Low molecular weight dispersants

Abstract

The present disclosure describes a lubricating oil composition. The composition includes a major amount of a base oil; and a lubricant additive having the following structure: (I) wherein each R1 is 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 R2 is independently a hydrocarbyl group having 1 to 9 carbons; z is nitrogen, oxygen or sulfur; and each R3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3. # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of U.S. Provisional Patent Application No. 63 / 339,569, filed on May 9, 2022, which is incorporated herein by reference in its entirety. Technical Field

[0003] The present disclosure relates to lubricant additive compositions and lubricating oil compositions containing the lubricant additive compositions. More specifically, the present disclosure describes low molecular weight dispersants that improve engine cleanliness. Background Art

[0004] As automotive engines continue to improve, the development of new engine oils and additive packages offers a faster and / or more cost-effective path to improving performance factors such as fuel efficiency, oxidation stability, volatility, etc.

[0005] Oxidation stability is an important performance factor because poor oxidation stability often leads to deposit formation, which in turn can lead to stalling and poor acceleration. In addition, deposits can increase fuel consumption and increase the production of harmful exhaust pollutants. Summary of the invention

[0006] In another aspect, a lubricating oil composition is provided, comprising: a major amount of a base oil; and a lubricant additive having the following structure:

[0007]

[0008] Each R 1 is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

[0009] In another aspect, a method of lubricating an engine is provided, the method comprising lubricating the engine with a lubricating oil composition, the lubricating oil composition comprising: a major amount of a base oil; and a lubricant additive having the following structure:

[0010]

[0011] Each R 1is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

[0012] In yet another aspect, there is provided a method of improving piston cleanliness or oxidation inhibition in an engine, the method comprising lubricating the engine with a lubricating oil composition comprising: a major amount of a base oil;

[0013] Lubricant additives having the following structure:

[0014]

[0015] Each R 1 is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3. DETAILED DESCRIPTION

[0016] It should be understood that when combinations, subsets, groups, etc. of elements are disclosed (e.g., combinations of components in compositions, or combinations of steps in methods), while specific reference to each of the various individual and collective combinations and arrangements of these elements may not be explicitly disclosed, each is specifically contemplated and described herein.

[0017] The present disclosure relates to a lubricant additive that can prevent or reduce deposit formation (e.g., reduce soot deposits on pistons) to improve engine cleanliness. The lubricant additive can be formulated in a base oil with other lubricant additives to provide performance benefits to the resulting lubricating oil composition.

[0018] In some embodiments, the present disclosure is directed to engine flush products containing additives, mixed products containing additives and used lubricating oil compositions, and methods of using the same.

[0019] In some embodiments, the engine flush product is an aftermarket additive package wherein the additives are dissolved in a solvent. The aftermarket additive package is suitable for quickly cleaning or removing accumulated deposits, sludge, and other gunk in an internal combustion engine.

[0020] The engine flushing process removes sludge, heavy deposits, and / or other gunky materials that may have accumulated in the engine oil. A typical engine flushing process includes adding additives as aftermarket additives (e.g., engine flushing products) to an internal combustion engine through the filler port. After the engine is allowed to idle, the additives are added to mix with the existing lubricating oil composition with the "used base oil." The mixed product can dissolve or clean the sludge, heavy deposits, and / or gunky materials present in the engine. The mixed product is then discharged along with the dissolved sludge, deposits, and / or gunky materials.

[0021] In some embodiments, the lubricating oil compositions disclosed herein can be used as a quick cleaning fluid. The quick cleaning fluid can be used during a quick cleaning service to remove accumulated deposits, sludge, and other slimy materials in an internal combustion engine. The quick cleaning service can remove sludge, heavy deposits, and / or other insoluble materials that may accumulate over time.

[0022] The cleaning process may include using lubricants in the engine oil pan or crankcase, and circulating the lubricating oil without starting the engine. Additional steps include circulating the lubricating oil and allowing it to soak under static conditions 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 a week. Another cleaning step may include starting the engine and operating the engine under any operating conditions suitable for engine design and fuel 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 a week. In some embodiments, the lubricating oil compositions disclosed herein may be used to remove deposits present in crankcases, rocker covers, camshaft areas, timing gear covers, cylinder heads, combustion chambers, piston rings, and / or ring grooves in internal combustion engines.

[0023] When used during a quick cleaning service, the lubricating oil composition may require a higher concentration of lubricant additives than is typically used during regular maintenance. This lubricating oil with a higher amount of deposit-cleaning lubricant additives is used to lubricate and clean the engine. The resulting mixed product (concentrated lubricating oil and sediment) can then be flushed. The flushing step typically occurs after the cleaning step is completed.

[0024] In some embodiments, the cleaning step of the quick cleaning service includes 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 one week. The exact amount of 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, the desired cleanliness level, etc.

[0025] In some embodiments, flushing is performed after 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 is started. In some embodiments, the flushing step may be performed for a period of time up to about 25% of the OEM recommended oil change interval.

[0026] In some embodiments, the lubricating oil composition, quick clean fluid, or engine flush product disclosed herein has 2 mgKOH / g to 200 mgKOH / g, such as 2 mgKOH / g to 175 mgKOH / g, 2 mgKOH / g to 150 mgKOH / g, 2 mgKOH / g to 100 mg KOH / g, 5 mgKOH / g to 200 mgKOH / g, 5 mgKOH / g to 175 mgKOH / g, 5 mgKOH / g to 150 mgKOH / g, 5 mgKOH / g to 100 mgKOH / g, 10 mgKOH / g to 200 mgKOH / g, 10 mgKOH / g to 175 mgKOH / g, 10 mgKOH / g to 150 mgKOH / g, 10 mgKOH / g to 100 mgKOH / g, 50 mgKOH / g to 200 mgKOH / g. KOH / g, 50 mgKOH / g to 175 mgKOH / g, 50 mgKOH / g to 150 mgKOH / g, and 50 mgKOH / g to 100 mgKOH / g total base number (TBN).

[0027] Lubricant Additives

[0028] The lubricant additive composition of the present disclosure is a dispersant and can be represented by the following general chemical structure I:

[0029]

[0030] Each R 1is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbon group with 1 to 9 carbons functionalized with one or more nitrogen, oxygen or sulfur, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3. In some embodiments, X is a cyclic or acyclic alkyl group. In some embodiments, Y may include one or more hydrogens. In some preferred embodiments, Z is nitrogen.

