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WO1992010453A1 - 1,1-dichloro-1-fluoroethane stabilise - Google Patents

1,1-dichloro-1-fluoroethane stabilise Download PDF

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Publication number
WO1992010453A1
WO1992010453A1 PCT/US1991/008997 US9108997W WO9210453A1 WO 1992010453 A1 WO1992010453 A1 WO 1992010453A1 US 9108997 W US9108997 W US 9108997W WO 9210453 A1 WO9210453 A1 WO 9210453A1
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Prior art keywords
carbon atoms
dichloro
group
fluoroethane
phosphite
Prior art date
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Ceased
Application number
PCT/US1991/008997
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English (en)
Inventor
Kane David Cook
Chien Chi Li
Rajat Subhra Basu
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Honeywell International Inc
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AlliedSignal Inc
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Publication of WO1992010453A1 publication Critical patent/WO1992010453A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/42—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
    • 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
    • C11D7/5004—Organic solvents
    • C11D7/5018—Halogenated solvents
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • 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
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/263—Ethers
    • 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
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D7/267—Heterocyclic compounds
    • 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

Definitions

  • the present invention relates to stabilized 1,1-dichloro-l-fluoroethane.
  • Stabilized 1,1-dichloro-l-fluoroethane is useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing.
  • 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. Final evaporation of solvent from the object leaves behind no residue as would be the case where the object is simply washed in liquid solvent.
  • 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 1,1-dichloro-l-fluoroethane
  • 1,1-Dichloro-l-fluoroethane 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.
  • the art is continually seeking new hydrochlorofluorocarbon solvents which offer alternatives for new and special applications for vapor degreasing and other cleaning applications.
  • Solvents which are based on hydrochlorofluorocarbons are considered to be stratospherically safe substitutes for presently used fully halogenated chlorofluorocarbons. The latter are suspected of causing environmental problems in connection with the earth's protective ozone layer.
  • Mathematical models have substantiated that hydrochlorofluorocarbons, such as 1,1-dichloro-l-fluoroethane (known in the art as HCFC-141b), will not adversely affect atmospheric chemistry, being negligible contributors to ozone depletion and to green-house global warming in comparison to the fully halogenated species.
  • Hydrochlorofluorocarbons such as 1,1-dichloro-l-fluoroethane hydrolyze to form hydrogen chloride. While 1,1-dichloro-l-fluoroethane is useful as a cleaning solvent, the 1,1-dichloro-l-fluoroethane should be stabilized against possible changes during storage and use. When metallic materials are present such as occurs in many cleaning applications, the problem is worsened because the metal acts as a catalyst and causes the hydrolysis of 1,1-dichloro-l-fluoroethane to increase exponentially.
  • hydrolysis problem is common.
  • ultraviolet light decomposes hydrochlorofluorocarbons such as 1,1-dichloro-l-fluoroethane.
  • Hydrochlorofluorocarbons such as dichlorotrifluoroethane are known to react with water to form acids such as hydrogen chloride and hydrogen fluoride or to react with alcoholic hydroxyl groups to form aldehydes and ketones.
  • Known stabilizers for compositions of l,l-dichloro-2,2,2-trifluoroethane and alcohol include: epoxy compounds as taught by Kokai Patent Publication 56,630 published March 3, 1989; combinations of styrene and epoxy compounds as taught by Kokai Patent Publication 56,631 published March 3, 1989; combinations of styrene compounds and phenols as taught by Kokai Patent Publication 56,632 published March 3, 1989; combinations of epoxy and styrene compounds and phenols as taught by Kokai Patent Publication 128,943 published May 22, 1989; hydrocarbons containing nitro groups as taught by Kokai
  • Patent Publication 128,944 published May 22, 1989; combinations of hydrocarbons containing nitro groups and epoxy compounds as taught by Kokai Patent Publication
  • Kokai Patent Publication 139,539 teaches l,2-dichloro-l,l,2-trifluoroethane based azeotropic compositions which are stabilized with at least one of nitro compounds, phenols, amines, ethers, amylenes, esters, organic phosphites, epoxides, furans, alcohols, ketones, and triazoles.
