JP2020164767A - Additive for lubricant and lubricant composition - Google Patents

Abstract

To provide an additive for a lubricant and a lubricant composition thereof, capable of improving shudder prevention property and friction coefficient μ in good balance.SOLUTION: The additive for a lubricant and a lubricant composition thereof include a triimide type compound selected from one or more kinds represented by the formula below: [in the formula, Ra, Rb, and Rc are respectively and independently a straight chain hydrocarbon group or a branched chain hydrocarbon group of a carbon number of 6-30; x, y, and z are an integer of 1 or 2; La, Lb, and Lc is a divalent hydrocarbon group of a carbon of number 1-10].SELECTED DRAWING: Figure 1

Description

The present invention relates to a lubricating oil additive and a lubricating oil composition.

In recent years, due to increasing demand for improving fuel efficiency of vehicles such as automobiles, lockup clutches are often built into torque converters of automatic transmissions and stepless transmissions mounted on vehicles such as automobiles. It has become.
The lockup clutch has a function of directly transmitting engine torque to a transmission to drive it according to the running conditions of a vehicle such as an automobile. Hereinafter, driving the engine by directly transmitting the engine torque to the transmission is also referred to as "direct drive". Since the torque converter has a built-in lockup clutch, the lockup clutch operates to switch between drive via fluid (drive system oil) and direct drive in the torque converter at the optimum timing. Therefore, as compared with the case where the torque converter does not have a built-in lockup clutch, the stirring loss is reduced, the power transmission efficiency is improved, and the fuel efficiency is improved.

By the way, from the viewpoint of transmitting the input engine torque to the transmission without waste, it is required to impart a high friction coefficient μ to the lubricating oil.
As an additive for lubricating oil that imparts a high coefficient of friction μ to the lubricating oil, for example, it has one group derived from succinimide in the molecule, and the group derived from the succinimide is a polymer chain. A monoimide-type compound represented by the following general formula (A) having the above as a substituent is known (see Patent Document 1).

(In the general formula (A), R ¹ is an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000.)

In the present specification, the group derived from succinimide means a monovalent group represented by the following chemical structural formula (B). "*" In the following chemical structural formula (B) means a bond position with another atom.
In the following description, the group derived from imide succinate is also referred to as "imide succinate group".

Further, as another additive for lubricating oil for improving the friction coefficient μ of the lubricating oil, for example, it has two succinimide groups in the molecule, and the two succinimide groups contain a polymer chain. A succinimide-type compound represented by the following general formula (C), which is bound via a linker, is known (see Patent Document 2).

(In the general formula (C), ^{R 1} represents an alkyl group or a number-average molecular weight of 500 to 5000 than the alkenyl groups of less than 5000 number average molecular weight of 500 or more, two ^{R 1} in the same molecule are the same to each other May be different, and n indicates an integer of 3 or more and 20 or less.)

Japanese Unexamined Patent Publication No. 2014-015495 Japanese Unexamined Patent Publication No. 2014-015406

By the way, when the lockup clutch is activated, the riding comfort may be deteriorated due to the torque fluctuation of the engine. Therefore, a slip control method in which the lockup clutch is slipped to transmit engine torque is being adopted.

However, when the lockup clutch is slipped, an abnormal vibration called a shadder is generated, which causes a new problem that the riding comfort is deteriorated. To prevent the occurrence of shudder, the friction coefficient increases as the amount of slip (slip speed) between the friction plate and the clutch plate during slip control increases. Μ-V characteristics (μ: friction coefficient, V: slip) Velocity), that is, it is required to impart a positive gradient μ-V characteristic to the lubricating oil.

However, there is a trade-off relationship between the improvement of the friction coefficient μ during slip control of the lockup clutch and the positive gradient of the μ-V characteristic, and it is difficult to achieve both at a high level and in a well-balanced manner.

Therefore, the present invention provides a lubricating oil additive and an additive for the lubricating oil, which can achieve both ensuring shudder prevention performance and improving friction coefficient μ at a high level in a well-balanced manner during slip control of the lockup clutch. An object of the present invention is to provide a lubricating oil composition containing an agent and a lubricating oil base oil.

The present inventors have found that a specific triimide-type compound having three succinimide groups in the molecule can solve the above-mentioned problems, and have completed the present invention.

That is, the present invention relates to the following [1] to [8].
[1] An additive for a lubricating oil containing at least one selected from the triimide type compound (X) represented by the following general formula (1).

[In the general formula (1), R ^a , R ^b , and R ^c are independently linear hydrocarbon groups having 6 to 30 carbon atoms or branched chain hydrocarbon groups having 6 to 30 carbon atoms. Represents.
x, y, and z each independently represent an integer of 1 or 2.
When two R ^a , R ^b , and R ^c are present, they may be the same or different from each other.
L ^a , L ^b , and L ^c each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms. ]
[2] the Toriimido type compound in the lubricant additive in ^{(X), R a, R} b, and the total amount α of ^{R c, R a, R b} , and the number of carbon atoms from 6 contained as ^{R c} The additive for lubricating oil according to the above [1], wherein the ratio [α1 / α] of the amount α1 of the amount of branched chain hydrocarbon groups of 30 is 1/3 or more in terms of molar ratio.
[3] The additive for lubricating oil according to the above [1] or [2], which is used as a friction modifier.
[4] The lubricant additive according to the above [1] or [2], which is used as a shudder inhibitor.
[5] The additive for lubricating oil according to the above [1] or [2], which is used as an additive that also serves as a friction modifier and an anti-shudder agent.
[6] A lubricating oil composition containing the lubricating oil additive and the lubricating oil base oil according to any one of the above [1] to [5].
[7] The lubricating oil composition according to the above [6], which is used as a drive system oil.
[8] One or more succinic anhydride compounds (X1) represented by the following general formula (2) and one or more amine compounds (X2) represented by the following general formula (3) are anhydrous. Production of an additive for lubricating oil, which comprises a step of dehydrating and condensing the ratio [(X1) / (X2)] of the succinic anhydride compound (X1) to the amine compound (X2) to a molar ratio of 3.0 or more. Method.

[In the general formula (2), R independently represents a linear hydrocarbon group having 6 to 30 carbon atoms or a branched chain hydrocarbon group having 6 to 30 carbon atoms.
x represents an integer of 1 or 2.
If there are two R's, they may be the same or different from each other. ]

[In the general formula ^{(3), L a, L} b, and ^{L c} are each independently a divalent hydrocarbon group having 1 to 10 carbon atoms. ]

According to the present invention, when the lockup clutch is slip-controlled, a lubricating oil additive and an additive for the lubricating oil can achieve both ensuring shudder prevention performance and improving friction coefficient μ at a high level in a well-balanced manner. It becomes possible to provide a lubricating oil composition containing an agent and a lubricating oil base oil.

