Azeotrope-like composition, aerosol composition, cleaning agent, lubricant solution, heat transfer medium, method for producing composition, composition, cleaning method, and recovery method

Abstract

The present disclosure provides: an azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether; an aerosol composition, a cleaning agent, a lubricant solution and a heat transfer medium which contain said azeotrope-like composition; a method for producing a composition; a composition; a cleaning method using said cleaning agent; and a recovery method.

Description

Azeotrope-like compositions, aerosol compositions, cleaning agents, lubricant solutions, heat transfer media, methods of making compositions, compositions, cleaning methods, and recovery methods

[0001] The present disclosure relates to an azeotrope-like composition that has a small impact on the global environment and is resistant to compositional changes even when repeatedly evaporated and condensed, an aerosol composition, a cleaning agent, a lubricant solution, and a heat transfer medium containing 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.

[0002] Conventionally, chlorofluorocarbons (hereinafter referred to as "CFCs"), hydrochlorofluorocarbons (hereinafter referred to as "HCFCs"), and hydrofluorocarbons (hereinafter referred to as "HFCs") are non-flammable and have excellent stability, drying properties, etc., and therefore have been used in a variety of applications such as cleaning agents, solvents, heat transfer media, foaming agents, and fire extinguishing agents. However, there are concerns about the impact of CFCs, HCFCs, and HFCs on the ozone layer and global warming. Fluoroolefins have been proposed as alternatives to CFCs, HCFCs, and HFCs. Fluoroolefins have a carbon-carbon double bond in their molecules, and therefore have a short lifespan in the atmosphere and little impact on the global environment.

[0003] However, when fluoroolefins are used alone for the above applications, the desired performance may not be fully exhibited in some cases. To solve such problems, the use of fluoroolefins in combination with other components depending on the purpose has been investigated. For example, Patent Document 1 proposes a composition containing monochlorotrifluoropropene (HCFO-1233) and an additional component. Furthermore, 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.

[0004] International Publication No. 2011 / 031697 Japanese Patent Application Laid-Open No. 2020-132688

[0005] However, when multiple components are used in combination, the boiling points of the components differ, which can cause the composition to change during use and prevent sufficient performance from being achieved. The present disclosure aims to provide an azeotrope-like composition that has a small impact on the global environment and is resistant to compositional changes even when repeatedly evaporated and condensed. The present disclosure also aims to provide an aerosol composition, a cleaning agent, a lubricant solution, and a heat transfer medium containing the azeotrope-like composition, as well as a method for producing the composition, the composition, a cleaning method using the cleaning agent, and a recovery method.

[0006] As a result of extensive investigations, the present inventors have found that the above problems can be solved by the following means.

[0007] [1] An azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. [2] The azeotrope-like composition according to [1], which consists of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. [3] The azeotrope-like composition according to [1] or [2], 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, relative to the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, or 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, relative to the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. [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, relative to the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.[6] The azeotrope-like composition according to any one of [1] to [5], wherein the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether is 80% by mass or more based on the total amount of the composition. [7] The azeotrope-like composition according to any one of [1] and [3] to [6], further comprising water. [8] The azeotrope-like composition according to [7], comprising 0.0001 to 1.00% by 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. [9] The azeotrope-like composition according to [7] or [8], consisting of (Z)-1-chloro-3,3,3-trifluoropropene, 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, and water.

[10] A method for producing a composition, comprising the steps of preparing an azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, and adding at least one selected from the group consisting of stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors to the azeotrope-like composition.

[11] 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 stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors.

[12] An aerosol composition comprising the azeotrope-like composition according to any one of [1] to [9] and a propellant gas.

[13] A cleaning agent comprising the azeotrope-like composition according to any one of [1] to [9].

[14] A cleaning agent comprising the aerosol composition according to

[12] .

[15] The cleaning agent according to

[13] or

[14] , which is for cleaning vehicles or transportation means.

[16] A method for cleaning an article, comprising a step of contacting the cleaning agent according to

[13] or

[14] with an article to be cleaned.

[17] A method for recovering a cleaning agent, comprising a step of cleaning an article with the cleaning agent according to

[13] or

[14] , and a step of purifying the cleaning agent after cleaning.

[18] A lubricant solution, comprising the azeotrope-like composition according to any one of [1] to [9], and a lubricant.

[19] A heat transfer medium comprising the azeotrope-like composition according to any one of [1] to [9] or the aerosol composition according to

[12] .

[0008] The present disclosure can provide an azeotrope-like composition that has a small impact on the global environment and is resistant to compositional changes even when repeatedly evaporated and condensed.The present disclosure also provides an aerosol composition, a cleaning agent, a lubricant solution, and a heat transfer medium containing the azeotrope-like composition, as well as a method for producing the composition, the composition, a cleaning method using the cleaning agent, and a recovery method.

[0009] In this specification, for halogenated hydrocarbons, the abbreviation for the compound is written in parentheses after the compound name, but in this specification, this abbreviation will be used in place of the compound name as necessary. Also, the abbreviation may use only the number and lowercase alphabet portion following the hyphen (-) (e.g., "1233zd" for "HCFO-1233zd"). Furthermore, in the names and abbreviations of compounds having geometric isomers, the (E) attached to the compound's name indicates the E-form, and the (Z) attached to the abbreviation indicates the Z-form (e.g., "(Z)-1-chloro-3,3,3-trifluoropropene" may be used as "HCFO-1233zd(Z)" or "1233zd(Z)"). When the E-form or the Z-form is not specified in the name or abbreviation of the compound, the name or abbreviation collectively refers to the E-form, the Z-form, and a mixture of the E- and Z-forms.

[0010] In this specification, a compound in which some of the hydrogen atoms of a saturated hydrocarbon compound have been replaced with fluorine atoms is referred to as hydrofluorocarbon (HFC), a compound in which some of the hydrogen atoms of a saturated hydrocarbon compound have been replaced with fluorine atoms and chlorine atoms is referred to as hydrochlorofluorocarbon (HCFC), a compound in which all of the hydrogen atoms of a saturated hydrocarbon compound have been replaced with fluorine atoms and chlorine atoms is referred to as chlorofluorocarbon (CFC), a compound having a carbon-carbon double bond and composed of carbon, fluorine, and hydrogen atoms is referred to as hydrofluoroolefin (HFO), and a compound having a carbon-carbon double bond and composed of carbon, chlorine, fluorine, and hydrogen atoms is referred to as hydrochlorofluoroolefin (HCFO).

