WO2023189293A1 - Huile de base pour huile lubrifiante, huile lubrifiante et fluide de travail - Google Patents

Huile de base pour huile lubrifiante, huile lubrifiante et fluide de travail Download PDF

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Publication number
WO2023189293A1
WO2023189293A1 PCT/JP2023/008627 JP2023008627W WO2023189293A1 WO 2023189293 A1 WO2023189293 A1 WO 2023189293A1 JP 2023008627 W JP2023008627 W JP 2023008627W WO 2023189293 A1 WO2023189293 A1 WO 2023189293A1
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Prior art keywords
lubricating oil
acid
mass
oil
fatty acid
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PCT/JP2023/008627
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English (en)
Japanese (ja)
Inventor
祐也 水谷
由真 関
素也 岡崎
英俊 尾形
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Ｅｎｅｏｓ株式会社
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Publication of WO2023189293A1 publication Critical patent/WO2023189293A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • 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
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • 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

Definitions

  • the present invention relates to a base oil for lubricating oil, a lubricating oil, and a working fluid.
  • Refrigerating machines such as refrigerators, car air conditioners, room air conditioners, and vending machines are equipped with a compressor to circulate refrigerant within the refrigeration cycle.
  • the compressor is filled with lubricating oil (refrigerating machine oil) for lubricating the sliding members.
  • Lubricating oils generally contain a base oil and additives selected depending on the desired properties.
  • Patent Document 1 describes a refrigerating machine oil for hydrocarbon refrigerants that is capable of achieving both low viscosity and maintaining the refrigerant dissolution viscosity, as well as maintaining the refrigerant compatibility and refrigerant dissolution viscosity of the refrigerating machine oil.
  • Refrigerating machine oil for a hydrocarbon refrigerant is disclosed, which is characterized by containing an ester of a fatty acid and a polyhydric alcohol in which the ratio of straight chain fatty acids of No. 22 is 50 to 100 mol %.
  • esters of certain fatty acids and polyhydric alcohols are known as base oils used in lubricating oils such as refrigerating machine oils, but according to the studies of the present inventors, There is room for further improvement in the stability of lubricating oil base oils containing such esters when water is mixed in.
  • one aspect of the present invention is to provide a base oil for lubricating oil that has excellent stability even when water is mixed in.
  • the ester used as the base oil should preferably be a complete ester from the viewpoint of excellent hydrolytic stability.
  • the present inventors found that in esters of trihydric alcohols and fatty acids having 14 to 20 carbon atoms, if the amount of triester, which is a complete ester, is too large, the stability will be significantly deteriorated when water is mixed in. (The peroxide value increases). If the above-mentioned ester contains diester, which is a partial ester, and the amount of triester is below a certain amount, even when water is mixed in, the increase in peroxide value is suppressed and excellent stability can be obtained. It has been found.
  • One aspect of the present invention is a base oil for lubricating oil containing an ester of a trihydric alcohol and a fatty acid having 14 to 20 carbon atoms, wherein the ester includes a diester and a triester, and the content of the triester is It is a base oil for lubricating oils, which has a content of 93 mol% or less based on the total amount of ester and triester.
  • the fatty acid having 14 to 20 carbon atoms may include oleic acid.
  • the content of oleic acid may be 80% by mass or more based on the total amount of fatty acids having 14 to 20 carbon atoms.
  • the fatty acid having 14 to 20 carbon atoms may further include a saturated fatty acid having 14 to 20 carbon atoms.
  • the fatty acid having 14 to 20 carbon atoms may further contain an unsaturated fatty acid having 14 to 20 carbon atoms other than oleic acid.
  • Another aspect of the present invention is a lubricating oil containing the above-described base oil for lubricating oil.
