EP0609125A1 - Stabilized cleaning composition based on 1,1-dichloro-1-fluoroethane and methanol - Google Patents
Stabilized cleaning composition based on 1,1-dichloro-1-fluoroethane and methanol Download PDFInfo
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- EP0609125A1 EP0609125A1 EP94400141A EP94400141A EP0609125A1 EP 0609125 A1 EP0609125 A1 EP 0609125A1 EP 94400141 A EP94400141 A EP 94400141A EP 94400141 A EP94400141 A EP 94400141A EP 0609125 A1 EP0609125 A1 EP 0609125A1
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- European Patent Office
- Prior art keywords
- methanol
- fluoroethane
- dichloro
- composition
- dioxolane
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Classifications
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
- C23G5/02825—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine containing hydrogen
- C23G5/02829—Ethanes
- C23G5/02832—C2H3Cl2F
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- 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
- C23G5/02854—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 characterised by the stabilising or corrosion inhibiting additives
- C23G5/02861—Oxygen-containing compounds
- C23G5/02877—Ethers
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/267—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing halogen
Definitions
- the present invention relates to the field of chlorofluorinated hydrocarbons and more particularly relates to a stabilized composition based on 1,1-dichloro-1-fluoroethane and methanol, usable as an agent for cleaning and degreasing solid surfaces, in particular in the defluxing of printed circuits and degreasing of mechanical parts.
- 1,1,2-Trichloro-1,2,2-trifluoroethane known in the art under the designation F113, is widely used in the industry for cleaning and degreasing solid surfaces. It is, however, one of the perhalogenated chlorofluorocarbons (CFCs) suspected of attacking and degrading stratospheric ozone, and will therefore have to be replaced in the short term by substitutes having little or no ozone-destroying effect. , such as 1,1-dichloro-1-fluoroethane.
- CFCs perhalogenated chlorofluorocarbons
- F141b has, like F113, the advantage of forming with methanol an azeotropic composition which is particularly useful for cleaning operations (patents EP 325 265, US 4 842 764 and JP 2 273 632 ).
- chlorofluorinated hydrocarbon associated with methanol is F113 or F141b
- Nitromethane is usually used to stabilize the azeotropic composition F113-methanol and this same compound has also been proposed in US Pat. No. 4,816,174 as a stabilizer for the azeotropic composition F141b-methanol.
- 4,842,764 mentions secondary and tertiary amines, olefins and cycloolefins, alkylene oxides, sulfoxides, sulfones, nitrites and nitriles, and acetylenic alcohols or ethers.
- dimethoxymethane and 1,3-dioxolane are excellent stabilizers of the F141b-methanol compositions. They indeed make it possible to inhibit the reaction of methanol with light metals such as aluminum and magnesium (very sensitive) and exhibit in this respect a behavior very different from that of very similar compounds such as dimethoxyethane, diethyl ether, methyl tert-butyl ether, furan and tetrahydrofuran.
- the subject of the invention is therefore a cleaning composition based on F141b and methanol, characterized in that it contains, as stabilizer, from 0.01 to 1% (preferably 0.1 to 0.5% ) of dimethoxymethane or of 1,3-dioxolane relative to the total weight of methanol and of F141b.
- the weight proportion of methanol is advantageously between 0.2 and 10% and that of F141b between 99.8 and 90%.
- a more particularly preferred composition is that in which the respective proportions of methanol and of F141b correspond substantially to the azeotropic composition, that is to say 3 to 5% of methanol and 97 to 95% of F141b.
- compositions according to the invention do not have a flash point under the standard determination conditions and can therefore be used without danger in the machines usually used for cleaning weld fluxes, degreasing heavy metal parts or cleaning mechanical parts. high quality and high precision such as, for example, gyroscopes and military or aerospace equipment.
- a composition according to the invention is prepared by adding 0.2% by weight (ie 12 g) of 1,3-dioxolane to 5 liters of azeotropic mixture F141b-methanol (96% of F141b and 4% of methanol), then introduce this composition into a small BRANSON cleaning machine and bring it to reflux for 4 hours so that the system is in balance.
