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
  • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
  • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
  • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
• • 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
  • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
  • C10M171/008—Lubricant compositions compatible with refrigerants
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/283—Esters of polyhydroxy compounds
  • C10M2207/2835—Esters of polyhydroxy compounds used as base material
• • 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
  • C10N2020/02—Viscosity; Viscosity index
• • 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
  • C10N2020/09—Characteristics associated with water
  • C10N2020/097—Refrigerants
  • C10N2020/101—Containing Hydrofluorocarbons
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/02—Pour-point; Viscosity index
• • 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 esters for refrigerating machine oils, base oils for refrigerating machine oils, refrigerating machine oils, and working fluid compositions.
• Refrigeration units such as refrigerators, car air conditioners, room air conditioners, and vending machines are equipped with compressors to circulate refrigerant through the refrigeration cycle.
• the compressors are filled with refrigeration oil to lubricate the sliding parts.
• Refrigeration oil contains a base oil and additives.
• the base oil in the refrigeration oil is appropriately selected depending on the properties such as compatibility with the refrigerant.
• Patent Document 1 discloses a pentaerythritol tetraester used in refrigeration oils, etc., which has excellent compatibility with difluoromethane refrigerants.
• the kinetic viscosity of the oil decreases, which can cause problems such as poor lubrication of sliding parts, seizure, and increased wear.
• One solution to this problem is to increase the kinetic viscosity of the refrigeration oil itself (the kinetic viscosity of the refrigerant oil when the refrigerant is not dissolved in the oil), but if the kinetic viscosity of the refrigeration oil itself is too high, the oil may easily accumulate in the evaporator or evaporator tube in the refrigeration cycle, or the start-up performance of the refrigeration machine may decrease, resulting in a decrease in the efficiency of the refrigeration machine. Therefore, it is necessary to increase the refrigerant dissolution viscosity of the refrigeration oil without increasing the kinetic viscosity of the refrigeration oil itself too much.
• one aspect of the present invention aims to provide an ester for refrigeration oil, a base oil for refrigeration oil, and a refrigeration oil that can increase the refrigerant dissolution viscosity when difluoromethane is dissolved in the refrigeration oil, without making the kinetic viscosity of the refrigeration oil itself too high.
• the inventors have found through their research that a mixed ester of two types of polyol esters and a complex ester is suitable as an ester for refrigeration oil, as it can increase the refrigerant dissolution viscosity when difluoromethane is dissolved in the refrigeration oil, without excessively increasing the kinetic viscosity of the refrigeration oil itself.
• An ester for a refrigerating machine oil comprising: a first ester which is an ester of a polyhydric alcohol and a fatty acid having 6 to 9 carbon atoms; a second ester which is an ester of pentaerythritol and a fatty acid; and a third ester which is an ester of pentaerythritol, a dicarboxylic acid, and a fatty acid, wherein the fatty acid constituting the second ester and the fatty acid constituting the third ester are both mixed fatty acids of at least one selected from the group consisting of branched butanoic acid, branched pentanoic acid, and linear pentanoic acid, and either branched octanoic acid or branched nonanoic acid.
• a base oil for a refrigerating machine oil comprising a first ester which is an ester of a polyhydric alcohol and a fatty acid having 6 to 9 carbon atoms, a second ester which is an ester of pentaerythritol and a fatty acid, and a third ester which is an ester of pentaerythritol, a dicarboxylic acid, and a fatty acid, wherein the fatty acid constituting the second ester and the fatty acid constituting the third ester are both mixed fatty acids of at least one selected from the group consisting of branched butanoic acid, branched pentanoic acid, and linear pentanoic acid, and either branched octanoic acid or branched nonanoic acid.
• a working fluid composition comprising the refrigerating machine oil according to [5] or [6] and a refrigerant.
• the working fluid composition according to [7] wherein the refrigerant comprises difluoromethane.
