EP0443911A1 - Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel - Google Patents

Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel Download PDF

Info

Publication number: EP0443911A1
Authority: EP; European Patent Office
Prior art keywords: ethylene; composition according; weight; perfluorobutyl; perfluoroalkyl
Prior art date: 1990-02-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP19910400353

Other languages

English (en)

French (fr)

Other versions

EP0443911B1 (de

Inventor

Daniel Desbiendras

Jean-Jacques Martin

Pascal Michaud

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Arkema France SA

Original Assignee

Elf Atochem SA

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.)

1990-02-20

Filing date

1991-02-12

Publication date

1991-08-28

1991-02-12 Application filed by Elf Atochem SA filed Critical Elf Atochem SA

1991-08-28 Publication of EP0443911A1 publication Critical patent/EP0443911A1/de

1995-01-18 Application granted granted Critical

1995-01-18 Publication of EP0443911B1 publication Critical patent/EP0443911B1/de

2011-02-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000004140 cleaning Methods 0.000 title claims abstract description 19
125000005010 perfluoroalkyl group Chemical group 0.000 title claims abstract description 14
239000012459 cleaning agent Substances 0.000 title description 2
239000002274 desiccant Substances 0.000 title description 2
239000005977 Ethylene Substances 0.000 claims abstract description 26
238000001035 drying Methods 0.000 claims abstract description 9
239000007787 solid Substances 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
239000000203 mixture Substances 0.000 claims description 54
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 15
238000009835 boiling Methods 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
239000003381 stabilizer Substances 0.000 claims description 6
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 5
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
150000001241 acetals Chemical class 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
125000004971 nitroalkyl group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 5
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 6
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 5
239000012808 vapor phase Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 4
230000004907 flux Effects 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
238000005238 degreasing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
-1 perfluoroalkyl radical Chemical class 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000002131 composite material Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910000679 solder Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000002604 ultrasonography Methods 0.000 description 2
238000003466 welding Methods 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
YVLLFYIFMKAGCT-KHPPLWFESA-N 1-n-[(z)-octadec-9-enyl]propane-1,2-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCC(C)N YVLLFYIFMKAGCT-KHPPLWFESA-N 0.000 description 1
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
238000001159 Fisher's combined probability test Methods 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000007605 air drying Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000005914 dehydroiodination reaction Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
150000001470 diamides Chemical class 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000002529 flux (metallurgy) Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
238000007654 immersion Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004506 ultrasonic cleaning Methods 0.000 description 1
238000012795 verification Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

