WO2018198645A1 - Additif destiné à un lubrifiant, composition lubrifiante, et mécanisme coulissant - Google Patents

Additif destiné à un lubrifiant, composition lubrifiante, et mécanisme coulissant Download PDF

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Publication number
WO2018198645A1
WO2018198645A1 PCT/JP2018/012512 JP2018012512W WO2018198645A1 WO 2018198645 A1 WO2018198645 A1 WO 2018198645A1 JP 2018012512 W JP2018012512 W JP 2018012512W WO 2018198645 A1 WO2018198645 A1 WO 2018198645A1
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Prior art keywords
acid
lubricating oil
mass
additive
general formula
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PCT/JP2018/012512
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English (en)
Japanese (ja)
Inventor
八木下　和宏
直史 置塩
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Ｊｘｔｇエネルギー株式会社
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Priority claimed from JP2017090492A external-priority patent/JP2018188519A/ja
Priority claimed from JP2017090498A external-priority patent/JP2018188521A/ja
Priority claimed from JP2017090496A external-priority patent/JP2018188520A/ja
Application filed by Ｊｘｔｇエネルギー株式会社 filed Critical Ｊｘｔｇエネルギー株式会社
Publication of WO2018198645A1 publication Critical patent/WO2018198645A1/fr

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    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • 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
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons

Definitions

  • the present invention relates to an additive for lubricating oil, a lubricating oil composition, and a sliding mechanism.
  • Lubricating oil is used in industrial machines having mechanical elements such as hydraulic machines, compression machines, turbines, gear elements, and bearings. Industrial machines have been operated under more severe conditions as the speed, pressure, and size have been reduced. For this reason, the lubricating oil used in industrial machines is required to have excellent lubricating performance that can sufficiently guarantee the mechanical life for a long time even when used under high pressure, high speed, high load, and high temperature.
  • Patent Document 1 discloses a lubricating oil composition in which a phosphorus compound having a group in which hydroxyl groups are bonded to adjacent carbon atoms is blended with a base oil mainly composed of an oxygen-containing compound. .
  • the present invention has been made in view of such circumstances, has excellent lubricity, and has sufficient solubility even when applied to a hydrocarbon base oil.
  • the main purpose is to provide an agent.
  • the present invention provides an additive for lubricating oil shown in [1] below, a lubricating oil composition shown in [2] below, use (application) of a compound shown in [3] below, and production of a compound shown in [4] below Provides use (application) for.
  • R 1 represents an alkylene group, and R 2 and R 3 each independently represent a hydrocarbon group. m represents 0 or 1, and n represents 0 or 1. However, m + n is 1.
  • R 2 and R 3 each independently represent a hydrocarbon group. m represents 0 or 1, and n represents 0 or 1. However, m + n is 1.
  • R 1 represents an alkylene group
  • R 2 and R 3 each independently represent a hydrocarbon group
  • m represents 0 or 1
  • n represents 0 or 1.
  • m + n is 1.
  • the present invention also provides the lubricating oil composition shown in the following [5] and [6].
  • a lubricating oil composition comprising an ester base oil and an additive for lubricating oil represented by the following general formula (1) (the lubricating base oil is an ester base oil; [2 ] The lubricating oil composition as described in.].
  • R 1 represents an alkylene group, and R 2 and R 3 each independently represent a hydrocarbon group.
  • m represents 0 or 1
  • n represents 0 or 1.
  • m + n is 1.
  • the present invention provides a lubricating oil composition shown in the following [7] to [9], a sliding mechanism shown in the following [10], use (application) of the composition shown in the following [11], and the following [12].
  • a hydrocarbon base oil and an additive for a lubricating oil represented by the following general formula (1) are used for lubricating a pair of sliding members that move relative to each other,
  • a lubricating oil composition in which at least one of the sliding members has a sliding surface covered with a diamond-like carbon film (a pair of lubricating base oil is a hydrocarbon base oil and moves relatively oppositely)
  • R 1 represents an alkylene group
  • R 2 and R 3 each independently represent a hydrocarbon group.
  • m represents 0 or 1
  • n represents 0 or 1.
  • m + n is 1.
  • Use which has a sliding surface and the composition contains a hydrocarbon base oil and an additive for lubricating oil represented by the following general formula (1).
  • R 1 represents an alkylene group
  • R 2 and R 3 each independently represent a hydrocarbon group.
  • m represents 0 or 1
  • n represents 0 or 1.
  • m + n is 1.
  • Use which has a coated sliding surface and the composition contains a hydrocarbon base oil and an additive for lubricating oil represented by the following general formula (1).
  • R 1 represents an alkylene group
  • R 2 and R 3 each independently represent a hydrocarbon group.
  • m represents 0 or 1
  • n represents 0 or 1.
  • m + n is 1.
  • the 40 ° C. and 100 ° C. kinematic viscosity and the viscosity index mean values measured in accordance with JIS K2283: 2000 “Crude oil and petroleum products—Kinematic viscosity test method and viscosity index calculation method”, respectively.
  • an ashless lubricating oil additive which has excellent lubricity and has sufficient solubility even when applied to a hydrocarbon base oil.
  • the lubricating oil composition using such an additive for lubricating oil is provided.
  • the lubricating oil composition capable of reducing the friction torque of the sliding surface between the sliding members and the sliding using the same A mechanism is provided.
  • Example 2 is an IR spectrum of glyceryl (n-hexyl) phosphonate (n-hexyl) obtained in Example 1-1.
  • 3 is an IR spectrum of glyceryl (2-ethylhexyl) phosphonate (2-ethylhexyl) obtained in Example 1-2.
  • 3 is an IR spectrum of (glyceryl) phosphonic acid di (n-hexyl) obtained in Example 1-3.
  • the additive for lubricating oil according to the first embodiment is composed of a compound represented by the general formula (1).
  • the additive for lubricating oil according to the first embodiment has excellent lubricity and has sufficient solubility even when applied to a hydrocarbon base oil.
  • the additive for lubricating oils may be used individually by 1 type, and may be used combining 2 or more types by arbitrary ratios.