[0011] In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits.

[0012] [Azeotropic Composition or Azeotrope-Like Composition] Before describing the composition of the present disclosure, azeotropic compositions and azeotrope-like compositions will be described. Fluorine-containing olefins are highly compatible with various solvents, making it easy to prepare homogeneous compositions. However, such simple compositions inherently suffer from the problem of "liquid composition susceptibility to fluctuation." That is, even if multiple types of liquids are mixed and compatibility is ensured, the problem of liquid composition susceptibility to fluctuation due to differences in volatility of each component is unavoidable. For example, when a binary liquid composition is placed in an ultrasonic cleaner and used as a cleaning agent, generally, highly volatile low-boiling-point components (components with high vapor pressure) volatilize preferentially, and low-volatility high-boiling-point components are concentrated in the cleaning tank. For example, in the case of a composition containing a low-boiling-point component with high detergency and a high-boiling-point component with low detergency, the concentration of the low-boiling-point component in the cleaning liquid decreases over time, which may cause poor cleaning. In particular, when a non-flammable composition is prepared by blending a flammable solvent with a non-flammable solvent, the cleaning liquid may become a flammable composition if the non-flammable component volatilizes preferentially.

[0013] Furthermore, from the viewpoints of both environmental protection and economy, it is desirable to recover and reuse the cleaning solvent after use by an operation such as distillation. However, in the case of a two-component liquid, the two component liquids, which generally have different boiling points, must be recovered separately, and recovery and reuse can easily impose an operational burden.

[0014] The same problem occurs when used as a working fluid in a thermodynamic cycle. That is, even when used as a working fluid in a thermodynamic cycle, the liquid composition may change over time. If the liquid composition changes, the heat capacity, viscosity, or affinity with the lubricant of the liquid may change, which may result in a deterioration in the operating performance of the thermodynamic cycle.

[0015] Therefore, when using a binary (multi-component) liquid composition as a cleaning agent or working fluid, the liquid composition must be frequently analyzed, and the liquid must be constantly mixed in the appropriate ratio to maintain the appropriate composition range, and volatilized components must be replenished. However, such liquid composition management can be a significant workload.

[0016] In contrast, an azeotropic composition evaporates with the same composition as the liquid, making it a very desirable composition whose liquid composition does not change during use. In this specification, "azeotrope" refers to an azeotrope in the strict thermodynamic sense. For example, in the case of a water / ethanol mixture, 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 identical to the liquid composition. This phenomenon is called "azeotropy." At a specific temperature and pressure, the composition of an azeotropic composition is unique.

[0017] "Azeotrope-like," also known as "quasi-azeotrope," refers to a phenomenon in which, although not strictly azeotropic from a thermodynamic perspective, for liquids within a certain range of compositions, the liquid composition is substantially equal to the composition of the gas in equilibrium. Even if the compositions of the gas and liquid phases do not completely match, those skilled in the art can treat it as an azeotropic composition as long as the compositions of the gas and liquid phases are substantially the same. In this case, the smaller the difference in vapor-liquid equilibrium composition between the gas and liquid phases, the better. For example, in a binary system composition, the difference in composition between the gas and liquid phases of one component is preferably 8.00% by mass or less, more preferably 7.00% by mass or less, and particularly preferably 4.00% by mass or less. This phenomenon in which the vapor-liquid equilibrium compositions of the gas and liquid phases substantially match is called azeotrope-like or pseudo-azeotrope, and such a composition is called an azeotrope-like composition or pseudo-azeotropic composition. Furthermore, a composition having an azeotrope-like composition (or pseudo-azeotropic composition) is called an azeotrope-like composition (or pseudo-azeotropic composition). The phrase "it is sufficient if the gas-liquid equilibrium compositions of the gas phase and liquid phase are substantially the same" means that the difference in gas-liquid equilibrium composition between the gas phase and liquid phase is small, and when the composition of the present disclosure is a binary (or ternary or higher) composition, the difference in composition between the gas phase and 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 each 8.00% by mass or less, and the above composition difference is preferably 7.00% by mass or less, and more preferably 4.00% by mass or less.

[0018] The term "azeotrope-like" is not theoretically derived, but is discovered only when vapor-liquid equilibrium is experimentally investigated for various types and composition ratios of liquids, and by chance the composition of the vapor phase and the composition of the liquid phase are found to be substantially identical. In the present invention, a vapor-liquid equilibrium experiment was conducted on 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 were substantially identical was found. The vapor-liquid equilibrium experiment was specifically conducted based on the <Measurement of Vapor-Liquid Equilibrium> described in the Examples.

[0019] [Composition] The 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 composition of the present disclosure may consist solely of HFE-356mmz and 1233zd(Z). Hereinafter, in this specification, unless otherwise specified, reference to the "composition of the present disclosure" refers to an azeotrope-like composition containing 1233zd(Z) described below and HFE-356mmz described below. Specifically, 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. In a composition of 1233zd(Z) and HFE-356mmz, the compositions of the gas phase and liquid phase are close in composition within this composition range, and therefore composition fluctuations are unlikely to occur. More preferably, 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. More preferably, 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. In this composition range, the compositions of the gas phase and liquid phase are closer to each other, making composition fluctuation less likely to occur.

[0020] Specifically, 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. In a composition of 1233zd(Z) and HFE-356mmz, the compositions of the gas phase and liquid phase are close in composition within this composition range, and therefore composition fluctuations are unlikely to occur. More preferably, 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. More preferably, 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. In this composition range, the compositions of the gas phase and liquid phase are closer to each other, making composition fluctuation less likely to occur.

[0021] In the composition of the present disclosure, the total amount of 1233zd(Z) and HFE-356mmz 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 composition. The composition of the present disclosure may be composed essentially of 1233zd(Z) and HFE-356mmz. "The composition of the present disclosure is composed essentially of 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% by mass or more, based on the total amount of the composition. In addition, in one preferred embodiment, the composition of the present disclosure is preferably composed only of 1233zd(Z) and HFE-356mmz.

[0022] The composition of the present disclosure contains 80% by mass or more of 1233zd(Z) and HFE-356mmz in total, and therefore has a small impact on the global environment, undergoes only small changes in composition when repeatedly evaporated and condensed, and can be handled in a manner almost equivalent 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 being able to obtain stable performance equivalent to the above-mentioned azeotrope-like composition.

