EP1040179B1 - Perfluorobutylmethylether enthaltende zusammensetzungen und deren verwendung - Google Patents

Perfluorobutylmethylether enthaltende zusammensetzungen und deren verwendung Download PDF

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Publication number
EP1040179B1
EP1040179B1 EP98965826A EP98965826A EP1040179B1 EP 1040179 B1 EP1040179 B1 EP 1040179B1 EP 98965826 A EP98965826 A EP 98965826A EP 98965826 A EP98965826 A EP 98965826A EP 1040179 B1 EP1040179 B1 EP 1040179B1
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EP
European Patent Office
Prior art keywords
weight
approximately
compositions
methyl ether
boiling point
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
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EP98965826A
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English (en)
French (fr)
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EP1040179A1 (de
Inventor
Pierre Barthelemy
Pierre Dournel
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Solvay SA
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Solvay SA
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Publication of EP1040179A1 publication Critical patent/EP1040179A1/de
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G11/00—Selection of substances for use as fixing agents
    • 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
    • C11D7/5063—Halogenated hydrocarbons containing heteroatoms, e.g. fluoro alcohols
    • 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
    • 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 invention relates to compositions comprising perfluorobutyl methyl ether (C 4 F 9 -O-CH 3 ) and the use of these compositions, especially as a cleaning or drying agent for solid surfaces.
  • CFCs Fully halogenated chlorofluorocarbons
  • CFC-113 1,1,2-trichloro-1,2,2-trifluoroethane
  • CFC-113 is widely used as solvents in industry for degreasing and surface cleaning various, particularly for solid parts of complicated shape and difficult to clean.
  • CFC-113 is most often associated with other organic solvents, preferably in the form of azeotropic or pseudoazeotropic compositions having substantially the same composition in the vapor phase and in the liquid phase, so that they can be easily used at reflux.
  • compositions based on CFC-113 are also conventionally used as a desiccant, in order to eliminate the water adsorbed on the surface of solid parts.
  • hydrofluorinated chlorine-free compounds are completely inert with respect to the stratospheric ozone layer and there is an increasing use of these compounds in many applications to the detriment of compounds carrying chlorine atoms. .
  • the patent application WO 96/36689 provides azeotropic compositions of perfluorobutyl methyl ether with one or more organic solvents selected from linear or branched cyclic or acyclic alkanes comprising 6 to 8 carbon atoms, cyclic or acyclic ethers comprising 4 to 6 carbon atoms, ketones comprising 3 carbon atoms, chlorinated alkanes comprising 1.3 or 4 carbon atoms, chlorinated alkenes comprising 2 to 4 carbon atoms, 3 carbon atoms, alcohols comprising 1 to 4 carbon atoms, partially fluorinated alcohols comprising 2 to 3 carbon atoms, 1-bromopropane, acetonitrile, HCFC-225ea, and HCFC-225cb.
  • organic solvents selected from linear or branched cyclic or acyclic alkanes comprising 6 to 8 carbon atoms, cyclic or acyclic ethers comprising 4 to 6 carbon atoms,
  • compositions for cleaning and degreasing metal parts comprising mixtures based on alkoxy-substituted perfluorinated compounds and cosolvents, such as, in particular, the esters; the use of a mixture of perfluorobutyl methyl ether and methyl decanoate is specifically described therein.
  • WO 96/36688 discloses pseudo-azeotropic compositions based on perfluorobutyl ethyl ether and, inter alia, esters containing 4 carbon atoms, which can be used for the formulation of composition for surface coating.
  • EPC discloses the use as a toner fixing agent for a recording medium of a mixture of perfluorobutyl methyl ether and 5% by weight of methyl acetate.
  • compositions optionally forming azeotropes or pseudoazeotropes, which are particularly effective when used as a cleaning agent in solvent cleaning processes.
  • the invention also relates to such compositions having properties particularly suitable for cleaning printed circuit boards.
  • Another object of the invention is to provide such compositions devoid of destructive effect vis-à-vis the ozone layer.
  • the invention also relates to compositions having particularly suitable properties as a toner fixing agent to a recording medium in a printing apparatus or reproduction of documents.
  • the present invention therefore relates to azeotropic or pseudo-azeotropic compositions comprising at least one perfluorobutyl methyl ether of general formula C 4 F 9 -O-CH 3 where C 4 F 9 is a linear or branched perfluorinated chain and at least one ester chosen of, methyl acetate, ethyl formate and methyl formate, said compositions containing about 21 to 52% by weight of methyl acetate or about 22 to 53% by weight of ethyl formate or about 40 to 92% by weight of methyl formate CF 3 - (CF 2 ) 3 -O-CH 3 , the (CF 3 ) 2 CF-CF 2 -O-CH 3 and mixtures thereof are the preferred perfluorobutyl methyl ethers.
  • the term "perfluorobutyl methyl ether" is used to designate a mixture of these 2 compounds, marketed by 3M under the name HFE-7100.
  • thermodynamic state of a fluid is defined by four interdependent variables: pressure (P), temperature (T), composition the liquid phase (X) and the composition of the gas phase (Y).
  • a true azeotrope is a particular 2 or more component system for which, at a given temperature and at a given pressure, the composition of the liquid phase X is exactly equal to the composition of the gas phase Y.
  • a pseudoazeotrope is a two or more component system for which, at a given temperature and at a given pressure, X is substantially equal to Y. In practice, this means that the constituents of such azeotropic and pseudo-azeotropic systems can not They can not be separated easily by distillation and therefore their composition remains substantially constant in the solvent cleaning operations, as well as in the recovery operations of solvents used by distillation.