  • R 1 represents an alkylene group
  • R 2 and R 3 each independently represent a hydrocarbon group
  • m represents 0 or 1
  • n represents 0 or 1.
  • m + n is 1.
  • the alkylene group as R 1 may be a linear or branched alkylene group having 1 to 10 carbon atoms.
  • the alkylene group may have 1 to 5, 1 to 3, 1 or 2, or 1.
  • the hydrocarbon group as R 2 and R 3 may be a linear, branched or cyclic alkyl group or alkenyl group. R 2 and R 3 may be the same as or different from each other.
  • Examples of the hydrocarbon group include n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, neopentyl group, Examples include n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, nonyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, hexanyl group, cyclohexyl group, and oleyl group.
  • the hydrocarbon group is a linear or branched alkyl group having 3 to 18 carbon atoms, a linear or branched alkyl group having 4 to 12 carbon atoms, or a linear or branched alkyl group. It may be an alkyl group having 6 to 10 carbon atoms.
  • the compound represented by the general formula (1) is a compound represented by the general formula (A) (a compound in which m is 1 and n is 0 in the general formula (1)) or the general formula (B). (A compound in which m in general formula (1) is 0 and n is 1).
  • R 1A , R 2A , and R 3A have the same meanings as R 1 , R 2 , and R 3 described above.
  • the additive for lubricating oil represented by the general formula (A) is obtained by, for example, reacting a compound represented by the general formula (A-1) with a compound represented by the general formula (A-2). Obtainable.
  • the compound represented by the general formula (A-1) and the compound represented by the general formula (A-2) can be used as they are for the compound represented by the general formula (A-1) and the compound represented by the general formula (A-2).
  • the ratio when the compound represented by the general formula (A-1) and the compound represented by the general formula (A-2) are reacted is 1 mol of the compound represented by the general formula (A-2).
  • the amount of the compound represented by the general formula (A-1) may be 0.8 mol or more, or 0.9 to 1 mol.
  • R 1B , R 2B , and R 3B have the same meanings as R 1 , R 2 , and R 3 described above.
  • the additive for lubricating oil represented by the general formula (B) is, for example, Bulletin de la Societye Chimique de France 1983-5-6, Pt. 2, 125-130. More specifically, an epoxy compound (B-3) is obtained by reacting a compound represented by the general formula (B-1) with a compound represented by the general formula (B-2). It can be obtained by ring-opening an epoxy compound by acid treatment or the like.
  • R 4B has the same meaning as R 2 and R 3 described above.
  • R 2B , R 3B , and R 4B may be the same as or different from each other.
  • the compound represented by the general formula (B-1) and the compound represented by the general formula (B-2) can be used as they are for the compound represented by the general formula (B-1) and the compound represented by the general formula (B-2).
  • the ratio when the compound represented by the general formula (B-1) and the compound represented by the general formula (B-2) are reacted is based on 1 mol of the compound represented by the general formula (B-2).
  • the amount of the compound represented by the general formula (B-1) may be 0.8 mol or more, or 0.9 to 1 mol.
  • reaction conditions for synthesizing the lubricant additive represented by the general formula (1) can be appropriately selected according to the raw materials used.
  • examples of the reaction conditions include stirring at 40 to 200 ° C. for 0.5 to 48 hours in the absence or presence of a solvent.
  • the lubricating oil composition according to the second embodiment contains a lubricating base oil and the lubricating oil additive represented by the general formula (1) according to the first embodiment.
  • the lubricating oil composition according to the second embodiment can reduce wear, seizure, and the like under severe conditions under high loads, and exhibits excellent lubricity.
  • a lubricating base oil used in a normal lubricating oil field can be used.
  • specific examples of the lubricating base oil include a mineral base oil, a synthetic base oil, or a mixture of both.
  • Mineral oil base oils include, for example, kerosene fractions obtained by distillation of paraffinic, naphthenic, or aromatic crude oils; normal paraffins obtained by extraction operations from kerosene fractions; and paraffinic, naphthenic, Or a Fischer-Tropsch wax obtained by a lubricating oil fraction obtained by distillation of an aromatic crude oil, or a wax such as slack wax obtained by a lubricating oil dewaxing process and / or a gas-to-liquid (GTL) process, etc.
  • kerosene fractions obtained by distillation of paraffinic, naphthenic, or aromatic crude oils
  • normal paraffins obtained by extraction operations from kerosene fractions
  • paraffinic, naphthenic or a Fischer-Tropsch wax obtained by a lubricating oil fraction obtained by distillation of an aromatic crude oil
  • a wax such as slack wax obtained by a lubricating oil dewaxing process and / or a gas-
  • Synthetic wax such as GTL wax is used as a raw material, and solvent purification, solvent extraction, hydrocracking, hydroisomerization, solvent dewaxing, catalytic dewaxing, hydrorefining, sulfuric acid washing, clay treatment, etc.
  • These mineral oil base oils may be used alone or in combination of two or more at any ratio.
  • Synthetic base oils include, for example, poly ⁇ -olefins or hydrides thereof; olefin oligomers such as propylene oligomers, isobutylene oligomers, polybutenes, 1-octene oligomers, 1-decene oligomers, ethylene-propylene oligomers or hydrides thereof; alkylbenzenes Alkyl naphthalene; diester (ditridecyl glutarate, di-2-ethylhexyl adipate, di-2-ethylhexyl azelate, diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl sebacate, etc.); polyol ester (trimethylolpropane capri) Rate, trimethylolpropane pelargonate, trimethylolpropane oleate, pentaerythritol 2-eth
  • the additive for lubricating oil according to the first embodiment is excellent in solubility even when applied to a hydrocarbon base oil, it can be suitably applied to a hydrocarbon base oil.
  • the hydrocarbon base oil include mineral oil hydrocarbon oil, synthetic hydrocarbon oil, or a mixture of both.
  • group base oil can be used for mineral oil type hydrocarbon oil.
  • Synthetic hydrocarbon oils include, for example, poly ⁇ -olefins or hydrides thereof; olefin oligomers such as propylene oligomers, isobutylene oligomers, polybutenes, 1-octene oligomers, 1-decene oligomers, ethylene-propylene oligomers, or hydrides thereof; Alkylbenzene; alkylnaphthalene. These synthetic hydrocarbon oils may be used alone or in combination of two or more at any ratio.
