Solvent composition, cleaning method, method for manufacturing coated articles, aerosol composition, heat transfer medium

Abstract

Provided are: a solvent composition capable of suppressing corrosion of metal; a rinsing method using said solvent composition; and a coating film-provided article manufacturing method.　This solvent composition contains: 1-chloro-2,3,3-trifluoropropene as a first component; and, as a second component, at least one selected from the group consisting of 1,2,3,3-tetrachloropropene, 1,2,3-trichloro-3-fluoropropene, 1,3,3-trichloro-2-fluoropropene, 1,3-dichloro-2,3-difluoropropene, 2-chloro-3,3-difluoropropene, 2,3,3-trifluoropropene, 1,3-dichloro-1,2,2-trifluoropropane, 1-chloro-1,2,2,3-tetrafluoropropane, and the like. The solvent composition is characterized in that the proportion of the total contained amount of the second component with respect to the total of the contained amount of 1-chloro-2,3,3-trifluoropropene and the total contained amount of the second component is 0.0001-1.0 mass%.

Description

Technical Field

[0001] The present invention relates to a solvent composition, a cleaning method using the solvent composition, and a method for producing an article with a coating film.

Background Art

[0002] Conventionally, as a cleaning solvent for oil stain cleaning, flux cleaning, dust cleaning, etc., a diluting solvent for a moisture removing solvent, a dry cleaning solvent, a reaction solvent, a lubricant, etc., a hydro chlorofluorocarbon (hereinafter also referred to as HCFC) having excellent nonflammability, low toxicity, and stability has been used. However, since HCFC has a concern of adversely affecting the ozone layer, the production of HCFC was completely abolished in developed countries in 2020.

[0003] As a solvent that does not adversely affect the ozone layer, perfluorocarbon (hereinafter also referred to as PFC), hydrofluorocarbon (hereinafter also referred to as HFC), hydrofluoroether (hereinafter also referred to as HFE), etc. are known.

[0004] However, since HFC and PFC have a large global warming potential, they are substances subject to the regulations of the Kyoto Protocol. In addition, compared with HCFC, the solubility of oils is low, and the application ranges of HFC, HFE, and PFC are limited.

[0005] As a compound useful for various applications such as a heat transfer medium, a foaming agent, a solvent, a cleaning agent, etc. without adversely affecting the global environment, 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd, hereinafter also referred to as 1233yd) has been proposed (Patent Document 1).

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] The inventors of this invention have found a problem in that when 1233yd, as described in Patent Document 1, is brought into contact with metal, corrosion of the metal may progress. In view of the above problems, the present invention aims to provide a solvent composition that can suppress metal corrosion, a cleaning method using the solvent composition, a coating film forming composition, a method for manufacturing a coated article, an aerosol composition, and a heat transfer medium.

[0008] As a result of diligent research to solve the above problems, the inventors of this invention have found that the above problems can be solved by the following configuration.

[0009] (1) The first component is 1-chloro-2,3,3-trifluoropropene, A solvent composition comprising, as a second component, at least one selected from the group consisting of 1,2,3,3-tetrachloropropene, 1,2,3-trichloro-3-fluoropropene, 1,3,3-trichloro-2-fluoropropene, 1,3-dichloro-2,3-difluoropropene, 2-chloro-3,3-difluoropropene, 2,3,3-trifluoropropene, 1,3-dichloro-1,2,2-trifluoropropane, 1-chloro-1,2,2,3-tetrafluoropropane, 2-chloro-1,1,3,3-tetrafluoropropane, 2-chloro-1,1,2-trifluoropropane, and chloroform, A solvent composition characterized in that the ratio of the total amount of the second component to the sum of the amount of 1-chloro-2,3,3-trifluoropropene and the total amount of the second component is 0.0001 to 1.0% by mass. (2) The solvent composition according to (1), wherein the second component comprises at least one selected from the group consisting of 1,2,3,3-tetrachloropropene, 1,2,3-trichloro-3-fluoropropene, 1,3,3-trichloro-2-fluoropropene, 1,3-dichloro-2,3-difluoropropene, 2-chloro-3,3-difluoropropene, and 2,3,3-trifluoropropene. (3) The solvent composition according to (1) or (2), further comprising as a third component at least one selected from the group consisting of trans-1,2-dichloroethylene, nonafluorobutoxymethane, nonafluorobutoxyethane, ethanol, isopropanol, 1,2-dichloro-2,3,3-trifluoropropane, and 1,2-dichloro-3,3-difluoropropene. (4) The solvent composition according to any one of (1) to (3), wherein the proportion of 1-chloro-2,3,3-trifluoropropene in the solvent composition is 30% by mass or more. (5) A cleaning method characterized by bringing a solvent composition described in any of (1) to (4) into contact with an article to remove dirt adhering to the surface of the article. (6) The cleaning method according to (5), wherein at least a portion of the material of the surface of the article that comes into contact with the solvent composition is metal. (7) A coating film-forming composition characterized by comprising a non-volatile organic compound and a solvent composition according to any one of (1) to (4). (8) A method for producing a coated substrate, characterized by applying the coating film-forming composition described in (7) to the surface of the substrate, and then evaporating and removing the solvent composition to form a coating film containing a non-volatile organic compound. (9) The method for producing a coated substrate according to (8), wherein at least a portion of the material of the substrate surface that comes into contact with the solvent composition is metal. (10) An aerosol composition comprising a propellant and a solvent composition according to any one of (1) to (4). (11) A heat transfer medium for a thermal cycle system comprising the solvent composition described in any of (1) to (4). [Effects of the Invention]