  • the lubricating oil may further contain antioxidants.
  • the lubricating oil may further contain an acid scavenger.
  • the lubricating oil may further contain anti-wear agents.
  • the content of the base oil for lubricating oil may be 80% by mass or more based on the total amount of lubricating oil.
  • Another aspect of the present invention is a working fluid containing the above lubricating oil and refrigerant.
  • the refrigerant may include hydrocarbons.
  • One embodiment of the present invention is a base oil for lubricating oil containing an ester of a trihydric alcohol and a fatty acid having 14 to 20 carbon atoms.
  • a trihydric alcohol is an alcohol that has three hydroxyl groups.
  • the trihydric alcohol may be an aliphatic alcohol.
  • Examples of trihydric alcohols include trimethylolethane, trimethylolpropane, trimethylolbutane, glycerin, and 1,3,5-pentanetriol.
  • the trihydric alcohol is preferably trimethylolpropane.
  • the fatty acid having 14 to 20 carbon atoms may be a saturated fatty acid or an unsaturated fatty acid.
  • the C14 to C20 fatty acids preferably include unsaturated fatty acids, more preferably unsaturated fatty acids having 18 carbon atoms (C18 unsaturated fatty acids), and even more preferably oleic acid.
  • the content of unsaturated fatty acids is 70% by mass or more, 75% by mass or more, 80% by mass or more, or 85% by mass or more, based on the total amount of C14 to C20 fatty acids. It may be 95% by mass or less, 93% by mass or less, or 90% by mass or less.
  • the C14-C20 fatty acid further includes a saturated fatty acid having 14-20 carbon atoms (hereinafter also referred to as "C14-C20 saturated fatty acid”) in addition to the unsaturated fatty acid.
  • C14-C20 saturated fatty acids include tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptahexadecanoic acid, octadecanoic acid, nonadecanoic acid and eicosanoic acid. These C14 to C20 saturated fatty acids may be linear or branched.
  • the C14-C20 saturated fatty acid preferably includes at least one selected from the group consisting of linear C14-C20 saturated fatty acids, and more preferably linear tetradecanoic acid (myristic acid) and linear hexadecanoic acid. (palmitic acid), and linear octadecanoic acid (stearic acid), and more preferably linear tetradecanoic acid (myristic acid), linear hexadecanoic acid (palmitic acid), acid), and linear octadecanoic acid (stearic acid).
  • linear tetradecanoic acid myristic acid
  • linear hexadecanoic acid palmitic acid
  • acid linear octadecanoic acid
  • the C14-C20 fatty acid further contains, in addition to oleic acid, an unsaturated fatty acid having 14-20 carbon atoms other than oleic acid (hereinafter also referred to as "C14-C20 unsaturated fatty acid").
  • C14-C20 unsaturated fatty acids other than oleic acid may have, for example, 1 to 4, 1 to 3, 1 to 2, or 1 carbon-carbon unsaturated bonds.
  • C14-C20 unsaturated fatty acids other than oleic acid examples include physeteric acid, myristoleic acid, palmitoleic acid, heptadecenylenic acid, petroselaidic acid, elaidic acid, vaccenic acid, linoleic acid, linoleraidic acid, hyragonic acid, and linolenic acid. , and arachidonic acid.
  • the C14 to C20 unsaturated fatty acids other than oleic acid preferably include at least one selected from the group consisting of unsaturated fatty acids having 16 to 18 carbon atoms, and more preferably include palmitoleic acid.
  • the C14-C20 fatty acids in addition to oleic acid, further include both C14-C20 saturated fatty acids and C14-C20 unsaturated fatty acids other than oleic acid.
  • the C14 to C20 saturated fatty acids preferably include at least one selected from the group consisting of linear C14 to C20 saturated fatty acids and at least one selected from the group consisting of unsaturated fatty acids having 16 to 18 carbon atoms, More preferably, it contains at least one selected from the group consisting of myristic acid, palmitic acid, and stearic acid, and palmitoleic acid, and even more preferably, it contains myristic acid, palmitic acid, stearic acid, and palmitoleic acid.
  • the content of C14-C20 saturated fatty acids may be 1% by mass or more, 3% by mass or more, or 5% by mass or more, and 15% by mass or less, 12% by mass or less, based on the total amount of C14-C20 fatty acids. , or 10% by mass or less.
