+

WO1992011351A1 - Compositions de type azeotrope - Google Patents

Compositions de type azeotrope Download PDF

Info

Publication number
WO1992011351A1
WO1992011351A1 PCT/US1991/009578 US9109578W WO9211351A1 WO 1992011351 A1 WO1992011351 A1 WO 1992011351A1 US 9109578 W US9109578 W US 9109578W WO 9211351 A1 WO9211351 A1 WO 9211351A1
Authority
WO
WIPO (PCT)
Prior art keywords
dichloro
weight percent
azeotrope
trifluoroethane
compositions
Prior art date
Application number
PCT/US1991/009578
Other languages
English (en)
Inventor
Ellen Louise Swan
Peter Brian Logsdon
Leonard Michael Stachura
Rajat Subhra Basu
Original Assignee
Allied-Signal Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US07/690,016 external-priority patent/US5124064A/en
Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Publication of WO1992011351A1 publication Critical patent/WO1992011351A1/fr

Links

Classifications

    • 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
    • C23G5/02829—Ethanes
    • C23G5/02832—C2H3Cl2F
    • 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
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/509—Mixtures of hydrocarbons and oxygen-containing solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents

Definitions

  • This invention relates to azeotrope-like mixtures of 1 ,1-dichloro-l-fluoroethane; dichlorotrifluoroethane; ethanol; and alkane having 5 or 6 carbon atoms. These mixtures are useful in a variety of vapor degreasing, cold cleaning and solvent cleaning applications including defluxing and dry cleaning.
  • Vapor degreasing and solvent cleaning with fluorocarbon based solvents have found widespread use in industry for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.
  • vapor degreasing or solvent cleaning consists of exposing a room temperature object to be cleaned to the vapors of a boiling solvent.
  • Vapors condensing on the object provide clean distilled solvent to wash away grease or other contamination.
  • the conventional operation of a vapor degreaser consists of immersing the part to be cleaned in a sump of boiling solvent which removes the bulk of the soil, thereafter immersing the part in a sump containing freshly distilled solvent near room temperature, and finally exposing the part to solvent vapors over the boiling sump which condense on the cleaned part.
  • the part can also be sprayed with distilled solvent before final rinsing.
  • Vapor degreasers suitable in the above-described operations are well known in the art.
  • Sherliker et al. in U.S. Patent 3,085,918 disclose such suitable vapor degreasers comprising a boiling sump, a clean sump, a water separator, and other ancillary equipment.
  • Cold cleaning is another application where a number of solvents are used.
  • the soiled part is either immersed in the fluid or wiped with rags or similar objects soaked in solvents and allowed to air dry.
  • Fluorocarbon solvents such as trichlorotrifluoroethane, have attained widespread use in recent years as effective, nontoxic, and nonflammable agents useful in degreasing applications and other solvent cleaning applications.
  • Trichlorotrifluoroethane has been found to have satisfactory solvent power for greases, oils, waxes and the like. It has therefore found widespread use for cleaning electric motors, compressors, heavy metal parts, delicate precision metal parts, printed circuit boards, gyroscopes, guidance systems, aerospace and missile hardware, aluminum parts and the like.
  • azeotrope or azeotrope-like compositions including the desired fluorocarbon components such as trichlorotrifluoroethane which include components which contribute additionally desired characteristics, such as polar functionality, increased solvency power, and stabilizers.
  • Azeotropic or azeotrope-like compositions are desired because they do not fractionate upon boiling. This behavior is desirable because in the previously described vapor degreasing equipment with which these solvents are employed, redistilled material is generated for final rinse-cleaning. Thus, the vapor degreasing system acts as a still.
  • solvent composition exhibits a constant boiling point, i.e., is azeotrope-like, fractionation will occur and undesirable solvent distribution may act to upset the cleaning and safety of processing.
  • Preferential evaporation of the more volatile components of the solvent mixtures which would be the case if they were not azeotrope-like, would result in mixtures with changed compositions which may have less desirable properties, such as lower solvency towards soils, less inertness towards metal, plastic or elastomer components, and increased flammability and toxicity.
  • hydrochlorofluorocarbons such as 1,1-dichloro-l-fluoroethane (known in the art as HCFC-141b) and dichlorotrifluoroethane (HCFC-123 or HCFC-123a)
  • HCFC-141b 1,1-dichloro-l-fluoroethane
  • HCFC-123 or HCFC-123a dichlorotrifluoroethane
  • U.S. Patent 4,836,947 discloses azeotrope-like mixtures of l,l-dichloro-l-fluoroethane and ethanol.
  • Commonly assigned U.S. Patent 4,842,764 discloses azeotrope-like mixtures of 1,1-dichloro-l-fluoroethane and methanol.
  • Commonly assigned U.S. Patent 4,863,630 discloses azeotrope-like mixtures of 1,1-dichloro-l-fluoroethane; dichlorotrifluoroethane; and ethanol.
  • Patent 4,894,176 discloses azeotrope-like mixtures of 1,1-dichloro-l-fluoroethane; dichlorotrifluoroethane; and methanol.