Examples 1 to 6 have the ratio [μ1 / μ100] as the μ-V characteristic for defining the shudder prevention performance of the lockup clutch during slip control as the X-axis and the friction coefficient μ100 during slip control as the Y-axis. It is a graph which plotted the results of Comparative Examples 1 to 5.

[Aspects of Additives for Lubricants of the Present Invention]
The additive for lubricating oil of the present invention contains one or more selected from the triimide type compound (X) represented by the following general formula (1).

[In the general formula (1), R ^a , R ^b , and R ^c are independently linear hydrocarbon groups having 6 to 30 carbon atoms or branched chain hydrocarbon groups having 6 to 30 carbon atoms. Represents.
x, y, and z each independently represent an integer of 1 or 2.
When two R ^a , R ^b , and R ^c are present, they may be the same or different from each other.
L ^a , L ^b , and L ^c each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms. ]

By containing the triimide compound (X) in the lubricating oil composition, it is possible to achieve both ensuring shudder prevention performance and improving the friction coefficient μ at a high level in a well-balanced manner during slip control of the lockup clutch. Can be done.
In the following description, the "shudder prevention performance during slip control" is also simply referred to as "shudder prevention performance".
The triimide type compound (X) has a branched structure branched into three from the same nitrogen atom, and an imide succinimide group is present at the end of the three branches via a linker group. It is presumed that such a structure contributes to achieving a good balance between ensuring the shudder prevention performance and improving the friction coefficient μ during slip control at a high level.
When a bisimide-type compound having one less succinimide group than the triimide-type compound (X) is used, even if the shudder prevention performance can be ensured, the slip is as much as when the triimide-type compound (X) is used. The friction coefficient μ during control cannot be improved. The same applies when a monoimide-type compound having two fewer succinimide groups than the triimide-type compound (X) is used.
Further, even if a bisimide type compound having a structure in which a plurality of nitrogen atoms are present between two succinimide groups is used, it is possible to secure the shudder prevention performance and improve the friction coefficient μ during slip control at a high level. It is not possible to achieve a good balance.
The details of the triimide compound (X) will be described below.

<Triimide type compound (X)>
The triimide type compound (X) is represented by the general formula (1).
In the general formula (1), ^Ra , R ^b , and R ^c are independently designated as a linear hydrocarbon group having 6 to 30 carbon atoms or a branched chain hydrocarbon group having 6 to 30 carbon atoms. There is.
When the number of carbon atoms is less than 6, the solubility in the lubricating oil base oil is poor.
Further, if the number of carbon atoms exceeds 30, the shudder prevention performance may not be ensured.

As the linear hydrocarbon group having 6 to 30 carbon atoms, a linear alkyl group having 6 to 30 carbon atoms or a linear alkenyl group having 6 to 30 carbon atoms is preferable.
Linear alkyl groups having 6 to 30 carbon atoms include hexyl groups, heptyl groups, octyl groups, nonyl groups, decyl groups, undecyl groups, dodecyl groups, tridecyl groups, tetradecyl groups, pentadecyl groups, hexadecyl groups and heptadecyl groups. , Octadecyl group, nonadesyl group, icosyl group, eicosyl group, henicosyl group, heneicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, and triacocyl group. Among the alkyl groups, an alkyl group having "n-" as a prefix can be mentioned.
The linear alkenyl group having 6 to 30 carbon atoms includes a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group and a heptadecenyl group. , Octadesenyl group, nonadesenyl group, icosenyl group, eicosenyl group, henicosenyl group, heneicosenyl group, docosenyl group, tricosenyl group, tetracosenyl group, pentacosenyl group, hexacosenyl group, heptacosenyl group, octacosenyl group, nonacosenyl group, and triacenyl group. Among the alkenyl groups to be used, an alkenyl group having "n-" as a prefix can be mentioned. The position of the double bond in the alkenyl group is not limited, but it is an alkenyl group having a double bond at the 2- or 3-position when the position of the carbon atom bonded to the succinimide group is the 1-position. It is preferably an alkenyl group having a double bond at the 2-position, and more preferably.

As the branched chain hydrocarbon group having 6 to 30 carbon atoms, a branched chain alkyl group having 6 to 30 carbon atoms or a branched chain alkenyl group having 6 to 30 carbon atoms is preferable.
The branched alkyl group having 6 to 30 carbon atoms includes a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group and a heptadecyl group. , Octadecyl group, nonadesyl group, icosyl group, eicosyl group, henicosyl group, heneicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, and triacocyl group. Among the alkyl groups, an alkyl group having "sec-, tert-, isо-, or neо-" as a prefix can be mentioned. Although the position of the branch in the alkyl group is not limited, it is preferable to have a branch at the 1st or 2nd position when the position of the carbon atom bonded to the succinimide group is the 1st position, and the branch is preferably at the 1st position. It is more preferable to have.
The branched alkenyl group having 6 to 30 carbon atoms includes a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group and a heptadecenyl group. , Octadesenyl group, nonadesenyl group, icosenyl group, eicosenyl group, henicosenyl group, heneicosenyl group, docosenyl group, tricosenyl group, tetracosenyl group, pentacosenyl group, hexacosenyl group, heptacosenyl group, octacosenyl group, nonacosenyl group, and triacenyl group. Among the alkenyl groups to be used, alkenyl groups having "sec-, tert-, isо-, or neо-" as a prefix can be mentioned. The position of the double bond in the alkenyl group is not limited, but it is an alkenyl group having a double bond at the 2- or 3-position when the position of the carbon atom bonded to the succinimide group is the 1-position. It is preferably an alkenyl group having a double bond at the 2-position, and more preferably.
The position of the branch in the alkenyl group is not limited, but when the position of the carbon atom bonded to the succinimide group is set to the 1-position, it is preferable to have a branch at the 1-position or the 2-position, and the branch is formed at the 1-position. It is more preferable to have.

Here, from the viewpoint of improving the solubility in the lubricating oil base oil and ensuring the shudder prevention performance more reliably, the carbon number of the linear hydrocarbon group and the branched chain hydrocarbon group is preferably 8 to 8. 26, more preferably 10 to 22, still more preferably 12 to 20, and even more preferably 16 to 20.

