JP7352483B2 - Friction modifiers and lubricating oil compositions - Google Patents

Description

The present invention relates to a friction modifier and a lubricating oil composition containing the friction modifier.

The viscosity of lubricating oils, hydraulic oils, etc. used in automobiles and the like has been decreasing in recent years due to the pursuit of fuel efficiency. Lower viscosity reduces frictional resistance in the fluid lubrication area and improves fuel efficiency, but wear tends to occur under high pressure in the mixed lubrication area and boundary lubrication area, so friction modifiers are used to prevent such wear. It is common to do so.
Friction modifiers that improve fuel efficiency are mainly classified into four types: oiliness improvers that form an oil film on friction surfaces under low loads to reduce friction and wear; Wear inhibitors that form a protective film and prevent wear; Extreme pressure agents that prevent seizure and scuffing in extreme pressure lubrication conditions; Friction control agents that physically and chemically adsorb to friction surfaces and control the coefficient of friction. It is a drug.

Currently, commonly used friction modifiers include long-chain fatty acid esters and fatty acid amides as oiliness improvers, phosphate esters and zinc dithiophosphate as anti-wear agents, and organic sulfur, organic halogen compounds, and friction control agents as extreme pressure agents. Examples include organic molybdenum compounds.
Examples of polymer-type friction modifiers include copolymers consisting of α-olefins and fumaric esters (Patent Document 1), acrylic ester copolymers having hydroxyl groups (Patent Document 2), hydrophilic polymer units and polyolefins. polyester having a unit (Patent Document 3), a methacrylic acid ester copolymer having a block structure consisting of a polar segment unit and a hydrophobic segment unit (Patent Document 4), a phosphorus-functionalized methacrylic acid ester copolymer (Patent Document 3) Document 5), a chain polymethacrylate polymer having a carboxyl group (Patent Document 6), and the like are known.

However, the polymeric friction modifiers of Patent Documents 1 to 5 have a problem in that their friction reducing effects are not yet sufficient when used under conditions in the low to medium temperature range. Further, the friction modifier of Patent Document 6 exhibits an effect under sliding friction conditions at low temperatures, but there is a problem in that the friction reducing effect is not sufficient under rolling friction conditions.

Patent No. 3730660 Patent No. 5822706 Patent No. 5684832 Japanese Patent Application Publication No. 4686444 Special Publication No. 2014-518925 JP2016-210941A

The object of the present invention is to provide a friction modifier that is excellent in reducing sliding friction and rolling friction even when used under conditions of low to medium temperature ranges of around 40 to 80°C; a lubricating oil containing the friction modifier. An object of the present invention is to provide a composition.

［一般式（１）中のＲ^１は水素原子又はメチル基；－Ｘ^１－は－Ｏ－で表される基；Ｒ^２は炭素数１～１０のアルキレン基を表す。ｓは１～１５の整数であり、ｓが２以上の場合のＲ^２は同一でも異なっていてもよい。］ The present inventors conducted studies to achieve the above object, and as a result, they arrived at the present invention.
That is, the present invention provides a friction modifier containing a (co)polymer (A) containing a monomer (a) represented by the following general formula (1) as a constituent monomer; and at least one member selected from the group consisting of viscosity index improvers, detergents, dispersants, antioxidants, oiliness improvers, extreme pressure agents, antifoaming agents, demulsifiers, corrosion inhibitors, and pour point effect agents. A lubricating oil composition containing an additive.

[R ¹ in general formula (1) is a hydrogen atom or a methyl group; -X ¹ - is a group represented by -O-; R ² represents an alkylene group having 1 to 10 carbon atoms. s is an integer from 1 to 15, and when s is 2 or more, R ² may be the same or different. ]

The lubricating oil composition containing the friction modifier of the present invention exhibits the effect of being excellent in sliding friction and rolling friction under conditions in the low to medium temperature range.

The friction modifier of the present invention contains a (co)polymer (A) containing a monomer (a) represented by the following general formula (1) as a constituent monomer.
By containing the (co)polymer (A) containing the monomer (a) as a constituent monomer, the friction modifier of the present invention has a strong adsorption ability of carboxyl groups to the metal surface, which improves the friction modifier compared to conventional friction modifiers. It is presumed that the effect of reducing friction (sliding friction and rolling friction) under conditions in the low to medium temperature range can be achieved better than that of the modifier.

[R ¹ in general formula (1) is a hydrogen atom or a methyl group; -X ¹ - is a group represented by -O-; R ² represents an alkylene group having 1 to 10 carbon atoms. s is an integer from 1 to 15, and when s is 2 or more, R ² may be the same or different. ]

Among the constituent monomers of the (co)polymer (A) contained in the friction modifier of the present invention, monomer (a) has one carboxyl group represented by the above general formula (1). It is a monomer.
R ¹ in the general formula (1) is a hydrogen atom or a methyl group, and among these, both a hydrogen atom and a methyl group are preferable from the viewpoint of reducing friction.

-X ¹ - in general formula (1) is a group represented by -O-.
In the present invention, since -X ¹ - is a group represented by -O- rather than -NH-, adsorption to the metal surface and oil film formation are promoted in the boundary lubrication region where metals are likely to come into contact with each other. , it is presumed that friction reduction can be achieved.

R ² in general formula (1) is an alkylene group having 1 to 10 carbon atoms.
Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, and 1,10-decylene group. Among these, from the viewpoint of reducing friction, an alkylene group having 1 to 8 carbon atoms is preferred, an alkylene group having 2 to 6 carbon atoms is more preferred, and an alkylene group having 2 to 5 carbon atoms is particularly preferred.

In general formula (1), s is an integer of 1 to 15, preferably an integer of 1 to 14, more preferably an integer of 1 to 12, particularly preferably an integer of 1 to 10, from the viewpoint of reducing friction. A plurality of R ² may be the same or different.

Specific examples of monomer (a) include carboxypolyacetolactone mono(meth)acrylate (adding 1 to 15 moles of α-acetolactone), carboxypolypropiolactone mono(meth)acrylate (adding β-propiolactone), carboxypolybutyrolactone mono(meth)acrylate (addition of 1 to 15 moles of γ-butyrolactone), carboxypolyvalerolactone mono(meth)acrylate (addition of 1 to 15 moles of δ-valerolactone), carboxy Examples include polycaprolactone mono(meth)acrylate (addition of 1 to 15 moles of ε-caprolactone).

Monomer (a) is, for example, a lactone having 2 to 11 carbon atoms (for example, α-acetolactone, β-propiolactone, γ-butyrolactone, β-butyrolactone, δ-valerolactone, γ-valerolactone, ε -caprolactone, δ-caprolactone, γ-caprolactone, etc.) and (meth)acrylic acid.
In addition, as the monomer (a), β-carboxyethyl acrylate (product name "β-CEA", manufactured by Daicel Allnex Corporation), ω-carboxy-polycaprolactone (2 molar adduct) monoacrylate (product name ""AronixM-5300" (manufactured by Toagosei Co., Ltd.) and the like are commercially available.

The (co)polymer (A) in the present invention further comprises a monomer (b) represented by the following general formula (2) from the viewpoint of compatibility between (A) and base oil and friction reduction. It is preferable to use a monomer.

[R ³ in general formula (2) is a hydrogen atom or a methyl group; -X ² - is a group represented by -O- or -NH-; R ⁴ is a linear or branched alkyl group having 5 to 44 carbon atoms represents. ]

R ³ in the general formula (2) is a hydrogen atom or a methyl group, and both a hydrogen atom and a methyl group are preferable from the viewpoint of reducing friction.

-X ² - in general formula (2) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of reducing friction.

R ⁴ in the general formula (2) is a straight-chain or branched alkyl group having 5 to 44 carbon atoms.
Specifically, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, n-heptyl group, isoheptyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, isononyl group, n-decyl group. group, isodecyl group, n-undecyl group, isoundecyl group, n-dodecyl group, isododecyl group, n-tridecyl group, isotridecyl group, n-tetradecyl group, 2-ethyldodecyl group, n-pentadecyl group, 2-methyltetradecyl group group, n-hexadecyl group, isohexadecyl group, n-heptadecyl group, isoheptadecyl group, 2-ethylpentadecyl group, 2-octylnonyl group, 2-(3-methylhexyl)-7-methyl-nonyl group, n -Octadecyl group, isooctadecyl group, 2-hexylundecyl group, 2-ethylheptadecyl group, 1-hexyltridecyl group, n-icosyl group, 2-octylundecyl group, isoicosyl group, 1-undecyldodecyl group , 1-octylpentadecyl group, 2-decyltridecyl group, n-tetraicosyl group, 2-decyltetradecyl group, 2-dodecylpentadecyl group, 2-heptylicosyl group, 2-dodecylhexadecyl group, n-triacontyl group, 2 -tetradecyl octadecyl group, n-hexatriacontyl group, n-tetracontyl group, 2-ethyltetracontyl group and polyolefins [e.g. propylene oligomer (dimer to 14-mer), ethylene/propylene oligomer (di- to 20-mer) ) and isobutene oligomers (dimers to decamers), etc.], and residues obtained by removing the hydroxyl group from oxo alcohols.

