Succinimide dispersants post-treated with heteroaromatic glycidyl ethers exhibit good soot handling performance

Abstract

A dispersant composition is described. The composition has the structure: Formula (I): [Chemical Formula I] JPEG2023535706000017.jpg2225 wherein R1 is a heteroaryl or heteroarylalkyl group having from 4 to 20 carbon atoms, and R2 and R3 are independently a hydrogen atom, an alkyl group, or an aryl group.

Description

[Technical Field]

[0001] Technical Field This disclosure relates to lubricating oil additive compositions. More specifically, this disclosure describes dispersant additive compositions, lubricating oil compositions containing same, and methods for using those compositions. [Background technology]

[0002] background Dispersants may be added to lubricating oils to keep critical engine parts clean, extend their life, maintain proper emissions, and achieve good fuel economy.

[0003] Perhaps the most widely used dispersants are succinimides. Succinimide dispersants typically have a polar head and a long hydrocarbon tail. The polar head can attach to insoluble materials such as soot, sludge, and other impurities, while the long hydrocarbon tail keeps the dispersant suspended in the oil. Once some dispersant polar heads attach to solid particles, they can no longer combine with other impurities to form larger particles, which can deposit on engine surfaces and are then removed from the engine when the oil is changed.

[0004] Conversely, lack of adequate dispersibility can lead to sludge flocculation, precipitation of insoluble materials, clumping of soot particles, deposit formation, filter plugging, oil thickening, abrasion, and the like.

[0005] There are many ongoing efforts in the lubricant industry aimed at improving dispersancy. Summary of the Invention

[0006] summary In one aspect, there is provided a dispersant composition comprising: structure: [ka] wherein R1 is a heteroaryl or heteroarylalkyl group having from 4 to 20 carbon atoms, and R2 and R3 are independently a hydrogen atom, an alkyl group, or an aryl group.

[0007] In another aspect, there is provided a lubricating oil composition comprising: Base oil; structure: [ka] wherein R1 is heteroaryl or heteroarylalkyl having from 4 to 20 carbon atoms, and R2 and R3 are independently hydrogen atoms, alkyl groups, or aryl groups.

[0008] In another aspect, there is provided a method of reducing soot induced viscosity increase in an engine, the method comprising: introducing into the engine a dispersant composition, the dispersant composition having the structure: [ka] wherein R1 is a heteroaryl or heteroarylalkyl group having from 4 to 20 carbon atoms, and R2 and R3 are independently a hydrogen atom, an alkyl group, or an aryl group), and a polyalkenyl succinimide; and To operate the engine. DETAILED DESCRIPTION OF THE INVENTION

[0009] Detailed Description definition As used herein, the following terms are so defined.

[0010] The term "succinimide" is understood in the art to include many of the amide, imide, and amidine species that can be formed in the reaction of succinic anhydride with an amine. However, the primary product is succinimide, and the term is generally accepted to refer to the product of the reaction of an alkenyl- or alkyl-substituted succinic acid or anhydride with an amine. Alkenyl or alkyl succinimides are disclosed in numerous references and are well known in the art. Certain basic types of succinimides and related materials encompassed by the term "succinimide" are taught in U.S. Pat. Nos. 2,992,708; 3,018,291; 3,024,237; 3,100,673; 3,219,666; 3,172,892; and 3,272,746.

[0011] The term "post-treating agent" refers to a reagent capable of functionalizing a succinimide.

[0012] The term "hydrocarbyl" refers to a chemical group or moiety derived from a hydrocarbon, including saturated and unsaturated hydrocarbons. Examples of hydrocarbyl groups include alkenyl, alkyl, polyalkenyl, polyalkyl, phenyl, and the like.

[0013] The term "PIBSA" is an abbreviation for polyisobutenyl or polyisobutyl succinic anhydride.

[0014] The terms "oil-soluble" or "oil-dispersible" as used herein do not necessarily indicate that a compound or additive is soluble, dissolvable, miscible, or suspendable in oil in all proportions. However, they do mean, for example, that the compound or additive is soluble or stably dispersible in oil to a sufficient degree to exert its intended effect in the environment in which the oil is used. Furthermore, the incorporation of other additives may allow for higher levels of incorporation of a particular additive, if desired.

[0015] Where combinations, subsets, groups, etc. of elements (e.g., combinations of components in a composition or combinations of steps in a method) are disclosed, it is understood that specific reference to each of the various individual and collective combinations and permutations of those elements is specifically contemplated and described herein, even though it may not be explicitly disclosed.

