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WO1991005035A1 - Compositions de dichloropentafluoropropane semblables a l'azeotrope et un alcanol possedant entre 1 et 4 atomes carbone - Google Patents

Compositions de dichloropentafluoropropane semblables a l'azeotrope et un alcanol possedant entre 1 et 4 atomes carbone Download PDF

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Publication number
WO1991005035A1
WO1991005035A1 PCT/US1990/005384 US9005384W WO9105035A1 WO 1991005035 A1 WO1991005035 A1 WO 1991005035A1 US 9005384 W US9005384 W US 9005384W WO 9105035 A1 WO9105035 A1 WO 9105035A1
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WO
WIPO (PCT)
Prior art keywords
compositions
weight percent
azeotrope
dichloro
pentafluoropropane
Prior art date
Application number
PCT/US1990/005384
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English (en)
Inventor
Hillel Magid
David Paul Wilson
Dennis M. Lavery
Richard M. Hollister
Richard E. Eibeck
Michael Van Der Puy
Rajat Basu
Ellen Louise Swan
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 US07/526,748 external-priority patent/US5124065A/en
Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Priority to KR1019920700785A priority Critical patent/KR0145743B1/ko
Priority to AT90915683T priority patent/ATE101194T1/de
Priority to BR909007715A priority patent/BR9007715A/pt
Priority to DE69006508T priority patent/DE69006508T2/de
Publication of WO1991005035A1 publication Critical patent/WO1991005035A1/fr
Priority to NO921254A priority patent/NO178438C/no

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Classifications

    • 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
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5081—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being alcohols only
    • 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
    • C23G5/02851—C2HCl2F5

