WO2022009801A1 - Composition et utilisation correspondante - Google Patents

Composition et utilisation correspondante Download PDF

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Publication number
WO2022009801A1
WO2022009801A1 PCT/JP2021/025155 JP2021025155W WO2022009801A1 WO 2022009801 A1 WO2022009801 A1 WO 2022009801A1 JP 2021025155 W JP2021025155 W JP 2021025155W WO 2022009801 A1 WO2022009801 A1 WO 2022009801A1
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Prior art keywords
mass
content
isomer
chloro
coordinate
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English (en)
Japanese (ja)
Inventor
洋輝 速水
宏明 光岡
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AGC Inc
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Asahi Glass Co Ltd
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Priority to CN202180044125.2A priority Critical patent/CN115702235B/zh
Priority to JP2022535299A priority patent/JPWO2022009801A1/ja
Publication of WO2022009801A1 publication Critical patent/WO2022009801A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/08—Liquid soap, e.g. for dispensers; capsuled
    • 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

Definitions

  • the present invention relates to a composition and its use.
  • hydrochlorofluorocarbon (hereinafter, also referred to as HCFC) having excellent nonflammability, low toxicity, and stability has been used as a diluting solvent for cleaning liquids, lubricants, and the like used for cleaning oil stains and dust.
  • HCFCs have an adverse effect on the ozone layer, HCFC production is scheduled to be completely abolished in 2020 in developed countries.
  • perfluorocarbon hereinafter, also referred to as PFC
  • hydrofluorocarbon hereinafter, also referred to as HFC
  • hydrofluoroether hereinafter, also referred to as HFE
  • HFCs and PFCs are regulated substances under the Kyoto Protocol. Further, HFCs, HFEs and PFCs have lower solubility of fats and oils as compared with HCFCs, and their application range is narrow as a solvent application.
  • Patent Document 1 proposes a solvent composition that does not adversely affect the global environment, has a small effect on the resin material, has sufficient drying property, and has excellent solubility in oils and fats.
  • Patent Document 1 When the cleaning liquid used for cleaning oil stains and dust is used as an aerosol together with a propellant, it is required that the liquid does not easily remain, the cleaning property of the target object is excellent, and the influence on the material of the target article is small.
  • the solvent composition described in Patent Document 1 could not solve the above three problems at the same time.
  • the present invention provides a composition and its use which does not adversely affect the global environment, does not leave a liquid easily when used as an aerosol, has excellent detergency of an object, and has a small effect on the material of the object. Is the subject.
  • the phase diagram of the three values of the content (% by mass) of 1 and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene In the phase diagram of the three values of the content (% by mass) of 1 and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene.
  • the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene, the nonafluorobutoxymethane (B) and the 1-chloro-3,3,3-trifluoropropene The content (% by mass) of the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene with respect to the total mass of the Z isomer (C) and the nonafluorobutoxymethane.
  • the phase diagram of the three values of the content (% by mass) of (B) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene In the phase diagram of the three values of the content (% by mass) of (B) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene.
  • the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene, the nonafluorobutoxymethane (B) and the 1-chloro-3,3,3-trifluoropropene The content (% by mass) of the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene with respect to the total mass of the Z isomer (C) and the nonafluorobutoxymethane.
  • the phase diagram of the three values of the content (% by mass) of (B) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene In the phase diagram of the three values of the content (% by mass) of (B) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene.
  • the phase diagram of the three values of the content (% by mass) of 1 and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene In the phase diagram of the three values of the content (% by mass) of 1 and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene.
  • the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene, the nonafluorobutoxyethane (D) and the 1-chloro-3,3,3-trifluoropropene The content (% by mass) of the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene with respect to the total mass of the Z isomer (C) and the nonafluorobutoxyethane.
  • the phase diagram of the three values of the content (% by mass) of (D) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene In the phase diagram of the three values of the content (% by mass) of (D) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene.
  • the composition according to [5] which is a value in a region surrounded by a line connecting 6 straight lines in this order (% by mass, 27.4% by mass).
