Aminoalkanediols and Carboxylate Salts as Additives for Improving Fuel Efficiency

Abstract

Friction modifiers and compositions containing the friction modifiers as fuel additives are provided, as are methods for improving fuel efficiency using these compositions.

Description

[Technical field]

[0001] The present disclosure relates to fuel or lubricating oil additives, and compositions containing the additives, that improve engine fuel economy by reducing friction and / or reducing wear. [Background technology]

[0002] In a typical fuel-based internal combustion engine, less than 40% of the energy of the fuel is converted into mechanical power. From there, roughly one-third of the converted mechanical power is lost due to friction. To counter this loss of fuel efficiency, fuel or lubricating oil compositions can contain additives that reduce friction ("friction modifiers") to increase fuel efficiency. Friction modifiers can also function to protect high-pressure fuel pumps and injectors from wear caused by the fuel.

[0003] There are several classes of friction modifiers, the major class being organic friction modifiers. Organic friction modifiers are generally long, thin molecules with a polar head attached to a long hydrocarbon chain. The polar head is attracted to the metal and allows the friction modifier to adhere to the metal surface while the hydrocarbon chain remains perpendicular to the surface, thereby preventing asperity contact and reducing friction and / or wear.

[0004] Among organic friction modifiers, certain fatty acids and their derivatives (esters and amides) are commonly used. These include glycerol derivatives such as glycerol monooleate (GMO or "Glymo"). Due to the fatty and sometimes waxy nature of fatty acids and their derivatives, concentrated additive packages containing such materials are prone to the formation of solids, sediments and / or thick gels in additive packages containing these materials. This non-ideal low temperature storage stability results in reduced handling characteristics of packages containing these additives, especially in areas where the packages may be periodically exposed to lower temperatures.

[0005] It is also common to add separate anti-wear additives (especially to lubricating oils) to reduce the effect of friction on hard surfaces. The most popular or widely used anti-wear additive is zinc dialkyldithiophosphate (ZDDP). ZDDP is a versatile compound that is often used in formulated oils as an anti-fatigue additive, anti-wear additive, and extreme pressure additive. While the benefits of zinc-based additives typically outweigh the risks, a drawback of ZDDP is that ZDDP tends to corrode certain metals. ZDDP is also generally considered non-biodegradable. Moreover, additives containing metals typically produce ash that is acceptable in small amounts when produced from lubricating oils, but much less when produced from fuels. Increasingly, regulatory agencies are seeking to reduce or eliminate the adverse environmental impacts from automobile engines. Therefore, there is a need to develop more environmentally friendly friction modifier additives for fuels that are easy to formulate and exhibit excellent low temperature stability. Summary of the Invention

[0006] The present disclosure relates to fuel or lubricating oil additives, compositions containing said additives for internal combustion engines, and methods for improving the fuel efficiency of engines.

[0007] In one aspect, a fuel composition is provided that includes: (1) greater than 50 wt. % of a hydrocarbon fuel boiling in the gasoline or diesel range; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of primary or secondary aminoalkanediols.

[0008] In another embodiment, a mixture of (1) greater than 50% by weight of a hydrocarbon fuel boiling in the gasoline or diesel range and (2) a minor amount of an alkyl carboxylate salt of a primary or secondary aminoalkanediol, the primary or secondary aminoalkanediol being [ka] wherein R1 is H or a saturated or unsaturated aliphatic group.

[0009] In a further aspect, a method for improving fuel economy in an internal combustion engine is provided, comprising supplying to the engine a fuel composition comprising: (1) greater than 50 wt. % of a hydrocarbon fuel boiling in the gasoline or diesel range; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of primary or secondary aminoalkanediols.

[0010] In yet a further aspect, there is provided a lubricating oil composition comprising: (1) greater than 50 wt. % of a base oil; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of primary or secondary aminoalkanediols.

[0011] In a still further aspect, a method of improving the fuel efficiency of an internal combustion engine is provided, comprising supplying to the engine a lubricating oil composition comprising: (1) greater than 50 wt. % of a base oil; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of primary or secondary aminoalkanediols. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] definition In this specification, the following words and expressions, if used, have the meanings ascribed to them below.

[0013] The term "friction modifier" or related terms refer to compositions that change the friction characteristics between surfaces. The term "anti-wear additive" refers to compositions that reduce surface damage caused by friction. It is not uncommon for additives to have both friction modifying and wear reducing properties.

[0014] An "engine" or "combustion engine" or related terms is a heat engine in which combustion of a fuel occurs in a combustion chamber. An "internal combustion engine" is a heat engine in which combustion of a fuel occurs within an enclosed space (the "combustion chamber").