  • the sulfur content of the lubricating base oil may be 100 mass ppm or less, 50 mass ppm or less, or 10 mass ppm or less, based on the total amount of the base oil.
  • the sulfur content in the present specification means a value measured according to JIS K2541 “Crude oil and petroleum products—sulfur content test method”.
  • the kinematic viscosity at 40 ° C. of the lubricating base oil is not particularly limited, but may be 1 mm 2 / s or more, 10 mm 2 / s or more, or 15 mm 2 / s or more.
  • the kinematic viscosity at 40 ° C. of the lubricating base oil may be 100 mm 2 / s or less, 80 mm 2 / s or less, or 60 mm 2 / s or less.
  • the viscosity index of the lubricating base oil is not particularly limited, but may be 70 or more, 90 or more, or 110 or more. When the viscosity index is within the above range, the stability of the viscosity with respect to the external temperature is ensured, so that the oil film tends to be stably formed even with respect to the external temperature change during use.
  • the total aromatic content of the lubricating base oil is not particularly limited, but may be 30% by mass or less, 15% by mass or less, 5% by mass or less, or 2% by mass or less. When the total aromatic content of the lubricating base oil is 30% by mass or less, the oxidation stability tends to be superior.
  • the total aromatic content in this specification means the aromatic fraction content measured based on ASTMD2549. Usually, this aromatic fraction includes alkylbenzene, alkylnaphthalene, anthracene, phenanthrene, and alkylated products thereof, compounds in which four or more benzene rings are condensed, or pyridines, quinolines, phenols, naphthols, etc. Compounds having heteroaromatics and the like are included.
  • the content of the additive for lubricating oil represented by the general formula (1) is not particularly limited, but from the viewpoint of improving the wear resistance, 0.005% by mass in terms of phosphorus element based on the total amount of the composition. (50 mass ppm) or more, 0.01 mass% (100 mass ppm) or more, or 0.03 mass% (300 mass ppm) or more. Further, from the viewpoint of suppression of catalyst poisoning and suppression of corrosion of non-ferrous metals, 0.20 mass% (2000 mass ppm) or less and 0.10 mass% (1000 mass) in terms of phosphorus element based on the total amount of the composition. ppm) or less, or 0.08 mass% (800 mass ppm) or less.
  • the lubricating oil composition according to the second embodiment can further contain any commonly used additive depending on the purpose.
  • additives include viscosity modifiers, metal detergents, ashless dispersants, friction modifiers, and antiwear agents (extreme pressure agents) other than the lubricant additive represented by the general formula (1). ), Antioxidants, corrosion inhibitors, rust inhibitors, pour point depressants, demulsifiers, metal deactivators, antifoaming agents, and the like.
  • the viscosity modifier may be a non-dispersed or dispersed ester group-containing viscosity modifier.
  • the viscosity modifier include a non-dispersed or dispersed poly (meth) acrylate viscosity modifier, a non-dispersed or dispersed olefin- (meth) acrylate copolymer viscosity modifier, and a styrene-maleic anhydride copolymer. Examples thereof include a polymer system viscosity modifier and a mixture thereof.
  • the viscosity modifier may be a non-dispersed or dispersed poly (meth) acrylate viscosity modifier, or a non-dispersed or dispersed polymethacrylate viscosity modifier.
  • viscosity modifiers include non-dispersed or dispersed ethylene- ⁇ -olefin copolymers or hydrogenated products thereof, polyisobutylene or hydrogenated products thereof, styrene-diene hydrogenated copolymers, and polyalkylstyrenes. be able to.
  • metal detergents include sulfonate detergents, salicylate detergents, phenate detergents, and the like, neutral salts with alkali metals or alkaline earth metals, basic salts, and overbased salts. Any of them can be blended. In use, one kind or two or more kinds arbitrarily selected from these can be blended.
  • any ashless dispersant used in lubricating oils can be used, for example, a mono- or mono-chain alkyl group or alkenyl group having 40 to 400 carbon atoms in the molecule.
  • a bissuccinimide, a benzylamine having at least one alkyl group or alkenyl group having 40 to 400 carbon atoms in the molecule, a polyamine having at least one alkyl group or alkenyl group having 40 to 400 carbon atoms in the molecule examples include boron compounds, carboxylic acids, phosphoric acids, and the like. In use, one kind or two or more kinds arbitrarily selected from these can be blended.
  • the friction modifier examples include ashless friction modifiers such as fatty acid esters, aliphatic amines, and fatty acid amides, and metal friction modifiers such as molybdenum dithiocarbamate and molybdenum dithiophosphate.
  • the friction modifier is, for example, an amine compound, an imide compound having at least one alkyl group or alkenyl group having 6 to 30 carbon atoms, particularly a linear alkyl group or linear alkenyl group having 6 to 30 carbon atoms in the molecule, Fatty acid esters, fatty acid amides, fatty acid metal salts and the like may be used.
  • an anti-wear agent other than the additive for lubricating oil represented by the general formula (1)
  • a sulfur-based, phosphorus-based, sulfur-phosphorus-based extreme pressure agent and the like can be used.
  • antioxidants examples include ashless antioxidants such as phenols and amines, and metal antioxidants such as copper and molybdenum.
  • phenol-based ashless antioxidants include 4,4′-methylenebis (2,6-di-tert-butylphenol), 4,4′-bis (2,6-di-tert-
  • amine-based ashless antioxidants include phenyl- ⁇ -naphthylamine, alkylphenyl- ⁇ -naphthylamine, dialkyldiphenylamine, and diphenylamine.
  • corrosion inhibitor examples include benzotriazole, tolyltriazole, thiadiazole, and imidazole compounds.
  • rust preventive examples include petroleum sulfonate, alkylbenzene sulfonate, dinonylnaphthalene sulfonate, alkenyl succinic acid ester, and polyhydric alcohol ester.
  • pour point depressant for example, a polymethacrylate polymer compatible with the lubricating base oil to be used can be used.
