WO2024053734A1 - 重合体、潤滑油用摩擦低減剤、及び潤滑油組成物 - Google Patents

重合体、潤滑油用摩擦低減剤、及び潤滑油組成物 Download PDF

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WO2024053734A1
WO2024053734A1 PCT/JP2023/032862 JP2023032862W WO2024053734A1 WO 2024053734 A1 WO2024053734 A1 WO 2024053734A1 JP 2023032862 W JP2023032862 W JP 2023032862W WO 2024053734 A1 WO2024053734 A1 WO 2024053734A1
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parts
meth
acrylate
yubase4
polymer
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English (en)
French (fr)
Japanese (ja)
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洋 徳江
一成 松村
絵理 増田
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Mitsubishi Chemical Corp
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Mitsubishi Chemical Corp
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Priority to EP23863272.3A priority Critical patent/EP4585625A4/en
Priority to CN202380063011.1A priority patent/CN119816532A/zh
Priority to JP2024543066A priority patent/JP7652345B2/ja
Publication of WO2024053734A1 publication Critical patent/WO2024053734A1/ja
Priority to US19/071,551 priority patent/US20250197546A1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10—Esters
    • C08F120/12—Esters of monohydric alcohols or phenols
    • C08F120/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F120/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to polymers used in lubricating oils, friction reducers for lubricating oils, and lubricating oil compositions.
  • Lubricating oils such as automobile engine oils and drive system oils, contain various friction reducing agents for the purpose of reducing energy loss due to friction and extending the life of equipment by preventing seizure.
  • Friction reducing agents include oiliness improvers such as long-chain fatty acid esters and fatty acid amides, anti-wear agents such as phosphoric acid esters and zinc dithiophosphate, extreme pressure agents such as organic sulfur compounds and organic halogen compounds, organic molybdenum compounds, etc.
  • Friction modifiers and the like can be mentioned, but depending on the usage conditions and usage environment, there is a problem that these additives alone may not be sufficient in reducing friction. To overcome this problem, studies are underway to use polymeric materials as friction reducers.
  • Patent Document 1 discloses that a (meth)acrylic graft copolymer can be suitably used as a friction modifier.
  • Patent Document 1 has an insufficient effect of reducing friction. Furthermore, the viscosity of the lubricating oil composition is high, and energy loss due to stirring resistance becomes large, resulting in poor fuel efficiency.
  • An object of the present invention is to provide a polymer, and a polymer lubricating oil additive having a high friction reducing effect and low viscosity, a friction reducing agent for lubricating oil, and a lubricating oil composition using the polymer.
  • the objective is to provide a polymer that can provide the following properties.
  • the present invention has the following aspects.
  • [1] Has a main chain polymer structure and a side chain polymer structure,
  • the side chain polymer structure contains a structural unit derived from an alkyl (meth)acrylate (a) in which the alkyl group has 11 to 30 carbon atoms, A polymer having a mass average molecular weight of 90,000 or less.
  • a base oil solution containing 2% by mass of the polymer is prepared, and the kinematic viscosity at 40°C measured according to ASTM D7279 (D445) method is 22.4 cSt or less, 2.
  • the polymer of claim 1, wherein the base oil is API Standard Group III Plus.
  • the side chain polymer structure contains a structural unit derived from an alkyl (meth)acrylate (a) in which the alkyl group has 11 to 30 carbon atoms, A base oil solution containing 2% by mass of the polymer is prepared, and the kinematic viscosity at 40°C measured according to ASTM D7279 (D445) method is 22.4 cSt or less, The base oil is a polymer that is API standard Group III plus.
  • [5] The polymer according to any one of [1] to [4], further comprising a structural unit derived from an alkyl (meth)acrylate (b) whose alkyl group has 1 to 10 carbon atoms.
  • the proportion of the main chain polymer structure is preferably 5 to 98% by mass, more preferably 10 to 95% by mass, and even more preferably 20 to 90% by mass, based on the total mass of the polymer.
  • the proportion of the side chain polymer structure is preferably 2 to 95% by mass, more preferably 5 to 90% by mass, and even more preferably 10 to 80% by mass, based on the total mass of the polymer.
  • the alkyl (meth)acrylate (a) is preferably an alkyl (meth)acrylate in which the alkyl group has 11 to 20 carbon atoms, more preferably an alkyl (meth)acrylate in which the alkyl group has 11 to 18 carbon atoms.
  • the copolymer according to any one of [1] to [8] more preferably an alkyl (meth)acrylate in which the alkyl group has 11 to 14 carbon atoms.
  • the content of the structural unit derived from the alkyl (meth)acrylate (a) is preferably 50 to 100% by mass, and preferably 60 to 100% by mass, based on the total mass of the side chain polymer structure.
  • the content of the structural unit derived from the alkyl (meth)acrylate (a) is preferably 20 to 98% by mass, more preferably 25 to 95% by mass, based on the total mass of the polymer.
  • [13] Furthermore, it contains a structural unit derived from an alkyl (meth)acrylate (b) whose alkyl group has 1 to 10 carbon atoms, and the content of the structural unit derived from the (meth)acrylate (b) is equal to the total amount of the polymer. Any one of [1] to [12], based on the mass, preferably 3 to 80% by mass, more preferably 5 to 75% by mass, and even more preferably 10 to 70% by mass.
  • the radically polymerizable vinyl compound (c) containing a structural unit derived from a polymerizable vinyl compound (c) is an alkyl (meth)acrylate having a polar group, such as a hydroxyl group, a carboxy group, or an amino group.
  • X 1 to X n-1 each independently represent a hydrogen atom, a methyl group, or CH 2 OH
  • Y 1 to Y n each independently represent a monomer of the macromonomer (M).
  • M macromonomer
  • Z represents a terminal group, and n is an integer from 2 to 10,000. represent.
  • the content of the structural unit derived from the alkyl (meth)acrylate (a) is preferably 50 to 100% by mass, and preferably 60 to 100% by mass, based on the total mass of the macromonomer (M).
  • the macromonomer (M) contains a structural unit derived from an alkyl (meth)acrylate (b) in which the alkyl group has 1 to 10 carbon atoms, and the content of the structural unit derived from the (meth)acrylate (b) is is more preferably contained in an amount of 0.5 to 40% by mass, still more preferably contained in an amount of 1 to 30% by mass, and more preferably contained in an amount of 1.5 to 20% by mass, based on the total mass of the macromonomer (M). is particularly preferred, the polymer according to any one of [16] to [20].
