Amine-enhanced cleaning agent

Abstract

A process for preparing a low ash detergent is described which comprises mixing a surfactant composition containing a hydroxybenzoate, sulfonate, or phosphonate detergent with an ashless nitrogen-containing compound to enhance the base number of the hydroxybenzoate, sulfonate, or phosphonate detergent.

Description

[Technical Field]

[0001] This disclosure relates to detergent additive compositions. More specifically, this disclosure describes amine-enhanced detergent compositions and lubricating oil compositions containing the same. [Background technology]

[0002] Metal cleaning additives are often used in automotive lubricants to provide important benefits such as preventing deposit formation and improving fuel efficiency.

[0003] In particular, over-basicating the cleaning agent can provide a metal base reserve that neutralizes corrosive acids generated in the engine environment. In the case of calcium-based cleaning agents, the degree to which the cleaning agent is over-basicated depends on the level of calcium carbonate (CaCO3) present.

[0004] Over-basicated calcium-based metal detergents are oil-soluble particles with a surfactant shell and a calcium carbonate core. The degree of over-basication is indicated by the total base number (TBN). Generally, the higher the TBN, the longer the operating period under harsh conditions before lubrication oil replacement is required.

[0005] One drawback of these types of cleaning agents is that the presence of metals can generate sulfated ash, which can contaminate exhaust gas treatment catalysts. Calcium carbonate contributes to TBN, but it can also lead to the formation of sulfated ash. One way to address this problem is to limit the metal content in the additive package. [Overview of the project]

[0006] In one embodiment, a process is provided for preparing a low-ash detergent, comprising mixing a surfactant composition containing a hydroxybenzoate, sulfonate, or phosphonate detergent with an ash-free nitrogen-containing compound to enhance the base number of the hydroxybenzoate, sulfonate, or phosphonate detergent.

[0007] In another embodiment, a process for preparing a low-ash cleaner is provided, comprising mixing a hydroxybenzoate, sulfonate, or phosphonate cleaner with an amine or amine derivative, wherein the amine or amine derivative is added to overbase or enhance the base value of the hydroxybenzoate, sulfonate, or phosphonate cleaner.

[0008] In yet another embodiment, a lubricating oil composition is provided comprising: a main amount of lubricating viscosity oil; and a small amount of low-ash detergent produced by a process comprising mixing a hydroxybenzoate, sulfonate, or phosphonate detergent with an amine or amine derivative, wherein the amine or amine derivative is added to overbase or enhance the base number of the hydroxybenzoate, sulfonate, or phosphonate detergent.

[0009] Detailed description In this specification, the following words and expressions have the following meanings when used and when used:

[0010] The term "alkyl" or related terms refer to a saturated hydrocarbon group that may be linear, branched, cyclic, or a combination of cyclic, linear, and / or branched. The term "alkenyl" or related terms refer to an unsaturated hydrocarbon group that may be linear, branched, cyclic, or a combination of cyclic, linear, and / or branched.

[0011] In hydrocarbon-based formulations (particularly lubricants), the term "ash" or related terms refers to the metallic compounds remaining after the combustion of hydrocarbons. This ash primarily originates from chemicals and solids used in certain additives. The term "sulfated ash" refers to the combustion products of metals commonly found in detergents. As a characteristic of lubricants, sulfated ash serves as an indicator of the metal content (usually Zn, Ca, and Mg).

[0012] The term "ash-free" or related terms refers to formulations or additives that do not produce ash or limit ash production. Ash-free additives generally do not contain metals (including boron), silicon, or halogens, or contain these elements at concentrations below the detection limits of typical instruments.

[0013] "Small amount" or related terms mean less than 50 wt% of the composition, expressed as the active ingredient of the additive, with respect to the listed additive and with respect to the total weight of the composition.

[0014] "Major amount" or related terms refer to an amount exceeding 50 wt% based on the total weight of the composition.

[0015] The term "calcium content" refers to calcium hydroxide, also known as slaked lime or hydrated lime.

[0016] The term "Total Base Number" or "TBN" refers to the level of alkalinity of an oil sample, indicating the ability of a composition to continue neutralizing corrosive acids, according to ASTM standard number D2896 or an equivalent procedure. The test measures the change in electrical conductivity, and the result is expressed as mgKOH / g (the number of equivalent milligrams of KOH required to neutralize 1 gram of product). Therefore, a high TBN reflects strong over-basication of the product, resulting in a large base reserve for neutralizing acids.

[0017] This invention describes a low-ash detergent that, when used as an additive in lubricating oil under engine operating conditions, produces less sulfated ash per base number (BN) compared to conventional over-basic detergents. The low-ash detergent of this invention comprises 1) a surfactant and 2) a nitrogen-containing compound. The nitrogen-containing compound, such as an amine or amine derivative, is used to over-basicate the detergent and enhance the TBN. In one embodiment, this invention relates to an amine-enhanced detergent in which the nitrogen-containing compound is an amine or amine derivative. In another embodiment, the nitrogen-containing compound is ash-free.

[0018] The low-ash detergent of the present invention generally contains less metal salts compared to conventional detergents that rely heavily on metal salts (e.g., CaCO3) to neutralize acids during engine operation. As a result, the detergent of the present invention generates less sulfated ash. Nitrogen-containing compounds contribute to the total base number but do not contribute to the formation of sulfated ash.

[0019] Particularly useful surfactants suitable for the present invention include metal cleaners such as hydroxybenzoates, sulfonates, and phosphonates. Some non-limiting examples of suitable metal cleaners include alkyl or alkenyl aromatic sulfonates, borated sulfonates, sulfurized or non-sulfurized metal salts of polyhydroxyalkyl or alkenyl aromatic compounds, metal salts of alkyl or alkenyl hydroxybenzoic acid, alkyl or alkenyl hydroxy aromatic sulfonates, sulfurized or non-sulfurized alkyl or alkenyl naphthenates, metal salts of alkanic acid, metal salts of alkyl or alkenyl polyacids, and chemical and physical mixtures thereof. Other non-limiting examples of suitable metal cleaners include salicylates and thiophosphonates. Non-limiting examples of suitable metals include alkali metals, alkali metals, and transition metals. In some embodiments, the metals are Ca, Mg, Ba, K, Na, Li, etc.

[0020] Particularly useful nitrogen-containing compounds suitable for the present invention include amines and amine derivatives such as carbamates, urea, amides, and imides. The nitrogen-containing compounds may also contain heteroatoms (e.g., alcohols), saturated groups, aromatic groups, etc.

[0021] Examples of amines or amine derivatives include alkylated amines (e.g., 2-ethylhexyl (tallow) methylamine, ethylhexylamine, octylamine), hydrocarbylamines, ethylenediamine, N-methylethanolamine, 1,1-dimethylethylenediamine, 2-methoxyethylamine, ethanolamine (e.g., diethanolamine), N-methylpropylenediamine, piperazine (e.g., dodecylpiperazine), urea, tetramethylurea, diphenylamine, alkylated diphenylamine, benzylamine, N-phenylphenylenediamine, triethylenetetraamine, triethanolamine, 1,4-diazabicyclo[2.2.2]-octane, N,N'-bis(3-aminopropyl)ethylenediamine ("N4 amine"), phenoxyamine (e.g., 2-phenoxyethylamine, C20-C24 alkyl-2-phenoxyethylamine), 2-(2-aminoethoxy)naphthalene, N-(3-(dimethylamino)propyl)benzamide, phenylamine (e.g., 3-phenylpropylamine), benzamide, amino acids, and phthalimide.

[0022] More specifically, suitable phthalimides include N-(2-hydroxyethyl)phthalimide, N-(2-aminoethyl)phthalimide, N-(3-hydroxypropyl)phthalimide, N-(3-aminopropyl)phthalimide, N-(2-(methylamino)ethyl)phthalimide, N-(3-(methylamino)propyl)phthalimide, N-(2-(dimethylamino)ethyl)phthalimide, and N-(3-(dimethylamino)propyl)phthalimide.

[0023] In some embodiments, the low-ash detergent of the present invention may contain a mixture of nitrogen-containing compounds such as amines and carbamates.

[0024] Synthesis of Detergent The low-ash detergent of the present invention can be synthesized by any suitable method. However, one advantage is that the production of the low-ash detergent of the present invention is compatible with conventional detergent production processes, such as the following: For example, the production of conventional over-basicated alkylhydroxybenzoate calcium detergents often begins with the reaction of alkylphenol with a metal base. The product is then carboxylated (i.e., treated with CO2) and acidified. The resulting acid product can be neutralized with lime and over-basicated. Some of these steps (e.g., the second neutralization and over-basication) can be carried out simultaneously. A more detailed description of this process can be found in US8,030,258, which is incorporated herein by reference.

[0025] The cleaning agent of the present invention can be synthesized using any suitable method. In one embodiment, the synthesis of the cleaning agent of the present invention differs from the synthesis of conventional cleaning agents in that the low-ash cleaning agent of the present invention is reinforced with a nitrogen-containing compound (e.g., an amine or amine derivative) instead of a metal base (e.g., calcium carbonate).