The lubricating oil additive of one embodiment of the present invention, for Toriimido type compound in the lubricant additive in ^{(X), R a, R} b, and the total amount of ^{R c α, R a, R} b , and the ratio of the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms [alpha] 1 included as R ^c [α1 / α] is a molar ratio, is preferably 1/3 or more.
Note that ^"R a, ^{R b,} and the total amount of ^{R c} alpha", Toriimido type compound contained in the lubricant additive in (X) group the total ^amount, R a, ^{R b,} and the total amount of ^{R c} means.
Further, "amount α1 of branched-chain hydrocarbon groups having 6 to 30 carbon atoms contained as R ^a , R ^b , and R ^c " is the total amount of the triimide compound (X) group contained in the additive for lubricating oil. Among them, it means the total amount of branched-chain hydrocarbon groups having 6 to 30 carbon atoms contained as R ^a , R ^b , and R ^c .

The above specification using the ratio [α1 / α] reflects the structure of the triimide compound (X), and the smaller the ratio [α1 / α], the more it accounts for the total amount of ^Ra , R ^b , and R ^c. It means that there are few branched chain hydrocarbon groups having 6 to 30 carbon atoms, and the larger the ratio [α1 / α], the more branched chains having 6 to 30 carbon atoms in the total amount of ^Ra , R ^b , and R ^c. It means that there are many state hydrocarbon groups.
According to the study by the present inventor, it has been confirmed that the larger the ratio [α1 / α], the higher the effect of improving the friction coefficient μ during slip control while ensuring the shudder prevention performance. Therefore, the ratio [α1 / α] is more preferably 2/3 or more, still more preferably 2/3, from the viewpoint of imparting a higher friction coefficient μ to the lubricating oil during slip control while ensuring the shudder prevention performance. Super, most preferably 1.
According to the study by the present inventor, the smaller the ratio [α1 / α], the higher the friction coefficient μ during slip control, but the positive gradient of μ−V characteristics during slip control. It has been confirmed that it is easy to increase the size and improve the shudder prevention performance. Therefore, the ratio [α1 / α] is preferably 1 or less, more preferably 2/3 or less, still more preferably 2/3 or less, from the viewpoint of improving the shudder prevention performance while keeping the friction coefficient μ during slip control at a certain value or more. It is 1/3 or less, and most preferably 0.

Next, the structure of the triimide compound (X) will be discussed based on the ratio [α1 / α].
The additive for lubricating oil according to one aspect of the present invention has ^Ra and R in the general formula (1) from the viewpoint of imparting a higher friction coefficient μ to the lubricating oil during slip control while ensuring shudder prevention performance. ^b, and of R ^c, it is preferred that at least one is a branched chain hydrocarbon group having 6 to 30 carbon atoms. More preferably, there are two or more branched chain hydrocarbon groups having 6 to 30 carbon atoms, and most preferably all of them are branched chain hydrocarbon groups having 6 to 30 carbon atoms.
Further, from the viewpoint of improving the shudder prevention performance while setting the friction coefficient μ during slip control to a certain value or more, at least one of R ^a , R ^b , and R ^{c in} the general formula (1) is 6 to 6 to 6. It is preferably 30 linear hydrocarbon groups. More preferably, there are two or more linear hydrocarbon groups having 6 to 30 carbon atoms, and most preferably all of them are linear hydrocarbon groups having 6 to 30 carbon atoms.

Here, from the viewpoint of facilitating the effect of the present invention, x, y, and z in the general formula (1) are preferably 1.
When x, y, and z are 1, ^Ra , R ^b in the general formula (1), from the viewpoint of imparting a higher friction coefficient μ to the lubricating oil during slip control while ensuring shudder prevention performance. , and R ^c is preferably at least one is a branched chain hydrocarbon group having 6 to 30 carbon atoms, more preferably two of a branched chain hydrocarbon group having 6 to 30 carbon atoms, most preferably 3 One is a branched chain hydrocarbon group having 6 to 30 carbon atoms.
Further, when x, y, and z are 1, ^Ra , R ^b in the general formula (1), from the viewpoint of improving the shudder prevention performance while keeping the friction coefficient μ during slip control at a certain value or more. , and R ^c is preferably at least one linear hydrocarbon group having 6 to 30 carbon atoms, more preferably two of a straight chain hydrocarbon group having 6 to 30 carbon atoms, most preferably 3 One is a linear hydrocarbon group having 6 to 30 carbon atoms.
The preferable range of the carbon number of the linear hydrocarbon group having 6 to 30 carbon atoms and the branched chain hydrocarbon group having 6 to 30 carbon atoms is as described above. Further, among these hydrocarbon groups, an alkenyl group is preferable.

Then, the linker group having Toriimido type compound (X) is ^(L a, ^{L b,} and ^{L c)} will be described.
In Formula ^{(1), L a, L} b, and ^{L c} are each independently is a divalent hydrocarbon group having 1 to 10 carbon atoms.
Examples of the divalent hydrocarbon group having 1 to 10 carbon atoms include a divalent linear aliphatic hydrocarbon group having 1 to 10 carbon atoms and a divalent branched chain aliphatic hydrocarbon group having 3 to 10 carbon atoms. , A divalent alicyclic hydrocarbon group having 3 to 10 carbon atoms, or a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms. The divalent linear aliphatic hydrocarbon group, the divalent branched chain aliphatic hydrocarbon group, and the divalent alicyclic hydrocarbon group may be saturated or unsaturated. Further, the divalent hydrocarbon group having 1 to 10 carbon atoms may be substituted with a substituent or may be unsubstituted. Examples of the substituent include a nitrogen-containing functional group such as a primary amino group, a secondary amino group, and an amide; an oxygen-containing functional group having an ether structure or an ester structure.
^Further, L a, ^{L b,} and ^{L c} may be the same or different from each other.
Here, from the viewpoint of easy effect is exhibited more of the present invention, it L ^{a, L b,} and L ^c are each independently a divalent linear hydrocarbon group having 1 to 5 carbon atoms Is preferable.
Examples of the divalent linear hydrocarbon group having 1 to 5 carbon atoms include a linear alkylene group having 1 to 5 carbon atoms and a linear alkenylene group having 2 to 5 carbon atoms.
Examples of the divalent linear alkylene group having 1 to 5 carbon atoms include a methylene group, an ethylene group, an n-propylene group, an n-butylene group, and an n-pentylene group.
Examples of the divalent linear alkenylene group having 2 to 5 carbon atoms include a vinylene group, an n-propenylene group, an n-butenylene group, and an n-pentenylene group.
Among these, a divalent linear hydrocarbon group having 2 to 3 carbon atoms is preferable, and a divalent linear hydrocarbon group having 2 to 3 carbon atoms is preferable from the viewpoint of imparting a higher friction coefficient μ to the lubricating oil during slip control while ensuring the shudder prevention performance. A few linear alkylene groups are more preferred, and an alkylene group having 2 carbon atoms is even more preferred.