  • the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene, the nonafluorobutoxyethane (D) and the 1-chloro-3,3,3-trifluoropropene The content (% by mass) of the Z isomer (A) of the 1-chloro-2,3,3,3-tetrafluoropropene with respect to the total mass of the Z isomer (C) and the nonafluorobutoxyethane.
  • the phase diagram of the three values of the content (% by mass) of (D) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene In the phase diagram of the three values of the content (% by mass) of (D) and the content (% by mass) of the Z isomer (C) of 1-chloro-3,3,3-trifluoropropene.
  • composition of the present invention does not adversely affect the global environment, and when used as an aerosol, the liquid does not easily remain, the cleaning property of the object is excellent, and the influence on the material of the object is small.
  • FIG. 1 shows the Z isomer of 1-chloro-2,3,3,3-tetrafluoropropene (hereinafter, also referred to as HCFO-1224yd (Z)) of the component (A) and the nonafluorobutoxy of the component (B).
  • FIG. 2 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 3 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 4 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 5 shows HCFO-1224yd (Z) of the component (A), nonafluorobutoxyethane (C 4 F 9 OC 2 H 5 , hereinafter also referred to as HFE-569sf 2) of the component (D), and the component (C).
  • FIG. 6 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 7 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 8 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • composition 1 of the present invention is a Z isomer of 1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd (Z)).
  • A nonafluorobutoxymethane
  • B nonafluorobutoxymethane
  • C the optional component 1-chloro-3,3,3-trifluoropropene Z isomer
  • composition 1 of the present invention is a two-component composition containing HCFO-1224yd (Z) of the component (A) and HFE-449s1 of the component (B), or HCFO-1224yd (Z) of the component (A). ), HFE-449s1 of the component (B) and HCFO-1233zd (Z) of the component (C).
  • HCFO-1224yd is known to have a stereoisomer
  • HCFO-1224yd (Z) has a boiling point of 15 ° C.
  • HCFO-1224yd E isomer hereinafter, also referred to as HCFO-1224yd (E)
  • the boiling point of.) Is 17 ° C.
  • a known production method gives HCFO-1224yd (Z) and HCFO-1224yd (E) and mixtures thereof (usually a high proportion of HCFO-1224yd (Z)), which can be separated by distillation.
  • the composition 1 of the present invention contains HCFO-1224yd (Z) among these isomers.
  • HCFO-1224yd (Z) Since it has the above boiling point, HCFO-1224yd (Z) is excellent in volatility. HCFO-1224yd (Z) has no flash point. HCFO-1224yd (Z) has low surface tension and viscosity, and easily evaporates even at room temperature. HCFO-1224yd (Z) is excellent for use as a cleaning agent or coating solvent. HCFO-1224yd (Z) is intended for cleaning and removing mineral oil, silicone oil, fluorine oil, synthetic oil, mold release agent, dust, etc., and dissolving lubricants such as mineral oil, silicone oil, fluorine oil, synthetic oil, etc. Excellent applicability to objects.
  • Examples of the method for producing HCFO-1224yd include (1) a method of dehydrochlorinating 1,2-dichloro-2,3,3,3-tetrafluoropropane (hereinafter, also referred to as HCFC-234bb). And (2) a method of hydrogen-reducing 1,1-dichloro-2,3,3,3-tetrafluoropropene (hereinafter, also referred to as CFO-1214ya) and the like can be mentioned.
  • CFO-1214ya hydrogen-reducing 1,1-dichloro-2,3,3,3-tetrafluoropropene
  • HCFC-234bb is brought into contact with a base dissolved in a solvent, that is, a base in a solution state to carry out a dehydrochlorination reaction of HCFC-234bb.
  • HCFC-234bb can be produced, for example, by reacting 2,3,3,3-tetrafluoropropene (hereinafter, also referred to as HFO-1234yf) with chlorine in a solvent.
  • CFO-1214ya is prepared from, for example, 3,3-dichloro-1,1,1,2,2-pentafluoropropane (hereinafter, also referred to as HCFC-225ca) in an alkaline aqueous solution in the presence of a phase transfer catalyst.
  • a catalyst such as chromium, iron, copper, or activated carbon
  • HFE-449s1 means a compound represented by C 4 F 9 OCH 3.
