WO2021131810A1 - Composition de solvant et son utilisation - Google Patents

Composition de solvant et son utilisation Download PDF

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Publication number
WO2021131810A1
WO2021131810A1 PCT/JP2020/046356 JP2020046356W WO2021131810A1 WO 2021131810 A1 WO2021131810 A1 WO 2021131810A1 JP 2020046356 W JP2020046356 W JP 2020046356W WO 2021131810 A1 WO2021131810 A1 WO 2021131810A1
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WO
WIPO (PCT)
Prior art keywords
solvent composition
chloro
trifluoro
propene
mass
Prior art date
Application number
PCT/JP2020/046356
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English (en)
Japanese (ja)
Inventor
宏明 光岡
Original Assignee
Ａｇｃ株式会社
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Filing date
Publication date
Application filed by Ａｇｃ株式会社 filed Critical Ａｇｃ株式会社
Priority to JP2021567248A priority Critical patent/JPWO2021131810A1/ja
Priority to CN202080090298.3A priority patent/CN114846129B/zh
Publication of WO2021131810A1 publication Critical patent/WO2021131810A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
    • B08B3/00—Cleaning by methods involving the use or presence of liquid or steam
    • B08B3/04—Cleaning involving contact with liquid
    • B08B3/08—Cleaning involving contact with liquid the liquid having chemical or dissolving effect
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen
    • C11D7/30—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds

Definitions

  • the present invention relates to solvent compositions and their uses.
  • hydrofluorochlorocarbon (hereinafter, also referred to as HCFC) having excellent nonflammability, low toxicity, and stability. ) has been used.
  • HCFCs have an adverse effect on the ozone layer, production of HCFCs is scheduled to be completely abolished in 2020 in developed countries.
  • perfluorocarbon hereinafter, also referred to as PFC
  • HFC hydrofluorocarbon
  • HFE hydrofluoroether
  • HCFO-1233yd 1-Chloro-2,3,3-trifluoro-1-propene
  • the HCFO-1233yd Since the HCFO-1233yd has a chlorine atom in the molecule, it has a performance as an oil stain cleaner. However, when the HCFO-1233yd alone comes into contact with the resin material, there may be an effect on the resin material such as whitening or cracking of the resin material or dissolution of the resin. Therefore, there is a problem that the HCFO-1233yd is difficult to use when cleaning a part containing such a resin material or when applying a lubricant or the like to a part containing the resin material. In order to overcome the above problems, a method of adding a chlorine-free fluorine-based solvent such as HFC and HFE has been known as in Patent Document 1. However, there is a problem that the solubility of the processing oil is lowered by the addition of HFC and HFE.
  • the present invention has a solvent composition, a cleaning agent, and a coating film forming composition that do not adversely affect the global environment, have a small effect on the resin material, have sufficient volatility, and have excellent solubility in oils and the like.
  • the present invention provides a solvent composition having the following constitution and its use.
  • the ratio of 1-chloro-2,3,3-trifluoro-1-propene to the total amount of 1-chloro-2,3,3-trifluoro-1-propene and the hydrofluoroether is 25 to 75% by mass.
  • the total content of 1-chloro-2,3,3-trifluoro-1-propene and the hydrofluoroether is 70% by mass or more.
  • a solvent composition characterized by that.
  • Nonaflate butoxymethane is 1-methoxy-2-trifluoromethyl-1,1,2,3,3,3-hexafluoropropane and 1-methoxy-1,1,2,2,3,3.
  • 4,4-Consists of at least one selected from the group consisting of nonaflate butane Nonaflate butane is 1-ethoxy-2-trifluoromethyl-1,1,2,3,3,3-hexafluoropropane and 1-ethoxy-1,1,2,2,3,3,4.
  • the solvent composition according to any one of [1] to [4], which comprises at least one selected from the group consisting of 4,4-nonafluorobutane.
  • a cleaning agent comprising the solvent composition according to any one of [1] to [7].
  • a cleaning method comprising bringing the solvent composition according to any one of [1] to [7] into contact with an article to remove stains adhering to the surface of the article.
  • the solvent composition of the present invention does not adversely affect the global environment, reduces the influence on the resin material, has sufficient volatility, and is excellent in the solubility of hydrophobic solutes such as oils.
  • the method for cleaning an article of the present invention does not adversely affect the global environment, reduces the influence on the resin material, and can clean the dirt adhering to the article. According to the method for producing a coated article of the present invention, the coated article can be produced without adversely affecting the global environment and reducing the influence on the article.
  • the solvent composition of the present invention includes HCFO-1233yd, nonafluorobutoxymethane (C 4 F 9 OCH 3 , hereinafter also referred to as HFE-449s1), nonafluorobutoxyethane (C 4 F 9 OC 2 H 5 , hereinafter). , HFE-569sf), and at least one HFE selected from the group.
  • HFE nonafluorobutoxymethane
  • HFE-569sf nonafluorobutoxyethane
  • the content ratio of HCFO-1233yd to the total amount of HCFO-1233yd and HFE (A) is 25 to 75% by mass, and HCFO-1233yd and HFE (A) with respect to the solvent composition of the present invention.