[0016] The present invention describes novel dispersant additive compositions and lubricating oil compositions containing the same. According to one or more embodiments, the invention provides dispersant formulations comprising a first dispersant (or primary dispersant) and, optionally, a second dispersant (or secondary dispersant). The first dispersant (or primary dispersant) is a succinimide that has been post-treated with a heteroaromatic glycidyl ether, as shown in Structure I below. The second dispersant (or secondary dispersant) is a succinimide, with or without post-treatment. In some embodiments, the dispersant formulation comprises a third dispersant, which is a Mannich dispersant.

[0017] The present invention also describes a method for reducing soot-induced viscosity increase in an engine, wherein a dispersant formulation or a lubricating oil composition containing the same is introduced into the engine to provide superior soot dispersancy. The dispersant formulation comprises a first succinimide dispersant and, optionally, a second succinimide dispersant, wherein the first and second succinimide dispersants are different. The first dispersant is a succinimide that has been post-treated with a heteroaromatic glycidyl ether, as shown in Structure I below. The second dispersant is a succinimide with or without post-treatment. In some embodiments, the dispersant formulation comprises a third dispersant, wherein the third dispersant is a Mannich dispersant.

[0018] In some embodiments, the first and second dispersants may be different in that the first dispersant is post-treated with a heteroaromatic glycidyl ether, while the second dispersant is either not post-treated or is post-treated with a secondary post-treating agent. Generally, the secondary post-treating agent will be different from the heteroaromatic glycidyl ether (Structure I) used to post-treat the primary succinimide dispersant. Suitable examples of secondary post-treating agents include reactive boron compounds, organic carbonates (e.g., ethylene carbonate), organic oxides (e.g., alkylene oxides), glycidol, glycidyl ethers, or other post-treating reagents known in the technical literature.

[0019] Suitable boron compounds that can be used as boron sources include, for example, boric acid, borate salts, and borate esters. Representative examples of boric acid include orthoboric acid, metaboric acid, and paraboric acid. Representative examples of borates include ammonium borates, such as ammonium metaborate, ammonium tetraborate, ammonium pentaborate, and ammonium octaborate. Representative examples of borate esters include monomethyl borate, dimethyl borate, trimethyl borate, monoethyl borate, diethyl borate, triethyl borate, monopropyl borate, dipropyl borate, tripropyl borate, monobutyl borate, dibutyl borate, and tributyl borate.

[0020] Suitable organic carbonates include, for example, cyclic carbonates such as 1,3-dioxolan-2-one (ethylene carbonate); 4-methyl-1,3-dioxolan-2-one (propylene carbonate); 4-ethyl-1,3-dioxolan-2-one (butylene carbonate); 4-hydroxymethyl-1,3-dioxolan-2-one; 4,5-dimethyl-1,3-dioxolan-2-one; 4-ethyl-1,3-dioxolan-2-one; 4,4-dimethyl-1,3-dioxolan-2-one; 4-methyl-5-ethyl-1,3-dioxolan-2-one; 4,5-diethyl-1,3-dioxolan-2-one; 4,4-diethyl-1,3-dioxolan-2-one; 1,3-dioxan-2-one; 4,4-dimethyl 5-hydroxymethyl-5-methyl-1,3-dioxan-2-one; 5,5-diethyl-1,3-dioxan-2-one; 5-methyl-5-propyl-1,3-dioxan-2-one; 4,6-dimethyl-1,3-dioxan-2-one; 4,4,6-trimethyl-1,3-dioxan-2-one, and spiro[1,3-oxa-2-cyclohexanone-5,5'-1',3'-oxa-2'-cyclohexanone]. Other suitable cyclic carbonates can be prepared from sugars such as sorbitol, glucose, fructose, galactose, etc., and from vicinal diols prepared from C1-C30 olefins by methods known in the art.

[0021] Suitable organic oxides include hydrocarbyl oxides (e.g., alkylene oxides), such as ethylene oxide, propylene oxide, styrene oxide, etc. A more detailed description of organic oxides can be found in U.S. Patent Nos. 3,373,111 and 3,367,943, which are incorporated herein by reference.

