JP5558486B2 - Lubricating oil additive composition and method for producing the same - Google Patents

Description

  The present invention relates to an improved dispersant composition for use in engine oils and also relates to a method for producing the same.

  It is known to use nitrogen-containing dispersants and / or detergents in the formulation of lubricating oil compositions. A number of known detergent dispersant compounds are based on reacting an alkenyl succinic acid or anhydride with an amine or polyamine to produce an alkenyl succinimide or alkenyl succinamic acid as determined by selected reaction conditions. Yes. One problem faced by lubricant manufacturers is the dispersibility of particulate matter in internal combustion engines. Failure to obtain sufficient particulate dispersibility can result in filter clogging, sludge accumulation, and oil thickening.

  The combination of certain aromatic anhydrides with ethylene post-treated dispersants has been found to provide improved dispersibility, as shown in the soot thickening bench test and diesel engine fuel injector flow loss improvement test. It was issued.

  In Patent Document 1, (i) at least one polyamine is at least one acyclic hydrocarbon-substituted succinic acylating agent, and the acyclic hydrocarbon substituent contains an average of at least 40 carbon atoms. Reacting with an acylating agent, provided that the reaction is carried out using a ratio such that the acylating agent reacts with the polyamine at a molar ratio of 1.05 to 2.85 moles per mole of polyamine, and (ii) (A) at least one aliphatic adjacent dicarboxylic acid acylation containing 4 to 30 carbon atoms in the molecule and two carboxyl groups separated from each other by two aliphatic carbon atoms. Reaction with an agent, or (b) an anhydride, acid halide or ester of at least one dicarboxylic acylating agent, or (c) a combination of (a) and (b). Provided that the reaction of (ii) uses a ratio such that the molar ratio of the acylating agent is 0.10 to 2.50 moles per mole of the polyamine, wherein the acyls of (i) and (ii) There is disclosed a lubricating oil comprising a dispersant produced by subjecting the total molar ratio of the agent to be in the range of 2.40 to 4.50 per mole of the polyamine.

  Patent Document 2 discloses (a) polybasic aromatic carboxylic acids (phthalic acid, terephthalic acid, trimesic acid, trimellitic acid, pyromellitic acid, etc.) and anhydrides thereof, and (b) alkenyl having a molecular weight of about 300-3000. The alkenyl succinic acid having an attached group or an anhydride thereof and (c) a polyalkylene polyamine are treated at a molar ratio of (a) :( b) :( c) = 1: 1-4: 1-4, A lubricating oil composition produced by adding an effective amount of a reaction product having a mass ratio of boron to nitrogen of about 0.05-1 obtained by treating the intermediate obtained in FIG. It is disclosed.

  Patent Document 3 discloses a lubricating oil composition containing an amine carboxylic acid product.

  Patent Document 4 discloses a nitrogen-containing composition obtained from the reaction of an amine with a monocarboxylic acid and a high molecular weight carboxylic acid such as alkylene or arylene dicarboxylic acid.

  Patent Document 5 discloses terephthalic acid dispersed in a hydrocarbon medium containing acylated alkylenepolyamines having a high degree of steric hindrance.

  Patent Document 6 discloses (1) a product obtained by reacting an alkenyl succinimide with an aromatic dianhydride, or (2) an alkenyl succinimide and a low molecular weight fat. Products obtained by reacting anhydrides or dianhydrides of aromatic, cycloaliphatic or aromatic mono- or polycarboxylic acids, but the product obtained is An additive composition is disclosed which is reacted with at least one organic compound having a group and / or an amine group. These dispersion additive compositions can be added to the lubricating oil at a ratio of, for example, 0.1 to 20% by mass.

  Patent Document 7 discloses an oil-soluble dispersant obtained by reacting a reaction product of a polyamine with a long-chain hydrocarbon-substituted dicarboxylic acid, its anhydride or ester with a polyanhydride, and containing 2% w / w Active substance and shear rate upper limit 0.26 s-1 Pa. s, the viscosity increase of the oil was 8 Pa.s. Dispersants characterized by being limited to less than s, and lubricating oil and fuel compositions and additive concentrates containing such dispersants are disclosed.

  Patent Document 8 includes (A) (i) at least one substantially aliphatic polymer of at least one lower olefin, and (ii) a general formula wherein R and R ′ are independently —OH, Reacting with an acidic reactant or a mixture of two or more acidic reactants represented by -O-lower alkyl, a halogen atom, or a single oxygen atom together, and (B ) Succinimides and succinates by reacting an acylating agent with at least one alcohol (preferably a polyhydric alcohol) or amine (preferably a polyamine having at least one primary amino group). And the production of succinate amides.

  Patent Document 9 discloses polyaminoalkenyl or alkyl succinimides containing carbamate functional groups that can be used as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic fluids.

  Patent Document 10 discloses polyaminoalkenyl or alkyl succinimides containing carbamate functional groups that can be used as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic fluids.

  Patent Document 11 discloses a reaction product of a high molecular weight alkenyl or alkyl-substituted succinic anhydride and a polyalkylene polyamine having an average of more than 4 nitrogen atoms per mole, which is post-treated with a cyclic carbonate. Alkenyl or alkyl succinimide additives that are compatible with fluorocarbon engine seals and have improved dispersion and / or cleaning properties when used in lubricating oils and fuels at concentration levels to obtain fluorocarbon seal compatibility Is disclosed.

  Patent Document 12 discloses a reaction product of a high molecular weight alkenyl or alkyl-substituted succinic anhydride and a polyalkylene polyamine having an average of more than 4 nitrogen atoms per mole, which is post-treated with a cyclic carbonate. Alkenyl or alkyl succinimide additives that are compatible with fluoroelastomer engine seals and used in chlorine-free lubricating oils at a concentration level to obtain fluoroelastomer seal compatibility can improve dispersion and / or cleaning properties. It is disclosed that there is.

  In Patent Document 13, a mixture of an alkenyl or alkyl succinic acid derivative, an unsaturated acidic reagent copolymer and a polyamine is reacted under reaction conditions, and then the reaction product is a cyclic carbonate, linear mono- or polycarbonate, or boron compound. In any case, it is disclosed that a succinimide composition is produced by treatment under reaction conditions.

  In Patent Document 14, a copolymer of a first unsaturated acidic reagent and a 1,1-disubstituted olefin, a second unsaturated acidic reagent and a copolymer of 1-olefin, and a polyamine are reacted under reaction conditions. After reacting, it is disclosed to produce a polysuccinimide composition by treating the reaction product with a cyclic carbonate, linear mono or polycarbonate or boron compound under reaction conditions.