[0026] In one exemplary example, a process for preparing a hyperalkalized amine-enhanced alkaline earth metal alkylaryl sulfonate comprises: (a) neutralizing an alkyltoluene / benzene sulfonic acid with an alkaline earth metal base (e.g., MgO) to form an alkaline earth metal alkyltoluene / benzene sulfonate; (b) contacting the alkaline earth metal alkyltoluene / benzene sulfonate and the alkaline earth metal base from step (a) with at least one carboxylic acid having from about 1 to 4 carbon atoms to form a mixture of an alkaline earth metal alkylaryl sulfonate and at least one alkaline earth metal carboxylate, and (c) hyperalkalizing the alkaline earth metal alkylaryl sulfonate from step (b) with an amine or amine derivative and at least one acidic hyperalkalizing material in the presence of at least one alkaline earth metal carboxylate from step (b). A more detailed description of the production of alkaline earth metal alkylaryl sulfonates can be found in US6,479,440, which is incorporated herein by reference.

[0027] As an exemplary example, a process for preparing a hyperalkalized amine-enhanced alkaline earth metal alkylaryl sulfonate comprises: (a) neutralizing an alkyltoluene / benzene sulfonic acid with an alkaline earth metal base (e.g., CaO or Ca(OH)2) to form an alkaline earth metal alkylaryl sulfonate, and (b) hyperalkalizing the alkaline earth metal alkylaryl sulfonate from step (a) with an amine or amine derivative. A more detailed description of the production of alkaline earth metal alkylaryl sulfonates can be found in U.S.Pat.No.8,076,272, which is incorporated herein by reference.

[0028] As an exemplary example, a process for preparing an overbasized amine-enhanced alkaline earth metal alkyl hydroxybenzoate is: (a) reacting an alkylphenol with an alkali metal base to produce an alkali metal alkylphenate; (b) carboxylating the alkali metal alkylphenate obtained in step (a) with carbon dioxide such that at least 50 mol% of the starting alkylphenol is converted to an alkali metal alkyl hydroxybenzoate; (c) acidifying the alkali metal alkyl hydroxybenzoate obtained in step (b) with an aqueous solution of a strong acid to produce an alkyl hydroxybenzoic acid; (d) neutralizing the alkyl hydroxybenzoic acid from step (c) with a molar excess of an alkaline earth metal base and at least one solvent selected from aromatic hydrocarbons, aliphatic hydrocarbons, monoalcohols, and mixtures thereof. (e) Forming an alkaline earth metal alkyl hydroxybenzoate; (f) Contacting the alkaline earth metal alkyl hydroxybenzoate and alkaline earth metal base from step (d) with at least one carboxylic acid having about 1 to 4 carbon atoms (i.e., an aromatic hydrocarbon, an aliphatic hydrocarbon, a monoalcohol, or a mixture thereof) in the presence of a solvent to form a mixture of the alkaline earth metal alkyl hydroxybenzoate and at least one alkaline earth metal carboxylate; and (f) Overbasting the alkaline earth metal alkyl hydroxybenzoate from step (e) with an amine or amine derivative and at least one acidic overbasic material in the presence of at least one alkaline earth metal carboxylate from step (e) and a solvent (i.e., an aromatic hydrocarbon, an aliphatic hydrocarbon, a monoalcohol, or a mixture thereof).

[0029] In another embodiment, the amine may be added during neutralization before the overbasement step.

[0030] It is understood that the specific order of one or more steps in the synthesis route of a cleaning agent (e.g., alkylaryl sulfonates, alkyl hydroxybenzoates, etc.) may be rearranged, combined, or slightly modified as desired, as long as it is compatible with the present invention and adheres to the present invention. For illustrative purposes, the following embodiments are provided for the synthesis of cleaning agents comprising alkyl hydroxybenzoic acid, alkyl aromatic sulfonic acid, and alkenyl aromatic sulfonic acid. These modifications may also be applicable to other cleaning agent synthesis routes compatible with the present invention.

[0031] For example, in the alkylhydroxybenzoate detergent synthesis pathway, the alkylhydroxybenzoic acid may be neutralized with a lime slurry (i.e., Ca(OH)2). Optionally, the amine may be present in the lime slurry during the neutralization step. The lime slurry and the amine or amine derivative may be introduced into the reactor while both react with CO2.

[0032] According to one embodiment, the amine treatment can be carried out after the alkylhydroxybenzoic acid is neutralized by a lime slurry, and the excess lime reacts with CO2 to form a metal carbonate (e.g., calcium carbonate).

[0033] According to one embodiment, the amine treatment can be performed after the alkylhydroxybenzoic acid is neutralized by the lime slurry and before the lime slurry reacts with CO2.

[0034] According to one embodiment, the amine can be charged into the reactor after neutralizing the alkylhydroxybenzoic acid with a lime slurry. The amine or amine derivative may be dispersed by the neutralized surfactant without further treatment.

[0035] According to one embodiment, alkylhydroxybenzoic acid can be neutralized with an excess amount of amine compared to the amount required to neutralize it. The excess amine can react with CO2 to form a carbamate.

[0036] According to one embodiment, alkylhydroxybenzoic acid can be neutralized with an excess amount of amine compared to the amount required to neutralize it.

[0037] According to one embodiment, alkylhydroxybenzoic acid can be neutralized with a lime slurry, after which the amine is treated with ethylene carbonate. In some embodiments, a metal base may be used in addition to or in addition to lime. Suitable metal bases include alkali metal bases and alkaline earth metal bases. An example of a suitable metal base is MgO.

[0038] According to one embodiment, in the alkyl or alkenyl aromatic sulfonate cleaning agent synthesis route, the alkyl or alkenyl aromatic sulfonic acid may be neutralized with a lime slurry (i.e., Ca(OH)2). Optionally, the amine may be present in the lime slurry during the neutralization step. The lime slurry and the amine or amine derivative may be introduced into the reactor while both react with CO2.

[0039] According to one embodiment, the amine treatment can be carried out after the alkyl or alkenyl aromatic sulfonic acid has been neutralized by a lime slurry, and the excess lime has reacted with CO2 to form a metal carbonate (e.g., calcium carbonate).

[0040] According to one embodiment, the amine treatment can be carried out after the alkyl or alkenyl aromatic sulfonic acid has been neutralized by the lime slurry, but before the lime slurry reacts with CO2.

[0041] According to one embodiment, the amine can be charged into the reactor after the alkyl or alkenyl aromatic sulfonic acid has been neutralized with a lime slurry. The amine or amine derivative may be dispersed by the neutralized surfactant without further treatment.

[0042] According to one embodiment, an alkyl or alkenyl aromatic sulfonic acid can be neutralized with an excess of amine in an amount greater than the amount required to neutralize it. The excess amine can react with CO2 to form a carbamate.

[0043] According to one embodiment, an alkyl or alkenyl aromatic sulfonic acid can be neutralized with an amine in excess of the amount required to neutralize it.

[0044] According to one embodiment, alkyl or alkenyl aromatic sulfonic acid can be neutralized with a lime slurry, after which the amine is treated with ethylene carbonate. In some embodiments, a metal base may be used in addition to or in addition to lime. Suitable metal bases include alkali metal bases and alkaline earth metal bases. An example of a suitable metal base is MgO.

[0045] The products of amine treatment include ammonium carbamate and calcium carbonate. The production volume of the latter is lower compared to the production and synthesis of conventional cleaning agents.

[0046] Any amine or amine derivative reagent suitable for the present invention can be used. Examples of these amines include primary amines, secondary amines, tertiary amines, and their derivatives. The amine may contain heteroatoms (e.g., alcohols), saturated groups, aromatic groups, etc.

[0047] Suitable primary amines or amine derivatives include, for example, glycine, 2-ethylhexylamine, octylamine, 2-methoxyethylamine, 2-phenoxyethylamine, 2-(2-aminoethoxy)naphthalene, 3-phenylpropylamine, and benzamide.

[0048] Suitable secondary amines or amine derivatives include, for example, ethylenediamine, diphenylamine, alkylated diphenylamine, triethylenetetraamine, N-phenylphenylenediamine, N-ethylbutylamine, isopropylmethylamine, N-ethylhexylamine, N-methylethanolamine, diethanolamine, and phthalimide.

[0049] Suitable tertiary amines or amine derivatives include, for example, triethanolamine, 1,4-diazabicyclo[2.2.2]octane, dialkylpiperazine, 2-ethylhexyl(fat)methylamine, and tetramethylurea.

[0050] Some amines or amine derivatives may have multiple amines or amine derivatives that are independently primary, secondary, or tertiary amines. Examples include 1,1-dimethylethylenediamine, N-methylpropylenediamine, 1-dodecylpiperazine, N,N'-bis(3-aminopropyl)ethylenediamine ("N4 amine"), and N-(3-(dimethylamino)propyl)benzamide.

