Corrosion inhibition for electric driveline fluids

Abstract

A method for reducing or preventing corrosion in an electric or hybrid vehicle is described. The method involves lubricating an engine of the electric or hybrid vehicle with a lubricating oil composition. The composition includes base oil and a corrosion inhibitor according to Formula (I), Formula (II), or Formula (III) represented by the following: (I), (II), (III), where X is C or N, each R1, R2, R3, R4 and R5 is H or independently a linear or branched-chain hydrocarbyl group having one to about twenty carbon atoms.

Description

T-11920-W001CORROSION INHIBITION FOR ELECTRIC DRIVELINE FLUIDS CROSS-REFERENCE TO RELATED APPLICATION

[0001] The application claims the benefit of U.S. Provisional Patent Application No.63 / 720,641, filed November 14, 2024, which is incorporated by reference herein in its entirety.FIELD OF INVENTION

[0002] The present disclosure relates to electric driveline fluids. More particularly, the present disclosure relates to corrosion inhibitors useful to prevent or reduce corrosion in electric driveline fluids.BACKGROUND OF INVENTION

[0003] Corrosion is a key issue in many types of engines and machines, given the use of metals and metal alloys such as copper, lead and steel for many of their components. In the automotive industry, corrosion has been and remains a concern in conventional gasoline or diesel internal combustion engines, even as alternative engine technologies and alternatively fueled engines are being developed. For example, hydrogen fueled, methanol fueled, or ammonia fueled engines, which typically operate at lower temperatures, may produce or retain more water compared to conventional gasoline or diesel fueled internal combustion engines which may render metal components more susceptible to corrosion. In electric and hybrid vehicles, the engine continually goes through stop-start cycles during normal operation. Therefore, the engine in a hybrid vehicle typically operates for short periods of time, which can lead to the problem of accumulating water (and sometimes fuel) in, for example, the engine oil, as the engine is less able to evaporate water and fuel through prolonged use. Further, there has been a move toward the electrification of vehicle drivelines, either in the form of full electric vehicles, hybrid vehicles or even internal combustion vehicles. While typicalT-11920-W001transmission oils are formulated to prevent or reduce corrosion of metal parts submerged in the oil, corrosion remains a problem for metal surfaces and electrical equipment that are not submerged. Updates to transmissions have led to more sensors being added that reside in the oil’s vapor space. Corrosive species in the vapor phase may interact with these electrical parts and cause corrosion to these elements. Corrosion inhibitory performance for non-submerged electronics is not currently encompassed in vehicle lubricant specifications, but it is anticipated that vapor phase corrosion performance will become increasingly important, particularly with respect to sensitive electronics where even slight corrosion can interrupt the function of the electronics. Corrosion has been studied in the vapor phase, however the corrosion phenomena that have thus far been described are primarily due to atmospheric corrosion (e.g. based on humidity, oxidation and salts), while the corrosion with respect to electronics in the headspace above an automotive lubricant will have significantly different set of environmental contributors (e.g., low humidity, low oxygen, volatile lubricant and lubricant degradation products).

[0004] There is therefore a need to develop further improved compounds for corrosion inhibition, which can be utilized in in both the oil phase and the vapor phase, particularly for electric and hybrid vehicles.SUMMARY OF INVENTION

[0005] In one aspect, there is a method for reducing or preventing corrosion in an electric or hybrid vehicle, the method comprising lubricating an engine of the electric or hybrid vehicle with a lubricating oil composition comprising: base oil; and a corrosion inhibitor according to Formula I, Formula II, or Formula III represented by the following:T-11920-W001wherein X is C or N, each Ri, R2, R3, R4 and Rs is H or independently a linear or branched-chain hydrocarbyl group having one to about twenty carbon atoms.

[0006] In another aspect, there is provided a use of a compound according to Formula I, II, or III,wherein X is C or N, each Ri, R2, R3, R4 and Rs is H or independently a linear or branched-chain hydrocarbyl group having one to about twenty carbon atoms, to inhibit corrosion in an electric vehicle or hybrid electric vehicle, wherein the compound is present in a lubricating oil composition, used to operate the electric vehicle or hybrid electric vehicle.T-11920-W001DETAILED DESCRIPTION OF THE INVENTION

[0007] To facilitate the understanding of the subject matter disclosed herein, a number of terms, abbreviations or other shorthand as used herein are defined below. Any term, abbreviation or shorthand not defined is understood to have the ordinary meaning used by a skilled artisan contemporaneous with the submission of this application.

[0008] As used herein, the following terms have the following meanings, unless expressly stated to the contrary. In this specification, the following words and expressions, if and when used, have the meanings given below.

[0009] As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of features is not necessarily limited only to those features but may include other features not expressly listed or other features that are inherent to such process, method, article, or apparatus. Further, unless expressly stated to the contrary, “or” refers to an inclusive-or and not to an exclusive-or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0010] The use of “a” or “an” is employed to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the embodiments of the disclosure. This description should be read to include one or at least one and the singular also includes the plural, or vice versa, unless it is clear that it is meant otherwise. The term “averaged,” when referring to a value, is intended to mean an average, a geometric mean, or a median value. Group numbers corresponding to columns within the Periodic Table of the elements use the “New Notation” convention as seen in the CRC Handbook of Chemistry and Physics, 81st Edition (2000-2001).T-11920-W001

[0011] All percentages reported are weight % on an active ingredient basis (i.e., without regard to carrier or diluent oil) unless otherwise stated.

