Low molecular weight dispersants

Abstract

The present disclosure describes a lubricating oil composition comprising a major amount of a base oil; [Formula 1] TIFF2025515825000035.tif37165 (In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R 3 are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. and a lubricant additive having the formula:

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Patent Application No. 63 / 339,569, filed May 9, 2022, which is incorporated by reference in its entirety.

[0002] The present disclosure relates to lubricant additive compositions and lubricating oil compositions containing same. More specifically, the present disclosure describes low molecular weight dispersants that improve engine cleanliness. [Background technology]

[0003] Automotive engines are constantly being improved, and developing new engine oils and additive packages provides a faster and / or more cost-effective direction for improving performance factors such as fuel efficiency, oxidation stability, and volatility.

[0004] Oxidative stability is an important performance factor because poor oxidative stability often leads to the formation of deposits that can cause engine stalling and poor acceleration. Furthermore, deposits can increase fuel consumption as well as the production of harmful exhaust pollutants. Summary of the Invention

[0005] In one embodiment, a major amount of a base oil; and a solvent having the following structure: [ka] (In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R 3are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. and a lubricant additive having the formula:

[0006] In another aspect, a method of lubricating an engine comprises: [ka] (In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R 3 are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. and a lubricant additive having the formula:

[0007] In yet another aspect, a method for improving piston cleanliness or oxidation control in an engine comprises: a major amount of a base oil; The following structure: [ka] (In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R3 are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. and a lubricant additive having the formula: DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] Where combinations, subsets, groups, etc. of elements (e.g., combinations of components in a composition or combinations of steps in a method) are disclosed, it is understood that specific reference to each of the various individual and collective combinations and permutations of those elements is specifically contemplated and described herein, although it may not be explicitly disclosed.

[0009] The present disclosure relates to lubricant additives that prevent or reduce the formation of deposits (e.g., reduce soot deposits on pistons), thus improving engine cleanliness. The lubricant additives can be blended into a base oil along with other lubricant additives to impart performance benefits to the resulting lubricant composition.

[0010] In some embodiments, the present disclosure relates to engine flush products containing the additives, mixed products containing the additives and used lubricant oil compositions, and methods of use thereof.

[0011] In some embodiments, the engine flush product is an aftermarket additive package in which the additives are dissolved in a solvent. The aftermarket additive package is suitable for rapidly cleaning or removing accumulated deposits, sludge, and other contaminants from an internal combustion engine.

[0012] The engine flush process can remove sludge, heavy deposits, and / or other contaminants that may have accumulated from the engine oil. A typical engine flush process involves adding an additive as an aftermarket additive (such as an engine flush product) to an internal combustion engine through the fuel filler. After idling the engine, the additive is added and mixed with an existing lubricating oil composition having a "used base oil". This mixed product can dissolve or clean the sludge, heavy deposits, and / or contaminants present in the engine. The mixed product is then discharged with the dissolved sludge, deposits, and / or contaminants.

[0013] In some embodiments, the lubricating oil compositions disclosed herein can be used as a quick-wash fluid. The quick-wash fluid can be used during a quick-wash service to remove accumulated deposits, sludge, and other soils from an internal combustion engine. The quick-wash service can remove sludge, heavy deposits, and / or other insoluble materials that may have accumulated over time.

[0014] The cleaning process may consist of circulating the lubricant with the lubricant in the engine sump or crankcase without starting the engine. An additional step may include circulating the lubricant and allowing it to soak for 15 minutes, 30 minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 16 hours, 20 hours, 24 hours, 2 days, 3 days, 4 days, 5 days, 6 days, or 1 week under stationary conditions. Another cleaning step may include starting the engine and running it for 15 minutes, 30 minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 16 hours, 20 hours, 24 hours, 2 days, 3 days, 4 days, 5 days, 6 days, or 1 week under any operating conditions appropriate for the engine design and fuel. In some embodiments, the lubricating oil compositions disclosed herein may be used to remove existing deposits from the crankcase, rocker covers, camshaft areas, timing gear covers, cylinder heads, combustion chambers, piston rings, and / or ring grooves of an internal combustion engine.

[0015] When used during a quick flush service, the lubricating oil composition may require a higher concentration of lubricant additive than is typically used during scheduled maintenance. This lubricating oil with the higher amount of deposit cleaning lubricant additive is used to lubricate and clean the engine. The resulting mixed product (concentrated lubricant and sediments) can then be flushed. The flushing step typically occurs after the completion of the cleaning step.

[0016] In some embodiments, the wash step of the rapid wash service involves lubricating the engine with the lubricating oil composition for 15 minutes, 30 minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 16 hours, 20 hours, 24 hours, 2 days, 3 days, 4 days, 5 days, 6 days, or 1 week. The exact time can vary depending on many factors, such as, but not limited to, the size of the engine, the amount of deposits in the engine, and the level of cleanliness desired.

[0017] In some embodiments, flushing occurs 5 minutes, 15 minutes, 30 minutes, 45 minutes, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 8 hours, 12 hours, 16 hours, 24 hours, 2 days, 3 days, 4 days, 1 week, 2 weeks, 3 weeks, 4 weeks, 6 weeks, 8 weeks after the cleaning step. In some embodiments, the flushing step can occur up to a period corresponding to about 25% of the OEM recommended oil change interval period.

[0018] In some embodiments, the lubricating oil compositions, quick wash fluids, or engine flush products disclosed herein have a total base number (TBN) of 2 to 200 mg KOH / g, such as 2 to 175, 2 to 150, 2 to 100, 5 to 200, 5 to 175, 5 to 150, 5 to 100, 10 to 200, 10 to 175, 10 to 150, 10 to 100, 50 to 200, 50 to 175, 50 to 150, and 50 to 100.

[0019] Lubricant Additives The lubricant additive compositions of the present disclosure have the following generalized chemical structure I: [ka] (In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R 3 are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. In some embodiments, X is a cyclic or non-cyclic alkyl group. In some embodiments, Y can include one or more hydrogens. In some preferred embodiments, Z is nitrogen.