Of ^R4 , from the viewpoint of compatibility with the base oil (A) and friction reduction effect, straight chain or branched alkyl groups having 8 to 34 carbon atoms are preferred, and straight chain or branched alkyl groups are more preferred. is an alkyl group having 8 to 32 carbon atoms, particularly preferred is a straight chain or branched alkyl group having 10 to 32 carbon atoms, and most preferred is a straight chain alkyl group having 10 to 22 carbon atoms and a straight chain alkyl group having 12 to 22 carbon atoms. ~32 branched alkyl groups.

From the viewpoint of reducing friction, the (co)polymer (A) in the present invention preferably has a monomer (c) represented by the following general formula (3) as a constituent monomer.

[R ⁵ in general formula (3) is a hydrogen atom or a methyl group; -X ³ - is a group represented by -O- or -NH-; R ⁶ is an alkylene group having 1 to 10 carbon atoms; R ⁷ is a Represents an alkylene group having 1 to 10 carbon atoms. t is an integer from 1 to 15, and when t is 2 or more, R ⁷ may be the same or different. ]

R ⁵ in general formula (3) is a hydrogen atom or a methyl group, and both a hydrogen atom and a methyl group are preferred from the viewpoint of reducing friction.

-X ³ - in general formula (3) is a group represented by -O- or -NH-, and among these, -O- is preferable from the viewpoint of reducing friction.

R ⁶ in general formula (3) is an alkylene group having 1 to 10 carbon atoms.
Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, and 1,10-decylene group. Among these, from the viewpoint of reducing friction, an alkylene group having 1 to 8 carbon atoms is preferred, an alkylene group having 2 to 6 carbon atoms is more preferred, and an alkylene group having 2 to 5 carbon atoms is particularly preferred.

R ⁷ in general formula (3) is an alkylene group having 1 to 10 carbon atoms.
Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, and 1,10-decylene group. Among these, from the viewpoint of reducing friction, an alkylene group having 1 to 8 carbon atoms is preferred, an alkylene group having 2 to 6 carbon atoms is more preferred, and an alkylene group having 2 to 5 carbon atoms is particularly preferred.

In the general formula (3), t is an integer of 1 to 15, preferably an integer of 1 to 14, more preferably an integer of 1 to 12, particularly preferably an integer of 1 to 10, from the viewpoint of reducing friction. A plurality of R ⁷ 's may be the same or different.

Specific examples of monomer (c) include α-acetolactone modified (1 to 15 mole addition) hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylate, β-propiolactone modified (1 to 15 mole addition) )Hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylate, γ-butyrolactone modified (1 to 15 moles added)Hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylate, δ-valerolactone modified (1 to 15 moles) addition) hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylate (δ-valerolactone 1 to 15 mol adduct), ε-caprolactone modified (1 to 15 mol addition) hydroxyalkyl (1 to 10 carbon atoms) (meth) ) acrylate (adduct of 1 to 15 moles of ε-caprolactone), and the like.

The monomer (c) is, for example, a lactone having 2 to 11 carbon atoms (for example, α-acetolactone, β-propiolactone, γ-butyrolactone, β-butyrolactone, δ-valerolactone, γ-valerolactone, ε -caprolactone, δ-caprolactone, γ-caprolactone, etc.) to hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylate or hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylamide.
In addition, as the monomer (c), ε-caprolactone adducts of hydroxyethyl methacrylate (product names "Plaxel FM1", "Plaxel FM2D", "Plaxel FM3", etc., all manufactured by Daicel Corporation), hydroxyethyl acrylate ε-caprolactone adducts (product names "Plaxel FA1", "Plaxel FA2D", "Plaxel FA5", "Plaxel FA10L", etc., all manufactured by Daicel Corporation) are commercially available.

The (co)polymer (A) in the present invention has an alkyl group in addition to monomer (a) which is an essential constituent monomer, monomer (b) and monomer (c) which are preferably used together. (Meth)acrylic acid alkyl ester (d) (hereinafter sometimes abbreviated as monomer (d)), which is a linear alkyl group having 1 to 4 carbon atoms, may be used in combination as a constituent monomer. .

Examples of the (meth)acrylic acid alkyl ester (d) in which the alkyl group is a straight-chain alkyl group having 1 to 4 carbon atoms include methyl (meth)acrylate, ethyl (meth)acrylate, and n-propyl (meth)acrylate. and n-butyl (meth)acrylate.
Preferred monomers (d) are methyl (meth)acrylate, ethyl (meth)acrylate, and n-butyl (meth)acrylate.

(A) is nitrogen other than monomers (b) to (c) in addition to monomer (a), monomer (b), monomer (c), and monomer (d). Atom-containing vinyl monomer (e), hydroxyl group-containing vinyl monomer (f) other than monomer (c), phosphorus atom-containing vinyl monomer (g), and carboxyl group-containing monomer other than monomer (a) Monomer (h) may be used in combination as a constituent monomer.

As the nitrogen atom-containing vinyl monomer (e), amide group-containing vinyl monomers (e1) such as (meth)acrylamide and monoalkylamino (meth)acrylamide; nitro group-containing monomers such as 4-nitrostyrene; (e2); Vinyl monomer containing primary to tertiary amino groups such as (meth)allylamine, methylaminoethyl (meth)acrylate, and dimethylaminoethyl (meth)acrylate (e3); Containing nitrile group such as (meth)acrylonitrile Examples include vinyl monomer (e4).

Examples of the hydroxyl group-containing vinyl monomer (f) include N,N-dihydroxymethyl (meth)acrylamide, (meth)allyl alcohol, and 2-hydroxyethyl (meth)acrylate.

Examples of the phosphorus atom-containing monomer (g) include phosphate group-containing monomers (g1) such as (meth)acryloyloxyethyl phosphate and isopropenyl phosphate; (meth)acryloyloxyethylphosphonic acid, allylphosphonic acid; Examples include phosphono group-containing monomers (g2) such as acids.

The carboxyl group-containing monomer (h) includes (meth)acrylic acid, a monomer (h1) represented by the following general formula (4), and a monomer (h2) represented by the following general formula (5). ) and a monomer (h3) represented by the following general formula (65).

[R ⁸ in general formula (4) is a hydrogen atom or a methyl group; -X ⁴ - is a group represented by -O- or -NH-; R ⁹ is an alkylene group having 1 to 10 carbon atoms; R ¹⁰ O represents an alkyleneoxy group having 2 to 4 carbon atoms; R ¹¹ represents an alkylene group having 1 to 12 carbon atoms. p is an integer from 0 to 10, and when p is 2 or more, R ¹⁰ O may be the same or different. ]

[R ¹² in general formula (5) is a hydrogen atom or a methyl group; -X ⁵ - is a group represented by -O- or -NH-; R ¹³ is an alkylene group having 1 to 10 carbon atoms; R ¹⁴ O is an alkyleneoxy group having 2 to 4 carbon atoms; R ¹⁵ each independently represents a hydrogen atom or a carboxyl group, and at least one represents a carboxyl group. q is an integer from 0 to 10, and when q is 2 or more, R ¹⁴ O may be the same or different. ]

[R ¹⁶ in general formula (6) is a hydrogen atom or a methyl group; -X ⁶ - is a group represented by -O- or -NH-; R ¹⁷ is an alkylene group having 1 to 10 carbon atoms; R ¹⁸ O is an alkyleneoxy group having 2 to 4 carbon atoms; R ¹⁹ each independently represents a hydrogen atom or a carboxyl group, and at least one represents a carboxyl group. r is an integer from 0 to 10, and when r is 2 or more, R ¹⁸ O may be the same or different. ]

Monomer (h1) is a monomer having one carboxyl group represented by the above general formula (4).
R ⁸ in general formula (4) is a hydrogen atom or a methyl group, and among these, both a hydrogen atom and a methyl group are preferred from the viewpoint of reducing friction.

-X ⁴ - in general formula (4) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of reducing friction.