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
- 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
- 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
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/5059—Mixtures containing (hydro)chlorocarbons
- 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
- C11D7/5086—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being different from alcohols, e.g. mixtures of water and 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
- C11D7/50—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
- 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
- C23G5/02803—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 fluorine
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
- C11D7/266—Esters or carbonates
- 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 the field of fluorinated hydrocarbons and more particularly relates to the use of (perfluoroalkyl) -ethylenes as cleaning or drying agents for solid surfaces.
F113 1,1,2-trichloro-1,2,2-trifluoroethane Due to its physicochemical characteristics, in particular its non-flammability, its high wetting power, its low solvent power and its low boiling point, 1,1,2-trichloro-1,2,2-trifluoroethane (known in the art under the designation F113) is currently widely used in the industry for cleaning and degreasing a wide variety of solid surfaces (metallic, glass, plastic or composite). In electronics, the F113 has notably found an important application in defluxing and cold cleaning of printed circuits. Other examples of applications of F113 include the degreasing of metal parts and the cleaning of high quality and high precision mechanical parts such as, for example, gyroscopes and military, aerospace or medical equipment.
F113 is often combined with other organic solvents (for example methanol), in particular in the form of azeotropic or pseudo-azeotropic mixtures which do not demix and which, when used at reflux, have substantially the same composition in the vapor phase than in the liquid phase.
organic solvents for example methanol
F113 is also used in industry for drying various solid substrates (metal parts, plastics, composites or glasses) after cleaning in an aqueous medium.
F113 is often added with one or more surfactants (see in particular the patents FR 2 353 625, FR 2 527 625, EP 0 090 677 and 0 189 436 and the references cited in these patents).
F113 is one of the completely halogenated chlorofluorocarbons that are currently suspected attack or degrade stratospheric ozone. We are therefore looking for products devoid of a destructive effect vis-à-vis ozone and capable of replacing F113 in its various applications.
R F -CH CH2 in which R F represents a perfluoroalkyl radical, linear or branched, containing from 3 to 6 carbon atoms, having physicochemical characteristics similar to those of F113 and, unlike the latter, are not liable to degrade stratospheric ozone.
these compounds are particularly stable to oxidation and do not damage plastics (polystyrene, ABS, ...) or elastomers such as ethylene-propylene copolymers.
the subject of the invention is therefore the use of a (perfluoroalkyl) -ethylene of formula (I) as a substitute for F113 in the various applications of the latter. Also part of the present invention, the cleaning or drying compositions based on a (perfluoroalkyl) -ethylene.
the (perfluoroalkyl) -ethylene of formula (I) can be used alone or as a mixture with one another or with other organic solvents which are liquid at room temperature, for example with alcohols such as methanol, ethanol, and isopropanol, ketones like acetone, esters like methyl or ethyl acetate and ethyl formate, ethers like methyl tert-butyl ether and tetrahydrofuran, acetals like dimethoxy- 1.1 ethane and 1,3-dioxolane, chlorinated or non-chlorinated hydrocarbons such as methylene chloride, trichlorethylene and 1,1,1 trichloroethane, 2-methyl pentane, 2,3-dimethyl butane, n.hexane and hexene-1.
alcohols such as methanol, ethanol, and isopropanol
ketones like acetone
esters like methyl or
the mixture has a pseudo-azeotropic behavior, that is to say that the composition of the vapor and liquid phases is substantially the same, which is particularly advantageous for the intended applications.
Such a mixture also has the important advantage of not having a flash point under the standard conditions of determination (standard ASTM-D 3828) and is therefore non-flammable.
the cleaning compositions based on (perfluoroalkyl) -ethylene according to the invention can, if desired, be stabilized against hydrolysis and / or free radical attacks likely to occur.
a usual stabilizer such as, for example, a nitroalkane (nitromethane, nitroethane, ...) an alkylene oxide (propylene, butylene, isoamylene, ...) or a mixture of these compounds, the proportion of stabilizer can range from 0.01 to 5% relative to the total weight of the composition.
a grid of 100% polyamide fabric weighing 8.4 mg / cm2 and dimensions 5 x 2 cm is immersed in water for 30 seconds, then allowed to drip without stirring and then immersed for 10 seconds in 50 ml of absolute alcohol.
the alcohol water concentration is then determined by the Karl-Fisher method and this concentration serves as a control.
compositions intended for drying (elimination of water) of the solid substrates after cleaning in an aqueous medium can contain, in a proportion ranging from 0.01 to 5% in by weight (preferably from 0.1 to 3%), the same additives as the drying compositions based on F113.
additives are generally surfactants such as, for example, mono- or dialkylphosphates of amines, salts of the dioleate type of N-oleylpropylenediamine, diamides of the dioleyl-oleylamidopropyleneamide type, cationic compounds derived from l imidazoline, or compounds resulting from the reaction of a quaternary ammonium hydrochloride with an alkylphosphoric acid in the presence of a fluorinated amine or not.
surfactants such as, for example, mono- or dialkylphosphates of amines, salts of the dioleate type of N-oleylpropylenediamine, diamides of the dioleyl-oleylamidopropyleneamide type, cationic compounds derived from l imidazoline, or compounds resulting from the reaction of a quaternary ammonium hydrochloride with an alkylphosphoric acid in the presence of a fluorinated amine or not.
This azeotrope used for cleaning welding fluxes or degreasing mechanical parts, gives good results.
Example 2 is repeated using 0.1% nitromethane and 0.1% propylene oxide. The following results are obtained:
Example 2 The procedure is as in Example 1, but replacing the methanol with other solvents.
the following table shows the normal boiling point (at 1.013 bar) and the composition of the azeotropes.
composition and normal boiling point of three other ternary azeotropes are shown in the following table.

