JP2020139146A - Friction modifier and lubricant composition - Google Patents

Abstract

To provide a friction modifier which has excellent effect of reducing the friction under conditions from a low temperature range to a moderate temperature range.SOLUTION: A friction reducer contains a (co)polymer (A) comprising, as a constituent monomer, a monomer (a) represented by the specified general formula (1). [In the general formula (1), R1 represents a hydrogen atom or methyl group; -X1- is a group represented by -O-; R2 represents a C1-10 alkylene group; and s represents an integer from 1 to 15, where, if s is 2 or more, R2 can be identical to or different from each other.]SELECTED DRAWING: None

Description

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

Lubricating oils and hydraulic oils used in automobiles and the like have been reduced in viscosity in recent years in pursuit of fuel efficiency. The low viscosity reduces the frictional resistance in the fluid lubrication region and improves fuel efficiency, while wear is likely to occur under high pressure in the mixed lubrication region and boundary lubrication region, and a friction modifier is used to prevent such wear. It is common to do.
Friction modifiers that improve fuel efficiency are mainly classified into four types: oiliness improvers that form an oil film on the friction surface under low load to reduce friction and wear, and secondary compounds on the friction surface. An anti-wear agent that forms a protective film to prevent wear, an extreme pressure agent that prevents seizure and scuffing in extreme pressure lubrication conditions, and friction control that physically and chemically adsorbs to the friction surface to control the friction coefficient. It is an agent.

Currently commonly used antiwear additives are long-chain fatty acid esters and fatty acid amides as oiliness improvers, phosphate esters and zinc dithiophosphates as anti-wear agents, organic sulfur as extreme pressure agents, organic halogen compounds, and friction control agents. Examples thereof include organic molybdenum compounds.
Examples of the polymer type friction modifier include a copolymer composed of α-olefin and fumaric acid ester (Patent Document 1), an acrylic acid ester copolymer having a hydroxyl group (Patent Document 2), a hydrophilic polymer unit and a polyolefin. Polyester having a unit (Patent Document 3), a methacrylate ester copolymer having a block structure composed of a polar segment unit and a hydrophobic segment unit (Patent Document 4), and a phosphorus-functionalized methacrylate copolymer (Patent). Document 5), chain polymethacrylate polymer having a carboxyl group (Patent Document 6) and the like are known.

However, the polymer friction modifiers of Patent Documents 1 to 5 have a problem that the friction reducing effect is not yet sufficient when used under the conditions of low temperature to medium temperature. Further, the friction modifier of Patent Document 6 is effective under sliding friction conditions under low temperature conditions, but has a problem that the friction reducing effect is not sufficient under rolling friction conditions.

Japanese Patent No. 3730660 Japanese Patent No. 5822706 Japanese Patent No. 5648832 Japanese Unexamined Patent Publication No. 4686444 Special Table 2014-518925 Japanese Unexamined Patent Publication No. 2016-210941

An object of the present invention is a friction modifier having an excellent effect of reducing sliding friction and rolling friction even when used under conditions of a low temperature range to a medium temperature range of about 40 to 80 ° C.; a lubricating oil containing a friction modifier. To provide the 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 have arrived at the present invention as a result of studies for achieving the above object.
That is, the present invention is a friction modifier containing a (co) polymer (A) containing a monomer (a) represented by the following general formula (1) as a constituent monomer; and the friction modifier. At least one selected from the group consisting of agents, viscosity index improvers, detergents, dispersants, antioxidants, oiliness improvers, extreme pressure agents, defoamers, anti-emulsifiers, corrosion inhibitors and pour point effectors. It is a lubricating oil composition containing the additive of.

[R ¹ in the 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 of 1 to 15, and R ² when s is 2 or more may be the same or different. ]

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

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.
The friction modifier of the present invention contains the (co) polymer (A) containing the monomer (a) as a constituent monomer, and thus has a strong ability to adsorb carboxyl groups to the metal surface, thereby causing conventional friction. It is presumed that the effect of reducing friction (sliding friction and rolling friction) under the conditions of low temperature to medium temperature can be achieved more than that of the modifier.

[R ¹ in the 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 of 1 to 15, and R ² when s is 2 or more may be the same or different. ]

Among the constituent monomers of the (co) polymer (A) contained in the friction modifier of the present invention, the 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 the} general formula (1) is a group represented by -O-.
In the present invention, since -X ^1- is a group represented by -O-instead of -NH-, adsorption to the metal surface and formation of an oil film are promoted in the boundary lubrication region where metals are remarkably likely to come into contact with each other. , It is presumed that friction reduction can be achieved.

R ² in the 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group and a 1,10-decylene group. Of these, from the viewpoint of reducing friction, an alkylene group having 1 to 8 carbon atoms is preferable, an alkylene group having 2 to 6 carbon atoms is more preferable, and an alkylene group having 2 to 5 carbon atoms is particularly preferable.

In the 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, and 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 the monomer (a) include carboxypolyacetlactone mono (meth) acrylate (adding 1 to 15 mol of α-acetlactone) and carboxypolypropiolactone mono (meth) acrylate (β-propiolactone). 1 to 15 mol addition), carboxypolybutyrolactone mono (meth) acrylate (1 to 15 mol addition of γ-butyrolactone), carboxypolyvalerolactone mono (meth) acrylate (addition 1 to 15 mol of δ-valerolactone), carboxy Examples thereof include polycaprolactone mono (meth) acrylate (adding 1 to 15 mol of ε-caprolactone).

The 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.) can be obtained by reaction with (meth) acrylic acid.
As the monomer (a), β-carboxyethyl acrylate (product name “β-CEA”, manufactured by Daicel Ornex Co., Ltd.) ω-carboxy-polycaprolactone (2 mol adduct) monoacrylate (product name “” Aronix M-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 the base oil and reduction of friction. It is preferably a monomer.

[R ³ in the 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 the general formula (2) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of friction reduction.

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, 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, 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-tetricosyl group, 2-decyltetradecyl group, 2-dodecylpentadecyl group, 2-heptyl icosyl group, 2-dodecylhexadecyl group, n-triacontyl group, 2 -Tetradecyl octadecyl group, n-hexatriacontyl group, n-tetracontyl group, 2-ethyltetracontyl group and polyolefin [eg propylene oligomer (2-14 mer), ethylene / propylene oligomer (2-20 mer) ) And isobutene oligomers (2-10 mer), etc.], and residues obtained by removing the hydroxyl group from the oxoalcohol obtained from the above.

