WO2024004763A1 - Composition améliorant l'indice de viscosité et composition d'huile lubrifiante - Google Patents

Composition améliorant l'indice de viscosité et composition d'huile lubrifiante Download PDF

Info

Publication number
WO2024004763A1
WO2024004763A1 PCT/JP2023/022777 JP2023022777W WO2024004763A1 WO 2024004763 A1 WO2024004763 A1 WO 2024004763A1 JP 2023022777 W JP2023022777 W JP 2023022777W WO 2024004763 A1 WO2024004763 A1 WO 2024004763A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
viscosity index
group
lubricating oil
carbon atoms
Prior art date
Application number
PCT/JP2023/022777
Other languages
English (en)
Japanese (ja)
Inventor
展洋 内藤
真之介 木口
直弘 鳥居
和樹 尾形
義光 杉山
Original Assignee
三洋化成工業株式会社
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 三洋化成工業株式会社 filed Critical 三洋化成工業株式会社
Publication of WO2024004763A1 publication Critical patent/WO2024004763A1/fr

Links

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
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
    • 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
    • C10M129/04—Hydroxy compounds
    • C10M129/06—Hydroxy compounds having hydroxy 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
    • 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
    • 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
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group

Definitions

  • the present invention relates to a viscosity index improver composition and a lubricating oil composition.
  • Hydraulic oils used as power transmission media in hydraulic equipment include synthetic hydraulic oils, water-containing hydraulic oils, and mineral oil-based hydraulic oils, but when used in environments with high-temperature heat sources, , flame-retardant synthetic hydraulic oil or water-containing hydraulic fluid is used.
  • phosphate ester hydraulic fluid which is a synthetic hydraulic fluid, has excellent fire resistance, lubricity, oxidation stability, and low compressibility, so it has excellent responsiveness to actuators, etc., so it is used in power plants, aircraft, etc. Used in hydraulic systems. In particular, hydraulic fluids used in aircraft need to have good hydrolytic stability and low-temperature fluidity.
  • Patent Document 1 Since it is used in a wide temperature range, it needs to have a low low-temperature viscosity, but it must also maintain a certain level of acceptable viscosity even at high temperatures, and a high viscosity index is required (Patent Document 1). It is known to use a viscosity index improver (Patent Document 2) in order to obtain a high viscosity index, and for example, lubricating oil compositions using polybutyl methacrylate, polyhexyl methacrylate (Patent Document 3), etc. are known. It is being However, the above-mentioned lubricating oil composition has a problem in that the effect of improving the viscosity index is not yet sufficient.
  • phosphate ester hydraulic fluids are highly hydrophilic and easily decompose into acids and alcohols in the presence of moisture, which are known to corrode metals. Substances can also corrode metals.
  • the products generated as a result of deterioration of the hydraulic oil due to moisture cause poor control due to damage to machines and equipment, and cause problems such as further acceleration of deterioration of the hydraulic oil (Patent Document 4).
  • Patent Document 5 it is widely known to use an alicyclic epoxy ester compound as an acid scavenger
  • Non-Patent Document 1 alicyclic epoxy ester-based acid scavengers have the problem of being hydrolyzed themselves (Patent Document 5), and alicyclic epoxy compounds have higher reactivity with acids and cations than epoxy compounds.
  • Non-Patent Document 1 since the alicyclic epoxy ester acid scavenger is used as an epoxy curing agent (Non-Patent Document 1), it is difficult to react with the acid generated by hydrolysis of phosphoric acid ester or alicyclic epoxy ester.
  • the curing reaction does not end with a simple 1:1 reaction and a high molecular weight epoxy resin is produced. This poses a problem in that the viscosity characteristics of the lubricating oil deteriorate and sludge is generated as an insoluble substance, resulting in deterioration in lubricity.
  • An object of the present invention is to obtain a lubricating oil composition that has an excellent effect of improving the viscosity index, an excellent effect of suppressing hydrolysis of phosphate ester, and is free from precipitates even at low temperatures (-60°C) and has a low viscosity at low temperatures. It is an object of the present invention to provide a viscosity index improver composition capable of improving the viscosity index.
  • the present invention provides a viscosity index improver composition for a lubricating oil composition containing a phosphoric acid ester (C), which essentially comprises a monomer (a) represented by the following general formula (1).
  • R 1 is a hydrogen atom or a methyl group
  • -X 1 - is a group represented by -O- or -NH-
  • R 2 is an alkylene group having 2 to 4 carbon atoms
  • R 3 is a straight group having 1 to 17 carbon atoms
  • p is an integer of 0 to 20, and when p is 2 or more, R 2 may be the same or different.
  • the viscosity index improver composition of the present invention has an excellent effect of improving the viscosity index, an excellent effect of suppressing the hydrolysis of phosphate ester, and is free from precipitates even at low temperatures (-60°C), making it a lubricating oil with low viscosity at low temperatures. This has the effect that a composition can be obtained.
  • the viscosity index improver composition of the present invention is a viscosity index improver composition for lubricating oil compositions containing a phosphoric acid ester (C), and includes a monomer ( The (co)polymer (A) containing a) as an essential constituent monomer and a chain aliphatic alcohol (B) having an HLB value of 2.5 to 7.0, This is a viscosity index improver composition in which the solubility parameter of aggregate (A) is 9.00 to 9.80 (cal/cm 3 ) 1/2 .
  • “(co)polymer” means “homopolymer and/or copolymer”.
  • monomer (a) may be used alone or in combination of two or more.