  Patent Document 15 discloses that a succinimide composition is produced by reacting a mixture of an alkenyl or alkyl succinic acid derivative, an unsaturated acidic reagent copolymer and a polyamine under reaction conditions.

  In Patent Document 16, after reacting a mixture of an alkenyl or alkyl succinic acid derivative, an unsaturated acidic reagent copolymer and a polyamine under reaction conditions, the reaction product is a cyclic carbonate, linear mono- or polycarbonate, or boron compound. In any case, it is disclosed that a succinimide composition is produced by treatment under reaction conditions.

  Patent Document 17 discloses a method for producing a mixture of (1) a copolymer of a polyalkene and an unsaturated acidic reagent, and (2) a polyalkenyl derivative of an unsaturated acidic reagent, comprising (a) (1) an alkyl (B) copolymerizing a polyalkene containing a vinylidene isomer and a non-alkyl vinylidene isomer with an unsaturated acidic reagent in the presence of a radical initiator under polymerization conditions; and (b) the product of step (a). It is disclosed to provide a method comprising reacting with an unsaturated acidic reagent at an elevated temperature in the presence of a strong acid.

  In US Pat. No. 6,057,059, an alkenyl or alkyl succinimide was treated with an oil-soluble strong acid and the treated succinimide was contacted with a cyclic carbonate to produce a non-cloudy post-treated succinimide. A non-cloudy post-treated succinimide is disclosed.

European Patent Application No. 0438848 JP 51-130408 A US Pat. No. 3,287,271, Stuart, et al. US Pat. No. 3,374,174, Rusur US Pat. No. 3,696,2681, Liston U.S. Pat. No. 4,747,964, Durand, et al. US Pat. No. 6,255,258, Clark, et al. US Pat. No. 524,003, Digonia, outside U.S. Pat. No. 4,612,132 Ullenberg, et al. U.S. Pat. No. 4,747,850, Ullenberg, et al. US Pat. No. 5,334,321, Harrison, et al. US Pat. No. 5,356,552, Harrison, et al. US Pat. No. 5,716,912, Harrison, et al. US Pat. No. 5,753,597, Harrison, et al. US Pat. No. 5,889,676, Harrison, et al. US Pat. No. 6,358,892, Harrison, et al. US Pat. No. 6,451,920, Harrison, et al. US Pat. No. 6,214,775, Harrison

  The present invention relates to an improved dispersant composition for use in engine oils and also relates to a method for producing the same.

In its broadest aspect, the present invention provides:
A lubricating oil additive composition produced by a method comprising the following steps:
(A) reacting polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms, thereby producing succinimide or succinamide or a mixture thereof. ,
(B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof, whereby the first post-treated succinimide or succinamide or a mixture thereof And (C) reacting the product of step (B) with a cyclic carbonate, thereby producing a final post-treated succinimide or succinamide or mixture thereof, provided that the final At least one basic nitrogen remains in the post-treated succinimide or succinamide or a mixture thereof.

The present invention also provides:
It also relates to a lubricating oil composition comprising a major amount of oil of lubricating viscosity and a small amount of lubricating oil additive composition produced by a process comprising the following steps:
(A) reacting polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms, thereby producing succinimide or succinamide or a mixture thereof. ,
(B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof, whereby the first post-treated succinimide or succinamide or a mixture thereof And (C) reacting the product of step (B) with a cyclic carbonate, thereby producing a final post-treated succinimide or succinamide or mixture thereof, provided that the final At least one basic nitrogen remains in the post-treated succinimide or succinamide or a mixture thereof.

The present invention also provides
It also relates to a method for producing a lubricating oil additive composition comprising the following steps:
(A) reacting polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms, thereby producing succinimide or succinamide or a mixture thereof. ,
(B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof, whereby the first post-treated succinimide or succinamide or a mixture thereof And (C) reacting the product of step (B) with a cyclic carbonate, thereby producing a final post-treated succinimide or succinamide or mixture thereof, provided that the final At least one basic nitrogen remains in the post-treated succinimide or succinamide or a mixture thereof.

  Accordingly, the present invention relates to a multifunctional lubricant additive useful as a dispersant in internal combustion engines.

  While the invention is susceptible to various modifications and alternative forms, specific details of the invention are described in detail herein. However, the description herein of specific embodiments is not intended to limit the invention to the particular forms disclosed, but on the contrary, the invention is not limited to the invention as defined by the appended claims. All modifications, equivalents, and alternatives that fall within the spirit and scope are intended to be embraced.

[Definition]
The following terms used in the description are defined as follows.

  “PIB” is an abbreviation for polyisobutene.

  “PIBSA” is an abbreviation for polyisobutenyl succinic anhydride.

  The “succinic acid group” means a group having the following formula.

  In the formula, W and Z are independently selected from the group consisting of —OH, —Cl, —O-lower alkyl, or are together —O— to form a succinic anhydride group. “—O-lower alkyl” means that alkoxy having 1 to 6 carbon atoms is included.

  “Succinimide” is understood in the art to include a number of amides, imides, and the like, as well as those formed by the reaction of succinic anhydride and amines. However, the main product is succinimide, and this term is generally taken to mean the product of the reaction of an alkenyl or alkyl substituted succinic acid or anhydride with an amine. Alkenyl or alkyl succinimides are disclosed in numerous references and are well known in the art. For certain basic types of succinimides and related substances included in the technical term “succinimide”, see US Pat. Nos. 2,992,708, 3,018,291, 3024237, 3100673, 3,219,666, Nos. 3172892 and 3272746 are taught, and the disclosures thereof are also incorporated herein by reference.

  “Alkenyl or alkyl succinic acid derivative” means a structure having the formula:

  Wherein L and M are independently selected from the group consisting of —OH, —Cl, —O-lower alkyl, or together are —O— to form an alkenyl or alkyl succinic anhydride group. ing.

  “Soluble in lubricating oil” means the ability of a substance to dissolve in aliphatic and aromatic hydrocarbons, such as lubricating oils and fuels, in essentially any proportion.

  “High molecular weight olefins” means olefins (including polymerized olefins with residual unsaturation) having a molecular weight and chain length sufficient to render their reaction products soluble in lubricating oils. In general, olefins having about 30 or more carbon atoms are sufficient.

  “Alkyl” means both straight and branched chain alkyl groups.