[0010] The solvent composition of the present invention has sufficient volatility, excellent solubility for hydrophobic solutes such as oils, and can suppress metal corrosion. The cleaning method of the present invention can suppress metal corrosion and has excellent cleaning performance. The present invention provides a method for manufacturing coated articles that can suppress metal corrosion and form a uniform coating. The aerosol composition of the present invention can suppress metal corrosion and can spray the solvent composition of the present invention or a solute dissolved in the solvent composition of the present invention. The heat transfer medium of the present invention can suppress metal corrosion, has excellent solubility with lubricating oil (refrigeration oil), and has excellent cycle performance, making it suitable for use in thermal cycle systems. [Modes for carrying out the invention]

[0011] The meanings of the terms used in this invention are as follows: Compound 1233yd has two geometric isomers, the Z and E, depending on the position of the substituent on the double bond. In this specification, unless otherwise specified, when a compound name or abbreviation is used, it refers to at least one selected from the group consisting of the Z and E areomers, and more specifically, it refers to the Z or E isomer, or a mixture of the Z and E isomers in any proportion. Furthermore, (E) attached to the name and abbreviation of a compound having geometric isomers refers to the E isomer, and (Z) refers to the Z isomer.

[0012] <Solvent composition> The solvent composition of the present invention is a solvent composition comprising a first component, 1233yd, and a second component described later, wherein the ratio of the total amount of the second component to the sum of the content of 1233yd and the total amount of the second component is 0.0001 to 1.0% by mass.

[0013] In the solvent composition of the present invention, 1233yd is a component having excellent properties as a solvent, and the second component described above is a component included in the solvent composition as a stabilizer that stabilizes 1233yd. When the present inventors stored 1233yd at normal temperature and pressure for several days, they found a new problem that a trace amount of 1233yd decomposed to generate chloride ions, and metal corrosion might progress. Therefore, in the solvent composition of the present invention, by containing a predetermined amount of the above-mentioned second component together with 1233yd, the stabilization of 1233yd is achieved. The reason why 1233yd can be stabilized by containing a predetermined amount of the above-mentioned second component is not necessarily clear, but it is considered to have a function as a stabilizer that suppresses the decomposition of 1233yd and stabilizes it due to an effect presumed to be radical capture.

[0014] (1233yd) As described above, 1233yd means 1-chloro-2,3,3-trifluoropropene (CHF2CF=CHCl). The content of 1233yd in the solvent composition of the present invention is preferably 30% by mass or more, more preferably 50% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass or more based on the total mass of the solvent composition. If it is above the above lower limit value, it has excellent solubility of various organic substances in the solvent composition and excellent detergency. The upper limit is preferably 99.9999% by mass or less, and more preferably 99% by mass or less. In 1233yd, 1233yd(Z) and 1233yd(E) exist. Either 1233yd(Z) or 1233yd(E) may be used alone, or a mixture of 1233yd(Z) and 1233yd(E) may be used. The mass ratio (1233yd(Z) / 1233yd(E)) of 1233yd(Z) and 1233yd(E) is preferably 50 / 50 to 100 / 0, and more preferably 80 / 20 to 100 / 0. 1233yd can be produced, for example, by the method described in the following examples. Examples of commercially available products of 1233yd include the following. 「AMOLEA (registered trademark) AS-300」 (manufactured by AGC Inc.)

[0015] (Second component) The second component in the present invention is exemplified below. 1,2,3,3 - Tetrachloropropene (HFO - 1230xd. Hereinafter, also referred to as 1230xd.), 1,2,3 - Trichloro - 3 - fluoropropene (HCFO - 1231xd. Hereinafter, also referred to as 1231zd.), 1,3,3 - Trichloro - 2 - fluoropropene (HCFO - 1231yd. Hereinafter, also referred to as 1231yd.), 1,3 - Dichloro - 2,3 - difluoropropene (HCFO - 1232yd. Hereinafter, also referred to as 1232yd.), 2 - Chloro - 3,3 - difluoropropene (HCFO - 1242xf. Hereinafter, also referred to as 1242xf.), 2,3,3 - Trifluoropropene (HFO - 1243yf. Hereinafter, also referred to as 1243yf.), 1,3 - Dichloro - 1,2,2 - trifluoropropane (HCFC - 243ca. Hereinafter, also referred to as 243ca.), 1 - Chloro - 1,2,2,3 - tetrafluoropropane (HCFC - 244cb. Hereinafter, also referred to as 244cb.), 2 - Chloro - 1,1,3,3 - tetrafluoropropane (HCFC - 244da. Hereinafter, also referred to as 244da.), 2 - Chloro - 1,1,2 - trifluoropropane (HCFC - 253bb. Hereinafter, also referred to as 253bb.), Chloroform (hereinafter, also referred to as CHCl3).

[0016] (1230xd) 1230xd is a compound soluble in 1233yd. 1230xd can be produced, for example, by reacting 1,3 - dichloropropene with chlorine in a carbon tetrachloride solvent to obtain a mixture of 1,1,1,2,2,3 - hexafluoropropane, 1,1,1,2,3,3 - hexafluoropropane, and 1,1,2,2,3,3 - hexafluoropropane, distilling and purifying the 1,1,2,2,3,3 - hexafluoropropane obtained, mixing it with zinc powder in a DMF solvent, and performing a dechlorination reaction.

[0017] (1231xd) 1231xd is a compound soluble in 1233yd. 1231xd can be produced, for example, by reacting 1,2-dichloroethylene with dichlorofluoromethane in the presence of a zirconium chloride catalyst to obtain 1,2,3,3-tetrachloro-1-fluoropropane, which is then mixed with an aqueous sodium hydroxide solution in the presence of a tetrabutylammonium bromide catalyst and subjected to a dehydrochlorination reaction.