R ⁹ in general formula (4) is an alkylene group having 1 to 10 carbon atoms.
Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, and 1,10-decylene group. Among these, from the viewpoint of reducing friction, ethylene groups, 1,2-propylene groups and 1,3-propylene groups are preferred, and ethylene groups are more preferred.

R ¹⁰ O in general formula (4) is an alkyleneoxy group having 2 to 4 carbon atoms. Examples of the alkyleneoxy group having 2 to 4 carbon atoms include ethyleneoxy group, propyleneoxy group and butyleneoxy group. Examples of the propylene group in the propyleneoxy group include 1,2-propylene group and 1,3-propylene group, and examples of the butylene group in the butyleneoxy group include 1,2-butylene group and 1,3-butylene group. and 1,4-butylene group. From the viewpoint of reducing friction, the alkyleneoxy group is preferably an ethyleneoxy group or a propyleneoxy group, and more preferably an ethyleneoxy group.

In general formula (4), p is an integer of 0 to 10, preferably an integer of 0 to 7, more preferably an integer of 0 to 5, particularly preferably an integer of 0 to 3, from the viewpoint of reducing friction.
When p is 2 or more, a plurality of R ¹⁰ O's may be the same or different.

R ¹¹ in the general formula (4) is a residue obtained by removing two carboxyl groups from a dicarboxylic acid having 3 to 14 carbon atoms, and is an alkylene group having 1 to 12 carbon atoms.
Examples of the alkylene group having 1 to 12 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, 1,10-decylene group, 1,11-undecylene group, 1,12-dodecylene group, and the like. Among these, from the viewpoint of reducing friction, an alkylene group having 1 to 6 carbon atoms is preferred, and an alkylene group having 1 to 4 carbon atoms is more preferred.
Examples of dicarboxylic acids having 3 to 14 carbon atoms include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, and alkylsuccinic acids (including 1 to 10 carbon atoms). succinic acid having an alkyl group, etc.).

Specific examples of the monomer (h1) include monoesters of hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylates and dicarboxylic acids having 3 to 14 carbon atoms {for example, malonic acid mono(2-(meth) ) acryloyloxyethyl), mono(meth)acryloyloxy-n-propyl malonate, mono(meth)acryloyloxyisopropyl malonate, mono(4-(meth)acryloyloxy-n-butyl) malonate, Mono(meth)acryloyloxyisobutyl malonate, mono(6-(meth)acryloyloxy-n-hexyl) malonate, mono(8-(meth)acryloyloxy-n-octyl) malonate, mono(10- (meth)acryloyloxy-n-decyl), mono(meth)acryloyloxyisodecyl malonate, mono(2-(meth)acryloyloxyethyl) succinate, mono(3-(meth)acryloyloxy-n- succinate) propyl), mono(meth)acryloyloxyisopropyl succinate, mono(4-(meth)acryloyloxy-n-butyl) succinate, mono(meth)acryloyloxyisobutyl succinate, mono(6-(meth)acryloyl succinate) oxy-n-hexyl), mono(meth)acryloyloxy-n-octyl succinate, mono(meth)acryloyloxy-n-decyl succinate, mono(meth)acryloyloxyisosuccinate Decyl, mono(meth)acryloyloxyethyl glutarate, mono(3-(meth)acryloyloxy-n-propyl) glutanate, mono(meth)acryloyloxyisopropyl glutanate, mono(4-(meth)acryloyloxyisopropyl glutanate), meth)acryloyloxy-n-butyl), mono(meth)acryloyloxyisobutyl glutarate, mono(6-(meth)acryloyloxy-n-hexyl) glutarate, mono(8-(meth)acryloyloxy-n) glutarate -octyl), mono(meth)acryloyloxy-n-decyl glutanate, mono(meth)acryloyloxyisodecyl glutanate, mono(2-(meth)acryloyloxyethyl) adipate, mono(meth)acryloyloxyethyl adipate, 3-(meth)acryloyloxy-n-propyl), mono(meth)acryloyloxyisopropyl adipate, mono(meth)acryloyloxy-n-butyl adipate, mono(meth)acryloyloxyisobutyl adipate, Monoadipate (6-(meth)acryloyloxy-n-hexyl), monoadipate (8-(meth)acryloyloxy-n-octyl), monoadipate (10-(meth)acryloyloxy-n-decyl) , mono(meth)acryloyloxyisodecyl adipate, mono(meth)acryloyloxyethyl pimelic acid, mono(meth)acryloyloxy-n-propyl pimelic acid, mono(meth)acryloyl pimelic acid Oxyisopropyl, pimelic acid mono(4-(meth)acryloyloxy-n-butyl), pimelic acid mono(meth)acryloyloxyisobutyl, pimelic acid mono(6-(meth)acryloyloxy-n-hexyl), pimelic acid mono (8-(meth)acryloyloxy-n-octyl), pimelic acid mono(10-(meth)acryloyloxy-n-decyl), pimelic acid mono(meth)acryloyloxyisodecyl, suberic acid mono(2-(meth) ) acryloyloxyethyl), suberic acid mono(3-(meth)acryloyloxy-n-propyl), suberic acid mono(meth)acryloyloxyisopropyl, suberic acid mono(4-(meth)acryloyloxy-n-butyl), Mono(meth)acryloyloxyisobutyl suberic acid, mono(6-(meth)acryloyloxy-n-hexyl) suberic acid, mono(8-(meth)acryloyloxy-n-octyl) suberic acid, mono(10- (meth)acryloyloxy-n-decyl), mono(meth)acryloyloxyisodecyl suberate, mono(meth)acryloyloxyethyl azelaate, mono(meth)acryloyloxy-n-azelaate propyl), mono(meth)acryloyloxyisopropyl azelaate, mono(4-(meth)acryloyloxy-n-butyl) azelaate, mono(meth)acryloyloxyisobutyl azelaate, mono(6-(meth)acryloyloxyisobutyl azelaate) azelaic acid mono(8-(meth)acryloyloxy-n-octyl), azelaic acid mono(10-(meth)acryloyloxy-n-decyl), azelaic acid mono(meth)acryloyloxy Isodecyl, mono(meth)acryloyloxyethyl sebacate, mono(meth)acryloyloxy-n-propyl sebacate, mono(meth)acryloyloxyisopropyl sebacate, mono(4-(meth)acryloyloxyethyl sebacate) (meth)acryloyloxy-n-butyl), mono(meth)acryloyloxyisobutyl sebacate, mono(6-(meth)acryloyloxy-n-hexyl) sebacate, mono(8-(meth)acryloyloxy- n-octyl), mono(10-(meth)acryloyloxy-n-decyl) sebacate, mono(meth)acryloyloxyisodecyl sebacate, mono(meth)acryloyloxyethyl dodecanedioate, mono(meth)acryloyloxyethyl dodecanedioate, Acid mono(3-(meth)acryloyloxy-n-propyl), dodecanedioic acid mono(meth)acryloyloxyisopropyl, dodecanedioic acid mono(4-(meth)acryloyloxy-n-butyl), dodecanedioic acid mono( meth)acryloyloxyisobutyl, dodecanedioic acid mono(6-(meth)acryloyloxy-n-hexyl), dodecanedioic acid mono(8-(meth)acryloyloxy-n-octyl), dodecanedioic acid mono(10-( (meth)acryloyloxy-n-decyl), mono(meth)acryloyloxyisodecyl dodecanedioate, etc.};
Monoesterified product of alkylene (carbon number 2 to 4) oxide adduct (additional mole number 1 to 10) of hydroxyalkyl (carbon number 1 to 10) (meth)acrylate and carbon number 3 to 14 dicarboxylic acid {for example, Monoesterified product of malonic acid and (meth)acryloyloxyethyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide), monoesterified product of malonic acid and (meth)acryloyloxy-n-propyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide) Monoesterified product, monoesterified product of malonic acid and (meth)acryloyloxyisopropyl polyethylene glycol (1 to 10 moles of ethylene oxide added), malonic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (1 to 10 moles of ethylene oxide added) monoesterified product of malonic acid and (meth)acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of malonic acid and (meth)acryloyloxyethyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), Monoesterified product of succinic acid and (1 to 10 moles of ethylene oxide added), monoesterified product of succinic acid and (meth)acryloyloxy-n-propyl polyethylene glycol (added 1 to 10 moles of ethylene oxide), succinic acid and (meth)acryloyloxyisopropyl polyethylene Monoesterified product with glycol (1 to 10 moles of ethylene oxide added), monoesterified product of succinic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (added 1 to 10 moles of ethylene oxide), monoesterified product of succinic acid and (1 to 10 moles of ethylene oxide added), ) Monoesterified product with acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of glutanic acid and (meth)acryloyloxyethyl polyethylene glycol (addition of 1 to 10 mole of ethylene oxide), monoesterified product of glutanic acid and Monoester of (meth)acryloyloxy-n-propyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoester of glutanic acid and (meth)acryloyloxyisopropyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide) Monoesterified product of glutanic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide), Monoesterified product of glutanic acid and (meth)acryloyloxyisobutyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide) ), monoesterified products of adipic acid and (meth)acryloyloxyethyl polyethylene glycol (1 to 10 moles of ethylene oxide added), monoesterified products of adipic acid and (meth)acryloyloxy-n-propylpolyethylene glycol (added 1 to 10 moles of ethylene oxide), Monoesterified product of adipic acid and meth)acryloyloxyisopropyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of adipic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide) (addition of 1 to 10 moles of ethylene oxide), monoester of adipic acid and (meth)acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), pimelic acid and (meth)acryloyloxyethyl Monoesterified products with polyethylene glycol (1 to 10 moles of ethylene oxide added), monoesterified products of pimelic acid and (meth)acryloyloxy-n-propyl polyethylene glycol (1 to 10 moles of ethylene oxide added), and monoesterified products of pimelic acid and (1 to 10 moles of ethylene oxide added). Monoesterified product of meth)acryloyloxyisopropyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of pimelic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (addition of 1 to 10 mole of ethylene oxide) , monoesterified product of pimelic acid and (meth)acryloyloxyisobutyl polyethylene glycol (1 to 10 moles of ethylene oxide added), monoesterified product of suberic acid and (meth)acryloyloxyethyl polyethylene glycol (added 1 to 10 moles of ethylene oxide) Esterified product, monoesterified product of suberic acid and (meth)acryloyloxy-n-propyl polyethylene glycol (1 to 10 moles of ethylene oxide added), suberic acid and (meth)acryloyloxyisopropyl polyethylene glycol (1 to 10 moles of ethylene oxide added) monoesterified product of suberic acid and (meth)acryloyloxy-n-butylpolyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of suberic acid and (meth)acryloyloxyisobutylpolyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoester of azelaic acid and (meth)acryloyloxyethyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), azelaic acid and (meth)acryloyloxy-n- Monoesterified product with propyl polyethylene glycol (1 to 10 moles of ethylene oxide added), monoesterified product of azelaic acid and (meth)acryloyloxyisopropyl polyethylene glycol (added 1 to 10 moles of ethylene oxide), azelaic acid and (meth) Monoesterified product of acryloyloxy-n-butyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide), monoesterified product of azelaic acid and (meth)acryloyloxyisobutyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide), sebacin Monoesterified products of acid and (meth)acryloyloxyethyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide), sebacic acid and (meth)acryloyloxy-n-propyl polyethylene glycol (added with 1 to 10 moles of ethylene oxide) Monoesterified product, monoesterified product of sebacic acid and (meth)acryloyloxyisopropyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of sebacic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (added 1 to 10 moles of ethylene oxide) monoesterified product of sebacic acid and (meth)acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of dodecanedioic acid and (meth)acryloyloxyethyl polyethylene glycol (added 1 to 10 moles of ethylene oxide) monoesterified product of dodecanedioic acid and (meth)acryloyloxy-n-propyl polyethylene glycol (added 1 to 10 moles of ethylene oxide), monoesterified product of dodecanedioic acid and (meth)acryloyl Monoesterified product of oxyisopropyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), monoesterified product of dodecanedioic acid and (meth)acryloyloxy-n-butyl polyethylene glycol (addition of 1 to 10 mole of ethylene oxide), dodecane A monoester of a diacid and (meth)acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 moles of ethylene oxide), etc.

