IE64735B1 - An azeotropic mixture with a low boiling point based on fluoroalkanes - Google Patents
An azeotropic mixture with a low boiling point based on fluoroalkanesInfo
- Publication number
- IE64735B1 IE64735B1 IE404990A IE404990A IE64735B1 IE 64735 B1 IE64735 B1 IE 64735B1 IE 404990 A IE404990 A IE 404990A IE 404990 A IE404990 A IE 404990A IE 64735 B1 IE64735 B1 IE 64735B1
- Authority
- IE
- Ireland
- Prior art keywords
- azeotrope
- boiling point
- employed
- perfluoropropane
- low boiling
- Prior art date
Links
- 238000009835 boiling Methods 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims abstract description 25
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229960004065 perflutren Drugs 0.000 claims abstract description 7
- 239000012530 fluid Substances 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 3
- 239000002984 plastic foam Substances 0.000 claims abstract description 3
- 239000003380 propellant Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 description 6
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- MEXUFEQDCXZEON-UHFFFAOYSA-N bromochlorodifluoromethane Chemical compound FC(F)(Cl)Br MEXUFEQDCXZEON-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004781 supercooling Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0028—Liquid extinguishing substances
- A62D1/0057—Polyhaloalkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2207/00—Foams characterised by their intended use
- C08J2207/04—Aerosol, e.g. polyurethane foam spray
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/128—Perfluorinated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/32—The mixture being azeotropic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Business, Economics & Management (AREA)
- Thermal Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Emergency Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fire-Extinguishing Compositions (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Detergent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
An azeotrope of minimum boiling point, capable of being employed as refrigerating fluid replacing chlorofluorocarbons or as an extinguishing agent replacing bromofluorocarbons and chlorobromofluorocarbons. The azeotrope according to the invention is a mixture of 1,1,1,2-tetrafluoroethane and perfluoropropane. At normal boiling point (approximately -41.1 DEG C at 1.013 bar) its perfluoropropane content is approximately 76 mass% and that of 1,1,1,2-tetrafluoroethane is 24 %. This azeotrope can also be employed as an aerosol propellant or as a blowing agent for plastic foams.
Description
The present invention relates to a mixture of fluoroalkanes with a low boiling point, vhich has little or no effect on the environment and is capable of being employed to replace chlorofluorocarbons (CFCs) in lowtemperature compression refrigeration systems and to replace trifluorobromomethane and difluorochlorobromomethane as extinguishing agent.
It is now established that because of their effect on ozone, CFCs will have, in the longer or shorter term, to be replaced with refrigerating fluids containing less chlorine which are, consequently, less aggressive towards the environment. Bearing in mind its very small effect on the environment, 1,1,1,2-tetrafluoroethane (R 134a) has already been proposed as a substitute for CFCs. However, because of its high boiling point (-26.5°C), the use of R 134a by itself is restricted to intermediate evaporation temperature.applications (-25°C; -26°C) and cannot be used in low boiling temperature applications (for example -40°C). In fact, the minimum temperature reached in the evaporator is in practice limited by the normal boiling temperature of the refrigerating fluid in order to avoid the entry of air or brine into the plant in case of leakages at the evaporator, as this would present the risk of disturbing the normal operation of the system.
In the field of extinguishing and of firefighting, - 3 use is made principally of chlorobromofluoroalkanes and bromofluoroalkanes, particularly trifluorobromomethane, difluorochlorobromomethane and 1,1,2,2-tetrafluoro-1,2* dibromoethane. These compounds are employed especially in premises where corrosion-sensitive electrical and electronic equipment is to be found (e.q. data processing rooms, telephone exchanges, engine rooms aboard ships). However, like the CFCs, these compounds have high ODPs (ozone depletion potentials).
It has now been found that 1,1,1,2tetrafluoroethane (R 134a) and perfluoropropane (R 218) form an azeotrope with a minimum boiling point of approximately -41.1°C at 1.013 bars and whose R 218 content at the normal boiling point is approximately 76 % on a mass basis. This composition naturally varies as a function of the pressure of the mixture and, at a given pressure, can be easily determined by well-known methods. Accordingly the present invention provides a minimum boiling point azeotrope which is a mixture of 1,1,1,2-tetrafluoroethane and perfluoropropane such that at its normal boiling point it contains approximately 76 % on a mass basis of perfluoropropane and 24 % on a mass basis of 1,1,1,2tetrafluoroethane.
„ The azeotrope according to the invention has the advantage of exhibiting substantially zero ODP. This means that it is devoid of destructive action on the stratospheric ozone layer. The ODP is defined as the ratio betveen the lowering of the ozone column recorded during * the emission of a unit mass of substance and the same lowering in the case of trichlorofluoromethane, chosen as * reference (ODP = 1). By way of indication, trifluorobromomethane has an ODP of 10.