[0031] Each R 110 to 400 carbon atoms, such as 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 70 0, 10 to 60, 10 to 50, 10 to 40, 10 to 30, 10 to 20, 20 to 400, 20 to 390, 20 to 380, 20 to 370, 20 to 360, 20 to 350, 20 to 340, 20 to 330, 20 to 320, 20 to 310, 20 to 300, 20 to 290, 20 to 280, 2 0 to 270, 20 to 260, 20 to 250, 20 to 240, 20 to 230, 20 to 220, 20 to 210, 20 to 200, 20 to 190, 20 to 180, 20 to 170, 20 to 160, 20 to 150, 20 to 140, 20 to 130, 20 to 120, 20 to 110, 20 to 100, 20 to 90, 20 to 80, 20 to 70, 20 to 60, 20 to 50, 20 to 40, 20 to 30, 30 to 400, 30 to 390, 30 to 380, 30 to 370, 30 to 360, 30 to 350, 30 to 340, 30 to 330, 30 to 320, 30 to 310, 30 to 300, 30 to 29 0, 30 to 280, 30 to 270, 30 to 260, 30 to 250, 30 to 240, 30 to 230, 30 to 220, 30 to 210, 30 to 200, 30 to 190, 30 to 180, 30 to 170, 30 to 160, 30 to 150, 30 to 140, 30 to 130, 30 to 120, 30 to 1 10, 30 to 100, 30 to 90, 30 to 80, 30 to 70, 30 to 60, 30 to 50, 30 to 40, 40 to 400, 40 to 390, 40 to 380, 40 to 370, 40 to 360, 40 to 350, 40 to 340, 40 to 330, 40 to 320, 40 to 310, 40 to 300, 40 to 390 0 to 290, 40 to 280, 40 to 270, 40 to 260, 40 to 250, 40 to 240, 40 to 230, 40 to 220, 40 to 210, 40 to 200, 40 to 190, 40 to 180, 40 to 170, 40 to 160, 40 to 150, 40 to 140, 40 to 130, 40 to 120,40 to 110, 40 to 100, 40 to 90, 40 to 80, 40 to 70, 40 to 60, 40 to 50, 50 to 400, 50 to 390, 50 to 380, 50 to 370, 50 to 360, 50 to 350, 50 to 340, 50 to 330, 50 to 320, 50 to 310, 50 to 300, 50 to 2 90, 50 to 280, 50 to 270, 50 to 260, 50 to 250, 50 to 240, 50 to 230, 50 to 220, 50 to 210, 50 to 200, 50 to 190, 50 to 180, 50 to 170, 50 to 160, 50 to 150, 50 to 140, 50 to 130, 50 to 120, 50 to 110, 50 to 100, 50 to 90, 50 to 80, 50 to 70, 50 to 60, 60 to 400, 60 to 390, 60 to 380, 60 to 370, 60 to 360, 60 to 350, 60 to 340, 60 to 330, 60 to 320, 60 to 310, 60 to 300, 60 to 290, 60 to 280 , 60 to 270, 60 to 260, 60 to 250, 60 to 240, 60 to 230, 60 to 220, 60 to 210, 60 to 200, 60 to 190, 60 to 180, 60 to 170, 60 to 160, 60 to 150, 60 to 140, 60 to 130, 60 to 120, 60 to 110, 60 to 10 0, 60 to 90, 60 to 80, 60 to 70, 70 to 400, 70 to 390, 70 to 380, 70 to 370, 70 to 360, 70 to 350, 70 to 340, 70 to 330, 70 to 320, 70 to 310, 70 to 300, 70 to 290, 70 to 280, 70 to 270, 70 to 260, 70 to 250, 70 to 240, 70 to 230, 70 to 220, 70 to 210, 70 to 200, 70 to 190, 70 to 180, 70 to 170, 70 to 160, 70 to 150, 70 to 140, 70 to 130, 70 to 120, 70 to 110, 70 to 100, 70 to 90, 70 to 80, 80 0 to 400, 80 to 390, 80 to 380, 80 to 370, 80 to 360, 80 to 350, 80 to 340, 80 to 330, 80 to 320, 80 to 310, 80 to 300, 80 to 290, 80 to 280, 80 to 270, 80 to 260, 80 to 250, 80 to 240, 80 to 230, 80 to 220, 80 to 210, 80 to 200, 80 to 190, 80 to 180, 80 to 170, 80 to 160, 80 to 150, 80 to 140, 80 to 130, 80 to 120, 80 to 110, 80 to 100, 80 to 90, 90 to 400, 90 to 390, 90 to 380, 90 to 370,90 to 360, 90 to 350, 90 to 340, 90 to 330, 90 to 320, 90 to 310, 90 to 300, 90 to 290, 90 to 280, 90 to 270, 90 to 260, 90 to 250, 90 to 240, 90 to 230, 90 to 220, 90 to 210, 90 to 200, 90 to 190 0, 90 to 180, 90 to 170, 90 to 160, 90 to 150, 90 to 140, 90 to 130, 90 to 120, 90 to 110, 90 to 100, 100 to 400, 100 to 390, 100 to 380, 100 to 370, 100 to 360, 100 to 350, 100 to 340, 100 to 330, 100 to 320, 100 to 310, 100 to 300, 100 to 290, 100 to 280, 100 to 270, 100 to 260, 100 to 250, 100 to 240, 100 to 230, 100 to 220, 100 to 210, 100 to 200, 100 to 190, 100 to 180, 100 to 170, 100 to 160, 100 to 150, 100 to 140, 100 to 130, 100 to 120, 100 to 110, 110 to 400, 110 to 390, 110 to 380, 110 to 370, 110 to 360, 110 to 350, 110 to 340, 110 to 330, 110 to 3 20, 110 to 310, 110 to 300, 110 to 290, 110 to 280, 110 to 270, 110 to 260, 110 to 250, 110 to 240, 110 to 230, 110 to 220, 110 to 210, 110 to 200, 110 to 190, 110 to 180, 110 to 170, 1 10 to 160, 110 to 150, 110 to 140, 110 to 130, 110 to 120, 120 to 400, 120 to 390, 120 to 380, 120 to 370, 120 to 360, 120 to 350, 120 to 340, 120 to 330, 120 to 320, 120 to 310, 120 to 30 0, 120 to 290, 120 to 280, 120 to 270, 120 to 260, 120 to 250, 120 to 240, 120 to 230, 120 to 220, 120 to 210, 120 to 200, 120 to 190, 120 to 180, 120 to 170, 120 to 160, 120 to 150, 120 to 140, 120 to 130, 130 to 400, 130 to 390, 130 to 380, 130 to 370, 130 to 360, 130 to 350, 130 to 340, 130 to 330, 130 to 320, 130 to 310, 130 to 300, 130 to 290, 130 to 280, 130 to 270,130 to 260, 130 to 250, 130 to 240, 130 to 230, 130 to 220, 130 to 210, 130 to 200, 130 to 190, 130 to 180, 130 to 170, 130 to 160, 130 to 150, 130 to 140, 140 to 400, 140 to 390, 140 to 3 80, 140 to 370, 140 to 360, 140 to 350, 140 to 340, 140 to 330, 140 to 320, 140 to 310, 140 to 300, 140 to 290, 140 to 280, 140 to 270, 140 to 260, 140 to 250, 140 to 240, 140 to 230, 140 to 290 0 to 220, 140 to 210, 140 to 200, 140 to 190, 140 to 180, 140 to 170, 140 to 160, 140 to 150, 150 to 400, 150 to 390, 150 to 380, 150 to 370, 150 to 360, 150 to 350, 150 to 340, 150 to 330 , 150 to 320, 150 to 310, 150 to 300, 150 to 290, 150 to 280, 150 to 270, 150 to 260, 150 to 250, 150 to 240, 150 to 230, 150 to 220, 150 to 210, 150 to 200, 150 to 190, 150 to 180, 150 to 170, 150 to 160, 160 to 400, 160 to 390, 160 to 380, 160 to 370, 160 to 360, 160 to 350, 160 to 340, 160 to 330, 160 to 320, 160 to 310, 160 to 300, 160 to 290, 160 to 280, 160 to 270, 1 60 to 260, 160 to 250, 160 to 240, 160 to 230, 160 to 220, 160 to 210, 160 to 200, 160 to 190, 160 to 180, 160 to 170, 170 to 400, 170 to 390, 170 to 380, 170 to 370, 170 to 360, 170 to 350 0, 170 to 340, 170 to 330, 170 to 320, 170 to 310, 170 to 300, 170 to 290, 170 to 280, 170 to 270, 170 to 260, 170 to 250, 170 to 240, 170 to 230, 170 to 220, 170 to 210, 170 to 200, 170 to 190, 170 to 180, 180 to 400, 180 to 390, 180 to 380, 180 to 370, 180 to 360, 180 to 350, 180 to 340, 180 to 330, 180 to 320, 180 to 310, 180 to 300, 180 to 290, 180 to 280, 180 to 270,180 to 260, 180 to 250, 180 to 240, 180 to 230, 180 to 220, 180 to 210, 180 to 200, 180 to 190, 190 to 400, 190 to 390, 190 to 380, 190 to 370, 190 to 360, 190 to 350, 190 to 340, 190 to 3 30, 190 to 320, 190 to 310, 190 to 300, 190 to 290, 190 to 280, 190 to 270, 190 to 260, 190 to 250, 190 to 240, 190 to 230, 190 to 220, 190 to 210, 190 to 200, 200 to 400, 200 to 390, 20 0 to 380, 200 to 370, 200 to 360, 200 to 350, 200 to 340, 200 to 330, 200 to 320, 200 to 310, 200 to 300, 200 to 290, 200 to 280, 200 to 270, 200 to 260, 200 to 250, 200 to 240, 200 to 230 , 200 to 220, 200 to 210, 210 to 400, 210 to 390, 210 to 380, 210 to 370, 210 to 360, 210 to 350, 210 to 340, 210 to 330, 210 to 320, 210 to 310, 210 to 300, 210 to 290, 210 to 280, 210 to 270, 210 to 260, 210 to 250, 210 to 240, 210 to 230, 210 to 220, 220 to 400, 220 to 390, 220 to 380, 220 to 370, 220 to 360, 220 to 350, 220 to 340, 220 to 330, 220 to 320, 220 to 310, 2 20 to 300, 220 to 290, 220 to 280, 220 to 270, 220 to 260, 220 to 250, 220 to 240, 220 to 230, 230 to 400, 230 to 390, 230 to 380, 230 to 370, 230 to 360, 230 to 350, 230 to 340, 230 to 33 0, 230 to 320, 230 to 310, 230 to 300, 230 to 290, 230 to 280, 230 to 270, 230 to 260, 230 to 250, 230 to 240, 240 to 400, 240 to 390, 240 to 380, 240 to 370, 240 to 360, 240 to 350, 240 to 340, 240 to 330, 240 to 320, 240 to 310, 240 to 300, 240 to 290, 240 to 280, 240 to 270, 240 to 260, 240 to 250, 250 to 400, 250 to 390, 250 to 380, 250 to 370, 250 to 360, 250 to 350,250 to 340, 250 to 330, 250 to 320, 250 to 310, 250 to 300, 250 to 290, 250 to 280, 250 to 270, 250 to 260, 260 to 400, 260 to 390, 260 to 380, 260 to 370, 260 to 360, 260 to 350, 260 to 340, 260 to 330, 260 to 320, 260 to 310, 260 to 300, 260 to 290, 260 to 280, 260 to 270, 270 to 400, 270 to 390, 270 to 380, 270 to 370, 270 to 360, 50, 270 to 340, 270 to 330, 270 to 320, 270 to 310, 270 to 300, 270 to 290, 270 to 280, 280 to 400, 280 to 390, 280 to 380, 280 to 370, 280 to 360, 280 to 350, 280 to 340, 280 to 330, 280 to 320, 280 to 310, 280 to 300, 280 to 290, 290 to 400, 290 to 390, 290 to 380, 290 to 370, 290 to 360, 290 to 350, 290 to 340, 290 to 330, 290 to 320, 0 to 310, 290 to 300, 300 to 400, 300 to 390, 300 to 380, 300 to 370, 300 to 360, 300 to 350, 300 to 340, 300 to 330, 300 to 320, 300 to 310, 310 to 400, 310 to 390, 310 to 380, 310 to 370, 310 to 360, 310 to 350, 310 to 340, 310 to 330, 310 to 320, 320 to 400, 320 to 390, 320 to 380, 320 to 370, 320 to 360, 320 to 350, 320 to 340, 320 to 330 330 to 400, 330 to 390, 330 to 380, 330 to 370, 330 to 360, 330 to 350, 330 to 340, 340 to 400, 340 to 390, 340 to 380, 340 to 370, 340 to 360, 340 to 350, 350 to 400, 350 to 390, 350 to 380, 350 to 370, 350 to 360, 360 to 400, 360 to 390, 360 to 380, 360 to 370, 370 to 400, 370 to 390, 370 to 380, 380 to 400, 380 to 390, or 390 to 400 carbon atoms.