[0012] The abbreviation “ppm” means parts per million by weight, based on the total weight of the lubricating oil composition.

[0013] The term “metal” refers to transition metals, post-transition metals, alkali metals, alkaline earth metals, metalloids, or mixtures thereof. Transition metals include any metal found in Groups 3-12 of the periodic table, including titanium, iron, copper, zinc, molybdenum, palladium, and platinum. Post-transition metals include aluminum, gallium, tin and lead. Alkali metals include lithium, sodium and potassium. Alkaline earth metals include calcium, barium, magnesium and strontium. Metalloids include silicon, germanium, and antimony.

[0014] All ASTM standards referred to herein are the most current versions as of the filing date of the present application.

[0015] Unless otherwise specified, all percentages are in weight percent.Compound for use as corrosion inhibitors

[0016] The present disclosure relates to a compound that is particularly useful as a corrosion inhibitor which may be used as additives for lubricating oil compositions.

[0017] Without wishing to be bound by theory, it is believed that the compounds of the present disclosure are able to inhibit corrosion in the vapor phase under performance conditions (i.e., engine environment temperatures) whereby a portion of the compound, may cleave from the compound, and can volatilize such that it exists in the vapor phase and can therefore act as a corrosion inhibitor in the vapor phase as well as the oil phase. As such, the compounds may be used / implemented in a method to inhibit corrosion in an electric vehicle or hybrid electric vehicle, wherein the compound is present in a lubricating oil composition, used to operate theT-11920-W001hybrid electric vehicle. The lubricating oil composition may be an electric vehicle driveline fluid (EDF).

[0018] The compound may be present in the lubricating oil composition used to operate the engine in suitable amounts to maintain, inhibit, reduce or otherwise improve corrosion performance. Reference is made to the description of the lubricating oil compositions above and the various embodiments describing suitable amounts of the compound.

[0019] The corrosion to be inhibited may be copper corrosion. The corrosion to be inhibited may be lead corrosion. The corrosion to be inhibited may be copper and lead corrosion.

[0020] In accordance with one or more aspects of this disclosure, the compound has a structure according to Formula I, II, or III as shown below:Formula IT-11920-W001Formula IIIwherein X is C or N, each Rl, R2, R3, R4 and R5 is H or independently a linear or branched-chain hydrocarbyl group having one to about twenty carbon atoms.

[0021] The term “hydrocarbyl” refers to a moiety that includes both carbon and hydrogen atoms (“hydrocarbon”). Hydrocarbyl may refer to saturated or unsaturated moieties, aliphatic or aromatic moieties, cyclic or acyclic moieties, branched or unbranched moieties.

[0022] The corrosion inhibitor may be present from about 0.01 wt. % to about 20.0 wt. %, including mixtures thereof, based on the total weight of the lubricating oil composition,T-11920-W001such as from about 0.025 wt.% to about 17.50 wt.%, or 0.05 wt.% to about 15.0 wt.%, or about 0.075 wt.% to about 12.50 wt.%, or about 0.1 wt.% to about 10 wt.%, or about 0.2 wt.% to about 7.5 wt.%, or about 0.25 wt.% to about 5.0 wt.%, or about 0.3 wt.% to about 2.5 wt.%, or about 0.35 wt.% to about 1.00 wt.%, or about 0.40 wt.% to about 0.75 wt.% of the compound, including mixtures thereof, based on the total weight of the lubricating oil composition. The compound may be present in about 0.05 wt.% to about 2.50 wt.%, or about 0.075 wt.% to about 2.000 wt.%, or about 0.1 wt.% to about 1.5 wt.%, or about 0.2 wt.% to about 1.0 wt.%, or about 0.3 wt.% to about 0.8 wt.% of the compound, including mixtures thereof, based on the total weight of the lubricating oil composition.Lubricating Oil Composition

[0023] The lubricating oil composition may be suitable for use in an electric vehicle or a hybrid electric vehicle.

[0024] The lubricating oil may comprise an oil of lubricating viscosity (sometimes referred to as “base stock” or “base oil”). The oil of lubricating viscosity may act as the primary liquid constituent of the lubricating oil composition, into which compound, other optional additives and possibly other oils are blended, for example to produce a final lubricant (or lubricating oil 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) lubricating oils, synthetic lubricating oils or mixtures thereof.

[0025] 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. The multigrade oil may have a Society of Automotive Engineers (SAE) viscosity grade of 0W-8, 0W-12, OW-16, 0W-20, 0W-30, 0W-40, 0W-50, 0W-60, 5W, 5W-20, 5W-30, 5W-40, 5W- 50, SWT-11920-W00160, 10W, 10W-20, 10W-30, 10W-40, 10W-50, 15W, 15W-20, 15W-30, 15W-40, 20W-40 or 20W-50. The lubricating oil composition may have an SAE grade of 15W-40.

[0026] Definitions for the 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,” February 2022). 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-l. 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-l. 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-l. 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.

[0027] 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.

[0028] 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 ethylene-alphaolefin copolymers). Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oil. By wayT-11920-W001of example, PAOs derived from C8 to C14 olefins, e.g., C8, CIO, C12, C14 olefins or mixtures thereof, may be utilized.

[0029] Other useful fluids for use as base oils include non-conventional or unconventional base stocks that have been processed, preferably catalytically, or synthesized to provide high performance characteristics.

[0030] 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 non-petroleum 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.

[0031] 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.