[0020] Each R 1are independently 10 to 400 carbon atoms, e.g., 10 to 390, 10 to 380, 10 to 370, 10 to 360, 10 to 350, 10 to 340, 10 to 330, 10 to 320, 10 to 310, 10 to 300, 10 to 290, 10 to 280, 10 to 270, 10 to 260, 10 to 250, 10 to 240, 10 to 230, 10 to 220, 10 to 210, 10 to 200, 10 to 190, 10 to 180, 10 to 170, 10 to 160, 10 to 150, 10 to 140, 10 to 130, 10 to 120, 10 to 110, 10 to 100, 10 to 90, 10 to 80, 10 to 7 0, 10~60, 10~50, 10~40, 10~30, 10~20, 20~400, 20~390, 20~380, 20~370, 20~360, 20~350, 20~340, 20~330, 20~320, 20~310, 20~300, 20~290, 20~280, 2 0~270, 20~260, 20~250, 20~240, 20~230, 20~220, 20~210, 20~200, 20~190, 20~180, 20~170, 20~160, 20~150, 20~140, 20~130, 20~120, 20~110, 20~100, 20~90, 20~80, 20~70, 20~60, 20~50, 20~40, 20~30, 30~400, 30~390, 30~380, 30~370, 30~360, 30~350, 30~340, 30~330, 30~320, 30~310, 30~300, 30~29 0, 30~280, 30~270, 30~260, 30~250, 30~240, 30~230, 30~220, 30~210, 30~200, 30~190, 30~180, 30~170, 30~160, 30~150, 30~140, 30~130, 30~120, 30~1 10, 30~100, 30~90, 30~80, 30~70, 30~60, 30~50, 30~40, 40~400, 40~390, 40~380, 40~370, 40~360, 40~350, 40~340, 40~330, 40~320, 40~310, 40~300, 4 0~290, 40~280, 40~270, 40~260, 40~250, 40~240, 40~230, 40~220, 40~210, 40~200, 40~190, 40~180, 40~170, 40~160, 40~150, 40~140, 40~130, 40~120,40~110、40~100、40~90、40~80、40~70、40~60、40~50、50~400、50~390、50~380、50~370、50~360、50~350、50~340、50~330、50~320、50~310、50~300、50~290、50~280、50~270、50~260、50~250、50~240、50~230、50~220、50~210、50~200、50~190、50~180、50~170、50~160、50~150、50~140、50~130、50~120、50~110、50~100、50~90、50~80、50~70、50~60、60~400、60~390、60~380、60~370、60~360、60~350、60~340、60~330、60~320、60~310、60~300、60~290、60~280、60~270、60~260、60~250、60~240、60~230、60~220、60~210、60~200、60~190、60~180、60~170、60~160、60~150、60~140、60~130、60~120、60~110、60~100、60~90、60~80、60~70、70~400、70~390、70~380、70~370、70~360、70~350、70~340、70~330、70~320、70~310、70~300、70~290、70~280、70~270、70~260、70~250、70~240、70~230、70~220、70~210、70~200、70~190、70~180、70~170、70~160、70~150、70~140、70~130、70~120、70~110、70~100、70~90、70~80、80~400、80~390、80~380、80~370、80~360、80~350、80~340、80~330、80~320、80~310、80~300、80~290、80~280、80~270、80~260、80~250、80~240、80~230、80~220、80~210、80~200、80~190、80~180、80~170、80~160、80~150、80~140、80~130、80~120、80~110、80~100、80~90、90~400、90~390、90~380、90~370、90~360、90~350、90~340、90~330、90~320、90~310、90~300、90~290、90~280、90~270、90~260、90~250、90~240、90~230、90~220、90~210、90~200、90~190、90~180、90~170、90~160、90~150、90~140、90~130、90~120、90~110、90~100、100~400、100~390、100~380、100~370、100~360、100~350、100~340、100~330、100~320、100~310、100~300、100~290、100~280、100~270、100~260、100~250、100~240、100~230、100~220、100~210、100~200、100~190、100~180、100~170、100~160、100~150、100~140、100~130、100~120、100~110、110~400、110~390、110~380、110~370、110~360、110~350、110~340、110~330、110~320、110~310、110~300、110~290、110~280、110~270、110~260、110~250、110~240、110~230、110~220、110~210、110~200、110~190、110~180、110~170、110~160、110~150、110~140、110~130、110~120、120~400、120~390、120~380、120~370、120~360、120~350、120~340、120~330、120~320、120~310、120~300、120~290、120~280、120~270、120~260、120~250、120~240、120~230、120~220、120~210、120~200、120~190、120~180、120~170、120~160、120~150、120~140、120~130、130~400、130~390、130~380、130~370、130~360、130~350、130~340、130~330、130~320、130~310、130~300、130~290、130~280、130~270、130~260、130~250、130~240、130~230、130~220、130~210、130~200、130~190、130~180、130~170、130~160、130~150、130~140、140~400、140~390、140~380、140~370、140~360、140~350、140~340、140~330、140~320、140~310、140~300、140~290、140~280、140~270、140~260、140~250、140~240、140~230、140~220、140~210、140~200、140~190、140~180、140~170、140~160、140~150、150~400、150~390、150~380、150~370、150~360、150~350、150~340、150~330、150~320、150~310、150~300、150~290、150~280、150~270、150~260、150~250、150~240、150~230、150~220、150~210、150~200、150~190、150~180、150~170、150~160、160~400、160~390、160~380、160~370、160~360、160~350、160~340、160~330、160~320、160~310、160~300、160~290、160~280、160~270、160~260、160~250、160~240、160~230、160~220、160~210、160~200、160~190、160~180、160~170、170~400、170~390、170~380、170~370、170~360、170~350、170~340、170~330、170~320、170~310、170~300、170~290、170~280、170~270、170~260、170~250、170~240、170~230、170~220、170~210、170~200、170~190、170~180、180~400、180~390、180~380、180~370、180~360、180~350、180~340、180~330、180~320、180~310、180~300、180~290、180~280、180~270、180~260、180~250、180~240、180~230、180~220、180~210、180~200、180~190、190~400、190~390、190~380、190~370、190~360、190~350、190~340、190~330、190~320、190~310、190~300、190~290、190~280、190~270、190~260、190~250、190~240、190~230、190~220、190~210、190~200、200~400、200~390、200~380、200~370、200~360、200~350、200~340、200~330、200~320、200~310、200~300、200~290、200~280、200~270、200~260、200~250、200~240、200~230、200~220、200~210、210~400、210~390、210~380、210~370、210~360、210~350、210~340、210~330、210~320、210~310、210~300、210~290、210~280、210~270、210~260、210~250、210~240、210~230、210~220、220~400、220~390、220~380、220~370、220~360、220~350、220~340、220~330、220~320、220~310、220~300、220~290、220~280、220~270、220~260、220~250、220~240、220~230、230~400、230~390、230~380、230~370、230~360、230~350、230~340、230~330、230~320、230~310、230~300、230~290、230~280、230~270、230~260、230~250、230~240、240~400、240~390、240~380、240~370、240~360、240~350、240~340、240~330、240~320、240~310、240~300、240~290、240~280、240~270、240~260、240~250、250~400、250~390、250~380、250~370、250~360、250~350、250~340, 250~330, 250~320, 250~310, 250~300, 250~290, 250~280, 250~270, 250~260, 260~400, 260~390, 260~380, 260~370, 260~360, 260~35, 0, 260~340, 260~330, 260~320, 260~310, 260~300, 260~290, 260~280, 260~270, 270~400, 270~390, 270~380, 270~370, 270~360, 270~350, 270~340, 270~330, 270~320, 270~310, 270~300, 270~290, 270~280, 280~400, 280~390, 280~380, 280~370, 280~360, 280~350, 280~340, 280~330, 280~320, 280~310, 280~300, 280~290, 290~400, 290~390, 290~380, 290~370, 290~360, 290~350, 290~340, 290~330, 290~320, 290~310, 290~300, 300~400, 300~390, 300~380, 300~370, 300~360, 300~350, 300 ~340, 300~330, 300~320, 300~310, 310~400, 310~390, 310~380, 310~370, 310~360, 310~350, 310~340, 310~330, 310~320, 320~400, 320~390, 320~380, 320~370, 320~360, 320~350, 320~340, 320~330, 330~400, 330~390, 330~380, 330~370, 330~36 A moiety containing 0, 330-350, 330-340, 340-400, 340-390, 340-380, 340-370, 340-360, 340-350, 350-400, 350-390, 350-380, 350-370, 350-360, 360-400, 360-390, 360-380, 360-370, 370-400, 370-390, 370-380, 380-400, 380-390, or 390-400 carbon atoms.

[0021] In some embodiments, R 1 may include, for example, saturated and unsaturated hydrocarbon groups, straight and branched chain alkyl groups, and polyalkyl groups (e.g., polyisobutenyl groups or "PIB", polyethylene, polypropylene, etc.) The polyalkyl groups may be those resulting from polymerization reactions using olefin monomers (e.g., isobutylene).

[0022] In some preferred embodiments, R 1 is a polyisobutenyl group. In some preferred embodiments, the polyisobutenyl group has an average molecular weight of about 350 to about 5000. In some preferred embodiments, the polyisobutenyl group has an average molecular weight of about 150 to about 1250, for example, about 200 to about 1200, about 300 to about 1100, about 400 to about 1000, about 500 to about 900, and about 600 to about 800. In some preferred embodiments, the polyisobutenyl group has an average molecular weight of about 250 to about 1000, for example, about 300 to about 900, about 400 to about 800, and about 500 to about 700.

[0023] In some preferred embodiments, the polyisobutenyl group is about 500 to about 4000, for example, about 600 to about 5000, about 700 to about 5000, about 800 to about 5000, about 900 to about 5000, about 1000 to about 5000, about 500 to about 4000, for example, about 600 to about 4000, about 700 to about 4000, about 800 to about 4000, about 900 to about 4000, about 1000 to about 4000, about 1100 to about 4000, about 1200 to about 4000, about 1300 to about 4000, about 1400 to about 4000, about 1500 to about 4000, about 1600 to about 4000, about 170 0 to about 4000, about 1800 to about 4000, about 1900 to about 4000, about 2000 to about 4000, about 2100 to about 4000, about 2200 to about 4000, about 2300 to about 4000, about 2400 to about 4000, about 2500 to about 4000, about 2600 to about 4000, about 2700 to about 4000, about 2800 to about 4000, about 2900 to about 4000, about 3000 to about 4000, about 500 to about 3500, for example, 600 to about 3500, about 700 to about 3500, about 800 to about 3500, about 900 to about 3500, about 1000 to about 3500, about 1100 to about 3500, about 1200 to about 3500, about 1300 to about 3500, about 1400 to about 3500, about 1500 to about 3500, about 1600 to about 3500, about 1700 to about 3500, about 1800 to about 3500, about 1900 to about 3500, about 2000 to about 3500, about 2100 to about 3500, about 2200 to about 3500, about 2300 to about 3500, about 2400 to about 3500, about 2500 to about 3500, about 2600 to about 3500, about 2700 to about 3500, about 2800 to about 3500, about 2900 to about 3500, about 3000 to about 3500, about 500 to about 3000, for example, about 60 The average molecular weight of the copolymer is from 0 to about 3000, from about 700 to about 3000, from about 800 to about 3000, from about 900 to about 3000, from about 1000 to about 3000, from about 1100 to about 3000, from about 1200 to about 3000, from about 1300 to about 3000, from about 1400 to about 3000, from about 1500 to about 3000, from about 1600 to about 3000, from about 1700 to about 3000, from about 1800 to about 3000, from about 1900 to about 3000, from about 2000 to about 3000, from about 2100 to about 3000, from about 2200 to about 3000, from about 2300 to about 3000, from about 2400 to about 3000, and from about 2500 to about 3000.

