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WO2025041739A1 - Composition de type azéotrope, composition d'aérosol, agent de nettoyage, solution lubrifiante, milieu de transfert de chaleur, procédé de production de composition, composition, procédé de nettoyage et procédé de récupération - Google Patents

Composition de type azéotrope, composition d'aérosol, agent de nettoyage, solution lubrifiante, milieu de transfert de chaleur, procédé de production de composition, composition, procédé de nettoyage et procédé de récupération Download PDF

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Publication number
WO2025041739A1
WO2025041739A1 PCT/JP2024/029319 JP2024029319W WO2025041739A1 WO 2025041739 A1 WO2025041739 A1 WO 2025041739A1 JP 2024029319 W JP2024029319 W JP 2024029319W WO 2025041739 A1 WO2025041739 A1 WO 2025041739A1
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WO
WIPO (PCT)
Prior art keywords
composition
azeotrope
mass
present disclosure
cleaning
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/JP2024/029319
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English (en)
Japanese (ja)
Inventor
夏奈子 長舩
俊希 毛利
伊吹 向原
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Central Glass Co Ltd
Original Assignee
Central Glass Co Ltd
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Filing date
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Publication of WO2025041739A1 publication Critical patent/WO2025041739A1/fr
Pending legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/192—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing halogen
    • 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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • 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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen

Definitions

  • the present disclosure relates to an azeotrope-like composition that has a small impact on the global environment and is unlikely to undergo compositional changes even when repeatedly evaporated and condensed, an aerosol composition, a cleaning agent, a lubricant solution, and a heat transfer medium that contain the composition, as well as a method for producing the composition, the composition, a cleaning method using the cleaning agent, and a method for recovering the cleaning agent.
  • chlorofluorocarbons hereinafter referred to as "CFCs”
  • hydrochlorofluorocarbons hereinafter referred to as “HCFCs”
  • hydrofluorocarbons hereinafter referred to as “HFCs”
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbons
  • HFCs hydrofluorocarbons
  • Fluoroolefins have been proposed as alternatives to CFCs, HCFCs, and HFCs. Fluoroolefins have a short life in the atmosphere and have a small impact on the global environment because they have a carbon-carbon double bond in their molecules.
  • Patent Document 1 proposes a composition containing monochlorotrifluoropropene (HCFO-1233) and an additional component.
  • Patent Document 2 specifically discloses a composition containing 40 to 70 mass % of (Z)-1-chloro-3,3,3-trifluoropropene and 30 to 60 mass % of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • An object of the present disclosure is to provide an azeotrope-like composition that has a small impact on the global environment and is less likely to undergo compositional changes even when repeatedly evaporated and condensed. It is also an object of the present disclosure to provide aerosol compositions, cleaning agents, lubricant solutions, heat transfer media, and methods of making the compositions, compositions, cleaning methods using the cleaning agents, and recovery methods that include the azeotrope-like compositions.
  • [4] The azeotrope-like composition according to any one of [1] to [3], comprising 70.01 to 99.99 mass% of (Z)-1-chloro-3,3,3-trifluoropropene and 0.01 to 29.99 mass% of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, based on the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • [5] The azeotrope-like composition according to any one of [1] to [3], comprising 0.01 to 28.00 mass% of (Z)-1-chloro-3,3,3-trifluoropropene and 72.00 to 99.99 mass% of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, based on the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • the azeotrope-like composition according to [7], comprising 0.0001 to 1.00 mass% of water based on the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether; adding to the azeotrope-like composition at least one selected from the group consisting of a stabilizer, a surfactant, a flame retardant, a metal passivator, and a rust inhibitor; Method for producing the composition.
  • a composition comprising the azeotrope-like composition according to any one of [1] to [9], and at least one selected from the group consisting of a stabilizer, a surfactant, a flame retardant, a metal passivator, and a rust inhibitor.
  • [12] An aerosol composition comprising the azeotrope-like composition according to any one of [1] to [9] and a propellant gas.
  • a cleaning agent comprising the azeotrope-like composition according to any one of [1] to [9].
  • a cleaning agent comprising the aerosol composition according to [12].
  • the cleaning agent according to [13] or [14] which is for cleaning vehicles or transport vehicles.
  • a method for cleaning an article comprising a step of contacting an article to be cleaned with the cleaning agent according to [13] or [14].
  • [17] [13] or [14], and cleaning an article with the cleaning agent according to the present invention Purifying the cleaning agent after cleaning. How to recover cleaning agents.
  • a lubricant solution comprising the azeotrope-like composition according to any one of [1] to [9] and a lubricant.
  • a heat transfer medium comprising the azeotrope-like composition according to any one of [1] to [9], or the aerosol composition according to [12].
  • the present disclosure can also provide aerosol compositions, cleaning agents, lubricant solutions, heat transfer media, and methods of making the compositions, cleaning methods using the cleaning agents, and recovery methods that include the azeotrope-like compositions.
  • a compound in which some of the hydrogen atoms of a saturated hydrocarbon compound are replaced with fluorine atoms is called a hydrofluorocarbon (HFC)
  • a compound in which some of the hydrogen atoms of a saturated hydrocarbon compound are replaced with fluorine atoms and chlorine atoms is called a hydrochlorofluorocarbon (HCFC)
  • HCFC hydrochlorofluorocarbon
  • CFC chlorofluorocarbon
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • a numerical range expressed using “ ⁇ ” means a range that includes the numerical values written before and after " ⁇ " as the lower and upper limits.
  • azeotropic or azeotrope-like compositions Before describing the compositions of the present disclosure, azeotropic compositions and azeotrope-like compositions will be described. Since fluorine-containing olefins are highly compatible with various solvents, it is possible to easily prepare a uniform composition. However, in the case of such a simple composition, there is an inherent problem that the liquid composition is easily variable. That is, even if multiple types of liquids are mixed and compatibility is ensured, the problem that the liquid composition is easily variable due to the difference in volatility of each component cannot be avoided.
  • a binary liquid composition when placed in an ultrasonic cleaner and used as a cleaning agent, generally, a low-boiling point component with high volatility (a component with a high vapor pressure) volatilizes preferentially, and a high-boiling point component with low volatility is concentrated in the cleaning tank.
  • a concentration of the low-boiling point component in the cleaning liquid decreases over time, which may cause poor cleaning.
  • the cleaning liquid may become a flammable composition if the non-flammable component volatilizes preferentially.
  • the liquid composition may fluctuate over a long period of time. Fluctuations in the liquid composition can cause changes in the heat capacity, viscosity, or affinity with lubricants of the liquid, which can reduce the operating performance of the thermodynamic cycle.
  • liquid composition when using a binary (multi-component) liquid composition as a cleaning agent or working fluid, the liquid composition must be frequently analyzed, and the appropriate ratio must be constantly mixed to ensure that the composition is within the appropriate range, and any volatilized components must be replenished.
  • managing the liquid composition in this way can be a significant burden on the workforce.