[0015] "Gasoline" or "gasoline boiling range components" or related terms means gasoline boiling range components consisting of at least primarily C4 to C6 12 In one embodiment, the gasoline or gasoline boiling range components further comprise at least primarily C4-C 12 is defined to refer to a composition that contains hydrocarbons and further has a boiling range of about 37.8° C. (100° F.) to about 204° C. (400° F.). In an alternative embodiment, the gasoline or gasoline boiling range components are at least primarily C4 to C6 12 It is defined to refer to a composition that contains hydrocarbons and has a boiling range of about 37.8° C. (100° F.) to about 204° C. (400° F.), and is further defined as meeting ASTM D4814.

[0016] The term "diesel" or related terms are used at least primarily in 10 ~C 25 Diesel refers to a middle distillate fuel that contains hydrocarbons. In one embodiment, diesel further comprises at least primarily C 10 ~C 25 Diesel is defined as a composition that contains hydrocarbons and has a boiling range of about 165.6° C. (330° F.) to about 371.1° C. (700° F.). In an alternative embodiment, diesel is at least primarily composed of C 10 ~C 25 As previously defined, it refers to a composition that contains hydrocarbons and has a boiling range of about 165.6° C. (330° F.) to about 371.1° C. (700° F.), and is further defined as meeting ASTM D975.

[0017] The term "oil-soluble" means that for a given additive, the amount required to provide a desired level of activity or performance can be incorporated by dissolving, dispersing or suspending in an oil of lubricating viscosity. Typically, this means that at least 0.001 wt. % of the additive can be incorporated into a lubricating oil composition. The term "fuel-soluble" is a similar expression for an additive that is dissolved, dispersed or suspended in a fuel.

[0018] The term "aliphatic" or related terms refers to a hydrocarbon non-aromatic group. An aliphatic group can be saturated or unsaturated, straight-chained or branched, and can be non-aromatic cyclic.

[0019] The term "alkyl" or related terms refers to a saturated hydrocarbon group which can be linear, branched, cyclic, or a combination of cyclic, linear, and / or branched.

[0020] "Minor amount" or related term means less than 50% by weight of the composition, expressed with respect to the listed additive and with respect to the total weight of the composition that is considered the active ingredient of the additive.

[0021] In the context of hydrocarbon-based formulations (especially lubricants), the term "ash" or related terms refers to metal compounds remaining after the hydrocarbon is calcined. This ash comes primarily from chemicals and solids used in certain additives. The term "ashless" or related terms refers to formulations or additives that do not produce ash or that limit ash production. Ashless additives generally do not contain metals (including boron), silicon, halogens, or contain these elements at concentrations below typical instrumental detection limits.

[0022] An "analog" or related term is a compound that has a similar structure from another compound, but differs from that compound with respect to certain components, such as one or more atoms, functional groups, substructures, etc., replaced with other atoms, groups, or substructures.

[0023] A "homolog" or related term is a compound that belongs to a set of compounds that differ from each other by a repeating unit. Alkanes are examples of homologs. For example, ethane and propane are homologs because they differ only in the length of the repeating unit (-CH2-). Homologs can be considered as specific types of analogues.

[0024] A "derivative" or related term is a compound derived from a similar compound via a chemical reaction (e.g., acid-base reaction, hydrogenation, etc.). In the context of a substituent, a derivative may be a combination of one or more moieties. For example, a phenol moiety may be considered a derivative of an aryl moiety and a hydroxyl moiety. One of ordinary skill in the art would know the scope and boundaries of what is considered a derivative.

[0025] Introduction Most gasoline detergents and dispersants do not exhibit significant friction reducing properties when utilized as low concentration additives in fuel. When these additives are used in higher concentrations, friction reduction is observed, but with detrimental unintended effects, such as unacceptable levels of deposits in the combustion chamber. To mitigate the detrimental effects, friction modifiers can be added to reduce engine friction and increase fuel economy. Some friction modifiers also have anti-wear properties, protecting engine surfaces from frictional wear.

[0026] Traditionally, esters of fatty acids and glycerol, such as glycerol monooleate (GMO), and amides of fatty acids and amines have been employed as friction modifier compounds. However, glycerol monoester compounds and fatty amides can have solidification problems (even at ambient temperatures), making these compounds particularly difficult to handle in the field (e.g., storage, transportation, etc.). These friction modifiers are difficult to formulate into additive concentrates that remain fluid and homogeneous at low temperatures. This difficulty in preparing friction modifiers can be further exacerbated by detergent additives that are typically used in fuel additive concentrates. Since additive concentrates are usually added to blend fuel additive components into fuels, it is essential that the fuel additive concentrate is homogeneous and remains fluid at low temperatures (down to about -20°C or lower) for ease of handling.

