WO2006025246A1 - Additif pour lubrifiant - Google Patents

Additif pour lubrifiant Download PDF

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Publication number
WO2006025246A1
WO2006025246A1 PCT/JP2005/015400 JP2005015400W WO2006025246A1 WO 2006025246 A1 WO2006025246 A1 WO 2006025246A1 JP 2005015400 W JP2005015400 W JP 2005015400W WO 2006025246 A1 WO2006025246 A1 WO 2006025246A1
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WO
WIPO (PCT)
Prior art keywords
zinc
additive
compound
lubricant
carbon atoms
Prior art date
Application number
PCT/JP2005/015400
Other languages
English (en)
Japanese (ja)
Inventor
Hiroaki Koshima
Shinya Iizuka
Motoharu Ishikawa
Original Assignee
Idemitsu Kosan Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Priority to EP05780924A priority Critical patent/EP1783196A4/fr
Priority to US11/661,354 priority patent/US20080161215A1/en
Priority to CN2005800292329A priority patent/CN101010418B/zh
Priority to KR1020077004644A priority patent/KR101252867B1/ko
Publication of WO2006025246A1 publication Critical patent/WO2006025246A1/fr

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Classifications

    • 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
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • 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
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants

Definitions

  • the present invention relates to a lubricant additive, more specifically, excellent in oxidation stability, thermal stability and NOx degradation resistance, and an extreme pressure additive has an excellent function as an antiwear agent.
  • New phosphoric acid ester derivative, reaction product of phosphoric acid ester derivative and zinc compound, or additive for lubricant comprising mixture of phosphoric acid ester derivative and organic zinc compound, and lubrication containing these additives It relates to an oil composition.
  • Lubricating oils are required to have an ability to prevent wear of metal surfaces due to sliding or rolling contact between parts when a mechanical device is operated and an ability to control wear. The Therefore, the role of the additive becomes extremely important in order to improve the wear resistance of the lubricating oil and extend the life of the equipment.
  • the base oil alone cannot have many special properties required for the use of other lubricating oil compositions including internal combustion engine lubricating oil and drive system lubricating oil. Therefore, it is necessary to improve the performance of the lubricating oil composition by using a lubricating oil additive to impart each specific property. For this reason, there has been a search for lubricating oils having one or more properties suitable for use in these lubricating oil compositions.
  • Patent Document 1 describes a general formula as a lubricating oil.
  • R represents a saturated aliphatic hydrocarbon group having 2 to 3 carbon atoms
  • X represents O or S, respectively
  • a plurality of R ′ are each an alkyl group having 1 to 18 carbon atoms, etc. is there.
  • the phosphorus and sulfur-containing phosphate ester compounds represented by are disclosed, there is no description of specific uses.
  • Patent Document 2 includes a general formula
  • A is an alkylene group having 2 to 6 carbon atoms
  • R ′ is an alkyl group having 2 to 4 carbon atoms, respectively.
  • the phosphoric acid ester derivative represented by the formula (1) is further disclosed and used as a flameproofing agent by copolymerizing with an acrylic ester.
  • Patent Document 3 describes an aromatic amine and a general formula.
  • X is O or S (at least one is S), m is 0 or 1 (at least three m is 1), and a plurality of R are alkyl groups or aromatic groups. is there. ]
  • An ester-based lubricating composition consisting of organic thiophosphoric acid or phosphorous acid represented by the formula S is disclosed and used as an antioxidant.
  • Patent Document 4 includes a general formula
  • Z is a hydrocarbyl group
  • R is a hydrocarbyl group, a hydrocarbyloxy group, etc.
  • R ' is a hydrogen atom or a divalent hydrocarbyl group.
  • X is S or O.
  • Yb is a hydrocarbyl group or the like.
  • the phosphorus- and sulfur-containing compounds represented by are described, and are used as oxidation stabilizers and antiwear agents.
  • Patent Document 5 includes a general formula
  • R is an alkyl group, a cycloalkyl group, etc.
  • R ′ represents an alkyl group
  • X is 1 to 4
  • m is 1 or 2
  • m + m ′ 3.
  • Is used as a corrosion inhibitor for ferrous metals are used as a corrosion inhibitor for ferrous metals.
  • Patent Document 6 includes a general formula
  • R is an alkyl group or alkenyl
  • R ′ is OH, alkoxy or the like
  • X is 2-4.
  • An alkoxypolyethyleneoxyphosphate phosphite ester represented by the formula (1) is disclosed and used as an additive to improve water tolerance for oils.
  • Patent Document 7 includes a general formula
  • R is alkyl or the like, R ′ is an alkylene group, and X represents O, NH or S.
  • m is 1 to 3
  • m ′ is 1 to 12
  • m ′′ is 0 or 1.
  • Patent Document 8 discloses sulfur obtained by reacting at least one sulfur composition with a di- or tri-hydrocarbyl phosphite and / or an amine compound as a useful additive in fuel and lubricating and functional fluid compositions.
  • the phosphorus and nitrogen-containing derivatives of the containing compounds are disclosed.
  • Patent Document 9 and Patent Document 10 include (1) ⁇ -hydroxythioether reactant, (2) dihydrocarbyl hydrogen phosphite, trihydrocarbyl phosphite, and mixtures thereof, (3) Reaction products of reaction mixtures containing nucleophilic reactants are disclosed and used as antiwear and antioxidant agents.