[0022] Glycidol is a commercially available reagent of the formula: [ka]

[0023] Glycidol can also be prepared from glycerol-1-monochlorohydrin by the action of potassium hydroxide in alcohol. See, e.g., Rider et al., JACS, 52, 1521 (1930), incorporated herein by reference.

[0024] When formulated together in a lubricating oil, the first dispersant and the second dispersant act synergistically to provide improved dispersancy to the lubricating oil.

[0025] In some embodiments, the lubricating oil comprises a third dispersant, and the third dispersant is a Mannich dispersant.

[0026] Primary dispersant The primary dispersant of the present invention is a succinimide that has been post-treated with a heteroaromatic glycidyl ether. More specifically, the primary dispersant is the reaction product of (i) a polyalkenyl succinimide and (ii) a heteroaromatic glycidyl ether having the following structure: [ka] wherein R1 is a heteroaryl or heteroarylalkyl group having from about 4 to about 20 carbon atoms. R2 and R3 are independently a hydrogen atom, an alkyl group, or an aryl group. In some embodiments, at least one of R2 and R3 is a hydrogen atom.

[0027] Heteroaryl or heteroarylalkyl groups can be provided by heteroaryl or heteroarylalkyl compounds.Heteroaryl or heteroarylalkyl compounds are generally polycyclic compounds incorporating one or more heterocycles.Specific examples of heteroaryl or heteroarylalkyl compounds include, but are not limited to, carbazole, indole, quinoline, indolizine, xanthene, purine, chromene, phenothiazine, benzimidazole, benzotriazole, benzothiazole, dibenzofuran, or derivatives thereof.

[0028] The reaction between succinimides and heteroaromatic glycidyl ethers can proceed under a variety of conditions, and a detailed discussion of this reaction is disclosed in U.S. Pat. No. 4,617,137, which is incorporated herein by reference.

[0029] Generally, the reaction between the succinimide and the heteroaromatic glycidyl ether is carried out at a temperature sufficient to cause the heteroaromatic glycidyl ether to react with the succinimide. According to one method, the reaction temperature can range from about 0°C to about 250°C. In some embodiments, the reaction temperature can range from about 50°C to about 200°C. In some embodiments, the reaction temperature can range from about 100°C to about 200°C.

[0030] The reaction between succinimide and heteroaromatic glycidyl ether can proceed in the presence of a catalyst, such as an acidic, basic, or Lewis acid catalyst, such as boron trifluoride, an alkanesulfonic acid, an alkali, or an alkaline carbonate.

[0031] Alternatively, the reaction between the succinimide and the heteroaromatic glycidyl ether can be carried out in a diluent, where the reactants are mixed in a solvent such as toluene, xylene, base oil, etc. Once the reaction is complete, the volatile components can be removed.

[0032] In some embodiments, the primary succinimide dispersants may be further post-treated with optional post-treating agents to add additional functionality, such as organic oxides, reactive boron compounds, organic carbonates, and the like.

[0033] Hydrocarbyl succinimide Hydrocarbyl succinimides can be prepared by any known method, for example, as described in U.S. Patent Publication No. 20180034635 and U.S. Patent No. 7,091,306, which are incorporated herein by reference.

[0034] Hydrocarbyl succinimides can be obtained as the reaction product of alkyl-substituted succinic anhydrides with polyamines. In lubricant applications, the succinic anhydrides are usually alpha-substituted with alkyl chains, such as polyisobutylene (PIBSA) or PIBSA-type moieties. However, any alkyl group compatible with the present invention can be contemplated.

[0035] In lubricating oil applications, polyalkylene polyamines are commonly used as the polyamine, however, any polyamine compatible with the present invention may be contemplated.

[0036] Polyamines can be reacted with alkyl-substituted succinic anhydrides to give monosuccinimides, bissuccinimides, trissuccinimides, or mixtures thereof, depending on the molar ratio.

[0037] In one embodiment, the structure [ka] Hydrocarbyl-substituted succinic anhydrides of the formula (wherein R is a hydrocarbyl substituent derived from a polyalkene group having a number average molecular weight of about 500 to about 3000) can be reacted with polyamines to obtain hydrocarbyl bissuccinimides.

[0038] In one embodiment, R is a hydrocarbyl substituent derived from a polyalkene group having a number average molecular weight of from about 1000 to about 2500. In one embodiment, R is a polyisobutenyl substituent derived from polyisobutene having a number average molecular weight of from about 500 to about 3000. In another embodiment, R is a polyisobutenyl substituent derived from polyisobutene having a number average molecular weight of from about 1000 to about 2500.