[0024] R 1 Specific examples include: [ka] In the formula, x is an integer such that the total number of carbon atoms is 10 to 400 as described herein.

[0025] X is a moiety containing 1 to 10 carbon atoms, for example 1 to 9, 1 to 8, 1 to 7, 1 to 6, 1 to 5, 1 to 4, 1 to 3, 1 to 2, 2 to 10, 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, 2 to 4, 2 to 3, 3 to 10, 3 to 9, 3 to 8, 3 to 7, 3 to 6, 3 to 5, 3 to 4, 4 to 10, 4 to 9, 4 to 8, 4 to 7, 4 to 6, 4 to 5, 5 to 10, 5 to 9, 5 to 8, 5 to 7, 5 to 6, 6 to 10, 6 to 9, 6 to 8, 6 to 7, 7 to 10, 7 to 9, 7 to 8, 8 to 10, 8 to 9, or 9 to 10 carbon atoms.

[0026] Specific examples of X include: [ka]

[0027] Examples of Y include, for example: [ka]

[0028] Each R 2 are independently a moiety containing 1 to 9 carbon atoms, for example 1 to 8, 1 to 7, 1 to 6, 1 to 5, 1 to 4, 1 to 3, 1 to 2, 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, 2 to 4, 2 to 3, 3 to 9, 3 to 7, 3 to 6, 3 to 5, 3 to 4, 4 to 9, 4 to 8, 4 to 7, 4 to 6, 4 to 5, 5 to 9, 5 to 8, 5 to 7, 5 to 6, 6 to 9, 6 to 8, 6 to 7, 7 to 9, 7 to 8, or 8 to 9 carbon atoms.

[0029] R 2Suitable examples of include, for example, saturated and unsaturated hydrocarbon groups, and straight-chain and branched-chain alkyl groups.

[0030] R 2 Specific examples include: [ka]

[0031] Z is a nitrogen, oxygen, or sulfur atom.

[0032] Each R 3 are independently a hydrogen atom or a moiety containing 1 to 9 carbon atoms, e.g., 1 to 8, 1 to 7, 1 to 6, 1 to 5, 1 to 4, 1 to 3, 1 to 2, 2 to 9, 2 to 8, 2 to 7, 2 to 6, 2 to 5, 2 to 4, 2 to 3, 3 to 9, 3 to 7, 3 to 6, 3 to 5, 3 to 4, 4 to 9, 4 to 8, 4 to 7, 4 to 6, 4 to 5, 5 to 9, 5 to 8, 5 to 7, 5 to 6, 6 to 9, 6 to 8, 6 to 7, 7 to 9, 7 to 8, or 8 to 9 carbon atoms. 3 The moieties contain one or more nitrogen, oxygen, or sulfur functionalizations.

[0033] R 3 Specific examples include: [ka]

[0034] In some preferred embodiments, the lubricant additive may have the following generalized structure 2: [ka] In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; Y is nitrogen, oxygen, or sulfur; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R 3are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3.

[0035] In some embodiments, Y can include one or more hydrogens.

[0036] In some preferred embodiments, the lubricant additive may have the following generalized structure 3: [ka] In the formula, each R 1 are independently a hydrocarbyl group having 10 to 400 carbons; each R 2 are independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R 3 are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3.

[0037] In some preferred embodiments, the lubricant additive can have the following generalized structure 4: [ka] In the formula, each R 1 is a hydrocarbyl group having 10 to 400 carbons; each R 2 is independently a hydrocarbyl group having 1 to 9 carbons; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3 and n is 1 to 20.