  • demulsifier examples include polyalkylene glycol nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene alkyl naphthyl ether.
  • metal deactivator examples include imidazoline, pyrimidine derivatives, alkylthiadiazole, mercaptobenzothiazole, benzotriazole or derivatives thereof, 1,3,4-thiadiazole polysulfide, 1,3,4-thiadiazolyl-2,5-bis.
  • metal deactivator examples include dialkyldithiocarbamate, 2- (alkyldithio) benzimidazole, ⁇ - (o-carboxybenzylthio) propiononitrile.
  • antifoaming agents examples include silicone oils having a kinematic viscosity at 25 ° C. of 1,000 to 100,000 mm 2 / s, alkenyl succinic acid derivatives, esters of polyhydroxy aliphatic alcohols and long chain fatty acids, methyl salicylates and o-hydroxys. Examples include esters with benzyl alcohol.
  • each content may be 0.01 to 20% by mass based on the total amount of the composition.
  • the kinematic viscosity at 40 ° C. of the lubricating oil composition according to the second embodiment is not particularly limited, but may be 5 mm 2 / s or more, 10 mm 2 / s or more, or 20 mm 2 / s or more.
  • the kinematic viscosity at 40 ° C. of the lubricating oil composition may be 90 mm 2 / s or less, 70 mm 2 / s or less, or 50 mm 2 / s or less.
  • the lubricating oil composition according to the third embodiment contains an ester base oil and the lubricating oil additive represented by the general formula (1) according to the first embodiment.
  • the lubricating oil composition according to the third embodiment can reduce wear, seizure, and the like under severe conditions under high loads, and exhibits excellent lubricity.
  • ester base oil an ester base oil used in a normal lubricating oil field can be used.
  • Specific examples of the ester base oil include monoesters, diesters, and polyol esters.
  • the alcohol constituting the ester base oil may be a monohydric alcohol or a polyhydric alcohol.
  • the acid constituting the ester base oil may be a monobasic acid or a polybasic acid.
  • the ester base oil may be a complex ester composed of a mixed alcohol of a monohydric alcohol and a polyhydric alcohol and a mixed acid of a monobasic acid and a polybasic acid.
  • An ester base oil may be used individually by 1 type, and may be used combining 2 or more types by arbitrary ratios.
  • the monohydric alcohol an alcohol having 1 to 24 carbon atoms or 1 to 12 carbon atoms is used. Such monohydric alcohols may be linear or branched, and may be saturated or unsaturated. Examples of such monohydric alcohols include methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, and tetradecanol.
  • polyhydric alcohol 2 to 10 or 2 to 6 alcohols are used.
  • examples of such polyhydric alcohols include ethylene glycol, propylene glycol, neopentyl glycol, glycerin, trimethylol ethane, trimethylol propane, pentaerythritol, and sorbitan.
  • the monobasic acid a fatty acid having 2 to 24 carbon atoms is usually used.
  • Such monobasic acids may be linear or branched, and may be saturated or unsaturated.
  • Examples of such monobasic acids include methanoic acid, ethanoic acid (acetic acid), propanoic acid (propionic acid), butanoic acid (butyric acid, isobutyric acid, etc.), pentanoic acid (valeric acid, isovaleric acid, pivalic acid, etc.) ), Hexanoic acid (such as caproic acid), heptanoic acid, octanoic acid (such as caprylic acid), nonanoic acid (such as pelargonic acid), decanoic acid, undecanoic acid, dodecanoic acid (such as lauric acid), tridecanoic acid, tetradecanoic acid (myristine) Acid), pentadecanoic acid, hexadecanoic acid (such
  • dibasic acids having 2 to 16 carbon atoms dibasic acids having 2 to 16 carbon atoms, benzenedicarboxylic acid, benzenetricarboxylic acid, and benzenetetracarboxylic acid are usually used.
  • dibasic acids may be linear or branched, and may be saturated or unsaturated.
  • dibasic acid having 2 to 16 carbon atoms examples include ethanedioic acid (oxalic acid), propanedioic acid (malonic acid), butanedioic acid (succinic acid), pentanedioic acid (glutaric acid), hexanedioic acid ( Adipic acid), heptanedioic acid (pimelic acid), octanedioic acid (suberic acid), nonanedioic acid (azeleic acid), decanedioic acid (sebacic acid), undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanediic acid Acids, saturated basic acids such as heptadecanedioic acid, hexadecanedioic acid; hexenedioic acid, heptenedioic acid, octenedioic acid, nonened
  • ester of the following combination can be mentioned. These combinations of esters may be used singly or in combination of two or more.
  • (d) polyhydric alcohol (E) A mixture of a monohydric alcohol and a polyhydric alcohol and a monobasic acid
  • f) A mixture of a monohydric alcohol and a polyhydric alcohol and a polybasic acid (2) Mixed ester with basic acid)
  • the ester base oil may contain the polyol ester (b), (d), or (h), which is an ester with a polyhydric alcohol, and contains the polyol ester (b). May be.
  • the polyol ester may be a partial ester in which some of the hydroxyl groups of the polyhydric alcohol are not esterified, or may be a complete ester in which all of the hydroxyl groups of the polyhydric alcohol are esterified.
  • the kinematic viscosity at 40 ° C. of the ester base oil is not particularly limited, but may be 5 mm 2 / s or more, 10 mm 2 / s or more, or 20 mm 2 / s or more.
  • the kinematic viscosity at 40 ° C. of the ester base oil may be 1000 mm 2 / s or less, 500 mm 2 / s or less, or 350 mm 2 / s or less.
  • the additive for lubricating oil represented by the general formula (1) is the additive for lubricating oil according to the first embodiment.
  • the content of the additive for lubricating oil represented by the general formula (1) is not particularly limited, but is 0.005 in terms of phosphorus element, based on the total amount of the composition, from the viewpoint of improving frictional characteristics and wear characteristics. It may be not less than mass% (50 mass ppm), not less than 0.01 mass% (100 mass ppm), or not less than 0.02 mass% (200 mass ppm).