  • HFE-449s1 has four structural isomers, and the HFE-449s1 contained in the composition of the present invention may be only one of them or a mixture of two or more thereof. ..
  • the HFE-449s1 contained in the composition of the present invention includes 1-methoxy-2-trifluoromethyl-1,1,2,3,3,3-hexafluoropropane and 1-methoxy-1,1,2, A mixture with 2,3,3,4,4,4-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 that even parts that are easily affected by heat, such as rubber parts and 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 has a small effect on rubber materials and resin materials.
  • 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 fluoride are available from Aldrich Chemical Company at ADOGEN 464. It can be produced by reacting with an alkylating agent such as dimethyl fluoride in an anhydrous polar aprotic solvent in the presence of a quaternary ammonium compound such as dimethylsulfate.
  • an alkylating agent such as dimethyl fluoride in an anhydrous polar aprotic solvent
  • a quaternary ammonium compound such as dimethylsulfate.
  • HCFO-1233zd is known to have a stereoisomer, HCFO-1233zd (Z) has a boiling point of about 40 ° C., and HCFO-1233zd has an E isomer (hereinafter, also referred to as HCFO-1233zd (E)).
  • the boiling point of) is about 18 ° C.
  • HCFO-1233zd (Z) and HCFO-1233zd (E) and a mixture thereof usually, the ratio of HCFO-1233zd (Z) is high
  • the composition 1 of the present invention contains HCFO-1233zd (Z) among these isomers.
  • HCFO-1233zd (Z) Since it has the above boiling point, HCFO-1233zd (Z) is excellent in volatility. Although HCFO-1233zd (Z) is an olefin, it is difficult to decompose even in the presence of oxygen and has high stability. HCFO-1233zd (Z) has no flash point. HCFO-1233zd (Z) has low surface tension and viscosity, and easily evaporates even at room temperature. HCFO-1233zd (Z) 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-1233zd can be produced by a known method.
  • a method of defluoridating hydrogenating 3-chloro-1,1,1,3-tetrafluoropropane (hereinafter, also referred to as HCFC-244fa) in the presence of a catalyst can be mentioned (Japanese Patent Laid-Open No. 2009-263365). Gazette).
  • FIG. 1 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C). 3 of the content (mass%) of (Z), the content (mass%) of HFE-449s1 of the component (B), and the content (mass%) of HCFO-1233zd (Z) of the component (C). It is a phase diagram of two values and shows the range of these three values of the composition 1 of this invention. In FIG.
  • the upper left coordinate is defined as the first coordinate, and the second coordinate, the third coordinate, the fourth coordinate, the fifth coordinate, and the sixth coordinate counterclockwise from the first coordinate.
  • the contents of HCFO-1224yd (Z) of the component (A), HFE-449s1 of the component (B) and HCFO-1233zd (Z) of the component (C) are the first in FIG.
  • the contents of HCFO-1224yd (Z) of the component (A), HFE-449s1 of the component (B) and HCFO-1233zd (Z) of the component (C) satisfy the above ranges.
  • the liquid does not easily remain, the object has excellent detergency, and the effect on the resin material is small.
  • FIG. 2 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • the phase diagram of three values of (Z) content (mass%), (B) component HFE-449s1 content (mass%), and (C) component HCFO-1233zd content (mass%) Yes, it shows a suitable range of these three values of the composition 1 of the present invention.
  • the upper left coordinate is defined as the seventh coordinate, and the eighth coordinate, the third coordinate, the fourth coordinate, the fifth coordinate, and the sixth coordinate counterclockwise from the seventh coordinate.
  • the content of HCFO-1233zd (Z) of the component (C) is 5.0% by mass or more.
  • HCFO-1233zd (Z) of the component (C) is 5.0% by mass or more, in the examples described later, HCFO-1224yd (Z) and HCFO-1224yd (Z) of the component (A) in the composition 1 of the present invention.
  • the kauributanol value hereinafter , KB value
  • FIG. 3 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 3 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • the upper left coordinate is the ninth coordinate, and the tenth coordinate, the eleventh coordinate, the twelfth coordinate, the thirteenth coordinate, the third coordinate, and the fourth coordinate counterclockwise from the ninth coordinate. Coordinates, the fifth coordinate, and the sixth coordinate.