  • the content of C14-C20 unsaturated fatty acids other than oleic acid may be 1% by mass or more, 3% by mass or more, or 4% by mass or more, and 10% by mass or less, based on the total amount of C14-C20 fatty acids. , 8% by mass or less, or 6% by mass or less.
  • each fatty acid mentioned above is measured by the following procedure.
  • the ester is dissolved in ethanol and subjected to alkaline hydrolysis, followed by trimethylsilyl (TMS) derivatization using N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).
  • TMS trimethylsilyl
  • BSTFA N,O-bis(trimethylsilyl)trifluoroacetamide
  • BSTFA N,O-bis(trimethylsilyl)trifluoroacetamide
  • the type of fatty acid constituting the ester is confirmed as a TMS derivatized product by GC/MS analysis of the obtained TMS derivatized fatty acid.
  • each fatty acid is quantified by GC analysis under the following GC conditions.
  • GC conditions ⁇ Column: DB-5, 50°C ⁇ 320°C (15°C/min) ⁇ Injection: 300°C, 1 ⁇ L, split ratio 50:1 ⁇ Detector: FID, 320°C - Standard sample for calibration curve: Palmitic acid (reagent) is used for C14 fatty acids and C16 fatty acids, and stearic acid (reagent) is used for C18 fatty acids. Note that fatty acid ethylation may be generated during the TMS derivatization process, and the amount of fatty acid is calculated by adding up the amount of fatty acid TMS derivatization and the amount of fatty acid ethylation.
  • Esters of trihydric alcohols and C14 to C20 fatty acids include diesters and triesters.
  • a diester is a partial ester in which two of the three hydroxyl groups of a trihydric alcohol are esterified with a C14 to C20 fatty acid, with one hydroxyl group remaining intact.
  • Triesters are complete esters in which all three hydroxyl groups of a trihydric alcohol are esterified with C14-C20 fatty acids.
  • the content of triester is 93 mol% or less based on the total amount of diester and triester. In other words, the content of diester is 7 mol% or more based on the total amount of diester and triester. As a result, a base oil for lubricating oil that has excellent stability even when water is mixed in can be obtained.
  • the content of triester may be preferably 92 mol% or less, 91 mol% or less, 90 mol% or less, or 89 mol% or less, and 70 mol% or less, based on the total amount of diester and triester.
  • the content may be 75 mol% or more, 80 mol% or more, or 85 mol% or more.
  • the content of diester is preferably 8 mol% or more, 9 mol% or more, 10 mol% or more, or 11 mol% or more, and 30 mol% or less, based on the total amount of diester and triester. , 35 mol% or less, 20 mol% or less, or 15 mol% or less.
  • the above-mentioned diester content C2 and triester content C3 (based on the total amount of diester and triester, mol%) have a peak around 40.5 ppm in the 13 C-NMR spectrum measured under the following conditions. It is calculated by the following formula, with a peak caused by triester (area value P3) and a peak observed around 42.5 ppm being defined as a peak caused by diester (area value P2).
  • the above-mentioned ester of a trihydric alcohol containing a specific amount of diester and triester and a C14 to C20 fatty acid can be produced, for example, by the following method.
  • a polyhydric alcohol and a C14 to C20 fatty acid slightly in excess of the equivalent amount are distilled off at a temperature of 120 to 250°C under a nitrogen stream until the hydroxyl value is about 15 mgKOH/g.
  • the reaction is carried out until the crude ester is obtained.
  • a catalyst such as a Lewis acid catalyst or a reducing agent such as a phosphorus reducing agent may be used.
  • the obtained crude ester is treated with an alkali such as potassium hydroxide to remove excess acid, and if necessary is treated with an aqueous solution such as sulfite. After washing with water and dehydration, it is treated with activated clay, aluminum oxide, etc.
  • an alkali such as potassium hydroxide
  • an aqueous solution such as sulfite
  • activated clay aluminum oxide, etc.
  • a purification process such as adsorption with an adsorbent and filtration
  • a mixture containing diesters and triesters including monoesters in some cases
  • the above steps are carried out according to known methods (for example, see Japanese Patent Application Publication No. 2002-193882, International Publication No. 2002/022548, Japanese Patent Application Publication No. 2007-332134, and Japanese Patent Application Publication No. 2013-227255).