  “Polyalkyl” means an alkyl group generally derived from mono-olefins, especially 1-mono-olefins, for example polyolefins which are polymers or copolymers such as ethylene, propylene and butylene. Preferably, the mono-olefin used has 2 to about 24 carbon atoms, more preferably about 3 to 12 carbon atoms. More preferred mono-olefins include propylene, butylene, especially isobutylene, 1-octene, and 1-decene. Preferred polyolefins made from such mono-olefins include polypropylene, polybutene, especially polyisobutene.

  “Basic nitrogen” means a nitrogen atom capable of accepting a proton.

  Both “alkenyl succinic acid or anhydride” and “alkyl succinic acid or anhydride” can be used.

  One aspect of the present invention is a post-treated oil-soluble lubricating oil additive composition. In one embodiment, the composition is made by a process comprising the steps of: (A) reacting a polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms. Step thereby producing succinimide or succinamide or a mixture thereof, (B) reacting the product of step (A) with a first post-treatment agent, whereby the first post-treated succinic acid Forming an imide or succinamide or a mixture thereof, and (C) reacting the product of step (B) with a second post-treatment agent, whereby the final post-treated succinimide or succinic acid Forming an amide or a mixture thereof, provided that the final post-treated succinimide or succinamide or a mixture thereof The object, the basic nitrogen is left at least one.

  In one embodiment, the composition is made by a process comprising the steps of: (A) reacting a polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms. Step of producing succinimide or succinamide or a mixture thereof, (B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof; Producing a first post-treated succinimide or succinamide or a mixture thereof, and (C) reacting the product of step (B) with a cyclic carbonate, whereby the final post-treated succinic acid Producing an acid imide or succinamide or a mixture thereof, provided that the final post-treatment The Haq succinimide or succinic acid amide or mixtures thereof, the basic nitrogen is left at least one.

(A) Polyalkenyl succinic acid or polyalkenyl succinic anhydride A polyalkenyl succinic acid or polyalkenyl succinic anhydride is a reaction product of a polyalkenyl reactant and an unsaturated acidic reagent. Polyalkenyl succinic acid or anhydride is produced by either the chlorination reaction method or the thermal reaction method.

(Polyalkene)
The polyalkenyl reactant is a polyalkene that may be a polymer of a single olefin or a copolymer of two or more olefins. Main polyalkenyl group sources include olefin polymers, particularly polymers made from mono-olefins having 2 to about 30 carbon atoms. Particularly useful are polymers of 1-mono-olefins such as ethylene, propene, 1-butene and isobutene. Polymers of isobutene are preferred.

  In addition to the pure polyalkenyl substituents described above, “polyalkenyl” as used herein and in the claims also includes materials that are substantially polyalkenyl. “Substantially polyalkenyl” as used herein refers to non-hydrocarbon substitutions that significantly affect the polyalkenyl properties of the polyalkenyl substituent with respect to the use of such polyalkenyl substituents in the present invention. Neither groups nor non-carbon atoms means no polyalkenyl groups. For example, polyalkenyl substituents may contain one or more ether, oxo, nitro, thia, carbohydrocarbyloxy or other non-hydrocarbon groups so long as these groups do not significantly affect the polyalkenyl properties of the substituent. You can also.

  Another important aspect of the present invention is that the polyalkenyl substituent of the polyalkenyl succinic compound is substantially saturated, i.e., at least about 95% of the total number of carbon-carbon covalent bonds is saturated. It is in. The extra portion of unsaturated bonds makes the molecule susceptible to oxidation, degradation and polymerization, resulting in a product that is unsuitable for use in hydrocarbon oils in many applications.

  It is understood that the size of the polyalkenyl substituent of the succinic compound determines the effectiveness of the additive of the present invention in a lubricating oil. Olefin polymers having a molecular weight of about 500 to 5000 (ie polyalkenes) are preferred. More preferably, the molecular weight of the olefin polymer is about 700 to 3000. In a preferred embodiment, the olefin polymer has a molecular weight of about 1000. In another preferred embodiment, the molecular weight of the olefin is about 2300. The most common sources of these polyalkenes are polyolefins such as polyethylene, polypropylene and polyisobutene. A particularly preferred polyolefin is polyisobutene having a molecular weight of about 900 to about 2500.

(Unsaturated acidic reagent)
“Unsaturated acidic reagent” means a maleic acid or fumaric acid reactant of the general formula:

In the formula, at least one of X and X ′ reacts to esterify an alcohol, form ammonia or an amine with an amide or amine salt, or react with a reactive metal or base as a metal compound and a metal salt. X and X ′ may be the same or different as long as it is a group that can form or function as an acylating agent. In general, X and / or X ′ are —OH, —O-hydrocarbon, —OM ⁺ (wherein M ⁺ represents one equivalent of a metal, ammonium or amine cation), —NH ₂ , —Cl, —Br. And together X and X ′ may be —O— to form an anhydride. Preferably X and X ′ are such that both carboxyl functions can be part of the acylation reaction. Maleic anhydride is a preferred unsaturated acidic reactant. Other suitable unsaturated acidic reactants include electron deficient olefins such as monophenylmaleic anhydride; monomethyl, dimethyl, monochloro, monobromo, monofluoro, dichloro and difluoromaleic anhydride; N-phenylmaleimide and others Mention may be made of substituted maleimides; isomaleimides; fumaric acid, maleic acid, maleic acid and alkyl hydrogen fumarate, fumaric acid and dialkyl maleates, fumaranilide acids and maleamic acids; and maleonitrile and fumaronitrile.

(Method for producing polyalkenyl derivative)
In general, polyalkenyl succinic acids and anhydrides can be made by two different types of reactions or processes.

  The first type of reaction or process includes pre-reacting the polyalkene with a halogen, such as chlorine, and reacting the halogenated polyalkene with maleic acid or anhydride, or the polyalkene with maleic anhydride or maleic acid, such as halogen. Contacting in the presence of chlorine is included. This type of reaction or process is known in the art as a “chlorination” reaction and is described in US Pat. No. 3,172,892 (Rusul, et al., Issued March 9, 1965), all of which are also incorporated herein by reference. The contents of this specification are used as reference contents.

  A second type of reaction or process that can be used to produce polyalkenyl succinic anhydrides or acids involves simply contacting hydrocarbons with maleic anhydride or maleic acid (in the absence of halogen) at elevated temperatures. Included. This type of reaction or method is known in the art as a thermal reaction. For the purposes of this specification and claims, “thermal methods” and “thermal reactions” are disclosed in US Pat. No. 3,361,673 (Stuart, et al., Issued January 2, 1968). There are methods such as methods, and all the contents thereof are described in this specification as reference contents. In addition, US Pat. No. 3,912,764 (Palmer, issued on Oct. 14, 1975) reacts a hydrocarbon with a substantial part of maleic anhydride or maleic acid by a thermal method and then reacts by a chlorination reaction. It includes a combination of thermal and chlorination methods by completing the process. U.S. Pat. No. 3,912,764 is also incorporated herein by reference.