  • the content of HCFO-1224yd (Z) of the component (A), HFE-449s1 of the component (B) and HCFO-1233zd (Z) of the component (C) is the ninth coordinate (Z).
  • A, B, C 12.9% by mass, 67.0% by mass, 20.1% by mass)
  • 10th coordinate (A, B, C 16.4% by mass, 65.8% by mass, 17.
  • FIG. 4 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 4 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-449s1 of the component (B), and the HCFO-1233zd (Z) of the component (C).
  • the upper left coordinate is the 14th coordinate, and the 15th coordinate, the 16th coordinate, and the 17th coordinate counterclockwise from the 14th coordinate.
  • the content of HCFO-1224yd (Z) of the component (A), HFE-449s1 of the component (B), and HCFO-1233zd (Z) of the component (C) is the 14th coordinate (Z).
  • A, B, C 24.2% by mass, 43.1% by mass, 32.7% by mass)
  • 15th coordinate (A, B, C 15.0% by mass, 26.7% by mass, 58.
  • the value, material influence evaluation, and solubility evaluation in various oils are all judged as A.
  • composition 2 of the present invention In the second embodiment of the composition of the present invention (hereinafter referred to as composition 2 of the present invention), HCFO-1224yd (Z) as a component (A) and nonafluorobutoxyethane (HFE-569sf2) as a component (D) are used. ) And HCFO-1233zd (Z), which is an optional component (C). That is, the composition 2 of the present invention is a two-component composition containing HCFO-1224yd (Z) of the component (A) and HFE-569sf2 of the component (D), or HCFO-1224yd (A). Z), a three-component composition comprising HFE-569sf2 as a component (D) and HCFO-1233zd (Z) as a component (C).
  • HCFO-1224yd (Z) and HCFO-1233zd (Z) are omitted because they have been described above.
  • HFE-569sf2 means a compound represented by C 4 F 9 OC 2 H 5.
  • HFE-569sf2 has four structural isomers, and the HFE-569sf2 contained in the composition of the present invention may be only one of them or a mixture of two or more thereof. ..
  • the HFE-569sf2 contained in the composition of the present invention includes 1-ethoxy-2-trifluoromethyl-1,1,2,3,3,3-hexafluoropropane and 1-ethoxy-1,1,2, A mixture of 2,3,3,4,4,4-nonafluorobutane is preferred. Examples of this mixture include the product "Novec7200" (manufactured by 3M).
  • HFE-569sf2 has a boiling point of 76 ° C., and even if it is boiled to become steam, it is 76 ° C., so that even parts that are easily affected by heat, such as rubber parts and resin parts, are unlikely to have an adverse effect. HFE-569sf2 has no flash point. HFE-569sf2 has low surface tension and viscosity, and easily evaporates even at room temperature. HFE-569sf2 has a small effect on rubber materials and resin materials.
  • HFE-569sf2 can be produced by a known method.
  • ADOGEN 464 available from Aldrich Chemical Company with 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 fluoride. It can be produced by reacting with an alkylating agent such as diethyl fluoride in an anhydrous polar aprotic solvent in the presence of a quaternary ammonium compound such as.
  • FIG. 5 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • the upper left coordinate is set as the first coordinate
  • the second coordinate, the third coordinate, the fourth coordinate, the fifth coordinate, and the sixth coordinate are set counterclockwise from the first coordinate.
  • the contents of HCFO-1224yd (Z) of the component (A), HFE-569sf2 of the component (D) and HCFO-1233zd (Z) of the component (C) are the first in FIG.
  • the contents of HCFO-1224yd (Z) of the component (A), HFE-569sf2 of the component (D) and HCFO-1233zd (Z) of the component (C) satisfy the above ranges.
  • the liquid does not easily remain, the object has excellent detergency, and the effect on the material of the object is small.
  • FIG. 6 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • Yes it shows a suitable range of these three values of the composition 2 of the present invention.
  • the upper left coordinate is defined as the seventh coordinate, and the second coordinate, the third coordinate, the fourth coordinate, the fifth coordinate, and the sixth coordinate counterclockwise from the seventh coordinate.
