JP7301017B2 - Lubricating oil additive and lubricating oil composition for drive system - Google Patents

Description

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

In recent years, due to the increasing demand for improved fuel efficiency in vehicles such as automobiles, lockup clutches are often incorporated in the torque converters of automatic transmissions and continuously variable transmissions mounted in vehicles such as automobiles. It's becoming
A lock-up 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, direct transmission of engine torque to the transmission to drive the transmission is also referred to as "direct drive." By incorporating a lockup clutch into the torque converter, the operation of the lockup clutch enables the switching between drive via fluid (drive system oil) and direct drive at the optimum timing. Therefore, compared to the case where the torque converter does not incorporate the lockup clutch, the agitation loss is reduced, the power transmission efficiency is improved, and the fuel efficiency is improved.

By the way, when the lockup clutch is operated, the torque fluctuation of the engine may deteriorate the ride comfort. Therefore, a slip control method is being adopted in which the lockup clutch is slipped to transmit the engine torque.
However, when the lock-up clutch is slipped, an abnormal vibration called shudder occurs, which causes a new problem of deteriorating ride comfort. In order to prevent shudder, the μ-V characteristic (μ: friction coefficient, V: slip velocity), that is, to impart a positive slope μ-V characteristic to the lubricant.

In order to meet such demands, various additives for preventing shudder (hereinafter also referred to as "anti-shudder") have been developed. For example, Patent Documents 1 to 3 propose to prevent shudder by blending a compound having a monoimide skeleton or a compound having a bisimide skeleton into a lubricating oil composition.

JP 2001-288489 A Japanese Patent Application Laid-Open No. 2002-105478 JP 2009-35737 A

By the way, in a lubricating oil composition for a drive system, sludge caused by deterioration (oxidative deterioration) of additives is one of the causes of clogging of clutch materials. Therefore, it is considered desirable to impart the ability to improve the detergency of the drive system lubricating oil composition to the anti-shudder agent, which is an additive with a large content in the lubricating oil composition for the drive system.
However, such consideration is not made in Patent Documents 1 to 3.

The present invention provides a lubricating oil additive that can greatly improve detergency while imparting shudder prevention performance to a lubricating oil composition for a drive system, and a driving system containing the lubricating oil additive. An object of the present invention is to provide a system lubricating oil composition.

As a result of intensive studies, the inventors of the present invention have found that a nitrogen-containing compound having a specific structure can solve the above-described problems, and have completed the present invention through further studies.

［前記一般式（ａ）中、Ｒ^ａ１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ａ２、Ｒ^ａ３、Ｒ^ａ４、及びＲ^ａ５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ａ６は、炭素数８～２０の直鎖状の脂肪族炭化水素基である。Ｒ^ａ７は、水素原子、炭素数１～３のアルキル基、又は炭素数１～３のアルキレン基である。Ｒ^ａ７が、炭素数１～３のアルキレン基である場合、Ｒ^ａ７はＲ^ａ６に結合する炭素原子Ｃ^ａｘと結合し、環構造を形成する。］

［前記一般式（ｂ）中、Ｒ^ｂ１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｂ２、Ｒ^ｂ３、Ｒ^ｂ４、及びＲ^ｂ５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｂ６は、炭素数８～２０の脂肪族炭化水素基である。Ｒ^ｂ７は、水素原子、炭素数１～２０のアルキル基、又は炭素数２～４のアルキレン基である。Ｒ^ｂ７が、炭素数２～４のアルキレン基である場合、Ｒ^ｂ７はＲ^ｂ６に結合する炭素原子Ｃ^ｂｘと結合し、環構造を形成する。］
［２］ 前記含窒素化合物（Ａ）は、下記一般式（ａ１）で表される含窒素化合物（Ａ１）を含有する、［１］に記載の潤滑油用添加剤。

［前記一般式（ａ１）中、Ｒ^ａ１１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、及びＲ^ａ１５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ａ１６は、炭素数８～２０の直鎖状の脂肪族炭化水素基である。
［３］ 前記含窒素化合物（Ｂ）は、下記一般式（ｂ１）で表される含窒素有化合物（Ｂ１）を含有する、［１］又は［２］に記載の潤滑油用添加剤。

［前記一般式（ｂ１）中、Ｒ^ｂ１１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｂ１２、Ｒ^ｂ１３、Ｒ^ｂ１４、及びＲ^ｂ１５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｂ１６は、炭素数８～２０の脂肪族炭化水素基である。Ｒ^ｂ１７は、水素原子又は炭素数１～２０のアルキル基である。］
［４］ 前記成分（Ｘ_ＡＢ）の含有量が、前記潤滑油用添加剤の全量基準で、５０質量％以上である、［１］～［３］のいずれかに記載の潤滑油用添加剤。
［５］ 下記一般式（ｃ）で表される含窒素化合物（Ｃ）から選択される１種以上の成分（Ｘ_Ｃ）の含有量が、前記潤滑油用添加剤の全量基準で、１０質量％未満である、［１］～［４］のいずれかに記載の潤滑油用添加剤。

［前記一般式（ｃ）中、Ｒ^ｃ１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｃ２、Ｒ^ｃ３、Ｒ^ｃ４、及びＲ^ｃ５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｃ６は、炭素数８～２０の分岐鎖状の脂肪族炭化水素基である。Ｒ^ｃ７は、水素原子、炭素数１～３のアルキル基、又は炭素数１～３のアルキレン基である。Ｒ^ｃ７が、炭素数１～３のアルキレン基である場合、Ｒ^ｃ７はＲ^ｃ６に結合する炭素原子Ｃ^ｃｘと結合し、環構造を形成する。］
［６］ 前記成分（Ｘ_ＡＢ）と前記成分（Ｘ_Ｃ）との含有比率［（Ｘ_ＡＢ）／（Ｘ_Ｃ）］が、質量比で、５／１超である、［５］に記載の潤滑油用添加剤。
［７］ ［１］～［６］のいずれかに記載の潤滑油用添加剤と、潤滑油基油（Ｐ）とを含有する、駆動系用潤滑油組成物。
［８］ ［１］～［６］のいずれか１項に記載の潤滑油用添加剤を含有する駆動系用潤滑油組成物を用いて、自動車のロックアップクラッチ機構のシャダーを防止する方法。
［９］ ［７］に記載の駆動系用潤滑油組成物を用いて、自動車のロックアップクラッチ機構のシャダーを防止する方法。 That is, the present invention relates to the following [1] to [12].
[1] One or more components (X _AB ) and used as an anti-shudder additive for lubricating oils.

[In the general formula (a), R ^a1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a2 , R ^a3 , R ^a4 and R ^a5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a6 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^a7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^a7 is an alkylene group having 1 to 3 carbon atoms, R ^a7 bonds with the carbon atom C ^ax bonded to R ^a6 to form a ring structure. ]

[In the general formula (b), R ^b1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b2 , R ^b3 , R ^b4 and R ^b5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b6 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^b7 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkylene group having 2 to 4 carbon atoms. When R ^b7 is an alkylene group having 2 to 4 carbon atoms, R ^b7 bonds with the carbon atom C ^bx bonding to R ^b6 to form a ring structure. ]
[2] The additive for lubricating oil according to [1], wherein the nitrogen-containing compound (A) contains a nitrogen-containing compound (A1) represented by the following general formula (a1).

[In the general formula (a1), R ^a11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a12 , R ^a13 , R ^a14 and R ^a15 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a16 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms.
[3] The lubricating oil additive according to [1] or [2], wherein the nitrogen-containing compound (B) contains a nitrogen-containing compound (B1) represented by the following general formula (b1).

[In the general formula (b1), R ^b11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b12 , R ^b13 , R ^b14 and R ^b15 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b16 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^b17 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. ]
[4] The lubricating oil additive according to any one of [1] to [3], wherein the content of the component (X _AB ) is 50% by mass or more based on the total amount of the lubricating oil additive. .
[5] The content of one or more components (X C ) selected from nitrogen-containing compounds ( _C ) represented by the following general formula (c) is 10 mass based on the total amount of the additive for lubricating oil %, the lubricating oil additive according to any one of [1] to [4].

[In the general formula (c), R ^c1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^c2 , R ^c3 , R ^c4 and R ^c5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^c6 is a branched aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^c7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^c7 is an alkylene group having 1 to 3 carbon atoms, R ^c7 bonds with the carbon atom C ^cx bonding to R ^c6 to form a ring structure. ]
[6] The content ratio [(X _AB )/(X _C )] of the component (X _AB ) and the component (X _C ) is greater than 5/1 in terms of mass ratio. Additive for lubricating oil.
[7] A lubricating oil composition for a drive system, comprising the lubricating oil additive according to any one of [1] to [6] and a lubricating base oil (P).
[8] A method for preventing shudder in a lock-up clutch mechanism of an automobile, using a drive system lubricating oil composition containing the lubricating oil additive according to any one of [1] to [6].
[9] A method for preventing shudder of a lock-up clutch mechanism of an automobile using the lubricating oil composition for a drive system according to [7].