<Content of triimide compound (X)>
From the viewpoint of facilitating the effect of the present invention, the lubricating oil additive of one aspect of the present invention has a triimide compound (X) content of preferably 50 based on the total mass of the lubricating oil additive. It is mass% or more, more preferably 60% by mass or more, still more preferably 70% by mass or more, still more preferably 80% by mass or more, still more preferably 90% by mass or more, still more preferably 95% by mass or more. Considering the purity of the triimide compound (X) by purification, the content of the triimide compound (X) is usually 98% by mass or less.
Moreover, the additive for lubricating oil of one aspect of the present invention may contain a compound other than the triimide type compound (X) as long as the effect of the present invention is not impaired. For example, a by-product generated when synthesizing the triimide type compound (X) and a raw material remaining without contributing to the reaction may be contained, or a compound different from these may be contained. For example, a bisimide-type compound having one less succinimide group than the triimide-type compound (X) and a monoimide-type compound having one less succinimide group than the triimide-type compound (X) may be contained. As described above, when the additive for lubricating oil according to one aspect of the present invention contains a compound other than the triimide type compound (X), the content of the triimide type compound (X) is based on the total amount of the additive for lubricating oil. , 90% by mass or less. However, also in this case, the content of the triimide compound (X) is preferably 50% by mass or more.
The additive for lubricating oil according to one aspect of the present invention may be diluted with a diluting solvent from the viewpoint of solubility in the lubricating oil base oil and handleability.

<Use of Additive for Lubricating Oil of the Present Invention>
The additive for lubricating oil of the present invention can achieve both ensuring shudder prevention performance and improving the friction coefficient μ during slip control at a high level in a well-balanced manner. Therefore, it is useful as a friction modifier for lubricating oils. It is also useful as a shudder inhibitor for lubricating oils.
Further, the additive for lubricating oil of the present invention is particularly useful as an additive having both a friction modifier for lubricating oil and an anti-shudder agent.

[Manufacturing method of additives for lubricating oil]
Hereinafter, a method for producing the additive for lubricating oil of the present invention will be described.
The additive for lubricating oil of the present invention is, for example, one or more succinic anhydride compounds (X1) represented by the following general formula (2) and one or more amines represented by the following general formula (3). A step of dehydrating and condensing the compound (X2) by setting the ratio [(X1) / (X2)] of the succinic anhydride compound (X1) to the amine compound (X2) to 3.0 or more in terms of molar ratio. It is manufactured by the manufacturing method that it has.

[In the general formula (2), R independently represents a linear hydrocarbon group having 6 to 30 carbon atoms or a branched chain hydrocarbon group having 6 to 30 carbon atoms.
x represents an integer of 1 or 2.
If there are two R's, they may be the same or different from each other. ]

[In the general formula ^{(3), L a, L} b, and ^{L c} are each independently a divalent hydrocarbon group having 1 to 10 carbon atoms. ]

By the above production method, the triamine compound (X) contained in the additive for lubricating oil of the present invention can be synthesized as a dehydration condensation reaction product of the succinic anhydride compound (X1) and the amine compound (X2).
Here, in order to synthesize the triamine compound (X), 3 mol or more of the succinic anhydride compound (X1) is required for 1 mol of the amine compound (X2). From this point of view, the ratio [(X1) / (X2)] of the succinic anhydride compound (X1) and the amine compound (X2) is set to 3.0 or more in terms of molar ratio. From the viewpoint of suppressing the amount of unreacted material, the ratio is preferably 3.5 or less.

The reaction temperature when the dehydration condensation reaction of the succinic anhydride compound and the amine compound is carried out is usually 100 to 200 ° C., preferably 110 to 190 ° C., and more preferably 120 to 180 ° C. The reaction time is usually 1 to 10 hours, preferably 2 to 8 hours, more preferably 2 to 6 hours.

From the viewpoint of allowing the dehydration condensation reaction to proceed smoothly, it is preferable to dissolve the succinic anhydride compound (X1) and the amine compound (X2) in an organic solvent to carry out the dehydration condensation reaction. As the organic solvent, for example, one or more selected from xylene, toluene, heptane, alcohols and the like can be used. However, the dehydration condensation reaction may be carried out without a solvent.

After the dehydration condensation reaction is completed, it is preferable to carry out heating under reduced pressure, if necessary, to remove the solvent and light components for purification.

Wherein the carbon in the above manufacturing method, Toriimido type compound in the lubricant additive in ^(X), R a, for ^{R b,} and the total amount of ^{R c alpha,} contained as R a, ^{R b,} and ^{R c} From the viewpoint of controlling the ratio [α1 / α] of the amount α1 of the branched chain hydrocarbon groups of numbers 6 to 30 as described above, one or more succinic anhydride compounds represented by the general formula (2) (2). X1) is preferably adjusted as follows.
That is, the ratio [β1 / β] of the amount β1 of the branched chain hydrocarbon group having 6 to 30 carbon atoms contained as R to the total amount β of R contained in the succinic anhydride compound (X1) used in the above production method. , [Α1 / α] is preferably adjusted in the same manner.
Specifically, the ratio [β1 / β] is preferably 1/3 or more, more preferably 2 from the viewpoint of imparting a higher friction coefficient μ to the lubricating oil during slip control while ensuring the shudder prevention performance. It is adjusted to 3/3 or more, more preferably more than 2/3, and most preferably 1.
Further, the ratio [β1 / β] is preferably 1 or less, more preferably 2/3 or less, still more preferably 2/3 or less, from the viewpoint of improving the shudder prevention performance while keeping the friction coefficient μ during slip control at a certain value or more. It is 1/3 or less, and most preferably adjusted to 0.

The preferred range of the linear hydrocarbon group having 6 to 30 carbon atoms or the branched chain hydrocarbon group having 6 to 30 carbon atoms selected as R is selected as ^Ra , R ^b , and R ^c. This is the same as the preferable range of the linear hydrocarbon group having 6 to 30 carbon atoms or the branched chain hydrocarbon group having 6 to 30 carbon atoms.
Further, x is preferably 1 from the viewpoint of facilitating the effect of the present invention.
The preferred ranges of L ^a , L ^b , and L ^c are the same as described above.