  • the total amount of is 70% by mass or more.
  • the total amount of HCFO-1233yd and HFE (A) in the solvent composition is preferably 90% by mass or more based on the total amount of the solvent composition. Further, in the solvent composition of the present invention, the influence on the resin material described later is reduced by optimizing the composition ratio of the solvent composition.
  • the mass ratio of HCFO-1233yd and HFE (A) is within the range of 25 to 75% by mass in the content ratio of HCFO-1233yd to the total amount of HCFO-1233yd and HFE (A).
  • the mass ratio for forming a pseudo-azeotropic mixture is preferable, and the mass ratio for forming an azeotropic mixture is preferable. More preferred.
  • the pseudo-azeotropic mixture means a mixture having a specific azeotrope of 0.5 to 2, which will be described later, and the azeotropic mixture means a mixture having a specific azeotrope of 1.
  • HCFO-1233yd and HFE The specific volatility of the mixture of both HCFO-1233yd and HFE (A) varies depending on the type and composition of each (for example, steric isomer ratio and structural isomer ratio), but HCFO-1233yd and HFE (A) Many mixtures in the range in which the content ratio of HCFO-1233yd to the total amount of azeotrope is 25 to 75% by mass are pseudo-azeotropic mixtures and may be azeotropic mixtures.
  • HCFO-1233yd is an olefin having a carbon atom-carbon atom double bond. Therefore, the life in the atmosphere is short, and the ozone depletion potential and global warming potential are small. It is known that HCFO-1233yd has a stereoisomer, and the boiling point of the Z isomer of HCFO-1233yd (hereinafter, also referred to as HCFO-1233yd (Z)) is 54 ° C., and that of HCFO-1233yd. The boiling point of the E isomer (hereinafter, also referred to as HCFO-1233yd (E)) is 46 ° C.
  • HCFO-1233yd (Z) and HCFO-1233yd (E) and a mixture thereof can be obtained, and both can be separated by distillation. it can.
  • the HCFO-1233yd contained in the solvent composition of the present invention may be only one of both isomers, but in consideration of productivity, it is a mixture of isomers having a high proportion of HCFO-1233yd (Z). preferable.
  • the content of HCFO-1233yd (Z) is preferably 50% by mass or more, more preferably 75 to 98% by mass, and 90 to 98%. It is particularly preferably mass%.
  • HCFO-1233yd Since it has the above boiling point, HCFO-1233yd has excellent volatility and is easy to handle. HCFO-1233yd has no flash point. HCFO-1233yd has low surface tension and viscosity, and easily evaporates even at room temperature. HCFO-1233yd is excellent in cleaning and removing processing oil, fluorine oil, silicone oil, synthetic oil, mold release agent, dust and the like, and solubility of lubricants such as fluorine oil and silicone oil.
  • HCFO-1233yd has excellent solubility of various hydrophobic solutes and has sufficient performance as a diluting solvent for detergents and lubricants. Further, since HCFO-1233yd has a boiling point suitable for a solvent, it is easy to handle at the time of use, and since it does not volatilize when used at room temperature, it can be recovered and reused, and the cost can be suppressed.
  • HCFO-1233yd for example, industrially stably available 1-chloro-2,2,3,3-tetrafluoro-propane (CHF 2 -CF 2 -CHFCl. Hereinafter referred to as HCFC-244ca.)
  • the It can be produced by a hydrogen fluoride reaction at a temperature of 50 to 80 ° C. using potassium hydroxide or sodium hydroxide as a reactant.
  • the solvent composition of the present invention contains HCFO-1233yd and a stabilizer that suppresses its decomposition.
  • a stabilizer nitro compounds, amines, phenols, benzotriazoles, epoxide compounds and hydrocarbons are preferable. Since the solvent composition of the present invention contains such a stabilizer, the solvent composition can be used without decomposition even under harsh conditions such as heating conditions.
  • the stabilizer one kind may be used, or two or more kinds may be used.
  • the amount of the stabilizer is preferably 1 mass ppm or more, preferably 3 mass ppm or more, based on the total amount of HCFO-1233 yd in the solvent composition. It is more preferable that there is, and it is particularly preferable that it is 5 mass ppm or more.
  • the upper limit of the amount of the stabilizer is preferably 5% by mass, particularly preferably 1% by mass.
  • the stabilizer examples include nitro compounds such as nitromethane, nitroethane, nitropropane and nitrobenzene, diethylamine, triethylamine, isopropylamine, diisopropylamine, butylamine, isobutylamine, tert-butylamine, ⁇ -picolin, N-methylbenzylamine and diallylamine.
  • nitro compounds such as nitromethane, nitroethane, nitropropane and nitrobenzene, diethylamine, triethylamine, isopropylamine, diisopropylamine, butylamine, isobutylamine, tert-butylamine, ⁇ -picolin, N-methylbenzylamine and diallylamine.