[0032] In some embodiments, R 1It may include, for example, saturated and unsaturated hydrocarbon groups, linear and branched alkyl groups, and polyalkyl groups (eg, polyisobutylene groups or "PIB", polyethylene, polypropylene, etc.) The polyalkyl groups may be obtained by polymerization using olefin monomers such as isobutylene.

[0033] In some preferred embodiments, R 1 In some preferred embodiments, the polyisobutylene group has an average molecular weight of about 350 to about 5000. In some preferred embodiments, the polyisobutylene group has an average molecular weight of about 150 to about 1250, such as 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 polyisobutylene group has an average molecular weight of about 250 to about 1000, such as about 300 to about 900, about 400 to about 800, and about 500 to about 700.

[0034] In some preferred embodiments, the polyisobutylenyl group has an average molecular weight of about 500 to about 4000, such as 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, such as 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 1700 to about 4000, about 1800 to about 4000, about 1900 to about 4000, about 2000 to about 2500 00 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, such as about 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 about 1500 to about 1500, about 1200 to about 1500, about 1300 to about 1500, about 1400 to about 1500, about 1500 to about 1500, about 1600 to about 1500, about 1700 to about 1500, about 1800 to about 1500, about 1900 to about 1500, about 2000 to about 1500, about 2100 to about 1500, about 2200 to about 1500, about 2300 to about 1500, about 2400 to about 1500, about 2500 to about 1500, about 2600 to about 1500, about 2700 to about 1500, about 2800 to about 1500, about 2900 to about 1500, about 3000 to about 3500, about 500 to about 3000 00, such as about 600 to about 3000, about 700 to about 3000, about 800 to about 3000, about 900 to about 3000, about 1000 to about 3000, about 1100 to about 3000, about 1200 to about 3000, about 1300 to about 3000, about 1400 to about 3000, about 1500 to about 3000, about 1600 to about 3000, about 1700 to about 3000, about 1800 to about 3000, about 1900 to about 3000, about 2000 to about 3000, about 2100 to about 3000, about 2200 to about 3000, about 2300 to about 3000, about 2400 to about 3000, and about 2500 to about 3000.

[0035] R 1Specific examples include the following:

[0036]

[0037] wherein x is an integer such that the total number of carbons is from 10 to 400 as described herein.

[0038] X is a moiety comprising 1 to 10 carbon atoms, such as 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.

[0039] Specific examples of X include the following:

[0040]

[0041] Examples of Y include, for example, the following:

[0042]

[0043] Each R 2 are independently moieties comprising 1 to 9 carbon atoms, such as 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.

[0044] R 2 Suitable examples of include, for example, saturated and unsaturated hydrocarbon groups and straight-chain and branched alkyl groups.

[0045] R 2 Specific examples include the following:

[0046]

[0047] Z is a nitrogen, oxygen or sulfur atom.

[0048] Each R 3R is independently a hydrogen atom or a moiety comprising 1 to 9 carbon atoms, such as 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. Each R 3 The moieties include one or more nitrogen, oxygen or sulfur functionalizations.

[0049] R 3 Specific examples include the following:

[0050]

[0051] In some preferred embodiments, the lubricant additive may have the following general structure 2:

[0052]

[0053] Each R 1 is independently a hydrocarbon group having 10 to 400 carbon atoms; Y is nitrogen, oxygen or sulfur; each R 2 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

[0054] In some embodiments, Y may include one or more hydrogens.

[0055] In some preferred embodiments, the lubricant additive may have the following general structure 3:

[0056]

[0057] Each R 1 is independently a hydrocarbon group having 10 to 400 carbon atoms; each R 2 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

[0058] In some preferred embodiments, the lubricant additive may have the following general structure 4:

[0059]

[0060] Each R 1 is a hydrocarbon group having 10 to 400 carbon atoms; each R 2 is independently a hydrocarbyl group having 1 to 9 carbon atoms; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3 and n is 1 to 20.