  • a pseudo-azeotropic mixture is understood to mean a mixture of two constituents whose boiling point (at a given pressure) differs from the boiling point of the true azeotrope of 0.5.degree. maximum. Mixtures whose boiling point differs from the boiling point of the true azeotrope of up to 0.2 ° C are preferred. Mixtures whose boiling point differs from the boiling point of the true azeotrope by up to 0.1 ° C are particularly preferred.
  • compositions according to the invention can vary widely, depending on the intended use.
  • compositions according to the invention contain at least 1% by weight of perfluorobutyl methyl ether. They advantageously contain at least 5%. In a particularly preferred manner, they contain at least 10%. They can contain up to 99%. Most often, they contain at most 95%.
  • compositions according to the invention are those which contain perfluorobutyl methyl ether and an ester in proportions in which they form a minimum boiling azeotrope or pseudoazeotrope.
  • compositions of the azeotropic mixtures according to the invention were estimated on the basis of the results of the experimental measurements presented in the examples below.
  • Perfluorobutyl methyl ether and methyl acetate form a binary azeotrope or pseudo-azeotrope when their mixture contains about 21 to 52% by weight of methyl acetate.
  • the binary compositions containing about 28 to 48% by weight of methyl acetate are preferred.
  • the binary composition consisting essentially of about 61% by weight of perfluorobutyl methyl ether and about 39% by weight of methyl acetate constitutes a true azeotrope, whose boiling point is about 52.6 ° C. This composition is very particularly preferred.
  • Perfluorobutyl methyl ether and ethyl formate form a binary azeotrope or pseudoazeotrope when their mixture contains about 22 to 53% by weight of ethyl formate.
  • Binary compositions containing about 26 to 46% by weight of ethyl formate are preferred.
  • the binary composition consisting essentially of about 68% by weight of perfluorobutyl methyl ether and about 32% by weight of ethyl formate constitutes a true azeotrope, whose boiling point is about 50.2 ° C. This composition is very particularly preferred.
  • Perfluorobutyl methyl ether and methyl formate form a binary azeotrope or pseudoazeotrope when their mixture contains about 40 to 92% by weight of methyl formate.
  • Binary compositions containing about 59 to 80% by weight of methyl formate are preferred. Under a pressure of 102.2 kPa, the binary composition consisting essentially of about 36% by weight of perfluorobutyl methyl ether and about 64% by weight of methyl formate constitutes a true azeotrope whose boiling point is about 31.2 ° C. This composition is very particularly preferred.
  • compositions according to the invention may optionally be present in the compositions according to the invention.
  • the compositions according to the invention may thus contain stabilizers, surfactants or any other additives making it possible to improve the performance of the compositions according to the invention during their use.
  • the nature and the quantity of these additives depend on the intended use and are easily defined by those skilled in the art.
  • the amount of additives present in the compositions according to the invention does not exceed about 20% of the weight of the composition, most often not more than 10%.
  • compositions according to the invention have a boiling point suitable for replacing CFC-113-based compositions in existing cleaning apparatus. As regards its impact on the environment, perfluorobutyl methyl ether appears to be particularly interesting since it has a zero ozone destruction potential.
  • the compositions according to the invention are further inert against the different types of surfaces to be treated, whether they are metal, plastic or glass.
  • compositions according to the invention can therefore be used in the same applications and according to the same techniques as the prior compositions based on CFC-113.
  • the compositions according to the invention can be used as a cleaning agent, solvent, degreasing agent, defluxant or desiccant.
  • the invention therefore also relates to the use of the compositions according to the invention as a cleaning agent, as a degreasing agent for solid surfaces, as a cleaning agent for printed circuit boards, contaminated with a stripping flux and residues thereof. as a desiccant to remove adsorbed water on the surface of solid objects.
  • the compositions according to the invention can also be used as a toner fixing agent for a recording medium in a printing or copying apparatus.
  • Perfluorobutyl methyl ether compositions useful as a toner fixing agent are compositions containing a C3-C6 hydrofluorocarbon.
  • C3-C6 hydrofluorocarbon is meant saturated hydrocarbons, aliphatic or alicyclic, consisting solely of carbon, fluorine and hydrogen, comprising from 3 to 6 carbon atoms, at least one fluorine atom and at least one atom hydrogen.
  • C 3 -C 6 hydrofluorocarbons are hydrofluoroalkanes such as 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1,1,1,3,3-pentafluorobutane (HFC-365mfc) and 1,1,1,2,2,3,4,6,6,6-decafluoropentane (HFC-43-10mee).
  • 1,1,1,3,3-Pentafluorobutane is particularly suitable.
  • C3-C6 perfluorobutyl methyl ether / ester / hydrofluorocarbon terefinal compositions are used.
  • the invention therefore also relates to the use of the compositions according to the invention as a toner fixing agent to a recording medium in a printing device or reproduction of documents.
  • azeotropic or pseudoazeotropic compositions according to the invention between perfluorobutyl methyl ether and an ester, a glass apparatus consisting of a 50 ml boiler flask surmounted by a reflux condenser was used. . The temperature of the liquid was measured by means of a thermometer immersed in the flask.
  • the determination of the azeotropic composition was carried out by recording the evolution of the boiling point of the mixture as a function of its composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)

