JP6302416B2 - Lubricating oil composition - Google Patents

Description

  The present invention relates to a lubricating oil composition, and more particularly to a lubricating oil composition suitable for an internal combustion engine such as a gasoline engine, a diesel engine, or an engine or gas engine fueled with dimethyl ether.

  In recent years, in order to reduce energy loss and carbon dioxide emission while driving a car, it has been studied to improve the fuel efficiency of the car. As measures to improve the fuel efficiency of automobiles, the weight of automobile bodies has been reduced. However, lubricating oils are also required to contribute to fuel efficiency. Further improvement of friction reduction characteristics by oil is being studied.

  Conventionally, the use of a friction reducing agent has been studied in order to further improve the friction reduction characteristics of the lubricating oil. As friction reducers, ashless friction modifiers such as fatty acid amides, fatty acid esters and aliphatic ethers, and molybdenum friction reducers represented by molybdenum dithiocarbamate are known (for example, see Patent Document 1). Molybdenum-based friction reducers have a higher friction reducing effect than ashless friction modifiers, particularly in the boundary lubrication region, and are therefore blended in many engine oils.

  Conventionally, boric acid-based lubricating additives are known as additives having wear resistance and lubricating properties. For example, Patent Document 2 discloses that an organic borate ester is blended in a lubricating oil composition together with a 1,3,4-thiadiazole compound, dithiocarbamate, and a non-sulfur molybdenum compound, and exhibits synergistic anti-wear properties together with these compounds. Is described. The organic borate ester used in Patent Document 2 is a reaction product obtained by reacting fatty oil and diethanolamine and then reacting with boric acid.

JP 2011-12213 A JP-T-2006-502287

In recent years, there has been an increasing demand for fuel savings, and lubricating oils are also required to have lower viscosity and higher friction reduction characteristics. However, simply adding a molybdenum friction reducer to the lubricating oil is not sufficient to reduce the friction coefficient of the lubricating oil, and a lubricant additive and a combination of additives that can further reduce friction are required. ing.
On the other hand, the conventional boron compound as disclosed in Patent Document 2 is relatively excellent in wear resistance, but has little effect of reducing the friction coefficient. However, it hardly contributed to lowering the friction of the lubricating oil.
The present invention has been made in view of the above problems, and it is an object of the present invention to provide a lubricating oil composition having high fuel saving properties by increasing the friction reduction performance and reducing the friction of the lubricating oil. .

As a result of intensive studies to solve the above problems, the present inventors have surprisingly found that if a specific boron-containing compound is blended with a lubricating oil, the lubricating oil can be reduced in friction, and the present invention is applied. It came.
That is, the present invention provides the following (1) to (14).
(1) When using BF ₃ · OEt ₂ as an external standard (0 ppm) and measuring ¹¹ B-NMR in deuterated chloroform, the peak of the chemical shift of 5 to 25 ppm with respect to the integrated value of the peak of the chemical shift of -10 ppm to 25 ppm. A lubricating oil composition comprising a boron-containing compound having an integral value ratio of 0.5 to 1.0.
(2) The said boron containing compound is a lubricating oil composition as described in said (1) whose ratio of the amount of boron atoms with respect to the amount of nitrogen atoms is 0.6 or more on a mass basis.
(3) The lubricating oil composition according to (1) or (2) above, wherein the boron-containing compound is obtained by allowing boric acid or a boric acid derivative to act on an organic compound having a hydroxyl group or an amino group.
(4) The organic compound is an amine compound (A), an amide compound (B) having a hydroxyl group, an imide compound (C) having an amino group, an ester compound (D) having a hydroxyl group, and an alcohol having a hydroxyl group. The lubricating oil composition according to the above (3), which is at least one compound selected from the compound (E).
(5) The lubricating oil composition according to any one of (1) to (4), wherein 0.01 to 30% by weight of the boron-containing compound is blended.
(6) In addition to the boron-containing compound, a viscosity index improver, a molybdenum compound, a zinc dialkyldithiophosphate, an antioxidant, a metallic detergent, and an ashless dispersion in a base oil composed of mineral oil and / or synthetic oil The lubricating oil composition according to any one of the above (1) to (5), wherein at least one of the agents is blended.
(7) The lubricating oil composition according to any one of (1) to (6), which is a lubricating oil composition for an internal combustion engine.
(8) A lubricating oil composition comprising an organic compound having a hydroxyl group or an amino group and a boron-containing compound obtained by heating and stirring boric acid or a boric acid derivative at a temperature of 100 ° C. or higher and 150 ° C. or lower.
(9) When ¹¹ B-NMR is measured in deuterated chloroform using BF ₃ · OEt ₂ as an external standard (0 ppm), the peak of the chemical shift is 5 to 25 ppm with respect to the integrated value of the peak of the chemical shift of −10 ppm to 25 ppm. A lubricating oil composition containing a boron-containing compound having an integral value ratio of 0.5 to 1.0.
(10) A lubricating oil composition comprising a boron-containing compound obtained by heating and stirring an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative at a temperature of 100 ° C. or higher and 150 ° C. or lower.
(11) Further, at least one of a base oil composed of mineral oil and / or synthetic oil, a viscosity index improver, a molybdenum compound, zinc dialkyldithiophosphate, an antioxidant, a metal detergent, and an ashless dispersant. The lubricating oil composition according to (9) or (10), comprising
(12) When BF ₃ · OEt ₂ is used as an external standard (0 ppm) and ¹¹ B-NMR measurement is performed in deuterated chloroform, the peak of the chemical shift is 5 to 25 ppm with respect to the integrated value of the peak of the chemical shift of −10 ppm to 25 ppm. A method for producing a lubricating oil composition comprising producing a lubricating oil composition by blending a boron-containing compound having an integral value ratio of 0.5 or more and 1.0 or less into a base oil composed of mineral oil and / or synthetic oil .
(13) A boron-containing compound is obtained by heating and stirring an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative at a temperature of 100 ° C. or higher and 150 ° C. or lower. Or the manufacturing method of the lubricating oil composition which manufactures a lubricating oil composition by mix | blending with the base oil which consists of synthetic oils.
(14) The above base oil further contains at least one of a viscosity index improver, a molybdenum compound, zinc dialkyldithiophosphate, an antioxidant, a metallic detergent, and an ashless dispersant. ) Or the method for producing the lubricating oil composition according to (13).

  In the lubricating oil composition of the present invention, when a specific boron-containing compound is blended, the friction coefficient is lowered and the friction is reduced, and the fuel efficiency of an internal combustion engine or the like can be improved.

Hereinafter, preferred embodiments of the present invention will be described in detail.
The lubricating oil composition of the present invention is obtained by blending a boron-containing compound with a lubricating base oil (hereinafter sometimes simply referred to as “base oil”).

[Boron-containing compounds]
The boron-containing compound of the present invention is a boron-based lubricant additive obtained by allowing boric acid or a boric acid derivative to act on an organic compound having a hydroxyl group or an amino group. Specifically, the boron-containing compound has a hydroxyl group or an amino group. A boron-containing compound obtained by heating and stirring an organic compound having boric acid or a boric acid derivative at 100 ° C. or higher and 150 ° C. or lower.
The boron-containing compound of the present invention lowers the friction coefficient of the lubricating oil composition and lowers the friction while improving the wear resistance of the lubricating oil composition.

The boron-containing compound of the present invention uses BF ₃ · OEt ₂ as an external standard (0 ppm), and when measured by ¹¹ B-NMR in deuterated chloroform, the chemical shift is relative to the integrated value of the peak of chemical shift -10 to 25 ppm. The ratio of the integrated values of the peaks of 5 to 25 ppm is 0.50 or more and 1.0 or less.
In ¹¹ B-NMR measurement using BF ₃ · OEt ₂ standard (0 ppm), it is known that a peak of a tricoordinate boron compound appears at a chemical shift of 5 to 25 ppm. However, when it becomes 0.50 or more, the ratio of the tricoordinate boron-containing compound increases.
In addition, it is known that the peak of the tetracoordinate boron-containing compound appears at −10 to 5 ppm. Therefore, the boron-containing compound of the present invention is obtained by converting the tricoordinate boron-containing compound into the tricoordinate and 4-coordinate. It is contained in a molar ratio of 0.50 or more with respect to the total amount of the coordinated boron-containing compound.
The tricoordinate boron-based compound is a component that contributes to low friction. Therefore, when the ratio of the integrated values or the molar ratio is less than 0.50, the friction coefficient of the lubricating oil composition increases, and the lubricating oil The composition cannot be reduced in friction.
In addition, from the viewpoint of lowering the friction coefficient, the ratio of the integrated values (or the molar ratio) is preferably 0.55 or more.

When the boron-containing compound of the present invention contains a nitrogen atom, the ratio of the boron atom amount to the nitrogen atom amount (B / N ratio) contained in the compound is preferably 0.6 or more on a mass basis. More preferably, it is 7 or more. Further, the B / N ratio is not particularly limited, but is preferably 2.0 or less, and more preferably 1.5 or less. In the present invention, the friction ratio of the lubricating oil composition can be appropriately reduced by setting the B / N ratio to 0.6 or more.
Moreover, in a boron containing compound, content of a boron atom becomes like this. Preferably it is 0.1-3 mass%, More preferably, it is 1-3 mass%.

In the lubricating oil composition, the boron-containing compound of the present invention is usually added in an amount of 0.01 to 30% by mass, preferably 0.1 to 15% by mass, and more preferably 0.5 to 5% by mass.
In this invention, the function which reduces a friction coefficient can be suitably exhibited by setting it as the said lower limit or more.

  The above boric acid derivatives include orthoboric acid, metaboric acid, tetraboric acid, boron oxide, boron trifluoride, boron tribromide, boron trichloride, and other boron halides, trimethyl borate, triethyl borate, tributyl borate Boric acid esters such as triisopropyl borate and tributyl borate.

  In the present invention, examples of the organic compound having a hydroxyl group or amino group include an amine compound (A), an amide compound (B) having a hydroxyl group, an imide compound (C) having an amino group, and a hydroxyl group. Examples include at least one compound selected from an ester compound (D) and an alcohol compound (E) having a hydroxyl group.

