WO2010040928A1 - Fluide de transfert de chaleur - Google Patents

Fluide de transfert de chaleur Download PDF

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Publication number
WO2010040928A1
WO2010040928A1 PCT/FR2009/051814 FR2009051814W WO2010040928A1 WO 2010040928 A1 WO2010040928 A1 WO 2010040928A1 FR 2009051814 W FR2009051814 W FR 2009051814W WO 2010040928 A1 WO2010040928 A1 WO 2010040928A1
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WO
WIPO (PCT)
Prior art keywords
weight
tetrafluoropropene
difluoromethane
difluoroethane
heat transfer
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.)
Ceased
Application number
PCT/FR2009/051814
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English (en)
French (fr)
Inventor
Wissam Rached
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
Arkema France SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40627376&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2010040928(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to PL09759757T priority Critical patent/PL2331651T3/pl
Priority to ES09759757.9T priority patent/ES2663548T3/es
Priority to US13/122,606 priority patent/US20110186772A1/en
Priority to JP2011530523A priority patent/JP5591246B2/ja
Priority to CN200980138906.7A priority patent/CN102171309B/zh
Application filed by Arkema France SA filed Critical Arkema France SA
Priority to EP09759757.9A priority patent/EP2331651B1/fr
Publication of WO2010040928A1 publication Critical patent/WO2010040928A1/fr
Anticipated expiration legal-status Critical
Priority to US14/873,855 priority patent/US9599381B2/en
Priority to US15/396,855 priority patent/US20170145276A1/en
Priority to US16/142,492 priority patent/US11130893B2/en
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
    • C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B31/00—Compressor arrangements
    • F25B31/002—Lubrication
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B45/00—Arrangements for charging or discharging refrigerant
    • 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
    • C09K2205/122—Halogenated 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
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/126—Unsaturated fluorinated 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
    • C09K2205/22—All components of a mixture being fluoro 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/40—Replacement mixtures
    • 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
    • C09K2205/40—Replacement mixtures
    • C09K2205/43—Type R22
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C10M2203/065—Well-defined aromatic compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • C10M2209/043—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/097—Refrigerants
    • C10N2020/101—Containing Hydrofluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to compositions containing hydrofluoroolefins and their uses as heat transfer fluids, blowing agents, solvents and aerosols.
  • ODP ozone depletion potential
  • HFCs hydrofluorocarbons
  • GWP 1300
  • GWP Global Warming Potentials
  • Carbon dioxide being non-toxic, non-flammable and having a very low GWP has been proposed as refrigerant air conditioning systems replacing HFC-134a.
  • the use of carbon dioxide has several disadvantages, particularly related to the very high pressure of its implementation as a refrigerant in existing devices and technologies.
  • the R-404A mixture consisting of 44% by weight of pentafluoroethane, 52% by weight of trifluoroethane and 4% by weight of HFC-134a is widely used as a refrigeration fluid for large surfaces (supermarket) and in refrigerated transport .
  • this mixture has a GWP of 3900.
  • the mixture R-407C consisting of 52% by weight of HFC-134a, 25% by weight of pentafluoroethane and 23% by weight of difluoromethane, is used as a heat transfer fluid in the water. air conditioning and heat pumps. This mixture however has a GWP of 1800.
  • WO2004 / 037913 discloses the use of compositions comprising at least one fluoroalkene having three or four carbon atoms, especially pentafluoropropene and tetrafluoropropene, preferably having a GWP of at most 150, as heat transfer fluids.
  • WO 2005/105947 teaches the addition to tetrafluoropropene, preferably 1, 3,3,3 tetrafluoropropene, of a co-blowing agent such as difluoromethane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoropropane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water and carbon dioxide.
  • a co-blowing agent such as difluoromethane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoropropane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water and carbon dioxide.
  • WO 2006/094303 discloses an azeotropic composition containing 7.4% by weight of 2,3,3,3-tetrafluoropropene (1234yf) and 92.6% by weight of difluoromethane (HFC-32). This document also discloses an azeotropic composition containing 91% by weight of 2,3,3,3-tetrafluoropropene and 9% by weight of difluoroethane (HFC-152a).
  • compositions containing hydrofluoropropenes, used as a heat transfer fluid do not have the aforementioned drawbacks and having both an ODP zero and GWP lower than existing heat transfer fluids such as R-404A or R-407C or R22 (chlorodifluoromethane).
  • compositions according to the present invention are characterized in that they comprise from 60 to 90% by weight of 2,3,3,3-tetrafluoropropene and from 10 to 40% by weight of at least one compound chosen from difluoroethane and difluoromethane.
  • the compositions comprise from 60 to 79% by weight of 2,3,3,3-tetrafluoropropene and from 21 to 40% by weight of a compound chosen from difluoroethane and difluoromethane.
  • the compositions according to this first embodiment preferably comprise from 60 to 70% by weight of 2,3,3,3-tetrafluoropropene and from 30 to 40% by weight of a compound chosen from difluoroethane and difluoromethane.
  • compositions according to this first embodiment comprise from 60 to 65% by weight of 2,3,3,3-tetrafluoropropene and from 35 to 40% by weight of a compound chosen from difluoroethane and difluoromethane.
  • compositions according to this first embodiment include 2,3,3,3-tetrafluoropropene and difluoromethane.