Among R ^4, in view of compatibility and friction reducing effect of the base oil (A), preferred are alkyl groups of straight or branched carbon atoms from 8 to 34, more preferably is a linear or branched Alkyl groups having 8 to 32 carbon atoms are particularly preferable, linear or branched alkyl groups having 10 to 32 carbon atoms are most preferable, and linear alkyl groups having 10 to 22 carbon atoms and 12 carbon atoms are most preferable. ~ 32 branched alkyl groups.

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

[R ⁵ in the 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. Represents an alkylene group having 1 to 10 carbon atoms. t is an integer of 1 to 15, and when t is 2 or more, R ⁷ may be the same or different. ]

R ⁵ in the general formula (3) 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 ^3- in the general formula (3) is a group represented by -O- or -NH-, and among these, -O- is preferable from the viewpoint of friction reduction.

R ⁶ in the 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group and a 1,10-decylene group. Of these, from the viewpoint of reducing friction, an alkylene group having 1 to 8 carbon atoms is preferable, an alkylene group having 2 to 6 carbon atoms is more preferable, and an alkylene group having 2 to 5 carbon atoms is particularly preferable.

R ⁷ in the 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group and a 1,10-decylene group. Of these, from the viewpoint of reducing friction, an alkylene group having 1 to 8 carbon atoms is preferable, an alkylene group having 2 to 6 carbon atoms is more preferable, and an alkylene group having 2 to 5 carbon atoms is particularly preferable.

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, and particularly preferably an integer of 1 to 10 from the viewpoint of reducing friction. A plurality of R ⁷ may be the same or different.

Specific examples of the monomer (c) include α-acetlactone-modified (1 to 15 mol addition) hydroxyalkyl (1 to 10 carbon atoms) (meth) acrylate and β-propiolactone modification (1 to 15 mol addition). ) Hydroxyalkyl (1-10 carbon atoms) (meth) acrylate, γ-butylolactone modified (1 to 15 mol added) Hydroxyalkyl (1-10 carbon atoms) (meth) acrylate, δ-valerolactone modified (1 to 15 mol) Addition) Hydroxyalkyl (1-10 molar additions) (meth) Acrylate (δ-valerolactone 1-15 molar addition), ε-caprolactone modified (1-15 molar addition) hydroxyalkyl (1-10 molar additions) (meth) ) Acrylate (1 to 15 mol 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). It can be obtained by an addition reaction of −caprolactone, δ-caprolactone, γ-caprolactone, etc.) to hydroxyalkyl (1 to 10 carbon atoms) (meth) acrylate or hydroxyalkyl (1 to 10 carbon atoms) (meth) acrylamide.
Further, as the monomer (c), an ε-caprolactone adduct of hydroxyethyl methacrylate (product names “Plaxel FM1”, “Plaxel FM2D”, “Plaxel FM3”, etc., all manufactured by Daicel Corporation), hydroxyethyl acrylate. Ε-Caprolactone adduct (product names "Plaxel FA1", "Plaxel FA2D", "Plaxel FA5", "Plaxel FA10L", etc., all manufactured by Daicel Co., Ltd.) and the like are commercially available.

The (co) polymer (A) in the present invention contains an alkyl group in addition to the essential constituent monomer (a), the monomer (b) and the monomer (c) preferably used in combination. A (meth) acrylic acid alkyl ester (d) (which may be abbreviated as monomer (d) below), 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 linear 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 and the like.
Of the monomer (d), methyl (meth) acrylate, ethyl (meth) acrylate and n-butyl (meth) acrylate are preferable.

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

The nitrogen atom-containing vinyl monomer (e) includes an amide group-containing vinyl monomer (e1) such as (meth) acrylamide and monoalkylamino (meth) acrylamide; and a nitro group-containing monomer such as 4-nitrostyrene. (E2); 1st to 3rd grade amino group-containing vinyl monomer (e3) such as (meth) allylamine, methylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate; and containing nitrile group such as (meth) acrylonitrile. Vinyl monomer (e4) can be mentioned.

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 a phosphate group-containing monomer (g1) such as (meth) acryloyloxyethyl phosphate and isopropenyl phosphate; (meth) acryloyloxyethylphosphonic acid and allylphosphone. Examples thereof include a phosphono group-containing monomer (g2) such as an acid.

Examples of the carboxyl group-containing monomer (h) include (meth) acrylic acid, the monomer (h1) represented by the following general formula (4), and the monomer (h2) represented by the following general formula (5). ) And the monomer (h3) represented by the following general formula (65).

[Formula (4) ^{R 8} in the 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 Is 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 R ¹⁰ O when p is 2 or more may be the same or different. ]

[R ¹² in the 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 is an independently 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 the 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 is an independently 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. ]

The monomer (h1) is a monomer having one carboxyl group represented by the above general formula (4).
R ⁸ in the general formula (4) 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 ⁴ in the general formula (4) - is a group represented by -O- or NH-, among these, are preferred from the viewpoint of friction reduction is -O-.

R ⁹ in the 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group and a 1,10-decylene group. Of these, from the viewpoint of reducing friction, an ethylene group, a 1,2-propylene group and a 1,3-propylene group are preferable, and an ethylene group is more preferable.

R ¹⁰ O in the 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 an ethyleneoxy group, a propyleneoxy group and a butyleneoxy group. Examples of the propylene group in the propyleneoxy group include a 1,2-propylene group and a 1,3-propylene group, and examples of the butylene group in the butyleneoxy group include a 1,2-butylene group and a 1,3-butylene group. And 1,4-butylene group and the like. The alkyleneoxy group is preferably an ethyleneoxy group or a propyleneoxy group from the viewpoint of reducing friction, and more preferably an ethyleneoxy group.

P in the general formula (4) is an integer of 0 to 10, preferably an integer of 0 to 7, more preferably an integer of 0 to 5, and 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 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group, a 1,10-decylene group, a 1,11-undecylene group and a 1,12-dodecylene group. Of these, from the viewpoint of reducing friction, an alkylene group having 1 to 6 carbon atoms is preferable, and an alkylene group having 1 to 4 carbon atoms is more preferable.
Examples of the dicarboxylic acid 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 acid (1 to 10 carbon atoms). (Succinic acid having an alkyl group, etc.) and the like.