- Example 1 is repeated, replacing the 12 g of 1,3-dioxolane with 24 g of dimethoxymethane (0.4% by weight). After 4 hours of reflux so that the system is in equilibrium, the analysis of a fraction of the condensate returns by gas chromatography indicates that the vapor phase is stabilized.
- COMPOSITION (% by weight) F141b Methanol dimethoxymethane Initial mix 95.62 3.98 0.40 Collected fraction 95.77 3.99 0.24
- Example 1 In a small single-tank laboratory machine equipped with an ultrasonic generator, 125 ml of the composition of Example 1 are introduced, then the liquid is brought to the boil.
- the quality of the cleaning is evaluated by determining the ionic residue rate according to the standard procedure IPC-TM 650 n ° 2.3.25 and 2.3.26 and according to the MIL-STD-2000 standard.
- the value obtained 1.87 ⁇ g eq.NaCl / cm2, is much lower than the threshold (2.5 ⁇ g eq. NaCl / cm2) tolerated in the field of electronics.
- Example 4 is repeated, but with the composition of Example 2 stabilized with dimethoxymethane.
- the rate of ionic residue is then 1.86 ⁇ g eq. NaCl / cm2.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Cleaning Or Drying Semiconductors (AREA)
- Manufacturing Of Printed Wiring (AREA)
Abstract
Description
La présente invention concerne le domaine des hydrocarbures chlorofluorés et a plus particulièrement pour objet une composition stabilisée à base de 1,1-dichloro-1-fluoroéthane et de méthanol, utilisable comme agent de nettoyage et de dégraissage de surfaces solides, en particulier dans le défluxage des circuits imprimés et le dégraissage de pièces mécaniques.The present invention relates to the field of chlorofluorinated hydrocarbons and more particularly relates to a stabilized composition based on 1,1-dichloro-1-fluoroethane and methanol, usable as an agent for cleaning and degreasing solid surfaces, in particular in the defluxing of printed circuits and degreasing of mechanical parts.
Le 1,1,2-trichloro-1,2,2-trifluoroéthane, connu dans le métier sous la désignation F113, est largement utilisé dans l'industrie pour le nettoyage et le dégraissage des surfaces solides. Il fait cependant partie des chlorofluorocarbures perhalogénés (CFC) suspectés d'attaquer et de dégrader l'ozone stratosphérique, et devra donc à brève échéance être remplacé par des substituts ayant peu ou pas d'effet destructeur vis-à-vis de l'ozone, tel que le 1,1-dichloro-1-fluoroéthane.1,1,2-Trichloro-1,2,2-trifluoroethane, known in the art under the designation F113, is widely used in the industry for cleaning and degreasing solid surfaces. It is, however, one of the perhalogenated chlorofluorocarbons (CFCs) suspected of attacking and degrading stratospheric ozone, and will therefore have to be replaced in the short term by substitutes having little or no ozone-destroying effect. , such as 1,1-dichloro-1-fluoroethane.
Ce dernier composé, connu dans le métier sous la désignation F141b, présente comme le F113 l'avantage de former avec le méthanol une composition azéotropique particulièrement utile pour les opérations de nettoyage (brevets EP 325 265, US 4 842 764 et JP 2 273 632).The latter compound, known in the trade under the designation F141b, has, like F113, the advantage of forming with methanol an azeotropic composition which is particularly useful for cleaning operations (patents EP 325 265, US 4 842 764 and JP 2 273 632 ).
