US20210403837A1 - Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same - Google Patents
Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same Download PDFInfo
- Publication number
- US20210403837A1 US20210403837A1 US17/470,597 US202117470597A US2021403837A1 US 20210403837 A1 US20210403837 A1 US 20210403837A1 US 202117470597 A US202117470597 A US 202117470597A US 2021403837 A1 US2021403837 A1 US 2021403837A1
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- US
- United States
- Prior art keywords
- oil
- composition
- solvent
- detergent
- solvents
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 239000002904 solvent Substances 0.000 title claims abstract description 73
- 239000003599 detergent Substances 0.000 title claims abstract description 44
- 238000004140 cleaning Methods 0.000 title description 15
- 238000000034 method Methods 0.000 title description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 238000009835 boiling Methods 0.000 claims abstract description 18
- 239000003921 oil Substances 0.000 claims description 58
- 239000010687 lubricating oil Substances 0.000 claims description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004519 grease Substances 0.000 claims description 6
- 239000001993 wax Substances 0.000 claims description 6
- 229920002545 silicone oil Polymers 0.000 claims description 5
- QSSVZVNYQIGOJR-UHFFFAOYSA-N 1,1,2-trichloro-3,3,3-trifluoroprop-1-ene Chemical group FC(F)(F)C(Cl)=C(Cl)Cl QSSVZVNYQIGOJR-UHFFFAOYSA-N 0.000 claims description 3
- AYRPZBVEKSYAAD-UHFFFAOYSA-N 1,1,3-trichloro-2,3,3-trifluoroprop-1-ene Chemical compound ClC(Cl)=C(F)C(F)(F)Cl AYRPZBVEKSYAAD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 4
- 230000001988 toxicity Effects 0.000 abstract description 4
- 230000003287 optical effect Effects 0.000 description 6
- 238000005461 lubrication Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
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- 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
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/38—Lubricating compositions characterised by the base-material being a macromolecular compound containing halogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
- C10M131/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only
- C10M131/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only aliphatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
- C11D3/245—Organic compounds containing halogen containing fluorine
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- 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
- C11D7/26—Organic compounds containing oxygen
- C11D7/261—Alcohols; Phenols
-
- 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
- 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
- C11D7/5004—Organic solvents
- C11D7/5022—Organic solvents containing oxygen
-
- 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
- C23G5/028—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
- C23G5/02809—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 containing chlorine and fluorine
-
- 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
- C23G5/02809—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 containing chlorine and fluorine
- C23G5/02812—Perhalogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
- C10M2213/023—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
- C10M2229/025—Unspecified siloxanes; Silicones used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
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- C11D2111/16—
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- C11D2111/20—
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- C11D2111/22—
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- 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
- C23G5/02809—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 containing chlorine and fluorine
- C23G5/02825—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 containing chlorine and fluorine containing hydrogen
- C23G5/02841—Propanes
Definitions
- the present invention relates to a detergent composition, a cleaning method, a solvent composition, use thereof as a solvent for oil, and an oil composition containing the same.
- oils including lubricating oils, such as silicone oil, fluorine-based oil, mineral-based oil, grease, and wax, are used for various applications. These oils can be singly applied to substrate surfaces or machine part surfaces in need of lubrication; however, in consideration of predetermined necessity or purpose, they are often used after being dissolved in solvents. For example, these oils are used when it is necessary to adjust viscosity etc., or used for the purpose of forming lubricating films of the oils on the surfaces to which the oils are applied.
- lubricating oils such as silicone oil, fluorine-based oil, mineral-based oil, grease, and wax
- those that have the same composition as these solvents and that are used to dissolve various oils for cleaning are particularly called detergents, cleaning solvents, etc.
- non-flammable solvents are fluorine-based solvents with low toxicity, represented by trade names “Asahilkin AK-225,” “Zeorola H,” “Novec,” etc.
- Examples include chlorofluoroolefin (boiling point: 46° C.) (PTL 1), hydrochlorofluoroolefin (boiling point: 53° C.) (PTL 2), 1,2-dichloroethylene (boiling point: 48° C.), a mixture of 1,2-dichloroethylene and hydrofluoroolefin mentioned above, and cyclic hydrofluorocarbon (boiling point; 83° C.) (PTL 3), and the like.