[0039] Suitable polyamines may have a linear or branched chain structure and may be cyclic, acyclic, or a combination thereof.

[0040] In some embodiments, polyalkylene polyamines can be used to prepare bissuccinimide dispersants. 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 include those having the formula: HN—(R′NH) x -H, where R' is a straight or branched chain alkylene group having 2 or 3 carbon atoms and x is 1 to 9. Representative examples of suitable polyalkylene polyamines include diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), and heavier polyalkyleneamines (HPA).

[0041] In some embodiments, the polyamine may contain a cyclic group. Specific examples include N,N'-bis-(2-aminoethyl)piperazine (Bis AEP), N-[(2-aminoethyl)2-aminoethyl]piperazine (PEEDA), 1-(2-aminoethyl)-4-[(2-aminoethyl)amino]ethyl]-piperazine) (AEPEEDA), and 1-[2-[[2-[(2-aminoethyl)amino]ethyl]amino]ethyl]-piperazine (PEDETA).

[0042] Many of the polyamines suitable for use in the present invention are commercially available, and others can be prepared by methods well known in the art. For example, methods for preparing amines and their reactants are detailed in Sidgewick's "The Organic Chemistry of Nitrogen," Clarendon Press, Oxford, 1966; Noller's "Chemistry of Organic Compounds," Saunders, Philadelphia, 2nd Ed., 1957; and Kirk-Othmer's "Encyclopedia of Chemical Technology," 2nd Ed., especially Volume 2, pp. 99-116.

[0043] Typically, the hydrocarbyl-substituted succinic anhydride is reacted with the polyamine at a temperature of about 130°C to 220°C (e.g., 135°C to 200°C, 145°C to 175°C, etc.). The reaction can be carried out under an inert atmosphere, such as nitrogen or argon. Generally, the molar charge of the polyamine relative to the polyalkenyl-substituted succinic anhydride is preferably about 0.35:1 to about 1:1 (e.g., 0.4:1 to 0.75:1). As used herein, "molar charge of the polyamine relative to the polyalkenyl-substituted succinic anhydride" refers to the ratio of the number of moles of polyamine to the number of succinic groups in the succinic anhydride reactant.

[0044] One class of suitable hydrocarbyl succinimides can be represented by the following structure: [ka] wherein R and R' are as described herein above, and y is 1 to 11.

[0045] Heteroaromatic Glycidyl Ethers Heteroaromatic glycidyl ethers may be prepared by any known method, for example, as described in US Pat. No. 7,265,232, which is incorporated herein by reference.

[0046] According to one method, heteroaromatic glycidyl ethers can be obtained by reacting heteroaryl or heteroarylalkyl alcohols with epihalohydrins. The reaction can be carried out in a multi-solvent system containing both aqueous and non-aqueous solvents. The reaction can also include an aqueous base, such as an alkali hydroxide. Additionally, the reaction can be facilitated by the presence of a quaternary ammonium salt. The reaction temperature can range from about 0°C to about 50°C.

[0047] Secondary Dispersant The secondary dispersant of the present invention is a different succinimide dispersant than the primary dispersant of the present invention. According to one embodiment, the secondary succinimide dispersant may be a hydrocarbyl succinimide as shown in Structure III.

[0048] In some embodiments, the secondary dispersant is not post-treated. In other embodiments, the secondary dispersant is post-treated with a secondary post-treating agent. Generally, the secondary post-treating agent includes any post-treating agent compatible with the present invention, including one or more of the agents described above. However, the secondary post-treating agent is different from the heteroaromatic glycidyl ether described in Structure I.

[0049] Mannich Dispersant The lubricating oil composition of the present invention may also contain a Mannich dispersant. A Mannich dispersant is a dispersant obtained as a product of the Mannich reaction. The Mannich dispersant may be present in an amount of from about 1.5 wt% to about 20 wt%, based on the total weight of the lubricating oil composition.

[0050] Particularly useful Mannich dispersants are described in U.S. Patent No. 9,528,074, which is incorporated herein by reference. The Mannich dispersants can be prepared by the condensation of a polyisobutyl-substituted hydroxyaromatic compound, the polyisobutyl group being derived from polyisobutene containing at least about 70 wt. % methylvinylidene isomer and having a number average molecular weight ranging from about 400 to about 2500, an aldehyde, an amino acid, or an ester derivative thereof, and an alkali metal base.

