WO2014136907A1 - Friction modifier and lubricating-oil composition - Google Patents

Abstract

A succinimide compound that can be represented by general formula (1), a friction modifier containing such a succinimide compound, and a lubricating-oil composition containing such a succinimide compound. (1) (In formula (1), R represents a C_8-30 hydrocarbyl group and X represents a group that can be represented by one of general formulas (2) to (5).) (2) (In formula (2), m represents an integer from 1 to 4, n represents an integer from 0 to 3, and m+n is less than or equal to 5.) (3) (In formula (3), q represents an integer from 1 to 7.) (4) (In formula (4), the hydroxy substituent on the aromatic ring may be in the ortho position, the meta position, or the para position.)

Description

Friction modifier and lubricating oil composition

The present invention relates to a novel compound exhibiting friction adjusting ability, a friction adjusting agent, and a lubricating oil composition having excellent friction characteristics.

Many of automatic transmissions and continuously variable transmissions have a torque converter, and engine torque is transmitted to the transmission via lubricating oil. The torque converter is structurally unable to transmit power unless there is a differential rotation between the input side (engine side) and the output side (transmission side), and this differential rotation causes the power transmission efficiency of the transmission to decrease. It has become. In recent years, there has been an increasing demand for saving fuel in automobiles, and transmissions are also required to have improved power transmission efficiency than ever before. As a means of improving power transmission efficiency in a transmission having a torque converter, a lock-up clutch is built into the torque converter, and in addition to power transmission via lubricating oil, engine torque is directly shifted according to driving conditions. Many techniques for transmitting to the mechanism have been adopted in recent years.

However, when the lock-up clutch is operated, engine torque fluctuations deteriorate the ride comfort. With the conventional lock-up mechanism, the lock-up clutch is operated only in the high speed range where the engine torque fluctuation is small, and is operated in the low speed range. It wasn't. For this reason, there is a transmission loss of the torque converter in the low speed range such as when starting, so there is still room for improvement in terms of overall fuel consumption.

In order to reduce this transmission loss, recently, a slip control (slip control) method is being introduced in which a lock-up clutch is operated even in a low speed range and engine torque fluctuations are absorbed by the relative slip of the clutch. However, when slip control of the clutch is performed, an abnormal vibration (shudder) due to a slip stick phenomenon occurs on the friction surface of the lockup clutch, and the ride quality of the automobile may be impaired. In order to prevent the occurrence of shudder, it is extremely important to adjust the μ-V characteristics so that the friction coefficient (μ) becomes higher as the sliding speed (V) increases in the lock-up clutch. V-characteristic adjustment capability (shudder prevention performance) is assigned to lubricating oil (transmission oil) (see, for example, Patent Document 1). Since the anti-shudder performance of the lubricating oil decreases as the lubricating oil deteriorates, there is a demand for a lubricating oil that has excellent ability to maintain the anti-shudder performance (shudder prevention life). In pursuit of improved fuel efficiency, the low speed range in which slip control is performed is increasingly advanced, and further improvement in the anti-shudder life is desired.

Also, automatic transmissions and continuously variable transmissions have a wet transmission clutch in the transmission mechanism and the forward / reverse switching mechanism. When the friction characteristics of the speed change clutch are poor, for example, when the difference between the dynamic friction coefficient and the static friction coefficient is too large, a shock is generated at the time of speed change and the riding comfort of the automobile is impaired. Therefore, it is required that the lubricating oil used in these transmissions be given good shift characteristics to the shift clutch in order to reduce shock when the shift clutch is engaged.

Giving lubricating oil anti-shudder performance and improving friction characteristics of the transmission clutch are generally performed by adding a friction modifier to the lubricating oil. Therefore, in order to improve the anti-shudder life and the speed change characteristics of the lubricating oil, it can be considered as one means to add a large amount of a friction modifier. However, depending on the type of friction modifier to be blended, the friction coefficient (for example, the friction coefficient between metals in a continuously variable transmission, etc.) may be significantly reduced, and this time the transmission torque capacity in the transmission cannot be secured sufficiently. Occurs. Thus, in the approach by blending the friction modifier with the lubricating oil, the shudder prevention life, the speed change characteristic, and the transmission torque capacity are generally in a trade-off relationship.

JP 2004-155924 A

Therefore, an object of the present invention is to provide a compound capable of increasing both the anti-shudder life, the speed change characteristic and the transmission torque capacity to a satisfactory level when contained in a lubricating oil. Also provided are a friction modifier containing the compound and a lubricating oil composition containing the friction modifier.

The first aspect of the present invention is a succinimide compound represented by the following general formula (A1).

[In the formula (A1), R ^a represents a hydrocarbyl group having 8 to 30 carbon atoms, m is an integer of 1 to 4, n is an integer of 0 to 3, and m + n is 5 or less. ]

The second aspect of the present invention is a friction modifier containing the succinimide compound according to the first aspect of the present invention.

A third aspect of the present invention is a lubricating oil composition containing a lubricating base oil and the friction modifier according to the second aspect of the present invention. The lubricating oil composition according to the third aspect of the present invention can be particularly preferably used as a continuously variable transmission oil.

A fourth aspect of the present invention is a succinimide compound represented by the following general formula (B1).

[In formula (B1), R ^b represents a hydrocarbyl group having 8 to 30 carbon atoms, and the hydroxy group in the aromatic ring may be substituted at any of the ortho, meta, and para positions. ]

A fifth aspect of the present invention is a friction modifier containing a succinimide compound according to the fourth aspect of the present invention.

A sixth aspect of the present invention is a lubricating oil composition containing a lubricating base oil and the friction modifier according to the fifth aspect of the present invention. The lubricating oil composition according to the sixth aspect of the present invention can be particularly preferably used as a continuously variable transmission oil.

A seventh aspect of the present invention is a succinimide compound represented by the following general formula (C1).

[In the formula (C1), R ^c represents a hydrocarbyl group having 8 to 30 carbon atoms, and q is an integer of 1 to 7. ]

The eighth aspect of the present invention is a friction modifier containing a succinimide compound according to the seventh aspect of the present invention.

A ninth aspect of the present invention is a lubricating oil composition containing a lubricating base oil and the friction modifier according to the eighth aspect of the present invention. The lubricating oil composition according to the ninth aspect of the present invention can be particularly preferably used as a continuously variable transmission oil.

The succinimide compounds according to the first, fourth and seventh aspects can be comprehensively represented by the following general formula (1).

[In the formula (1), R represents a hydrocarbyl group having 8 to 30 carbon atoms, and X represents a group represented by any one of the following general formulas (2) to (5). ]

[In the formula (2), m is an integer of 1 to 4, n is an integer of 0 to 3, and m + n is 5 or less. ]

[In Formula (3), q is an integer of 1-7. ]

[In the formula (4), the substitution position of the hydroxy group in the aromatic ring may be any of the ortho, meta and para positions. ]

According to the succinimide compound according to the first, fourth, and seventh aspects of the present invention, the inclusion of the lubricant in the lubricant prevents the anti-shudder life, the speed change characteristic, and the friction coefficient (transmission torque capacity) of the lubricant. Can be raised to a satisfactory level together. Therefore, these compounds can be preferably contained as a friction modifier in the lubricating oil composition.