  • 1,1-dichloro-l-fluoroethane is considered one of the leading substitutes for chlorofluorocarbons and thus, will be used in many applications in large quantities, it would be useful to have a stabilized 1,1-dichloro-l-fluoroethane which can be used and stored without loss of acceptable properties.
  • the present invention provides a composition comprising 1,1-dichloro-l-fluoroethane and an effective stabilizing amount of stabilizer selected from the group consisting of alkanol having 4 to 7 carbon atoms, nitroalkane having 1 to 3 carbon atoms, 1,2-epoxyalkane having 2 to 7 carbon atoms, phosphite ester having 12 to 30 carbon atoms, ether having 3 or 4 carbon atoms, unsaturated compound having 4 to 6 carbon atoms, acetal having 4 to 7 carbon atoms, ketone having 3 to 5 carbon atoms, or amine having 6 to 8 carbon atoms alone or in mixtures thereof in any proportions.
  • stabilizer selected from the group consisting of alkanol having 4 to 7 carbon atoms, nitroalkane having 1 to 3 carbon atoms, 1,2-epoxyalkane having 2 to 7 carbon atoms, phosphite ester having 12 to 30 carbon atoms, ether having 3 or 4 carbon atoms
  • the stabilized 1,1-dichloro-l-fluoroethane undergoes minimal hydrolysis.
  • the stabilized 1,1-dichloro-l-fluoroethane is especially useful in cleaning applications wherein a solvent is typically exposed to water and metallic materials.
  • the 1,1-dichloro-l-fluoroethane used in the present invention can be prepared by any known method including the reaction of commercially available vinylidene chloride with anhydrous hydrogen fluoride or the reaction of commercially available 1,1,1-trichloroethane with anhydrous hydrogen fluoride.
  • Examples of useful alkanols having 4 to 7 carbon atoms are 2-methyl-2-pro ⁇ anol; 2-methyl-2-butanol; 1-pentanol; 2-pentanol; 3-pentanol; and 3-ethyl-3- ⁇ entanol.
  • the preferred alkanols are 2-methyl-2- ⁇ ropanol and 3-pentanol.
  • alkanol preferably, about 0.01 to about 2 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and alkanol is alkanol. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and alkanol is alkanol.
  • nitroalkanes having 1 to 3 carbon atoms include nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane.
  • the preferred nitroalkanes are nitromethane and nitroethane. If a nitroalkane is used, preferably, about 0.01 to about 2 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and nitroalkane is nitroalkane. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and nitroalkane is nitroalkane.
  • Examples of useful 1,2-e ⁇ oxyalkanes having 2 to 7 carbon atoms include epoxyethane; 1,2-epoxypropane; 1,2-epoxybutane; 2,3-epoxybutane; 1,2-epoxy ⁇ entane; 2,3-epoxypentane; 1,2-epoxyhexane; and 1,2-epoxyheptane.
  • the preferred 1,2-epoxyalkanes are 1,2-epoxybutane and 1,2-epoxypro ⁇ ane.
  • 1,2-epoxyalkane preferably, about 0.01 to about 2 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and 1,2-epoxyalkane is 1,2-epoxyalkane. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and 1,2-epoxyalkane is 1,2-epoxyalkane.
  • 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 5 are triisodecyl phosphite (hereinafter TDP) and triisooctyl phosphite (hereinafter TOP) . If a phosphite ester is used, preferably, about 0.01 to about 2 percent based on the total weight of the
  • 1,1-dichloro-l-fluoroethane and phosphite ester is Q phosphite ester. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and phosphite ester is phosphite ester.
  • 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. If an ether is used, preferably, about 0.01 to about 2 percent based on the total weight of the 0
  • 1,1-dichloro-l-fluoroethane and ether is ether. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and ether is ether. 5
  • Examples of useful unsaturated compounds having 4 to 6 carbon atoms include 1,4-butyne diol; 1,5- ⁇ entyne diol; and 1,6-hexyne diol.
  • the preferred unsaturated compounds are 1,4-butyne diol and 1,5-pentyne diol. If an unsaturated compound is used, preferably, about 0.01 to 0 about 2 percent based on the total weight of the
  • 1,1-dichloro-l-fluoroethane and unsaturated compound is unsaturated compound. More preferably, about 0.02 to about 1 percent based on the total weight of the
  • 1,1-dichloro-l-fluoroethane and unsaturated compound is unsaturated compound.
  • useful acetals having 4 to 7 carbon atoms include dimethoxyethane; 1,1-diethyoxyethane; and dipropoxymethane.
  • the preferred acetals are dimethoxyethane and dipropoxymethane. If an acetal is used, preferably, about 0.01 to about 2 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and acetal is acetal. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and acetal is acetal.
  • ketones having 3 to 5 carbon atoms examples include 2-propanone; 2-butanone; and 3-pentanone.
  • the preferred ketones are 2- ⁇ ropanone and 2-butanone.