Definitions

  • This invention relates to azeotrope-like mixtures of dichloropentafluoropropane and an alkanol having 1-4 carbon atoms. These mixtures are useful in ' a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.
  • Fluorocarbon based solvents have been used extensively 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. Final evaporation of solvent from the object leaves the object free of residue. This is contrasted with liquid solvents which leave deposits on the object after rinsing.
  • a vapor degreaser is used for difficult to remove soils where elevated temperature is necessary to improve the cleaning action of the solvent, or for large volume assembly line operations where the cleaning of metal parts and assemblies must be done efficiently.
  • 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 cloths soaked in solvents and allowed to air dry.
  • nontoxic nonflammable fluorocarbon solvents like trichlorotrifluoroethane, have been used extensively in degreasing applications and other solvent cleaning applications.
  • Trichlorotrifluoro ⁇ ethane 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, etc.
  • azeotropic compositions having fluorocarbon components because the fluorocarbon components contribute additionally desired characteristics, like polar functionality, increased solvency power, and stabilizers.
  • Azeotropic 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. Therefore, unless the solvent composition is essentially constant boiling, 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 an azeotrope or 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 flam ability and toxicity.
  • fluorocarbon-based azeotrope-like mixtures are of particular interest because they are considered to be stratospherically safe substitutes for presently used fully halogenated chlorofluorocarbons.
  • the latter have been implicated in causing environmental problems associated with the depletion of the earth's protective ozone layer.
  • Mathematical models have substantiated that hydrochlorofluorocarbons, like dichloropentafluoro ⁇ propane, have a much lower ozone depletion potential and global warming potential than the fully halogenated species.
  • the invention relates to novel azeotrope-like compositions which are useful in a variety of industrial cleaning applications. Specifically the invention relates to compositions of dichloropenta- fluoropropane and an alkanol having 1-4 carbon atoms which are essentially constant boiling, environmentally acceptable and which remain liquid at room temperature.
  • novel azeotrope-like compositions consisting essentially of from about 82 to about 99.99 weight percent dichloropentafluoropropane and from about 0.01 to about 18 weight percent of an alkanol having 1-4 carbon atoms wherein the azeotrope-like components of the composition consist of dichloropentafluoropropane and an alkanol having 1-4 carbon atoms which boil at about 50.6°C ⁇ about 5.6°C at 760 mm Hg.
  • Dichloropentafluoropropane exists in nine iso eric forms: (1) 2,2-dichloro-l,1,1,3,3-penta- fluoropropane (HCFC-225a) ; (2) 1,2-dichloro-l,2,3,3,3- pentafluoropropane (HCFC-225ba) ; (3) 1,2-dichloro- 1,1,2,3,3-pentafluoropropane (HCFC-225bb) ; (4) 1,l-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) ; (5) l,3-dichloro-l,l,2,2,3-pentafluoropropane (HCFC-225cb) ; (6) 1,1-dichloro-l,2,2,3,3-penta- fluoropropane (HCFC-225cc) ; (7) 1,2-dichloro-l, 1,3,3,3- pentafluoro
  • dichloropenta- fluoropropane will refer to any of the isomers or an admixture of the isomers in any proportion.
  • the dichloropentafluoropropane component of the invention has good solvent properties.
  • the alkanol component also has good solvent capabilities; dissolving polar organic materials and amine hydrochlorides . Thus, when these components are combined in effective amounts, an efficient azeotropic solvent results.
  • the azeotrope-like compositions of the invention consist essentially of from about 82 to about 97 weight percent dichloropenta- fluoropropane and from about 3 to about 18 weight percent methanol and boil at about 47.2°C ⁇ about 1.9°C at 760 mm Hg .
  • the azeotrope-like compositions of the invention consist essentially of from about 86 to about 99 weight percent dichloropentafluoropropane and from about 1 to about 14 weight percent ethanol and boil at about 52.1 C ⁇ about 2.2°C at 760. mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 96 to about 99.99 weight percent dichloropentafluoropropane and from about 0.01 to about 4 weight percent 1-propanol and boil at about 53.6°C ⁇ about 2.5°C at 760 mm Hg .
  • the azeotrope-like compositions of the invention consist essentially of from about 94 to about 99.99 weight percent dichloropentafluoropropane and from about 0.01 to about 6 weight percent 2-pro ⁇ anol and boil at about
  • the azeotrope-like compositions of the invention consist essentially of from about 98 to about 99.99 weight -1- percent dichloropentafluoropropane and from about 0.01 to about 2 weight percent 2-methyl-2-propanol and boil at about 53.6°C ⁇ about 2.5°C at "760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 82 to about 97 weight percent 1, l-dichloro-2,2,3,3,3- ⁇ entafluoropropane and from about 3 to about 18 weight percent methanol and boil at about 45.4°C ⁇ about 0.5°C at 752 mm Hg.