According to the present invention, a lubricating oil additive that can greatly improve detergency while imparting anti-shudder performance to a lubricating oil composition for a drive system, and further containing the lubricating oil additive It becomes possible to provide a lubricating oil composition for a drive system.

In this specification, for preferred numerical ranges (for example, ranges of content etc.), the lower and upper limits described stepwise can be independently combined. For example, from the statement "preferably 10 to 90, more preferably 30 to 60", combining "preferred lower limit (10)" and "more preferred upper limit (60)" to "10 to 60" be able to.
In this specification, numerical values in the examples are numerical values that can be used as upper or lower limits.
In the present specification, the numerical range expressed as "AA to BB" means "AA or more and BB or less" unless otherwise specified.
As used herein, the term "based on the total amount of the additive for lubricating oil" means based on the total amount of the additive for lubricating oil of the present invention alone, excluding other additives described later.

[Aspect of the Lubricating Oil Additive of the Present Invention]
The lubricating oil additive of the present invention is selected from the group consisting of a nitrogen-containing compound (A) represented by the following general formula (a) and a nitrogen-containing compound (B) represented by the following general formula (b) It contains one or more components (X _AB ) and is used as an anti-shudder agent.

［前記一般式（ａ）中、Ｒ^ａ１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ａ２、Ｒ^ａ３、Ｒ^ａ４、及びＲ^ａ５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ａ６は、炭素数８～２０の直鎖状の脂肪族炭化水素基である。Ｒ^ａ７は、水素原子、炭素数１～３のアルキル基、又は炭素数１～３のアルキレン基である。Ｒ^ａ７が、炭素数１～３のアルキレン基である場合、Ｒ^ａ７はＲ^ａ６に結合する炭素原子Ｃ^ａｘと結合し、環構造を形成する。］

[In the general formula (a), R ^a1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a2 , R ^a3 , R ^a4 and R ^a5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a6 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^a7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^a7 is an alkylene group having 1 to 3 carbon atoms, R ^a7 bonds with the carbon atom C ^ax bonded to R ^a6 to form a ring structure. ]

［前記一般式（ｂ）中、Ｒ^ｂ１は、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｂ２、Ｒ^ｂ３、Ｒ^ｂ４、及びＲ^ｂ５は、各々独立に、水素原子又は炭素数１～３のアルキル基である。Ｒ^ｂ６は、炭素数８～２０の脂肪族炭化水素基である。Ｒ^ｂ７は、水素原子、炭素数１～２０のアルキル基、又は炭素数２～４のアルキレン基である。Ｒ^ｂ７が、炭素数２～４のアルキレン基である場合、Ｒ^ｂ７はＲ^ｂ６に結合する炭素原子Ｃ^ｂｘと結合し、環構造を形成する。］

[In the general formula (b), R ^b1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b2 , R ^b3 , R ^b4 and R ^b5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b6 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^b7 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkylene group having 2 to 4 carbon atoms. When R ^b7 is an alkylene group having 2 to 4 carbon atoms, R ^b7 bonds with the carbon atom C ^bx bonding to R ^b6 to form a ring structure. ]

The inventors of the present invention conducted intensive studies to find a lubricating oil additive capable of greatly improving detergency while imparting anti-shudder performance to a lubricating oil composition for drive systems. As a result, it was found that the bisimide compounds conventionally used as anti-shudder agents are excellent in anti-shudder performance, but are poor in performance for improving the cleanliness of lubricating oil compositions for drive systems.
Therefore, as a result of further intensive studies by the present inventors, among nitrogen-containing compounds in which a group having a piperidine skeleton is directly bonded to the nitrogen atom of a compound having an imide structure or an amide structure, a specific compound has anti-shudder performance. In addition to being excellent in the performance of improving the cleanliness of the lubricating oil composition for drive systems. Based on this knowledge, the present inventors have made further intensive studies and completed the present invention.

In addition, in the lubricating oil additive of one aspect of the present invention, the content of the component (X _AB ) is preferably 50 based on the total amount of the lubricating oil additive, from the viewpoint of making it easier to exhibit the effects of the present invention. % by mass or more, more preferably 60% by mass or more, still more preferably 70% by mass or more, even more preferably 80% by mass or more, and still more preferably 85% by mass or more.
Further, the upper limit of the content of the component (X _AB ) may be 100% by mass, but when other components other than the component (X _AB ) are contained, it is adjusted in consideration of the other components. preferably less than 100% by mass, more preferably less than 99% by mass, even more preferably less than 98% by mass, and even more preferably less than 97% by mass.
In addition, the lubricating oil additive of one aspect of the present invention contains, as the other components, by-products generated when synthesizing the lubricating oil additive and raw materials remaining without contributing to the reaction. or may contain compounds different from these. In addition, the additive for lubricating oil according to one aspect of the present invention may be diluted with a diluent solvent from the viewpoint of solubility in the base oil of lubricating oil and handleability. The content of each component in the additive for lubricating oil means the content relative to the total amount of the active ingredient in the additive for lubricating oil, excluding the diluent solvent.

The component (X _AB ) will be described in detail below.

[Component (X _AB )]
Component (X _AB ) is one or more selected from the group consisting of nitrogen-containing compounds (A) and nitrogen-containing compounds (B).
That is, the component (X _AB ) may be composed only of one or more selected from the nitrogen-containing compounds (A), or composed only of one or more selected from the nitrogen-containing compounds (B). It may be a combination of one or more selected from the nitrogen-containing compounds (A) and one or more selected from the nitrogen-containing compounds (B).
From the viewpoint of making it easier to exhibit the effects of the present invention, the component (X _AB ) preferably contains at least one selected from the nitrogen-containing compounds (A), and selected from the nitrogen-containing compounds (A). It is more preferable to be composed of only one or more types of
The nitrogen-containing compound (A) and the nitrogen-containing compound (B) are described in detail below.

<Nitrogen-containing compound (A)>
The nitrogen-containing compound (A) is a compound represented by the following general formula (a).

In the general formula (a), R ^a1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a1 is preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms (methyl group or ethyl group), more preferably a hydrogen atom or an alkyl group having 1 carbon atoms, from the viewpoint of making it easier to improve anti-shudder performance. a group (methyl group), more preferably a hydrogen atom.

In general formula (a), R ^a2 , R ^a3 , R ^a4 and R ^a5 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a2 , R ^a3 , R ^a4 , and R ^a5 are each independently preferably an alkyl group having 1 to 3 carbon atoms from the viewpoint of facilitating the improvement of the detergency of the lubricating oil composition for drive trains. , more preferably an alkyl group having 1 or 2 carbon atoms (methyl group or ethyl group), more preferably an alkyl group having 1 carbon atom (methyl group).

Since the nitrogen-containing compound (A) has a piperidine skeleton, excellent detergency for the nitrogen-containing compound (A) can be obtained without reducing the anti-shudder performance exhibited by the imide structure of the nitrogen-containing compound (A). It is speculated that this is one of the reasons for the grant.

In the general formula (a), R ^a6 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms.
When R ^a6 is a branched aliphatic hydrocarbon group, the anti-shudder performance is lowered.
When the number of carbon atoms in the aliphatic hydrocarbon group is less than 8, the solubility in lubricating base oil is reduced.
If the aliphatic hydrocarbon group has more than 20 carbon atoms, the anti-shudder performance may not be ensured.
Here, the linear aliphatic hydrocarbon group having 8 to 20 carbon atoms includes a linear alkyl group having 8 to 20 carbon atoms or a linear alkenyl group having 8 to 20 carbon atoms. . Among these, R ^a6 is a linear alkyl group having 8 to 20 carbon atoms from the viewpoint of improving the base number retention of the lubricating oil composition for a drive system and making it easier to improve detergency. is preferred.

The number of carbon atoms in the straight-chain alkyl group that can be selected as R ^a6 is preferably 9 to 19, more preferably 10 to 18, from the viewpoint of making it easier to exhibit the effects of the present invention.
The number of carbon atoms in the linear alkenyl group that can be selected as R ^a6 is preferably 9 to 19, more preferably 10 to 18, from the viewpoint of making it easier to exhibit the effects of the present invention.