Because of its low boiling point, the azeotropic mixture according to the invention can be employed as a refrigerating fluid in applications at low boiling temperatures (-40eC; -41°C), as in the case of low temperature commercial refrigeration where R 218 by itself has mediocre thermodynamic properties and where R 134a by itself cannot be employed for the reasons set out above.
It has also been found that this azeotrope can be employed as an extinguishing agent, especially to replace trifluorobromomethane and difluorochlorobromomethane. In fact, it has a Cup Burner value lower than 10 % and consequently exhibits a high extinguishing power.
The azeotrope according to the invention can be employed for firefighting according to the same techniques as trifluorobromomethane and difluorochlorobromomethane.
Thus, it can be advantageously employed for the protection of premises using the so-called complete immersion technique. It can be pressurized with inert gases such as « nitrogen, and this allows its discharge speed to be increased. It can also be employed in portable extinguisher techniques.
Given its physical properties which are close to those of the CFCs, the mixture according to the invention can also be employed as an aerosol propellant or as a blowing agent for plastic foams.
The following Examples further illustrate the present invention.
KXAMJPJLE 1 The azeotrope according to the invention was 10 investigated experimentally at various temperatures by analysis of the liquid phase and vapour phase compositions, using gas phase chromatography, for various mixtures of R 134a and R 218.
The pressures were measured with an accuracy 15 greater than 0.02 bar by means of a Heise manometer. The temperatures were measured to within 0.02°C by means of a 1,000-ohm platinum probe.
Graph 1 of the accompanying Figure shows the liquid/vapour equilibrium curve for R 218/R 134a mixtures, established at a temperature of 20.3°C. On this graph the abscissa shows the mass fraction of R 218 and the ordinate the absolute pressure in bars; the - signs correspond to the experimental points. s A curve similar to that of Graph 1 can be obtained for each temperature. On successively adding R 218 to R 134a the pressure developed by the mixture increases steadily, then passes through a maximum and decreases steadily, which demonstrates the existence of the azeotrope vith a minimum boiling point.
Table 1, which follows, gives the pressuretemperature relationship for this azeotrope, compared vith that for the pure substances.
Temperature (°C) Absolute pressure (bars) R 218/R 134a azeotrope Pure R 134a Pure R 218 -40.0 1.10 0.53 0.87 0.3 4.92 2.94 4.20 20.3 9.08 5.78 7.66 39.9 15.10 10.26 12.98 The vapour pressure of the azeotrope remains higher than the vapour pressure of the pure substances over a wide range of temperature. These data show that the mixture remains azeotropic throughout this temperature range.
EXAMPLE 2 The characterization of the azeotrope at the normal boiling point vas carried out by direct measurement of the ·> boiling temperature of various R 218/R 134a mixtures by means of an ebulliometer.
Table 2 summarizes the results obtained and enables the azeotrope to be characterized by: - its normal boiling point, which ..is equalto-------approximately -41.1°C, - its mass content of R 218, which is equal to approximately 76 %.
TABLE 2 Temperature (°C) Mass content of R 218 -26.5 0 -40.4 70.9 -40.8 74.6 -41.0 75.2 -41.0 76.4 -40.9 78.3 -36.7 100.0 EXAMPLE 3 This Example illustrates the use of the azeotrope according to the invention as a refrigerating fluid.
The thermodynamic performance of the azeotropic 25 mixture according to the invention was compared with the performance of the two constituents by themselves, under conditions close to those encountered in commercial refrigeration systems, namely the following: - condensation temperature : +30°C - evaporation temperature : -30°C - liquid supercooling : - 5°C - vapour superheating at the compressor : +15°C Table 3 summarizes the thermodynamic performance 10 observed under these conditions for pure R 134a, pure R 218 and the azeotropic mixture according to the invention.
TABLE 3 R 218/R 134a azeotrope Pure R 218 Pure R 134a Evaporation pressure (bars) 1.69 1.36 0.85 Condensation pressure (bars) 11.58 10.1 7.70 Oanopression ratio 6.85 7.43 9.06 20 Refrigerating capacity (kJ/m3) 877 710 640 Coefficient of performance 2.7 2.4 3.1 It can be seen that the azeotropic mixture according to the invention offers a number of advantages ti over pure R 134a or R 218, especially: - a lower compression ratio and therefore an improvement in the volumetric efficiency of the compressor and consequently lower plant running costs - a considerably higher available volumetric refrigerating capacity which, in practice, for a given refrigerating capacity, makes it possible to employ a smaller compressor than that required for pure R 134a or R 218.
In the case of the azeotrope according to the 10 invention, this increase in available volumetric refrigerating capacity also makes it possible to increase by 37 % the available refrigerating capacity of an existing plant using R 134a.