[0051] In one embodiment, the Mannich condensation product can be represented by the structure of Formula IV: [ka] wherein each R is independently -CHR'-, R' is a branched or straight chain alkyl having from 1 carbon atom to about 10 carbon atoms, a cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, an aryl having from about 6 carbon atoms to about 10 carbon atoms, an alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or an aralkyl having from about 7 carbon atoms to about 20 carbon atoms, R1 is a polyisobutyl group derived from polyisobutene containing at least about 70 wt% methylvinylidene isomer and having a number average molecular weight in the range of from about 400 to about 2,500; X is hydrogen, an alkali metal ion, or W is -[CHR"]-m, where each R" is independently H, alkyl having 1 carbon atom to about 15 carbon atoms, or substituted alkyl having 1 carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfido, or thiol; and m is an integer from 1 to 4; Y is hydrogen, alkyl having 1 carbon atom to about 10 carbon atoms, -CHR'OH, where R' is as defined above, or [ka] wherein Y′ is —CHR′OH, where R′ is as defined above; R, X, and W are as defined above; and Z is hydroxyl, a hydroxyphenyl group of the formula: [ka] (wherein R, R1, Y', X, and W are as defined above), n is an integer from 0 to 20, with the proviso that when n=0, Z must be: [ka] (wherein R, R1, Y', X, and W are as defined above).

[0052] Lubricating oil The lubricating oil compositions of the present invention comprise a base oil; and a primary succinimide dispersant. In some embodiments, the lubricating oil compositions comprise a secondary succinimide dispersant. In some embodiments, the lubricating oil compositions comprise a Mannich dispersant.

[0053] The succinimide dispersants of the present disclosure can be useful as dispersant additives in lubricating oils. When used in this manner, the additives are typically present in the lubricating oil composition at concentrations ranging from 0.001 to 20 wt % (including, but not limited to, 0.01 to 5 wt %, 0.2 to 4 wt %, 0.5 to 3 wt %, 1 to 2 wt %, etc.) (based on the total weight of the lubricating oil composition). If other dispersants are present in the lubricating oil composition, lesser amounts of the additive may be used.

[0054] To obtain a lubricating oil composition of a desired grade of engine oil, for example, 0W, 0W-8, 0W-16, 0W-20, 0W-30, 0W-40, 0W-50, 0W-60, 5W, 5W-20, 5W-30, 5W-40, 5W-50, 5W-60, 10W, 10W-20, 10W-30, 10W-40, 10W-50, 15W, 15W-20, 15W-30, or 15W-40 Society of Automotive Engineers (SAE) viscosity grade, the oils used as base oils will be selected or blended depending on the desired end use and the additives in the final oil.

[0055] An oil of lubricating viscosity (sometimes called a "base stock" or "base oil") is the primary liquid component of a lubricant, e.g., with which additives and, optionally, other oils are blended to obtain 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.

[0056] The definitions of base stock and base oil in this disclosure are the same as those found in American Petroleum Institute (API) Publication 1509 Annex E (“API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils,” December 2016). Group I base stocks contain less than 90% saturates and / or greater than 0.03% sulfur and have a viscosity index (using the test methods specified in Table E-1) of 80 or greater and less than 120. Group II base stocks contain 90% or greater saturates and 0.03% or less sulfur and have a viscosity index (using the test methods specified in Table E-1) of 80 or greater and less than 120. Group III base stocks contain 90% or greater saturates and 0.03% or less sulfur and have a viscosity index (using the test methods specified in Table E-1) of 120 or greater. 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.

[0057] Natural oils include animal oils, vegetable oils (e.g., castor oil and lard oil), and mineral oils. Animal and vegetable oils with favorable thermo-oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely in terms of their crude source, for example, whether they are paraffinic, naphthenic, or mixed paraffinic-naphthenic. Oils derived from coal or shale are also useful. Natural oils also vary by the method used for production and refinement, for example, the distillation range and whether they are straight run or cracked, hydrotreated, or solvent extracted.

[0058] Synthetic oils include hydrocarbon oils, such as polymerized and copolymerized olefin oils (e.g., polybutylene, polypropylene, propylene-isobutylene copolymers, ethylene-olefin copolymers, and ethylene-alphaolefin copolymers). Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oils. Examples include C8 to C9 14 Olefins, e.g., C8, C 10 , C 12 , C 14 PAOs derived from olefins or mixtures thereof can be utilized.