(B) Amine Compound In one embodiment of the present invention, an amine is reacted with the above-described poralkenyl succinic acid or anhydride. The amine is preferably a polyalkylene polyamine containing at least two primary amines. More preferably, the polyalkylene polyamine compound has at least 3 nitrogen atoms.

  In some embodiments, the polyalkylene polyamine is diethylenetriamine (DETA), triethylenetetraamine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), heavy polyamine (HPA), or mixtures thereof. . High molecular weight polyethylene amines can also be used. The polyalkylene polyamines may contain a branched structure, a cyclic structure or a mixture thereof.

  In some embodiments, the polyalkylene polyamine may be a polyether amine that includes both primary and secondary amines.

  Both the initial and final post-treatment agents require primary or secondary nitrogen sites to be reacted. After both post-treatment steps, some of the nitrogen atoms are preferably basic nitrogen.

(C) Post-treatment of succinimide In one aspect of the invention, the succinimide is post-treated with a first post-treatment agent, whereby the first post-treated succinimide or succinamide or their A mixture is formed. The first post-treated succinimide or succinamide or mixture thereof is then reacted with a second post-treatment agent.

  In one embodiment, the first post-treated succinimide is produced by reacting the succinimide with an aromatic carboxylic anhydride. The aromatic carboxylic acid anhydride may be substituted (ie, with a methyl, nitro, or hydroxyl group depending on the aromatic ring). Representative aromatic anhydrides include trimellitic anhydride, phthalic anhydride, and naphthalic anhydride. Preferably, the aromatic anhydride is phthalic anhydride or naphthalic anhydride.

  In some embodiments, the final post-treated succinimide is produced by reacting the first post-treated succinimide with a second post-treatment agent, preferably a cyclic carbonate.

Representative cyclic carbonates used in the present invention include the following: 1,3-dioxolan-2-one (ethylene carbonate), 4-methyl-1,3-dioxolan-2-one ( Propylene carbonate), 4-ethyl-1,3-dioxolan-2-one (butylene carbonate), 4-hydroxymethyl-1,3-dioxolan-2-one, 4,5-dimethyl-1,3-dioxolane-2 -One, 4-ethyl-1,3-dioxolan-2-one, 4,4-dimethyl-1,3-dioxolan-2-one, 4-methyl-5-ethyl-1,3-dioxolan-2-one 4,5-diethyl-1,3-dioxolan-2-one, 4,4-diethyl-1,3-dioxolan-2-one, 1,3-dioxane-2-one, 4,4-dimethyl 1,3-dioxane-2-one, 5,5-dimethyl-1,3-dioxan-2-one, 5,5-dihydroxymethyl-1,3-dioxan-2-one, 5-methyl-1 , 3-dioxan-2-one, 4-methyl-1,3-dioxan-2-one, 5-hydroxy-1,3-dioxan-2-one, 5-hydroxymethyl-5-methyl-1,3- Dioxane-2-one, 5,5-diethyl-1,3-dioxan-2-one, 5-methyl-5-propyl-1,3-dioxan-2-one, 4,6-dimethyl-1,3- Dioxane-2-one, 4,4,6-trimethyl-1,3-dioxan-2-one, and spiro [1,3-oxa-2-cyclohexanone-5,5′-1 ′, 3′-oxa- 2'-cyclohexanone]. Other suitable cyclic carbonates, sorbitol, glucose, from saccharides such as fructose and galactose, also from the proximity diols prepared from C ₁ -C ₃₀ olefins, prepared by methods known in the art be able to.

  Some of these cyclic carbonates, such as 1,3-dioxolan-2-one or 4-methyl-1,3-dioxolan-2-one, are commercially available. Cyclic carbonates can be easily produced by known reactions. For example, by reaction of phosgene with a suitable alpha alkanediol or alkane-1,3-diol, as in US Pat. No. 4,115,206, the contents of which are hereby incorporated by reference. Carbonates are produced which can be used within the scope of the present invention.

  Similarly, cyclic carbonates that can be used in the present invention can also be produced by transesterification of suitable alpha alkanediols or alkane-1,3-diols under transesterification conditions, for example with diethyl carbonate. See, for example, U.S. Pat. Nos. 4,384,115 and 4,423,205, the contents of which are hereby incorporated by reference with respect to the teachings of cyclic carbonate production.

  Representative linear monocarbonates include diethyl carbonate, dimethyl carbonate, dipropyl carbonate, and the like. Typical linear polycarbonates include poly (propylene carbonate).

  Representative aromatic carboxylic acid anhydrides include 2,3-pyrazinedicarboxylic acid anhydride, 2,3-pyridinedicarboxylic acid anhydride, 3,4-pyridinedicarboxylic acid anhydride, diphenic acid anhydride, isatoic acid anhydride, Examples thereof include phenyl succinic anhydride, 1-naphthalene acetic anhydride, and 1,2,4-benzenetricarboxylic anhydride. Representative aromatic carboxylic acids include the above anhydride acids.

  Representative aromatic carboxylic acid esters include dimethyl phthalate, diethyl phthalate, dimethyl hexyl phthalate, monomethyl hexyl phthalate, monoethyl phthalate, and monomethyl phthalate.

  In some embodiments, the second post-treatment agent is a cyclic carbonate or a linear monocarbonate. In some embodiments, the first post-treatment agent is an aromatic carboxylic acid, acid anhydride, or ester.

  In general, the first post-treatment agent (ie, phthalic anhydride or 1,8-naphthalic anhydride) is added to the reactor containing the succinimide and heated so that the first post-treated succinimide is obtained. Generate. The first post-treated succinimide is further reacted with a second post-treatment agent such as ethylene carbonate.

(D) Method for Producing Post-Processed Succinimide Polyalkenyl succinic acid or polyalkenyl succinic anhydride is charged to the reactor, optionally purged with nitrogen, and at a temperature of about 80 ° C to about 170 ° C. Succinimide is produced by a method comprising heating. Optionally, the diluent oil may be placed in the same reactor while being purged with nitrogen. The amine compound is charged to the reactor, optionally purged with nitrogen. The mixture is heated to a temperature in the range of about 130 ° C. to about 200 ° C. under a nitrogen purge. Optionally, the mixture is depressurized for about 0.5 to about 2.0 hours to remove any moisture produced in the reaction.