- these environmentally friendly solvents have various problems such that they have low solubility; the solvents themselves are flammable; when they are mixed with second non-flammable solvents to reduce the flammability of the solvents themselves, it is necessary to adjust the composition ratio so that the mixed solvents are azeotropic; their boiling point is not suitable; and reduction in the global warming potential is not sufficient.
- An object of the present invention is to provide a solvent and a detergent that have excellent basic properties as solvents or detergents, such as solubility, and that have a boiling point, flammability, toxicity, GWP, and ODP that are all within preferable ranges.
- a solvent composition or detergent composition comprising a hydrochlorofluoropropene represented by the formula: CX 3 CX ⁇ CX 2 , wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
- the present invention has been completed upon further trial and error based on the above finding.
- the present invention includes the following aspects.
- a solvent composition or detergent composition comprising a hydrochlorofluoropropene represented by the formula: CX 3 CX ⁇ CX 2 , wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
- Item 2 The solvent composition or detergent composition according to Item 1, wherein the hydrochlorofluoropropene is 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa) and/or 1,1,3-trichloro-2,3,3-trifluoropropene (CFO-1213ya).
- the hydrochlorofluoropropene is 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa) and/or 1,1,3-trichloro-2,3,3-trifluoropropene (CFO-1213ya).
- Item 4 The solvent composition or detergent composition according to Item 3, wherein the one or more other solvents are 1,2-dichloroethylene and/or isopropanol.
- Item 5 The solvent composition or detergent composition according to any one of Items 1 to 4, for use as a solvent or detergent for oil.
- Item 6 The solvent composition according to Item 5, wherein the oil is a lubricating oil.
- Item 7 The solvent composition according to Item 6, wherein the lubricating oil is at least one lubricating oil selected from the group consisting of silicone-based oil, fluorine-based oil, mineral oil-based oil, grease, and wax.
- Item 8 An oil composition comprising oil and the solvent composition according to any one of Items 1 to 4.
- Item 9 The oil composition according to Item 8, wherein the oil is a lubricating oil.
- Item 10 The oil composition according to Item 9, wherein the lubricating oil is at least one lubricating oil selected from the group consisting of silicone-based oil, fluorine-based oil, mineral oil-based oil, grease, and wax.
- a cleaning method comprising the step of applying the detergent composition according to any one of Items 1 to 4 to a surface to be treated.
- the present invention can provide a solvent or a detergent that have excellent basic properties as solvents or detergents, such as solubility, and that have a boiling point, flammability, toxicity, GWP, and ODP that are all within preferable ranges.
- the present invention uses a hydrochlorofluoropropene represented by the formula: CX 3 CX ⁇ CX 2 , wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
- hydrochlorofluoropropenes represented by the above formula are suitable as solvent components or detergent components that have excellent basic properties as solvents or detergents, such as solubility, and that have flammability, toxicity, GWP, and ODP that are all are within preferable ranges.
- These hydrochlorofluoropropenes often have an atmospheric pressure boiling point of 50° C. or more, and are also preferably used as solvent components or detergent components in terms of boiling point. Examples of hydrochlorofluoropropenes that have an atmospheric pressure boiling point of 50° C.
- CFO-1213xa 1,1,2-trichloro-3,3,3-trifluoropropene
- CFO-1213ya 1,1,3-trichloro-2,3,3-trifluoropropene
- the atmospheric pressure boiling point of CFO-1213xa is 88° C.
- the atmospheric pressure boiling point of CFO-1213ya is 87° C.
- the solvent composition or detergent composition of the present invention may further comprise one or more other solvents.
- the one or more other solvents are mixed for the purpose of, for example, further improving the solubility of the object.
- the one or more other solvents are not limited, and can be widely used. Examples include 1,2-dichloroethylene, isopropanol, and the like.
- the solvent composition or detergent composition of the present invention comprises one or more other solvents in an amount of 1 to 90 wt. %, and preferably 5 to 50 wt. %, based on the total amount of the solvents.