  • (meth)acrylate means acrylate or methacrylate
  • (meth)acrylamide means acrylamide or methacrylamide
  • (meth)acrylic acid means acrylic acid or methacrylic acid.
  • R 1 is a hydrogen atom or a methyl group
  • -X 1 - is a group represented by -O- or -NH-
  • R 2 is an alkylene group having 2 to 4 carbon atoms
  • R 3 is a straight group having 1 to 17 carbon atoms
  • p is an integer of 0 to 20, and when p is 2 or more, R 2 may be the same or different.
  • R 1 is a hydrogen atom or a methyl group, and is preferably a methyl group from the viewpoint of improving the viscosity index.
  • the viscosity index improver composition of the present invention contains a (co)polymer (A) having the monomer (a) represented by the general formula (1) as an essential constituent monomer.
  • -X 1 - is a group represented by -O- or -NH-, and from the viewpoint of improving the viscosity index, it is preferably a group represented by -O-.
  • R 2 is an alkylene group having 2 to 4 carbon atoms, such as an ethylene group, a propylene group, a butylene group, and the like. Among these, from the viewpoint of improving the viscosity index, ethylene groups are preferred.
  • p is an integer of 0 to 20, and when p is 2 or more, R 2 may be the same or different, and from the viewpoint of improving the viscosity index, it is preferably 0 to 4. , more preferably 0 to 2.
  • R 3 is a straight chain or branched alkyl group having 1 to 17 carbon atoms, such as a methyl group, an ethyl group, a straight chain alkyl group ⁇ for example, an n-propyl group, an n-butyl group , n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group , n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, etc. ⁇ , branched alkyl group ⁇ for example, isopropyl group, isobutyl group, sec-butyl group, tert-buty
  • straight chain or branched alkyl groups having 1 to 15 carbon atoms are preferred, and straight chain or branched alkyl groups having 1 to 13 carbon atoms are more preferred.
  • straight chain or branched alkyl groups having 1 to 13 carbon atoms are more preferred.
  • a combination of one having a straight chain or branched alkyl group having 1 to 3 carbon atoms and one having a straight chain or branched alkyl group having 4 to 17 carbon atoms is preferred, and more preferably.
  • an alkyl (meth)acrylate having a straight chain or branched alkyl group having 1 to 17 carbon atoms [for example, an alkyl (meth)acrylate (a1) having a straight chain or branched alkyl group having 1 to 3 carbon atoms ⁇ for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, etc. ⁇ , alkyl (meth)acrylate (a2) having a straight chain or branched alkyl group having 4 to 17 carbon atoms ⁇
  • N-alkyl (meth)acrylamide having a straight chain or branched alkyl group having 1 to 17 carbon atoms ⁇ for example, methyl (meth)acrylamide, ethyl (meth)acrylamide, n-propyl (meth)acrylamide, n-butyl ( meth)acrylamide, n-pentyl(meth)acrylamide, n-hexyl(meth)acrylamide, n-heptyl(meth)acrylamide, n-octyl(meth)acrylamide, n-nonyl(meth)acrylamide, n-decyl(meth)acrylamide ) acrylamide, n-undecyl (meth)acrylamide, n-dodecyl (meth)acrylamide, n-tridecyl (meth)acrylamide, n-tetradecyl (meth)acrylamide, n-p
  • the monomer (a) is preferably one in which -X 1 - in general formula (1) is -O-, and more preferably a linear or branched alkyl having 1 to 17 carbon atoms.
  • alkyl (meth)acrylate having a chain or branched alkyl group and particularly preferably a combination of an alkyl (meth)acrylate (a1) having a straight chain or branched alkyl group having 1 to 3 carbon atoms and an alkyl (meth)acrylate having 6 to 13 carbon atoms. It is a combination with an alkyl (meth)acrylate having a straight chain or branched alkyl group.
  • Neodol (registered trademark) 23 mixture of linear and branched alkyl alcohols having 12 to 13 carbon atoms, manufactured by SHELL
  • Neodol (registered trademark) 45 straight chain and branched alkyl alcohols having 14 to 15 carbon atoms
  • (Meth)acrylic acid esters of mixtures of alkyl alcohols, such as mixtures of chain and branched alkyl alcohols (SHELL) may also be used.
  • the (co)polymer (A) includes, in addition to the monomer (a), a hydroxyl group-containing monomer (e) and a nitrogen atom-containing monomer (f) (excluding monomer (a)).
  • ) may be a copolymer whose constituent monomer is one or more selected from the group consisting of:
  • hydroxyl group-containing monomer (e) include the following. Hydroxyl group-containing aromatic monomer (p-hydroxystyrene, etc.), hydroxyalkyl (2-6 carbon atoms) (meth)acrylate [2-hydroxyethyl (meth)acrylate, and 2- or 3-hydroxypropyl (meth)acrylate etc.], mono- or di-hydroxyalkyl (1 to 4 carbon atoms) substituted (meth)acrylamides [N,N-dihydroxymethyl (meth)acrylamide, N,N-dihydroxypropyl (meth)acrylamide, N,N-dihydroxypropyl (meth)acrylamide, -2-hydroxybutyl (meth)acrylamide, etc.], vinyl alcohol, alkenol having 3 to 12 carbon atoms [(meth)allyl alcohol, crotyl alcohol, isocrotyl alcohol, 1-octenol and 1-undecenol, etc.], carbon number 4 to 12 alkene monools or alk
  • Examples of the nitrogen atom-containing monomer (f) include the following monomers (f1) to (f4).
  • Acrylamide [two alkyl groups having 1 to 4 carbon atoms bonded to a nitrogen atom; for example, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-diisopropyl(meth) acrylamide and N,N-di-n-butyl (meth)acrylamide, etc.], dialkylaminoalkyl (meth)acrylamide [aminoalkyl group in which two alkyl groups having 1 to 4 carbon atoms are bonded to a nitrogen atom (2 to 4 carbon atoms) 6); for example, N,N-dimethylaminoethyl (meth)acrylamide, N,N-diethylaminoethyl (meth)acrylamide, N,N-dimethylaminopropyl (meth)acrylamide and N,N-di-n- butylaminobutyl (meth)acrylamide, etc.], N-vinylcar
  • Nitro group-containing monomer (f2) examples include 4-nitrostyrene.
  • tertiary amino group-containing monomer (f3) Vinyl monomers containing primary amino groups ⁇ alkenylamines having 3 to 6 carbon atoms [(meth)allylamine, crotylamine, etc.], aminoalkyl (meth)acrylates (having 2 to 6 carbon atoms) [aminoethyl (meth)acrylate, etc.] ⁇ ; Secondary amino group-containing vinyl monomer ⁇ monoalkylaminoalkyl (meth)acrylate [those having an aminoalkyl group (having 2 to 6 carbon atoms) in which one alkyl group having 1 to 6 carbon atoms is bonded to the nitrogen atom ; For example, t-butylaminoethyl (meth)acrylate and methylaminoethyl (meth)acrylate, etc.], dialkenylamine having 6 to 12 carbon atoms [di(meth)allylamine, etc.]; Tertiary amino group-containing vinyl monomer