The lubricating oil compositions according to the third, sixth, and ninth aspects of the present invention containing the friction modifiers according to the second, fifth, and eighth aspects of the present invention have improved shudder prevention life and While having good transmission characteristics, the transmission torque capacity can also be improved by increasing the coefficient of friction between metals. Therefore, it can be preferably used as an automatic transmission oil or a continuously variable transmission oil.

2 is an infrared absorption spectrum of succinimide compound A-1 produced in Production Example A-1. It is an infrared absorption spectrum of succinimide compound B-1 produced in Production Example B-1. It is an infrared absorption spectrum of the succinimide compound C-1 produced in Production Example C-1.

Hereinafter, the present invention will be described in detail. Unless otherwise specified, the notation “A to B” in the numerical range means “A or more and B or less”. In this notation, when a unit is attached to only the numerical value B, the unit is also applied to the numerical value A.

<(1) A-1. Succinimide compound>
(Construction)
The succinimide compound according to the first aspect of the present invention has a structure represented by the following general formula (A1).

In the general formula (A1), R ^a represents a hydrocarbyl group having 8 to 30 carbon atoms, m is an integer of 1 to 4, n is an integer of 0 to 3, and m + n is 5 or less.
In the above general formula (A1), m is preferably 1 to 3, more preferably 1 to 2. N is preferably 0 to 2, more preferably 0 to 1.

Here, specific examples of the hydrocarbyl group having 8 to 30 carbon atoms that can be employed as ^Ra include an alkyl group (which may have a ring structure) and an alkenyl group (the position of the double bond is arbitrary). And may have a ring structure.), Aryl groups, alkylaryl groups, alkenylaryl groups, arylalkyl groups, arylalkenyl groups, and the like.

Examples of the alkyl group include linear or branched alkyl groups. Examples of the alkyl group having a ring structure include an alkylcycloalkyl group and a cycloalkylalkyl group. Examples of the cycloalkyl group include cycloalkyl groups having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The substitution position on the cycloalkyl ring is arbitrary.

Examples of the alkenyl group include various linear or branched alkenyl groups. Examples of the alkenyl group having a ring structure include an alkylcycloalkenyl group, an alkenylcycloalkyl group, a cycloalkenylalkyl group, and a cycloalkenylalkenyl group. The cycloalkyl group is the same as described above. Examples of the cycloalkenyl group include cycloalkyl groups having 5 to 7 carbon atoms, such as a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The substitution position on the cycloalkenyl ring and the substitution position on the cycloalkyl ring are arbitrary.

Examples of the aryl group include a phenyl group (having a hydrocarbyl substituent), a naphthyl group, and the like. In the alkylaryl group, alkenylaryl group, arylalkyl group, and arylalkenyl group, the substitution position on the aryl group is arbitrary.

R ^a has 8 to 30 carbon atoms, preferably 10 or more, and more preferably 12 or more. Further, it is preferably 20 or less. R ^a is preferably an aliphatic hydrocarbyl group (an alkyl or alkenyl group optionally having a ring structure), and more preferably, the aliphatic hydrocarbyl group has a chain portion. The chain portion may be linear or branched. However, it is particularly preferred that the maximum chain length in the carbon chain contained in the chain portion (however, the chain length from the end closest to the nitrogen atom of the carbon chain) is 8 carbons or more (for example, 4- ( The maximum chain length of the carbon chain contained in the chain portion of the 2-ethyldecyl) cyclohexyl group (the chain length of the carbon chain from the end closest to the nitrogen atom) is 10 carbons, and 4- (9-cyclopentyl) (The maximum of the chain length of the carbon chain contained in the chain portion of the (decan-3-yl) cyclohexyl group (the chain length of the carbon chain from the end closest to the nitrogen atom) is 8 carbons).

Examples of the form of the succinimide compound according to the first aspect of the present invention include the following [a1] to [a14].
[A1] In the formula (A1), R ^a is a hydrocarbyl group having 8 to 30 carbon atoms, m is an integer of 1 to 4, n is an integer of 0 to 3, and m + n is 5 or less .
[A2] In the above [a1], m is an integer of 1 to 3.
[A3] In the above [a1], m is 1 or 2.
[A4] In the above [a1], m is 1.
[A5] A form in which n is an integer of 0 to 2 in any one of [a1] to [a4] above.
[A6] The form in which n is 0 or 1 in any one of the above [a1] to [a4].
[A7] The form in which n is 0 in any one of the above [a1] to [a4].
[A8] The form in which in any one of the above [a1] to [a7], R ^a has 10 or more carbon atoms.
[A9] The form in which in any one of the above [a1] to [a7], R ^a has 12 or more carbon atoms.
[A10] The form in which in any one of the above [a1] to [a9], R ^a has 20 or less carbon atoms.
[A11] The form in which R ^a is an aliphatic hydrocarbyl group in any one of the above [a1] to [a10].
[A12] The form in which R ^a has a chain portion in the above [a11].
[A13] In the above [a12], the chain length in the carbon chain contained in the chain portion (however, the maximum chain length from the end closest to the nitrogen atom of the carbon chain) is 8 carbons or more. .
[A14] The form in which any one of [a1] to [a10] above, wherein R ^a is a linear or branched alkyl group or alkenyl group.

(Production of succinimide compound)
The method for producing the succinimide compound according to the first aspect of the present invention is not particularly limited. For example, it can be manufactured as follows. That is, it can be obtained by a reaction between a diol compound having an amino group and 2-hydrocarbyl succinic anhydride (the following formula (A2)). The imidation reaction of the formula (A2) is performed by removing water from the reaction system by azeotropic distillation with an organic solvent (eg, o-xylene, etc.) and phase separation using a Dean-Stark apparatus under heating and reflux conditions, for example. Can do. Further, for example, after confirming disappearance of 2-hydrocarbyl succinic anhydride, an imide ring may be formed by adding an imidizing agent (for example, acetic anhydride and pyridine).

In the reaction of the above formula (A2), the hydroxy group of the diol compound having an amino group is subjected to the reaction without protection. However, the hydroxy group is imidized in a protected state, and then deprotected to remove the hydroxy group. May be regenerated (the following formulas (A3) to (A6)).

If the necessary dihydroxyalkylamine or dihydroxyalkyl halide is not commercially available, it can be produced, for example, as follows.

When m = 1, starting from ω-alkenol in which the hydroxy group is protected with a silyl protecting group such as tert-butyldimethylsilyl (TBS) group, dimethyldioxirane (DMDO: acetone and 2KHSO ₅ · KHSO ₄ · K Epoxidize the C═C double bond with an oxidizing agent such as ₂ SO ₄ (Oxone®) (formula (A7) below) and open the epoxide by nucleophilic attack of an alkali metal azide. The epoxide-derived hydroxy group is similarly protected (for example, a silyl protecting group such as a triethylsilyl (TES) group. The following formula (A9)), and the azide group is catalytically reduced (H ₂ / Pd) or converted to an amino group by a Staudinger reaction (the following formula (A10)). Thereafter, similar to the above formulas (A5) to (A6), condensation with 2-hydrocarbyl succinic anhydride is performed, and the silyl protecting group may be deprotected by treatment with tributylammonium fluoride (TBAF), HF-pyridine or the like. .