  • Commonly assigned U.S. Patent 4,960,535 discloses azeotrope-like mixtures of 1,1-dichloro-l-fluoroethane, dichlorotrifluoroethane, and a mono- or di-chlorinated C 2 or C 3 alkane.
  • Commonly assigned U.S. Patent 4,965,011 discloses azeotrope-like mixtures of 1,1-dichloro-l-fluoroethane, dichlorotrifluoroethane, and nitromethane.
  • Kokai Patent Publication 136,982 published May 30, 1989, discloses a buff-grinding cleaning agent of an azeotropic mixture of 67 weight percent l,l-dichloro-2,2,2-trifluoroethane and 33 weight percent 1,1-dichloro-l-fluoroethane, plus hydrocarbons, alcohols, ketones, chlorinated hydrocarbons, and esters.
  • Kokai Patent Publication 137,259 published May 30, 1989, discloses a resist separating agent of an azeotropic composition of 67 weight percent l,l-dichloro-2,2,2-trifluoroethane and 33 weight percent 1,1-dichloro-l-fluoroethane, plus hydrocarbons, alcohols, ketones, chlorinated hydrocarbons, aromatics, and esters.
  • Kokai Patent Publication 138,300 discloses a flux cleaning agent of an azeotrope of 67 weight percent 1,l-dichloro-2,2,2-trifluoroethane and 33 weight percent 1,1-dichloro-l-fluoroethane, plus hydrocarbons, alcohols, ketones, and chlorinated hydrocarbons.
  • Kokai Patent Publication 139,104 published May 31, 1989, discloses a solvent of an azeotropic mixture of 67 weight percent 1,l-dichloro-2,2,2-trifluoroethane and 33 weight percent l,l-dichloro-l-fluoroethane, plus hydrocarbons, alcohols, ketones, chlorinated hydrocarbons, and surfactants.
  • Kokai Patent Publication 139,104 published May 31, 1989, discloses a solvent of an azeotropic mixture of 67 weight percent 1,l-dichloro-2,2,2-trifluoroethane and 33 weight percent l,l-dichloro-l-fluoroethane, plus hydrocarbons, alcohols, ketones, chlorinated hydrocarbons, and surfactants.
  • Publication 139,861 published June 1, 1989, discloses a dry-cleaning agent of 67 weight percent l,l-dichloro-2,2,2-trifluoroethane and 33 weight percent 1,1-dichloro-l-fluoroethane, plus hydrocarbons, alcohols, ketones, chlorinated hydrocarbons, and surfactants.
  • Another object of the invention is to provide novel environmentally acceptable solvents for use in the aforementioned applications.
  • alkane having 5 or 6 carbon atoms is selected from the group consisting of n-pentane; 2-methylbutane; n-hexane; 2-methylpentane; 3-methylpentane;
  • the dichlorotrifluoroethane component can be one of its isomers: l,l-dichloro-2,2,2-trifluoroethane (known in the art as HCFC-123) ; l,2-dichloro-l,l,2-trifluoroethane (known in the art as
  • the preferred isomer of dichlorotrifluoroethane is HCFC-123.
  • "commercial HCFC-123” which is available as “pure” HCFC-123 containing about 90 to about 95 weight percent of HCFC-123, about 5 to about 10 weight percent of HCFC-123a, and impurities such as trichloromonofluoro ethane, trichlorotrifluoroethane, and methylene chloride which due to their presence in insignificant amounts, have no deleterious effects on the properties of the azeotrope-like compositions, is used.
  • Communication HCFC-123 is also available as “ultra-pure” HCFC-123 which contains about 95 to about 99.5 weight percent of HCFC-123, about 0.5 to about 5 weight percent of HCFC-123a, and impurities as listed above.
  • the novel azeotrope-like compositions comprise effective amounts of 1,1-dichloro-l-fluoroethane; dichlorotrifluoroethane; ethanol; and alkane having 5 or 6 carbon atoms.
  • effective amounts means the amount of each component which upon combination with the other component, results in the formation of the present azeotrope-like composition.
  • novel azeotrope-like compositions comprise 1,1-dichloro-l-fluoroethane; dichlorotrifluoroethane; ethanol; and alkane having 5 or 6 carbon atoms selected from the group consisting of n-pentane; 2-methylbutane; 2-methylpentane;
  • novel azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about l to about 38 weight percent of dichlorotrifluoroethane selected from the group consisting of 1,l-dichloro-2,2,2-trifluoroethane, 1,2-dichloro-l,1,2-trifluoroethane, or mixtures thereof; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of alkane having 5 or 6 carbon atoms selected from the group consisting of n-pentane; 2-methylbutane; 2-methylpentane; 3-methylpentane; 2,2-dimethylbutane; 2,3-dimethylbutane; and mixtures thereof which boil at about 31.2°C ⁇ about 0.8°C at 760 mm Hg (101 kPa) .
  • novel azeotrope-like compositions preferably comprise 1,1-dichloro-l-fluoroethane; l,l-dichloro-2,2,2-trifluoroethane; ethanol; and n-pentane which boil at about 30.9 ⁇ C, and more preferably, about 30.9°C + about 0.1°C at 760 mm Hg (101 kPa) .
  • Novel azeotrope-like compositions also preferably comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 32 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of n-pentane which boil at about 30.9°C at 760 mm Hg (101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 55 to about 95.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 32 weight percent of l,l-dichloro-2, 2 , 2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 1 to about 10 weight percent of n-pentane.
  • the azeotrope-like compositions of the invention comprise from about 56.5 to about 93.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 32 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 2.5 weight percent of ethanol; and from about l to about 9 weight percent of n-pentane.