[0061] When the additive composition is formulated in an engine oil (i.e., a lubricating oil composition), used as part of an aftermarket additive package during an engine flush, or used during a quick clean service, the additive composition is typically present in a concentration of about 0.1 wt % to about 50.0 wt %, such as 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 % to about 50 wt %, about 30 wt % to about 50 wt %, about 35 wt % to about 50 wt %, about 40 wt % to about 50 wt %, about 45 wt % to about 50 wt %, based on the total weight of the lubricating oil composition (which may be a blended product). % to about 50% by weight, about 0.1% to about 45% by weight, about 1% to about 45% by weight, about 5% to about 45% by weight, about 10% to about 45% by weight, about 15% to about 45% by weight, about 20% to about 45% by weight, about 25% to about 45% by weight, about 30% to about 45% by weight, about 35% to about 45% by weight, about 40% to about 45% by weight, about 0.1% to about 40% by weight, about 1% to about 40% by weight, about 5% to about 40% by weight, about 10% to about 40% by weight, about 15% to about 40% by weight, about 20% to about 40 ...0% by weight, about 30% to about 45% by weight % to about 40% by weight, about 35% by weight to about 40% by weight, about 0.1% by weight to about 35% by weight, about 1% by weight to about 35% by weight, about 5% by weight to about 35% by weight, about 10% by weight to about 35% by weight, about 15% by weight to about 35% by weight, about 20% by weight to about 35% by weight, about 25% by weight to about 35% by weight, about 30% by weight to about 35% by weight, about 0.1% by weight to about 30% by weight, about 1% by weight to about 30% by weight, about 5% by weight to about 30% by weight, about 10% by weight to about 30% by weight, about 15% by weight to about 30% by weight, about 20% by weight to about 30% by weight, about 25% by weight to about 30% by weight, about 0.1% by weight to about 25% by weight, about 1 % to about 25 wt %, about 5 wt % to about 25 wt %, about 10 wt % to about 25 wt %, about 15 wt % to about 25 wt %, and about 20 wt % to about 25 wt %, about 0.1 wt % to about 20.0 wt %, about 0.1 wt % to about 19.0 wt %, about 0.1 wt % to about 18.0 wt %, about 0.1 wt % to about 17.0 wt %, about 0.1 wt % to about 16.0 wt %, about 0.1 wt % to about 15.0 wt %, about 0.1 wt % to about 14.0 wt %, about 0.1 wt % to about 13.0 wt %, about 0.1 wt % to about 12.0 wt %, about 0.1 wt % to about 11.0 wt %, about 0.1 wt % to about 10.0 wt %, about 0.1 wt % to about 9.0 wt %, about 0.1 wt % to about 8.0 wt %, about 0.1 wt % to about 7.0 wt %, about 0.1 wt % to about 6.0 wt %, about 0.1 wt % to about 5.0 wt %, about 0.1 wt % to about 4.0 wt %, about 0.1 wt % to about 3.0 wt %, about 0.1 wt % to about 2.0 wt %, about 0.1 wt % to about 1.0 wt %, about 1.0 wt % to about 20.0 wt %, about 1.0 wt % to about 19.0 wt %, about 1.0 wt % to about 18.0 wt %, about 1.0 wt % to about 17.0 wt %, about 1.0 wt % to about 16.0 wt %, about 1.0 wt % to about 15.0 wt % %, about 1.0 wt % to about 14.0 wt %, about 1.0 wt % to about 13.0 wt %, about 1.0 wt % to about 12.0 wt %, about 1.0 wt % to about 11.0 wt %, about 1.0 wt % to about 10.0 wt %, about 1.0 wt % to about 9.0 wt %, about 1.0 wt % to about 8.0 wt %, about 1.0 wt % to about 7.0 wt %, about 1.0 wt % to about 6.0 wt %, about 1.0 wt % to about 5.0 wt %, about 1.0 wt % to about 4.0 wt %, about 1.0 wt % to about 3.0 wt %, about 1.0 wt % to about 2.0 wt %, about 2.0 wt % to about 20.0 wt %, about 2.0 wt % to about 19.0 wt %, about 2 .0 wt % to about 18.0 wt %, about 2.0 wt % to about 17.0 wt %, about 2.0 wt % to about 16.0 wt %, about 2.0 wt % to about 15.0 wt %, about 2.0 wt % to about 14.0 wt %, about 2.0 wt % to about 13.0 wt %, about 2.0 wt % to about 12.0 wt %, about 2.0 wt % to about 11.0 wt %, about 2.0 wt % to about 10.0 wt %, about 2.0 wt % to about 9.0 wt %, about 2.0 wt % to about 8.0 wt %, about 2.0 wt % to about 7.0 wt %, about 2.0 wt % to about 6.0 wt %, about 2.0 wt % to about 5.0 wt %, about 2.0 wt % to about 4.0 wt %, about 2. 0 wt % to about 3.0 wt %, about 3.0 wt % to about 20.0 wt %, about 3.0 wt % to about 19.0 wt %, about 3.0 wt % to about 18.0 wt %, about 3.0 wt % to about 17.0 wt %, about 3.0 wt % to about 16.0 wt %, about 3.0 wt % to about 15.0 wt %, about 3.0 wt % to about 14.0 wt %, about 3.0 wt % to about 13.0 wt %, about 3.0 wt % to about 12.0 wt %, about 3.0 wt % to about 11.0 wt %, about 3.0 wt % to about 10.0 wt %, about 3.0 wt % to about 9.0 wt %, about 3.0 wt % to about 8.0 wt %, about 3.0 wt % to about 7.0 wt %, about 3.% to about 15.0 wt %, about 5.0 wt % to about 14.0 wt %, about 5.0 wt % to about 16.0 wt %, about 5.0 wt % to about 17.0 wt %, about 5.0 wt % to about 18.0 wt %, about 5.0 wt % to about 19.0 wt %, about 5.0 wt % to about 19.0 wt %, about 5.0 wt % to about 18.0 wt %, about 5.0 wt % to about 17.0 wt %, about 5.0 wt % to about 16.0 wt %, about 5.0 wt % to about 15.0 wt %, about 5.0 wt % to about 14.0 wt %, about 5.0 wt % to about 13.0 wt %, about 5.0 wt % to about 12.0 wt %, about 5.0 wt % to about 11.0 wt %, about 5.0 wt % to about 10.0 wt %, about 5.0 wt % to about 9.0 wt %, about 5.0 wt % to about 8.0 wt %, about 5.0 wt % to about 7.0 wt %, about 5.0 wt % to about 6.0 wt %, about 6.0 wt % to about 20.0 wt %, about 6.0 wt % to about 19.0 wt %, about 6.0 wt % to about 18.0 wt %, about 6.0 wt % to about 17.0 wt %, about 6.0 wt % to about 16.0 wt %, about 6.0 wt % to about 15.0 wt %, about 6.0 wt % to about 14.0 wt %, about 6.0 wt % to about 13.0 wt %, about 6.0 wt % to about 12.0 wt %, about 6.0 wt % to about 11.0 wt %, about 6.0 wt % to about 10.0 wt % %, about 6.0 wt % to about 9.0 wt %, about 6.0 wt % to about 8.0 wt %, about 6.0 wt % to about 7.0 wt %, about 7.0 wt % to about 20.0 wt %, about 7.0 wt % to about 19.0 wt %, about 7.0 wt % to about 18.0 wt %, about 7.0 wt % to about 17.0 wt %, about 7.0 wt % to about 16.0 wt %, about 7.0 wt % to about 15.0 wt %, about 7.0 wt % to about 14.0 wt %, about 7.0 wt % to about 13.0 wt %, about 7.0 wt % to about 12.0 wt %, about 7.0 wt % to about 11.0 wt %, about 7.0 wt % to about 10.0 wt %, about 7.0 wt % to about 9.0 wt %. %, about 7.0 wt % to about 8.0 wt %, about 8.0 wt % to about 20.0 wt %, about 8.0 wt % to about 19.0 wt %, about 8.0 wt % to about 18.0 wt %, about 8.0 wt % to about 17.0 wt %, about 8.0 wt % to about 16.0 wt %, about 8.0 wt % to about 15.0 wt %, about 8.0 wt % to about 14.0 wt %, about 8.0 wt % to about 13.0 wt %, about 8.0 wt % to about 12.0 wt %, about 8.0 wt % to about 11.0 wt %, about 8.0 wt % to about 10.0 wt %, about 8.0 wt % to about 9.0 wt %, about 9.0 wt % to about 20.0 wt %, about 9.0 wt % to about 19.0 wt %, about 9.0 wt % to about 18.0 wt %, about 9.0 wt % to about 17.0 wt %, about 9.0 wt % to about 16.0 wt %, about 9.0 wt % to about 15.0 wt %, about 9.0 wt % to about 14.0 wt %, about 9.0 wt % to about 13.0 wt %, about 9.0 wt % to about 12.0 wt %, about 9.0 wt % to about 11.0 wt %, about 9.0 wt % to about 10.0 wt %, about 10.0 wt % to about 20.0 wt %, about 10.0 wt % to about 19.0 wt %, about 10.0 wt % to about 18.0 wt %, about 10.0 wt % to about 17.0 wt %, about 10.0 wt % to about 16.0 wt %, about % to about 15.0 wt %, about 10.0 wt % to about 14.0 wt %, about 10.0 wt % to about 13.0 wt %, about 10.0 wt % to about 12.0 wt %, about 10.0 wt % to about 11.0 wt %, about 11.0 wt % to about 20.0 wt %, about 11.0 wt % to about 19.0 wt %, about 11.0 wt % to about 18.0 wt %, about 11.0 wt % to about 17.0 wt %, about 11.0 wt % to about 16.0 wt %, about 11.0 wt % to about 15.0 wt %, about 11.0 wt % to about 14.0 wt %, about 11.0 wt % to about 13.0 wt %, about 11.0 wt % to about 12.0 wt % %, about 12.0 wt % to about 20.0 wt %, about 12.0 wt % to about 19.0 wt %, about 12.0 wt % to about 18.0 wt %, about 12.0 wt % to about 17.0 wt %, about 12.0 wt % to about 16.0 wt %, about 12.0 wt % to about 15.0 wt %, about 12.0 wt % to about 14.0 wt %, about 12.0 wt % to about 13.0 wt %, about 13.0 wt % to about 20.0 wt %, about 13.0 wt % to about 19.0 wt %, about 13.0 wt % to about 18.0 wt %, about 13.0 wt % to about 17.0 wt %, about 13.0 wt % to about 16.0 wt %, about 13.0 wt % to about 15.0 wt %, %, about 13.0 wt % to about 14.0 wt %, about 14.0 wt % to about 20.0 wt %, about 14.0 wt % to about 19.0 wt %, about 14.0 wt % to about 18.0 wt %, about 14.0 wt % to about 17.0 wt %, about 14.0 wt % to about 16.0 wt %, about 14.0 wt % to about 15.0 wt %, about 15.0 wt % to about 20.0 wt %, about 15.0 wt % to about 19.0 wt %, about 15.0 wt % to about 18.0 wt %, about 15.0 wt % to about 17.0 wt %, about 15.0 wt % to about 16.0 wt %, about 16.0 wt % to about 20.0 wt %, about 16.0 wt % to about 19.0 wt %.0 wt %, about 16.0 wt % to about 18.0 wt %, about 16.0 wt % to about 17.0 wt %, about 17.0 wt % to about 20.0 wt %, about 17.0 wt % to about 19.0 wt %, about 17.0 wt % to about 18.0 wt %, about 18.0 wt % to about 20.0 wt %, about 18.0 wt % to about 19.0 wt %, or about 19.0 wt % to about 20.0 wt %. .