  • the ratio represented by [content of structural units derived from] is preferably 0.001 to 0.1, more preferably 0.005 to 0.05, and even more preferably 0.01 to 0.03, [1] -
  • the content of the structural unit derived from the macromonomer (M) is preferably 1 to 70% by mass, more preferably 2 to 60% by mass, and further preferably 5 to 50% by mass, based on the total mass of the polymer.
  • the mass average molecular weight (Mw) of the macromonomer (M) measured by gel permeation chromatography is preferably 5,000 or more and 50,000 or less, more preferably 8,000 or more and 40,000 or less, and 10,000 or more and 30,000 or less. is more preferred, the polymer according to any one of [16] to [23].
  • the number average molecular weight (Mn) of the macromonomer (M) measured by gel permeation chromatography (GPC) is preferably 500 to 30,000, more preferably 1,000 to 25,000, and particularly preferably 2,000 to 20,000. ] to [24].
  • the molecular weight distribution (Mw/Mn) of the macromonomer (M) measured by gel permeation chromatography is preferably 1.0 or more and 10 or less, more preferably 1.2 or more and 8 or less, 1.
  • the mass average molecular weight (Mw) of the polymer measured by GPC is preferably 90,000 or less, more preferably 10,000 or more and 90,000 or less, even more preferably 12,000 to 85,000, and particularly preferably 15,000 to 80,000.
  • the number average molecular weight (Mn) of the polymer measured by gel permeation chromatography (GPC) is preferably 5,000 or more and 50,000 or less, more preferably 7,000 or more and 40,000 or less, and 10,000 or more and 30,000 or less. is more preferred, the polymer according to any one of [1] to [27].
  • the molecular weight distribution (Mw/Mn) of the polymer measured by gel permeation chromatography (GPC) is preferably 1.0 or more and 20 or less, more preferably 1.5 or more and 15 or less, 2.
  • a base oil solution containing 2% by mass of the polymer is prepared, and the friction coefficient measured at 40°C using an SRV5 tester (manufactured by Optimol Instruments Pruftechnik GmbH) is preferably 0.16 or less, and 0.
  • a base oil solution containing 2% by mass of the polymer is prepared, and the kinematic viscosity at 40°C measured according to the ASTM D7279 (D445) method is preferably 0 to 22.4 cSt, and preferably 5 cSt or more 22 It is more preferably less than .25 cSt, even more preferably 10 cSt or more and 22.00 cSt or less, particularly preferably 15 to 21.50 cSt, The polymer according to any one of [1] to [30], wherein the base oil is API standard Group III plus.
  • a lubricating oil additive comprising the polymer according to any one of [1] to [31].
  • a friction reducing agent for lubricating oil comprising the polymer according to any one of [1] to [31] and a base oil.
  • the friction reducing agent for lubricating oil according to [33] wherein the base oil is a base oil of API Standard Group III, a base oil of API Standard Group III Plus, or a base oil of API Group IV.
  • the content of the polymer is preferably 10 to 80% by mass, more preferably 15 to 70% by mass, and 20 to 60% by mass when the total mass of the lubricating oil additive is 100% by mass. More preferably, the friction reducing agent for lubricating oil according to [33] or [34].
  • a lubricating oil composition comprising the friction reducing agent for lubricating oil according to any one of [33] to [35].
  • the content of the polymer is preferably 0.01 to 30% by mass, more preferably 0.05 to 25% by mass, and 0.01 to 30% by mass, more preferably 0.05 to 25% by mass, when the total mass of the lubricating oil composition is 100% by mass.
  • the lubricating oil composition according to [36] more preferably 1 to 20% by mass.
  • [40] Use of the polymer according to any one of [1] to [31] for improving lubricity.
  • [41] Use of a composition comprising the polymer according to any one of [1] to [31] for reducing friction.
  • [42] Use of a composition comprising the polymer according to any one of [1] to [31] for improving lubricity.
  • [43] The use according to [41] or [42], wherein the composition contains a solvent.
  • the solvent is a base oil.
  • the use according to [44], wherein the base oil is an API standard Group III base oil, an API standard Group III plus base oil, or an API standard Group IV base oil.
  • the content of the polymer is preferably 0.01 to 30% by mass, more preferably 0.05 to 25% by mass, and 0.1 to 25% by mass, when the total mass of the composition is 100% by mass.
  • a friction reducing agent for lubricating oil containing a (meth)acrylic graft copolymer A having a main chain polymer structure and a side chain polymer structure
  • the (meth)acrylic graft copolymer A contains a structural unit derived from alkyl (meth)acrylate (a) in which the alkyl group has 11 to 30 carbon atoms in the side chain polymer structure, and has a mass average molecular weight of 10,000. ⁇ 90,000 friction reducing agent for lubricating oil.
  • the (meth)acrylic graft copolymer A further contains a structural unit derived from an alkyl (meth)acrylate (b) in which the alkyl group has 1 to 10 carbon atoms. Friction reducer.
  • the (meth)acrylic graft copolymer A contains a structural unit derived from a vinyl radically polymerizable monomer (m1) and a structural unit derived from a macromonomer (M). Friction reducer for lubricating oils as described.
  • X 1 to X n-1 each independently represent a hydrogen atom, a methyl group, or CH 2 OH
  • Y 1 to Y n each independently represent a monomer of the macromonomer (M).
  • M macromonomer
  • Z represents a terminal group, and n is an integer from 2 to 10,000. represent.
  • [6] A lubricating oil composition containing the friction reducing agent for lubricating oil according to any one of [1] to [5].
  • the polymer of the present invention it is possible to provide a polymer that has a high friction-reducing effect and can provide a low-viscosity polymer lubricating oil additive, a friction reducing agent for lubricating oil, and a lubricating oil composition.
  • (meth)acrylic is a general term for “acrylic” and “methacrylic”.
  • (Meth)acrylate is a generic term for “acrylate” and “methacrylate.”
  • "Macromonomer” means a polymer having a radically polymerizable group or an addition-reactive functional group.
  • "Vinyl-based radically polymerizable monomer means a monomer having an ethylenically unsaturated bond that is not a macromonomer.
  • the polymer in the first aspect of the present invention has a main chain polymer structure and a side chain polymer structure, and the side chain polymer structure is an alkyl (meth)acrylate (having an alkyl group having 11 to 30 carbon atoms) ( Contains a structural unit derived from a) and has a mass average molecular weight of 90,000 or less.