  • a ketone preferably, about 0.01 to about 2 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and ketone is ketone. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and ketone is ketone.
  • 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. If an amine is used, preferably, about 0.01 to about 2 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and amine is amine. More preferably, about 0.02 to about 1 percent based on the total weight of the 1,1-dichloro-l-fluoroethane and amine is amine.
  • effective stabilizing amounts means that amount of each of the alkanols, nitroalkanes, 1,2-epoxyalkanes, phosphite esters, ethers, unsaturated compounds, acetals, ketones, and amines which in combination with the 1,1-dichloro-l-fluoroethane component allows the composition to be used and stored without loss of acceptable properties.
  • the stabilizers are effective in preventing the hydrolysis of the 1,1-dichloro-l-fluoroethane component in the presence of Aluminum-2024, copper, cold rolled steel, galvanized steel, and various grades of stainless steel.
  • the Cl " concentration is less than about 50 parts per million. Also, the metallic surface remains shiny.
  • the stabilized 1,1-dichloro-l-fluoroethane of the present invention may be prepared in any known manner including weighing each component and then mixing the components together.
  • Stabilized 1,1-dichloro-l-fluoroethane is useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing.
  • the present stabilized 1,1-dichloro-l-fluoroethane may also be blended with at least one common solvent component such as other hydrochlorofluorocarbons, hydrofluorocarbons, alkanols having 1 or 2 carbon atoms, alkanes, and dichloroethylene.
  • these other components may be used in amounts of up to about 50 weight percent based on the total weight of the stabilized 1,1-dichloro-l-fluoroethane and the at least one other component.
  • Examples of useful hydrochlorofluorocarbons include chlorodifluoromethane (known in the art as HCFC-22); dichlorotrifluoroethane (known in the art as HCFC-123 or
  • HCFC-123a l-chloro-l,l-difluoroethane (known in the art as HCFC-142b); 2,2-dichloro-l,l,1,3,3-pentafluoropropane
  • HCFC-225bb 1,2-dichloro-l,1,2,3,3-pentafluoropropane
  • HCFC-225ca 1,2-dichloro-2,2,3,3,3-pentafluoropropane
  • HCFC-225cb 1,3-dichloro-l,1,2,2,3-pentafluoropropane
  • HCFC-225cc 1,1-dichloro-l,2,2,3,3-pentafluoropropane
  • hydrofluorocarbons examples include pentafluoroethane (known in the art as HFC-125); 1,1,1-trifluoroethane (known in the art as HFC-143a); and 1,1-difluoroethane (known in the art as HFC-152a) .
  • Examples of useful alkanols having 1 or 2 carbon atoms are methanol and ethanol.
  • Examples of useful alkanes include propane; butane; 2-methylpropane; pentane; 2-methylbutane; and 2,2--dimethylpro ⁇ ane.
  • Examples of dichloroethylene are trans-l,2-dichloroethylene and cis-1,2-dichloroethylene.
  • the stabilized 1,1-dichloro-l-fluoroethane of the invention may be used to clean solid surfaces by treating the surfaces with the compositions in any manner well known in the art such as by dipping or spraying or use of conventional degreasing apparatus.
  • the 1,1-dichloro-l-fluoroethane and stabilizers should be used in sufficiently high purity so as to avoid the introduction of adverse influences upon the solvency properties of the system.
  • HCFC-141b is saturated with water at room temperature. Each of the stabilizers listed below is combined in an effective amount with the HCFC-141b. 125 ml of HCFC-141b is transferred into a 250 ml Pyrex flask which is connected to a water/glycol cooled condenser.
  • a "Drierite” desiccant On top of the condenser, a "Drierite” desiccant is provided to prevent ambient moisture leaking into the solvent.
  • a metal coupon is situated in the middle of the liquid-vapor phase.
  • Five common metallic alloys are investigated. They are: Aluminum-2024(hereinafter
  • Each stabilized HCFC-141b solvent system is under total reflux at its boiling temperature for a two week period. Observation is made daily on the change of the metal surface including the loss of luster of the metal surface and stain or corrosion on the metal surface, if any and the solvent including coloration of the solvent, increased viscosity of the solvent and most importantly, the rate of change of the viscosity.
  • the pH values are determined for each stabilized HCFC-141b solvent system before and after the test.
  • the Cl ion concentration in each stabilized HCFC-141b solvent system is determined by ion chromatography.
  • the chloride level is below 50 ppm in each stabilized HCFC-141b solvent system.
  • diphenyl phosphite triphenyl phosphite 5
  • triisodecyl phosphite 22
  • triisooctyl phosphite 23
  • diisooctyl phosphite 24
  • diethylene oxide 25
  • Each of the stabilized 1,1-dichloro-l-fluoroethane compositions of Examples 1 through 39 is combined with up to 50 weight percent of 1,l-dichloro-2,2,2-trifluoroethane to form a solvent blend.