[0018] (1231 yards) 1231yd is a compound soluble in 1233yd. 1231yd can be produced, for example, by reacting 1,2-dichloro-2-fluoropropane obtained by reacting 2,3-dichloropropene with hydrogen fluoride to obtain 1,2-dichloro-2-fluoropropane, then reacting chlorine with 1,1,1,2,3-pentachloro-2-fluoropropane and 1,1,2,3,3-pentachloro-2-fluoropropane in a carbon tetrachloride solvent, and purifying the mixture of these by distillation to obtain 1,1,2,3,3-pentachloro-2-fluoropropane, which is then mixed with zinc powder in a DMF solvent and subjected to a dechlorination reaction.

[0019] (1232 yards) 1232yd is a compound soluble in 1233yd. 1232yd can be produced, for example, by reacting 1231yd with antimony trifluoride.

[0020] (1242xf) 1242xf is a compound soluble in 1233yd. 1242xf can be produced, for example, by distillation purification of a mixture of 2,2-dichloro-1,1-difluoropropene, obtained by chlorinating 1,1-difluoroacetone with phosphorus pentachloride, mixed with an aqueous sodium hydroxide solution in the presence of a tetrabutylammonium bromide catalyst, and subjected to a dehydrochlorination reaction, resulting in 2-chloro-1,1-difluoropropene and 1242xf.

[0021] (1243yf) 1243yf is a compound soluble in 1233yd. 1243yf can be produced, for example, by distillation purification of a mixture of 1,1,2-trifluoropropane obtained by reducing 1233yd with hydrogen in the presence of a palladium-carbon catalyst, and 1243yf.

[0022] (243ca) 243ca is a compound soluble in 1233yd. 243ca can be produced, for example, by reacting 3-chloro-2,2,3-trifluoropropanol with p-toluenesulfonic acid chloride to obtain a tosylate, which is then reacted with lithium chloride in a diethylene glycol solvent.

[0023] (244cb) 244cb is a compound soluble in 1233yd. 244cb can be produced, for example, by reacting 3-chloro-2,2,3-trifluoropropanol with p-toluenesulfonic acid chloride to obtain a tosylate, which is then reacted with potassium fluoride in a diethylene glycol solvent.

[0024] (244da) 244da is a compound soluble in 1233yd. 244da can be produced, for example, by chlorinating 1,1,3,3-tetrafluoro-2-propanol with thionyl chloride.

[0025] (253bb) 253bb is a compound soluble in 1233yd. 253bb can be produced, for example, by reacting 1233yd with chlorine.

[0026] (CHCl3) CHCl3 is a compound soluble in 1233 yd. CHCl3 can be obtained, for example, by reacting methane with chlorine in the gas phase, and can also be produced by distillation purification of a mixture of dichloromethane and CHCl3.

[0027] In this specification, the statement that a substance is soluble in 1233 yd means that when the substance is mixed with 1233 yd to a desired concentration and stirred at room temperature (25°C), it dissolves uniformly without causing two-layer separation or turbidity.

[0028] The stability of the solvent composition of the present invention can be evaluated, for example, by the difference between the initial pH of the solvent composition and the pH after the solvent composition has been stored for a certain period of time. In this invention, the pH of the solvent composition refers to the pH of the upper aqueous layer when the solvent composition is mixed with pure water at pH 7, shaken for a predetermined time, and then allowed to stand to separate into two layers. The specific pH measurement conditions can be those described in the pH measurement section of the examples described below.

[0029] When the solvent composition of the present invention is stored for 7 days at the boiling point of 1233yd (approximately 54°C) where the mass ratio of 1233yd(Z) to 1233yd(E) (1233yd(Z) / 1233yd(E)) is 90 / 10, the decrease in pH of the solvent composition after storage can be kept to less than 1.0 compared to the pH of the solvent composition before storage. In other words, the generation of acid due to the decomposition of 1233yd can be suppressed. It is more preferable that the decrease in pH due to storage be 0.8 or less, even more preferable that it be 0.5 or less, and particularly preferable that it be 0.0.

[0030] As the second component, olefins such as 1230xd, 1231xd, 1231yd, 1232yd, 1242xf, and 1243yf are more preferred because they act as excellent stabilizers for 1233yd.

[0031] In terms of further suppressing metal corrosion, the solvent composition of the present invention preferably uses a combination of 244da and CHCl3, a combination of 1230xd and 1231xd, a combination of 1242xf and 1243yf, or a combination of 1242xf and 253bb as the second component.

[0032] The solvent composition of the present invention contains at least one of the compounds exemplified above as a second component. In the solvent composition of the present invention, the ratio of the total amount of the second component to the sum of the content of 1233yd and the total amount of the second component is 0.0001 to 1.0% by mass, preferably 0.0005 to 1.0% by mass, and more preferably 0.0005 to 0.5% by mass.

[0033] As a method for preparing the solvent composition of the present invention, commercially available products of 1233yd and the second component may be obtained and mixed in the above proportions, or 1233yd and the second component may be manufactured separately and mixed in the above proportions, or the solvent composition may be manufactured by a method in which both 1233yd and the second component are produced and the obtained solvent composition may be used.