  • compositional ranges for azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; 1,l-dichloro-2,2,2-trifluoroethane; ethanol; and n-pentane also apply to azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; l,2-dichloro-l,l,2-trifluoroethane; ethanol; and n-pentane which would boil at about 31.4°C at 760 mm Hg (101 kPa) .
  • 1,l-dichloro-2,2,2-trifluoroethane is so close to the boiling point of l,2-dichloro-l,l,2-trifluoroethane, it is also believed that azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; a mixture of 1,l-dichloro-2,2,2-trifluoroethane and 1,2-dichloro-l,1,2-trifluoroethane; ethanol; and n-pentane would form.
  • azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 32 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of n-pentane.
  • These compositions would boil at about 31.4°C at 760 mm Hg (101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 57 to about 97.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 32 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3.0 weight percent of ethanol; and from about 1 to about 8 weight percent of n-pentane.
  • the azeotrope-like compositions of the invention comprise from about 57.0 to about 93.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 32 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 1 to about 8 weight percent of n-pentane.
  • dichlorotrifluoroethane used is 1,l-dichloro-2,2,2-trifluoroethane
  • novel azeotrope-like compositions preferably comprise 1,1-dichloro-l-fluoroethane; l,l-dichloro-2,2,2-trifluoroethane; ethanol; and 2-methylbutane which boil at about 30.4°C and more preferably, about 30.4°C + about 0.1°C at 760 mm Hg (101 kPa) .
  • Novel azeotrope-like compositions also preferably comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 32 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of 2-methylbutane which boil at about 30.4 ⁇ C at 760 mm Hg (101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 61 to about 95.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 31 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 1 to about 5 weight percent of 2-methylbutane.
  • the azeotrope-like compositions of the invention comprise from about 62 to about 93.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 31 weight percent of l,l-dichloro-2,2,2-tri luoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 1 to about 5 weight percent of 2-methylbutane.
  • 1,l-dichloro-2, 2,2-trifluoroethane; ethanol; and 2-methylbutane also apply to azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; l,2-dichloro-l,l,2-trifluoroethane; ethanol; and
  • 1,l-dichloro-2,2,2-trifluoroethane is so close to the boiling point of l,2-dichloro-l,l,2-trifluoroethane, it is also believed that azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; a mixture of 1,l-dichloro-2,2,2-trifluoroethane and 1,2-dichloro-l,1,2-trifluoroethane; ethanol; and 2-methylbutane would form.
  • azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 32 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of 2-methylbutane.
  • These compositions boil at about 30.9°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention comprise from about 61 to about 95.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 31 weight percent of a mixture of l,l-dichloro-2, 2 ,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent ethanol; and from about 1 to about 5 weight percent 2-methylbutane.
  • the azeotrope-like compositions of the invention comprise from about 62 to about 93.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 31 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 2 weight percent ethanol; and from about 1 to about 5 weight percent 2-methylbutane.
  • dichlorotrifluoroethane used is l,l-dichloro-2,2,2-trifluoroethane
  • novel azeotrope-like compositions preferably comprise
  • 2-methylpentane which boil at about 31.0°C and more preferably, at about 31.0°C + about 0.5 ⁇ C at 760 mm Hg (101 kPa) .
  • Novel azeotrope-like compositions also preferably comprise from about 55 to about 98 weight percent of 1,l-dichloro-1-fluoroethane; from about 1 to about 37 weight percent of 1,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 5 weight percent of 2-methylpentane which boil at about 31.0°C at 760 mm Hg (101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 59 to about 97.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 35 weight percent of
  • 1,l-dichloro-2,2,2-trifluoroethane from about 0.5 to about 3 weight percent of ethanol; and from about 1 to about 3 weight percent of 2-methylpentane.
  • the azeotrope-like compositions of the invention comprise from about 62 to about 95.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 33 weight percent of 1,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 1 to about 3 weight percent of 2-methylpentane.
  • 1,l-dichloro-2,2,2-trifluoroethane is 27.8°C and the boiling point of l,2-dichloro-l,l,2-trifluoroethane is
  • 1,l-dichloro-2, 2 ,2-trifluoroethane; ethanol; and 2-methylpentane also apply to azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; l,2-dichloro-l,l,2-trifluoroethane; ethanol; and
  • azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 37 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 5 weight percent of 2-methylpentane.
  • These compositions would boil at about 31.8°C at 760 mm Hg(10l kPa) .