Specific examples of the monomer (h1) include a monoesterified product of hydroxyalkyl (1 to 10 carbon atoms) (meth) acrylate and dicarboxylic acid having 3 to 14 carbon atoms {for example, mono (2- (meth) malonic acid). ) Acryloyloxyethyl), mono (3- (meth) acryloyloxy-n-propyl), mono (meth) acryloyloxyisopropyl malonic acid, mono (4- (meth) acryloyloxy-n-butyl), Mono (meth) acryloyloxyisobutyl malonic acid, mono (6- (meth) acryloyloxy-n-hexyl), mono (8- (meth) acryloyloxy-n-octyl), mono (10-) malonic acid. (Meta) acryloyloxy-n-decyl), mono (meth) malonic acid acryloyloxyisodecyl, mono succinate (2- (meth) acryloyloxyethyl), mono succinate (3- (meth) acryloyloxy-n-) Propyl), mono (meth) succiloyloxyisopropyl, mono (4- (meth) acryloyloxy-n-butyl), mono (meth) acryloyloxyisobutyl succinate, mono (6- (meth) acryloyl) Oxy-n-hexyl), monosuccinate (8- (meth) acryloyloxy-n-octyl), monosuccinate (10- (meth) acryloyloxy-n-decyl), mono (meth) acryloyloxyiso Decyl, mono (2- (meth) acryloyloxyethyl), mono-glutanate (3- (meth) acryloyloxy-n-propyl), mono (meth) acryloyloxyisopropyl glutanate, mono-glutarate (4-( Meta) acryloyloxy-n-butyl), mono (meth) acryloyloxyisobutyl, mono (6- (meth) acryloyloxy-n-hexyl), mono (8- (meth) acryloyloxy-n) -Octyl), monoglutanate (10- (meth) acryloyloxy-n-decyl), mono (meth) acryloyloxyisodecyl, monoadipate (2- (meth) acryloyloxyethyl), mono (adipate) 3- (Meta) acryloyloxy-n-propyl), mono (meth) acryloyloxyisopropyl adipate, mono (4- (meth) acryloyloxy-n-butyl), mono (meth) acryloyloxyisobutyl adipate, Horse mackerel Mono pinate (6- (meth) acryloyloxy-n-hexyl), mono adipate (8- (meth) acryloyloxy-n-octyl), mono adipate (10- (meth) acryloyloxy-n-decyl) , Mono (meth) acryloyloxyisodecyl adipate, Mono (2- (meth) acryloyloxyethyl), Mono (3- (meth) acryloyloxy-n-propyl), Mono (meth) acryloyl Oxyisopropyl, mono (4- (meth) acryloyloxy-n-butyl), mono (meth) acryloyloxyisobutyl, mono (6- (meth) acryloyloxy-n-hexyl), mono-pymelicate (8- (meth) acryloyloxy-n-octyl), monopimericate (10- (meth) acryloyloxy-n-decyl), mono (meth) acryloyloxyisodecyl, mono-svericate (2- (meth) ) Acryloyloxyethyl), mono-svericate (3- (meth) acryloyloxy-n-propyl), mono-svericate (meth) acryloyloxyisopropyl, mono-svericate (4- (meth) acryloyloxy-n-butyl), Mono (meth) acryloyloxyisobutyl subericate, mono (6- (meth) acryloyloxy-n-hexyl) mono-svericate, mono (8- (meth) acryloyloxy-n-octyl) mono-svericate (10-) (Meta) acryloyloxy-n-decyl), mono-svericate (meth) acryloyloxyisodecyl, mono-acryloylate (2- (meth) acryloyloxyethyl), mono-(3- (meth) acryloyloxy-n-) Propyl), mono (meth) acryloyloxyisopropyl, mono (4- (meth) acryloyloxy-n-butyl), mono- (meth) acryloyloxyisobutyl, mono (6- (meth)) Acryloyloxy-n-hexyl), mono (8- (meth) acryloyloxy-n-octyl), mono (10- (meth) acryloyloxy-n-decyl), mono (meth) acryloyloxy Isodecyl, mono-sevacinate (2- (meth) acryloyloxyethyl), mono-sevacinate (3- (meth) acryloyloxy-n-) Propyl), mono (meth) acryloyloxyisopropyl sebacate, mono (4- (meth) acryloyloxy-n-butyl), mono (meth) acryloyloxyisobutyl sebacate, mono (6- (meth) acryloyl sebacate) Oxy-n-hexyl), mono-sevacinate (8- (meth) acryloyloxy-n-octyl), mono-sevacinate (10- (meth) acryloyloxy-n-decyl), mono-sevacinate (meth) acryloyloxyiso Decyl, mono-dodecanedioic acid (2- (meth) acryloyloxyethyl), mono-dodecanedioate (3- (meth) acryloyloxy-n-propyl), mono-dodecanedioate (meth) acryloyloxyisopropyl, mono-dodecanedioate (4- (Meta) acryloyloxy-n-butyl), mono-dodecanedioate (meth) acryloyloxyisobutyl, mono-dodecanedioate (6- (meth) acryloyloxy-n-hexyl), mono-dodecanedioate (8-) (Meta) acryloyloxy-n-octyl), dodecanedioic acid mono (10- (meth) acryloyloxy-n-decyl), dodecanedioic acid mono (meth) acryloyloxyisodecyl, etc.};
A monoester product of an alkylene (2-4 carbon atoms) oxide adduct (1-10 molar additions) of a hydroxyalkyl (1-10 carbon atoms) (meth) acrylate and a dicarboxylic acid having 3-14 carbon atoms {for example. Monoesteride of malonic acid and (meth) acryloyloxyethyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), maloic acid and (meth) acryloyloxy-n-propyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide) Monoesteride, monoesteride with malonic acid and (meth) acryloyloxyisopropyl polyethylene glycol (with 1-10 mol of ethylene oxide added), malesterate and (meth) acryloyloxy-n-butyl polyethylene glycol (ethyleneoxide 1-10) Monoesteride with (molar addition), monoesteride with malonic acid and (meth) acryloyloxyisobutyl polyethylene glycol (ethylene oxide 1-10 molar addition), succinic acid and (meth) acryloyloxyethyl polyethylene glycol (ethylene oxide 1) Monoesteride with 10 mol addition), monoesteride with succinic acid and (meth) acryloyloxy-n-propyl polyethylene glycol (with 1-10 mol addition of ethylene oxide), succinic acid and (meth) acryloyloxyisopropyl polyethylene Monoesteride with glycol (1-10 mol of ethylene oxide added), monoesteride with succinic acid and (meth) acryloyloxy-n-butyl polyethylene glycol (with 1-10 mol of ethylene oxide added), succinic acid and (meth) ) Monoesteride with acryloyloxyisobutyl polyethylene glycol (with 1-10 mol of ethylene oxide added), monoesteride with glutanoic acid and (meth) acryloyloxyethyl polyethylene glycol (with 1-10 mol of ethylene oxide added), with glutanic acid Monoester of (meth) acryloyloxy-n-propyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), monoester of glutanic acid and (meth) acryloyloxyisopropyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide) Glutane, a monoester product of glutanic acid and (meth) acryloyloxy-n-butyl polyethylene glycol (with 1 to 10 mol of ethylene oxide added) Monoesteride of acid with (meth) acryloyloxyisobutyl polyethylene glycol (with 1-10 mol of ethylene oxide added), monoesteride of adipic acid with (meth) acryloyloxyethyl polyethylene glycol (with 1-10 mol of ethylene oxide added) , Adiponic acid and meta) monoesteride with acryloyloxy-n-propyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), adiponic acid and meta) with acryloyloxyisopropylpolyethylene glycol (addition of 1 to 10 mol of ethylene oxide) Monoesteride, monoesteride with adipic acid and (meth) acryloyloxy-n-butyl polyethylene glycol (with 1-10 mol of ethylene oxide added), adipate and (meth) acryloyloxyisobutylpolyethylene glycol (ethylene oxide 1-10) Monoesteride with (molar addition), monoesteride with pimeric acid and (meth) acryloyloxyethyl polyethylene glycol (with 1 to 10 molar addition of ethylene oxide), pimeric acid and (meth) acryloyloxy-n-propyl polyethylene glycol (meta) Monoesteride with ethylene oxide 1-10 mol addition), monoesteride with pimeric acid and (meth) acryloyloxyisopropylpolyisopropyl (ethylene oxide 1-10 mol addition), pimeric acid and (meth) acryloyloxy-n − Monoesteride with butyl polyethylene glycol (with 1-10 mol of ethylene oxide), monoesteride with piceric acid and (meth) acryloyloxyisobutyl polyethylene glycol (with 1-10 mol of ethylene oxide), with Sveric acid (meth) ) Monoesteride with acryloyloxyethyl polyethylene glycol (with 1-10 mol of ethylene oxide added), monoesteride with suberic acid and (meth) acryloyloxy-n-propyl polyethylene glycol (with 1-10 mol of ethylene oxide added), Monoesteride of suberic acid and (meth) acryloyloxyisopropyl polyethylene glycol (with 1 to 10 mol of ethylene oxide added), with suberic acid and (meth) acryloyloxy-n-butyl polyethylene glycol (with 1 to 10 mol of ethylene oxide added) Monoesters, Sveric acid and (meth) acryloy Monoesteride with luoxyisobutyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), monoesteride of azelaic acid with (meth) acryloyloxyethyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), azelaic acid and ( Meta) Monoesteride with acryloyloxy-n-propyl polyethylene glycol (with 1-10 mol of ethylene oxide added), monoesteride with azelaic acid with (meth) acryloyloxyisopropylpolyethylene glycol (with 1-10 mol of ethylene oxide added) , Monoesteride of azelaic acid and (meth) acryloyloxy-n-butyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), Azelaic acid and (meth) acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide) Monoesteride with sebacic acid and (meth) acryloyloxyethyl polyethylene glycol (with 1 to 10 mol of ethylene oxide added), sebacic acid and (meth) acryloyloxy-n-propyl polyethylene glycol (ethylene oxide 1) Monoesteride with 10 mol addition), monoesteride with sebacic acid and (meth) acryloyloxyisopropylpolyethylene glycol (ethylene oxide 1-10 mol addition), sebacic acid and (meth) acryloyloxy-n-butyl polyethylene Monoesteride with glycol (addition of 1-10 mol of ethylene oxide), monoesteride with sebacic acid and (meth) acryloyloxyisobutyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), dodecanedioic acid and (meth) acryloyl Monoesteride with oxyethyl polyethylene glycol (with 1-10 mol of ethylene oxide added), monoesteride with dodecanedioic acid with (meth) acryloyloxy-n-propyl polyethylene glycol (with 1-10 mol of ethylene oxide added), dodecane Monoesterified product of diacid and (meth) acryloyloxyisopropyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide), dodecanedioic acid and (meth) acryloyloxy-n-butyl polyethylene glycol (addition of 1 to 10 mol of ethylene oxide) Monoesters with, dodecanedioic acid and (meth) acryloyloxyisobutyl Monoesterified products with polyethylene glycol (addition of 1 to 10 moles of ethylene oxide)} and the like can be mentioned.

