EP0217181A2 - Azeotropähnliche Zusammensetzungen von Trichlorfluoräthan, Methanol, Nitromethan, Hexan und Azeton - Google Patents
Azeotropähnliche Zusammensetzungen von Trichlorfluoräthan, Methanol, Nitromethan, Hexan und Azeton Download PDFInfo
- Publication number
- EP0217181A2 EP0217181A2 EP86112426A EP86112426A EP0217181A2 EP 0217181 A2 EP0217181 A2 EP 0217181A2 EP 86112426 A EP86112426 A EP 86112426A EP 86112426 A EP86112426 A EP 86112426A EP 0217181 A2 EP0217181 A2 EP 0217181A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- azeotrope
- weight percent
- hexane
- nitromethane
- compositions
- 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.)
- Withdrawn
Links
Classifications
-
- 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
-
- 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
- C23G5/02809—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
- C23G5/02812—Perhalogenated hydrocarbons
- C23G5/02816—Ethanes
- C23G5/02819—C2Cl3F3
Definitions
- This invention relates to azeotrope-like mixtures of trichlorotrifluoroethane, methanol, nitromethane, hexane and, optionally, acetone. These mixtures are useful as vapor degreasing agents and as solvents to remove rosin fluxes from printed circuit boards.
- Fluorocarbon solvents such as trichlorotrifluoroethane
- Trichlorotrifluoroethane have attained widespread use in recent years as effective, nontoxic, and nonflammable agents useful in degreasing applications.
- Trichlorotrifluoroethane in particular has been found to have satisfactory solvent power for greases, oils, waxes and the like.
- Trichlorotrifluoroethane also finds wide use in removing solder fluxes from printed wiring boards and printed wiring assemblies in the electronics industry.
- Such circuit boards normally consist of a glass fiber reinforced plate of electrically resistant plastic having electrical circuit traces on one or both sides thereof.
- the circuit traces are thin flat strips of conductive metal, usually copper, which serve to interconnect the electronic components attached to the printed wiring board. The electrical integrity of the contacts between the circuit traces and the components is assured by soldering.
- soldering circuit boards involve coating the entire circuit side of the board with a flux and thereafter passing the coated side of the board through molten solder.
- the flux cleans the conductive metal parts and promotes a reliable intermetallic bond between component leads and circuit traces and lands on the printed wiring board.
- the preferred fluxes consist, for the most part, of rosin used alone or with activating additives such as dimethylamine hydrochloride, trimethylamine hydrochloride, or an oxalic acid derivative.
- the flux is removed from the board by means of an organic solvent.
- Trichlorotrifluoroethane being non-polar, adequately cleans rosin fluxes; however, it does not easily remove polar contaminants such as the activating additives.
- trichlorotrifluoroethane has been mixed with polar components such as aliphatic alcohols or chlorocarbons such as methylene chloride.
- polar components such as aliphatic alcohols or chlorocarbons such as methylene chloride.
- U.S. Patent No. 2,999,816 discloses the use of mixtures of 1,1,2-trichloro-1,2,2-trifluoroethane and methanol as defluxing solvents.
- azeotropic compositions including the desired fluorocarbon components, such as trichlorotrifluoroethane, which include components which contribute additionally desired characteristics, such as polar functionality, increased solvency power, and stability.
- Azeotropic compositions are desired because they exhibit a minimum boiling point and do not fractionate upon boiling. This is desirable because in vapor degreasing equipment with which these solvents are employed, redistilled material is generated for final rinse-cleaning. Thus, the vapor degreasing system acts as a still.
- solvent composition exhibits a constant boiling point, i.e., is an azeotrope or is azeotrope-like, fractionation will occur and undesirable solvent distribution may act to upset the cleaning and safety of processing.
- Preferential evaporation of the more volatile components of the solvent mixtures which would be the case if they were not azeotrope or azeotrope-like, would result in mixtures with changed compositions which may have less desirable properties, such as lower solvency for rosin fluxes, less inertness towards the electrical components soldered on the printed circuit board, and increased flammability.
- 3,960,746 discloses azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, and nitromethane;
- Japanese Pat. Nos. 81-34,798 and 81-34,799 disclose azeotropes of l,l,2-trichloro-l,2,2-trifluoroethane, ethanol, nitromethane and 2,2-dimethylbutane or 2,3-dimethylbutane or 3-methylpentane; and Japanese Pat. No.
