EP0974642A1 - Reinigungs- und Trocknungsmittel auf Basis von 1,1,1,2,3,4,4,5,5,5-Decafluorpentan - Google Patents

Reinigungs- und Trocknungsmittel auf Basis von 1,1,1,2,3,4,4,5,5,5-Decafluorpentan Download PDF

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Publication number
EP0974642A1
EP0974642A1 EP99401419A EP99401419A EP0974642A1 EP 0974642 A1 EP0974642 A1 EP 0974642A1 EP 99401419 A EP99401419 A EP 99401419A EP 99401419 A EP99401419 A EP 99401419A EP 0974642 A1 EP0974642 A1 EP 0974642A1
Authority
EP
European Patent Office
Prior art keywords
cleaning
azeotropic
compositions
mee
decafluoropentane
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.)
Granted
Application number
EP99401419A
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English (en)
French (fr)
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EP0974642B1 (de
Inventor
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
Atofina SA
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Filing date
Publication date
Application filed by Elf Atochem SA, Atofina SA filed Critical Elf Atochem SA
Publication of EP0974642A1 publication Critical patent/EP0974642A1/de
Application granted granted Critical
Publication of EP0974642B1 publication Critical patent/EP0974642B1/de
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
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/505—Mixtures of (hydro)fluorocarbons
    • 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