Hereinafter, the compounds (A) to (E) will be described in detail.
[Amine compound (A)]
The amine compound (A) is an amine compound (a1) having one or more hydroxyl groups and one or more amino groups, an amine compound (a2) having two or more amino groups, or an amine having only one amino group A compound (a3) etc. are mentioned.
Among the above, as the amine compound (a1), more specifically, compounds represented by the following general formulas (A1) and (A2) can be mentioned, and as the amine compound (a1) or the amine compound (a2), The compound represented by general formula (A3) or (A4) is mentioned. Moreover, as an amine compound (a3), the compound represented by the following general formula (A5) is mentioned.

In formulas (A1) to (A5), R ₁ , R ₁₀ , R ₁₁ , R ₁₆ , R _{29 and} R ₄₇ are each a hydrocarbon group having 1 to 32 carbon atoms, and R ₁₀ and R ₁₁ are the same as each other. But it may be different. Such a hydrocarbon group may be saturated or unsaturated, may be aliphatic or aromatic, may be linear, branched or cyclic, for example, an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, Or an aromatic hydrocarbon group is mentioned.
Specific examples of the hydrocarbon group include methyl, ethyl, propyl, butyl, butenyl, hexyl, hexenyl, octyl, octenyl, 2-ethylhexyl, nonyl, decyl, undecyl. Group, decenyl group, dodecyl group, dodecenyl group, tridecyl group, tetradecyl group, tetradecenyl group, pentadecyl group, hexadecyl group, hexadecenyl group, heptadecyl group, octadecyl group, octadecenyl group, stearyl group, isostearyl group, oleyl group, linol group , Nonadecyl group, icosyl group, eicosyl group, heicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl , Decene trimer group, polybutene group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, trimethylcyclohexyl group and other aliphatic hydrocarbon groups, phenyl group, methylphenyl group, ethylphenyl Groups, aromatic hydrocarbon groups such as dimethylphenyl group, propylphenyl group, trimethylphenyl group, butylphenyl group and naphthyl group.
The hydrocarbon group is preferably a hydrocarbon group having 4 to 22 carbon atoms, and more preferably a hydrocarbon group having 6 to 18 carbon atoms.

R _{2 to} R ₉ , R _{12 to} R ₁₅ , R _{17 to} R ₂₈ , R _{30 to} R ₄₅ , R _{48 to} R ₄₉ are a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, or an ether bond or an ester bond. These are oxygen-containing hydrocarbon groups that may be the same or different from each other, but are preferably hydrogen atoms or hydrocarbon groups.
The hydrocarbon group may be saturated or unsaturated, aliphatic or aromatic, linear, branched or cyclic, for example, an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, or an aromatic group Group hydrocarbon group. More specifically, methyl group, ethyl group, propyl group, butyl group, butenyl group, hexyl group, hexenyl group, octyl group, octenyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, decenyl group, Dodecyl, dodecenyl, tridecyl, tetradecyl, tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, stearyl, isostearyl, oleyl, linole, cyclopentyl, cyclohexyl Group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, aliphatic hydrocarbon group such as trimethylcyclohexyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group Group, propylphenyl group, trimethylphenyl group, butylphenyl group, an aromatic hydrocarbon group and a naphthyl group.
As this hydrocarbon group, a C1-C18 thing is preferable, a C1-C16 thing is more preferable, and a C1-C12 thing is especially preferable.
Examples of the oxygen-containing hydrocarbon group containing an ether bond or an ester bond are those having 1 to 18 carbon atoms, such as a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, an isopropoxymethyl group, an n-butoxymethyl group, t-butoxymethyl group, hexyloxymethyl group, octyloxymethyl group, 2-ethylhexyloxymethyl group, decyloxymethyl group, dodecyloxymethyl group, 2-butyloctyloxymethyl group, tetradecyloxymethyl group, hexadecyloxy group Methyl group, 2-hexyldecyloxymethyl group, allyloxymethyl group, phenoxy group, benzyloxy group, methoxyethyl group, methoxypropyl group, 1,1-bismethoxypropyl group, 1,2-bismethoxypropyl group, ethoxy Propyl group, (2-methoxy Ethoxy) propyl group, (1-methyl-2-methoxy) propyl group, acetyloxymethyl group, propanoyloxymethyl group, butanoyloxymethyl group, hexanoyloxymethyl group, octanoyloxymethyl group, 2-ethylhexa Noyloxymethyl group, decanoyloxymethyl group, dodecanoyloxymethyl group, 2-butyloctanoyloxymethyl group, tetradecanoyloxymethyl group, hexadecanoyloxymethyl group, 2-hexyldodecanoyloxymethyl group, benzoyl An oxymethyl group etc. can be mentioned.

Moreover, a, b, c, e, f, g, j, k, w, m each represents an integer of 0-20, d, h, i each represents an integer of 1-6, and a + b = 1-20, e + f + g = 0-20, j + k + w + m = 0-20.
(A + b) is preferably 1 to 12, more preferably 1 to 10. C, (e + f + g), and (j + k + w + m) are each preferably 0 to 12, more preferably 0 to 10. d, h, and i are each preferably 2-4.

In the general formula (A1), R _{2 to} R ₅ and R _{6 to} R ₉ are all hydrogen atoms, or R _{2 to} R ₄ and R _{6 to} R ₈ are all hydrogen atoms, and R ₅ and It is preferable that one or both of R ₉ is a hydrocarbon group.
In general formula (A2), it is preferable that all of R _{12 to} R ₁₄ are hydrogen atoms, and R ₁₅ is a hydrogen atom or a hydrocarbon group.
In the general formula (A3), each of e, f, and g is 1 or more, and R _{17 to} R ₂₈ are preferably all hydrogen atoms, and more preferably, all of e, f, and g are 1. Of course, in general formula (A3), all of e, f, and g are 0, and it does not need to have a hydroxyl group.
Moreover, in general formula (A4), it is preferable that j, k, w, and m are all 0.
Furthermore, in the general formula (A5), R ₄₇ is preferably an alkyl group, and at least one of R ₄₈ and R ₄₉ may be a hydrocarbon group, and the hydrocarbon group is an alkyl group. preferable.

Specific compounds of the general formula (A1) include octylethanolamine, decylethanolamine, dodecylethanolamine, tetradecylethanolamine, hexadecylethanolamine, stearylethanolamine, oleylethanolamine, coconut oil ethanolamine, palm oil. An amine compound having one 2-hydroxyalkyl group such as hydroxyethyl group exemplified by ethanolamine, rapeseed oil ethanolamine, beef tallow ethanolamine and the like; octyldiethanolamine, decyldiethanolamine, dodecyldiethanolamine, tetradecyldiethanolamine, hexadecyldiethanolamine, Stearyl diethanolamine, oleyl diethanolamine, coconut oil diethanolamine, palm oil diethanolamine Rapeseed oil diethanolamine, beef tallow diethanolamine, 1- [cyclohexyl (2-hydroxyethyl) amino] dodecan-2-ol, N, N-bis (2-hydroxydodecyl) -N-cyclohexylamine, 1- [N- (2 -Hydroxyethyl) anilino] dodecan-2-ol, N, N-bis (2-hydroxydodecyl) -N-octylamine, N, N-bis (2-hydroxypropyl) -N-oleylamine, N, N-bis (2-hydroxydodecyl) -amine compounds having two 2-hydroxyalkyl groups exemplified by aniline and the like; polyoxyethylene octylamine, polyoxyethylene decylamine, polyoxyethylene dodecylamine, polyoxyethylene tetradecylamine, Polyoxyethylene hexadecylami , Polyoxyethylene stearylamine, polyoxyethylene oleylamine, polyoxyethylene beef tallow amine, polyoxyethylene coconut oil amine, polyoxyethylene palm oil amine, polyoxyethylene laurylamine, polyoxyethylene stearylamine, polyoxyethylene oleylamine, ethylene oxide Examples thereof include amine compounds having a polyalkylene oxide structure such as propylene oxide stearylamine, and among these, amine compounds having two 2-hydroxyalkyl groups are preferred.
In the case of an amine compound having two 2-hydroxyalkyl groups, the ratio of the integrated value of the chemical shift peak of 5 to 25 ppm to the integrated value of the chemical shift peak of 10 to 25 ppm is relatively high. For example, it can be 0.70 or more, and further can be 0.80 or more. Note that the amine compound having two 2-hydroxyalkyl groups is a compound in which each of a and b is 1 in the formula (A1).
Moreover, as a commercial item of the compound shown by general formula (A1), Amit 105, Amit 308, Amit 320 (above, Kao Corporation make), Nimine L-202, Nimeen L-207, Nimine S-202, Nymin S-204, Nymeen S-210, Nymeen S-215, Nymeen S-220, Nymeen T2-202, Nymeen T2-206, Nymeen T2-210, Nymeen T2-230, Nymeen T2-260, Nymeen DT-203, Nymeen DT-208 (above, manufactured by NOF Corporation), Kawasoft EP59S (Kawaken Fine Chemical), Esomin T / 15, Esomin S / 15, Esomin O / 15 (above, manufactured by Lion Corporation) and the like are available.

  Specific examples of the general formula (A2) include, for example, N-methyl-octylethanolamine, N-methyl-decylethanolamine, N-methyl-dodecylethanolamine, N-methyl-tetradecylethanolamine, N- Methyl-hexadecylethanolamine, N-methyl-stearylethanolamine, N-methyl-oleylethanolamine, N-methyl-coconut oil ethanolamine, N-methyl-palm oil ethanolamine, N-methyl-rapeseed oil ethanolamine, Alkylamine compounds having one 2-hydroxyalkyl group such as hydroxyethyl group exemplified by N-methyl-tallow ethanolamine; polyoxyethylene N-methyl-decylamine, polyoxyethylene N-methyl-dodecylamine, poly Oxyethylene Alkylamines having a polyalkylene oxide structure exemplified by N-methyl-tetradecylamine, polyoxyethylene N-methyl-hexadecylamine, polyoxyethylene N-methyl-stearylamine, polyoxyethylene N-methyl-oleylamine and the like Compounds.