[0023] [1233zd(Z)] 1233zd(Z) is an olefin having a carbon-carbon double bond, and therefore has a short lifetime in the atmosphere and low ozone depletion potential and global warming potential. 1233zd(Z) has a boiling point of 39°C, making it suitable for use on heat-sensitive components. Furthermore, 1233zd(Z) has no flash point, excellent drying properties, and excellent penetration due to its low surface tension and viscosity, making it an excellent cleaning agent and solvent. Furthermore, 1233zd(Z) has low viscosity, resulting in low resistance when passing through piping, excellent transport properties, and excellent performance as a heat transfer medium. 1233zd(Z) can be produced, for example, based on the description in JP 2017-110020 A.

[0024] By containing 1233zd(Z) in the above-mentioned amounts, each composition of the present disclosure has a small impact on the global environment and can exhibit performance suitable for various applications such as cleaning agents, solvents, aerosols, and heat transfer media.

[0025] [1,1,1,3,3,3-Hexafluoroisopropyl methyl ether] 1,1,1,3,3,3-Hexafluoroisopropyl methyl ether (HFE-356mmz) has a boiling point of approximately 51°C and can be used on heat-sensitive components. Furthermore, HFE-356mmz has excellent drying properties and excellent penetration due to its low surface tension and viscosity, making it an excellent cleaning agent and solvent. Furthermore, due to its low viscosity, HFE-356mmz has low resistance when passing through piping, excellent transport properties, and excellent performance as a heat transfer medium. Furthermore, HFE-356mmz has minimal impact on resin materials such as acrylonitrile-butadiene-styrene copolymer resin (hereinafter also referred to as ABS resin), polycarbonate (PC), and polystyrene resin (PS). 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).

[0026] By including HFE-356mmz in the above-mentioned amount, the composition of the present disclosure has excellent performance in various aspects, such as cleaning properties, solubility, transport properties, etc. Furthermore, while 1233zd(Z) may cause strong chemical attack (erosion) on resins and the like when used alone, its combined use with HFE-356mmz can reduce chemical attack.

[0027] The composition of the present disclosure may contain water. Even when containing water, the composition of the present disclosure can form an azeotrope-like composition. 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%, relative to the total amount of 1233zd(Z) and HFE-356mmz. The inclusion of water has the effect of improving the cleaning performance for water-soluble processing oils.

[0028] In one preferred embodiment, 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.

[0029] The composition of the present disclosure may further contain other components, such as 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 purification processes of 1233zd(Z) and HFE-356mmz.

[0030] The hydrocarbon is preferably a hydrocarbon having 5 or more carbon atoms. The hydrocarbon may be linear or cyclic, and may be saturated or unsaturated. Preferred hydrocarbons are n-pentane, cyclopentane, n-hexane, cyclohexane, and n-heptane.

[0031] The alcohol is preferably an alcohol having 1 to 16 carbon atoms. The alcohol may be chain or cyclic, and may be saturated or unsaturated. The alcohol is preferably methanol, ethanol, or isopropyl alcohol.

[0032] The ketone is preferably a ketone having 3 to 9 carbon atoms. The ketone may be a chain or cyclic ketone, and may be a saturated or unsaturated ketone. Preferred ketones are acetone and methyl ethyl ketone.

[0033] The non-fluorinated ether is preferably an ether having 2 to 8 carbon atoms. The non-fluorinated ether may be linear or cyclic, and may be a saturated or unsaturated ether. Preferred ethers are diethyl ether, diisopropyl ether, and tetrahydrofuran.

[0034] The ester is preferably an ester having 2 to 19 carbon atoms. The ester may be linear or cyclic, and may be a saturated ester or an unsaturated ester. The ester is preferably methyl acetate or ethyl acetate.

[0035] The chlorocarbon is preferably a chlorocarbon having 1 to 3 carbon atoms. The chlorocarbon may be chain or cyclic, and may be saturated or unsaturated. The chlorocarbon is more preferably methylene chloride, trans-1,2-dichloroethylene, or trichloroethylene.

[0036] 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. Preferred HFCs include 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.

[0037] As the HFE, an HFE other than 1,1,1,3,3,3-hexafluoroisopropyl methyl ether is preferred, for example, 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 O.C. 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 )CF ３ , hereinafter also referred to as HFE-7300), 2-(trifluoromethyl)-3-ethoxydodecafluorohexane (C ３ F ７ CF (OC ２ H ５ )CF(CF ３ )CF ３ (hereinafter also referred to as HFE-7500), 1,1,2,3,3,3-hexafluoropropyl methyl ether (HFE-356mec), and the like are preferred.

[0038] In addition, raw materials, materials, 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), chlorotrifluoropropane ...1223), chloropentafluoropropane (HCFC-235), chlorotrifluoropropane (HCFO-1223), chlorotetrafluoropropane (HCFC-1223), chloropentafluoropropane (HCFC-1223), chlorotetrafluoropropane (HCFC-1223), chloropentafluoropropane (HCFC-1223), chlorotetrafluoropropane (HCFC-1223), chloropentafluoropropane (HCFC-1223), chlorotetrafluoropropane (HCFC-1223), chloropentafluoro dichlorotetrafluoropropene (HCFO-1224), dichlorotetrafluoropropene (HCFO-1214), pentafluoropropane (HFC-245), tetrafluoropropene (HFO-1234), trifluoropropyne, water, hexafluoropropene, tetrafluoroethylene, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), dimethyl ether, halomethanes, and methyl paratoluenesulfonate, paratoluenesulfonic acid, paratoluenesulfonic acid salts, C ４ H ３ F ５ O and 2,2,2-trifluoroethyl methyl ether. When these components have geometrical isomers or positional isomers, any of the isomers may be used as a single component or a mixture.

[0039] 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.

[0040] [Compositions Comprising Azeotrope-Like Compositions] The present disclosure also relates to compositions comprising the azeotrope-like composition of the present disclosure described above and at least one selected from the group consisting of stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors. When used in various applications, compositions comprising the azeotrope-like composition of the present disclosure and at least one of the additives described above have the advantage of providing stable performance equivalent to that of the azeotrope-like composition.

[0041] The content of at least one component selected from stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors is preferably 20 mass% or less, more preferably 10 mass% or less, even more preferably 5 mass% or less, and particularly preferably 1 mass% or less, relative to the total amount of the composition.