When m is 2 or more, the succinimide compound of the above formula (A1) can be produced, for example, as follows. That is, a C—C bond is formed by allowing a Grignard reagent derived from an ω-haloalkene to act on a ω-hydroxyalkanal in which a hydroxy group is protected (for example, silyl protection such as TBS protection) (formula (A11 )), And the resulting hydroxy group is protected (for example, silyl protection such as TES protection, the following formula (A12)). The terminal alkene is converted into a primary alcohol by hydroboration and subsequent basic hydrogen peroxide treatment (the following formula (A13)), and the alcohol is converted into a halide (the following formula (A14)). The halide is reacted with an alkali metal salt of phthalimide (PhthN ⁻ K ⁺ etc., Phth represents a phthaloyl group) to form a CN bond (formula (A15) below), and the phthaloyl group is deprotected (for example, By performing hydrazine treatment or methylamine treatment, etc., a primary amine serving as an intermediate is obtained (the following formula (A16)). The condensation reaction of the amine with 2-hydrocarbyl succinic anhydride and the deprotection of the hydroxy group are the same as described above. The introduction of an amino group may be carried out by introduction of an azide group and subsequent catalytic reduction or conversion to an amino group by a Staudinger reaction, as in the above formulas (A8) and (A10).

If 2-hydrocarbyl succinic anhydride having a desired hydrocarbyl group is not commercially available, it can be prepared, for example, as follows. That is, the desired hydrocarbyl group is introduced at the α-position of the carbonyl group by reacting an organocopper reagent derived from the corresponding hydrocarbyl halide (or Grignard reagent in the presence of a monovalent copper salt) with tert-butyl haloacetate. Then, the ester enolate is further reacted with tert-butyl haloacetate to obtain 2-hydrocarbyl succinic acid having a protected carboxy group (following formula (A18)). The carboxy group is deprotected (for example, 85% phosphoric acid aqueous solution treatment or trifluoroacetic acid (TFA) treatment) and then cyclized by heating or the action of acetic anhydride to obtain 2-hydrocarbyl succinic anhydride (described below). Formula (A19)).

<(2) A-2. Friction modifier>
The friction modifier according to the second aspect of the present invention comprises the succinimide compound according to the first aspect of the present invention.

(Content)
The content of the succinimide compound according to the first aspect of the present invention in the friction modifier according to the second aspect of the present invention is not particularly limited, but preferably based on the total amount of the friction modifier, It is 50 weight% or more, More preferably, it is 80 weight% or more, More preferably, it is 90 weight% or more, and 100 weight% may be sufficient.

Examples of the form of the friction modifier according to the second aspect of the present invention include the following [a15] to [a19].
[A15] A form containing the succinimide compound according to any one of [a1] to [a14].
[A16] A form containing the succinimide compound of any one of the above [a1] to [a14] in an amount of 50% by weight or more based on the total amount of the friction modifier.
[A17] A form containing the succinimide compound of any one of the above [a1] to [a14] in an amount of 80% by weight or more based on the total amount of the friction modifier.
[A18] A form containing the succinimide compound of any one of the above [a1] to [a14] in an amount of 90% by weight or more based on the total amount of the friction modifier.
[A19] A form comprising the succinimide compound of any one of [a1] to [a15] above.

<(3) A-3. Lubricating oil composition>
The lubricating oil composition according to the third aspect of the present invention comprises a base oil and the friction modifier according to the second aspect of the present invention (hereinafter referred to as “polyfunctional succinimide friction modifier (A)”). In some cases).

(Lubricant base oil)
The lubricating base oil in the lubricating oil composition according to the third aspect of the present invention is not particularly limited, and mineral base oils and synthetic base oils used for ordinary lubricating oils can be used.

Specifically, as the mineral base oil, the lubricating oil fraction obtained by subjecting the crude oil to atmospheric distillation obtained under reduced pressure is subjected to solvent removal, solvent extraction, hydrocracking, A method of isomerizing GTL WAX (gas-to-liquid wax) produced by one or more treatments such as solvent dewaxing or hydrorefining, or wax isomerized mineral oil, Fischer-Tropsch process, etc. The lubricating base oil produced in (1) can be exemplified.

Synthetic lubricating oils include poly α-olefins such as 1-octene oligomers and 1-decene oligomers or their hydrides, isobutene oligomers or their hydrides, paraffins, alkylbenzenes, alkylnaphthalenes, diesters (ditridecylglutarate, di- 2-ethylhexyl adipate, diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl sebacate, etc., polyol ester (trimethylolpropane caprylate, trimethylolpropane pelargonate, pentaerythritol-2-ethylhexanoate, pentaerythritol pelargo Acid), polyoxyalkylene glycol, dialkyl diphenyl ether, polyphenyl ether and the like. Other examples include aromatic synthetic oils such as alkylnaphthalene, alkylbenzene, and aromatic esters, or mixtures thereof.

In the lubricating oil composition of the present invention, a mineral base oil, a synthetic base oil, or an arbitrary mixture of two or more kinds of lubricating oils selected from these can be used as the lubricating base oil. Examples thereof include one or more mineral base oils, one or more synthetic base oils, a mixed oil of one or more mineral base oils and one or more synthetic base oils, and the like.

The kinematic viscosity, NOACK evaporation amount, and viscosity index of the lubricating base oil in the lubricating oil composition of the present invention can be appropriately set according to the use of the lubricating oil composition.

(Multifunctional succinimide friction modifier (A))
The friction modifier according to the second aspect of the present invention is as already described. The content is not particularly limited. The content of the succinimide compound represented by the general formula (A1) based on the total amount of the lubricating oil composition can be, for example, 0.1 to 10% by weight. The preferred content can vary depending on the application. For example, when a lubricating oil composition for an automatic transmission or a continuously variable transmission is used, it is preferably 0.1% by weight or more, and more preferably 5% by weight or less.

(Other additives)
The lubricating oil composition according to the third aspect of the present invention includes an ashless dispersant, an antioxidant, and the succinic acid according to the first aspect of the present invention, in addition to the above-described lubricating base oil and friction modifier. Friction modifiers other than imide compounds, antiwear agents, extreme pressure agents, metallic detergents, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, metal deactivators, antifoaming agents and coloring It is preferable to further include at least one selected from the group consisting of agents.

As the ashless dispersant, known ashless dispersants can be used. When the lubricating oil composition of the present invention contains an ashless dispersant, its content is usually 0.01% by weight or more based on the total amount of the lubricating oil composition, that is, the total amount of the lubricating oil composition is 100% by weight. The content is preferably 0.1% by weight or more. Moreover, it is 20 weight% or less normally, Preferably it is 10 weight% or less.

As the antioxidant, a known antioxidant can be used. When the antioxidant is contained in the lubricating oil composition of the present invention, the content is usually 5.0% by weight or less, preferably 3.0% by weight or less, based on the total amount of the lubricating oil composition. Moreover, it is preferably 0.1% by weight or more, more preferably 0.5% by weight or more.

As the friction modifier other than the succinimide compound of the present invention, known friction modifiers can be used. Examples include oil-based friction modifiers such as fatty acid esters, sulfur-containing molybdenum complexes such as molybdenum dithiocarbamate and molybdenum dithiophosphate, molybdenum complexes that do not contain sulfur such as molybdenum amine complexes and molybdenum-succinimide complexes, and molybdenum disulfide. And molybdenum-based friction modifiers. When these friction modifiers are contained in the lubricating oil composition of the present invention, the content is usually 0.005 wt% or more and 5 wt% or less based on the total amount of the lubricating oil composition.

