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WO2025169833A1 - Huile de base lubrifiante, composition d'huile lubrifiante et système de refroidissement - Google Patents

Huile de base lubrifiante, composition d'huile lubrifiante et système de refroidissement

Info

Publication number
WO2025169833A1
WO2025169833A1 PCT/JP2025/003020 JP2025003020W WO2025169833A1 WO 2025169833 A1 WO2025169833 A1 WO 2025169833A1 JP 2025003020 W JP2025003020 W JP 2025003020W WO 2025169833 A1 WO2025169833 A1 WO 2025169833A1
Authority
WO
WIPO (PCT)
Prior art keywords
base oil
refrigerant
lubricating base
carbon atoms
lubricating
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
PCT/JP2025/003020
Other languages
English (en)
Japanese (ja)
Inventor
豪明 荒井
吉 竹田
亮平 小口
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AGC Inc
Original Assignee
Asahi Glass 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 Asahi Glass Co Ltd filed Critical Asahi Glass Co Ltd
Publication of WO2025169833A1 publication Critical patent/WO2025169833A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • 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
    • C10M105/18—Ethers, e.g. epoxides
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to lubricating base oils, lubricating oil compositions, and cooling systems.
  • Various lubricating base oils are used to ensure smooth circulation of the refrigerant in compression-type refrigerators.
  • Compounds such as polyalkylene glycols, polyol esters, and polyvinyl ethers can be used as lubricating base oils depending on the type of refrigerant.
  • Patent Document 1 discloses in its working examples that a lubricating base oil containing an epoxy compound such as 1,2-epoxyhexadecane and a polyalkylene glycol is mixed with the refrigerant.
  • the refrigerant and lubricating base oil are sealed and used within the refrigerator for long periods of time, they must be stable enough to prevent the formation of precipitates even after long-term use.
  • the present invention provides a lubricating base oil that improves the chemical stability of refrigerants blended with the lubricating base oil when used over an extended period of time, and a lubricating oil composition containing the lubricating base oil.
  • a lubricating oil composition comprising the lubricating base oil according to any one of [1] to [6], and either or both of a refrigerant and an additive.
  • the lubricating oil composition according to [7], wherein the refrigerant is propane.
  • the chemical stability of refrigerants blended with lubricating base oils is improved when used over long periods of time.
  • active hydrogen refers to a hydrogen atom derived from an active hydrogen-containing group and a hydrogen atom derived from a hydroxyl group of water.
  • active hydrogen-containing group refers to at least one group selected from the group consisting of a hydroxyl group bonded to a carbon atom, a carboxyl group, an amino group, a monovalent functional group formed by removing one hydrogen atom from a primary amine, and a sulfanyl group.
  • initiator residue refers to a group obtained by removing one or more active hydrogens from an initiator.
  • "Unit” means an atomic group formed directly by polymerization of a monomer.
  • volume resistivity is a value measured in accordance with the "volume resistivity test method" of JIS C2101:2010 "Electrical insulating oil.”
  • the use of "to” to indicate a range of values means that the values before and after "to” are included as the lower and upper limits.
  • the ranges of values disclosed in this specification can be combined in any way to create new ranges of values.
  • the refrigerant to be mixed with the lubricating base oil of the present invention contains a hydrocarbon compound having 1 to 8 carbon atoms.
  • the hydrocarbon compound of the refrigerant preferably has 1 to 5 carbon atoms, more preferably 3 to 5 carbon atoms, even more preferably 3 or 4 carbon atoms, and most preferably 3 carbon atoms.
  • the aliphatic monoalcohol may be a saturated aliphatic monool, an unsaturated aliphatic monool, or a cyclic aliphatic monool. Of these, saturated aliphatic monools are preferred. Examples of saturated aliphatic monools include methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, n-hexanol, octyl alcohol, and 2-ethylhexanol. However, saturated aliphatic monools are not limited to these examples.
  • Examples of amines include alkanolamines, heterocyclic amines, aliphatic amines, and aromatic amines.
  • alkanolamines include monoethanolamine, diethanolamine, triethanolamine, and isopropanolamine.