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Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Emergency Medicine (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Materials Engineering (AREA)
Mechanical Engineering (AREA)
Metallurgy (AREA)
Detergent Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Extraction Or Liquid Replacement (AREA)
Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

EP91400353A 1990-02-20 1991-02-12 Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel Expired - Lifetime EP0443911B1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9002011		1990-02-20
FR9002011A FR2658532B1 (fr)	1990-02-20	1990-02-20	Application des (perfluoroalkyl)-ethylenes comme agents de nettoyage ou de sechage, et compositions utilisables a cet effet.

Publications (2)

Publication Number	Publication Date
EP0443911A1 true EP0443911A1 (de)	1991-08-28
EP0443911B1 EP0443911B1 (de)	1995-01-18

Family

ID=9393900

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP91400353A Expired - Lifetime EP0443911B1 (de)	1990-02-20	1991-02-12	Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel

Country Status (13)

Country	Link
US (1)	US5302212A (de)
EP (1)	EP0443911B1 (de)
JP (1)	JPH0615003B2 (de)
KR (1)	KR930007225B1 (de)
AT (1)	ATE117362T1 (de)
AU (1)	AU635387B2 (de)
CA (1)	CA2035687C (de)
DE (1)	DE69106740T2 (de)
FI (1)	FI98827C (de)
FR (1)	FR2658532B1 (de)
IE (1)	IE68777B1 (de)
NO (1)	NO176673C (de)
PT (1)	PT96811B (de)

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EP0525266A1 (de) *	1991-07-31	1993-02-03	Elf Atochem S.A.	Zusammensetzung auf der Basis von N-Perfluorbutylethylen zum Reinigen von festen Oberflächen
FR2694942A1 (fr) *	1992-08-21	1994-02-25	Atochem Elf Sa	Composition à base de 1,1,1,3,3-pentafluorobutane et de chlorure de méthylène, pour le nettoyage et/ou le séchage de surfaces solides.
EP0607969A1 (de) *	1993-01-22	1994-07-27	Canon Kabushiki Kaisha	Lösungsmittelgemisch sowie Reinigungsverfahren und -vorrichtung, die es verwenden
US5458800A (en) *	1990-02-20	1995-10-17	Societe Atochem	Use of (perfluoroalkyl) ethylenes as cleaning or drying agents, and compositions which can be used for this purpose
EP0731162A1 (de) *	1995-03-09	1996-09-11	Elf Atochem S.A.	Verwendung von Hydrofluoroalkenen als Reinigungsmittel und doese enthaltende Zusammensetzungen
FR2766837A1 (fr) *	1997-07-31	1999-02-05	Atochem Elf Sa	Compositions azeotropiques a base de (n.perfluorohexyl) ethylene pour le traitement de surfaces solides
EP2287282A3 (de) *	2002-10-25	2011-05-25	Honeywell International Inc.	Zusammensetzungen mit fluorsubsttuierten Olefinen
EP4098729A1 (de)	2021-06-01	2022-12-07	Cipelia	Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung

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JP3390245B2 (ja) *	1993-06-01	2003-03-24	富士通株式会社	洗浄液及び洗浄方法
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US6372705B1 (en)	1995-03-24	2002-04-16	Bayer Corporation	Azeotropic compositions of perfluorohexane and hydrocarbons having 5 carbon atoms and the use thereof in the production of foams
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JPH08330266A (ja) *	1995-05-31	1996-12-13	Texas Instr Inc <Ti>	半導体装置等の表面を浄化し、処理する方法
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EP1349972B1 (de) *	2000-12-22	2007-01-24	E.I. Du Pont De Nemours And Company	Azeotrope mischungen mit perfluorbutylethylen
US7745369B2 (en) *	2003-12-19	2010-06-29	Shell Oil Company	Method and catalyst for producing a crude product with minimal hydrogen uptake
US7153448B2 (en) *	2004-05-26	2006-12-26	E.I. Du Pont De Nemours And Company	1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof
CN101166805B (zh) *	2005-04-26	2011-06-08	纳幕尔杜邦公司	含有3,3,4,4,5,5,6,6,6-九氟-1-己烯和氢氟烃的热传递和制冷组合物
US7553985B2 (en) *	2005-11-02	2009-06-30	E.I. Du Pont De Nemours And Company	Fluorinated surfactants
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EP2152833B1 (de) *	2007-06-12	2014-07-23	E. I. Du Pont de Nemours and Company	Azeotrope und azeotropenähnliche zusammensetzungen aus e-1,1,1,4,4,4-hexafluor-2-buten
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- 1991-02-14 NO NO910596A patent/NO176673C/no unknown
- 1991-02-19 IE IE56091A patent/IE68777B1/en not_active IP Right Cessation
- 1991-02-19 PT PT96811A patent/PT96811B/pt not_active IP Right Cessation
- 1991-02-19 FI FI910800A patent/FI98827C/fi active
- 1991-02-20 JP JP3026414A patent/JPH0615003B2/ja not_active Expired - Lifetime
- 1991-02-20 US US07/658,270 patent/US5302212A/en not_active Expired - Fee Related
- 1991-02-20 KR KR1019910002732A patent/KR930007225B1/ko not_active Expired - Fee Related