[0042] Stabilizers include nitromethane, nitroethane, nitropropane, nitrobenzene, diethylamine, triethylamine, isopropylamine, diisopropylamine, butylamine, isobutylamine, tert-butylamine, α-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, Examples of such an alkyl acrylate include 2,6-di-tert-butyl-p-cresol, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 1,2,3-benzotriazole, 1-[(N,N-bis-2-ethylhexyl)aminomethyl]benzotriazole, 1,2-propylene oxide, 1,2-butylene oxide, 1,4-dioxane, butyl glycidyl ether, phenyl glycidyl ether, isoamylene, octene, 2,4,4-trimethyl-1-pentene, 2,4,4-trimethyl-2-pentene, and 2-methylpentene. Among these, 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. One type of stabilizer may be used, or two or more types may be used.

[0043] Preferred surfactants include sorbitan aliphatic esters such as sorbitan monooleate and sorbitan trioleate; polyoxyethylene sorbit fatty acid esters such as polyoxyethylene sorbit tetraoleate; polyethylene glycol fatty acid esters such as polyoxyethylene monolaurate; polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether; polyoxyethylene alkylphenyl ethers such as polyoxyethylene nonylphenyl ether; and polyoxyethylene alkylamine fatty acid amides such as polyoxyethylene oleic acid amide. One or more types of surfactants may be used.

[0044] Preferred flame retardants include phosphates, halogenated aromatic compounds, fluorinated iodocarbons, fluorinated bromocarbons, etc. One type of flame retardant may be used, or two or more types may be used.

[0045] The compositions of the present disclosure described above have a small impact on the global environment, are resistant to compositional changes even when repeatedly evaporated and condensed, and exhibit excellent performance suitable for a variety of applications, such as cleaning agents, solvents, aerosols, and heat transfer media. 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, and composite materials thereof. Among these, metals such as iron, copper, nickel, gold, silver, and platinum, sintered metals, glass, fluororesins, polyimides, polyphenylene sulfide, liquid crystal polymers, and engineering plastics such as PEEK are preferred.

[0046] (Method for Producing a Composition) The present disclosure also relates to a method for producing a composition, comprising the steps of: preparing an azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether; and 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. Examples of the stabilizer, surfactant, flame retardant, metal passivator, and rust inhibitor include the stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors described above.

[0047] The content of at least one component selected from stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors is preferably 20 mass% or less, more preferably 10 mass% or less, even more preferably 5 mass% or less, and particularly preferably 1 mass% or less, relative to the total amount of the composition.

[0048] [Aerosol and aerosol composition] 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 has a pressure of atmospheric pressure (1.013 x 10) at 0°C. ５ The pressure is preferably 100 Pa or more. As the propellant gas, a liquefied gas or a compressed gas can be used. Examples include 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, etc., and these can be used alone or in combination of two or more. For example, air can also be suitably used. As the propellant gas, either a liquefied gas or a compressed gas can be used, or a combination of a liquefied gas and a compressed gas can be used.

[0049] The aerosol of the present disclosure is filled with the composition of the present disclosure and a propellant gas. The composition of the present disclosure may be filled in a container together with the propellant gas, or may be filled in a container separately from the propellant gas. The propellant gas contained in the aerosol preferably has an internal pressure of 0.2 to 1 MPa at 35°C when sealed in a nebulizer.

[0050] 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 the container separately from the composition of the present disclosure and the propellant gas. Examples of the solute include surface treatment agents such as lubricants, rust inhibitors, moisture-proof coating agents, and antifouling coating agents. When filling the aerosol with a solute, it is preferable to fill the aerosol so that the concentration of the solute is 0.01 to 50 mass % relative to the total of the composition of the present disclosure and the solute.

[0051] The aerosol of the present disclosure may contain a stabilizer, other solvents, etc., as necessary. Specific examples of stabilizers include the stabilizers described above. Examples of 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, 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.

[0052] [Cleaning Agent] The composition of the present disclosure has excellent cleaning properties and can be used as a cleaning agent for degreasing, flux removal, precision cleaning, draining, rinsing, 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 containing the above-mentioned composition of the present disclosure or the aerosol composition.

[0053] Examples of articles to which the cleaning agent of the present disclosure can be applied include optical components, 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, and glass substrates. Examples of medical instruments include catheters and syringe needles. The cleaning agent of the present disclosure can also be applied to various parts such as brakes, wheels, and suspensions in various vehicles and transportation such as automobiles, bicycles, construction machinery, aircraft, and railway vehicles, and can be suitably used as a so-called brake cleaner or parts cleaner. In other words, the cleaning agent of the present disclosure is also preferably used for cleaning vehicles or transportation.

[0054] The cleaning method is not particularly limited, but one method for cleaning an article involves contacting the cleaning agent of the present disclosure with the article to be cleaned and removing dirt adhering to the article. The present disclosure also relates to a method for cleaning an article, including a step of contacting the cleaning agent of the present disclosure with the article to be cleaned. Examples include immersing the article to be cleaned in the cleaning agent of the present disclosure and rinsing the dirt, wiping with a rag, or spray cleaning, and these methods may be used in combination. Placing the cleaning agent of the present disclosure in an ultrasonic cleaner, immersing the article to be cleaned in the solution, and performing ultrasonic cleaning is a particularly preferred embodiment. Another preferred embodiment is spray cleaning, for example, spraying a cleaning agent containing the above-described aerosol composition onto various articles to be cleaned. It is expected that water will gradually be incorporated into the composition during use in an open system. The azeotrope-like composition of the present disclosure exhibits azeotropic properties even when containing water, thereby achieving the aforementioned effects.

[0055] 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. Examples of processing oil 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 detergency and is therefore particularly suitable for use in cleaning processing oil, pitch, and asphalt.

[0056] In the above-described cleaning method, cleaning conditions such as contact time with the article and temperature can be appropriately selected depending on the cleaning method. Also, a known cleaning device can be appropriately selected. For example, the method and cleaning device described in WO 2008 / 149907 can be used.

[0057] As described above, the composition of an azeotrope-like composition hardly changes even when used in an open system, and therefore, a cleaning agent using the composition of the present disclosure containing such a composition exhibits stable detergency without the need for frequent composition control, which is a great practical advantage.

[0058] The cleaning agent can be recovered by the following process. The method for recovering the cleaning agent is not particularly limited, but includes the step of cleaning an article using the cleaning agent of the present disclosure and the 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 examples thereof include the following distillation operation. Distillation operation can separate and remove oils and foreign matter (particles), allowing the cleaning agent of the present disclosure (as an example, the azeotrope-like composition constituting the cleaning agent) to be recovered. Since distillation recycling devices for general cleaning agents are simple distillation systems, an azeotrope-like composition consisting of 1233zd(Z) and HFE-356mmz can be recycled using a commercially available distillation recycling device with substantially no change in composition. In particular, azeotrope-like compositions are preferred because no change in composition occurs even when a distillation column with a large number of plates is used.