EXAMPLE 4 This Example illustrates the use of the azeotrope according to the invention as an extinguishing agent.
The extinguishing efficiency is generally measured by the so-called Cup Burner method.
This method, described in draft standard 20 ISO/DIS 7075-1, shows the minimum percentage of extinguishing compound (measured by volume) in a mixture of air plus extinguishing compound needed to extinguish a flaming liquid fuel.
The lower the Cup Burner value, the more effective 25 is the extinguishing compound.
We employed ethanol as the liquid fuel.
The Cup Burner value for the R 218/R 134a azeotropic mixture according to the invention is equal to
Claims (7)
1. A minimum boiling point azeotrope which is a mixture of 1,1,1,2-tetrafluoroethane and perfluoropropane such that at its normal boiling point it contains 5 approximately 76 % on a mass basis of perfluoropropane and 24 % on a mass basis of 1,1,1,2-tetrafluoroethane.
2. Use of the azeotrope according to Claim 1 as a refrigerating fluid.
3. Use of the azeotrope according to Claim 1 as 10 an aerosol propellant.
4. Use of the azeotrope according to Claim 1 as a blowing agent for plastic foams.
5. Use of the azeotrope according to Claim 1 as an extinguishing agent.
6. A minimum boiling point azeotrope according to Claim 1, substantially as hereinbefore described and exemplified.
7. Use according to any one of Claims 2-5, substantially as hereinbefore described and exemplified.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8914788A FR2654427B1 (en) | 1989-11-10 | 1989-11-10 | NEW AZEOTROPIC MIXTURE WITH LOW BOILING POINT BASED ON FLUOROALKANES AND ITS APPLICATIONS. |
| FR909007153A FR2662944B2 (en) | 1989-11-10 | 1990-06-08 | NEW AZEOTROPIC MIXTURE WITH LOW BOILING POINT BASED ON FLUOROALKANES AND ITS APPLICATIONS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE904049A1 IE904049A1 (en) | 1991-05-22 |
| IE64735B1 true IE64735B1 (en) | 1995-09-06 |
Family
ID=26227656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE404990A IE64735B1 (en) | 1989-11-10 | 1990-11-09 | An azeotropic mixture with a low boiling point based on fluoroalkanes |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0427604B1 (en) |
| JP (1) | JPH0729956B2 (en) |
| KR (1) | KR920009972B1 (en) |
| AT (1) | ATE88452T1 (en) |
| AU (1) | AU633648B2 (en) |
| CA (1) | CA2028735A1 (en) |
| DE (1) | DE69001423T2 (en) |
| DK (1) | DK0427604T3 (en) |
| ES (1) | ES2069717T3 (en) |
| FI (1) | FI97053C (en) |
| FR (1) | FR2662944B2 (en) |
| IE (1) | IE64735B1 (en) |
| NO (1) | NO173230C (en) |
| PT (1) | PT95848B (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0439579T3 (en) * | 1989-08-21 | 1996-01-29 | Great Lakes Chemical Corp | Procedure for extinguishing a fire |
| FR2682395B1 (en) * | 1991-10-09 | 1993-12-10 | Atochem | MIXTURES OF 1,1,1-TRIFLUOROETHANE, PERFLUOROPROPANE AND PROPANE, AND THEIR APPLICATIONS AS REFRIGERANTS, AS AEROSOL PROPELLANTS OR AS PLASTIC FOAM EXPANDING AGENTS. |
| US5236611A (en) * | 1991-10-28 | 1993-08-17 | E. I. Du Pont De Nemours And Company | Mixtures of perfluoropropane and trifluoroethane |
| AU668534B2 (en) * | 1991-12-03 | 1996-05-09 | United States Environmental Protection Agency | Refrigerant compositions and processes for using same |
| FR2686092B1 (en) * | 1992-01-13 | 1994-09-16 | Atochem Elf Sa | MIXTURES OF 1,1,1-TRIFLUOROETHANE AND PERFLUOROPROPANE AND THEIR APPLICATIONS AS REFRIGERANTS, AS AEROSOL PROPELLERS OR AS PLASTIC FOAM EXPANSION AGENTS. |
| EP0556722A1 (en) * | 1992-02-19 | 1993-08-25 | Hoechst Aktiengesellschaft | Method of decreasing the total pressure in aerosol containers |
| US5248433A (en) * | 1992-04-30 | 1993-09-28 | E. I. Du Pont De Nemours And Company | Binary azeotropic mixtures of octafluoropropane and fluoroethane |