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5458800A (en) *	1990-02-20	1995-10-17	Societe Atochem	Use of (perfluoroalkyl) ethylenes as cleaning or drying agents, and compositions which can be used for this purpose
EP0525266A1 (de) *	1991-07-31	1993-02-03	Elf Atochem S.A.	Zusammensetzung auf der Basis von N-Perfluorbutylethylen zum Reinigen von festen Oberflächen
FR2694942A1 (fr) *	1992-08-21	1994-02-25	Atochem Elf Sa	Composition à base de 1,1,1,3,3-pentafluorobutane et de chlorure de méthylène, pour le nettoyage et/ou le séchage de surfaces solides.
EP0607969A1 (de) *	1993-01-22	1994-07-27	Canon Kabushiki Kaisha	Lösungsmittelgemisch sowie Reinigungsverfahren und -vorrichtung, die es verwenden
US5431837A (en) *	1993-01-22	1995-07-11	Canon Kabushiki Kaisha	Azeotropic mixtures of perfluoro-n-hexane with diisopropyl ether or isohexane
US5490894A (en) *	1993-01-22	1996-02-13	Canon Kabushiki Kaisha	Cleaning method using azeotropic mixtures of perfluoro-n-hexane with diisopropyl ether or isohexane and cleaning apparatus using same
EP0731162A1 (de) *	1995-03-09	1996-09-11	Elf Atochem S.A.	Verwendung von Hydrofluoroalkenen als Reinigungsmittel und doese enthaltende Zusammensetzungen
FR2731436A1 (fr) *	1995-03-09	1996-09-13	Atochem Elf Sa	Utilisation d'hydrofluoroalcenes comme agents de nettoyage, et compositions utilisables a cet effet
FR2766837A1 (fr) *	1997-07-31	1999-02-05	Atochem Elf Sa	Compositions azeotropiques a base de (n.perfluorohexyl) ethylene pour le traitement de surfaces solides
EP2287282A3 (de) *	2002-10-25	2011-05-25	Honeywell International Inc.	Zusammensetzungen mit fluorsubsttuierten Olefinen
EP2287282B1 (de)	2002-10-25	2016-11-23	Honeywell International Inc.	Zusammensetzungen mit fluorsubsttuierten olefinen
EP4098729A1 (de)	2021-06-01	2022-12-07	Cipelia	Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung
WO2022253857A1 (en)	2021-06-01	2022-12-08	Cipelia	Non-flammable, volatile and aqueous cleaning composition

Also Published As

Publication number	Publication date
AU635387B2 (en)	1993-03-18
PT96811A (pt)	1991-10-31
FI910800A0 (fi)	1991-02-19
EP0443911B1 (de)	1995-01-18
FR2658532B1 (fr)	1992-05-15
DE69106740D1 (de)	1995-03-02
FI910800L (fi)	1991-08-21
NO910596D0 (no)	1991-02-14
IE910560A1 (en)	1991-08-28
FI98827C (fi)	1997-08-25
JPH0615003B2 (ja)	1994-03-02
ATE117362T1 (de)	1995-02-15
JPH04227803A (ja)	1992-08-17
CA2035687C (fr)	1998-05-05
US5302212A (en)	1994-04-12
FI98827B (fi)	1997-05-15
FR2658532A1 (fr)	1991-08-23
NO176673B (no)	1995-01-30
PT96811B (pt)	1998-07-31
KR930007225B1 (ko)	1993-08-04
NO910596L (no)	1991-08-21
KR910021472A (ko)	1991-12-20
DE69106740T2 (de)	1995-08-10
CA2035687A1 (fr)	1991-08-21
IE68777B1 (en)	1996-07-10
NO176673C (no)	1995-05-10
AU7098991A (en)	1991-08-22