[0051] In the amine treatment stage, one or more solvents are used. Suitable solvents include xylene, toluene, and methanol.

[0052] The alkyl or alkenyl group of amine-enhanced alkaline earth metal alkyl hydroxybenzoates or alkylaryl sulfonates can be derived from alkyl substituents having C10-40 alkyl groups, preferably C12-C30, C14-C18, C18-30, C20-28, or C20-24 alkyl groups, or mixtures thereof.

[0053] In one embodiment, the alkyl substituent is a residue derived from an α-olefin having 14 to 28 carbon atoms per molecule. In one embodiment, the alkyl substituent is a residue derived from an α-olefin having 14 to 18 carbon atoms per molecule. In one embodiment, the alkyl substituent is a residue derived from an α-olefin having 20 to 28 carbon atoms per molecule. In one embodiment, the alkyl substituent is a residue derived from an α-olefin having 20 to 24 carbon atoms per molecule. In one embodiment, the alkyl substituent is a residue derived from an olefin containing a C12-C40 oligomer of a monomer selected from propylene, butylene, or a mixture thereof. Examples of such olefins include propylene tetramers, butylene trimers, and isobutylene oligomers.

[0054] The olefin may be linear, isomerized linear, branched, or partially branched linear. The olefin may be a mixture of linear olefins, a mixture of isomerized linear olefins, a mixture of branched olefins, a mixture of partially branched linear olefins, or any of the aforementioned mixtures. The α-olefin may be a regular α-olefin, an isomerized regular α-olefin, or a mixture thereof.

[0055] In one embodiment, where the alkyl substituent is a residue derived from the isomerized α-olefin, the α-olefin may have an isomerization level (I) of 0.1 to 0.4 (e.g., 0.1 to 0.3, or 0.1 to 0.2). The isomerization level (I) is, 1 This can be determined by 1H NMR spectroscopy and represents the relative amount of methyl groups (-CH3) (chemical shift 0.30-1.01 ppm) bonded to methylene skeleton groups (-CH2-) (chemical shift 1.01-1.38 ppm), and is defined by the following formula:

number

[0056] The amine-enhanced alkaline earth metal alkyl hydroxybenzoates of this disclosure have a TBN of 90 to 600 mg KOH / g based on the active substance, for example, 90 to 500 mg KOH / g, 90 to 450 mg KOH / g, or 90 to 400 mg KOH / g, 90 to 350 mg KOH / g, 90 to 300 mg KOH / g, 150 to 590 mg KOH / g, 150 to 500 mg KOH / g, 150 to 450 mg KOH / g, 150 to 400 mg KOH / g, 150 to 350 mg KOH / g, 150 to 300 mg KOH / g, 200 to 590 mg KOH / g, 200 to 500 mg KOH / g, 200 to 450 mg KOH / g, 200 to 400 mg KOH / g, or 200 to 350 mg KOH / g.

[0057] The amine-enhanced alkaline earth metal alkylaryl sulfonates of this disclosure have a TBN of 20 to 700 mg KOH / g based on the active substance, for example, 20 to 650 mg KOH / g, 20 to 600 mg KOH / g, 20 to 550 mg KOH / g, 20 to 500 mg KOH / g, 150 to 700 mg KOH / g, 150 to 650 mg KOH / g, 150 to 550 mg KOH / g, 150 to 500 mg KOH / g, 200 to 700 mg KOH / g, 250 to 700 mg KOH / g, 300 to 700 mg KOH / g, 200 to 600 mg KOH / g, 250 to 550 mg KOH / g, 300 to 500 mg KOH / g, or 350 to 450 mg KOH / g.

[0058] In another embodiment, the amine-enhanced alkaline earth metal cleaner comprises two or more surfactants, which are often known in the art as composite or hybrid cleaners. For example, the amine-enhanced overbasic alkaline earth metal cleaner contains both alkylhydroxybenzoates and alkylarylsulfonates in its surfactant system.

[0059] lubricating oil composition The cleaning agent compositions of this disclosure may be used in lubricating oils. When used in this manner, the cleaning agent is typically present in the lubricating oil composition at a concentration ranging from 0.05 wt% to 10 wt% (including, but not limited to, 0.1 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 cleaning agents are present in the lubricating oil composition, a smaller amount of the cleaning agent of the present invention may be used.

[0060] The oil material used as the base oil is selected or blended according to the desired end use and additives contained in the finished oil material to give a lubricating oil composition having the desired grade of engine oil, for example, the Society of Automotive Engineers (SAE) viscosity grades 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.

[0061] Lubricating viscosity oils (sometimes referred to as "base materials" or "base oils") are the main liquid components of lubricating oils, and are blended with additives and, optionally, other oils to produce, for example, the final lubricating oil (or lubricating oil composition). Base oils are useful for producing concentrates and from which lubricating oil compositions are produced, and can be selected from natural (vegetable, animal, or mineral) and synthetic lubricating oils, as well as mixtures thereof.

[0062] The definitions of base oils and base materials in this disclosure are the same as those 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 materials contain less than 90% saturation and / or more than 0.03% sulfur and have a viscosity index of 80 or more and less than 120 as determined by the test method specified in Table E-1. Group II base materials contain 90% or more saturation and 0.03% or less sulfur and have a viscosity index of 80 or more and less than 120 as determined by the test method specified in Table E-1. Group III base materials contain 90% or more saturation and 0.03% or less sulfur and have a viscosity index of 120 or more as determined by the test method specified in Table E-1. Group IV base materials are poly-α-olefins (PAOs). Group V base materials include all other base materials not included in Groups I, II, III, or IV.

[0063] Natural oils include animal oils, vegetable oils (e.g., castor oil and lard), and mineral oils. Animal and vegetable oils with good thermal oxidative stability can be used. Among natural oils, mineral oils are preferred. Mineral oils vary greatly depending on their crude source, such as whether they are paraffinic, naphthenic, or a mixture of paraffinic and naphthenic oils. Oils derived from coal and shale are also useful. Natural oils also vary depending on the methods used in their production and refining, such as the extent of distillation and whether they are straight-run, cracked, hydrolyzed, or solvent-extracted.

[0064] Synthetic oils include hydrocarbon oils. Hydrocarbon oils include oil materials such as polymerized and crosspolymerized olefins (e.g., polybutylene, polypropylene, propylene-isobutylene copolymer, ethylene-olefin copolymer, and ethylene-α-olefin copolymer). Poly-α-olefin (PAO) oil base is a commonly used synthetic hydrocarbon oil material. As an example, C8-C 14 Olefins, for example, C8, C10 , C 12 , C 14 PAO derived from olefins, or mixtures thereof, may be used.

[0065] Other useful fluids for use as base oils include non-conventional or unconventional base materials that have been processed (preferably catalytically) or synthesized to provide high performance characteristics.

[0066] Non-conventional or unconventional base materials / base oils include one or more mixtures of one or more base materials (s) derived from one or more gas-to-liquids (GTL) materials, as well as isomers / isodewaxed base materials (s) derived from natural waxes or waxy feedstocks, waxy feedstocks of mineral and / or non-mineral oils such as slack wax, natural waxes, and waxy base materials such as gas oils, bottoms fractions of wax hydrocracking units, waxy raffinates, hydrocrackates, pyrolyzates, or other wax-like materials obtained from minerals, mineral oils, or coal liquefaction or shale oil, and mixtures of such base materials.

[0067] The base oil for use in the lubricant compositions of the present disclosure is any of the various oil materials corresponding to API Group I, Group II, Group III, Group IV, and Group V oil materials, and mixtures thereof, preferably API Group II, Group III, Group IV, and Group V oil materials, and mixtures thereof, and more preferably Group III to Group V base oils due to their excellent volatility, stability, viscosity, and cleanliness characteristics.

[0068] Typically, the base oil has a kinematic viscosity (ASTM D445) in the range of 2.5 to 20 mm 2 / s (e.g., 3 to 12 mm 2 / s, 4 to 10 mm 2 [[ID=...]] / s, or 4.5 to 8 mm 2 / s) at 100 °C.

[0069] The lubricating oil composition of the present invention may also contain conventional lubricating oil additives to provide auxiliary functions, giving a finished product of the lubricating oil composition in which these additives are dispersed or dissolved. For example, the lubricating oil composition may contain antioxidants, ashless dispersants, anti-wear agents, detergents, rust inhibitors, de-fogging agents, de-emulsifiers, friction modifiers, metal deactivators, pour point depressants, viscosity modifiers, defoaming agents, co-solvents, package compatibilizers, corrosion inhibitors, dyes, extreme pressure agents, and mixtures thereof. Various additives are known and commercially available. These additives or analogous compounds can be used in the preparation of the lubricating oil composition of the present invention by conventional compounding procedures.

[0070] Each of the aforementioned additives, when used, is used in a functionally effective amount to impart the desired properties to the lubricant. Therefore, for example, if the additive is an ashless dispersant, the functionally effective amount of this ashless dispersant is sufficient to impart the desired dispersion properties to the lubricant. Generally, the concentration of each of these additives, when used, may range from about 0.001 to about 20 wt%, for example, from about 0.01 to about 10 wt%, unless otherwise specified.