  • an azeotropic composition evaporates with the same composition as the liquid, making it a very desirable composition in which the liquid composition does not change during use.
  • azeotrope refers to azeotropy in the strict thermodynamic sense.
  • a composition of ethanol (96% by mass) and water (4% by mass) is an azeotrope, and the vapor that exists in vapor-liquid equilibrium with this is also "ethanol (96% by mass): water (4% by mass)", which is completely consistent with the liquid composition.
  • This phenomenon is called “azeotropy.”
  • azeotropy At a specific temperature and pressure, there is only one composition of the azeotropic composition.
  • Azeotrope-like is also called “quasi-azeotrope” and is not a strict azeotrope thermodynamically, but for a liquid with a certain range of compositions, the liquid composition may be substantially equal to the composition of the gas in equilibrium, and refers to such a phenomenon. Even if the compositions of the gas phase and liquid phase do not completely match, as long as the compositions of the gas phase and liquid phase are substantially the same, those skilled in the art can treat it in the same way as an azeotropic composition. In this case, the smaller the difference in the gas-liquid equilibrium composition between the gas phase and liquid phase, the better.
  • the difference in the composition between the gas phase and liquid phase of one component is preferably 8.00 mass% or less, more preferably 7.00 mass% or less, and particularly preferably 4.00 mass% or less.
  • the phenomenon in which the gas-liquid equilibrium composition of the gas phase and liquid phase is substantially the same is called azeotrope-like or pseudo-azeotrope, and the composition is called azeotrope-like composition or pseudo-azeotrope composition.
  • a composition having an azeotrope-like composition (or pseudo-azeotrope composition) is called an azeotrope-like composition (or pseudo-azeotrope composition).
  • the phrase "it is sufficient if the gas-liquid equilibrium composition of the gas phase and the liquid phase is substantially the same” means that the gas-liquid equilibrium composition difference between the gas phase and the liquid phase is small, and when the composition of the present disclosure is a binary (or ternary or higher) composition, the composition difference between the gas phase and the liquid phase of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether contained in the composition of the present disclosure is 8.00 mass% or less, respectively, and the composition difference is preferably 7.00 mass% or less, and more preferably 4.00 mass% or less.
  • azeotrope-like is not derived theoretically, but is found only when vapor-liquid equilibrium is experimentally investigated for various types and composition ratios of liquids, and the composition of the vapor phase and the composition of the liquid phase coincidentally substantially coincide.
  • a vapor-liquid equilibrium experiment was carried out for a mixture of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, and an azeotrope-like composition in which the vapor and liquid compositions are substantially the same was found.
  • the vapor-liquid equilibrium experiment was specifically carried out based on the ⁇ Measurement of Vapor-Liquid Equilibrium> described in the Examples.
  • composition of the present disclosure is an azeotrope-like composition containing 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (hereinafter also referred to as HFE-356mmz) and (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) (also referred to as the "azeotrope-like composition of the present disclosure”).
  • the compositions of the present disclosure may consist solely of HFE-356mmz and 1233zd(Z).
  • reference to “the composition of the present disclosure” refers to an azeotrope-like composition containing 1233zd(Z) described below and HFE-356mmz described below.
  • the composition contains 70.01 to 99.99 mass% of 1233zd(Z) and 0.01 to 29.99 mass% of HFE-356mmz relative to the total amount of 1233zd(Z) and HFE-356mmz contained in the composition.
  • the composition of the gas phase portion and the composition of the liquid phase portion are close to each other in this composition range, so that composition fluctuations are unlikely to occur.
  • the composition contains 85.00 to 99.99 mass% of 1233zd(Z) and 0.01 to 15.00 mass% of HFE-356mmz relative to the total amount of 1233zd(Z) and HFE-356mmz contained in the composition.
  • the composition contains 90.00 to 99.99 mass% of 1233zd(Z) and 0.01 to 10.00 mass% of HFE-356mmz relative to the total amount of 1233zd(Z) and HFE-356mmz contained in the composition.
  • the composition of the gas phase portion and the liquid phase portion are even closer to each other in composition, so that composition fluctuations are unlikely to occur.
  • the composition contains 0.01 to 28.00 mass% of 1233zd(Z) and 72.00 to 99.99 mass% of HFE-356mmz relative to the total amount of 1233zd(Z) and HFE-356mmz contained in the composition.
  • the composition of the gas phase portion and the composition of the liquid phase portion are close to each other in this composition range, so that composition fluctuations are unlikely to occur.
  • the composition contains 0.01 to 15.00 mass% of 1233zd(Z) and 85.00 to 99.99 mass% of HFE-356mmz relative to the total amount of 1233zd(Z) and HFE-356mmz contained in the composition.
  • the composition contains 0.01 to 11.00 mass% of 1233zd(Z) and 89.00 to 99.99 mass% of HFE-356mmz relative to the total amount of 1233zd(Z) and HFE-356mmz contained in the composition.
  • the composition of the gas phase portion and the liquid phase portion are even closer to each other in composition, so that composition fluctuations are unlikely to occur.
  • the total amount of 1233zd(Z) and HFE-356mmz is preferably 80 mass% or more, more preferably 90 mass% or more, and even more preferably 95 mass% or more, based on the total amount of the composition.
  • the composition of the present disclosure may be substantially composed of only 1233zd(Z) and HFE-356mmz. "The composition of the present disclosure is substantially composed of only 1233zd(Z) and HFE-356mmz" means that in the composition of the present disclosure, the total amount of 1233zd(Z) and HFE-356mmz is 98 mass% or more based on the total amount of the composition.
  • the composition of the present disclosure is preferably composed of only 1233zd(Z) and HFE-356mmz.
  • composition of the present disclosure contains 80% by mass or more of 1233zd(Z) and HFE-356mmz in total, which means that it has a small impact on the global environment, undergoes small changes in composition when repeatedly evaporated and condensed, and can be handled in a manner similar to the above-mentioned azeotrope-like composition. Therefore, when the composition of the present disclosure is used in various applications such as cleaning agents, solvents, aerosols, and heat transfer media, it has the advantage of providing stable performance equivalent to the above-mentioned azeotrope-like composition.
  • 1233zd(Z) is an olefin having a carbon-carbon double bond, and therefore has a short lifetime in the atmosphere and a small ozone depletion potential and global warming potential.
  • 1233zd(Z) has a boiling point of 39°C, making it suitable for use on parts that are easily affected by heat.
  • 1233zd(Z) has no flash point, excellent drying properties, and excellent penetration due to its low surface tension and viscosity, making it an excellent cleaner and solvent.
  • 1233zd(Z) since 1233zd(Z) has a low viscosity, it experiences little resistance when passing through piping, has excellent transport characteristics, and has excellent performance as a heat transfer medium. 1233zd(Z) can be produced, for example, based on the description in JP 2017-110020 A.
  • compositions disclosed herein contain the above-mentioned amounts of 1233zd(Z), which reduces the impact on the global environment and provides performance suitable for a variety of applications, such as cleaning agents, solvents, aerosols, and heat transfer media.