Specific compounds of the general formula (A3) include, as the amine compound (a2) having two or more amino groups, for example, N-lauryl-1,3-diaminopropane, N-stearyl-1,3-diaminopropane, Alkyl such as N-oleyl-1,3-diaminopropane, N-coconut oil alkyl-1,3-diaminopropane, N-tallow alkyl-1,3-diaminopropane, N-cured tallow-1,3-diaminopropane Or an alkenyl diamine etc. are mentioned.
Commercially available alkyl or alkenyl diamines include Duomin CD, Duomin T, Duomin HT Flakes (above, Lion Corporation) Nissan Amine DT, Nissan Amine DT-H, Nissan Amine DOB-R (above, NOF Corporation) ) Etc. are commercially available.

  In addition, specific compounds of the general formula (A3) include tris (2-hydroxyethyl) laurylpropylenediamine, tris (1) as a compound (a1) having one or more hydroxy groups and one or more amino groups. 2-hydroxyethyl) stearylpropylenediamine, tris (2-hydroxyethyl) oleylpropylenediamine, tris (2-hydroxyethyl) coconut oil propylenediamine, tris (2-hydroxyethyl) palm oil propylenediamine, tris (2-hydroxyethyl) ) Diamine compounds having three 2-hydroxyalkyl groups such as 2-hydroxyethyl groups exemplified by beef tallow propylene diamine; polyoxyethylene lauryl propylene diamine, polyoxyethylene stearyl propylene diamine, polyoxyethylene Yl propylenediamine, polyoxyethylene coconut oil propylene diamine, polyoxyethylene palm oil propylene diamine, diamine compounds having a polyalkylene oxide structure illustrated polyoxyethylene beef tallow propylene diamine, and the like. Further, Esododumin T / 13, Esododumine T / 25 (above, manufactured by Lion Corporation), Naimine DT-203, Naimine DT-208 (above, manufactured by NOF Corporation) and the like are commercially available.

  Specific compounds represented by the general formula (A4) include, for example, lauryl dipropylene triamine, stearyl dipropylene triamine, oleyl dipropylene triamine, coconut oil alkyldipropylene triamine as the compound (a2) having two or more amino groups. Alkyl or alkenyltriamines such as palm oil alkyldipropylenetriamine, beef tallow alkyldipropylenetriamine, hardened beef tallowalkyldipropylenetriamine, and the like, and triamine Y12D, triamine T (above, manufactured by Lion Co., Ltd.) and the like are available as commercial products it can.

  In addition, the compound represented by the general formula (A5) is an amine compound (a3) having only one amino group, such as hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, or Primary amines such as oleylamine; secondary amines such as dihexylamine, dioctylamine, didecylamine, didodecylamine, ditetradecylamine, dihexadecylamine, dioctadecylamine, dioleylamine: trihexylamine, trioctylamine, tridecyl Examples include amines having about 6 to 18 carbon atoms such as tertiary amines such as amine, tridodecylamine, tritetradecylamine, trihexadecylamine, trioctadecylamine, and trioleylamine. Is, secondary or tertiary amines are preferred, more preferably a tertiary amine.

  Of the amine compounds (A) described above, the amine compound (amino alcohol compound) (a1) having a hydroxyl group and an amino group is the total number of carbon atoms of the hydrocarbon group in consideration of solubility in the lubricating base oil. Is preferably 12 or more. Moreover, the compound shown by general formula (A1) is preferable from a viewpoint which can make the solubility with respect to lubricating base oil, and a friction coefficient lower among the said amine compounds (A).

The amine compound (amino alcohol compound) (a1) having a hydroxyl group and an amino group includes a compound (Aa) having at least one of a primary amino group and a secondary amino group, and a compound (Ae) having an epoxy group. ) Is preferably obtained.
Specific examples of the compound (Aa) having at least one of a primary amino group and a secondary amino group include a primary amine or a secondary amine, and the primary amine has a total carbon number of 1 or more. It preferably has 32 or less hydrocarbon groups, and may further contain an oxygen atom. The secondary amine preferably has a hydrocarbon group having 2 to 40 carbon atoms in total, and may further contain an oxygen atom.
In the primary amine or the secondary amine, if the total carbon number of the hydrocarbon group is not less than the above lower limit, the amino alcohol compound obtained from the primary amine or the secondary amine is sufficiently dissolved in the lubricating base oil. If it is less than the above upper limit, a high base number amino alcohol compound can be obtained.

  The hydrocarbon group possessed by the primary amine and the secondary amine may be saturated or unsaturated, may be aliphatic or aromatic, and may be linear, branched or cyclic. Specifically, methyl group, ethyl group, propyl group, butyl group, butenyl group, hexyl group, hexenyl group, octyl group, octenyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, decenyl group, dodecyl group Group, dodecenyl group, tridecyl group, tetradecyl group, tetradecenyl group, pentadecyl group, hexadecyl group, hexadecenyl group, heptadecyl group, octadecyl group, octadecenyl group, stearyl group, isostearyl group, oleyl group, linole group, nonadecyl group, icosyl group Eicosyl group, heicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl group, decentrimer , Polybutene group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group and other aliphatic hydrocarbon groups, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl Groups, aromatic hydrocarbon groups such as a trimethylphenyl group, a butylphenyl group, and a naphthyl group.

Specific examples of the primary amine include methylamine, ethylamine, butylamine, hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, 2-ethylhexylamine, 2-decyltetradecylamine, Examples include oleylamine, ethanolamine, propanolamine, octadecyloxyethylamine, 3- (2-ethylhexyloxy) propylamine, 12-hydroxystearylamine, cyclohexylamine, and aniline.
Specific examples of secondary amines include dimethylamine, diethylamine, dibutylamine, dihexylamine, dioctylamine, didecylamine, didodecylamine, ditetradecylamine, dihexadecylamine, dioctadecylamine, di-2-ethylhexylamine, di- Mention may be made of oleylamine, methylstearylamine, ethylstearylamine, methyloleylamine, diethanolamine, dipropanolamine, 2-butylaminoethanol, hexylaminoethanol, phenylaminoethanol, cyclohexylethanolamine. In addition, cyclic secondary amines such as piperidine, piperazine and morpholine can also be mentioned.

  The compound (Ae) having an epoxy group is preferably a compound in which an epoxy group and a hydrocarbon group are directly bonded, and the hydrocarbon group may be saturated or unsaturated, and may be aliphatic or aromatic. It may be linear, branched or cyclic, and examples thereof include an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, or an aromatic hydrocarbon group. More specifically, the hydrocarbon group includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a hexenyl group, an octyl group, an octenyl group, a decyl group, a decenyl group, a dodecyl group, and a dodecenyl group. , Tetradecyl group, tetradecenyl group, hexadecyl group, hexadecenyl group, octadecyl group, octadecenyl group, isostearyl group, decene trimer group, polybutene group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl Aliphatic hydrocarbon groups such as phenyl groups, phenyl groups, methylphenyl groups, ethylphenyl groups, dimethylphenyl groups, propylphenyl groups, trimethylphenyl groups, butylphenyl groups, naphthyl groups, etc. It is.

  Specific examples of the compound (Ae) having an epoxy group include ethylene oxide, propylene oxide, 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyoctane, 1,2 -Epoxydecane, 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane, 1,2-epoxydodecane, 1,2 -Epoxytetradecene, 1,2-epoxyhexadecene, 1,2-epoxyoctadecene, 1,2-epoxy-2-octyldodecane and the like.

The amino alcohol compound is preferably a compound obtained by reacting the amine compound (Aa) and the epoxy compound (Ae) in a ratio (molar ratio) of 1: 0.7 to 1:12. More preferably, the compound is obtained by reacting at a ratio of 10: 1 to 10: 1.
The reaction of the amine compound (Aa) and the epoxy compound (Ae) is preferably performed at a temperature of about 50 ° C. to 250 ° C., more preferably about 80 ° C. to 200 ° C.

[Amide compound (B)]
The amide compound (B) having a hydroxyl group is an amide alcohol compound having one or more amide groups in the molecule and one or more hydroxyl groups in the molecule, and is represented by the following general formula (B1) or general formula (B2): It is preferable that it is a compound shown by these.

In the formulas (B1) and (B2), R ₅₁ , R ₆₁ and R ₆₂ are each a hydrocarbon group having 1 to 32 carbon atoms, and R ₆₁ and R ₆₂ may be the same as or different from each other.
The hydrocarbon group for R ₅₁ , R ₆₁ , and R ₆₂ may be saturated or unsaturated, may be aliphatic or aromatic, may be linear, branched or cyclic, and may be, for example, an alkyl group or an alkenyl group. Examples thereof include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. Specifically, methyl group, ethyl group, propyl group, butyl group, butenyl group, hexyl group, hexenyl group, octyl group, octenyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, decenyl group, dodecyl group Group, dodecenyl group, tridecyl group, tetradecyl group, tetradecenyl group, pentadecyl group, hexadecyl group, hexadecenyl group, heptadecyl group, octadecyl group, octadecenyl group, stearyl group, isostearyl group, oleyl group, linole group, nonadecyl group, icosyl group Eicosyl group, heicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl group, decentrimer , Polybutene group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, aliphatic hydrocarbon group such as trimethylcyclohexyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl Groups, aromatic hydrocarbon groups such as propylphenyl group, trimethylphenyl group, butylphenyl group and naphthyl group.
_Here, the carbon number of the hydrocarbon groups _{R 51} and _{R 61} is preferably 4 to 22, 6 to 18 is more preferable. _The number of carbon atoms of the hydrocarbon group _{R 62} is preferably 1 to 18, more preferably 1 to 10, 1 to 4 are particularly preferred.

R _{52 to} R ₅₉ and R _{63 to} R ₆₆ are a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, and may be the same as or different from each other. The hydrocarbon group may be saturated or unsaturated, aliphatic or aromatic, linear, branched or cyclic, for example, an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, or an aromatic group A hydrocarbon group is mentioned. More specifically, methyl group, ethyl group, propyl group, butyl group, butenyl group, hexyl group, hexenyl group, octyl group, octenyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, decenyl group, Dodecyl, dodecenyl, tridecyl, tetradecyl, tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, stearyl, isostearyl, oleyl, linole, cyclopentyl, cyclohexyl Group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, aliphatic hydrocarbon group such as trimethylcyclohexyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group Group, propylphenyl group, trimethylphenyl group, butylphenyl group, and aromatic hydrocarbon groups such as a naphthyl group.
Examples of the hydrocarbon group _{R 52 ~R 59, R 63 ~R} 66, preferably has 1 to 16 carbon atoms, more preferably those having 1 to 12 carbon atoms, particularly preferably from 1 to 10 carbon atoms.