  • Nitrile group-containing monomer (f4) examples include (meth)acrylonitrile.
  • amide group-containing monomers (f1) preferred are amide group-containing monomers (f1) and monomers containing primary to tertiary amino groups from the viewpoint of copolymerizability with other monomers.
  • (f3) and more preferred are N,N-diphenylaminoethyl (meth)acrylamide, dimethylaminoethyl (meth)acrylamide, diethylaminoethyl (meth)acrylamide, dimethylaminopropyl (meth)acrylamide, dimethylaminoethyl (meth)acrylate and diethylaminoethyl (meth)acrylate.
  • the polymer (A) may include the following monomers (g) to (n) as constituent monomers.
  • Alicyclic hydrocarbon monomer (h) examples include cyclohexene, (di)cyclopentadiene, pinene, limonene, vinylcyclohexene and ethylidenebicycloheptene.
  • Vinyl esters, vinyl ethers, vinyl ketones (j): Vinyl esters of saturated fatty acids with 2 to 12 carbon atoms (vinyl acetate, vinyl propionate, vinyl butyrate, vinyl octoate, etc.), alkyl, aryl or alkoxyalkyl vinyl ethers with 1 to 12 carbon atoms (methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether) , butyl vinyl ether, 2-ethylhexyl vinyl ether, phenyl vinyl ether, vinyl-2-methoxyethyl ether, vinyl-2-butoxyethyl ether, etc.) and alkyl or aryl vinyl ketones having 1 to 8 carbon atoms (methyl vinyl ketone, ethyl vinyl ketone, phenyl vinyl ketone, etc.).
  • Epoxy group-containing monomer (k) examples include glycidyl (meth)acrylate and glycidyl (meth)allyl ether.
  • Halogen element-containing monomer (l) examples include vinyl chloride, vinyl bromide, vinylidene chloride, (meth)allyl chloride, and halogenated styrene (dichlorostyrene, etc.).
  • Esters of unsaturated polycarboxylic acids (m): Alkyl, cycloalkyl or aralkyl esters of unsaturated polycarboxylic acids [alkyl diesters having 1 to 8 carbon atoms of unsaturated dicarboxylic acids (maleic acid, fumaric acid, itaconic acid, etc.) (dimethyl maleate, dimethyl fumarate, diethyl maleate) and dioctyl maleate)].
  • the proportion of monomer (a) constituting the (co)polymer (A) is determined from the viewpoint of improving the viscosity index and solubility at low temperature (-60°C). Preferably it is 70 to 100% by weight, more preferably 78 to 100% by weight, particularly preferably 85 to 100% by weight, based on the total weight of the monomers.
  • the ratio of the alkyl (meth)acrylate (a1) having a straight chain or branched alkyl group having 1 to 3 carbon atoms constituting the (co)polymer (A) is determined by the viscosity index improvement effect and low temperature (-60°C) From the viewpoint of solubility, it is preferably 10 to 70% by weight, more preferably 15 to 60% by weight, and particularly preferably It is 20 to 55% by weight.
  • the proportion of the alkyl (meth)acrylate (a2) having a linear or branched alkyl group having 4 to 17 carbon atoms constituting the (co)polymer (A) is determined by the viscosity index improvement effect and low temperature (-60°C) From the viewpoint of solubility, it is preferably 10 to 90% by weight, more preferably 20 to 85% by weight, and particularly preferably It is 30 to 80% by weight.
  • the total proportion of monomers (e) to (f) constituting the (co)polymer (A) is determined by the total weight of the monomers constituting the (co)polymer (A) from the viewpoint of improving the viscosity index.
  • the total proportion of monomers (g) to (n) constituting the (co)polymer (A) is determined based on the composition of the (co)polymer (A) from the viewpoint of solubility at low temperature (-60°C). It is preferably at most 10% by weight, more preferably at most 7% by weight, particularly preferably at most 5% by weight, based on the total weight of the monomers.
  • the solubility parameter (hereinafter abbreviated as SP value) of the (co)polymer (A) is 9.00 to 9.0 from the viewpoint of low temperature viscosity, solubility at low temperature (-60°C), and viscosity index improvement effect. .80 (cal/cm 3 ) 1/2 , preferably 9.00 to 9.50 (cal/cm 3 ) 1/2 , more preferably 9.10 to 9.40 (cal/cm 3 ) ) 1/2 , more preferably 9.20 to 9.40 (cal/cm 3 ) 1/2 , particularly preferably 9.25 to 9.40 (cal/cm 3 ) 1/2 .
  • the SP value of the (co)polymer (A) is 9.00 (cal/cm 3 ) 1/2 or more, the low-temperature viscosity is low and it is difficult to precipitate at low temperatures, and it is 9.80 (cal/cm 3 ) 1/ When it is 2 or less, the viscosity index improving effect is good.
  • the SP value in the present invention is determined by the numerical value (atom or functional group (heat of vaporization and molar volume at 25° C.), it means the value calculated by formula (28) on page 153 of the same.
  • the constituent units derived from methyl methacrylate are 2 CH 3 , 1 CH 2 , 1 C, and 1 CO 2 as atomic groups.
  • the SP value of the structural unit derived from methyl methacrylate is 9.933 (cal/cm 3 ) 1/2 .
  • Similar calculations show that the SP value of the structural unit derived from dodecyl methacrylate is 9.017 (cal/cm 3 ) 1/2 .
  • the SP value of the polymer is as follows: It is calculated by arithmetic averaging based on the weight fraction of the SP value.
  • the SP value of the (co)polymer (A) can be adjusted to a desired range by appropriately adjusting the monomers and weight fractions used. Specifically, the SP value can be reduced by using many monomers with a long alkyl group carbon number, and the SP value can be increased by using many monomers with a short alkyl group carbon number. can do.
  • the weight fraction is calculated based on the SP value of each (co)polymer (A), and the arithmetic average value is the above SP value. It is preferable to satisfy the following.
  • the weight average molecular weight (Mw) of the (co)polymer (A) is preferably 5,000 to 300,000, more preferably 10,000 to 250, from the viewpoint of improving the viscosity index and shear stability. 000, particularly preferably from 30,000 to 200,000, particularly preferably from 50,000 to 150,000.