[0032] The base oil may be a renewable base oil. Renewable as used herein means any biologically derived composition, including fatty alcohols, olefins, or oligomers. Such compositions may be made, for nonlimiting example, from biological organisms designed to manufacture specific oils, as discussed in WO 2012 / 141784, but do not include petroleum distilled or processed oils such as, for non-limiting example, mineral oils. A suitable method to assess materials derived from renewable resources is through "Standard Test Methods for Determining the Biobased Content of Solid, Liquid, and Gaseous Samples Using RadiocarbonT-11920-W001Analysis" (ASTM D6866-12 or ASTM D6866-11). Counts from 14C in a sample can be compared directly or through secondary standards to SRM 4990C. A measurement of 0% 14C relative to the appropriate standard indicates carbon originating entirely from fossils (e.g., petroleum based). A measurement of 100% 14C indicates carbon originating entirely from modern sources (see, e.g., WO 2012 / 141784, incorporated herein by reference).

[0033] The lubricating oil composition will typically comprise at least about 50 wt. % of base oil based on the total weight of the lubricating oil composition, for example, at least about 60 wt.%, or at least about 70 wt. %, or at least about 80 wt. %, or from about 50 wt. % to about 99 wt. %, or from about 50 wt. % to about 95 wt. %, or from about 50 wt. % to about 90 wt.%, or from about 60 wt. % to about 90 wt. %, or from about 70 wt. % to about 90 wt. %, or from about 80 wt. % to about 90 wt.%.

[0034] The lubricating oil composition may have a high temperature high shear (HTHS) viscosity at 150° C (measured in accordance with ASTM D4683) of 5.2 cP or less, such as 5.1 cP or less, 5.0 cP or less, 4.5 cP or less, 4.0 cP or less, 3.9 cP or less, 3.8 cP or less, 3.7 cP or less, 3.6 cP or less, 3.5 cP or less, 3.4 cP or less, 3.3 cP or less, 3.2 cP or less, 3.1 cP or less, 3.0 cP or less, 2.9 cP or less, 2.8 cP or less, 2.7 cP or less, 2.6 cP or less, 2.5 cP or less, 2.4 cP or less, 2.3 cP or less, 2.2 cP or less, 2.1 cP or less, 2.0 cP or less, 1.9 cP or less, 1.8 cP or less, 1.7 cP or less, 1.6 cP or less, 1.5 cP or less, 1.4 cP or less, 1.3 cP or less, 1.2 cP or less, 1.1 cP or less, or 1.0 cP or less. In some embodiments, the lubricating oil composition may have a HTHS at 150°C from 1.0 to 5.2 cP, such as from 1.0 to 4.5 cP, 1.0 to 4.0 cP, 1.0 to 2.9 cP, 1.3 to 2.9 cP, 1.0 to 2.6 cP, 1.3 to 2.6 cP, 1.0 cP to 2.3 cP, 1.3 cP to 2.3 cP, 1.0 cP to 2.0 cP, 1.3 cP to 2.3 cP, 1.0 cP to 1.7 cP, or 1.3 cP to 1.7 cP. The lubricating oil composition may have a viscosity index of at least 135 (e.g., 135 to 400, or 135 to 250), at least 150 (e.g., 150 to 400, 150 to 250), at least 165 (e.g., 165 to 400, or 165 to 250), at least 190 (e.g., 190 to 400, or 190 to 250), or at least 200 (e.g., 200 to 400, or 200 to 250).T-11920-W001

[0035] The base oil may have a kinematic viscosity at 100°C (measured in accordance with ASTM D445) in a range of 1.4 to 20 mm2 / s such as 3 to 12 mm2 / s, such as 3 to 11 mm2 / s, 3 to 10 mm2 / s, 3 to 9 mm2 / s, 3 to 8 mm2 / s, 3 to 7 mm2 / s, 3 to 6 mm2 / s, 3 to 5 mm2 / s, 3 to 4 mm2 / s, 4 to 12 mm2 / s, 4 to 11 mm2 / s, 4 to 10 mm2 / s, 4 to 9 mm2 / s, 4 to 8 mm2 / s, 4 to 7 mm2 / s, 4 to 6 mm2 / s, 4 to 5 mm2 / s, 5 to 12 mm2 / s, 5 to 11 mm2 / s, 5 to 10 mm2 / s, 5 to 9 mm2 / s, 5 to 8 mm2 / s, 5 to 7 mm2 / s, 5 to 6 mm2 / s, 6 to 12 mm2 / s, 6 to 11 mm2 / s, 6 to 10 mm2 / s, 6 to 9 mm2 / s, 6 to 8 mm2 / s, 6 to 7 mm2 / s, 7 to 12 mm2 / s, 7 to 11 mm2 / s, 7 to 10 mm2 / s, 7 to 9 mm2 / s, 7 to 10 mm2 / s, 7 to 9 mm2 / s, 7 to 8 mm2 / s, 8 to 12 mm2 / s, 8 to 11 mm2 / s, 8 to 10 mm2 / s, 8 to 9 mm2 / s, 9 to 12 mm2 / s, 9 to 11 mm2 / s, 9 to 10 mm2 / s, 10 to 12 mm2 / s, 10 to 11 mm2 / s, or 11 to 12 mm2 / s.

[0036] The lubricating oil composition may comprise one or more further additives. Such additives when present are either dispersed or dissolved in the lubricating oil composition. The one or more further additives may be selected from a detergent, dispersant, e.g., ashless dispersants, antioxidant, viscosity modifier, anti-wear / extreme-pressure agent, molybdenum succinimide, friction modifier, corrosion inhibitor other than the compound according to the first aspect, pour point depressant, foam inhibitor, dehazing agents, demulsifying agents, cosolvents, package compatibilizers, dyes and the like and mixtures thereof.