  • the azeotrope-like compositions of the invention comprise from about 59 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 35 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 2-methylpentane.
  • the azeotrope-like compositions of the invention comprise from about 62 to about 96 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 33 weight percent of a mixture of l,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 2-methylpentane.
  • dichlorotrifluoroethane used is 1,l-dichloro-2,2,2-trifluoroethane
  • novel azeotrope-like compositions preferably comprise 1,l-dichloro-1-fluoroethane; 1,l-dichloro-2,2,2-trifluoroethane; ethanol; and 3-methylpentane which boil at about 31°C and more preferably, about 31°C ⁇ about 0.5°C at 760 mm Hg (101 kPa) .
  • Novel azeotrope-like compositions also preferably comprise from about 55 to about 98 weight percent of
  • 1,1-dichloro-l-fluoroethane from about 1 to about 37 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 5 weight percent of 3-methylpentane which boil at about 31°C at 760 mm Hg
  • the azeotrope-like compositions of the invention comprise from about 59 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 35 weight percent of
  • 1,l-dichloro-2, 2 ,2-trifluoroethane from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 3-methylpentane.
  • the azeotrope-like compositions of the invention comprise from about 62 to about 96 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 33 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 3-methylpentane.
  • compositional ranges for azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; 1,l-dichloro-2,2,2-trifluoroethane; ethanol; and 3-methylpentane also apply to azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; l,2-dichloro-l,l,2-trifluoroethane; ethanol; and 3-methylpentane which would boil at about 31°C at 760 mm Hg (101 kPa) .
  • azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about l to about 37 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 5 weight percent of 3-methylpentane.
  • These compositions would boil at about 31°C at 760 mm Hg(101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 59 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 35 weight percent of a mixture of
  • 1,2-dichloro-l,1,2-trifluoroethane from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 3-methylpentane.
  • the azeotrope-like compositions of the invention comprise from about 62 to about 96 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 33 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 3-methylpentane.
  • dichlorotrifluoroethane used is 1,l-dichloro-2,2,2-trifluoroethane
  • novel azeotrope-like compositions preferably comprise 1,1-dichloro-l-fluoroethane;
  • 1,l-dichloro-2,2,2-trifluoroethane 1,l-dichloro-2,2,2-trifluoroethane; ethanol; and 2,2-dimethylbutane which boil at about 31.9°C and more preferably, about 31.9°C + about 0.2°C at 760 mm Hg (101 kPa) .
  • Novel azeotrope-like compositions also preferably comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 37 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 5 weight percent of 2,2-dimethylbutane which boil at about 31.9°C at 760 mm Hg (101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 57 to about 95.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 37 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 1 to about 4 weight percent of 2,2-dimethylbutane.
  • the azeotrope-like compositions of the invention comprise from about 63.2 to about 92.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 32 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 1.6 weight percent of ethanol; and from about 2 to about 3.2 weight percent of 2,2-dimethylbutane.
  • 1,1-dichloro-l-fluoroethane; ethanol; and 2,2-dimethylbutane would form. It should be understood that the aforementioned compositional ranges for azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; 1,l-dichloro-2,2,2-trifluoroethane; ethanol; and 2,2-dimethylbutane also apply to azeotrope-like compositions of l,l-dichloro-l-fluoroethane; 1,2-dichloro-l,1,2-trifluoroethane; ethanol; and 2,2-dimethylbutane. These compositions boil at about 31.9°C at 760 mm Hg (101 kPa) .
  • azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 37 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 5 weight percent of 2,2-dimethylbutane.
  • These compositions would boil at about 31.9°C at 760 mm Hg(101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 57.2 to about 95.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 37 weight percent of a mixture of 1,l-dichloro-2, 2.2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 1 to about 4 weight percent of 2,2-dimethylbutane.
  • the azeotrope-like compositions of the invention comprise from about 63.2 to about 92.5 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 32 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 1.6 weight percent of ethanol; and from about 2 to about 3.2 weight percent of 2,2-dimethylbutane.
  • dichlorotrifluoroethane used is 1,l-dichloro-2,2,2-trifluoroethane
  • novel azeotrope-like compositions preferably comprise
  • 2,3-dimethylbutane which boil at about 31.9°C and more preferably, about 31.9°C ⁇ about 0.2°C at 760 mm Hg