The monomer (h1) is, for example, an alkyldicarboxylic acid having 3 to 14 carbon atoms (for example, malonic acid, succinic acid, glutaric acid, adipic acid, pimeric acid, suberic acid, azelaic acid, sebacic acid and alkyl (carbon number). 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) ) The acrylate can be obtained by monoesterification with an alkylene (2-4 carbon atoms) oxide 1-10 mol addition. 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 hydroxyalkyls (1 to 10 carbon atoms). ) (Meta) Acryrylamide can be obtained by monoesterification with an alkylene (2-4 carbon atoms) oxide 1-10 mol addition.
The monomers (h1) include monosuccinate (2-acryloyloxyethyl) (manufactured by Tokyo Chemical Industry Co., Ltd.) and monosuccinate (2-acryloyloxyethyl) (product name "HOA-MS (N)). , Kyoeisha Chemical Co., Ltd.), etc. are commercially available.

The monomer (h2) is a monomer having 1 to 5 carboxyl groups represented by the above general formula (5).
R ¹² in the general formula (5) 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 ^{5- in the} general formula (5) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of friction reduction.

R ¹³ in the 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group and a 1,10-decylene group.
Of these, from the viewpoint of reducing friction, an ethylene group, a 1,2-propylene group and a 1,3-propylene group are preferable, and an ethylene group is more preferable.