Que l'hydrocarbure chlorofluoré associé au méthanol soit le F113 ou le F141b, il est nécessaire de stabiliser la composition azéotropique pour éviter une attaque des métaux par le méthanol conduisant à la formation d'hydrogène. Le nitrométhane est habituellement utilisé pour stabiliser la composition azéotropique F113-méthanol et ce même composé a aussi été proposé dans le brevet US 4 816 174 comme stabilisant de la composition azéotropique F141b-méthanol. Comme autres composés susceptibles d'être utilisés pour stabiliser cette composition azéotropique, le brevet US 4 842 764 mentionne les amines secondaires et tertiaires, les oléfines et cyclooléfines, les oxydes d'alkylène, les sulfoxydes, les sulfones, les nitrites et nitriles, et les alcools ou éthers acétyléniques.Whether the chlorofluorinated hydrocarbon associated with methanol is F113 or F141b, it is necessary to stabilize the azeotropic composition to avoid attack of the metals by methanol leading to the formation of hydrogen. Nitromethane is usually used to stabilize the azeotropic composition F113-methanol and this same compound has also been proposed in US Pat. No. 4,816,174 as a stabilizer for the azeotropic composition F141b-methanol. As other compounds capable of being used to stabilize this azeotropic composition, US Pat. No. 4,842,764 mentions secondary and tertiary amines, olefins and cycloolefins, alkylene oxides, sulfoxides, sulfones, nitrites and nitriles, and acetylenic alcohols or ethers.
Le document JP 2 273 632 précité indique, sans préciser leur rôle, que d'autres constituants peuvent être ajoutés à la composition azéotropique F141b-méthanol et, à ce titre, énumére divers composés incluant des éthers comme le méthylcellosolve, le tétrahydrofurane et le 1,4-dioxane. Ces deux derniers éthers ont par ailleurs été étudiés, en même temps qu'une soixantaine d'autres composés de nature très diverse, comme inhibiteurs de la réaction de l'aluminium avec les solvants chlorés tels que le 1,1-dichloroéthane, le 1,1,1-trichloroéthane, le 1,1,2-trichloroéthane ou le mélange 10/90 toluène/dichlorométhane (W. L.Archer, "Comparaison of chlorinated solvent-aluminiumm reaction inhibitors", Ind. Eng. Chem. Prod. Res. Dev., Vol.18 (2) 1979, 131-135).Document JP 2 273 632 cited above indicates, without specifying their role, that other constituents can be added to the azeotropic composition F141b-methanol and, as such, lists various compounds including ethers such as methylcellosolve, tetrahydrofuran and 1 , 4-dioxane. These last two ethers have also been studied, together with sixty other compounds of very diverse nature, as inhibitors of the reaction of aluminum with chlorinated solvents such as 1,1-dichloroethane, 1 , 1,1-trichloroethane, 1,1,2-trichloroethane or the 10/90 toluene / dichloromethane mixture (WLArcher, "Comparison of chlorinated solvent-aluminumm reaction inhibitors", Ind. Eng. Chem. Prod. Res. Dev. , Vol. 18 (2) 1979, 131-135).
Il a maintenant été trouvé que le diméthoxyméthane et le 1,3-dioxolane sont d'excellents stabilisants des compositions F141b-méthanol. Ils permettent en effet d'inhiber la réaction du méthanol avec les métaux légers tels que l'aluminium et le magnésium (très sensible) et présentent à cet égard un comportement très différent de celui de composés très voisins tels que le diméthoxyéthane, le diéthyléther, le méthyl tert-butyl éther, le furane et le tétrahydrofurane.It has now been found that dimethoxymethane and 1,3-dioxolane are excellent stabilizers of the F141b-methanol compositions. They indeed make it possible to inhibit the reaction of methanol with light metals such as aluminum and magnesium (very sensitive) and exhibit in this respect a behavior very different from that of very similar compounds such as dimethoxyethane, diethyl ether, methyl tert-butyl ether, furan and tetrahydrofuran.
L'invention a donc pour objet une composition de nettoyage à base de F141b et de méthanol, caractérisée en ce qu'elle contient, à titre de stabilisant, de 0,01 à 1 % (de préférence 0,1 à 0,5 %) de diméthoxyméthane ou de 1,3-dioxolane par rapport au poids total de méthanol et de F141b.The subject of the invention is therefore a cleaning composition based on F141b and methanol, characterized in that it contains, as stabilizer, from 0.01 to 1% (preferably 0.1 to 0.5% ) of dimethoxymethane or of 1,3-dioxolane relative to the total weight of methanol and of F141b.