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Abstract

Cette invention concerne des compositions stabilisées comprenant du 1,1-dichloro-1-fluoroéthane et des quantités efficaces au niveau de la stabilisation d'un stabilisateur choisi dans le groupe constitué d'alcanol comprenant de 4 à 7 atomes de carbone, de nitroalcane comprenant de 1 à 3 atomes de carbone, de 1,2-époxyalcane comprenant de 2 à 7 atomes de carbone, d'ester de phosphite comprenant de 12 à 30 atomes de carbone, d'éther comprenant 3 ou 4 atomes de carbone, d'un composé non saturé comprenant de 4 à 6 atomes de carbone, d'acétal comprenant de 4 à 7 atomes de carbone, de cétone comprenant de 3 à 5 atomes de carbone, ou d'amine comprenant de 6 à 8 atomes de carbone, de manière indépendante ou dans des mélanges suivant toutes les proportions possibles. Le 1,1-dichloro-1-fluoroéthane stabilisé est utile dans diverses applications de dégraissage par la vapeur, de nettoyage par le froid et de nettoyage par solvant comprenant également le défluxage.
PCT/US1991/008997 1990-12-14 1991-11-27 1,1-dichloro-1-fluoroethane stabilise Ceased WO1992010453A1 (fr)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0539720A1 (fr) * 1991-10-09 1993-05-05 Elf Atochem North America, Inc. 141b inhibé
EP0539719A1 (fr) * 1991-10-09 1993-05-05 Elf Atochem North America, Inc. 141b stabilisé
FR2689885A1 (fr) * 1992-04-14 1993-10-15 Atochem North America Elf Procédé pour inhiber la décomposition du 1,1-dichloro-1-fluoréthane.
FR2696172A1 (fr) * 1992-09-29 1994-04-01 Solvay Compositions stabilisées comprenant des hydrofluoroalcanes et utilisation de ces compositions.
FR2696173A1 (fr) * 1992-09-29 1994-04-01 Solvay 1,1-dichloro-1-fluoroéthane stabilisé, prémélanges destinés à la préparation de mousses polymériques et mousses polymériques obtenues par leur mise en Óoeuvre.
EP0590709A1 (fr) * 1992-09-29 1994-04-06 SOLVAY (Société Anonyme) Compositions stabilisées comprenant des hydrofluoroalcanes, prémélanges destinés à la préparation de mousses polymériques et mousses polymériques obtenues par leur mise en oeuvre
WO1994011329A1 (fr) * 1992-11-10 1994-05-26 Daikin Industries, Ltd. Inhibiteur de decomposition d'hydrofluorocarbone et procede
FR2700776A1 (fr) * 1993-01-27 1994-07-29 Atochem Elf Sa Composition de nettoyage stabilisée à base de 1,1-dichloro-1-fluoroéthane et de méthanol.
BE1006879A3 (fr) * 1993-03-01 1995-01-17 Solvay Compositions comprenant du 1,1-dichloro-1-fluoroethane et procede d'elimination d'eau d'une surface solide.
WO2003050344A1 (fr) * 2001-12-06 2003-06-19 The Procter & Gamble Company Compositions et procedes permettant d'enlever les souillures accidentelles d'articles en tissu par la modification de la souillure
EP1139911A4 (fr) * 1998-12-15 2003-07-23 Av Healing Llc Methode de fixation de tissus
EP2420546B1 (fr) 2006-09-01 2017-04-26 The Chemours Company FC, LLC Stabilisateurs de téréphtalate pour fluoroléfines

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EP0381216A1 (fr) * 1989-02-01 1990-08-08 Asahi Glass Company Ltd. Mélange azéotropique ou semblable à un mélange azéotropique à base d'hydrocarbures hydrogénés, chlorés et fluorés
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Cited By (22)