[0037] The lubricating oil may further comprise one or more detergents. Detergents utilized in lubricating oil compositions generally comprise a polar head comprising a metal salt of an organic acid and a hydrophobic, oil-soluble tail. The detergent may be a metal detergent. The metal may be an alkali or alkaline earth metal. The metal may be Li, Na, K, Mg, or Ca, or a combination thereof. The metal may be Mg or Ca, or a combination thereof. The one or more detergents may be selected from a metal sulfonate, metal phenate, metal salicylate, or metal alkyl hydroxybenzoate or combinations thereof. The one or more detergents may be selected from a metal sulfonate, a metal phenate or a combination thereof. The metal of theT-11920-W001one or more detergents selected from a metal sulfonate, a metal phenate or a combination thereof may be Ca or Mg. The lubricating oil composition may comprise a Ca phenate detergent. The lubricating oil composition may comprise a Mg sulfonate detergent. The lubricating oil composition may comprise a Ca sulfonate detergent.

[0038] The one or more detergents may be neutral. Detergents that contain a stoichiometric amount of the metal are described as neutral. The one or more metal detergents may be overbased. Detergents that contain an excess of metal (i.e., greater than the stoichiometric amount) are described as overbased. The one or more detergents may be overbased and have a TBN of 10 to 650 mg KOH / g, such as 10 to 600 mg KOH / g, 10 to 550 mg KOH / g, 10 to 500 mg KOH / g, 10 to 450 mg KOH / g, 10 to 400 mg KOH / g, 10 to 350 mg KOH / g, 10to300mgKOH / g,10to250mgKOH / g, 10 to 200 mg KOH / g, 10 to 150 mg KOH / g, 10 to 100 mg KOH / g, 10 to 50 mg KOH / g, 10 to 40 mg KOH / g, 10 to 30 mg KOH / g, 10 to 20 mg KOH / g, 50 to 650 mg KOH / g, 50 to 600 mg KOH / g, 50 to 550 mg KOH / g, 50 to 500 mg KOH / g, 50 to 450 mg KOH / g, 50 to 400 mg KOH / g, 50 to 350 mg KOH / g, 50 to 300 mg KOH / g, 50 to 250 mg KOH / g, 50 to 200 mg KOH / g, 50 to 150 mg KOH / g, 50 to 100 mg KOH / g, 100 to 650 mg KOH / g, 100 to 600 mg KOH / g, 100 to 550 mg KOH / g, 100 to 500 mg KOH / g, 100 to 450 mg KOH / g, 100 to 400 mg KOH / g, 100 to 350 mg KOH / g, 100 to 300 mg KOH / g, 100 to 250 mg KOH / g, 100 to 200 mg KOH / g, 100 to 150 mg KOH / g, 150 to 650 mg KOH / g, 150 to 600 mg KOH / g, 150 to 550 mg KOH / g, 150 to 500 mg KOH / g, 150 to 450 mg KOH / g, 150 to 400 mg KOH / g, 150 to 350 mg KOH / g, 150 to 300 mg KOH / g, 150 to 250 mg KOH / g, 150 to 200 mg KOH / g, 200 to 650 mg KOH / g, 200 to 600 mg KOH / g, 200 to 550 mg KOH / g, 200 to 500 mg KOH / g, 200 to 450 mg KOH / g, 200 to 400 mg KOH / g, 200 to 350 mg KOH / g, 200 to 300 mg KOH / g, , 250 to 650 mg KOH / g, 250 to 600 mg KOH / g, 250 to 550 mg KOH / g, 250 to 500 mg KOH / g, 250 to 450 mg KOH / g, 250 to 400 mg KOH / g, 250 to 350 mg KOH / g, 250 to 300 mg KOH / g, 300 to 650 mg KOH / g, 300 to 600 mg KOH / g, 300 to 550T-11920-W001mg KOH / g, 300 to 500 mg KOH / g, 300 to 450 mg KOH / g, 300 to 400 mg KOH / g, 350 to 650 mg KOH / g, 350 to 600 mg KOH / g, 350 to 550 mg KOH / g, 350 to 500 mg KOH / g, 350 to 450 mg KOH / g, 350 to 400 mg KOH / g, 400 to 650 mg KOH / g, 400 to 600 mg KOH / g, 400 to 550 mg KOH / g, 400 to 500 mg KOH / g, 400 to 450 mg KOH / g.

[0039] The term “Total Base Number” or “TBN” as used herein refers to the amount of base equivalent to milligrams of KOH in one gram of sample. Thus, higher TBN numbers reflect more alkaline products, and therefore greater alkalinity. TBN may be determined using the ASTM D2896 test.

[0040] The one or more detergents may comprise an overbased Ca phenate detergent. The overbased Ca phenate detergent may have a TBN of about 50 mg KOH / g to about 600 mg KOH / g, about 100 mg KOH / g to about 500 mg KOH / g, for example, about 150 mg KOH / g to about 400 mg KOH / g, about 200 mg KOH / g to about 300 mg KOH / g, or about 240 mg KOH / g to about 280 mg KOH / g.