- the solvent composition or detergent composition of the present invention may further comprise one or more other components.
- Examples of the one or more other components common in the solvent composition and detergent composition of the present invention include antioxidants, stabilizers, preservatives, surfactants, and the like.
- the solvent composition or detergent composition of the present invention may comprise at least one member selected from the above group as the one or more other components.
- the solvent composition of the present invention may further comprise at least one member selected from the group consisting of a lubricant for improving lubrication performance, and a dispersant.
- the detergent composition of the present invention may further comprise a surfactant etc.
- the solvent composition or detergent composition of the present invention comprises the above hydrochlorofluoropropene in a total amount of 1 to 100 wt. % based on the entire composition.
- the hydrochlorofluoropropene is preferably contained in a total amount of 5 to 100 wt. %, and more preferably 50 to 100 wt. %, based on the entire composition.
- the solvent composition or detergent composition of the present invention is not limited, and can be used for a wide range of applications.
- the solvent composition or detergent composition of the present invention is used as a solvent or detergent for oil.
- the oil is not limited, and the solvent composition or detergent composition of the present invention can be used for a wide range of oils, In particular, one use of the solvent composition, for example, is being effectively used as a solvent for lubricating oils.
- the lubricating oils are not limited, and the solvent composition can be used for a wide range of lubricating oils, Examples of lubricating oils include silicone-based oil, fluorine-based oil, mineral oil-based oil, grease, wax, and the like.
- the solvent composition of the present invention may be used for one of these lubricating oils, or may be used for a combination of two or more lubricating oils.
- the specific use of the detergent composition is not limited to oil, and a wide range of contaminants can be used as cleaning objects. Examples include photoresist, solder flux, resin processing waste, mold releasing agent, working oil, dust, ink, dye, and the like. Moreover, the detergent composition can also be widely used in cleaning methods targeted for oil. Examples include cleaning of precision machinery components, automobile components, electronic components, such as ICs, printed circuit boards, liquid crystal display devices, and magnetic recording devices, as well as optical components, such as optical lenses and optical sensors; cleaning in the production process, assembling process, finishing process, etc., of resin processed products, metal molded products, etc.; and cleaning of processing molds etc.
- the oil composition of the present invention comprises oil and the above solvent composition.
- the oil composition of the present invention is not limited, and may generally comprise 1 to 50 wt. % of oil based on the entire composition, although it depends on the type of oil, application, etc.
- the oil composition of the present invention is not limited, and can be used for a wide range of applications.
- the oil composition of the present invention is used for lubrication of substrate surfaces or machine part surfaces.
- the oil composition can be applied to substrate surfaces or machine part surfaces in need of lubrication in such a manner that the oil composition directly exhibits lubricating action.
- a lubricating film comprising the oil composition can be formed on these surfaces.
- the cleaning method of the present invention comprises the step of applying the detergent composition of the present invention to a surface to be treated.
- the surface to be treated is not limited, and can be widely selected.
- Articles that have a surface to be treated are not limited.
- the entirety of an article may be used as a surface to be treated, or at least one portion can be used as a surface to be treated.
- cleaning method examples include cleaning of solder flux, dust, photoresist, etc., in the production process of electronic components, such as ICs, printed circuit boards, liquid crystal display devices, and magnetic recording devices, as well as in the production process of optical components, such as optical lenses and optical sensors; and cleaning of mold releasing agents, working oil, etc., in the production process of precision machinery components, automobile components, resin processed products, metal molded products, etc.
- CFO-1213ya When 50 g of silicone oil having a viscosity at 25° C. of about 10,000 cP and 100 g of CFO-1213ya are mixed, the two components are compatible with each other, and a homogeneous solution can be obtained.
- the GWP of CFO-1213ya is 10 or less. Further, when measurement using a Setaflash closed-cup tester is carried out, CFO-1213ya has no flash point and is non-flammable.
Abstract
An object of the present invention is to provide a solvent and a detergent that have excellent basic properties as solvents or detergents, such as solubility, and that have a boiling point, flammability, toxicity, GWP, and ODP that are all within preferable ranges.