  • HFE-356mmz 1,1,1,3,3,3-hexafluoroisopropyl methyl ether
  • HFE-356mmz has a boiling point of about 51°C and can be used on parts that are sensitive to heat. Furthermore, HFE-356mmz has excellent drying properties and excellent penetration properties due to its low surface tension and viscosity, and therefore has excellent performance as a cleaning agent and solvent. Furthermore, since HFE-356mmz has a low viscosity, it experiences little resistance when passing through piping, has excellent transport characteristics, and has excellent performance as a heat transfer medium.
  • HFE-356mmz has little effect on resin materials such as acrylonitrile-butadiene-styrene copolymer resin (hereinafter also referred to as ABS resin), polycarbonate (PC), and polystyrene resin (PS).
  • ABS resin acrylonitrile-butadiene-styrene copolymer resin
  • PC polycarbonate
  • PS polystyrene resin
  • HFE-356mmz is a known compound and can be obtained, for example, by reacting 1,1,1,3,3,3-hexafluoroisoproalcohol with dimethyl sulfate in the presence of an alkali (US Pat. No. 3,346,448).
  • composition of the present disclosure contains the above-mentioned amount of HFE-356mmz, and thus has excellent performance in various areas, such as cleaning properties, solubility, and transport properties.
  • HFE-356mmz the above-mentioned amount of HFE-356mmz
  • 1233zd(Z) when used alone, it may cause strong chemical attack (erosion) on resins, etc., but by using it in combination with HFE-356mmz, it is possible to reduce chemical attack.
  • compositions of the present disclosure may contain water. Even when containing water, the compositions of the present disclosure may form azeotrope-like compositions.
  • the water content is not particularly limited, but is preferably 0.0001 to 1.00 mass%, more preferably 0.0001 to 0.5 mass%, and even more preferably 0.0001 to 0.1 mass%, based on the total amount of 1233zd(Z) and HFE-356mmz.
  • the inclusion of water has the effect of improving the cleaning performance against water-soluble processing oil.
  • the composition of the present disclosure is an azeotrope-like composition consisting of (Z)-1-chloro-3,3,3-trifluoropropene, 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, and water.
  • compositions of the present disclosure may further comprise other ingredients.
  • other components include hydrocarbons, alcohols, ketones, non-fluorinated ethers, esters, chlorocarbons, HFCs, HFEs, and the like, as well as raw materials, materials, and by-products used in the production and refining processes of 1233zd(Z) and HFE-356mmz.
  • the hydrocarbon is preferably a hydrocarbon having a carbon number of 5 or more.
  • the hydrocarbon may be linear or cyclic, and may be a saturated or unsaturated hydrocarbon.
  • n-pentane, cyclopentane, n-hexane, cyclohexane, and n-heptane are preferred.
  • the alcohol is preferably an alcohol having a carbon number of 1 to 16.
  • the alcohol may be a chain or cyclic alcohol, and may be a saturated or unsaturated alcohol.
  • methanol, ethanol, and isopropyl alcohol are preferred.
  • the ketone is preferably a ketone having a carbon number of 3 to 9.
  • the ketone may be a chain or cyclic ketone, and may be a saturated or unsaturated ketone.
  • As the ketone acetone and methyl ethyl ketone are preferred.
  • the non-fluorinated ether is preferably an ether having a carbon number of 2 to 8.
  • the non-fluorinated ether may be a chain or cyclic ether, and may be a saturated or unsaturated ether.
  • As the ether diethyl ether, diisopropyl ether, and tetrahydrofuran are preferable.
  • the ester is preferably an ester having a carbon number of 2 to 19.
  • the ester may be linear or cyclic, and may be a saturated ester or an unsaturated ester.
  • methyl acetate and ethyl acetate are preferred.
  • the chlorocarbon is preferably a chlorocarbon having a carbon number of 1 to 3.
  • the chlorocarbon may be a chain or cyclic chlorocarbon, and may be a saturated or unsaturated chlorocarbon.
  • As the chlorocarbon methylene chloride, trans-1,2-dichloroethylene, and trichloroethylene are more preferable.
  • the HFC is preferably a chain or cyclic HFC having 4 to 8 carbon atoms, and more preferably an HFC in which the number of fluorine atoms in one molecule is equal to or greater than the number of hydrogen atoms.
  • HFC 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, and 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane are preferred.
  • the HFE is preferably an HFE other than 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, and examples thereof include 1,1,2,2-tetrafluoroethoxy-1-(2,2,2-trifluoro)ethane (CF 3 CH 2 OCF 2 CF 2 H, hereinafter also referred to as HFE-347pc-f), methoxynonafluorobutane (C 4 F 9 OCH 3 , hereinafter also referred to as HFE-449s1), ethoxynonafluorobutane (C 4 F 9 OC 2 H 5 , hereinafter also referred to as HFE-569sf), methoxyheptafluoropropane (C 3 F 7 OCH 3 , hereinafter also referred to as HFE-347mcc), methoxy, 2-(trifluoromethyl)-3-methoxynonafluoropentane (C 2 F 5 CF(OCH 3 )CF(CF 3 )
  • raw materials, supplies, by-products, etc. used in the production and purification processes of 1233zd(Z) and HFE-356mmz include, for example, chlorotrifluoropropenes other than 1233zd(Z) (for example, (E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E), or also referred to as "1233zd(E)”)), dichlorotrifluoropropene (HCFO-1223), chlorotetrafluoropropane (HCFC-244), chloropentafluoropropane (HCFC-235 ...44), Examples of such isomers include dichlorotetrafluoropropene (HCFO-1224), dichlorotetrafluoropropene (HCFO-1214), pentafluoropropane (HFC-245), tetrafluoropropene (HFO-1234), trifluoropropyne, water, hexafluor
  • the content of other components is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, based on the total amount of the composition.
  • compositions containing azeotrope-like compositions The present disclosure also relates to a composition comprising the azeotrope-like composition of the present disclosure described above and at least one selected from the group consisting of a stabilizer, a surfactant, a flame retardant, a metal passivator, and a rust inhibitor.
  • a composition containing the above-mentioned azeotrope-like composition of the present disclosure and at least one of the above-mentioned additives is used for various applications, it has the advantage that stable performance equivalent to that of the above-mentioned azeotrope-like composition can be obtained.
  • the content of at least one component selected from stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 1% by mass or less, based on the total amount of the composition.
  • stabilizers include nitromethane, nitroethane, nitropropane, nitrobenzene, diethylamine, triethylamine, isopropylamine, diisopropylamine, butylamine, isobutylamine, tert-butylamine, ⁇ -picoline, N-methylbenzylamine, diallylamine, N-methylmorpholine, phenol, o-cresol, m-cresol, p-cresol, thymol, p-tert-butylphenol, tert-butylcatechol, catechol, isoeugenol, o-methoxyphenol, p-methoxyphenol, 4,4'-dihydroxyphenyl-2,2-propiisoamyl, benzyl salicylate, methyl salicylate,
  • the glycidyl ether include 2,6-di-tert-butyl-p-cresol, 2-(2'-hydroxy-5'-methyl-
  • 2,6-di-tert-butyl-p-cresol, p-methoxyphenol, 1,2-butylene oxide, isoamylene, octene, 2,4,4-trimethyl-1-pentene, 2,4,4-trimethyl-2-pentene, and 2-methylpentene are preferred.