[0071] The following exemplary embodiments are intended to be non-limiting. [Examples]

[0072] The examples provide low-ash purifying agents synthesized from alkylhydroxybenzoate or sulfonate compositions. The reaction was carried out in a 5-liter four-necked glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 300-350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser under nitrogen gas.

[0073] Example 1 Ethylenediamine In Example 1, ethylenediamine was introduced simultaneously with a lime slurry to neutralize alkylhydroxybenzoic acid, which was then reacted with CO2.

[0074] 175.8 grams of methanol, 222.5 grams of xylene solvent, and 175.8 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0075] The lime slurry and 76.1 g of ethylenediamine were charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. The mixture was stirred for several minutes. Next, 1820.4 g of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The resulting mixture was stirred at 40°C for 15 minutes. The reactor was cooled to 30°C in 15 minutes. 56.9 g of CO2 was introduced at a rate of 0.95 g / min over 60 minutes. Subsequently, 55.5 g of CO2 was introduced at a rate of 0.95 g / min over 58 minutes. During the reaction with CO2, the reactor temperature rose from 30°C to 40°C.

[0076] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and finally from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 g of 140N lubricating oil was charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C under a vacuum of 30 mmHg for approximately 45 minutes, and the xylene was distilled off by holding at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0077] Example 2 diphenylamine In Example 2, diphenylamine was introduced simultaneously with the lime slurry to neutralize the alkylhydroxybenzoic acid, which was then reacted with CO2.

[0078] 150 grams of methanol, 222.5 grams of xylene solvent, and 150 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0079] The lime slurry and 200 g of diphenylamine were charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction tube (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. The mixture was stirred for several minutes. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) were introduced. The mixture was stirred at 40°C for 15 minutes. The stirred mixture was cooled to 30°C in 15 minutes. Next, 48.5 grams of CO2 were introduced at a rate of 0.95 g / min over 51 minutes. The temperature rose from 30°C to 35°C. Next, 52 grams of CO2 were introduced at a rate of 0.95 g / min over 55 minutes. The temperature rose from 35°C to 40°C.

[0080] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product.

[0081] The liquid portion was placed in a 4-liter round-bottom reactor, the product was heated to 170°C, and xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0082] Example 3 diphenylamine In Example 3, alkylhydroxybenzoic acid was neutralized with lime, then diphenylamine was introduced and reacted with CO2.

[0083] 150 grams of methanol, 222.5 grams of xylene solvent, and 150 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0084] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at 40°C for 15 minutes. Then, 200 grams of diphenylamine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. Next, 48.5 grams of CO2 were introduced at a rate of 0.95 g / min over 51 minutes. The temperature rose from 30°C to 35°C. Next, 52 grams of CO2 were introduced at a rate of 0.95 g / min over 55 minutes. The temperature rose from 35°C to 40°C.

[0085] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product.

[0086] The liquid portion was placed in a 4-liter round-bottom reactor, the product was heated to 170°C, and xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0087] Example 4 Ethanolamine In Example 4, alkylhydroxybenzoic acid was neutralized with lime, then ethanolamine was introduced and reacted with CO2.

[0088] 130 grams of methanol, 222.5 grams of xylene solvent, and 130 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0089] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at 40°C for 15 minutes. Then, 70 grams of ethanolamine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. Next, 25 grams of CO2 were introduced at a rate of 0.95 g / min over 26 minutes. The temperature rose from 30°C to 34°C. Next, 51.3 grams of CO2 were introduced at a rate of 0.95 g / min over 54 minutes. The temperature rose from 34°C to 40°C.

[0090] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product.

[0091] The liquid portion was placed in a 4-liter round-bottom reactor, the product was heated to 170°C, and xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0092] Example 5 N-phenylphenylenediamine In Example 5, alkylhydroxybenzoic acid was neutralized with lime, then N-phenylphenylenediamine was introduced and reacted with CO2.

[0093] 85 grams of methanol, 222.5 grams of xylene solvent, and 85 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0094] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at 40°C for 15 minutes. Then, 200 grams of N-phenylphenylenediamine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. Next, 16.4 grams of CO2 were introduced at a rate of 0.95 g / min over 17 minutes. The temperature rose from 30°C to 32°C. Next, 47.8 grams of CO2 were introduced at a rate of 0.95 g / min over 55 minutes. The temperature rose from 32°C to 40°C.

[0095] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product.

[0096] The liquid portion was placed in a 4-liter round-bottom reactor, the product was heated to 170°C, and xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0097] Example 6 Triethylenetetraamine In Example 6, alkylhydroxybenzoic acid was neutralized with lime, then triethylenetetraamine was introduced and reacted with CO2.

[0098] 65 grams of methanol, 115.7 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0099] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at 40°C for 15 minutes. Then, 50 grams of triethylenetetramine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 20 minutes. Subsequently, 15 grams of CO2 were introduced at a rate of 0.95 g / min over 16 minutes. The temperature rose from 30°C to 35°C.

[0100] 60 grams of methanol, 106.8 grams of xylene solvent, and 60 grams of calcium hydroxide were charged into a beaker and stirred for several minutes to obtain a lime slurry. This lime slurry was then charged into the reactor. Next, 24.1 grams of CO2 were introduced at a rate of 0.95 g / min over 25 minutes. The temperature was raised from 35°C to 40°C. Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35000G to separate the insoluble solid product. The liquid portion was placed in a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was then removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0101] Example 7 1,4-Diazabicyclo[2.2.2]octane In Example 7, alkylhydroxybenzoic acid was neutralized with lime, then 1,4-diazabicyclo[2.2.2]octane was introduced and reacted with CO2.

[0102] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0103] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 190 grams of 1,4-diazabicyclo[2.2.2]octane was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. Subsequently, 74.5 grams of CO2 were introduced at a rate of 0.95 g / min (for 79 minutes). The temperature rose from 30°C to 40°C. Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0104] Example 8 1,4-Diazabicyclo[2.2.2]octane In Example 8, alkylhydroxybenzoic acid was neutralized with lime, then 1,4-diazabicyclo[2.2.2]octane was introduced and reacted with ethylene carbonate.

[0105] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0106] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 200 grams of 1,4-diazabicyclo[2.2.2]octane was introduced into the glass reactor, and the stirred mixture was heated to 45°C for 20 minutes. Subsequently, 314 grams of ethylene carbonate was introduced over 30 minutes. The temperature rose from 45 to 50°C. Subsequently, the reactor was heated from 50°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0107] Example 9 1,4-Diazabicyclo[2.2.2]octane In Example 9, alkylhydroxybenzoic acid was neutralized with lime, and then 1,4-diazabicyclo[2.2.2]octane was introduced.

[0108] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0109] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical agitator with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the agitator blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylphenol) was introduced. The mixture was stirred at 40°C for 15 minutes. Then, 190 grams of 1,4-diazabicyclo[2.2.2]octane was introduced into the glass reactor, and the stirred mixture was held at 40°C for 15 minutes. Subsequently, the reactor was heated from 40°C to 65°C in 15 minutes, then from 65°C to 93°C in 60 minutes, and then from 93°C to 128°C in 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0110] Example 10 1,4-Diazabicyclo[2.2.2]octane In Example 10, alkylhydroxybenzoic acid was neutralized with lime, and then 1,4-diazabicyclo[2.2.2]octane was introduced.

[0111] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0112] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical agitator with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the agitator blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% branched alkylhydroxybenzoic acid) were added. The mixture was stirred at 40°C for 15 minutes. Then, 190 grams of 1,4-diazabicyclo[2.2.2]octane were added to the glass reactor, and the stirred mixture was held at 40°C for 30 minutes. Subsequently, the reactor was heated from 40°C to 65°C in 15 minutes, then from 65°C to 93°C in 60 minutes, and then from 93°C to 128°C in 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0113] Example 11 1,4-Diazabicyclo[2.2.2]octane In Example 11, alkylhydroxybenzoic acid was neutralized with lime, then 1,4-diazabicyclo[2.2.2]octane was introduced and reacted with CO2.

[0114] 62 grams of methanol, 115.7 grams of xylene solvent, and 62 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0001] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% branched alkylhydroxybenzoic acid) were introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 170 grams of 1,4-diazabicyclo[2.2.2]octane were introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. Subsequently, 66.7 grams of CO2 were introduced at a rate of 0.95 g / min over 70 minutes. The temperature rose from 30°C to 37°C.

[0115] 38 grams of methanol, 106.8 grams of xylene solvent, and 38 grams of calcium hydroxide were charged into a beaker and stirred for several minutes to obtain a lime slurry. This lime slurry was then charged into the reactor. Subsequently, 12.2 grams of CO2 were introduced at a rate of 0.95 g / min over 13 minutes. The temperature was raised from 37°C to 40°C. The reactor was then heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35000 G to separate the insoluble solid product. The liquid portion was placed in a 4-liter round-bottom reactor, the product was heated to 170°C, and xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0116] Example 12 Triethylenetetraamine In Example 12, alkylhydroxybenzoic acid was neutralized with lime, then triethylenetetraamine was introduced and reacted with ethylene carbonate.