To achieve the above object, the present invention provides a solvent composition or detergent composition comprising a hydrochlorofluoropropene represented by the formula: CX3CX═CX2, wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or higher.
Description
- The present invention relates to a detergent composition, a cleaning method, a solvent composition, use thereof as a solvent for oil, and an oil composition containing the same.
- Various oils, including lubricating oils, such as silicone oil, fluorine-based oil, mineral-based oil, grease, and wax, are used for various applications. These oils can be singly applied to substrate surfaces or machine part surfaces in need of lubrication; however, in consideration of predetermined necessity or purpose, they are often used after being dissolved in solvents. For example, these oils are used when it is necessary to adjust viscosity etc., or used for the purpose of forming lubricating films of the oils on the surfaces to which the oils are applied.
- Moreover, those that have the same composition as these solvents and that are used to dissolve various oils for cleaning are particularly called detergents, cleaning solvents, etc.
- Some solvents or detergents are required to be non-flammable. Conventionally used non-flammable solvents are fluorine-based solvents with low toxicity, represented by trade names “Asahilkin AK-225,” “Zeorola H,” “Novec,” etc.
- However, it is indicated that these conventional fluorine-based solvents or detergents, which are advantageous in non-flammability and low toxicity, have problems in terms of environmental destruction, such as possibility of ozone layer depletion and possibility of contribution to global warming. In consideration of these circumstances, products, such as various hydrofluoroolefins and 1,2-dichloroethylene, have been developed as environmentally friendly solvents. Examples include chlorofluoroolefin (boiling point: 46° C.) (PTL 1), hydrochlorofluoroolefin (boiling point: 53° C.) (PTL 2), 1,2-dichloroethylene (boiling point: 48° C.), a mixture of 1,2-dichloroethylene and hydrofluoroolefin mentioned above, and cyclic hydrofluorocarbon (boiling point; 83° C.) (PTL 3), and the like.
- In contrast, however, these environmentally friendly solvents have various problems such that they have low solubility; the solvents themselves are flammable; when they are mixed with second non-flammable solvents to reduce the flammability of the solvents themselves, it is necessary to adjust the composition ratio so that the mixed solvents are azeotropic; their boiling point is not suitable; and reduction in the global warming potential is not sufficient.
- PTL 1: JP2013-224383A
- PTL 2: JP2016-98334A
- PTL 3: JP2001-354985A
- An object of the present invention is to provide a solvent and a detergent that have excellent basic properties as solvents or detergents, such as solubility, and that have a boiling point, flammability, toxicity, GWP, and ODP that are all within preferable ranges.
- The present inventor found that the above object can be achieved by a solvent composition or detergent composition comprising a hydrochlorofluoropropene represented by the formula: CX3CX═CX2, wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
- The present invention has been completed upon further trial and error based on the above finding. The present invention includes the following aspects.
- Item 1. A solvent composition or detergent composition comprising a hydrochlorofluoropropene represented by the formula: CX3CX═CX2, wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
- Item 2. The solvent composition or detergent composition according to Item 1, wherein the hydrochlorofluoropropene is 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa) and/or 1,1,3-trichloro-2,3,3-trifluoropropene (CFO-1213ya).
- Item 3. The solvent composition or detergent composition according to Item 1 or 2, further comprising one or more other solvents.
- Item 4. The solvent composition or detergent composition according to Item 3, wherein the one or more other solvents are 1,2-dichloroethylene and/or isopropanol.
- Item 5. The solvent composition or detergent composition according to any one of Items 1 to 4, for use as a solvent or detergent for oil.
- Item 6. The solvent composition according to Item 5, wherein the oil is a lubricating oil.
- Item 7. The solvent composition according to Item 6, wherein the lubricating oil is at least one lubricating oil selected from the group consisting of silicone-based oil, fluorine-based oil, mineral oil-based oil, grease, and wax. Item 8. An oil composition comprising oil and the solvent composition according to any one of Items 1 to 4.
- Item 9. The oil composition according to Item 8, wherein the oil is a lubricating oil.