  • the polymer according to the second aspect of the present invention has a main chain polymer structure and a side chain polymer structure, and the side chain polymer structure is an alkyl (meth)acrylate (having an alkyl group having 11 to 30 carbon atoms)
  • a base oil solution containing the structural unit derived from a) and 2% by mass of the polymer is prepared, and the kinematic viscosity at 40°C measured according to ASTM D7279 (D445) method is 22.4 cSt or less, and the above-mentioned
  • the base oil is API standard Group III plus.
  • the polymer is preferably a graft copolymer in which at least some of the structural units are structural units derived from (meth)acrylic monomers.
  • the polymer may further contain a structural unit derived from a monomer other than the (meth)acrylic monomer (for example, styrene, etc.).
  • the polymer is preferably a graft copolymer composed of a main chain polymer structure and a side chain polymer structure (branch polymer structure) chemically bonded to the main chain polymer structure (stem polymer structure).
  • a graft copolymer is a polymer having one or more types of blocks connected to a main chain polymer structure as a side chain polymer structure.
  • the structures of the main chain polymer and the side chain polymer may be different or the same.
  • the method for producing the graft copolymer is not particularly limited, but includes a method in which a macromonomer having a radically polymerizable double bond at the terminal is produced as a side chain polymer structure, and then radically polymerized with a monomer that becomes a constituent unit of the main chain polymer.
  • a method in which a main chain polymer having a reactive site and a macromonomer having a reactive site are produced in advance and then reacted, or a method in which a main chain polymer is produced and then an initiator having hydrogen abstracting ability is used to inject onto the main chain polymer. Examples include a method of producing a side chain polymer structure by generating radicals and reacting monomers serving as constitutional units of the side chain polymer.
  • the polymer includes a structural unit derived from an alkyl (meth)acrylate (a) (hereinafter also referred to as “component (a)”) having an alkyl group having 11 to 30 carbon atoms in the side chain polymer structure, and has a mass average molecular weight. is preferably 10,000 to 90,000. Furthermore, a structural unit derived from an alkyl (meth)acrylate (b) (hereinafter also referred to as “component (b)”) having an alkyl group having 1 to 10 carbon atoms can be included.
  • the total content of components (a) and (b) as structural units is preferably 70% by mass or more, more preferably 75% by mass or more, and 80% by mass or more based on the total mass of the polymer. It is even more preferable to contain it.
  • the polymer includes a structural unit derived from component (a) in the side chain polymer structure. Both the side chain polymer structure and the main chain polymer structure may contain structural units derived from component (a).
  • Examples of the component (a) include n-undecyl (meth)acrylate, i-undecyl (meth)acrylate, n-dodecyl (meth)acrylate, i-dodecyl (meth)acrylate, and n-tridecyl (meth)acrylate.
  • Acrylate i-tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, i-tetradecyl (meth)acrylate, n-cetyl (meth)acrylate, i-cetyl (meth)acrylate, n-stearyl (meth)acrylate
  • Examples include i-stearyl (meth)acrylate, n-octadecyl (meth)acrylate, i-octadecyl (meth)acrylate, n-behenyl (meth)acrylate, and i-behenyl (meth)acrylate. Two or more of these may be used in combination.
  • component (a) is preferably an alkyl (meth)acrylate in which the alkyl group has 11 to 20 carbon atoms; ) acrylate is more preferred, and alkyl (meth)acrylate in which the alkyl group has 11 to 14 carbon atoms is even more preferred.
  • component (a) is preferably an alkyl (meth)acrylate in which the alkyl group has 11 to 20 carbon atoms; Methacrylate is more preferred, alkyl methacrylate in which the alkyl group has 11 to 18 carbon atoms is even more preferred, and alkyl methacrylate in which the alkyl group has 11 to 14 carbon atoms is particularly preferred.
  • the content of the structural unit derived from component (a) is 20 to 98% by mass based on the total mass of the polymer, from the viewpoint of increasing the friction reduction effect and reducing the viscosity of the lubricating oil composition.
  • the content is preferably 25 to 95% by mass, more preferably 30 to 90% by mass.
  • component (b) for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl ( Alkyl (meth)acrylates having a linear alkyl group such as meth)acrylate, n-heptyl(meth)acrylate, n-octyl(meth)acrylate, n-nonyl(meth)acrylate; i-propyl(meth)acrylate , i-butyl (meth)acrylate, t-butyl (meth)acrylate, i-nonyl (meth)acrylate, n-decyl (meth)acrylate, i-decyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, etc.
  • Alkyl (meth)acrylate having a branched alkyl group cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, isobornyl (meth)acrylate, 4-t-butylcyclohexyl (meth)acrylate
  • alkyl (meth)acrylates having a cyclic alkyl group such as. Two or more of these may be used in combination.
  • component (b) is preferably a (meth)acrylate having a linear or branched alkyl group, more preferably an alkyl acrylate in which the alkyl group has 2 to 8 carbon atoms.
  • Alkyl acrylates in which the alkyl group has 2 to 4 carbon atoms are more preferred, and n-butyl acrylate is particularly preferred.
  • the content of the structural unit derived from component (b) is 3 to 80% by mass based on the total mass of the polymer, from the viewpoint of increasing the friction reduction effect and reducing the viscosity of the lubricating oil composition.
  • the content is preferably from 5 to 75% by mass, more preferably from 10 to 70% by mass.
  • the polymer preferably contains a structural unit derived from the component (a) in the side chain polymer structure, and the side chain polymer structure and the main It is more preferable to include both a chain polymer structure and a chain polymer structure.
  • the polymer preferably contains a structural unit derived from the component (b) in the side chain polymer structure, and more preferably in both the side chain polymer structure and the main chain polymer structure.
  • the mass average molecular weight (Mw) of the polymer is preferably 90,000 or less. From the viewpoint of reducing the viscosity of the lubricating oil composition, the mass average molecular weight of the polymer is more preferably 10,000 to 90,000, even more preferably 12,000 to 85,000, and 1. It is particularly preferably from 50,000 to 80,000, and most preferably from 20,000 to 75,000.
  • the polymer may contain structural units derived from other radically polymerizable vinyl compounds (hereinafter also referred to as "component (c)”) other than component (a) and component (b).