  Here, n shows the integer of 0-20, o and p show the integer of 1-20, respectively. Moreover, n + o = 1-20 is shown. In addition, (n + o) and p are each preferably 1 to 12, more preferably 1 to 10.

In the general formula (B1), all of R _{52 to} R ₅₅ and R _{56 to} R ₅₉ are hydrogen atoms, or R _{52 to} R ₅₄ and R _{56 to} R ₅₈ are all hydrogen atoms and R ₅₅ , it is preferred one or both of R ₅₉ is a hydrocarbon group.
In General Formula (B2), it is preferable that all of R _{63 to} R ₆₅ are hydrogen atoms, and R ₆₆ is a hydrogen atom or a hydrocarbon group.

Specific compounds of the general formula (B1) include octyl diethanolamide, decyl diethanolamide, dodecyl diethanolamide, stearyl diethanolamide, oleyl diethanolamide, coconut oil fatty acid diethanolamide, palm oil fatty acid diethanolamide, rapeseed oil fatty acid diethanolamide. And fatty acid dialkanolamides such as fatty acid diethanolamide exemplified by beef tallow fatty acid diethanolamide.
These fatty acid dialkanolamides are known as Starhome F, Starhome T, Starhome FK, Starhome DL, Starhome DF-1, Starhome DF-2, Starhome DF-4, Starhome DFC, Starhome DO, Starhome Home DOS (above, manufactured by NOF Corporation), Amizole CDE, Amizole FDE, Amizole KD-1, Amizole KD-3, Amizole CD, Amizole FD, Amizole CDC, Amizole M, Amizole LDE, Amizole LMDE, Amizole MDE, Amizole SDE, amizole SDHE, amizole ODE, amizole ODHE (manufactured by Kawaken Fine Chemical Co., Ltd.), polynon DAO, polynon DAL-C, polynon DAT (manufactured by Shoei Pharmaceutical Co., Ltd.) and the like are commercially available.
Specific compounds represented by the general formula (B1) include polyoxyethylene octanoic acid amide, polyoxyethylene decanoic acid amide, polyoxyethylene lauric acid amide, polyoxyethylene myristic acid amide, polyoxyethylene palmitic acid amide. , Polyoxyethylene stearic acid amide, polyoxyethylene oleic acid amide, polyoxyethylene coconut oil fatty acid amide, polyoxyethylene palm oil fatty acid amide, polyoxyethylene rapeseed oil fatty acid amide, polyoxyethylene beef tallow fatty acid amide, etc. Examples include fatty acid amides having a polyalkylene oxide structure such as polyoxyalkylene fatty acid amide, and these are usually monoalkanolamides in which only one of n and o is 1 or more, It may be a di-alkanolamides any of o is 1 or more, or a mixture thereof.

Specific compounds of the general formula (B2) include N-methyl-octylethanolamide, N-methyl-decylethanolamide, N-methyl-dodecylethanolamide, N-methyl-oleylethanolamide, coconut oil fatty acid N- Fatty acid N-alkyl monoalkanolamides such as fatty acid N-alkylethanolamides exemplified by methylethanolamide, palm oil fatty acid N-methylethanolamide, rapeseed oil fatty acid N-methylethanolamide, beef tallow fatty acid N-methylethanolamide, etc. Can be mentioned. Fatty acid N-alkyl monoalkanol amides are: Esomide HT / 15, Esomide HT / 60, Esomide O / 15 (above, manufactured by Lion Co., Ltd.), Amizole CME, Amizole SME, Amizole PCME, Amizole PLME-A, Amidette 2C, Amidette 5C, Amidette 10C, Amidette 2L-Y, Aminex HO (manufactured by Kawaken Fine Chemical Co., Ltd.), Stahome MF pellet, Stahome LIPA (manufactured by NOF Corporation), Aminone C-11S (manufactured by Kao Corporation) ) Is commercially available.
Of the amide compounds (B), the compound represented by the general formula (B2) is preferable from the viewpoint of reducing the friction coefficient.

[Imide compound (C)]
The imide compound (C) has one or more imide groups in the molecule, and is preferably a succinimide. Examples of the succinimide include compounds represented by the following general formula (C1).

In the formula (C1), R ₆₉ is a hydrocarbon group having 20 to 150 carbon atoms, which may be saturated or unsaturated, aliphatic or aromatic, linear or branched, For example, an alkenyl group or an alkyl group can be mentioned. Moreover, s is an integer of 0-5.
As the alkenyl group or alkyl group having 20 to 150 carbon atoms, a polymer or copolymer of monoolefin or diolefin having 2 to 16 carbon atoms or a hydrogenated product thereof is usually used. Specific examples of the monoolefin include ethylene, propylene, butene, butadiene, decene, dodecene, hexadecene and the like. Among these monoolefins, in the present invention, butene is particularly preferred from the viewpoint of improving the cleanliness at high temperature and being easily available, and is a polybutenyl group which is a polymer thereof, and an alkyl group obtained by hydrogenating it. Hydrogenated polybutenyl groups are preferred. By setting the carbon number of the alkenyl group or alkyl group to 20 or more, the alkenyl group or the alkyl group can be sufficiently dissolved in a lubricating base oil and the like, and the dispersibility, which is the original function of succinimide, can also be exhibited. Moreover, it can prevent that a viscosity becomes high by setting it as 150 or less.
In the case of the imide compound (C), the ratio of the integral value of the chemical shift peak of 5 to 25 ppm to the integral value of the chemical shift peak of −10 to 25 ppm tends to be relatively low. 0.80 is better, especially 0.55 to 0.70.

In the succinimide represented by the general formula (C1), an alkene having 20 to 150 carbon atoms and maleic anhydride are reacted under the conditions of a reaction temperature of 50 to 280 ° C., and the following general formula (C2): It can be obtained by heating and stirring the polyamine represented at a reaction temperature of 50 to 250 ° C.
At this time, the molar ratio of alkene having 20 to 150 carbon atoms and maleic anhydride can be adjusted at a ratio of 1: 5 to 5: 1, and the ratio of alkenyl succinic anhydride to polyamine (D2) is 1: 5. It can be adjusted at a ratio of ˜5: 1.

（なお、一般式（Ｃ２）において、ｔは０〜５の整数である。）

(In general formula (C2), t is an integer of 0 to 5.)

  Examples of the polyamine (C2) include, for example, ethylenediamine, propanediamine, butanediamine, alkylenediamine such as N-methyl-1,3-propanediamine, N, N-dimethyl-1,3-propanediamine, and diethylenetriamine, Examples include polyalkylene polyamines such as triethylenetetramine and tetraethylenepentamine, and polyalkylene polyamines having cyclic alkylene amines such as aminoethylpiperazine.

[Ester compound (D)]
The ester compound (D) is a compound having one or more hydroxyl groups in the molecule, and examples thereof include compounds represented by the following general formula (D1) or (D2).

In the formulas (D1) and (D2), R ₈₁ and R ₁₀₁ are each a hydrocarbon group having 1 to 32 carbon atoms. Such a hydrocarbon group may be saturated or unsaturated, and may be aliphatic or aromatic. It may be a straight chain, branched or cyclic, and examples thereof include an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, or an aromatic hydrocarbon group.
Examples of the hydrocarbon group of R ₈₁ and R ₁₀₁ include a methyl group, an ethyl group, a propyl group, a butyl group, a butenyl group, a hexyl group, a hexenyl group, an octyl group, an octenyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, Undecyl, decenyl, dodecyl, dodecenyl, tridecyl, tetradecyl, tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, stearyl, isostearyl, oleyl, linole Group, nonadecyl group, icosyl group, eicosyl group, heicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotri Contyle group, decent trimer group, polybutene group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, trimethylcyclohexyl group and other aliphatic hydrocarbon groups, phenyl group, methylphenyl group, Examples thereof include aromatic hydrocarbon groups such as ethylphenyl group, dimethylphenyl group, propylphenyl group, trimethylphenyl group, butylphenyl group, and naphthyl group.
_Here, the carbon number of the hydrocarbon groups _{R 81} and _{R 101} is preferably 8 to 32, 12 to 24 is more preferable.

R _{82 to} R ₈₅ and R _{102 to} R ₁₀₆ are each a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, and may be the same as or different from each other. Such a hydrocarbon group may be saturated or unsaturated. It may be aliphatic or aromatic, and may be linear, branched or cyclic, and examples thereof include an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, or an aromatic hydrocarbon group. More specifically, methyl group, ethyl group, propyl group, butyl group, butenyl group, hexyl group, hexenyl group, octyl group, octenyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, decenyl group, Dodecyl, dodecenyl, tridecyl, tetradecyl, tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, stearyl, isostearyl, oleyl, linole, cyclopentyl, cyclohexyl Group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, aliphatic hydrocarbon group such as trimethylcyclohexyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group Group, propylphenyl group, trimethylphenyl group, butylphenyl group, and aromatic hydrocarbon groups such as a naphthyl group.
Moreover, r shows the integer of 1-20, Preferably it is 1-12, More preferably, it is 1-10.
In the general formula (D1), it is preferable that all of R _{82 to} R ₈₅ are hydrogen atoms, or that R _{82 to} R ₈₄ are all hydrogen atoms and R ₈₅ is a hydrocarbon group. In the general formula _(D2), it is preferable that all of R 102 _{to R 106} is a hydrogen atom.