[0041] The one or more detergents may comprise an overbased Mg sulfonate detergent. The overbased Mg sulfonate detergent may have a TBN of about 50 mg KOH / g to about 800 mg KOH / g, for example, about 100 mg KOH / g to about 700 mg KOH / g, about 200 mg KOH / g to about 600 mg KOH / g, about 300 mg KOH / g to about 500 mg KOH / g, or about 350 mg KOH / g to about 450 mg KOH / g.

[0042] The one or more detergents may comprise an overbased Ca sulfonate detergent. The overbased Ca sulfonate detergent may have a TBN of about 50 mg KOH / g to about 300 mg KOH / g, for example about 70 mg KOH / g to about 280 mg KOH / g, about 90 mg KOH / g to about 260 mg KOH / g, about 100 mg KOH / g to about 240 mg KOH / g, about 120 mg KOH / g to about 220 mg KOH / g, about 140 to about 200 mg KOH / g, or about 160 mg KOH / g to about 180 mg KOH / g.T-11920-W001

[0043] The one or more detergents may individually be present in the lubricating oil composition in an amount of about 100 ppm to about 2500 ppm, such as about 100 ppm to about 2500 ppm, or about 150 ppm to about 1800 ppm, or about 200 ppm to about 1500 ppm, or about 300 ppm to about 1100 ppm, or about 350 ppm to about 1000 ppm, or about 400 ppm to about 900 ppm in terms of metal content.

[0044] The one or more detergents may comprise an overbased Ca phenate detergent present in the lubricating oil composition in an amount of about 100 ppm to about 2000 ppm, for example, about 200 ppm to about 1800 ppm, about 300 ppm to about 1600 ppm, about 400 ppm to about 1400 ppm, about 500 ppm to about 1200 ppm, about 600 ppm to about 1000 ppm, about 700 ppm to 1000 ppm, about 750 ppm to about 950 ppm, or about 800 ppm to about 900 ppm in terms of calcium content.

[0045] The one or more detergents may comprise an overbased Mg sulfonate detergent present in the lubricating oil composition in an amount of about 100 ppm to about 1500 ppm, for example, about 200 ppm to about 1250 ppm, about 300 ppm to about 1000 ppm, about 400 ppm to about 900 ppm, about 500 ppm to about 800 ppm, about 550 ppm to about 750 ppm, or about 600 ppm to about 700 ppm, in terms of magnesium content.

[0046] The one or more detergents may comprise an overbased Ca sulfonate detergent present in the lubricating oil composition in an amount of about 100 ppm to about 900 ppm, for example about 150 ppm to about 800 ppm, about 200 ppm to about 700 ppm, about 250 ppm to about 600 ppm, about 300 ppm to about 500 ppm, or about 350 ppm to about 450 ppm, in terms of calcium content.

[0047] The lubricating oil composition may comprise one or more detergents such that the total amount of metal from the one or more detergents is less than about 4000 ppm, for example, less than about 3000 ppm, or less than about 2500 ppm, or less than about 2000 ppm, for example, from about 500 ppm to about 3000 ppm, or from about 750 ppm to 2500 ppm, orT-11920-W001from about 1000 to about 2000 ppm, or from about 1500 ppm to about 2000 ppm. The total metal content may be all calcium, all magnesium or a mixture of magnesium and calcium, for example, in a ratio of calcium to magnesium of from about 10:1 to about 1:10, for example, from about 10:1 to about 1:5, or from about 10:1 to about 10:1 to about 1:1, or from about 5:1 to about 1 : 1 or from about 3 : 1 to 1 : 1 or from about 3 : 1 to about 3 :2, or from about 3 : 1 to about 2:1.

[0048] The lubricating oil composition may comprise up to about 20.0 wt. % of detergent, based on the total weight of the lubricating oil composition, for example, from about 0.1 to about 20.0 wt. %, or from about 0.1 to 15.0 wt.%, or from about 0.1 to 10.0 wt. %, or from about 0.2 to about 7.5 wt. %, or from about 0.5 to about 5.0 wt. %, or from about 0.5 to about 3,0 wt.%, or from about 0.5 to about 2.0 wt. %.

[0049] The lubricating oil may further comprise one or more dispersants. The one or more dispersants may be selected from hydrocarbyl succinimides, mixed ester / amides of hydrocarbyl-substituted succinic acids, hydroxyesters of hydrocarbyl -substituted succinic acids, and Mannich condensation products of hydrocarbyl-substituted phenols, formaldehydes, polyamines or combinations thereof. The one or more dispersants may be selected from condensation products of polyamines and hydrocarbyl-substituted phenyl acids. The one or more dispersants may be bis-succinimide dispersants derived from polyalkenyl succinic anhydrides, such as polyisobutenyl succinic anhydride (PIBSA).

[0050] The one or more dispersants may be post-treated by conventional methods by reaction with any of a variety of agents. Among these agents are boron compounds (e.g., boric acid) and cyclic carbonates (ethylene carbonate).

[0051] The one or more dispersants may be a non-borated succinimide dispersant, a borated succinimide dispersant or a combination thereof.T-11920-W001

[0052] The one or more dispersants may be present in an amount of about 0.1 wt. % to about 10 wt. % based on the total weight of the lubricating oil composition, for example, about 0.25 wt.% to about 9.5 wt.%, about 0.5 wt.% to about 9.0 wt.%, about 0.75 wt.% to about 8.5 wt.%, about 1.0 wt.% to about 8.0 wt.%, about 1.5 wt.% to about 7.5 wt.%, about 2.0 wt.% to about 6.5 wt.%, about 2.5 wt.% to about 5.5 wt.%, about 3.5 wt.% to about 4.5 wt.%.