• an ester for refrigeration oil, a base oil for refrigeration oil, and a refrigeration oil that can increase the refrigerant dissolution viscosity when difluoromethane is dissolved in the refrigeration oil without making the kinetic viscosity of the refrigeration oil itself too high.
• an ester for refrigeration oil, a base oil for refrigeration oil, and a refrigeration oil that have excellent compatibility with difluoromethane.
• One embodiment of the present invention is an ester for refrigeration oil that contains a first ester that is an ester of a polyhydric alcohol and a fatty acid having 6 to 9 carbon atoms, a second ester that is an ester of pentaerythritol and a fatty acid, and a third ester that is an ester of pentaerythritol, a dicarboxylic acid, and a fatty acid.
• the first ester is represented by the following formula (1).
• PO represents a residue obtained by removing an H atom from each of m -OH groups in a polyhydric alcohol
• R 1 represents a residue obtained by removing an -OH group from a -COOH group in a fatty acid having 6 to 9 carbon atoms
• m represents an integer of 2 or more.
• a plurality of R 1s may be the same or different from each other.
• the polyhydric alcohol constituting the first ester may be, for example, a polyhydric alcohol having 2 to 6 hydroxyl groups. That is, m in formula (1) may be an integer from 2 to 6.
• the number of carbon atoms in the polyhydric alcohol may be, for example, 4 or more or 5 or more and 12 or less or 10 or less.
• the polyhydric alcohol may be, for example, a hindered alcohol such as neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, di-(trimethylolpropane), tri-(trimethylolpropane), pentaerythritol, or dipentaerythritol, and is preferably neopentyl glycol or pentaerythritol, more preferably pentaerythritol, since these have particularly excellent compatibility with difluoromethane.
• a hindered alcohol such as neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, di-(trimethylolpropane), tri-(trimethylolpropane), pentaerythritol, or dipentaerythritol
• neopentyl glycol or pentaerythritol more
• the ester for refrigeration oil may contain one type of the first ester, may contain two types of the first ester, or may contain three or more types of the first ester.
• the polyhydric alcohol constituting the first ester is preferably pentaerythritol.
• the ester for refrigeration oil contains two types of the first ester, it is preferable that the polyhydric alcohol constituting one of the first esters is neopentyl glycol, and the polyhydric alcohol constituting the other first ester is pentaerythritol.
• the fatty acid having 6 to 9 carbon atoms constituting the first ester may be a saturated fatty acid.
• the number of carbon atoms of the fatty acid may be 7 to 9 or 8 to 9.
• Examples of the fatty acid include hexanoic acid, heptanoic acid, octanoic acid, and nonanoic acid. These fatty acids may be linear or branched, preferably branched, and more preferably have branches at the ⁇ -position and/or ⁇ -position.
• the fatty acid is preferably at least one selected from the group consisting of 2-methylpentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-methylheptanoic acid, 2-ethylhexanoic acid, and 3,5,5-trimethylhexanoic acid, and more preferably at least one selected from the group consisting of 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid.
• the second ester is an ester of pentaerythritol and a fatty acid, the fatty acid being a mixed fatty acid of at least one selected from the group consisting of branched butanoic acid, branched pentanoic acid, and linear pentanoic acid, and either branched octanoic acid or branched nonanoic acid.
• the second ester is represented by the following formula (2).
• PE represents a residue obtained by removing an H atom from each of the four -OH groups in pentaerythritol
• R 2 represents a residue obtained by removing an -OH group from a -COOH group in a branched butanoic acid (also referred to as an iC4 acid residue), a residue obtained by removing an -OH group from a -COOH group in a branched pentanoic acid (also referred to as an iC5 acid residue), a residue obtained by removing an -OH group from a -COOH group in a linear pentanoic acid (also referred to as an nC5 acid residue), a residue obtained by removing an -OH group from a -COOH group in a branched octanoic acid (also referred to as an iC8 acid residue), or a residue obtained by removing an -OH group from a -COOH group in a branched nonanoic
• the branched butanoic acid constituting the second ester is preferably 2-methylpropanoic acid.