[0059] Other useful fluids for use as base oils include unconventional or unconventional base stocks that have been treated, preferably catalytically treated or synthetic, to provide high performance properties.

[0060] Unconventional or unconventional base stocks / base oils include one or more of 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 feedstocks, mineral oil and / or non-mineral oil waxy feedstocks such as slack wax, natural wax, and waxy stocks such as gas oil, waxy fuel hydrocracker bottoms, wax raffinate, hydrocrackates, thermal crackers, or other mineral, mineral oil, or non-petroleum derived waxy materials such as waxy materials obtained from coal liquids or shale oil, and blends of such base stocks.

[0061] The base oils used in the lubricating oil compositions of the present disclosure can be any of a variety of oils corresponding to API Group I, Group II, Group III, Group IV, and Group V oils and mixtures thereof, preferably API Group II, Group III, Group IV, and Group V oils and mixtures thereof, more preferably Group III-Group V base oils, due to their excellent volatility, stability, viscosity, and cleanliness characteristics.

[0062] 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 to 8 mm 2 / sec).

[0063] The lubricating oil composition may also contain conventional lubricating oil additives to provide auxiliary functions in order 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, surfactants such as metal surfactants, rust inhibitors, dehazing agents, demulsifiers, friction modifiers, metal deactivators, pour point depressants, viscosity modifiers, antifoam agents, cosolvents, package compatibilizers, corrosion inhibitors, dyes, extreme pressure additives, and the like, and mixtures thereof. A variety of additives are known and commercially available. These additives or their analogous compounds can be used to prepare the lubricating oil composition of the present invention using conventional blending procedures.

[0064] Each of the above-described additives, when used, is used in a functionally effective amount to impart the desired characteristics to the lubricant. 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 characteristics to the lubricant. Generally, the concentration of each of these additives, when used, may range from about 0.001 to about 20 wt %, e.g., from about 0.01 to about 10 wt %, unless otherwise specified.

[0065] example The following examples are for illustrative purposes only and do not limit the scope of the present disclosure in any way.

[0066] Lubricant Baseline Formulation A An initial baseline lubricating oil composition was prepared by blending the following components together to obtain an SAE 10W-30 viscosity grade formulation: (a) a mixture of primary and secondary zinc dialkyldithiophosphates; (b) bissuccinimide dispersants; (c) magnesium sulfonate surfactant; (d) calcium phenate and calcium sulfonate; (e) alkylated diphenylamine and hindered phenol antioxidants; (f) molybdenum succinimide antioxidant; (g) pour point depressants, viscosity index improvers, and foam suppressants, and (h) Group II base oil blends.

[0067] Comparative Example 1 Comparative Example 1 was formulated by adding 2.875 wt% of a non-post-treated succinimide dispersant to baseline Formulation A.

[0068] Comparative Example 2 Comparative Example 2 was formulated by adding 2.875 wt% of a glycidol post-treated succinimide dispersant to Baseline Formulation A. The preparation of the glycidol post-treated succinimide dispersant is described below.

[0069] A stirred 250 mL, three-necked, round-bottom flask was charged with 122.24 g of bissuccinimide, the reaction product of 2300 MW hot PIBSA and HPA (1.24 wt% nitrogen). The bissuccinimide was then heated to 35°C using a heating mantle under a nitrogen purge. 2.45 g of glycidol (molecular weight = 74.08 g / mol, glycidol:HPA CMR = 2) was added dropwise to the bissuccinimide over 30 minutes using a syringe. The temperature of the mixture was maintained at 35°C for 16.5 hours. The diluent oil content of the final product was 33.8 wt%.

[0070] Comparative Example 3 Comparative Example 3 was formulated by adding 2.875 wt% of a glycidol post-treated succinimide dispersant to Baseline Formulation A. The preparation of the glycidol post-treated succinimide is described below.

[0071] A stirred 250 mL, three-necked round-bottom flask was charged with 122 g of bissuccinimide, the reaction product of 2300 MW hot PIBSA and HPA (1.24 wt% nitrogen). The bissuccinimide was then heated to 35°C using a heating mantle under a nitrogen purge. Using an addition funnel, 4.88 g of glycidol (molecular weight = 74.08 g / mol, glycidol:HPA CMR = 4) was added dropwise to the bissuccinimide over 2 hours. The temperature of the mixture was maintained at 35°C for 16.5 hours. The diluent oil content of the final product was 33.1 wt%.

