EP0443911B1 - Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel - Google Patents

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

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Publication number
EP0443911B1
EP0443911B1 EP91400353A EP91400353A EP0443911B1 EP 0443911 B1 EP0443911 B1 EP 0443911B1 EP 91400353 A EP91400353 A EP 91400353A EP 91400353 A EP91400353 A EP 91400353A EP 0443911 B1 EP0443911 B1 EP 0443911B1
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EP
European Patent Office
Prior art keywords
ethylene
composition according
weight
perfluorobutyl
perfluoroalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP91400353A
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English (en)
French (fr)
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EP0443911A1 (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
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Publication of EP0443911A1 publication Critical patent/EP0443911A1/de
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Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • 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
  • 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 any destructive effect with respect to ozone and capable of replacing F113 in its various applications.
  • 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 significant advantage of not having a flash point under the standard conditions of determination (standard ASTM-D 3828) and is therefore non-flammable.
  • compositions according to the invention containing (perfluoroalkyl) -ethylenes intended for drying (elimination of water) from the solid substrates after cleaning in an aqueous medium may contain, in a proportion ranging from 0.01 to 5% by by weight (preferably from 0.1 to 3%), the same additives as the drying compositions based on F113.
  • additives are generally surface-active agents 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.
  • surface-active agents 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
  • This azeotrope used for cleaning solder flux 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)

Claims (18)

  1. Verwendung von Perfluoralkylethylen der Formel:



            RFCH=CH₂   (I)



    in der RF einen linearen oder verzweigten Perfluoralkylrest mit 3 bis 6 Kohlenstoffatomen enthält, als Reinigungs- oder Trockungsmittel für Feststoffoberflächen.
  2. Verwendung nach Anspruch 1, wobei die Verbindung der Formel (I) n-Perfluorbutylethylen C₄F₉CH=CH₂ ist.
  3. Zusammensetzung zur Reinigung von Feststoffoberflächen, dadurch gekennzeichnet, daß sie aus einer Mischung eines Perfluoralkylethylens nach Anspruch 1 oder 2 mit wenigstens einem organischen Lösemittel, ausgewählt aus Alkoholen, Ketonen, Estern, Ethern, Acetalen und chlorierten oder nicht-chlorierten Kohlenwasserstoffen besteht.
  4. Zusammensetzung nach Anspruch 3, die 85 bis 98 Gew.-% n-Perfluorbutylethylen und 2 bis 15 Gew.-% Methanol umfaßt.
  5. Zusammensetzung nach Anspruch 4, die 90 bis 95 Gew.-% n-Perfluorbutylethylen und 5 bis 10 Gew.-% Methanol umfaßt.
  6. Zusammensetzung nach Anspruch 4, das als Azeotrop mit einem Siedepunkt von 46,3 °C bei Atmosphärendruck vorliegt.
  7. Zusammensetzung nach Anspruch 3, die 91 bis 98 Gew.-% n-Perfluorbutylethylen und 2 bis 9 Gew.-% Isopropanol umfaßt.
  8. Zusammensetzung nach Anspruch 3, die 41 bis 51 Gew.-% n-Perfluorbutylethylen und 49 bis 59 Gew.-% Methylenchlorid umfaßt.
  9. Zusammensetzung nach Anspruch 3, die 89 bis 97 Gew.-% n-Perfluorbutylethylen und 3 bis 11 Gew.-% Trichlorethylen umfaßt.
  10. Zusammensetzung nach Anspruch 3, die 83 bis 90 Gew.-% n-Perfluorbutylethylen und 10 bis 17 Gew.-% 1,3-Dioxolan umfaßt.
  11. Zusammensetzung nach Anspruch 3, die 84,8 bis 97,8 Gew.-% n-Perfluorbutylethylen, 2 bis 15 Gew.-% Methanol und 0,2 bis 2,2 Gew.-% Methylacetat umfaßt.
  12. Zusammensetzung nach Anspruch 3, die 90 bis 98 Gew.-% n-Perfluorbutylethylen, 1 bis 9 Gew.-% Isopropanol und 1 bis 7 Gew.-% 1,3-Dioxolan umfaßt.
  13. Zusammensetzung nach Anspruch 3, die 90,95 bis 97,95 Gew.-% n-Perfluorbutylethylen, 2 bis 9 Gew.-% Isopropanol und 0,05 bis 1 Gew.-% 1,1-Dimethoxyethan umfaßt.
  14. Zusammensetzung nach einem der Ansprüche 3 bis 13, die ferner wenigstens einen Stabilisator umfaßt.
  15. Zusammensetzung nach Anspruch 14, wobei der Stabilisator ein Nitroalkan, ein Alkylenoxid oder eine Mischung dieser Verbindungen ist.
  16. Zusammensetzung nach Anspruch 14 oder 15, wobei der Anteil des Stabilisators 0,01 bis 5 % in bezug auf das Gesamtgewicht der Zusammensetzung beträgt.
  17. Zusammensetzung für die Trocknung von Feststoffoberflächen, dadurch gekennzeichnet, daß sie aus einer Mischung aus Perfluoralkylethylen nach Anspruch 1 oder 2 und wenigstens einem oberflächenaktiven Mittel besteht.
  18. Zusammensetzung nach Anspruch 17, wobei der Gehalt des oberflächenaktiven Mittels 0,01 bis 5 Gew.-%, vorzugsweise 0,1 bis 3 Gew.-% beträgt.
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 EP0443911A1 (de) 1991-08-28
EP0443911B1 true EP0443911B1 (de) 1995-01-18

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

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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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US5614565A (en) * 1995-03-24 1997-03-25 Bayer Corporation Azeotropic compositions of perfluorohexane and hydrocarbons having 6 carbon atoms and the use thereof in the production of foams
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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KR20080114757A (ko) * 2006-02-28 2008-12-31 이 아이 듀폰 디 네모아 앤드 캄파니 세정 분야를 위한 플루오르화 화합물을 포함하는 공비 조성물
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EP4098729A1 (de) 2021-06-01 2022-12-07 Cipelia Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung

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Also Published As

Publication number Publication date
NO910596D0 (no) 1991-02-14
NO176673C (no) 1995-05-10
PT96811A (pt) 1991-10-31
EP0443911A1 (de) 1991-08-28
JPH04227803A (ja) 1992-08-17
ATE117362T1 (de) 1995-02-15
FI98827C (fi) 1997-08-25
IE910560A1 (en) 1991-08-28
FR2658532A1 (fr) 1991-08-23
NO176673B (no) 1995-01-30
PT96811B (pt) 1998-07-31
FI910800A (fi) 1991-08-21
IE68777B1 (en) 1996-07-10
FI910800A0 (fi) 1991-02-19
AU635387B2 (en) 1993-03-18
DE69106740D1 (de) 1995-03-02
NO910596L (no) 1991-08-21
US5302212A (en) 1994-04-12
KR910021472A (ko) 1991-12-20
AU7098991A (en) 1991-08-22
FI98827B (fi) 1997-05-15
JPH0615003B2 (ja) 1994-03-02
CA2035687A1 (fr) 1991-08-21
DE69106740T2 (de) 1995-08-10
CA2035687C (fr) 1998-05-05
KR930007225B1 (ko) 1993-08-04
FR2658532B1 (fr) 1992-05-15

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