• the branched pentanoic acid constituting the second ester is preferably 2-methylbutanoic acid.
• the branched octanoic acid constituting the second ester is preferably 2-ethylhexanoic acid.
• the branched nonanoic acid constituting the second ester is preferably 3,5,5-trimethylhexanoic acid.
• At least one of R2 is an iC4 acid residue and at least one of R2 is an iC8 acid residue, and more preferred that both of R2 are iC4 acid residues or iC8 acid residues (provided that at least one of R2 is an iC4 acid residue and at least one of R2 is an iC8 acid residue).
• the molar ratio of iC4 acid residues/iC8 acid residues may be 50/50 or more, 60/40 or more, 70/30 or more, or 75/25 or more, and may be 95/5 or less, 90/10 or less, or 85/15 or less.
• the third ester is an ester (complex ester) of pentaerythritol, a divalent carboxylic acid, and a fatty acid, the fatty acid being a mixed fatty acid of at least one selected from the group consisting of branched butanoic acid, branched pentanoic acid, and linear pentanoic acid, and either branched octanoic acid or branched nonanoic acid.
• the third ester is represented by the following formula (3):
• PE represents a residue in which an H atom has been removed from each of the four -OH groups in pentaerythritol
• DCA represents a residue in which an -OH group has been removed from each of the two -COOH groups in a divalent carboxylic acid
• R3 represents a residue in which an -OH group has been removed from a -COOH group in a branched butanoic acid (iC4 acid residue), a residue in which an -OH group has been removed from a -COOH group in a branched pentanoic acid (also referred to as an iC5 acid residue), a residue in which an -OH group has been removed from a -COOH group in a linear pentanoic acid (also referred to as an nC5 acid residue), a residue in which an -OH group has been removed from a -COOH group in a branched octanoic
• the molar ratio of iC4 acid residues/iC8 acid residues, or the molar ratio of iC4 acid residues/iC9 acid residues may be 50/50 or more, 60/40 or more, 70/30 or more, 75/25 or more, 84/16 or more, or 86/14 or more, and may be 95/5 or less, 90/10 or less, or 85/15 or less.
• the dicarboxylic acid constituting the third ester may be a divalent aliphatic carboxylic acid.
• the dicarboxylic acid may be linear or branched.
• the number of carbon atoms in the dicarboxylic acid may be 4 or more or 6 or more, and 12 or less or 10 or less.
• Examples of the dicarboxylic acid include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and phthalic acid.
• the dicarboxylic acid is preferably adipic acid.
• the fatty acid having 6 to 9 carbon atoms constituting the first ester may be a mixture of two or more fatty acids, for example, a mixture of a fatty acid having 5 to 8 carbon atoms and a fatty acid having 9 carbon atoms, and preferably a mixture of a fatty acid having 8 carbon atoms and a fatty acid having 9 carbon atoms.
• the molar ratio (iC4 acid/iC8 acid ratio) of branched butanoic acid (preferably 2-methylpropanoic acid)/branched octanoic acid (preferably 2-ethylhexanoic acid) in the fatty acid having 6 to 9 carbon atoms constituting the first ester and the fatty acid constituting the second ester may be 5/95 or more, 10/90 or more, or 20/80 or more, and may be 95/5 or less, 60/40 or less, 50/50 or less, 40/60 or less, or 35/65 or less.
• the molar ratio of branched butanoic acid (preferably 2-methylpropanoic acid)/branched octanoic acid (preferably 2-ethylhexanoic acid) in the fatty acids constituting the pentaerythritol tetraester may be 5/95 or more, 10/90 or more, or 20/80 or more, and may be 95/5 or less, 60/40 or less, 50/50 or less, 40/60 or less, 35/65 or less, or 34/66 or less.
• the kinetic viscosity of the first ester at 40°C may be smaller than the kinetic viscosity of the second ester at 40°C.