R ¹⁴ O in the 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 an ethyleneoxy group, a propyleneoxy group and a butyleneoxy group. Examples of the propylene group in the propyleneoxy group include a 1,2-propylene group and a 1,3-propylene group, and examples of the butylene group in the butyleneoxy group include a 1,2-butylene group, a 1,3-butylene group and the like. Examples include 1,4-butylene group.
The alkyleneoxy group is preferably an ethyleneoxy group or a propyleneoxy group from the viewpoint of reducing friction, and more preferably an ethyleneoxy group.

Q in the general formula (5) is an integer of 0 to 10, preferably an integer of 0 to 7, more preferably an integer of 0 to 5, and 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 may be the same or different.

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

Specific examples of the monomer (h2) include monohydroxyethyl (meth) acrylate, monohydroxy-n-propyl (meth) acrylate phthalate, monohydroxyisopropyl (meth) acrylate phthalate, and monohydroxy phthalate. n-butyl (meth) acrylate, monohydroxyisobutyl (meth) phthalate, monohydroxy-n-hexyl (meth) phthalate, monohydroxy-n-octyl (meth) phthalate, monohydroxy-n phthalate -Decil (meth) acrylate, monoesteride of phthalic acid and hydroxyalkyl (2-10 carbon atoms) (meth) acrylate alkylene (2-4 carbon atoms) oxide 1-10 mol adduct, monohydroxy trimellitic acid Ethyl (meth) acrylate, monohydroxy-n-propyl (meth) trimellitic acid acrylate, monohydroxyisopropyl (meth) trimellitic acid, monohydroxy-n-butyl (meth) trimellitic acid, monohydroxy trimellitic acid Isobutyl (meth) acrylate, monohydroxy-n-hexyl (meth) acrylate of trimellitic acid, monohydroxy-n-octyl (meth) acrylate of trimellitic acid, monohydroxy-n-decyl (meth) acrylate of trimellitic acid, trimerit Monoesteride of acid and hydroxyalkyl (2-10 carbons) (meth) acrylate alkylene (2-4 carbons) oxide 1-10 mol adduct, monohydroxyethyl (meth) acrylate, monopyromeridoate Hydroxy-n-propyl (meth) acrylate, monohydroxyisopropyl (meth) pyromerideate, monohydroxy-n-butyl (meth) pyromerideate, monohydroxyisobutyl (meth) acrylate, monohydroxy-n-pyromerideate Hexyl (meth) acrylate, monohydroxy-n-octyl (meth) acrylate of pyromeridate, monohydroxy-n-decyl (meth) acrylate of pyromeridate, alkylene of pyromeridic acid and hydroxyalkyl (2-10 carbon atoms) (meth) acrylate (2-4 carbon atoms) Monoesteride with 1-10 mol of oxide, monohydroxyethyl (meth) benzenepentacarboxylic acid, monohydroxy-n benzenepentacarboxylic acid -Propyl (meth) acrylate, benzenepentacarboxylic 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 (carbon) Numbers 2-10) Monoesters of alkylene (2-4 carbons) oxides of (meth) acrylate with 1-10 molar adducts, monohydroxyethyl (meth) acrylate, monohydroxy-n-propyl melitate (monohydroxy-n-propyl melitate) Meta) acrylate, monohydroxyisopropyl (meth) acrylate, monohydroxy-n-butyl (meth) acrylate, monohydroxyisobutyl (meth) acrylate, monohydroxy-n-hexyl (meth) acrylate, Mellitic acid monohydroxy-n-octyl (meth) acrylate, mellitic acid monohydroxy-n-decyl (meth) acrylate, mellitic acid and hydroxyalkyl (carbon number 2-10) (meth) acrylate alkylene (carbon number 2-4) ) A monoesterified product with 1 to 10 mol of oxide is mentioned.

The monomer (h2) is, for example, an aromatic polyvalent (2 to 6 valent) carboxylic acid (for example, phthalic acid, isophthalic acid, terephthalic acid, hemmellitic acid, trimellitic acid, trimesic acid, melophanic acid, planar acid , Pyromellitic acid and mellitic 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 monoesterification of a meta) acrylate with an adduct of 1-10 mol of an alkylene (2-4 carbon atoms) oxide. In addition, aromatic polyvalent (2 to 6 valent) carboxylic acids or their anhydrides or lower alkyl (1 to 4 carbon atoms) esters and hydroxyalkyl (1 to 10 carbon atoms) (meth) acrylamide or hydroxyalkyl (carbon atoms). It can be obtained by monoesterification of 1-10) (meth) acrylamide with an additive of 1-10 mol of an alkylene (2-4 carbon atoms) oxide.
The monomer (h2) includes mono (2-methacryloyloxyethyl) phthalate (manufactured by Tokyo Chemical Industry Co., Ltd.) and mono (2-acryloyloxyethyl) phthalate (product name "HOA-MPL (N)). , Kyoeisha Chemical Co., Ltd.), etc. are commercially available.

The monomer (h3) is a monomer having 1 to 5 carboxyl groups represented by the above general formula (6).
R ¹⁶ in the general formula (6) 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 ^{6- in the} general formula (6) is a group represented by -O- or NH-, and among these, -O- is preferable from the viewpoint of friction reduction.

R ¹⁷ in the 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 a methylene group, an ethylene group, an isopropylene group, a 1,2- or 1,3-propylene group, an 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 Examples thereof include a group, an isononylene group, a 1,9-nonylene group, an isodecylene group and a 1,10-decylene group.
Of these, from the viewpoint of reducing friction, an ethylene group, a 1,2-propylene group and a 1,3-propylene group are preferable, and an ethylene group is more preferable.

R ¹⁸ O in the 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 an ethyleneoxy group, a propyleneoxy group and a 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 , 4-butylene group and the like. The alkyleneoxy group is preferably an ethyleneoxy group or a propyleneoxy group from the viewpoint of reducing friction, 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, and 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 may be the same or different.