  • Novel azeotrope-like compositions also preferably comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 38 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of 2,3-dimethylbutane which boil at about 31.9°C at 760 mm Hg (101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 57 to about 96 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 37 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 4 weight percent of 2,3-dimethylbutane.
  • the azeotrope-like compositions of the invention comprise from about 63 to about 93 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 32 weight percent of l,l-dichloro-2,2,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 2,3-dimethylbutane.
  • 1,l-dichloro-2,2,2-trifluoroethane is 27.8°C and the boiling point of 1,2-dichloro-l,1,2-trifluoroethane is
  • 2,3-dimethylbutane also apply to azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; l,2-dichloro-l,l,2-trifluoroethane; ethanol; and
  • 1,l-dichloro-2,2,2-trifluoroethane is so close to the boiling point of l,2-dichloro-l,l,2-trifluoroethane, it is also believed that azeotrope-like compositions of 1,1-dichloro-l-fluoroethane; a mixture of 1,l-dichloro-2,2,2-trifluoroethane and
  • azeotrope-like compositions comprise from about 55 to about 98 weight percent of 1,1-dichloro-l-fluoroethane; from about 1 to about 38 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 3 weight percent of ethanol; and from about 0.5 to about 10 weight percent of 2,3-dimethylbutane.
  • These compositions would boil at about 31.9°C at 760 mm Hg(101 kPa) .
  • the azeotrope-like compositions of the invention comprise from about 57 to about 96 weight percent of 1,1-dichloro-l-fluoroethane; from about 3 to about 37 weight percent of a mixture of 1,l-dichloro-2 , 2 ,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 4 weight percent of 2,3-dimethylbutane.
  • the azeotrope-like compositions of the invention comprise from about 63 to about 93 weight percent of 1,1-dichloro-l-fluoroethane; from about 5 to about 32 weight percent of a mixture of 1,l-dichloro-2,2,2-trifluoroethane and 1,2-dichloro-l,1,2-trifluoroethane; from about 0.5 to about 2 weight percent of ethanol; and from about 0.5 to about 3 weight percent of 2,3-dimethylbutane.
  • the preferred dichlorotrifluoroethane component is "commercial HCFC-123".
  • the azeotrope-like compositions of the invention containing a mixture of HCFC-123 and HCFC-123a are azeotrope-like in that they are constant-boiling or essentially constant-boiling. It is not known whether this is the case because the separate quaternary azeotrope-like compositions with HCFC-123 and HCFC-123a have boiling points so close to one another as to be indistinguishable for practical purposes or whether HCFC-123 and HCFC-123a form a five-component azeotrope with 1,1-dichloro-l-fluoroethane; ethanol; and n-pentane; 2-methylbutane; 2-methylpentane; 3-methylpentane; 2,2-dimethylbutane; or 2,3-dimethylbutane.
  • compositions within the indicated ranges, as well as certain compositions outside the indicated ranges, are azeotrope-like, as defined more particularly below.
  • the 1,1-dichloro-l-fluoroethane and dichlorotrifluoroethane components of the invention have good solvent properties.
  • the ethanol and alkane components also have good solvent capabilities. Thus, when these components are combined in effective amounts, an efficient azeotrope-like solvent results.
  • compositions with the indicated ranges, as well as certain compositions outside the indicated ranges are azeotrope-like, as defined more particularly below.
  • thermodynamic state of a fluid is defined by four variables: pressure, temperature, liquid composition and vapor composition, or P-T-X-Y, respectively.
  • An azeotrope is a unique characteristic of a system of two or more components where X and Y are equal at the stated P and T. In practice, this means that the components of a mixture cannot be separated during distillation, and therefore are useful in vapor phase solvent cleaning as described above.
  • azeotrope-like composition is intended to mean that the composition behaves like an azeotrope, i.e. has constant-boiling characteristics or a tendency not to fractionate upon boiling or evaporation.
  • the composition of the vapor formed during boiling or evaporation is identical or substantially identical to the original liquid composition.
  • the liquid composition if it changes at all, changes only to a minimal or negligible extent. This is to be contrasted with non-azeotrope-like compositions in which during boiling or evaporation, the liquid composition changes to a substantial degree.
  • one way to determine whether a candidate mixture is "azeotrope-like" within the meaning of this invention is to distill a sample thereof under conditions (i.e. resolution - number of plates) which would be expected to separate the mixture into its separate components. If the mixture is non-azeotrope-like, the mixture will fractionate, i.e. separate into its various components with the lowest boiling component distilling off first, and so on. If the mixture is azeotrope-like, some finite amount of a first distillation cut will be obtained which contains all of the mixture components and which is constant-boiling or behaves as a single substance. This phenomenon cannot occur if the mixture is not azeotrope-like, i.e. it does not behave like an azeotrope. Of course, upon distillation of an azeotrope-like composition such as in a vapor degreaser, the true azeotrope will form and tend to concentrate.