In the general formula (a), R ^a7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^a7 is an alkylene group having 1 to 3 carbon atoms, R ^a7 bonds with the carbon atom C ^ax bonded to R ^a6 to form a ring structure.
Examples of alkylene groups having 1 to 3 carbon atoms include -CH ₂ -, -CH(CH ₃ )-, -CH ₂ CH ₂ -, and -CH ₂ CH(CH ₃ )-.
Among these, from the viewpoint of making it easier to exhibit the effects of the present invention, R ^a7 is an alkylene group having 1 to 3 carbon atoms, and is bonded to the carbon atom C ^ax bonded to R ^a6 to form a ring structure. is preferred. Moreover, R ^a7 is —CH ₂ — (methylene group), and is preferably bonded to the carbon atom C ^ax that is bonded to R ^a6 to form a ring structure.
That is, the nitrogen-containing compound (A) represented by the general formula (a) is preferably a nitrogen-containing compound (A1) represented by the following general formula (a1).

(Nitrogen-containing compound (A1))
The nitrogen-containing compound (A1) is a compound represented by the following general formula (a1).

In general formula (a1), R ^a11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a11 can be selected from the same group as R ^a1 in the general formula (a), and the preferred range is also the same as R ^a1 .

In general formula (a1), R ^a12 , R ^a13 , R ^a14 and R ^a15 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a12 , R ^a13 , R ^a14 and R ^a15 can be selected from the same groups as R ^a2 , R ^a3 , R ^a4 and R ^a5 in the general formula (a), and the preferred ranges are also R ^a2 and R Same as ^a3 , R ^a4 and R ^a5 .

In the general formula (a1), R ^a16 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^a16 can be selected from the same group as R ^a6 in the general formula (a), and the preferred range is also the same as that of R ^a6 .

Here, from the viewpoint of making it easier to exhibit the effects of the present invention, the content of the nitrogen-containing compound (A1) is preferably 50% by mass to 100% by mass, more preferably 50% by mass to 100% by mass, based on the total amount of the nitrogen-containing compound (A). Is 60% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, even more preferably 80% by mass to 100% by mass, still more preferably 90% by mass to 100% by mass, still more preferably 100% by mass is.

The nitrogen-containing compound (A1) may be used alone or in combination of two or more.

Here, in the nitrogen-containing compound (A1), the balance between anti-shudder performance and detergency can be changed depending on the carbon number of R ^a16 in the general formula (a1). Specifically, for the linear aliphatic hydrocarbon group having 8 to 20 carbon atoms that can be selected as R ^a16 in the general formula (a1), within the range of 8 to 20 carbon atoms, aliphatic carbonization If the number of carbon atoms in the hydrogen group is reduced, the anti-shudder performance can be further improved. Conversely, if the number of carbon atoms is increased, the detergency will be improved.
From this viewpoint, in one aspect of the present invention, in the general formula (a1), R ^a16 is a linear aliphatic hydrocarbon group having 8 to 13 carbon atoms (preferably a linear aliphatic hydrocarbon group having 8 to 13 carbon atoms A nitrogen-containing compound (A1α) which is an alkyl group, more preferably a linear alkyl group having 10 to 12 carbon atoms), and in the general formula (a1), R ^a16 is a linear linear alkyl group having 14 to 20 carbon atoms Used in combination with a nitrogen-containing compound (A1β) which is an aliphatic hydrocarbon group (preferably a straight-chain alkyl group having 14 to 20 carbon atoms, more preferably a straight-chain alkyl group having 14 to 18 carbon atoms) may
In this case, the content ratio [(A1α)/(A1β)] of the nitrogen-containing compound (A1α) and the nitrogen-containing compound (A1β) is preferably 1/10 to 10/1, more preferably 1/ 5 to 5/1, more preferably 1/2 to 2/1.
The nitrogen-containing compound (A1α) may be used singly or in combination of two or more. The nitrogen-containing compound (A1β) may also be used singly or in combination of two or more.

<Nitrogen-containing compound (B)>
The nitrogen-containing compound (B) is a compound represented by the following general formula (b).

In the general formula (b), R ^b1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b1 is preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms (methyl group or ethyl group), more preferably a hydrogen atom or an alkyl group having 1 carbon atoms, from the viewpoint of making it easier to improve anti-shudder performance. a group (methyl group), more preferably a hydrogen atom.

In general formula (b), R ^b2 , R ^b3 , R ^b4 and R ^b5 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b2 , R ^b3 , R ^b4 , and R ^b5 are each independently preferably an alkyl group having 1 to 3 carbon atoms from the viewpoint of making it easier to improve the detergency of the lubricating oil composition for drive trains. , more preferably an alkyl group having 1 or 2 carbon atoms (methyl group or ethyl group), more preferably an alkyl group having 1 carbon atom (methyl group).

Since the nitrogen-containing compound (A) has a piperidine skeleton, excellent detergency for the nitrogen-containing compound (A) can be obtained without reducing the anti-shudder performance exhibited by the amide structure of the nitrogen-containing compound (A). It is speculated that this is one of the reasons for the grant.

In the general formula (b), R ^b6 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms.
When the number of carbon atoms in the aliphatic hydrocarbon group is less than 8, the solubility in lubricating base oil is lowered.
If the aliphatic hydrocarbon group has more than 20 carbon atoms, the anti-shudder performance may not be ensured.
Here, the aliphatic hydrocarbon group having 8 to 20 carbon atoms includes an alkyl group having 8 to 20 carbon atoms and an alkenyl group having 8 to 20 carbon atoms. These may be linear or branched. Here, among these, from the viewpoint of improving the base number maintenance property of the lubricating oil composition for drive trains and making it easier to improve detergency, R ^a6 is a straight-chain alkyl having 8 to 20 carbon atoms. It is preferably a group.

The number of carbon atoms in the alkyl group that can be selected as R ^b6 is preferably 9 to 19, more preferably 10 to 18, from the viewpoint of making it easier to exhibit the effects of the present invention.
The number of carbon atoms in the alkenyl group that can be selected as R ^b6 is preferably 9 to 19, more preferably 10 to 18, from the viewpoint of making it easier to exhibit the effects of the present invention.

In the general formula (b), R ^b7 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkylene group having 2 to 4 carbon atoms. When R ^b7 is an alkylene group having 2 to 4 carbon atoms, R ^b7 bonds with the carbon atom C ^bx bonding to R ^b6 to form a ring structure.
Examples of alkylene groups having 2 to 4 carbon atoms are -CH ₂ CH ₂ -, -CH ₂ CH(CH ₃ )-, -CH ₂ CH ₂ CH ₂ -, -CH ₂ CH(CH ₃ )CH ₂ -, or -CH ₂ CH ₂ CH(CH ₃ )- and the like.
Among these, from the viewpoint of making it easier to exhibit the effects of the present invention, from the viewpoint of improving the solubility of the nitrogen-containing compound (b) in the lubricating base oil, and from the viewpoint of suppressing sludge generation, R ^b7 is hydrogen It is preferably an atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and further preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. preferable. That is, the nitrogen-containing compound (B) represented by the general formula (b) is preferably a nitrogen-containing compound (B1) represented by the following general formula (b1).

(Nitrogen-containing compound (B1))
The nitrogen-containing compound (B1) is a compound represented by the following general formula (b1).

In general formula (b1), ^Rb11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b11 can be selected from the same group as R ^b1 in the general formula (b), and the preferred range is also the same as that of R ^b1 .

In general formula (b1), R ^b12 , R ^b13 , R ^b14 and R ^b15 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b12 , R ^b13 , R ^b14 and R ^b15 can be selected from the same groups as R ^b2 , R ^b3 , R ^b4 and R ^b5 in the general formula (b), and the preferred ranges are also R ^b2 and R Same as ^b3 , R ^b4 , and R ^b5 .

In general formula (b1), R ^b16 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^b16 can be selected from the same group as R ^b6 in the general formula (b), and the preferred range is also the same as that of R ^b6 .

In general formula (b1), R ^b17 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. Here, from the viewpoint of making it easier to exhibit the effects of the present invention, from the viewpoint of improving the solubility of the nitrogen-containing compound (b1) in the lubricating base oil, and from the viewpoint of suppressing sludge generation, R ^b17 is preferably is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more More preferably, it is a hydrogen atom.

Here, from the viewpoint of making it easier to exhibit the effects of the present invention, the content of the nitrogen-containing compound (B1) is preferably 50% by mass to 100% by mass, more preferably 50% by mass to 100% by mass, based on the total amount of the nitrogen-containing compound (B). Is 60% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, even more preferably 80% by mass to 100% by mass, still more preferably 90% by mass to 100% by mass, still more preferably 100% by mass is.