  • the (co)polymer (A) can be obtained by a known production method, specifically a method of solution polymerizing the above-mentioned monomers in a solvent in the presence of a polymerization catalyst.
  • the solvent include toluene, xylene, alkylbenzene having 9 to 10 carbon atoms, methyl ethyl ketone, ethyl acetate, 2-propanol, and phosphoric acid ester (C).
  • polymerization catalysts examples include azo catalysts (azobisisobutyronitrile and azobisvaleronitrile, etc.), peroxide catalysts (benzoyl peroxide, cumyl peroxide, lauryl peroxide, etc.), and redox catalysts (benzoyl peroxide, etc.). and tertiary amine). Furthermore, if necessary, a known chain transfer agent (such as an alkyl mercaptan having 2 to 20 carbon atoms) may be used.
  • the polymerization temperature is preferably 25 to 140°C, more preferably 50 to 120°C.
  • the (co)polymer (A) can be obtained by bulk polymerization, emulsion polymerization, or suspension polymerization.
  • the polymerization form may be either a random addition polymer or an alternating copolymer, or a graft copolymer or a block copolymer. .
  • the viscosity index improver composition of the present invention contains a chain aliphatic alcohol (B) having an HLB value of 2.5 to 7.0.
  • HLB value 2.5 or more
  • precipitates are less likely to be generated at low temperatures (-60° C.), and when it is 7.0 or less, the effect of suppressing the hydrolysis of phosphate ester is excellent.
  • HLB of (B) is 7.0 or less
  • micelles can be formed against the water mixed in the lubricating oil and hydrolysis of the phosphate ester can be suppressed, and when the HLB is 2.5 or more.
  • the HLB value of the chain aliphatic alcohol (B) is preferably 3.0 to 6.0, more preferably 4.0 to 5.0.
  • the HLB value is an index indicating the balance between hydrophilicity and lipophilicity, and is described, for example, in "Introduction to Surfactants” [published by Sanyo Chemical Industries, Ltd., 2007, written by Takehiko Fujimoto], page 212. This is known as the value calculated by the Oda method, and not the value calculated by the Griffin method.
  • the organic value and inorganic value for deriving HLB are determined as 20 per carbon atom as the organic value, and the inorganic value is determined as Calculated using the values in the table described on page 213 of "Introduction to Drugs".
  • chain aliphatic alcohol (B) from the viewpoint of improving the stability of the lubricating oil composition over time (suppressing hydrolysis of phosphate ester), a straight chain or branched aliphatic alcohol having 8 to 17 carbon atoms is used.
  • straight-chain or branched aliphatic alcohols having 9 to 16 carbon atoms are preferred, and straight-chain or branched aliphatic alcohols having 10 to 15 carbon atoms are particularly preferred.
  • the SP value of the chain aliphatic alcohol (B) is preferably 9.00 to 10.20 (cal/cm 3 ) 1/2 , more preferably 9.50 to 1/2, from the viewpoint of improving the stability of the lubricating oil over time. 10.00 (cal/cm 3 ) 1/2 . Further, when a plurality of chain aliphatic alcohols (B) having different SP values are contained, it is preferable that the arithmetic average value based on the weight fraction is within the above range.
  • the viscosity index improver composition of the present invention has an excellent effect of improving the viscosity index, an excellent effect of suppressing hydrolysis of phosphate ester, and is free from precipitates even at low temperatures (-60°C), and has a good viscosity at low temperatures for lubricating. Since an oil composition can be obtained, it can be used as a viscosity index improver composition for lubricating oil compositions containing phosphate ester (C).
  • Examples of the phosphoric acid ester (C) include those represented by the following general formula (2).
  • R 4 OP(O)-(OR 4 ) 2 (2) [In general formula (2), R 4 each independently represents a hydrocarbon group having 1 to 10 carbon atoms. ]
  • the hydrocarbon group having 1 to 10 carbon atoms includes an alkyl group having 1 to 10 carbon atoms ⁇ for example, a straight chain alkyl group (for example, a methyl group, an ethyl group, an n-propyl group, an n- butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, etc.), branched alkyl group (e.g.
  • the hydrocarbon group having 1 to 10 carbon atoms is preferably a hydrocarbon group having 1 to 6 carbon atoms, and more preferably a hydrocarbon group having 2 to 4 carbon atoms.
  • Examples of the phosphate ester (C) include tri(isopropyl) phosphate, tri(n-butyl) phosphate, tri(isobutyl) phosphate, tri(sec-butyl) phosphate, and tert-butyl phosphate.
  • n-butyldiisobutyl phosphate di-n-butylisobutyl phosphate, diisobutylpentyl phosphate, tri(n-pentyl) phosphate, tri(isopentyl) phosphate, tri(2-ethylhexyl) phosphate, phosphoric acid
  • examples include n-butyldiphenyl, isobutyldiphenyl phosphate, triphenyl phosphate, tri(isopropylphenyl) phosphate, and tri(isobutylphenyl) phosphate.
  • tri(n-butyl) phosphate, tri(isobutyl) phosphate, tri(sec-butyl) phosphate, tri(tert-butyl) phosphate, tri(t-butyl) phosphate, Phenyl and tri(isopropylphenyl) phosphate are preferred, and tri(n-butyl) phosphate and tri(isobutyl) phosphate are more preferred.
  • the kinematic viscosity (measured according to ASTM D 445) at 100°C of the phosphoric acid ester (C) is preferably 1 to 5 mm 2 /s, more preferably 1 to 4 mm 2 /s from the viewpoint of low-temperature viscosity. , particularly preferably 1 to 3.5 mm 2 /s.
  • the kinematic viscosity (measured according to ASTM D 445) at 40°C of the phosphoric acid ester (C) is preferably 1 to 40 mm 2 /s, more preferably 1 to 25 mm 2 /s from the viewpoint of low-temperature viscosity. , particularly preferably 1 to 20 mm 2 /s.
  • the viscosity index improver composition of the present invention is a viscosity index improver composition containing the (co)polymer (A) and the chain aliphatic alcohol (B).
  • the viscosity index improver composition of the present invention can improve the viscosity index of the lubricating oil composition when added to a lubricating oil composition containing the phosphate ester (C).
  • the improvement effect is high, and by containing the chain aliphatic alcohol (B), the effect of suppressing the hydrolysis of the phosphoric acid ester (C) is excellent.