[0062] In some embodiments, the additive is present at about 0.1 wt % to about 4.5 wt %, such as about 0.5 wt % to about 4.0 wt %, about 0.5 wt % to about 3.5 wt %, about 0.5 wt % to about 3.0 wt %, about 0.5 wt % to about 2.5 wt %, about 0.5 wt % to about 2.0 wt %, about 0.5 wt % to about 1.5 wt %, about 0.5 wt % to about 1.0 wt %, about 1.0 wt % to about 5.0 wt %, about 1.0 wt % to about 5.0 wt %, and about 1.0 wt % to about 2.5 wt %. 4.5 wt%, about 1.0 wt% to about 4.0 wt%, about 1.0 wt% to about 3.5 wt%, about 1.0 wt% to about 3.0 wt%, about 1.0 wt% to about 2.5 wt%, about 1.0 wt% to about 2.0 wt%, about 1.0 wt% to about 1.5 wt%, about 1.5 wt% to about 5.0 wt%, about 1.5 wt% to about 4.5 wt%, about 1.5 wt% to about 4.0 wt%, about 1.5 wt% to about 3.5 wt%, about 1.5 wt% to about 3.0 wt%, about 1.5 wt % to about 2.5 wt %, about 1.5 wt % to about 2.0 wt %, about 2.0 wt % to about 5.0 wt %, about 2.0 wt % to about 4.5 wt %, about 2.0 wt % to about 4.0 wt %, about 2.0 wt % to about 3.5 wt %, about 2.0 wt % to about 3.0 wt %, about 2.0 wt % to about 2.5 wt %, about 2.5 wt % to about 5.0 wt %, about 2.5 wt % to about 4.5 wt %, about 2.0 wt % to about 4.0 wt %, about 2.5 wt % to about 3.5 wt %, about 2.0 wt % to about 3.0 wt %, about 2.0 wt % to about 2.5 wt %, about 2.5 wt % to about 5.0 wt %, about 2.5 wt % to about 4.5 wt %, about 2.5 wt % to about 4.0 wt %, about 2.5 wt % to about About 3.5 weight %, about 2.5 weight % to about 3.0 weight %, about 3.0 weight % to about 5.0 weight %, about 3.0 weight % to about 4.5 weight %, about 3.0 weight % to about 4.0 weight %, about 3.0 weight % to about 3.5 weight %, about 3.5 weight % to about 5.0 weight %, about 3.5 weight % to about 4.5 weight %, about 3.5 weight % to about 4.0 weight %, about 4.0 weight % to about 5.0 weight %, about 4.0 weight % to about 4.5 weight %, or about 4.5 weight % to about 5.0 weight %.

[0063] Specific non-limiting examples of lubricant additive compositions include the following:

[0064]

[0065]

[0066] The lubricant additive composition can be synthesized by any compatible method. For example, U.S. Patent No. 5,669,939 describes in detail the general synthesis of Compound 1, which is incorporated herein by reference. Such reactions generally produce a product comprising Compound 1 dissolved in an organic solvent. In some embodiments, it may be desirable to evaporate the organic solvent before using Compound 1.

[0067] In some embodiments, compound 1 can be used as a starting material for synthesizing other lubricant additive compounds (e.g., compounds 4, 5, 6). An overview of how compounds 4, 5, and 6 are derived is shown below. In each reaction, the starting materials are the same. Only the feed molar ratio (compound 1 to glycidol) is different. In addition to glycidol, other reagents may also be considered. In addition, the lubricant additive is not necessarily a reaction product of glycidol or derived from glycidol.

[0068]

[0069] Succinimide dispersant

[0070] 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 %, such as 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 8 wt %, about 0.5 wt % to about 7 wt %, about 0.5 wt % to about 6 wt %, about 0.5 wt % to about 5 wt %, about 0.5 wt % to about 4 wt %, about 0.5 wt % to about 3 wt %, about 0.5 wt % to about 2 wt %, about 0.5 wt % to about 1 wt %, about 1 wt % to about 10 wt %, about 1 wt % to about 9 wt %, about 1 wt % to about 8 wt %, about 1 wt % to about 7 wt %, about 1 wt % to about 6 wt %, about 1 wt % to about 5 wt %, about 1 wt % to about 4 wt %, about 1 wt % to about 3 wt %, about 1 wt % to about 2 wt %, about 2 wt % From about 10 wt %, from about 2 wt % to about 9 wt %, from about 2 wt % to about 8 wt %, from about 2 wt % to about 7 wt %, from about 2 wt % to about 6 wt %, from about 2 wt % to about 5 wt %, from about 2 wt % to about 4 wt %, from about 2 wt % to about 3 wt %, from about 3 wt % to about 10 wt %, from about 3 wt % to about 9 wt %, from about 3 wt % to about 8 wt %, from about 3 wt % to about 7 wt %, from about 3 wt % to about 6 wt %, from about 3 wt % to about 5 wt %, from about 3 wt % to about 4 wt %, from about 4 wt % to about 10 wt %, from about 4 wt % to about 9 wt %, from about 4 wt % to about 8 ... % to about 7 weight %, about 4 weight % to about 6 weight %, about 4 weight % to about 5 weight %, about 5 weight % to about 10 weight %, about 5 weight % to about 9 weight %, about 5 weight % to about 8 weight %, about 5 weight % to about 7 weight %, about 5 weight % to about 6 weight %, about 6 weight % to about 10 weight %, about 6 weight % to about 9 weight %, about 6 weight % to about 8 weight %, about 6 weight % to about 7 weight %, about 7 weight % to about 10 weight %, about 7 weight % to about 9 weight %, about 7 weight % to about 8 weight %, about 8 weight % to about 10 weight %, about 8 weight % to about 9 weight %, or about 9 weight % to about 10 weight %.

[0071] In one embodiment, the polyalkenyl bissuccinimide can be obtained by reacting the following polyalkenyl substituted succinic anhydride with a polyamine:

[0072]

[0073] wherein R is a polyalkenyl substituent derived from a polyolefin radical having a number average molecular weight of about 500 to about 3000. In one embodiment, R is a polyalkenyl substituent derived from a polyolefin radical having a number average molecular weight of about 1000 to about 2500.

[0074] In one embodiment, R is a polyisobutylene substituent derived from polyisobutylene having a number average molecular weight of about 500 to about 3000. In another embodiment, R is a polyisobutylene substituent derived from polyisobutylene having a number average molecular weight of about 1000 to about 2500.

[0075] Suitable polyamines for preparing the bis-succinimide dispersant include 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 are those having the formula: H2N—(R′NH)x—H, wherein R′ is a linear or branched alkylene group having 2 or 3 carbon atoms and x is 1 to 9. Representative examples of suitable polyalkylene polyamines include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, and heavy polyamines (e.g., ethyleneamine E-100 available from Huntsman Company).

[0076] In general, 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. In general, a suitable molar charge of the polyamine to 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, "molar charge of polyamine to polyalkenyl-substituted succinic anhydride" means the ratio of the number of moles of polyamine to the number of succinic acid groups in the succinic anhydride reactant.

[0077] One class of suitable polyalkenyl succinimides can be represented by the following structure:

[0078]

[0079] wherein R and R' are as described herein above and y is 1 to 11.

[0080] Post-treatment of polyalkenyl succinimide

[0081] In some embodiments, the succinimide dispersant may be post-treated with an organic carbonate.