  • the stabilizer may be used alone or in combination of two or more kinds.
  • Preferred surfactants are nonionic surfactants such as sorbitan aliphatic esters such as sorbitan monooleate and sorbitan trioleate; polyoxyethylene sorbitol fatty acid esters such as polyoxyethylene sorbitol tetraoleate; polyethylene glycol fatty acid esters such as polyoxyethylene monolaurate; polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether; polyoxyethylene alkyl phenyl ethers such as polyoxyethylene nonylphenyl ether; and polyoxyethylene alkylamine fatty acid amides such as polyoxyethylene oleic acid amide.
  • the surfactant one type may be used, or two or more types may be used.
  • phosphates halogenated aromatic compounds, fluorinated iodocarbons, fluorinated bromocarbons, etc. are preferred.
  • the flame retardant one type may be used, or two or more types may be used.
  • compositions disclosed hereinabove has a small impact on the global environment, is resistant to compositional changes even when repeatedly evaporated and condensed, and can exhibit excellent performance suitable for various applications such as a cleaning agent, solvent, aerosol, and heat transfer medium.
  • the compositions of the present disclosure are preferably used as cleaning agents, solvents, aerosols, heat transfer media, fire extinguishing agents, foaming agents, and the like.
  • Materials to which the compositions of the present disclosure can be applied include resin materials, metals, plastics, elastomers, glass, ceramics, fibers, composite materials thereof, etc.
  • metals such as iron, copper, nickel, gold, silver, platinum, etc., sintered metals, glass, fluororesins, polyimides, polyphenylene sulfide, liquid crystal polymers, engineering plastics such as PEEK, etc. are preferred.
  • the present disclosure relates to a process for producing an azeotrope-like composition
  • a process for producing an azeotrope-like composition comprising: providing an azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether; adding to the azeotrope-like composition at least one selected from the group consisting of a stabilizer, a surfactant, a flame retardant, a metal passivator, and a rust inhibitor; Methods for making the compositions are also disclosed.
  • the stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors include the stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors described above.
  • the content of at least one component selected from stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 1% by mass or less, based on the total amount of the composition.
  • Aerosols and aerosol compositions The composition of the present disclosure can be used as an aerosol by combining it with a propellant gas.
  • the present disclosure also relates to an aerosol composition comprising the composition of the present disclosure and a propellant gas.
  • the propellant gas used in the present disclosure preferably has a pressure of atmospheric pressure (1.013 ⁇ 10 5 Pa) or higher at 0° C.
  • the propellant gas may be a liquefied gas or a compressed gas, such as dimethyl ether (DME), propane, butane, isobutane, 1,1-difluoroethane (HFC-152a), 1,1,1,2-tetrafluoroethane (HFC-134a), 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,3,3,3-tetrafluoropropene (HFO-1234ze), nitrogen, carbon dioxide, nitrous oxide, trifluoroiodomethane, or the like, which may be used alone or in combination of two or more kinds, and for example, air may also be suitably used.
  • the propellant gas may be either liquefied gas or compressed gas, or a combination of liquefied gas and compressed gas.
  • the aerosol may further be filled with a solute.
  • the solute may be dissolved in the composition of the present disclosure and filled into the aerosol, or may be filled into a container separately from the composition of the present disclosure and the propellant gas.
  • the solute include surface treatment agents such as lubricants, rust inhibitors, moisture-proof coating agents, and antifouling coating agents.
  • the aerosol of the present disclosure may contain a stabilizer, other solvents, etc., as necessary.
  • the stabilizer include the stabilizers described above.
  • the other solvents include the solvent (A) described below.
  • the content of the stabilizer in the aerosol of the present disclosure is preferably 5% by mass or less, and more preferably 1% by mass or less, based on the total of the composition of the present disclosure and the stabilizer.
  • the content of the other solvent in the aerosol of the present disclosure is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, based on the total of the composition of the present disclosure and the other solvent.
  • composition of the present disclosure has excellent cleaning properties and can be used as a cleaning agent for degreasing, flux cleaning, precision cleaning, draining cleaning, rinsing cleaning, dry cleaning, etc. It is also preferable to use the above-mentioned aerosol composition instead of the composition of the present disclosure.
  • the present disclosure also relates to a cleaning agent comprising the composition or aerosol composition of the present disclosure described above.
  • Examples of articles to which the cleaning agent of the present disclosure can be applied include optical parts, medical instruments, electrical equipment, precision machinery, textile products, and parts thereof.
  • Examples of electrical equipment, precision machinery, optical articles, and parts thereof include ICs, capacitors, printed circuit boards, micromotors, relays, bearings, optical lenses, glass substrates, etc.
  • Examples of medical instruments include catheters, injection needles, etc.
  • the cleaning agent according to the present disclosure can also be applied to various parts, such as brakes, wheels, and suspensions, in various vehicles and transport means, such as automobiles, bicycles, construction machines, aircraft, and railroad cars, and can be suitably used as a so-called brake cleaner or parts cleaner.
  • the cleaning agent according to the present disclosure is also preferably used for cleaning vehicles or transport means.
  • the cleaning method is not particularly limited, but an example of a method for cleaning an article is a method in which the cleaning agent of the present disclosure is brought into contact with an article to be cleaned to remove dirt adhering to the article.
  • the present disclosure also relates to a method for cleaning an article, comprising a step of contacting the cleaning agent of the present disclosure with an article to be cleaned.
  • the method may include immersing the article to be cleaned in the cleaning agent of the present disclosure to wash off the dirt, wiping with a rag, spray cleaning, etc., and these may be used in combination.
  • One particularly preferred embodiment is to put the cleaning agent of the present disclosure into an ultrasonic cleaner, immerse the article to be cleaned in the liquid, and perform ultrasonic cleaning treatment.
  • Examples of dirt that adheres to articles include grease, processing oil, silicone oil, flux, wax, ink, mineral oil, release agents containing silicone oil, oils and fats such as pitch and asphalt, dust, etc.
  • processing oils include cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, press processing oil, punching oil, drawing oil, assembly oil, wire drawing oil, etc.
  • the cleaning agent of the present disclosure has excellent cleaning properties and can be particularly suitably used for cleaning processing oil, pitch, and asphalt.
  • the cleaning conditions in the above cleaning method can be appropriately selected depending on the cleaning method.
  • a known cleaning device can be appropriately selected.
  • the method and cleaning device described in WO 2008/149907 can be used.
  • azeotrope-like compositions undergo almost no compositional fluctuations even when used in an open system, so cleaning agents using the compositions disclosed herein that contain these exhibit stable cleaning power without the need for frequent composition control. This is a major practical advantage.