The compound represented by the general formula (D1) is obtained, for example, by a reaction between a fatty acid and an alkylene oxide.
Here, examples of the fatty acid for obtaining the compound represented by the general formula (D1) include lauric acid, myristic acid, palmitic acid, oleic acid, beef tallow fatty acid, coconut oil fatty acid and the like.
Examples of the alkylene oxide include alkylene oxides having 2 to 12 carbon atoms, such as ethylene oxide, propylene oxide, butylene oxide, hexylene oxide, octylene oxide, decylene oxide, and dodecylene oxide. Is mentioned.
Examples of the compound of the general formula (D1) include polyoxyethylene monolaurate, polyoxyethylene monostearate, and polyoxyethylene monooleate. Moreover, the compound of general formula (D1) is nonion (L-2, L-4, S-2, S-4, S-6, S-10, S-15, S-15K, S-15.4. , O-2, O-3, O-4, O-5, O-6) (manufactured by Lion Corporation), Ionette series (MS-400, MS-1000, DL-200 and DS-4000, MO-400) , MO-600, DO-400, DO-600) (manufactured by Sanyo Chemical Industries, Ltd.) is commercially available.

Examples of the compound represented by the general formula (D2) include glycerol fatty acid monoesters such as glycerol monolaurate, glycerol monostearate, glycerol monomysterate, and glycerol monooleate.
The compound represented by the general formula (D2) includes, as commercially available products, UNIGURI GO-102R, UNIGURI GO-106, UNIGLY GL-106, UNIGLY GS-106 (manufactured by NOF Corporation), Ryoto Polyglycerester L- 10D, Ryoto-polyglyceryl ester L-7D, Ryoto-polyglycerol ester M-10D, Ryoto-polyglycerol ester M-7D, Ryoto-polyglycerol ester P-8D, Ryoto-polyglycerol ester SWA-20D, Ryoto-polyglycerol ester Ryoto-polyglycerol ester SWA-10D, Ryoto polyglycerester O-50D, Ryoto polyglycerester O-15D, Ryoto polyglycerate ER-60D (manufactured by Mitsubishi Chemical Foods Co., Ltd.), NIKKOL DGMO-CV, NIKKOL DGMO-90V, IKKOL Tetraglyn1-OV, NIKKOL Decaglyn1-OV, NIKKOL Decaglyn 1-LN, NIKKOL Decaglyn 5-HS, NIKKOL Decaglyn 5-OV, NIKKOL Decaglyn 7-OV, NIKKOL Decaglyn 10-OV, NIKKOL Decaglyn 10-MAC, NIKKOL Decaglyn PR- 20 (above, manufactured by Nikko Chemicals Co., Ltd.) can be obtained.

[Alcohol compound (E)]
The alcohol compound (E) is a compound having one or more hydroxyl groups in the molecule, and examples thereof include compounds represented by the following general formulas (E1), (E2), and (E3).

In the general formulas (E1) to (E3), R ₇₁ , R ₉₁ and R ₁₁₁ are each a hydrocarbon group having 1 to 32 carbon atoms. Such a hydrocarbon group may be saturated or unsaturated, It may be aliphatic or aromatic, and may be linear, branched or cyclic, and examples thereof include an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, or an aromatic hydrocarbon group. Examples of the hydrocarbon group in R ₇₁ , R ₉₁ and R ₁₁₁ include a methyl group, an ethyl group, a propyl group, a butyl group, a butenyl group, a hexyl group, a hexenyl group, an octyl group, an octenyl group, a 2-ethylhexyl group, a nonyl group, Decyl, undecyl, decenyl, dodecyl, dodecenyl, tridecyl, tetradecyl, tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, stearyl, isostearyl, oleyl Group, linole group, nonadecyl group, icosyl group, eicosyl group, heicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriaco group Aliphatic hydrocarbon groups such as til group, dotriacontyl group, decentrimer group, polybutene group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, and trimethylcyclohexyl group, phenyl group, methyl group Examples thereof include aromatic hydrocarbon groups such as phenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, trimethylphenyl group, butylphenyl group, and naphthyl group.
As the hydrocarbon group for R ₇₁ , R ₉₁ , and R _111, a hydrocarbon group having 8 to 24 carbon atoms is preferable, and a hydrocarbon group having 8 to 18 carbon atoms is more preferable.

R _{72 to} R ₇₅ , R _{92 to} R _{98, and} R _{112 to} R ₁₁₈ are each a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, and may be the same as or different from each other. Such a hydrocarbon group may be saturated or unsaturated, may be aliphatic or aromatic, may be linear, branched or cyclic, for example, an aliphatic hydrocarbon group such as an alkyl group or an alkenyl group, Or an aromatic hydrocarbon group is mentioned. More specifically, methyl group, ethyl group, propyl group, butyl group, butenyl group, hexyl group, hexenyl group, octyl group, octenyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group, decenyl group, Dodecyl, dodecenyl, tridecyl, tetradecyl, tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, stearyl, isostearyl, oleyl, linole, cyclopentyl, cyclohexyl Group, methylcyclohexyl group, ethylcyclohexyl group, propylcyclohexyl group, dimethylcyclohexyl group, aliphatic hydrocarbon group such as trimethylcyclohexyl group, phenyl group, methylphenyl group, ethylphenyl group, dimethylphenyl group Group, propylphenyl group, trimethylphenyl group, butylphenyl group, an aromatic hydrocarbon group and a naphthyl group.
As this hydrocarbon group, a C1-C16 thing is preferable, A C1-C12 thing is more preferable, A C1-C10 thing is especially preferable.
Moreover, although q shows the integer of 0-20, Preferably it is 0-12, More preferably, it is 0-10.
In General Formula (E1), it is preferable that all of R _{72 to} R ₇₅ are hydrogen atoms, or any one is a hydrocarbon group and the other is a hydrogen atom. In the general formula (E2), A is preferably an oxygen atom, and any of R _{92 to} R ₉₈ is preferably a hydrogen atom. In general formula (E3), it is preferable that all of R _{112 to} R ₁₁₇ are hydrogen atoms, and R ₁₁₇ is a hydrocarbon group.

  The specific compound of the general formula (E1) is a compound having q of 0 and having one hydroxyl group in the molecule, such as hexanol, heptanol, octanol, nonaol, decanol, undecanol, dodecanol, tridecanol, tetradecanol. , Pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, docosanol, tricosanol, tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nonacosanol, triacosanol, etc. Chain alkanols; hexenol, heptenol, octenol, nonenol, decenol, undecenol, dodecenol, tridecenol, tetradecenol, pentadeceno Straight chain alkenols such as hexadecenol, pentadecenol, hexadecenol, hexadecenol, heptadecenol, octadecenol, nonadecenol, eisenol, docosenol, tetracosenol, pentacosenol, hexacosenol, heptacosenol, heptacosenol, octacosenol, nonacosenol and triaconsenol; 2-ethylhexanol; 1-methylheptadecanol, 1-hexylheptanol, isodecanol, isotridecanol and other branched alkanols; isohexenol, 2-ethylhexenol, isotridecenol, 1-methylheptadecenol, 1-hexylheptenol And alcohol compounds such as branched alkenols such as isotridecenol and isooctadecenol.

Moreover, as a specific compound shown by General formula (E1) whose q is 1-20, the alkylene oxide adduct and styrene oxide adduct of said various alcohol compound are mentioned. Here, examples of the alkylene oxide include alkylene oxides having 2 to 8 carbon atoms. Specific examples include ethylene oxide, propylene oxide, butylene oxide, hexylene oxide, octylene oxide, decylene oxide, and dodecylene oxide. Can be mentioned.
The number of moles of alkylene oxide added is preferably 1-20, more preferably 1-10, and particularly preferably 1-7, per mole of alcohol. Within this range, the solubility in mineral oil is further improved.
The alkylene oxide may be added singly or in combination of two or more, and when mixed and added, the alkylene oxide may be in a block form, a random form, or a combination thereof. Specifically, polyoxyethylene glycol, polyoxypropylene glycol, polyoxypropylene / ethylene glycol (bonding mode of oxypropylene and oxyethylene: random), polyoxybutylene / ethylene glycol (bonding mode of oxypropylene and oxyethylene: Random), polyoxyethylene / polyoxypropylene / polyoxyethylene glycol (bonding mode of oxypropylene and oxyethylene: block).
Further, the carbon number of the alcohol compound (E) is preferably C12 to C30, preferably C12 to C24, and particularly preferably C12 to C18. When the carbon number is within these ranges, the solubility in mineral oil is good.

  Compounds represented by general formula (E1) in which q is 1 to 20 are commercially available as nonion (K-204, K-220, K-230), persoft (NK-60, NK-60C, NK- 100, NK-100C), nonion (P-208, P-210, P-213, E-202, E-202S, E-205, E-205S, E-212, E-215, E-230, S -202, S-207, S-215, S-220, EH-204, EH-208, ID-203, ID-206, ID-209, EAD-13, TA-405, TA-407, TA-409 TA-411, TA-412, TA-413, TA-415, TA-418) (above, manufactured by Lion Corporation), BLAUNON series (EL-1303, EN-1502, EN-905, EH) 2, EH-4, DAL-2, DAH-3, NDB-2040, DAP-1008, ELP-0809B, ELP-1608B, EHP-4, BPO-3), FINESURF series (NDB-800, IDEP-608, IDEP-604, IDEP-802, IDEP-560, IDEP-580, IDEP-9161, IDEP-5010, IDEP-9010, IDEP-7045, IDEP-7085, 5010, 7045, 7085, 9010, TDP-0108, TDP- 0109, TDP-0255, TDP-0633K, TDP-1033, TDP-1055), WONDERSURF series (100, 140, NDR-800, NDR-1000, NDR-1400, RL-80, RL-100, RL-80, RL 100, RL-140, ID-50, ID-70, ID-90, S-800, S-1000, S-1400 (above, manufactured by Aoki Yushi Kogyo Co., Ltd.), Lionol series (TDL-20, TDL) -30, TDL-50) (above, manufactured by Lion Corporation), New Pole Series (LB-285, LB-625, LB-1715, 50HB-100, 50HB-260, 50HB-400, 50B-2000, 50HB- 5100, PP-400) (manufactured by Sanyo Chemical Industries, Ltd.).

  Examples of the compound represented by the general formula (E2) include 3- (dodecyloxy) propane-1,2-diol, 3- (tetradecyloxy) propane-1,2-diol, 3- (hexadecyloxy) propane- 1,2-diol, 3- (octadecyloxy) propane-1,2-diol, 3- (oleyloxy) propane-1,2-diol, 1,2-dodecanediol, 1,2-tetradecanediol, 1, Examples include 2-hexadecanediol and 1,2-octadecanediol.