• the low-temperature side refrigerant compatibility region of the first ester may be narrower than the low-temperature side refrigerant compatibility region of the second ester, for example, the maximum low-temperature side two-phase separation temperature of the first ester when mixed with difluoromethane may be higher than that of the second ester.
• the content of the third ester may be 2% by mass or more, 5% by mass or more, or 10% by mass or more, and may be 65% by mass or less, 40% by mass or less, 30% by mass or less, or 20% by mass or less, based on the total amount of the ester for the refrigerating machine oil. Furthermore, the total content of the second ester and the third ester may be 7% by mass or more, 10% by mass or more, 20% by mass or more, or 30% by mass or more, based on the total amount of the esters for the refrigerating machine oil, and may be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, or 50% by mass or less.
• the kinematic viscosity of the first ester at 40°C may be, for example, 5 mm2 /s or more, 100 mm2 /s or less, 20 mm2 /s or more, 30 mm2 /s or more, or 40 mm2 /s or more, and 80 mm2 /s or less, 60 mm2 /s or less, or 50 mm2 /s or less.
• the kinematic viscosity of the first ester at 100°C may be 1 mm2 /s or more, 3 mm2 /s or more, or 5 mm2 /s or more, and 20 mm2 /s or less, 10 mm2 /s or less, or 8 mm2 /s or less.
• the viscosity index of the first ester may be 50 or more, 60 or more, or 70 or more, and 120 or less, 110 or less, or 100 or less.
• the kinematic viscosity and viscosity index in this specification refer to those measured in accordance with JIS K2283:2000.
• the acid value of the first ester may be 0.1 mgKOH/g or less, or 0.05 mgKOH/g or less.
• the hydroxyl value of the first ester may be 15 mgKOH/g or less, 10 mgKOH/g or less, or 5 mgKOH/g or less.
• the pour point of the first ester may be -20°C or less, or -40°C or less.
• the acid value means the acid value measured in accordance with JIS K2501:2003.
• the hydroxyl value means the hydroxyl value measured in accordance with JIS K0070:1992.
• the pour point means the pour point measured in accordance with JIS K2269:1987.
• ester for refrigeration oil described above is suitable for use as a base oil for refrigeration oil. Therefore, the "ester for refrigeration oil” in the above description can be read as "base oil for refrigeration oil.”
• another embodiment of the present invention is a base oil for refrigeration oil that contains the above first ester, second ester, and third ester.
• Another embodiment of the present invention is a refrigeration oil containing the above-mentioned refrigeration oil base oil (refrigeration oil ester).
• the content of the refrigeration oil base oil (refrigeration oil ester) may be 50 mass% or more, 60 mass% or more, 70 mass% or more, 80 mass% or more, or 90 mass% or more based on the total amount of the refrigeration oil.
• the refrigeration oil may further contain other base oils.
• the other base oils include mineral oils and synthetic oils.
• the mineral oils may be paraffinic mineral oils, naphthenic mineral oils, etc.
• the synthetic oils include synthetic hydrocarbon oils such as poly-alpha-olefins and alkylbenzenes, and oxygen-containing oils such as esters other than the above-mentioned esters for refrigeration oils, polyvinyl ethers, and polyalkylene glycols.
• the kinetic viscosity of the refrigerating machine oil at 40° C. may be 20 mm 2 /s or more, 30 mm 2 /s or more, or 40 mm 2 /s or more, and may be 200 mm 2 /s or less, 100 mm 2 /s or less, or 80 mm 2 /s or less.
• the kinetic viscosity of the refrigerating machine oil at 100° C. may be 1 mm 2 /s or more, 3 mm 2 /s or more, or 5 mm 2 /s or more, and may be 30 mm 2 /s or less, 20 mm 2 /s or less, or 10 mm 2 /s or less.
• the viscosity index of the refrigerating machine oil may be 50 or more, 60 or more, or 70 or more, and may be 120 or less, 110 or less, or 100 or less.
• the refrigeration oil may be present in the refrigerator as a working fluid composition for the refrigerator mixed with a refrigerant. That is, in one embodiment, the refrigeration oil is used together with the refrigerant.