  • Amines such as N-methylmorpholin and N-methylpyrrole, phenol, o-cresol, m-cresol, p-cresol, timol, p-tert-butylphenol, tert-butylcatechol, catechol, isooigenol, o-methoxyphenol , 4,4'-Dihydroxyphenyl-2,2-propane, isoamyl salicylate, benzyl salicylate, methyl salicylate, phenols such as 2,6-di-t-butyl-p-cresol, 2- (2'-hydroxy- 5'-Methylphenyl) benzotriazole, 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 1,2,3-benzotriazole, 1-[( N, N-bis-2-ethylhexyl) aminomethyl] benzotriazoles such as benzotriazoles, 1,2-propylene oxide, 1,
  • HFE (A) By containing HFE (A), the solvent composition of the present invention reduces the influence on the resin material and has excellent solubility of oils and the like.
  • HFE-449s1 means a compound represented by C 4 F 9 OCH 3.
  • HFE-449s1 has four types of structural isomers, and the HFE-449s1 contained in the solvent composition of the present invention may be only one of them, or a mixture of two or more of them. May be good.
  • the HFE-449s1 contained in the solvent composition of the present invention includes 1-methoxy-2-trifluoromethyl-1,1,2,3,3,3-hexafluoropropane and 1-methoxy-1,1,.
  • a mixture with 2,2,3,3,4,5,4-nonafluorobutane is preferred. Examples of this mixture include the product "Novec7100" (manufactured by 3M Ltd.).
  • HFE-449s1 has a boiling point of 61 ° C., and even if it is boiled to become steam, it is 61 ° C., so even parts that are easily affected by heat, such as resin parts, are unlikely to have an adverse effect. HFE-449s1 has no flash point. HFE-449s1 has low surface tension and viscosity, and easily evaporates even at room temperature. HFE-449s1 can be used for resin materials such as acrylic resin, ABS resin, polycarbonate, and polyethylene, which are less affected by the resin material and cannot use HCFO-1233yd. On the other hand, since HFE-449s1 does not have a chlorine atom in its molecule, the solubility of oils such as processing oil and lubricating oil is not sufficient.
  • HFE-449s1 has no flash point except that the solubility of oils is not sufficient, has a small effect on the resin material, and is excellent in volatility.
  • HFE-449s1 can be produced by a known method.
  • CF 3 CF 2 CF 2 C (O) F, CF 3 CF (CF 3 ) C (O) F and C 2 F 5 C (O) CF 3 and any suitable source of anhydrous fluoride ions, such as anhydrous alkali metal fluoride (eg, potassium fluoride or cesium fluoride), or anhydrous silver fluoride, are obtained from the Aldrich Chemical Company. It can be prepared by reacting with an alkylating agent such as dimethylsulfate in an anhydrous polar aproton solvent in the presence of a possible quaternary ammonium compound such as ADOGEN464.
  • an alkylating agent such as dimethylsulfate
  • an anhydrous polar aproton solvent in the presence of a possible quaternary ammonium compound such as ADOGEN464.
  • HFE-569sf means a compound represented by C 4 F 9 OC 2 H 5.
  • HFE-569sf has four types of structural isomers, and the HFE-569sf contained in the solvent composition of the present invention may be only one of them, or a mixture of two or more of them. May be good.
  • the HFE-569sf contained in the solvent composition of the present invention includes 1-ethoxy-2-trifluoromethyl-1,1,2,3,3,3-hexafluoropropane and 1-ethoxy-1,1,.
  • a mixture of 2,2,3,3,4,5,4-nonafluorobutane is preferred. Examples of this mixture include the product "Novec7200" (manufactured by 3M).
  • HFE-569sf has a boiling point of 76 ° C., and even if it is boiled to become steam, it is at 76 ° C., so even parts that are easily affected by heat, such as resin parts, are unlikely to have an adverse effect.
  • HFE-569sf has no flash point.
  • HFE-569sf has low surface tension and viscosity, and easily evaporates even at room temperature.
  • HFE-569sf can be used for resin materials such as acrylic resin, ABS resin, polycarbonate, and polyethylene, which are less affected by the resin material and cannot use HCFO-1233yd.
  • HFE-569sf does not have a chlorine atom in its molecule, the solubility of oils such as processing oils and lubricating oils is not sufficient.
  • HFE-569sf has no flash point except that the solubility of oils is not sufficient, has a small effect on the resin material, and is excellent in volatility.
  • HFE-569sf can be produced by a known method.
  • CF 3 CF 2 CF 2 C (O) F, CF 3 CF (CF 3 ) C (O) F, and C 2 F 5 C (O) CF 3 ADOGEN 464 as well as mixtures thereof and any suitable source of anhydrous fluoride ions such as anhydrous alkali metal fluoride (eg, potassium fluoride or cesium fluoride) or anhydrous silver fluoride are available from the Aldrich Chemical Company. It can be prepared by reacting with an alkylating agent such as diethyl fluoride in an anhydrous polar aproton solvent in the presence of a quaternary ammonium compound such as.
  • an alkylating agent such as diethyl fluoride in an anhydrous polar aproton solvent in the presence of a quaternary ammonium compound such as.