The monomer (h1) is, for example, an alkyl dicarboxylic acid having 3 to 14 carbon atoms (for example, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid) (1 to 10) succinic acid, etc.) or their anhydrides or lower alkyl (1 to 4 carbon atoms) esters and hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylates or hydroxyalkyl (1 to 10 carbon atoms) (meth) ) can be obtained by monoesterification of acrylate with an adduct of 1 to 10 moles of alkylene (carbon number 2 to 4) oxide. In addition, alkyl dicarboxylic acids having 3 to 14 carbon atoms or their anhydrides or lower alkyl (1 to 4 carbon atoms) esters and hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylamides or hydroxyalkyl (1 to 10 carbon atoms) ) (meth)acrylylamide with an adduct of 1 to 10 moles of alkylene (carbon number 2 to 4) oxide.
In addition, as the monomer (h1), mono(2-acryloyloxyethyl) succinate (manufactured by Tokyo Chemical Industry Co., Ltd.), mono(2-acryloyloxyethyl) succinate (product name "HOA-MS (N)") ”, manufactured by Kyoeisha Chemical Co., Ltd.), etc. are commercially available.

Monomer (h2) is a monomer having 1 to 5 carboxyl groups represented by the above general formula (5).
R ¹² in general formula (5) is a hydrogen atom or a methyl group, and among these, both a hydrogen atom and a methyl group are preferred from the viewpoint of reducing friction.

-X ⁵ - in general formula (5) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of reducing friction.

R ¹³ in general formula (5) is an alkylene group having 1 to 10 carbon atoms. Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, and 1,10-decylene group.
Among these, from the viewpoint of reducing friction, ethylene groups, 1,2-propylene groups and 1,3-propylene groups are preferred, and ethylene groups are more preferred.

R ¹⁴ O in general formula (5) is an alkyleneoxy group having 2 to 4 carbon atoms. Examples of the alkyleneoxy group having 2 to 4 carbon atoms include ethyleneoxy group, propyleneoxy group and butyleneoxy group. Examples of the propylene group in the propyleneoxy group include 1,2-propylene group and 1,3-propylene group, and examples of the butylene group in the butyleneoxy group include 1,2-butylene group, 1,3-butylene group, and Examples include 1,4-butylene group.
From the viewpoint of reducing friction, the alkyleneoxy group is preferably an ethyleneoxy group or a propyleneoxy group, and more preferably an ethyleneoxy group.

In general formula (5), q is an integer of 0 to 10, preferably an integer of 0 to 7, more preferably an integer of 0 to 5, particularly preferably an integer of 0 to 3 from the viewpoint of reducing friction.
When q is 2 or more, a plurality of R ¹⁴ O's may be the same or different.

R ¹⁵ in general formula (5) each independently represents a hydrogen atom or a carboxyl group, at least one of which is a carboxyl group, and among these, from the viewpoint of reducing friction, preferably 1 to 5 carboxyl groups, More preferably, the number of carboxyl groups is 1 to 4, particularly preferably 1 to 3.

Specific examples of the monomer (h2) include monohydroxyethyl phthalate (meth)acrylate, monohydroxy phthalate n-propyl (meth)acrylate, monohydroxyisopropyl phthalate (meth)acrylate, monohydroxy phthalate. n-butyl (meth)acrylate, monohydroxyisobutyl phthalate (meth)acrylate, monohydroxy-n-hexyl phthalate (meth)acrylate, monohydroxy-n-octyl phthalate (meth)acrylate, monohydroxy-n phthalate - Decyl (meth)acrylate, monoester of phthalic acid and hydroxyalkyl (2-10 carbon atoms) (meth)acrylate with 1-10 mole adduct of alkylene (2-4 carbon atoms) oxide, trimellitic acid monohydroxy Ethyl (meth)acrylate, monohydroxy trimellitate n-propyl (meth)acrylate, monohydroxy trimellitate isopropyl (meth)acrylate, monohydroxy trimellitate n-butyl (meth)acrylate, monohydroxy trimellitate Isobutyl (meth)acrylate, monohydroxy-n-hexyl (meth)acrylate trimellitate, monohydroxy-n-octyl (meth)acrylate trimellitate, monohydroxy-n-decyl (meth)acrylate trimellitate, trimellitate Monoesterified product of acid and hydroxyalkyl (2-10 carbon atoms) (meth)acrylate with 1-10 mole adduct of alkylene (2-4 carbon atoms) oxide, pyromellitic acid monohydroxyethyl (meth)acrylate, pyromellitic acid mono Hydroxy-n-propyl (meth)acrylate, pyromellitic acid monohydroxyisopropyl (meth)acrylate, pyromellitic acid monohydroxy-n-butyl (meth)acrylate, pyromellitic acid monohydroxyisobutyl (meth)acrylate, pyromellitic acid monohydroxy-n- Hexyl (meth)acrylate, pyromellitic acid monohydroxy-n-octyl (meth)acrylate, pyromellitic acid monohydroxy-n-decyl (meth)acrylate, alkylene of pyromellitic acid and hydroxyalkyl (2-10 carbon atoms) (meth)acrylate Monoesterified product with 1 to 10 mole adduct of (2 to 4 carbon atoms) oxide, benzenepentacarboxylic acid monohydroxyethyl (meth)acrylate, benzenepentacarboxylic acid monohydroxy-n-propyl (meth)acrylate, benzenepentacarboxylic acid Acid monohydroxyisopropyl (meth)acrylate, benzenepentacarboxylic acid monohydroxy-n-butyl (meth)acrylate, benzenepentacarboxylic acid monohydroxyisobutyl (meth)acrylate, benzenepentacarboxylic acid monohydroxy-n-hexyl (meth)acrylate , benzenepentacarboxylic acid monohydroxy-n-octyl (meth)acrylate, benzenepentacarboxylic acid monohydroxy-n-decyl (meth)acrylate, benzenepentacarboxylic acid and hydroxyalkyl (2-10 carbon atoms) (meth)acrylate Monoesterified product with 1-10 mole adduct of alkylene (2-4 carbon atoms) oxide, monohydroxyethyl (meth)acrylate mellitic acid, monohydroxy-n-propyl (meth)acrylate mellitic acid, monohydroxyisopropyl mellitic acid ( meth)acrylate, monohydroxy-n-butyl mellitic acid (meth)acrylate, monohydroxyisobutyl mellitic acid (meth)acrylate, monohydroxy-n-hexyl mellitic acid (meth)acrylate, monohydroxy-n-octyl mellitic acid (meth)acrylate ) acrylate, mellitic acid monohydroxy-n-decyl (meth)acrylate, mellitic acid and hydroxyalkyl (carbon number 2 to 10) (meth)acrylate with alkylene (carbon number 2 to 4) oxide 1 to 10 mole adduct Examples include monoesterified products.