  • the cleaning agent can be recovered by the following steps.
  • the method for recovering the cleaning agent is not particularly limited, but includes a step of cleaning an article with the cleaning agent of the present disclosure and a step of purifying the cleaning agent after cleaning.
  • the method for cleaning an article using the cleaning agent of the present disclosure is not particularly limited, but as described above, there is a method in which the cleaning agent of the present disclosure is brought into contact with the article to be cleaned to remove dirt adhering to the article.
  • the method for purifying the cleaning agent after cleaning is not particularly limited, but may be, for example, the following distillation operation.
  • an azeotrope-like composition constituting the cleaning agent, as an example. Since a typical distillation regeneration apparatus for cleaning agents is a simple distillation type, an azeotrope-like composition consisting of 1233zd(Z) and HFE-356mmz can be regenerated with a commercially available distillation regeneration apparatus without substantial change in composition. In particular, an azeotrope-like composition is preferable because there is no change in composition even when a distillation column with a large number of stages is used.
  • the two liquid components 1233zd(Z) and HFE-356mmz, maintain their properties as an azeotrope-like composition, so the recovered liquid can be reused as a cleaning solvent without undergoing extensive composition adjustment.
  • the “other components” may be removed by distillation, so in that case it is desirable to supplement them separately.
  • the cleaning agent can be used as a rinse agent for removing the high-boiling-point cleaning agent adhering to an article after a cleaning process using the high-boiling-point cleaning agent.
  • the cleaning agent is preferably a rinse agent.
  • the content of the composition of the present disclosure in the cleaning agent of the present disclosure is preferably 80 mass% or more, more preferably 90 mass% or more, and even more preferably 95 mass% or more, based on the total amount of the cleaning agent.
  • the upper limit is 100 mass%.
  • the content ratio of the composition of the present disclosure relative to the total amount of the cleaning agent components excluding the propellant gas is in the above-mentioned range.
  • the cleaning agent of the present disclosure may contain a stabilizer, etc., as necessary.
  • the stabilizer may be any of the stabilizers described above.
  • the content of the stabilizer in the cleaning agent of the present disclosure is preferably 5 mass % or less, and more preferably 1 mass % or less, based on the total amount of the cleaning agent.
  • the cleaning agent of the present disclosure may contain other solvents (hereinafter also referred to as solvent (A)) as necessary.
  • the solvent (A) is appropriately selected depending on various purposes such as increasing solubility and adjusting the evaporation rate.
  • Examples of the solvent (A) include hydrocarbons, alcohols, ketones, non-fluorinated ethers, esters, chlorocarbons, HFCs, and HFEs.
  • the content of the solvent (A) in the cleaning agent of the present disclosure is preferably 20 mass % or less, more preferably 10 mass % or less, further preferably 5 mass % or less, and particularly preferably 1 mass % or less, based on the total amount of the cleaning agent.
  • the above compounds may be used for hydrocarbons, alcohols, ketones, non-fluorinated ethers, esters, chlorocarbons, HFCs, and HFEs.
  • the solvent (A) may be one type or two or more types. Furthermore, when two or more types of solvents (A) are included, the combination may be a combination of solvents in the same category, or a combination of solvents in different categories. For example, it may be a combination of two types selected from hydrocarbons, or a combination of one type selected from hydrocarbons and one type selected from alcohols.
  • the solvent (A) is a solvent that does not have a flash point.
  • organic solvents that do not have a flash point include HFCs such as 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, and 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane, and HFEs such as 1,1,2,2-tetrafluoroethoxy-1-(2,2,2-trifluoro)ethane, methoxynonafluorobutane, ethoxynonafluorobutane, methoxyheptafluoropropane, methoxy, 2-(trifluoromethyl)-3-methoxynonafluoropentane, and 2-(trifluoromethyl)-3-ethoxydodecafluorohexane.
  • HFCs such as 1,1,1,2,2,3,4,5,5,5-decafluoropen
  • the composition of the present disclosure can be used as a draining agent.
  • Articles handled in various industrial fields such as automobiles, machines, precision instruments, electricity, electronics, and optics may be washed with water such as pure water in the manufacturing process, or washed with an aqueous cleaner, a quasi-aqueous cleaner obtained by blending an aqueous cleaner with a water-soluble solvent, an alcohol-based cleaner, a glycol ether-based cleaner, a hydrocarbon-based cleaner obtained by blending a surfactant with a hydrocarbon, or the like.
  • a draining process is generally performed after the washing process to remove water with a draining agent.
  • the composition of the present disclosure can be suitably used as a draining agent used in such a draining process.
  • the composition of the present disclosure can be suitably used as a rinse agent to remove the high-boiling-point cleaner attached to the article after the washing process with the high-boiling-point cleaner.
  • the present disclosure also relates to a draining agent comprising the composition or aerosol composition of the present disclosure described above.
  • the draining method is not particularly limited except that the composition of the present disclosure is used as a draining agent, and any conventionally known method can be used. For example, there is a method in which the item to be drained is brought into contact with the composition of the present disclosure and dried.
  • the composition of the present disclosure exhibits a cleaning action as well as a draining action, so that the cleaning process and the draining process can be performed at the same time. That is, by performing the cleaning process, dirt attached to the object to be cleaned can be removed, and moisture that may adhere to the object to be cleaned can be removed. Therefore, it is more productive because it is not necessary to use a cleaning agent and a draining agent separately for the cleaning process and the draining process. Note that this does not prevent the cleaning agent and the draining agent from being used separately for the cleaning process and the draining process, and if desired, the composition of the present disclosure may be used as a cleaning agent and/or a draining agent in each process.
  • the composition of the present disclosure is suitable for cleaning an article (an object to be cleaned) to which dirt containing water (e.g., water-soluble oil) is attached.
  • dirt containing water e.g., water-soluble oil
  • moisture can be removed together with dirt attached to the object to be cleaned.
  • the content of the composition of the present disclosure in the draining agent or rinse agent is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on the total amount of the draining agent or rinse agent.
  • the upper limit is 100% by mass.
  • the content ratio of the composition of the present disclosure relative to the total amount of the draining agent or rinse agent components excluding the propellant gas is preferably within the above-mentioned range.
  • the draining agent or rinsing agent of the present disclosure may contain a stabilizer, other solvents, etc. as necessary. Specific examples of the stabilizer include the stabilizers described above. Examples of the other solvents include the solvent (A) described above.
  • the content of the stabilizer in the draining agent or rinse agent of the present disclosure is preferably 5 mass % or less, and more preferably 1 mass % or less, based on the total amount of the draining agent or rinse agent.
  • the content of other solvents in the draining agent or rinsing agent of the present disclosure is preferably 20 mass % or less, more preferably 10 mass % or less, and even more preferably 5 mass % or less, based on the total amount of the draining agent or rinsing agent.
  • the solvents of the present disclosure include the compositions of the present disclosure.