  • the solvent composition of the present invention is an organic solvent other than HCFO-1233yd and HFE (A) (hereinafter, organic) in an amount of 30% by mass or less, preferably 10% by mass or less based on the total amount of the solvent composition, if necessary. It may also contain a solvent (B)).
  • the organic solvent (B) is an organic solvent that is soluble in HCFO-1233yd and HFE (A).
  • the organic solvent (B) is appropriately selected according to various purposes such as increasing the solubility and adjusting the volatilization rate.
  • Examples of the organic solvent (B) include HCFO-1233yd, hydrocarbons soluble in HFE (A), alcohols, ketones, non-fluorinated ethers, esters, chlorocarbons, HFCs, and HFEs (excluding HFE (A)). Examples thereof include HFO and HCFO other than HCFO-1233yd.
  • the organic solvent (B) is preferably 10% by mass or less, more preferably 7% by mass or less, and particularly preferably 5% by mass or less, based on the total amount of the solvent composition.
  • hydrocarbon a hydrocarbon having 5 or more carbon atoms is preferable.
  • the hydrocarbon may be chain-like, cyclic, saturated hydrocarbon, or unsaturated hydrocarbon.
  • n-pentane, cyclopentane, n-hexane, cyclohexane, and n-heptane are preferable.
  • an alcohol having 1 to 16 carbon atoms is preferable.
  • the alcohol may be chain-like, cyclic, saturated alcohol, or unsaturated alcohol.
  • methanol, ethanol and isopropyl alcohol are preferable.
  • ketone a ketone having 3 to 9 carbon atoms is preferable.
  • the ketone may be chain-like, cyclic, saturated ketone, or unsaturated ketone.
  • acetone and methyl ethyl ketone are preferable.
  • non-fluorine-based ether an ether having 2 to 8 carbon atoms is preferable.
  • the non-fluorine-based ether may be chain-like, cyclic, saturated ether, or unsaturated ether.
  • ether diethyl ether, diisopropyl ether and tetrahydrofuran are preferable.
  • ester an ester having 2 to 19 carbon atoms is preferable.
  • the ester may be chain-like, cyclic, saturated ester, or unsaturated ester.
  • methyl acetate and ethyl acetate are preferable.
  • chlorocarbon chlorocarbon having 1 to 3 carbon atoms is preferable.
  • the chlorocarbon may be chain-like, cyclic, saturated chlorocarbon, or unsaturated chlorocarbon.
  • methylene chloride, trans-1,2-dichloroethylene and trichlorethylene are more preferable.
  • HFC a chain or cyclic HFC having 4 to 8 carbon atoms is preferable, and an HFC having a fluorine atom number in one molecule of hydrogen atoms or more is more preferable.
  • HFC 1,1,1,2,2,3,4,5,5-decafluoropentane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, 1,1,1,2,2,3,3,4,5,5,6,6-tridecafluorohexane is preferable.
  • HFE other than HFE (A) 1,1,2,2-tetrafluoroethoxy-1- (2,2,2-trifluoro) ethane (hereinafter, also referred to as HFE-347pc-f) and the like are preferable.
  • HCFO other than HFO and HCFO-1233yd a chain HFO having 3 or 4 carbon atoms and an HCFO other than HCFO-1233yd are preferable.
  • the HFO is preferably the E isomer or the Z isomer of 1,1,1,4,4,4-hexafluoro-2-butene, and the HCFO other than HCFO-1233yd is 1-chloro-3,3,3.
  • the E or Z isomer of 3-trifluoropropene is preferred.
  • the organic solvent (B) may be one kind or two or more kinds.
  • the combination thereof may be a combination of solvents in the same category or a combination of solvents in different categories.
  • it may be a combination of two kinds selected from hydrocarbons, or a combination of one kind selected from hydrocarbons and one kind selected from alcohols.
  • the organic solvent (B) is a solvent having no flash point.
  • Organic solvents that do not have a flammable point include 1,1,1,2,2,3,4,5,5-decafluoropentane, 1,1,1,2,2,3,3,4.
  • HFCs such as 4-nonafluorohexane, 1,1,1,2,2,3,3,4,5,5,6,6-tridecafluorohexane, and HFEs such as HFE-347pc-f
  • HFO such as E isomer or Z isomer of 1,1,1,4,4,4-hexafluoro-2-butene, E isomer or Z isomer of 1-chloro-3,3,3-trifluoropropene HCFO and the like of the body and the like can be mentioned.
  • a solvent having a flash point is used as the organic solvent (B)
  • the solvent composition of the present invention does not adversely affect the global environment, reduces the influence on the resin material, has sufficient volatility, and has excellent solubility of hydrophobic substances such as oils and mineral oils. Since the solvent composition of the present invention has excellent performance as a solvent, it can be used as a cleaning agent for removing hydrophobic substances such as oil stain cleaning, flux cleaning, precision cleaning, dry cleaning of clothes and stain removal. Further, the solvent composition of the present invention includes a silicone-based lubricant, a lubricant such as a fluorine-based lubricant, a rust preventive made of mineral oil, synthetic oil, etc., a moisture-proof coating agent for water-repellent treatment, and an antifouling treatment.