- Item 10. The oil composition according to Item 9, wherein the lubricating oil is at least one lubricating oil selected from the group consisting of silicone-based oil, fluorine-based oil, mineral oil-based oil, grease, and wax.
- Item 11. A cleaning method comprising the step of applying the detergent composition according to any one of Items 1 to 4 to a surface to be treated.
- The present invention can provide a solvent or a detergent that have excellent basic properties as solvents or detergents, such as solubility, and that have a boiling point, flammability, toxicity, GWP, and ODP that are all within preferable ranges.
- The present invention uses a hydrochlorofluoropropene represented by the formula: CX3CX═CX2, wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl; the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
- The examination by the present inventor revealed that hydrochlorofluoropropenes represented by the above formula are suitable as solvent components or detergent components that have excellent basic properties as solvents or detergents, such as solubility, and that have flammability, toxicity, GWP, and ODP that are all are within preferable ranges. These hydrochlorofluoropropenes often have an atmospheric pressure boiling point of 50° C. or more, and are also preferably used as solvent components or detergent components in terms of boiling point. Examples of hydrochlorofluoropropenes that have an atmospheric pressure boiling point of 50° C. or more include 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa), 1,1,3-trichloro-2,3,3-trifluoropropene (CFO-1213ya), and the like. The atmospheric pressure boiling point of CFO-1213xa is 88° C., and the atmospheric pressure boiling point of CFO-1213ya is 87° C.
- The solvent composition or detergent composition of the present invention may further comprise one or more other solvents.
- The one or more other solvents are mixed for the purpose of, for example, further improving the solubility of the object.
- The one or more other solvents are not limited, and can be widely used. Examples include 1,2-dichloroethylene, isopropanol, and the like. The solvent composition or detergent composition of the present invention comprises one or more other solvents in an amount of 1 to 90 wt. %, and preferably 5 to 50 wt. %, based on the total amount of the solvents.
- The solvent composition or detergent composition of the present invention may further comprise one or more other components.
- Examples of the one or more other components common in the solvent composition and detergent composition of the present invention include antioxidants, stabilizers, preservatives, surfactants, and the like. The solvent composition or detergent composition of the present invention may comprise at least one member selected from the above group as the one or more other components.
- As a component different from the above components, the solvent composition of the present invention may further comprise at least one member selected from the group consisting of a lubricant for improving lubrication performance, and a dispersant.
- As a component different from the above components, the detergent composition of the present invention may further comprise a surfactant etc.
- The solvent composition or detergent composition of the present invention comprises the above hydrochlorofluoropropene in a total amount of 1 to 100 wt. % based on the entire composition.
- In terms of the performance of dissolving an object and/or reducing the flammability as the entire composition, the hydrochlorofluoropropene is preferably contained in a total amount of 5 to 100 wt. %, and more preferably 50 to 100 wt. %, based on the entire composition.
- The solvent composition or detergent composition of the present invention is not limited, and can be used for a wide range of applications. For example, the solvent composition or detergent composition of the present invention is used as a solvent or detergent for oil.
- The oil is not limited, and the solvent composition or detergent composition of the present invention can be used for a wide range of oils, In particular, one use of the solvent composition, for example, is being effectively used as a solvent for lubricating oils.
- The lubricating oils are not limited, and the solvent composition can be used for a wide range of lubricating oils, Examples of lubricating oils include silicone-based oil, fluorine-based oil, mineral oil-based oil, grease, wax, and the like. The solvent composition of the present invention may be used for one of these lubricating oils, or may be used for a combination of two or more lubricating oils.
- The specific use of the detergent composition is not limited to oil, and a wide range of contaminants can be used as cleaning objects. Examples include photoresist, solder flux, resin processing waste, mold releasing agent, working oil, dust, ink, dye, and the like. Moreover, the detergent composition can also be widely used in cleaning methods targeted for oil. Examples include cleaning of precision machinery components, automobile components, electronic components, such as ICs, printed circuit boards, liquid crystal display devices, and magnetic recording devices, as well as optical components, such as optical lenses and optical sensors; cleaning in the production process, assembling process, finishing process, etc., of resin processed products, metal molded products, etc.; and cleaning of processing molds etc.