  Alternatively, a succinimide can be prepared using a process that includes charging the reactor all of the reactants-polyalkenyl succinic acid or polyalkenyl succinic anhydride and amine compound in the desired ratio simultaneously. . One or more of the reactants can be charged at elevated temperatures to facilitate mixing and reaction. A static mixer can be used to facilitate the mixing of the reactants into the reactor. The reaction is carried out at a temperature of about 130 ° C. to 200 ° C. for about 0.5 to 2 hours. Optionally, the reaction mixture is depressurized during the reaction time to remove any moisture produced in the reaction.

  The first post-treated succinimide is prepared by a process comprising charging the reactor with succinimide optionally purged with nitrogen and heating at a temperature of about 80 ° C to about 170 ° C. Optionally, the diluent oil may be placed in the same reactor while being purged with nitrogen. The aromatic carboxylic acid anhydride is charged to the reactor, optionally purged with nitrogen. The mixture is heated to a temperature in the range of about 130 ° C. to about 200 ° C. under a nitrogen purge. Optionally, the mixture is depressurized for about 0.5 to about 2.0 hours to remove any moisture generated in the reaction and produce the first post-treated succinimide.

  A final post-treated succinic acid is obtained by a process comprising charging the reactor with the first post-treated succinimide, optionally purged with nitrogen, and heating at a temperature of about 80 ° C to about 200 ° C. An imide is produced. Optionally, the diluent oil may be placed in the same reactor while being purged with nitrogen. The cyclic carbonate is charged to the reactor, optionally purged with nitrogen, thereby producing the final post-treated succinimide.

(E) Lubricating Oil Composition The final post-treated succinimide described above is generally added to a base oil that can sufficiently lubricate moving parts such as internal combustion engines, gears and transmissions. Generally, the lubricating oil composition of the present invention contains a major amount of oil of lubricating viscosity and a minor amount of lubricating oil additive composition.

The base oil used may be any of a variety of lubricating viscosities. The base oil of lubricating viscosity used in such a composition may be a mineral oil or a synthetic oil. Base oils with a viscosity of at least 2.5 cSt at 40 ° C. and a pour point of less than 20 ° C., preferably 0 ° C. or less are desirable. Base oils can be derived from synthetic or natural sources. Examples of the mineral oil used as the base oil in the present invention include paraffinic, naphthenic and other oils that are usually used in lubricating oil compositions. Synthetic oils include, for example, both hydrocarbon synthetic oils and synthetic esters having a desired viscosity and mixtures thereof. Examples of the hydrocarbon synthetic oil include an oil produced by polymerization of ethylene, a polyalphaolefin or PAO oil, or a hydrocarbon synthetic method using carbon monoxide gas and hydrogen gas as in the Fischer-Tropsch process. Oil can be mentioned. Synthetic hydrocarbon oils that can be used include alpha olefin liquid polymers having the proper viscosity. Particularly useful are hydrogenated liquid oligomers of C ₆ -C ₁₂ alpha olefins such as 1-decene trimer. Similarly, alkylbenzenes of appropriate viscosity, such as didodecylbenzene, can be used. Synthetic esters that can be used include esters of monocarboxylic and polycarboxylic acids with monohydroxyalkanols and polyols. Representative examples include didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, and dilauryl sebacate. Complex esters made from mixtures of mono and dicarboxylic acids and mono and dihydroxy alkanols can also be used. A blend of mineral and synthetic oils can also be used.

  Thus, the base oil may be a refined paraffinic base oil, a refined naphthenic base oil, or a synthetic or non-hydrocarbon oil of lubricating viscosity. The base oil may be a mixture of mineral oil and synthetic oil.

(F) Concentrates Lubricating oil concentrates are also conceivable. These concentrates are usually from about 90% to about 10%, preferably from about 90% to about 50% by weight of oil of lubricating viscosity and from about 10% to about 90% by weight of the final post-treatment described above. Contains the finished succinimide. In general, the concentrate contains sufficient diluent to facilitate handling during shipping and storage. Suitable diluents for the concentrate include any inert diluent, preferably an oil of lubricating viscosity, whereby the concentrate can be easily mixed with the lubricating oil to produce a lubricating oil composition. Although any lubricating viscosity oil can be used, the viscosity of a suitable lubricating oil that can be used as a diluent is generally from about 35 to about 500 Saybolt Universal Viscosity (SUS) at 100 ° F. (38 ° C.). It is in the range.

(G) Other Additives In one aspect of the present invention, the following additive components are some examples of components that can be preferably used in a lubricating oil composition.

  Examples of these additives are provided to illustrate the present invention and are not intended to limit the present invention.

1) Metal detergents Sulfurized or unsulfurized alkyl or alkenyl phenates, alkyl or alkenyl aromatic sulfonates, borated sulfonates, sulfurized or unsulfurized metal salts of polyhydroxyalkyl or alkenyl aromatic compounds, alkyl or alkenyl hydroxy aroma Sulfonates, sulfurized or unsulfurized alkyl or alkenyl naphthenates, metal salts of alkanolic acids, metal salts of alkyl or alkenyl polyacids, and chemical and physical mixtures thereof.

2) Antioxidants Antioxidants reduce the tendency of oils to deteriorate when exposed to oxygen and heat. Evidence of this degradation is in the formation of sludge and varnish deposits, increased oil viscosity and increased corrosion or wear. Examples of antioxidants that can be used in the present invention include, but are not limited to, phenolic (phenolic) antioxidants such as 4,4′-methylene-bis (2,6-di-tert). -Butylphenol), 4,4'-bis (2,6-di-tert-butylphenol), 4,4'-bis (2-methyl-6-tert-butylphenol), 2,2'-methylene-bis (4 -Methyl-6-tert-butylphenol), 4,4'-butylidene-bis (3-methyl-6-tert-butylphenol), 4,4'-isopropylidene-bis (2,6-di-tert-butylphenol) 2,2′-methylene-bis (4-methyl-6-nonylphenol), 2,2′-isobutylidene-bis (4,6-dimethylphenol), 2,2′-5-methylene Bis (4-methyl-6-cyclohexylphenol), 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,4-dimethyl-6 tert-butylphenol, 2,6-di-tert-1-dimethylamino-p-cresol, 2,6-di-tert-4- (N, N′-dimethylaminomethylphenol), 4,4′-thiobis ( 2-methyl-6-tert-butylphenol), 2,2′-thiobis (4-methyl-6-tert-butylphenol), bis (3-methyl-4-hydroxy-5-tert-10-butylbenzyl) -sulfide And bis (3,5-di-tert-butyl-4-hydroxybenzyl). Diphenylamine type antioxidants include, but are not limited to, alkylated diphenylamine, phenyl-alpha-naphthylamine, and alkylated alpha-naphthylamine. Sulfur-containing antioxidants include ashless sulfides and polysulfides, metal dithiocarbamates (eg, zinc dithiocarbamate), and 15-methylenebis (dibutyldithiocarbamate). Phosphorus compounds, especially alkyl phosphites, sulfur / phosphorus compounds, and copper compounds can also be used as antioxidants.