  • the contents of HCFO-1224yd (Z) of the component (A), HFE-569sf2 of the component (D) and HCFO-1233zd (Z) of the component (C) are the seventh in FIG.
  • the content of HCFO-1233zd (Z) of the component (C) is 5.0% by mass or more.
  • HCFO-1224yd (Z) and HCFO-1224yd (Z) of the component (A) in the composition 2 of the present invention are 5.0% by mass or more.
  • the KB value is improved as compared with the two-component composition having the same HFE-569sf2 content ratio (HCFO-1224yd (Z) (mass%): HFE-569sf2 (mass%)) of the component (D). .. Therefore, it is expected that the detergency of the object will be further improved.
  • FIG. 7 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 1 shows a more suitable range of these three values of the composition 2 of the present invention.
  • the composition 2 of the present invention contains HCFO-1224yd (Z) as a component (A), HFE-569sf2 as a component (D), and HCFO-1233zd (Z) as a component (C).
  • the value in the region surrounded by the line connected by 10 straight lines is the value of the HCFO-1224yd (Z) and (D) components of the component (A) in the composition 2 of the present invention in the examples described later.
  • the KB value is improved by 10% or more as compared with the two-component composition having the same HFE-569sf2 content ratio (HCFO-1224yd (Z) (mass%): HFE-569sf2 (mass%)). Therefore, it is expected that the detergency of the object will be further improved.
  • FIG. 8 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • FIG. 8 shows the HCFO-1224yd of the component (A) with respect to the total mass of the HCFO-1224yd (Z) of the component (A), the HFE-569sf2 of the component (D), and the HCFO-1233zd (Z) of the component (C).
  • composition 2 of the present invention contains HCFO-1224yd (Z) as a component (A), HFE-569sf2 as a component (D), and HCFO-1233zd (Z) as a component (C).
  • compositions 1 and 2 of the present invention do not adversely affect the global environment, and when used as an aerosol composition, the liquid does not easily remain, the object is excellent in detergency, and the effect on the material of the object is small.
  • the aerosol composition of the present invention contains the composition 1 or 2 of the present invention.
  • the aerosol composition of the present invention preferably contains a propellant, and more preferably contains at least one propellant selected from the group consisting of 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), 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.
  • the compressed gas include nitrogen, carbon dioxide, compressed air, and nitrous oxide.
  • the cleaning method of the present invention is characterized in that the composition 1 or 2 of the present invention is brought into contact with the surface of the article to remove stains adhering to the surface of the article.
  • the composition 1 or 2 of the present invention may be brought into contact with the surface of the article.
  • a method of hand wiping, dipping, spraying, shaking, ultrasonic waves, steam cleaning, or a combination thereof can be adopted.
  • the aerosol composition may be sprayed on the surface of the article.
  • the material of the article to which the compositions 1 and 2 of the present invention are applicable at least one selected from the group consisting of fibers, metals, resins, rubbers, glasses, and ceramics is preferable, and the fibers are natural fibers and synthetic fibers. Fiber is mentioned.
  • 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 compositions 1 and 2 of the present invention use a rubber material such as styrene-butadiene rubber (SBR) or a resin material such as a polycarbonate (PC) resin or a polyphenylene ether (PPE) resin, which is affected by HCFO-1233zd (Z). It can also be used for articles containing.
  • SBR styrene-butadiene rubber
  • PC polycarbonate
  • PPE polyphenylene ether
  • 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 composition contains a rubber material such as SBR and a resin material such as PC resin and PPE resin.
  • the stains to be washed and removed include carbon, flux, processing oil, mold release agent, sebum, food oil, cosmetic oil, and other oils and fats adhering to various objects to be cleaned. Examples include dust and the like that have adhered to the surface.
  • 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, brake fluid and the like.
  • cosmetics include manicure and lipstick. Two or more of the above-mentioned stains may be attached to various objects to be cleaned. Since the composition of the present invention is superior in solubility in these oils, silicone oil, fluorine oil, etc. as compared with conventional solvent compositions such as HFC and HFE, it is used for cleaning stains composed of these oils. Is preferable. It was
  • the liquid does not easily remain, the influence on the material of the target article is small, and both the evaporation rate evaluation and the KB value evaluation shown in Examples described later are performed. Due to its superiority, it can also be used as a solvent for forming a coating film of a non-volatile organic compound by an aerosol (hereinafter, also referred to as a coating film forming solvent).