  • the azeotrope-like compositions consist essentially of from about 86 to about 96 weight percent 1, l-dichloro-2,2,3,3,3-penta- fluoropropane and from about 4 to about 14 weight percent methanol.
  • the azeotrope-like compositions consist essentially of from about 88 to about 96 weight percent 1,l-dichloro-2,2,3,3,3-penta- fluoropropane and from about 4 to about 12 weight percent methanol.
  • the azeotrope-like compositions consist essentially of from about 89 to about 95 weight percent 1,l-dicz ⁇ Loro-2,2,3,3,3-penta- fluoropropane and from about 5 to about 11 weight percent methanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 92 to about 99 weight percent 1,1-dichloro- 2,2,3,3,3-pentafluoropropane and from about 1 to about 8 weight percent ethanol and boil at about 50.0 C ⁇ about 0.5°C at 752 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 94 to about 99 weight percent 1,l-dichloro-2,2,3,3,3-pentafluoro ⁇ propane and from about 1 to about 6 weight percent ethanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 94 to about 98.5 weight percent 1,l-dichloro-2,2,3,3,3-pentafluoro ⁇ propane and from about 1.5 to about 6 weight percent ethanol.
  • the azeotrope-like compositions of the invention consist essentially of
  • the azeotrope-like compositions of the invention consist essentially of from about 97.5 to about 99.99 weight percent 1, l-dichloro-2,2,3,3,3-penta- fluoropropane and from about 0.01 to about 2.5 weight percent 2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 98 to about 99.99 weight percent 1,l-dichloro-2,2,3,3,3-penta- fluoropropane and from about 0.01 to about 2 weight percent 2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 82 to about 97 weight percent 1,3-dichloro- 1,1,2,2,3-pentafluoropropane and from about 3 to about 18 weight percent methanol and boil at about 47.9 C ⁇ about 0.8°C at 736 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 84 to about 96 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane and from about 4 to about 16 weight percent methanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 86 to about 96 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane and from about 4 to about 14 weight percent methanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 88 to about 95 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane and from about 5 to about 12 weight percent methanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 86 to about 97 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoropropane and from about . 3 to about 14 weight percent ethanol and boil at about 53.1°C ⁇ about 0.4°C at 738 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 88 to about 97 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane and from about 3 to about 12 weight percent ethanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 89 to about 97 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane and from about 3 to about 11 weight percent ethanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 96 to about 99.99 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoropropane and from about 0.01 to about 4 weight percent 1-pro ⁇ anol and boil at about 55.5°C ⁇ about 0.2°C at 747 ram Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 97 to about 99.99 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane and from about 0.01 to about 3 weight percent 1-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 98 to about 99.99 weight percent 1,3-dichloro-l,1,2,2,3-penta- fluoropropane and from about 0.01 to about 2 weight percent 1-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 94 to about 99 weight percent 1,3-dichloro- 1, 1,2,2,3-pentafluoropropane and from about 1 to about 6 weight percent 2-propanol and boil at about 55.0 C ⁇ about 0.3°C at 744 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 95 to about 98.5 weight percent 1,3-dichloro-l, 1,2,2,3-pentafluoro ⁇ propane and from about 1.5 to about 5 weight percent 2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 95.5 to about 98.5 weight percent 1,3-dichloro-l, 1,2,2,3-penta- fluoropropane and from about 1.5 to about 4.5 weight percent 2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 98 to about q 9.99 weight percent 1,3-dichloro-l,1,2,2,3-pentafluoropropane and from about 0.01 to about 2 weight percent 2-methyl-2-propanol and boil at about 55.7°C ⁇ about 0.2°C at 749.1 mm Hg.
  • compositions within 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 a 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 0 described above.
  • azeotrope- like composition is intended to mean that the composition behaves like a true azeotrope in terms of 5 its constant-boiling characteristics or tendency not to fractionate upon boiling or evaporation. Such compositions may or may not be a true azeotrope.
  • the composition of the vapor formed during boiling or evaporation is identical or substantially identical to the original liquid
  • 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-azeotropic or non-azeotrope-like, the mixture will fractionate, i.e., separate into its various components with the lowest boiling component distilling off first, and so