As the antiwear agent or extreme pressure agent, known antiwear agents or extreme pressure agents can be used. Examples thereof include phosphorus compounds such as (mono, di, tri-thio) (sub) phosphate esters and zinc dithiophosphate, and sulfur-containing compounds such as disulfides, sulfurized olefins, sulfurized fats and oils, and dithiocarbamates. . When these lubricants are contained in the lubricating oil composition of the present invention, the content thereof is usually 0.005 wt% or more and 5 wt% or less based on the total amount of the lubricating oil composition.

As the metal detergent, a known metal detergent can be used. Examples include alkali metal sulfonates, alkaline earth metal sulfonates, alkali metal phenates, alkaline earth metal phenates, alkali metal salicylates, alkaline earth metal salicylates, and mixtures thereof. These metallic detergents may be overbased. When the metallic detergent is contained in the lubricating oil composition of the present invention, the content is not particularly limited. However, in the case of an automatic transmission or a continuously variable transmission, the metal element conversion amount is usually 0.01% by weight or more and 5% by weight or less based on the total amount of the lubricating oil composition.

A known viscosity index improver can be used as the viscosity index improver. For example, various methacrylic acids containing a so-called non-dispersible viscosity index improver such as a polymer or copolymer of one or more monomers selected from various methacrylic esters and hydrogenated products thereof, and further a nitrogen compound So-called dispersed viscosity index improver copolymerized with ester, non-dispersed or dispersed ethylene-α-olefin copolymer and hydride thereof, polyisobutylene and hydrogenated product thereof, hydride of styrene-diene copolymer Styrene-maleic anhydride ester copolymer, polyalkylstyrene, and the like. The average molecular weight of the viscosity index improver is usually 5,000 or more and 1,000,000 or less in terms of weight average molecular weight in the case of, for example, dispersed and non-dispersed polymethacrylates. For example, when polyisobutylene or a hydride thereof is used for an internal combustion engine, the number average molecular weight is usually 800 or more and 5,000 or less. For example, when an ethylene-α-olefin copolymer or a hydride thereof is used for an internal combustion engine, the number average molecular weight is usually 800 or more and 500,000 or less.
When these viscosity index improvers are contained in the lubricating oil composition of the present invention, the content thereof is usually 0.1% by weight or more and 20% by weight or less based on the total amount of the lubricating oil composition.

As the pour point depressant, a known pour point depressant such as a polymethacrylate polymer can be appropriately used depending on the properties of the lubricating base oil to be used. When the lubricating oil composition of the present invention contains a pour point depressant, the content thereof is usually 0.01% by weight or more and 1% by weight or less based on the total amount of the lubricating oil composition.

As the corrosion inhibitor, for example, known corrosion inhibitors such as benzotriazole, tolyltriazole, thiadiazole, and imidazole compounds can be used. When these corrosion inhibitors are contained in the lubricating oil composition of the present invention, the content is usually 0.005 wt% or more and 5 wt% or less based on the total amount of the lubricating oil composition.

As the rust inhibitor, for example, known rust inhibitors such as petroleum sulfonate, alkylbenzene sulfonate, dinonylnaphthalene sulfonate, alkenyl succinate, and polyhydric alcohol ester can be used. When these antirust agents are contained in the lubricating oil composition of the present invention, the content is usually 0.005 wt% or more and 5 wt% or less based on the total amount of the lubricating oil composition.

Examples of metal deactivators include imidazoline, pyrimidine derivatives, alkylthiadiazoles, mercaptobenzothiazoles, benzotriazoles and derivatives thereof, 1,3,4-thiadiazole polysulfide, 1,3,4-thiadiazolyl-2,5-bis. Known metal deactivators such as dialkyldithiocarbamate, 2- (alkyldithio) benzimidazole, and β- (o-carboxybenzylthio) propiononitrile can be used. When these metal deactivators are contained in the lubricating oil composition of the present invention, the content is usually 0.005 wt% or more and 1 wt% or less based on the total amount of the lubricating oil composition.

As the antifoaming agent, for example, known antifoaming agents such as silicone, fluorosilicone, and fluoroalkyl ether can be used. When these antifoaming agents are contained in the lubricating oil composition of the present invention, the content thereof is usually 0.0005 wt% or more and 1 wt% or less based on the total amount of the lubricating oil composition.

As the colorant, for example, a known colorant such as an azo compound can be used.

Examples of the form of the lubricating oil composition according to the third aspect of the present invention include the following [a20] to [a29].
[A20] A form containing a lubricant base oil and the friction modifier of any one of the above [a15] to [a19].
[A21] A form in which the succinimide compound of any one of the above [a1] to [a14] is contained in the above [a20] in an amount of 0.1 to 10% by weight based on the total amount of the composition.
[A22] A form in which the succinimide compound of any one of the above [a1] to [a14] is contained in the above [a20] in an amount of 0.1 to 5% by weight based on the total amount of the composition.
[A23] In any one of the above [a20] to [a22], an ashless dispersant, an antioxidant, a friction modifier other than the succinimide compound represented by the general formula (A1), an antiwear agent, an extreme pressure Further containing at least one selected from the group consisting of an agent, a metal detergent, a viscosity index improver, a pour point depressant, a corrosion inhibitor, a rust inhibitor, a metal deactivator, an antifoaming agent and a colorant. Form.
[A24] A form of any one of the above [a20] to [a23], wherein the ashless dispersant is contained in an amount of 0.01% by weight to 20% by weight based on the total amount of the composition.
[A25] The form of any one of [a20] to [a24] above, wherein the antioxidant is contained in an amount of 0.1% by weight to 5.0% by weight based on the total amount of the composition.
[A26] The form of any one of the above [a20] to [a25], wherein the antiwear agent or extreme pressure agent is contained in an amount of 0.005 wt% to 5 wt% based on the total amount of the composition.
[A27] In any one of the above [a20] to [a26], the metallic detergent is contained in an amount of 0.01% by weight to 5% by weight based on the total amount of the composition.
[A28] In any one of the above [a20] to [a27], the form used in the automatic transmission.
[A29] The form used in the continuously variable transmission according to any one of [a20] to [a27].

(Use)
The lubricating oil composition according to the third aspect of the present invention is improved by containing the friction modifier (polyfunctional succinimide friction modifier (A)) according to the second aspect of the present invention. While having an anti-shudder life and good speed change characteristics, the transmission torque capacity can also be improved by increasing the coefficient of friction between metals. Therefore, it can be preferably used as an automatic transmission oil or a continuously variable transmission oil.

<(4) B-1. Succinimide compound>
(Construction)
The succinimide compound according to the fourth aspect of the present invention has a structure represented by the following general formula (B1).

In the above general formula (B1), R ^b represents a hydrocarbyl group having 8 to 30 carbon atoms. The substitution position of the hydroxy group in the aromatic ring may be any of ortho, meta and para positions. The succinimide compound according to the seventh aspect of the present invention may be a mixture of a plurality of isomers having different hydroxy group substitution positions in the aromatic ring.