  • the hydrophobic substance is dissolved in the solvent composition of the present invention to obtain a coating film forming composition, the coating film forming composition is applied to the surface of an article, and then the solvent is evaporated and removed to obtain the hydrophobic substance.
  • the coating film can be formed.
  • the solvent composition of the present invention is also suitable as a heat transfer medium for heating or cooling an article.
  • the cleaning agent of the present invention is characterized by comprising the solvent composition of the present invention.
  • the cleaning method of the present invention is characterized in that the solvent composition of the present invention is brought into contact with an article to remove stains adhering to the article.
  • the solvent composition of the present invention may be brought into contact with the surface of the article.
  • hand wiping, immersion, spraying, shaking, ultrasonic waves, steam cleaning, or a method combining these may be adopted.
  • cleaning devices, cleaning conditions, and the like can be appropriately selected.
  • the temperature of the solvent composition of the present invention in the first immersion tank is 25 ° C. or higher, and the solvent composition It is preferable that the temperature is lower than the boiling point of the product. Within the above temperature range, dirt such as processing oil can be easily washed, and the cleaning effect by ultrasonic waves is high. Further, it is preferable that the temperature of the solvent composition of the present invention in the second immersion tank is 10 to 35 ° C. If it is within the above temperature range, the rinsing and cleaning effect is high. Further, from the viewpoint of detergency, it is preferable that the temperature of the solvent composition of the present invention in the first immersion tank is higher than the temperature of the solvent composition in the second immersion tank.
  • the material of the article to which the solvent composition of the present invention can be applied examples include metals, resins, elastomers, glass, and ceramics.
  • the article may be an article made of a composite material having these two or more kinds of materials. Examples of the composite material include a laminate of metal and resin.
  • the solvent composition of the present invention relates to an article made of a material containing a resin such as ABS resin, polycarbonate (PC), polystyrene (PS), and polyether sulfone (PES), for which HCFO-1233yd could not be used. Can also be used.
  • Specific examples of the articles include textile products, medical equipment, electrical / electronic equipment, precision machinery, optical equipment, transportation machinery, and parts thereof.
  • the solvent composition of the present invention can also be used for an article in which at least a part of the material on the surface of the article in contact with the solvent composition is a resin material such as the above resin.
  • the solvent composition of the present invention is characterized by reducing the influence on the resin material. It is preferable to change the content ratio of the composition for each resin material to be cleaned.
  • the content ratio of HCFO-1233yd to the total amount of HCFO-1233yd and HFE (A) as the solvent composition is 25 to 50% by mass.
  • the composition is preferred.
  • the solvent composition is preferably a composition in which the content ratio of HCFO-1233yd is 50 to 75% by mass. With these solvent compositions, the influence on each resin material can be reduced.
  • examples of the deposits to be washed and removed include flux, processing oil, mold release agent, dust and the like adhering to various objects to be cleaned.
  • examples of the processing oil include cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, press processing oil, punching oil, drawing oil, assembly oil, drawing oil and the like. Since this solvent composition is superior in solubility in these oils as compared with conventional solvent compositions such as HFC and HFE, it is preferable to use this solvent composition for cleaning stains composed of these oils.
  • composition for forming a coating film, method for producing a base material with a coating film can also be used as a solvent for forming a coating film of a non-volatile organic compound.
  • the coating film forming composition of the present invention is characterized by containing a non-volatile organic compound and the solvent composition of the present invention.
  • the coating film-forming composition of the present invention is applied to the surface of the substrate, and then the solvent composition of the present invention is evaporated and removed to remove the non-volatile organic material. It is characterized by forming a coating film of a compound.
  • the coating film forming composition is usually prepared as a solution-like composition in which a non-volatile organic compound is dissolved in the solution composition of the present invention.
  • the method for preparing the coating film forming composition is not particularly limited as long as it is a method capable of uniformly dissolving the non-volatile organic compound in the solvent composition of the present invention in a predetermined ratio.
  • the coating film forming composition is basically composed only of a non-volatile organic compound and the solvent composition of the present invention.
  • the content of the non-volatile organic compound in the coating film forming composition (100% by mass) is preferably 0.01 to 50% by mass, more preferably 0.05 to 30% by mass, and 0.1 to 20% by mass. % Is particularly preferable.
  • the film thickness of the coating film when the coating film forming composition is applied and the non-volatile after evaporation removal (hereinafter, also referred to as drying) of the solvent composition It is easy to adjust the thickness of the organic compound coating film within an appropriate range.
  • the non-volatile organic compound in the present invention has a boiling point higher than that of the solvent composition of the present invention, and the organic compound remains on the surface even after the solvent composition evaporates.
  • the non-volatile organic compound include a lubricant for imparting lubricity to an article, a rust inhibitor for imparting a rust preventive effect on metal parts, and a moisture-proof coating agent for imparting water repellency to an article.