[0072] Comparative Example 3 differs from Comparative Example 2 in the molar ratio of the feed used.

[0073] Example 1 Inventive Example 1 was formulated by adding 2.875% of the 4-glycidyloxycarbazole post-treated dispersant described above to Baseline Formulation A. The preparation of 4-glycidyloxycarbazole is described below.

[0074] A stirred 250 mL, three-necked, round-bottom flask was charged with 137.78 g of bissuccinimide. This was the reaction product of 2300 MW hot PIBSA and HPA (1.21 wt% nitrogen). The bissuccinimide was then heated to 135°C using a heating mantle under a nitrogen purge. 8.72 g of 4-glycidyloxycarbazole (molecular weight = 239.27 g / mol, 4-glycidyloxycarbazole:HPA = 2) was charged to the bissuccinimide over 2 hours. The temperature of the mixture was maintained at room temperature for 30 minutes. The product had the following properties: TBN = 19.8 mg KOH / g, nitrogen = 1.50 wt%, diluent oil = 33.8 wt%.

[0075] Soot thickening bench test Inventive Example 1 and Comparative Examples 1-4 were evaluated for soot dispersancy. Bench tests were conducted to measure the formulation's ability to disperse and control the viscosity increase resulting from the addition of carbon black, a soot substitute. For this test, each fresh oil sample was treated with VULCAN® XC72R carbon black (Cabot Corporation) and homogenized for 4 minutes using a Resodyn LabRAM II acoustic mixer to completely disperse the carbon black. The KV100 of each lubricating oil sample was then measured at 100°C using a Zeitfuchs countercurrent cross-arm viscometer (Cannon Instrument Company) in a PMT TV4000 temperature bath (Tamson Instruments) according to ASTM D445. Viscosity increases are reported relative to a reference oil sample containing no carbon black. A small viscosity increase indicates improved soot dispersancy, while a large viscosity increase or gelation of the sample indicates poor dispersancy. The results of the soot thickening bench tests are summarized in Table 1 below. [Table 1]

[0076] As can be seen in Table 1, Example 1 of the present invention (Ex. 1) exhibited a lower viscosity increase compared to the comparative example (Comp. Ex.), indicating that the aromatic after-treatment agent of Example 1 provides superior soot dispersancy capabilities.

[0077] All documents described herein are incorporated herein by reference, including any priority documents and / or test procedures, unless inconsistent with the text. As is apparent from the general description and specific embodiments above, forms of the present disclosure have been illustrated and described, but various modifications can be made without departing from the spirit and scope of the present disclosure. Accordingly, the present disclosure is not intended to be limited thereby.

[0078] Similarly, the term "comprising" is considered synonymous with the term "comprising." Similarly, whenever a composition, element, or group of elements is preceded by the transitional phrase "comprising," it is understood that the inventors also contemplate the same composition, or group of elements where the transitional phrase "consisting essentially of," "consisting of," "selected from the group consisting of," or "is" precedes the recitation of the composition, element(s), and vice versa.

[0079] As used herein, the terms "a" and "the" are understood to encompass the plural as well as the singular.

[0080] Various terms are defined above. To the extent a term used in the claims is not defined above, it should be given the broadest definition that those of ordinary skill in the art would give that term, as reflected in at least one publication or issued patent. Furthermore, all patents, test procedures, and other documents cited in this application are incorporated by reference in their entirety to the extent such disclosure is not inconsistent with this application and for all jurisdictions where such incorporation is permitted.

[0081] The foregoing description of the present disclosure illustrates and describes the present disclosure. Moreover, while the present disclosure shows and describes only preferred embodiments, it should be understood that the present disclosure is capable of use in various other combinations, modifications, and environments, as noted above, and that changes or modifications are possible within the scope of the concepts expressed herein, commensurate with the above teachings and / or skill or knowledge of the relevant art. While the foregoing relates to embodiments of the present disclosure, other and further embodiments of the present disclosure may be devised without departing from the basic scope thereof, which scope is determined by the following claims.

[0082] The embodiments described herein above further illustrate the best modes known for practicing the same, and are intended to enable those skilled in the art to utilize the present disclosure in such or other embodiments, and with various modifications as required by a particular application or use. Therefore, the description is not intended to be limited to the forms disclosed herein. Also, it is intended that the appended claims be construed to include alternative embodiments.