Examples of the compound represented by the general formula (E3) include lauryl glycol hydroxypropyl ether, myristyl glycol hydroxypropyl ether, stearyl glycol hydroxypropyl ether, oleyl glycol hydroxypropyl ether, and the like. Moreover, as a commercial item of the compound shown by general formula (E3), Visco Safe LPE, Visco Safe LMPE (above, Kawaken Fine Chemical Co., Ltd. product) etc. are mentioned.
Among the alcohol compounds (E), a compound represented by the general formula (E2) is preferable from the viewpoint of reducing the friction coefficient.
Further, among the compounds (A) to (E), the compounds (A) to (C) are preferable from the viewpoint of reducing friction and improving the wear resistance.

[Method for producing boron-containing compound]
The boron-containing compound according to the present invention is a boron-containing compound obtained by heating and stirring an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative at a temperature of 100 ° C. or higher and 150 ° C. or lower. Although it contains a tricoordinate boron-containing compound and a mixture of tetracoordinate boron-containing compounds, it may consist only of a tricoordinate boron-containing compound. The obtained boron-containing compounds include those in which boric acid or a boric acid derivative is bonded to a compound having a hydroxyl group or an amino group, or those in a state where they are dispersed without being bonded.
When the organic compound and boric acid are heated and stirred at a temperature higher than 150 ° C., the amount of tri-coordinate boron compound is reduced, the effect of reducing the friction coefficient is difficult to obtain, and the viscosity may increase. is there. In particular, when the amide compound (B) is treated at a high temperature, the friction coefficient tends to increase.
In addition, if heating and stirring is not performed at a temperature of 100 ° C. or higher, moisture generated by the dehydration reaction remains, and the remaining moisture causes fuel oil, lubricating oil, and the like to cause hydrolysis of other additives, thereby causing fuel oil. It promotes the deterioration of oil and lubricating oil, etc., causing unstable performance.

In the present invention, the organic compound having a hydroxyl group or amino group and boric acid are preferably heated and stirred for 30 minutes to 30 hours in the temperature range of 100 to 150 ° C., and heated and stirred for 30 minutes to 10 hours. More preferably.
In the present invention, boric acid or a boric acid derivative is added to the organic compound by heating and stirring an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative at a temperature of 100 ° C. or higher and 130 ° C. or lower. It is preferable to act to obtain the boron-containing compound of the present invention.

Specifically, in the present invention, first, an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative are mixed and stirred and mixed at less than 100 ° C. (for example, around 80 ° C.). By dehydrating, borate and boric acid dispersions are obtained. Thereafter, the temperature is increased gradually or stepwise, and dehydrated while stirring and mixing within a temperature range of 100 to 150 ° C., preferably 100 to 130 ° C., thereby borate and borate esters. , Boric acid amide, and a boron-containing compound consisting of a dispersion of boric acid and a boric acid dehydration condensate, or a boron-containing compound consisting of a mixture thereof.
In this operation, it is preferable to raise the temperature stepwise or gradually even in the temperature range of 100 to 150 ° C.
The heating and stirring of the organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative may be performed in the presence of a solvent, for example, an organic solvent such as hydrocarbon oil.
The timing of adding the solvent is not particularly limited, and may be added to the organic compound before mixing the boric acid or boric acid derivative with the organic compound, or added after mixing the boric acid or boric acid derivative with the organic compound. Also good. Moreover, after heating for a predetermined time in the temperature range of 100-150 degreeC, a solvent may be added and it may heat for a predetermined time further in the temperature range of 100-150 degreeC after that.
In addition, when stirring with heating, the pressure may be reduced to facilitate removal of moisture.
However, in the present invention, an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative are mixed and heated and stirred to obtain a boron-containing compound. And it is preferably not heated to a temperature higher than 130 ° C. Thus, in the present invention, since it is not heated at a high temperature, a large amount of tricoordinate boron compounds can be generated.

  The boron-containing compound is heated and stirred at a ratio of 1: 0.01 or more and 1:10 or less of the number of moles of the organic compound having a hydroxyl group or amino group and the number of moles of boric acid or boric acid derivative. The obtained compound is preferable, and the above ratio is more preferably a compound obtained by heating and stirring at a ratio of 1: 0.05 or more and 1: 8 or less. Here, when the ratio of the number of moles is 1: 0.01 or more, a boron-containing compound excellent in a low friction coefficient and wear resistance can be obtained. On the other hand, when the molar ratio is 1:10 or less, the solubility of the boron-containing compound in the lubricating base oil and fuel oil can be improved.

[Lubricant base oil]
There is no restriction | limiting in particular in the base oil used by this invention, The well-known mineral oil and / or synthetic oil which are used conventionally can be used.
As mineral oil, for example, distillate obtained by subjecting paraffin-based crude oil, intermediate-based crude oil or naphthenic-based crude oil to atmospheric distillation, or distilling the residual oil of atmospheric distillation under reduced pressure, or this according to a conventional method Examples of the refined oil obtained by refining include solvent refined oil, hydrogenated refined oil, hydrocracked oil, dewaxed oil, and clay-treated oil. Furthermore, isomerized oils of waxes (such as slack wax) can also be used.
On the other hand, examples of the synthetic oil include poly α-olefins, polybutenes, polybutenes, polyol esters, and alkylbenzenes, which are α-olefin oligomers having 8 to 14 carbon atoms.
In this invention, 1 type of the said mineral oil may be used as a base oil, and may be used in combination of 2 or more type. Moreover, the said synthetic oil may be used 1 type and may be used in combination of 2 or more type. Further, one or more mineral oils and one or more synthetic oils may be used in combination.
The lubricating oil composition of the present invention usually contains a base oil in addition to the boron-containing compound, but the content of the base oil in the composition is preferably 70% by mass or more, and 80% by mass or more. Is more preferable.

As the base oil, the kinematic viscosity at 100 ° C., usually 1.5~50mm ² / s, preferably 3 to 30 mm ² / s. When the kinematic viscosity at 100 ° C. is 1.5 mm ² / s or more, the evaporation loss is small, and when it is 50 mm ² / s or less, the power loss due to the viscous resistance is suppressed, and the fuel efficiency improvement effect is exhibited well.
The base oil preferably has a viscosity index of 80 or more, more preferably 90 or more, and particularly preferably 100 or more. When the viscosity index is 80 or more, the viscosity change due to the temperature of the base oil is small, and stable lubricating performance is exhibited.
Moreover, as a base oil, the thing whose sulfur content measured based on JISK2541 is 50 mass ppm or less is preferable. If the sulfur content is 50 mass ppm or less, there is an effect of improving the wear resistance of the low friction sliding material. A more preferable sulfur content is 30 mass ppm or less, and further 20 mass ppm or less.

The lubricating oil composition of the present invention further contains one or more of a viscosity index improver, a molybdenum compound, a zinc dialkyldithiophosphate, an antioxidant, a metal detergent, and an ashless dispersant in the base oil. It is preferable that The boron-containing compound of the present invention can sufficiently reduce the friction coefficient of a lubricating oil composition containing these additives.
Hereinafter, each additive will be described in detail.

[Viscosity index improver]
Examples of the viscosity index improver include non-dispersed polymethacrylates, dispersed polymethacrylates, olefin copolymers (for example, ethylene-propylene copolymers), dispersed olefin copolymers, styrene copolymers. (For example, styrene-diene hydrogenated copolymer and the like) and the like, and non-dispersed polymethacrylates such as polyalkyl methacrylate are preferable. The weight average molecular weight of the viscosity index improver is, for example, 10,000 to 1,000,000, preferably 50,000 to 600,000.
The viscosity index improver is usually blended in the lubricating oil composition at about 0.5 to 30% by mass, preferably about 2 to 20% by mass.

[Molybdenum compound]
A molybdenum compound is used as a friction modifier, for example, is shown by the following general formula (F).

In Formula (F), R _{151 to} R ₁₅₄ represent a hydrocarbon group having 4 to 22 carbon atoms, and R _{151 to} R ₁₅₄ may be the same or different. When the number of carbon atoms is 4 or more, the oil solubility is improved, and when it is 22 or less, the melting point becomes an appropriate value, the handling property is improved, and the friction reducing ability is improved. From the above viewpoint, the carbon number is preferably 4-18.

Examples of the hydrocarbon group include an alkyl group, an alkenyl group, an alkylaryl group, a cycloalkyl group, and a cycloalkenyl group, and a branched or straight chain alkyl group or alkenyl group is preferable, and a branched or straight chain group is preferred. An alkyl group is more preferred. Examples of the branched or straight chain alkyl group having 4 to 18 carbon atoms include various butyl groups, various hexyl groups, various octyl groups, various nonyl groups, various decyl groups, various dodecyl groups, various tetradecyl groups, various hexadecyl groups, Examples include various octadecyl groups. Solubility in base oil, in view of storage stability and friction reducing _{ability, R 151} and _{R 152} are the same alkyl _{group, R 153} and _{R 154} are the same alkyl _group, the alkyl of _{R 151} and _{R 152} It is preferred that the group and the alkyl group of R ₁₅₃ and R ₁₅₄ are different.
In the formula (F), X ^{1 to} X ⁴ represent a sulfur atom or an oxygen atom, and X ^{1 to} X ⁴ may be the same or different. The ratio of sulfur atom to oxygen atom is preferably sulfur atom / oxygen atom = 1/3 to 3/1, more preferably 1.5 / 2.5 to 3/1. Within the above range, good performance can be obtained in terms of corrosion resistance and solubility in base oil. Further, all of X ^{1 to} X ⁴ may be sulfur atoms or oxygen atoms.
In the present invention, the friction coefficient of the lubricating oil composition can be satisfactorily reduced by blending a molybdenum compound in addition to the boron-containing compound.
The organomolybdenum compound is preferably blended in the lubricating oil composition in an amount of usually 0.005 to 0.5% by mass, preferably about 0.01 to 0.15% by mass.