The nitrogen-containing compound (B1) may be used alone or in combination of two or more.
Here, in the nitrogen-containing compound (B1), the balance between anti-shudder performance and detergency can be changed depending on the number of carbon atoms of ^Rb16 in the general formula (b1). Specifically, for an aliphatic hydrocarbon group having 8 to 20 carbon atoms that can be selected as R ^b16 in the general formula (b1), within the range of 8 to 20 carbon atoms, the carbon of the aliphatic hydrocarbon group Decreasing the number can further improve the anti-shudder performance, and conversely, increasing the number of carbons improves cleanliness.
From this viewpoint, in one aspect of the present invention, in the general formula (b1), R ^b16 is a linear aliphatic hydrocarbon group having 8 to 13 carbon atoms (preferably a linear aliphatic hydrocarbon group having 8 to 13 carbon atoms a nitrogen-containing compound (B1α) which ^is an alkyl group, more preferably a straight-chain alkyl group having 10 to 12 carbon atoms; Use in combination with a nitrogen-containing compound (B1β) that is an aliphatic hydrocarbon group (preferably a straight-chain alkyl group having 14 to 20 carbon atoms, more preferably a straight-chain alkyl group having 14 to 18 carbon atoms) may
In this case, the content ratio [(B1α)/(B1β)] of the nitrogen-containing compound (B1α) and the nitrogen-containing compound (B1β) is preferably 1/10 to 10/1, more preferably 1/ 5 to 5/1, more preferably 1/2 to 2/1.
The nitrogen-containing compound (B1α) may be used singly or in combination of two or more. The nitrogen-containing compound (B1β) may also be used singly or in combination of two or more.

[Component (X _C )]
The lubricating oil additive of one aspect of the present invention may contain component (X _C ).
Component (X _C ) is one or more selected from nitrogen-containing compounds (C).
Here, in the lubricating oil additive of one aspect of the present invention, the content of the component (X _C ) is preferably small from the viewpoint of making the lubricating oil additive more excellent in anti-shudder performance.
Specifically, the content of component (X _C ) is preferably less than 10% by mass, more preferably less than 1.0% by mass, and still more preferably 0.1% by mass, based on the total amount of the additive for lubricating oil. less than, and even more preferably, no component (X _C ).
In addition, the content ratio [(X _AB )/(X _C )] of the component (X _AB ) and the component (X _C ) is preferably more than 5/1, more preferably 10/1 or more, and further It is preferably 100/1 or more, and more preferably 1000/1 or more.
The nitrogen-containing compound (C) will be described in detail below.

<Nitrogen-containing compound (C)>
The nitrogen-containing compound (C) is a compound represented by the following general formula (c).

In general formula (c), R ^c1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^c2 , R ^c3 , R ^c4 and R ^c5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^c6 is a branched aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^c7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^c7 is an alkylene group having 1 to 3 carbon atoms, R ^c7 bonds with the carbon atom C ^cx bonding to R ^c6 to form a ring structure.

According to the studies of the present inventors, in the general formula (c), when R ^c6 is a branched aliphatic hydrocarbon group having 8 to 20 carbon atoms, the anti-shudder performance is greatly reduced. ing.
Therefore, the content of the nitrogen-containing compound (C), which is a compound similar to the nitrogen-containing compound (A), is preferably small as described above.
[Component (X _D )]
The lubricating oil additive of one aspect of the present invention may contain component (X _D ).
Component (X _D ) is one or more nitrogen-containing compounds (D) selected from the group consisting of nitrogen-containing compounds (D1) and nitrogen-containing compounds (D2).
However, in the lubricating oil additive of one aspect of the present invention, the content of the component (X _D ) is preferably small from the viewpoint of making the lubricating oil additive more excellent in anti-shudder performance.
Specifically, the content of component (X _D ) is preferably less than 10% by mass, more preferably less than 1.0% by mass, and still more preferably 0.1% by mass, based on the total amount of the additive for lubricating oil. less than, and even more preferably not containing component (X _D ).
In addition, the content ratio [(X _AB )/(X _D )] of the component (X _AB ) and the component (X _D ) is preferably more than 5/1, more preferably 10/1 or more, and further It is preferably 100/1 or more, and more preferably 1000/1 or more.
The nitrogen-containing compound (D1) and the nitrogen-containing compound (D2) are described in detail below.

(Nitrogen-containing compound (D1))
The nitrogen-containing compound (D1) is a compound represented by the following general formula (d1).

In general formula (d1), R ^d1 is an acyl group. R ^d2 , R ^d3 , R ^d4 and R ^d5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
R ^d16 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. The aliphatic hydrocarbon group may be linear or branched.
R ^d17 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^d17 is an alkylene group having 1 to 3 carbon atoms, R ^d17 bonds with the carbon atom C ^d1x that bonds to R ^d16 to form a ring structure.

(Nitrogen-containing compound (D2))
The nitrogen-containing compound (D2) is a compound represented by the following general formula (d2).

In general formula (d2), R ^d1 , R ^d2 , R ^d3 , R ^d4 , and R ^d5 are as described in general formula (d1).
R ^d26 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. The aliphatic hydrocarbon group may be linear or branched.
R ^d27 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkylene group having 2 to 4 carbon atoms. When R ^d27 is an alkylene group having 2 to 4 carbon atoms, R ^d27 bonds with the carbon atom C ^d2x bonding to R ^d26 to form a ring structure.

[Physical properties of lubricating oil additives]
<Shudder prevention performance>
The lubricating oil additive of one aspect of the present invention is measured and calculated by a method performed by adding the lubricating oil additive only to the base oil, among the methods described in the examples described later. Performance parameter (μ1/μ100) is preferably 1.0 or less, more preferably 0.95 or less, still more preferably 0.90 or less, even more preferably 0.85 or less, and still more preferably 0.80 It is below.
In addition, the lubricating oil composition of one aspect of the present invention is measured and implemented by adding a lubricating oil additive only to the base oil, among the methods described in the examples described later. Slip control The parameter (μ100) indicating the coefficient of friction μ at time is preferably 0.080 or more, more preferably 0.090 or more, still more preferably 0.10 or more, still more preferably 0.11 or more, and still more preferably 0 .12 or greater.

<Cleanliness>
The lubricating oil additive of one aspect of the present invention has a base number residual rate measured by a method performed by adding the lubricating oil additive only to mineral oil among the methods described in the examples described later. , preferably 10% or more, more preferably 15% or more, and still more preferably 18% or more.
In addition, the lubricating oil additive of one aspect of the present invention is measured by a method performed by adding the lubricating oil additive only to mineral oil, among the methods described in the examples described later. is preferably 6.0 or higher, more preferably 7.0 or higher, and still more preferably 8.0 or higher.
Furthermore, the lubricating oil additive of one aspect of the present invention has an acid value measured by a method performed by adding the lubricating oil additive only to mineral oil among the methods described in the examples described later, It is preferably 15.0 mgKOH/g or less, more preferably 14.0 mgKOH/g or less, even more preferably 13.0 mgKOH/g or less, still more preferably 12.5 mgKOH/g or less.

[Use of the additive for lubricating oil of the present invention]
The lubricating oil additive of the present invention can greatly improve detergency while imparting anti-shudder performance to a lubricating oil composition for a drive system.
Therefore, the lubricating oil additive of the present invention is useful as an anti-shudder agent. Furthermore, the lubricating oil additive of one aspect of the present invention is useful as a lubricating oil additive that serves both as an anti-shudder agent and a detergent.

[Method for producing additive for lubricating oil]
Although the method for producing the lubricating oil additive of the present invention is not particularly limited, it can be produced, for example, by the following production method.

［化学反応式（１）中、Ｒ^ａ１、Ｒ^ａ２、Ｒ^ａ３、Ｒ^ａ４、Ｒ^ａ５、Ｒ^ａ６、及びＲ^ａ７は、上記一般式（ａ）において説明したとおりである。］ Specifically, the nitrogen-containing compound (A) represented by the general formula (a) is a carboxylic anhydride compound represented by the following general formula (ax), as shown in the chemical reaction formula (1) below. AX) and an amino group-containing piperidine compound (AY) represented by the following general formula (ay).

[In chemical reaction formula (1), R ^a1 , R ^a2 , R ^a3 , R ^a4 , R ^a5 , R ^a6 , and R ^a7 are as described in general formula (a) above. ]

［化学反応式（２）中、Ｒ^ｂ１、Ｒ^ｂ２、Ｒ^ｂ３、Ｒ^ｂ４、Ｒ^ｂ５、Ｒ^ｂ６、及びＲ^ｂ７は、上記一般式（ｂ）の説明において説明したとおりである。］ Further, the nitrogen-containing compound (B) represented by the above general formula (b) is, as shown in the following chemical reaction formula (2), a carboxylic acid compound (BX) represented by the following general formula (bx), It can be produced by reacting with an amino group-containing piperidine compound (BY) represented by the following general formula (by).

[In chemical reaction formula (2), R ^b1 , R ^b2 , R ^b3 , R ^b4 , R ^b5 , R ^b6 , and R ^b7 are as explained in the explanation of general formula (b) above. ]

The reaction temperature of the chemical reaction formulas (1) and (2) is usually 100 to 200°C, preferably 110 to 190°C, more preferably 120 to 180°C. The reaction time is generally 1 to 10 hours, preferably 2 to 8 hours, more preferably 2 to 6 hours.