  • azeotrope-like compositions there is a range of compositions containing the same components in varying proportions which are azeotrope- like. All such compositions are intended to be covered by the term azeotrope-like as used herein.
  • azeotrope-like As an example, it is well known that at different pressures, the composition of a given azeotrope will vary at least slightly as does the boiling point of the composition.
  • an azeotrope of A and B represents a unique type of relationship but with a variable composition depending on temperature and/or pressure.
  • azeotrope-like within the meaning of the invention is to state that such mixtures boil within about ⁇ 5.6 C (at 760 mm Hg) of the 50.6 C boiling point disclosed herein.
  • the boiling point of the azeotrope will vary with the pressure.
  • the azeotrope-like compositions of the invention may be used to clean solid surfaces by treating said surfaces with said compositions in any manner well known in the art such as by dipping or spraying or use of conventional degrea.sing apparatus.
  • the azeotrope-like compositions discussed herein are useful as solvents for a variety of cleaning applications including vapor degreasing, defluxing, cold cleaning, dry cleaning, dewatering, decontamination, spot cleaning, aerosol propelled rework, extraction, particle removal, and surfactant cleaning applications. These azeotrope-like compositions are also useful as blowing agents, Rankine cycle and absorption refrigerants, and power fluids.
  • the dichloropentafluoropropane and alkanol components of the invention are known materials. Preferably, they should be used in sufficiently high purity so as to avoid the introduction of adverse influences upon the solvent or constant boiling properties of the system.
  • alkanols may be used in the present invention.
  • Most dichloropentafluoropropane isomers like the preferred HCFC-225ca isomer, are not available in commercial quantities, therefore until such time as they become commercially available, they may be prepared by following the organic syntheses disclosed herein.
  • 1, l-dichloro-2, 2, 3, 3,3- pentafluoropropane may be prepared by reacting 2, 2, 3 , 3 , 3-pentafluorol-propanol and p-toluenesulfonate chloride together to form 2 ,2,3 , 3,3-penta luoro- propyl-p-toluenesulfonate.
  • the l-(trimethylsiloxy)-2 ,2-dichloro- 3,3,3-trifluoro-N,N-dimethyl propylamine is reacted with sulfuric acid to form 2,2-dichloro-3 ,3,3-trifluoro- propionaldehyde.
  • Part B Synthesis of 1, 1,2,2, 3- ⁇ entafluoro ⁇ propane.
  • a 500 ml flask was equipped with a mechanical stirrer and a Vigreaux distillation column, which in turn was connected to a dry-ice trap, and maintained under a nitrogen atmosphere.
  • the flask was charged with 400 ml N-methylpyrrolidone, 145 gm (0.507 mol) 2,2,3,3-tetrafluoropropy -p-toluenesulfonate (produced in Part A above), and 87 gm (1.5 mol) spray-dried KF.
  • This compound may be prepared by reacting trifluoroethylene with dichlorotri- fluoromethane to produce 1,3-dichloro-l,1,2,3,3,- pentafluoropropane and 1,1-dichloro-l,2,3,3,3-penta-
  • 225eb 1.1-dichloro-l.2,3.3,3-pentafluoro- 30 propane (225eb) .
  • This compound may be prepared by reacting trifluoroethylene with dichlorodifluoromethane to produce 1,3-dichloro-l,1,2,3,3-pentafluoropropane and 1,1-dichloro-l,2,3,3,3-pentafluoropropane.
  • the 1,1-dichloro-l,2,3,3,3-pentafluoropropane is separated 3 **- * from its isomer using fractional distillation and/or preparative gas chromatography.
  • 225eb may be prepared by a synthesis disclosed by 0. Paleta et al., Bull.
  • compositions may include additional components which form new azeotrope-like 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.
  • 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: epoxy compounds such as propylene oxide; nitroalkanes such as nitromethane; ethers such as 1-4-dioxane; unsaturated compounds such as 1,4-butyne diol; acetals or ketals such as dipropoxy methane; ketones such as methyl ethyl ketone; alcohols such as tertiary amyl alcohol; esters such as triphenyl phosphite; and amines such as triethyl amine.
  • Other suitable inhibitors will readily occur to those skilled in the art.
  • This example is directed to the preparation of the preferred dichloropentafluoropropane component of the invention 1, l-dichloro-2,2,3,3,3-pentafluoropropane
  • the compositional range over which 225ca and methanol exhibit constant boiling behavior was determined. This was accomplished by charging measured quantities of 225ca into an ebulliometer.
  • the ebulliometer consisted of a heated sump in which the 5 HCFC-225ca was brought to a boil. The upper part of the ebulliometer connected to the sump was cooled thereby acting as a condenser for the boiling vapors, allowing the system to operate at total . reflux.
  • ⁇ measured amounts of methanol were titrated into the ebulliometer. The change in boiling point was measured with a platinum resistance thermometer.
  • compositions of 5 225ca/methanol ranging from about 82-97/3-18 and preferably 89-95/5-11 weight percent respectively would exhibit constant boiling behavior at 45.4°C ⁇ about 0.5 C C at 760 mm Hg.