[0027] Friction modifiers Provided herein are friction modifiers that are useful as fuel additives or lubricating oil additives.Traditionally, friction modifiers have been used as additives in lubricating oils, but modern gasoline engine designs provide the opportunity for fuel additives to assist the lubricant in adjusting friction.

[0028] In engines, the friction modifiers of the present invention reduce friction and / or reduce the effects of wear on various engine surfaces. Friction modifier additives can generally be used in internal combustion engines that burn liquid fuels, particularly carbon-compound spark ignition gasoline engines, port fuel injection (PFI) engines, direct injection gasoline (DIG) engines, and diesel engines. These compositions can improve the overall fuel economy of internal combustion engines.

[0029] The friction modifier includes a primary or secondary aminoalkanediol or an analog, homolog or derivative thereof according to the generalized structure shown in Formula 1. According to another embodiment, the friction modifier is an alkyl carboxylate salt of a primary or secondary aminoalkanediol or an analog, homolog or derivative thereof.

[0030] Without being limited by theory, the additives of the present invention have favorable friction modifying and / or anti-wear properties. In addition, the additives of the present invention have excellent low temperature compatibility (Tables 1A-1B). This allows for easy handling of these compositions, especially in concentrated form and in cold climates. Friction modifiers often help maintain a fluid film or fluid coating on the surface of a material (usually metal in an engine) that has a much lower coefficient of friction than bare metal would. Anti-wear additives often come into play when the oil film is compromised and insufficient to keep two surfaces in hydrodynamic lubrication and enter boundary lubrication.

[0031] Aminoalkanediol The aminoalkanediols of the present disclosure are ashless and compositionally limited to the elements C, N, O, and H. In some cases, trace amounts of heteroatoms (non-C, non-N, non-O, non-H) may be tolerated. The general structure of an aminoalkanediol (Formula 1) is: [ka] is given by wherein R1 is H or a saturated or unsaturated aliphatic group, and the main carbon backbone of R1 is 1 to 25 carbons, 2 to 20 carbons, 3 to 15 carbons, 4 to 10 carbons, etc. Suitable aliphatic groups include linear or branched versions of the following aliphatic groups: pentyl (Formula 1A), hexyl (Formula 1B), heptan-2-yl (Formula 1C), octyl (Formula 1D), oleyl (Formula 1E), 2-methylhexyl (Formula 1F), 2-ethylhexyl (Formula 1G), H (Formula 1H), 4-methylhexyl (Formula 1I), etc. [ka]

[0032] Alkyl Carboxylic Acid The alkyl carboxylic acids of the present disclosure are ashless and compositionally limited to the elements C, N, O, and H. In some cases, trace amounts of heteroatoms (non-C, non-N, non-O, non-H) may be tolerated. The general structure of an alkyl carboxylic acid is represented by formula 2: [ka] is given by wherein R2 is an alkyl group and the main backbone chain of R2 is 1 to 25 carbons, 2 to 20 carbons, 3 to 15 carbons, 4 to 10 carbons, etc. Suitable alkyl carboxylic acids include the following: 2-ethylhexanoic acid (Formula 2A), 2-propylhexanoic acid (Formula 2B), 2-ethylheptanoic acid (Formula 2C), 2-propylheptanoic acid (Formula 2D), butyric acid (Formula 2E), hexanoic acid (Formula 2F), 3-methylhexanoic acid (Formula 2G), 2-methyloctanoic acid (Formula 2H), 2-ethylnonanoic acid (Formula 2I). [ka]

[0033] Alkyl carboxylates of primary or secondary aminoalkanediols Alkyl carboxylates of primary or secondary aminoalkanediols are salts of aminoalkanediols coordinated to alkyl carboxylates. The salts can be synthesized by a relatively simple two-step reaction. The synthesis of 2-ethylhexanoate of aminoheptanylpropanediol (AHPD) is shown below for illustrative purposes, without being intended to be limiting. Other synthetic routes may be envisaged to obtain the desired alkyl carboxylates of primary or secondary aminoalkanediols. [ka] The first step (step 1) involves reacting one equivalent of aminopropanediol with one equivalent of glycidol in the presence of ethanol solvent. Other suitable solvents include glycerol, propylene, glycol, glycol ether, ethylene glycol monobutyl ether, and the like. In step 2, the resulting product from step 1 can be blended with 2-ethylhexanoic acid in the presence of dichloromethane solvent to form aminopropanediol carboxylate salt. Other suitable solvents include benzene, toluene, xylene, hexane, chlorobenzene, methylene chloride, chloroform, dichloroethane, and the like.