[0034] 1233yd can also be produced, for example, by following the procedure below, using 2,2,3,3-tetrafluoropropanol (hereinafter also referred to as TFPO) as the starting material. In the presence of N,N-dimethylformamide (hereinafter also referred to as DMF), 3-chloro-1,1,2,2-tetrafluoropropane (HCFC-244ca; hereinafter also referred to as 244ca) can be produced by a chlorination reaction with thionyl chloride (SOCl2). The obtained 244ca can then be dehydrofluorinated in the presence of a base, either in the liquid or gas phase, to produce 1233yd. Furthermore, 1233yd can also be produced using, for example, 245ca as the starting material by following the procedure below. 244ca can be produced by a gas-phase reaction between 245ca and a Cl compound such as hydrogen chloride, carbon tetrachloride, or chloroform in the presence of a metal catalyst containing oxides or fluorides of Cr or Al. The obtained 244ca can then be subjected to a dehydrofluoridation reaction in the presence of a base, either in the liquid or gas phase, to produce 1233yd. Furthermore, methods for producing 1233yd include a dehydrochlorination reaction of 1,2-dichloro-2,3,3-trifluoropropane (HCFC-243ba; hereinafter also referred to as 243ba), a reaction of 1,1,3,3-tetrachloro-2-fluoropropane (HCFC-241ea; hereinafter also referred to as 241ea), 1,1,2,3-tetrachloro-2-fluoropropane (HCFC-241ba; hereinafter also referred to as 241ba), or 1231yd with hydrogen fluoride. The solvent composition of the present invention may be prepared by the above procedure, which includes 1233yd as the first component and at least one of the above-described compounds as the second component as a by-product.

[0035] The solvent composition of the present invention may contain components other than 1233yd and the second component, to the extent that it does not impair the effects of the present invention. Examples of components other than 1233yd and the second component include trans-1,2-dichloroethylene (tDCE), nonafluorobutoxymethane, nonafluorobutoxyethane, ethanol, isopropanol, 243ba, and 1,2-dichloro-3,3-difluoropropene (HCFO-1232xd; hereinafter also referred to as 1232xd). Among the compounds exemplified above, tDCE, nonafluorobutoxymethane, nonafluorobutoxyethane, ethanol, and isopropanol are preferred.

[0036] When the solvent composition of the present invention contains 1233yd and tDCE as a component other than the second component, the ratio of the total amount of 1233yd and tDCE to the total amount of the solvent composition is preferably 90% by mass or more, and more preferably 95% by mass or more. The mass ratio of 1233yd to tDCE (1233yd / tDCE) is preferably 28 / 72 to 41 / 59. If the total amount and mass ratio of 1233yd and tDCE are within the above range, the solubility is further improved.

[0037] When the solvent composition of the present invention contains 1233yd and HFE, which is nonafluorobutoxymethane or nonafluorobutoxyethane, as a component other than the second component, the ratio of the total amount of 1233yd and HFE to the total amount of the solvent composition is preferably 70% by mass or more, and more preferably 90% by mass or more. The ratio of HFE to the total amount of 1233yd and HFE is preferably 25 to 75% by mass. If the total amount of 1233yd and HFE and the ratio of HFE are within the above ranges, the solubility is even better.

[0038] When the solvent composition of the present invention contains 1233yd and an alcohol other than the second component, such as ethanol or isopropanol, the ratio of the total amount of 1233yd and alcohol to the total amount of the solvent composition is preferably 80% by mass or more, and more preferably 90% by mass or more. For every 100% by mass of the total amount of 1233yd and alcohol, the content of 1233yd is preferably 75-99% by mass, the content of alcohol is preferably 1-25% by mass, and the content of 1233yd is preferably 90-98% by mass, and the content of alcohol is preferably 2-10% by mass. If the content of 1233yd and alcohol is within the above range, the solubility is even better.

[0039] For example, if the solvent composition of the present invention comes into contact with copper or a copper alloy, the solvent composition of the present invention may contain nitro compounds or triazoles to avoid corrosion of those metals.

[0040] The solvent composition of the present invention is a stable solvent composition that exhibits excellent solubility and cleaning properties for various organic substances, does not adversely affect the global environment, and is stabilized and has suppressed decomposition. It is preferably used for cleaning applications such as degreasing, pipe cleaning, flux cleaning, water draining, precision cleaning, dry cleaning of clothing, and stain removal. The solvent composition of the present invention can also be used as a coating-forming composition by dissolving lubricants such as silicone-based lubricants and fluorine-based lubricants, rust inhibitors made of mineral oils and synthetic oils, moisture-proof coating agents for water-repellent treatment, and antifouling coating agents such as fingerprint-resistant agents for antifouling treatment, and applying it to the surface of articles to form a coating film. Furthermore, the solvent composition of the present invention is also suitable as a heat transfer medium for heating and cooling articles.

[0041] The solvent composition of the present invention can be applied to a wide range of articles, including electronic components such as capacitors, diodes, and circuit boards on which they are mounted; medical devices such as hypodermic needles and catheters; optical components such as lenses and polarizers; automotive parts such as fuel injection needles and drive gears used in automobile engines; mechanical parts such as drive components and exterior parts used in industrial robots; and carbide tools used in machine tools such as cutting tools. Furthermore, the solvent composition of the present invention can be applied to a wide range of materials, including metals, plastics, elastomers, glass, ceramics, and fabrics. Among these, it is particularly suitable for metals such as iron, copper, nickel, gold, silver, and platinum, as well as sintered metals, glass, fluororesins, and engineering plastics such as PEEK. The solvent composition of the present invention is particularly suitable for cleaning, diluting, and coating applications of metals or composite materials with metals.