  • a coating film forming solvent the content of the non-volatile organic compound is preferably 0.01 to 50% by mass in the total of 100% by mass of the composition 1 or 2 of the present invention and the non-volatile organic compound. , 0.05 to 30% by mass, more preferably 0.1 to 20% by mass.
  • the film thickness of the coating film when the non-volatile organic compound is applied and the non-volatile after evaporative removal of the coating film forming solvent (hereinafter, also referred to as drying). It is easy to adjust the thickness of the organic compound coating film to an appropriate range.
  • the non-volatile organic compound has a boiling point higher than that of the coating film forming solvent and remains even after the coating film forming solvent evaporates.
  • Specific examples of 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.
  • examples thereof include an antifouling coating agent such as a fingerprint adhesion preventive agent for imparting antifouling performance to an article.
  • Lubricants are meant to be used to reduce friction on the contact surfaces and prevent heat generation and frictional damage when the two members move 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, and a silicone-based lubricant are preferable because of their excellent solubility in a coating film-forming solvent.
  • 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 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 "Critex (registered trademark) GPL102" manufactured by DuPont Co., Ltd.
  • Daikin "Daikin # 3"
  • Daikin # 10 "Daikin # 20", “Daikin # 50”
  • Examples thereof include “Daifuroil # 100" and "Demonum S-65” (manufactured by Daikin Industries, Ltd.).
  • a fluorine oil such as a low polymer of perfluoropolyether or chlorotrifluoroethylene is preferably 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
  • a polytetrafluoroethylene powder or other thickener is blended.
  • product names "Kritex (registered trademark) Grease 240AC” manufactured by DuPont Co., Ltd.
  • Difloyl Grease DG-203 "Demnum L65”, “Demnum L100”, “Demnum L200” (above, Daikin shares).
  • silicone-based lubricant examples include silicone oil and silicone grease.
  • silicone oil dimethyl silicone, methyl hydrogen silicone, methyl phenyl silicone, cyclic dimethyl silicone, and modified silicone oil having an organic group introduced into a side chain or a terminal are preferable.
  • silicone grease a product containing various silicone oils listed above as a base oil, a thickener such as metal soap, and various additives is preferable.
  • product names “Shin-Etsu Silicone G-30 Series", “Shin-Etsu Silicone G-40 Series”, “Shin-Etsu Silicone FG-720 Series", “Shin-Etsu Silicone G-411", “Shin-Etsu Silicone G-501", “Shin-Etsu Silicone” “G-6500", “Shin-Etsu Silicone G-330", “Shin-Etsu Silicone G-340", “Shin-Etsu Silicone G-350", “Shin-Etsu Silicone G-630” (all manufactured by Shin-Etsu Chemical Co., Ltd.), "Moricoat (Moricoat) "Moricoat (registered trademark) 41", “Moricoat (registered trademark) 41", “Moricoat (registered trademark) 44”, "Moricoat (Moricoat
  • the rust inhibitor 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 prevent the metal material from rusting by blocking the metal surface and oxygen.
  • examples of the rust preventive include mineral oils, polyol esters, polyalkylene glycols, and synthetic oils such as polyvinyl ether.
  • moisture-proof coating agents examples 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). (Made by Chemicals), SFE-DP02H, SNF-DP20H (all manufactured by Seimi Chemicals) and the like.
  • 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 Fluoro Technology) SR-4000A (above, Seimi Chemical). (Manufactured by the company) and the like.
  • the base material for forming the coating film of the non-volatile organic compound a base material made of various materials such as metal, resin, rubber, glass and ceramics is adopted. Further, the solvent for forming a coating film can form a coating film of a non-volatile organic compound without affecting an article containing a rubber material or a resin material. It was
  • the base material on which the coating film of the non-volatile organic compound is formed include those using a fluorine-based lubricant, such as CD and DVD tray parts, printers, and copy equipment in industrial equipment, personal computers, and audio equipment. , Household equipment such as flux equipment, office equipment, and the like.