[0034] If the above reaction is carried out using octadecenylaminopropanediol (OAPD) instead of AHPD, 2-ethylhexanoate and a salt of OAPD are produced (Equation 4). [ka]

[0035] fuel composition The friction modifiers of the present disclosure may be useful as additives in hydrocarbon fuels to reduce friction and / or reduce wear to improve fuel efficiency in internal combustion engines. When used in a fuel, the appropriate concentration of the additive required to achieve the desired friction reduction and / or wear reduction will depend on a variety of factors, including the type of fuel used, the presence of other detergents or dispersants or other additives, the solubility of the additive in the fuel, etc. Generally, the concentration of the additives of the present disclosure in a hydrocarbon fuel may range from 25 to 5000 parts per million by weight (ppmw) (including but not limited to 50 to 4000 ppm, 100 to 3500, 150 to 3000, 200 to 2500, 250 to 2000, 300 to 1500, 350 to 1000, etc.) or 0.0025% to 0.5% by weight (including but not limited to 0.005 to 0.4% by weight, 0.01 to 0.35% by weight, 0.015 to 0.3% by weight, 0.02 to 0.25% by weight, 0.025 to 0.2% by weight, 0.03 to 0.15% by weight, 0.035 to 0.1% by weight, etc.). Generally, fuel additives should not be added in amounts greater than the fuel solubility. If other friction modifiers are present in the fuel composition, lesser amounts of the additive may be used.

[0036] In some embodiments, the compounds of the present disclosure can be formulated as concentrates using an inert, stable, oleophilic (i.e., soluble in hydrocarbon fuels) organic solvent boiling in the range of 65°C to 205°C. Aliphatic or aromatic hydrocarbon solvents such as benzene, toluene, xylene, or higher boiling aromatic compounds or aromatic thinners can be used. Aliphatic alcohols containing 2 to 8 carbon atoms, such as ethanol, isopropanol, methyl isobutyl carbinol, n-butanol, in combination with a hydrocarbon solvent, are also suitable for use with the present additives. In the concentrates, the amount of additive can range from 10 to 70% by weight, 15 to 60% by weight, 20 to 50% by weight, 25 to 45% by weight, 30 to 40% by weight, etc.

[0037] In gasoline or gasoline fuels, other well-known additives may be employed, including oxygenates (e.g., ethanol, methyl tert-butyl ether), other anti-knock agents, and detergent / dispersants (e.g., hydrocarbyl amines, hydrocarbyl poly(oxyalkylene) amines, succinimides, Mannich reaction products, aromatic esters of polyalkylphenoxyalkanols, or polyalkylphenoxyaminoalkanes). In addition, low speed pre-ignition additives, antioxidants, metal deactivators, and demulsifiers may also be present.

[0038] In diesel fuels, other well-known additives can be employed, such as pour point depressants, flow improvers, cetane improvers, etc. Gasoline fuels that may be employed with the additive compositions used in this invention also include clean burning gasolines having typical to only trace levels of sulfur, aromatics and olefins.

[0039] A fuel-soluble non-volatile carrier fluid or non-volatile oil may also be used with the compounds of the present disclosure.The carrier fluid is a chemically inert hydrocarbon-soluble liquid vehicle that substantially increases the non-volatile residue (NVR) or solvent-free liquid fraction of the fuel additive composition without overwhelmingly contributing to the increase in octane requirements.The carrier fluid may be natural or synthetic oil, such as mineral oil, refined petroleum oil, synthetic polyalkanes and synthetic alkenes, including hydrogenated and non-hydrogenated polyalphaolefins, synthetic polyoxyalkylene-derived oils, such as those described in U.S. Pat. Nos. 3,756,793, 4,191,537 and 5,004,478, and in European Patent Publication Nos. 356,726 and 382,159.

[0040] The carrier fluid may be employed in an amount ranging from 35 to 5000 ppm by weight of the hydrocarbon fuel (e.g., 50 to 3000 ppm of the fuel). When employed in a fuel concentrate, the carrier fluid may be present in an amount ranging from 20 to 60% by weight (e.g., 30 to 50% by weight).