The monomer (h2) is, for example, an aromatic polyvalent (di- to hexavalent) carboxylic acid (e.g., phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, trimesic acid, merophonic acid, prenitic acid) , pyromellitic acid, mellitic acid, etc.) or their anhydrides or lower alkyl (carbon numbers 1 to 4) esters and hydroxyalkyl (carbon numbers 1 to 10) (meth)acrylates or hydroxyalkyl (carbon numbers 1 to 10) ( It can be obtained by monoesterifying meth)acrylate with an adduct of 1 to 10 moles of alkylene (having 2 to 4 carbon atoms) oxide. In addition, aromatic polyvalent (2-6-valent) carboxylic acids or their anhydrides or lower alkyl (1-4 carbon atoms) esters and hydroxyalkyl (1-10 carbon atoms) (meth)acrylamides or hydroxyalkyl (1-10 carbon atoms) 1 to 10) It can be obtained by monoesterifying (meth)acrylamide with a 1 to 10 mole adduct of alkylene (carbon number 2 to 4) oxide.
In addition, as the monomer (h2), mono(2-methacryloyloxyethyl) phthalate (manufactured by Tokyo Chemical Industry Co., Ltd.), mono(2-acryloyloxyethyl) phthalate (product name "HOA-MPL (N)") ”, manufactured by Kyoeisha Chemical Co., Ltd.), etc. are commercially available.

Monomer (h3) is a monomer having 1 to 5 carboxyl groups represented by the above general formula (6).
R ¹⁶ in general formula (6) is a hydrogen atom or a methyl group, and among these, both a hydrogen atom and a methyl group are preferred from the viewpoint of reducing friction.

-X ⁶ - in general formula (6) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of reducing friction.

R ¹⁷ in general formula (6) is an alkylene group having 1 to 10 carbon atoms.
Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, isopropylene group, 1,2- or 1,3-propylene group, isobutylene group, 1,2-, 1,3- or 1,4- Butylene group, isopentylene group, 1,2-, 1,3-, 1,4- or 1,5-pentylene group, isohexylene group, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexylene group, isoheptylene group, 1,2-, 1,3-, 1,4-, 1,5-, 1,6- or 1,7-heptylene group, isooctylene, 1,8-octylene group, isononylene group, 1,9-nonylene group, isodecylene group, and 1,10-decylene group.
Among these, from the viewpoint of reducing friction, ethylene groups, 1,2-propylene groups and 1,3-propylene groups are preferred, and ethylene groups are more preferred.

R ¹⁸ O in general formula (6) is an alkyleneoxy group having 2 to 4 carbon atoms. Examples of the alkyleneoxy group having 2 to 4 carbon atoms include ethyleneoxy group, propyleneoxy group and butyleneoxy group. Examples of the propylene group in the propyleneoxy group include 1,2-propylene group and 1,3-propylene group, and examples of the butylene group in the butyleneoxy group include 1,2-butylene group, 1,3-butylene group, and 1,2-propylene group. , 4-butylene group, etc. From the viewpoint of reducing friction, the alkyleneoxy group is preferably an ethyleneoxy group or a propyleneoxy group, and more preferably an ethyleneoxy group.

In the general formula (6), r is an integer of 0 to 10, preferably an integer of 0 to 7, more preferably an integer of 0 to 5, particularly preferably an integer of 0 to 3 from the viewpoint of reducing friction.
When r is 2 or more, a plurality of R ¹⁸ O's may be the same or different.

R ¹⁹ in general formula (6) is each independently a hydrogen atom or a carboxyl group, at least one of which is a carboxyl group, and from the viewpoint of reducing friction, preferably 1 to 5 carboxyl groups. The number of carboxyl groups is more preferably 1 to 4, particularly preferably 1 to 3.

Specific examples of the monomer (h3) include hexahydrophthalate monohydroxyethyl (meth)acrylate, hexahydrophthalate monohydroxy-n-propyl (meth)acrylate, and hexahydrophthalate monohydroxyisopropyl (meth)acrylate. , hexahydrophthalic acid monohydroxy-n-butyl (meth)acrylate, hexahydrophthalic acid monohydroxy-isobutyl (meth)acrylate, hexahydrophthalic acid monohydroxy-n-hexyl (meth)acrylate, hexahydrophthalic acid monohydroxy- n-octyl (meth)acrylate, monohydroxy-n-decyl (meth)acrylate hexahydrophthalate, alkylene (2-4 carbon atoms) of hexahydrophthalic acid and hydroxyalkyl (1-10 carbon atoms) (meth)acrylate Monoesterified product with 1 to 10 mole oxide adduct, 1,2,4-cyclohexanetricarboxylic acid monohydroxyethyl (meth)acrylate, 1,2,4-cyclohexanetricarboxylic acid monohydroxy-n-propyl (meth)acrylate, 1,2,4-Cyclohexanetricarboxylic acid monohydroxyisopropyl (meth)acrylate, 1,2,4-cyclohexanetricarboxylic acid monohydroxy-n-butyl (meth)acrylate, 1,2,4-cyclohexanetricarboxylic acid monohydroxyisobutyl ( meth)acrylate, 1,2,4-cyclohexanetricarboxylic acid monohydroxy-n-hexyl (meth)acrylate, 1,2,4-cyclohexanetricarboxylic acid monohydroxy-n-octyl (meth)acrylate, 1,2,4- Cyclohexanetricarboxylic acid monohydroxy-n-decyl (meth)acrylate, alkylene (carbon number 2-4) oxide of 1,2,4-cyclohexanetricarboxylic acid and hydroxyalkyl (carbon number 1-10) (meth)acrylate 1-10 Monoesterified products with molar adducts, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxyethyl (meth)acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxy-n-propyl (meth)acrylate Acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxyisopropyl (meth)acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxy-n-butyl (meth)acrylate, 1,2,4 , 5-cyclohexanetetracarboxylic acid monohydroxyisobutyl (meth)acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxy-n-hexyl (meth)acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid Monohydroxy-n-octyl (meth)acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxy-n-decyl (meth)acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid and hydroxyalkyl ( Monoesterified product of (meth)acrylate (having 1 to 10 carbon atoms) with 1 to 10 mole adduct of alkylene (having 2 to 4 carbon atoms) oxide, monohydroxyethyl 1,2,3,4,5-cyclohexanepentacarboxylate ( meth)acrylate, 1,2,3,4,5-cyclohexanepentacarboxylic acid monohydroxy-n-propyl (meth)acrylate, 1,2,3,4,5-cyclohexanepentacarboxylic acid monohydroxyisopropyl (meth)acrylate , 1,2,3,4,5-cyclohexanepentacarboxylic acid monohydroxy-n-butyl (meth)acrylate, 1,2,3,4,5-cyclohexanepentacarboxylic acid monohydroxyisobutyl (meth)acrylate, 1, 2,3,4,5-Cyclohexanepentacarboxylic acid monohydroxy-n-hexyl (meth)acrylate, 1,2,3,4,5-cyclohexanepentacarboxylic acid monohydroxy-n-octyl (meth)acrylate, 1, 2,3,4,5-Cyclohexanepentacarboxylic acid monohydroxy-n-decyl (meth)acrylate, 1,2,3,4,5-cyclohexanepentacarboxylic acid and hydroxyalkyl (1 to 10 carbon atoms) (meth) Monoesterified product of acrylate with 1 to 10 mole adduct of alkylene (carbon number 2 to 4) oxide, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxyethyl (meth)acrylate, 1,2 , 3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n-propyl (meth)acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxyisopropyl (meth)acrylate, 1, 2,3,4,5,6-Cyclohexanehexacarboxylic acid monohydroxy-n-butyl (meth)acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxyisobutyl (meth)acrylate, 1 , 2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n-hexyl (meth)acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n-octyl (meth)acrylate ) acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n-decyl (meth)acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid and hydroxyalkyl ( Examples include monoesters of (meth)acrylates (having 1 to 10 carbon atoms) with 1 to 10 mol adducts of alkylene (having 2 to 4 carbon atoms) oxides.