  • the composition of the present disclosure has excellent solubility for organic substances, and therefore can be used as a solvent for dissolving surface treatment agents such as lubricants, rust inhibitors, moisture-proof coating agents, and antifouling coating agents and applying them to the surface of an article.
  • Articles include, for example, the same articles to which a cleaning agent can be applied.
  • Examples of a method for applying the surface treatment agent to the surface of an article include a method in which a solution of the surface treatment agent, in which the surface treatment agent is dissolved in the solvent of the present disclosure, is applied to the surface of the article, and then the solvent is evaporated to form a coating film on the surface of the article.
  • a solution of the surface treatment agent in which the surface treatment agent is dissolved in the solvent of the present disclosure, is applied to the surface of the article, and then the solvent is evaporated to form a coating film on the surface of the article.
  • it is preferable to dissolve the surface treatment agent so that the concentration of the surface treatment agent becomes 0.01 to 50 mass %, for example.
  • Examples of application methods include application by brush, application by spray, application by immersion, etc.
  • the surface treatment agent may be dissolved in a solvent, and the surface treatment agent solution obtained may be sucked up to apply the surface treatment agent to the inner wall.
  • spray application may be performed in the form of an aerosol in which the surface treatment agent, the solvent of the present disclosure, and liquefied gas or compressed gas are enclosed.
  • Methods for evaporating the solvent include air drying, drying by heating, etc. The drying temperature is preferably 20 to 100°C.
  • the content of the composition of the present disclosure in the solvent of the present disclosure is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on the total amount of the solvent.
  • the upper limit is 100% by mass.
  • the solvent of the present disclosure may contain a stabilizer, other solvents, etc., as necessary. Specific examples of the stabilizer include the stabilizers described above. Examples of the other solvents include the solvent (A) described above.
  • the content of the stabilizer in the solvent of the present disclosure is preferably 5 mass % or less, and more preferably 1 mass % or less, based on the total amount of the solvent.
  • the content of the other solvent in the solvent of the present disclosure is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, based on the total amount of the solvent.
  • the present disclosure also relates to a lubricant solution comprising the composition of the present disclosure described above and a lubricant.
  • a lubricant refers to a substance used to lubricate a friction surface and improve the mechanical efficiency of the friction surface, and is used to reduce friction at the contact surface and prevent heat generation and wear damage when two members move with their surfaces in contact with each other.
  • a lubricant is required to have appropriate viscosity, physical and chemical stability, oiliness, and oxidation stability.
  • the form of the lubricant may be liquid (oil), semi-solid (grease), or solid.
  • Types of lubricants include mineral oil-based lubricants, synthetic oil-based lubricants, fluorine-based lubricants, and silicone-based lubricants.
  • a fluorine-based lubricant or a silicone-based lubricant is preferred because of their excellent solubility or dispersibility in the composition of the present disclosure.
  • Fluorine-based lubricants refer to lubricants that have fluorine atoms in their molecules, and examples of such lubricants include fluorine-based solid lubricants such as fluorine oil, fluorine grease, and polytetrafluoroethylene resin powder.
  • Preferred fluorine oils are perfluoropolyethers (hereinafter also referred to as PFPE) and oligomers of chlorotrifluoroethylene, such as those with the product names "Krytox (registered trademark) GPL102" (manufactured by DuPont Co., Ltd.), "Daifloil #1", “Daifloil #3", “Daifloil #10", “Daifloil #20", “Daifloil #50", “Daifloil #100", and “Demnum S-65” (all manufactured by Daikin Industries, Ltd.), the "Fomblin (registered trademark) Y” series, the “Fomblin (registered trademark) M” series, the “Fomblin (registered trademark) W” series, and the “Fomblin (registered trademark) Z” series (all manufactured by Solvay Specialty Polymers).
  • PFPE perfluoropolyethers
  • Preferable fluorine greases are those that use fluorine oils such as PFPE or oligomers of chlorotrifluoroethylene as a base oil, and are blended with polytetrafluoroethylene powder or other thickeners.
  • fluorine oils such as PFPE or oligomers of chlorotrifluoroethylene as a base oil
  • examples include products with the names “Krytox (registered trademark) Grease 240AC” (manufactured by DuPont), "Daifloil Grease DG-203", “Demnum L65”, “Demnum L100", and “Demnum L200” (all manufactured by Daikin Corporation), “Sumitec F936” (manufactured by Sumitomo Lubricants Co., Ltd.), "Molycoat (registered trademark) HP-300", “Molycoat (registered trademark) HP-500", “Molycoat (registered trademark) HP-870", and “Molycoat (registered
  • silicone-based lubricants refer to lubricants that contain silicone, such as silicone oil and silicone grease.
  • silicone oils include straight silicones, and modified silicones such as reactive silicones and non-reactive silicones. More specifically, straight silicones include dimethyl silicones, methylphenyl silicones, and methylhydrogen silicones, which are bonded with methyl groups, phenyl groups, and hydrogen atoms as substituents.
  • straight silicones include dimethyl silicones, methylphenyl silicones, and methylhydrogen silicones, which are bonded with methyl groups, phenyl groups, and hydrogen atoms as substituents.
  • reactive silicones include amino-modified, epoxy-modified, carboxy-modified, carbinol-modified, methacryl-modified, phenol-modified, and heterogeneous functional group-modified.
  • non-reactive silicones include polyether-modified, methylstyryl-modified, alkyl-modified, higher fatty acid ester-modified, special hydrophilic modified, and fluorine-modified.
  • silicone oils may be one type or a mixture of two or more types.
  • silicone oils include products with the names "Shin-Etsu Silicone KF-96,” “Shin-Etsu Silicone KF-965,” “Shin-Etsu Silicone KF-968,” “Shin-Etsu Silicone KF-99,” “Shin-Etsu Silicone KF-50,” “Shin-Etsu Silicone KF-54,” “Shin-Etsu Silicone HIVACF-4,” “Shin-Etsu Silicone HIVACF-5,” “Shin-Etsu Silicone KF-56A,” and “Shin-Etsu Silicone KF-995" (all manufactured by Shin-Etsu Chemical Co., Ltd.), “SH200” (manufactured by Dow Corning Toray Co., Ltd.), and “MDX4-4159” (manufactured by Dow Corning Corporation).
  • silicone grease products that use the above-mentioned silicone oils as base oils, thickeners such as metal soaps, and various additives are preferred.
  • the lubricant solution may contain one type of lubricant or two or more types.
  • the lubricant solution disclosed herein is environmentally friendly, has excellent lubricant solubility, and dries quickly enough, making it suitable for forming a lubricant coating.
  • the composition of the composition of the present disclosure and the lubricant are not particularly limited and can be appropriately selected as desired.
  • the lubricant is 0.1 mass % or more and 50 mass % or less relative to 100 mass % of the lubricant solution of the present disclosure, but is not limited to this.
  • One embodiment of the present invention is a method for producing an article with a lubricant coating, which comprises applying the lubricant solution of the present disclosure to a surface of an article, and volatilizing a volatile component such as the azeotrope-like composition of the present disclosure, thereby forming a lubricant coating on the surface of the article.