  • a silicone-based lubricant examples include syringes, cylinders, medical tube parts, metal blades, catheters and the like.
  • Examples 15-21, 26-32, 67-70, 72-74, 76-78, 80-83, 86-88, 90-92, 94-97, 99-103, 106, 107, 110-133, 135 136, 138 to 170 are examples of the compositions of the present invention
  • Examples 1 to 14, 22 to 25, 33 to 66, 71, 75, 79, 84, 85, 89, 93, 98, 104, 105, 108. , 109, 134, 137 are comparative examples.
  • HCFO-1224yd (Z) An isomer mixture of HCFO-1224yd (E) and HCFO-1224yd (Z) was prepared according to the method described in WO 2017/118541. The above isomer mixture was purified by the method described in International Publication No. 2017/146190 to prepare HCFO-1224yd (Z) having a purity of 99.5%.
  • HFE-449s1 or HFE-569sf2 3M TM NOVEC TM 7100 high-performance liquid (3M Japan Ltd., Japan) is used as HFE-449s1 for HFE-based nonflammable fluorine-based solvent, and 3M is used as HFE-569sf2 for HFE-based nonflammable fluorine-based solvent.
  • TM NOVEC TM 7200 High-performance liquid (3M Japan Ltd., Japan) was purchased respectively.
  • HCFO-1233zd (Z) was produced by the method described in JP2013-87066A. After production, the product was purified to obtain HCFO-1233zd (Z) having a purity of 99.5%.
  • HCFO-1224yd (Z), HCFO-1233zd (Z), and HFE-449s1 or HFE-569sf2 are filled in an aerosol container in order from the component having the highest boiling point so as to have the mass ratio shown in the table below. did.
  • the filling amount was adjusted so that the liquid phase volume of the composition was about 80% by volume of the aerosol container volume.
  • the pressure in the aerosol container was adjusted by pressurizing with nitrogen and carbon dioxide so as to be 0.5 MPaG. In a room at a temperature of 25 ° C. ⁇ 2 ° C., the composition filled in the aerosol container was continuously sprayed from the liquid phase until it could not be sprayed from the aerosol container.
  • the above-mentioned evaporation rate evaluation and KB value evaluation are used as indicators of the detergency of the object.
  • the detergency of the object is excellent.
  • test piece was taken out and the appearance was evaluated according to the following criteria.
  • a three-component composition comprising HCFO-1224yd (Z) as a component (A), HFE-449s1 as a component (B), and HCFO-1233zd (Z) as a component (C), and HCFO as a component (C).
  • Examples 67 to 70, 72 to 74, 76 to 78, 80 to 83, 106 to 107, 110 to 117, 119 to 133 in which the content of -1233 zd (Z) is 5.0% by mass or more are HCFO-1224yd ( The KB value was improved as compared with the two-component composition having the same content ratio of Z) and HFE-449s1 (HCFO-1224yd (Z) (mass%): HFE-449s1 (mass%)).
  • Example 115 where HCFO-1224yd (Z) (mass%): HFE-449s1 (mass%) is 38.0: 57.0
  • HCFO-1224yd (Z) (mass%): HFE-449s1 (mass%) is 38.0: 57.0.
  • Example 18 of 40.0: 60.0 A three-component composition comprising HCFO-1224yd (Z) as a component (A), HFE-569sf2 as a component (D), and HCFO-1233zd (Z) as a component (C), and HCFO as a component (C).
  • HCFO-1224yd (Z) (% by mass): HFE-569sf2 is 38.0: 57.0, HCFO-1224yd (Z) (mass%): HFE-569sf2 (% by mass)) is 40.
  • the KB value was improved as compared with Example 143 of 0.0: 60.0.
  • 72-74, 76-78, 80-83, 106, 107, 111-114, 116, 117, 120, 121, 128-133 contain the contents of HCFO-1224yd (Z) and HFE-449s1 (HCFO-).
  • the KB value was improved by 10% or more as compared with the composition of the two-component system in which 1224yd (Z) (mass%): HFE-449s1 (mass%)) was similar.