  • component (c) radically polymerizable vinyl compounds
  • examples of other radically polymerizable vinyl compounds include styrene, ⁇ -methylstyrene, pt-butylstyrene, vinyltoluene, vinyl acetate, and (meth)acrylate compounds other than components (a) and (b). can be mentioned.
  • (Meth)acrylate compounds other than component (a) and (b) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl Alkyl (meth)acrylates with hydroxyl groups such as (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, glycerin mono(meth)acrylate, ethylene glycol mono(meth)acrylate, propylene glycol mono(meth)acrylate; ) Acrylic acid, 2-(meth)acryloyloxyethyl succinate, 2-(meth)acryloyloxyethyl maleate, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, etc.
  • Alkyl (meth)acrylate containing a carboxyl group phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate, phenoxypolypropylene glycol (meth)acrylate, phenyl phenyl (meth)acrylate, phenylphenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, phenylbenzyl (meth)acrylate, naphthyl (meth)acrylate, (1 - Alkyl (meth)acrylates having an aromatic ring structure such as naphthyl)methyl (meth)acrylate; having a heterocyclic structure such as tetrahydrofurfuryl (meth)acrylate, glycidyl
  • the content of the structural unit derived from component (c) is 0 to 20% by mass based on the total mass of the polymer, from the standpoint of increasing the friction reduction effect and decreasing the viscosity of the lubricating oil composition.
  • the content is preferably from 0 to 10% by weight, more preferably from 0 to 5% by weight.
  • the total amount of the structural units derived from the components (a) to (c) does not exceed 100% by mass based on the total mass of the polymer.
  • the polymer contains a structural unit derived from a vinyl radically polymerizable monomer (m1) (hereinafter also referred to as “component (m1)”) and a macromonomer (M) (hereinafter also referred to as “component (M)”). ) may also include a structural unit derived from.
  • component (m1) vinyl radically polymerizable monomer
  • M macromonomer
  • Examples of the component (m1) include styrene, vinyl acetate, (meth)acrylate compounds, and the like.
  • Examples of (meth)acrylate compounds include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl ( meth)acrylate, n-heptyl(meth)acrylate, n-octyl(meth)acrylate, n-nonyl(meth)acrylate, n-decyl(meth)acrylate, n-undecyl(meth)acrylate, n-dodecyl(meth)acrylate Straight chain alkyl groups such as acrylate, n-tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, n-cety
  • alkyl (meth)acrylate alkyl (meth)acrylate; i-propyl (meth)acrylate, i-butyl (meth)acrylate, t-butyl (meth)acrylate, s-butyl (meth)acrylate, isoamyl (meth)acrylate, 2-ethylhexyl ) acrylate, i-nonyl (meth)acrylate, i-decyl (meth)acrylate, 3-i-propylheptyl (meth)acrylate, i-undecyl (meth)acrylate, 2-t-butylheptyl (meth)acrylate, i - Alkyl (meth)acrylates having a branched alkyl group such as dodecyl (meth)acrylate, i-tridecyl (meth)acrylate, i-tetradecyl (meth)acrylate, i-behenyl (meth)
  • Alkyl (meth)acrylate having an alkyl group 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl Alkyl (meth)acrylates with hydroxyl groups such as (meth)acrylate, glycerin mono(meth)acrylate, ethylene glycol mono(meth)acrylate, propylene glycol mono(meth)acrylate; (meth)acrylic acid, succinic acid 2-( Alkyl (meth) containing a carboxy group such as meth)acryloyloxyethyl, 2-(meth)acryloyloxyethyl maleate, 2-(meth)acryloyloxyethyl phthalate, and 2-(meth)acryloyloxyethyl hexahydrophthalate.
  • hydroxyl groups such as (meth)acrylate, glycerin mono
  • acrylate phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate, phenoxypolypropylene glycol ( meth)acrylate, phenyl phenyl (meth)acrylate, phenylphenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, phenylbenzyl (meth)acrylate, naphthyl (meth)acrylate, (1-naphthyl)methyl (meth)acrylate, etc.
  • Alkyl (meth)acrylates having an aromatic ring structure Alkyl (meth)acrylates having a heterocyclic structure such as tetrahydrofurfuryl (meth)acrylate, glycidyl (meth)acrylate, (meth)acryleoylmorpholine; Methoxyethyl ( Alkoxyalkyl (meth)acrylates such as meth)acrylate, ethoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate; allyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 2-(meth)acryloyloxyethyl acid phosphate, trifluoroethyl(meth)acrylate, heptadecafluorodec
  • the component (b) as the component (m1) is preferable to contain the component (b) as the component (m1), more preferably an alkyl acrylate having an alkyl group having 2 to 8 carbon atoms, and an alkyl acrylate having an alkyl group having 2 to 8 carbon atoms. -4 alkyl acrylates are more preferred, and n-butyl acrylate is particularly preferred. From the viewpoint of increasing the solubility of the polymer in base oil, it is preferable to contain the above-mentioned (a) component as the (m1) component, and an alkyl (meth)acrylate having an alkyl group having 11 to 20 carbon atoms is more preferable. , alkyl (meth)acrylates in which the alkyl group has 11 to 18 carbon atoms are more preferred, and alkyl (meth)acrylates in which the alkyl group has 11 to 14 carbon atoms are particularly preferred.
  • the component (M) contains two or more structural units derived from a monomer (m2) having a vinyl radically polymerizable group (hereinafter also referred to as "component (m2)"), and has a radically polymerizable group at the end. It is a compound having the above-mentioned (a) component as the (m2) component. Examples of the (m2) component other than the (a) component include the compounds listed above as the (m1) component.
  • the component (m2) is preferably an alkyl (meth)acrylate whose alkyl group has 11 to 20 carbon atoms; are more preferred, alkyl methacrylates in which the alkyl group has 11 to 18 carbon atoms are even more preferred, and alkyl methacrylates in which the alkyl group has 11 to 14 carbon atoms are particularly preferred.
  • (meth)acrylate having a linear or branched alkyl group is preferable as the component (m2), and an alkyl methacrylate in which the alkyl group has 1 to 8 carbon atoms. are more preferred, alkyl methacrylates in which the alkyl group has 1 to 4 carbon atoms are even more preferred, and methyl methacrylate is particularly preferred.
  • the structural unit derived from the component (a) be contained in an amount of 50% by mass or more, and preferably 60% by mass or more based on the total mass of the component (M). It is more preferable to contain 70% by mass or more, and it is particularly preferable to contain 80% by mass or more. Further, from the viewpoint of radical polymerizability, the component (M) preferably has a structure represented by the following formula (1).