[0082] Suitable organic carbonates include, for example, cyclic carbonates such as 1,3-dioxolane-2-one (ethylene carbonate or "EC"); 4-methyl-1,3-dioxolane-2-one (propylene carbonate); 4-ethyl-1,3-dioxolane-2-one (butylene carbonate); 4-hydroxymethyl-1,3-dioxolane-2-one; 4,5-dimethyl-1,3-dioxolane-2-one; 4-ethyl-1,3-dioxolane-2-one; 4,4-dimethyl-1,3-dioxolane-2-one; 4-methyl-5-ethyl-1,3-dioxolane-2-one; 4,5-diethyl-1,3-dioxolane-2-one; 4,4-diethyl-1,3-dioxolane-2-one; 1,3-dioxane-2-one; 4, 4-dimethyl-1,3-dioxane-2-one; 5,5-dimethyl-1,3-dioxane-2-one; 5,5-dihydroxymethyl-1,3-dioxane-2-one; 5-methyl-1,3-dioxane-2-one; 4-methyl-1,3-dioxane-2-one; 5-hydroxy-1,3-dioxane-2-one; 5-hydroxymethyl-5-methyl-1,3-dioxane-2-one; 5,5-diethyl-1,3-dioxane-2-one; 5-methyl-5-propyl-1,3-dioxane-2-one; 4,6-dimethyl-1,3-dioxane-2-one; 4,4,6-trimethyl-1,3-dioxane-2-one and spiro[1,3-oxa-2-cyclohexanone-5,5'-1',3'-oxa-2'-cyclohexanone]. Other suitable cyclic carbonates can be prepared by methods known in the art from sugars such as sorbitol, glucose, fructose, galactose, etc. and from C1 to C 30 Preparation of vicinal diols from olefin preparation.

[0083] lubricating oil

[0084] The lubricating oil composition of the present invention includes one or more base oils (e.g., Group I, II, III, IV, or V). In addition, the one or more base oils may include base oils from the same group (e.g., Group II Chevron neutral oils). Group II Chevron Neutral Oil and Group II Chevron Neutral Oil ). The base oil is present in an amount of about 50 wt. % or greater (a "major amount") based on the total weight of the lubricating oil composition.

[0085] The oil of lubricating viscosity (sometimes referred to as "base stock" or "base oil") is the main liquid component of the lubricant into which additives and possibly other oils are blended, for example, to produce the final lubricant (or lubricant composition). The base oils useful for preparing the concentrates and for preparing the lubricating oil compositions therefrom may be selected from natural (vegetable, animal or mineral) lubricating oils and synthetic lubricating oils and mixtures thereof.

[0086] The oil used as the base oil will be selected or blended according to the desired end use and additives in the finished oil to obtain a desired grade of engine oil, such as a lubricating oil composition having a standard of the Society of Automotive Engineers (SAE). In one embodiment, the lubricating oil composition is a multigrade oil for heavy-duty vehicles or passenger cars. The multigrade oil can have an SAE viscosity grade 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.

[0087] The definitions of base stocks and base oils in this disclosure are the same as those in Appendix E of American Petroleum Institute (API) Publication 1509 ("API Base Oil Interchangeability Guidelines for Pas senger Car Motor Oils and Diesel Engine Oils," December 2016). Group I base stocks contain less than 90% saturated hydrocarbons and / or greater than 0.03% sulfur, and have a viscosity index greater than or equal to 80 and less than 120, using the test methods specified in Table E-1. Group II base stocks contain greater than or equal to 90% saturated hydrocarbons and less than or equal to 0.03% sulfur, and have a viscosity index greater than or equal to 80 and less than 120, using the test methods specified in Table E-1. Group III base stocks contain greater than or equal to 90% saturated hydrocarbons and less than or equal to 0.03% sulfur, and have a viscosity index greater than or equal to 120, using the test methods specified in Table E-1. Group IV base stocks are polyalphaolefins (PAOs). Group V base stocks include all other base stocks not included in Group I, Group II, Group III or Group IV.

[0088] Natural oils include animal oils, vegetable oils (e.g., castor oil and lard) and mineral oils. Animal oils and vegetable oils with good thermal oxidation stability can be used. Among natural oils, mineral oils are preferred. Mineral oils vary greatly in their crude oil sources (e.g., whether they are paraffinic, cycloparaffinic or mixed paraffinic-cycloparaffinic). Oils derived from coal or shale are also useful. Natural oils also vary in their production and purification methods (e.g., their distillation ranges) and whether they are straight run or cracked, hydrofined or solvent extracted.

[0089] Synthetic oils include hydrocarbon oils. Hydrocarbon oils include oils such as polymerized and interpolymerized olefins (e.g., polybutene, polypropylene, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene-α-olefin copolymers). Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oils. For example, a C8 to C6 derivative may be used. 14 Olefins, such as C8, C 10 , C 12 , C 14 PAO of olefins or mixtures thereof.

[0090] Other useful fluids for use as base oils include non-conventional or unconventional base stocks which have been processed (preferably catalytically processed) or synthesized to provide high performance properties.

[0091] Unconventional or extra-conventional base stocks / base oils include one or more of the following: mixtures of base stocks derived from one or more natural gas to liquids (GTL) materials, and isomerate / isodewaxate base stocks derived from natural waxes or waxy feeds, mineral and or non-mineral oil waxy feeds such as slack wax, natural waxes and waxy feeds such as gas oils, waxy fuel hydrocracker bottoms, waxy raffinates, hydrocracked products, thermal cracked products or other mineral, mineral oil or even non-petroleum derived waxy materials such as waxy materials obtained from coal liquefaction or shale oil, and mixtures of such base stocks. Other base oils include coal to liquids (CTL) products and alkylated naphthalenes.

[0092] The base oil used in the lubricating oil composition of the present disclosure is any kind of oil 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 Group III to Group V base oils, due to their superior volatility, stability, viscosity and cleanliness characteristics.

[0093] The high temperature shear (HTHS) viscosity of the lubricating oil composition at 150° C. may be 2.9 cP or less, such as 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, 1.6 cP or less, 1.7 cP or less, 1.8 cP or less, 1.9 cP or less, 1.9 cP or less, 1.8 ... 1.4cP or less, 1.3cP or less, 1.2cP or less, 1.1cP or less, 1.0cP or less, 1.0cP to 2.9cP, 1.3cP to 2.9cP, 1.0cP to 2.6cP, 1.3cP to 2.6cP, 1.0cP to 2.3cP, 1.3cP to 2.3cP, 1.0cP to 2.0cP, 1.3cP to 2.3cP, 1.0cP to 1.7cP or 1.3cP to 1.7cP.

[0094] 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). If the viscosity index of the lubricating oil composition is less than 135, it may be difficult to improve fuel efficiency while maintaining HTHS viscosity at 150° C. If the viscosity index of the lubricating oil composition exceeds 400, evaporation characteristics may be reduced, and defects may be caused due to insufficient solubility of additives and matching characteristics with sealing materials.

[0095] The kinematic viscosity of the base oil at 100°C (ASTM D445) can be between 3 and 12 mm 2 / s range, such as 3 to 11mm 2 / s, 3 to 10 mm 2 / s, 3 to 9 mm 2 / s, 3 to 8 mm 2 / s, 3 to 7 mm 2 / s, 3 to 6 mm 2 / s, 3 to 5 mm 2 / s, 3 to 4 mm 2 / s, 4 to 12 mm 2 / s, 4 to 11 mm 2 / s, 4 to 10 mm 2 / s, 4 to 9 mm 2 / s, 4 to 8 mm 2 / s, 4 to 7 mm 2 / s, 4 to 6 mm2 / s, 4 to 5 mm 2 / s, 5 to 12 mm 2 / s, 5 to 11 mm 2 / s, 5 to 10 mm 2 / s, 5 to 9 mm 2 / s, 5 to 8 mm 2 / s, 5 to 7 mm 2 / s, 5 to 6 mm 2 / s, 6 to 12 mm 2 / s, 6 to 11 mm 2 / s, 6 to 10 mm 2 / s, 6 to 9 mm 2 / s, 6 to 8 mm 2 / s, 6 to 7 mm 2 / s, 7 to 12 mm 2 / s, 7 to 11 mm 2 / s, 7 to 10 mm 2 / s, 7 to 9 mm 2 / s, 7 to 10 mm 2 / s, 7 to 9 mm 2 / s, 7 to 8 mm 2 / s, 8 to 12 mm 2 / s, 8 to 11 mm 2 / s, 8 to 10 mm 2 / s, 8 to 9 mm 2 / s, 9 to 12 mm 2 / s, 9 to 11 mm 2 / s, 9 to 10 mm 2 / s, 10 to 12 mm 2 / s, 10 to 11 mm 2 / s or 11 to 12 mm 2 / s.

[0096] Other additives

[0097] The lubricating oil composition of the present invention may also contain conventional additives for imparting auxiliary functions to obtain a 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, cleaning agents (such as metal cleaning agents), rust inhibitors, demisters, demulsifiers, friction modifiers, metal deactivators, pour point depressants, viscosity modifiers, defoamers, cosolvents, packaging extenders, corrosion inhibitors, dyes, extreme pressure agents, etc. and mixtures thereof. A variety of additives are known and commercially available. These additives or their analogous compounds may be used to prepare the lubricating oil composition of the present invention by conventional blending procedures.