From the viewpoint of smoothly proceeding the reactions shown in the chemical reaction formulas (1) and (2), the carboxylic anhydride compound (AX), the amino group-containing piperidine compound (AY), the carboxylic acid compound (BX), and the amino The group-containing piperidine compound (BY) is preferably dissolved in an organic solvent. As the organic solvent, for example, one or more selected from the group consisting of xylene, toluene, heptane, alcohols, and the like can be used. However, the reactions shown in the chemical reaction formulas (1) and (2) may be carried out without a solvent.

After the reaction is completed, it is preferable to purify by removing the solvent and light components by heating under reduced pressure, if necessary.

From the viewpoint of increasing the solubility of the carboxylic anhydride compound (AX) and the carboxylic acid compound (BX) in the solvent and lowering the reaction temperature, R ^a6 in the general formula (ax) and the general formula (bx) ) may be an unsaturated ^aliphatic hydrocarbon group. After completion of the reaction, a hydrogenation reaction may be performed to hydrogenate R ^a6 in the general formula (a) and R ^b6 in the general formula (b) to form a saturated aliphatic hydrocarbon group.

[Lubricating oil composition for drive system]
The lubricating oil composition for a drive system of the present invention contains the lubricating oil additive and a lubricating oil base oil (P).
In the lubricating oil composition for a drive system of one aspect of the present invention, the content of the lubricating oil additive is the component (X _AB ) from the viewpoint of better exhibiting the addition effect of the lubricating oil additive. The content is based on the total amount of the lubricating oil composition for the drive system, preferably 0.01 to 20% by mass, more preferably 0.05 to 15% by mass, still more preferably 0.1 to 10% by mass, more More preferably, it is adjusted to 0.1 to 5.0% by mass.
Further, in the lubricating oil composition for a drive system of one aspect of the present invention, the content of the lubricating oil additive is, from the viewpoint of better exhibiting the addition effect of the lubricating oil additive, the component (X The content of _C ) is preferably less than 0.1% by mass, more preferably less than 0.01% by mass, and still more preferably less than 0.001% by mass, based on the total amount of the lubricating oil composition for a drive system. adjusted to
Furthermore, in the lubricating oil composition for a drive system of one aspect of the present invention, the content of the lubricating oil additive is, from the viewpoint of better exhibiting the addition effect of the lubricating oil additive, the component (X The content of _D ) is preferably less than 0.1% by mass, more preferably less than 0.01% by mass, and still more preferably less than 0.001% by mass, based on the total amount of the drive system lubricating oil composition. adjusted to

Further, in the lubricating oil composition for a drive system of one aspect of the present invention, the content of the lubricating oil additive is, from the viewpoint of better exhibiting the addition effect of the lubricating oil additive, the component (X _AB )-derived nitrogen content is preferably 7 mass ppm to 14,000 mass ppm, more preferably 35 mass ppm to 10,500 mass ppm, and still more preferably 70 mass ppm, based on the total amount of the drive system lubricating oil composition. ppm to 7,000 ppm by weight.

<Lubricating base oil>
The lubricating base oil may be one or more selected from the group consisting of mineral oils and synthetic oils.
The kinematic viscosity at 100° C. of the lubricating base oil is preferably in the range of 1 to 50 mm ² /s, more preferably in the range of 2 to 20 mm ² /s. Also, the viscosity index is preferably 80 or more, more preferably 90 or more, and even more preferably 100 or more.
The kinematic viscosity and viscosity index of the lubricating base oil are values measured and calculated according to JIS K2283:2000.
Specific examples of lubricating base oils are given below.
Mineral oils include, for example, distillates obtained by atmospheric distillation and/or vacuum distillation of paraffin-based crude oils, intermediate-based crude oils, or naphthenic-based crude oils; oil; and the like. Refining methods for obtaining refined oil include, for example, solvent dewaxing, hydroisomerization, hydrofinishing, and clay treatment.
Synthetic oils include, for example, hydrocarbon oils, aromatic oils, ester oils, ether oils and the like. As the synthetic oil, GTL (Gas To Liquids) obtained by isomerizing wax (GTL wax, Gas To Liquids WAX) produced from natural gas by the Fischer-Tropsch process or the like may be used.

<Other additives>
The lubricating oil composition for a drive system according to one aspect of the present invention includes antioxidants, oiliness agents, extreme pressure agents, detergent dispersants, viscosity index improvers, flow One or more other additives selected from point depressants, rust inhibitors, metal deactivators, defoamers, and the like may also be included.
Further, as one aspect of the present invention, together with the lubricating oil additive of the present invention, other additives (antioxidants, oiliness agents, extreme pressure agents, detergent dispersants, viscosity index improvers, rust inhibitors, metal Also included are additive packages for driveline lubricating oil compositions containing deactivators, one or more selected from antifoaming agents, and the like.

(Antioxidant)
As antioxidants, amine-based antioxidants, phenol-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants can be used.
These antioxidants can be used singly or in combination of two or more.
Examples of amine antioxidants include monoalkyldiphenylamine compounds such as monooctyldiphenylamine and monononyldiphenylamine; ,4'-diheptyldiphenylamine, 4,4'-dioctyldiphenylamine, and 4,4'-dinonyldiphenylamine; dialkyldiphenylamine compounds; tetrabutyldiphenylamine, tetrahexyldiphenylamine, tetraoctyldiphenylamine, and tetranonyldiphenylamine 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 phenolic antioxidants include monophenolic compounds such as 2,6-di-tert-butyl-4-methylphenol and 2,6-di-tert-butyl-4-ethylphenol; -methylenebis(2,6-di-tert-butylphenol) and 2,2'-methylenebis(4-ethyl-6-tert-butylphenol) and other bisphenol compounds Phosphorus-based antioxidants include, for example, tri phenyl phosphite and diethyl[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]phosphonate;
Examples of sulfur-based antioxidants include 2,6-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino)phenol, phosphorus pentasulfide and Thioterpene compounds such as reaction products with pinene, dilauryl thiodipropionate, dialkyl thiodipropionate such as distearyl thiodipropionate, and the like.
The content of the antioxidant may be the minimum amount required to maintain the oxidation stability of the drive system lubricating oil composition. Specifically, for example, it is preferably 0.01 to 1% by mass based on the total amount of the lubricating oil composition for drive system.

(oily agent)
Oily agents include fatty 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 for a drive system, from the viewpoint of the effect of addition.

(extreme pressure agent)
Extreme pressure agents include sulfur-based extreme pressure agents, phosphorus-based extreme pressure agents, extreme pressure agents containing sulfur and metals, and extreme pressure agents containing phosphorus and metals. These extreme pressure agents can be used singly or in combination of two or more. Any extreme pressure agent may be used as long as it contains at least one of a sulfur atom and a phosphorus atom in its molecule and can exhibit load bearing properties and wear resistance.
Examples of extreme pressure agents containing sulfur in the molecule include sulfurized fats and oils, sulfurized fatty acids, sulfurized esters, sulfurized olefins, dihydrocarbyl polysulfides, thiadiazole compounds, alkylthiocarbamoyl compounds, triazine compounds, thioterpene compounds, and dialkylthiodipropionate compounds. etc. can be mentioned.
Typical 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, dialkyldithioline zinc acid (Zn-DTP), molybdenum dialkyldithiophosphate (Mo-DTP), sodium sulfonate, and calcium sulfonate.
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 for drive trains, from the viewpoint of addition effect and economy. %.

(detergent dispersant)
Detergent-dispersants include metal sulfonates, metal salicylates, and metal phenates, as well as succinimides and borated succinimides.
The content of the detergent-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 for a drive system, from the viewpoint of addition effect.

(Viscosity index improver)
Viscosity index improvers include, for example, polymethacrylates, dispersed polymethacrylates, olefin copolymers (e.g., ethylene-propylene copolymers), dispersed olefin copolymers, styrene copolymers (e.g., styrene-diene hydrogenated copolymer, etc.).
The content of the viscosity index improver is preferably 0.3 to 5% by mass based on the total amount of the drive system lubricating oil composition.

(Pour point depressant)
Examples of pour point depressants include ethylene-vinyl acetate copolymers, condensates of chlorinated paraffin and naphthalene, condensates of chlorinated paraffin and phenol, and polymers such as polymethacrylate and polyalkylstyrene. . The mass average molecular weight (Mw) of these polymers is preferably 50,000 to 150,000.
The content of the pour point depressant is preferably 0.01 mass% to 5.0 mass%, more preferably 0.02 mass% to 2.0% by mass.

(anti-rust)
Rust inhibitors include metal sulfonates, succinate esters, and alkanolamines such as alkylamines and monoisopropanolamine.
The content of the rust inhibitor 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 for a drive system, from the viewpoint of the effect of addition.

(metal deactivator)
Examples of metal deactivators include benzotriazole and thiadiazole.
A 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 for the drive system, from the viewpoint of the effect of addition. .