The monomer (h3) is, for example, cyclohexane polyvalent (2-6) carboxylic acid (for example, 1,2-cyclohexanedicarboxylic acid (also described as hexahydrophthalic acid), 1,3-cyclohexanedicarboxylic acid, 1 , 4-cyclohexanedicarboxylic acid, 1,2,3-cyclohexanetricarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, 1,2,3,4-cyclohexanetetracarboxylic acid, 1,2,4,5-cyclohexanetetracarboxylic acid, 1,2,3,5-cyclohexanetetracarboxylic acid, 1,2,3,4,5-cyclohexanepentacarboxylic acid, 1,2,3,4,5 , 6-cyclohexanehexacarboxylic acid, etc.) or their anhydrides or lower alkyl (1 to 4 carbon atoms) esters and hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylates or hydroxyalkyl (1 to 10 carbon atoms) ( It can be obtained by monoesterifying meth)acrylate with an adduct of 1 to 10 moles of alkylene (having 2 to 4 carbon atoms) oxide. In addition, polyhydric cyclohexane or anhydrides thereof or lower alkyl (1 to 4 carbon atoms) esters and hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylamides or hydroxyalkyl (1 to 10 carbon atoms) (meth)acrylamides may be used. It can be obtained by monoesterification with an adduct of 1 to 10 moles of alkylene (carbon number 2 to 4) oxide.
In addition, as the monomer (h3), mono(2-methacryloyloxyethyl) hexahydrophthalate (manufactured by Tokyo Chemical Industry Co., Ltd.), mono(2-acryloyloxyethyl) hexahydrophthalate (product name: "Light Acrylate") HOA-HH(N)'' (manufactured by Kyoeisha Kagaku Co., Ltd.) and the like are commercially available.

The weight ratio of the monomer (a) constituting the (co)polymer (A) is preferably 1 to 70% by weight, more preferably 1 to 70% by weight, based on the weight of (A) from the viewpoint of reducing friction. 60% by weight, next more preferably 1 to 50% by weight, particularly preferably 1 to 40% by weight, and most preferably 1 to 35% by weight.
The weight ratio of monomer (b) constituting (A) is preferably 30 to 99% by weight, more preferably 40 to 99% by weight, based on the weight of (A), from the viewpoint of friction reduction and base oil solubility. 99% by weight, next more preferably 50 to 99% by weight, particularly preferably 60 to 99% by weight, and most preferably 60 to 98% by weight.
From the viewpoint of reducing friction, the weight proportion of monomer (c) constituting (A) is preferably 50% by weight or less, more preferably 45% by weight or less, particularly Preferably it is 1 to 39% by weight.
From the viewpoint of reducing friction, the weight proportion of monomer (d) constituting (A) is preferably 20% by weight or less, more preferably 15% by weight or less, particularly Preferably it is 1 to 10% by weight.
From the viewpoint of reducing friction, the weight proportion of monomer (e) constituting (A) is preferably 15% by weight or less, more preferably 10% by weight or less, particularly Preferably it is 1 to 5% by weight.
From the viewpoint of reducing friction, the weight proportion of monomer (f) constituting (A) is preferably 15% by weight or less, more preferably 10% by weight or less, particularly Preferably it is 1 to 5% by weight.
From the viewpoint of reducing friction, the weight proportion of the monomer (g) constituting (A) is preferably 15% by weight or less, more preferably 10% by weight or less, particularly Preferably it is 1 to 5% by weight.
From the viewpoint of reducing friction, the weight proportion of monomer (h) constituting (A) is preferably 20% by weight or less, more preferably 15% by weight or less, particularly Preferably it is 1 to 10% by weight.
The molar fraction of monomer (a) constituting (co)polymer (A) is 1 to 40 mol based on the total number of moles of monomers constituting (A) from the viewpoint of reducing friction. %, more preferably 3 to 30 mol %, particularly preferably 5 to 20 mol %.

The solubility parameter (hereinafter abbreviated as SP value) of the (co)polymer (A) is preferably 8.5 to 11.5 (cal/cm ³ ) ^1/2 , and more preferably from the viewpoint of reducing friction. is 8.7 to 11.0 (cal/cm ³ ) ^1/2 , more preferably 8.8 to 10.5 (cal/cm ³ ) ^1/2 , particularly preferably 9.0 to 10.2. (cal/cm ³ ) ^1/2 .
Note that the SP value in the present invention is a value calculated by the method described in the Fedors method (Polymer Engineering and Science, February, 1974, Vol. 14, No. 2P. 147 to 154).

In the case of a (co)polymer consisting of two or more types of monomers, the SP value of (A) is determined by calculating the SP value of each monomer constituting (A) using the method described above, It is a value obtained by averaging the SP values of the mer based on the molar fraction of the constituent monomer units. The SP value of (A) can be adjusted to 8.5 to 11.5 (cal/cm ³ ) ^1/2 by appropriately adjusting the SP value and molar fraction of the monomers used.

The weight average molecular weight (hereinafter abbreviated as Mw) of (A) is preferably 3,000 to 2,000,000, more preferably 5,000 to 1,000,000 from the viewpoint of reducing friction. It is particularly preferably from 10,000 to 600,000, most preferably from 15,000 to 500,000. The Mw of the (co)polymer (A) can be measured by gel permeation chromatography (hereinafter sometimes abbreviated as GPC) under the following conditions.
<Measurement conditions for Mw of (co)polymer (A)>
Device: “HLC-802A” [manufactured by Tosoh Corporation]
Column: 2 “TSK gel GMH6” [manufactured by Tosoh Corporation] Measurement temperature: 40°C
Sample solution: 0.5% by weight tetrahydrofuran solution Solution injection volume: 200μl
Detection device: Refractive index detector Reference material: Standard polystyrene (TSK standard POLYSTYRENE)
12 points (molecular weight: 500, 1,050, 2,800, 5,970, 9,100, 18,100, 37,900, 96,400, 190,000, 355,000, 1,090,000, 2 , 890,000) [manufactured by Tosoh Corporation]

(A) can be obtained by a known production method, specifically a method in which the above-mentioned monomers are solution-polymerized in a solvent in the presence of a polymerization catalyst.
Examples of the solvent include toluene, xylene, alkylbenzene having 9 to 10 carbon atoms, methyl ethyl ketone, ethyl acetate, 2-propanol, mineral oil, synthetic oil, and the like.
Examples of polymerization catalysts include azo catalysts (azobisisobutyronitrile and azobisvaleronitrile, etc.), peroxide catalysts (benzoyl peroxide, cumyl peroxide, lauryl peroxide, etc.), and redox catalysts (benzoyl peroxide, etc.). and tertiary amine). Furthermore, if necessary, a known chain transfer agent (such as an alkyl mercaptan having 2 to 20 carbon atoms) may be used.
The polymerization temperature is preferably 25 to 140°C, more preferably 50 to 120°C. In addition to the solution polymerization described above, (A) can be obtained by bulk polymerization, emulsion polymerization, or suspension polymerization.
When (A) is a copolymer, the polymerization form may be either a random polymer or an alternating copolymer, or a graft copolymer or a block copolymer, but From this point of view, random polymers are preferred.

In addition to the essential (co)polymer (A), the friction modifier of the present invention may contain other commonly used known types of friction modifiers, such as molybdenum-based and zinc-based compounds. (molybdenum dithiophosphate, molybdenum dithiocarbamate, zinc dialkyl dithiophosphate), and the like.