| US5494601A (en) * | 1993-04-01 | 1996-02-27 | Minnesota Mining And Manufacturing Company | Azeotropic compositions |
| US5401429A (en) * | 1993-04-01 | 1995-03-28 | Minnesota Mining And Manufacturing Company | Azeotropic compositions containing perfluorinated cycloaminoether |
| GB9522701D0 (en) * | 1995-11-07 | 1996-01-10 | Star Refrigeration | Centrifugal compression refrigerant composition |
| CZ298309B6 (en) | 1997-07-15 | 2007-08-22 | E.I.Du Pont De Nemours And Company | Refrigerant compositions and use thereof |
| US7258813B2 (en) | 1999-07-12 | 2007-08-21 | E.I. Du Pont De Nemours And Company | Refrigerant composition |
| RU2169597C1 (en) * | 2000-04-20 | 2001-06-27 | Федеральное государственное учреждение Всероссийский научно-исследовательский институт противопожарной обороны МВД России | Composition for prevention of inflammation and explosion of combustion mixtures |
| DE10121544B4 (en) * | 2001-05-03 | 2007-08-16 | Axima Refrigeration Gmbh | Process for the liquefaction of a reactive gas |
| GB0223724D0 (en) | 2002-10-11 | 2002-11-20 | Rhodia Organique Fine Ltd | Refrigerant compositions |
| JP4838513B2 (en) | 2002-11-29 | 2011-12-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Cryogenic refrigerant |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3607755A (en) * | 1968-11-25 | 1971-09-21 | Allied Chem | Novel halocarbon compositions |
| US4101467A (en) * | 1976-02-27 | 1978-07-18 | The Dow Chemical Company | Soft ethylenic polymer foams |
| US4810403A (en) * | 1987-06-09 | 1989-03-07 | E. I. Du Pont De Nemours And Company | Halocarbon blends for refrigerant use |
| US4944890A (en) * | 1989-05-23 | 1990-07-31 | E. I. Du Pont De Nemours And Company | Compositions and process of using in refrigeration |
-
1990
- 1990-06-08 FR FR909007153A patent/FR2662944B2/en not_active Expired - Lifetime
- 1990-10-29 CA CA002028735A patent/CA2028735A1/en not_active Abandoned
- 1990-10-31 NO NO904726A patent/NO173230C/en unknown
- 1990-11-05 ES ES90403117T patent/ES2069717T3/en not_active Expired - Lifetime
- 1990-11-05 EP EP90403117A patent/EP0427604B1/en not_active Expired - Lifetime
- 1990-11-05 DE DE9090403117T patent/DE69001423T2/en not_active Expired - Fee Related
- 1990-11-05 AT AT90403117T patent/ATE88452T1/en not_active IP Right Cessation
- 1990-11-05 DK DK90403117.6T patent/DK0427604T3/en active
- 1990-11-07 JP JP2302314A patent/JPH0729956B2/en not_active Expired - Lifetime
- 1990-11-09 FI FI905565A patent/FI97053C/en not_active IP Right Cessation
- 1990-11-09 PT PT95848A patent/PT95848B/en not_active IP Right Cessation
- 1990-11-09 IE IE404990A patent/IE64735B1/en not_active IP Right Cessation
- 1990-11-10 KR KR1019900018190A patent/KR920009972B1/en not_active Expired
- 1990-11-12 AU AU66549/90A patent/AU633648B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| FR2662944B2 (en) | 1992-09-04 |
| DK0427604T3 (en) | 1993-05-17 |
| DE69001423T2 (en) | 1993-09-09 |
| EP0427604B1 (en) | 1993-04-21 |
| KR920009972B1 (en) | 1992-11-09 |
| EP0427604A1 (en) | 1991-05-15 |
| FI97053C (en) | 1996-10-10 |
| CA2028735A1 (en) | 1991-05-11 |
| NO173230C (en) | 1993-11-17 |
| JPH0729956B2 (en) | 1995-04-05 |
| ES2069717T3 (en) | 1995-05-16 |
| NO904726D0 (en) | 1990-10-31 |
| FR2662944A2 (en) | 1991-12-13 |
| JPH03173839A (en) | 1991-07-29 |
| DE69001423D1 (en) | 1993-05-27 |
| ATE88452T1 (en) | 1993-05-15 |
| KR910009620A (en) | 1991-06-28 |
| NO904726L (en) | 1991-05-13 |
| FI97053B (en) | 1996-06-28 |
| AU6654990A (en) | 1991-05-16 |
| FI905565A0 (en) | 1990-11-09 |
| NO173230B (en) | 1993-08-09 |
| PT95848B (en) | 1997-11-28 |
| AU633648B2 (en) | 1993-02-04 |
| PT95848A (en) | 1991-09-13 |
| IE904049A1 (en) | 1991-05-22 |
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| Date | Code | Title | Description |
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| MM4A | Patent lapsed |