[0038] When incorporated into engine oils (i.e., lubricating oil compositions), when used in engine flush processes as part of an aftermarket additive package, or when used during quick wash services, the additive compositions are typically present in a concentration ranging from about 0.1 to about 50.0 wt.%, based on the total weight of the lubricating oil composition (which may be a blended product), such as, for example, about 1 wt.% to about 50 wt.%, about 5 wt.% to about 50 wt.%, about 10 wt.% to about 50 wt.%, about 15 wt.% to about 50 wt.%, about 20 wt.% to about 50 wt.%, about 25 wt.%. ~50wt.%, approximately 30wt.%~50wt.%, approximately 35wt.%~50wt.%, approximately 40wt.%~50wt.%, approximately 45wt .% ~ approx. 50wt.%, approx. 0.1wt.% ~ approx. 45wt.%, approx. 1wt.% ~ approx. 45wt.%, approx. 5wt.% ~ approx. 45wt.%, approx. 10wt .% ~ approx. 45wt.%, approx. 15wt.% ~ approx. 45wt.%, approx. 20wt.% ~ approx. 45wt.%, approx. 25wt.% ~ approx. 45wt.%, approx. 30 wt.% ~ approx. 45wt.%, approx. 35wt.% ~ approx. 45wt.%, approx. 40wt.% ~ approx. 45wt.%, approx. 0.1wt.% ~ approx. 40wt.%, approx. 1wt.% ~ approx. 40wt.%, approx. 5wt.% ~ approx. 40wt.%, approx. 10wt.% ~ approx. 40wt.%, approx. 15wt.% ~ approx. 40wt.%, approx. 20wt.%~about 40wt.%, about 25wt.%~about 40wt.%, about 30wt.%~about 40wt.%, about 35wt.%~about 40wt.%, Approx. 0.1wt.%~Approx. 35wt.%, Approx. 1wt.%~Approx. 35wt.%, Approx. 5wt.%~Approx. 35wt.%, Approx. 10wt.%~Approx. 35wt.% , about 15wt.% to about 35wt.%, about 20wt.% to about 35wt.%, about 25wt.% to about 35wt.%, about 30wt.% to about 35wt. %, about 0.1wt.% to about 30wt.%, about 1wt.% to about 30wt.%, about 5wt.% to about 30wt.%, about 10wt.% to about 30wt .%, about 15wt.% to about 30wt.%, about 20wt.% to about 30wt.%, about 25wt.% to about 30wt.%, about 0.1wt.% to about 25 wt.%, about 1wt.% to about 25wt.%, about 5wt.% to about 25wt.%, about 10wt.% to about 25wt.%, about 15wt.% to about 25w t.%, and about 20wt.% to about 25wt.%, about 0.1wt.% to about 20.0wt.%, about 0.1wt.% to about 19.0wt.%, about 0.1wt.%~approx.18.0wt.%, approx.0.1wt.%~approx.17.0wt.%, approx.0.1wt.%~approx.16.0wt.%, approx.0.1wt.%~approx.15.0wt.%, approx.0.1wt.%~approx.14.0wt.%, approx.0.1wt.%~approx.13.0wt.%, approx.0.1wt.%~approx.12. 0wt.%, about 0.1wt.% to about 11.0wt.%, about 0.1wt.% to about 10.0wt.%, about 0.1wt.% to about 9.0wt.%, about 0.1wt.% to about 8.0wt.%, about 0.1wt.% to about 7.0wt.%, about 0.1wt.% to about 6.0wt.%, about 0.1wt.% to About 5.0wt.%, About 0.1wt.% to about 4.0wt.%, About 0.1wt.% to about 3.0wt.%, About 0.1wt.% to about 2.0wt.%, About 0.1wt.% to about 1.0wt.%, About 1.0wt.% to about 20.0wt.%, About 1.0wt.% to about 19.0wt.%, About 1.0wt .% to about 18.0wt.%, about 1.0wt.% to about 17.0wt.%, about 1.0wt.% to about 16.0wt.%, about 1.0wt.% to about 15.0wt.%, about 1.0wt.% to about 14.0wt.%, about 1.0wt.% to about 13.0wt.%, about 1.0wt.% to about 12.0wt. %, about 1.0wt.% to about 11.0wt.%, about 1.0wt.% to about 10.0wt.%, about 1.0wt.% to about 9.0wt.%, about 1.0wt.% to about 8.0wt.%, about 1.0wt.% to about 7.0wt.%, about 1.0wt.% to about 6.0wt.%, about 1.0wt.% to about 5. 0wt.%, about 1.0wt.% to about 4.0wt.%, about 1.0wt.% to about 3.0wt.%, about 1.0wt.% to about 2.0wt.%, about 2.0wt.% to about 20.0wt.%, about 2.0wt.% to about 19.0wt.%, about 2.0wt.% to about 18.0wt.%, about 2.0wt.% ~17.0wt.%, ~2.0wt.%~16.0wt.%, ~2.0wt.%~15.0wt.%, ~2.0wt.%~14.0wt.%, ~2.0wt.%~13.0wt.%, ~2.0wt.%~12.0wt.%, ~2.0wt.%~11.0wt.%, About 2.0wt.% to about 10.0wt.%, about 2.0wt.% to about 9.0wt.%, about 2.0wt.% to about 8.0wt.%, about 2.0wt.% to about 7.0wt.%, about 2.0wt.% to about 6.0wt.%, about 2.0wt.% to about 5.0wt.%, about 2.0wt.% to about 4.0wt.%, about 2.0wt.% to about 3.0wt.%, about 3.0wt.% to about 20.0wt.%, about 3.0wt.% to about 19.0wt.%, about 3.0wt.% to about 18.0wt.%, about 3.0wt.% to about 17.0wt.%, about 3.0wt.% to about 16.0wt.%, about 3.0wt.% to about 15.0wt.%, about 3.0wt.% to about 14.0wt.%, about 3.0wt.% to about 13.0wt.%, about 3.0wt.% to about 12.0wt.%, about 3.0wt.% to about 11.0wt.%, about 3.0wt.% to about 10.0wt.%, about 3.0wt.% to about 9.0wt.%, about 3. 0wt.%~approx.8.0wt.%, approx.3.0wt.%~approx.7.0wt.%, approx.3.0wt.%~approx.6.0wt.%, approx.3.0wt.%~approx.5.0wt.%, approx.3.0wt.%~approx.4.0wt.%, approx.4.0wt.%~approx.20.0wt.%, approx.5.0wt.%~approx.20.0wt.%, approx. 5.0wt.%~approx.19.0wt.%, approx.5.0wt.%~approx.18.0wt.%, approx.5.0wt.%~approx.17.0wt.%, approx.5.0wt.%~approx.16.0wt.%, approx.5.0wt.%~approx.15.0wt.%, approx.5.0wt.%~approx.14.0wt.%, approx.5.0wt.%~approx.13 .0wt.%, about 5.0wt.% to about 12.0wt.%, about 5.0wt.% to about 11.0wt.%, about 5.0wt.% to about 10.0wt.%, about 5.0wt.% to about 9.0wt.%, about 5.0wt.% to about 8.0wt.%, about 5.0wt.% to about 7.0wt.%, about 5.0wt. % to about 6.0wt.%, about 6.0wt.% to about 20.0wt.%, about 6.0wt.% to about 19.0wt.%, about 6.0wt.% to about 18.0wt.%, about 6.0wt.% to about 17.0wt.%, about 6.0wt.% to about 16.0wt.%, about 6.0wt.% to about 15.0wt.%, Approximately 6.0wt.% to approximately 14.0wt.%, approximately 6.0wt.% to approximately 13.0wt.%, approximately 6.0wt.% to approximately 12.0wt.%, approximately 6.0wt.% to approximately 11.0wt.%, approximately 6.0wt.% to approximately 10.0wt.%, approximately 6.0wt.% to approximately 9.0wt.%, approximately 6.0wt.% to approximately 8. 0wt.%, about 6.0wt.% to about 7.0wt.%, about 7.0wt.% to about 20.0wt.%, about 7.0wt.% to about 19.0wt.%, about 7.0wt.% to about 18.0wt.%, about 7.0wt.% to about 17.0wt.%, about 7.0wt.% to about 16.0wt.%, about 7.0wt.%~approx. 15.0wt.%, approx. 7.0wt.%~approx. 14.0wt.%, approx. 7.0wt.%~approx. 13.0wt.%, approx. 7.0wt.%~approx. 12.0wt.%, approx. 7.0wt.%~approx. 11.0wt.%, approx. 7.0wt.%~approx. 10.0wt.%, approx. 7.0wt.%~approx. 9.0wt.% , about 7.0wt.% to about 8.0wt.%, about 8.0wt.% to about 20.0wt.%, about 8.0wt.% to about 19.0wt.%, about 8.0wt.% to about 18.0wt.%, about 8.0wt.% to about 17.0wt.%, about 8.0wt.% to about 16.0wt.%, about 8.0wt.% to about 1 5.0wt.%, about 8.0wt.% to about 14.0wt.%, about 8.0wt.% to about 13.0wt.%, about 8.0wt.% to about 12.0wt.%, about 8.0wt.% to about 11.0wt.%, about 8.0wt.% to about 10.0wt.%, about 8.0wt.% to about 9.0wt.%, about 9. 0wt.%~approx.20.0wt.%, approx.9.0wt.%~approx.19.0wt.%, approx.9.0wt.%~approx.18.0wt.%, approx.9.0wt.%~approx.17.0wt.%, approx.9.0wt.%~approx.16.0wt.%, approx.9.0wt.%~approx.15.0wt.%, approx.9.0wt.%~approx.14.0 wt.%, about 9.0wt.% to about 13.0wt.%, about 9.0wt.% to about 12.0wt.%, about 9.0wt.% to about 11.0wt.%, about 9.0wt.% to about 10.0wt.%, about 10.0wt.% to about 20.0wt.%, about 10.0wt.% to about 19.0wt.%, about 10 .0wt.%~approx.18.0wt.%, approx.10.0wt.%~approx.17.0wt.%, approx.10.0wt.%~approx.16.0wt.%, approx.10.0wt.%~approx.15.0wt.%, approx.10.0wt.%~approx.14.0wt.%, approx.10.0wt.%~approx.13.0wt.%, approx.10.0wt. % to about 12.0wt.%, about 10.0wt.% to about 11.0wt.%, about 11.0wt.% to about 20.0wt.%, about 11.0wt.% to about 19.0wt.%, about 11.0wt.% to about 18.0wt.%, about 11.0wt.% to about 17.0wt.%, about 11.0wt.% to about 16 .0wt.%, about 11.0wt.% to about 15.0wt.%, about 11.0wt.% to about 14.0wt.%, about 11.0wt.% to about 13.0wt.%, about 11.0wt.% to about 12.0wt.%, about 12.0wt.% to about 20.0wt.%, about 12.0wt.% to about 19.0wt.%, about 12.0wt.% to about 18.0wt.%, about 12.0wt.% to about 17.0wt.%, about 12.0wt.% to about 16.0wt.%, about 12.0wt.% to about 15.0wt.%, about 12.0wt.% to about 14.0wt.%, about 12.0wt.% to about 13.0wt.%, about 13.0wt.% to about 20.0wt.%, about 13.0wt.% to about 19.0wt.%, about 13.0wt.% to about 1 8.0wt.%, about 13.0wt.% to about 17.0wt.%, about 13.0wt.% to about 16.0wt.%, about 13.0wt.% to about 15.0wt.%, about 13.0wt.% to about 14.0wt.%, about 14.0wt.% to about 20.0wt.%, about 14.0wt.% to about 19.0wt.%, about 14.0wt.% to about 18.0wt.%, about 14.0wt.% to about 17.0wt.%, about 14.0w t.% to about 16.0wt.%, about 14.0wt.% to about 15.0wt.%, about 15.0wt.% to about 20.0wt.%, about 15.0wt.% to about 19.0wt.%, about 15.0wt.% to about 18.0wt.%, about 15.0wt.% to about 17.0wt.%, about 15.0wt.% to about 16.0wt.%, about 16.0wt.% to about 20.0wt.%, about 16.0wt.% to about 19.0wt.%, It is present in a concentration ranging from about 16.0 wt.% to about 18.0 wt.%, from about 16.0 wt.% to about 17.0 wt.%, from about 17.0 wt.% to about 20.0 wt.%, from about 17.0 wt.% to about 19.0 wt.%, from about 17.0 wt.% to about 18.0 wt.%, from about 18.0 wt.% to about 20.0 wt.%, from about 18.0 wt.% to about 19.0 wt.%, or from about 19.0 wt.% to about 20.0 wt.%.