Here, specific examples of the hydrocarbyl group having 8 to 30 carbon atoms that can be employed as R ^b include an alkyl group (which may have a ring structure) and an alkenyl group (the position of the double bond is arbitrary). And may have a ring structure.), Aryl groups, alkylaryl groups, alkenylaryl groups, arylalkyl groups, arylalkenyl groups, and the like.

Examples of the alkyl group include linear or branched alkyl groups. Examples of the alkyl group having a ring structure include an alkylcycloalkyl group and a cycloalkylalkyl group. Examples of the cycloalkyl group include cycloalkyl groups having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The substitution position on the cycloalkyl ring is arbitrary.

Examples of the alkenyl group include linear or branched alkenyl groups. Examples of the alkenyl group having a ring structure include an alkylcycloalkenyl group, an alkenylcycloalkyl group, a cycloalkenylalkyl group, and a cycloalkenylalkenyl group. The cycloalkyl group is the same as described above. Examples of the cycloalkenyl group include cycloalkyl groups having 5 to 7 carbon atoms, such as a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The substitution position on the cycloalkenyl ring and the substitution position on the cycloalkyl ring are arbitrary.

Examples of the aryl group include a phenyl group (having a hydrocarbyl substituent), a naphthyl group, and the like. In the alkylaryl group, alkenylaryl group, arylalkyl group, and arylalkenyl group, the substitution position on the aryl group is arbitrary.

R ^b has 8 to 30 carbon atoms, preferably 10 or more, and more preferably 12 or more. Further, it is preferably 20 or less. R ^b is preferably an aliphatic hydrocarbyl group (an alkyl or alkenyl group optionally having a ring structure), and more preferably, the aliphatic hydrocarbyl group has a chain portion. The chain portion may be linear or branched. However, it is particularly preferred that the maximum chain length of the carbon chain contained in the chain portion (however, the chain length from the end closest to the nitrogen atom of the carbon chain) is 8 carbons or more (for example, 4- ( The maximum chain length of the carbon chain contained in the chain portion of the 2-ethyldecyl) cyclohexyl group (the chain length of the carbon chain from the end closest to the nitrogen atom) is 10 carbons, and 4- (9-cyclopentyl) (The maximum of the chain length of the carbon chain contained in the chain portion of the (decan-3-yl) cyclohexyl group (the chain length of the carbon chain from the end closest to the nitrogen atom) is 8 carbons).

Examples of the form of the succinimide compound according to the fourth aspect of the present invention include the following [b1] to [b10].
[B1] In the formula (B1), R ^b is a hydrocarbyl group having 8 to 30 carbon atoms, and the substitution position of the hydroxy group in the aromatic ring may be any of the ortho, meta, and para positions. The form which may be a mixture of several isomers from which the substitution position of a hydroxy group differs.
[B2] A form containing the isomer in [b1] above, wherein the substitution position of the hydroxy group in the aromatic ring is the para position.
[B3] In the above [b1], the substitution position of the hydroxy group in the aromatic ring is in the para position.
[B4] An embodiment in which in any one of the above [b1] to [b3], R ^b has 10 or more carbon atoms.
[B5] An embodiment in which in any one of the above [b1] to [b3], R ^b has 12 or more carbon atoms.
[B6] An embodiment in which in any one of the above [b1] to [b3], R ^b has 20 or less carbon atoms.
[B7] The form in which ^Rb is an aliphatic hydrocarbyl group in any one of the above [b1] to [b6].
[B8] In the above [b7], R ^b has a chain portion.
[B9] In the above [b8], the maximum chain length in the carbon chain contained in the chain portion (however, the chain length from the end closest to the nitrogen atom of the carbon chain) is 8 carbons or more. .
[B10] The form in which any one of the above [b1] to [b6], wherein R ^b is a linear or branched alkyl group or alkenyl group.

(Production of succinimide compound)
The method for producing the succinimide compound according to the fourth aspect of the present invention is not particularly limited. For example, it can be obtained by reacting aminophenol with 2-hydrocarbyl succinic anhydride (the following formula (B2)).

The imidation reaction of the formula (B2) is performed by removing water from the reaction system by azeotropic distillation and phase separation with an organic solvent (for example, o-xylene etc.) using a Dean-Stark apparatus under heating and reflux conditions, for example. Can do. Further, for example, after confirming disappearance of 2-hydrocarbyl succinic anhydride, an imide ring may be formed by adding an imidizing agent (for example, acetic anhydride and pyridine). In the reaction of formula (B2), the hydroxy group of aminophenol is used for the reaction without protection, but the hydroxy group is protected by an appropriate protecting group (for example, a silyl protecting group such as tert-butyldimethylsilyl group). In such a state, it may be imidized and then deprotected to regenerate the hydroxy group.

<(5) B-2. Friction modifier>
The friction modifier according to the fifth aspect of the present invention comprises the succinimide compound according to the fourth aspect of the present invention.

(Content)
The content of the succinimide compound according to the fourth aspect of the present invention in the friction modifier according to the fifth aspect of the present invention is not particularly limited, but preferably based on the total amount of the friction modifier, It is 50 weight% or more, More preferably, it is 80 weight% or more, More preferably, it is 90 weight% or more, and 100 weight% may be sufficient.

Examples of the form of the friction modifier according to the fifth aspect of the present invention include the following [b11] to [b15].
[B11] A form containing the succinimide compound of any one of [b1] to [b10] above.
[B12] A form containing the succinimide compound of any one of the above [b1] to [b10] in an amount of 50% by weight or more based on the total amount of the friction modifier.
[B13] A form containing the succinimide compound of any one of [b1] to [b10] above in an amount of 80% by weight or more based on the total amount of the friction modifier.
[B14] A form containing the succinimide compound of any one of the above [b1] to [b10] in an amount of 90% by weight or more based on the total amount of the friction modifier.
[B15] A form comprising the succinimide compound according to any one of [b1] to [b10] above.

<(6) B-3. Lubricating oil composition>
The lubricating oil composition according to the sixth aspect of the present invention comprises a base oil and the friction modifier according to the fifth aspect of the present invention (hereinafter referred to as “polyfunctional succinimide friction modifier (B)”). In some cases).

(Lubricant base oil)
The lubricating base oil in the lubricating oil composition according to the sixth aspect of the present invention is the same as the base oil described above in relation to the lubricating oil composition according to the third aspect of the present invention.

The kinematic viscosity, NOACK evaporation amount, and viscosity index of the lubricating base oil in the lubricating oil composition according to the sixth aspect of the present invention can be appropriately set according to the use of the lubricating oil composition.

(Multifunctional succinimide friction modifier (B))
The friction modifier according to the fifth aspect of the present invention is as already described. The content is not particularly limited. The content of the succinimide compound represented by the general formula (B1) based on the total amount of the lubricating oil composition can be, for example, 0.1 to 10% by weight. The preferred content can vary depending on the application. For example, when a lubricating oil composition for an automatic transmission or a continuously variable transmission is used, it is preferably 0.1% by weight or more, and more preferably 5% by weight or less.

(Other additives)
The lubricating oil composition according to the sixth aspect of the present invention comprises, in addition to the above-described lubricating base oil and friction modifier, an ashless dispersant, an antioxidant, and the succinic acid according to the fourth aspect of the present invention. Friction modifiers other than imide compounds, antiwear agents, extreme pressure agents, metallic detergents, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, metal deactivators, antifoaming agents and coloring It is preferable to further include at least one selected from the group consisting of agents. The specific aspects of these additives and the contents of each additive are the same as the additives and contents described above in relation to the lubricating oil composition according to the third aspect of the present invention.