The friction modifier of the present invention may contain base oil.
Base oils include mineral oils (solvent refined oils, paraffin oils, high viscosity index oils containing isoparaffins, high viscosity index oils obtained by hydrogenolysis of isoparaffins, naphthenic oils, etc.), synthetic lubricating oils [hydrocarbon-based synthetic lubricating oils] (poly-α-olefin-based synthetic lubricating oil, GTL base oil, etc.) and ester-based synthetic lubricating oil, etc.] and mixtures thereof. Among these, preferred are mineral oil, polyα-olefin synthetic lubricating oil, GTL base oil, and ester oil.

The kinematic viscosity (measured according to JIS-K2283) at 100° C. of the base oil is preferably 1 to 15 mm ² /s, more preferably 2 to 8 mm ² /s from the viewpoint of reducing friction.
The viscosity index (measured according to JIS-K2283) of the base oil is preferably 90 or more, more preferably 100 or more from the viewpoint of improving the viscosity index.

The cloud point (measured according to JIS-K2269) of the base oil is preferably -5°C or lower, more preferably -15°C or lower. When the cloud point of the base oil is within this range, the lubricating oil composition has good low-temperature viscosity.

The SP value of the base oil is preferably 7.0 to 11.0 (cal/cm ³ ) ^1/2 , more preferably 7.5 to 10.5 (cal/cm ³ ) ^1/2 , particularly preferably is 8.0 to 10.0 (cal/cm ³ ) ^1/2 , most preferably 8.0 to 9.8 (cal/cm ³ ) ^1/2 .

The absolute value of the difference between the SP value of the (co)polymer (A) and the SP value of the base oil is preferably 0.5 to 3.0 (cal/cm ³ ) ^1/ from the viewpoint of friction reduction and solubility. ² , more preferably 0.6 to 2.5 (cal/cm ³ ) ^1/2 , particularly preferably 0.6 to 2.1 (cal/cm ³ ) ^1/2 , most preferably 0 .7 to 1.9 (cal/cm ³ ) ^1/2 .
When the absolute value of the difference is less than 0.5 (cal/cm ³ ) ^1/2 or more, the friction reduction effect is high, and when it is 3.0 (cal/cm ³ ) ^1/2 or less, the base oil of (A) has good solubility in

The content of the (co)polymer (A) in the friction modifier is preferably 10 to 99% by weight from the viewpoint of ease of manufacturing the lubricating oil composition.

The lubricating oil composition of the present invention comprises the friction modifier of the present invention, a viscosity index improver, a detergent, a dispersant, an antioxidant, an oiliness improver, an extreme pressure agent, an antifoaming agent, a demulsifier, and a corrosion inhibitor. and at least one additive selected from the group consisting of pour point effect agents.
The weight proportion of the friction modifier in the lubricating oil composition of the present invention is preferably 0.1 to 30% by weight, more preferably 0.1 to 30% by weight, based on the weight of the lubricating oil composition, from the viewpoint of friction reduction effect. The amount is 2 to 20% by weight, particularly preferably 0.5 to 10% by weight.
The weight proportion of the (co)polymer (A) in the lubricating oil composition of the present invention is preferably 0.05 to 15% by weight based on the weight of the lubricating oil composition from the viewpoint of friction reduction effect, More preferably 0.1 to 10% by weight, particularly preferably 0.2 to 7% by weight.

The lubricating oil composition of the present invention includes gear oil (differential oil, industrial gear oil, etc.), MTF, transmission oil [ATF and belt-CVTF, etc.], traction oil (toroidal-CVTF, etc.), shock absorber oil, power steering oil, etc. Suitable for use in oil, hydraulic oil (hydraulic oil for construction machinery, industrial hydraulic oil, etc.), engine oil, etc. Preferable among these are gear oil, MTF, transmission oil, traction oil, and engine oil, more preferable are differential oil, MTF, ATF, belt-CVTF, and engine oil, and particularly preferable are MTF, ATF, and engine oil. , belt-CVTF and engine oil.

In the lubricating oil composition of the present invention, the viscosity index improver, detergent, dispersant, antioxidant, oiliness improver, extreme pressure agent, antifoaming agent, demulsifier, corrosion inhibitor, and pour point effect agent include: These include:
(1) Viscosity index improver:
(C1-7) alkyl (meth)acrylate / (C8-40) linear or branched alkyl (meth)acrylate copolymer, dispersion monomer (amine monomer etc.) / (C1-7) alkyl (meth)acrylate / (C8 ~40) Straight chain or branched alkyl (meth)acrylate copolymer, hydroxy group-containing monomer/(C1-7) alkyl (meth)acrylate/(C8-40) straight chain or branched alkyl (meth)acrylate copolymer, Comb-shaped polymer [(C1-7) alkyl (meth)acrylate/(C8-40) linear or branched alkyl (meth)acrylate/polyolefin macromonomer], ethylene/(C1-18) alkyl (meth)acrylate copolymer, Polyisobutylene, polyalkylstyrene, ethylene/propylene copolymer, styrene/maleic acid ester copolymer, styrene/isoprene hydrogenated copolymer, etc.;
(2) Cleaning agent:
Basic, overbased or neutral metal salts [overbased or alkaline earth metal salts of sulfonates (petroleum sulfonates, alkylbenzene sulfonates, alkylnaphthalene sulfonates, etc.)], salicylates, phenates, naphthenates carbonates, phosphonates and mixtures thereof;
(3) Dispersant:
Succinimides (bis- or mono-polybutenyl succinimides), Mannich condensates, borates, etc.;
(4) Antioxidant:
Hindered phenols and aromatic secondary amines, etc.;
(5) Oiliness improver:
Long chain fatty acids and their esters (oleic acid and oleic esters, etc.), long chain amines and amides thereof (oleylamine, oleylamide, etc.);
(6) Extreme pressure agent:
Sulfur compounds (mono- or disulfide, sulfoxide and sulfur phosphide compounds), phosphide compounds and chlorine compounds (chlorinated paraffins, etc.);
(7) Antifoaming agent:
Silicone oil, metal soap, fatty acid ester, phosphate compound, etc.;
(8) Demulsifier:
Quaternary ammonium salts (tetraalkylammonium salts, etc.), sulfated oils and phosphates (phosphates of polyoxyethylene-containing nonionic surfactants, etc.), etc.;
(9) Corrosion inhibitor:
Nitrogen atom-containing compounds (benzotriazole and 1,3,4-thiodiazolyl-2,5-bisdialkyldithiocarbamate, etc.);
(10) Pour point effect agent:
Polyalkyl methacrylate, polyalkyl acrylate, polyalkyl styrene, polyvinyl acetate, etc.

The total weight proportion of the additives is preferably 5 to 40% by weight, more preferably 7 to 35% by weight, particularly preferably 10 to 30% by weight, based on the weight of the lubricating oil composition. .

EXAMPLES Hereinafter, the present invention will be explained in detail with reference to Examples, but the present invention is not limited thereto.

<Examples 1 to 5, Comparative Examples 1 to 7>
185 parts by weight of ethyl acetate, 100 parts by weight of the monomer mixture listed in Table 1, and 2,2'-azobis(2,4 - 0.5 parts by weight of 2,2'-azobis(2-methylbutyronitrile) and 0.2 parts by weight of 2,2'-azobis(2-methylbutyronitrile) were added, and after nitrogen substitution (gas phase oxygen concentration 100 ppm), the mixture was sealed. The temperature was raised to 76° C. while stirring, and the polymerization reaction was carried out at the same temperature for 7 hours.
Add 100 parts by weight of mineral oil [SP value: 8.3 (cal/cm ³ ) ^1/2 , kinematic viscosity at 100°C: 4.2 mm ² /s, viscosity index: 122] and raise the temperature to 120 to 130°C. After that, unreacted monomers and ethyl acetate were removed at the same temperature under reduced pressure (0.027 to 0.040 MPa) over a period of 2 hours to obtain polymers (A-1) to (A-5) of the present invention, and friction modifiers (R-1) to (R-5) and (R'-1) to (R'-7) containing polymers (A'-1) to (A'-7) for comparison. ) was obtained.