  • the chain aliphatic alcohol (B) tends to precipitate in the phosphoric ester (C) especially at low temperatures (-60°C), and the (co)polymer (A) and the chain aliphatic alcohol (B) tend to precipitate in the phosphate ester (C). ) can be made to be difficult to precipitate in the phosphoric ester (C). Therefore, the viscosity index improver composition of the present invention improves the viscosity index of the lubricating oil composition by containing the (co)polymer (A) and the chain aliphatic alcohol (B). It is possible to suppress deterioration of lubricity due to hydrolysis of ester (C) and suppress precipitation at low temperatures.
  • the weight ratio (A/B) of the above-mentioned (co)polymer (A) and the above-mentioned chain aliphatic alcohol (B) in the viscosity index improver composition has the effect of improving the stability over time and improving the viscosity index of the lubricating oil. From this point of view, it is preferably 10 to 5,000, more preferably 10 to 3,000, particularly preferably 10 to 500.
  • the absolute value of the difference between the SP value of the (co)polymer (A) and the SP value of the chain aliphatic alcohol (B) is 0.10 to 1.00 ( It is preferably 0.20 to 0.90 (cal/cm 3 ) 1/2 , more preferably 0.20 to 0.90 (cal/cm 3 ) 1/2 .
  • the absolute value of the difference in arithmetic average values based on the respective weight fractions should be within the above range. It is preferable that there be.
  • the viscosity index improver composition of the present invention only needs to contain the above-mentioned (co)polymer (A) and the above-mentioned chain aliphatic alcohol (B). ) may also be included.
  • the content of the (co)polymer (A) in the viscosity index improver composition is 10 to 70% by weight based on the weight of the viscosity index improver composition, from the viewpoint of ease of handling the viscosity index improver composition. %, more preferably 20 to 60% by weight.
  • the content of the chain aliphatic alcohol (B) in the viscosity index improver composition is based on the weight of the viscosity index improver composition, from the viewpoint of stability over time when producing a lubricating oil composition.
  • the content of the phosphoric acid ester (C) in the viscosity index improver composition is preferably 25 to 89% by weight, more preferably 35% by weight, based on the weight of the viscosity index improver composition. It is 5 to 79% by weight.
  • the viscosity index improver composition of the present invention has an excellent viscosity index improvement effect and a phosphate ester hydrolysis inhibiting effect, and furthermore, there is no precipitate even at low temperatures (-60°C), and the viscosity at low temperatures is good for lubricants.
  • the oil composition can be obtained, it can be used as a viscosity index improver for lubricating oil compositions containing phosphoric ester (C), and further containing phosphoric ester (C) as a base oil. It is particularly useful as a viscosity index improver for aircraft hydraulic fluids that may be used in the sky (under low-temperature environments).
  • the lubricating oil composition of the present invention contains the viscosity index improver composition and a phosphoric acid ester (C).
  • the content of the (co)polymer (A) in the lubricating oil composition is preferably 1 to 15% by weight based on the weight of the lubricating oil composition from the viewpoint of low-temperature viscosity and kinematic viscosity at 100 ° C. More preferably, it is 2 to 10% by weight.
  • the content of the chain aliphatic alcohol (B) in the lubricating oil composition is from 0.01 to 0.6% by weight based on the weight of the lubricating oil composition from the viewpoint of stability over time of the lubricating oil.
  • the content of phosphate ester (C) in the lubricating oil composition is preferably 75% by weight or more, more preferably 75 to 98.99% by weight, based on the weight of the lubricating oil composition, from the viewpoint of low-temperature viscosity. , more preferably 80 to 97.95% by weight.
  • the weight ratio (A/B) of the (co)polymer (A) and the chain aliphatic alcohol (B) in the lubricating oil composition is preferably 10 to 5,000 from the viewpoint of improving the viscosity index, and It is preferably 10 to 3,000, particularly preferably 10 to 500.
  • the phosphoric ester (C) contained in the lubricating oil composition may be the phosphoric ester (C) contained in the viscosity index improver composition, or may be the phosphoric ester (C) that is derived from a source other than the viscosity index improver composition. It may also be an acid ester (C).
  • the phosphoric ester (C) contained in the lubricating oil composition is the phosphoric ester (C) derived from a source other than the phosphoric ester (C) contained in the viscosity index improver composition and the viscosity index improver composition. ) may be a mixture.
  • the phosphoric ester (C) contained in the lubricating oil composition the above-mentioned phosphoric ester (C) can be used.
  • the phosphoric acid ester (C) derived from a source other than the viscosity index improver composition tri(n-butyl) phosphate is preferred, and a mixture of tri(isopropylphenyl) phosphate and triphenyl phosphate is also preferred. It is preferable that the phosphoric acid ester (C) contained in the lubricating oil composition has a kinematic viscosity at 40° C. of 1 to 40 mm 2 /s.
  • ⁇ Method for measuring the content of chain aliphatic alcohol (B) in the viscosity index improver composition and lubricating oil composition Using a Soxhlet extractor, 1 g of the viscosity index improver composition or lubricating oil composition of the present invention is separated and extracted into the (co)polymer (A) component and other components soluble in the hexane solvent using 300 ml of hexane solvent. Since the chain aliphatic alcohol (B) is dissolved in hexane, it is included in the other extracted components. The hexane solvent in the solution containing the extracted other components is distilled off under reduced pressure using an evaporator.