[0059] During the distillation operation, the two liquid components, 1233zd(Z) and HFE-356mmz, maintain the properties of an azeotrope-like composition, so the recovered liquid can be reused as a cleaning solvent without undergoing extensive composition adjustment. Note that when the composition of the present disclosure contains the above-mentioned "other components," these "other components" may be removed by distillation, and in such cases, it is desirable to supplement them separately.

[0060] One of the substances removed (or reduced) by a cleaning agent is water. Removing (or reducing) water is also called draining cleaning. The method of draining cleaning is not particularly limited, and a conventionally known method can be used. For example, a method of contacting an item to be drained with the composition of the present disclosure and drying it can be used. As mentioned above, it is also preferable to use the above-mentioned aerosol composition instead of the composition of the present disclosure. In addition, in one preferred embodiment, the cleaning agent can be suitably used as a rinse agent to remove high-boiling-point detergent adhering to an item after a cleaning process with the high-boiling-point detergent. In this case, the cleaning agent is preferably a rinse agent.

[0061] The content of the composition of the present disclosure in the cleaning agent 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 cleaning agent. The upper limit may be 100% by mass. When the cleaning agent contains an aerosol composition, the content of the composition of the present disclosure relative to the total amount of cleaning agent components excluding the propellant gas is preferably within the above-mentioned range.

[0062] The cleaning agent of the present disclosure may contain a stabilizer or the like as needed. 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% by mass or less, more preferably 1% by mass or less, based on the total amount of the cleaning agent.

[0063] The cleaning agent of the present disclosure may contain other solvents (hereinafter also referred to as solvent (A)) as needed. The solvent (A) is appropriately selected depending on various purposes, such as increasing solubility or 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, still more preferably 5 mass% or less, and particularly preferably 1 mass% or less, based on the total amount of the cleaning agent. For hydrocarbons, alcohols, ketones, non-fluorinated ethers, esters, chlorocarbons, HFCs, and HFEs, the above-mentioned compounds may be used.

[0064] The solvent (A) may be one type or two or more types. When two or more types of solvents (A) are contained, the combination may be a combination of solvents from the same category or a combination of solvents from 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.

[0065] It is more preferable that the solvent (A) is a solvent that does not have a flash point. Examples of 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. When a solvent that has a flash point is used as the solvent (A), it is preferably used within a range that does not have a flash point as a cleaning agent.

[0066] [Draining Agent, Rinse Agent] The composition of the present disclosure can be used as a draining agent. Articles used in various industrial fields, such as automobiles, machinery, precision instruments, electrical, electronics, and optics, are sometimes cleaned with water, such as pure water, during their manufacturing process, or with aqueous cleaners, semi-aqueous cleaners in which an aqueous cleaner is blended with a water-soluble solvent, alcohol-based cleaners, glycol ether-based cleaners, hydrocarbon cleaners in which a hydrocarbon is blended with a surfactant, and the like. When aqueous or semi-aqueous cleaners are used, water adheres to the article after cleaning, and a draining process is generally performed after the cleaning process to remove the water using a draining agent. The composition of the present disclosure can be suitably used as a draining agent for such a draining process. Similarly, the composition of the present disclosure can be suitably used as a rinse agent to remove high-boiling-point cleaners adhering to articles after a cleaning process with the high-boiling-point cleaner. 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 draining agent containing the above-mentioned composition of the present disclosure or the aerosol composition.

[0067] The method for draining water 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, a method in which an article to be drained is brought into contact with the composition of the present disclosure and then dried.

[0068] In some embodiments, the composition of the present disclosure exhibits both cleaning and draining properties, allowing the cleaning process and draining process to be carried out simultaneously. That is, by carrying out the cleaning process, dirt adhering to the object to be cleaned can be removed, and moisture that may adhere to the object to be cleaned can also be removed. Therefore, it is not necessary to use a detergent and a draining agent separately in the cleaning process and the draining process, which is more productive. Note that this does not preclude the detergent and draining agent used in the cleaning process and the draining process from being used separately, and if desired, the composition of the present disclosure may be used as a detergent and / or a draining agent in each process. In some embodiments, the composition of the present disclosure is suitable for cleaning an article (an article to be cleaned) having moisture-containing soiling (e.g., water-soluble oil) attached thereto. By using the composition of the present disclosure, moisture can be removed along with dirt adhering to the article to be cleaned.

[0069] The content of the composition of the present disclosure in the draining agent or rinse 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. The upper limit can be 100% by mass. When the draining agent or rinse contains an aerosol composition, the content of the composition of the present disclosure relative to the total amount of the draining agent or rinse components excluding the propellant gas is preferably within the above-mentioned range. The draining agent or rinse may contain a stabilizer, other solvents, etc. as needed. Specific examples of stabilizers include the stabilizers described above. Examples of other solvents include solvent (A) described above. The content of the stabilizer in the draining agent or rinse is preferably 5% by mass or less, more preferably 1% by mass or less, based on the total amount of the draining agent or rinse. The content of other solvents in the draining agent or rinse aid 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 draining agent or rinse aid.

[0070] [Solvent] The solvent of the present disclosure includes the composition 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. Examples of the article include the same articles to which a cleaning agent can be applied.

[0071] A method for applying the surface treatment agent to the surface of an article includes applying a solution of the surface treatment agent to the surface of the article, in which the surface treatment agent is dissolved in the solvent of the present disclosure, and then evaporating the solvent to form a coating film on the surface of the article. When dissolving the surface treatment agent in the solvent of the present disclosure, it is preferable to dissolve the surface treatment agent so that the concentration of the surface treatment agent is 0.01 to 50 mass %, for example.

[0072] Examples of application methods include brush application, spray application, and immersion application. When the article is tubular, the surface treatment agent may be dissolved in a solvent and the resulting solution may be sucked up and applied to the inner wall. Alternatively, spray application may be performed in the form of an aerosol containing the surface treatment agent, the solvent of the present disclosure, and a liquefied or compressed gas. Examples of methods for evaporating the solvent include air drying and drying by heating. The drying temperature is preferably 20 to 100°C.