  • the articles may be made of various materials such as metal, resin, elastomer, ceramics, and glass. Examples include industrial equipment in which fluorine-based lubricants are used, CD and DVD tray parts in personal computers and audio equipment, and home and office equipment such as printers, copy machines, and flux machines. In addition, the articles may be suitably used in syringe needles and cylinders, medical tube parts, and the like in which silicone-based lubricants are used.
  • the method for applying the lubricant solution of the present disclosure to the surface of an article is not particularly limited, and examples include application with a brush, application with a spray, and application by immersing the article in the lubricant composition.
  • compositions disclosed herein can also be used as reaction solvents, extractants, drying agents, refrigerants, etc.
  • the composition of the present disclosure can be used as a heat transfer medium for a heat cycle system. It is also preferable to use the above-mentioned aerosol composition instead of the composition of the present disclosure.
  • the present disclosure also relates to a heat transfer medium comprising the composition or aerosol composition of the present disclosure described above.
  • the heat cycle system include a Rankine cycle system, a heat pump cycle system, a refrigeration cycle system, a heat transport system, a secondary circulation cooling system, etc. More specifically, examples of the heat cycle system include refrigeration and freezing equipment, air conditioning equipment, power generation systems, heat transport devices, and secondary cooling machines.
  • a refrigeration cycle system will be described below as an example of a heat cycle system.
  • a refrigeration cycle system is a system in which a heat transfer medium removes thermal energy from a load fluid in an evaporator, thereby cooling the load fluid to a lower temperature.
  • the refrigeration cycle system is a system that includes a compressor that compresses the vapor of the heat transfer medium to produce a high-temperature, high-pressure heat transfer medium vapor, a condenser that cools the compressed vapor of the heat transfer medium to produce a low-temperature, high-pressure heat transfer medium liquid, an expansion valve that expands the liquid of the heat transfer medium discharged from the condenser to produce a low-temperature, low-pressure heat transfer medium liquid, an evaporator that heats the heat transfer medium discharged from the expansion valve to produce a high-temperature, low-pressure heat transfer medium vapor, a pump that supplies the load fluid to the evaporator, and a pump that supplies the load fluid to the condenser.
  • the compositions of the present disclosure can be particularly advantageously used as secondary refrigerants for secondary circulation cooling systems.
  • the secondary circulation cooling system is a system having a primary cooling means for cooling a primary refrigerant made of ammonia or a hydrocarbon refrigerant, a secondary circulation cooling means for circulating the secondary refrigerant for the secondary circulation cooling system to cool the object to be cooled, and a heat exchanger for exchanging heat between the primary refrigerant and the secondary refrigerant to cool the secondary refrigerant.
  • the object to be cooled can be cooled by this secondary circulation cooling system.
  • the heat transfer medium of the present disclosure includes the composition of the present disclosure.
  • the content ratio of the composition of the present disclosure in the heat transfer medium of the present disclosure is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on the total amount of the heat transfer medium.
  • the upper limit can be 100% by mass.
  • the content ratio of the composition of the present disclosure relative to the total amount of the heat transfer medium components excluding the propellant gas is preferably within the above-mentioned range.
  • the heat transfer medium of the present disclosure may contain a stabilizer, other solvents, etc., as necessary.
  • the stabilizer include the stabilizers described above.
  • the other solvents include the solvent (A) described above.
  • the content of the stabilizer in the heat transfer medium of the present disclosure is preferably 5 mass % or less, and more preferably 1 mass % or less, based on the total amount of the heat transfer medium.
  • the content of other solvents in the heat transfer medium of the present disclosure is preferably 20 mass % or less, more preferably 10 mass % or less, and even more preferably 5 mass % or less, based on the total amount of the heat transfer medium.
  • the heat transfer medium of the present disclosure is generally used as a heat transfer medium composition containing the heat transfer medium and a refrigerating machine oil.
  • the refrigerating machine oil may be polyalkylene glycols, polyol esters, polyvinyl ethers, or the like.
  • the content of the refrigerating machine oil in the heat transfer medium composition is preferably 10 to 100 parts by mass, and more preferably 20 to 50 parts by mass, per 100 parts by mass of the heat transfer medium.
  • azeotrope-like composition consisting of 70.01 to 99.99% by weight of (Z)-1-chloro-3,3,3-trifluoropropene and 0.01 to 29.99% by weight of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • Azeotrope-like composition A can be formed from a composition consisting of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether (hereinafter also referred to as HFE-356mmz), in which 1233zd(Z) and HFE-356mmz are present in amounts effective to form an azeotrope-like composition.
  • the present disclosure also relates to an azeotrope-like composition (hereinafter also referred to as “azeotrope-like composition B”) consisting of 0.01 to 28.00 mass % of (Z)-1-chloro-3,3,3-trifluoropropene and 72.00 to 99.99 mass % of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • azeotrope-like composition B consisting of 0.01 to 28.00 mass % of (Z)-1-chloro-3,3,3-trifluoropropene and 72.00 to 99.99 mass % of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.
  • Azeotrope-like composition B can be formed by a composition consisting of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, in which 1233zd(Z) and HFE-356mmz are present in amounts effective to form an azeotrope-like composition.
  • a preferred embodiment of the cleaning agent containing the aerosol composition according to the composition of the present disclosure is a cleaning agent containing the aerosol composition A as a cleaning agent.
  • the azeotrope-like composition A of the present disclosure has excellent solubility for organic substances, and therefore can be used as a solvent for dissolving surface treatment agents such as lubricants, rust inhibitors, moisture-proof coating agents, and stain-proof coating agents, and applying the same to the surface of an article.
  • a preferred embodiment of using the composition of the present disclosure as a solvent is the use of the composition as a solvent for the azeotrope-like composition A.
  • the present disclosure also relates to a heat transfer medium comprising the above-mentioned azeotrope-like composition B of the present disclosure or aerosol composition B.
  • a preferred embodiment of the heat transfer medium comprising the above-mentioned composition of the present disclosure is a heat transfer medium comprising the azeotrope-like composition B.
  • a preferred embodiment of the heat transfer medium comprising the above-mentioned aerosol composition according to the composition of the present disclosure is a heat transfer medium comprising the above-mentioned aerosol composition B.
  • the present disclosure also relates to a composition
  • a composition comprising the azeotrope-like composition A or B of the present disclosure and at least one selected from the group consisting of a stabilizer, a surfactant, a flame retardant, a metal passivator, and a rust inhibitor.
  • the stabilizer, surfactant, flame retardant, metal passivator, and rust inhibitor may be the same as those described above, respectively.
  • the content of at least one component selected from stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 1% by mass or less, based on the total amount of the composition.
  • compositions 1 to 5 and 8 to 11 are examples, and compositions 6 and 7 are comparative examples.
  • compositions 1 to 11 were each prepared using 1233zd(Z) with a water content of 0.0026% by mass and HFE-356mmz with a water content of 0.0359% by mass, and the water content of each composition can be calculated from the contents of 1233zd(Z) and HFE-356mmz.