  • the content of chain aliphatic alcohol (B) in the composition can be calculated from the amount of the viscosity index improver composition or lubricating oil composition used, the amount X of other component extracts, and the peak area ratio.
  • GC-MS measurement conditions Equipment: "GC-2010" [manufactured by Shimadzu Corporation] Column: “ZB-5 (column length: 30 m, column inner diameter: 0.25 mm, film thickness: 0.25 ⁇ m)” [manufactured by Shimadzu GLC Co., Ltd.] Vaporization chamber temperature: 250°C Pressure: 1000kPa Split ratio: 50 Temperature raising conditions: Hold at 40°C for 5 minutes, raise temperature to 300°C (10°C/min), hold at 300°C for 10 minutes. (MS measurement conditions) Equipment: "GCMS QP-2010 Plus” [manufactured by Shimadzu Corporation] Ion source: CI Ion source temperature: 170°C Interface temperature: 250°C Introduced reagent gas: I
  • the lubricating oil composition of the present invention contains, in addition to the viscosity index improver composition and the phosphate ester (C), other additives ⁇ an antioxidant, a friction modifier, an antifoaming agent, a rust preventive, and a corrosion preventive agent. at least one kind of additive selected from the group consisting of various additives such as additives.
  • Antioxidant For example, 2,6-di-tert-butylphenol (hereinafter, tert-butyl is abbreviated as t-butyl), 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-Butyl-4-ethylphenol, 2,4-dimethyl-6-t-butylphenol, 4,4'-methylenebis(2,6-di-t-butylphenol), 4,4'-bis(2,6-di- t-butylphenol), 4,4'-bis(2-methyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4- ethyl-6-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 4,4'-isopropylidenebis(2,6-di-t-butylphenol), 2,2 '-Methylenebis
  • Friction modifier For example, higher alcohols such as oleyl alcohol, stearyl alcohol, and lauryl alcohol; fatty acids such as oleic acid, stearic acid, and lauric acid; glyceryl oleate, glyceryl stearate, glyceryl laurate, alkyl glyceryl ester, alkenyl glyceryl ester, alkynyl Esters such as glyceryl ester, ethylene glycol oleate, ethylene glycol stearate, ethylene glycol laurate, propylene glycol oleate, propylene glycol stearate, and propylene glycol laurate; oleylamide, stearylamide, lauryl Amides such as amides, alkylamides, alkenylamides and alkynylamides; oleylamine, stearylamine, laurylamine, alkylamine, alkenylamine, alkynyl
  • Antifoaming agent examples include polydimethyl silicone, dimethyl silicone oil, trifluoropropyl methyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy/propoxylate, fatty acid ethoxy/propoxylate, and sorbitan partial fatty acid ester.
  • Rust inhibitor For example, sodium nitrite, oxidized paraffin wax calcium salt, oxidized paraffin wax magnesium salt, tallow fatty acid alkali metal salt, alkaline earth metal salt, alkaline earth amine salt, alkenyl succinic acid, alkenyl succinic acid half ester (molecular weight of alkenyl group (about 100 to 300), sorbitan monoester, nonylphenol ethoxylate, and lanolin fatty acid calcium salt.
  • Corrosion inhibitor For example, 2-ethylhexyl 7-oxabicyclo[4.1.0]heptane-3-carboxylic acid, 7-oxabicyclo[4.1.0]heptane as the alicyclic epoxide as disclosed in Patent Document 2 2-Hydroxy-N-(1H-1,2,4-triazole- 3-yl)benzamide, N,N-bis(2-ethylhexyl)-[(1,2,4-triazol-1-yl)methyl]amine, N,N-bis(2-ethylhexyl)-[(1, 2,4-triazol-1-yl)methyl]amine and 2,2'-[[(4 or 5 or 1)-(2-ethylhexyl)-methyl-1H-benzotriazol-1-methyl]imino]bisethanol
  • Other examples include bis(poly-2-carboxyethyl)phosphinic acid, hydroxyphosphonoacetic acid, tetraalky
  • additives may include one type, two or more types may be used in combination, and a package additive containing multiple types may be used as the additive.
  • the content of other additives is preferably 1 to 15% by weight, more preferably 2 to 10% by weight, based on the weight of the lubricating oil composition.
  • the viscosity index (measured according to ASTM D 445) of the lubricating oil composition is preferably 300 or more, more preferably 320 or more, and particularly preferably 330 or more.
  • the low-temperature viscosity of the lubricating oil composition is preferably 1200 mPa ⁇ s or less, more preferably 1100 mPa ⁇ s or less. , particularly preferably 1050 mPa ⁇ s or less.
  • the lubricating oil composition of the present invention has a high viscosity index, suppresses the hydrolysis of phosphoric acid ester, and has no precipitates even at low temperatures (-60°C), and has good viscosity at low temperatures. It is useful as an aircraft hydraulic fluid that is sometimes used in low-temperature environments.
  • the present disclosure (1) is a viscosity index improver composition for a lubricating oil composition containing a phosphate ester (C), A (co)polymer (A) having monomer (a) represented by the following general formula (1) as an essential constituent monomer, and a chain aliphatic compound having an HLB value of 2.5 to 7.0.
  • the present invention is a viscosity index improver composition containing alcohol (B) and in which the (co)polymer (A) has a solubility parameter of 9.00 to 9.80 (cal/cm 3 ) 1/2 .
  • R 1 is a hydrogen atom or a methyl group
  • -X 1 - is a group represented by -O- or -NH-
  • R 2 is an alkylene group having 2 to 4 carbon atoms
  • R 3 is a straight group having 1 to 17 carbon atoms
  • p is an integer of 0 to 20, and when p is 2 or more, R 2 may be the same or different.
  • the present disclosure (2) is the viscosity index improver composition according to the present disclosure (1), wherein the (co)polymer (A) has a weight average molecular weight of 5,000 to 300,000.
  • the present disclosure (3) provides the present disclosure (1) or (2), wherein the weight ratio (A/B) of the (co)polymer (A) and the chain aliphatic alcohol (B) is 10 to 5000.
  • the present disclosure (4) relates to any one of the present disclosure (1) to (3), wherein the chain aliphatic alcohol (B) is a linear or branched aliphatic alcohol having 8 to 17 carbon atoms.
  • the present disclosure (5) is the viscosity index improver composition according to any one of the present disclosure (1) to (4), which further contains a phosphoric acid ester (C).
  • the present disclosure (6) is a lubricating oil composition containing the viscosity index improver composition according to any one of the present disclosures (1) to (5) and a phosphoric acid ester (C).