[0041] lubricating oil composition The primary or secondary aminoalkanediols or alkyl carboxylates of primary or secondary aminoalkanediols of the present disclosure may also be used in lubricating oils to prevent or reduce undesirable ignition events in combustion engines. When employed in this manner, the additives are typically present in the lubricating oil composition at a concentration in the range of 0.001 to 10 wt. %, including but not limited to 0.01 to 5 wt. %, 0.2 to 4 wt. %, 0.5 to 3 wt. %, 1 to 2 wt. %, etc., based on the total weight of the lubricating oil composition. Lesser amounts of the additives may be used when other friction modifiers and / or antiwear additives are present in the lubricating oil composition.

[0042] Oils used as base oils are selected or blended depending on the desired end use and additives in the finished oil to obtain a lubricating oil composition having a desired grade of engine oil, for example, a Society of Automotive Engineers (SAE) viscosity grade of 0W, 0W-20, 0W30, 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.

[0043] An oil of lubricating viscosity (sometimes called a "base stock" or "base oil") is the primary liquid component of a lubricant, e.g., into which additives and possibly other oils are blended to produce the final lubricant (or lubricant composition). Base oils useful for making concentrates and lubricating oil compositions therefrom can be selected from natural (vegetable, animal or mineral) and synthetic lubricating oils and mixtures thereof.

[0044] 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 specified in Table E-1. Group II base stocks contain 90% or greater saturates and 0.03% or less sulfur and have a viscosity index of 80 or greater and less than 120 using the test methods specified in Table E-1. Group III base stocks contain 90% or greater saturates and 0.03% or less sulfur and have a viscosity index of 120 or greater 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 Groups I, II, III, or IV.

[0045] Natural oils include animal oils, vegetable oils (e.g., castor oil and lard oil), and mineral oils. Animal and vegetable oils with good thermo-oxidative stability can be used. Among natural oils, mineral oils are preferred. Mineral oils vary widely with respect to their crude source, e.g., whether they are paraffinic, naphthenic, or paraffinic-naphthenic mixtures. Oils derived from coal or shale are also useful. Natural oils also vary with respect to the methods used to produce and refine them, e.g., their distillation range, and whether they are straight run or cracked, hydrorefined, or solvent extracted.

[0046] Synthetic oils include hydrocarbon oils. Hydrocarbon oils include oils such as polymerized olefins 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. Examples include C8 to C 14 Olefins, e.g., C8, C 10 , C 12 , C 14 PAOs derived from olefins or mixtures thereof can be utilized.

[0047] Other useful fluids for use as base oils include unconventional or non-conventional base stocks that have been processed, preferably catalytically processed or synthetically, to provide high performance properties.

[0048] Unconventional or unconventional base stocks / base oils include one or more blends of base stock(s) derived from one or more Gas-to-Liquids (GTL) materials, as well as isomerate / isodewaxate base stock(s) derived from natural wax or waxy feeds, mineral oil and or non-mineral oil waxy sources such as slack wax, natural wax, and further non-petroleum derived waxy materials such as gas oil, waxy fuels hydrocracker bottoms, waxy raffinate, hydrocrackates, pyrolysates, or other mineral, mineral oil, or waxy materials received from coal liquids or shale oils, as well as blends of such base stocks.

[0049] The base oils for use in the lubricating oil compositions of this disclosure are any of the oil types corresponding to API Group I, II, III, IV, and V oils, and mixtures thereof, preferably API Group II, III, IV, and V oils, and mixtures thereof, more preferably Group III-V base oils, due to their exceptional volatility, stability, viscosity and cleanliness characteristics.

[0050] Typically, the base oil has a viscosity of 2.5 to 20 mm at 100°C (ASTM D445). 2 / sec (e.g., 3 to 12 mm 2 / sec, 4~10mm 2 / sec, or 4.5-8mm 2 / sec).

[0051] The lubricating oil composition can also contain conventional lubricating oil additives to provide auxiliary functions and obtain the finished lubricating oil composition in which these additives are dispersed or dissolved.For example, the lubricating oil composition can be blended with antioxidants, ashless dispersants, antiwear agents, detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifiers, friction modifiers, metal deactivators, pour point depressants, viscosity modifiers, antifoam agents, cosolvents, package compatibilizers, corrosion inhibitors, dyes, extreme pressure agents, and the like, and mixtures thereof.Various additives are known and commercially available.These additives or similar compounds of the additives can be used to prepare the lubricating oil composition of the present invention by conventional blending procedures.

[0052] Each of the above-mentioned additives is used in a functionally effective amount to impart the desired properties to the lubricant when in use. Thus, for example, if the additive is an ashless dispersant, a functionally effective amount of the ashless dispersant would be an amount sufficient to impart the desired dispersant properties to the lubricant. Generally, the concentration of each of these additives when in use can range from about 0.001 to about 20% by weight, such as from about 0.01 to about 10% by weight, unless otherwise specified.