[Lubricating oil composition]
The lubricating oil composition of the present invention contains the lubricating oil additive and the lubricating oil base oil.
In the lubricating oil composition of one aspect of the present invention, the content of the lubricating oil additive is included in the lubricating oil additive from the viewpoint of better exerting the additive effect of the lubricating oil additive. The content of one or more selected from the triimide type compound (X) represented by the general formula (1) is preferably 0.01 to 20% by mass, more preferably 0.05 to 15% by mass, and further. It is preferably adjusted to 0.1 to 10% by mass.

<Lubricating oil base oil>
The lubricating oil base oil may be one or more selected from mineral oils and synthetic oils.
Kinematic viscosity at 100 ° C. of the lubricating base oil is preferably in the range of 1 to 50 mm ² / s, and more preferably in the range of 2 to 20 mm ² / s. Further, the viscosity index is preferably 80 or more, more preferably 100 or more, and even more preferably 120 or more.
The kinematic viscosity and viscosity index of the lubricating oil base oil are values measured and calculated according to JIS K2283-2000.
Specific examples of the lubricating oil base oil are given below.
The mineral oil is, for example, a distillate obtained by distilling paraffin-based crude oil, intermediate-based crude oil, or naphthenic-based crude oil at atmospheric pressure and / or vacuum distillation; refining obtained by refining the distillate according to a conventional method. Oil; etc. Examples of the refining method for obtaining the refined oil include solvent dewaxing treatment, hydrogenation isomerization treatment, hydrogenation finishing treatment, and white clay treatment.
Examples of synthetic oils include hydrocarbon oils, aromatic oils, ester oils, ether oils and the like. Further, as the synthetic oil, GTL (Gas To Liquids) obtained by isomerizing a wax (GTL wax, Gas To Liquids WAX) produced by the Fischer-Tropsch method or the like from natural gas may be used.

<Other additives>
The lubricating oil composition according to one aspect of the present invention comprises an antioxidant, an oily agent, an extreme pressure agent, a cleaning dispersant, a viscosity index improver, and a rust preventive, as long as the effects of the lubricating oil additive are not impaired. It may contain an additive such as a metal inactivating agent and an antifoaming agent. These may be used individually by 1 type or in combination of 2 or more type.

(Antioxidant)
As the antioxidant, an amine-based antioxidant, a phenol-based antioxidant, a phosphorus-based antioxidant, and a sulfur-based antioxidant used in conventional hydrocarbon-based lubricating oils can be used. These antioxidants can be used alone or in combination of two or more.
Examples of the amine-based antioxidant include monoalkyldiphenylamine-based compounds such as monooctyldiphenylamine and monononyldiphenylamine; 4,4'-dibutyldiphenylamine, 4,4'-dipentyldiphenylamine, 4,4'-dihexyldiphenylamine, and 4 , 4'-Diheptyldiphenylamine, 4,4'-dioctyldiphenylamine, and 4,4'-dinonyldiphenylamine and other dialkyldiphenylamine compounds; tetrabutyldiphenylamine, tetrahexyldiphenylamine, tetraoctyldiphenylamine, tetranonyldiphenylamine and the like. Polyalkyldiphenylamine compounds; α-naphthylamine, phenyl-α-naphthylamine, butylphenyl-α-naphthylamine, pentylphenyl-α-naphthylamine, hexylphenyl-α-naphthylamine, heptylphenyl-α-naphthylamine, octylphenyl-α-naphthylamine , And naphthylamine compounds such as nonylphenyl-α-naphthylamine.
Examples of the phenolic antioxidant include monophenolic compounds such as 2,6-di-tert-butyl-4-methylphenol and 2,6-di-tert-butyl-4-ethylphenol; 4,4'. Examples of phosphorus-based antioxidants include bisphenol-based compounds such as −methylenebis (2,6-di-tert-butylphenol) and 2,2′-methylenebis (4-ethyl-6-tert-butylphenol). Examples thereof include phenylphosphite and diethyl [3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] phosphonate.
Examples of the sulfur-based antioxidant include 2,6-di-tert-butyl-4- (4,6-bis (octylthio) -1,3,5-triazine-2-ylamino) phenol and phosphorus pentasulfide. Examples thereof include thioterpene compounds such as a reaction product with pinene, dilaurylthiodipropionate, and dialkylthiodipropionate such as distearylthiodipropionate.
The content of the antioxidant may be the minimum amount required to maintain the oxidative stability of the lubricating oil composition. Specifically, for example, 0.01 to 1% by mass is preferable based on the total amount of the lubricating oil composition.

(Oil agent)
Examples of the oily agent include aliphatic alcohols; fatty acid compounds such as fatty acids and fatty acid metal salts; ester compounds such as polyol esters, sorbitan esters, and glycerides; amine compounds such as aliphatic amines.
The content of the oily agent is usually 0.1 to 20% by mass, preferably 0.5 to 10% by mass, based on the total amount of the lubricating oil composition from the viewpoint of the addition effect.

(Extreme pressure agent)
Examples of the extreme pressure agent include a sulfur-based extreme pressure agent, a phosphorus-based extreme pressure agent, an extreme pressure agent containing sulfur and a metal, and an extreme pressure agent containing phosphorus and a metal. These extreme pressure agents may be used alone or in combination of two or more. The extreme pressure agent may be any one containing at least one of a sulfur atom and a phosphorus atom in the molecule and capable of exhibiting load resistance and wear resistance.
Examples of extreme pressure agents containing sulfur in the molecule include sulfide oils and fats, sulfide fatty acids, sulfide esters, sulfide olefins, dihydrocarbyl polysulfide, thiadiazol compounds, alkylthiocarbamoyl compounds, triazine compounds, thioterpene compounds, and dialkylthiodipropionate compounds. And so on.
Typical examples of extreme pressure agents containing phosphorus in the molecule include phosphoric acid esters such as tricresyl phosphate and amine salts thereof.
Extreme pressure agents containing sulfur, phosphorus, and metals include zinc dialkylthiocarbamate (Zn-DTC), molybdenum dialkylthiocarbamate (Mo-DTC), lead dialkylthiocarbamate, tin dialkylthiocarbamate, and dialkyldithiophosphate. Examples thereof include zinc acid (Zn-DTP), molybdenum dialkyldithiophosphate (Mo-DTP), sodium sulfonate, calcium sulfonate and the like.
The content of these extreme pressure agents is usually 0.01 to 10% by mass, more preferably 0.1 to 5% by mass, based on the total amount of the lubricating oil composition, from the viewpoint of addition effect and economy. ..