  • the two were purified and fractionated using the difference in boiling point between the diester and triester, and then the mixture was purified as described above.
  • a diester/triester mixture in the desired proportion is obtained.
  • an ester mainly consisting of triester can be obtained, and C14 to C20 fatty acid is added to 1 mole of trihydric alcohol.
  • An ester consisting mainly of diester can be obtained by reacting about 2 moles of esters, but these may be mixed in the desired proportions mentioned above.
  • the ester of trihydric alcohol and C14 to C20 fatty acid may further contain a monoester.
  • a monoester is a partial ester in which one of the three hydroxyl groups of a trihydric alcohol is esterified with a C14 to C20 fatty acid, and two hydroxyl groups remain as they are.
  • the monoester content is preferably as low as possible, and is preferably 10 mol% or less based on the total amount of the ester of trihydric alcohol and C14 to C20 fatty acid. It may be 0 mol%.
  • the base oils described above are used as base oils for lubricating oils. That is, another embodiment of the present invention is a lubricating oil containing the above-described base oil for lubricating oil.
  • the content of the ester of trihydric alcohol and C14 to C20 fatty acid is 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of lubricating oil. It may be % by mass or more.
  • the lubricating oil may further contain other base oils than esters of trihydric alcohols and C14 to C20 fatty acids.
  • Other base oils may be, for example, hydrocarbon oils or oxygenated oils.
  • the hydrocarbon oil include mineral oil, olefin polymers, naphthalene compounds, alkylbenzenes, and the like.
  • oxygen-containing oils include monoesters (esters of monoalcohols), polyol esters other than esters of trihydric alcohols and C14 to C20 fatty acids (esters of polyols having two or more hydroxyl groups), esters such as complex esters, and polyesters such as complex esters.
  • Examples include ethers such as alkylene glycol, polyvinyl ether, polyphenyl ether, and perfluoroether.
  • the lubricating oil may further contain additives depending on the desired properties.
  • additives include antioxidants, acid scavengers, antiwear agents, oil agents, antifoaming agents, metal deactivators, viscosity index improvers, and the like.
  • the total content of additives is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and preferably 5% by mass or less or 2% by mass, based on the total amount of lubricating oil. It may be the following.
  • the lubricating oil preferably further contains an antioxidant, more preferably a phenolic antioxidant.
  • an antioxidant more preferably a phenolic antioxidant.
  • phenolic antioxidants include 2,6-di-tert-butyl-4-methylphenol.
  • the content of the antioxidant may be 0.1% by mass or more and 3% by mass or less based on the total amount of lubricating oil.
  • the lubricating oil preferably further contains an acid scavenger, more preferably an epoxy acid scavenger.
  • an acid scavenger preferably an epoxy acid scavenger.
  • the epoxy acid scavenger include glycidyl ester compounds, glycidyl ether compounds, and alicyclic epoxy compounds.
  • the content of the acid scavenger may be 0.1% by mass or more and 3% by mass or less based on the total amount of lubricating oil.
  • the lubricating oil preferably further contains an anti-wear agent, more preferably a phosphorus-based anti-wear agent.
  • the phosphorus-based wear inhibitor include orthophosphoric acid ester compounds, phosphorous acid ester compounds, and thiophosphoric acid ester compounds.
  • the phosphorus anti-wear agent is preferably an orthophosphoric acid ester compound, more preferably at least one selected from tricresyl phosphate, triphenyl phosphate, trialkyl phosphate, and tri(alkylphenyl) phosphate.
  • the content of the anti-wear agent may be 0.1% by mass or more and 3% by mass or less based on the total amount of lubricating oil.
  • the lubricating oil may further contain an antioxidant, an acid scavenger, and an antiwear agent, and may further contain a phenolic antioxidant, an epoxy acid scavenger, and a phosphorus antiwear agent. .