  • antifouling coating agents such as anti-fingerprint agents for imparting antifouling performance to articles.
  • Lubricant means a lubricant used to reduce friction on the contact surface and prevent heat generation and friction damage when the two members move with their surfaces in contact with each other.
  • the lubricant may be in the form of a liquid (oil), a semi-solid (grease), or a solid.
  • a mineral oil-based lubricant a synthetic oil-based lubricant, a fluorine-based lubricant or a silicone-based lubricant is preferable because of its excellent solubility in the solvent composition of the present invention.
  • the fluorine-based lubricant means a lubricant having a fluorine atom in the molecule.
  • the silicone-based lubricant means a lubricant containing silicone.
  • the lubricant contained in the coating film forming composition may be one kind or two or more kinds.
  • the fluorine-based lubricant and the silicone-based lubricant may be used alone or in combination.
  • fluorine-based lubricant examples include fluorine-based solid lubricants such as fluorine oil, fluorine grease, and resin powder of polytetrafluoroethylene.
  • fluorine oil a low polymer of perfluoropolyether or chlorotrifluoroethylene is preferable.
  • the product names "Clitex (registered trademark) GPL102" manufactured by DuPont Co., Ltd.
  • Daikin "Daikin # 3"
  • Daikin # 10 "Daikin # 20", “Daikin # 50”
  • Examples thereof include “Daifuroil # 100" and "Demnum S-65” (manufactured by Daikin Industries, Ltd.).
  • fluorine grease it is preferable that a fluorine oil such as a low polymer of perfluoropolyether or chlorotrifluoroethylene is used as a base oil, and a polytetrafluoroethylene powder or other thickener is blended.
  • a fluorine oil such as a low polymer of perfluoropolyether or chlorotrifluoroethylene is used as a base oil, and a polytetrafluoroethylene powder or other thickener is blended.
  • silicone-based lubricants examples include silicone oil and silicone grease.
  • silicone oil dimethyl silicone, methyl hydrogen silicone, methyl phenyl silicone, cyclic dimethyl silicone, and modified silicone oil in which an organic group is introduced into a side chain or a terminal are preferable.
  • silicone grease a product containing various silicone oils mentioned above as a base oil, a thickener such as metal soap, and various additives is preferable.
  • product names “Shinetsu Silicone G-30 Series", “Shinetsu Silicone G-40 Series", “Shinetsu Silicone FG-720 Series", “Shinetsu Silicone G-411", “Shinetsu Silicone G-501", “Shinetsu Silicone” “G-6500", “Shinetsu Silicone G-330", “Shinetsu Silicone G-340", “Shinetsu Silicone G-350", “Shinetsu Silicone G-630” (all manufactured by Shinetsu Chemical Industry Co., Ltd.), “Moricoat (Moricoat) "Registered trademark) SH33L”, “Moricoat (registered trademark) 41", “Moricoat (registered trademark) 44", “Moricoat (registered trademark) 822M”, “Moricoat (registered trademark) 111", "Moricoat
  • the rust preventive agent means an agent used to cover the surface of a metal that is easily oxidized by oxygen in the air to generate rust and to block the metal surface from oxygen to prevent rusting of the metal material.
  • examples of the rust preventive include mineral oils, polyol esters, polyalkylene glycols, and synthetic oils such as polyvinyl ether.
  • Examples of products of the moisture-proof coating agent include Topas 5013, Topas 6013, Topas 8007 (above, manufactured by Polyplastics), Zeonoa 1020R, Zeonoa 1060R (above, manufactured by Nippon Zeon), Appel 6011T, Appel 8008T (above, Mitsui). (Manufactured by Chemicals), SFE-DP02H, SNF-DP20H (all manufactured by AGC Seimi Chemicals).
  • Examples of antifouling coating agents such as anti-fingerprint agents include Optool DSX, Optool DAC (above, manufactured by Daikin Industries, Ltd.) Fluorosearch FG-5000 (above, manufactured by Fluorotechnology) SR-4000A (above, AGC). (Manufactured by Seimi Chemical Co., Ltd.).
  • the coating film forming composition is applied to the surface of the base material to form a film of the coating film forming composition on the surface of the base material, and then the solvent composition is formed from the film of the coating film forming composition formed on the surface of the base material.
  • the solvent composition is formed from the film of the coating film forming composition formed on the surface of the base material.
  • Examples of the coating method of the coating film forming composition include coating by a brush, coating by spraying, coating by immersing an article in the coating film forming composition, and tube or injection by sucking up the coating film forming composition. Examples thereof include a coating method in which the coating film forming composition is brought into contact with the inner wall of the needle.
  • drying method As a method for evaporating and removing the solvent composition from the coating film forming composition, a known drying method can be mentioned. Examples of the drying method include air drying and drying by heating. The drying temperature is preferably 20 to 100 ° C.
  • the method for producing a base material with a coating film of the present invention it is possible to produce a base material with a coating film having a coating film containing a lubricant, a rust preventive, a moisture-proof coating agent, an antifouling coating agent, etc. it can. That is, as the base material to which the coating film forming composition is applied, a base material made of various materials such as metal, resin, rubber, glass, and ceramics is adopted. Further, the coating film forming composition of the present invention can be applied to an article containing a resin material without any influence.