- The oil composition of the present invention comprises oil and the above solvent composition.
- For the oil, the same explanation as for the solvent. composition is applied.
- The oil composition of the present invention is not limited, and may generally comprise 1 to 50 wt. % of oil based on the entire composition, although it depends on the type of oil, application, etc.
- The oil composition of the present invention is not limited, and can be used for a wide range of applications. For example, the oil composition of the present invention is used for lubrication of substrate surfaces or machine part surfaces. In that case, the oil composition can be applied to substrate surfaces or machine part surfaces in need of lubrication in such a manner that the oil composition directly exhibits lubricating action. Alternatively, a lubricating film comprising the oil composition can be formed on these surfaces.
- The cleaning method of the present invention comprises the step of applying the detergent composition of the present invention to a surface to be treated.
- The surface to be treated is not limited, and can be widely selected. Articles that have a surface to be treated are not limited. The entirety of an article may be used as a surface to be treated, or at least one portion can be used as a surface to be treated.
- Specific examples of the cleaning method include cleaning of solder flux, dust, photoresist, etc., in the production process of electronic components, such as ICs, printed circuit boards, liquid crystal display devices, and magnetic recording devices, as well as in the production process of optical components, such as optical lenses and optical sensors; and cleaning of mold releasing agents, working oil, etc., in the production process of precision machinery components, automobile components, resin processed products, metal molded products, etc.
- The present invention is described in detail below with reference to Examples and Comparative Examples; however, the present invention is not limited thereto.
- When 50 g of silicone oil having a viscosity at 25° C. of about 10,000 cP and 100 g of CFO-1213ya are mixed, the two components are compatible with each other, and a homogeneous solution can be obtained. The GWP of CFO-1213ya is 10 or less. Further, when measurement using a Setaflash closed-cup tester is carried out, CFO-1213ya has no flash point and is non-flammable.
- When 100 g of silicone oil having a viscosity at 25° C. of about 10,000 cP, 85 g of CFO-1213ya, and 15 g of 1,2-dichloroethylene are mixed, the three components are compatible with each other, and a homogeneous solution can be obtained.
- When 3 g of fluorine polymer oil having a viscosity at 25° C. of about 15,000 cP and 100 g of CFO-1213ya are mixed, the two components are compatible with each other, and a homogeneous solution can be obtained.
- When 3 g of fluorine-based oil having a viscosity at 25° C. of about 15,000 cP and 100 g of 1,2-dichloroethylene are mixed, the two components are not compatible with each other, and are separated.
Claims (11)
1. A solvent composition or detergent composition comprising a hydrochlorofluoropropene represented by the formula: CX3CX═CX2, wherein each X is the same or different and is F or Cl, at least one X is F, and at least three X are Cl;
the hydrochlorofluoropropene having an atmospheric pressure boiling point of 50° C. or more.
2. The solvent composition or detergent composition according to claim 1 , wherein the hydrochlorofluoropropene is 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa) and/or 1,1,3-trichloro-2,3,3 -trifluoropropene (CFO-1213ya).
3. The solvent composition or detergent composition according to claim 1 , further comprising one or more other solvents.
4. The solvent composition or detergent composition according to claim 3 , wherein the one or more other solvents are 1,2-dichloroethylene and/or isopropanol.
5. The solvent composition or detergent composition according to claim 1 , for use as a solvent or detergent for oil.
6. The solvent composition according to claim 5 , wherein the oil is a lubricating oil.
7. The solvent composition according to claim 6 , wherein the lubricating oil is at least one lubricating oil selected from the group consisting of silicone oil, fluorine oil, mineral-based oil, grease, and wax.
8. An oil composition comprising oil and the solvent composition according to claim 1 .
9. The oil composition according to claim 8 , wherein the oil is a lubricating oil.
10. The oil composition according to claim 9 , wherein the lubricating oil is at least one lubricating oil selected from the group consisting of silicone oil, fluorine oil, mineral-based oil, grease, and wax.