  • azeotrope-like compositions there is a range of compositions containing the same components in varying proportions which are azeotrope-like or constant-boiling. All such compositions are intended to be covered by the term azeotrope-like or constant-boiling as used herein.
  • azeotrope-like or constant-boiling As an example, it is well known that at differing pressures, the composition of a given azeotrope-like composition will vary at least slightly as does the boiling point of the composition.
  • an azeotrope-like composition of A and B represents a unique type of relationship but with a variable composition depending on temperature and/or pressure.
  • 1,l-dichloro-2,2,2-trifluoroethane; ethanol; and n-pentane the mixtures boil within + about 0.1 ⁇ C (at about 760 mm Hg (101 kPa) ) of the 30.9°C boiling point.
  • the mixtures boil within + about 0.5°C (at about 760 mm Hg (101 kPa) ) of the 31 ⁇ C boiling point.
  • 1,1-dichloro-l-fluoroethane; l,l-dichloro-2,2,2-trifluoroethane; ethanol; and 2,2-dimethylbutane the mixtures boil within + about 0.2°C(at about 760 mm Hg (101 kPa)) of the 31.9°C boiling point.
  • the boiling point of the azeotrope-like composition will vary with the pressure.
  • azeotrope-like compositions of the invention are useful as solvents in a variety of vapor degreasing, cold cleaning and solvent cleaning applications including defluxing and dry cleaning and as blowing agents.
  • the azeotrope-like compositions of the invention may be used to clean solid surfaces by treating the surfaces with the compositions in any manner well known to the art such as by dipping or spraying or use of conventional degreasing apparatus.
  • the 1,1-dichloro-l-fluoroethane; dichlorotrifluoroethane; ethanol; n-pentane; 2-methylbutane; 2-methylpentane; 3-methylpentane; 2,2-dimethylbutane; and 2,3-dimethylbutane components of the novel solvent azeotrope-like compositions of the invention are known materials and are commercially available.
  • the materials should be used in sufficiently high purity so as to avoid the introduction of adverse influences upon the desired properties or constant boiling properties of the system.
  • compositions may include additional components so as to form new azeotrope-like or constant-boiling compositions. Any such compositions are considered to be within the scope of the present invention as long as the compositions are constant-boiling or essentially constant-boiling and contain all of the essential components described herein.
  • a 5-plate Oldershaw distillation column with a cold water condensed automatic liquid dividing head was used for this example.
  • the distillation column was charged with HCFC-141b, commercially available ultra-pure HCFC-123, ethanol, and n-pentane in the amounts indicated in Table I below for the starting material.
  • the composition was heated under total reflux for about an hour to ensure equilibration.
  • a reflux ratio of 3:1 was employed for this particular distillation.
  • Approximately 50 percent of the original charges were collected in four similar-sized overhead fractions.
  • the compositions of these fractions were analyzed using gas chromatography. The averages of the distillate fractions and the overhead temperatures are quite constant within the uncertainty associated with determining the compositions, indicating that the mixture is constant-boiling or azeotrope-like.
  • Examples l and 2 are repeated except that l,2-dichloro-l,l,2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • Examples 1 and 2 are repeated except that a mixture of l,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • a 5-plate Oldershaw distillation column with a cold water condensed automatic liquid dividing head was used for these examples.
  • the distillation column was charged with HCFC-141b, commercially available ultra-pure HCFC-123, ethanol, and 2-methylbutane in the amounts indicated in Table II below for the starting material.
  • Each composition was heated under total reflux for about an hour to ensure equilibration.
  • a reflux ratio of 5:1 was employed for this particular distillation.
  • Approximately 50 percent of the original charges were collected in four similar-sized overhead fractions.
  • the compositions of these fractions were analyzed using gas chromatography. The averages of the distillate fractions and the overhead temperatures are quite constant within the uncertainty associated with determining the compositions, indicating that the mixtures are constant-boiling or azeotrope-like.
  • Examples 7 and 8 are repeated except that l,2-dichloro-l,l,2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • 1,2-dichloro-l,1,2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • Examples 13 and 14 are repeated except that l,2-dichloro-l,l,2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • Examples 13 and 14 are repeated except that a mixture of 1,l-dichloro-2,2,2-trifluoroethane and l,2-dichloro-l,l,2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • Examples 19 and 20 are repeated except that l,2-dichloro-l,l,2-trifluoroethane is used instead of l,l-dichloro-2,2,2-trifluoroethane.
  • Examples 19 and 20 are repeated except that a mixture of l,l-dichloro-2,2,2-trifluoroethane and 1,2-dichloro-l,1,2-trifluoroethane is used instead of 1,l-dichloro-2 , 2 ,2-trifluoroethane.
  • a 5-plate Oldershaw distillation column with a cold water condensed automatic liquid dividing head was used for these examples.