[0117] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0118] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical agitator with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the agitator blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxy acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Next, 110 grams of triethylenetetraamine was introduced into the glass reactor, and the stirred mixture was heated to 45°C for 20 minutes. Next, 132.5 grams of ethylene carbonate was introduced, and the mixture was stirred for 30 minutes and heated to 50°C. Subsequently, the reactor was heated from 50°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene are vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0119] Example 13 C9 alkylated diphenylamine In Example 13, alkylhydroxybenzoic acid was neutralized with lime, then C9 alkylated diphenylamine was introduced and reacted with CO2.

[0120] 65 grams of methanol, 115.7 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0121] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction tube (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 570 grams of C9 alkylated diphenylamine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 20 minutes. Subsequently, 67.5 grams of CO2 were introduced at a rate of 0.95 g / min over 71 minutes. The temperature rose from 30°C to 36°C. 110.8 grams of methanol, 106.8 grams of xylene solvent, and 110.8 grams of calcium hydroxide were charged into a beaker and stirred for several minutes to obtain a lime slurry. This lime slurry was charged into the reactor. Next, 56.4 grams of CO2 were introduced at a rate of 0.95 g / min over 59 minutes. The temperature rose from 36°C to 40°C. The first distillation step was then initiated under atmospheric pressure by heating the reactor from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 600 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, and the xylene was removed by distillation by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the device was cooled to ambient temperature.

[0122] Example 14 C9 alkylated diphenylamine In Example 14, alkylhydroxybenzoic acid was neutralized with lime, then C9 alkylated diphenylamine was introduced and reacted with CO2.

[0123] 62 grams of methanol, 115.7 grams of xylene solvent, and 62 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0124] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet tube (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% branched) was added. The mixture was stirred for 15 minutes at a temperature of 40°C. Then, 570 grams of C9 alkylated diphenylamine was added to the glass reactor, and the stirred mixture was cooled to 30°C in 20 minutes. Next, 67.5 grams of CO2 were added at a rate of 0.95 g / min over 71 minutes. The temperature rose from 30°C to 36°C. 113.8 grams of methanol, 106.8 grams of xylene solvent, and 113.8 grams of calcium hydroxide were charged into a beaker and stirred for several minutes to obtain a lime slurry. This lime slurry was charged into the reactor. Next, 56.4 grams of CO2 were introduced at a rate of 0.95 g / min over 59 minutes. The temperature rose from 36°C to 40°C. The first distillation step was then initiated under atmospheric pressure by heating the reactor from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 500 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, and the xylene was removed by distillation by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the device was cooled to ambient temperature.

[0125] Example 15 C9 alkylated diphenylamine In Example 15, alkylhydroxybenzoic acid was neutralized with lime, and then C9 alkylated diphenylamine was introduced.

[0126] 62 grams of methanol, 115.7 grams of xylene solvent, and 62 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0127] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% branched) was introduced. The mixture was stirred for 15 minutes at a temperature of 40°C. Then, 1100 grams of C9 alkylated diphenylamine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. 113.8 grams of methanol, 106.8 grams of xylene solvent, and 113.8 grams of calcium hydroxide were charged into a beaker and stirred for several minutes to obtain a lime slurry. This lime slurry was charged into the reactor. Subsequently, 56.4 grams of CO2 were introduced at a rate of 0.95 g / min over 59 minutes. The temperature rose from 30°C to 40°C. The first distillation step was then initiated under atmospheric pressure by heating the reactor from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes. During this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 500 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35000G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the mixture was cooled to ambient temperature.

[0128] Example 16 benzylamine In Example 16, alkylhydroxybenzoic acid was neutralized with lime, then benzylamine was introduced and reacted with CO2.

[0129] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0130] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 400 grams of benzylamine was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 20 minutes. Next, 164.3 grams of CO2 were introduced at a rate of 0.95 g / min over 173 minutes. The temperature rose from 30°C to 40°C. Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. Next, the product was subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0131] Example 17 urea In Example 17, alkylhydroxybenzoic acid was neutralized with lime, then urea was introduced and reacted with CO2.

[0132] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0133] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 1820.4 grams of alkylhydroxybenzoic acid (C14-16-18 alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 85 grams of urea was introduced into the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. Next, 62.3 grams of CO2 were introduced at a rate of 0.95 g / min over 67 minutes. The temperature rose from 30°C to 40°C. Subsequently, the reactor was heated from 40°C to 65°C in 15 minutes, then from 65°C to 93°C in 60 minutes, and then from 93°C to 128°C in 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene are vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0134] Example 18 Dimethylpiperazine In Example 18, alkylhydroxybenzoic acid was neutralized with lime, then dimethylpiperazine was introduced and reacted with CO2.

[0135] 100 grams of methanol, 222.5 grams of xylene solvent, and 100 grams of calcium hydroxide were placed in a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0136] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 150 grams of dimethylpiperazine was introduced into the glass reactor, and the stirred mixture was held at 40°C for 15 minutes and cooled to 30°C in 20 minutes. Subsequently, 11.6 grams of CO2 were introduced at a rate of 0.95 g / min over 13 minutes. The temperature rose from 30°C to 36°C. Next, 57.8 grams of CO2 were introduced at a rate of 0.95 g / min over 61 minutes. The temperature rose from 36°C to 60°C. Subsequently, the reactor was heated from 60°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0137] Example 19 Dimethylpiperazine In Example 19, alkylhydroxybenzoic acid was neutralized with lime, and then dimethylpiperazine was introduced.

[0138] 62 grams of methanol, 222.5 grams of xylene solvent, and 62 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0139] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical agitator with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the agitator blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) were added. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 150 grams of dimethylpiperazine were added to the glass reactor, and the stirred mixture was held at 40°C for 15 minutes and heated to 50°C in 30 minutes. Subsequently, the reactor was heated from 50°C to 65°C in 15 minutes, then from 65°C to 93°C in 60 minutes, and then from 93°C to 128°C in 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 425 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0140] Example 20 N-ethylbutylamine In Example 20, alkylhydroxybenzoic acid was neutralized with lime, then N-ethylbutylamine was introduced and reacted with CO2.

[0141] 100 grams of methanol, 222.5 grams of xylene solvent, and 100 grams of calcium hydroxide were placed in a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0142] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) were introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 200 grams of N-ethylbutylamine were introduced into the glass reactor and cooled to 30°C in 20 minutes. Next, 11.6 grams of CO2 were introduced at a rate of 0.95 g / min over 12 minutes. The temperature rose from 30°C to 34°C. Subsequently, 87 grams of CO2 were introduced at a rate of 0.95 g / min over 92 minutes. The temperature rose from 34°C to 60°C. Subsequently, the reactor was heated from 60°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0143] Example 21 N-ethylbutylamine In Example 21, alkylhydroxybenzoic acid was neutralized with lime, then N-ethylbutylamine was introduced and reacted with ethylene carbonate.

[0144] 100 grams of methanol, 222.5 grams of xylene solvent, and 100 grams of calcium hydroxide were placed in a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0145] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas introduction pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) was introduced. The mixture was stirred at a temperature of 40°C for 15 minutes. Then, 200 grams of N-ethylbutylamine was introduced into the glass reactor, and the mixture was held at 40°C for 15 minutes. Next, 433.9 grams of ethylene carbonate was introduced over 30 minutes. The temperature rose from 40°C to 50°C. The mixture was then held at 50°C for 15 minutes. Subsequently, the reactor was heated from 50°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0146] Example 22 N-ethylbutylamine In Example 22, alkylhydroxybenzoic acid was neutralized with lime, and then N-ethylbutylamine was introduced.

[0147] 65 grams of methanol, 222.5 grams of xylene solvent, and 65 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0148] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical agitator with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the agitator blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) were added. The mixture was stirred at 40°C for 15 minutes. Then, 290 grams of N-ethylbutylamine were added to the glass reactor, and the mixture was held at 40°C for 15 minutes. The temperature was raised from 40°C to 50°C over 30 minutes. Subsequently, the reactor was heated from 50°C to 65°C over 15 minutes, then from 65°C to 93°C over 60 minutes, and then from 93°C to 128°C over 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0149] Example 23 Isopropylmethylamine In Example 23, alkylhydroxybenzoic acid was neutralized with lime, and then isopropylmethylamine was introduced.

[0150] 62 grams of methanol, 222.5 grams of xylene solvent, and 62 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0151] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical agitator with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the agitator blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) were added. The mixture was stirred at 40°C for 15 minutes. Then, 250 grams of isopropylmethylamine were added to the glass reactor, and the mixture was held at 40°C for 15 minutes. The temperature was raised from 40°C to 50°C over 30 minutes. Subsequently, the reactor was heated from 50°C to 65°C over 15 minutes, then from 65°C to 93°C over 60 minutes, and then from 93°C to 128°C over 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 613.4 grams of 140N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C for 60 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0152] Example 24 C9 alkylated diphenylamine In Example 24, an alkyl or alkenyl aromatic sulfonic acid was neutralized with lime, and then a C9 alkylated diphenylamine was introduced and reacted with CO2.