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Abstract

Des compositions stables, semblables à l'azéotrope, et essentiellement constituées de dichloropentafluoropropane et d'un alcanol possédant entre 1 et 4 atomes de carbone, sont utiles à diverses applications de nettoyage industriel telles que le nettoyage à froid et le défluxage des plaquettes à circuits imprimés.
PCT/US1990/005384 1989-10-06 1990-09-20 Compositions de dichloropentafluoropropane semblables a l'azeotrope et un alcanol possedant entre 1 et 4 atomes carbone WO1991005035A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1019920700785A KR0145743B1 (ko) 1989-10-06 1990-09-20 디클로로펜타플루오로프로판과 (c1-c4) 알칸올의 공비성 조성물
AT90915683T ATE101194T1 (de) 1989-10-06 1990-09-20 Azeotropaehnliche zusammensetzungen von 1,3dichlor-1,1,2,2,3-pentafluorpropan und 2-methyl-2-propanol.
BR909007715A BR9007715A (pt) 1989-10-06 1990-09-20 Composicoes do tipo azeotropo de dicloropentafluoropropano e um alcanol com 1 a 4 atomos de carbono
DE69006508T DE69006508T2 (de) 1989-10-06 1990-09-20 Azeotropähnliche zusammensetzungen von 1,3-dichlor-1,1,2,2,3-pentafluorpropan und 2-methyl-2-propanol.
NO921254A NO178438C (no) 1989-10-06 1992-03-31 Azeotroplignende blandinger av diklorpentafluorpropan og en C1-4-alkanol

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US417,983 1982-09-14
US41800889A 1989-10-06 1989-10-06
US41798389A 1989-10-06 1989-10-06
US418,008 1989-10-06
US526,748 1990-05-22
US07/526,748 US5124065A (en) 1989-10-06 1990-05-22 Azeotrope-like compositions of dichloropentafluoropropane and an alkanol having 1-4 carbon atoms

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JP (1) JP2853900B2 (fr)
AU (1) AU641700B2 (fr)
BR (1) BR9007715A (fr)
CA (1) CA2067218A1 (fr)
DE (1) DE69006508T2 (fr)
ES (1) ES2062560T3 (fr)
IE (1) IE64912B1 (fr)
MY (1) MY107105A (fr)
NO (1) NO178438C (fr)
WO (1) WO1991005035A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000402A3 (fr) * 1990-06-25 1992-02-20 Allied Signal Inc Compositions du type azeotrope a base de dichloropentafluoropropane, de 2-propanol et d'un hydrocarbure contenant six atomes de carbone
US5102563A (en) * 1990-05-10 1992-04-07 Societe Atochem Cleaning composition based on 1,1,1,2,2-pentafluoro-3,3-dichloropropane and methyl tert-butyl ether
WO1992011400A1 (fr) * 1990-12-18 1992-07-09 Allied-Signal Inc. Composition semblable a des azeotropes de dichloropentafluoropropane, un alcanol ayant de 1 a 3 atomes de carbone et 2-methyl-2-propanol
US5320683A (en) * 1989-02-06 1994-06-14 Asahi Glass Company Ltd. Azeotropic or azeotropic-like composition of hydrochlorofluoropropane
US5607912A (en) * 1989-02-01 1997-03-04 Asahi Glass Company Ltd. Hydrochlorofluorocarbon azeotropic or azeotropic-like mixture

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4735537B2 (ja) * 2004-02-24 2011-07-27 旭硝子株式会社 水切り方法

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AU6547890A (en) 1991-04-28
JPH05500979A (ja) 1993-02-25
NO178438C (no) 1996-03-27
DE69006508T2 (de) 1994-05-26
IE64912B1 (en) 1995-09-20
DE69006508D1 (de) 1994-03-17
BR9007715A (pt) 1992-07-07
AU641700B2 (en) 1993-09-30
JP2853900B2 (ja) 1999-02-03
CA2067218A1 (fr) 1991-04-07
EP0494975B1 (fr) 1994-02-02
ES2062560T3 (es) 1994-12-16
IE903207A1 (en) 1991-04-10
NO921254L (no) 1992-03-31
MY107105A (en) 1995-09-30
NO178438B (no) 1995-12-18
EP0494975A1 (fr) 1992-07-22
NO921254D0 (no) 1992-03-31

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