  • Patent Document 11 includes a general formula
  • X ′ represents S (sulfur) and Y ′ represents S (sulfur) or 0 (oxygen).
  • R represents an organic group having 6 to 20 carbon atoms, and R ′ represents an organic group having 1 to 6 carbon atoms.
  • m is an integer of 1 to 3.
  • Patent Document 12 includes a general formula
  • A is H or OH, m is 0 or 1, m is 0, A is OH, m is 1, A is H or OH, R and R 'are H or at least one, respectively.
  • O represents hydrocarbons containing S or O]
  • a composition obtained by heat-treating phosphoric acid and Z or phosphorous acid represented by formula (I) and an imide dispersant containing boron is disclosed.
  • Patent Document 13 includes a general formula
  • R is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms
  • X is O or S, respectively
  • Z is a metal atom.
  • Patent Document 1 US Patent No. 2750342
  • Patent Document 2 US Patent No. 2960523 Specification
  • Patent Document 3 US Patent No. 3446738
  • Patent Document 4 US Patent No. 4081387
  • Patent Document 5 US Patent No. 4511480
  • Patent Document 6 US Patent No. 4579672
  • Patent Document 7 US Patent No. 4776969
  • Patent Document 8 WO88Z03554 pamphlet
  • Patent Document 9 Pamphlet of W089Z12666
  • Patent Document 10 Japanese Patent Publication No. 3-500061
  • Patent Document 11 JP-A-11 171892
  • Patent Document 12 U.S. Pat.No. 6352962
  • Patent Document 13 Japanese Patent Application Laid-Open No. 2002-294271
  • the present invention has been made under such circumstances, and provides a novel thio-containing organophosphorus compound, and an additive for lubricating oil containing the compound, and further includes an internal combustion engine, a drive train machine, etc.
  • An object of the present invention is to provide a lubricating oil composition excellent in extreme pressure properties, wear resistance and friction characteristics even under severe operating conditions under high loads.
  • the specific phosphate ester derivative is excellent in thermal stability, oxidation stability, NOx resistance and base number maintenance.
  • the present invention has been found to be useful as an extreme pressure agent, an antiwear agent and a friction property modifier, and the present invention has been completed.
  • the present invention provides the following additives for lubricants and the like.
  • R 1 represents a monovalent organic group having 24 carbon atoms and R 2 represents a divalent organic group having 1 to 6 carbon atoms.
  • n represents an integer of 1 to 3.
  • a lubricant additive comprising a phosphate ester derivative (A) represented by the formula: 2.—General formula [I]
  • Y represents S (sulfur) or 0 (oxygen).
  • R 1 represents a monovalent organic group having 24 carbon atoms and R 2 represents a divalent organic group having 1 to 6 carbon atoms.
  • n represents an integer of 1 to 3.
  • a lubricant additive comprising a reaction product of a phosphate ester derivative (A) and a zinc compound (B) represented by the formula:
  • R 1 represents a monovalent organic group having 24 carbon atoms and R 2 represents a divalent organic group having 1 to 6 carbon atoms.
  • n represents an integer of 1 to 3.
  • a lubricant additive comprising a mixture of a phosphate ester derivative (A) represented by the formula (A) and an organic zinc compound (C).
  • the zinc compound (B) is at least one compound selected from the group forces of metal zinc, zinc oxide, organic zinc compound, zinc oxyacid salt, zinc, rogenyzinc and zinc complex.
  • C organic zinc compound
  • a lubricant additive composition comprising the lubricant additive according to any one of 1 to 8 above.
  • Lubricating oil yarn composition comprising a lubricating base oil containing 0.001 to 0.5 mass% of the additive for lubricant according to any one of 1 to 8 above in terms of a phosphorus element conversion amount. .
  • a lubricating oil thread for an internal combustion engine wherein the lubricating base oil contains 0.001 to 0.5 mass% of the additive for lubricant according to any one of 1 to 8 above in terms of a phosphorus element conversion amount. And adult.
  • a method for producing an additive for lubricant which is obtained by reacting the phosphate ester derivative (A) or the zinc compound (B) described in 2 or 4 above.
  • the lubricating oil composition of the present invention is extremely excellent in base number maintenance in an NOx atmosphere, that is, long drain performance, and further has excellent wear prevention performance and high temperature cleaning performance.
  • lubricating oil for internal combustion engines with high NOx gas concentration and relatively high force such as gasoline engines, diesel engines, and gas engines, natural gas, LPG (liquid petroleum gas), cracked gas It is effectively used as crankcase oil for internal combustion engines that use coal cracked gas as fuel.
  • the lubricating oil composition of the present invention is a lubricating oil that requires base number maintenance, wear prevention performance, and high temperature cleanliness, such as lubricating oil for power transmission, gear oil, bearing oil, shock oil. It can also be used as absorber oil, industrial lubricating oil, etc.
  • a first invention of the present application is an additive for a lubricant which also has a phosphate ester derivative (A) force represented by the above general formula [I].