Examples of the form of the lubricating oil composition according to the sixth aspect of the present invention include the following [b16] to [b25].
[B16] A form containing the lubricating base oil and the friction modifier of any one of the above [b11] to [b15].
[B17] A form in which the succinimide compound of any one of the above [b1] to [b10] is contained in the above [b16] in an amount of 0.1 to 10% by weight based on the total amount of the composition.
[B18] A form in which the succinimide compound of any one of [b1] to [b10] is contained in the above [b16] in an amount of 0.1 to 5% by weight based on the total amount of the composition.
[B19] In any one of the above [b16] to [b18], an ashless dispersant, an antioxidant, a friction modifier other than the succinimide compound represented by the general formula (B1), an antiwear agent, an extreme pressure Further containing at least one selected from the group consisting of an agent, a metal detergent, a viscosity index improver, a pour point depressant, a corrosion inhibitor, a rust inhibitor, a metal deactivator, an antifoaming agent and a colorant. Form.
[B20] A form in which any one of the above [b16] to [b19] contains the ashless dispersant in an amount of 0.01 wt% to 20 wt% based on the total amount of the composition.
[B21] The form of any one of the above [b16] to [b20], wherein the antioxidant is contained in an amount of 0.1% by weight to 5.0% by weight based on the total amount of the composition.
[B22] The form of any one of the above [b16] to [b21], wherein the antiwear agent or the extreme pressure agent is contained in an amount of 0.005 wt% to 5 wt% based on the total amount of the composition.
[B23] A form in which in any one of the above [b16] to [b22], the metallic detergent is contained in an amount of 0.01% by weight to 5% by weight based on the total amount of the composition.
[B24] The configuration used in any of the above [b16] to [b23] in the automatic transmission.
[B25] The form used in the continuously variable transmission according to any one of [b16] to [b24].

(Use)
The lubricating oil composition according to the sixth aspect of the present invention has been improved by containing the friction modifier (polyfunctional succinimide friction modifier (B)) according to the fifth aspect of the present invention. While having an anti-shudder life and good speed change characteristics, the transmission torque capacity can also be improved by increasing the coefficient of friction between metals. Therefore, it can be preferably used as an automatic transmission oil or a continuously variable transmission oil.

<(7) C-1. Succinimide compound>
(Construction)
The succinimide compound according to the seventh aspect of the present invention has a structure represented by the following general formula (C1).

In the above general formula (C1), R ^c represents a hydrocarbyl group having 8 to 30 carbon atoms. q is an integer of 1 to 7, more preferably an integer of 2 to 4.

Here, specific examples of the hydrocarbyl group having 8 to 30 carbon atoms that can be employed as R ^c include an alkyl group (which may have a ring structure) and an alkenyl group (the position of the double bond is arbitrary). And may have a ring structure.), Aryl groups, alkylaryl groups, alkenylaryl groups, arylalkyl groups, arylalkenyl groups, and the like.

Examples of the alkyl group include linear or branched alkyl groups. Examples of the alkyl group having a ring structure include an alkylcycloalkyl group and a cycloalkylalkyl group. Examples of the cycloalkyl group include cycloalkyl groups having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The substitution position on the cycloalkyl ring is arbitrary.

Examples of the alkenyl group include various linear or branched alkenyl groups. Examples of the alkenyl group having a ring structure include an alkylcycloalkenyl group, an alkenylcycloalkyl group, a cycloalkenylalkyl group, and a cycloalkenylalkenyl group. The cycloalkyl group is the same as described above. Examples of the cycloalkenyl group include cycloalkyl groups having 5 to 7 carbon atoms, such as a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The substitution position on the cycloalkenyl ring and cycloalkyl ring is arbitrary.

Examples of the aryl group include a phenyl group (having a hydrocarbyl substituent), a naphthyl group, and the like. In the alkylaryl group, alkenylaryl group, arylalkyl group, and arylalkenyl group, the substitution position on the aryl group is arbitrary.

R ^c has 8 to 30 carbon atoms, preferably 10 or more, and more preferably 12 or more. Further, it is preferably 20 or less. R ^c is preferably an aliphatic hydrocarbyl group (an alkyl or alkenyl group optionally having a ring structure), and more preferably, the aliphatic hydrocarbyl group has a chain portion. The chain portion may be linear or branched. However, it is particularly preferred that the maximum chain length of the carbon chain contained in the chain portion (however, the chain length from the end closest to the nitrogen atom of the carbon chain) is 8 carbons or more (for example, 4- ( The maximum chain length of the carbon chain contained in the chain portion of the 2-ethyldecyl) cyclohexyl group (the chain length of the carbon chain from the end closest to the nitrogen atom) is 10 carbons, and 4- (9-cyclopentyl) (The maximum of the chain length of the carbon chain contained in the chain portion of the (decan-3-yl) cyclohexyl group (the chain length of the carbon chain from the end closest to the nitrogen atom) is 8 carbons).

Examples of the form of the succinimide compound according to the seventh aspect of the present invention include the following [c1] to [c10].
[C1] In the above formula (C1), R ^c is a hydrocarbyl group having 8 to 30 carbon atoms, and q is an integer of 1 to 7.
[C2] In the above [c1], q is an integer of 2 to 4.
[C3] In the above [c1], q is 2.
[C4] The form in which in any one of the above [c1] to [c3], R ^c has 10 or more carbon atoms.
[C5] The form in which the carbon number of R ^c is 12 or more in any one of the above [c1] to [c3].
[C6] The form in which the carbon number of R ^c is 20 or less in any one of the above [c1] to [c3].
[C7] the [c1] In any of the ~ [c6], form ^{R c} is an aliphatic hydrocarbyl group.
[C8] In the above [c7], R ^c has a chain portion.
[C9] In the above [c8], the maximum chain length in the carbon chain contained in the chain portion (however, the chain length from the end closest to the nitrogen atom of the carbon chain) is 8 carbons or more. .
[C10] The form according to any one of the above [c1] to [c6], wherein R ^c is a linear or branched alkyl group or alkenyl group.

(Production of succinimide compound)
The method for producing the succinimide compound according to the seventh aspect of the present invention is not particularly limited. For example, it can be manufactured as follows. That is, it can be obtained by the reaction of ω-aminoalkanonitrile and 2-hydrocarbyl succinic anhydride (the following formula (C2)).

The imidation reaction of the formula (C2) is performed by removing water from the reaction system by azeotropic distillation with an organic solvent (eg, o-xylene, etc.) and phase separation using a Dean-Stark apparatus under heating and reflux conditions, for example. Can do. Further, for example, after confirming disappearance of 2-hydrocarbyl succinic anhydride, an imide ring may be formed by adding an imidizing agent (for example, acetic anhydride and pyridine).

<(8) C-2. Friction modifier>
The friction modifier according to the eighth aspect of the present invention comprises the succinimide compound according to the seventh aspect of the present invention.

(Content)
The content of the succinimide compound according to the seventh aspect of the present invention in the friction modifier according to the eighth aspect of the present invention is not particularly limited, but preferably based on the total amount of the friction modifier, It is 50 weight% or more, More preferably, it is 80 weight% or more, More preferably, it is 90 weight% or more, and 100 weight% may be sufficient.