一般式（Ｇ）において、Ｒ_１５５〜Ｒ_１５８は、それぞれ独立にアルキル基を示し、好ましくは炭素数１〜２４のアルキル基が用いられる。
炭素数１〜２４のアルキル基は直鎖状、分岐鎖状、環状のいずれであってもよく、具体的にはメチル基、エチル基、各種プロピル基、各種ブチル基、各種ペンチル基、各種ヘキシル基、各種ヘプチル基、各種オクチル基、各種ノニル基、各種デシル基、各種ウンデシル基、各種ドデシル基、各種トリデシル基、各種テトラデシル基、各種ペンタデシル基、各種ヘキサデシル基、各種ヘプタデシル基、各種オクタデシル基、各種ノナデシル基、各種イコシル基、各種ヘンイコシル基、各種ドコシル基、各種トリコシル基及び各種テトラコシル基、あるいはシクロペンチル基、シクロヘキシル基、シクロヘプチル基及びこれらのアルキル置換体などが挙げられる。
ジアルキルジチオリン酸亜鉛は、潤滑油組成物に、通常０．０１〜１０質量％、好ましくは０．１〜５質量％程度配合されることが好ましい。[Zinc dialkyldithiophosphate]
Zinc dialkyldithiophosphate is used as an antiwear agent, and examples thereof include compounds represented by the following general formula (G).

In General Formula (G), R _{155 to} R ₁₅₈ each independently represent an alkyl group, and preferably an alkyl group having 1 to 24 carbon atoms.
The alkyl group having 1 to 24 carbon atoms may be linear, branched or cyclic, and specifically, methyl group, ethyl group, various propyl groups, various butyl groups, various pentyl groups, various hexyls. Group, various heptyl groups, various octyl groups, various nonyl groups, various decyl groups, various undecyl groups, various dodecyl groups, various tridecyl groups, various tetradecyl groups, various pentadecyl groups, various hexadecyl groups, various heptadecyl groups, various octadecyl groups, Examples include various nonadecyl groups, various icosyl groups, various heicosyl groups, various docosyl groups, various tricosyl groups and various tetracosyl groups, or cyclopentyl group, cyclohexyl group, cycloheptyl group, and alkyl substituted products thereof.
The zinc dialkyldithiophosphate is preferably added to the lubricating oil composition in an amount of usually 0.01 to 10% by mass, preferably about 0.1 to 5% by mass.

[Antioxidant]
Examples of the antioxidant include phenolic antioxidants and amine antioxidants.
Examples of the phenolic antioxidant include 4,4′-methylenebis (2,6-di-t-butylphenol); 4,4′-bis (2,6-di-t-butylphenol); 4,4′- Bis (2-methyl-6-tert-butylphenol); 2,2′-methylenebis (4-ethyl-6-tert-butylphenol); 2,2′-methylenebis (4-methyl-6-tert-butylphenol); 4 4,4′-butylidenebis (3-methyl-6-tert-butylphenol); 4,4′-isopropylidenebis (2,6-di-tert-butylphenol); 2,2′-methylenebis (4-methyl-6- Nonylphenol); 2,2′-isobutylidenebis (4,6-dimethylphenol); 2,2′-methylenebis (4-methyl-6-cyclohexylphenol); 2,6-di-t-butyl- 2,6-di-t-butyl-4-ethylphenol; 2,4-dimethyl-6-t-butylphenol; 2,6-di-t-amyl-p-cresol; Di-t-butyl-4- (N, N′-dimethylaminomethylphenol); 4,4′-thiobis (2-methyl-6-tert-butylphenol); 4,4′-thiobis (3-methyl-6) -T-butylphenol); 2,2'-thiobis (4-methyl-6-t-butylphenol); bis (3-methyl-4-hydroxy-5-t-butylbenzyl) sulfide; bis (3,5-di-) -T-butyl-4-hydroxybenzyl) sulfide; n-octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate; 2,2'-thio [diethyl-bis-3- ( 3, - di -t- butyl-4-hydroxyphenyl) propionate] and the like.

Examples of amine-based antioxidants include monoalkyl diphenylamines such as monooctyldiphenylamine and monononyldiphenylamine; 4,4′-dibutyldiphenylamine; 4,4′-dipentyldiphenylamine, 4,4′-dihexyldiphenylamine, 4, Dialkyldiphenylamines such as 4′-diheptyldiphenylamine, 4,4′-dioctyldiphenylamine, 4,4′-dinonyldiphenylamine; polyalkyldiphenylamines such as tetrabutyldiphenylamine, tetrahexyldiphenylamine, tetraoctyldiphenylamine, tetranonyldiphenylamine; Naphthylamine such as naphthylamine; phenyl-α-naphthylamine; butylphenyl-α-naphthylamine, pentylphenyl-α-naphth Triethanolamine, hexylphenyl -α- naphthylamine, heptylphenyl -α- naphthylamine, octylphenyl -α- naphthylamine, alkyl-substituted phenyl -α- naphthylamine, such as nonylphenyl -α- naphthylamine.
The said antioxidant may select 1 type or may use it in combination of 2 or more type. Of the above antioxidants, dialkyldiphenylamine is preferred.
The antioxidant is usually mixed in the lubricating oil composition at about 0.05 to 10% by mass, preferably about 0.1 to 5% by mass.

[Metal-based detergent]
As the metallic detergent, any alkaline earth metal detergent used in lubricating oils can be used, for example, alkaline earth metal sulfonates, alkaline earth metal phenates, alkaline earth metal salicylates, and the like. And a mixture of two or more selected from.
Alkaline earth metal sulfonates include alkaline earth metal salts of alkyl aromatic sulfonic acids obtained by sulfonated alkyl aromatic compounds having a molecular weight of 300 to 1,500, preferably 400 to 700, particularly magnesium salts and / or Or a calcium salt etc. are mentioned, A calcium salt is used preferably especially.
Alkaline earth metal phenates include alkylphenols, alkylphenol sulfides, alkaline earth metal salts of Mannich reactants of alkylphenols, especially magnesium salts and / or calcium salts, among which calcium salts are particularly preferred.
Examples of the alkaline earth metal salicylate include alkaline earth metal salts of alkyl salicylic acid, particularly magnesium salts and / or calcium salts, among which calcium salts are preferably used.
Of these metallic detergents, calcium salicylate is preferably used.
In the present invention, the total base number of the metal detergent is usually 10 to 500 mgKOH / g, preferably 20 to 450 mgKOH / g.
The total base number referred to here is the total base number measured by JIS K-2501: perchloric acid method.
In the lubricating oil composition, the metal detergent is usually added in an amount of 0.1 to 10% by mass, preferably 0.5 to 5.0% by mass.

[Ashless dispersant]
As the ashless dispersant, an imide dispersant that does not contain boron is preferably used. As the imide-based dispersant, succinimide represented by the above general formula (C1) is preferable, and polybutenyl succinimide in which R ₆₉ is a polybutenyl group is more preferable.
The ashless dispersant is usually added to the lubricating oil composition in an amount of about 0.1 to 10% by mass, preferably about 1 to 5% by mass.

[Other additives]
The lubricating composition of the present invention may be formed by blending a pour point depressant, a rust inhibitor, a corrosion inhibitor, an antifoaming agent and the like in addition to the above additives.
As the pour point depressant, for example, polymethacrylate having a weight average molecular weight of about 10,000 to 150,000 can be used. Examples of the rust inhibitor include alkylbenzene sulfonate, dinonyl naphthalene sulfonate, alkenyl succinate, polyhydric alcohol ester and the like. Examples of the corrosion inhibitor include benzotriazole, benzimidazole, benzothiazole, and thiadiazole. Examples of the antifoaming agent include dimethylpolysiloxane and polyacrylate.

As mentioned above, boron-containing compounds, and further, viscosity index improvers, molybdenum compounds, zinc dialkyldithiophosphates, antioxidants, metal-based detergents, ashless dispersants, and other, if necessary Lubricating oil compositions formed by blending various additives selected from additives and the like usually contain those blended, but in some cases, at least part of the blended additives May react to form another compound.
The method for producing a lubricating oil composition of the present invention is to produce a lubricating oil composition by blending the above boron-containing compound into a base oil. Moreover, the manufacturing method of the lubricating oil composition of this invention may manufacture a lubricating oil composition by mix | blending the boron containing compound obtained by the manufacturing method of an above-described boron containing compound with base oil. . In these production methods, the above base oil contains viscosity index improver, molybdenum compound, zinc dialkyldithiophosphate, antioxidant, metal detergent, ashless dispersant, and other additives as necessary. At least one of the various additives may be further blended.

The kinematic viscosity at 100 ° C. of the lubricating oil composition of the present invention is usually 1 to 30 mm ² / s, preferably ² to 15 mm ² / s, and the kinematic viscosity at 40 ° C. is usually 5 to 100 mm ² / s. , Preferably 20 to 80 mm ² / s. The viscosity index is usually 90 or more, preferably about 100 or more.
The lubricating oil composition of the present invention is a lubricating oil composition that has low friction with a boron-containing compound and has good wear resistance, and can be suitably used for an internal combustion engine. The lubricating oil composition of the present invention can improve fuel efficiency, for example, by reducing the friction of sliding parts in the engine.

EXAMPLES Hereinafter, although an Example demonstrates this invention in detail, this invention is not limited at all by these examples. In addition, various physical properties of the boron-containing compound, the base oil, and the lubricating oil composition were measured according to the following methods.
(1) ¹¹ B-NMR
BF ₃ · OEt ₂ was used as an external standard (0 ppm) and measured in deuterated chloroform at a pulse width of 90 °.
(2) Measurement of boron content and nitrogen content in boron-containing compound The boron content is a value measured according to ASTM D4951. The nitrogen content is a value measured according to JISK2609.
(3) Kinematic viscosity, viscosity index These are values measured according to JIS K2283.
(4) Friction coefficient Using an MTM (Mini Traction Machine) testing machine (PCS Instruments), the oil temperature is 80 ° C., the load is 30 N, the speed is 1000 mm / s, and the slip rate (SRR) is 50%. Then, a test was conducted at an oil temperature of 80 ° C., a load of 30 N, a speed of 10 m / s, and an SRR of 50%, and the friction coefficient at that time was measured.