  • X 1 to X n-1 each independently represent a hydrogen atom, a methyl group, or CH 2 OH
  • Y 1 to Y n each independently represent a monomer of the macromonomer (M).
  • M a monomer of the macromonomer
  • Z represents a terminal group
  • n represents an integer from 2 to 10,000.
  • X 1 to X n-1 and Y 1 to Y n are each independently substituents bonded to the vinyl group of component (m2).
  • Y 1 to Y n represent, for example, OR 1 , a halogen atom, COR 2 , COOR 3 , CN, CONR 4 R 5 , NHCOR 6 , or R 7 , and R 1 to R 7 each independently represent a hydrogen atom, Indicates an alkyl group, an aryl group, a heteroaryl group, etc.
  • the terminal group Z includes a group derived from a hydrogen atom and a radical polymerization initiator, similar to the terminal group of a polymer obtained by known radical polymerization.
  • the content of the structural units derived from the component (M) should be 1 to 1 with respect to the total mass of the polymer. It is preferably 70% by weight, more preferably 2 to 60% by weight, even more preferably 5 to 50% by weight.
  • the polymer may contain two or more types of structural units derived from the component (M).
  • the structural unit derived from the component (b) be contained in an amount of more than 0% by mass and not more than 50% by mass, based on the total mass of the component (M).
  • the content is more preferably .5 to 40% by mass, even more preferably 1 to 30% by mass, and particularly preferably 1.5 to 20% by mass.
  • the ratio represented by is preferably 0.001 to 0.1, more preferably 0.005 to 0.05, and even more preferably 0.01 to 0.03.
  • the mass average molecular weight (Mw) of the macromonomer (M) measured by gel permeation chromatography (GPC) is 5000 or more, since it can increase the solubility of the polymer in base oil and increase the friction reduction effect. It is preferably 50,000 or less, more preferably 8,000 or more and 40,000 or less, and even more preferably 10,000 or more and 30,000 or less.
  • the number average molecular weight (Mn) of the component (M) measured by gel permeation chromatography is preferably from 500 to 30,000, from the viewpoint of increasing the solubility of the polymer in the base oil and increasing the friction reduction effect. More preferably 1000 to 25000, particularly preferably 2000 to 20000.
  • the molecular weight distribution (Mw/Mn) of the macromonomer (M) measured by gel permeation chromatography (GPC) is 1 from the viewpoint of increasing the solubility of the polymer in base oil and increasing the friction reduction effect. It is preferably .0 or more and 10 or less, more preferably 1.2 or more and 8 or less, and even more preferably 1.5 or more and 5 or less.
  • the component (M) may be produced by a known method or may be commercially available.
  • Methods for producing the M component include, for example, a method using a cobalt chain transfer agent (US Pat. No. 4,680,352), a method using an ⁇ -substituted unsaturated compound such as ⁇ -bromomethylstyrene as a chain transfer agent. (International Publication No. 88/04304), a method of chemically bonding polymerizable groups (Japanese Unexamined Patent Publication No. 60-133007 and US Pat. No. 5,147,952), and a method using thermal decomposition (Japanese Unexamined Patent Publication No. 11-240854) ).
  • a method of manufacturing using a cobalt chain transfer agent is preferable because it requires fewer manufacturing steps and uses a catalyst with a high chain transfer constant. Since the cobalt chain transfer agent has a high chain transfer constant, a macromonomer with a controlled molecular weight can be obtained by adding a small amount.
  • cobalt chain transfer agent known cobalt complexes can be used.
  • the amount of the cobalt chain transfer agent is preferably 0.00001 to 0.1 part by mass, more preferably 0.00005 to 0.05 part by mass, based on 100 parts by mass of component (m2). Particularly preferred is 0.0001 to 0.02 parts by mass.
  • the number average molecular weight (Mn) measured by gel permeation chromatography (GPC) of the polymer contained in the friction reducing agent for lubricating oil of the present invention is important because it can increase the solubility of the polymer in base oil and reduce friction. From the viewpoint of increasing the effect, it is preferably 5,000 or more and 50,000 or less, more preferably 7,000 or more and 40,000 or less, and even more preferably 10,000 or more and 30,000 or less.
  • the molecular weight distribution (Mw/Mn) measured by gel permeation chromatography (GPC) of the polymer contained in the friction reducing agent for lubricating oil of the present invention shows that the solubility of the polymer in the base oil can be increased and the friction From the viewpoint of increasing the reduction effect, it is preferably 1.0 or more and 20 or less, more preferably 1.5 or more and 15 or less, and even more preferably 2.0 or more and 10 or less.
  • the friction reducing agent for lubricating oil of the present invention can be produced by polymerizing a monomer mixture containing the component (m1) and the component (M) in a base oil by a known method.
  • the base oil is not particularly limited, but includes API standard Group III base oil such as YUBASE3 manufactured by SK Lubricants, API standard Group III plus base oil such as YUBASE4 manufactured by SK Lubricants, and API standard Group IV base oil such as polyalphaolefin. etc.
  • the component (M) is preferably a macromonomer obtained by polymerizing a monomer mixture containing a vinyl radically polymerizable monomer in the base oil using a cobalt chain transfer agent. Since the cobalt chain transfer agent has a high chain transfer constant, a macromonomer with a controlled molecular weight can be obtained by adding a small amount.
  • the polymerization may be carried out under known conditions, it is preferable to use ⁇ -methylstyrene dimer as the chain transfer agent because it has a particularly excellent effect of suppressing heat generation during polymerization.
  • the friction reducing agent for lubricating oils containing the polymer of the present invention is suitable for use in engine oils, drive system oils (gear oils, transmission oils), hydraulic oils, etc. used in mobility such as automobiles and ships, industrial machinery, robots, etc. It can be used as a friction reducer added to lubricating oils such as metal working oils.
  • Examples of the base oil of the lubricating oil include mineral base oils refined from crude oil and chemically synthesized synthetic oils, such as API standard Group III base oils such as YUBASE3 manufactured by SK Lubricants, Examples include API standard Group III plus base oils such as YUBASE4 manufactured by Manufacturer Co., Ltd., and API standard Group IV base oils such as polyalphaolefin.
  • the lubricating oil composition of the present invention contains the lubricating oil friction reducing agent of the present invention.