[0039] In some embodiments, the additive is present in an amount of from about 0.1 wt.% to about 4.5 wt.%, for example, from about 0.5 wt.% to about 4.0 wt.%, from about 0.5 wt.% to about 3.5 wt.%, from about 0.5 wt.% to about 3.0 wt.%, from about 0.5 wt.% to about 2.5 wt.%, from about 0.5 wt.% to about 2.0 wt.%, from about 0.5 wt.% to about 1.5 wt.%, from about 0.5 wt.% to about 1.0 wt.%, from about 1.0 wt.% to about 5 ... About 4.5wt.%, about 1.0wt.% to about 4.0wt.%, about 1.0wt.% to about 3.5wt.%, about 1.0wt.% to about 3.0wt.%, about 1.0wt.% to about 2.5wt.%, about 1.0wt.% to about 2.0wt.%, about 1.0wt.% to about 1.5wt.%, about 1.5wt.% to about 5.0wt.%, about 1.5wt.% to about 4.5wt.%, about 1.5wt.% to about 4.0wt.%, about 1.5wt.% to about 3.5wt.%, about 1.5wt.% to about 3.0wt.%, about 1. 5wt.%~approx. 2.5wt.%, approx. 1.5wt.%~approx. 2.0wt.%, approx. 2.0wt.%~approx. 5.0wt.%, approx. 2.0wt.%~approx. 4.5wt.%, approx. 2.0wt.%~approx. 4.0wt.%, approx. 2.0wt.%~approx. 3.5wt.%, approx. 2.0wt.%~approx. 3.0wt.%, approx. 2.0wt.%~approx. 2.5wt.%, approx. 2.5wt.%~approx. 5.0wt.%, approx. 2.5wt.%~approx. 4.5wt.%, approx. 2.5wt.%~approx. 4.0wt.%, approx. 2.5wt.%~approx. 3.5wt. .%, about 2.5 wt.% to about 3.0 wt.%, about 3.0 wt.% to about 5.0 wt.%, about 3.0 wt.% to about 4.5 wt.%, about 3.0 wt.% to about 4.0 wt.%, about 3.0 wt.% to about 3.5 wt.%, about 3.5 wt.% to about 5.0 wt.%, about 3.5 wt.% to about 4.5 wt.%, about 3.5 wt.% to about 4.0 wt.%, about 4.0 wt.% to about 5.0 wt.%, about 4.0 wt.% to about 4.5 wt.%, or about 4.5 wt.% to about 5.0 wt.%.

[0040] Specific non-limiting examples of lubricant additive compositions include the following: [ka] [ka] [ka] [ka] [ka] [ka]

[0041] The lubricant additive composition can be synthesized by any suitable method. For example, the general synthesis of compound 1 is described in detail in U.S. Pat. No. 5,669,939, which is incorporated herein by reference. Such reactions typically yield products that include compound 1 dissolved in an organic solvent. In some embodiments, it may be desirable to evaporate the organic solvent before utilizing compound 1.

[0042] In some embodiments, compound 1 can be used as a starting material to synthesize other lubricant additive compounds (e.g., compounds 4, 5, 6). Below is an outline of how compounds 4, 5, and 6 can be derivatized. The starting material is the same in each reaction. Only the charge molar ratio (compound 1 to glycidol) is varied. Other reagents besides glycidol may be contemplated. Furthermore, lubricant additives are not necessarily reaction products of glycidol, nor are they necessarily derivatized with glycidol. [ka]

[0043] Succinimide Dispersants The lubricating oil composition may include a succinimide dispersant. The succinimide dispersant may be present in an amount of about 0.1 wt% to about 10 wt%, for example, about 0.1 wt% to about 9 wt%, about 0.1 wt% to about 8 wt%, about 0.1 wt% to about 7 wt%, about 0.1 wt% to about 6 wt%, about 0.1 wt% to about 6 wt%, about 0.1 wt% to about 5 wt%, about 0.1 wt% to about 4 wt%, about 0.1 wt% to about 3 wt%, about 0.1 wt% to about 2 wt%, about 0.1 wt% to about 1 wt%, about 0.5 wt% to about 10 wt%, about 0.5 wt% to about 9 wt%, about 0.5 wt% to about 10 ... Approximately 8wt%, approximately 0.5wt% to approximately 7wt%, approximately 0.5wt% to approximately 6wt%, approximately 0.5wt% to approximately 5wt%, approximately 0.5wt% to approximately 4wt%, approximately 0.5wt% to approximately 3wt%, approximately 0.5wt% to approximately 2wt%, approximately 0.5wt% to approximately 1wt%, approximately 1wt% to approximately 10wt%, about 1wt% to about 9wt%, about 1wt% to about 8wt%, about 1wt% to about 7wt%, about 1wt% to about 6wt%, about 1wt% to about 5wt%, about 1wt% to about 4wt%, about 1wt% to about 3wt%, about 1wt% to about 2wt%, about 2wt% to about 10w t%, about 2wt% to about 9wt%, about 2wt% to about 8wt%, about 2wt% to about 7wt%, about 2wt% to about 6wt%, about 2wt% to about 5wt%, about 2wt% to about 4wt%, about 2wt% to about 3wt%, about 3wt% to about 10wt%, about 3wt% to about 9wt% , about 3wt% to about 8wt%, about 3wt% to about 7wt%, about 3wt% to about 6wt%, about 3wt% to about 5wt%, about 3wt% to about 4wt%, about 4wt% to about 10wt%, about 4wt% to about 9wt%, about 4wt% to about 8wt%, about 4wt% to about 7wt%, about It can be present at 4 wt% to about 6 wt%, about 4 wt% to about 5 wt%, about 5 wt% to about 10 wt%, about 5 wt% to about 9 wt%, about 5 wt% to about 8 wt%, about 5 wt% to about 7 wt%, about 5 wt% to about 6 wt%, about 6 wt% to about 10 wt%, about 6 wt% to about 9 wt%, about 6 wt% to about 8 wt%, about 6 wt% to about 7 wt%, about 7 wt% to about 10 wt%, about 7 wt% to about 9 wt%, about 7 wt% to about 8 wt%, about 8 wt% to about 10 wt%, about 8 wt% to about 9 wt%, or about 9 wt% to about 10 wt%.

[0044] In one embodiment, the polyalkenyl bis-succinimide is a polyalkenyl substituted succinic anhydride: [ka] (wherein R is a polyalkenyl substituent derived from a polyalkene group having a number average molecular weight of about 500 to about 3000) with a polyamine. In one embodiment, R is a polyalkenyl substituent derived from a polyalkene group having a number average molecular weight of about 1000 to about 2500.

[0045] In one embodiment, R is a polyisobutenyl substituent derived from a polyisobutene having a number average molecular weight of about 500 to about 3000. In another embodiment, R is a polyisobutenyl substituent derived from a polyisobutene having a number average molecular weight of about 1000 to about 2500.

[0046] Suitable polyamines for use in preparing the bis-succinimide dispersants include the polyalkylene polyamines. Such polyalkylene polyamines typically contain from about 2 to about 12 nitrogen atoms and from about 2 to 24 carbon atoms. Particularly suitable polyalkylene polyamines have the formula: 2 They have the formula N-(R'NH)xH, where R' is a straight or branched chain alkylene group having 2 or 3 carbon atoms and x is 1 to 9. Representative examples of suitable polyalkylene polyamines include ethylenediamine, diethylenetriamine, triethylenetetraamine, tetraethylenepentamine, pentaethylenehexamine, and heavy polyamines (e.g., Ethyleneamine E-100 available from Huntsman Company).

[0047] Generally, the polyalkenyl-substituted succinic anhydride is reacted with the polyamine at a temperature of about 130° C. to about 220° C. (e.g., 145° C. to 175° C.). The reaction can be carried out under an inert atmosphere such as nitrogen or argon. Generally, a suitable molar charge between the polyamine and the polyalkenyl-substituted succinic anhydride is about 0.35:1 to about 0.6:1 (e.g., 0.4:1 to 0.5:1). As used herein, the "molar charge between the polyamine and the polyalkenyl-substituted succinic anhydride" refers to the ratio of the number of moles of polyamine to the number of succinic acid groups in the succinic anhydride reactant.

[0048] One class of suitable polyalkenyl succinimides can be represented by: [ka] wherein R and R' are as described hereinabove, and y is 1-11.

[0049] Post-treatment of polyalkenyl succinimide In some embodiments, the succinimide dispersant may be post-treated with an organic carbonate.