  • the present disclosure (7) is the lubricating oil composition according to the present disclosure (6), wherein the content of the phosphate ester (C) in the lubricating oil composition is 75% by weight or more.
  • the present disclosure (8) is the lubricating oil composition according to the present disclosure (6) or (7), wherein the phosphoric acid ester (C) has a kinematic viscosity of 1 to 40 mm 2 /s at 40° C.
  • the present disclosure (9) is the lubricating oil composition according to any one of the present disclosure (6) to (8), which is used as an aircraft hydraulic fluid.
  • Examples 1 to 14, Comparative Examples 1 to 5> In a reaction vessel equipped with a stirring device, a heating and cooling device, a thermometer, a dropping funnel, a nitrogen introduction pipe, and a pressure reducing device, add 100 weight phosphoric acid esters (C) of the types and amounts listed in Tables 2-1 to 2-3. Into another glass beaker, add chain aliphatic alcohol (B) or comparative compound (B') of the types and amounts listed in Tables 2-1 to 2-3, and polymer ( The constituent monomers of A), a chain transfer agent, and a polymerization initiator were added, stirred and mixed at 20°C to prepare a monomer solution, and the solution was added to a dropping funnel.
  • C phosphoric acid esters
  • the monomer solution was converted into phosphate ester (C) over a period of 3 hours while keeping the system temperature at 70 to 80°C under closed conditions. was added dropwise to the reaction vessel containing the solution. At this time, each raw material was charged so that the liquid level of the reaction solution was 70% of the capacity of the reaction container. After aging at 90°C for 2 hours from the end of dropping, the temperature was raised to 120°C, and at the same temperature, the degree of vacuum was reduced to 0.027 to 0.040 MPa until the liquid level reached 90% of the capacity of the reaction vessel. The pressure was gradually reduced so as not to exceed the pressure, and then unreacted monomers were removed until the generation of bubbles completely disappeared.
  • gas phase oxygen concentration 100 ppm
  • viscosity index improver compositions (R1) to (R14), (S1) containing the (co)polymer (A) and the chain aliphatic alcohol (B) or the comparative compound (B') were prepared. ⁇ (S5) was obtained.
  • the Mw of the copolymers (A1) to (A11) and (A'1) to (A'2) and the content of the chain aliphatic alcohol (B) in the obtained viscosity index improver composition were determined as above. The results measured by this method are shown in Tables 2-1 to 2-3. In addition, the appearance at low temperatures and hydrolytic stability of the viscosity index improver composition were measured by the following methods, and the results are shown in Tables 2-1 to 2-3.
  • Monomer (a), monomer (e), monomer (f), chain transfer agent, polymerization initiator, chain aliphatic alcohol ( B), comparative compound (B'), phosphoric acid ester (C), and additive (antifoaming agent) were as follows.
  • ⁇ Method for measuring hydrolytic stability of viscosity index improver composition The acid value of the viscosity index improver composition was measured according to JIS K0070. Further, 1% by weight of water was added to the prepared viscosity index improver composition, and the mixture was heated at 100° C. for 100 hours. The acid value after heating was measured according to JIS K0070. The difference between the acid value before heating and the acid value after heating is listed as the degree of change in acid value in Tables 2-1 to 2-3.
  • Examples 15 to 28 and Comparative Examples 6 to 10 evaluation of lubricating oil composition
  • a stainless steel container equipped with a stirring device add the viscosity index improver composition in the amount listed in Table 3 to prepare a lubricating oil composition so that the kinematic viscosity at 100° C. is 3.50 mm 2 /s. did.
  • the obtained lubricating oil composition was evaluated for its kinematic viscosity at 100°C, kinematic viscosity at 40°C, viscosity index, shear stability, low temperature viscosity (-54°C), appearance at low temperature (-60°C), and hydrolytic stability as follows. It was measured by the method. The results are shown in Table 3.
  • ⁇ Method for measuring low-temperature viscosity (-54°C) of lubricating oil composition The viscosity of the sample after cooling at -54°C for 3 hours was measured using a Brookfield viscometer according to JPI-5S-26-99. The smaller the number, the lower the low-temperature viscosity and the higher the low-temperature properties.
  • ⁇ Method for measuring hydrolytic stability of lubricating oil composition The acid value of the lubricating oil composition was measured according to JIS K0070. Further, 1% by weight of water was added to the prepared lubricating oil composition, and the mixture was heated at 100° C. for 100 hours. The acid value after heating was measured according to JIS K0070. The difference between the acid value before heating and the acid value after heating is shown in Table 3 as the degree of change in acid value.
  • the lubricating oil composition containing the viscosity index improver of the present invention has an excellent viscosity index, no precipitates even at low temperatures, low viscosity at low temperatures, and excellent viscosity due to aging. It can be seen that hydrolysis of the acid ester is small and the properties are excellent.
  • the viscosity index improver composition of the present invention has an excellent viscosity index improvement effect and a phosphate ester hydrolysis inhibiting effect, and furthermore, there is no precipitate even at low temperatures (-60°C), and the viscosity at low temperatures is good for lubricants. Since the lubricating oil composition containing the viscosity index improver composition of the present invention has a low viscosity index and phosphoric acid ester hydrolysis, it also has no precipitates even at low temperatures (-60°C). Since it has a good viscosity at low temperatures, it is particularly useful as an aircraft hydraulic fluid that may be used in the sky (in a low-temperature environment).