[0053] The following illustrative examples are intended to be non-limiting.

[0054] Examples 1-3 Cold test solutions were made by blending the friction modifier candidates with the appropriate stock solution. Depending on the test, the stock solution may or may not contain 2-ethylhexanol. The friction modifier and stock solution were added to a 30 mL glass vial in an amount resulting in a final test solution of 19.03 wt %. The vial was capped, shaken by hand until the solution was homogenous, and then placed in a cold well set at -20°C. The test solutions were visually inspected to monitor solution clarity and sediment retention at set time intervals for 28 days. A summary of the results for AHPD, 2-EH and AHPD salts, and GMO over a 5-day period can be found in Table 1A. A key to the results in Table 1 can be found in Table 1B. With respect to Table 1B, values ​​of 3, 4, 5, and 6 are considered failing ratings for the liquid phase, while values ​​of 2 and 3 are considered failing ratings for sediment. Both AHPD and the salt of 2-EH with AHPD performed better than GMO over the 5 day period.

[0055] The structure of GMO is shown in Formula 5 below. [ka] [Table 1A] [Table 1B]

[0056] Examples 4 to 18 Bench test samples containing various friction modifiers were generated by adding the desired blended friction modifiers to the baseline oil formulation to the desired weight percent. The final dosage of friction modifier in the baseline oil formulation ranged from 0.25% to 1.0% by weight. The baseline oil formulation in Group 2 base oil consisted of 4.0% polyisobutenyl succinimide, 7.0 mmol / kg dialkyl zinc dithiophosphate, 48.5 mmol / kg calcium sulfonate detergent, 0.5% alkylated diphenylamine antioxidant, 0.05% antifoam agent, and 0.3% viscosity index improver.

[0057] The friction modifiers containing the baseline oils described above were then tested for friction performance in a Mini Traction Tester (MTM) bench test. The MTM is manufactured and commercially available by PCS Instruments (London, UK). The MTM operates with a ball (0.75 inch 8620 steel ball) loaded against a rotating disc (52100 steel). Conditions employ a load of approximately 10-30 Newtons, a speed of approximately 10-2000 mm / sec, at a temperature of approximately 125-150°C. A wide variety of characteristics (test methods) can be designed for different applications.

[0058] In this bench test, friction performance was tested by comparing the total area under the second Stribeck curve (mixed lubrication regime) generated with a baseline formulation to the second Stribeck curve generated with a baseline formulation top-treated with a friction modifier. Lower total area values ​​correspond to better friction performance. The MTM results are summarized in Table 2 below. [Table 2] Note that the following [1] to

[35] are all embodiments or aspects of the present invention. [1] A fuel composition comprising: (1) greater than 50% by weight of a hydrocarbon fuel boiling in the gasoline or diesel range; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of primary or secondary aminoalkanediols. [2] The structure of the aminoalkanediol is [ka] and In the formula, R 1 is H or an aliphatic group. [3] 3. The fuel composition according to claim 2, wherein the aliphatic group is one of the following hydrocarbon chains: H, pentyl, hexyl, heptan-2-yl, octyl, oleyl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl. [4] The fuel composition according to [1], wherein the alkyl carboxylate of the primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid. [5] 5. The fuel composition according to claim 4, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, 2-propylheptanoic acid, butyric acid, hexanoic acid, 3-methylhexanoic acid, 2-methyloctanoic acid, or 2-ethylnonanoic acid. [6] The fuel composition according to [1], wherein the aminoalkanediol of the primary or secondary aminoalkanediol or the alkyl carboxylate of the primary or secondary aminoalkanediol is present in an amount of about 25 to 5000 ppm by weight. [7] 10. The fuel composition of claim 1, further comprising an oxygenate, an anti-knock agent, a detergent, a dispersant, a friction modifier, an antioxidant, a metal deactivator, a demulsifier, a pour point depressant, a flow improver, a cetane improver, or a lubricity additive. [8] The fuel composition according to [1], wherein the alkyl carboxylate salt of the primary or secondary aminoalkanediol is compositionally limited to the following elements: C, N, O, and H. [9] (1) greater than 50% by weight of a hydrocarbon fuel boiling within the gasoline or diesel range; and (2) a minor amount of an alkyl carboxylate salt of said primary or secondary aminoalkanediol, said primary or secondary aminoalkanediol being:

change

[10] [9] The fuel composition according to [9], wherein the aliphatic group is one of the following hydrocarbon chains: propyl group, butyl group, pentyl group, hexyl group, septyl group, octyl group, or oleyl group.