(Antifoaming agent)
Antifoaming agents include methylsilicone oil, fluorosilicone oil, polyacrylate, and the like.
The content of the antifoaming agent is usually 0.0005 to 0.01% by mass, based on the total amount of the lubricating oil composition for a drive system, from the viewpoint of addition effect.

[Use of lubricating oil composition for drive system]
The drive system lubricating oil composition of the present invention is excellent in anti-shudder performance and detergency.
Therefore, the lubricating oil composition for a drive system of the present invention can be suitably used for drive system oils such as automatic transmission oils and continuously variable transmission oils, and prevents shudder and clogging of the clutch material due to sludge. prevented.

Therefore, one aspect of the method of using the drive system lubricating oil composition of the present invention includes a method of using the drive system lubricating oil composition in an automatic transmission and a continuously variable transmission. In addition, as one aspect of the method of using the lubricating oil composition for a drive system of the present invention, there is a method of preventing shudder of a lock-up clutch mechanism of an automobile using the lubricating oil composition for a drive system.
Moreover, one aspect of the present invention includes an automatic transmission or a continuously variable transmission containing the lubricating oil composition for a drive system. It also includes a lock-up clutch mechanism for an automobile containing the drive system lubricating oil composition.
Furthermore, one aspect of the present invention includes an automobile equipped with an automatic transmission or a continuously variable transmission containing the lubricating oil composition for a drive system. Further, an automobile equipped with a lock-up clutch mechanism containing the lubricating oil composition for a drive system can be mentioned.

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

[Methods for measuring various physical property values]
It was carried out according to the procedure shown below.
<Kinematic viscosity at 40°C of base oil (X)>
Measured according to JIS K2283:2000.

[Examples 1 to 7 and Comparative Examples 1 to 5]
<Manufacture of various compounds>
The compounds used as lubricating oil additives in Examples 1 to 7 and Comparative Examples 2 and 4 were produced by the method described below.

上記式（１）で表される含窒素化合物（Ａ１）－１は、上記一般式（ａ１）中、Ｒ^ａ１１、Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５、Ｒ^ａ１６が以下の基である化合物である。
・Ｒ^ａ１１：水素原子
・Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５：炭素数１のアルキル基（メチル基）
・Ｒ^ａ１６：炭素数１２の直鎖状アルキル基（ｎ－ドデシル基） [Production Examples 1 to 9, Comparative Production Examples 1 to 4]
(1) Production Example 1: Nitrogen-containing compound (A1)-1
59 g (0.22 mol) of 2-dodecen-1-ylsuccinic anhydride and 10 mL of xylene were added to a 200 mL four-necked flask, and the solution in the flask was heated to 80°C, and then maintained at 80°C. 34 g (0.22 mol) of 4-amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 10 mL of methanol and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. under a hydrogen pressure of 2 MPa for 4 hours to form a nitrogen-containing compound (A1)-1, a red color. 85 g of an oily product were obtained. Nitrogen-containing compound (A1)-1 is a compound represented by the following chemical structural formula (1).

In the nitrogen-containing compound (A1)-1 represented by the above formula (1), in the above general formula (a1), R ^a11 , R ^a12 , R ^a13 , R ^a14 , R ^a15 and R ^a16 are the following groups. is a compound.
・R ^a11 : hydrogen atom ・R ^a12 , R ^a13 , R ^a14 , R ^a15 : alkyl group having 1 carbon atom (methyl group)
・R ^a16 : a linear alkyl group having 12 carbon atoms (n-dodecyl group)

上記式（２）で表される含窒素化合物（Ａ１）－２は、上記一般式（ａ１）中、Ｒ^ａ１１、Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５、Ｒ^ａ１６が以下の基である化合物である。
・Ｒ^ａ１１：水素原子
・Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５：炭素数１のアルキル基（メチル基）
・Ｒ^ａ１６：炭素数１２の直鎖状アルケニル基（ｎ－ドデセニル基） (2) Production Example 2: Nitrogen-containing compound (A1)-2
59 g (0.22 mol) of 2-dodecen-1-ylsuccinic anhydride and 10 mL of xylene were added to a 200 mL four-necked flask, and the solution in the flask was heated to 80°C, and then maintained at 80°C. 34 g (0.22 mol) of 4-amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After stirring, while maintaining the temperature of the solution at 140 ° C., the pressure in the flask was reduced for 3 hours with a vacuum pump to remove the solvent and light components to obtain a nitrogen-containing compound (A1)-2, which was a red oil. 89 g of a crystalline product were obtained. Nitrogen-containing compound (A1)-2 is a compound represented by the following chemical structural formula (2).

In the nitrogen-containing compound (A1)-2 represented by the formula (2), in the general formula (a1), R ^a11 , R ^a12 , R ^a13 , R ^a14 , R ^a15 and R ^a16 are the following groups. is a compound.
・R ^a11 : hydrogen atom ・R ^a12 , R ^a13 , R ^a14 , R ^a15 : alkyl group having 1 carbon atom (methyl group)
・R ^a16 : a linear alkenyl group having 12 carbon atoms (n-dodecenyl group)

上記式（３）で表される含窒素化合物（Ａ１）－３は、上記一般式（ａ１）中、Ｒ^ａ１１、Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５、Ｒ^ａ１６が以下の基である化合物である。
・Ｒ^ａ１１：水素原子
・Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５：炭素数１のアルキル基（メチル基）
・Ｒ^ａ１６：炭素数１０の直鎖状アルキル基（ｎ－デシル基） (3) Production Example 3: Nitrogen-containing compound (A1)-3
41 g (0.17 mol) of decenylsuccinic anhydride and 15 mL of xylene were added to a 200 mL four-necked flask, the solution in the flask was heated to 80 ° C., and then, while maintaining the state of 80 ° C., 4- 27 g (0.17 mol) of amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 10 mL of methanol and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. under a hydrogen pressure of 2 MPa for 4 hours to give a nitrogen-containing compound (A1)-3 as a red oil. 46 g of a crystalline product were obtained. Nitrogen-containing compound (A1)-3 is a compound represented by the following chemical structural formula (3).

In the nitrogen-containing compound (A1)-3 represented by the formula (3), in the general formula (a1), R ^a11 , R ^a12 , R ^a13 , R ^a14 , R ^a15 and R ^a16 are the following groups. is a compound.
・R ^a11 : hydrogen atom ・R ^a12 , R ^a13 , R ^a14 , R ^a15 : alkyl group having 1 carbon atom (methyl group)
・R ^a16 : a linear alkyl group having 10 carbon atoms (n-decyl group)

上記式（４）で表される含窒素化合物（Ａ１）－４は、上記一般式（ａ１）中、Ｒ^ａ１１、Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５、Ｒ^ａ１６が以下の基である化合物である。
・Ｒ^ａ１１：水素原子
・Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５：炭素数１のアルキル基（メチル基）
・Ｒ^ａ１６：炭素数１４の直鎖状アルキル基（ｎ－テトラデシル基） (4) Production Example 4: Nitrogen-containing compound (A1)-4
50 g (0.17 mol) of tetradecenylsuccinic anhydride and 20 mL of xylene were added to a 200-mL four-necked flask, and the solution in the flask was heated to 80°C, and the temperature was maintained at 80°C. 27 g (0.17 mol) of 4-amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 10 mL of methanol and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. under a hydrogen pressure of 2 MPa for 5 hours to obtain a nitrogen-containing compound (A1)-4 as a red oil. 58 g of a crystalline product were obtained. Nitrogen-containing compound (A1)-4 is a compound represented by the following chemical structural formula (4).

In the nitrogen-containing compound (A1)-4 represented by the formula (4), in the general formula (a1), R ^a11 , R ^a12 , R ^a13 , R ^a14 , R ^a15 and R ^a16 are the following groups. is a compound.
・R ^a11 : hydrogen atom ・R ^a12 , R ^a13 , R ^a14 , R ^a15 : alkyl group having 1 carbon atom (methyl group)
・R ^a16 : a linear alkyl group having 14 carbon atoms (n-tetradecyl group)

上記式（５）で表される含窒素化合物（Ａ１）－５は、上記一般式（ａ１）中、Ｒ^ａ１１、Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５、Ｒ^ａ１６が以下の基である化合物である。
・Ｒ^ａ１１：水素原子
・Ｒ^ａ１２、Ｒ^ａ１３、Ｒ^ａ１４、Ｒ^ａ１５：炭素数１のアルキル基（メチル基）
・Ｒ^ａ１６：炭素数１８の直鎖状アルキル基（ｎ－オクタデシル基） (5) Production Example 5: Nitrogen-containing compound (A1)-5
42 g (0.12 mol) of octadecenylsuccinic anhydride and 20 mL of xylene were added to a 200 mL four-necked flask, the solution in the flask was heated to 80°C, and the temperature was maintained at 80°C. Then, 19 g (0.12 mol) of 4-amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 50 mL of methanol, 10 mL of hexane and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. for 4 hours at a hydrogen pressure of 2 MPa to obtain a nitrogen-containing compound (A1)-5. 46 g of a yellow solid product were obtained. Nitrogen-containing compound (A1)-5 is a compound represented by the following chemical structural formula (5).