  • Examples of heterocyclic amines include N-(2-aminoethyl)piperazine and N-aminomethylpiperazine.
  • Examples of the aliphatic amine include ethylenediamine, propylenediamine, and hexamethylenediamine.
  • Examples of aromatic amines include tolylenediamine and diaminodiphenylmethane.
  • the amines are not limited to these examples.
  • One type of amine may be used alone, or two or more types may be used in combination.
  • n R 3s is an alkyl group having 1 to 4 carbon atoms. All of the n R 3s may be alkyl groups having 1 to 4 carbon atoms.
  • the n R 3s may be the same as or different from one another. In other words, the R 3s bonded to the ends of the n (R 2 O) m chains may be the same as or different from one another.
  • alkylene oxide can be addition polymerized to an initiator in the presence of a catalyst.
  • Metal elements derived from the catalyst used in this synthesis reaction may remain in the lubricating base oil. In order to keep the metal content of the lubricating base oil to 10 ppm or less, it is preferable to thoroughly remove the catalyst after the synthesis reaction of compound 1.
  • the viscosity index of the lubricating base oil is preferably 50 or higher, more preferably 80 or higher, and even more preferably 100 or higher, as this improves viscosity characteristics.
  • the volume resistivity of the lubricating base oil is not particularly limited, but may be, for example, 1 ⁇ 10 10 to 1 ⁇ 10 15 ⁇ cm, 6 ⁇ 10 10 to 1 ⁇ 10 14 ⁇ cm, or 1 ⁇ 10 11 to 1 ⁇ 10 14 ⁇ cm.
  • the volume resistivity is equal to or greater than the lower limit of the above-mentioned range, electrical insulation properties are improved.
  • the volume resistivity is equal to or less than the upper limit of the above-mentioned range, static electricity generation is easily prevented.
  • the lubricating base oil is obtained by addition polymerizing an alkylene oxide to an initiator in the presence of a catalyst to elongate the oxyalkylene chain ((R 2 O) m ) to introduce an alkyl group having 1 to 4 carbon atoms at the end of the chain, thereby obtaining Compound 1, and then removing the catalyst from the reaction solution containing Compound 1. Details and preferred embodiments of the initiator are as described above.
  • the catalyst examples include alkali metal catalysts and double metal cyanide complex catalysts (hereinafter referred to as "DMC catalysts"), but the catalyst is not limited to these examples.
  • the catalyst may be used alone or in combination of two or more kinds.
  • the DMC catalyst is believed to have at least a metal element and an organic ligand.
  • metal elements of the DMC catalyst include Zn, Fe, Co, Ni, Al, Sr, Mn, Cr, Cu, Sn, Pb, Mo, W, and V.
  • the metal elements of the DMC catalyst are not limited to these examples.
  • the DMC catalyst may contain one or more metal elements.
  • organic ligands for DMC catalysts include t-butyl alcohol (hereinafter referred to as "TBA"), n-butyl alcohol, iso-butyl alcohol, t-pentyl alcohol, iso-pentyl alcohol, N,N-dimethylacetamide, ethylene glycol mono-t-butyl ether, ethylene glycol dimethyl ether (glyme), diethylene glycol dimethyl ether (diglyme), triethylene glycol dimethyl ether (triglyme), iso-propyl alcohol, and dioxane.
  • Dioxane may be 1,4-dioxane or 1,3-dioxane.
  • the organic ligand is not limited to these examples.
  • the organic ligands may be used alone or in combination of two or more.
  • alkylene oxides examples include ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, methyl glycidyl ether, 2,3-epoxy-1-propanol, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, lauryl glycidyl ether, hexyl glycidyl ether, tetrahydrofuran, epichlorohydrin, styrene oxide, and cyclohexene oxide.
  • Preferred alkylene oxides are ethylene oxide and propylene oxide, with propylene oxide being more preferred. However, alkylene oxides are not limited to these examples.
  • Alkylene oxides may be used singly or in combination of two or more.
  • one type of alkylene oxide may be homopolymerized using an initiator, or two or more types of alkylene oxides may be copolymerized using an initiator.