Claims (9)

  1. Azeotrope oder pseudoazeotrope Zusammensetzung, umfassend mindestens einen Perfluorbutylmethylether der Formel C4F9-O-CH3, worin C4F9 für eine lineare oder verzweigte perfluorierte Kette steht, und mindestens einen Ester, dadurch gekennzeichnet, daß der Ester unter Essigsäuremethylester, Ameisensäureethylester und Ameisensäuremethylester ausgewählt ist, wobei die Zusammensetzung ungefähr 21 bis 52 Gew.- % Essigsäuremethylester oder ungefähr 22 bis 53 Gew.- % Ameisensäureethylester oder ungefähr 40 bis 92 Gew.- % Ameisensäuremethylester enthält.
  2. Zusammensetzung nach Anspruch 1, wobei der Perfluorbutylmethylether unter CF3-(CF2)3-O-CH3, (CF3)2CF-CF2-O-CH3 und Mischungen davon ausgewählt ist.
  3. Zusammensetzung nach Anspruch 1 oder 2, enthaltend ungefähr 28 bis 48 Gew.- % Essigsäuremethylester oder ungefähr 26 bis 46 Gew.- % Ameisensäureethylester oder ungefähr 59 bis 80 Gew.- % Ameisensäuremethylester.
  4. Azeotrope Zusammensetzung mit minimalem Siedepunkt nach Anspruch 1 oder 2, die aus ungefähr 61 Gew.- % Perfluorbutylmethylether und ungefähr 39 Gew.- % Essigsäuremethylester besteht und einen Siedepunkt von ungefähr 52,6°C unter einem Druck von 102,3 kPa aufweist.
  5. Azeotrope Zusammensetzung mit minimalem Siedepunkt nach Anspruch 1 oder 2, die aus ungefähr 68 Gew.- % Perfluorbutylmethylether und ungefähr 32 Gew.- % Ameisensäureethylester besteht und einen Siedepunkt von ungefähr 50,2°C unter einem Druck von 102,6 kPa aufweist.
  6. Azeotrope Zusammensetzung mit minimalem Siedepunkt nach Anspruch 1 oder 2, die aus ungefähr 36 Gew.- % Perfluorbutylmethylether und ungefähr 64 Gew.- % Ameisensäuremethylester besteht und einen Siedepunkt von ungefähr 31,2°C unter einem Druck von 102,2 kPa aufweist.
  7. Verwendung der Zusammensetzungen nach einem der Ansprüche 1 bis 6 als Reinigungsmittel, Entfettungsmittel für feste Oberflächen, Reinigungsmittel für Leiterplatten, die durch ein Lötflußmittel und Reste dieses Flußmittels verunreinigt sind, oder Trocknungsmittel zur Entfernung von an der Oberfläche fester Objekte adsorbiertem Wasser.
  8. Zusammensetzung nach einem der Ansprüche 1 bis 6, die ferner einen teilfluorierten C3-C6-Fluorkohlenwasserstoff enthält.
  9. Verwendung der Zusammensetzungen nach einem der Ansprüche 1 bis 6 und 8 als Mittel zur Fixierung eines Toners auf einem Aufzeichnungsträger in einer Druck- oder Dokumentenvervielfältigungsvorrichtung.
EP98965826A 1997-12-15 1998-12-12 Perfluorobutylmethylether enthaltende zusammensetzungen und deren verwendung Expired - Lifetime EP1040179B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
BE9701016 1997-12-15
BE9701016A BE1011609A3 (fr) 1997-12-15 1997-12-15 Compositions comprenant du perfluorobutyl methyl ether et utilisation de ces compositions.
PCT/EP1998/008160 WO1999031214A1 (fr) 1997-12-15 1998-12-12 Compositions comprenant du perfluorobutyl methyl ether et utilisation de ces compositions