• Another embodiment of the present invention is a working fluid composition containing the above-mentioned refrigeration oil and a refrigerant.
• the refrigeration oil of this embodiment contains the above-mentioned refrigeration base oil (refrigeration ester), and therefore has excellent compatibility with difluoromethane and refrigerant dissolution viscosity characteristics, and therefore the refrigerant is preferably a refrigerant containing difluoromethane (R32).
• the difluoromethane content may be 50 mass% or more, 60 mass% or more, 70 mass% or more, 80 mass% or more, or 90 mass% or more based on the total amount of the refrigerant.
• the refrigerant may consist solely of difluoromethane, or may further contain other refrigerants in addition to difluoromethane.
• Other refrigerants include saturated fluorohydrocarbons (also called HFCs) other than difluoromethane, unsaturated fluorohydrocarbons (also called HFOs), hydrocarbons, fluorinated ethers, bis(trifluoromethyl)sulfide, trifluoroiodomethane, ammonia (R717), and carbon dioxide (R744).
• esters for refrigeration oils base oils for refrigeration oils
• Table 1 The following first ester, second ester, and third ester were used to prepare esters for refrigeration oils (base oils for refrigeration oils) with the composition shown in Table 1.
• (First Ester) 1A Diester of neopentyl glycol and 2-ethylhexanoic acid (kinematic viscosity at 40° C.: 7.4 mm 2 /s, kinematic viscosity at 100° C.: 2.0 mm 2 /s, viscosity index: 52, acid value: less than 0.01 mgKOH/g, hydroxyl value: less than 2 mgKOH/g, pour point: less than ⁇ 45° C.) 1B: Tetraester of pentaerythritol and 2-ethylhexanoic acid/3,5,5-trimethylhexanoic acid (molar ratio: 70/30) (40°C kinematic viscosity: 56.5 mm 2 /s, 100°C kinematic viscosity: 7.43 mm 2 /s, viscosity index: 90, acid value: less than 0.01 mgKOH/g, hydroxyl value: less than 2 mgKOH/g, pour point
• (The Third Ester) 3A Complex ester represented by the following formula (3a) (molar ratio of iC4 acid residue/iC8 acid residue in the group represented by R3a : 76/24)
• PE represents a residue in which an H atom has been removed from each of the four -OH groups in pentaerythritol
• AA represents a residue in which an -OH group has been removed from each of the two -COOH groups in adipic acid
• R3a represents a residue in which an -OH group has been removed from the -COOH group in 2-methylpropanoic acid (iC4 acid residue) or a residue in which an -OH group has been removed from the -COOH group in 2-ethylhexanoic acid (iC8 acid residue).
• 3B Complex ester represented by the above formula (3a) (molar ratio of iC4 acid residue/iC8 acid residue in the group represented by R3a : 87/13)
• 3C Complex ester represented by the above formula (3a) (molar ratio of iC4 acid residue/iC8 acid residue in the group represented by R3a : 82/18)
• 3D Complex ester represented by the above formula (3a) (molar ratio of iC4 acid residue/iC8 acid residue in the group represented by R3a : 88/12)
• the iC4 acid tetraester of pentaerythritol, the iC8 acid tetraester of pentaerythritol, and the iC9 acid tetraester of pentaerythritol were used as standard samples, and necessary parameters such as the area, mass and molar-based relative sensitivity, and correction coefficient of each fatty acid obtained from the calibration curve were used.
• the results are shown in Table 1 as "iC4 acid/iC8 acid ratio" and "iC4 acid/iC9 acid ratio".
• the refrigerant dissolution viscosity (mm 2 /s) was calculated from parameters such as the refrigerant gas density, the amount of oil and refrigerant filled, and the mass of the working fluid. The results are shown in Table 1. The refrigerant dissolution viscosity when the first ester 1C was used alone as the base oil was also evaluated in the same manner, and was found to be 2.7 mm 2 /s.

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