Production Example 1
550 g of polybutene (Mn: 960), 1.5 g of cetyl bromide and 59 g (0.6 mol) of maleic anhydride were placed in a 1 L autoclave, and the reaction was carried out at 240 ° C. for 5 hours after purging with nitrogen. The temperature was lowered to 215 ° C., unreacted maleic anhydride and cetyl bromide were distilled off under reduced pressure, the temperature was lowered to 140 ° C. and filtered. The yield of the obtained polybutenyl succinic anhydride was 550 g, and the saponification value was 86 mgKOH / g.
In a 500 mL separable flask, 200 g of polybutenyl succinic anhydride, 7.2 g (0.056 mol) of aminoethylpiperazine (AEP), 4.3 g (0.042 mol) of diethylenetriamine (DETA), triethylenetetraamine ( TETA) 6.1 g (0.042 mol) and 150 neutral mineral oil 100 g were added and reacted at 150 ° C. for 2 hours under a nitrogen stream. The temperature was raised to 200 ° C., and unreacted AEP, DETA and produced water were distilled off under reduced pressure. The yield of the obtained polybutenyl succinimide was 315 g, and the base value (hydrochloric acid method) was 30.8 mg KOH / g.
A separable flask reaction vessel equipped with a stirrer, a heating device, a thermometer, a Dean-Stark tube, a Dimroth condenser tube and a nitrogen blowing tube was charged with 110 g of polybutenyl succinimide and heated to 70-80 ° C. under a nitrogen stream. did. To this mixture, 19.1 g (0.308 mol) of boric acid was gradually added and stirred at 80 ° C. for 2 hours. Further, the mixture was heated and stirred at 90 to 100 ° C. for 2 hours and at 150 ° C. for 2 hours while dehydrating. The obtained mixture is subjected to pressure filtration (pressure 4.0 kg / cm ² ) using a filter plate (NA-600, retained particle size 0.4 μm, manufactured by Advantech Toyo Co., Ltd.), thereby containing 110 g of boron. Polybutenyl succinimide (boron-containing compound 1) was obtained. This boron-containing polybutenyl succinimide had a boron content of 2.1 mass%, a nitrogen content of 2.1 mass%, and a boron atom / nitrogen atom mass ratio of 1.0.

Production Example 2
A boron-containing polybutenyl succinimide (boron-containing compound 2) was obtained in the same manner as in Production Example 1 except that the amount of boric acid was changed to 13.6 g (0.220 mol). This boron-containing polybutenyl succinimide had a boron content of 1.5% by mass, a nitrogen content of 2.1% by mass, and a boron / nitrogen atom mass ratio of 0.7.

Production Example 3
In a separable flask reaction vessel equipped with a stirrer, a heating device, a thermometer, a Dean-Stark tube, a Dimroth condenser tube and a nitrogen blowing tube, 129.2 g (1.00 mol) of 1-octylamine and 1,2-epoxide decane 368 .6 g (2.00 mol) was charged, and the mixture was heated and stirred at 80 ° C. for 2 hours and 120 ° C. for 2 hours, and further heated and stirred at 160 ° C. for 12 hours, and N, N-bis (2 -Hydroxydodecyl) -N-octylamine was obtained.
Under a nitrogen stream, 61.8 g (1.00 mol) of boric acid was gradually added to the reaction product and stirred at 80 ° C. for 2 hours. Furthermore, it heated and stirred at 90-100 degreeC for 2 hours and 110 degreeC-120 degreeC for 3 hours, spin-dry | dehydrating. 113 g of mineral oil A (kinematic viscosity at 100 ° C. = 4.12 mm ² / s, viscosity index = 134) was added, and the mixture was heated and stirred at 120 ° C. for 30 minutes. By subjecting the obtained mixture to pressure filtration (pressure 4.0 kg / cm ² ) using a filter plate (NA-600, retention particle size 0.4 μm, manufactured by Advantech Toyo Co., Ltd.), 609 g of boron-containing N , N-bis (2-hydroxydodecyl) -N-octylamine (boron-containing compound 3) was obtained. The obtained boron-containing compound had a boron content of 1.7 mass%, a nitrogen content of 2.1 mass%, and a mass ratio of boron atom / nitrogen atom was 0.79.

Production Comparative Example 1
After adding boric acid and stirring at 80 ° C. for 2 hours, the mixture was stirred at 90 to 100 ° C. for 2 hours, 110 to 120 ° C. for 2 hours, and 150 to 160 ° C. for 3 hours, and then filtered in the same manner as in Production Example 2. Except for the above, the same procedure as in Production Example 2 was carried out to obtain a boron-containing polybutenyl succinimide (boron-containing compound 4).

Production Comparative Example 2
A separable flask reaction vessel equipped with a stirrer, a heating device, a thermometer, a Dean-Stark tube, a Dimroth condenser tube and a nitrogen blowing tube was charged with 123.78 g (0.35 mol) of 2-decyltetradecan-1-amine and nitrogen. It heated at 70-80 degreeC under airflow. To this mixture, 21.64 g (0.35 mol) of boric acid was gradually added and stirred at 80 ° C. for 2 hours. Furthermore, it heated and stirred at 90-100 degreeC for 2 hours, 110 to 120 degreeC for 2 hours, and 150 to 160 degreeC for 3 hours, spin-dry | dehydrating. The obtained mixture is subjected to pressure filtration (pressure 4.0 kg / cm ² ) using a filter plate (NA-600, retained particle size 0.4 μm, manufactured by Advantech Toyo Co., Ltd.), thereby containing 125 g of boron. 2-decyltetradecan-1-amine (boron-containing compound 5) was obtained. The boron-containing 2-decyltetradecan-1-amine had a boron content of 2.7% by mass, a nitrogen content of 2.8% by mass, and a boron atom / nitrogen atom mass ratio of 1.0.

About the boron-containing compounds 1 to 5 obtained in each of Production Examples 1 to 3 and Comparative Examples 1 and 2, the boron atom content and the nitrogen atom content were measured to obtain the boron atom weight / nitrogen atom weight (mass basis). It was. Further, ¹¹ B-NMR was measured for the boron-containing compounds 1 to 5 obtained in each of Production Examples 1 to 3 and Comparative Examples 1 and 2, and [the integrated value of the peak of chemical shift 5 to 25 ppm / chemical shift −10]. ˜25 ppm peak integral value] was calculated. The integration ratio is shown in Table 1.

Examples 4 to 6, Comparative Examples 3 and 4
Using the boron-containing compounds 1 to 5 produced in each of Production Examples 1 to 3 and Comparative Examples 1 and 2, a lubricating oil composition having the composition shown in Table 2 below was prepared. About each lubricating oil composition, the friction coefficient was computed by said method. The results are shown in Table 2.

Each component in Table 2 is as follows.
(1) Base oil: Mineral oil (100N), 40 ° C. kinematic viscosity 19.5 mm ² / s, 100 ° C. kinematic viscosity 4.2 mm ² / s, viscosity index 120, sulfur content 10 mass ppm or less (2) Improved viscosity index Agent: Polyalkylmethacrylate (weight average molecular weight: 475,000)
(3) Pour point depressant: polyalkyl methacrylate (weight average molecular weight: 62,000)
(4) Antioxidant: Dialkyldiphenylamine (nitrogen content 4.6% by mass)
(5) Metal detergent: calcium salicylate (total base number 225 mg KOH / g, calcium content 7.8% by mass)
(6) Ashless dispersant: polybutenyl succinimide (nitrogen content 0.7 mass%)
(7) Antiwear agent: zinc dialkyldithiophosphate (Zn content: 0.11% by mass, phosphorus content: 0.10% by mass, alkyl group: mixture of secondary butyl group and secondary hexyl group)
(8) Friction modifier: Molybdenum dithiocarbamate (Mo content: 10% by mass)
(9) Other additives: rust inhibitor, corrosion inhibitor and antifoaming agent

  As is apparent from Tables 1 and 2, in each example in which the boron NMR integration ratio is 0.5 to 1.0 and the boron atom weight / nitrogen atom weight is 0.6 or more, the friction coefficient is 0.06 to As a result, the lubricating oil composition was reduced in friction. On the other hand, in each comparative example having a boron NMR integration ratio of less than 0.50, the friction coefficient was 0.09 to 0.10, and the lubricating oil composition could not be sufficiently reduced in friction.

  According to the present invention, it is possible to obtain a lubricating oil composition having a reduced friction coefficient and reduced friction and improved wear resistance, and the lubricating oil composition is particularly suitable as a lubricating oil for an internal combustion engine. Can be used.

Claims (8)

When BF ₃ · OEt ₂ is used as an external standard (0 ppm) and ¹¹ B-NMR is measured in deuterated chloroform, the integrated value of the chemical shift peak is 5 to 25 ppm with respect to the integrated value of the chemical shift peak of −10 ppm to 25 ppm. A lubricating oil composition comprising a boron-containing compound and a molybdenum compound that have a ratio of 0.5 to 1.0.   2. The lubricating oil composition according to claim 1, wherein the boron-containing compound has a ratio of boron atom weight to nitrogen atom weight of 0.6 or more on a mass basis.   The lubricating oil composition according to claim 1 or 2, wherein the boron-containing compound is obtained by allowing boric acid or a boric acid derivative to act on an organic compound having a hydroxyl group or an amino group.   The organic compound is an amine compound (A), an amide compound (B) having a hydroxyl group, an imide compound (C) having an amino group, an ester compound (D) having a hydroxyl group, and an alcohol compound having an hydroxyl group (E The lubricating oil composition according to claim 3, which is at least one compound selected from the group consisting of:   The lubricating oil composition according to any one of claims 1 to 4, comprising 0.01 to 30% by weight of the boron-containing compound. A base oil consisting of a mineral oil and / or synthetic oils, in addition to the boron-containing compound and the molybdenum compound, viscosity index improvers, di alkyl zinc dithiophosphate, antioxidant, metallic detergents, and ashless dispersant The lubricating oil composition according to any one of claims 1 to 5, comprising at least one of the following.   The lubricating oil composition according to any one of claims 1 to 6, which is a lubricating oil composition for an internal combustion engine. By mixing an organic compound having a hydroxyl group or an amino group and boric acid or a boric acid derivative at a temperature of 100 ° C. or higher and 150 ° C. or lower to obtain a boron-containing compound, and blending the boron-containing compound and the molybdenum compound A method for producing a lubricating oil composition for producing a lubricating oil composition .