  • the lubricating oil composition of the present invention may contain other additives other than the lubricating oil friction reducing agent of the present invention.
  • Other additives include antioxidants, viscosity index improvers, pour point depressants, detergent dispersants, corrosion inhibitors, rust inhibitors, antifoaming agents, emulsifiers, fungicides, demulsifiers, and the like.
  • friction reducing agents other than those of the present invention include oiliness improvers such as long-chain fatty acid esters and fatty acid amides, anti-wear agents such as phosphoric acid esters and zinc dithiophosphate, and extreme pressure agents such as organic sulfur compounds and organic halogen compounds. , a friction modifier such as an organic molybdenum compound.
  • the lubricating oil composition of the present invention may be a grease containing a thickener.
  • the thickener include soap-based (lithium soap, calcium soap, sodium soap, aluminum soap, etc.), inorganic-based (bentonite, silica gel, etc.), organic-based (polyurea, polyurethane, etc.), and the like.
  • the content of the polymer of the present invention contained in the lubricating oil composition is preferably 0.01 to 30% by mass, more preferably 0.05 to 25% by mass, based on 100% by mass of the lubricating oil composition. More preferably 0.1 to 20% by mass.
  • a base oil solution containing 2% by mass of the polymer is prepared, and the friction coefficient measured at 40°C using an SRV5 tester (manufactured by Optimol Instruments Pruftechnik GmbH) is preferably 0.16 or less, and preferably less than 0.138. is more preferable, and even more preferably 0.135 or less.
  • a base oil solution containing 2% by mass of the polymer is prepared, and the kinematic viscosity at 40°C measured according to the ASTM D7279 (D445) method is preferably 0 to 22.4 cSt, preferably 5 to 22.25 cSt. It is more preferably 10 to 22.00 cSt, and particularly preferably 15 to 21.50 cSt.
  • the base oil is API standard Group III plus.
  • TSKgel SuperHZM-M inner diameter 4.6 mm, length 15 cm
  • HZM-M inner diameter 4.6 mm, length 15 cm
  • HZ-2000 inner diameter 4.6 mm, length 15 cm
  • TSKguardcolumn SuperHZ-L inner diameter 4.6 mm, length 3.5 cm
  • ⁇ Kinematic viscosity at 40°C> A YUBASE4 solution containing 2% by mass of the obtained polymer was prepared, and according to the ASTM D7279 (D445) method, using a fully automatic simple kinematic viscometer (manufactured by Cannon, trade name: Simple-VIS type), The kinematic viscosity at 40°C was evaluated.
  • a mixed solution consisting of YUBASE4 (2 parts) and 0.1 part of t-amylperoxy-2-ethylhexanoate (manufactured by Arkema Yoshitomi, trade name: Luperox 575) as a polymerization initiator was added, and the temperature of the liquid was raised to 90°C. After raising the temperature to .degree. C. and stirring for 2.5 hours, a mixed solution consisting of YUBASE 4 (10 parts) and Luperox 26 (0.7 parts) was added dropwise over 1 hour.
  • a mixed solution consisting of YUBASE4 (2 parts) and Luperox 26 (0.2 parts) as a polymerization initiator was added, the temperature of the solution was raised to 90°C, and after stirring for 2.5 hours, YUBASE4 (10 parts)
  • a mixed solution consisting of and Luperox 26 (0.7 parts) was added dropwise over 1 hour. After the dropwise addition, the temperature was raised to 105°C and held for 1.5 hours, and then 20 parts of YUBASE4 was added and cooled to obtain a YUBASE4 solution containing 52.6% by mass of macromonomer M3.
  • Table 1 shows the GPC results of the obtained macromonomer M3.
  • a mixed solution consisting of YUBASE4 (2 parts) and Luperox 26 (0.4 parts) as a polymerization initiator was added, the temperature of the solution was raised to 90°C, and after stirring for 2.5 hours, YUBASE4 (10 parts)
  • a mixed solution consisting of and Luperox 26 (0.7 parts) was added dropwise over 1 hour. After the dropwise addition, the temperature was raised to 105°C and held for 1.5 hours, and then 20 parts of YUBASE4 was added and cooled to obtain a YUBASE4 solution containing 52.6% by mass of macromonomer M4.
  • Table 1 shows the GPC results of the obtained macromonomer M4.
  • a mixed solution consisting of YUBASE4 (2 parts) and 0.1 part of t-amylperoxy-2-ethylhexanoate (manufactured by Arkema Yoshitomi, trade name: Luperox 575) as a polymerization initiator was added, and the temperature of the liquid was raised to 90°C. After raising the temperature to .degree. C. and stirring for 2.5 hours, a mixed solution consisting of YUBASE 4 (10 parts) and Luperox 26 (0.7 parts) was added dropwise over 1 hour.
  • Example 1 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 56 parts of n-butyl acrylate, 19 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • a mixed solution of YUBASE4 (50 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours.
  • YUBASE4 58.1 parts was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 2 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • the polymer composition also includes the structural unit in the macromonomer (M).
  • Example 2 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 56 parts of n-butyl acrylate, 19 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 3 30 parts of YUBASE4 and 9.5 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 71 parts of n-butyl acrylate, 24 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • a mixed solution of YUBASE4 (50 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours. After raising the temperature to 110° C. and maintaining it for 1 hour, YUBASE4 (56.1 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 2 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • Example 4 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 40 parts of YUBASE4, 66.7 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3, 49 parts of n-butyl acrylate, and 16 parts of lauryl acrylate. 0.03 parts of Luperox 26 as a polymerization initiator and 0.7 parts of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • Example 5 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, 45 parts of n-butyl acrylate, and 30 parts of lauryl acrylate were added. 0.03 parts of Luperox 26 as a polymerization initiator and 0.9 parts of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • Example 6 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, 30 parts of n-butyl acrylate, and 45 parts of lauryl acrylate. 0.03 parts of Luperox 26 as a polymerization initiator and 0.9 parts of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • Example 7 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, 20 parts of n-butyl acrylate, and 55 parts of lauryl acrylate. 0.03 parts of Luperox 26 as a polymerization initiator and 0.9 parts of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • Example 8> In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, 30 parts of ethyl acrylate (manufactured by Mitsubishi Chemical Corporation), Add 45 parts of lauryl acrylate, 0.03 parts of Luperox 26 as a polymerization initiator, and 0.9 parts of ⁇ -methylstyrene dimer (manufactured by NOF Corporation, trade name: NOFUMER MSD) as a chain transfer agent, and add nitrogen while stirring. was bubbled to remove dissolved oxygen. The liquid temperature was raised to 85° C.