3) Abrasion resistant additives Abrasion resistant additives reduce the wear of moving metal parts under continuous moderate loading conditions. Examples of such additives include, but are not limited to, phosphate esters and thiophosphate esters and salts thereof, carbamates, esters, and molybdenum complexes. Particularly preferred antiwear compounds are amine phosphates.

4) Rust prevention additive (rust prevention agent)
Anticorrosive additives improve the corrosion of ferrous metals. These include (a) nonionic polyoxyethylene surfactants such as polyoxyethylene lauryl ether, polyoxyethylene higher alcohol ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene octyl stearyl. Ethers, polyoxyethylene oleyl ether, polyoxyethylene sorbitol monostearate, polyoxyethylene sorbitol monooleate, and polyethylene glycol monooleate; and (b) other compounds such as stearic acid and other fatty acids, dicarboxylic acids Metal soaps, fatty acid amine salts, heavy sulfonic acid metal salts, polyhydric alcohol partial carboxylic acid esters, and phosphate esters. That.

5) Demulsifiers Demulsifiers promote the separation of oil from water that can come into contact with the oil by incorporation. Examples of the demulsifier include adducts of alkylphenol and ethylene oxide, polyoxyethylene alkyl ethers, and polyoxyethylene sorbitan esters.

6) Extreme pressure agent (EP agent)
Extreme pressure agents reduce wear of moving metal parts under high load conditions. Examples of EP agents include sulfurized olefins, zinc dialkyl-1-dithiophosphates (primary alkyl type, secondary alkyl type and aryl type), diphenyl sulfide, methyl trichlorostearate, chlorinated naphthalene, fluoroalkyl poly Mention may be made of siloxane, lead naphthenate, neutralized or partially neutralized phosphate esters, dithiophosphate esters, and sulfur-free phosphate esters.

7) Friction modifiers Fatty alcohols, fatty acids (stearic acid, isostearic acid, oleic acid and other fatty acids or their salts), amines, borated esters, other esters, phosphate esters, tri- and dihydrocarbon derivatives Phosphites other than phosphate esters, and phosphonate esters.

8) Multifunctional additives Some additives work to confer multiple functions simultaneously. In particular, the aryl and zinc alkyldithiophosphates can simultaneously impart wear resistance, extreme pressure and antioxidant properties. Particularly preferred are alkaryl, primary alkyl and secondary alkyl zinc dithiophosphates. Primary alkyl zinc dithiophosphates are particularly preferred.

9) Viscosity index improver Viscosity index improvers are used to increase the viscosity index of lubricating oils, thereby reducing oil viscosity drop due to increased temperature. Polymethacrylate polymers, ethylene / propylene copolymers, styrene / isoprene copolymers, hydrated styrene / isoprene copolymers, and polyisobutylene can all be used as viscosity index improvers. Polymers having nitrogen and oxygen functional groups, so-called dispersed viscosity index improvers can also be used.

10) Pour point depressant The pour point depressant lowers the temperature at which the wax deposits from the lubricating oil, thereby expanding the temperature range in which the lubricating oil can act before the oil flow is hindered. Examples of the pour point depressant include polymethyl methacrylates, ester / olefin copolymers, and particularly ethylene / vinyl acetate copolymers.

11) Antifoaming agent The antifoaming agent acts to promote the release of gas mixed in the lubricant during operation. Common antifoaming agents include alkyl methacrylate polymers and dimethylsiloxane polymers.

12) Metal deactivators Metal deactivators prevent corrosion of the metal surface and also chelate metal ions to dissolve them in the lubricating oil, thereby reducing oxidation caused by the catalytic effect of metal ions. Common metal deactivators include salicylidene propylene diamine, triazole derivatives, mercaptobenzothiazoles, thiadiazole derivatives, and mercaptobenzimidazoles.

13) Dispersants Alkenyl succinimides, alkenyl succinimides modified with other organic compounds, alkenyl succinimides modified by post-treatment with ethylene carbonate or boric acid, polyalcohol and polyisobutenyl succinic anhydride Esters, phenate-salicylates and post-treated analogs thereof, alkali metals or mixed alkali metals, alkaline earth metal borates, dispersions of hydrated alkali metal borates, alkaline earth metal borates Acid salt dispersions, polyamide ashless dispersants, etc., or mixtures of such dispersants.

(H) Method of Use of the Invention The final post-treated succinimide of the invention can be added to an oil of lubricating viscosity thereby producing a lubricating oil composition. The final post-treated succinimide added to the oil of lubricating viscosity is used in the internal combustion engine, thereby improving the dispersibility of soot and sludge.

  The following examples serve to illustrate certain embodiments of the present invention and should in no way be construed as limiting the scope of the invention.

Example 1 Mono-succinimide derived from MW 1000 PIBSA and diethylenetriamine (amine: PIBSA loading molar ratio 0.90: 1)
A 1 L reactor was charged with MW1000 PIBSA (Chevron Oronite LLC) 549.94 g and Chevron RLOP100N base oil 263 g. A distillation head equipped with a condenser and a 250 mL round bottom flask was attached to the 1 L reactor. The apparatus was placed in a nitrogen atmosphere and the mixture was heated to 160 ° C. Diethylenetriamine (41.80 g, Sigma-Aldrich) was then added to the mixture over 30 minutes. The mixture was heated at 160 ° C. for an additional 90 minutes. Next, a vacuum of <0 mmHg was applied for 30 minutes. The product had the following properties.
TBN = 31.2mgKOH / g
Nitrogen = 1.85% by mass

Example 2 Mono-succinimide post-treated with phthalic anhydride derived from MW 1000 PIBSA and DETA (phthalic anhydride: PIBSA loading molar ratio 0.80: 1)
The product of Example 1 was heated to 160 ° C. in a nitrogen atmosphere in the apparatus described in Example 1. Phthalic anhydride (53.25 g, Sigma-Aldrich) was added over 15 minutes. The reaction mixture was heated at 160 ° C. for an additional 90 minutes. Next, a vacuum state of ≦ 0 mmHg was applied for 30 minutes. The product had the following properties.
TBN = 16.5 mgKOH / g
Nitrogen = 1.85% by mass