11. (canceled)
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US17/470,597 US20210403837A1 (en) | 2016-11-11 | 2021-09-09 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
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JP2016-220620 | 2016-11-11 | ||
JP2016220620A JP6361721B2 (en) | 2016-11-11 | 2016-11-11 | Cleaning composition and cleaning method, and solvent composition, its use as a solvent for oils, and oil compositions containing it |
PCT/JP2017/040206 WO2018088418A1 (en) | 2016-11-11 | 2017-11-08 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
US201916347899A | 2019-05-07 | 2019-05-07 | |
US17/470,597 US20210403837A1 (en) | 2016-11-11 | 2021-09-09 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
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US16/347,899 Division US11220658B2 (en) | 2016-11-11 | 2017-11-08 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
PCT/JP2017/040206 Division WO2018088418A1 (en) | 2016-11-11 | 2017-11-08 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
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US16/347,899 Active US11220658B2 (en) | 2016-11-11 | 2017-11-08 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
US17/470,597 Abandoned US20210403837A1 (en) | 2016-11-11 | 2021-09-09 | Detergent composition, cleaning method, solvent composition, use thereof as solvent for oil, and oil composition containing same |
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CN (2) | CN114874861A (en) |
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CN111662792A (en) * | 2020-06-15 | 2020-09-15 | 上海锐一环保科技有限公司 | Halogenated olefin combined solvent containing 1-chloro-2, 3, 3-trifluoropropene and application thereof |
KR20220159701A (en) | 2021-05-26 | 2022-12-05 | (주)이노센스 | Oil Scale Treatment |
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US2673173A (en) * | 1950-05-26 | 1954-03-23 | Dow Chemical Co | Preparation of 1, 1, 3-trichloro-2, 3, 3-trifluoropropene and method of fumigating therewith |
GB1087873A (en) | 1964-06-26 | 1967-10-18 | Laporte Chemical | Halogenation of branched-chain hydrocarbons |
JP2001354985A (en) | 2000-06-16 | 2001-12-25 | Nippon Zeon Co Ltd | Solvent composition, lubricating polymer-containing liquid and article containing this lubricating polymer film |
US9499729B2 (en) * | 2006-06-26 | 2016-11-22 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
US7438825B1 (en) * | 2008-03-07 | 2008-10-21 | Arkema Inc. | Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and dimethoxymethane |
JP2013224383A (en) | 2012-04-23 | 2013-10-31 | Asahi Glass Co Ltd | Solvent composition for cleaning |
DE112013002166T5 (en) * | 2012-04-23 | 2015-01-15 | Asahi Glass Company, Limited | A lubricant solution and method for producing an article equipped with a lubricant coating film |
JP6019759B2 (en) * | 2012-05-30 | 2016-11-02 | セントラル硝子株式会社 | Heat transfer medium containing fluoroalkene |
KR20150128912A (en) * | 2013-03-15 | 2015-11-18 | 트레인 인터내셔날 인코포레이티드 | Lubricant defoaming additives and compositions |
WO2014178352A1 (en) * | 2013-04-30 | 2014-11-06 | 旭硝子株式会社 | Composition containing trifluoroethylene |
TW201542847A (en) | 2014-04-07 | 2015-11-16 | Tosoh Smd Inc | Boron doped N-type silicon target |
KR101944603B1 (en) * | 2014-09-03 | 2019-01-31 | 다이킨 고교 가부시키가이샤 | Antifouling article |
FR3027303B1 (en) | 2014-10-16 | 2016-10-07 | Arkema France | COMPOSITIONS BASED ON 1,1,1,2,3-PENTACHLOROPROPANE |
JP6115550B2 (en) * | 2014-11-17 | 2017-04-19 | ダイキン工業株式会社 | Method for separating both compounds from a composition comprising HFC-245cb and (E) -HFO-1234ze |
JP6432306B2 (en) | 2014-11-21 | 2018-12-05 | セントラル硝子株式会社 | Azeotropic-like composition comprising fluorine-containing olefin as a constituent |
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CN114874861A (en) | 2022-08-09 |
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KR20190077023A (en) | 2019-07-02 |
KR102220989B1 (en) | 2021-02-26 |
JP6361721B2 (en) | 2018-07-25 |
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