[0098] When used, each of the aforementioned additives is used in a functionally effective amount to impart the desired properties to the lubricant. Thus, for example, if the additive is an ashless dispersant, the functionally effective amount of such ashless dispersant will be an amount sufficient to impart the desired dispersion characteristics to the lubricant. Generally speaking, unless otherwise indicated, when used, the concentration of each of these additives may be in the range of about 0.001 wt % to about 20 wt %, such as about 0.01 wt % to about 10 wt %.

[0099] Preparation

[0100] Typically, the sulfur level in the lubricating oil composition of the present invention is less than or equal to about 0.7 wt %, based on the total weight of the lubricating oil composition, for example, the sulfur level is from about 0.01 wt % to about 0.70 wt %, 0.01 wt % to 0.6 wt %, 0.01 wt % to 0.5 wt %, 0.01 wt % to 0.4 wt %, 0.01 wt % to 0.3 wt %, 0.01 wt % to 0.2 wt %, 0.01 wt % to 0.10 wt %. In one embodiment, the sulfur level in the lubricating oil composition of the present invention is less than or equal to about 0.60 wt %, less than or equal to about 0.50 wt %, less than or equal to about 0.40 wt %, less than or equal to about 0.30 wt %, less than or equal to about 0.20 wt %, less than or equal to about 0.10 wt %, based on the total weight of the lubricating oil composition.

[0101] In one embodiment, the phosphorus level in the lubricating oil composition of the present invention is less than or equal to about 0.12 wt % based on the total weight of the lubricating oil composition, such as a phosphorus level of about 0.01 wt % to about 0.12 wt %. In one embodiment, the phosphorus level in the lubricating oil composition of the present invention is less than or equal to about 0.11 wt % based on the total weight of the lubricating oil composition, such as a phosphorus level of about 0.01 wt % to about 0.11 wt %. In one embodiment, the phosphorus level in the lubricating oil composition of the present invention is less than or equal to about 0.10 wt % based on the total weight of the lubricating oil composition, such as a phosphorus level of about 0.01 wt % to about 0.10 wt %. In one embodiment, the phosphorus level in the lubricating oil composition of the present invention is less than or equal to about 0.09 wt % based on the total weight of the lubricating oil composition, such as a phosphorus level of about 0.01 wt % to about 0.09 wt %. In one embodiment, the phosphorus level in the lubricating oil composition of the present invention is less than or equal to about 0.08 wt % based on the total weight of the lubricating oil composition, such as a phosphorus level of about 0.01 wt % to about 0.08 wt %. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is less than or equal to about 0.07 wt %, based on the total weight of the lubricating oil composition, such as a level of phosphorus ranging from about 0.01 wt % to about 0.07 wt %. In one embodiment, the level of phosphorus in the lubricating oil composition of the present invention is less than or equal to about 0.05 wt %, based on the total weight of the lubricating oil composition, such as a level of phosphorus ranging from about 0.01 wt % to about 0.05 wt %.

[0102] In one embodiment, the level of sulfated ash produced by the lubricating oil composition of the present invention is less than or equal to about 1.60 wt % as determined by ASTM D 874, for example, the level of sulfated ash is from about 0.10 to about 1.60 wt % as determined by ASTM D 874. In one embodiment, the level of sulfated ash produced by the lubricating oil composition of the present invention is less than or equal to about 1.00 wt % as determined by ASTM D 874, for example, the level of sulfated ash is from about 0.10 to about 1.00 wt % as determined by ASTM D 874. In one embodiment, the level of sulfated ash produced by the lubricating oil composition of the present invention is less than or equal to about 0.80 wt % as determined by ASTM D 874, for example, the level of sulfated ash is from about 0.10 to about 0.80 wt % 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 D874, for example, the sulfated ash level is from about 0.10 to about 0.60 wt % as determined by ASTM D 874.

[0103] Suitably, the lubricating oil composition of the present invention may have a total base number (TBN) of 4 to 15 mg KOH / g (eg, 5 to 12 mg KOH / g, 6 to 12 mg KOH / g, or 8 to 12 mg KOH / g).

[0104] The following non-limiting examples are illustrative of the present invention. A brief description of how the examples were prepared is provided.

[0105] Example

[0106] Benchmark formulation

[0107] The baseline formulation is a SAE 5W-40 viscosity grade lubricating oil composition prepared by blending the following components:

[0108] a) 0.017 wt. % of calcium borosulfonate calculated as boron, TBN 160

[0109] b) 0.02 wt% of highly basic calcium phenate, calculated as calcium, TBN 260

[0110] c) 0.074 wt% ZnDTP calculated as P

[0111] d) 0.13 wt. % of overbased calcium sulfonate, TBN 410

[0112] e) Antioxidants

[0113] f) Ethylene-propylene viscosity modifier

[0114] The remainder of the lubricating oil composition comprises a small amount of a foam inhibitor, 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.

[0115] Example 1

[0116] The following components were added to the baseline formulation to prepare Example 1:

[0117] 6.5 wt% EC treated succinimide

[0118] 2 wt% of compound 2

[0119] Example 2

[0120] The following components were added to the baseline formulation to prepare Example 2:

[0121] 6.5 wt% EC treated succinimide

[0122] 2 wt% of compound 1

[0123] Example 3

[0124] The following components were added to the baseline formulation to prepare Example 3:

[0125] 6.5 wt% EC treated succinimide

[0126] 2 wt% of compound 3

[0127] Example 4

[0128] The following components were added to the baseline formulation to prepare Example 4:

[0129] 6.5 wt% EC treated succinimide

[0130] 2 wt% of compound 4

[0131] Example 5

[0132] The following components were added to the baseline formulation to prepare Example 5:

[0133] 4 wt% EC treated succinimide

[0134] 2 wt% of compound 4

[0135] Example 6

[0136] The following components were added to the baseline formulation to prepare Example 6:

[0137] 4 wt% EC treated succinimide

[0138] 1 wt% of compound 2

[0139] The remainder of the lubricating oil composition includes minor amounts of foam inhibitor, pour point depressant and base oil.

[0140] Example 7

[0141] The following components were added to the baseline formulation to prepare Example 7: 8 wt% EC treated succinimide

[0142] Example 8

[0143] The following components were added to the baseline formulation to prepare Example 8: 6 wt% EC treated succinimide 2 wt% Compound 2

[0144] Example 9

[0145] The following components were added to the baseline formulation to prepare Example 9: 6 wt% EC treated succinimide 2 wt% Compound 3

[0146] Example 10

[0147] The following components were added to the baseline formulation to prepare Example 10: 6 wt% EC treated succinimide 2 wt% Compound 5

[0148] Embodiment 11

[0149] The following components were added to the baseline formulation to prepare Example 11: 6 wt% EC treated succinimide 2 wt% Compound 4

[0150] Example 12

[0151] The following components were added to the baseline formulation to prepare Example 12:

[0152] 4 wt% EC treated succinimide

[0153] 2 wt% of compound 2

[0154] Embodiment 13

[0155] The following components were added to the baseline formulation to prepare Example 13:

[0156] 4 wt% EC treated succinimide

[0157] 1 wt% of compound 2

[0158] Embodiment 14

[0159] The following components were added to the baseline formulation to prepare Example 14:

[0160] 2 wt% of compound 1

[0161] TDI 3 engine test

[0162] Piston cleanliness and ring adhesion were evaluated by the TDI 3 engine test, which is very similar to the Volkswagen turbocharged DI test, a European passenger car diesel engine test (CEC-L-78-T-99) and part of the ACEA A / B and C specifications issued by the European Automobile Manufacturers Association in 2004. The test is used to simulate repeated cycles of idling after high-speed operation. A Volkswagen 1.9-liter inline four-cylinder turbocharged direct injection automotive diesel engine (VWTDi) was mounted on an engine dynamometer stand. A 54-hour, two-stage program was performed without intermediate oil replenishment, cycling between idling at 40°C sump for 30 minutes and full power (4150 rpm) at 145°C sump for 150 minutes. After the program, the pistons were evaluated for carbon and lacquer deposits and groove carbon filling. Ring adhesion of the piston rings was evaluated. Table 1 summarizes the TDI 3 results.