  • Example 9 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M3 obtained in Production Example 4, 56 parts of n-butyl acrylate, and 19 parts of lauryl acrylate. 0.03 parts of Luperox 26 as a polymerization initiator and 0.9 parts of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • Example 10 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M4 obtained in Production Example 5, 56 parts of n-butyl acrylate, and 19 parts of lauryl acrylate. 1 part, 0.03 part of Luperox 26 as a polymerization initiator and 0.9 part of ⁇ -methylstyrene dimer (manufactured by NOF Corporation, trade name: NOFUMER MSD) as a chain transfer agent were added, and nitrogen was bubbled while stirring. Dissolved oxygen was excluded. The liquid temperature was raised to 85° C.
  • Example 11 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 56 parts of n-butyl acrylate, 19 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (1.5 parts as a chain transfer agent) were added. A mixed solution consisting of 2 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 12 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 50 parts of n-butyl acrylate, 25 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 13 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded.
  • the liquid temperature was raised to 85°C, 25 parts of YUBASE4, 20 parts of n-butyl acrylate, 25 parts of lauryl acrylate, 30 parts of n-butyl methacrylate (manufactured by Mitsubishi Chemical Corporation, trade name: Acryester B), A mixed solution consisting of 0.1 part of Luperox 575 as a polymerization initiator and Nofumar MSD (0.9 part) as a chain transfer agent was added dropwise over 4 hours. After holding at 85° C. for 1 hour, a mixed solution of YUBASE4 (50 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours. After raising the temperature to 110° C.
  • YUBASE4 (58.1 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 3 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • Example 14 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded.
  • the liquid temperature was raised to 85°C, 25 parts of YUBASE4, 20 parts of n-butyl acrylate, 25 parts of lauryl acrylate, 30 parts of Acryester B, 0.1 part of Luperox 575 as a polymerization initiator, and chain transfer.
  • a liquid mixture consisting of Nohumer MSD (0.9 parts) as an agent was added dropwise over 4 hours. After holding at 85° C.
  • Example 15 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 45 parts of n-butyl acrylate, 30 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 16 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 60 parts of n-butyl acrylate, 15 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (1.5 parts as a chain transfer agent) were added. A mixed solution consisting of 2 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 17 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 64 parts of n-butyl acrylate, 11 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (1.5 parts as a chain transfer agent) were added. A mixed solution consisting of 2 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 18 30 parts of YUBASE4 and 95.2 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and a mixture consisting of 25 parts of YUBASE4, 50 parts of n-butyl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nohumer MSD (1.2 parts) as a chain transfer agent was prepared. The liquid was added dropwise over 4 hours. After holding at 85° C.
  • Example 19 30 parts of YUBASE4 and 38.1 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 60 parts of n-butyl acrylate, 20 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • a mixed solution of YUBASE4 (50 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours.
  • YUBASE4 (62.5 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 3 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • Example 20 30 parts of YUBASE4 and 19 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. .
  • the liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 67 parts of n-butyl acrylate, 23 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added.
  • a mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 21 50 parts of YUBASE4 and 9.5 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 71 parts of n-butyl acrylate, 24 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 22 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M5 obtained in Production Example 6 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 56 parts of n-butyl acrylate, 19 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (1.5 parts as a chain transfer agent) were added. A mixed solution consisting of 2 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 23 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M5 obtained in Production Example 6 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 45 parts of n-butyl acrylate, 30 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0.1 part as a chain transfer agent) were added. A mixed solution consisting of 9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 24 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M5 obtained in Production Example 6 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 64 parts of n-butyl acrylate, 11 parts of lauryl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (1.5 parts as a chain transfer agent) were added. A mixed solution consisting of 2 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 25 30 parts of YUBASE4 and 95.2 parts of the YUBASE4 solution of macromonomer M5 obtained in Production Example 6 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded.
  • the liquid temperature was raised to 85°C, and a mixture consisting of 25 parts of YUBASE4, 50 parts of n-butyl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nohumer MSD (1.2 parts) as a chain transfer agent was prepared. The liquid was added dropwise over 4 hours. After holding at 85° C.
  • Example 26 In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3, and 56 parts of 2-ethylhexyl acrylate (manufactured by Mitsubishi Chemical Corporation) were added. 19 parts of lauryl acrylate, 0.03 parts of Luperox 26 as a polymerization initiator, and 1.2 parts of ⁇ -methylstyrene dimer as a chain transfer agent, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • Example 27 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, 25 parts of YUBASE4, 56 parts of n-butyl acrylate, 19 parts of lauryl acrylate, 1 part of Luperox 575 as a polymerization initiator, and Nofumer MSD (1.9 parts) as a chain transfer agent. ) was added dropwise over 4 hours. After holding at 85° C.
  • Example 28 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded.
  • the liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 56 parts of n-butyl acrylate, 18 parts of lauryl acrylate, 4-hydroxybutyl acrylate (manufactured by Mitsubishi Chemical Corporation, trade name: 4HBA) (1 part), A liquid mixture consisting of 0.1 part of Luperox 575 as a polymerization initiator and Nohumer MSD (1.9 parts) as a chain transfer agent was added dropwise over 4 hours. After holding at 85° C. for 1 hour, a mixed solution of YUBASE4 (50 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours. After raising the temperature to 110° C.
  • YUBASE4 (58.1 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 4 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • Example 29 30 parts of YUBASE4 and 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded.
  • the liquid temperature was raised to 85°C, and 25 parts of YUBASE4, 54 parts of n-butyl acrylate, 18 parts of lauryl acrylate, 4-hydroxybutyl acrylate (manufactured by Mitsubishi Chemical Corporation, trade name: 4HBA) (3 parts), A liquid mixture consisting of 3 parts of Luperox 575 as a polymerization initiator and Nofumar MSD (4 parts) as a chain transfer agent was added dropwise over 4 hours. After holding at 85° C. for 1 hour, a mixed solution of YUBASE4 (50 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours. After raising the temperature to 110° C.