Definitions

  • the present invention relates to the field of fluorinated hydrocarbons and to more particularly for subject of new compositions usable for cleaning or dry solid surfaces.
  • 1,1,2-Trichloro-1,2,2-trifluoroethane (known in the trade under the designation F113) has been widely used in the industry for cleaning and degreasing of very diverse solid surfaces (metal parts, glasses, plastics, composites), for which an absence - or at least a content residual as low as possible - in impurities, especially organic, is required.
  • the F 113 was particularly suitable for this use because of its non-aggressive character with regard to the materials used.
  • This product was notably used in the manufacturing of printed circuits, to eliminate residues of substances used to improve the quality of welds (designated by the term weld flux). This disposal operation is designated in the trade by the term "defluxing".
  • F113 to degreasing heavy metal parts and high quality mechanical parts cleaning and with great precision like, for example, gyroscopes and military equipment, aerospace or medical.
  • the F113 is most often combined with other organic solvents (eg methanol), to improve its cleaning capacity.
  • azeotropic mixtures or almost azeotropic By quasi-azeotropic mixture is understood within the meaning of present invention a mixture of generally miscible chemical compounds which, under certain particular conditions of proportions, temperature and pressure, tip at substantially constant temperature while retaining substantially the same composition. When heated to reflux, such a mixture almost azeotropic is in equilibrium with a vapor phase whose composition is substantially the same as that of the liquid phase.
  • Such behavior azeotropic or near azeotropic is desirable to ensure functioning satisfactory of the machines in which the operations of cleaning mentioned above, and in particular to ensure recycling by distillation of the cleaning fluid.
  • F113 is also used in the fields, in particular in optics, for which it is required to have water-free surfaces, i.e. surfaces where water is only present as traces undetectable by the method of measurement (Karl Fisher method).
  • the F113 is for this purpose implemented in drying operations (or dewetting) of said surfaces, in combination with hydrophobic surfactants.
  • compositions based on F113 are now prohibited because F113 is one of the chlorofluorocarbons (CFCs) suspected of attacking or degrade stratospheric ozone.
  • CFCs chlorofluorocarbons
  • F113 can be replaced by 1,1-dichloro-1-fluoroethane (known as F141b), but the use of this substitute is already regulated because, although weak, its destructive effect on of ozone is not zero.
  • F141b 1,1-dichloro-1-fluoroethane
  • Application EP 0512885 describes a composition comprising from 93 to 99% by weight of 1,1,1,3,3-pentafluorobutane and from 1 to 7% of methanol, usable as a substitute for F113.
  • 1,1,1,3,3-pentafluorobutane also known in the trade under the name of F365mfc, is devoid of destructive effect vis-à-vis of ozone.
  • the object of the invention is to propose other compositions capable of to be used as a substitute for F113 or F141b, and without effect destructive to ozone.
  • the present invention therefore has for subject of azeotropic or quasi-azeotropic compositions comprising from 1 to 25% of 1,1,1,2,3,4,4,5,5,5,5-decafluoropentane, preferably from 5 to 20%, and 75 to 99% of 1,1,1,3,3-pentafluorobutane, preferably 80 to 95%. Except otherwise indicated, the percentages used in this text to indicate the content of the compositions according to the invention are percentages by weight.
  • the 1,1,1,2,3,4,4,5,5,5-decafluoropentane is a compound (also known as denomination 43-10 mee) completely devoid of destructive effect with respect to ozone.
  • compositions according to the invention make it possible to obtain very good results for cleaning and degreasing solid surfaces, as well as in drying and dewetting operations.
  • these compositions do not show a flash point under standard determination conditions (ASTM D 3828 standard) and therefore allow you to work in complete safety.
  • compositions according to the invention can be easily prepared by simple mixing of the constituents.
  • the 43-10 mee is commercially available; 365mfc can be prepared by at least one of the following methods: Zh. Org. Khim. 1980, 1401-1408 and 1982, 946 and 1168 ;. Zh. Org. Khim. 1988, 1558. J. Chem. Soc Perk. I, 1980, 2258; J Chem. Soc Perk. Trans, 2. 1983, 1713; J. Chem. Soc. C Perk. Trans, 2.198, 1713: J. Chem. Soc. C 1969, 1739: Chem. Soc. 1949, 2860: Zh. Anal. Khim, 1981 36 (6), 1125; J. Fluorite Chem.
  • a ternary composition according to the invention includes 5 to 20% of 43-10 mee, 75 to 90% of 365 mfc, and 1 to 10% of methanol. More particularly preferred is a ternary composition containing 10 15% from 43-10 mee, 80 to 85% from 365 mfc, and 2 to 8% methanol. In this field, there is an azeotrope with a boiling point of 33.2 ° C at normal atmospheric pressure.
  • the cleaning compositions based on 43-10 mee and 365 mfc according to the invention can, if desired, be protected from chemical attack resulting from their contact with water (hydrolysis), with light metals (constituting the solid surfaces to be cleaned), and / or against radical attacks likely to occur in cleaning processes, adding a usual stabilizer such as, for example, nitroalkanes (in particular nitromethane, nitroethane, nitropropane), acetals (dimethoxymethane) and ethers (1,4-dioxane, 1,3-dioxolane).
  • a usual stabilizer such as, for example, nitroalkanes (in particular nitromethane, nitroethane, nitropropane), acetals (dimethoxymethane) and ethers (1,4-dioxane, 1,3-dioxolane).
  • the proportion of stabilizer can range from 0.01 to 5% per relative to the total weight of the composition.
  • compositions according to the invention can be used in the same applications and be implemented in the same manner as previous compositions based on F113 or F141b. They are therefore suitable particularly for use in cleaning and degreasing surfaces solids, preferably for defluxing printed circuits, as well as for surface drying operations.
  • compositions can also be used as blowing agent polyurethane foams, as an agent for dry cleaning textiles, and as a refrigerant.
  • 100 g are introduced into the distiller of a distillation column (30 trays) of 43-10 mee and 100 g of 365mfc. The mixture is then heated at reflux for one hour to bring the system to balance.
  • This azeotrope used for cleaning solder flux or in degreasing of mechanical parts, gives good results.
  • 200 g are introduced into the distiller of a distillation column (30 trays) of a mixture comprising 9% of 43-10 mee and 91% of 365mfc. The mixture is then heated at reflux for an hour to bring the system to equilibrium.
  • 150g of a mixture containing by weight 9% of 43-10 mee, 90.5% of 365mfc and 0.5% of methylal as stabilizer are introduced into a small ultrasonic cleaning tank. After heating the system at reflux for one hour, an aliquot of the vapor phase is taken. Its analysis, by gas chromatography, shows the presence of methylal, which indicates that the mixture is also stabilized in the vapor phase.
  • 100 g are introduced into the distiller of a distillation column (30 trays) of 43-10 mee, 100 g of 365mfc and 50g of methanol. The mixture is then heated at reflux for one hour to bring the system to balance. When a temperature plateau is observed, a fraction of approximately 20 g is collected. This fraction and the fraction of the bottom remaining in the boiler are analyzed. by gas chromatography.
  • This azeotrope used for cleaning solder flux or in degreasing of mechanical parts, gives good results.
  • Example 2 the above azeotropic composition can be stabilized with 0.5% dimethoxymethane.
  • test circuits conforming to the IPC-B-25 standard described in the manual for test methods of the IPC (Institute for Interconnecting and Packaging Electronic Circuits; Lincolnwood, IL, USA). These circuits are coated with rosin-based solder flux (product marketed by ALPHAMETAL under the name R8F flow) and annealed in an oven at 220 ° C for 30 seconds.
  • rosin-based solder flux product marketed by ALPHAMETAL under the name R8F flow
  • these circuits are cleaned using of the azeotropic composition of Example 3, in a small machine ultrasound for 3 minutes by immersion in the liquid phase and 3 minutes by vapor phase.
  • the cleaning is evaluated according to the standardized procedure IPC 2.3.26 (also described in the manual cited above) using a precision conductivity meter.
  • the value obtained, 2.2 ⁇ g / cm 2 eq.NaCl, is lower than the ionic impurity threshold tolerated by the profession (2.5 ⁇ g / cm 2 eq.NaCl).