[0042] [Washing method] The cleaning method of the present invention is a method of removing dirt adhering to an article by bringing the solvent composition of the present invention into contact with the article. Examples of contaminants that adhere to articles include grease, processing oil, silicone oil, flux, wax, ink, mineral oil, mold release agents containing silicone oil, pitch, asphalt and other oils and fats, and dust. Specific examples of processing oils include cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, press working oil, punching oil, drawing oil, assembly oil, and wire drawing oil. Because the solvent composition of the present invention has high cleaning power, it can be used particularly well for cleaning processing oils, pitch, and asphalt.

[0043] Specific examples of the cleaning methods of the present invention include manual wiping, immersion cleaning, spray cleaning, immersion agitation cleaning, immersion ultrasonic cleaning, steam cleaning, and methods combining these. For example, spray cleaning may be performed in the form of an aerosol containing the solvent composition of the present invention and a liquefied or compressed gas. Cleaning conditions such as contact time and temperature in these cleaning methods can be appropriately selected depending on the cleaning method. In addition, known cleaning equipment can be appropriately selected. The cleaning method of the present invention can be carried out, for example, using the method and cleaning apparatus described in International Publication No. 2008 / 149907.

[0044] [Composition for forming a coating film, method for manufacturing articles with a coating film] The present invention provides a method for manufacturing a coated article, which involves applying a coating-forming composition containing the solvent composition of the present invention and a non-volatile organic compound to the surface of the article, and then evaporating the solvent composition to form a coating film containing the non-volatile organic compound on the surface of the article.

[0045] Methods for applying the coating-forming composition include, for example, application by brush, application by spray, and application by immersion. If the article is a tube or injection needle, the coating-forming composition may be applied to the inner wall by drawing it up. Furthermore, spray application can also be performed in the form of an aerosol containing the solvent composition of the present invention, a non-volatile organic compound, and a liquefied or compressed gas.

[0046] Methods for evaporating the solvent composition include, for example, air drying and heating. The drying temperature is preferably 20 to 100°C.

[0047] In this invention, a non-volatile organic compound refers to an organic compound whose boiling point is higher than that of the solvent composition of the present invention, and which remains on the surface even after the solvent composition has evaporated. Specific examples of non-volatile organic compounds include lubricants for providing lubricity to articles, rust inhibitors for providing rust prevention effects to metal parts, moisture-proof coatings for providing water repellency to articles, and anti-fouling coatings such as fingerprint-resistant agents for providing anti-fouling properties to articles. The solvent composition of the present invention is suitable for this application because it has excellent solubility of organic compounds.

[0048] The method for preparing the coating film-forming composition is not particularly limited as long as it allows for the uniform dissolution of the non-volatile organic compound in the solvent composition.

[0049] The content of non-volatile organic compounds is preferably 0.01 to 50% by mass, more preferably 0.05 to 30% by mass, and even more preferably 0.1 to 20% by mass, based on the total amount of the coating film-forming composition. If the content of non-volatile organic compounds is within the above range, it is easy to adjust the thickness of the coating film when the coating film-forming composition is applied to an appropriate range.

[0050] [Aerosol composition] The solvent composition of the present invention can be used as an aerosol composition by mixing it with a propellant. Alternatively, in another embodiment, it can be used as an aerosol composition containing the solvent composition of the present invention, a propellant, and a solute dissolved in the solvent composition. Examples of propellants include liquefied gases and compressed gases. Examples of liquefied gases in the aerosol composition include dimethyl ether (DME), liquefied petroleum gas (LPG), propane, butane, isobutane, 1,1-difluoroethane (HFC-152a), 1,1,1,2-tetrafluoroethane (HFC-134a), 2,3,3,3-tetrafluoropropene (HFO-1234yf), and 1,3,3,3-tetrafluoropropene (HFO-1234ze). Examples of compressed gases include nitrogen, carbon dioxide, and nitrous oxide. The solute dissolved in the solvent composition can be any substance that can be applied to the surface of a substrate, such as lubricating oil, dye, or adhesive. The solute content is preferably 0.1 to 10% by mass, more preferably 0.1 to 5% by mass, and even more preferably 0.1 to 1% by mass, relative to 100% by mass of the total of the solvent composition and solute.

[0051] [Heat transfer medium] The solvent composition of the present invention exhibits excellent solubility with lubricating oil (refrigeration oil) and excellent cycle performance, making it suitable for use as a heat transfer medium in thermal cycle systems. Examples of thermal cycle systems include Rankine cycle systems, heat pump cycle systems, refrigeration cycle systems, heat transport systems, and secondary refrigerant cooling systems. Specifically, these include refrigeration and freezing equipment, air conditioning equipment, power generation systems, heat transport devices, and secondary coolers.

[0052] Below, we will describe a refrigeration cycle system as an example of a thermal cycle system. A refrigeration cycle system is a system that cools a load fluid to a lower temperature by removing thermal energy from the load fluid using a heat transfer medium in an evaporator. A refrigeration cycle system consists of a compressor that compresses the vapor of the heat transfer medium into high-temperature, high-pressure vapor of the heat transfer medium, a condenser that cools the compressed vapor of the heat transfer medium into low-temperature, high-pressure liquid of the heat transfer medium, an expansion valve that expands the liquid heat transfer medium discharged from the condenser into low-temperature, low-pressure liquid of the heat transfer medium, an evaporator that heats the heat transfer medium discharged from the expansion valve into high-temperature, low-pressure vapor of the heat transfer medium, a pump that supplies the load fluid to the evaporator, and a pump that supplies the load fluid to the condenser.