[11] [9] The fuel composition according to claim 9, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

[12] 11. The fuel composition according to claim 10, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, 2-propylheptanoic acid, butyric acid, hexanoic acid, 3-methylhexanoic acid, 2-methyloctanoic acid, or 2-ethylnonanoic acid.

[13] A method for improving fuel economy in an internal combustion engine, comprising supplying to the engine a fuel composition comprising: (1) greater than 50 wt. % of a hydrocarbon fuel boiling in the gasoline or diesel range; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of said primary or secondary aminoalkanediols.

[14] The structure of the aminoalkanediol is

change

[13] , wherein:

[15] 13. The method of claim 12, wherein the aliphatic group is one of the following hydrocarbon chains: H, pentyl, hexyl, heptan-2-yl, octyl, oleyl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

[16] The method of claim 13, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

[17] 16. The method according to claim 15, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, or 2-propylheptanoic acid.

[18] The method of claim 13, wherein the aminoalkanediol or alkylcarboxylate salt of a primary or secondary aminoalkanediol is present in an amount of about 25 to 5000 ppm by weight.

[19] The method of claim 13, wherein the fuel composition further comprises an oxygenate, an anti-knock agent, a detergent, a dispersant, a friction modifier, an antioxidant, a metal deactivator, a demulsifier, a pour point depressant, a flow improver, a cetane improver, or a lubricity additive.

[20] The method of claim 13, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol is compositionally limited to the following elements: C, N, O, and H.

[21] A lubricating oil composition comprising: (1) greater than 50 weight percent of a base oil; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of said primary or secondary aminoalkanediols.

[22] The structure of the aminoalkanediol is

change

[23]

[22] The lubricating oil composition according to

[22] , wherein the aliphatic group is one of the following hydrocarbon chains: H, pentyl, hexyl, heptan-2-yl, octyl, oleyl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

[24]

[21] The lubricating oil composition according to

[21] , wherein the alkyl carboxylate of the primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

[25]

[24] The lubricating oil composition according to

[24] , wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, 2-propylheptanoic acid, butyric acid, hexanoic acid, 3-methylhexanoic acid, 2-methyloctanoic acid, or 2-ethylnonanoic acid.

[26] The lubricating oil composition according to

[21] , wherein the aminoalkanediol or alkylcarboxylate salt of a primary or secondary aminoalkanediol is present in an amount of about 0.001 to 10 wt %.

[27] The lubricating oil composition according to

[21] , wherein the aminoalkanediol or alkylcarboxylate salt of a primary or secondary aminoalkanediol is present in an amount of about 0.5 to 5 wt. %.

[28] 21. The lubricating oil composition of claim 20, further comprising an antioxidant, an ashless dispersant, an antiwear agent, a detergent, a rust inhibitor, an antifog agent, a demulsifier, a friction modifier, a metal deactivator, a pour point depressant, a viscosity modifier, an antifoam agent, a cosolvent, a package compatibilizer, a corrosion inhibitor, a dye, or an extreme pressure agent.

[29]

[21] The lubricating oil composition according to

[21] , wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol is compositionally limited to the following elements: C, N, O, and H.

[30] 1. A method for improving the fuel efficiency of an internal combustion engine comprising supplying to said engine a lubricating oil composition comprising: (1) greater than 50 weight percent of a base oil; and (2) a minor amount of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of said primary or secondary aminoalkanediols.

[31] The method according to

[30] , wherein the internal combustion engine is spark ignition.

[32] The structure of the aminoalkanediol is

change

[30] , wherein:

[33] 30. The method of claim 30, wherein the aliphatic group is one of the following hydrocarbon chains: H, pentyl, hexyl, heptan-2-yl, octyl, oleyl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

[34] The method of claim 30, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

[35] 30. The method of claim 30, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, or 2-propylheptanoic acid.

Claims

1. 1. A fuel composition comprising: (1) greater than 50 wt. % of a hydrocarbon fuel boiling in the gasoline or diesel range; and (2) 25 to 5000 ppm by weight of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of primary or secondary aminoalkanediols, The structure of the aminoalkanediol is 【Chemistry 1】 and In the formula, R １ is H or an aliphatic group, said aliphatic group being one of the following hydrocarbon chains: pentyl, hexyl, heptan-2-yl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

2. 2. The fuel composition according to claim 1, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

3. 3. The fuel composition of claim 2, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, 2-propylheptanoic acid, butyric acid, hexanoic acid, 3-methylhexanoic acid, 2-methyloctanoic acid, or 2-ethylnonanoic acid.