[0153] 21 grams of methanol, 147.5 grams of xylene solvent, and 21 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0154] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet tube (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 313.4 grams of alkyl or alkenyl aromatic sulfonic acid (C20-24 alkyl or alkenyl aromatic sulfonic acid) was introduced over 15 minutes to 30°C. The mixture was then held at 30°C for 15 minutes. Next, 570 grams of C9 alkylated diphenylamine was introduced into the glass reactor, and the stirred mixture was held at 30°C for 40 minutes. Then, 67.5 grams of CO2 was introduced at a rate of 1.0 g / min over 68 minutes. The temperature rose from 30°C to 36°C. 90 grams of methanol, 200 grams of xylene solvent, and 90 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry. The lime slurry, previously prepared in a beaker, was charged into a glass reactor. Then, 48.8 grams of CO2 were introduced at a rate of 1.0 g / min over 49 minutes. The temperature rose from 36°C to 40°C. The first distillation step was then initiated under atmospheric pressure by heating the reactor from 40°C to 65°C over 15 minutes, then from 65°C to 93°C over 60 minutes, and then from 93°C to 128°C over 30 minutes. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 400 grams of 600N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35000G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 204°C. Xylene was removed by distillation by holding the product at 204°C under a vacuum of 30 mmHg for 10 minutes. The vacuum was broken with air, and the device was cooled to ambient temperature.

[0155] Example 25 C9 alkylated diphenylamine In Example 25, an alkyl or alkenyl aromatic sulfonic acid was neutralized with lime, and then a C9 alkylated diphenylamine was introduced.

[0156] 211 grams of methanol, 347.5 grams of xylene solvent, and 211 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0157] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 311.2 grams of alkyl or alkenyl aromatic sulfonic acid (C20-24 alkyl or alkenyl aromatic sulfonic acid) was introduced over 15 minutes to 30°C. The mixture was then held at 30°C for 15 minutes. Then, 800 grams of C9 alkylated diphenylamine was introduced into the glass reactor, and the stirred mixture was held at 30°C for 40 minutes. Subsequently, 92.8 grams of CO2 were introduced at a rate of 1.0 g / min over 93 minutes. The temperature rose from 30°C to 40°C.

[0158] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 390 grams of 600N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 204°C. Xylene was removed by distillation by holding the product at 204°C under a vacuum of 30 mmHg for 10 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0159] Example 26 1,4-Diazabicyclo[2.2.2]octane In Example 26, an alkyl or alkenyl aromatic sulfonic acid was neutralized with lime, and then 1,4-diazabicyclo[2.2.2]octane was introduced.

[0160] 21 grams of methanol, 247.5 grams of xylene solvent, and 21 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0161] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 305.8 grams of alkyl or alkenyl aromatic sulfonic acid (C20-24 alkyl or alkenyl aromatic sulfonic acid) was introduced over 15 minutes to 30°C. The temperature of the mixture was then raised from 30°C to 40°C over 20 minutes. Subsequently, 160 grams of 1,4-diazabicyclo[2.2.2]octane was introduced into the glass reactor, and the stirred mixture was held at 40°C for 20 minutes.

[0162] Subsequently, the reactor was heated from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 400 grams of 600N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 204°C. Xylene was removed by distillation by holding the product at 204°C for 10 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0163] Example 27 Alkylated diphenylamine In Example 27, the C9 alkylated diphenylamine was introduced after the formation of calcium carbonate and the neutralization of the alkyl or alkenyl aromatic sulfonic acid with lime.

[0164] 211 grams of methanol, 347.5 grams of xylene solvent, and 211 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0165] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 311.2 grams of alkyl or alkenyl aromatic sulfonic acid (C20-24 alkyl or alkenyl aromatic sulfonic acid) was introduced over 15 minutes until the temperature reached 32°C. The mixture was then cooled to 25°C. Subsequently, 92.8 grams of CO2 were introduced at a rate of 1.0 g / min over 93 minutes. The temperature rose from 25°C to 32°C.

[0166] Subsequently, 800 grams of C9 alkylated diphenylamine were introduced into a glass reactor over 15 minutes, and the reactor was cooled to 30°C.

[0167] Subsequently, 94.7 grams of CO2 were introduced at a rate of 1.0 g / min over 95 minutes. The temperature rose from 30°C to 41°C.

[0168] Subsequently, the reactor was heated from 41°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 390 grams of 600N lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 204°C. Xylene was removed by distillation by holding the product at 204°C for 10 minutes under a vacuum of 30 mmHg. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0169] Example 28 2-Phenoxyethylamine In Example 28, alkylhydroxybenzoic acid was neutralized with lime, and then 2-phenoxyethylamine was introduced.

[0170] 12.7 grams of methanol, 54.7 grams of xylene, and 19.3 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0171] The lime slurry was charged into a 1 L glass reactor equipped with a stainless steel mechanical stirrer with a heating function that rotated at 350 rpm, a CO2 addition gas spray tube located directly above the stirring blades, a Claisen tube, and a condenser. Next, 200 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) was added dropwise over 15 minutes. The mixture was stirred at a temperature of 40°C for 15 minutes. Next, 23.9 grams of 2-phenoxyethylamine was added to the glass reactor, and the mixture was held at 40°C for 15 minutes. During this holding time, a mixture of 30.7 grams of methanol, 121.3 grams of xylene, and 46.4 grams of calcium hydroxide was stirred in a beaker to obtain a second lime slurry. Over the next 156 minutes, of the 29.2 grams of CO2, 1.7 grams were supplied to the reactor via a glass spray tube over 11 minutes at 40°C, 14.5 grams over 76 minutes from 40°C to 53°C, and finally 13.0 grams over 69 minutes from 53°C to 58°C, while the slurry was dripped into the glass reactor using a peristaltic pump.

[0172] Subsequently, the reactor was heated from 58°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 69.2 grams of 100R lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 10,000 RPM to separate the insoluble solid product. The liquid portion was returned to the 1 L reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0173] Example 29 C20-24 alkylated 2-phenoxyethylamine In Example 29, alkylhydroxybenzoic acid was neutralized with lime, and then C20-24 alkylated phenoxyethylamine was introduced.

[0174] 12.7 grams of methanol, 54.7 grams of xylene, and 19.3 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0175] The lime slurry was charged into a 1 L glass reactor equipped with a stainless steel mechanical stirrer with a heating function that rotated at 350 rpm, a CO2 addition gas spray tube located directly above the stirring blades, a Claisen tube, and a condenser. Next, 200 grams of alkylhydroxybenzoic acid (C20-24, 23% isomerized alkylhydroxybenzoic acid) was added dropwise over 15 minutes. The mixture was stirred at a temperature of 40°C for 15 minutes. Next, 74.9 grams of C20-24 alkylated 2-phenoxyethylamine was added to the glass reactor, and the mixture was held at 40°C for 15 minutes. During this holding time, a mixture of 30.7 grams of methanol, 121.3 grams of xylene, and 46.4 grams of calcium hydroxide was stirred in a beaker to obtain a second lime slurry. Over the next 156 minutes, of the 29.2 grams of CO2, 1.7 grams were supplied to the reactor via a glass spray tube over 11 minutes at 40°C, 14.5 grams over 76 minutes from 40°C to 53°C, and finally 13.0 grams over 69 minutes from 53°C to 58°C, while the slurry was dripped into the glass reactor using a peristaltic pump.

[0176] Subsequently, the reactor was heated from 58°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes to initiate the first distillation step under atmospheric pressure. At this stage, methanol, water, and some metaxylene were vaporized. At the end of this distillation step, 69.2 grams of 100R lubricating oil were charged into the reactor. The product was then subjected to a laboratory centrifuge operating at 10,000 RPM to separate the insoluble solid product. The liquid portion was returned to the 1 L reactor, and the product was heated to 170°C, where xylene was distilled off by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0177] Example 30 C9 alkylated diphenylamine and glycine In Example 30, alkylhydroxybenzoic acid was neutralized with lime. Subsequently, after neutralizing the benzoic acid, 16 grams of glycine were introduced into the reactor. Then, C9 alkylated diphenylamine was introduced.

[0178] 70 grams of methanol, 130.6 grams of xylene solvent, and 70 grams of calcium hydroxide were charged into a beaker. The mixture was stirred for several minutes to obtain a lime slurry.