In the nitrogen-containing compound (A1)-5 represented by the formula (5), in the general formula (a1), R ^a11 , R ^a12 , R ^a13 , R ^a14 , R ^a15 and R ^a16 are the following groups. is a compound.
・R ^a11 : hydrogen atom ・R ^a12 , R ^a13 , R ^a14 , R ^a15 : alkyl group having 1 carbon atom (methyl group)
・R ^a16 : a linear alkyl group having 18 carbon atoms (n-octadecyl group)

上記式（６）で表される含窒素化合物（Ｂ１）－１は、上記一般式（ｂ１）中、Ｒ^ｂ１１、Ｒ^ｂ１２、Ｒ^ｂ１３、Ｒ^ｂ１４、Ｒ^ｂ１５、Ｒ^ｂ１６、Ｒ^ｂ１７が以下の基である化合物である。
・Ｒ^ｂ１１：水素原子
・Ｒ^ｂ１２、Ｒ^ｂ１３、Ｒ^ｂ１４、Ｒ^ｂ１５：炭素数１のアルキル基（メチル基）
・Ｒ^ｂ１６：炭素数１６の直鎖状アルキル基（ｎ－ヘキサデシル基）
・Ｒ^ｂ１７：水素原子 (6) Production Example 6: Nitrogen-containing compound (B1)-1
34 g (0.22 mol) of 4-amino-2,2,6,6-tetramethylpiperidine and 30 mL of xylene were added to a 200 mL four-necked flask, and the solution in the flask was heated to 80° C. C., 61 g (0.22 mol) of oleic acid was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 20 mL of methanol and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. under a hydrogen pressure of 2 MPa for 4 hours to give a nitrogen-containing compound (B1)-1 as a red oil. 78 g of a crystalline product were obtained. Nitrogen-containing compound (B1)-1 is a compound represented by the following chemical structural formula (6).

In the nitrogen-containing compound (B1)-1 represented by the formula (6), in the general formula (b1), R ^b11 , R ^b12 , R ^b13 , R ^b14 , R ^b15 , R ^b16 and R ^b17 are the following It is a compound that is a group.
・R ^b11 : hydrogen atom ・R ^b12 , R ^b13 , R ^b14 , R ^b15 : alkyl group having 1 carbon atom (methyl group)
・R ^b16 : a linear alkyl group having 16 carbon atoms (n-hexadecyl group)
・R ^b17 : hydrogen atom

上記式（７）中、「ｉＣ_１８」は、イソオクタデセニル基である。 (7) Comparative Production Example 1
56 g (0.16 mol) of isooctadecenylsuccinic anhydride and 20 mL of xylene were added to a 200-mL four-necked flask, and the solution in the flask was heated to 80°C, and then maintained at 80°C. 12 g (0.08 mol) of diethylenetriamine was added dropwise over 30 minutes. After dropping diethylenetriamine, the solution in the flask was heated to 150° C. and stirred for 3 hours. After stirring, while maintaining the temperature of the solution at 140° C., the pressure in the flask was reduced by a vacuum pump for 3 hours to remove the solvent and light components, thereby obtaining 55 g of a red oily product as a bisimide compound. . A bisimide compound is a compound represented by the following chemical structural formula (7).

In formula (7) above, “iC ₁₈ ” is an isooctadecenyl group.

上記式（８）で表される含窒素化合物（Ｃ）－１は、上記一般式（ｃ）中、Ｒ^ｃ１、Ｒ^ｃ２、Ｒ^ｃ３、Ｒ^ｃ４、Ｒ^ｃ５、Ｒ^ｃ６、Ｒ^ｃ７が以下の基である化合物である。
・Ｒ^ｃ１：水素原子
・Ｒ^ｃ２、Ｒ^ｃ３、Ｒ^ｃ４、Ｒ^ｃ５：炭素数１のアルキル基（メチル基）
・Ｒ^ｃ６：炭素数１８の分岐鎖状アルキル基（イソオクタデシル基）
・Ｒ^ｃ７：－ＣＨ_２－ (8) Comparative Production Example 2: Nitrogen-containing compound (C)-1
42 g (0.12 mol) of isooctadecenylsuccinic anhydride and 20 mL of xylene were added to a 200-mL four-necked flask, and the solution in the flask was heated to 80°C and then maintained at 80°C. 19 g (0.12 mol) of 4-amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 10 mL of methanol, 20 mL of hexane and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. for 4 hours at a hydrogen pressure of 2 MPa to obtain a nitrogen-containing compound (C)-1. , 56 g of a red oily product were obtained. Nitrogen-containing compound (C)-1 is a compound represented by the following chemical structural formula (8).

The nitrogen-containing compound (C)-1 represented by the formula (8) has the following R ^c1 , R ^c2 , R ^c3 , R ^c4 , R ^c5 , R ^c6 and R ^c7 in the general formula (c) It is a compound that is a group.
・R ^c1 : hydrogen atom ・R ^c2 , R ^c3 , R ^c4 , R ^c5 : alkyl group having 1 carbon atom (methyl group)
・R ^c6 : a branched alkyl group having 18 carbon atoms (isooctadecyl group)
・R ^c7 : —CH ₂ —

上記式（９）中、「ｉＣ_１８」は、イソオクタデセニル基である。 (9) Comparative Production Example 3
A red oil was produced as a monoimide compound in the same manner as in Comparative Production Example 1, except that the amount of isooctadecenylsuccinic anhydride 28 g (0.08 mol) was changed to 28 g (0.08 mol). 42 g of product was obtained. A monoimide compound is a compound represented by the following chemical structural formula (9).

In formula (9) above, “iC ₁₈ ” is an isooctadecenyl group.

上記式（１０）で表される含窒素化合物（Ｄ１）－１は、上記一般式（ｄ１）中、Ｒ^ｄ１、Ｒ^ｄ２、Ｒ^ｄ３、Ｒ^ｄ４、Ｒ^ｄ５、Ｒ^ｄ１６、Ｒ^ｄ１７が以下の基である化合物である。
・Ｒ^ｄ１：炭素数２のアシル基
・Ｒ^ｄ２、Ｒ^ｄ３、Ｒ^ｄ４、Ｒ^ｄ５：炭素数１のアルキル基（メチル基）
・Ｒ^ｄ１６：炭素数１２の直鎖状アルキル基（ｎ－ドデシル基）
・Ｒ^ｄ１７：－ＣＨ_２－ (10) Comparative Production Example 4: Nitrogen-containing compound (D1)-1
42 g (0.12 mol) of isooctadecenylsuccinic anhydride and 20 mL of xylene were added to a 200-mL four-necked flask, and the solution in the flask was heated to 80°C and then maintained at 80°C. 19 g (0.12 mol) of 4-amino-2,2,6,6-tetramethylpiperidine was added dropwise over 30 minutes. After dropping, the solution in the flask was heated to 150° C. and stirred for 3 hours. After the stirring was completed, the pressure in the flask was reduced by a vacuum pump for 3 hours while maintaining the temperature of the solution at 140° C., and the imidized intermediate was obtained by removing the solvent and light components. Put the obtained intermediate in a 150 mL autoclave, add 10 mL of methanol, 20 mL of hexane and 1 g of 10% palladium on carbon, and hydrogenate at 55 ° C. for 4 hours at a hydrogen pressure of 2 MPa to obtain a nitrogen-containing compound (D1)-1. , 56 g of a red oily product were obtained. Nitrogen-containing compound (D1)-1 is a compound represented by the following chemical structural formula (10).

The nitrogen-containing compound (D1)-1 represented by the formula (10) has the following R ^d1 , R ^d2 , R ^d3 , R ^d4 , R ^d5 , R ^d16 and R ^d17 in the general formula (d1). It is a compound that is a group.
・R ^d1 : acyl group having 2 carbon atoms ・R ^d2 , R ^d3 , R ^d4 , R ^d5 : alkyl group (methyl group) having 1 carbon atom
・R ^d16 : a linear alkyl group having 12 carbon atoms (n-dodecyl group)
・R ^d17 : —CH ₂ —

<Preparation of lubricating oil composition>
(1) Preparation of Lubricating Oil Compositions for Evaluation of Detergency In Examples 1 to 6 and Comparative Examples 1 to 4, mineral oils having a 40° C. kinematic viscosity of 90.5 mm ² /s (American Petroleum Institute (API) category: A nitrogen-containing compound was added to Group II) to prepare a lubricating oil composition for detergency testing. The amount of the nitrogen-containing compound added was adjusted so that the amount of nitrogen derived from the nitrogen-containing compound was 1,000 ppm by mass based on the total amount of the lubricating oil composition.
In addition, in Example 7 and Comparative Example 5, lubricating oil compositions were prepared according to the formulations shown in Table 1. The amount of the nitrogen-containing compound added was adjusted so that the amount of nitrogen derived from the nitrogen-containing compound was 1,700 mass ppm based on the total amount of the lubricating oil composition.