Dans les compositions selon l'invention, la proportion pondérale de méthanol est avantageusement comprise entre 0,2 et 10 % et celle de F141b entre 99,8 et 90 %. Une composition plus particulièrement préférée est celle dans laquelle les proportions respectives de méthanol et de F141b correspondent sensiblement à la composition azéotropique, c'est à dire 3 à 5 % de méthanol et 97 à 95 % de F141b.In the compositions according to the invention, the weight proportion of methanol is advantageously between 0.2 and 10% and that of F141b between 99.8 and 90%. A more particularly preferred composition is that in which the respective proportions of methanol and of F141b correspond substantially to the azeotropic composition, that is to say 3 to 5% of methanol and 97 to 95% of F141b.
Les compositions selon l'invention ne présentent pas de point éclair dans les conditions standard de détermination et peuvent donc être employées sans danger dans les machines habituellement utilisées pour le nettoyage des flux de soudure, le dégraissage de pièces métalliques lourdes ou le nettoyage de pièces mécaniques de haute qualité et de grande précision comme, par exemple, les gyroscopes et le matériel militaire ou aérospatial.The compositions according to the invention do not have a flash point under the standard determination conditions and can therefore be used without danger in the machines usually used for cleaning weld fluxes, degreasing heavy metal parts or cleaning mechanical parts. high quality and high precision such as, for example, gyroscopes and military or aerospace equipment.
Les exemples suivants illustrent l'invention sans la limiter.The following examples illustrate the invention without limiting it.
On prépare une composition selon l'invention en ajoutant 0,2 % en poids (soit 12 g) de 1,3-dioxolane à 5 litres de mélange azéotropique F141b-méthanol (96 % de F141b et 4 % de méthanol), puis on introduit cette composition dans une petite machine de nettoyage BRANSON et la porte au reflux pendant 4 heures pour que le système soit en équilibre.A composition according to the invention is prepared by adding 0.2% by weight (ie 12 g) of 1,3-dioxolane to 5 liters of azeotropic mixture F141b-methanol (96% of F141b and 4% of methanol), then introduce this composition into a small BRANSON cleaning machine and bring it to reflux for 4 hours so that the system is in balance.
On prélève alors un aliquat du retour des condensats et on l'analyse par chromatographie en phase vapeur. L'examen des résultats rapportés dans le tableau suivant montre la présence de 1,3-dioxolane dans la fraction recueillie, ce qui indique que la composition selon l'invention est également stabilisée en phase vapeur.
On répète l'exemple 1 en remplaçant les 12 g de 1,3-dioxolane par 24 g de diméthoxyméthane (0,4 % en poids). Après 4 heures de reflux pour que le système soit en équilibre, l'analyse d'une fraction des retours des condensats par chromatographie en phase gazeuse indique que la phase vapeur est stabilisée.
Dans un ballon de 250 ml, on introduit 100 ml de la composition de l'exemple 1 et 0,25 g de magnésium activé, puis on porte le mélange au reflux. Après une semaine de reflux, l'analyse de la composition ne révèle aucune différence par rapport à la composition initiale, démontrant ainsi l'effet inhibiteur du 1,3-dioxolane sur la réaction du magnésium et du méthanol.100 ml of the composition of Example 1 and 0.25 g of activated magnesium are introduced into a 250 ml flask, then the mixture is brought to reflux. After a week of reflux, the analysis of the composition reveals no difference compared to the initial composition, thus demonstrating the inhibitory effect of 1,3-dioxolane on the reaction of magnesium and methanol.
Il en est de même si l'on remplace le 1,3-dioxolane par la même proportion de diméthoxyméthane.The same is true if the 1,3-dioxolane is replaced by the same proportion of dimethoxymethane.
Au contraire, si l'on remplace le 1,3-dioxolane par la même proportion de méthyl tert-butyléther, de furane, de diéthyléther, de diméthoxyéthane ou de tétrahydrofurane, la réaction entre le magnésium et le méthanol démarre au reflux.On the contrary, if the 1,3-dioxolane is replaced by the same proportion of methyl tert-butyl ether, furan, diethyl ether, dimethoxyethane or tetrahydrofuran, the reaction between magnesium and methanol starts at reflux.