Publications (2)

Publication Number Publication Date
EP1040179A1 EP1040179A1 (de) 2000-10-04
EP1040179B1 true EP1040179B1 (de) 2011-03-09

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EP98965826A Expired - Lifetime EP1040179B1 (de) 1997-12-15 1998-12-12 Perfluorobutylmethylether enthaltende zusammensetzungen und deren verwendung

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US (1) US6753304B1 (de)
EP (1) EP1040179B1 (de)
JP (1) JP4515632B2 (de)
AT (1) ATE501241T1 (de)
AU (1) AU2161499A (de)
BE (1) BE1011609A3 (de)
DE (1) DE69842170D1 (de)
WO (1) WO1999031214A1 (de)

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JP2017043680A (ja) * 2015-08-25 2017-03-02 株式会社カネコ化学 洗浄用溶剤組成物
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US11478987B2 (en) 2016-12-14 2022-10-25 Carbon, Inc. Methods and apparatus for washing objects produced by stereolithography
WO2018118832A1 (en) 2016-12-23 2018-06-28 Carbon, Inc. Adhesive sheet for securing 3d object to carrier platform and method of using same
WO2018169821A1 (en) 2017-03-15 2018-09-20 Carbon, Inc. Integrated additive manufacturing systems
WO2019083876A1 (en) 2017-10-26 2019-05-02 Carbon, Inc. REDUCTION OF WITHDRAWAL OR LOWERING IN OBJECTS PRODUCED BY ADDITIVE MANUFACTURING
US11535714B2 (en) 2017-11-20 2022-12-27 Carbon, Inc. Light-curable siloxane resins for additive manufacturing
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WO2019165052A1 (en) 2018-02-21 2019-08-29 Carbon, Inc. Methods of reducing distortion of additively manufactured objects
JP6872082B2 (ja) 2018-02-21 2021-05-19 カーボン，インコーポレイテッド 付加製造中のキャリアへの物体の付着の強化
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WO2020023823A1 (en) 2018-07-27 2020-01-30 Carbon, Inc. Branched reactive blocked prepolymers for additive manufacturing
WO2020028498A1 (en) 2018-08-01 2020-02-06 Carbon, Inc. Method for rapid encapsulation of microelectronic devices
CN112703101B (zh) 2018-08-01 2023-01-31 卡本有限公司 通过增材制造生产低密度产品
US20210242097A1 (en) 2018-08-02 2021-08-05 Carbon, Inc. Method of Packaging an Integrated Circuit
CN114364467A (zh) 2019-09-20 2022-04-15 卡本有限公司 通过真空循环成核而增材制造的物体的清洁
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Also Published As

Publication number Publication date
AU2161499A (en) 1999-07-05
WO1999031214A1 (fr) 1999-06-24
EP1040179A1 (de) 2000-10-04
DE69842170D1 (de) 2011-04-21
JP4515632B2 (ja) 2010-08-04
ATE501241T1 (de) 2011-03-15
BE1011609A3 (fr) 1999-11-09
US6753304B1 (en) 2004-06-22
JP2002508439A (ja) 2002-03-19

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