[0163] Table 1

[0164]

[0165] Paint board coker test

[0166] The lacquer plate coker test is a method for determining the relative stability of a lubricant. It is commonly used to evaluate the deposit formation or lacquering tendency of lubricants in contact with hot metal surfaces, thereby simulating deposit formation in engine cylinders and pistons. The test apparatus includes a rectangular stainless steel reservoir, tilted 25° from the horizontal. The test plate (95mm×45mm) is held in place by a heating element equipped with a thermocouple probe to control the temperature of the aluminum or steel test plate. A horizontal shaft equipped with a series of sharp teeth is positioned above the oil and rotated at 1000rpm. 300ml of the lubricating oil to be evaluated is placed in the lacquer plate coker apparatus and the oil temperature is controlled at 100°C, while the test plate is heated to 300°C. During the rotation of the shaft, the sharp teeth sweep over the test lubricant, and the lubricant droplets are thrown onto the heated test lacquer plate. At the end of the 3-hour test duration, the test lacquer plate is reweighed and the amount of deposit formed is determined. The weight gain of the test painted panels 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.

[0167] Table 2

[0168]

[0169] Quickly removes clean deposits

[0170] Examples 15 to 17 and Comparative Example A were formulated to provide lubricating oil compositions meeting the following specifications: SAE 30 viscosity grade (Kv @100℃: about 15.0mm 2 / s).

[0171] Examples 15 to 17 were blended with the following components:

[0172] a) Group II base oil

[0173] b) 9.7 wt % of an engine oil additive package (including, for example, dispersants, detergents, antioxidants, friction modifiers)

[0174] c) Compound A (diluted in 30 wt% C9 aromatic solvent) at various treatment rates (Table 4):

[0175]

[0176] Comparative Example B (Table 3) is similar to Examples 15 to 17, but does not include Compound A.

[0177] Experimental Procedure I

[0178] In the first set of experiments, various concentrations of Compound A were blended with finished oil to observe its solubility and tendency to dissolve carbocyclic deposits. The blending of Compound A and finished oil was carried out at ambient temperature for 20 minutes.

[0179] Compound A was added in varying amounts to a finished oil containing an engine oil additive package. Actual ring segments from an internal combustion engine containing high concentrations of carbonaceous deposits were used in the experiment. The ring was pre-washed with hexane, dried, and then weighed to 4 decimal places. Next, the ring segment was carefully placed in a beaker containing the finished oil (i.e., Examples 4 to 6 and Comparative Example B). The samples were allowed to sit in the finished oil for 4, 6, and 24 hours without stirring. The approximate temperature of the finished oil was ~22°C. A turbidity formed around the segmented ring pieces, indicating that some of the deposits were removed. The ring segments were removed, rinsed with hexane, air dried, and then weighed again.

[0180] As shown in Table 3, the concentration of Compound A in the finished oil correlated well with the removal of deposits, as did the soaking / residence time. The cumulative ring weight loss corresponding to the deposit removal is reported in mg (higher mg values ​​indicate better deposit removal performance).

[0181] Table 3

[0182]

[0183] TBN Boost

[0184] The effect of compound A on total base number (TBN) was observed by JIS K-2501:2003 8 (ASTM D2896) method (DH-2). As shown in Table 4 below, although compound A is a soft base component (containing only N), it increases TBN more. High TBN is usually required to neutralize acidic byproducts of combustion and oxidation.

[0185] Table 4

[0186]

[0187] Sediment testing

[0188] The 0W-20 formulated oils containing Compound A (invention) and comparative 0W-20 formulated oils were evaluated using the Daimler OM471LA Heavy Duty Engine Oil Performance Test. This engine test provides an assessment of piston cleanliness, cylinder bore polish, oil consumption, general engine deposits, engine sludge, general engine wear, cylinder wear, piston ring sticking, and / or turbocharger deposits.

[0189] The OM 471LA Euro VI engine is a mature production engine that represents Euro 6 heavy-duty engine technology. The 6-cylinder in-line engine features steel pistons, 12.8 litres displacement, turbocharger and wastegate.

[0190] The test duration is 600 hours (two consecutive 300 hour operating blocks) and includes stop / start events to represent the severe application of the vehicle in the field. To ensure good test repeatability, a known fuel (Coryton RF 99-21) is used. At the end of the test, piston deposits are assessed.

[0191] The only difference between the inventive 0W-20 formulated oil and the comparative 0W-20 formulated oil was that the inventive oil contained 2.7 wt % of Compound A, which replaced the 2.7 wt % of the ethylene carbonate treated bis-succinimide dispersant present in the comparative oil. The following table shows the deposit removal (in percent) observed under the piston crown and in the turbocharger housing.

[0192]

[0193] For the sake of brevity, only certain ranges are explicitly disclosed herein. However, the range from any lower limit can be combined with any upper limit to list a range that is not explicitly listed, and the range from any lower limit can be combined with any other lower limit to list a range that is not explicitly listed, and in the same manner, the range from any upper limit can be combined with any other upper limit to list a range that is not explicitly listed. In addition, each point or single value between the endpoints of the range is included in the range, even if it is not explicitly listed. Therefore, each point or single value can serve as its own lower limit or upper limit to be combined with any other point or single value or any other lower limit or upper limit to list a range that is not explicitly listed.

[0194] Likewise, the term "comprising" is considered synonymous with the term "including." Likewise, whenever a composition, an element, or a group of elements is preceded by the transitional phrase "comprising," it should be understood that we also contemplate the same composition or group of elements having the transitional phrases "consisting essentially of," "consisting of," "selected from the group consisting of," or "being" preceding the recitation of the composition, an element, or a plurality of elements, and vice versa.

[0195] As used herein, the terms "a", "an" and "the" should be construed to cover the plural as well as the singular.

[0196] Various terms have been defined above. If a term used in a claim is not defined above, it should be given the broadest definition that persons in the relevant art have given that term as reflected in at least one printed publication or issued patent. In addition, all patents, test procedures, and other documents cited in this application are fully incorporated by reference to the extent such disclosure is not inconsistent with this application and for all jurisdictions in which such incorporation is permitted.

[0197] The foregoing description of the present disclosure illustrates and describes the present disclosure. In addition, the present disclosure shows and describes only preferred embodiments, but as mentioned above, it should be understood that the present disclosure can be used in various other combinations, modifications and environments, and can be changed or modified within the scope of the concepts expressed herein commensurate with the above teachings and / or the technology or knowledge of the relevant field. Although the foregoing is directed to embodiments of the present disclosure, other and further embodiments of the present disclosure can be designed without departing from the basic scope of the present disclosure, and the scope of the present disclosure is determined by the appended claims.

[0198] It should be understood that when combinations, subsets, groups, etc. of elements are disclosed (e.g., combinations of components in compositions, or combinations of steps in methods), while specific reference to each of the various individual and collective combinations and arrangements of these elements may not be explicitly disclosed, each is specifically contemplated and described herein.

[0199] The embodiments described above are further intended to explain the best known modes of practicing it and to enable others skilled in the art to utilize the present disclosure in such or other embodiments and with various modifications required for a particular application or use. Therefore, this specification is not intended to be limited to the forms disclosed herein. In addition, the appended claims are intended to be interpreted as including alternative embodiments.

Claims

1. A lubricating oil composition, comprising: a major amount of base oil; and Lubricant additives having the following structure: Each R 1 is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

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

3. The lubricating oil composition according to claim 1, wherein R 1 A polyalkyl group.

4. The lubricating oil composition according to claim 1, wherein R 1 It is a polyisobutylene group. 5 . The lubricating oil composition according to claim 1 , further comprising a succinimide dispersant.

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

7. The lubricating oil composition of claim 1, wherein the lubricant additive has the following general structure: Each R 1 is independently a hydrocarbon group having 10 to 400 carbon atoms; Y is nitrogen, oxygen or sulfur; each R 2 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

8. A method of lubricating an engine, the method comprising lubricating the engine with a lubricating oil composition, the lubricating oil composition comprising: a major amount of base oil; and Lubricant additives having the following structure: Each R 1 is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

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

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

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

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

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

14. The method of claim 8, wherein the lubricant additive has the following general structure: Each R 1 is independently a hydrocarbon group having 10 to 400 carbon atoms; Y is nitrogen, oxygen or sulfur; each R 2 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

15. A method of improving piston cleanliness or oxidation inhibition in an engine, the method comprising lubricating the engine with a lubricating oil composition comprising: a major amount of base oil; and Lubricant additives having the following structure: Each R 1 is 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 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

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

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

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

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

20. The method of claim 15, wherein the lubricant additive has the following general structure: Each R 1 is independently a hydrocarbon group having 10 to 400 carbon atoms; Y is nitrogen, oxygen or sulfur; each R 2 is independently a hydrocarbyl group having 1 to 9 carbons; Z is nitrogen, oxygen or sulfur; and each R 3 is independently hydrogen or a hydrocarbyl group having 1 to 9 carbons with one or more nitrogen, oxygen or sulfur functionalizations, wherein p is 1 to 3, n is 1 to 20 and m is 0 to 3.

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