Examples of the form of the friction modifier according to the eighth aspect of the present invention include the following [c11] to [c15].
[C11] A form containing the succinimide compound of any one of [c1] to [c10] above.
[C12] A form containing the succinimide compound of any one of [c1] to [c10] above in an amount of 50% by weight or more based on the total amount of the friction modifier.
[C13] A form containing the succinimide compound of any one of [c1] to [c10] above in an amount of 80% by weight or more based on the total amount of the friction modifier.
[C14] A form containing the succinimide compound of any one of [c1] to [c10] above in an amount of 90% by weight or more based on the total amount of the friction modifier.
[C15] A form of the succinimide compound according to any one of [c1] to [c10] above.

<(9) C-3. Lubricating oil composition>
The lubricating oil composition according to the ninth aspect of the present invention comprises a base oil and the friction modifier according to the eighth aspect of the present invention (hereinafter referred to as “polyfunctional succinimide friction modifier (C)”). In some cases).

(Lubricant base oil)
The lubricating base oil in the lubricating oil composition according to the ninth aspect of the present invention is the same as the base oil described above in relation to the lubricating oil composition according to the third aspect of the present invention.

The kinematic viscosity, NOACK evaporation amount, and viscosity index of the lubricating base oil in the lubricating oil composition according to the ninth aspect of the present invention can be set as appropriate according to the intended use of the lubricating oil composition.

(Polyfunctional succinimide friction modifier (C))
The friction modifier according to the eighth aspect of the present invention is as already described. The content is not particularly limited. The content of the succinimide compound represented by the general formula (C1) based on the total amount of the lubricating oil composition can be, for example, 0.1 to 10% by weight. The preferred content can vary depending on the application. For example, when a lubricating oil composition for an automatic transmission or a continuously variable transmission is used, it is preferably 0.1% by weight or more, and more preferably 5% by weight or less.

(Other additives)
The lubricating oil composition according to the ninth aspect of the present invention comprises an ashless dispersant, an antioxidant, and succinic acid according to the seventh aspect of the present invention, in addition to the lubricating base oil and friction modifier described above. Friction modifiers other than imide compounds, antiwear agents, extreme pressure agents, metallic detergents, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, metal deactivators, antifoaming agents and coloring It is preferable to further include at least one selected from the group consisting of agents. The specific aspects of these additives and the contents of each additive are the same as the additives and contents described above in relation to the lubricating oil composition according to the third aspect of the present invention.

Examples of the form of the lubricating oil composition according to the ninth aspect of the present invention include the following [c16] to [c25].
[C16] A form containing a lubricating base oil and the friction modifier of any one of the above [c11] to [c15].
[C17] A form in which the succinimide compound of any one of the above [c1] to [c10] is contained in the above [c16] in an amount of 0.1 to 10% by weight based on the total amount of the composition.
[C18] A form in which the succinimide compound of any one of the above [c1] to [c10] is contained in the above [c16] in an amount of 0.1 to 5% by weight based on the total amount of the composition.
[C19] In any one of the above [c16] to [c18], an ashless dispersant, an antioxidant, a friction modifier other than the succinimide compound represented by the general formula (C1), an antiwear agent, an extreme pressure Further containing at least one selected from the group consisting of an agent, a metal detergent, a viscosity index improver, a pour point depressant, a corrosion inhibitor, a rust inhibitor, a metal deactivator, an antifoaming agent and a colorant. Form.
[C20] The form of any one of [c16] to [c19], wherein the ashless dispersant is contained in an amount of 0.01% by weight to 20% by weight based on the total amount of the composition.
[C21] The form of any one of [c16] to [c20] above, wherein the antioxidant is contained in an amount of 0.1% by weight or more and 5.0% by weight or less based on the total amount of the composition.
[C22] The form of any one of [c16] to [c21], wherein the antiwear agent or the extreme pressure agent is contained in an amount of 0.005 wt% to 5 wt% based on the total amount of the composition.
[C23] A form in which the metal detergent is contained in an amount of 0.01% by weight to 5% by weight based on the total amount of the composition according to any one of the above [c16] to [c22].
[C24] The form used in the automatic transmission according to any one of [c16] to [c23].
[C25] The form used in the continuously variable transmission according to any one of [c16] to [c24].

(Use)
The lubricating oil composition according to the ninth aspect of the present invention is improved by including the friction modifier (polyfunctional succinimide friction modifier (C)) according to the eighth aspect of the present invention. While having an anti-shudder life and good speed change characteristics, the transmission torque capacity can also be improved by increasing the coefficient of friction between metals. Therefore, it can be preferably used as an automatic transmission oil or a continuously variable transmission oil.

Hereinafter, the present invention will be described in more detail based on examples and comparative examples. However, the present invention is not limited to these examples.

<Production example>
Succinimide compounds A-1 to A-3 according to the first aspect of the present invention, succinimide compounds B-1 to B-3 according to the fourth aspect of the present invention, and a seventh aspect of the present invention The succinimide compounds C-1 and C-2 according to the above were produced. The IR spectrum was measured by using FT / IR-4100 manufactured by JASCO Corporation. For samples that were solid at room temperature, the sample was heated and melted, and a small amount was applied to the KBr plate. It measured by apply | coating to a KBr board.

(Production Example A-1)
The succinimide compound A-1 having an aspect in which R ^a = octadecenyl group, m = 1, and n = 0 in the general formula (A1) was produced by the following procedure.
In a 200 mL four-necked flask equipped with a Dean-Stark apparatus, 85.6 mmol (30 g) of octadecenyl succinic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 3-amino-1,2-propanediol (Tokyo Chemical Industry Co., Ltd.) 102.7 mmol (9.4 g) and 50 mL of o-xylene were added, and the interior was purged with nitrogen. The mixture was heated and stirred to reflux xylene, and water produced was removed from the system. After refluxing for 3 hours, the pressure was reduced while flowing a small amount of nitrogen to remove xylene and unreacted amine. Progress of the reaction was confirmed by IR spectrum. 37.8 g of the target compound was obtained. The IR spectrum (Neat) of the product is shown in FIG.

(Production Example A-2)
According to the following procedure, succinimide compound A-2 in an embodiment in which R ^a = 2,4,6,8,10-pentamethyltridecenyl group, m = 1, n = 0 in the above general formula (A1) Manufactured.
The reaction was conducted in the same manner as in Production Example A-1, except that the octadecenyl succinic anhydride in Production Example A-1 was changed to isooctadecenyl succinic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). 0.8 g of the desired compound was obtained.

(Production Example A-3)
In the above general formula (A1), R ^a = ^a mixture of isomers of ^a linear octadecenyl group (a mixture of octadecenyl group isomers having different free valence positions in the octadecene linear chain), m = 1, n = A succinimide compound A-3 having an aspect of 0 was produced.
The reaction was conducted in the same manner as in Production Example A-1, except that the octadecenyl succinic anhydride of Production Example A-1 was changed to an isomer mixed linear octadecenyl succinic anhydride (manufactured by Seiko PMC Co., Ltd.). And 37.8 g of the target compound was obtained.