  • two or more types of alkylene oxides may be block copolymerized using an initiator, or random copolymerized.
  • the reaction temperature, reaction time, and reactor pressure for the ring-opening addition polymerization reaction are not particularly limited.
  • the reaction temperature may be, for example, 80 to 150°C, or 90 to 140°C.
  • the reaction time may be, for example, 3 to 30 hours, or 5 to 20 hours.
  • the reactor pressure may be, for example, 0.01 to 0.9 MPaG, or 0.03 to 0.7 MPaG.
  • the method for introducing an alkyl group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include the following Method 1 and Method 2.
  • Method 1 A method in which an alkyl halide having 1 to 4 carbon atoms is reacted with the hydroxyl group at the end of an oxyalkylene chain.
  • Method 2 A method in which a metal alkoxide having an alkyl group having 1 to 4 carbon atoms is reacted with the hydroxyl group at the end of an oxyalkylene chain.
  • alkyl group of the metal alkoxide are the same as those explained for R 3.
  • Examples of the metal of the metal alkoxide include, but are not limited to, Na and K.
  • the reaction temperature, reaction time, and reactor pressure for Method 1 and Method 2 are not particularly limited.
  • the reaction temperature may be, for example, 30 to 150°C, or 40 to 140°C.
  • the reaction time may be, for example, 1 to 20 hours, or 2 to 10 hours.
  • the reactor pressure may be, for example, 0.01 to 5 MPaG, or 0.05 to 2 MPaG.
  • the conversion rate in the reaction for introducing an alkyl group having 1 to 4 carbon atoms into the terminal of the oxyalkylene chain ((R 2 O) m ) is not particularly limited, but may be, for example, 50 to 100%, 60 to 95%, or 70 to 90%.
  • the conversion rate in the reaction is equal to or greater than the lower limit of the above-mentioned range, at least one of the n R 3s is likely to be an alkyl group having 1 to 4 carbon atoms.
  • the conversion rate in the reaction is equal to or less than the upper limit of the above-mentioned range, compound 1 is easily synthesized.
  • the method for removing the catalyst is not particularly limited, and examples thereof include the following methods 3, 4, and 5.
  • Method 3 A method in which the catalyst is adsorbed using an adsorbent, and then the adsorbent with the adsorbed catalyst is removed by filtration.
  • Method 4 Neutralizing the catalyst with a neutralizing agent and then removing the neutralized catalyst by filtration.
  • Method 5 A method of removing the catalyst during filtration using a charged filter.
  • any of Method 3, Method 4, and Method 5 may be performed alone, or two or more of them may be combined as appropriate, or all of Methods 3, 4, and 5 may be performed.
  • the order in which they are performed is not particularly limited.
  • Methods 3 and 4 are preferred, with Method 3 being more preferred, from the viewpoint of further reducing the metal content.
  • Examples of adsorbents include synthetic silicates, ion exchange resins, activated clay, oxide salts, and acid clay.
  • Examples of synthetic silicates include magnesium silicate, aluminum silicate, and hydrotalcite.
  • Examples of oxide salts include magnesium oxide and aluminum oxide.
  • the adsorbents may be used alone or in combination of two or more.
  • Examples of the neutralizing agent include amines, alkali metal hydroxides, organic acids, inorganic acids, and salts thereof.
  • Examples of the inorganic acid include sulfuric acid, phosphoric acid, and hydrochloric acid.
  • Examples of the organic acid include lactic acid.
  • the neutralizing agents may be used alone or in combination of two or more.
  • charged filters may be used. Examples of commercially available charged filters include the Zeta Plus Adsorption Depth Filter Cartridge EC Series (a product of 3M), RO Wind (a product of Organo Corporation), and SupraCap 200 (a product of Seitz AKSJ). However, charged filters are not limited to these examples.
  • the lubricating oil composition of the present invention comprises the above-described lubricating base oil and either or both of a refrigerant and an additive.
  • the lubricating oil composition may comprise a lubricating base oil and a refrigerant, a lubricating base oil and an additive, or a lubricating base oil, a refrigerant, and an additive.