  • R 1 is preferably a hydrocarbon group having 4 to 24 carbon atoms, particularly an alkyl group having 8 to 16 carbon atoms. If the carbon number of R 1 is smaller, oil solubility, extreme pressure characteristics, wear resistance, friction characteristics, and lubrication characteristics are inferior and corrosivity increases.
  • R 1 is a butyl group, a pentyl group, various hexyl groups, various heptyl groups, various octyl groups, various nonyl groups, various decyl groups, various undecyl groups, various dodecyl groups, various tridecyl groups, various types. Tetradecyl group, various pentadecyl groups, various hexadecyl groups, various heptadecyl groups, various octadecyl groups, various nonadecyl groups, various eicodecyl groups, etc.
  • alkyl groups cyclohexyl group, various methylcyclohexyl groups, various ethylcyclohexyl groups Groups, various propyl cycloalkyl groups, various cycloalkyl groups such as dimethyl cycloalkyl groups; phenyl groups, various methyl phenyl groups, various ethyl phenyl groups, various propyl phenyl groups, various trimethyl phenyl groups, various butyl phenyl groups. Groups, aryl groups such as various naphthyl groups; benzyl groups, various phenyl groups And arylalkyl groups such as various methylbenzyl groups, various propyl groups, various butyl groups, and the like.
  • R 2 is preferably a hydrocarbon group having 1 to 6 carbon atoms, and particularly preferably an alkylene group having 1 to 4 carbon atoms.
  • R 2 is preferably a hydrocarbon group having 1 to 6 carbon atoms, and particularly preferably an alkylene group having 1 to 4 carbon atoms.
  • Examples include alicyclic groups having two bonding sites on alicyclic hydrocarbons such as cyclopentane, and various phenylene groups.
  • Y represents S (sulfur) or 0 (oxygen) and contains at least one or more S as the general formula [I].
  • n represents an integer of 1 to 3, preferably 1 or 2, and more preferably 2.
  • phosphoric acid ester derivative represented by the above general formula [I] include tri (hexylthioethoxy) phosphoric acid ester, tri (octylthioethoxy) phosphoric acid ester, tri (dodecylthioethoxy) phosphoric acid.
  • Acid ester tri (hexadecylthioethoxy) phosphate, di (hexylthioethoxy) phosphate, di (octylthioethoxy) phosphate, di (dodecylthioethoxy) phosphate, di (he Oxadecylthioethoxy) phosphate ester, mono (hexylthioethoxy) phosphate ester, mono (octylthioethoxy) phosphate Examples include acid esters, mono (dodecylthioethoxy) phosphate esters, and mono (hexadecylthioethoxy) phosphate esters.
  • the method for producing the phosphate ester derivative represented by the above general formula [I] is not particularly limited.
  • the phosphate ester derivative is represented by the general formula [II]
  • hydrocarbyl thioalkoxide represented by the formula and phosphorus oxychloride (POC1)
  • hydrocarbyl thioalkyl alcohol or hydrocarbyl thioalkoxide and phosphorus oxychloride are usually used in a molar ratio of 1 mole of phosphorus oxychloride per mole of hydrocarbyl thioalkyl alcohol or hydrocarbyl thioalkoxide 0.1-5.
  • the range is 0 monole, more preferably 1 to 3 monole, still more preferably 1.5 to 2.5 monole.
  • the reaction temperature is usually selected in the range of 60 to 100 ° C, preferably 30 to 50 ° C.
  • This reaction may be performed without a catalyst or in the presence of a base.
  • a base for example, triethylamine, pyridine and the like can be used.
  • a solvent such as xylene, toluene, tetrahydrofuran (THF), or jetyl ether can be used.
  • alkylthioalkyl alcohol 1 mol per mol of diphosphorus pentoxide in molar ratio 1 It is -12 mol, More preferably, it is 2-6 mol, More preferably, it is the range of 3-4 mol.
  • the reaction temperature is usually selected in the range of about 0 to 140 ° C, preferably 30 to 110 ° C, more preferably 50 to 90 ° C.
  • a solvent such as xylene, toluene, THF, jetyl ether, chloroform, etc. can be used.
  • a second invention of the present application is an additive for a lubricant comprising a reaction product of the phosphate ester derivative (A) and a zinc compound (B).
  • Zinc compounds (B) are preferably metal zinc, zinc oxide, organic zinc compounds, zinc oxygenates, zinc halides, zinc complexes, etc. Specifically, zinc, zinc oxide, hydroxide ⁇ ⁇ Zinc, zinc carbonate, dimethyl zinc, diphenyl zinc, zinc complexes, etc.
  • the reaction of the phosphate ester derivative (A) and the zinc compound (B) can be obtained by reacting in the absence of a catalyst or in the presence of a catalyst.
  • the proportion of the phosphoric acid ester derivative to the zinc compound is usually 0.1 to 5.0 mol of the phosphoric acid ester derivative per mol of the zinc compound.
  • it is 1-3 mol, More preferably, it is the range of 1.5-2.5 mol.
  • the reaction range is usually selected in the range of room temperature to 200 ° C, preferably 40 to 150 ° C.
  • a solvent such as xylene, toluene, hexane or the like can be used.
  • the third invention of the present application is an additive for a lubricant comprising a mixture of a phosphate ester derivative (A) and an organozinc compound (C).
  • organic zinc salt (C) alkyl or zinc zinc carboxylate, alkyl or zinc zinc carboxylate and the like are preferred.
  • zinc oleate, zinc isostearate, zinc stearate, alkylphenol Examples include zinc dicarboxylate and zinc alkylsalicylate.
  • the lubricant additive in the present invention as described above can be used only in the phosphoric acid ester derivative (A), but the reaction product of the component (A) and the zinc compound (B), or the component (A) It is preferably used as a mixture with the organic zinc compound (C).