[0073] 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, relative to the total amount of the solvent. The upper limit can be 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 other solvents include the solvent (A) described above. The content of the stabilizer in the solvent of the present disclosure is preferably 5% by mass or less, more preferably 1% by mass or less, relative to the total amount of the solvent. The content of other solvents 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, relative to the total amount of the solvent.

[0074] [Lubricant Solution] The present disclosure also relates to a lubricant solution containing the composition of the present disclosure and a lubricant. A lubricant refers to a substance used to lubricate friction surfaces and improve the mechanical efficiency of the friction surfaces. It is used to reduce friction at the contact surfaces and prevent heat generation and wear damage when two components move in contact with each other. Lubricants are required to have appropriate viscosity, physical and chemical stability, oiliness, and oxidation stability. The lubricant may be in the form of a 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.

[0075] As the lubricant, a fluorine-based lubricant or a silicone-based lubricant is preferred because of its excellent solubility or dispersibility in the composition of the present disclosure.

[0076] The fluorine-based lubricant refers to a lubricant having a fluorine atom in the molecule, and examples thereof include fluorine-based solid lubricants such as fluorine oil, fluorine grease, and polytetrafluoroethylene resin powder.

[0077] The fluorine oil is preferably perfluoropolyether (hereinafter also referred to as PFPE) or a low polymer of chlorotrifluoroethylene, and examples thereof include 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).

[0078] Preferred 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. Examples include products with the names "Krytox (registered trademark) Grease 240AC" (manufactured by DuPont Co., Ltd.), "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 trademark) 6169" (all manufactured by Dow Corning Toray Co., Ltd.).

[0079] Furthermore, the silicone-based lubricant refers to a lubricant containing silicone, and examples thereof include silicone oil and silicone grease.

[0080] Examples of silicone oils include straight silicones, as well as modified silicones such as reactive silicones and non-reactive silicones. More specifically, straight silicones include dimethyl silicones, methylphenyl silicones, and methylhydrogen silicones, each of which has a methyl group, a phenyl group, or a hydrogen atom bonded as a substituent. Examples of reactive silicones include amino-modified, epoxy-modified, carboxy-modified, carbinol-modified, methacrylic-modified, phenol-modified, and heterofunctional group-modified. Examples of non-reactive silicones include polyether-modified, methylstyryl-modified, alkyl-modified, higher fatty acid ester-modified, specially hydrophilic modified, and fluorine-modified. These silicones may be used alone or in combination of two or more. Examples of silicone oils include those with the product 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).

[0081] Preferred silicone greases are those containing the above-listed silicone oils as base oils, thickeners such as metal soaps, and various additives. Examples include products under the names "Shin-Etsu Silicone G-30 Series," "Shin-Etsu Silicone G-40 Series," "Shin-Etsu Silicone FG-720 Series," "Shin-Etsu Silicone G-411," "Shin-Etsu Silicone G-501," "Shin-Etsu Silicone G-6500," "Shin-Etsu Silicone G-330," "Shin-Etsu Silicone G-340," "Shin-Etsu Silicone G-350," and "Shin-Etsu Silicone G-630" (all manufactured by Shin-Etsu Chemical Co., Ltd.), "Molycoat (registered trademark) SH33L," "Molycoat (registered trademark) 41," "Molycoat (registered trademark) 44," "Molycoat (registered trademark) 822M," "Molycoat (registered trademark) 111," "Molycoat (registered trademark) High Vacuum Grease," and "Molycoat (registered trademark) Thermal Diffusion Compound" (all manufactured by Dow Corning Toray Co., Ltd.).

[0082] The lubricant solution may contain one type of lubricant or two or more types of lubricants.

[0083] The lubricant solution of the present disclosure is environmentally friendly, has excellent lubricant solubility, and dries quickly enough, making it suitable for forming a lubricant coating film.

[0084] In the lubricant solution of the present disclosure, the composition of the composition of the present disclosure and the lubricant are not particularly limited and can be appropriately selected as desired. For example, the lubricant may be present in an amount of 0.1 mass % or more and 50 mass % or less relative to 100 mass % of the lubricant solution of the present disclosure, but this is not limited thereto.

[0085] [Method for manufacturing an article coated with a lubricant] One embodiment of the present invention is a method for manufacturing an article coated with a lubricant, 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 to form a lubricant coating on the surface of the article.

[0086] The article can be made of various materials such as metal, resin, elastomer, ceramic, and glass. Examples include industrial equipment that uses fluorine-based lubricants, CD and DVD tray parts for personal computers and audio equipment, and home and office equipment such as printers, copy machines, and flux machines. The article can also be suitably used for syringe needles and cylinders, medical tubing parts, and the like that use silicone-based lubricants.

[0087] The method for applying the lubricant solution of the present disclosure to the surface of an article is not particularly limited, and examples thereof include application with a brush, application by spraying, and application by immersing the article in the lubricant composition of the present disclosure.

[0088] The compositions of the present disclosure may also be used as reaction solvents, extractants, desiccants, refrigerants, and the like.

[0089] [Heat Transfer Medium] 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 containing the above-mentioned composition of the present disclosure or the aerosol composition. Examples of heat cycle systems include Rankine cycle systems, heat pump cycle systems, refrigeration cycle systems, heat transport systems, and secondary circulation cooling systems. More specifically, examples include refrigeration and freezing equipment, air conditioning equipment, power generation systems, heat transport devices, and secondary cooling machines.

[0090] 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 includes a compressor that compresses heat transfer medium vapor to produce high-temperature, high-pressure heat transfer medium vapor; a condenser that cools the compressed heat transfer medium vapor to produce low-temperature, high-pressure heat transfer medium liquid; an expansion valve that expands the heat transfer medium liquid discharged from the condenser to produce low-temperature, low-pressure heat transfer medium liquid; an evaporator that heats the heat transfer medium discharged from the expansion valve to produce 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.

[0091] The composition of the present disclosure can be particularly preferably used as a secondary refrigerant for a secondary circulation refrigeration system. The secondary circulation refrigeration system is a system having a primary cooling means for cooling a primary refrigerant made of ammonia or a hydrocarbon refrigerant, a secondary circulation refrigeration means for circulating the secondary circulation refrigerant for the secondary circulation refrigeration system to cool a target object, and a heat exchanger for exchanging heat between the primary refrigerant and the secondary refrigerant to cool the secondary refrigerant. The target object can be cooled by this secondary circulation refrigeration system.

[0092] The heat transfer medium of the present disclosure comprises the composition of the present disclosure. The content 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. When the heat transfer medium comprises an aerosol composition, the content 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.