  • the lubricating oil composition of the present invention can, for example, impart lubricity to the sliding parts of a compressor supplied with a refrigerant.
  • the refrigerant is as described above.
  • additives examples include antioxidants, extreme pressure agents, stabilizers, copper deactivators, antifoaming agents, load-bearing additives, chlorine scavengers, oxygen scavengers, detergent-dispersants, viscosity index improvers, oiliness agents, rust inhibitors, corrosion inhibitors, and pour point depressants, but the additives are not limited to these examples.
  • the additives may be used alone or in combination of two or more.
  • antioxidants examples include phenol-based antioxidants and amine-based antioxidants.
  • examples of phenol-based antioxidants include 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, and 2,2'-methylenebis(4-methyl-6-tert-butylphenol).
  • examples of the amine antioxidant include phenyl- ⁇ -naphthylamine and N,N'-diphenyl-p-phenylenediamine. The antioxidants may be used alone or in combination of two or more.
  • extreme pressure agents include phosphorus-based extreme pressure agents such as phosphate esters, acid phosphate esters, phosphites, acid phosphites, and amine salts of these.
  • stabilizers include epoxy compounds such as phenyl glycidyl ether, alkyl glycidyl ether, alkylene glycol glycidyl ether, cyclohexene oxide, ⁇ -olefin oxide, and epoxidized soybean oil.
  • antifoaming agents examples include silicone oil and fluorinated silicone oil.
  • the proportion of the lubricating base oil may be 40 to 99.9 mass%, 45 to 90 mass%, or 50 to 80 mass% of the total amount of the lubricating oil composition. If the proportion of the lubricating base oil is equal to or greater than the lower limit of the above numerical range, chemical stability when mixed with a refrigerant is likely to be improved. If the proportion of the lubricating base oil is equal to or less than the upper limit of the above numerical range, compatibility with the refrigerant is preferred.
  • the proportion of the refrigerant may be 0.1 to 80 mass%, 10 to 60 mass%, or 20 to 50 mass% of the total amount of the lubricating oil composition.
  • a refrigerant proportion equal to or greater than the lower limit of the above numerical range is preferable in terms of compatibility with the lubricating base oil.
  • a refrigerant proportion equal to or less than the upper limit of the above numerical range is likely to improve chemical stability when mixed with the lubricating base oil.
  • the metal content of the lubricating base oil of the present invention as described above is 10 ppm or less. Therefore, even when the refrigerant is used for a long period of time under severe conditions, deposits are unlikely to occur. Thus, the lubricating base oil of the present invention improves the chemical stability of the refrigerant blended with the lubricating base oil when used for a long period of time.
  • Example 4 74 g of n-butanol and 12 g of sodium hydroxide (purity 95% by mass) as a catalyst were added to a 5 L autoclave, and the temperature was raised to 100°C. 1,500 g of propylene oxide was then introduced into the autoclave over 12 hours. It was confirmed that the pressure inside the autoclave became constant and all of the propylene oxide had reacted. After cooling to 50°C, 140 g of a 28% sodium methoxide methanol solution was added. After the addition, the temperature was raised to 120°C and a reduced pressure methanol removal treatment was carried out for 10 hours.
  • the temperature inside the system was then cooled to 80°C, and 51 g of methyl chloride was introduced over 4 hours to carry out terminal methylation. After confirming that the pressure in the system after the introduction of methyl chloride had stabilized and that the methyl chloride had reacted, the resulting compound was transferred to a 5 L separable flask. Then, 1500 g of distilled water was added, and the aqueous layer was removed by oil-water separation.
  • the temperature inside the system was then cooled to 100°C, and 51 g of methyl chloride was introduced over 2 hours to carry out terminal methylation. After confirming that the pressure in the system after the introduction of methyl chloride had stabilized and that the methyl chloride had reacted, 1800 g of the resulting compound was transferred to a 5 L separable flask. Then, 1800 g of distilled water and 40 g of sodium pyrophosphate were added, and the aqueous layer was removed by oil-water separation.