  • These reactants and mixtures may be one kind or two or more kinds.
  • the effective blending amount of these additives is usually based on the strength base oil standard that varies depending on the application.
  • the element content is preferably 0.001 to 1.0% by mass, more preferably 0.005 to 0.5% by mass.
  • mineral oil or synthetic oil can be used as the lubricating base oil.
  • mineral oils include paraffin-based mineral oils, naphthene-based mineral oils, intermediate-based mineral oils, etc., and specific examples include light-eutral oils, medium-eutral oils obtained by solvent refining or hydrorefining, Heavy-eutral oil, bright stock, etc.
  • synthetic oils include, for example, poly-a-olefin, a-olefin copolymer, polybutene, alkylbenzene, polyol ester, dibasic acid ester, polyhydric alcohol ester, polyoxyalkylene glycol, polyoxyalkylene glycol ester, polyoxy Examples include alkylene glycol ethers and cycloalkane compounds.
  • lubricating base oils can be used alone or in combination of two or more, and mineral oil and synthetic oil may be used in combination.
  • additive composition for lubricants of the present invention various additive components conventionally used in lubricant compositions, for example, cleaning dispersants, antioxidants, and the like, as long as the object of the present invention is not impaired.
  • Agents, antifungal agents, antifoaming agents, viscosity index improvers, pour point depressants, demulsifiers, other extreme pressure agents, antiwear agents, and the like can be blended.
  • Example 3 Into a 300 milliliter flask, put 45 g of octylthioethyl phosphoric acid obtained in Example 1, 50 milliliters of toluene, lg of water, 70. The temperature was raised to C. 104. lg (0. 05 mol) of acid was added. The reaction was carried out at 70 ° C for 3 hours. Toluene and water were distilled off under reduced pressure, diluted with 15 g of 150N mineral oil, and the reaction product was filtered. The yield of the obtained reaction product was 60 g.
  • Example 3 Example 3
  • Example 1 it carried out like Example 1 except having used 123.3 g (0.5 mol) of dodecyl thioethanol instead of octyl thioethanol.
  • the yield of the obtained reaction product was 92 g.
  • Example 2 Example 2 was used except that 55 g of the reaction product (dodecylthioethyl phosphoric acid) obtained in Example 3 was used instead of the reaction product obtained in Example 1. It was carried out in the same way. The yield of the obtained reaction product was 70 g.
  • Example 1 it carried out like Example 1 except having used hexyl thioethanol 81.lg (0.5 mol) instead of octyl thioethanol.
  • the yield of the obtained reaction product was 6 lg.
  • Example 2 except that 33 g of the reaction product (hexylthioethyl phosphoric acid) obtained in Example 5 was used instead of the reaction product obtained in Example 1. This was carried out in the same way as 2. The yield of the obtained reaction product was 50 g.
  • Example 7 The same procedure as in Example 1 was performed except that 42.2 g (0.275 mol) of phosphorus oxychloride was used instead of 38.3 g (0.25 mol) of phosphorus oxychloride in Example 1. The yield of the obtained reaction product (octylthioethyl phosphoric acid) was 62 g.
  • Example 2 Example 2 was used except that the reaction product (octylthioethyl phosphoric acid) obtained in Example 7 was used instead of the reaction product obtained in Example 1. It carried out like. The yield of the obtained reaction product was 60 g.
  • Example 2 The same procedure as in Example 1 was performed except that 34.5 g (0.225 mol) of phosphorus oxychloride was used instead of 38.3 g (0.25 mol) of phosphorus oxychloride in Example 1. The yield of the reaction product obtained was 78 g.
  • Example 2 except that the reaction product (octylthioethyl phosphoric acid) obtained in Example 9 was used instead of the reaction product obtained in Example 1, Example 2 was used. It carried out like. The yield of the reaction product obtained was 6 lg.
  • Example 12 it carried out like Example 12 except having used stearic acid 113.6g (0.4 mol) instead of oleic acid.
  • the yield of the reaction product obtained was 148 g Met.
  • Lubricating oil composition (parts by mass)
  • composition obtained above was subjected to a NOx resistance test, a valve wear test, and a Falex load resistance test by the following methods.
  • JASO M 328-95 valve train wear test was conducted, and the rocker arm pad scuff area, rocker arm wear, and cam wear after 100 hours test were measured. A value of 10 or less for each indicates a lubricating oil composition with excellent wear resistance.
  • Pin material AISI-3153, Block material; AISI-1137, Oil amount: 300ml, Rotation speed: 290rpm, Oil temperature: 100 ° C, Load 1112N After running-in for 5 minutes, oil The load is continuously increased at a temperature of 100 ° C, and seized according to ASTM D3233. The weight was measured. The higher the seizure load, the more excellent the load bearing capacity.
  • Comparative Example 2 shows excellent base number durability even in a nitrogen atmosphere (Table 2), and also has excellent wear resistance performance (Table 3), but the load bearing performance is the lubricating oil composition of the present invention. It is markedly inferior to the product (Examples 15 and 20)! /,! /, (Table 4).
  • the lubricating oil composition of the present invention can be used as, for example, an internal combustion engine lubricating oil, a power transmission lubricating oil, a gear oil, a bearing oil, a shock absorber oil, an industrial lubricating oil, and the like.