  • the content of the additive for lubricating oil represented by the general formula (1) is 0 in terms of phosphorus element, based on the total amount of the composition, from the viewpoint of suppression of catalyst poisoning and suppression of corrosion of nonferrous metals. .10 mass% (1000 mass ppm) or less, 0.08 mass% (800 mass ppm) or less, or 0.06 mass% (600 mass ppm) or less.
  • the lubricating oil composition according to the third embodiment can further contain any commonly used additive depending on the purpose.
  • additives include viscosity modifiers, metal detergents, ashless dispersants, friction modifiers, and antiwear agents (extreme pressure agents) other than the lubricant additive represented by the general formula (1). ), Antioxidants, corrosion inhibitors, rust inhibitors, pour point depressants, demulsifiers, metal deactivators, antifoaming agents, and the like.
  • Specific examples of these additives include the additives exemplified in the second embodiment. When these additives are contained in the lubricating oil composition, the respective contents may be 0.01 to 20% by mass based on the total amount of the composition.
  • the kinematic viscosity at 40 ° C. of the lubricating oil composition according to the third embodiment is not particularly limited, but may be 5 mm 2 / s or more, 10 mm 2 / s or more, or 20 mm 2 / s or more.
  • the kinematic viscosity at 40 ° C. of the lubricating oil composition may be 1000 mm 2 / s or less, 500 mm 2 / s or less, or 350 mm 2 / s or less.
  • the lubricating oil composition according to the fourth embodiment contains a hydrocarbon-based base oil and the additive for lubricating oil represented by the general formula (1) according to the first embodiment. Used to lubricate a pair of sliding members that move relatively. Here, at least one of the sliding members has a sliding surface covered with a diamond-like carbon film.
  • the lubricating oil composition according to the fourth embodiment is capable of reducing the friction torque of the sliding surface between the sliding members in the sliding member to which the diamond-like carbon material is applied, and has excellent lubricity. Indicates.
  • hydrocarbon base oil a hydrocarbon base oil used in a normal lubricating oil field can be used.
  • specific examples of the hydrocarbon base oil include mineral oil-based hydrocarbon oil, synthetic hydrocarbon oil, or a mixture of both.
  • mineral oil-based hydrocarbon oil and the synthetic hydrocarbon oil those similar to the mineral oil-based hydrocarbon oil and the synthetic hydrocarbon oil exemplified in the lubricating oil composition according to the second embodiment can be used.
  • the kinematic viscosity at 40 ° C. of the hydrocarbon base oil is not particularly limited, but may be 1 mm 2 / s or more, 10 mm 2 / s or more, or 15 mm 2 / s or more.
  • the kinematic viscosity at 40 ° C. may be 100 mm 2 / s or less, 80 mm 2 / s or less, or 60 mm 2 / s or less.
  • the kinematic viscosity at 100 ° C. of the hydrocarbon base oil is not particularly limited, but may be 1 mm 2 / s or more, 2 mm 2 / s or more, or 3 mm 2 / s or more.
  • the kinematic viscosity at 100 ° C. may be 20 mm 2 / s or less, 15 mm 2 / s or less, or 8 mm 2 / s or less.
  • the viscosity index of the hydrocarbon base oil is not particularly limited, but may be 70 or more, 100 or more, or 120 or more. When the viscosity index is within the above range, the stability of the viscosity with respect to the external temperature is ensured, so that the oil film tends to be stably formed even with respect to the external temperature change during use.
  • the total aromatic content of the hydrocarbon base oil is not particularly limited, but may be 10% by mass or less, 5% by mass or less, 3% by mass or less, or 1% by mass or less.
  • the total aromatic content in this specification means the aromatic fraction content measured based on ASTMD2549.
  • aromatic fractions include alkylbenzene, alkylnaphthalene, anthracene, phenanthrene, and alkylated products thereof, compounds in which four or more benzene rings are condensed, or pyridines, quinolines, phenols, naphthols, etc. Compounds having heteroaromatics and the like are included.
  • the lubricating oil composition according to the fourth embodiment may contain a synthetic base oil other than the hydrocarbon base oil.
  • a synthetic base oil other than the hydrocarbon base oil When using together the hydrocarbon base oil and a synthetic base oil other than the hydrocarbon base oil, the proportion of the hydrocarbon base oil in the mixed base oil is 50% by mass or more, 70% by mass or more, Or it may be 80 mass% or more.
  • Examples of synthetic base oils other than hydrocarbon base oils include diesters (ditridecyl glutarate, di-2-ethylhexyl adipate, di-2-ethylhexyl azelate, diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl).
  • Polyol ester (trimethylolpropane caprylate, trimethylolpropane pelargonate, trimethylolpropane oleate, pentaerythritol 2-ethylhexanoate, pentaerythritol pelargonate, etc.); polyoxyalkylene glycol, dialkyldiphenyl ether, poly And phenyl ether.
  • the additive for lubricating oil represented by the general formula (1) is the additive for lubricating oil according to the first embodiment.
  • the content of the additive for lubricating oil represented by the general formula (1) is not particularly limited, but is 0.005 in terms of phosphorus element, based on the total amount of the composition, from the viewpoint of improving frictional characteristics and wear characteristics. It may be not less than mass% (50 mass ppm), not less than 0.01 mass% (100 mass ppm), or not less than 0.03 mass% (300 mass ppm).
  • the content of the additive for lubricating oil represented by the general formula (1) is 0 in terms of phosphorus element, based on the total amount of the composition, from the viewpoint of suppression of catalyst poisoning and suppression of corrosion of nonferrous metals. 20 mass% (2000 mass ppm) or less, 0.15 mass% (1500 mass ppm) or less, or 0.12 mass% (1200 mass ppm) or less.
  • the lubricating oil composition according to the fourth embodiment may further contain an antioxidant.
  • the antioxidant examples include ashless antioxidants such as phenols and amines, and metal antioxidants such as copper and molybdenum.
  • the antioxidant may be an ashless antioxidant.
  • phenol-based ashless antioxidants include 4,4′-methylenebis (2,6-di-tert-butylphenol), 4,4′-bis (2,6-di-tert- Butylphenol), benzenepropanoic acid-3,5-bis (1,1-dimethyl-ethyl) -4-hydroxy-C7-C9 side chain alkyl ester, etc.