(Cleaning dispersant)
Examples of the cleaning dispersant include metal sulfonate, metal salicylate, metal phenate, and succinimide.
The content of the cleaning dispersant is usually 0.01 to 10% by mass, preferably 0.1 to 5% by mass, based on the total amount of the lubricating oil composition from the viewpoint of the addition effect.

(Viscosity index improver)
Examples of the viscosity index improver include polymethacrylate, dispersed polymethacrylate, olefin-based copolymer (for example, ethylene-propylene copolymer, etc.), dispersed olefin-based copolymer, and styrene-based copolymer (for example,). Styrene-diene hydride copolymer, etc.) and the like.
The content of the viscosity index improver may be added so that the viscosity at 100 ° C. is 5 mm ² / s or more, for example. Preferably, it is 0.3 to 5% by mass based on the total amount of the lubricating oil composition.

(anti-rust)
Examples of the rust preventive include metal-based sulfonates, succinic acid esters, and alkanolamines such as alkylamines and monoisopropanolamines.
The content of the rust preventive is usually 0.01 to 5% by mass, preferably 0.03 to 3% by mass, based on the total amount of the lubricating oil composition from the viewpoint of the addition effect.

(Metal inactivating agent)
Examples of the metal deactivator include benzotriazole and thiadiazole.
The preferable content of the metal deactivator is usually 0.01 to 5% by mass, preferably 0.01 to 1% by mass, based on the total amount of the lubricating oil composition from the viewpoint of the addition effect.

(Defoamer)
Examples of the defoaming agent include methyl silicone oil, fluorosilicone oil, and polyacrylate.
The content of the defoaming agent is usually 0.0005 to 0.01% by mass based on the total amount of the lubricating oil composition from the viewpoint of the addition effect.

[Physical properties of lubricating oil composition]
The lubricating oil composition according to one aspect of the present invention has a parameter (μ1 / μ100) indicating shudder prevention performance, which is measured and calculated by the method described in Examples described later, preferably 0.9 or less, more preferably. It is 0.8 or less, more preferably 0.7 or less.
Further, in the lubricating oil composition of one aspect of the present invention, the parameter (μ100) indicating the friction coefficient μ at the time of slip control, which is measured by the method described in Examples described later, is preferably 0.105 or more. It is preferably 0.110 or more, more preferably 0.115 or more, and even more preferably 0.120 or more.

[Use of lubricating oil composition]
The lubricating oil composition of the present invention achieves both ensuring shudder prevention performance and improving the friction coefficient μ during slip control at a high level in a well-balanced manner.
Therefore, the lubricating oil composition of the present invention can be suitably used for drive system oils such as automatic transmission fluids and continuously variable transmission oils.

Therefore, as one aspect of the method of using the lubricating oil composition of the present invention, there is a method of using the lubricating oil composition for an automatic transmission and a continuously variable transmission.
Moreover, one aspect of the present invention includes an automatic transmission or a continuously variable transmission containing the lubricating oil composition.
Further, as one aspect of the present invention, an automobile equipped with an automatic transmission or a stepless transmission containing the lubricating oil composition can be mentioned.

The present invention will be specifically described with reference to the following examples, but the present invention is not limited to the following examples.

[Production Examples 1 to 6 and Comparative Production Examples 1 to 5]
Compounds A to K were synthesized according to the methods described below.

<Manufacturing example 1>
72 g (0.21 mol) of isooctadecenyl succinic anhydride and 20 mL of xylene were put into a 200 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Until then, 10 g (0.068 mol) of tris (2-aminoethyl) amine was added dropwise over 30 minutes.
After dropping tris (2-aminoethyl) amine, the solution in the flask was heated to 150 ° C. and stirred for 3 hours.
After the stirring was completed, the inside of the flask was depressurized with a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, thereby obtaining 64 g of a red oily product as compound A. ..
Compound A is a compound represented by the following chemical structural formula (A).
Compound A, in the general formula ^{(1), R a, R} b, and ^{R c} are iso-octadecenyl group, x, y, and z are the ^1, L a, ^{L b,} and L A compound in which ^c is an ethylene group.
Incidentally, Compound ^A, R a, the total amount α of ^{R b,} and ^{R c,} the ratio of R a, ^{R b,} and the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms contained as ^{R c} [alpha] 1 [ α1 / α] is 1 in terms of molar ratio.

<Manufacturing example 2>
36 g (0.10 mol) of isooctadecenyl succinic anhydride and 30 mL of xylene were put into a 150 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Then, 5.8 g (0.031 mol) of tris (3-aminopropyl) amine was added dropwise over 30 minutes.
After dropping tris (3-aminopropyl) amine, the solution in the flask was heated to 150 ° C. and stirred for 3 hours to mix isooctadecenyl succinic anhydride and tris (3-aminopropyl) amine. It was reacted.
After the stirring was completed, the inside of the flask was depressurized with a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, whereby 36 g of a yellow solid product was obtained as Compound B. ..
Compound B, in the general formula ^{(1), R a, R} b, and ^{R c} are iso-octadecenyl group, x, y, and z are the ^1, L a, ^{L b,} and L ^c is a compound having a propylene group.
Incidentally, Compound ^B, R a, the total amount α of ^{R b,} and ^{R c,} the ratio of R a, ^{R b,} and the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms contained as ^{R c} [alpha] 1 [ α1 / α] is 1 in terms of molar ratio.

<Manufacturing example 3>
36 g (0.10 mol) of n-octadecenyl succinic anhydride and 30 mL of xylene were put into a 200 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Until then, 5 g (0.034 mol) of tris (2-aminoethyl) amine was added dropwise over 30 minutes.
After dropping tris (2-aminoethyl) amine, the solution in the flask was heated to 150 ° C. and stirred for 3 hours to prepare n-octadecenyl succinic anhydride and tris (2-aminoethyl) amine. Was reacted.
After the stirring was completed, the inside of the flask was depressurized with a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, thereby obtaining 32 g of a yellow solid product as compound C. ..
In the compound C, in the general formula (1), R ^a , R ^b , and R ^c are n-octadecenyl groups, x, y, and z are 1, and ^La , L ^b , and L ^c are. It is a compound that is an ethylene group.
Incidentally, Compound ^C, R a, for ^{R b,} and the total amount of ^{R c α, R a,} the ratio of ^{R b,} and the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms contained as ^{R c} [alpha] 1 [ α1 / α] is 0 in terms of molar ratio.