Claims

1. 1. A dispersant composition comprising: Structure I: [Chemical Formula I] (In the formula, R １ is a heteroaryl or heteroarylalkyl group having 4 to 20 carbon atoms, and R ２ and R ３ are independently a hydrogen atom, an alkyl group, or an aryl group), and a succinimide dispersant composition comprising the reaction product of a heteroaromatic glycidyl ether and a hydrocarbyl succinimide.

2. 2. The dispersant composition of claim 1, wherein the hydrocarbyl succinimide is a monosuccinimide, a bissuccinimide, a trissuccinimide, or a mixture thereof.

3. 10. The dispersant composition of claim 1, wherein said hydrocarbyl succinimide is a reaction product of at least one succinimide anhydride and a polyamine.

4. 4. The dispersant composition of claim 3, wherein the polyamine is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, or a polyalkyleneamine.

5. 10. The dispersant composition of claim 1, wherein the reaction product is further post-treated with an organic oxide, a reactive boron compound, or an organic carbonate.

6. 10. The dispersant composition of claim 1, further comprising a second succinimide.

7. 8. The dispersant composition of claim 7, wherein said second succinimide is post-treated with an organic carbonate, glycidol, a glycidyl ether different from Structure I, an organic oxide, or a reactive boron compound.

8. R ２ and R ３ 2. The dispersant composition of claim 1, wherein at least one of is a hydrogen atom.

9. 10. The dispersant composition of claim 1, further comprising a dispersant prepared by a Mannich reaction.

10. 1. A lubricating oil composition comprising: base oil, Structure I: [Chemical Formula I] (In the formula, R １ is a heteroaryl or heteroarylalkyl group having 4 to 20 carbon atoms, and R ２ and R ３ are independently a hydrogen atom, an alkyl group, or an aryl group), and a hydrocarbyl succinimide. The lubricating oil composition comprising:

11. 11. The lubricating oil composition of claim 10, wherein the hydrocarbyl succinimide is a monosuccinimide, a bissuccinimide, a trissuccinimide, or a mixture thereof.

12. 11. The lubricating oil composition of claim 10, wherein the hydrocarbyl succinimide is a reaction product of at least one succinimide anhydride and a polyamine.

13. 13. The lubricating oil composition of claim 12, wherein the polyamine is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, or a polyalkyleneamine.

14. 11. The lubricating oil composition of claim 10, wherein the reaction product is further post-treated with an organic oxide, a reactive boron compound, or an organic carbonate.

15. The lubricating oil composition of claim 10, further comprising a second succinimide.

16. 16. The lubricating oil composition of claim 15, wherein the second succinimide is post-treated with an organic carbonate, glycidol, a glycidyl ether different from Structure I, an organic oxide, or a reactive boron compound.

17. R ２ and R ３ The lubricating oil composition of claim 10, wherein at least one of is a hydrogen atom.

18. 11. The lubricating oil composition of claim 10, further comprising a Mannich reaction prepared dispersant.

19. 1. A method for reducing soot induced viscosity increase in an engine, said method comprising: introducing a dispersant composition into said engine, said dispersant composition comprising: Structure I: [Chemical Formula I] wherein R1 is a heteroaryl or heteroarylalkyl group having from 4 to 20 carbon atoms, and R2 and R3 are independently a hydrogen atom, an alkyl group, or an aryl group; and a succinimide dispersant comprising the reaction product of a heteroaromatic glycidyl ether and a polyalkenyl succinimide; operating the engine.

20. 20. The method of claim 19, wherein the hydrocarbyl succinimide is a monosuccinimide, a bissuccinimide, a trissuccinimide, or a mixture thereof.

21. 20. The method of claim 19, wherein the hydrocarbyl succinimide is a reaction product of at least one succinimide anhydride and a polyamine.

22. 22. The method of claim 21, wherein the polyamine is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, or a polyalkyleneamine.

23. 20. The method of claim 19, wherein the dispersant composition further comprises a second succinimide.

24. 24. The method of claim 23, wherein the second succinimide is post-treated with an organic oxide, a reactive boron compound, or an organic carbonate.

25. R ２ and R ３ 20. The method of claim 19, wherein at least one of is a hydrogen atom.

26. 20. The method of claim 19, further comprising a dispersant made by a Mannich reaction.

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