  • phenyl- ⁇ - examples thereof include naphthylamine, alkylphenyl- ⁇ -naphthylamine, alkylated diphenylamine, and diphenylamine.
  • the content of the antioxidant is not particularly limited, but from the viewpoint of oxidation stability, it is 0.3 mass% or more, 0.5 mass% or more, or 1.0 mass% or more based on the total amount of the composition. It's okay.
  • the content of the antioxidant may be 4.0% by mass or less, 3.0% by mass or less, or 2.0% by mass or less based on the total amount of the composition from the viewpoint of engine cleanliness.
  • the lubricating oil composition according to the fourth embodiment may further contain a viscosity modifier.
  • the viscosity modifier examples include a non-dispersed or dispersed ethylene- ⁇ -olefin copolymer or a hydride thereof, polyisobutylene or a hydride thereof, a styrene-diene hydrogenated copolymer, and a polyalkylstyrene. .
  • the viscosity modifier may be an ethylene- ⁇ -olefin copolymer or a hydride thereof.
  • non-dispersed or dispersed poly (meth) acrylate viscosity modifiers examples include a copolymer system viscosity modifier and a mixture thereof.
  • the content of the viscosity modifier is not particularly limited, but may be 3% by mass or more, 4% by mass or more, or 5% by mass or more based on the total amount of the composition from the viewpoint of improving the viscosity index. From the viewpoint of engine cleanliness, the content of the viscosity modifier may be 20% by mass or less, 15% by mass or less, or 10% by mass or less based on the total amount of the composition.
  • the lubricating oil composition according to the fourth embodiment can further contain any commonly used additive depending on the purpose.
  • additives include metal detergents, ashless dispersants, friction modifiers, anti-wear agents (extreme pressure agents) other than the lubricant additive represented by the general formula (1), and corrosion prevention.
  • Specific examples of these additives include the additives exemplified in the second embodiment. When these additives are contained in the lubricating oil composition, the respective contents may be 0.01 to 20% by mass based on the total amount of the composition.
  • the kinematic viscosity at 100 ° C. of the lubricating oil composition according to the fourth embodiment is not particularly limited, but may be 1 mm 2 / s or more, 2 mm 2 / s or more, or 3 mm 2 / s or more. Further, the kinematic viscosity at 100 ° C. of the lubricating oil composition according to the fourth embodiment may be 15 mm 2 / s or less, 12 mm 2 / s or less, or 10 mm 2 / s or less. When the kinematic viscosity at 100 ° C. of the lubricating oil composition is within the above range, an appropriate viscosity can be secured and the oil film retainability tends to be excellent.
  • the kinematic viscosity at 40 ° C. of the lubricating oil composition according to the fourth embodiment is not particularly limited, but may be 1 mm 2 / s or more, 10 mm 2 / s or more, or 15 mm 2 / s or more. Further, the kinematic viscosity at 40 ° C. of the lubricating oil composition according to the fourth embodiment may be 100 mm 2 / s or less, 80 mm 2 / s or less, or 60 mm 2 / s or less. When the kinematic viscosity at 40 ° C. of the lubricating oil composition is within the above range, an appropriate viscosity can be secured and the oil film retainability tends to be excellent.
  • the viscosity index of the lubricating oil composition according to the fourth embodiment is not particularly limited, but may be 70 or more, 100 or more, or 120 or more. When the viscosity index is within the above range, the stability of the viscosity with respect to the external temperature is ensured, so that the oil film tends to be stably formed even with respect to the external temperature change during use.
  • the friction coefficient can be reduced in the sliding member to which the diamond-like carbon material is applied.
  • it can be used with the form which does not mix
  • the sliding mechanism which concerns on 5th Embodiment is provided with a pair of sliding member which moves relatively facing, and the lubricating oil composition which concerns on 4th Embodiment which lubricates a sliding member.
  • At least one of the sliding members has a sliding surface covered with a diamond-like carbon film (DLC film).
  • the sliding member may have a sliding surface, both of which are covered with a DLC film.
  • DLC diamond-like carbon constituting the DLC film
  • DLC diamond-like carbon
  • the bonding form between carbons is a diamond structure (sp 3 bond structure) and a graphite bond (sp 2). Carbon).
  • aC amorphous carbon
  • ta-C tetrahedral amorphous carbon
  • H hydrogenated amorphous carbon
  • ta-C A film made of MeC (metal carbon) partially including metal atoms such as H (hydrogenated tetrahedral amorphous carbon), titanium (Ti), molybdenum (Mo), or DLC-Si partially including silicon atoms Is mentioned.
  • Examples of the base material for the sliding member include metal materials such as iron materials, aluminum materials, and magnesium materials.
  • iron-based materials not only high-purity iron, but also, for example, carbon, nickel, copper, zinc, chromium, cobalt, molybdenum, lead, silicon, titanium, or a combination of two or more of these with iron in any proportion
  • Various iron-based alloys may be used. More specifically, carburized steel SCM420, SCr420 (JIS), etc. are mentioned.
  • the aluminum-based material not only high-purity aluminum but also various aluminum-based alloys can be used, for example, 4 to 20% by mass of silicon (Si) and 1.0 to 5.0% by mass of copper (Cu). It may be a hypoeutectic aluminum alloy or a hypereutectic aluminum alloy. Examples of the aluminum alloy include AC2A, AC8A, ADC12, and ADC14 (JIS).
  • magnesium-based materials include magnesium-aluminum-zinc (Mg-Al-Zn), magnesium-aluminum-rare earth metal (Mg-Al-REM), and magnesium-aluminum-calcium (Mg-Al-Ca).
  • Magnesium-zinc-aluminum-calcium (Mg-Zn-Al-Ca), magnesium-aluminum-calcium-rare earth metal (Mg-Al-Ca-REM), magnesium-aluminum-strontium (Mg-Al-Sr) ,
  • Magnesium-aluminum-silicon (Mg-Al-Si), magnesium-rare earth metal-zinc (Mg-REM-Zn), magnesium-silver-rare earth metal (Mg-Ag-REM), magnesium-yttrium- Rare earth metal (Mg-Y-REM Systems; and a combination at any ratio thereof can be used.