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

Specific examples of the monomer (h3) include monohydroxyethyl (meth) acrylate of hexahydrophthalate, monohydroxy-n-propyl (meth) acrylate of hexahydrophthalate, and monohydroxyisopropyl (meth) acrylate of hexahydrophthalate. , Hexahydrophthalate monohydroxy-n-butyl (meth) acrylate, hexahydrophthalate monohydroxyisobutyl (meth) acrylate, hexahydrophthalate monohydroxy-n-hexyl (meth) acrylate, hexahydrophthalate monohydroxy- n-octyl (meth) acrylate, monohydroxy-n-decyl (meth) acrylate of hexahydrophthalic acid, alkylene (2-4 carbon atoms) of hexahydrophthalic acid and hydroxyalkyl (1-10 carbon atoms) (meth) acrylate Monoesteride with 1-10 mol of oxide, monohydroxyethyl (meth) acrylate of 1,2,4-cyclohexanetricarboxylic acid, monohydroxy-n-propyl (meth) acrylate of 1,2,4-cyclohexanetricarboxylic acid, Monohydroxyisopropyl (meth) acrylate of 1,2,4-cyclohexanetricarboxylic acid, monohydroxy-n-butyl (meth) acrylate of 1,2,4-cyclohexanetricarboxylic acid, monohydroxyisobutyl 1,2,4-cyclohexanetricarboxylic acid ( Meta) 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, 1,2,4-cyclohexanetricarboxylic acid and hydroxyalkyl (1-10 carbon atoms) (meth) acrylate alkylene (2-4 carbon atoms) oxide 1-10 Monoesteride with molar adduct, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxyethyl (meth) acrylate, 1,2,4,5-cyclohexanetetracarboxylic acid monohydroxy-n-propyl (meth) 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-shiku Lohexanetetracarboxylic 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 (carbon number) 1-10) Monoesteride of (meth) acrylate with 1-10 molar adduct of alkylene (2-4 carbon atoms) oxide, monohydroxyethyl 1,2,3,4,5-cyclohexanepentacarboxylic acid (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 (1-10 carbon atoms) (meth) acrylate Monoesteride with 1-10 molar adduct of alkylene (2-4 carbon atoms) oxide, monohydroxyethyl (meth) acrylate of 1,2,3,4,5,6-cyclohexanehexacarboxylic acid, 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, Monohydroxy-n-butyl (meth) acrylate of 3,4,5,6-cyclohexanehexacarboxylic acid, monohydroxyisobutyl (meth) a of 1,2,3,4,5,6-cyclohexanehexacarboxylic acid Clilate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n-hexyl (meth) acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n- With octyl (meth) acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydroxy-n-decyl (meth) acrylate, 1,2,3,4,5,6-cyclohexanehexacarboxylic acid Examples thereof include a monoesterified product of a hydroxyalkyl (1 to 10 carbon atoms) (meth) acrylate with an adduct of 1 to 10 mol of an alkylene (2 to 4 carbon atoms) oxide.

The monomer (h3) is, for example, a cyclohexane polyvalent (2 to 6-valent) carboxylic acid (for example, 1,2-cyclohexanedicarboxylic acid (also referred to 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 monoesterization of a meta) acrylate with an alkylene (2-4 carbon atoms) oxide 1-10 mol addition. In addition, cyclohexane polyvalent or anhydrides thereof or lower alkyl (carbons 1 to 4) esters and hydroxyalkyl (carbons 1 to 10) (meth) acrylamide or hydroxyalkyl (carbons 1 to 10) (meth) acrylamide. It can be obtained by monoesterification with 1-10 mol of alkylene (2-4 carbon atoms) oxide.
As the monomer (h3), hexahydrophthalate mono (2-methacryloyloxyethyl) (manufactured by Tokyo Chemical Industry Co., Ltd.) and hexahydrophthalate mono (2-acryloyloxyethyl) (product name "light acrylate"). "HOA-HH (N)", manufactured by Kyoeisha Chemical Co., Ltd.) and the like are commercially available and 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. It is 60% by weight, then 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 the monomer (b) constituting (A) is preferably 30 to 99% by weight, more preferably 40 to 40% by weight, based on the weight of (A), from the viewpoint of friction reduction and base oil solubility. It is 99% by weight, then more preferably 50 to 99% by weight, particularly preferably 60 to 99% by weight, and most preferably 60 to 98% by weight.
The weight ratio of the monomer (c) constituting (A) is preferably 50% by weight or less, more preferably 45% by weight or less, particularly preferably 45% by weight or less, based on the weight of (A) from the viewpoint of reducing friction. It is preferably 1 to 39% by weight.
The weight ratio of the monomer (d) constituting (A) is preferably 20% by weight or less, more preferably 15% by weight or less, particularly preferably 15% by weight or less, based on the weight of (A) from the viewpoint of reducing friction. It is preferably 1 to 10% by weight.
The weight ratio of the monomer (e) constituting (A) is preferably 15% by weight or less, more preferably 10% by weight or less, particularly preferably 10% by weight or less, based on the weight of (A) from the viewpoint of reducing friction. It is preferably 1 to 5% by weight.
The weight ratio of the monomer (f) constituting (A) is preferably 15% by weight or less, more preferably 10% by weight or less, particularly preferably 10% by weight or less, based on the weight of (A) from the viewpoint of reducing friction. It is preferably 1 to 5% by weight.
The weight ratio of the monomer (g) constituting (A) is preferably 15% by weight or less, more preferably 10% by weight or less, particularly preferably 10% by weight or less, based on the weight of (A) from the viewpoint of reducing friction. It is preferably 1 to 5% by weight.
The weight ratio of the monomer (h) constituting (A) is preferably 20% by weight or less, more preferably 15% by weight or less, particularly preferably 15% by weight or less, based on the weight of (A) from the viewpoint of reducing friction. It is preferably 1 to 10% by weight.
The mole fraction of the monomer (a) constituting the (co) polymer (A) is 1 to 40 mol based on the total number of moles of the monomers constituting (A) from the viewpoint of reducing friction. % Is preferable, more preferably 3 to 30 mol%, and particularly preferably 5 to 20 mol%.

The solubility parameter (hereinafter abbreviated as SP value) of the (co) copolymer (A) is preferably 8.5 to 11.5 (cal / cm ³ ) ^1/2 , 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 , and particularly preferably 9.0 to 10.2. (Cal / cm ³ ) ^1/2 .
The SP value in the present invention is a value calculated by the method described in the Fedors method (Polymer Engineering and Science, Polymery, 1974, Vol. 14, No. 2P. 147 to 154).