- 81,109,298 discloses an azeotrope of 1,1,2-trichloro-1,2,2-trifluoroethane, ethanol, n-hexane and nitromethane;
- U.S. Pat. No. 4,045,366 discloses the ternary azeotrope of 1,1,2-trichloro-1,2,2-trifluoroethane, nitromethane and acetone;
- Japanese Pat. No. 73-7,333,878 discloses the ternary azeotrope of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol and acetone;
- 4,279,664 discloses the ternary azeotrope of 1,1,2-tric hloro-1,2,2-trifluoroethane, acetone and hexane
- U.S. Pat. No. 4,476,306 discloses the azeotrope of 1,1,2-trichloro-1,2,2-trifluoroethane, acetone, hexane and nitromethane.
- Another object of the invention is to provide novel constant boiling or essentially constant boiling solvents which are liquid at room temperature, will not fractionate under conditions of use and also have the foregoing advantages.
- a further object is to provide azeotrope-like compositions which are relatively nontoxic and nonflammable both in the liquid phase and the vapor phase.
- novel azeotrope-like compositions comprising trichlorotrifluoroethane, methanol, nitromethane, hexane and, optionally, acetone, with 1,1,2-trichloro-1,2,2-trifluoroethane being the trichlorotrifluoroethane of choice.
- the azeotrope-like compositions comprise from about 86.5 to about 93.5 weight percent of 1,1,2-trichloro-1,2,2-trifluoroethane, from about 5.0 to about 6.2 weight percent of methanol, from about 0.03 to about 0.6 weight percent of nitromethane, from about 0.3 to about 6.0 weight percent of hexane and from about 0.6 to 4.5 weight percent acetone.
- the azeotrope-like compositions comprise from about 91.0 to about 91.6 weight percent of 1,1,2-tric hloro-1,2,2-trifluoroethane, from about 5.6 to about 6.1 weight percent of methanol, from about 0.05 to about 0.3 weight percent of nitromethane, from about 0.3 to about 4.1 weight percent of hexane and from about 0.6 to about 4.2 weight percent acetone.
- the most preferred embodiment of the invention without acetone comprises from about 90.2 to about 91.6 weight percent of 1,1,2-trichloro-1,2,2-trifluoroethane, from about 5.7 to about 6.0 weight percent of methanol, from about 0.05 to about 0.2 weight percent of nitromethane, from about 1.6 to about 2.1 weight percent of hexane and from about 0.6 to 2.1 weight percent acetone.
- Such compositions possess constant or essentially constant boiling points of about 39.8°C at 760 mm Hg.
- the azeotrope-like compositions comprise from about 84.3 to about 93.8 weight percent of 1,1,2-trichloro-l,2,2-trifluoroethane, from about 5.6 to about 6.6 weight percent of methanol, from about 0.05 to about 0.8 weight percent of nitromethane, and from about 0.1 to about 8.7 weight percent of hexane.
- the azeotrope-like compositions comprise from about 91.2 to about 93.8 weight percent of 1,1,2-trichloro-l,2,2-trifluoroethane, from about 5.8 to about 6.2 weight percent of methanol, from about 0.05 to about 0.4 weight percent of nitromethane, and from about U.1 to about 2.4 weight percent of hexane.
- the most preferred embodiment of the invention with acetone comprises from about 91.3 to about 92.0 weight percent of 1,1,2-trichloro-1,2,2-trifluoroethane, from about 6.0 to about 6.2 weight percent of methanol, from about 0.2 to about 0.4 weight percent of nitromethane, and from about 1.8 to about 2.0 weight percent of hexane.
- Such compositions possess constant or essentially constant boiling points of about 39.6°C at 760 mm Hg.
- compositions within the above-indicated ranges, as well as certain compositions outside the indicated ranges, are azeotrope-like, as defined more particularly below.
- these azeotrope-like compositions are stable, safe to use and that the preferred compositions of the invention are nonflammable (exhibit no flash point when tested by the Tag Open Cup test method - ASTM D 1310 or ASTM Dl 310-16) and exhibit excellent solvency power.
- These compositions have been found to be particularly effective when employed in conventional degreasing units for the dissolution of rosin fluxes and the cleaning of such fluxes from printed circuit boards.