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EP0539719A1 (fr) * 1991-10-09 1993-05-05 Elf Atochem North America, Inc. 141b stabilisé
EP0539720A1 (fr) * 1991-10-09 1993-05-05 Elf Atochem North America, Inc. 141b inhibé
FR2689885A1 (fr) * 1992-04-14 1993-10-15 Atochem North America Elf Procédé pour inhiber la décomposition du 1,1-dichloro-1-fluoréthane.
US5366946A (en) * 1992-09-29 1994-11-22 Solvay (Societe Anonyme) Stabilized 1,1-dichloro-1-fluoroethane, premixtures intended for the preparation of polymeric foams and polymeric foams obtained by the use thereof
FR2696172A1 (fr) * 1992-09-29 1994-04-01 Solvay Compositions stabilisées comprenant des hydrofluoroalcanes et utilisation de ces compositions.
FR2696173A1 (fr) * 1992-09-29 1994-04-01 Solvay 1,1-dichloro-1-fluoroéthane stabilisé, prémélanges destinés à la préparation de mousses polymériques et mousses polymériques obtenues par leur mise en Óoeuvre.
EP0590709A1 (fr) * 1992-09-29 1994-04-06 SOLVAY (Société Anonyme) Compositions stabilisées comprenant des hydrofluoroalcanes, prémélanges destinés à la préparation de mousses polymériques et mousses polymériques obtenues par leur mise en oeuvre
BE1006190A5 (fr) * 1992-09-29 1994-06-07 Solvay 1,1-dichloro-1-fluoroethane stabilise, premelanges destines a la preparation de mousses polymeriques et mousses polymeriques obtenues par leur mise en oeuvre.
BE1006189A5 (fr) * 1992-09-29 1994-06-07 Solvay Compositions stabilisees comprenant des hydrofluoroalcanes et utilisation de ces compositions.
BE1006188A5 (fr) * 1992-09-29 1994-06-07 Solvay Compositions stabilisees comprenant des hydrofluoroalcanes, premelanges destines a la preparation de mousses polymeriques et mousses polymeriques obtenues par leur mise en oeuvre.
US5366662A (en) * 1992-09-29 1994-11-22 Solvay (Societe Anonyme) Stabilized compositions comprising hydrofluoroalkanes, premixtures intended for the preparation of polymeric foams and polymeric foams obtained by the use thereof
CN1054834C (zh) * 1992-11-10 2000-07-26 大金工业株式会社 用于含氢和氟卤代烃的分解抑制剂和使用该抑制剂的方法
WO1994011329A1 (fr) * 1992-11-10 1994-05-26 Daikin Industries, Ltd. Inhibiteur de decomposition d'hydrofluorocarbone et procede
EP0609125A1 (fr) * 1993-01-27 1994-08-03 Elf Atochem S.A. Composition de nettoyage stabilisée à base de 1,1-dichloro-1-fluoréthane et de méthanol
FR2700776A1 (fr) * 1993-01-27 1994-07-29 Atochem Elf Sa Composition de nettoyage stabilisée à base de 1,1-dichloro-1-fluoroéthane et de méthanol.
BE1006879A3 (fr) * 1993-03-01 1995-01-17 Solvay Compositions comprenant du 1,1-dichloro-1-fluoroethane et procede d'elimination d'eau d'une surface solide.
EP1139911A4 (fr) * 1998-12-15 2003-07-23 Av Healing Llc Methode de fixation de tissus
WO2003050344A1 (fr) * 2001-12-06 2003-06-19 The Procter & Gamble Company Compositions et procedes permettant d'enlever les souillures accidentelles d'articles en tissu par la modification de la souillure
US6890892B2 (en) 2001-12-06 2005-05-10 Procter & Gamble Company Compositions and methods for removal of incidental soils from fabric articles via soil modification
US7435713B2 (en) 2001-12-06 2008-10-14 The Procter & Gamble Company Compositions and methods for removal of incidental soils from fabric articles via soil modification
EP2420546B1 (fr) 2006-09-01 2017-04-26 The Chemours Company FC, LLC Stabilisateurs de téréphtalate pour fluoroléfines
EP2420546B2 (fr) † 2006-09-01 2020-04-08 The Chemours Company FC, LLC Stabilisateurs de téréphtalate pour fluoroléfines

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