(Production Example B-1)
According to the following procedure, succinimide compound B-1 having an aspect in which R ^b = octadecenyl group in the general formula (B1) and the hydroxy group was substituted at the para position was produced.
In a 200 mL four-necked flask equipped with a Dean-Stark apparatus, octadecenyl succinic anhydride (Tokyo Chemical Industry Co., Ltd.) 57.1 mmol (20 g), 4-aminophenol (Tokyo Chemical Industry Co., Ltd.) 68. After adding 5 mmol (7.5 g) and 60 mL of o-xylene, the inside was purged with nitrogen. The mixture was heated and stirred to reflux xylene, and water produced was removed from the system. After refluxing for 3 hours, the pressure was reduced while flowing a small amount of nitrogen to remove o-xylene and unreacted amine. Progress of the reaction was confirmed by IR spectrum. About 25 g of the target compound was obtained. The IR spectrum (Neat) of the product is shown in FIG.

(Production Example B-2)
According to the following procedure, a succinimide compound in which R ^b = 2,4,6,8,10-pentamethyltridecenyl group in the above general formula (B1) and the hydroxy group is substituted at the para position B-2 was produced.
The reaction was conducted in the same manner as in Production Example B-1, except that the octadecenyl succinic anhydride in Production Example B-1 was changed to isooctadecenyl succinic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). 25 g of the target compound was obtained.

(Production Example C-1)
The succinimide compound C-1 having an aspect in which R ^c = octadecenyl group and q = 2 in the general formula (C1) was produced by the following procedure.
In a 200 mL four-necked flask equipped with a Dean-Stark apparatus, octadecenyl succinic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 57.1 mmol (20 g), 3-aminopropionitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) After adding 68.5 mmol (4.8 g) and 60 mL of o-xylene, the inside was purged with nitrogen. The mixture was heated and stirred to reflux xylene, and water produced was removed from the system. After refluxing for 3 hours, the pressure was reduced while flowing a small amount of nitrogen to remove o-xylene and unreacted amine. Progress of the reaction was confirmed by IR spectrum. About 24 g of the target compound was obtained.
The IR spectrum (Neat) of the product is shown in FIG.

<Examples 1 to 6 and Comparative Examples 1 to 3>
The lubricating oil compositions according to the third aspect of the present invention (Examples 1 to 3) and the lubricating oil compositions according to the sixth aspect of the present invention (Examples 4 to 5) A lubricating oil composition according to the ninth aspect of the present invention (Example 6) and a comparative lubricating oil composition (Comparative Examples 1 to 3) were prepared. In the table, the numerical values of the component amounts are all based on the total amount of the composition, and “wt.%” Means wt% and “wt. Ppm” means wt ppm for the unit.

(Evaluation of friction coefficient between metals)
Using a block-on-ring friction tester (LFW-1 manufactured by FALEX), the friction coefficient between metals was evaluated under the condition that the lubricating oil composition was present on the friction surface. The test conditions were a load of 889 N, a surface pressure of 0.54 GPa, a sliding speed of 0.125 m / s, a test temperature of 80 ° C., and a test time of 3 minutes. The average friction coefficient was evaluated. The results are also shown in Table 1. If the coefficient of friction between metals is 0.110 or more under the conditions of this test, it can be said that a good transmission torque capacity can be secured and that it has a good speed change characteristic.

(Evaluation of anti-shudder life)
Using a low-speed slip tester specified in JASO M349: 2010, the anti-shudder life of the lubricating oil composition was evaluated. The test method was based on JASO M349: 2010, and μ-V curves were measured at temperatures of 40 ° C., 80 ° C., and 120 ° C. Judgment of the anti-shudder life is based on JASO M315: 2004, and the μ-V curve at the above measured temperature is approximated by a least-square function using a quintic function, and the slip function (V) is 0.3 m / The gradient was obtained by differentiating at two points of s and 0.9 m / s, and the lifetime was determined when any of the four gradient values at 40 ° C. and 80 ° C. became negative. The results are also shown in Table 1. If the shudder prevention life is 100 hours or more under the conditions of this test, it can be said that the ability to maintain the shudder prevention performance is excellent.

(Evaluation results)
As the friction modifier, succinimide compounds A-1 to A-3 according to the first aspect of the present invention, succinimide compounds B-1 to B-2 according to the fourth aspect of the present invention, and The lubricating oil compositions of Examples 1 to 6 each containing the succinimide compound C-1 according to the seventh aspect showed excellent results in both the intermetal friction coefficient and the shudder prevention life.
The lubricating oil composition of Comparative Example 1 in which no friction modifier was blended did not have anti-shudder performance.
Further, the lubricating oil compositions of Comparative Examples 2 and 3 each containing glycerol monooleate and alkyldiethanolamine, which are conventionally known general friction modifiers, were remarkably inferior in the anti-shudder life. In addition, the lubricating oil composition of Comparative Example 3 did not reach a satisfactory level in the coefficient of friction between metals.

From the above results, according to the lubricating oil composition containing the succinimide compound of the present invention as a friction modifier, a long shudder prevention life and a good transmission torque capacity due to a high intermetal friction coefficient can be realized simultaneously. Indicated.

The lubricating oil composition using the succinimide compound of the present invention as a friction modifier can be preferably used as a transmission oil, and can be particularly preferably used as an automatic transmission oil or a continuously variable transmission oil. In particular, it can be preferably used as a lubricating oil used in a transmission having a torque converter having a lock-up mechanism, and particularly as a lubricating oil used in a transmission having a torque converter that performs slip control in a lock-up clutch.

Claims (9)

1. A succinimide compound represented by the following general formula (1).
   

   

   
   [In the formula (1), R represents a hydrocarbyl group having 8 to 30 carbon atoms, and X represents a group represented by any one of the following general formulas (2) to (5). ]
   

   

   
   [In the formula (2), m is an integer of 1 to 4, n is an integer of 0 to 3, and m + n is 5 or less. ]
   

   

   
   [In Formula (3), q is an integer of 1-7. ]
   

   

   
   [In the formula (4), the substitution position of the hydroxy group in the aromatic ring may be any of the ortho, meta and para positions. ]
2. The succinimide compound of Claim 1 represented by the following general formula (A1).
   

   

   
   [In the formula (A1), R ^a represents a hydrocarbyl group having 8 to 30 carbon atoms, m is an integer of 1 to 4, n is an integer of 0 to 3, and m + n is 5 or less. ]
3. A friction modifier containing the succinimide compound according to claim 2.
4. The succinimide compound of Claim 1 represented by the following general formula (B1).
   

   

   [In formula (B1), R ^b represents a hydrocarbyl group having 8 to 30 carbon atoms, and the hydroxy group in the aromatic ring may be substituted at any of the ortho, meta, and para positions. ]
5. A friction modifier containing the succinimide compound according to claim 4.
6. The succinimide compound of Claim 1 represented by the following general formula (C1).
   

   

   [In the formula (C1), R ^c represents a hydrocarbyl group having 8 to 30 carbon atoms, and q is an integer of 1 to 7. ]
7. A friction modifier containing the succinimide compound according to claim 6.
8. Lubricating base oil,
   A lubricating oil composition comprising the friction modifier according to claim 3, 5 or 7.
9. Lubricating base oil,
   A lubricating oil composition for a continuously variable transmission, comprising the friction modifier according to claim 3, 5 or 7.

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