  • the base material with a coating include those in which a fluorine-based lubricant is used, and household equipment such as CD and DVD tray parts, printers, copy equipment, and flux equipment in industrial equipment, personal computers, and audio equipment. Alternatively, office equipment and the like can be mentioned.
  • examples of those in which a silicone-based lubricant is used include syringes, cylinders, medical tube parts, metal blades, catheters and the like.
  • Examples of products to which a moisture-proof coating agent or an antifouling coating agent has been used include equipment used to impart moisture-proof and stain-proof properties to plastic materials, rubber materials, metal materials, glass materials, mounting recovery plates, etc. Be done.
  • the solvent composition of the present invention is characterized by reducing the influence on the resin material.
  • the material on the surface of the base material in contact with the solvent composition is a resin material, it is preferable to change the content ratio of the composition for each resin material.
  • the solvent composition contains 25 to 50% by mass of HCFO-1233yd with respect to the total amount of HCFO-1233yd and HFE (A).
  • the composition is preferred.
  • the solvent composition is preferably a composition in which the content ratio of HCFO-1233yd is 50 to 75% by mass. With these solvent compositions, the influence on each resin material can be reduced.
  • the solvent composition of the present invention can also be used as an aerosol composition containing a propellant and a solute dissolved in the solvent composition.
  • the propellant include liquefied gas and compressed gas.
  • the liquefied gas in the aerosol composition include dimethyl ether (DME), liquefied petroleum gas (LPG), propane, butane, isobutane, 1,1-difluoroethane (HFC-152a), and 1,1,1,2-tetrafluoroethane (1,1,1,2-tetrafluoroethane).
  • HFC-134a 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,3,3,3-tetrafluoropropene (HFO-1234ze) and the like.
  • examples of the compressed gas include nitrogen, carbon dioxide, nitrous oxide and the like.
  • the solvent composition of the present invention can be used as a working medium (heat transfer medium) for a thermodynamic cycle system. That is, the present invention provides a heat transfer medium containing the solvent composition of the present invention.
  • the heat transfer medium of the present invention can be applied to a thermodynamic cycle system for heating or cooling a substance.
  • Examples of the heat cycle system include a Rankine cycle system, a heat pump cycle system, a refrigeration cycle system, a heat transport system, a secondary refrigerant cooling system, and the like.
  • the refrigeration cycle system will be described as an example of the thermal cycle system.
  • the refrigeration cycle system is a system that cools the load fluid and cools it to a lower temperature by removing the thermal energy of the working refrigerant with the load fluid in the evaporator.
  • a compressor that compresses the working medium steam A into a high-temperature and high-pressure working medium steam B and a condenser that cools the compressed working medium steam B and liquefies it into a low-temperature and high-pressure working medium C.
  • An expansion valve that expands the working medium C discharged from the condenser to obtain a low-temperature and low-pressure working medium D
  • an evaporation valve that heats the working medium D discharged from the expansion valve to obtain a high-temperature and high-pressure working medium steam A.
  • It is a system including a vessel, a pump that supplies the load fluid E to the evaporator, and a pump that supplies the fluid F to the condenser.
  • the heat transfer medium of the present invention can also be applied to a secondary circulation cooling system.
  • the secondary circulation cooling system circulates a primary cooling means for cooling a primary refrigerant composed of ammonia or a hydrocarbon refrigerant and a secondary refrigerant for a secondary cooling means system (hereinafter referred to as "secondary refrigerant") to be covered. It is a system having a secondary circulation cooling means for cooling a cooled object and a heat exchanger for cooling the secondary refrigerant by exchanging heat between the primary refrigerant and the secondary refrigerant. This secondary circulation cooling system can cool the object to be cooled.
  • the heat transfer medium of the present invention is preferable for use as a secondary refrigerant.
  • Examples 1 to 24 are examples of the solvent composition of the present invention, and Examples 25 to 34 are comparative examples.
  • the HFE used for preparing the solvent composition is as shown below.
  • the reactor was heated to 100 ° C., and reactive distillation was carried out using a reflux timer at a reflux time / distillation time ratio of 5/1.
  • the distilled HCFC-244ca was neutralized with a 20 mass% potassium hydroxide aqueous solution.
  • the recovered HCFC-244ca (purity 100% by mass) was 979 g (6.50 mol).
  • HCFO-1233yd (Preparation of HCFO-1233yd)
  • the HCFO-1233yd used in the examples had a mass ratio of HCFO-1233yd (Z) to HCFO-1233yd (E) (1233yd (Z) / 1233yd (E)) of 95 / 5,80 / 20,55 / 45.
  • p-methoxyphenol was added so as to be 0.01% by mass.
  • MDX refers to MDX4-4159
  • KF refers to KF-96-500cs.