- azeotrope-like composition is intended to mean that the composition behaves like a true azeotrope in terms of its constant boiling characteristics or tendency not to fractionate upon boiling or evaporation. Such composition may or may not be a true azeotrope.
- the composition of the vapor formed during boiling or evaporation is identical or substantially identical to the original liquid composition.
- the liquid composition if it changes at all, changes only to a minimal or negligible extent. This is to be contrasted to non- azeotrope-like compositions in which during boiling or evaporation, the liquid composition changes to a substantial degree.
- azeotrope-like compositions As is well known in this art, another characteristic of azeotrope-like compositions is that there is a range of compositions containing the same components in varying proportions which are azeotrope-like. All such compositions are intended to be covered by the term azeotrope-like as used herein. As an example, it is well known that at differing pressures, the composition of a given azeotrope will vary at least slightly and changes in distillation pressures also change, at least slightly, the distillation temperatures. Thus, an azeotrope of A and B represents a unique type of relationship but with a variable composition depending on temperature and/or pressure.
- 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, acetone, and hexane components of the novel solvent azeotrope-like compositions of the invention are all commercially available.
- a suitable grade of 1,1,2-trichloro-1,2,2-trifluoroethane, for example, is sold by Allied Corporation under the trade name "GENESOLV® D".
- hexane is used herein as to mean any C 6 paraffin hydrocarbon (C6H14) (seehackh's Chemical Dictionary, 3 rd E d., McGraw Hill Book Co. (1944) p. 408).
- hexane includes n-hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane and any and all mixtures thereof.
- 2-Methylpentane is commonly referred to as isohexane.
- isohexane which is a mixture of isohexane with other hexane isomers, typically containing at least about 35 weight percent isohexane and usually from about 40-45 weight percent isohexane. It has been found that each hexane isomer, separately and in combination with other hexane isomers, form azeotrope-like compositions with 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, and nitromethane in accordance with the invention.
- the azeotrope-like compositions of the invention were determined through the use of distillation techniques designed to provide higher rectification of the distillate than found in the most demanding vapor degreaser systems. For this purpose a five theoretical plate Oldershaw distillation column was used with a cold water condensed, manual liquid dividing head. Typically, approximately 350 cc of liquid were charged to the distillation pot.
- the liquid was a mixture comprised of various combinations of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and hexane, with and without acetone. The mixture was heated at total reflux for about one hour to ensure equilibration.
- the distillate was obtained using a 5:1 reflux ratio at a boil-up rate of 250-300 grams per hr. Approximately 150 cc of product were distilled and 5 approximately equivalent sized overhead cuts were collected. The vapor temperature (of the distillate), pot temperature, and barometric pressure were monitored, A constant boiling fraction was collected and analyzed by gas chromatography to determine the weight percentages of its components.
- FC-113 1,1,2-trichloro-1,2,2-trifluoroethane
- FC-113 1,1,2-trichloro-1,2,2-trifluoroethane
- FC-113 1,1,2-trichioro-1,2,1-trifluoroethane
- acetone 1,1,2-trichioro-1,2,1-trifluoroethane
- each hexane isomer exhibits its own unique compositional identity in azeotrope-like mixtures with 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and optionally acetone and that each hexane isomer and mixtures thereof form azeotrope-like constant boiling mixtures at about 39.8 ⁇ 0.3°C with such components including acetone and form azeotrope-like constant boiling mixtures of about 39.6 ⁇ 05°C with such components without acetone.
- the hexane isomers and their boiling points are shown in the following Table II.
- constant boiling or essentially constant boiling for the purposes of this invention means constant boiling or essentially constant boiling in the environment of a vapor degreaser system such as utilized in the art. All such mixtures in accordance with the invention which are constant boiling or essentially constant boiling are "azeotrope-like" within the meaning of this invention.
- a vapor phase degreasing machine was charged with preferred azeotrope-like mixtures in accordance with the invention comprising about 91.1 weight percent 1,1,2-trichloro- l,2,2-trifluoroethane (FC-113), about 5.8 weight percent methanol, about 1.0 weight percent acetone, about 2.0 weight percent commercial grade isohexane and about 0.1 weight percent nitromethane.
- FC-113 1,1,2-trichloro- l,2,2-trifluoroethane
- the solvent charge was brought to reflux and the individual sump compositions were determined with a Hewlett Packard 5890 Gas Chromatograph. Refluxing was continued for 63 hours and sump compositions were monitored throughout this time. A mixture was considered constant boiling or non-segregating if the maximum concentration difference between sumps for any mixture component was less than 0.3%.