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Publication	Publication Date	Title
EP0443911B1 (de)	1995-01-18	Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel
EP0512885B1 (de)	1994-04-13	Zusammensetzung auf Basis von 1,1,1,3,3-Pentafluorbutan und Methanol zum Reinigen und/oder Trocknen von harten Oberflächen
EP0512884B1 (de)	1994-04-13	Zusammensetzung auf Basis von 1,1-Dichlor-1-fluorethan, 1,1,1,3,3-Pentafluorbutan und Methanol für die Reinigung und/oder Trocknung von harten Oberflächen
EP0731162A1 (de)	1996-09-11	Verwendung von Hydrofluoroalkenen als Reinigungsmittel und doese enthaltende Zusammensetzungen
FR2694943A1 (fr)	1994-02-25	Composition à base de 1,1,1,3,3-pentafluorobutane, de chlorure de méthylène et de méthanol, pour le nettoyage et/ou le séchage de surfaces solides.
FR2694942A1 (fr)	1994-02-25	Composition à base de 1,1,1,3,3-pentafluorobutane et de chlorure de méthylène, pour le nettoyage et/ou le séchage de surfaces solides.
EP1046703B1 (de)	2003-10-15	Reinigungs- oder Trocknungszusammensetzungen auf Basis von Pentafluorbutan, Methylenchlorid, Methanol und Decafluorpentan
EP0856578B1 (de)	2002-11-06	Reinigungs- oder Trocknungsmittel enthaltend 1,1,1,2,3,4,4,5,5,5-Decafluoropentan
EP0456551A1 (de)	1991-11-13	1,1,1,2,2-Pentafluor-3,3-Dichlor-Propan und Methyl Ter-Butyl-Aether enthaltende Reinigungsmittelzusammensetzung
EP0441663A1 (de)	1991-08-14	Reinigungsmittel auf der Grundlage von 1,1-Dichlor-1-Fluorethan und Methylformiat
FR2792648A1 (fr)	2000-10-27	COMPOSITIONS DE NETTOYAGE OU DE SECHAGE A BASE DE 43-10mee ET DE TRICHLORETHYLENE
EP0559264B1 (de)	1997-05-02	Verfahren zur Stabilisierung eines Fluorkohlenwasserstoffs und Mischungen, die mindestens einen Fluorkohlenwasserstoff enthalten
EP0609125B1 (de)	1999-05-12	Stabilisierte Reinigungsmittel auf Basis von 1,1, Dichloro-1-fluoroethan und Methanol
EP0441664A1 (de)	1991-08-14	Reinigungsmittel auf Basis von 1,1-Dichlor-1-Fluorethan, Methylformiat und Methanol
WO2003025109A1 (fr)	2003-03-27	Compositions de nettoyage ou de sechage a base de n-perfluorobutyl-ethylene et de hfc 365mfc
EP0525266A1 (de)	1993-02-03	Zusammensetzung auf der Basis von N-Perfluorbutylethylen zum Reinigen von festen Oberflächen
FR2792649A1 (fr)	2000-10-27	COMPOSITIONS DE NETTOYAGE OU DE SECHAGE A BASE DE 43-10mee, DE CH2CL2, DE CYCLOPENTANE ET DE CH3OH
FR2733247A1 (fr)	1996-10-25	Agent de nettoyage a base de cycloalcanes
EP0771865A1 (de)	1997-05-07	Reinigungsmittel auf Grundlage von 1,1,1,2,2,4,4-Heptafluorbutan und Alkoholen
EP0474528A1 (de)	1992-03-11	Reinigungsmittelzusammensetzung auf Basis von 1,1-Dichloro-1-fluoroethan, Methylenchlorid und Methanol
FR2656327A1 (fr)	1991-06-28	Composition nettoyage a base de 1,1-dichloro-2,2,2-trifluoroethane et de formiate de methyle.
FR2656328A1 (fr)	1991-06-28	Composition nettoyante a base de 1,1-dichloro-2,2,2-trifluoroethane, de formiate de methyle et de methanol.