※他の添加剤：粘度指数向上剤、流動点降下剤、酸化防止剤、極圧剤、清浄分散剤、金属不活性化剤、油性剤、及び消泡剤

*Other additives: Viscosity index improver, pour point depressant, antioxidant, extreme pressure agent, detergent dispersant, metal deactivator, oiliness agent, and antifoaming agent

(2) Preparation of lubricating oil composition for anti-shudder evaluation In Examples 1 to 6 and Comparative Examples ¹ to 4, a mineral oil (American Petroleum Institute (API) category : A nitrogen-containing compound was added to Group III) to prepare a lubricating oil composition for the anti-shudder property test. The amount of the nitrogen-containing compound added was adjusted so that the amount of nitrogen derived from the nitrogen-containing compound was 500 ppm by mass based on the total amount of the lubricating oil composition.
In addition, in Example 7 and Comparative Example 5, lubricating oil compositions were prepared according to the formulations shown in Table 1. The amount of the nitrogen-containing compound added was adjusted so that the amount of nitrogen derived from the nitrogen-containing compound was 1,700 ppm by mass based on the total amount of the lubricating oil composition, as described above.

<Evaluation of cleanliness and anti-shudder property>
Detergency and anti-shudder properties were evaluated by the methods described below.

(1) Detergency Evaluation (1-1) Hot Tube Test A hot tube test was performed in accordance with JPI-5S-55-99 to evaluate detergency.
Specifically, in Examples 1 to 6 and Comparative Examples 1 to 4, a glass tube having an inner diameter of 2 mm was filled with a lubricating oil composition at 0.3 mL/hour while maintaining the temperature of the glass tube at 230 ° C. and continued to flow air at 10 mL/min for 16 hours.
In Example 7 and Comparative Example 4, similar tests were conducted while maintaining the temperature of the glass tube at 280°C.
After the hot tube test, the lacquer adhering to the glass tube was compared with the color sample, and scored in increments of 0.5 points, with 10 points for colorless and transparent and 0 points for black. The higher the transparency, the higher the score, indicating higher cleanliness and stability at elevated temperatures.
A hot tube score of 6.0 or higher was considered acceptable.

(1-2) Evaluation of base number retention The lubricating oil composition after the above hot tube test is recovered, and the base number is measured by a potentiometric titration method (base number/hydrochloric acid method) in accordance with JIS K2501: 8 of 2003. bottom. The base number after the test (residual base number) was compared with the base number before the test (initial base number), expressed as a residual base number ratio (%), and base number retention was evaluated by the following formula. The higher the residual base number ratio, the higher the base number retention at high temperatures and the higher the detergency.
Percentage of residual base number (%) = (Residual base number/Initial base number) x 100
A residual base number of 10% or more was considered acceptable when no other additives were added. When other additives were blended, 20% or more was considered acceptable.

(1-3) Evaluation of acid value After the hot tube test, the lubricating oil composition was collected and the acid value was measured by potentiometric titration according to JIS K2501:2003-7. A lower acid number indicates higher cleanliness.
Acid value of 15.0 mgKOH/g or less was accepted when no other additives were added. When other additives were blended, 0.6 mgKOH/g or less was considered acceptable.

<Shudder prevention>
For the lubricating oil compositions prepared in Examples 1 to 7 and Comparative Examples 1 to 5, based on JASO M 349: 2012, using a low speed sliding friction tester (LVFA tester), a friction plate (A795.DOAK) and a steel plate (FZ132-8-Y2) were measured.
The test oil temperature during the measurement was set to 80° C., and the surface pressure was set to 1 MPa.
In JASO M 349:2012, the SWEEP method is usually used for measurement, but in order to improve the measurement accuracy of the friction coefficient, the STEP method stipulated in JASO M 349:1998 was used for evaluation.
Regarding the μ-V characteristic 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 and 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 μ100 at a rotational speed of 100 rpm.
If the ratio [μ1/μ100] as the μ-V characteristic for defining the shudder prevention performance during slip control of the lockup clutch is 1.0 or less, it is considered that the shudder prevention performance is secured. It was judged.
In order to ensure torque capacity, a coefficient of friction μ100 of 0.08 or more was accepted.

The results are shown in Tables 2-4.

Tables 2 and 3 show the following.
Nitrogen-containing compound (A1)-1, nitrogen-containing compound (A1)-2, nitrogen-containing compound (A1)-3, nitrogen-containing compound (A1)-4, and nitrogen-containing compound (A1)-5 of Examples 1 to 6 , and the nitrogen-containing compound (B1)-1 are excellent in anti-shudder performance and detergency.
On the other hand, the lubricating oil composition containing the bisimide compound of Comparative Example 1 can ensure anti-shudder performance, but is inferior in detergency.
It can be seen that the lubricating oil composition containing the nitrogen-containing compound (C)-1 of Comparative Example 2 is excellent in detergency but inferior in anti-shudder performance.
It can be seen that the lubricating oil composition containing the monoimide compound of Comparative Example 3 is inferior in both anti-shudder performance and detergency.
It can be seen that the lubricating oil composition containing the nitrogen-containing compound (E)-1 of Comparative Example 4 is excellent in detergency but inferior in anti-shudder performance.

Further, from the results shown in Table 4, even when the additive was added to bring the formulation closer to the actual drive system lubricating oil composition, when the nitrogen-containing compound (A1)-1 was used, the anti-shudder performance and It can be seen that while the cleanability is excellent, the cleanability is inferior when the bisimide compound is used.

Claims (9)

One or more components (X _AB ) selected from the group consisting of a nitrogen-containing compound (A) represented by the following general formula (a) and a nitrogen-containing compound (B) represented by the following general formula (b) A lubricating oil additive containing and used as an anti-shudder agent.

[In the general formula (a), R ^a1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a2 , R ^a3 , R ^a4 and R ^a5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a6 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^a7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^a7 is an alkylene group having 1 to 3 carbon atoms, R ^a7 bonds with the carbon atom C ^ax bonded to R ^a6 to form a ring structure. ]

[In the general formula (b), R ^b1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b2 , R ^b3 , R ^b4 and R ^b5 are each independently an alkyl group having 1 to 3 hydrogen atoms. R ^b6 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^b7 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkylene group having 2 to 4 carbon atoms. When R ^b7 is an alkylene group having 2 to 4 carbon atoms, R ^b7 bonds with the carbon atom C ^bx bonding to R ^b6 to form a ring structure. ] The lubricating oil additive according to claim 1, wherein the nitrogen-containing compound (A) contains a nitrogen-containing compound (A1) represented by the following general formula (a1).

[In the general formula (a1), R ^a11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a12 , R ^a13 , R ^a14 and R ^a15 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^a16 is a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms. ] The lubricating oil additive according to claim 1 or 2, wherein the nitrogen-containing compound (B) contains a nitrogen-containing compound (B1) represented by the following general formula (b1).

[In the general formula (b1), R ^b11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b12 , R ^b13 , R ^b14 and R ^b15 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^b16 is an aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^b17 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. ] The lubricating oil additive according to any one of claims 1 to 3, wherein the content of the component (X _AB ) is 50% by mass or more based on the total amount of the lubricating oil additive. The content of one or more components (X _C ) selected from nitrogen-containing compounds (C) represented by the following general formula (c) is less than 10% by mass, based on the total amount of the additive for lubricating oil. The lubricating oil additive according to any one of claims 1 to 4.

[In the general formula (c), R ^c1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^c2 , R ^c3 , R ^c4 and R ^c5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ^c6 is a branched aliphatic hydrocarbon group having 8 to 20 carbon atoms. R ^c7 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. When R ^c7 is an alkylene group having 1 to 3 carbon atoms, R ^c7 bonds with the carbon atom C ^cx bonding to R ^c6 to form a ring structure. ] The lubricating oil according to claim 5, wherein the content ratio [(X _AB )/(X _C )] of the component (X _AB ) and the component (X _C ) is more than 5/1 in mass ratio. Additive. A lubricating oil composition for a drive system, comprising the lubricating oil additive according to any one of claims 1 to 6 and a lubricating base oil (P). A method for preventing shudder in a lock-up clutch mechanism of an automobile using a drive system lubricating oil composition containing the lubricating oil additive according to any one of claims 1 to 6. A method for preventing shudder in a lock-up clutch mechanism of an automobile using the drive system lubricating oil composition according to claim 7 .