For the SP value of (A) in the case of a (co) polymer composed of two or more kinds of monomers, the SP value of each of the monomers constituting (A) is calculated by the above method, and each unit is used. The SP value of the polymer is an average value based on the mole fraction of the constituent monomer unit. The SP value of (A) can be reduced to 8.5 to 11.5 (cal / cm ³ ) ^1/2 by appropriately adjusting the SP value and mole fraction of the monomer 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 friction reduction. Yes, particularly preferably 10,000 to 600,000, most preferably 15,000 to 500,000. The Mw of the (co) polymer (A) can be measured by gel permeation chromatography (hereinafter, may be abbreviated as GPC) under the following conditions.
<Measurement conditions for Mw of (co) polymer (A)>
Equipment: "HLC-802A" [manufactured by Tosoh Corporation]
Column: 2 "TSK gel GMH6" [manufactured by Tosoh Corporation] Measurement temperature: 40 ° C
Sample solution: 0.5 wt% tetrahydrofuran solution Solution injection volume: 200 μl
Detection device: Refractive index detector Reference material: Standard polystyrene (TSKstandardPOLYSTYRENE)
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, and specific examples thereof include a method obtained by solution-polymerizing the above-mentioned monomer 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 the polymerization catalyst include azo catalysts (azobisisobutyronitrile, azobisvaleronitrile, etc.), peroxide catalysts (benzoyl peroxide, cumyl peroxide, lauryl peroxide, etc.), and redox catalysts (benzoyl peroxide). And a mixture of tertiary amines, etc.). Further, if necessary, a known chain transfer agent (alkyl mercaptan having 2 to 20 carbon atoms, etc.) can be used.
The polymerization temperature is preferably 25 to 140 ° C, more preferably 50 to 120 ° C. In addition to the above solution polymerization, (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 may be a graft copolymer or a block copolymer, but it has a friction reducing effect. From the viewpoint, a random polymer is preferable.

In addition to the essential (co) polymer (A), the friction modifier of the present invention may be used in combination with other commonly used friction modifiers of a known type, for example, molybdenum-based and zinc-based compounds. (Molybdenum dithiophosphate, molybdenum dithiopolymer and zinc dialkyl dithiophosphate) and the like.

The friction modifier of the present invention may contain a base oil.
Base oils include mineral oils (refined solvent oil, paraffin oil, high viscosity index oil containing isoparaffin, high viscosity index oil by hydrocracking of isoparaffin, naphthenic oil, etc.), synthetic lubricating oil [hydrocarbon synthetic lubricating oil] (Poly-α-olefin synthetic lubricating oil, GTL base oil, etc.) and ester synthetic lubricating oil, etc.] and mixtures thereof. Of these, mineral oils, poly-α-olefin synthetic lubricating oils, GTL base oils, and ester oils are preferable.

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

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

SP values of the base oil is preferably ^{7.0~11.0 (cal / cm 3) 1/2} , more preferably ^{7.5~10.5 (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 copolymer (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. It is 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 , and most preferably 0. It is 7.7 to 1.9 (cal / cm ³ ) ^1/2 .
If 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 if it is 3.0 (cal / cm ³ ) ^1/2 or less, the base oil of (A) 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 production of 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 cleaning agent, a dispersant, an antioxidant, an oiliness improver, an extreme pressure agent, a defoaming agent, an anti-emulsifier, and a corrosion inhibitor. And at least one additive selected from the group consisting of pour point effectors.
The weight ratio of the friction modifier in the lubricating oil composition of the present invention is preferably 0.1 to 30% by weight, more preferably 0.%, based on the weight of the lubricating oil composition from the viewpoint of the friction reducing effect. It is 2 to 20% by weight, particularly preferably 0.5 to 10% by weight.
The weight ratio of the (co) copolymer (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 the friction reducing effect. It is more preferably 0.1 to 10% by weight, and 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. It is suitably used for oils, hydraulic oils (hydraulics for construction machinery, industrial hydraulic oils, etc.) and engine oils. Of these, gear oils, MTFs, transmission oils, traction oils and engine oils are preferred, further preferred are differential oils, MTFs, ATFs, belt-CVTFs and engine oils, with particular preference being MTFs, ATFs. , 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, defoamer, anti-emulsifier, corrosion inhibitor and pour point effectant are used. The following can be mentioned.
(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) Linear or branched alkyl (meth) acrylate copolymer, hydroxy group-containing monomer / (C1-7) alkyl (meth) acrylate / (C8-40) linear or branched alkyl (meth) acrylate copolymer, Comb 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 hydride copolymer, etc.;
(2) Cleaner:
Basic, hyperbasic or neutral metal salts [superbasic or alkaline earth metal salts of sulfonates (petroleum sulfonates, alkylbenzenesulfonates, alkylnaphthalene sulfonates, etc.)], salicylates, phenates, naphthenates, etc. Classes, 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 acid esters, etc.), long-chain amines and their amides (oleylamine, oleylamide, etc.), etc .;
(6) Extreme pressure agent:
Sulfur compounds (mono or disulfide, sulfoxide and sulfur phosphide compounds), phosphide compounds and chlorinated compounds (chlorinated paraffin, etc.), etc.;
(7) Defoamer:
Silicone oil, metal soap, fatty acid ester, phosphate compound, etc .;
(8) Anti-emulsifier:
Quaternary ammonium salts (tetraalkylammonium salts, etc.), sulfated oils and phosphates (polyoxyethylene-containing nonionic surfactants, etc.);
(9) Corrosion inhibitor:
Nitrogen atom-containing compounds (benzotriazole and 1,3,4-thiodiazolyl-2,5-bisdialkyldithiocarbamate, etc.);
(10) Pour point effectant:
Polyalkyl methacrylate, polyalkyl acrylate, polyalkyl styrene, polyvinyl acetate, etc.