Example 3 Mono-succinimide derived from MW 1000 PIBSA and heavy polyamine (amine: PIBSA loading molar ratio 0.90: 1)
A 2 L reactor was charged with 1030.1 g MW1000 PIBSA and 321.3 g Chevron RLOP 100N base oil and placed in a nitrogen atmosphere. The mixture was heated to 160 ° C. Heavy polyamine (208.33 g) was then added to the mixture over 20 minutes. The mixture was heated at 160 ° C. for an additional 90 minutes. Next, the pressure was reduced to 10 mmHg for 30 minutes. The product had the following properties.
TBN = 125.3 mgKOH / g
Nitrogen = 4.58 mass%

Example 4 Mono-succinimide post-treated with phthalic anhydride derived from MW1000 PIBSA and HPA (phthalic anhydride: PIBSA loading molar ratio 0.80: 1)
A 1 L reactor was charged with 899.95 g of mono-succinimide prepared in Example 3 and heated to 160 ° C. in a nitrogen atmosphere. Then phthalic anhydride (58.12 g) was added. The reaction mixture was heated at 160 ° C. for an additional 90 minutes. Next, the pressure was reduced to 20 mmHg for 30 minutes. The product had the following properties.
TBN = 102.1mgKOH / g
Nitrogen = 4.51 mass%

Example 5 Mono-succinimide post-treated with ethylene carbonate and phthalic anhydride derived from MW 1000 PIBSA and HPA Mono-treated with phthalic anhydride prepared in Example 4 in a 500 mL reactor Filled with 466.45 g of succinimide and heated to 160 ° C. in a nitrogen atmosphere. Ethylene carbonate (79.58 g) was then added via syringe pump over 1 hour. The reaction mixture was heated at 160 ° C. for a further 2 hours. The product had the following properties.
TBN = 48.0 mgKOH / g
Nitrogen = 3.99% by mass

Example 6 Mono-succinimide derived from MW 2300 PIBSA and heavy polyamine (amine: PIBSA loading molar ratio 0.90: 1)
A 2 L reactor was charged with 1163.7 g of MW 2300 PIBSA (manufactured by Chevron Oronite) and 251.3 g of chevron RLOP100N base oil. The apparatus was placed in a nitrogen atmosphere and the mixture was heated to 160 ° C. Heavy polyamine (91.37 g) was then added to the mixture over 10 minutes. The mixture was heated at 160 ° C. for an additional 90 minutes. Next, the pressure was reduced to 10 mmHg for 30 minutes. The product had the following properties.
TBN = 83.9 mgKOH / g
Nitrogen = 2.12% by mass

Example 7 Mono-succinimide post-treated with phthalic anhydride derived from MW 2300 PIBSA and HPA (phthalic anhydride: PIBSA loading molar ratio 0.80: 1)
A 1 L reactor was charged with 890.44 g of Example 8, and heated to 160 ° C. in a nitrogen atmosphere. Phthalic anhydride (25.97 g) was added. The reaction mixture was heated at 160 ° C. for an additional 90 minutes. Next, the pressure was reduced to 10 mmHg for 30 minutes. The product had the following properties.
TBN = 40.94 mgKOH / g
Nitrogen = 2.05 mass%

[Example 8] Mono-succinimide post-treated with ethylene carbonate and phthalic anhydride derived from MW 2300 PIBSA and HPA Mono-treated with phthalic anhydride produced in Example 9 in a 500 mL reactor Filled with 404.05 g of succinimide and heated to 160 ° C. in nitrogen atmosphere. Ethylene carbonate (32.1 g) was then added via syringe pump over 1 hour. The reaction mixture was heated at 160 ° C. for a further 2 hours. The product had the following properties.
TBN = 26.0 mgKOH / g
Nitrogen = 1.89% by mass

Example 9 Mono-succinimide derived from MW 2300 PIBSA and heavy polyamine (amine: PIBSA loading molar ratio 0.60: 1)
A 2 L reactor was charged with 1000.9 g of MW 2300 PIBSA (manufactured by Chevron Oronite). The apparatus was placed in a nitrogen atmosphere and the mixture was heated to 160 ° C. Heavy polyamine (52.24 g) was then added to the mixture over 20 minutes. The mixture was heated at 160 ° C. for an additional 60 minutes. Next, the pressure was reduced to 30 minutes (<20 mmHg (absolute pressure)). The product had the following properties.
TBN = 43.8 mgKOH / g
Nitrogen = 1.68% by mass

Example 10 Mono-succinimide post-treated with naphthalic anhydride derived from MW 2300 PIBSA and HPA (Naphthalic anhydride: PIBSA loading molar ratio 0.60: 1)
A 1 L reactor was charged with 513.9 g of succinimide prepared in Example 13 and heated to 140 ° C. in a nitrogen atmosphere. Naphthalic anhydride (18.47 g) was added over 5 minutes. The reaction mixture was heated to 160 ° C and maintained at 160 ° C for an additional 60 minutes. Next, the pressure was reduced to 30 minutes (<20 mmHg (absolute pressure)). The product had the following properties.
TBN = 36.0 mgKOH / g
Nitrogen = 1.62% by mass

Example 11 Mono-succinimide post-treated with ethylene carbonate and naphthalic anhydride derived from MW 2300 PIBSA and HPA A 1 L reactor was charged with 325.80 g of succinimide prepared in Example 14. And heated to 160 ° C. in a nitrogen atmosphere. Ethylene carbonate (17.68 g) was then added via syringe pump over 1 hour. The reaction mixture was heated at 160 ° C. for an additional 60 minutes. The product had the following properties.
TBN = xxmgKOH / g
Nitrogen = 1.62% by mass

Example 12 Mono-succinimide post-treated with ethylene carbonate derived from MW 2300 PIBSA and HPA A 500 mL reactor was charged with 278.84 g of succinimide prepared in Example 13 and in a nitrogen atmosphere. At 160 ° C. Ethylene carbonate (20.08 g) was added. The reaction mixture was heated at 160 ° C. for an additional 60 minutes. Next, the pressure was reduced to 30 minutes (<10 mmHg (absolute pressure)). The product had the following properties.
TBN = 24.4 mgKOH / g
Nitrogen = 1.52% by mass