  • the distillation column was charged with HCFC-141b, commercially available ultra-pure HCFC-123, ethanol, and 2,2-dimethylbutane in the amounts indicated in Table VI below for the starting material.
  • Each composition was heated under total reflux for about an hour to ensure equilibration.
  • a reflux ratio of 3:1 was employed for this particular distillation. Approximately 50 percent of the original charges were collected in four similar-sized overhead fractions.
  • compositions of these fractions were analyzed using gas chromatography.
  • the averages of the distillate fractions and the overhead temperatures are quite constant within the uncertainty associated with determining the compositions, indicating that the mixtures are constant-boiling or azeotrope-like.
  • Examples 25 and 26 are repeated except that a mixture of l,l-dichloro-2,2,2-trifluoroethane and 1,2-dichloro-l-l-2-trifluoroethane is used instead of 1,l-dichloro-2,2,2-trifluoroethane.
  • Performance studies are conducted wherein metal coupons are cleaned using the present azeotrope-like compositions as solvents.
  • the metal coupons are soiled with various types of oils and heated to 93°C so as to partially simulate the temperature attained while machining and grinding in the presence of these oils.
  • the metal coupons thus treated are degreased in a three-sump vapor phase degreaser machine.
  • condenser coils around the lip of the machine are used to condense the solvent vapor which is then collected in a sump.
  • the condensate overflows into cascading sumps and eventually goes into the boiling sump.
  • the metal coupons are held in the solvent vapor and then vapor rinsed for a period of 15 seconds to 2 minutes depending upon the oils selected.
  • the azeotrope-like compositions of Examples 1 through 36 are used as the solvents. Cleanliness testing of coupons are done by measurement of the weight change of the coupons using an analytical balance to determine the total residual materials left after cleaning.
  • n-pentane 2-methylbutane; 2-methylpentane; 3-methylpentane; 2,2-dimethylbutane; and 2,3-dimethylbutane
  • Mixtures of n-pentane; 2-methylbutane; 2-methylpentane; 3-methylpentane; 2,2-dimethylbutane; and 2,3-dimethylbutane may be used in any proportions in the present invention as long as azeotrope-like compositions form.
  • Inhibitors may be added to the present azeotrope-like compositions to inhibit decomposition of the compositions; react with undesirable decomposition products of the compositions; and/or prevent corrosion of metal surfaces.
  • Any or all of the following classes of inhibitors may be employed in the invention: alkanols having 4 to 7 carbon atoms, nitroalkanes having 1 to 3 carbon atoms, 1,2-epoxyalkanes having 2 to 7 carbon atoms, phosphite esters having 12 to 30 carbon atoms, ethers having 3 or 4 carbon atoms, unsaturated compounds having 4 to 6 carbon atoms, acetals having 4 to 7 carbon atoms, ketones having 3 to 5 carbon atoms, and amines having 6 to 8 carbon atoms.
  • Other suitable inhibitors will readily occur to those skilled in the art.
  • Examples of useful alkanols having 4 to 7 carbon atoms are 2-methyl-2-propanol; 2-methy1-2-butanol; 1-pentanol; 2-pentanol; 3-pentanol; and 3-ethyl-3-pentanol.
  • the preferred alkanols are 2-methyl-2-propanol and 3-pentanol.
  • Examples of useful nitroalkanes having 1 to 3 carbon atoms include nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane.
  • the preferred nitroalkanes are nitromethane and nitroethane.
  • Examples of useful 1,2-epoxyalkanes having 2 to 7 carbon atoms include epoxyethane; 1,2-epoxypropane; 1,2-epoxybutane; 2,3-epoxybutane; 1,2-epoxypentane; 2,3-epoxypentane; 1,2-epoxyhexane; and 1,2-epoxyheptane.
  • the preferred 1,2-epoxyalkanes are 1,2-epoxybutane and 1,2-epoxypropane.
  • Examples of useful phosphite esters having 12 to 30 carbon atoms include diphenyl phosphite; triphenyl phosphite; triisodecyl phosphite; triisooctyl phosphite; and diisooctyl phosphite.
  • the preferred phosphite esters are triisodecyl phosphite (hereinafter TDP) and triisooctyl phosphite (hereinafter TOP) .
  • Examples of useful ethers having 3 or 4 carbon atoms include diethylene oxide; 1,2-butylene oxide; 2,3-butylene oxide; and dimethoxymethane.
  • the preferred ethers are diethylene oxide and dimethoxymethane.
  • Examples of useful unsaturated compounds having 4 to 6 carbon atoms include 1,4-butyne diol; 1,5-pentyne diol; and 1,6-hexyne diol.
  • the preferred unsaturated compounds are 1,4-butyne diol and 1,5-pentyne diol.
  • Examples of useful acetals having 4 to 7 carbon atoms include dimethoxyethane; 1,1-diethyoxyethane; and dipropoxy ethane.
  • the preferred acetals are dimethoxyethane and dipropoxymethane.
  • ketones having 3 to 5 carbon atoms examples include 2-propanone; 2-butanone; and 3-pentanone.
  • the preferred ketones are 2-propanone and 2-butanone.
  • Examples of useful amines having 6 to 8 carbon atoms include triethyl amine, dipropyl amine, and diisobutyl amine.
  • the preferred amines are triethyl amine and dipropyl amine.
  • the inhibitors may be used alone or in mixtures thereof in any proportions. Typically, up to about 2 percent based on the total weight of the azeotrope-like composition of inhibitor might be used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)