[0050] Suitable organic carbonates include cyclic carbonates such as 1,3-dioxolan-2-one (ethylene carbonate or "EC"); 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-dimethyl-1,3-dioxan-2-one; 5,5-dihydroxymethyl-1,3-dioxan-2-one; 5-methyl-1,3-dioxan-2-one; 4-methyl-1,3-dioxan-2-one; 5-hydroxy-1,3-dioxan-2-one; 5-hydroxymethyl-5-methyl-1,3-dioxan-2-one; 5,5-diethyl-1,3-dioxan-2-one; 5-methyl-5-propyl-1,3-dioxan-2-one; 4,6-dimethyl-1,3-dioxan-2-one; 4,4,6-trimethyl-1,3-dioxan-2-one and spiro[1,3-oxa-2-cyclohexanone-5,5'-1',3'-oxa-2'-cyclohexanone]. Other suitable cyclic carbonates can be prepared from sugars such as sorbitol, glucose, fructose, galactose, and C by methods known in the art. 1 -C 30 The vicinal diols can be prepared from vicinal diols prepared from olefins such as cyclohexyl ether, ...

[0051] lubricating oil The lubricating oil compositions of the present invention include one or more base oils (e.g., Group I, Group II, Group III, Group IV, or Group V). Further, the one or more base oils may include base oils from the same group (e.g., Group II Chevron Neutral Oil 600R®, Group II Chevron Neutral Oil 220R®, and Group I Chevron Neutral Oil 100R®). The amount of base oil(s) is about 50 wt.% or more (a "major amount") based on the total weight of the lubricating oil composition.

[0052] An oil of lubricating viscosity (sometimes referred to as a "base stock" or "base oil") is the primary liquid component of a lubricating oil into which additives and possibly other oils are blended, for example, to produce the final lubricating oil (or lubricating oil composition). Base oils useful for making concentrates and for making lubricating oil compositions therefrom may be selected from natural (vegetable, animal, or mineral) and synthetic lubricating oils and mixtures thereof.

[0053] The oils used as base oils are selected or blended according to the desired end use and additives in the finished oil to provide a lubricating oil composition having a desired grade of engine oil, e.g., Society of Automotive Engineers (SAE). In one embodiment, the lubricating oil composition is a multigrade oil for heavy duty or passenger vehicles. The multigrade oil has a viscosity grade SAE of 0W-12, 0W-16, 0W-20, 0W-26, 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.

[0054] The definitions of 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 more than 0.03% sulfur and have a viscosity index of 80 or greater and less than 120, using the test methods set forth in Table E-1. Group II base stocks contain 90% or greater saturates, 0.03% or less sulfur, and have a viscosity index of 80 or greater and less than 120, using the test methods set forth in Table E-1. Group III base stocks contain 90% or greater saturates, 0.03% or less sulfur, and have a viscosity index of 120 or greater, using the test methods set forth in Table E-1. Group IV base stocks are polyalphaolefins (PAOs). Group V base stocks include all other base stocks not included in Group I, II, III, or IV.

[0055] Natural oils include animal oils, vegetable oils (e.g., castor oil and lard oil), and mineral oils. Animal and vegetable oils with favorable thermo-oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely according to their crude source, e.g., paraffinic, naphthenic, or mixed paraffinic and naphthenic. Oils derived from coal or shale are also useful. Natural oils also vary according to the methods used for their production and purification, e.g., their distillation range, and whether they are straight run, cracked, hydrorefined, or solvent extracted.

[0056] Synthetic oils include hydrocarbon oils, including oils such as polymerized and copolymerized olefins (e.g., polybutylene, polypropylene, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene-alpha olefin copolymers). Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oils. As an example, C 8 -C 14 Olefins, e.g. C 8 , C 10 , C 12 , C 14 In some cases, PAOs derived from olefins, or mixtures thereof may be utilized.

[0057] Other useful fluids for use as base oils include unconventional or unconventional base stocks, preferably catalytically processed or synthetically prepared to provide high performance properties.

[0058] Unconventional or unconventional base stocks / base oils include base stock(s) derived from one or more gas-to-liquids (GTL) materials, as well as mixtures of isomerized / isomerized dewaxed base stock(s) derived from natural wax or waxy feedstocks, waxy raw stocks of mineral oils and / or non-mineral oils, such as slack wax, natural wax, and waxy stocks, such as gas oil, residues from hydrocracking of waxy fuels, waxy raffinates, hydrocracked oils, pyrolysis oils, or other minerals, mineral oils, or even non-petroleum derived waxy materials, such as waxy materials obtained from coal liquids or shale oil, as well as mixtures of these base stocks. Other base oils include coal-to-liquids (CTL) products and alkylnaphthalenes.

[0059] The base oils for use in the lubricating oil compositions of the present disclosure can be any of the various oils corresponding to API Group I, Group II, Group III, Group IV, and Group V oils, and mixtures thereof, with API Group II, Group III, Group IV, and Group V oils, and mixtures thereof, being preferred, and Group III to Group V base oils being more preferred due to their superior volatility, stability, viscosity, and detergency characteristics.

[0060] The lubricating oil composition has a high temperature shear viscosity (HTHS) at 150°C of 2.9 cP or less, for example, 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. P or less, 1.3 cP or less, 1.2 cP or less, 1.1 cP or less, 1.0 cP or less, 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.

[0061] The lubricating oil composition may have a viscosity index of at least 135 (e.g., 135-400, or 135-250), at least 150 (e.g., 150-400, 150-250), at least 165 (e.g., 165-400, or 165-250), at least 190 (e.g., 190-400, or 190-250), or at least 200 (e.g., 200-400, or 200-250). If the viscosity index of the lubricating oil composition is less than 135, it may be difficult to improve fuel efficiency while maintaining the HTHS viscosity at 150°C. If the viscosity index of the lubricating oil composition is more than 400, the evaporation characteristics may be reduced, and defects due to insufficient solubility of additives and insufficient matching with sealing materials may occur.

[0062] The base oil is 100 oDynamic viscosity at C (ASTMD445) is 3 to 12 mm 2 / s range, for example, 3 to 11 mm 2 / s, 3~10mm 2 / s, 3~9mm 2 / s, 3~8mm 2 / s, 3~7mm 2 / s, 3~6mm 2 / s, 3~5mm 2 / s, 3~4mm 2 / s, 4~12mm 2 / s, 4~11mm 2 / s, 4~10mm 2 / s, 4~9mm 2 / s, 4~8mm 2 / s, 4~7mm 2 / s, 4~6mm 2 / s, 4~5mm 2 / s, 5~12mm 2 / s, 5~11mm 2 / s, 5~10mm 2 / s, 5~9mm 2 / s, 5~8mm 2 / s, 5~7mm 2 / s, 5~6mm 2 / s, 6~12mm 2 / s, 6~11mm 2 / s, 6~10mm 2 / s, 6~9mm 2 / s, 6~8mm 2 / s, 6~7mm 2 / s, 7~12mm 2 / s, 7~11mm 2 / s, 7~10mm 2 / s, 7~9mm 2 / s, 7~10mm 2 / s, 7~9mm 2 / s, 7~8mm 2 / s, 8~12mm 2 / s, 8~11mm 2 / s, 8~10mm 2 / s, 8~9mm 2 / s, 9~12mm 2 / s, 9~11mm 2 / s, 9~10mm 2 / s, 10~12mm 2 / s, 10~11mm 2 / s, or 11-12mm 2 / s range.

[0063] Other Additives The lubricating oil composition of the present invention may also contain conventional additives to provide auxiliary functions, resulting in the finished lubricating oil composition in which these additives are dispersed or dissolved.For example, the lubricating oil composition may be blended with antioxidants, ashless dispersants, antiwear agents, detergents such as metal detergents, rust inhibitors, anti-foaming agents, demulsifiers, friction modifiers, metal deactivators, pour point depressants, viscosity modifiers, antifoaming agents, co-solvents, package compatibilizers, corrosion inhibitors, dyes, extreme pressure agents, etc., and mixtures thereof.Various additives are known and commercially available.These additives or their analogues may be used in the preparation of the lubricating oil composition of the present invention by conventional blending procedures.

[0064] Each of the aforementioned additives, when used, is used in a functionally effective amount to impart the desired properties to the lubricating oil. Thus, for example, if the additive is an ashless dispersant, a functionally effective amount of the ashless dispersant is an amount sufficient to impart the desired dispersant properties to the lubricating oil. In general, the concentration of each of these additives, when used, can range from about 0.001 to about 20 wt.%, for example, from about 0.01 to about 10 wt.%, unless otherwise specified.