[0093] The heat transfer medium of the present disclosure may contain stabilizers, other solvents, etc., as necessary. Specific examples of stabilizers include the stabilizers described above. Other solvents include solvent (A) described above. The content of the stabilizer in the heat transfer medium of the present disclosure is preferably 5% by mass or less, more preferably 1% by mass or less, based on the total amount of the heat transfer medium. The content of the other solvent in the heat transfer medium 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 heat transfer medium.

[0094] The heat transfer medium of the present disclosure is typically used as a heat transfer medium composition containing a heat transfer medium and a refrigerating machine oil. Examples of the refrigerating machine oil include polyalkylene glycols, polyol esters, and polyvinyl ethers. The content of the refrigerating machine oil in the heat transfer medium composition is preferably 10 to 100 parts by mass, more preferably 20 to 50 parts by mass, per 100 parts by mass of the heat transfer medium.

[0095] [Azeotrope-Like Composition] The present disclosure also relates to an azeotrope-like composition (hereinafter also referred to as "azeotrope-like composition A") consisting of 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. 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.

[0096] 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 can be formed from 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.

[0097] The azeotrope-like composition A of the present disclosure can be used as an aerosol by combining it with a propellant gas. A preferred embodiment of the above-mentioned aerosol is an aerosol using the azeotrope-like composition A. The present disclosure also relates to an aerosol composition (also referred to as aerosol composition A) comprising the azeotrope-like composition A and a propellant gas. A preferred embodiment of the above-mentioned aerosol composition is an aerosol composition using the azeotrope-like composition A.

[0098] The azeotrope-like composition A of the present disclosure has excellent cleaning properties and can be used as a cleaning agent for degreasing, flux removal, precision cleaning, draining, rinsing, dry cleaning, and the like. It is also preferable to use an aerosol composition (aerosol composition A) containing the above-described azeotrope-like composition A and a propellant gas instead of the azeotrope-like composition A of the present disclosure. The present disclosure also relates to a cleaning agent containing the above-described azeotrope-like composition A or aerosol composition A. A preferred embodiment of the use of the above-described composition of the present disclosure as a cleaning agent is the use of the above-described azeotrope-like composition A as a cleaning agent. A preferred embodiment of the cleaning agent containing the above-described aerosol composition according to the composition of the present disclosure is a cleaning agent containing the above-described aerosol composition A or aerosol composition A. The azeotrope-like composition A of the present disclosure has excellent solubility for organic substances and 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. A preferred embodiment of the use of the above-described composition of the present disclosure as a solvent is the use as a solvent for azeotrope-like composition A.

[0099] The present disclosure also relates to a lubricant solution comprising the above-described azeotrope-like composition A of the present disclosure and a lubricant. A preferred embodiment of the lubricant solution comprising the above-described composition of the present disclosure and a lubricant is a lubricant solution comprising the azeotrope-like composition A of the present disclosure and a lubricant. The azeotrope-like composition A of the present disclosure can be used as a heat transfer medium for a heat cycle system. It is also preferred to use the above-described aerosol composition A instead of the azeotrope-like composition A of the present disclosure. The present disclosure also relates to a heat transfer medium comprising the above-described azeotrope-like composition A of the present disclosure or aerosol composition A. A preferred embodiment of the heat transfer medium comprising the above-described composition of the present disclosure is a heat transfer medium comprising the azeotrope-like composition A. Furthermore, a preferred embodiment of the heat transfer medium comprising the above-described aerosol composition according to the composition of the present disclosure is a heat transfer medium comprising the above-described aerosol composition A.

[0100] The azeotrope-like composition B of the present disclosure can be used as an aerosol by combining it with a propellant gas. A preferred embodiment of the above-mentioned aerosol is an aerosol using the azeotrope-like composition B. The present disclosure also relates to an aerosol composition (also referred to as aerosol composition B) comprising the azeotrope-like composition B and a propellant gas. A preferred embodiment of the above-mentioned aerosol composition is an aerosol composition using the azeotrope-like composition B.

[0101] The azeotrope-like composition B of the present disclosure has excellent cleaning properties and can be used as a cleaning agent for degreasing, defluxing, precision cleaning, draining, rinsing, dry cleaning, and the like. It is also preferable to use an aerosol composition (aerosol composition B) containing the above-described azeotrope-like composition B and a propellant gas instead of the azeotrope-like composition B of the present disclosure. The present disclosure also relates to a cleaning agent containing the above-described azeotrope-like composition B or aerosol composition B. A preferred embodiment of the use of the above-described composition of the present disclosure as a cleaning agent is the use of the above-described azeotrope-like composition B as a cleaning agent. A preferred embodiment of the cleaning agent containing the above-described aerosol composition according to the composition of the present disclosure is a cleaning agent containing the above-described aerosol composition B. The azeotrope-like composition B of the present disclosure has excellent solubility for organic substances and 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. A preferred embodiment of the use of the above-described composition of the present disclosure as a solvent is the use as a solvent for azeotrope-like composition B.

[0102] The present disclosure also relates to a lubricant solution comprising the above-described azeotrope-like composition B of the present disclosure and a lubricant. A preferred embodiment of the lubricant solution comprising the above-described composition of the present disclosure and a lubricant is a lubricant solution comprising the azeotrope-like composition B of the present disclosure and a lubricant. The azeotrope-like composition B of the present disclosure can be used as a heat transfer medium for a heat cycle system. It is also preferred to use the above-described aerosol composition B instead of the azeotrope-like composition B of the present disclosure. The present disclosure also relates to a heat transfer medium comprising the above-described azeotrope-like composition B of the present disclosure or aerosol composition B. A preferred embodiment of the heat transfer medium comprising the above-described composition of the present disclosure is a heat transfer medium comprising the azeotrope-like composition B. Furthermore, a preferred embodiment of the heat transfer medium comprising the above-described aerosol composition according to the composition of the present disclosure is a heat transfer medium comprising the above-described aerosol composition B.

[0103] The present invention also relates to 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 stabilizer, surfactant, flame retardant, metal passivator, and rust inhibitor described above, respectively.

[0104] The content of at least one component selected from stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors is preferably 20 mass% or less, more preferably 10 mass% or less, even more preferably 5 mass% or less, and particularly preferably 1 mass% or less, relative to the total amount of the composition.

[0105] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited thereto. Compositions 1 to 5 and 8 to 11 are examples, and compositions 6 and 7 are comparative examples.