[0053] Furthermore, the solvent composition of the present invention can also be used as a heat transfer medium (also called a secondary refrigerant) for a secondary circulation cooling system. A secondary circulation cooling system is a system comprising a primary cooling means for cooling a primary refrigerant consisting of ammonia or hydrocarbon refrigerant, a secondary circulation cooling means for circulating a 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 and secondary refrigerants to cool the secondary refrigerant. This secondary circulation cooling system can cool the object to be cooled. [Examples]

[0054] The present invention will be described in detail below with reference to examples. The present invention is not limited to these examples. Examples 2-6, 10-14, 18-22, 26-30, 34-38, 42-46, 50-54, 58-62, 66-70, 74-78, 82-86, 90-94, 98-102, 106-110, 114-118, 122-126, 130-134, 138-142, 146-150, 154-158, 162-166, and 170-174 are examples of the solvent composition of the present invention. Examples 1, 7-9, 15-17, 23-25, 31-33, 39-41, 47-49, 55-57, 63-65, 71-73, 79-81, 87-89, 95-97, 103-105, 111-113, 119-121, 127-129, 135-137, 143-145, 151-153, 159-161, 167-169, 175, and 176 are comparative examples.

[0055] (Manufacturing example: Manufacturing of 244ca) 1204 g (9.12 mol) of 2,2,3,3-tetrafluoropropanol (TFPO) and 12 g (0.17 mol) of N,N-dimethylformamide (DMF) were added to a 2-liter four-necked flask equipped with a glass distillation column (measured at 5 stages) packed with a stirrer, a Liebig condenser, and a Laschig ring. 1078 g (9.12 mol) of thionyl chloride was added dropwise, and the mixture was stirred at room temperature for 12 hours. The reactor was heated to 100°C, and reaction distillation was carried out using a reflux timer with a reflux time / distillation time ratio of 5 / 1. The distilled 244ca was neutralized with a 20% by mass potassium hydroxide aqueous solution. The recovered 244ca (100% purity) amounted to 979 g (6.50 mol).

[0056] (Example of production: 1233yd produced) Using 2000g of 244Ca as a starting material, 19.9g of tetra-n-butylammonium chloride was added, and the reaction temperature was maintained at 50°C. 2792g of 40% potassium hydroxide aqueous solution was added dropwise over 30 minutes. The reaction was then continued for 52 hours, and the organic layer was recovered. The recovered organic layer was purified, yielding 1660g of 1233yd with a purity of 100% by mass. This test was repeated to produce the required amount of 1233yd. The mass ratio of 1233yd(Z) to 1233yd(E) (1233yd(Z) / 1233yd(E)) was 90 / 10.

[0057] (Examples 2-6, 10-14, 18-22, 26-30, 34-38, 42-46, 50-54, 58-62, 66-70, 74-78, 82-86: Preparation of solvent compositions (examples)) The 1233yd obtained above was added to one of the following as a second component: 1230xd, 1231xd, 1231yd, 1232yd, 1242xf, 1243yf, 243ca, 244cb, 244da, 253bb, or CHCl3, in the proportions shown in Table 1-1 or Table 1-2. 500g of each solvent composition was then prepared for Examples 2-6, 10-14, 18-22, 26-30, 34-38, 42-46, 50-54, 58-62, 66-70, 74-78, and 82-86, each containing 1233yd and the second component. The solvent compositions in Examples 2-6 are solvent compositions containing 1233yd and 1230xd as a second component. The solvent compositions in Examples 10-14 are solvent compositions containing 1233yd and 1231xd as a second component. The solvent compositions in Examples 18-22 are solvent compositions containing 1233yd and 1231yd as a second component. The solvent compositions in Examples 26-30 are solvent compositions containing 1233yd and 1232yd as a second component. The solvent compositions in Examples 34-38 are solvent compositions containing 1233yd and 1242xf as a second component. The solvent compositions in Examples 42-46 are solvent compositions containing 1233yd and 1243yf as a second component. The solvent compositions in Examples 50-54 are solvent compositions containing 1233yd and 243ca as a second component. The solvent compositions of Examples 58-62 are solvent compositions containing 1233yd and 244cb as a second component. The solvent compositions of Examples 66-70 are solvent compositions containing 1233yd and 244da as a second component. The solvent compositions of Examples 74-78 are solvent compositions containing 1233yd and 253bb as a second component. The solvent compositions of Examples 82-86 are solvent compositions containing 1233yd and CHCl3 as a second component.

[0058] (Examples 1, 7, 9, 15, 17, 23, 25, 31, 33, 39, 41, 47, 49, 55, 57, 63, 65, 71, 73, 79, 81, 87: Preparation of solvent compositions (comparative examples)) The 1233yd obtained above was added to one of the following as a second component: 1230xd, 1231xd, 1231yd, 1232yd, 1242xf, 1243yf, 243ca, 244cb, 244da, 253bb, or CHCl3, in the proportions shown in Table 1-1 or Table 1-2. 500g of each solvent composition was then prepared for Examples 1, 7, 9, 15, 17, 23, 25, 31, 33, 39, 41, 47, 49, 55, 57, 63, 65, 71, 73, 79, 81, and 87, each containing 1233yd and the second component. The solvent compositions in Examples 1 and 7 are solvent compositions containing 1233yd and 1230xd as a second component. The solvent compositions in Examples 9 and 15 are solvent compositions containing 1233yd and 1231xd as a second component. The solvent compositions in Examples 17 and 23 are solvent compositions containing 1233yd and 1231yd as a second component. The solvent compositions in Examples 25 and 31 are solvent compositions containing 1233yd and 1232yd as a second component. The solvent compositions in Examples 33 and 39 are solvent compositions containing 1233yd and 1242xf as a second component. The solvent compositions in Examples 41 and 47 are solvent compositions containing 1233yd and 1243yf as a second component. The solvent compositions in Examples 49 and 55 are solvent compositions containing 1233yd and 243ca as a second component. The solvent compositions in Examples 57 and 63 are solvent compositions containing 1233yd and 244cb as a second component. The solvent compositions in Examples 65 and 71 are solvent compositions containing 1233yd and 244da as a second component. The solvent compositions in Examples 73 and 79 are solvent compositions containing 1233yd and 253bb as a second component. The solvent compositions in Examples 81 and 87 are solvent compositions containing 1233yd and CHCl3 as a second component.