Example 13 Mono-succinimide post-treated with phthalic anhydride derived from MW 2300 PIBSA and HPA (phthalic anhydride: PIBSA loading molar ratio 0.60: 1)
A 4 L reactor was charged with 1592.0 g of succinimide as prepared in Example 13 (except that the reaction retention time was 90 minutes instead of 60 minutes) and brought to 160 ° C. in a nitrogen atmosphere. Heated. Phthalic anhydride (44.76 g) was added. The reaction mixture was heated at 160 ° C. for an additional 90 minutes. Next, the pressure was reduced to 30 minutes (<20 mmHg (absolute pressure)). The product had the following properties.
TBN = 30.5mgKOH / g
Nitrogen = 1.66% by mass

Example 14 Mono-succinimide post-treated with ethylene carbonate and phthalic anhydride derived from MW 2300 PIBSA and HPA A reactor of 500 mL was charged with 247.17 g of succinimide prepared in Example 17. And heated to 160 ° C. in a nitrogen atmosphere. Ethylene carbonate (13.53 g) was then added via syringe pump over 1 hour. The reaction mixture was heated at 160 ° C. for an additional hour. The product had the following properties.
TBN = xxmgKOH / g
Nitrogen = 1.61% by mass

(Results of soot thickening bench test)
The mono-succinimide of Examples 1 to 10 and the post-treated mono-succinimide were reacted in a soot thickening bench test. In this test, 98.0 g of a test sample was weighed into a 250 mL beaker. The test sample was 8% by weight based on 50% test dispersant activity, 50 millimolar overbased phenate detergent, 18 millimolar zinc dithiophosphate antiwear agent, and 7.3% by weight VI improver, 85% 150N oil. And 600N oil in 15%. To this was added 2.0 g of Vulcan XC-72 ™ carbon black (Cabot Co.). After the mixture was stirred, it was stored in a desiccator for 16 hours. A second sample without carbon black was mixed for 60 seconds using a Willems Polytron homogenizer, model PF45 / 6, and then degassed for 30 minutes at 50-55 ° C. in a vacuum oven. Next, the viscosities of the two samples were measured at 100 ° C. using a capillary viscometer. The percent increase in viscosity was calculated by comparing the viscosities of the samples with and without carbon black. Therefore, the lower the viscosity increase percentage, the better the dispersibility of the dispersant. Table 1 shows the results of the soot thickening table test.

  As a result of the soot thickening bench test, the percentage increase in viscosity of the blended oil using mono-succinimide after treatment with (ii) phthalic anhydride and ethylene carbonate or (ii) naphthalic anhydride and ethylene carbonate is It is shown that it was generally lower than the percent increase in viscosity of the blended oils without phthalic anhydride / ethylene carbonate or naphthalic anhydride / ethylene carbonate post-treated mono-succinimide. This test shows that the lubricating oil additive composition of the present invention has excellent dispersibility.

  It should be understood that modifications and variations can be made to the present invention without departing from the spirit and scope of the invention, but that such limitations are imposed only as set forth in the appended claims.

Claims (16)

Lubricating oil additive composition produced by a method comprising the following steps:
(A) reacting polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms, thereby producing succinimide or succinamide or a mixture thereof. ,
(B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof, whereby the first post-treated succinimide or succinamide or a mixture thereof And (C) reacting the product of step (B) with a cyclic carbonate, thereby producing a final post-treated succinimide or succinamide or mixture thereof, provided that the final At least one basic nitrogen remains in the post-treated succinimide or succinamide or a mixture thereof. Polyalkenyl succinic acid or polyalkenyl succinic anhydride, a number average molecular weight (M _{n) 5} 00乃lubricating oil additive composition of claim 1 is derived from the optimal 5 000 polyisobutene. Polyalkenyl succinic acid or polyalkenyl succinic anhydride, a number average molecular weight (M _{n) 7} 00乃lubricating oil additive composition of claim 2 Optimum 3 is derived from the 000 polyisobutene.   The lubricating oil additive composition according to claim 1, wherein the polyalkylene polyamine is selected from diethylenetriamine, triethylenetetraamine, tetraethylenepentamine, pentaethylenehexamine, heavy polyamine or a mixture thereof.   The lubricating oil additive composition according to claim 4, wherein the polyalkylene polyamine is a heavy polyamine.   The lubricating oil additive composition according to claim 4, wherein the polyalkylene polyamine is tetraethylenepentamine.   The lubricating oil additive composition according to claim 1, wherein the cyclic carbonate is selected from ethylene carbonate, propylene carbonate, or butylene carbonate. Oil lubrication viscosity, and a lubricating oil composition comprising a Jun Namerayu additive composition prepared by a method comprising the following steps:
(A) reacting polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms, thereby producing succinimide or succinamide or a mixture thereof. ,
(B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof, whereby the first post-treated succinimide or succinamide or a mixture thereof And (C) reacting the product of step (B) with a cyclic carbonate, thereby producing a final post-treated succinimide or succinamide or mixture thereof, provided that the final At least one basic nitrogen remains in the post-treated succinimide or succinamide or a mixture thereof. Polyalkenyl succinic acid or polyalkenyl succinic anhydride, a number average molecular weight (M _{n) 5} 00乃lubricating oil composition according to claim 8 is derived from the optimal 5 000 polyisobutene.   The lubricating oil composition according to claim 8, wherein the polyalkylene polyamine is selected from diethylenetriamine, triethylenetetraamine, tetraethylenepentamine, pentaethylenehexamine, heavy polyamine or a mixture thereof.   The lubricating oil composition according to claim 10, wherein the polyalkylene polyamine is a heavy polyamine.   The lubricating oil composition according to claim 10, wherein the polyalkylene polyamine is tetraethylenepentamine. A method for producing a lubricating oil additive composition comprising the following steps:
(A) reacting polyalkenyl succinic acid or polyalkenyl succinic anhydride with at least one polyalkylene polyamine having at least 3 nitrogen atoms, thereby producing succinimide or succinamide or a mixture thereof. ,
(B) reacting the product of step (A) with a phthalic anhydride or naphthalic anhydride post-treatment agent or a mixture thereof, whereby the first post-treated succinimide or succinamide or a mixture thereof And (C) reacting the product of step (B) with a cyclic carbonate, thereby producing a final post-treated succinimide or succinamide or mixture thereof, provided that the final At least one basic nitrogen remains in the post-treated succinimide or succinamide or a mixture thereof. Polyalkenyl succinic acid or polyalkenyl succinic anhydride, a number average molecular weight (M _{n) 5} 00乃method for producing a lubricating oil additive composition of claim 13 is derived from the optimal 5 000 polyisobutene .   A method for improving soot dispersibility in an internal combustion engine comprising operating the internal combustion engine with the lubricating oil composition of claim 8.   A concentrate comprising 10 to 90% by weight of the lubricating oil additive composition of claim 1 and 90 to 10% by weight of an organic diluent.