<Manufacturing example 4>
Put 5 g (0.034 mol) of tris (2-aminoethyl) amine and 30 mL of xylene into a 200 mL four-necked flask, heat the solution in the flask to 80 ° C, and then maintain the state at 80 ° C. , 12 g (0.034 mol) of isooctadecenyl succinic anhydride dissolved in 20 mL of xylene was added dropwise over 1 hour.
After dropping the solution, the temperature of the solution in the flask was raised to 150 ° C., and after stirring for 3 hours, the temperature of the solution in the flask was lowered to 80 ° C., and the n-octa was maintained at 80 ° C. 24 g (0.068 mol) of decenyl succinic anhydride was added dropwise over 30 minutes.
After dropping n-octadecenyl succinic anhydride, the solution in the flask was heated to 150 ° C. and stirred for 3 hours.
After the stirring was completed, the temperature inside the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, whereby 33 g of a yellow solid product was obtained as compound D. ..
In compound D, in the general formula (1), one of ^Ra , R ^b , and R ^c is an isooctadecenyl group, and the other two are n-octadeceenyl groups, and x, y, and z is ^1, L ^a, compound ^{L b,} and ^{L c} is an ethylene group is mainly.
Incidentally, Compound ^D, R a, the total amount α of ^{R b,} and ^{R c,} the ratio of R a, ^{R b,} and the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms contained as ^{R c} [alpha] 1 [ α1 / α] is 1/3 in molar ratio.

<Production example 5>
Put 5 g (0.034 mol) of tris (2-aminoethyl) amine and 30 mL of xylene into a 200 mL four-necked flask, heat the solution in the flask to 80 ° C, and then maintain the state at 80 ° C. Then, a solution prepared by dissolving 24 g (0.068 mol) of isooctadecenyl succinic anhydride in 20 mL of xylene was added dropwise over 1 hour.
After dropping the solution, the temperature of the solution in the flask was raised to 150 ° C., and after stirring for 3 hours, the temperature of the solution in the flask was lowered to 80 ° C., and the n-octa was maintained at 80 ° C. 12 g (0.034 mol) of decenyl succinic anhydride was added dropwise over 30 minutes.
After dropping n-octadecenyl succinic anhydride, the solution in the flask was heated to 150 ° C. and stirred for 3 hours.
After the stirring was completed, the inside of the flask was depressurized with a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, thereby obtaining 36 g of a yellow solid product as Compound E. ..
In compound E, in the general formula (1), two of ^Ra , R ^b , and R ^c are isooctadecenyl groups, and the remaining one is an n-octadeceenyl group, and x, y, And Z is 1, and ^La , L ^b , and L ^c are ethylene groups.
Incidentally, Compound ^E, R a, the total amount α of ^{R b,} and ^{R c,} the ratio of R a, ^{R b,} and the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms contained as ^{R c} [alpha] 1 [ α1 / α] is 2/3 in molar ratio.

<Manufacturing example 6>
45 g (0.17 mol) of 2-dodecene-1-ylsuccinic anhydride and 30 mL of xylene were put into a 150 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Until then, 7.8 g (0.053 mol) of tris (2-aminoethyl) amine was added dropwise over 30 minutes.
After dropping tris (2-aminoethyl) amine, the solution in the flask was heated to 150 ° C. and stirred for 3 hours.
After the stirring was completed, the temperature inside the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, whereby 42 g of a yellow solid product was obtained as Compound F. ..
Compound F is in the general formula ^(1), and R a, ^{R b,} and ^{R c} is n- dodecenyl, x, y, and z is ^1, is L a, ^{L b,} and ^{L c} It is a compound that is an ethylene group.
The compound F ^is, R a, for ^{R b,} and the total amount of ^{R c α, R a,} the ratio of ^{R b,} and the amount of branched chain hydrocarbon group having 6 to 30 carbon atoms contained as ^{R c} [alpha] 1 [ α1 / α] is 0 in terms of molar ratio.

<Comparative manufacturing example 1>
56 g (0.16 mol) of isooctadecenyl succinic anhydride and 20 mL of xylene were put into a 200 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Until then, 12 g (0.08 mol) of diethylenetriamine was added dropwise over 30 minutes.
After dropping diethylenetriamine, the temperature of the solution in the flask was raised to 150 ° C., and the mixture was stirred for 3 hours.
After the stirring was completed, the temperature inside the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, thereby obtaining 55 g of a red oily product as compound G. ..

<Comparative manufacturing example 2>
Red oily formation as compound H by the same method as in Comparative Production Example 1 except that the input amount of 28 g (0.08 mol) of isooctadecenyl succinic anhydride was changed to 28 g (0.08 mol). I got 42g of the thing.

<Comparative manufacturing example 3>
56 g (0.16 mol) of isooctadecenyl succinic anhydride and 20 mL of xylene were put into a 200 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Until then, 12 g (0.08 mol) of triethylenetetramine was added dropwise over 30 minutes.
After dropping triethylenetetramine, the temperature of the solution in the flask was raised to 150 ° C., and the mixture was stirred for 3 hours.
After the stirring was completed, 55 g of a red oily product was obtained as Compound I by reducing the pressure inside the flask for 3 hours with a vacuum pump while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components. ..

<Comparative manufacturing example 4>
58 g of a red oily product was obtained as Compound J by the same method as in Comparative Production Example 3 except that isooctadecenyl succinic anhydride was changed to n-octadecenyl succinic anhydride. ..

<Comparative manufacturing example 5>
56 g (0.16 mol) of isooctadecenyl succinic anhydride and 20 mL of xylene were put into a 200 mL four-necked flask, and the solution in the flask was heated to 80 ° C. and then maintained at 80 ° C. Up to this point, 9.4 g (0.08 mol) of 2,2'-diamino-N-methyldiethylamine was added dropwise over 30 minutes.
After adding 2,2'-diamino-N-methyldiethylamine, the solution in the flask was heated to 150 ° C. and stirred for 3 hours.
After the stirring was completed, the temperature inside the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140 ° C. to remove the solvent and light components, thereby obtaining 54 g of a red oily product as compound K. ..

<Compounds G to K obtained in Comparative Production Examples 1 to 5>
The compounds G to K obtained in Comparative Production Examples 1 to 5 are shown below.