Abstract

Compositions de type azéotrope comprenant 1,1-dichloro-1-fluoroéthane; dichlorotrifluoroéthane; éthanol, et alcane ayant 5 ou 6 atomes de carbone, ces compositions étant stables et utiles en tant qu'agents dégraissants et en tant que solvants dans une variété d'applications de nettoyage industriel y compris le nettoyage à froid et le défluxage de plaques de circuits imprimés et le nettoyage à sec.
PCT/US1991/009578 1990-12-19 1991-12-18 Compositions de type azeotrope WO1992011351A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US63012690A 1990-12-19 1990-12-19
US630,126 1990-12-19
US07/690,016 US5124064A (en) 1990-12-19 1991-04-23 Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; ethanol; and alkane having 5 or 6 carbon atoms
US690,016 1991-04-23

Publications (1)

Publication Number Publication Date
WO1992011351A1 true WO1992011351A1 (fr) 1992-07-09

Family

ID=27091087

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/009578 WO1992011351A1 (fr) 1990-12-19 1991-12-18 Compositions de type azeotrope

Country Status (1)

Country Link
WO (1) WO1992011351A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993009271A1 (fr) * 1991-11-08 1993-05-13 Allied-Signal Inc. Compositions de type azeotropique comprenant 1,1-dichloro-1-fluorethane; alcane contenant 6 atomes de carbone; et eventuellement alcanol et nitromethane
WO1993016163A1 (fr) * 1992-02-05 1993-08-19 Allied-Signal Inc. Compositions analogues a des azeotropes contenant du 1,1-dichloro-1-fluoroethane, de l'alcane c5 ou c6 ou du cycloalcane, du dichloromethane et eventuellement un alcanol et/ou du nitromethane

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01138300A (ja) * 1987-11-25 1989-05-31 Asahi Glass Co Ltd フラツクス洗浄剤
US4863630A (en) * 1989-03-29 1989-09-05 Allied-Signal Inc. Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane and ethanol
EP0379268A2 (fr) * 1989-01-17 1990-07-25 E.I. Du Pont De Nemours And Company Mélange type azéotrope à température d'ébullition constante, composé de dichlorotrifluoroéthane, 1,1-dichloro-1-fluoroéthane et de méthanol et/ou éthanol
US4994201A (en) * 1989-09-25 1991-02-19 Allied-Signal Inc. Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, methanol and cyclopentane

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01138300A (ja) * 1987-11-25 1989-05-31 Asahi Glass Co Ltd フラツクス洗浄剤
EP0379268A2 (fr) * 1989-01-17 1990-07-25 E.I. Du Pont De Nemours And Company Mélange type azéotrope à température d'ébullition constante, composé de dichlorotrifluoroéthane, 1,1-dichloro-1-fluoroéthane et de méthanol et/ou éthanol
US4863630A (en) * 1989-03-29 1989-09-05 Allied-Signal Inc. Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane and ethanol
US4994201A (en) * 1989-09-25 1991-02-19 Allied-Signal Inc. Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, methanol and cyclopentane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993009271A1 (fr) * 1991-11-08 1993-05-13 Allied-Signal Inc. Compositions de type azeotropique comprenant 1,1-dichloro-1-fluorethane; alcane contenant 6 atomes de carbone; et eventuellement alcanol et nitromethane
WO1993016163A1 (fr) * 1992-02-05 1993-08-19 Allied-Signal Inc. Compositions analogues a des azeotropes contenant du 1,1-dichloro-1-fluoroethane, de l'alcane c5 ou c6 ou du cycloalcane, du dichloromethane et eventuellement un alcanol et/ou du nitromethane

Similar Documents

Publication Publication Date Title
US4863630A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane and ethanol
US5219490A (en) Azeotrope-like compositions of 1,1,2,3,3-pentafluoropropane
US4894176A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane and methanol
US4816174A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane
US4960535A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane and a mono- or di-chlorinated C2 or C3 alkane
US5124063A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; methanol; and alkane having 5 or 6 carbon atoms
US5073206A (en) Method of cleaning using azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane
US5219488A (en) Azeotrope-like compositions of 2-trifluoromethyl-1,1,1,2-tetrafluorobutane and ethanol or isopropanol
US5120461A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; methanol; and alkene having 5 carbon atoms
US5085798A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, cyclopentane and optionally an alkanol
US4994201A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, methanol and cyclopentane
US5124064A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; ethanol; and alkane having 5 or 6 carbon atoms
WO1991009156A1 (fr) Compositions similaires aux azeotropes de 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloroethylene et alcanol ayant de 3 a 7 atomes de carbone
US5137651A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, 1,2-dichloroethylene, and optionally methanol or ethanol
US5122294A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; ethanol; and alkene having 5 carbon atoms
US5219489A (en) Azeotrope-like compositions of 2-trifluoromethyl-1,1,1,2-tetrafluorobutane and methanol
US4965011A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, and nitromethane
US5085797A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, a monochlorinated C3 alkane and optionally an alkanol
WO1992011351A1 (fr) Compositions de type azeotrope
US5145598A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluorethane, nitromethane and methanol or ethanol
AU7311791A (en) A method of cleaning using azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane
US5085796A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, ethanol and a mono- or di-chlorinated C2 or C3 alkane
WO1990007568A1 (fr) Compositions semblables a l'azeotrope contenant du 1,1-dichloro-1-fluoroethane, du dichlorotrifluoroethane et du methanol ou de l'ethanol
US5182042A (en) Azeotrope-like compositions of 1,1,1-trifluorohexane and perfluoromethylcyclohexane
US5024781A (en) Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, methanol and a mono- or di-chlorinated C2 or C3 alkane

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU MC NL SE

CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: IN PAT.BUL.17/92,UNDER INID (51) "IPC" REPLACE "C23G 5/022" BY "C23G 5/028"

NENP Non-entry into the national phase

Ref country code: CA

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载