[0053] The lubricating composition may comprise one or more antioxidants. The one or more antioxidants may be selected from alkylated phenols or diarylamines, sulfur-containing antioxidants, or combinations thereof. The one or more antioxidants may include phenolic antioxidants which may be selected from 2,6-di-tert-butylphenol, mixtures of tert-butylated phenols, 2,6-di-tert-butyl-4-methylphenol, ,6-di-tert-butyl-p-cresol, and 2,6-di-tert-butyl-4-(2-octyl-3 -propanoic) phenol, 4,4'-methylenebis(2,6-di-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and mixed methylene-bridged polyalkyl phenols, 4,4'-thiobis(2-methyl-6-tert-butylphenol) and combinations thereof. The one or more antioxidants may include aminic antioxidants which may be selected from 3 -hydroxy diphenylamine, N-phenyl-1 ,2-phenylenediamine, N-phenyl- 1 ,4-phenylenediamine, mono / dibutyldiphenylamine, mono / dioctyldiphenylamine, mono / dinonyldiphenylamine, mono / ditetradecyldiphenylamine, phenyl-alpha-naphthylamine, and combinations thereof. The one or more antioxidants may include a sulfur-containing antioxidant which may be selected from, sulfurized olefins derived from C4-C25 alpha-olefins and a sulfur source such as elemental sulfur, sulfur monochloride, sulfur dichloride, sodium sulfide, sodium polysulfide, and combinations thereof.

[0054] The one or more antioxidants may be present in an amount of about 0.1 wt.% to about 10.0 wt.%, based on the total weight of the lubricating oil compositions, for example, about 0.25 wt.% to about 9.5 wt.%, about 0.5 wt.% to about 9.0 wt.%, about 0.75 wt.% to about 8.5 wt.%, about 1.0 wt.% to about 8.0 wt.%, about 1.25 wt.% to about 7.0 wt.%, about 1.5 wt.%T-11920-W001to about 6.00 wt.%, about 1.75 wt.% to about 5.0 wt.%, about 2.0 wt.% to about 4.0 wt.%, or about 2.0 wt.% to about 3.0 wt.%.

[0055] The lubricating composition may comprise one or more viscosity modifiers (also known as viscosity index improvers). The one or more viscosity modifiers may be selected from polyolefins, olefin copolymers, ethyl ene / propylene copolymers, polyisobutenes, hydrogenated styrene-isoprene polymers, styrene / maleic ester copolymers, hydrogenated styrene / butadiene copolymers, hydrogenated isoprene polymers, alpha-olefin maleic anhydride copolymers, polymethacrylates, polyacrylates, polyalkyl styrenes, hydrogenated alkenyl aryl conjugated diene copolymers, or combinations thereof.

[0056] The one or more viscosity modifiers may be present in an amount of about 0.1 wt. % to about 20 wt. %, based on the total weight of the lubricating oil composition, for example, about 0.1 wt. % to about 15.0 wt. %, about 0.1 wt.% to about 10.0 wt. %, about 0.1 wt. % to about 5.0 wt. %, or about 0.5 wt. % to about 5.0 wt.

[0057] The lubricating composition may comprise one or more antiwear agents. The one or more antiwear agents may be selected from metal thiosphosphates, metal dialkyldithiophosphates, phosphoric acid esters or salts thereof, phosphate esters, phosphites, phosphonates, sulfurized olefins, thiocarbamate-containing compounds including, thiocarbamate esters, alkylene-coupled thiocarbamates, bis(S-alkyldithiocarbamyl) disulfides and combinations thereof. The one or more antiwear agents may comprise a metal dialkyldithiophosphate, for example, a zinc dialkyldithiophosphate.

[0058] The one or more antiwear agents may be or comprise a zinc dialkyldithiophosphate which may be present in the lubricating oil composition in an amount of 100 ppm to about 2000 ppm, such as about 150 ppm to about 1800 ppm, about 200 ppm to about 1500 ppm, about 300 ppm to about 1250 ppm, about 400 ppm to about 1000 ppm, aboutT-11920-W001500 ppm to about 900 ppm, about 600 ppm to about 800 ppm, or about 700 to about 800 ppm in terms of phosphorus.

[0059] The zinc dithiophosphate may have the following formula:

[0060] Zn[S-P(=S)(ORl)(OR2)]2, wherein R1 and R2 may be the same or different hydrocarbyl radicals having from 1 to 18 (e.g., 2 to 12) carbon atoms and including radicals such as alkyl, alkenyl, aryl, arylalkyl, alkaryl and cycloaliphatic radicals. The R1 and R2 groups may be alkyl groups having from 2 to 8 carbon atoms (e.g., the alkyl radicals may be ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, or 2-ethylhexyl). The zinc dihydrocarbyl dithiophosphate can therefore include zinc dialkyl dithiophosphates (ZDDP). The zinc dialkyl dithiophosphate can be a primary zinc dialkyl dithiophosphate containing primary alkyl groups, or secondary zinc dialkyl dithiophosphate containing secondary alkyl groups, or mixtures thereof.

[0061] The lubricating composition may comprise one or more friction modifiers. The one or more friction modifiers may comprise metal containing and metal-free friction modifiers and may include, but are not limited to, imidazolines, aliphatic fatty acid amides, aliphatic amines, succinimides, alkoxylated aliphatic amines, ether amines, alkoxylated ether amines, amine oxides, amidoamines, nitriles, betaines, quaternary amines, imines, amine salts, amino guanidine, alkanolamides, phosphonates, metal-containing compounds, glycerol esters, sulfurized fatty compounds and olefins, sunflower oil other naturally occurring plant or animal oils, dicarboxylic acid esters, esters or partial esters of a polyol and one or more aliphatic or aromatic carboxylic acids, and combinations thereof.