  • the kinematic viscosity at 40° C. of the lubricating oil may be 10 mm 2 /s or more, 20 mm 2 /s or more, 30 mm 2 /s or more, or 40 mm 2 /s or more, and 400 mm 2 / s or less, and 300 mm 2 /s or more. s or less, 200 mm 2 /s or less, 100 mm 2 /s or less, or 60 mm 2 /s or less.
  • the kinematic viscosity at 100° C. of the lubricating oil may be 4 mm 2 /s or more, 6 mm 2 /s or more, 8 mm 2 /s or more, or 9 mm 2 /s or more, and 40 mm 2 /s or less, 25 mm 2 /s or less. , 15 mm 2 /s or less, 12 mm 2 /s or less, or 10 mm 2 /s or less.
  • the viscosity index of the lubricating oil may be 110 or more, 140 or more, 150 or more, 160 or more, or 170 or more, and may be 300 or less, 250 or less, or 220 or less.
  • kinematic viscosity and viscosity index refer to kinematic viscosity and viscosity index measured in accordance with JIS K2283:2000.
  • the use of the lubricating oil is not particularly limited, it is preferably a refrigerating machine oil. That is, another embodiment of the present invention is a refrigerating machine oil containing the above-described base oil for lubricating oil. Moreover, “lubricating oil” in the above description can be read as “refrigerating machine oil”.
  • Refrigerating machine oil is used together with a refrigerant. That is, another embodiment of the present invention is a working fluid containing lubricating oil (refrigerating machine oil) and a refrigerant.
  • the refrigerant preferably contains hydrocarbons.
  • the hydrocarbon is preferably a hydrocarbon having 2 to 4 carbon atoms.
  • the hydrocarbon is, for example, at least one selected from the group consisting of ethylene, ethane, propane (R290), propylene, cyclopropane, normal butane, isobutane (R600a), cyclobutane, and methylcyclopropane, preferably propane ( R290) or isobutane (R600a), more preferably propane (R290).
  • the refrigerant may consist only of hydrocarbons, or may further contain other refrigerants in addition to hydrocarbons.
  • the content of hydrocarbons may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of the refrigerant.
  • the other refrigerants include saturated fluorinated hydrocarbons (HFC) such as R32, R134a, R125, R143a, and R152a, unsaturated fluorinated hydrocarbons (HFO) such as R1234yf and R1234ze, and perfluoroether.
  • HFC saturated fluorinated hydrocarbons
  • HFO unsaturated fluorinated hydrocarbons
  • R1234yf and R1234ze such as R1234yf and R1234ze
  • perfluoroether examples include fluorine ether, bis(trifluoromethyl)sulfide, trifluoroiodide me
  • the content of refrigerating machine oil in the working fluid may be 1 part by mass or more or 2 parts by mass or more, and 500 parts by mass or less or 400 parts by mass or less, based on 100 parts by mass of the refrigerant.
  • Each ester of trimethylolpropane and a C14 to C20 fatty acid having the fatty acid composition shown in Table 1 was used as base oils 1 to 4.
  • Table 1 shows the diester and triester contents in each ester (base oil) measured by the above procedure.
  • Stability evaluation Stability evaluation was performed in accordance with JIS K2211-09 (autoclave test). Specifically, base oils 1 to 4 (30 g) whose water content was adjusted to less than 10 ppm or 1000 ppm were weighed into an autoclave, and catalysts (iron, copper, and aluminum wires, each with an outer diameter of 1.6 mm and a length of A stability test was conducted by enclosing R290 (30 g) as a refrigerant and heating at 175° C. for 168 hours. The peroxide value of the base oil after the stability test was measured in accordance with JPI-5S-72. Table 1 shows the peroxide value after the stability test for each case where the water content was less than 10 ppm or 1000 ppm. If the peroxide value can be suppressed to 200 mg/kg or less without additives, stability can be easily maintained.
  • the peroxide value of all base oils 1 to 4 is 200 mg/kg or less. It's suppressed.
  • water content water content is 1000 ppm
  • the peroxide value of base oils 1 to 3 is suppressed to 200 mg/kg or less
  • the peroxide value of base oil 4 is suppressed to 200 mg/kg or less. The oxide value exceeded 200 mg/kg.
  • lubricating oils refrigerating machine oils
  • base oils 1 to 3 maintain stability even when water is mixed in because they have an excellent peroxide suppression effect. It's easy to do.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
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Abstract