[0059] (Examples 8, 16, 24, 32, 40, 48, 55, 64, 72, 80, 88: Preparation of solvent compositions (comparative examples)) Using the 1233yd obtained above, 500g each of the solvent compositions for Examples 8, 16, 24, 32, 40, 48, 55, 64, 72, 80, and 88, consisting solely of 1233yd, was prepared.

[0060] (Examples 90-94, 98-102, 106-110, 114-118, 122-126, 130-134, 138-142, 146-150, 154-158, 162-166, 170-174: Preparation of solvent composition (examples)) 1233yd obtained above, along with one of the following as a second component (1230xd, 1231xd, 1231yd, 1232yd, 1242xf, 1243yf, 243ca, 244cb, 244da, 253bb, CHCl3) and tDCE as a third component, were added in the proportions shown in Table 2-1 or Table 2-2 to prepare 500g each of the solvent compositions for Examples 90-94, 98-102, 106-110, 114-118, 122-126, 130-134, 138-142, 146-150, 154-158, 162-166, and 170-174, each containing 1233yd, the second component, and the third component. The solvent compositions of Examples 90-94 are solvent compositions containing 1233yd, 1230xd as a second component, and tDCE as a third component. The solvent compositions of Examples 98-102 are solvent compositions containing 1233yd, 1231xd as a second component, and tDCE as a third component. The solvent compositions of Examples 106-110 are solvent compositions containing 1233yd, 1231yd as a second component, and tDCE as a third component. The solvent compositions of Examples 114-118 are solvent compositions containing 1233yd, 1232yd as a second component, and tDCE as a third component. The solvent compositions of Examples 122-126 are solvent compositions containing 1233yd, 1242xf as a second component, and tDCE as a third component. The solvent compositions of Examples 130-134 are solvent compositions containing 1233yd, 1243yf as a second component, and tDCE as a third component. The solvent compositions of Examples 138-142 are solvent compositions containing 1233yd, 243ca as a second component, and tDCE as a third component. The solvent compositions of Examples 146-150 are solvent compositions containing 1233yd, 244cb as a second component, and tDCE as a third component. The solvent compositions of Examples 154-158 are solvent compositions containing 1233yd, 244da as a second component, and tDCE as a third component. The solvent compositions of Examples 162-166 are solvent compositions containing 1233yd, 253bb as a second component, and tDCE as a third component. The solvent compositions of Examples 170-174 are solvent compositions containing 1233yd, CHCl3 as a second component, and tDCE as a third component.

[0061] (Examples 89, 95, 97, 103, 105, 111, 113, 119, 121, 127, 129, 135, 137, 143, 145, 151, 153, 159, 161, 169, 175: Preparation of solvent compositions (comparative examples)) 1233yd obtained above, along with one of the following as a second component (1230xd, 1231xd, 1231yd, 1232yd, 1242xf, 1243yf, 243ca, 244cb, 244da, 253bb, CHCl3) and tDCE as a third component, were added in the proportions shown in Table 2-1 or Table 2-2 to prepare 500g each of the solvent compositions for Examples 89, 95, 97, 103, 105, 111, 113, 119, 121, 127, 129, 135, 137, 143, 145, 151, 153, 159, 161, 169, and 175, each containing 1233yd, the second component, and the third component. The solvent compositions in Examples 89 and 95 are solvent compositions containing 1233yd, 1230xd as a second component, and tDCE as a third component. The solvent compositions in Examples 97 and 103 are solvent compositions containing 1233yd, 1231xd as a second component, and tDCE as a third component. The solvent compositions in Examples 105 and 111 are solvent compositions containing 1233yd, 1231yd as a second component, and tDCE as a third component. The solvent compositions in Examples 113 and 119 are solvent compositions containing 1233yd, 1232yd as a second component, and tDCE as a third component. The solvent compositions in Examples 121 and 127 are solvent compositions containing 1233yd, 1242xf as a second component, and tDCE as a third component. The solvent compositions of Examples 129 and 135 are solvent compositions containing 1233yd, 1243yf as a second component, and tDCE as a third component. The solvent compositions of Examples 137 and 143 are solvent compositions containing 1233yd, 243ca as a second component, and tDCE as a third component. The solvent compositions of Examples 145 and 151 are solvent compositions containing 1233yd, 244cb as a second component, and tDCE as a third component. The solvent compositions of Examples 153 and 159 are solvent compositions containing 1233yd, 244da as a second component, and tDCE as a third component. The solvent compositions of Examples 161 and 167 are solvent compositions containing 1233yd, 253bb as a second component, and tDCE as a third component. The solvent compositions of Examples 169 and 175 are solvent compositions containing 1233yd, CHCl3 as a second component, and tDCE as a third component.

[0062] (Examples 96, 104, 112, 120, 128, 136, 144, 152, 160, 168, 176: Preparation of solvent compositions (comparative examples)) Using the 1233yd obtained above, 500g each of the solvent compositions for Examples 96, 104, 112, 120, 128, 136, 144, 152, 160, 168, and 176, each consisting of 1233yd and tDCE, was prepared.