[0062] The lubricating composition may comprise one or more further rust or corrosion inhibitors, other than the compound of the first aspect. Metal passivators are a type of corrosion inhibitor that binds to the surface of a metal to form a protective film, thereby passivating the metal surface.T-11920-W001

[0063] The one or more rust or corrosion inhibitors may be selected from ether amines, polyethoxylated compounds, mono- and polycarboxylic acids derived from fatty acids, and combinations thereof. Metal passivators may be selected from thiazoles, triazoles, and thiadiazoles such as benzotriazole, tolyltri azole, decyltriazole, dodecyltriazole, 2— mercaptobenzotriazole, 2,5-dimercapto-l,3,4-thiadiazoles, and combinations thereof.

[0064] The lubricating composition may comprise one or more foam inhibitors. Foam inhibitors are used to reduce or prevent stable foams in the lubricating oil composition. The one or more foam inhibitors may be selected from silicon-based polymers such as polysiloxanes. The one or more foam inhibitors may be selected from non-silicon-based organic polymers such as polyacrylates such as ethyl acrylate / 2-ethylhexylacrylate copolymers.

[0065] The one or more foam inhibitors may be present in the lubricating oil composition in an amount of about 1 ppm to about 100 ppm, for example, 2 ppm to about 90 ppm, about 5 ppm to about 80 ppm, about 7 ppm to about 70 ppm, about 10 ppm to about 60 ppm, about 15 ppm to about 50 ppm, about 20 ppm to about 40 ppm, or about 20 ppm to about 30 ppm.

[0066] The lubricating oil composition may comprise metal detergent (e.g., calcium and / or magnesium detergent), dispersant (e.g., borated and / or non-borated succinimide dispersant), antiwear agent (e.g., zinc dialkyldithiophosphate), molybdenum succinimide, antioxidant (e.g., phenolic antioxidant) and optionally foam inhibitor (e.g., silicon-based foam inhibitor). The amounts of each of these additives may be as described above for each individual additive.

[0067] The lubricating oil composition may comprise a total amount of additives of no more than about 50 wt. % of the total weight of the lubricating oil composition. For example, the lubricating oil composition may comprise from about 1.0 to about 25.0 wt. %., about 2.0T-11920-W001wt.% to about 20 wt.%, about 3.0 wt.% to about 15 wt.%, about 4.0 wt.% to about 12.5 wt.%, about 5.0 wt.% to about 10 wt.%.

[0068] Unless otherwise stated, each of the foregoing additives, when used, is used at a functionally effective amount to impart the desired properties to the lubricant. Thus, for example, if an additive is an ashless dispersant, a functionally effective amount of this ashless dispersant would be an amount sufficient to impart the desired dispersancy characteristics to the lubricant. Generally, 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. %.Uses of and methods utilizing the compound to inhibit corrosion

[0069] As described above, the corrosion inhibitor (i.e., to improve (i.e., inhibit / reduce) corrosion), for example, in a lubricating oil composition. As such, the lubricating oil may be formulated to maintain, enhance or improve corrosion performance. The compounds may be used as corrosion inhibitors to reduce corrosion of metal parts, (i.e., corrodible metal components), such as those made from or comprising the likes of iron, aluminum, copper, zinc, tin, lead and their alloys, as well as steel. Metal parts include the likes of cam followers and bearings. The compounds may be used to reduce corrosion of electrical components, (e.g., stator, sensors and the like).

[0070] The lubricating oil composition may be a function fluid or an engine lubricant. The lubricating oil composition may be a transmission oil. The lubricating oil composition may be a gear oil. The lubricating oil composition may be a hydraulic fluid. The lubricating oil composition may be a brake fluid. The lubricating oil composition may be a cooling fluid, for example, for an immersion cooling system.T-11920-W001

[0071] The following non-limiting examples are illustrative of the present invention. Brief descriptions of how the examples were prepared are provided.EXAMPLESSolution Phase Copper Corrosion Test

[0072] The copper strip corrosion test (ASTM D130) is designed to assess the relative degree of corrosivity of a petroleum product. A freshly polished copper strip is immersed in a specific volume of the sample being tested and heated under conditions of temperature and time that are specific to the class of material being tested. At the end of the heating period, the copper strip is removed, washed and the color and tarnish level assessed against the ASTM Copper Strip Corrosion Standard, summarized in the tables below.Vapor Phase Copper Corrosion Test

[0073] To assess the vapor phase corrosivity of the lubricating oil, a modified ASTM D130 method is utilized. A freshly polished copper strip is placed inside of a 100 mL jar, filled with lubricating oil (47g) to half-immerse the copper strip, sealed with a cork stopper and placed inside a temperature-controlled oven (150 °C). Corrosion of the vapor space (i.e. unimmersed) portion of the copper strip is assed per the ASTM Copper Strip Corrosion Standard after a period of time of 168 hours.

[0074] Compound 1 (shown below) was purchased from BASF Chemical Co.Compound 1T-11920-W001

[0075] Compound 2 (shown below) was purchased from Vanderbilt Chemicals, LLC.Compound 2

[0076] Compound 3 was synthesized according to the following.