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

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

<Examples 1 to 5, Comparative Examples 1 to 7>
In a reaction vessel equipped with a stirrer, a heating / cooling device, a thermometer and a nitrogen introduction tube, 185 parts by weight of ethyl acetate, 100 parts by weight of the monomer formulation shown in Table 1, 2,2'-azobis (2,4). -Dimethylvaleronitrile) 0.5 part by weight and 2,2'-azobis (2-methylbutyronitrile) 0.2 part by weight were added, nitrogen substitution (gas phase oxygen concentration 100 ppm) was performed, and then sealed. The temperature was raised to 76 ° C. with stirring, and the polymerization reaction was carried out at the same temperature for 7 hours.
Mineral oil [SP value: 8.3 (cal / cm ³ ) ^1/2 , kinematic viscosity at 100 ° C: 4.2 mm ² / s, viscosity index: 122] Add 100 parts by weight and heat to 120-130 ° C. After that, the unreacted monomer and ethyl acetate were removed under reduced pressure (0.027 to 0.040 MPa) at the same temperature over 2 hours to remove the 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 shown in Table 1 are as described below.
(A-1): β-carboxyethyl acrylate (“β-CEA” manufactured by Daicel Ornex Co., Ltd.) (R ¹ in the general formula (1) is a hydrogen atom, X ¹ is −O−, and R ² is an ethylene group. s is 1)
(A-2): ω-carboxypolycaprolactone (addition of 2 mol of caprolactone) monoacrylate (“Aronix M-5300” manufactured by Toa Synthetic Co., Ltd.) (R ¹ is a hydrogen atom and X ¹ is −O in the general formula (1). -, 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): a linear branched alcohol mixture having 12 to 13 carbon atoms. ("Neodor 23" manufactured by Shell Chemicals) and an esterified product of acrylic acid.
(B-5): An esterified product of a linear branched alcohol mixture having 12 to 13 carbon atoms (“Neodor 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 (“Neodor 45” manufactured by Shell Chemicals).
(B-7): An esterified product of a linear branched alcohol mixture having 14 to 15 carbon atoms (“Neodor 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): 50/50 weight ratio mixture of 2-dodecylhexadecyl acrylate and 2-tetradecyl octadecyl acrylate (b-12): 2-dodecylhexadecyl methacrylate and 2-tetradecyl octadecyl methacrylate 50/50 weight ratio mixture (c-1): 5 mol addition of caprolactone of 2-hydroxyethyl methacrylate (“Placel FM5” manufactured by Daicel)
(C-2): 10 mol of caprolactone of 2-hydroxyethyl acrylate (Daicel's "Plaxel FA10L")
(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): Acrylhexanoic 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 stirrer, 10 parts by weight of an additive package for engine oil (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 are added, and the friction modifiers (R-1) to (R-5) or comparative samples (R'-1) to (R'-7) Is added so that the content of the copolymer (A) or (A') is 1% by weight, and the HTHS viscosity at 150 ° C. of the obtained lubricating oil composition is 2.60 ± 0.05. A viscosity index improver (polyalkyl methacrylate, Mw 500,000, resin content 21% by weight) was added and mixed so as to be (mm ² / s), and the lubricating oil compositions (V-1) to (V-5) were mixed. ), And the lubricating oil compositions (V'-1) to (V'-7) were obtained.
The HTHS viscosity at this time was measured at 150 ° C. by the method of ASTM D 5484.
The engine oil additive package used was a metal-based cleaning agent (calcium-sulfurate-based), an ashless dispersant (succinimide), an anti-wear agent (phosphoric acid), an antioxidant (diphenylamine), and no metal. Includes activator (thiadiazole), sulfur-based additive (succinimide) and the like.

Lubricating oil compositions (V-1) to (V-5) and (V'-1) to (V'-7) under low to medium temperature conditions at 40 ° C, 60 ° C and 80 ° C. Friction evaluation was measured by the following method. The results are shown in Tables 2 and 3.
<Rolling friction characteristics-MTM (coefficient of friction)>
Equipment: PCS Instruments MTM-2
Disc: MTM polished disc (standard) (0.01 micron)
Ball: Drilled 3/4 AISI52100 precision steel ball
Speed: 10 mm / s to 3,000 mm / s
Temperature: 40 ° C, 60 ° C, 80 ° C
Sliding / rolling ratio: 50%
Load: 30N
A Stribeck curve was obtained as a result of the friction evaluation, and the friction coefficients of the velocities at each temperature: 10 mm / s, 100 mm / s, and 1,000 mm / s 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 carried out at m, a frequency of 20 Hz, and a test time of 60 min, 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) copolymer (A) containing the monomer (a) of the present invention as a constituent monomer. In Comparative Examples 8 to 12, the products (Examples 6 to 10) have substantially 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 Composition (Comparison between Example 6 and Comparative Example 8, Comparison between Example 7 and Comparative Example 9, Comparison between Example 8 and Comparative Example 10, Comparison between Example 9 and Comparative Example 11) (Comparison between Example 10 and Comparative Example 12), in terms of both rolling friction characteristics and sliding friction characteristics, Examples 6 to 10 which are the lubricating oil compositions of the present invention are 40 ° C., 60 ° C. and 80 ° C. It can be seen that the friction reducing effect is high at any of the above temperatures.
Further, a comparative example in which the SP value and Mw are almost the same except that (meth) acrylamide (i) having a carboxyalkyl group (in which -X ^1- in the general formula (1) is -NH-) is used. Comparing with the lubricating oil compositions of 13 to 14 (comparison between Example 6 and Comparative Example 13, comparison between Example 8 and Comparative Example 14), although the sliding friction characteristics are similar, the rolling friction characteristics It can be seen that Examples 6 and 8 of the present invention have a higher friction reducing effect at any of the temperatures of 40 ° C, 60 ° C and 80 ° C.

The lubricating oil composition containing the friction modifier of the present invention includes drive system lubricating oils (MTF, differential gear oil, ATF, belt-CVTF, etc.), hydraulic oils (machine hydraulic oils, power steering oils and shock absorbers). It is suitable as oil), engine oil (for gasoline and diesel, etc.) and traction oil.

Claims (8)

A friction modifier containing a (co) polymer (A) containing a monomer (a) represented by the following general formula (1) as a constituent monomer.

[R ¹ in the 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 of 1 to 15, and R ² when s is 2 or more 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 the 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) as a constituent monomer based on the total weight of the monomer (a) and the monomer (b). The friction modifier according to claim 2, which is a copolymer containing 30 to 99% by weight of the monomer (b). According to any one of claims 1 to 3, the (co) polymer (A) is a copolymer further containing the monomer (c) represented by the following general formula (3) as a constituent monomer. The described friction modifier.

[R ⁵ in the 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. Represents an alkylene group having 1 to 10 carbon atoms. t is an integer of 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, a viscosity index improver, a cleaning agent, a dispersant, an antioxidant, an oiliness improver, an extreme pressure agent, a defoaming agent, an antiemulsifier, and corrosion prevention. A lubricating oil composition containing at least one additive selected from the group consisting of an agent and a pour point effectant. The lubricating oil composition according to claim 7, wherein the base oil has a kinematic viscosity of 1 to 15 mm ² / s at 100 ° C., and the viscosity index of the base oil is 90 or more.