- compositions of this invention will not segregate in a commercial vapor degreaser, thereby avoiding potential safety, performance, and handling problems.
- the preferred composition tested was also found to not have a flash point according to recommended procedures ASTM D-56 (Tag Closed Cup) and ASTM D-1310 (Tag Open Cup).
- a vapor phase degreasing machine was charged with preferred azeotrope-like mixtures in accordance with the invention, comprising about 92.0 weight percent 1,1,2-trichloro-1,2,2-trifluoroethane (FC-113), about 5.8 weight percent methanol, about 1.9 weight percent isohexane (commercial grade), and about 0.3 weight percent nitromethane.
- FC-113 1,1,2-trichloro-1,2,2-trifluoroethane
- methanol methanol
- isohexane commercial grade
- nitromethane commercial grade
- the vapor phase degreasing machine utilized was a small water-cooled, three-sump vapor phase degreaser with an attached still, which represents a type of system configuration comparable to machine types in the field today which would present the most rigorous test of solvent segregating behavior.
- the degreaser employed to demonstrate the invention contains two overflowing rinse-sumps and a boil-sump.
- the boil-sump and the still are electrically heated, and each contains a low-level, shut-off switch.
- Solvent vapors in both the degreaser ana the still are condensed on water-cooled, stainless-steel coils.
- the still is fed by gravity from the boil-sump. Condensate from the still is returned to the first rinse-sump, also by gravity.
- the capacity of the unit is approximately 3.5 gallons.
- This degreaser is very similar to Baron-Blakeslee 2 LLV 3-sump degreasers with an attached still which are quite commonly used in commercial
- the solvent charge was brought to reflux and the compositions in the rinse sump containing the clear condensate from the still, the work sump containing the overflow from the rinse sump, the boil sump where the overflow from the work sump is brought to the mixture boiling point, and the still were determined with a Perkin Elmer Sigma 3 gas chromatograph.
- the temperature of the liquid in the boil sump and still was monitored with a thermocouple temperature sensing device accurate to ⁇ 0.2°C. Refluxing was continued for 48 hours and sump compositions were monitored throughout this time.
- a mixture was considered constant boiling or non-segregating if the maximum concentration difference between sumps for any mixture component was ⁇ 2 sigma around the mean value.
- Sigma is a standard deviation unit and it is our experience from many observations of vapor degreaser performance that commercial "azeotrope-like" vapor phase degreasing solvents exhibit at least a ⁇ 2 sigma variation in composition with time and yet proauce very satistactory non-segregating cleaning behavior.
- the mean value refers to the average of a component composition in each sump over the time period after refluxing has started, where the zero time, or initial concentration, is not considered in the calculation since the dynamic system is not at a steady- state condition.
- compositions of this invention will not segregate in any types of large-scale commercial vapor degreasers, thereby avoiding potential safety, performance, and handling problems.
- the preferred composition tested was also found to not have a flash point according to recommended procedures ASTM D-56 (Tag Closed Cup) and ASTM D-1310 (Tag Open Cup).
- This example illustrates the use of the preferred azeotrope-like composition of the invention to clear (deflux) printed wiring boards and printed wiring assemblies.
- the fluxes were Alpha 611F (manufactured by Alpha Metals Inc.), Kester 1585-MIL (manufactured by Kester Solder), and Kenco 885 (manufactured by Kenco Industries Inc.).
- Predesigned printed wiring boards were fluxed in a Hollis lU-inch TDL wave solder machine.
- Alpha 611F and Kester 1585-MIL fluxes altogether twelve such test boards were prepared for defluxing. Of these, six contained electronic components soldered to the board and the other six did not have any components on the board.
- Kenco 885 eight boards were run; four with components and the other four without any components.
- the printed wiring assemblies with electronic components were high density boards each having a one sided surface area of 18.97 square inches and containing two 36 pin dual in line packages (DIP), two 24 pin DIP's, five 16 pin DIP's and forty-one discrete components (resistors and capacitors).
- Refrigerated cooling coils line the upper wall of the apparatus to maintain a vapor blanket.