[0179] The lime slurry was charged into a glass reactor equipped with a stainless steel mechanical stirrer with heating and cooling functions, rotating at 350 rpm, a CO2 addition gas inlet pipe (2 mm inner diameter) located directly above the stirring blades, a distillation column, and a condenser. Next, 2007.5 grams of alkylhydroxybenzoic acid (C20-24, branched up to 23%) was added. The mixture was stirred at 40°C for 15 minutes. Then, 16 grams of glycine was added. The reactor was maintained at 43°C for 15 minutes. After that, 835 grams of C9 alkylated diphenylamine was added to the glass reactor, and the stirred mixture was cooled to 30°C in 15 minutes. 113.8 grams of methanol, 106.8 grams of xylene solvent, and 113.8 grams of calcium hydroxide were charged into a beaker and stirred for several minutes to obtain a lime slurry. This lime slurry was charged into the reactor. Subsequently, 56.4 grams of CO2 were introduced at a rate of 0.95 g / min over 59 minutes. The temperature rose from 30°C to 40°C. The first distillation step was then initiated under atmospheric pressure by heating the reactor from 40°C to 65°C for 15 minutes, then from 65°C to 93°C for 60 minutes, and then from 93°C to 128°C for 30 minutes. At this stage, methanol, water, and some metaxylene were vaporized. The product was then subjected to a laboratory centrifuge operating at 35,000 G to separate the insoluble solid product. The liquid portion was charged into a 4-liter round-bottom reactor, and the product was heated to 170°C. Xylene was removed by distillation by holding the product at 170°C under a vacuum of 30 mmHg for 60 minutes. The vacuum was broken with air, and the product was cooled to ambient temperature.

[0180] Comparative Examples A and B Comparative Example A is calcium salicylate (TBN175) without amine treatment.

[0181] Comparative Example B is calcium salicylate (TBN421) without amine treatment.

[0182] Tables 1 and 2 summarize the disclosed examples.

[0183] Table 3 summarizes the airtightness test results for Comparative Example A and Examples 3, 9, and 13 of the formulated engine oil (15W-40 grade). To ensure proper testing, the samples were formulated to include the same TBN level and the same SOAP content (measured organic acid metal salt content). [Table 1]

[0184] HTCBT ASTM D6594 The ASTM D6594 HTCBT test is used to test diesel engine lubricants and determine their tendency to corrode various metals, particularly lead-copper alloys commonly used in cam followers and bearings. Four metal samples—copper, lead, tin, and phosphor bronze—are immersed in a measured amount of engine oil. The oil, heated to a high temperature (170°C), is then sprayed with air (5 l / h) for a set period (168 hours). After the test, the copper test piece and the stressed oil are inspected to detect corrosion and corrosion products. The concentrations of copper, lead, and tin in the new and stressed oil, as well as the changes in the concentrations of each metal, are reported. To pass the test, the lead concentration must not exceed 120 ppm and the copper concentration must not exceed 20 ppm. [Table 2] [Table 3]

[0185] For the sake of brevity, this specification explicitly discloses only certain ranges. However, ranges from any lower bound may be combined with any upper bound to enumerate ranges not explicitly described, and similarly, ranges from any lower bound may be combined with other arbitrary lower bounds to enumerate ranges not explicitly described, and similarly, ranges from any upper bound may be combined with other arbitrary upper bounds to enumerate ranges not explicitly described. Furthermore, ranges include all points or individual values ​​between their endpoints, even if not explicitly listed. Thus, all points or individual values, combined with other points or individual values, or with other lower or upper bounds, may function as their own lower or upper bounds, enumerating ranges not explicitly described.

[0186] Similarly, the term “comprising” is considered synonymous with the term “including.” Likewise, whenever there is a transitional phrase “comprising” before a composition, element, or group of elements, it is understood that the description of that composition, element, or group of elements also assumes the same composition or group of elements that is preceded by a transitional phrase “essentially includes,” “consisting of,” “selected from the group including,” or “is,” and vice versa.

[0187] As used herein, the terms "a" and "the" are understood to include both singular and plural forms.

[0188] Various terms are defined above. To the extent that a term used in a claim is not defined above, the broadest definition given to that term by experts in the relevant art should be provided, as reflected in at least one printed publication or issued patent. Furthermore, all patents, test methods, and other documents cited in this application shall be fully incorporated by reference, to the extent that such disclosure does not conflict with this application and in all jurisdictions where such incorporation is permitted. The following is further disclosed regarding the present invention. [1] A process for preparing a low-ash cleaning material, The process comprising mixing a surfactant composition containing a hydroxybenzoate, sulfonate, or phosphonate cleaning agent with an ash-free nitrogen-containing compound to enhance the base value of the hydroxybenzoate, sulfonate, or phosphonate cleaning agent. [2] The process according to [1], wherein the mixing is carried out in the presence of carbon dioxide or ethylene carbonate. [3] The process according to [1], wherein the mixture neutralizes the hydroxybenzoate, sulfonate, or phosphonate cleaning agent. [4] The process according to [1], wherein the hydroxybenzoate, sulfonate, or phosphonate cleaning agent is neutralized by a metal base before or during the mixing. [5] The aforementioned metal base is Ca(OH) 2 The process described in [4], or MgO. [6] The process according to [1], wherein the nitrogen-containing compound is an alkylated amine, hydrocarbylamine, ethyleneamine, aromatic amine, ethanolamine, urea, diphenylamine, alkylated diphenylamine, benzylamine, piperazine, alkylpiperazine, dialkylpiperazine, phenoxyamine, benzamide, phenylamine, phthalimide, or an amino acid. [7] The nitrogen-containing compounds include C9 diphenylamine, 2-ethylhexyl(fat)methylamine, ethylhexylamine, octylamine, ethylenediamine, N-methylethanolamine, 1,1-dimethylethylenediamine, 2-methoxyethylamine, diethanolamine, N-methylpropylenediamine, tetramethylurea, N-phenylphenylenediamine, triethylenetetraamine, triethanolamine, 1,4-diazabicyclo[2.2.2]-octane, N,N'-bis(3-aminopropyl)ethylenediamine, 2-phenoxyethylamine, C20-C24 alkyl-2-phenyl The process described in [1], wherein the material is noxyamine, 2-(2-aminoethoxy)naphthalene, N-(3-(dimethylamino)propyl)benzamide, phenylpropylamine, N-(2-hydroxyethyl)phthalimide, N-(2-aminoethyl)phthalimide, N-(3-hydroxypropyl)phthalimide, N-(3-aminopropyl)phthalimide, N-(2-(methylamino)ethyl)phthalimide, N-(3-(methylamino)propyl)phthalimide, N-(2-(dimethylamino)ethyl)phthalimide, N-(3-(dimethylamino)propyl)phthalimide, or glycine. [8] The process according to [1], wherein the surfactant is a salt of an alkyl hydroxybenzoic acid, an alkyl aromatic sulfonic acid, or an alkenyl aromatic sulfonic acid. [9] The process according to [1], wherein the mixing is performed before or after the formation of the metal carbonate.

[10] A process for preparing a low-ash cleaning material, The process comprises mixing a hydroxybenzoate, sulfonate, or phosphonate cleaning agent with an amine or amine derivative, wherein the amine or amine derivative is added to overbase or enhance the base value of the hydroxybenzoate, sulfonate, or phosphonate cleaning agent.

[11] The process according to

[10] , wherein the mixing is carried out in the presence of carbon dioxide.

[12] The process according to

[10] , wherein the mixture neutralizes the hydroxybenzoate, sulfonate, or phosphonate cleaning agent.

[13] The process according to

[10] , wherein the hydroxybenzoate, sulfonate, or phosphonate cleaning agent is neutralized by a metal base before or during the mixing.

[14] The aforementioned metal base is Ca(OH) 2 The process described in

[13] , or MgO.

[15] The process according to

[10] , wherein the amine or amine derivative is an alkylated amine, hydrocarbylamine, ethyleneamine, aromatic amine, ethanolamine, urea, diphenylamine, alkylated diphenylamine, benzylamine, piperazine, alkylpiperazine, dialkylpiperazine, phenoxyamine, benzamide, phenylamine, phthalimide, or an amino acid.

[16] The amine or amine derivative is C9 diphenylamine, 2-ethylhexyl(fat)methylamine, ethylhexylamine, octylamine, ethylenediamine, N-methylethanolamine, 1,1-dimethylethylenediamine, 2-methoxyethylamine, diethanolamine, N-methylpropylenediamine, tetramethylurea, N-phenylphenylenediamine, triethylenetetraamine, triethanolamine, 1,4-diazabicyclo[2.2.2]-octane, N,N'-bis(3-aminopropyl)ethylenediamine, 2-phenoxyethylamine, C20-C24 alkyl-2- The process according to

[10] , wherein the material is phenoxyamine, 2-(2-aminoethoxy)naphthalene, N-(3-(dimethylamino)propyl)benzamide, phenylpropylamine, N-(2-hydroxyethyl)phthalimide, N-(2-aminoethyl)phthalimide, N-(3-hydroxypropyl)phthalimide, N-(3-aminopropyl)phthalimide, N-(2-(methylamino)ethyl)phthalimide, N-(3-(methylamino)propyl)phthalimide, N-(2-(dimethylamino)ethyl)phthalimide, N-(3-(dimethylamino)propyl)phthalimide, or glycine.