  • Examples 11 to 24, 27 to 34 Prepare HCFO-1233yd and the above HFE in the amounts shown in Table 3 so that the total amount of the solvent composition in the collection vial bottle is 4.5 g, and put the metalworking oil (manufactured by Idemitsu Kosan Co., Ltd., Daphni Marg) in the collection vial bottle. Plus LA-5) 0.5 g was added. Solubility was evaluated based on the above criteria for the state (solubility) of the solution after mixing the solvent composition and the metalworking oil and allowing it to stand at 40 ° C. for 10 minutes. The results are shown in Table 3. In addition, "LA-5" in Table 3 refers to the said Daphni Marg Plus LA-5.
  • HCFO-1233 yd and the HFE were each prepared in the amounts shown in Table 3 so that the total amount of the solvent composition was 80 g, and a test piece (20 mm ⁇ ) of polyether sulfone (PES) was prepared. 30 mm x 3 mm thick) were put in one by one. After allowing the screw cap heat-resistant bottle to stand at 54 ° C. for one day, the test piece was taken out and the appearance was evaluated according to the above criteria. The results are shown in Table 3.
  • the ratio of HCFO-1233yd to the total amount of HCFO-1233yd and HFE is 25 to 75% by mass, and the total amount of HCFO-1233yd and HFE is 70% by mass or more in Examples 1 to 24. It can be seen that all of the solvent compositions have excellent solubility of oils and the influence on the resin material is reduced.
  • Examples 11 to 24, 27 to 34 A cleaning post-flux (manufactured by Kouki Co., Ltd., JS-15CAT) is applied to a comb-shaped substrate (conductor width: 0.40 mm, conductor spacing: 0.19 mm, stacking allowance: 15.87 mm, overall substrate dimensions: 50 x 50 mm). After drying at 100 ° C. for 10 minutes, soldering was performed in a jet-type lead soldering tank at 260 ° C., and the substrate was allowed to stand overnight to prepare a soldered substrate. The substrate obtained as described above was subjected to a cleaning test by the following method using the solvent compositions of Examples 11 to 24 and 27 to 34 shown in Table 3.
  • a 500 ml glass beaker containing 500 ml of the solvent composition was subjected to immersion cleaning at an output of 200 W and an ultrasonic wave having a frequency of 35 kHz at a liquid temperature of 45 ° C. for 3 minutes, and further 500 ml of the solvent composition was added.
  • Rinsing was carried out by immersing in a 500 ml glass beaker for 3 minutes, and finally the above washing was carried out in a 2000 ml beaker equipped with a cooling coil for 3 minutes.
  • the residue could be removed from the substrate.
  • the solvent composition adhering to the test piece was immediately dried. In Examples 27 to 34, a residual was observed on the substrate after cleaning.
  • a coating film was formed.
  • the coating film was uniformly formed by visual evaluation.
  • the lubricating oil did not dissolve and the test could not be performed.
  • the solvent composition of the present invention has excellent performance as a solvent, it is useful as a cleaning solvent for removing stains such as oils and dust, and a solvent for forming a coating film. In particular, it is useful for removing dirt such as dust and oil that adheres to an article whose surface is made of a resin material.

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Abstract

La présente invention concerne : une composition de solvant qui n'exerce pas d'influence défavorable sur l'environnement global, exerce peu d'influence sur les matières résineuses, présente une aptitude au séchage suffisante, et présente une excellente solubilité dans les huiles, les graisses, etc ; un procédé de nettoyage d'un article à l'aide de la composition de solvant ; un procédé de production d'un article revêtu ; un milieu de transfert de chaleur comprenant la composition de solvant ; et un système de cycle thermique utilisant le milieu de transfert de chaleur.　La composition de solvant est caractérisée en ce qu'elle comprend du 1-chloro -2,3,3-trifluoro-1-propène et au moins un hydrofluoroéther choisi dans le groupe constitué par le nonafluorobutoxyméthane et le nonafluorobutoxyéthane, la proportion du 1-chloro -2,3,3-trifluoro-1-propène étant de 25 à 75 % en masse par rapport à la quantité totale du 1-chloro -2,3,3-trifluoro-1-propène et de l'hydrofluoroéther, la teneur totale du 1-chloro -2,3,3-trifluoro-1-propène et de l'hydrofluoroéther étant supérieure ou égale à 70 % en masse.
PCT/JP2020/046356 2019-12-24 2020-12-11 Composition de solvant et son utilisation WO2021131810A1 (fr)

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WO2023009358A1 (fr) * 2021-07-29 2023-02-02 Chemours-Mitsui Fluoroproducts Co., Ltd Composition de solvant à base de fluor
WO2023168268A1 (fr) * 2022-03-01 2023-09-07 Honeywell International Inc. Compositions azéotropes ou de type azéotrope de 1,1,1,3,3,3-hexafluoro-2-(2,2,2-trifluoroéthoxy)propane et leurs applications

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WO2023168268A1 (fr) * 2022-03-01 2023-09-07 Honeywell International Inc. Compositions azéotropes ou de type azéotrope de 1,1,1,3,3,3-hexafluoro-2-(2,2,2-trifluoroéthoxy)propane et leurs applications

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