Dans une petite machine de laboratoire mono-cuve équipée d'un générateur d'ultrasons, on introduit 125 ml de la composition de l'exemple 1, puis on porte le liquide à l'ébullition.In a small single-tank laboratory machine equipped with an ultrasonic generator, 125 ml of the composition of Example 1 are introduced, then the liquid is brought to the boil.
Cinq circuits tests normalisés (modèle IPC-B-25), enduits de flux de soudure à base colophane (flux R8F de la Société ALPHAMETAL), recuits à 230°C pendant 30 secondes et refroidis, sont immergés durant 3 minutes dans le liquide à I'ébullition sous ultrasons, puis rincés dans la phase vapeur pendant 3 minutes.Five standardized test circuits (IPC-B-25 model), coated with rosin-based solder flux (R8F flux from the company ALPHAMETAL), annealed at 230 ° C for 30 seconds and cooled, are immersed for 3 minutes in the boiling liquid under ultrasound, then rinsed in the vapor phase for 3 minutes.
Après séchage à l'air, la qualité du nettoyage est évaluée en déterminant le taux de résidu ionique selon la procédure normalisée IPC-TM 650 n°2.3.25 et 2.3.26 et selon la norme MIL-STD-2000. La valeur obtenue, 1,87 µg éq.NaCl/cm², est très inférieure au seuil (2,5 µg éq. NaCl/cm²) toléré dans le domaine de l'électronique.After air drying, the quality of the cleaning is evaluated by determining the ionic residue rate according to the standard procedure IPC-TM 650 n ° 2.3.25 and 2.3.26 and according to the MIL-STD-2000 standard. The value obtained, 1.87 µg eq.NaCl / cm², is much lower than the threshold (2.5 µg eq. NaCl / cm²) tolerated in the field of electronics.
On répète l'exemple 4, mais avec la composition de l'exemple 2 stabilisée au diméthoxyméthane.Example 4 is repeated, but with the composition of Example 2 stabilized with dimethoxymethane.
Le taux de résidu ionique est alors de 1,86 µg éq. NaCl/cm².The rate of ionic residue is then 1.86 μg eq. NaCl / cm².
Claims (5)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR9300781 | 1993-01-27 | ||
FR9300781A FR2700776A1 (en) | 1993-01-27 | 1993-01-27 | Stabilized cleaning composition based on 1,1-dichloro-1-fluoroethane and methanol. |
Publications (2)
Publication Number | Publication Date |
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EP0609125A1 true EP0609125A1 (en) | 1994-08-03 |
EP0609125B1 EP0609125B1 (en) | 1999-05-12 |
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EP94400141A Expired - Lifetime EP0609125B1 (en) | 1993-01-27 | 1994-01-24 | Stabilized cleaning composition based on 1,1-dichloro-1-fluoroethane and methanol |
Country Status (6)
Country | Link |
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EP (1) | EP0609125B1 (en) |
JP (1) | JP2510951B2 (en) |
KR (1) | KR960006562B1 (en) |
ES (1) | ES2133502T3 (en) |
FR (1) | FR2700776A1 (en) |
TW (1) | TW336956B (en) |
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CA2248265A1 (en) * | 1996-03-04 | 1997-09-12 | Burnell Lee | Stabilized brominated alkane solvent |
IT201900024901A1 (en) | 2019-12-19 | 2021-06-19 | Clean Consult Int S P A | Cleaning composition of dimethoxymethane and dioxolane |
Citations (11)
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EP0325265A1 (en) * | 1988-01-20 | 1989-07-26 | E.I. Du Pont De Nemours And Company | Azeotropic compositions of 1,1-Dichloro-1-Fluoroethane and Methanol/Ethanol |
WO1989010984A1 (en) * | 1988-05-03 | 1989-11-16 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane and methanol |
WO1991013144A1 (en) * | 1990-03-02 | 1991-09-05 | Allied-Signal Inc. | A method of cleaning using azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane |
WO1991013969A1 (en) * | 1990-03-13 | 1991-09-19 | E.I. Du Pont De Nemours And Company | Stabilized constant-boiling, azeotrope or azeotrope-like compositions of dichlorotrifluoroethane; 1,1-dichloro-1-fluoroethane; with methanol and/or ethanol |
US5124063A (en) * | 1990-12-20 | 1992-06-23 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; methanol; and alkane having 5 or 6 carbon atoms |
WO1992010453A1 (en) * | 1990-12-14 | 1992-06-25 | Allied-Signal Inc. | Stabilized 1,1-dichloro-1-fluoroethane |
US5137651A (en) * | 1990-12-19 | 1992-08-11 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, 1,2-dichloroethylene, and optionally methanol or ethanol |
JPH05155791A (en) * | 1991-12-04 | 1993-06-22 | Central Glass Co Ltd | Method for stabilizing azeotrope-like composition |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02273632A (en) * | 1989-04-14 | 1990-11-08 | Asahi Glass Co Ltd | Fluorinated hydrocarbon-based azeotropic mixture |
-
1993
- 1993-01-27 FR FR9300781A patent/FR2700776A1/en active Pending
-
1994
- 1994-01-21 TW TW083100500A patent/TW336956B/en active
- 1994-01-24 ES ES94400141T patent/ES2133502T3/en not_active Expired - Lifetime
- 1994-01-24 EP EP94400141A patent/EP0609125B1/en not_active Expired - Lifetime
- 1994-01-24 KR KR1019940001216A patent/KR960006562B1/en not_active IP Right Cessation
- 1994-01-27 JP JP6007542A patent/JP2510951B2/en not_active Expired - Fee Related
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US4016215A (en) * | 1970-08-21 | 1977-04-05 | Toyo Soda Manufacturing Co., Ltd. | Stabilization of 1,1,1-trichloroethane |
EP0325265A1 (en) * | 1988-01-20 | 1989-07-26 | E.I. Du Pont De Nemours And Company | Azeotropic compositions of 1,1-Dichloro-1-Fluoroethane and Methanol/Ethanol |
US4816174A (en) * | 1988-05-03 | 1989-03-28 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane |
US4842764A (en) * | 1988-05-03 | 1989-06-27 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane and methanol |
WO1989010984A1 (en) * | 1988-05-03 | 1989-11-16 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane and methanol |
WO1991013144A1 (en) * | 1990-03-02 | 1991-09-05 | Allied-Signal Inc. | A method of cleaning using azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane |
WO1991013969A1 (en) * | 1990-03-13 | 1991-09-19 | E.I. Du Pont De Nemours And Company | Stabilized constant-boiling, azeotrope or azeotrope-like compositions of dichlorotrifluoroethane; 1,1-dichloro-1-fluoroethane; with methanol and/or ethanol |
WO1992010453A1 (en) * | 1990-12-14 | 1992-06-25 | Allied-Signal Inc. | Stabilized 1,1-dichloro-1-fluoroethane |
US5137651A (en) * | 1990-12-19 | 1992-08-11 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, 1,2-dichloroethylene, and optionally methanol or ethanol |
US5124063A (en) * | 1990-12-20 | 1992-06-23 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; methanol; and alkane having 5 or 6 carbon atoms |
JPH05155791A (en) * | 1991-12-04 | 1993-06-22 | Central Glass Co Ltd | Method for stabilizing azeotrope-like composition |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Derwent World Patents Index; AN 93-232280 * |
Also Published As
Publication number | Publication date |
---|---|
KR960006562B1 (en) | 1996-05-17 |
TW336956B (en) | 1998-07-21 |
JPH06256796A (en) | 1994-09-13 |
FR2700776A1 (en) | 1994-07-29 |
KR940018459A (en) | 1994-08-18 |
EP0609125B1 (en) | 1999-05-12 |
JP2510951B2 (en) | 1996-06-26 |
ES2133502T3 (en) | 1999-09-16 |
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