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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)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
EP99401419A 1998-07-24 1999-06-11 Reinigungs- und Trocknungsmittel auf Basis von 1,1,1,2,3,4,4,5,5,5-Decafluorpentan und 1,1,1,3,3-pentafluorbutan Expired - Lifetime EP0974642B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9809464 1998-07-24
FR9809464A FR2781499B1 (fr) 1998-07-24 1998-07-24 Compositions de nettoyage ou de sechage a base de 1,1,1,2,3,4,4,5,5, 5 - decafluoropentane

Publications (2)

Publication Number Publication Date
EP0974642A1 true EP0974642A1 (de) 2000-01-26
EP0974642B1 EP0974642B1 (de) 2003-09-03

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EP99401419A Expired - Lifetime EP0974642B1 (de) 1998-07-24 1999-06-11 Reinigungs- und Trocknungsmittel auf Basis von 1,1,1,2,3,4,4,5,5,5-Decafluorpentan und 1,1,1,3,3-pentafluorbutan

Country Status (5)

Country Link
US (2) US6174850B1 (de)
EP (1) EP0974642B1 (de)
DE (1) DE69910916T2 (de)
ES (1) ES2207140T3 (de)
FR (1) FR2781499B1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2829773A1 (fr) * 2001-09-17 2003-03-21 Atofina COMPOSITION DE NETTOYAGE OU DE SECHAGE A BASE DE N-PERFLUOROBUTYL-ETHYLENE ET DE HFC 365 mfc
EP1163312B1 (de) * 1999-03-22 2004-12-29 E.I. Du Pont De Nemours And Company Azeotropähnliche zusammensetzungen von 1,1,1,3,3-pentafluorbutan

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2781499B1 (fr) * 1998-07-24 2000-09-08 Atochem Elf Sa Compositions de nettoyage ou de sechage a base de 1,1,1,2,3,4,4,5,5, 5 - decafluoropentane
US6660709B1 (en) * 1998-12-12 2003-12-09 Solvay (Societe Anonyme) Compositions comprising 1,1,1,3,3-pentafluorobutane and use of these compositions
FR2792647B1 (fr) * 1999-04-22 2001-06-08 Atochem Elf Sa COMPOSITIONS DE NETTOYAGE OU DE SECHAGE A BASE DE F365 mfc, CH2CL2, CH3OH ET 43-10mee
WO2002064724A1 (fr) * 2001-02-14 2002-08-22 Kaneko Chemical Co., Ltd. Compositions detergentes a base de solvants
GB0330010D0 (en) 2003-12-24 2004-01-28 Cavendish Kinetics Ltd Method for containing a device and a corresponding device
FR2873689B1 (fr) * 2004-07-29 2006-10-13 Arkema Sa Composition a base de 1,1,1,3,3,-pentafluorobutane
FR2874383B1 (fr) * 2004-08-18 2006-10-13 Arkema Sa Composition a base de 1,1,1,3,3 - pentafluorobutane, utilisable dans des applications de depot, nettoyage, degraissage et sechage
US7989262B2 (en) * 2008-02-22 2011-08-02 Cavendish Kinetics, Ltd. Method of sealing a cavity
US7993950B2 (en) * 2008-04-30 2011-08-09 Cavendish Kinetics, Ltd. System and method of encapsulation

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
EP1163312B1 (de) * 1999-03-22 2004-12-29 E.I. Du Pont De Nemours And Company Azeotropähnliche zusammensetzungen von 1,1,1,3,3-pentafluorbutan
JP2006169539A (ja) * 1999-03-22 2006-06-29 E I Du Pont De Nemours & Co １，１，１，３，３−ペンタフルオロブタンの共沸様組成物
US7531496B2 (en) 1999-03-22 2009-05-12 El And Micro Care Corp Azeotrope-like compositions of 1,1,1,3,3-pentafluorobutane
JP4499029B2 (ja) * 1999-03-22 2010-07-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー １，１，１，３，３−ペンタフルオロブタンの共沸様組成物
FR2829773A1 (fr) * 2001-09-17 2003-03-21 Atofina COMPOSITION DE NETTOYAGE OU DE SECHAGE A BASE DE N-PERFLUOROBUTYL-ETHYLENE ET DE HFC 365 mfc
WO2003025109A1 (fr) * 2001-09-17 2003-03-27 Atofina Compositions de nettoyage ou de sechage a base de n-perfluorobutyl-ethylene et de hfc 365mfc

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EP0974642B1 (de) 2003-09-03
US6174850B1 (en) 2001-01-16
FR2781499B1 (fr) 2000-09-08
DE69910916T2 (de) 2004-07-15
USRE39819E1 (en) 2007-09-04
DE69910916D1 (de) 2003-10-09
ES2207140T3 (es) 2004-05-16
FR2781499A1 (fr) 2000-01-28

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