4. 10. The fuel composition of claim 1, further comprising an oxygenate, an anti-knock agent, a detergent, a dispersant, a friction modifier, an antioxidant, a metal deactivator, a demulsifier, a pour point depressant, a flow improver, a cetane improver, or a lubricity additive.

5. 2. The fuel composition of claim 1, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol is compositionally limited to the following elements: C, N, O, and H.

6. 2. The fuel composition according to claim 1, wherein the (2) primary or secondary aminoalkanediol or alkyl carboxylate of a primary or secondary aminoalkanediol is an alkyl carboxylate of a primary or secondary aminoalkanediol.

7. 7. The fuel composition according to claim 6, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

8. 8. The fuel composition of claim 7, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, 2-propylheptanoic acid, butyric acid, hexanoic acid, 3-methylhexanoic acid, 2-methyloctanoic acid, or 2-ethylnonanoic acid.

9. 1. A method for improving fuel economy in an internal combustion engine comprising supplying to said engine a fuel composition comprising: (1) greater than 50 wt. % hydrocarbon fuel boiling in the gasoline or diesel range; and (2) 25 to 5000 ppm by weight of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of said primary or secondary aminoalkanediols, The structure of the aminoalkanediol is 【Chemistry 3】 Wherein R １ is H or an aliphatic group, said aliphatic group being one of the following hydrocarbon chains: pentyl, hexyl, heptan-2-yl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

10. 10. The method of claim 9, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

11. 11. The method of claim 10, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, or 2-propylheptanoic acid.

12. 10. The method of claim 9, wherein the fuel composition further comprises an oxygenate, an anti-knock agent, a detergent, a dispersant, a friction modifier, an antioxidant, a metal deactivator, a demulsifier, a pour point depressant, a flow improver, a cetane improver, or a lubricity additive.

13. 10. The method of claim 9, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol is compositionally limited to the following elements: C, N, O, and H.

14. 1. A lubricating oil composition comprising: (1) greater than 50 wt. % of a base oil; and (2) from 25 to 5000 ppm by weight of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of said primary or secondary aminoalkanediols, The structure of the aminoalkanediol is 【Chemistry 4】 Wherein R １ is H or an aliphatic group, said aliphatic group being one of the following hydrocarbon chains: pentyl, hexyl, heptan-2-yl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

15. 15. The lubricating oil composition of claim 14, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

16. 16. The lubricating oil composition of claim 15, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, 2-propylheptanoic acid, butyric acid, hexanoic acid, 3-methylhexanoic acid, 2-methyloctanoic acid, or 2-ethylnonanoic acid.

17. The lubricating oil composition of claim 14, wherein the aminoalkanediol or alkylcarboxylate salt of a primary or secondary aminoalkanediol is present at 0.001 to 10 wt %.

18. The lubricating oil composition of claim 14, wherein the aminoalkanediol or alkylcarboxylate salt of a primary or secondary aminoalkanediol is present at 0.5 to 5 weight percent.

19. 15. The lubricating oil composition of claim 14, further comprising an antioxidant, an ashless dispersant, an antiwear agent, a detergent, a rust inhibitor, an antifog agent, a demulsifier, a friction modifier, a metal deactivator, a pour point depressant, a viscosity modifier, an antifoam agent, a co-solvent, a package compatibilizer, a corrosion inhibitor, a dye, or an extreme pressure agent.

20. 15. The lubricating oil composition of claim 14, wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol is compositionally limited to the following elements: C, N, O, and H.

21. 1. A method for improving fuel efficiency of an internal combustion engine comprising supplying to said engine a lubricating oil composition comprising: (1) greater than 50 wt. % of a base oil; and (2) from 25 to 5,000 ppm by weight of one or more primary or secondary aminoalkanediols or alkyl carboxylate salts of said primary or secondary aminoalkanediols, The structure of the aminoalkanediol is 【Chemistry 5】 Wherein R １ is H or an aliphatic group, said aliphatic group being one of the following hydrocarbon chains: pentyl, hexyl, heptan-2-yl, 2-methylhexyl, 2-ethylhexyl, or 4-methylhexyl.

22. 22. The method of claim 21, wherein the internal combustion engine is spark ignition.

23. 22. The method of claim 21 , wherein the alkyl carboxylate salt of a primary or secondary aminoalkanediol comprises a carboxylate of an alkyl carboxylic acid.

24. 22. The method of claim 21, wherein the alkyl carboxylic acid is one of the following acids: 2-ethylhexanoic acid, 2-propylhexanoic acid, 2-ethylheptanoic acid, or 2-propylheptanoic acid.

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