  • Specific examples include AZ91, AE42, AX51, AXJ, ZAX85, AXE522, AJ52, AS21, QE22, or WE43 (ASTM).
  • Examples of the method for forming the DLC film on the sliding member include a known PVD (physical vapor deposition) method, CVD (chemical vapor deposition) method, and the like.
  • Examples of the base material of the sliding member having a sliding surface not covered with the DLC film include, for example, metal materials such as the iron-based material, aluminum-based material, and magnesium-based material described above, resin, plastic, and carbon. Examples thereof include metal materials. These base materials may have a sliding surface covered with various thin films such as TiN and CrN.
  • the sliding mechanism can lubricate the sliding member by supplying the above-described lubricating oil composition to the sliding surface according to the type of sliding mechanism such as a sealed type or a circulating type.
  • an internal combustion engine such as a 4-cycle, 2-cycle engine or the like can be cited. More specifically, at least one of the valve system, piston, piston ring, piston skirt, cylinder liner, connecting rod, crankshaft, bearing, bearing, metal gear, chain, belt, oil pump, etc. is covered with a DLC film.
  • An internal combustion engine provided with at least one sliding surface may be mentioned.
  • Example 1-1 ⁇ Glyceryl (n-hexyl) phosphonate (n-hexyl) (wherein m in the general formula (1) is 1, n is 0, R 1 is a methylene group, R 2 and R 3 are n- Synthesis of a compound having a hexyl group> 0.1 mol (25.0 g) of (n-hexyl) phosphonic acid (n-hexyl) (Johoku Chemical Co., Ltd.) and 0.1 mol (7.4 g) of glycidol (ALDRICH) were collected in a flask. By stirring this mixture at 50 ° C. for 60 minutes, 0.1 mol (32.0 g) of glyceryl (n-hexyl) phosphonate (n-hexyl) phosphonate was obtained.
  • the obtained (n-hexyl) glyceryl phosphonate (n-hexyl) was subjected to IR analysis (KBr sandwich method).
  • the IR spectrum is shown in FIG. In the IR spectrum, peaks attributed to the following were observed, confirming the synthesis of the target product.
  • Example 1-2 ⁇ Glyceryl (2-ethylhexyl) phosphonate (2-ethylhexyl) (wherein m in the above general formula (1) is 1, n is 0, R 1 is a methylene group, R 2 and R 3 are 2- Synthesis of a compound having an ethylhexyl group> 0.1 mol (30.6 g) of (2-ethylhexyl) phosphonic acid (2-ethylhexyl) (Tokyo Chemical Industry Co., Ltd.) and 0.1 mol (7.4 g) of glycidol (ALDRICH) were collected in a flask. The mixture was stirred at 50 ° C. for 60 minutes to obtain 0.1 mol (37.0 g) of the desired product, glyceryl (2-ethylhexyl) phosphonate (2-ethylhexyl).
  • Example 1-3 ⁇ (Glyceryl) phosphonic acid di (n-hexyl) (in the above general formula (1), m is 0, n is 1, R 1 is a methylene group, R 2 and R 3 are n-hexyl groups)
  • m is 0, n is 1, R 1 is a methylene group, R 2 and R 3 are n-hexyl groups
  • Synthesis of Compound> Epichlorohydrin (Tokyo Chemical Industry Co., Ltd.) 0.1 mol (9.2 g) and triphosphite (n-hexyl) phosphite (Tokyo Chemical Industry Co., Ltd.) 0.1 mol (33.4 g) were collected in a flask. The mixture was stirred under a nitrogen atmosphere at 130 ° C.
  • the obtained (glyceryl) phosphonic acid di (n-hexyl) was subjected to IR analysis (KBr sandwich method).
  • the IR spectrum is shown in FIG. In the IR spectrum, peaks attributed to the following were observed, confirming the synthesis of the target product.
  • the “phosphorus element conversion values” in Table 1 are the additives for lubricating oils 2-B-1 to 2-B-3 and 2-b-1 to 2-b— based on the total amount of the composition. 3 means phosphorus element equivalent content. “Phosphorus element conversion value” is the phosphorus content (theoretical value) contained in the additives 2-B-1 to 2-B-3 and 2-b-1 to 2-b-3 for lubricating oil and the respective preparations. It can be calculated from the quantity.
  • the wear characteristic test was conducted with a ball-on-disk (SRV) tester.
  • SRV ball-on-disk
  • SUJ-2 1/2 inch sphere
  • SUJ-2 24 ⁇ 6.9 mm
  • the SRV test was evaluated by measuring the wear scar diameter (mm) under conditions of a load of 34 N, an amplitude of 1.0 mm, a temperature of 80 ° C., and a test time of 0.5 hours. In this test, the smaller the wear scar diameter, the better the wear characteristics.
  • the lubricating oil compositions of Examples 2-1 to 2-6 containing the lubricating oil additives of Examples 1-1 to 1-3 are not turbid in the solubility test and have good wear characteristics. It was. On the other hand, in Comparative Example 2-1 using only the base oil, seizure occurred in the wear characteristic test. Further, the lubricating oil composition of Comparative Example 2-2 was observed to be turbid in the solubility test, was not sufficiently dissolved in the hydrocarbon base oil, and seizure occurred in the wear characteristic test. Further, the lubricating oil compositions of Comparative Examples 2-3 and 2-4 had larger wear scar diameters than the lubricating oil compositions of Examples 2-1 to 2-6.
  • the additive for lubricating oil of the present invention has sufficient solubility even when applied to a hydrocarbon base oil. Moreover, it was confirmed that the lubricating oil composition using the additive for lubricating oil of the present invention has excellent lubricity by reducing wear and seizure under severe conditions under high load.
  • the “phosphorus element conversion values” in Table 2 are the phosphorus element conversion values of the lubricating oil additives 3-B-1 to 3-B-3 and 3-b-1 based on the total amount of the composition. It means the total amount of content.