[17] The process according to

[10] , wherein the surfactant is a salt of an alkyl hydroxybenzoic acid, an alkyl aromatic sulfonic acid, or an alkenyl aromatic sulfonic acid.

[18] The process according to

[10] , wherein the mixing is performed before or after the formation of the metal carbonate.

[19] Lubricating oil with a major amount of viscosity; and, A small amount of low-ash cleaning agent produced by a process comprising mixing a hydroxybenzoate, sulfonate, or phosphonate cleaning agent with an amine or amine derivative. A lubricating oil composition comprising, The lubricating oil composition wherein the amine or amine derivative is added to overbase or enhance the base number of the hydroxybenzoate, sulfonate, or phosphonate detergent.

[20] The lubricating oil composition according to

[19] , wherein the mixing is carried out in the presence of carbon dioxide.

[21] The lubricating oil composition according to

[19] , wherein the mixture neutralizes the hydroxybenzoate, sulfonate, or phosphonate detergent.

[22] The lubricating oil composition according to

[19] , wherein the hydroxybenzoate, sulfonate, or phosphonate cleaning agent is neutralized by a metal base before or during the mixing.

[23] The aforementioned metal base is Ca(OH) 2 The lubricating oil composition according to

[19] , which is MgO or otherwise.

[24] The lubricating oil composition according to

[19] , wherein the amine or amine derivative is an alkylated amine, hydrocarbylamine, ethyleneamine, aromatic amine, ethanolamine, urea, diphenylamine, alkylated diphenylamine, benzylamine, piperazine, alkylpiperazine, dialkylpiperazine, phenoxyamine, benzamide, phenylamine, phthalimide, or an amino acid.

[25] The amine or amine derivative is C9 diphenylamine, 2-ethylhexyl(fat)methylamine, ethylhexylamine, octylamine, ethylenediamine, N-methylethanolamine, 1,1-dimethylethylenediamine, 2-methoxyethylamine, diethanolamine, N-methylpropylenediamine, tetramethylurea, N-phenylphenylenediamine, triethylenetetraamine, triethanolamine, 1,4-diazabicyclo[2.2.2]-octane, N,N'-bis(3-aminopropyl)ethylenediamine, 2-phenoxyethylamine, C20-C24 alkyl-2- The lubricating oil composition according to

[19] , wherein the composition is phenoxyamine, 2-(2-aminoethoxy)naphthalene, N-(3-(dimethylamino)propyl)benzamide, phenylpropylamine, N-(2-hydroxyethyl)phthalimide, N-(2-aminoethyl)phthalimide, N-(3-hydroxypropyl)phthalimide, N-(3-aminopropyl)phthalimide, N-(2-(methylamino)ethyl)phthalimide, N-(3-(methylamino)propyl)phthalimide, N-(2-(dimethylamino)ethyl)phthalimide, N-(3-(dimethylamino)propyl)phthalimide, or glycine.

[26] The lubricating oil composition according to

[19] , wherein the surfactant is a salt of alkyl hydroxybenzoic acid, alkyl aromatic sulfonic acid, or alkenyl aromatic sulfonic acid.

[27] The lubricating oil composition according to

[19] , wherein the mixing is performed before or after the formation of the metal carbonate.

[0189] The above description of the Disclosure is illustrative and illustrative. Furthermore, while the Disclosure illustrates and describes only preferred embodiments, as stated above, the Disclosure is applicable in a variety of other combinations, modifications, and environments, and it should be understood that changes or modifications are possible within the scope of the concepts expressed herein to match the art or knowledge of the above teachings and / or related art. Although the above is directed toward embodiments of the Disclosure, other further embodiments of the Disclosure can be devised without departing from its basic scope, the scope of which will be determined by the claims that follow.

Claims

1. A process for preparing a low-ash cleaning material, The process comprises mixing a hydroxybenzoate cleaning agent with an amine or amine derivative, wherein the amine or amine derivative is added to overbase or enhance the base value of the hydroxybenzoate cleaning agent, The process wherein the hydroxybenzoate cleaning agent is an alkylhydroxybenzoate derived from an isomerized α-olefin having 14 to 28 carbon atoms and an isomerization level of 0.1 to 0.

4.

2. The process according to claim 1, wherein the mixing is carried out in the presence of carbon dioxide.

3. The process according to claim 1, wherein the mixture neutralizes the hydroxybenzoate cleaning agent.

4. The process according to claim 1, wherein the hydroxybenzoate cleaning agent is neutralized by a metal base before or during the mixing.

5. The aforementioned metal base is Ca(OH) ２ The process according to claim 4, wherein the material is MgO.

6. The process according to claim 1, wherein the amine or amine derivative is an alkylated amine, hydrocarbylamine, ethyleneamine, aromatic amine, ethanolamine, urea, diphenylamine, alkylated diphenylamine, benzylamine, piperazine, alkylpiperazine, dialkylpiperazine, phenoxyamine, benzamide, phenylamine, phthalimide, or an amino acid.

7. The amine or amine derivative is C9 diphenylamine, 2-ethylhexyl(fat)methylamine, ethylhexylamine, octylamine, ethylenediamine, N-methylethanolamine, 1,1-dimethylethylenediamine, 2-methoxyethylamine, diethanolamine, N-methylpropylenediamine, tetramethylurea, N-phenylphenylenediamine, triethylenetetraamine, triethanolamine, 1,4-diazabicyclo[2.2.2]-octane, N,N'-bis(3-aminopropyl)ethylenediamine, 2-phenoxyethylamine, C20-C24 alkyl-2- The process according to claim 1, wherein the material is phenoxyamine, 2-(2-aminoethoxy)naphthalene, N-(3-(dimethylamino)propyl)benzamide, phenylpropylamine, N-(2-hydroxyethyl)phthalimide, N-(2-aminoethyl)phthalimide, N-(3-hydroxypropyl)phthalimide, N-(3-aminopropyl)phthalimide, N-(2-(methylamino)ethyl)phthalimide, N-(3-(methylamino)propyl)phthalimide, N-(2-(dimethylamino)ethyl)phthalimide, N-(3-(dimethylamino)propyl)phthalimide, or glycine.

8. The process according to claim 1, wherein the mixing is performed before or after the formation of the metal carbonate.

9. Lubricating oil with a major amount of viscosity; and, A small amount of low-ash cleaning agent produced by a process involving mixing a hydroxybenzoate cleaning agent with an amine or amine derivative. A lubricating oil composition comprising, The lubricating oil composition is characterized in that the amine or amine derivative is added to overbase or enhance the base value of the hydroxybenzoate detergent, The lubricating oil composition wherein the hydroxybenzoate cleaning agent is an alkylhydroxybenzoate derived from an isomerized α-olefin having 14 to 28 carbon atoms and an isomerization level of 0.1 to 0.

4.

10. The lubricating oil composition according to claim 9, wherein the mixing is carried out in the presence of carbon dioxide.

11. The lubricating oil composition according to claim 9, wherein the mixture neutralizes the hydroxybenzoate detergent.

12. The lubricating oil composition according to claim 9, wherein the hydroxybenzoate cleaning agent is neutralized by a metal base before or during the mixing.

13. The aforementioned metal base is Ca(OH) ２ The lubricating oil composition according to claim 12, wherein the lubricating oil is MgO.

14. The lubricating oil composition according to claim 9, wherein the amine or amine derivative is an alkylated amine, hydrocarbylamine, ethyleneamine, aromatic amine, ethanolamine, urea, diphenylamine, alkylated diphenylamine, benzylamine, piperazine, alkylpiperazine, dialkylpiperazine, phenoxyamine, benzamide, phenylamine, phthalimide, or an amino acid.

15. The amine or amine derivative is C9 diphenylamine, 2-ethylhexyl(fat)methylamine, ethylhexylamine, octylamine, ethylenediamine, N-methylethanolamine, 1,1-dimethylethylenediamine, 2-methoxyethylamine, diethanolamine, N-methylpropylenediamine, tetramethylurea, N-phenylphenylenediamine, triethylenetetraamine, triethanolamine, 1,4-diazabicyclo[2.2.2]-octane, N,N'-bis(3-aminopropyl)ethylenediamine, 2-phenoxyethylamine, C20-C24 alkyl-2- The lubricating oil composition according to claim 9, wherein the composition is phenoxyamine, 2-(2-aminoethoxy)naphthalene, N-(3-(dimethylamino)propyl)benzamide, phenylpropylamine, N-(2-hydroxyethyl)phthalimide, N-(2-aminoethyl)phthalimide, N-(3-hydroxypropyl)phthalimide, N-(3-aminopropyl)phthalimide, N-(2-(methylamino)ethyl)phthalimide, N-(3-(methylamino)propyl)phthalimide, N-(2-(dimethylamino)ethyl)phthalimide, N-(3-(dimethylamino)propyl)phthalimide, or glycine.

16. The lubricating oil composition according to claim 9, wherein the mixing is performed before or after the formation of the metal carbonate.

Images