  • Example 6 32 g of methanol and 13 g of potassium hydroxide (purity 95% by mass) as a catalyst were added to a 5 L autoclave, and the temperature was then raised to 100°C. Then, 1,180 g of propylene oxide was introduced into the autoclave over 10 hours. A mixture of 88 g of ethylene oxide was then introduced into the autoclave over 1 hour. The pressure inside the autoclave became constant, and it was confirmed that all the components had reacted. After cooling to 50°C, 180 g of a 28% sodium methoxide methanol solution was added. After the addition, the temperature was raised to 120°C, and a reduced pressure methanol removal treatment was carried out for 10 hours.
  • the temperature inside the system was then cooled to 100°C, and 63 g of methyl chloride was introduced over 2 hours to carry out terminal methylation.
  • 1300 g of the resulting compound was transferred to a 5 L separable flask. Then, 1300 g of distilled water and 40 g of sodium pyrophosphate were added, and the aqueous layer was removed by oil-water separation.
  • magnesium silicate adsorbent (Kyowado 600S, manufactured by Kyowa Chemical Industry Co., Ltd.) was added as an adsorbent to the polyether compound on the oil layer side, and the mixture was stirred at 110 ° C for 2 hours. The catalyst was then thoroughly removed by filtration of insoluble matter, yielding polyalkylene glycol butyl methyl ether. The amount of residual metal in the resulting polyalkylene glycol butyl methyl ether was 1.0 ppm, and the number average molecular weight determined by GPC was 1,250.
  • Example 7 32 g of methanol and 13 g of potassium hydroxide (purity 95% by mass) as a catalyst were added to a 5 L autoclave, and the temperature was then raised to 100°C. Then, 1,268 g of propylene oxide was introduced into the autoclave over 12 hours. It was confirmed that the pressure inside the autoclave became constant and all the components had reacted. After cooling to 50°C, 180 g of a 28% sodium methoxide methanol solution was added. After the addition, the temperature was raised to 120°C and a reduced pressure methanol removal treatment was carried out for 10 hours.
  • the temperature inside the system was then cooled to 100°C, and 63 g of methyl chloride was introduced over 2 hours to carry out terminal methylation.
  • 1300 g of the resulting compound was transferred to a 5 L separable flask. Then, 1300 g of distilled water and 40 g of sodium pyrophosphate were added, and the aqueous layer was removed by oil-water separation.
  • magnesium silicate adsorbent (Kyowado 600S, manufactured by Kyowa Chemical Industry Co., Ltd.) was added as an adsorbent to the polyether compound on the oil layer side, and the mixture was stirred at 110 ° C for 2 hours. The catalyst was then thoroughly removed by filtration of insoluble matter, yielding polyalkylene glycol butyl methyl ether. The amount of residual metal in the resulting polyalkylene glycol butyl methyl ether was 0.8 ppm, and the number average molecular weight determined by GPC was 1,250.
  • Example 8 After adding 162 g of powdered sodium methoxide to a 5 L autoclave, the temperature was raised to 110°C, and 4,350 g of propylene oxide was introduced into the autoclave over 10 hours. After introducing the propylene oxide, the pressure became constant, and it was confirmed that all of the propylene oxide had reacted. After cooling the temperature in the system to 100°C, 152 g of methyl chloride was introduced over 3 hours to carry out terminal methylation. After confirming that the pressure in the system after the introduction of methyl chloride had stabilized and that the methyl chloride had reacted, 2000 g of the resulting compound was transferred to a 5 L separable flask.
  • Example 9 After adding 162 g of powdered sodium methoxide to a 5 L autoclave, the temperature was raised to 110°C, and a mixture of 3,000 g of propylene oxide and 1,350 g of ethylene oxide was introduced into the autoclave over 10 hours. After the introduction of the mixture of propylene oxide and ethylene oxide, the pressure became constant, and it was confirmed that all of the propylene oxide and ethylene oxide had reacted. After cooling the temperature in the system to 70°C, 152 g of methyl chloride was introduced over 5 hours to carry out terminal methylation. After the introduction of methyl chloride, the pressure in the system became constant, and it was confirmed that the methyl chloride had reacted.