  • the water content of composition 2 is 0.0043% by mass.
  • Table 1 reveal that when 1233zd(Z) is in the range of 70.01 to 99.99 mass%, 0.01 to 28.00 mass%, and HFE-356mmz is in the range of 0.01 to 29.99 mass%, 72.00 to 99.99 mass%, the composition is an azeotrope-like composition in which the composition of the gas phase and liquid phase does not change substantially. Furthermore, even when it contains 0.0029 to 0.0356 mass% water, the azeotropic property is maintained.
  • Example 2 100 g of cutting oil (Reliacut AM30, manufactured by ENEOS Corporation) was placed in a 200 mL glass beaker. Next, one SUS316 test piece (30 mm x 15 mm x 2 mm) was completely immersed in the cutting oil. When the test piece was removed from the cutting oil and visually inspected, the cutting oil was found to be attached to the surface of the test piece.
  • the cleaning agent was placed in a 300 mL glass beaker, and the SUS test piece with the cutting oil attached was placed so as to be completely immersed, and ultrasonic cleaning was performed at 25°C for 2 minutes (ultrasonic oscillator: Neosonic manufactured by Alex Corporation, output 100 W, frequency 28 kHz).
  • the cleaning agent used was the same as the compositions 1 to 5 prepared in Examples 1-1 to 1-5.
  • the test pieces were taken out and dried at 80° C. for 5 minutes. The surfaces of the test pieces were then visually observed. No stains were observed on the surfaces of the test pieces regardless of which cleaning agent was used.
  • Example 3 100 g of cutting oil (Daphne Mag Plus S, manufactured by Idemitsu Kosan Co., Ltd.) was placed in a 200 mL glass beaker. Next, one SUS316 test piece (30 mm x 15 mm x 2 mm) was completely immersed in the cutting oil. When the test piece was removed from the cutting oil and visually inspected, the cutting oil was found to be attached to the surface of the test piece.
  • cutting oil Daphne Mag Plus S, manufactured by Idemitsu Kosan Co., Ltd.
  • cleaning agent 200 g was placed in a 300 mL glass beaker, and the SUS test piece with the cutting oil attached was placed so as to be completely immersed, and ultrasonic cleaning was performed at 25°C for 2 minutes (ultrasonic oscillator: Neosonic manufactured by Alex Corporation, output 100 W, frequency 28 kHz).
  • the test pieces were then removed and dried at 80° C. for 5 minutes, and the surfaces of the test pieces were visually observed. No stains were observed on the surfaces of the test pieces regardless of which cleaning agent was used.
  • Example 4 The components were mixed so that the ratio of 1233zd(Z)/HFE-356mmz/HFIP was 95.00% by mass/4.99% by mass/0.01% by mass to prepare a composition.
  • a cleaning test was carried out in the same manner as in Example 2. As a result, similar to Example 2, no stains were observed on the surface of the test piece.
  • the composition difference between the gas phase and liquid phase of 1233zd(Z) and HFE-356mmz was 8.00 mass% or less, respectively. Therefore, the composition is an azeotrope-like composition.
  • composition disclosed herein has a small impact on the global environment and is unlikely to undergo compositional changes even when repeatedly evaporated and condensed, making it suitable for a wide range of applications, including as a cleaning agent, solvent, aerosol, and heat transfer medium.

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  • Organic Chemistry (AREA)
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Abstract

La présente divulgation concerne : une composition de type azéotrope contenant du (Z)-1-chloro-3,3,3-trifluoropropène et du 1,1,1,3,3,3-hexafluoroisopropyl-méthyl-éther ; une composition d'aérosol, un agent de nettoyage, une solution lubrifiante et un milieu de transfert de chaleur qui contiennent ladite composition de type azéotrope ; un procédé de production d'une composition ; une composition ; un procédé de nettoyage utilisant ledit agent de nettoyage ; et un procédé de récupération.
PCT/JP2024/029319 2023-08-21 2024-08-19 Composition de type azéotrope, composition d'aérosol, agent de nettoyage, solution lubrifiante, milieu de transfert de chaleur, procédé de production de composition, composition, procédé de nettoyage et procédé de récupération Pending WO2025041739A1 (fr)

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JP2023-134119 2023-08-21

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008053656A1 (fr) * 2006-11-01 2008-05-08 Central Glass Company, Limited Composition azéotrope ou analogue à un azéotrope comprenant du 1,1,2,2-tétrafluoro-1-méthoxyéthane
JP2013249326A (ja) * 2012-05-30 2013-12-12 Central Glass Co Ltd フルオロアルケンを含有する熱伝達媒体
JP2014005419A (ja) * 2012-06-27 2014-01-16 Central Glass Co Ltd フッ素化エーテルを含む熱伝達作動媒体
JP2017043742A (ja) * 2015-08-28 2017-03-02 旭硝子株式会社 溶剤組成物
JP2017200989A (ja) * 2016-04-27 2017-11-09 神戸合成株式会社 洗浄剤組成物及びそのエアゾール組成物
JP2020132688A (ja) * 2019-02-14 2020-08-31 セントラル硝子株式会社 溶剤組成物
JP2022093150A (ja) * 2020-12-11 2022-06-23 株式会社カネコ化学 洗浄用溶剤組成物
WO2022215570A1 (fr) * 2021-04-09 2022-10-13 セントラル硝子株式会社 Composition, agent de nettoyage comprenant la composition, composition d'aérosol, agent de déshydratation, agent moussant ou milieu de transfert de chaleur, système utilisant le milieu de transfert de chaleur, et procédé de nettoyage d'article

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008053656A1 (fr) * 2006-11-01 2008-05-08 Central Glass Company, Limited Composition azéotrope ou analogue à un azéotrope comprenant du 1,1,2,2-tétrafluoro-1-méthoxyéthane
JP2013249326A (ja) * 2012-05-30 2013-12-12 Central Glass Co Ltd フルオロアルケンを含有する熱伝達媒体
JP2014005419A (ja) * 2012-06-27 2014-01-16 Central Glass Co Ltd フッ素化エーテルを含む熱伝達作動媒体
JP2017043742A (ja) * 2015-08-28 2017-03-02 旭硝子株式会社 溶剤組成物
JP2017200989A (ja) * 2016-04-27 2017-11-09 神戸合成株式会社 洗浄剤組成物及びそのエアゾール組成物
JP2020132688A (ja) * 2019-02-14 2020-08-31 セントラル硝子株式会社 溶剤組成物
JP2022093150A (ja) * 2020-12-11 2022-06-23 株式会社カネコ化学 洗浄用溶剤組成物
WO2022215570A1 (fr) * 2021-04-09 2022-10-13 セントラル硝子株式会社 Composition, agent de nettoyage comprenant la composition, composition d'aérosol, agent de déshydratation, agent moussant ou milieu de transfert de chaleur, système utilisant le milieu de transfert de chaleur, et procédé de nettoyage d'article

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