[0065] compound Typically, the level of sulfur in the lubricating oil composition of the present invention is about 0.7 wt.% or less, e.g., about 0.01 wt.% to about 0.70 wt.%, 0.01 to 0.6 wt.%, 0.01 to 0.5 wt.%, 0.01 to 0.4 wt.%, 0.01 to 0.3 wt.%, 0.01 to 0.2 wt.%, 0.01 wt.% to 0.10 wt.% sulfur, based on the total weight of the lubricating oil composition. In one embodiment, the level of sulfur in the lubricating oil composition of the present invention is about 0.60 wt.% or less, about 0.50 wt.% or less, about 0.40 wt.% or less, about 0.30 wt.% or less, about 0.20 wt.% or less, about 0.10 wt.% or less, based on the total weight of the lubricating oil composition.

[0066] In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.12 wt.% or less, for example, about 0.01 wt.% to about 0.12 wt.% phosphorus, based on the total weight of the lubricating oil composition. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.11 wt.% or less, for example, about 0.01 wt.% to about 0.11 wt.% phosphorus, based on the total weight of the lubricating oil composition. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.10 wt.% or less, for example, about 0.01 wt.% to about 0.10 wt.% phosphorus, based on the total weight of the lubricating oil composition. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.09 wt.% or less, for example, about 0.01 wt.% to about 0.09 wt.% phosphorus, based on the total weight of the lubricating oil composition. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.08 wt.% or less, for example, about 0.01 wt.% to about 0.08 wt.% phosphorus, based on the total weight of the lubricating oil composition. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.07 wt.% or less, for example, about 0.01 wt.% to about 0.07 wt.% phosphorus, based on the total weight of the lubricating oil composition. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is about 0.05 wt.% or less, for example, about 0.01 wt.% to about 0.05 wt.% phosphorus, based on the total weight of the lubricating oil composition.

[0067] In one embodiment, the sulfated ash level produced by the lubricating oil composition of the present invention is about 1.60 wt.% or less as determined by ASTM D 874, for example, about 0.10 to about 1.60 wt.% sulfated ash as determined by ASTM D 874. In one embodiment, the sulfated ash level produced by the lubricating oil composition of the present invention is about 1.00 wt.% or less as determined by ASTM D 874, for example, about 0.10 to about 1.00 wt.% sulfated ash as determined by ASTM D 874. In one embodiment, the sulfated ash level produced by the lubricating oil composition of the present invention is about 0.80 wt.% or less as determined by ASTM D 874, for example, about 0.10 to about 0.80 wt.% sulfated ash as determined by ASTM D 874. In one embodiment, the sulfated ash level produced by the lubricating oil composition of the present invention is less than or equal to about 0.60 wt.% as determined by ASTM D 874, for example, a sulfated ash level of from about 0.10 to about 0.60 wt.% as determined by ASTM D 874.

[0068] Suitably, the lubricating oil composition of the present invention may have a total base number (TBN) of from 4 to 15 mg KOH / g (eg, from 5 to 12 mg KOH / g, from 6 to 12 mg KOH / g, or from 8 to 12 mg KOH / g).

[0069] The following non-limiting examples are illustrative of the present invention. A brief description of how the examples were prepared is provided. EXAMPLES

[0070] Baseline Formulation The baseline formulation is an SAE 5W-40 viscosity grade lubricant composition prepared by blending the following components: a) Boronized Ca sulfonate with a TBN of 160 and a boron content of 0.017 wt% b) Overbased Ca phenate with a TBN of 260 and a Ca content of 0.02 wt% c) ZnDTP with 0.074 wt% P d) Overbased Ca sulfonate with a TBN of 410 and a Ca content of 0.13 wt% e) Antioxidants f) Ethylene-propylene viscosity modifier

[0071] The remainder of the lubricating oil composition comprises minor amounts of an antifoam agent, a pour point depressant, and a mixture of a Group III base oil having a KV100 of 4 cSt and a Group III base oil having a KV100 of 6 cSt.

[0072] Example 1 The following ingredients were added to the baseline formulation to produce Example 1: 6.5wt% EC treated succinimide 2wt% of compound 2

[0073] Example 2 The following ingredients were added to the baseline formulation to prepare Example 2: 6.5wt% EC treated succinimide 2wt% of compound 1

[0074] Example 3 The following ingredients were added to the baseline formulation to prepare Example 3: 6.5wt% EC treated succinimide 2wt% of compound 3

[0075] Example 4 The following ingredients were added to the baseline formulation to prepare Example 4: 6.5wt% EC treated succinimide 2wt% of compound 4

[0076] The following ingredients were added to the baseline formulation to prepare Example 5: Example 5 4wt% EC treated succinimide 2wt% of compound 4

[0077] The following ingredients were added to the baseline formulation to prepare Example 6: Example 6 4wt% EC treated succinimide 1wt% of compound 2

[0078] The remainder of the lubricating oil composition comprises minor amounts of antifoam agents, pour point depressants, and base oils.

[0079] Example 7 The following ingredients were added to the baseline formulation to prepare Example 7: 8wt% EC treated succinimide

[0080] The following ingredients were added to the baseline formulation to prepare Example 8: Example 8 6wt% EC treated succinimide 2wt% of compound 2

[0081] Example 9 The following ingredients were added to the baseline formulation to prepare Example 9: 6wt% EC treated succinimide 2wt% of compound 3

[0082] Example 10 The following ingredients were added to the baseline formulation to prepare Example 10: 6wt% EC treated succinimide 2wt% of compound 5

[0083] Example 11 The following ingredients were added to the baseline formulation to prepare Example 11: 6wt% EC treated succinimide 2wt% of compound 4

[0084] Example 12 The following ingredients were added to the baseline formulation to prepare Example 12: 4wt% EC treated succinimide 2wt% of compound 2

[0085] Example 13 The following ingredients were added to the baseline formulation to prepare Example 13: 4wt% EC treated succinimide 1wt% of compound 2

[0086] Example 14 The following ingredients were added to the baseline formulation to prepare Example 14: 2wt% of compound 1

[0087] TDI3 engine test Piston cleanliness and ring sticking were evaluated by the TDI3 engine test, which is very similar to the Volkswagen Turbocharged DI, European Passenger Car Diesel Engine Test (CEC-L-78-T-99) and is part of the ACEAA / B and C specifications published in 2004 by the Automobile Manufacturers Association. This test was used to simulate repeated cycles of high speed driving followed by idling. A Volkswagen 1.9 liter in-line 4-cylinder turbocharged direct injection automotive diesel engine (VWTDi) was mounted on an engine dynamometer stand. A 54-hour two-stage procedure was performed, cycling 30 minutes in 40°C oil sump at idle and 150 minutes in 145°C oil sump at full power (4150 rpm) without oil top-up in between. After the procedure, the pistons were evaluated for carbon and lacquer deposits, as well as carbon filling of the grooves. The piston rings were evaluated for ring sticking. Table 1 summarizes the results for the TDI3. [Table 1]

[0088] Panel Coker Test The Panel Coker Test is a method for determining the relative stability of lubricants. It is often used to evaluate the tendency of lubricants in contact with hot metal surfaces to form deposits or lacquer, simulating the formation of deposits in engine cylinders and pistons. The test apparatus includes a rectangular stainless steel reservoir inclined at 25° from the horizontal. The test panel (95mm x 45mm) is held in place by a heating element fitted with a thermocouple probe to control the temperature of the aluminium or steel test panel. A horizontal shaft fitted with a series of tines is placed above the oil and rotates at 1000 rpm. 300ml of the lubricant to be evaluated is placed in the panel coker apparatus and the test panel is heated to 300°C while the oil temperature is controlled at 100°C. As the shaft rotates, the tines pass through the test lubricant and droplets of lubricant are dropped onto the heated test panel. The test panel is weighed again at the end of the 3 hour test duration to determine the amount of deposits formed. The weight gain of the test panel and the amount of test lubricant consumed during the test are indicative of the performance of the lubricant under high temperature conditions. The results are summarized in Table 2. [Table 2]

[0089] Rapid cleaning to remove deposits Examples 15-17 and Comparative Example A were formulated to provide lubricating oil compositions meeting the following specifications: SAE 30 viscosity grade (K at 100° C.) v is about 15.0 mm 2 / s).

[0090] Examples 15-17 were blended with the following ingredients: a) Group II base oils b) 9.7 wt. % of an engine oil additive package (including, for example, dispersants, detergents, antioxidants, and friction modifiers) c) Various treat rates of compound A (diluted with 30 wt.% C9 aromatic solvent) (Table 4): [ka] Comparative Example B (Table 3) is similar to Examples 15-17, but does not contain Compound A.

[0091] Experimental Procedure I In the first set of experiments, various concentrations of Compound A were mixed with finished oil to observe its solubility and tendency to solubilize carbonaceous ring deposits. Compound A was blended with the finished oil for 20 minutes at ambient temperature.