  • the obtained compound was filtered to remove insoluble matter, and polyalkylene glycol dimethyl ether was obtained.
  • the amount of residual metal in the obtained polyalkylene glycol dimethyl ether was 500 ppm, and the number average molecular weight determined by GPC was 1,480.
  • Example 10 74 g of n-butanol and 12 g of sodium hydroxide (purity 95% by mass) as a catalyst were added to a 5 L autoclave, and the temperature was raised to 100°C. 1,500 g of propylene oxide was then introduced into the autoclave over 12 hours. It was confirmed that the pressure inside the autoclave became constant and all of the propylene oxide had reacted. After cooling to 50°C, 140 g of a 28% sodium methoxide methanol solution was added. After the addition, the temperature was raised to 120°C and a reduced pressure methanol removal treatment was carried out for 10 hours.
  • the temperature inside the system was then cooled to 80°C, and 51 g of methyl chloride was introduced over 4 hours to carry out terminal methylation.
  • the resulting compound was transferred to a 5 L separable flask, and 10 g of an aluminum silicate-based adsorbent (Kyowad 700, manufactured by Kyowa Chemical Industry Co., Ltd.) and 10 g of acidic sodium pyrophosphate were added as adsorbents, followed by stirring for 2 hours at 110° C. Thereafter, insoluble matter was filtered off to obtain polypropylene glycol butyl methyl ether.
  • the amount of residual metal in the resulting polypropylene glycol butyl methyl ether was 50 ppm, and the number average molecular weight determined by GPC was 1,500.
  • R 1 , R 2 O, R 3 , m, and n in formula 1 of the compounds obtained in each example are shown in Table 1.
  • PO represents propylene oxide
  • EO represents ethylene oxide.
  • the chemical stability of refrigerants blended with lubricating base oils is improved when used over long periods of time.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Combustion & Propulsion (AREA)
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  • Materials Engineering (AREA)
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  • Polymers & Plastics (AREA)
  • Lubricants (AREA)

Abstract

La présente invention concerne : une huile de base lubrifiante qui permet à un fluide frigorigène contenant l'huile de base lubrifiante d'avoir une stabilité chimique améliorée lorsqu'il est utilisé sur une longue période ; et une composition d'huile lubrifiante comprenant l'huile de base lubrifiante.　Cette huile de base lubrifiante est destinée à être mélangée avec un fluide frigorigène, le fluide frigorigène comprenant un composé hydrocarboné ayant de 1 à 8 atomes de carbone. L'huile de base lubrifiante contient un composé représenté par la formule 1 et a une teneur en métal inférieure ou égale à 10 ppm.　Formule 1 : R1\{(R2O)mR3\}n ; R1 est un résidu initiateur ; les fractions R2 sont chacune indépendamment un groupe hydrocarboné en C2-C4 ; les fractions R3 sont chacune indépendamment un atome d'hydrogène ou un groupe alkyle en C1-C4, au moins l'une des fractions R3 étant un groupe alkyle en C1-C4 ; m étant compris entre 1 et 200 ; et n étant compris entre 1 et 8.
PCT/JP2025/003020 2024-02-06 2025-01-30 Huile de base lubrifiante, composition d'huile lubrifiante et système de refroidissement Pending WO2025169833A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000169867A (ja) * 1998-12-08 2000-06-20 Asahi Glass Co Ltd 冷凍機油組成物および該組成物を用いた潤滑方法
WO2007026647A1 (fr) * 2005-08-31 2007-03-08 Idemitsu Kosan Co., Ltd. Composition d’huile de réfrigération
WO2018034189A1 (fr) * 2016-08-18 2018-02-22 出光興産株式会社 Composition lubrifiante

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000169867A (ja) * 1998-12-08 2000-06-20 Asahi Glass Co Ltd 冷凍機油組成物および該組成物を用いた潤滑方法
WO2007026647A1 (fr) * 2005-08-31 2007-03-08 Idemitsu Kosan Co., Ltd. Composition d’huile de réfrigération
WO2018034189A1 (fr) * 2016-08-18 2018-02-22 出光興産株式会社 Composition lubrifiante

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