[0077] A 2 L, 3-neck round bottom flask equipped with an overhead stirrer, Dean-Stark apparatus, nitrogen sparge tube inlet, and thermocouple was charged with bis(2-ethylhexyl)amine (714.67 g, 2.96 mol, 1 equiv.) and benzimidizole (350.08 g, 2.96 mol, 1 equiv.) at room temperature under N2 atmosphere. The reaction mixture was heated with stirring to 60°C. Paraformaldehyde (89.05 g, 2.96 mol, 1 equiv.) was added to the reaction mixture. The reaction was held at 60°C and stirred for 3 hr. Reaction progress was monitored by FT-IR, ESLMS, and 1H-NMR. Once complete, the reaction was held under vacuum to remove water. Once bubbles stopped forming in the reaction mixture, the reaction was confirmed complete by FT-IR and 1H-NMR. The product was collected as a colorless oil (1.1

[0078] Compound 5 (shown below) was purchased from BASF Chemical Co.T-11920-W001Compound 5

[0079] Compound 6 was synthesized according to the following.

[0080] A 500 mL, 4-neck round bottom flask equipped with an overhead stirrer, Dean- Stark apparatus, nitrogen sparge tube inlet, and thermocouple was charged with bis(nonylphenyl)amine (295 g, 0.7 mol, 1 equiv.) and 1,2,4-triazole (44.4 g, 0.63 mol, 0.9 equiv.) at room temperature under N2 atmosphere. The reaction mixture was heated with stirring to 80°C. Paraformaldehyde (19.9 g, 0.63 mol, 0.9 equiv.) was then added to the reaction mixture, which was held at 80°C and stirred for 24 hr. Reaction progress was monitored by FT-IR, ACPI-MS, and 1H-NMR. Once complete, the reaction was held under vacuum to remove water. Once bubbles stopped forming in the reaction mixture, the reaction was confirmed complete by FT-IR. The product was collected as a dark yellow oil (340.1 g).>

[0081] Compound 7 was synthesized according to the following.

[0082] A 2 L, 4-neck round bottom flask equipped with an overhead stirrer, Dean-Stark apparatus, nitrogen sparge tube inlet, and thermocouple was charged with OLOA 19022 (777.27 g, 1.843 mol, 1 equiv.) and imidazole (115.22 g, 1.659 mol, 0.9 equiv.) at roomT-11920-W001temperature under N2 atmosphere. The reaction mixture was heated with stirring to 80°C. Paraformaldehyde (52.443 g, 1.659 mol, 0.9 equiv.) was then added to the reaction mixture, which was held at 80°C and stirred for 26 hr. Reaction progress was monitored by FT-IR, ACPI-MS, and 1H-NMR. Once complete, the reaction was held under vacuum to remove water. Once bubbles stopped forming in the reaction mixture, the reaction was confirmed complete by FT-IR. The product was collected as a dark yellow oil (829.6 g).

[0083] The compounds were formulated into finished oils and tested for vapor rating and copper strip rating. The Vapor Rating and Copper Strip Rating results of Inventive Examples 1 to 3 (Inv Ex 1-3) demonstrate an enhanced ability to inhibit corrosion compared to Comparative Examples 1-3 (Comp Ex 1-3).TABLE: 1T-11920-W001

[0084] The Vapor Rating and Copper Strip Rating for Compounds 5-7 are represented in Table 2.

[0085] The Vapor Rating and Copper Strip Rating results of Inventive Examples 4-7 (Inv Ex 4-7) demonstrate an enhanced ability to inhibit corrosion compared to Comparative Examples 4 and 5 (Comp Ex 4 and 5).Table 2

Claims

T-11920-W001CLAIMS1. A method for reducing or preventing corrosion in an electric or hybrid vehicle, the method comprising lubricating an engine of the electric or hybrid vehicle with a lubricating oil composition comprising:base oil; anda corrosion inhibitor according to Formula I, Formula II, or Formula III represented by the following:wherein X is C or N, each Ri, R2, R3, R4 and Rs is H or independently a linear or branched-chain hydrocarbyl group having one to about twenty carbon atoms.

2. The method of claim 1, wherein the corrosion inhibitor is present in 0.01 wt. % to 20 wt. % based on the total weight of the lubricating oil composition.

3. The method of claim 1, wherein the base oil is present in 50 wt. % or greater, based on the total weight of the lubricating oil composition.T-11920-W0014. The method of claim 1, wherein the lubricating oil composition comprises one or more additives selected from a detergent, dispersant, antioxidant, molybdenum succinimide, viscosity modifier, antiwear / extreme-pressure agent, friction modifier, pour point depressant and foam inhibitor.

5. The method of claim 1, wherein the lubricating oil composition comprises a metal detergent (e.g., calcium and / or magnesium detergent), dispersant (e.g., borated and / or non-borated succinimide dispersant), antiwear agent, molybdenum succinimide, antioxidant and optionally a foam inhibitor.

6. The method of claim 1, wherein the lubricating oil is an electric driveline fluid.

7. The method of claim 1, wherein the corrosion is copper corrosion or lead corrosion.

8. Use of a compound according to Formula I, II, or III,wherein X is C or N, each Ri, R2, R3, R4 and Rs is H or independently a linear or branched-chain hydrocarbyl group having one to about twenty carbon atoms, to inhibit corrosion in anT-11920-W001electric vehicle or hybrid electric vehicle, wherein the compound is present in a lubricating oil composition, used to operate the electric vehicle or hybrid electric vehicle.

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