[0092] Compound A was added in various amounts to finished oils containing engine oil additive packages. Actual ring segments containing high concentrations of carbonaceous deposits from internal combustion engines were used in the experiments. The rings were pre-cleaned with hexane, dried, and then weighed to four decimal places. The ring segments were then carefully placed into beakers containing finished oils (Examples 4-6 and Comparative Example B). The samples were allowed to sit in the finished oils without stirring for 4, 6, and 24 hours. The approximate temperature of the finished oil was about 22°C. A white haze formed around the segmented ring pieces, indicating some of the sediment had been removed. The ring fragments were removed, rinsed with hexane, air-dried, and then re-weighed.

[0093] The concentration of Compound A in the finished oil correlates well with sediment removal, and soak / dwell time also correlates with sediment removal, as shown in Table 3. The cumulative ring weight loss, which corresponds to sediment removal, is reported in mg (higher mg values ​​indicate better sediment removal performance). [Table 3]

[0094] TBN Boost The effect of Compound A on total base number (TBN) was observed by JIS K-2501:20038 (ASTM D2896) method (DH-2). As shown in Table 4 below, Compound A, although a soft base component (containing only N), boosts TBN. Generally, a high TBN is desirable to neutralize acidic by-products of combustion and oxidation. [Table 4]

[0095] Sediment Testing The 0W-20 formulated oils containing Compound A (invention) and the comparative 0W-20 formulated oils were evaluated using the Daimler OM471LA performance test for heavy duty engine oils, which provides evaluation of piston cleanliness, bore polish, oil consumption, general engine deposits, engine sludge, general engine wear, cylinder wear, piston ring sticking, and / or turbocharger deposits.

[0096] The OM471LA Euro VI engine is a proven production engine that represents heavy-duty engine technology for Euro 6. This 6-cylinder in-line engine features steel pistons, a displacement of 12.8 liters, a turbocharger and a wastegate.

[0097] The test is run for a duration of 600 hours (two consecutive blocks of 300 hours operation) and includes stop / start events to replicate the harsh usage of the vehicle in the field. A known fuel (Coryton RF99-21) is used to ensure good test repeatability. At the end of the test, the pistons are evaluated for piston deposits.

[0098] The only difference between the inventive 0W-20 formulated oil and the comparative 0W-20 formulated oil is that instead of the 2.7 wt.% ethylene carbonate treated bissuccinimide dispersant in the comparative oil, the inventive oil contains 2.7 wt.% Compound A. The following table shows the deposit removal (as a percentage) observed in the undercrown and turbocharger housing. [Table 5]

[0099] For the sake of brevity, only certain ranges are explicitly disclosed herein. However, a range from any lower limit may be combined with any upper limit to enumerate a range that is not explicitly stated, and a range from any lower limit may be combined with any other lower limit to enumerate a range that is not explicitly stated, and a range from any upper limit may be combined with any other upper limit to enumerate a range that is not explicitly stated. Furthermore, a range includes every point or individual value between its endpoints, even if not explicitly enumerated. Thus, every point or individual value may be combined with other points or individual values, or with other lower or upper limits, to serve as its own lower or upper limit, to enumerate a range that is not explicitly stated.

[0100] Similarly, the term "comprising" is considered synonymous with the term "including." Similarly, whenever the transitional phrase "comprising" precedes a composition, element, or group of elements, it is understood to also contemplate the same composition or group of elements with the transitional phrase "consisting essentially of," "consisting of," "selected from the group consisting of," or "is," preceding the description of the composition, element, or group of elements, and vice versa.

[0101] As used herein, the terms "a" and "the" are understood to encompass the plural as well as the singular.

[0102] Various terms are defined above. To the extent that a term used in the claims is not defined above, it should be given the broadest definition that a person skilled in the relevant art would give that term, as reflected in at least one printed publication or issued patent. Furthermore, all patents, test methods, and other documents cited in this application are incorporated by reference in their entirety to the extent such disclosure is not inconsistent with this application and in all jurisdictions where such incorporation is permitted.

[0103] The foregoing description of the disclosure illustrates and describes the disclosure. Moreover, the disclosure shows and describes only the preferred embodiments, but as noted above, it is to be understood that the disclosure can be used in various other combinations, modifications, and environments, and that changes or modifications are possible within the scope of the concepts expressed herein, consistent with the teachings above and / or the skill or knowledge of the relevant art. While the foregoing is directed to embodiments of the disclosure, other and further embodiments of the disclosure can be devised without departing from the basic scope thereof, the scope of which is determined by the claims that follow.

[0104] Where combinations, subsets, groups, etc. of elements (e.g., combinations of components in a composition or combinations of steps in a method) are disclosed, it is understood that specific reference to each of the various individual and collective combinations and permutations of those elements is specifically contemplated and described herein, although it may not be explicitly disclosed.

[0105] The embodiments described herein above are further intended to further describe the best mode known for carrying out the invention and to enable others skilled in the art to utilize the present disclosure in such or other embodiments, with various modifications necessary for a particular application or use. Therefore, the description is not intended to be limited to the forms disclosed herein. Also, it is intended that the appended claims be construed to include alternative embodiments.

Claims

1. a major amount of base oil; The structure: 【Chemistry 1】 (In the formula, each R １ are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R ２ are independently hydrocarbyl groups having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R ３ are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. A lubricant additive having 1. A lubricating oil composition comprising:

2. 10. The lubricant composition of claim 1, wherein the lubricant additive is present in an amount of from about 0.1 to about 50.0 wt. %, based on the total weight of the lubricant composition.

3. R １ The lubricating oil composition of claim 1, wherein is a polyalkyl group.

4. R １ The lubricating oil composition of claim 1, wherein is a polyisobutenyl group.

5. 10. The lubricating oil composition of claim 1, further comprising a succinimide dispersant.

6. 6. The lubricating composition of claim 5, wherein the succinimide dispersant is post-treated with ethylene carbonate.

7. The lubricant additive has the following generalized structure: 【Chemistry 2】 (In the formula, each R １ are independently a hydrocarbyl group having 10 to 400 carbons; Y is nitrogen, oxygen, or sulfur; each R ２ are independently hydrocarbyl groups having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R ３ are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. The lubricating oil composition of claim 1 having

8. 1. A method of lubricating an engine, comprising: a major amount of base oil; The structure: 【Chemistry 3】 (In the formula, each R １ are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R ２ are independently hydrocarbyl groups having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R ３ are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. A lubricant additive having lubricating said engine with a lubricating oil composition comprising:

9. 9. The method of claim 8, wherein the lubricant additive is present at about 0.1 to about 50.0 wt. %, based on the total weight of the lubricating oil composition.

10. R １ The method of claim 8 , wherein is a polyalkyl group.

11. R １ The method of claim 8 , wherein is a polyisobutenyl group.

12. 9. The method of claim 8 further comprising a succinimide dispersant.

13. 13. The method of claim 12, wherein the succinimide is the succinimide dispersant post-treated with ethylene carbonate.

14. The lubricant additive has the following generalized structure: 【Chemistry 4】 (In the formula, each R １ are independently a hydrocarbyl group having 10 to 400 carbons; Y is nitrogen, oxygen, or sulfur; each R ２ are independently hydrocarbyl groups having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R ３ are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3.

9. The method of claim 8, comprising:

15. 1. A method for improving piston cleanliness or oxidation control in an engine, comprising: a major amount of base oil; The structure: 【Chemistry 5】 (In the formula, each R １ are independently a hydrocarbyl group having 10 to 400 carbons; X is an alkyl, aryl, or heteroaromatic group having 1 to 10 carbons; Y is nitrogen, oxygen, or sulfur; each R ２ are independently hydrocarbyl groups having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R ３ are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3. A lubricant additive having lubricating said engine with a lubricating oil composition comprising:

16. 16. The method of claim 15, wherein the lubricant additive is present at about 0.1 to about 5 wt. %, based on the total weight of the lubricating oil composition.

17. R １ The method of claim 15 , wherein is a polyalkyl group.

18. R １ The method of claim 15, wherein is a polyisobutenyl group.

19. 16. The method of claim 15 further comprising a succinimide dispersant.

20. The lubricant additive has the following generalized structure: 【Chemistry 6】 (In the formula, each R １ are independently a hydrocarbyl group having 10 to 400 carbons; Y is nitrogen, oxygen, or sulfur; each R ２ are independently hydrocarbyl groups having 1 to 9 carbons; Z is nitrogen, oxygen, or sulfur, and each R ３ are independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen, or sulfur functional groups, where p is 1 to 3, n is 1 to 20, and m is 0 to 3.

16. The method of claim 15, having the following structure:

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