[0063] [analysis] Analysis of solvent compositions In the production of various solvent compositions, the compositional analysis of the obtained solvent compositions was performed using gas chromatography (GC). The apparatus used was an Agilent 7890A (manufactured by Agilent Technologies, Inc.), the detector was an FID, the column was a DB-1301 (length 60m x inner diameter 250μm x thickness 1μm, manufactured by Agilent Technologies, Inc.), and helium was used as the carrier gas. The measurement conditions were 30°C → held for 10 minutes → temperature increased at 10°C / min → 240°C.

[0064] [evaluation] Stability testing and metal corrosion resistance testing 100g of each of the solvent compositions from Examples 1 to 176 was placed in a heat-resistant glass bottle containing a test piece of general-purpose cold-rolled steel sheet (SPCC) and stored for 7 days. The results of pH measurement of the solvent compositions immediately after preparation (before testing) and after 7 days of storage (after testing), as well as the evaluation results of the visual observation of the SPCC surface after 7 days of storage (after testing), are shown in Tables 1-1, 1-2, 2-1, and 2-2.

[0065] (pH measurement method) 40 g of each solvent composition from Examples 1-176 and 40 g of pure water prepared to pH 7 were placed in a 200 mL separatory funnel and shaken for 1 minute. After standing, the mixture was allowed to stand, and the upper aqueous layer, which separated into two layers, was separated and its pH was measured using a pH meter (model number: HM-30R, manufactured by Toa DKK Co., Ltd.).

[0066] (Evaluation method for observing the appearance of SPCC surfaces) Changes in the metal surface before and after testing were visually evaluated using untested samples of each metal as a comparison. The evaluation criteria were as follows:

[0067] "S (Excellent)": No change before and after the exam. "A (Good)": The gloss was lost after the test compared to before the test, but there are no practical problems. "B (Slightly Poor)": The surface is slightly rusted after testing. "× (Defective)": Rust was observed across the entire surface after testing.

[0068] [Table 1-1]

[0069] [Table 1-2]

[0070] [Table 2-1]

[0071] [Table 2-2]

[0072] The evaluation results shown in Tables 1-1, 1-2, 2-1, and 2-2 indicate that the solvent compositions in the examples of the present invention all exhibited suppressed acidification compared to the comparative examples. Furthermore, the corrosion of metal test pieces was suppressed in the examples compared to the comparative examples. This clearly demonstrates that the solvent compositions of the present invention not only possess excellent stability but also suppress metal corrosion. Furthermore, Examples 2, 10, 18, 26, 34, 42, 90, 98, 106, 114, 122, and 130, which contain 0.0001% by mass of olefins such as 1230xd, 1231xd, 1242xf, 1243yf, 1231yd, and 1232yd as the second component, show a smaller difference in pH before and after testing compared to examples containing 0.0001% by mass of other compounds as the second component, demonstrating superior stabilizing properties. Furthermore, the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2021-128276, filed on August 4, 2021, are incorporated herein by reference as disclosure of the specification of the present invention.

Claims

1. The first component is 1-chloro-2,3,3-trifluoropropene, A solvent composition comprising, as a second component, at least one selected from the group consisting of 1,2,3,3-tetrachloropropene, 1,2,3-trichloro-3-fluoropropene, 1,3,3-trichloro-2-fluoropropene, 1,3-dichloro-2,3-difluoropropene, 2-chloro-3,3-difluoropropene, 2,3,3-trifluoropropene, 1,3-dichloro-1,2,2-trifluoropropane, 1-chloro-1,2,2,3-tetrafluoropropane, 2-chloro-1,1,3,3-tetrafluoropropane, 2-chloro-1,1,2-trifluoropropane, and chloroform, A solvent composition characterized in that the ratio of the total amount of the second component to the sum of the amount of 1-chloro-2,3,3-trifluoropropene and the total amount of the second component is 0.0001 to 1.0% by mass.

2. The solvent composition according to claim 1, wherein the second component comprises at least one selected from the group consisting of 1,2,3,3-tetrachloropropene, 1,2,3-trichloro-3-fluoropropene, 1,3,3-trichloro-2-fluoropropene, 1,3-dichloro-2,3-difluoropropene, 2-chloro-3,3-difluoropropene, and 2,3,3-trifluoropropene.

3. The solvent composition according to claim 1 or 2, further comprising, as a third component, at least one selected from the group consisting of trans-1,2-dichloroethylene, nonafluorobutoxymethane, nonafluorobutoxyethane, ethanol, isopropanol, 1,2-dichloro-2,3,3-trifluoropropane, and 1,2-dichloro-3,3-difluoropropene.

4. The solvent composition according to any one of claims 1 to 3, wherein the proportion of 1-chloro-2,3,3-trifluoropropene in the solvent composition is 30% by mass or more.

5. A cleaning method characterized by bringing a solvent composition according to any one of claims 1 to 4 into contact with an article to remove dirt adhering to the surface of the article.

6. The cleaning method according to claim 5, wherein at least a portion of the material of the surface of the article that comes into contact with the solvent composition is metal.

7. A coating film-forming composition characterized by comprising a non-volatile organic compound and the solvent composition described in any one of claims 1 to 4.

8. A method for producing a coated substrate, characterized by applying the coating film-forming composition described in claim 7 to the surface of the substrate, and then evaporating and removing the solvent composition to form a coating film containing the non-volatile organic compound.

9. The method for manufacturing a coated substrate according to claim 8, wherein at least a portion of the material on the substrate surface that comes into contact with the solvent composition is metal.

10. An aerosol composition comprising a propellant and a solvent composition according to any one of claims 1 to 4.

11. A heat transfer medium for a thermal cycle system comprising the solvent composition according to any one of claims 1 to 4.

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