  • compositions essentially contain 2,3,3,3-tetrafluoropropene and difluoromethane.
  • compositions comprise from 60 to 90% by weight of 2,3,3,3-tetrafluoropropene and from 10 to 40% by weight of a mixture consisting of difluoromethane and difluoroethane.
  • compositions according to this second embodiment comprise from 60 to 80% by weight of 2,3,3,3-tetrafluoropropene and 20 to
  • compositions according to this second embodiment comprise from 60 to 75% by weight of 2,3,3,3-tetrafluoropropene and from 25 to 40% by weight of a mixture consisting of difluoromethane and difluoroethane.
  • Particularly preferred compositions comprise 60 to 80% by weight of 2,3,3,3-tetrafluoropropene and 5 to 35% by weight of difluoromethane and 5 to 35% by weight of difluoroethane.
  • compositions of interest are those comprising or containing essentially from 60 to 80% by weight of 2,3,3,3-tetrafluoropropene and from 10 to 30% by weight of difluoromethane and from 10 to 30% by weight of difluoroethane.
  • the compositions according to the present invention may comprise a 2,3,3,3-tetrafluoropropene stabilizer. The stabilizer represents at most 5% by weight relative to the total composition.
  • nitromethane ascorbic acid, terephthalic acid, azoles such as tolutriazole or benzotriazole, phenol compounds such as tocopherol, hydroquinone, t-butyl hydroquinone, 2 , 6-di-tert-butyl-4-methylphenol, epoxides (optionally fluorinated or perfluorinated alkyl or alkenyl or aromatic) such as n-butyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether, butylphenylglycidyl ether, phosphites, phosphates, phosphonates, thiols and lactones.
  • epoxides optionally fluorinated or perfluorinated alkyl or alkenyl or aromatic
  • compositions according to the present invention may comprise lubricants such as mineral oil, alkylbenzene, polyalkylene glycol and polyvinyl ether.
  • compositions according to the present invention are suitable for the replacement of R-404A in refrigeration and / or R-407C in air conditioning and heat pumps in current installations. They may also be suitable for replacing R-404A in refrigeration systems with cascade compression in which at least one stage is operated with the compositions according to the present invention.
  • compositions of particular interest for the replacement of R-404A in existing installations mention may be made of those comprising or essentially containing 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoromethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoromethane; 60% in 2,3,3,3-tetrafluoropropene, 30% by weight of difluoromethane and 10% by weight of difluoroethane.
  • compositions of particular interest for the replacement of R-404A in cascade compression systems comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight. difluoroethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoroethane; 75% by weight of 2,3,3,3-tetrafluoropropene, 20% by weight of difluoromethane and 5% by weight of difluoroethane.
  • the compositions according to the present invention can also be used instead of R-407C, for example in heat pumps.
  • compositions of particular interest for the replacement of R-407C in existing installations mention may be made of those comprising or essentially containing 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoromethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoromethane; 60% by weight of 2,3,3,3-tetrafluoropropene, 30% by weight of difluoromethane and 10% by weight of difluoroethane; 70% by weight of 2,3,3,3-tetrafluoropropene, 25% by weight of difluoromethane and 5% by weight of difluoroethane.
  • the compositions according to the present invention are furthermore usable as blowing agents, aerosols and solvents.
  • compositions according to the invention under the refrigeration operating conditions are given in Table 1.
  • values of the constituents (1234yf, 32 and 152a) for each composition are given in percent by weight.
  • the rated operating pressure is 18 bar
  • the volumetric capacity is 1500 kJ / m 3
  • the COP is 1.8 in the following operating conditions: Evaporation temperature: -20 0 C
  • Compressor inlet temperature -5 ° C
  • T comp output temperature at the compressor output
  • COP coefficient of performance and is defined when it comes to refrigeration as the useful cold power supplied by the system to the power supplied or consumed by the system.
  • % CAP or COP is the ratio of the value of the CAP or COP of the mixture compared to the same value for the R404A.
  • compositions according to the present invention in the heat pump and air conditioning operating conditions are given in Table 2.
  • values of the constituents (1234yf, 32 and 152a) for each composition are given in percent by weight.
  • the nominal operating pressure is 34 bar
  • the volumetric capacity is 1461 kJ / m 3
  • the COP is 2.1 under the following operating conditions: Evaporation temperature: -5 ° C
  • Compressor inlet temperature 5 ° C
  • T comp output temperature at the compressor output
  • COP coefficient of performance and is defined, in the case of a heat pump, as being the useful hot power supplied by the system on the power supplied or consumed by the system.
  • % CAP or COP is the ratio of the value of the CAP or COP of the mixture compared to the same value for the R-407C.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
PCT/FR2009/051814 2008-10-08 2009-09-24 Fluide de transfert de chaleur Ceased WO2010040928A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP09759757.9A EP2331651B1 (fr) 2008-10-08 2009-09-24 Fluide de transfert de chaleur
ES09759757.9T ES2663548T3 (es) 2008-10-08 2009-09-24 Fluido de transferencia de calor
US13/122,606 US20110186772A1 (en) 2008-10-08 2009-09-24 Heat transfer fluid
JP2011530523A JP5591246B2 (ja) 2008-10-08 2009-09-24 熱伝導流体
CN200980138906.7A CN102171309B (zh) 2008-10-08 2009-09-24 传热流体
PL09759757T PL2331651T3 (pl) 2008-10-08 2009-09-24 Czynnik do przenoszenia ciepła
US14/873,855 US9599381B2 (en) 2008-10-08 2015-10-02 Heat transfer fluid
US15/396,855 US20170145276A1 (en) 2008-10-08 2017-01-03 Heat transfer fluid
US16/142,492 US11130893B2 (en) 2008-10-08 2018-09-26 Heat transfer fluid