The monomers listed in Table 1 are as described below.
(a-1): β-carboxyethyl acrylate (“β-CEA” manufactured by Daicel Allnex Corporation) (R ¹ in general formula (1) is a hydrogen atom, X ¹ is -O-, R ² is an ethylene group, s is 1)
(a-2): ω-carboxypolycaprolactone (addition of 2 moles of caprolactone) monoacrylate (“Aronix M-5300” manufactured by Toagosei Co., Ltd.) (R ¹ in general formula (1) is a hydrogen atom, X ¹ is -O -, R ² is a pentylene group, s is 2)
(b-1): 2-ethylhexyl acrylate (b-2): n-dodecyl acrylate (b-3): n-dodecyl methacrylate (b-4): Linear branched alcohol mixture with 12 to 13 carbon atoms ("Neodor 23" manufactured by Shell Chemicals) and an ester of acrylic acid.
(b-5): An esterified product of a linear branched alcohol mixture having 12 to 13 carbon atoms ("Neodol 23" manufactured by Shell Chemicals) and methacrylic acid.
(b-6): An esterified product of acrylic acid with a linear branched alcohol mixture having 14 to 15 carbon atoms ("Neodol 45" manufactured by Shell Chemicals).
(b-7): An esterified product of a linear branched alcohol mixture having 14 to 15 carbon atoms ("Neodol 45" manufactured by Shell Chemicals) and methacrylic acid.
(b-8): 70/30 weight ratio mixture of n-hexadecyl acrylate and n-octadecyl acrylate (b-9): 2-decyltetradecyl acrylate (b-10): 2-decyltetradecyl methacrylate (b-11): A 50/50 weight ratio mixture of 2-dodecylhexadecyl acrylate and 2-tetradecyloctadecyl acrylate (b-12): A mixture of 2-dodecylhexadecyl methacrylate and 2-tetradecyloctadecyl methacrylate. 50/50 weight ratio mixture (c-1): 5 mol caprolactone adduct of 2-hydroxyethyl methacrylate (“Plaxel FM5” manufactured by Daicel)
(c-2): 10 mole caprolactone adduct of 2-hydroxyethyl acrylate (“Plaxel FA10L” manufactured by Daicel)
(d-1): Methyl methacrylate (d-2): n-butyl acrylate (d-3): n-butyl methacrylate (e-1): N,N-dimethylaminoethyl methacrylate (f-1) : 2-Hydroxyethyl acrylate (f-2): 2-hydroxyethyl methacrylate (i-1): Acrylamidohexanoic acid (i-2): Methacrylamide dodecanoic acid

Table 1 shows the SP value and weight average molecular weight (Mw) of the copolymer (A).

<Examples 6 to 10 and Comparative Examples 8 to 14>
In a stainless steel container equipped with a stirring device, 10 parts by weight of an engine oil additive package (manufactured by Infinium) and mineral oil [SP value: 8.3 (cal/cm ³ ) ^1/2 , kinematic viscosity at 100°C] : 4.2 mm ² /s, viscosity index: 122] 90 parts by weight, and friction modifiers (R-1) to (R-5) or comparison samples (R'-1) to (R'-7) were added so that the content of copolymer (A) or (A') was 1% by weight, and the resulting lubricating oil composition had an HTHS viscosity of 2.60±0.05 at 150°C. (mm ² /s), a viscosity index improver (polyalkyl methacrylate, Mw 500,000, resin content 21% by weight) was added and mixed, and lubricating oil compositions (V-1) to (V-5 ), and lubricating oil compositions (V'-1) to (V'-7) were obtained.
The HTHS viscosity at this time was measured at 150° C. according to the method of ASTM D 5481.
The engine oil additive package used includes a metal detergent (calcium sulfonate), an ashless dispersant (succinimide), an anti-wear agent (phosphoric acid), an antioxidant (diphenylamine), and a metal non-containing agent. Contains activator (thiadiazole), sulfur additive (sulfurized ester), etc.

The lubricating oil compositions (V-1) to (V-5) and (V'-1) to (V'-7) were tested at 40°C, 60°C and 80°C as conditions in the low to medium temperature range. Friction evaluation was measured by the following method. The results are shown in Tables 2 and 3.
<Rolling friction characteristics - MTM (friction coefficient)>
Equipment: PCS Instruments MTM-2
Disc: MTM polished disc (standard) (0.01micron)
Ball: Drilled 3/4 AISI52100 precision steel ball
Speed: 10mm/s ~ 3,000mm/s
Temperature: 40℃, 60℃, 80℃
Sliding/rolling ratio: 50%
Load: 30N
A Stribeck curve was obtained as a result of the friction evaluation, and the friction coefficients at speeds of 10 mm/s, 100 mm/s, and 1,000 mm/s at each temperature were used as the measurement results.

<Sliding friction characteristics - HFRR (coefficient of friction)>
High-Frequency-Reciprocating-Rig (HFRR P
(manufactured by CS Instruments), the material of the test steel ball was SUJ2, the diameter of the test steel ball was 6 mm, and the material of the test disk was SUJ2. Load 3.92N (400g), stroke 1000μ
The test was conducted at a frequency of 20 Hz and a test time of 60 minutes, and the coefficient of friction was measured.

As is clear from the results in Tables 2 and 3, a lubricating oil composition containing a friction modifier containing a (co)polymer (A) containing the monomer (a) of the present invention as a constituent monomer. The products (Examples 6 to 10) are the same as those of Comparative Examples 8 to 12, which have almost the same SP value and Mw except that the monomer (f) having a hydroxyl group is used instead of the monomer (a). Comparison with lubricating oil compositions (Comparison of Example 6 and Comparative Example 8, Comparison of Example 7 and Comparative Example 9, Comparison of Example 8 and Comparative Example 10, Comparison of Example 9 and Comparative Example 11) , Comparison of Example 10 and Comparative Example 12), Examples 6 to 10, which are the lubricating oil compositions of the present invention, have better properties at 40°C, 60°C, and 80°C in both rolling friction properties and sliding friction properties. It can be seen that the friction reduction effect is high at all temperatures.
In addition, a comparative example in which the SP value and Mw are almost the same except that (meth)acrylamide (i) having a carboxyalkyl group (-X ¹ - in general formula (1) is -NH-) is used. Comparisons with lubricating oil compositions Nos. 13 and 14 (comparison between Example 6 and Comparative Example 13, and comparison between Example 8 and Comparative Example 14) show that although the sliding friction properties are at the same level, the rolling friction properties are It can be seen that Examples 6 and 8 of the present invention have a higher friction reduction effect at all temperatures of 40°C, 60°C and 80°C.

The lubricating oil composition containing the friction modifier of the present invention can be used in drive system lubricating oils (MTF, differential gear oil, ATF, belt-CVTF, etc.), hydraulic oils (machine hydraulic oil, power steering oil, shock absorber oil, etc.). oil, etc.), engine oil (for gasoline, diesel, etc.), and traction oil.

Claims (7)

A friction modifier comprising a (co)polymer (A) containing a monomer (a) represented by the following general formula (1) as a constituent monomer.
[R ¹ in general formula (1) is a hydrogen atom or a methyl group; -X ¹ - is a group represented by -O-; R ² represents an alkylene group having 1 to 10 carbon atoms. s is an integer from 1 to 15, and when s is 2 or more, R ² may be the same or different. ] The friction modifier according to claim 1, wherein the (co)polymer (A) is a copolymer further containing a monomer (b) represented by the following general formula (2) as a constituent monomer.
[R ³ in general formula (2) is a hydrogen atom or a methyl group; -X ² - is a group represented by -O- or -NH-; R ⁴ is a linear or branched alkyl group having 5 to 44 carbon atoms represents. ] The (co)polymer (A) contains 1 to 70% by weight of the monomer (a) based on the total weight of the monomer (a) and the monomer (b) as constituent monomers, The friction modifier according to claim 2, which is a copolymer containing 30 to 99% by weight of monomer (b). According to any one of claims 1 to 3, the (co)polymer (A) is a copolymer further comprising a monomer (c) represented by the following general formula (3) as a constituent monomer. Friction modifier as described.
[R ⁵ in general formula (3) is a hydrogen atom or a methyl group; -X ³ - is a group represented by -O- or -NH-; R ⁶ is an alkylene group having 1 to 10 carbon atoms; R ⁷ is a Represents an alkylene group having 1 to 10 carbon atoms. t is an integer from 1 to 15, and when t is 2 or more, R ⁷ may be the same or different. ] The friction modifier according to any one of claims 1 to 4, wherein the (co)polymer (A) has a weight average molecular weight of 3,000 to 2,000,000. The friction modifier according to any one of claims 1 to 5, further comprising a base oil. The friction modifier according to any one of claims 1 to 6, and a viscosity index improver, a detergent, a dispersant, an antioxidant, an oiliness improver, an extreme pressure agent, an antifoaming agent, a demulsifier, and a corrosion inhibitor. A lubricating oil composition comprising at least one additive selected from the group consisting of a pour point effect agent and a pour point effect agent.