  • the “phosphorus element conversion value” can be calculated from the phosphorus content (theoretical value) contained in the lubricating oil additive and the respective charged amounts.
  • the wear characteristic test was conducted with a ball-on-disk (SRV) tester.
  • SRV ball-on-disk
  • SUJ-2 1/2 inch sphere
  • SUJ-2 24 ⁇ 6.9 mm
  • the SRV test was evaluated by measuring the wear scar diameter (mm) under conditions of a load of 25 N, an amplitude of 1.0 mm, a temperature of 80 ° C., and a test time of 0.5 hours. In this test, the smaller the wear scar diameter, the better the wear characteristics.
  • the lubricating oil compositions of Examples 3-1 to 3-6 containing the lubricating oil additives of Examples 1-1 to 1-3 are the same as the lubricating oil additives of Examples 1-1 to 1-3. Compared to the lubricating oil compositions of Comparative Examples 3-1 and 3-2 which do not contain, they had good wear characteristics. From these results, it was confirmed that the lubricating oil composition of the present invention reduced wear, seizure, and the like under severe conditions under high loads and had excellent lubricity.
  • the “phosphorus element conversion values” in Table 3 are the additives for lubricating oil 4-B-1 to 4-B-3 and 4-b-1, 4-b- It means the content of 2 in terms of phosphorus element.
  • “Phosphorus element equivalent value” is the phosphorus content (theoretical value) contained in additives 4-B-1 to 4-B-3, 4-b-1, and 4-b-2 for lubricating oil, and the respective preparations It can be calculated from the quantity.
  • the coefficient of friction was measured with a cylinder on disk (SRV) tester.
  • SRV cylinder on disk
  • a DLC-Si film formed on the surface of a cylinder (15 ⁇ 22 mm, induction hardening) and a disk (24 ⁇ 7.9 mm, carburizing and quenching) was used.
  • the film was formed in a chamber using tetramethylsilane (normal temperature liquid, gas at about 50 ° C.) as a source gas.
  • the DLC-Si film was formed by previously forming Ti as an intermediate layer on a Si (100) substrate at about 0.3 ⁇ m, and then forming a thin film at about 1.0 ⁇ m in the chamber.
  • the center line average roughness Ra was about 1.0 nm, and the maximum height roughness Ry was about 29.8 nm.
  • the cylinder and the disk were ultrasonically cleaned for 15 minutes using hexane and acetone before the friction characteristic test.
  • the friction characteristic test was performed under the conditions of a load of 400 N, an amplitude of 1.5 mm, a temperature of 80 ° C., a test time of 30 minutes, and a frequency of 50 Hz. The results are shown in Table 1.
  • the friction coefficient in Table 3 is an average value of the friction coefficients for a test time of 25 to 28 minutes. In this test, it means that it is excellent in a friction characteristic, so that a friction coefficient is small.
  • the lubricating oil compositions of Examples 4-1 to 4-8 containing the lubricating oil additive of Examples 1-1 to 1-3 are the sliding members to which the diamond-like carbon material is applied. The friction coefficient of the sliding surfaces between them was reduced.
  • the lubricating oil compositions of Comparative Examples 4-1 to 4-3 that do not contain the lubricating oil additive of Examples 1-1 to 1-3 are the lubricants of Examples 4-1 to 4-8. Compared to the oil composition, the friction coefficient was increased. From these results, the lubricating oil composition of the present invention can reduce the friction coefficient of the sliding surface between the sliding members in the sliding member to which the diamond-like carbon material is applied, and exhibits excellent lubricity. confirmed.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne un additif qui est destiné à un lubrifiant et qui est représenté par la formule générale (1). En outre, l'invention concerne une composition lubrifiante contenant : une huile de base lubrifiante ; et un additif qui est destiné à un lubrifiant et qui est représenté par la formule générale (1). [Dans la formule générale (1), R1 représente un groupe alkylène, R2 et R3 représentent chacun indépendamment un groupe hydrocarboné, m représente 0 ou 1, et n représente 0 ou 1, où m+n est égal à 1.]
PCT/JP2018/012512 2017-04-28 2018-03-27 Additif destiné à un lubrifiant, composition lubrifiante, et mécanisme coulissant WO2018198645A1 (fr)

Applications Claiming Priority (6)

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JP2017090492A JP2018188519A (ja) 2017-04-28 2017-04-28 潤滑油用添加剤及び潤滑油組成物
JP2017090498A JP2018188521A (ja) 2017-04-28 2017-04-28 潤滑油組成物
JP2017-090498 2017-04-28
JP2017-090492 2017-04-28
JP2017090496A JP2018188520A (ja) 2017-04-28 2017-04-28 潤滑油組成物及びこれを用いた摺動機構
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57164192A (en) * 1973-10-04 1982-10-08 Lubrizol Corp Functional fluid
WO1997010319A1 (fr) * 1995-09-13 1997-03-20 Kao Corporation Composition d'huile lubrifiante
JPH09165593A (ja) * 1995-10-09 1997-06-24 Kao Corp 潤滑油組成物
JPH09194767A (ja) * 1996-01-24 1997-07-29 Kao Corp 磁気記録媒体
JP2011032429A (ja) * 2009-08-05 2011-02-17 Toyota Central R&D Labs Inc 低摩擦摺動部材
WO2016170707A1 (fr) * 2015-04-24 2016-10-27 Ｊｘエネルギー株式会社 Composition d'huile de graissage

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57164192A (en) * 1973-10-04 1982-10-08 Lubrizol Corp Functional fluid
WO1997010319A1 (fr) * 1995-09-13 1997-03-20 Kao Corporation Composition d'huile lubrifiante
JPH09165593A (ja) * 1995-10-09 1997-06-24 Kao Corp 潤滑油組成物
JPH09194767A (ja) * 1996-01-24 1997-07-29 Kao Corp 磁気記録媒体
JP2011032429A (ja) * 2009-08-05 2011-02-17 Toyota Central R&D Labs Inc 低摩擦摺動部材
WO2016170707A1 (fr) * 2015-04-24 2016-10-27 Ｊｘエネルギー株式会社 Composition d'huile de graissage

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