[0106] Examples 1-1 to 1-9, Comparative Examples 1 and 2 Production Example of 1233zd(Z) 1233zd(Z) was produced based on the description in JP-A-2017-110020.

[0107] <Production Example of 1,1,1,3,3,3-Hexafluoroisopropyl methyl ether> 1,1,1,3,3,3-Hexafluoroisopropyl methyl ether was produced based on the description in US Pat. No. 3,346,448.

[0108] <Measurement of Vapor-Liquid Equilibrium> 250 g of compositions 1 to 11, obtained by mixing 1233zd(Z) and HFE-356mmz at various mass ratios, were placed in an Othmer-type vapor-liquid equilibrium apparatus. When the temperatures of the vapor and liquid phases reached equilibrium, liquid and vapor samples were collected in 10 mL vials pre-cooled with ice water, and the compositions of 1233zd(Z) and HFE-356mmz were analyzed by gas chromatography. The results are shown in Table 1. 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. The water content of each composition can be calculated from the contents of 1233zd(Z) and HFE-356mmz. For example, the water content of composition 2 was 0.0043% by mass.

[0109]

[0110] The results in Table 1 reveal that the azeotrope-like compositions show no substantial change in the composition of the gas phase and liquid phase when the 1233zd(Z) content is in the range of 70.01 to 99.99 mass% or 0.01 to 28.00 mass% and the HFE-356mmz content is in the range of 0.01 to 29.99 mass% or 72.00 to 99.99 mass%. Furthermore, the azeotropic nature was maintained even when the composition contained 0.0029 to 0.0356 mass% water.

[0111] <Detergency Test> [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 × 15 mm × 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. Then, 200 g of 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. Then, ultrasonic cleaning was performed at 25°C for 2 minutes (ultrasonic oscillator: Neosonic, manufactured by Alex Corporation, output 100 W, frequency 28 kHz). Here, the cleaning agent used was the same as Compositions 1 to 5 prepared in Examples 1-1 to 1-5. Thereafter, the test piece was taken out and dried at 80°C for 5 minutes, and the surface of the test piece was visually observed. No staining was observed on the surface of the test piece regardless of which cleaning agent was used.

[0112] 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, a SUS316 test piece (30 mm x 15 mm x 2 mm) was completely immersed in the cutting oil. The test piece was removed from the cutting oil and visually inspected. The cutting oil was found to be adhering to the surface of the test piece. Then, 200 g of the cleaning agent was placed in a 300 mL glass beaker, and the SUS test piece with the adhering cutting oil was placed in the beaker so that it was completely immersed. The beaker was subjected to ultrasonic cleaning at 25°C for 2 minutes (ultrasonic oscillator: Neosonic, manufactured by Alex Corporation, output 100 W, frequency 28 kHz). The cleaning agents used here were those prepared by replacing 1233zd(Z) in Compositions 1 to 5 prepared in Examples 1-1 to 1-5 with a 1233zd(Z) / 1233zd(E) ratio of 90 / 10 (mass ratio). The test pieces were then removed and dried at 80°C for 5 minutes. Visual observation of the test piece surfaces revealed no staining on the test piece surfaces, regardless of the cleaning agent used. In each of Compositions 1 to 5 prepared in Examples 1-1 to 1-5, where 1233zd(Z) was replaced with a 1233zd(Z) / 1233zd(E) ratio of 90 / 10 (mass ratio), the difference in composition between the gas phase and liquid phase of 1233zd(Z) and HFE-356mmz was 8.00 mass% or less. Therefore, each of the above compositions is an azeotrope-like composition. 1233zd(E) was produced based on the description in JP 2017-110020 A.

[0113] Example 4 A composition was prepared by mixing the components 1233zd(Z) / HFE-356mmz / HFIP to a ratio of 95.00% by mass / 4.99% by mass / 0.01% by mass, and a cleaning test was conducted in the same manner as in Example 2. As a result, no staining was observed on the surface of the test piece, as in Example 2. In the composition, the compositional difference between the gas phase and liquid phase of 1233zd(Z) and HFE-356mmz was 8.00% by mass or less, respectively. Therefore, the composition is an azeotrope-like composition.

[0114] The composition of the present disclosure has a small impact on the global environment and is resistant to compositional changes even when repeatedly evaporated and condensed, and therefore can be used in a wide range of applications, such as cleaning agents, solvents, aerosols, and heat transfer media.

[0115] Although the present disclosure has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present disclosure. This application is based on a Japanese patent application (Patent Application No. 2023-134119) filed on August 21, 2023, the contents of which are incorporated herein by reference.

Claims

1. An azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.

2. The azeotrope-like composition of claim 1 consisting of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether.

3. The azeotrope-like composition according to claim 1 or 2, 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, or 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.

4. The azeotrope-like composition according to claim 1 or 2, which contains 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 claim 1 or 2, 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.

6. The azeotrope-like composition according to claim 1, wherein the total amount of (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether is 80 mass% or more, based on the total amount of the composition.

7. The azeotrope-like composition of claim 1 further comprising water.

8. The azeotrope-like composition according to claim 7, which contains 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.

9. The azeotrope-like composition according to claim 7 or 8, which consists of (Z)-1-chloro-3,3,3-trifluoropropene, 1,1,1,3,3,3-hexafluoroisopropyl methyl ether, and water.

10. A method for producing a composition, comprising the steps of: preparing an azeotrope-like composition containing (Z)-1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3,3-hexafluoroisopropyl methyl ether; and 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.

11. A composition comprising the azeotrope-like composition of claim 1 and at least one selected from the group consisting of stabilizers, surfactants, flame retardants, metal passivators, and rust inhibitors.

12. An aerosol composition comprising the azeotrope-like composition of claim 1 and a propellant gas.

13. A cleaning agent comprising the azeotrope-like composition of claim 1.

14. A cleaning agent comprising the aerosol composition of claim 12.

15. A cleaning agent according to claim 13 or 14, for cleaning vehicles or transport vehicles.

16. A method for cleaning an article, comprising the step of contacting the cleaning agent according to claim 13 or 14 with the article to be cleaned.

17. A method for recovering a cleaning agent, comprising: cleaning an article with the cleaning agent according to claim 13 or 14; and purifying the cleaning agent after cleaning.

18. A lubricant solution comprising the azeotrope-like composition of claim 1 and a lubricant.

19. A heat transfer medium comprising the azeotrope-like composition of claim 1 or the aerosol composition of claim 12.

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