Landscapes

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

Abstract

La présente invention concerne une composition améliorant l'indice de viscosité pour une composition d'huile lubrifiante contenant un ester de phosphate (C), la composition améliorant l'indice de viscosité contenant : un (co)polymère (A) ayant un monomère (a) représenté par la formule générale (1) en tant que monomère constitutif essentiel ; et un alcool aliphatique à chaîne (B) ayant une valeur HLB de 2,5 à 7,0, le (co)polymère (A) ayant un paramètre de solubilité de 9,00 à 9,80 (cal/cm3)1/2. (R1 représente un atome d'hydrogène ou un groupe méthyle ; –X1– représente un groupe représenté par –O– ou –NH– ; R2 représente un groupe alkylène en C2-4 ; R3 représente un groupe alkyle linéaire ou ramifié en C1-17 ; p est un nombre entier de 0 à 20 ; et lorsque p vaut 2 ou plus, R2 peut être identique ou différent.)
PCT/JP2023/022777 2022-06-27 2023-06-20 Composition améliorant l'indice de viscosité et composition d'huile lubrifiante WO2024004763A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022102591 2022-06-27
JP2022-102591 2022-06-27

Publications (1)

Publication Number Publication Date
WO2024004763A1 true WO2024004763A1 (fr) 2024-01-04

Family

ID=89382226

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/022777 WO2024004763A1 (fr) 2022-06-27 2023-06-20 Composition améliorant l'indice de viscosité et composition d'huile lubrifiante

Country Status (1)

Country Link
WO (1) WO2024004763A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1077494A (ja) * 1996-08-08 1998-03-24 Rohm & Haas Co 油圧作動液組成物
JP2002529577A (ja) * 1998-11-10 2002-09-10 エクソンモービル リサーチ アンド エンジニアリング カンパニー ｎ−ブチル／イソブチルホスフェートエステル混合物からなるホスフェートエステル基油および該基油からなる航空機用油圧作動油
JP2003524673A (ja) * 1998-10-23 2003-08-19 エクソンモービル リサーチ アンド エンジニアリング カンパニー 燐酸エステル基油および該基油を含む航空機用油圧作動油
JP2008546871A (ja) * 2005-06-14 2008-12-25 ソリユテイア・インコーポレイテツド 高性能リン酸エステル油圧流体
JP2009503142A (ja) * 2005-07-19 2009-01-29 エクソンモービル リサーチ アンド エンジニアリング カンパニー 酸捕捉特性が強化された航空機のリン酸エステル機能性流体
JP2016017170A (ja) * 2014-07-11 2016-02-01 東亞合成株式会社 潤滑油用添加剤及び潤滑油組成物
WO2022039266A1 (fr) * 2020-08-20 2022-02-24 三洋化成工業株式会社 Composition améliorant l'indice de viscosité et composition d'huile lubrifiante

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1077494A (ja) * 1996-08-08 1998-03-24 Rohm & Haas Co 油圧作動液組成物
JP2003524673A (ja) * 1998-10-23 2003-08-19 エクソンモービル リサーチ アンド エンジニアリング カンパニー 燐酸エステル基油および該基油を含む航空機用油圧作動油
JP2002529577A (ja) * 1998-11-10 2002-09-10 エクソンモービル リサーチ アンド エンジニアリング カンパニー ｎ−ブチル／イソブチルホスフェートエステル混合物からなるホスフェートエステル基油および該基油からなる航空機用油圧作動油
JP2008546871A (ja) * 2005-06-14 2008-12-25 ソリユテイア・インコーポレイテツド 高性能リン酸エステル油圧流体
JP2009503142A (ja) * 2005-07-19 2009-01-29 エクソンモービル リサーチ アンド エンジニアリング カンパニー 酸捕捉特性が強化された航空機のリン酸エステル機能性流体
JP2016017170A (ja) * 2014-07-11 2016-02-01 東亞合成株式会社 潤滑油用添加剤及び潤滑油組成物
WO2022039266A1 (fr) * 2020-08-20 2022-02-24 三洋化成工業株式会社 Composition améliorant l'indice de viscosité et composition d'huile lubrifiante

Similar Documents

Publication Publication Date Title
EP2607464B1 (fr) Agent extrême pression pour huile lubrifiante, et composition d'huile lubrifiante le contenant
JP6429244B2 (ja) 潤滑剤組成物及びそれを含有する潤滑油組成物
JP4414123B2 (ja) 単量体及びそれからなる共重合体
US11008528B2 (en) Viscosity index improver and lubricating oil composition
BR102018076009A2 (pt) Polímero de polialquil(met)acrilato, seu método de produção, uso e composição
KR101982900B1 (ko) 윤활유용 마찰마모 저감제 및 그것을 함유하는 윤활유 조성물
WO2012081180A1 (fr) Améliorant de l'indice de viscosité et composition d'huile de graissage
JP2009173921A (ja) 潤滑油添加剤及び潤滑油組成物
CN115885026B (zh) 粘度指数改进剂组合物和润滑油组合物
JPWO2019111753A1 (ja) 潤滑剤組成物および該潤滑剤組成物を含有する潤滑油組成物
KR20010021514A (ko) 개선된 점도 특성을 갖는 자동차용 전동 유체 조성물
WO2024004763A1 (fr) Composition améliorant l'indice de viscosité et composition d'huile lubrifiante
JP2015038194A (ja) 粘度指数向上剤及び潤滑油組成物
JP5032029B2 (ja) 粘度指数向上剤および潤滑油組成物
CN112391222B (zh) 一种抗氧抗磨润滑油添加剂及其应用
JP2007262245A (ja) 流動点降下剤および炭化水素油組成物
JP2004002747A (ja) 潤滑油用摩擦調整剤及び潤滑油組成物
JP2017171882A (ja) 粘度指数向上剤及び潤滑油組成物
KR20100074049A (ko) 점도 특성이 개선된 파워 변속기 유체
JP2018172663A (ja) 流動点降下剤及び潤滑油組成物
JP2006124513A (ja) 粘度指数向上剤組成物および潤滑油組成物
JP2014169426A (ja) 粘度指数向上剤及びこれを含む潤滑油組成物
US20180142180A1 (en) Automatic transmission fluid
JP2014125580A (ja) 粘度指数向上剤及びこれを含む潤滑油組成物
JP2016079393A (ja) 潤滑油

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23831209

Country of ref document: EP

Kind code of ref document: A1