[Examples 1 to 6 and Comparative Examples 1 to 5]
Mineral oil (kinematic viscosity at 40 ° C.: 9.8 mm ² / s) classified in Group 3 of the API (American Petroleum Institute) base oil category is used as the base oil, and the base oil and compounds A to K are mixed. To prepare a lubricating oil composition. The blending amount of the compounds A to K was adjusted so that the content of nitrogen atoms derived from the compounds A to K was 500 mass ppm based on the total amount of the lubricating oil composition.
The kinematic viscosity of the base oil at 40 ° C. was measured according to JIS K2283: 2000.

[Evaluation method]
A friction plate (A795.D0AK) was used with respect to the lubricating oil compositions prepared in Examples 1 to 6 and Comparative Examples 1 to 5 using a low-speed slip friction tester (LVFA tester) based on JASO M 349: 2012. And the friction coefficient on the steel plate (FZ132-8-Y2) was measured.
The test oil temperature at the time of measurement was 80 ° C., and the surface pressure was 1 MPa.
In JASO M 349: 2012, the measurement is usually performed by using the SWEEP method, but in order to improve the measurement accuracy of the friction coefficient, the evaluation was carried out by the STEP method specified in JASO M 349: 1998.
Regarding the μ-V characteristics for defining the shudder prevention performance during slip control of the lockup clutch, the ratio of the friction coefficient μ1 at a rotation speed of 1 rpm to the friction coefficient μ100 at a rotation speed of 100 rpm [(μ1) / (μ100)). ] Was evaluated.
The friction coefficient μ during slip control was evaluated by the friction coefficient μ 100 at a rotation speed of 100 rpm.
Then, it is said that the shudder prevention performance can be secured when the ratio [μ1 / μ100] as the μ-V characteristic for defining the shudder prevention performance at the time of slip control of the lockup clutch is 0.9 or less. It was judged.
Further, when the ratio [μ1 / μ100] as the μ-V characteristic for defining the shudder prevention performance at the time of slip control of the lockup clutch is 0.7 to 0.9, the friction coefficient μ100 is 0. A case of 120 or more was regarded as a pass. If the ratio [μ1 / μ100] as the μ-V characteristic for defining the shudder prevention performance during slip control of the lockup clutch is less than 0.7, it becomes more difficult to improve the friction coefficient μ100. , 0.105 or more was judged to pass.

The results are shown in Tables 1 and 2.
Further, the ratio [μ1 / μ100] as the μ-V characteristic for defining the shudder prevention performance during slip control of the lockup clutch is defined as the X-axis, and the friction coefficient μ100 during slip control is defined as the Y-axis. A graph plotting the results of ~ 6 and Comparative Examples 1 to 5 is shown in FIG.

From the results shown in Tables 1 and 2, the following can be seen.
It can be seen that the lubricating oil compositions of Examples 1 to 6 are able to achieve both ensuring the shudder prevention performance and improving the friction coefficient μ during slip control at a high level in a well-balanced manner.
In particular, it can be seen that the lubricating oil compositions of Examples 1 and 2 have a very high friction coefficient μ of 0.120 or more during slip control while ensuring the shudder prevention performance.
Further, it can be seen that the lubricating oil compositions of Examples 3 to 6 can secure the shudder prevention performance at an extremely high level while having a high friction coefficient μ of 0.105 or more during slip control.
On the other hand, when the additive for lubricating oil is a bisimide type compound having two succinimide groups as in Comparative Examples 1 and 3 to 5, it is used for lubricating oil as in Comparative Example 2. When the additive is a monoimide-type compound having one succinimide group, it achieves a high level of balance between ensuring shudder prevention performance and improving the friction coefficient μ during slip control. It turns out that it cannot be done.
When a monoimide-type compound is used as in Comparative Example 2, or when a bisimide compound having two nitrogen atoms between two succinimide groups is used as in Comparative Examples 3 and 4, a bisimide compound is used. It can be seen that it is difficult to secure either one or both of the shudder prevention performance and the high friction coefficient μ during slip control.
Further, when a bisimide compound having one nitrogen atom between two succinimide groups as in Comparative Examples 1 and 5 is used, the shudder prevention performance can be ensured, but high friction during slip control can be ensured. It can be seen that the coefficient μ cannot be secured and is inferior to the friction coefficient μ at the time of slip control as compared with the lubricating oil compositions of Examples 1 and 2.

Claims (8)

An additive for a lubricating oil containing one or more selected from the triimide type compound (X) represented by the following general formula (1).

[In the general formula (1), R ^a , R ^b , and R ^c are independently linear hydrocarbon groups having 6 to 30 carbon atoms or branched chain hydrocarbon groups having 6 to 30 carbon atoms. Represents.
x, y, and z each independently represent an integer of 1 or 2.
When two R ^a , R ^b , and R ^c are present, they may be the same or different from each other.
L ^a , L ^b , and L ^c each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms. ] In the Toriimido type compound in the lubricating oil additive ^{(X), R a, R} b, and the total amount α of ^{R c, R a, R b} , and branched C6-30 contained as ^{R c} The additive for a lubricating oil according to claim 1, wherein the ratio [α1 / α] of the amount α1 of the chain hydrocarbon group is 1/3 or more in terms of molar ratio. The additive for lubricating oil according to claim 1 or 2, which is used as a friction modifier. The lubricant additive according to claim 1 or 2, which is used as a shudder inhibitor. The additive for lubricating oil according to claim 1 or 2, which is used as an additive that also serves as a friction modifier and an anti-shudder agent. A lubricating oil composition containing the lubricating oil additive and the lubricating oil base oil according to any one of claims 1 to 5. The lubricating oil composition according to claim 6, which is used as a drive system oil. One or more succinic anhydride compounds (X1) represented by the following general formula (2) and one or more amine compounds (X2) represented by the following general formula (3) are combined with the succinic anhydride compound. A method for producing an additive for lubricating oil, which comprises a step of dehydrating and condensing the ratio [(X1) / (X2)] of (X1) to the amine compound (X2) to a molar ratio of 3.0 or more.

[In the general formula (2), R independently represents a linear hydrocarbon group having 6 to 30 carbon atoms or a branched chain hydrocarbon group having 6 to 30 carbon atoms.
x represents an integer of 1 or 2.
If there are two R's, they may be the same or different from each other. ]

[In the general formula ^{(3), L a, L} b, and ^{L c} are each independently a divalent hydrocarbon group having 1 to 10 carbon atoms. ]