  • YUBASE4 (58.1 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 4 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • Example 30 30 parts of YUBASE4 and 95.2 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and a mixed solution consisting of 25 parts of YUBASE4, 50 parts of n-butyl acrylate, 1 part of Luperox 575 as a polymerization initiator, and Nofumer MSD (1.9 parts) as a chain transfer agent was added. The mixture was added dropwise over 4 hours. After holding at 85° C.
  • Example 31 30 parts of YUBASE4 and 95.2 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, 25 parts of YUBASE4, 47 parts of n-butyl acrylate, 3 parts of 4-hydroxybutyl acrylate, 0.5 part of Luperox 575 as a polymerization initiator, and Nofmar MSD as a chain transfer agent. (0.9 part) was added dropwise over 4 hours. After holding at 85° C.
  • Example 32 30 parts of YUBASE4 and 95.2 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, 25 parts of YUBASE4, 47 parts of n-butyl acrylate, 3 parts of 4-hydroxybutyl acrylate, 0.1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD as a chain transfer agent. (1.3 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 33 30 parts of YUBASE4 and 133.1 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and a mixture consisting of 30 parts of YUBASE4, 30 parts of n-butyl acrylate, 0.5 parts of Luperox 575 as a polymerization initiator, and Nofumer MSD (0.9 parts) as a chain transfer agent was prepared. The liquid was added dropwise over 4 hours. After holding at 85° C.
  • a mixed solution of YUBASE4 (20 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours. After raising the temperature to 110° C. and maintaining it for 1 hour, YUBASE4 (44.5 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of a (meth)acrylic graft copolymer.
  • Table 5 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • Example 34 30 parts of YUBASE4 and 133.1 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85°C, and 30 parts of YUBASE4, 27 parts of n-butyl acrylate, 3 parts of 4-hydroxybutyl acrylate, 1 part of Luperox 575 as a polymerization initiator, and Nofmar MSD (0 .9 parts) was added dropwise over 4 hours. After holding at 85° C.
  • Example 35 10 parts of YUBASE4 and 171.0 parts of the YUBASE4 solution of macromonomer M2 obtained in Production Example 3 were added to a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, and dissolved oxygen was removed by bubbling nitrogen while stirring. Excluded. The liquid temperature was raised to 85° C., and a mixed solution consisting of 30 parts of YUBASE4, 10 parts of n-butyl acrylate, and 0.3 parts of Luperox 575 as a polymerization initiator was added dropwise over 4 hours. After holding at 85° C. for 1 hour, a mixed solution of YUBASE4 (45 parts) and Luperox 575 (0.5 parts) was added dropwise over 1.5 hours.
  • YUBASE4 (22.5 parts) was added and cooled to obtain a YUBASE4 solution containing 35% by mass of (meth)acrylic graft copolymer.
  • Table 5 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • ⁇ Comparative example 1> In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 50 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, 56 parts of n-butyl acrylate, and 19 parts of lauryl acrylate. 0.03 part of Luperox 26 as a polymerization initiator and 0.1 part of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C.
  • ⁇ Comparative example 3> In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, add 72.6 parts of YUBASE4, 45 parts of n-butyl acrylate, 30 parts of lauryl acrylate, 24.5 parts of Acryester SL, and 0.5 parts of MMA. 0.03 parts of Luperox 26 as a polymerization initiator and 0.15 parts of ⁇ -methylstyrene dimer as a chain transfer agent were added, and dissolved oxygen was removed by bubbling nitrogen while stirring. The liquid temperature was raised to 85° C. and held for 3.5 hours, and then a mixed solution consisting of YUBASE 4 (42 parts) and Luperox 26 (0.015 parts) was added dropwise over 2 hours.
  • YUBASE4 60 parts
  • 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate manufactured by NOF Corporation, trade name: Perocta-O
  • a mixed solution consisting of 0.5 part was added dropwise over 1 hour. Thereafter, the temperature was raised to 110° C. and maintained for 1 hour, and then 11.1 parts of YUBASE4 was added and cooled to obtain a YUBASE4 solution containing 35% by mass of the polymer.
  • Table 6 shows the evaluation results of the obtained friction reducing agent for lubricating oil.
  • ⁇ Comparative example 4> In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 6.9 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, and n-butyl methacrylate (manufactured by Mitsubishi Chemical Corporation, Add 45 parts of product name: Acryester B), 30 parts of lauryl acrylate, 0.15 parts of Luperox 26 as a polymerization initiator, and 0.025 parts of ⁇ -methylstyrene dimer as a chain transfer agent, and add nitrogen while stirring. Dissolved oxygen was removed by bubbling. The liquid temperature was raised to 85° C.
  • ⁇ Comparative example 5> In a reaction vessel equipped with a stirrer, a cooling tube, and a thermometer, 6.9 parts of YUBASE4, 47.6 parts of the YUBASE4 solution of macromonomer M1 obtained in Production Example 2, and n-butyl methacrylate (manufactured by Mitsubishi Chemical Corporation, Add 35 parts of product name: Acryester B), 40 parts of lauryl acrylate, 0.15 parts of Luperox 26 as a polymerization initiator, and 0.025 parts of ⁇ -methylstyrene dimer as a chain transfer agent, and add nitrogen while stirring. Dissolved oxygen was removed by bubbling. The liquid temperature was raised to 85° C.
  • ⁇ SLMA A mixture of alkyl methacrylate whose alkyl group has 12 carbon atoms and alkyl methacrylate whose alkyl group has 13 carbon atoms (manufactured by Mitsubishi Chemical Corporation, product name: Acryester SL)
  • ⁇ SMA n-stearyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., product name: Light Ester S)
  • ⁇ LMA Lauryl methacrylate (manufactured by Mitsubishi Chemical Corporation, product name: Acryester L)
  • ⁇ MMA Methyl methacrylate (manufactured by Mitsubishi Chemical Corporation, product name: Acryester M)
  • ⁇ EHMA 2-ethylhexyl methacrylate (manufactured by Mitsubishi Chemical Corporation, trade name "Acryester EH”)
  • ⁇ M1 Macromonomer synthesized in Production Example 2
  • ⁇ M2 Macromonomer
  • the friction reducers for lubricating oils obtained in each example had low kinematic viscosity and a high effect of reducing the coefficient of friction.
  • the friction reducing agents for lubricating oils obtained in each comparative example had high kinematic viscosity and had a low effect of reducing the coefficient of friction.
  • a polymer that has a high friction reducing effect and can provide a low viscosity polymer lubricating oil additive, a friction reducing agent for lubricating oil, and a lubricating oil composition.

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