Huile de base pour une huile lubrifiante, l'huile de base comprenant un ester d'un alcool trivalent et d'un acide gras en C14 à C20, l'ester comprenant un diester et un triester, et la quantité de triester incluse n'étant pas supérieure à 93 % en moles par rapport à la quantité totale de diester et de triester.
PCT/JP2023/008627 2022-03-31 2023-03-07 Huile de base pour huile lubrifiante, huile lubrifiante et fluide de travail WO2023189293A1 (fr)

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JP2022-058601 2022-03-31
JP2022058601A JP2023149825A (ja) 2022-03-31 2022-03-31 潤滑油用基油、潤滑油及び作動流体

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Citations (7)

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Publication number Priority date Publication date Assignee Title
JP2001181662A (ja) * 1999-12-28 2001-07-03 Idemitsu Kosan Co Ltd 環状有機リン化合物を含有する潤滑油組成物
JP2008115301A (ja) * 2006-11-06 2008-05-22 Idemitsu Kosan Co Ltd 生分解性潤滑油組成物
WO2010064347A1 (fr) * 2008-12-01 2010-06-10 新日本石油株式会社 Composition d’huile hydraulique ignifuge
WO2013008172A1 (fr) * 2011-07-12 2013-01-17 Ecole D'ingenieurs Et D'architectes De Fribourg Liquide zwitterionique à titre de co-catalyseur pour l'estérification enzymatique
JP2016104858A (ja) * 2014-11-19 2016-06-09 日油株式会社 油圧作動油組成物
CN108707074A (zh) * 2018-07-06 2018-10-26 湖南理工学院 一种制备低酸值三羟甲基丙烷油酸酯的方法
WO2022114137A1 (fr) * 2020-11-30 2022-06-02 Ｅｎｅｏｓ株式会社 Fluide de travail, congélateur et huile de congélateur

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Publication number Priority date Publication date Assignee Title
JP2001181662A (ja) * 1999-12-28 2001-07-03 Idemitsu Kosan Co Ltd 環状有機リン化合物を含有する潤滑油組成物
JP2008115301A (ja) * 2006-11-06 2008-05-22 Idemitsu Kosan Co Ltd 生分解性潤滑油組成物
WO2010064347A1 (fr) * 2008-12-01 2010-06-10 新日本石油株式会社 Composition d’huile hydraulique ignifuge
WO2013008172A1 (fr) * 2011-07-12 2013-01-17 Ecole D'ingenieurs Et D'architectes De Fribourg Liquide zwitterionique à titre de co-catalyseur pour l'estérification enzymatique
JP2016104858A (ja) * 2014-11-19 2016-06-09 日油株式会社 油圧作動油組成物
CN108707074A (zh) * 2018-07-06 2018-10-26 湖南理工学院 一种制备低酸值三羟甲基丙烷油酸酯的方法
WO2022114137A1 (fr) * 2020-11-30 2022-06-02 Ｅｎｅｏｓ株式会社 Fluide de travail, congélateur et huile de congélateur

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ZHU LILI; ZHAO QIN; WU XINHU; ZHAO GAIQING; WANG XIAOBO: "A novel phosphate ionic liquid plays dual role in synthetic ester oil: From synthetic catalyst to anti-wear additive", TRIBOLOGY INTERNATIONAL, ELSEVIER LTD, AMSTERDAM, NL, vol. 97, 1 January 1900 (1900-01-01), AMSTERDAM, NL , pages 192 - 199, XP029450937, ISSN: 0301-679X, DOI: 10.1016/j.triboint.2015.12.047 *

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