- the cleaning schedule employed to demonstrate the usefulness of this invention was as follows: (i) two (2) minute exposure to the vapors over the boil sump, (ii) half a minute full immersion in the cold sump, (iii) half a minute re-exposure to the vapors over the boil sump.
- the azeotrope-like compositions used to illustrate the usefulness of the invention to deflux printed wiring boards were comprised of: (a) about 90.9 weight percent of 1,1,2-trichloro-1,2,2-trifluoroethane, about 5.9 weight percent of methanol, about 2.1 weight percent of pure (99%) isohexane, about 0.1 weight percent of nitromethane and about 1.0 weight percent acetone; and (b) about 93.0 weight percent of 1,1,2-trichloro-1,2,2-trifluoroethane, about 6.2 weight percent of methanol, about 0.7 weight percent of pure (99%) isohexane, and about 0.1 weight percent of nitromethane.
- the cleaning performance of this invention was also compared to that of two commercial defluxing solvents, Genesolv 8 DMS and Freon® TMS, where both commercial solvents consist of azeotrope-like compositions of trichlorotrifluoroethane, primary alcohol(s), and nitromethane.
- Genesolv . DMS is a blend of 92.0 weight percent trichlorotrifluoroethane, 4.0 weight percent of methanol, 2.0 weight percent of ethanol, 1.0 weight percent of isopropyl alcohol, and 1.0 weight percent of nitromethane. Freon.
- TMS is a blend of 94.05 weight percent of trichlorotrifluoroethane, 5.7 weight percent of methanol, and 0.25 weight percent of nitromethane.
- the following table summarizes the residual ionic contamination left on fluxed printed circuit boards cleaned by the above composition of this invention, Genesolv® DMS and Freon® TMS.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacturing Of Printed Wiring (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US782776 | 1985-10-02 | ||
US06/782,776 US4655956A (en) | 1985-10-02 | 1985-10-02 | Azeotrope-like compositions of trichlorotrifluoroethane, methanol, nitromethane and hexane |
US06/786,565 US4654160A (en) | 1985-10-11 | 1985-10-11 | Azeotrope-like compositions of trichlorotrifluoroethane, methanol, acetone, nitromethane and hexane |
US786565 | 1985-10-11 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19920101225 Division EP0490873A3 (de) | 1985-10-02 | 1986-09-08 | Azeopeotropähnliche Zusammensetzungen von Trichlortrifluoräther, Methanol, Nitromethan and Hexan |
EP92101225.8 Division-Into | 1986-09-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0217181A2 true EP0217181A2 (de) | 1987-04-08 |
EP0217181A3 EP0217181A3 (de) | 1988-08-31 |
Family
ID=27120044
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86112426A Withdrawn EP0217181A3 (de) | 1985-10-02 | 1986-09-08 | Azeotropähnliche Zusammensetzungen von Trichlorfluoräthan, Methanol, Nitromethan, Hexan und Azeton |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0217181A3 (de) |
KR (1) | KR890004173B1 (de) |
AU (1) | AU590334B2 (de) |
MX (1) | MX166646B (de) |
MY (1) | MY101172A (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988009833A1 (en) * | 1987-06-04 | 1988-12-15 | Allied-Signal Inc. | Azeotrope-like compositions of trichlorotrifluoroethane methanol, nitromethane and acetone |
EP0323616A1 (de) * | 1987-12-26 | 1989-07-12 | Daikin Industries, Limited | Unbrennbare azeotropähnliche Lösungsmittelzusammensetzungen |
EP0334384A1 (de) * | 1988-03-25 | 1989-09-27 | Daikin Industries, Limited | Unbrennbare azeotrop-ähnliche Lösungsmittelgemische |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4767561A (en) * | 1987-09-23 | 1988-08-30 | E. I. Du Pont De Nemours And Company | Azeotrope or azeotrope-like composition of trichlorotrifluoroethane, methanol and 1,2-dichloroethylene |
ATE87983T1 (de) * | 1988-02-02 | 1993-04-15 | Du Pont | Azeotrope oder azeotropaehnliche stabilisierte zusammensetzung von 1,1,2-trichlor-1,2,2trifluorethan, methanol und 1,2-dichloroethylen. |
