiliary functions to give a finished lubricating oil composition in which these additives are dispersed or dissolved.
  • the lubricating oil compositions can be blended with antioxidants, ashless dispersants, anti-wear agents, detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifying agents, friction modifiers, metal deactivating agents, pour point depressants, viscosity modifiers, antifoaming agents, co-solvents, package compatibilizers, corrosion-inhibitors, dyes, extreme pressure agents and the like and mixtures thereof.
  • a variety of the additives are known and commercially available. These additives, or their analogous compounds, can be employed for the preparation of the lubricating oil compositions of the invention by the usual blending procedures.
  • each of the foregoing additives when used, is used at a functionally effective amount to impart the desired properties to the lubricant.
  • a functionally effective amount of this ashless dispersant would be an amount sufficient to impart the desired dispersancy characteristics to the lubricant.
  • the concentration of each of these additives, when used may range, unless otherwise specified, from about 0.001 to about 20 wt. %, such as about 0.01 to about 10 wt. %.
  • Lubricating oil samples were evaluated for anti-wear performance. Each sample includes succinimide dispersant, a phosphorus additive (optional in some comparative examples), other lubricating oil additives (friction modifiers, ashless anti-wear additives, antioxidants, metal deactivators, seal swell additives, foam inhibitors, and viscosity modifiers), and base oil.
  • Borated Succinimide 1 is a boron-modified polyisobutenyl succinimide with a polyisobutylene number average molecular weight of 950 (N: 1.95 wt%; B: 0.63 wt%).
  • Borated Succinimide 2 is a boron-modified polyisobutenyl succinimide with a polyisobutylene number average molecular weight of 1,300 (N: 1.88 wt%; B: 0.36 wt%).
  • Succinimide 1 is a polyisobutenyl succinimide with a polyisobutylene number average molecular weight of 950 (N: 2.15 wt%).
  • Succinimide 2 is a polyisobutenyl succinimide with a polyisobutylene number average molecular weight of 950 (N: 2.0 wt%).
  • Succinimide 3 is a low molecular weight alkenyl succinimide (N: 4.6 wt%).
  • Phosphorus additive is a phosphorus-containing compound.
  • Monoalkyl phosphonic acid includes butyl phosphonic acid (P: 22.4 wt%), octyl phosphonic acid (P: 15.7 wt%), and octadecyl phosphonic acid (P: 9.3 wt%).
  • Phosphorus compound 1 is inorganic phosphoric acid H 3 PO 4 (P: 27.0 wt%).
  • Phosphorus compound 2 is 2-ethylhexyl phosphate ester (P: 11.1 wt%).
  • Phosphorus compound 3 is 3-bis(2- methylpropoxy)phosphinothioylthio-2-methyl-propanoic acid, commercially available from BASF under the trade name Irgalube® 353 (P: 9.3 wt%).
  • Phosphorus compound 4 is trilauryl trithiophosphite (P: 4.9 wt%)
  • Phosphorus compound 5 is a mixture of C12, C14, and C18 phosphate ester (P: 8.3 wt%).
  • Phosphorus compound 6 is isotridecyl phosphate ester (P: 8.2 wt%).
  • Phosphorus compound 7 is dimethyl octadecyl phosphonate (P: 8.6 wt%)
  • the anti-wear performance of each lubricating oil compositions was determined using the 4 ball wear scar test (ASTM D4172) at 1200 rpm and 1800 rpm, oil temperature of 80°C, and load of 392N for 60 min. After testing, the test balls were removed and the wear scars were measured. The wear scar diameters are reported in mm in Table 1 and Table 2. A smaller wear scar diameter indicates better anti-wear performance.
  • Comparative examples 1-8 which contain succinimide but do not contain alkyl phosphonic acid showed poor anti-wear performance.
  • inventive examples 1-4 which contain succinimide and C 4 -C 18 alkyl phosphonic acids showed superior anti-wear performance.
  • the electrical insulating ability of the lubricating oil compositions was determined in accordance with JIS C2101-1999-24.
  • the volume resistivity values of several examples were measured at an applied voltage of 250 V and reported in units of ⁇ cm in Table 3.
  • a volume resistivity of greater than 1 x 10 8 ⁇ cm at 80°C is preferred for adequate insulating properties in transmission fluids.
  • ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
  • ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
  • within a range includes every point or individual value between its end points even though not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.
  • compositions, an element or a group of elements are preceded with the transitional phrase “comprising,” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of,” “consisting of,” “selected from the group of consisting of,” or “is” preceding the recitation of the composition, element, or elements and vice versa.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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PCT/IB2021/058338 2020-09-14 2021-09-14 Lubricating oil containing alkyl phosphonic acid WO2022054023A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US18/023,945 US20240101923A1 (en) 2020-09-14 2021-09-14 Lubricating oil containing alkyl phosphonic acid
EP21783050.4A EP4211210A1 (en) 2020-09-14 2021-09-14 Lubricating oil containing alkyl phosphonic acid
AU2021340009A AU2021340009A1 (en) 2020-09-14 2021-09-14 Lubricating oil containing alkyl phosphonic acid
JP2023516492A JP2023541435A (ja) 2020-09-14 2021-09-14 アルキルホスホン酸を含有する潤滑油
CA3193618A CA3193618A1 (en) 2020-09-14 2021-09-14 Lubricating oil containing alkyl phosphonic acid
CN202180062873.3A CN116323878A (zh) 2020-09-14 2021-09-14 含烷基膦酸的润滑油

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AU2021340009A1 (en) 2023-03-30
CN116323878A (zh) 2023-06-23

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