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0856817A FR2936806B1 (fr) 2008-10-08 2008-10-08 Fluide refrigerant
FR08.56817 2008-10-08
FR0856836A FR2936807B3 (fr) 2008-10-08 2008-10-09 Fluide de transfert de chaleur
FR08.56836 2008-10-09

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US13/122,606 A-371-Of-International US20110186772A1 (en) 2008-10-08 2009-09-24 Heat transfer fluid
US14/873,855 Continuation US9599381B2 (en) 2008-10-08 2015-10-02 Heat transfer fluid

Publications (1)

Publication Number Publication Date
WO2010040928A1 true WO2010040928A1 (fr) 2010-04-15

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PCT/FR2009/051814 Ceased WO2010040928A1 (fr) 2008-10-08 2009-09-24 Fluide de transfert de chaleur

Country Status (10)

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US (4) US20110186772A1 (cg-RX-API-DMAC7.html)
EP (2) EP2586842A3 (cg-RX-API-DMAC7.html)
JP (5) JP5591246B2 (cg-RX-API-DMAC7.html)
CN (1) CN102171309B (cg-RX-API-DMAC7.html)
ES (1) ES2663548T3 (cg-RX-API-DMAC7.html)
FR (2) FR2936806B1 (cg-RX-API-DMAC7.html)
PL (1) PL2331651T3 (cg-RX-API-DMAC7.html)
PT (1) PT2331651T (cg-RX-API-DMAC7.html)
TW (1) TWI406934B (cg-RX-API-DMAC7.html)
WO (1) WO2010040928A1 (cg-RX-API-DMAC7.html)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011084813A1 (en) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company Compositions comprising tetrafluoropropene and difluoromethane and uses thereof
WO2011093521A1 (en) * 2010-01-27 2011-08-04 Daikin Industries, Ltd. Refrigerant composition comprising difluoromethane (hfc32) and 2,3,3,3-tetrafluoropropene (hfo1234yf)
US20120151959A1 (en) * 2009-09-11 2012-06-21 Arkema France Binary refrigerating fluid
WO2013084431A1 (ja) * 2011-12-08 2013-06-13 パナソニック株式会社 空気調和機
CN103282461A (zh) * 2010-11-12 2013-09-04 霍尼韦尔国际公司 低gwp的传热组合物
US9039922B2 (en) 2009-09-11 2015-05-26 Arkema France Low-temperature and average-temperature refrigeration
EP2475737B1 (fr) 2009-09-11 2016-05-18 Arkema France Procede de transfert de chaleur
US9540556B2 (en) 2008-11-19 2017-01-10 The Chemours Company Fc, Llc Tetrafluoropropene compositions and uses thereof
US9599381B2 (en) 2008-10-08 2017-03-21 Arkema France Heat transfer fluid
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
US12195664B2 (en) 2008-07-30 2025-01-14 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
US12203028B2 (en) 2009-07-29 2025-01-21 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2937328B1 (fr) 2008-10-16 2010-11-12 Arkema France Procede de transfert de chaleur
US20170080773A1 (en) 2008-11-03 2017-03-23 Arkema France Vehicle Heating and/or Air Conditioning Method
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JP5591246B2 (ja) 2014-09-17
JP2014141681A (ja) 2014-08-07
JP2016176082A (ja) 2016-10-06
TWI406934B (zh) 2013-09-01
ES2663548T3 (es) 2018-04-13
JP2021066889A (ja) 2021-04-30
FR2936806B1 (fr) 2012-08-31
US20110186772A1 (en) 2011-08-04
PL2331651T3 (pl) 2018-06-29
CN102171309B (zh) 2014-06-25
US20190203094A1 (en) 2019-07-04
CN102171309A (zh) 2011-08-31
JP2012505279A (ja) 2012-03-01

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