US4804493A (en) * | 1988-05-24 | 1989-02-14 | E. I. Du Pont De Nemours And Company | Stabilized azeotrope or azeotrope-like composition of 1,1,2-trichloro-1,2,2-trifluoroethane and trans-1,2-dichloroethylene |
KR101620958B1 (ko) | 2014-06-10 | 2016-05-24 | 주식회사 뉴텍 | 펠렛연소실이 구비된 관류형 보일러 제작 방법 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2279439A1 (fr) * | 1974-07-25 | 1976-02-20 | Du Pont | Compositions a base de methanol, de nitromethane et de trichlorotrifluoroethane analogues a des azeotropes |
JPS5634799A (en) * | 1979-08-29 | 1981-04-07 | Daikin Ind Ltd | Azeotropic mixed solvent composition |
JPS5634798A (en) * | 1979-08-29 | 1981-04-07 | Daikin Ind Ltd | Azeotropic mixed solvent composition |
GB2066840A (en) * | 1979-12-26 | 1981-07-15 | Daikin Ind Ltd | Solvent Mixture for Cleaning |
JPS56109298A (en) * | 1980-01-31 | 1981-08-29 | Daikin Ind Ltd | Azeotropic solvent composition |
EP0160854A1 (de) * | 1984-04-26 | 1985-11-13 | AlliedSignal Inc. | Azeotropähnliche Zusammensetzungen aus Trichlortrifluoräthan, Aceton, Nitromethan und Hexan |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4279664A (en) * | 1980-04-09 | 1981-07-21 | Allied Chemical Corporation | Azeotrope-like compositions of trichlorotrifluoroethane, acetone and n-hexane |
DE3361818D1 (en) * | 1982-03-18 | 1986-02-27 | Ici Plc | Cleaning compositions |
US4476036A (en) * | 1983-09-12 | 1984-10-09 | Allied Corporation | Quaternary 1,1,2-trichloro-1,2,2-trifluoro azeotropic cleaning composition |
-
1986
- 1986-09-08 EP EP86112426A patent/EP0217181A3/de not_active Withdrawn
- 1986-09-29 KR KR1019860008137A patent/KR890004173B1/ko not_active IP Right Cessation
- 1986-10-01 MX MX003903A patent/MX166646B/es unknown
- 1986-10-01 AU AU63464/86A patent/AU590334B2/en not_active Ceased
-
1987
- 1987-03-21 MY MYPI87000350A patent/MY101172A/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2279439A1 (fr) * | 1974-07-25 | 1976-02-20 | Du Pont | Compositions a base de methanol, de nitromethane et de trichlorotrifluoroethane analogues a des azeotropes |
JPS5634799A (en) * | 1979-08-29 | 1981-04-07 | Daikin Ind Ltd | Azeotropic mixed solvent composition |
JPS5634798A (en) * | 1979-08-29 | 1981-04-07 | Daikin Ind Ltd | Azeotropic mixed solvent composition |
GB2066840A (en) * | 1979-12-26 | 1981-07-15 | Daikin Ind Ltd | Solvent Mixture for Cleaning |
JPS56109298A (en) * | 1980-01-31 | 1981-08-29 | Daikin Ind Ltd | Azeotropic solvent composition |
EP0160854A1 (de) * | 1984-04-26 | 1985-11-13 | AlliedSignal Inc. | Azeotropähnliche Zusammensetzungen aus Trichlortrifluoräthan, Aceton, Nitromethan und Hexan |
Non-Patent Citations (3)
Title |
---|
CHEMICAL ABSTRACTS, vol. 95, no. 12, 21st September 1981, page 102, no. 99708h, Columbus, Ohio, US; & JP-A-81 34 799 (DAIKIN KOGYO CO., LTD.) 07-04-1981 * |
CHEMICAL ABSTRACTS, vol. 95, no. 12, 21st September 1981, page 102, no. 99709j, Columbus, Ohio, US; & JP-A-81 34 798 (DAIKIN KOGYO CO., LTD.) 07-04-1981 * |
CHEMICAL ABSTRACTS, vol. 96, no. 2, 11th January 1982, page 115, no. 8533d, Columbus, Ohio, US; & JP-A-81 109 298 (DAIKIN KOGYO CO., LTD.) 29-08-1981 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988009833A1 (en) * | 1987-06-04 | 1988-12-15 | Allied-Signal Inc. | Azeotrope-like compositions of trichlorotrifluoroethane methanol, nitromethane and acetone |
EP0323616A1 (de) * | 1987-12-26 | 1989-07-12 | Daikin Industries, Limited | Unbrennbare azeotropähnliche Lösungsmittelzusammensetzungen |
US5047176A (en) * | 1987-12-26 | 1991-09-10 | Daikin Industries, Ltd. | Incombustible azeotropic like solvent compositions |
EP0334384A1 (de) * | 1988-03-25 | 1989-09-27 | Daikin Industries, Limited | Unbrennbare azeotrop-ähnliche Lösungsmittelgemische |
Also Published As
Publication number | Publication date |
---|---|
AU6346486A (en) | 1987-04-09 |