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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

Cette invention a pour objet un additif pour lubrifiants présentant une stabilité d'oxydation, une stabilité thermique, une résistance au NOx ainsi que d'excellentes fonctions permettant de servir d’additif sous pression extrême ou d’agent résistant à l'usure. Cette invention a également pour objet une composition lubrifiante contenant ce type d’additif. Plus particulièrement, cette invention pour objet un additif pour lubrifiants d'un dérivé de phosphate représenté par la formule générale (I) mentionnée ci-dessous, et une composition lubrifiante contenant ce type d’additif. Dans la formule ci-dessous, Y représente S (soufre) ou O (oxygène); R1 représente un groupe organique monovalent possédant 4 à 24 atomes de carbone; R2 représente un groupe organique divalent possédant 1 à 6 atomes de carbone; et n représente un entier compris entre 1 et 3. (I)
PCT/JP2005/015400 2004-08-30 2005-08-25 Additif pour lubrifiant WO2006025246A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP05780924A EP1783196A4 (fr) 2004-08-30 2005-08-25 Additif pour lubrifiant
US11/661,354 US20080161215A1 (en) 2004-08-30 2005-08-25 Additive For Lubricant
CN2005800292329A CN101010418B (zh) 2004-08-30 2005-08-25 润滑油用添加剂
KR1020077004644A KR101252867B1 (ko) 2004-08-30 2005-08-25 윤활제용 첨가제