  • Example 116 in which HCFO-1224yd (Z) (% by weight): HFE-449s1 (% by weight) is 35.4: 53.0 has HCFO-1224yd (Z) (% by weight): HFE-449s1 (% by weight). )) was 40.0: 60.0, the KB value was improved by 10% as compared with Example 18.
  • HCFO-1224yd (Z) and HFE-569sf2 are the content ratios of HCFO-1224yd (Z) and HFE-569sf2 ( The KB value was improved by 10% or more as compared with the composition of the two-component system in which HCFO-1224yd (Z) (% by mass): HFE-569sf2 (% by mass)) was similar.
  • Example 145 where HCFO-1224yd (Z) (mass%): HFE-569sf2 is 35.4: 53.0, HCFO-1224yd (Z) (mass%): HFE-569sf2 (mass%)) is 40.
  • the KB value was improved by 10% as compared with Example 143 of 0.0: 60.0.
  • composition of the present invention does not adversely affect the global environment, and when used as an aerosol, the liquid does not easily remain, the cleaning property of the target object is excellent, and the influence on the material of the target article is small. Useful for use.

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Abstract

L'invention concerne une composition et son utilisation, la composition n'ayant pas d'effet indésirable sur l'environnement global, et, lorsqu'elle est utilisée comme aérosol, présentant d'exceptionnelles capacités de nettoyage d'objet et n'étant pas sujette à laisser du liquide derrière elle, et ayant en outre peu d'effet sur le matériau d'un article sur lequel est utilisée ladite composition.　Une composition comprenant des quantités prescrites : de l'isomère Z du 1-chloro-2,3,3,3-tétrafluoropropène ; de nonafluorobutoxyméthane ou de nonafluorobutoxyéthane ; et, selon les besoins, de l'isomère Z du 1-chloro-3,3,3-trifluoropropène.
PCT/JP2021/025155 2020-07-08 2021-07-02 Composition et utilisation correspondante Ceased WO2022009801A1 (fr)

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JP2017043742A (ja) * 2015-08-28 2017-03-02 旭硝子株式会社 溶剤組成物
WO2019036049A1 (fr) * 2017-08-18 2019-02-21 The Chemours Company, Fc, Llc Compositions et utilisations de z-1-chloro-2,3,3,3-tetrafluoroprop-1-ène
WO2019123759A1 (fr) * 2017-12-22 2019-06-27 Ａｇｃ株式会社 Composition de solvant, procédé de nettoyage, composition de formation de revêtement, procédé de fabrication de substrat revêtu, composition d'aérosol, composition de rinçage, procédé pour élément de nettoyage, et dispositif pour élément de nettoyage

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ATE528341T1 (de) * 2007-03-29 2011-10-15 Arkema Inc Blasmittelzusammensetzung aus hydrochlorfluorolefin und hydrofluorolefin
MX2014007308A (es) * 2011-12-19 2014-07-30 Honeywell Int Inc Composiciones de 1,1,1,3,3-pentafluoropropano y ciclopentano.
CN106715669B (zh) * 2014-10-02 2019-05-10 中央硝子株式会社 含有2-氯-1,3,3,3-四氟丙烯和1-氯-3,3,3-三氟丙烯的类共沸组合物
JP2019065223A (ja) * 2017-10-03 2019-04-25 神戸合成株式会社 洗浄剤組成物及びそのエアゾール組成物
CN108359121B (zh) * 2017-12-14 2019-03-15 浙江衢化氟化学有限公司 一种共沸和类共沸组合物

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Publication number Priority date Publication date Assignee Title
JP2017043742A (ja) * 2015-08-28 2017-03-02 旭硝子株式会社 溶剤組成物
WO2019036049A1 (fr) * 2017-08-18 2019-02-21 The Chemours Company, Fc, Llc Compositions et utilisations de z-1-chloro-2,3,3,3-tetrafluoroprop-1-ène
WO2019123759A1 (fr) * 2017-12-22 2019-06-27 Ａｇｃ株式会社 Composition de solvant, procédé de nettoyage, composition de formation de revêtement, procédé de fabrication de substrat revêtu, composition d'aérosol, composition de rinçage, procédé pour élément de nettoyage, et dispositif pour élément de nettoyage

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