KR890004173B1 (ko) | 1989-10-23 |
MX166646B (es) | 1993-01-26 |
MY101172A (en) | 1991-07-31 |
EP0217181A3 (de) | 1988-08-31 |
AU590334B2 (en) | 1989-11-02 |
KR870004169A (ko) | 1987-05-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5246617A (en) | Azeotropic compositions of 1,1-dichloro-1-fluoroethane and methanol/ethanol | |
EP0183110B1 (de) | Azeotrop-ähnliche Zusammensetzungen von Trichlortrifluoräthan, Äthanol, Aceton, Nitromethan und Hexan | |
US4816176A (en) | Azeotrope-like compositions of dichlorotrifluoroethane, methanol and nitromethane | |
US4654160A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, methanol, acetone, nitromethane and hexane | |
US4655956A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, methanol, nitromethane and hexane | |
EP0183109B1 (de) | Azeotrop-ähnliche Zusammensetzungen von Trichlortrifluoräthan, Äthanol, Nitromethan und 2-Methylpentan oder einer Mischung von Hexanen | |
US4816175A (en) | Azeotrope-like compositions of dichlorotrifluoroethane, methanol, cyclopentane and nitromethane | |
EP0217181A2 (de) | Azeotropähnliche Zusammensetzungen von Trichlorfluoräthan, Methanol, Nitromethan, Hexan und Azeton | |
EP0414804B1 (de) | Azeotropähnliche zusammensetzungen von 1,1-dichloro-1-fluoroethan, methanol und nitromethan | |
US4683075A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, methanol, nitromethane, acetone, and methyl acetate | |
US6010997A (en) | Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol | |
EP0160854B1 (de) | Azeotropähnliche Zusammensetzungen aus Trichlortrifluoräthan, Aceton, Nitromethan und Hexan | |
US4045366A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, nitromethane and acetone | |
US4062794A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, methanol, ethanol, isopropanol and nitromethane | |
CA1073312A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, ethanol, isopropanol and nitromethane | |
EP0429451B1 (de) | Azeotropähnliche bestandteile von dichlortrifluoräthan, methanol und nitromethan | |
US4045365A (en) | Azeotrope-like compositions of trichloro-trifluoroethane, acetonitrile and acetone | |
US4973362A (en) | Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene and hexane | |
US5085797A (en) | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, a monochlorinated C3 alkane and optionally an alkanol | |
US4873015A (en) | Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and dimethoxymethane | |
US4904407A (en) | Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene and 1-chloropropane | |
US4790955A (en) | Azeotrope-like compositions of trichlorotrifluoroethane, acetone, nitromethane and hexane | |
US4965011A (en) | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, dichlorotrifluoroethane, and nitromethane | |
US5064558A (en) | Azeotrope-like compositions of 1,1,2-tri-chloro-1,2,2-trifluoroethane, 1,2-dichloroethylene, cyclopentane, methanol, nitromethane and optionally diisopropylamine | |
WO1988009833A1 (en) | Azeotrope-like compositions of trichlorotrifluoroethane methanol, nitromethane and acetone |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): CH DE FR GB IT LI SE |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): CH DE FR GB IT LI SE |
|
17P | Request for examination filed |
Effective date: 19881219 |
|
17Q | First examination report despatched |
Effective date: 19891221 |
|
RTI1 | Title (correction) | ||
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: ALLIED-SIGNAL INC. (A DELAWARE CORPORATION) |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 19920915 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: BONNER, JOHN KIRKWOODC/O ALLIED CORP. Inventor name: LUND, EARL A. E.C/O ALLIED CORP. Inventor name: BASU, RAJAT SUBHRAC/O ALLIED CORP. Inventor name: WILSON, DAVID PAULC/O ALLIED CORP. Inventor name: PHAM, HANG THANHC/O ALLIED CORP. |