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004249807A JP4563114B2 (ja) 2004-08-30 2004-08-30 潤滑剤用添加剤
JP2004-249807 2004-08-30

Publications (1)

Publication Number Publication Date
WO2006025246A1 true WO2006025246A1 (fr) 2006-03-09

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PCT/JP2005/015400 WO2006025246A1 (fr) 2004-08-30 2005-08-25 Additif pour lubrifiant

Country Status (6)

Country Link
US (1) US20080161215A1 (fr)
EP (1) EP1783196A4 (fr)
JP (1) JP4563114B2 (fr)
KR (1) KR101252867B1 (fr)
CN (1) CN101010418B (fr)
WO (1) WO2006025246A1 (fr)

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WO2009061208A1 (fr) * 2007-11-09 2009-05-14 Pronova Biopharma Norge As Composés lipidiques à utiliser dans des produits cosmétiques, en tant que suppléments alimentaires ou en tant que médicaments
WO2009104682A1 (fr) * 2008-02-20 2009-08-27 出光興産株式会社 Composition d'huile lubrifiante pour moteur à combustion interne
JP2011037994A (ja) * 2009-08-12 2011-02-24 Hokkaido Univ 複合組成物及び光学プラスチック製品
WO2011034026A1 (fr) * 2009-09-15 2011-03-24 出光興産株式会社 Composition lubrifiante et mécanisme à glissement l'utilisant
US8735436B2 (en) 2009-05-08 2014-05-27 Pronova Biopharma Norge As Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas
US8759558B2 (en) 2008-07-15 2014-06-24 Pronova Biopharma Norge As Sulphur containing lipids for use as food supplement or as medicament
US9394228B2 (en) 2010-11-05 2016-07-19 Pronova Biopharma Norge As Methods of treatment using lipid compounds
US10722481B2 (en) 2015-04-28 2020-07-28 Basf As Substituted fatty acids for treating non-alcoholic steatohepatitis
US11351139B2 (en) 2013-02-28 2022-06-07 Basf As Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same
US11925614B2 (en) 2017-12-06 2024-03-12 Basf As Fatty acid derivatives for treating non-alcoholic steatohepatitis

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JP5638240B2 (ja) * 2007-04-26 2014-12-10 出光興産株式会社 潤滑油組成物
DE102010015207A1 (de) * 2010-04-16 2011-10-20 Schaeffler Technologies Gmbh & Co. Kg Verfahren zur Überwachung einer Linearführung
CN103805312A (zh) * 2012-11-14 2014-05-21 重庆工商大学 一种高效无硫磷多功能润滑添加剂
JP6247600B2 (ja) * 2014-06-16 2017-12-13 Ｊｘｔｇエネルギー株式会社 変速機用潤滑油組成物
WO2016109376A1 (fr) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante à protection contre l'usure du moteur
US10781397B2 (en) 2014-12-30 2020-09-22 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
JP7318164B2 (ja) * 2016-12-14 2023-08-01 出光興産株式会社 潤滑油組成物、潤滑方法及びギヤ
JP7475256B2 (ja) * 2020-10-09 2024-04-26 Ｅｎｅｏｓ株式会社 潤滑油組成物

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Cited By (20)

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US8741966B2 (en) 2007-11-09 2014-06-03 Pronova Biopharma Norge As Lipid compounds for use in cosmetic products, as food supplement or as a medicament
JP2011503057A (ja) * 2007-11-09 2011-01-27 プロノヴァ・バイオファーマ・ノルゲ・アーエス 化粧品において，食品サプリメントとして，または医薬品として用いるための脂質化合物
WO2009061208A1 (fr) * 2007-11-09 2009-05-14 Pronova Biopharma Norge As Composés lipidiques à utiliser dans des produits cosmétiques, en tant que suppléments alimentaires ou en tant que médicaments
WO2009104682A1 (fr) * 2008-02-20 2009-08-27 出光興産株式会社 Composition d'huile lubrifiante pour moteur à combustion interne
US9321981B2 (en) 2008-02-20 2016-04-26 Idemitsu Kosan Co., Ltd. Lubricating oil composition for internal combustion engine
JP5727701B2 (ja) * 2008-02-20 2015-06-03 出光興産株式会社 内燃機関用潤滑油組成物
JPWO2009104682A1 (ja) * 2008-02-20 2011-06-23 出光興産株式会社 内燃機関用潤滑油組成物
US8759558B2 (en) 2008-07-15 2014-06-24 Pronova Biopharma Norge As Sulphur containing lipids for use as food supplement or as medicament
US8735436B2 (en) 2009-05-08 2014-05-27 Pronova Biopharma Norge As Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas
JP2011037994A (ja) * 2009-08-12 2011-02-24 Hokkaido Univ 複合組成物及び光学プラスチック製品
JP2011084721A (ja) * 2009-09-15 2011-04-28 Idemitsu Kosan Co Ltd 摺動機構
EP2479247A4 (fr) * 2009-09-15 2013-06-26 Idemitsu Kosan Co Composition lubrifiante et mécanisme à glissement l'utilisant
JP2011084722A (ja) * 2009-09-15 2011-04-28 Idemitsu Kosan Co Ltd 潤滑油組成物、該潤滑油組成物を用いた摺動機構
WO2011034026A1 (fr) * 2009-09-15 2011-03-24 出光興産株式会社 Composition lubrifiante et mécanisme à glissement l'utilisant
US9394228B2 (en) 2010-11-05 2016-07-19 Pronova Biopharma Norge As Methods of treatment using lipid compounds
US11351139B2 (en) 2013-02-28 2022-06-07 Basf As Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same
US10722481B2 (en) 2015-04-28 2020-07-28 Basf As Substituted fatty acids for treating non-alcoholic steatohepatitis
US11234948B2 (en) 2015-04-28 2022-02-01 Basf As Substituted fatty acids for treating non-alcoholic steatohepatitis
US11911354B2 (en) 2015-04-28 2024-02-27 Basf Substituted fatty acids for treating non-alcoholic steatohepatitis
US11925614B2 (en) 2017-12-06 2024-03-12 Basf As Fatty acid derivatives for treating non-alcoholic steatohepatitis

Also Published As

Publication number Publication date
KR101252867B1 (ko) 2013-04-09
EP1783196A1 (fr) 2007-05-09
JP4563114B2 (ja) 2010-10-13
KR20070048745A (ko) 2007-05-09
CN101010418A (zh) 2007-08-01
EP1783196A4 (fr) 2010-07-21
CN101010418B (zh) 2011-07-06
US20080161215A1 (en) 2008-07-03
JP2006063248A (ja) 2006-03-09

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