CA2674256C - Compositions containing difluoromethane and fluorine substituted olefins - Google Patents

Compositions containing difluoromethane and fluorine substituted olefins Download PDF

Info

Publication number
CA2674256C
CA2674256C CA2674256A CA2674256A CA2674256C CA 2674256 C CA2674256 C CA 2674256C CA 2674256 A CA2674256 A CA 2674256A CA 2674256 A CA2674256 A CA 2674256A CA 2674256 C CA2674256 C CA 2674256C
Authority
CA
Canada
Prior art keywords
composition
weight
heat transfer
systems
percent
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.)
Expired - Fee Related
Application number
CA2674256A
Other languages
English (en)
French (fr)
Other versions
CA2674256A1 (en
Inventor
Ryan Hulse
Rajiv Ratna Singh
Justin Becker
Robert Gerard Richard
Rajat S. Basu
Hang T. Pham
Ian Shankland
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.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
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
Priority claimed from US12/511,954 external-priority patent/US20120097885A9/en
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Publication of CA2674256A1 publication Critical patent/CA2674256A1/en
Application granted granted Critical
Publication of CA2674256C publication Critical patent/CA2674256C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • 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
    • F25B9/00—Compression machines, plants or systems, in which the refrigerant is air or other gas of low boiling point
    • 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
    • C09K2205/10—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
    • C09K2205/22—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
    • C09K2205/32—The mixture being azeotropic
    • 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
    • C09K2205/34—The mixture being non-azeotropic
    • 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
    • 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
    • F25B1/00—Compression machines, plants or systems with non-reversible cycle
    • 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
    • F25B2400/00—Component parts or details not otherwise provided for in this subclass
    • F25B2400/12—Inflammable refrigerants
    • F25B2400/121—Inflammable refrigerants using R1234

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2674256A 2008-07-30 2009-07-30 Compositions containing difluoromethane and fluorine substituted olefins Expired - Fee Related CA2674256C (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US8499708P 2008-07-30 2008-07-30
US61/084,997 2008-07-30
US9938208P 2008-09-23 2008-09-23
US61/099,382 2008-09-23
US12/511,954 2009-07-29
US12/511,954 US20120097885A9 (en) 2003-10-27 2009-07-29 Compositions Containing Difluoromethane and Fluorine Substituted Olefins

Publications (2)

Publication Number Publication Date
CA2674256A1 CA2674256A1 (en) 2010-01-30
CA2674256C true CA2674256C (en) 2019-02-12

Family

ID=41611033

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2674256A Expired - Fee Related CA2674256C (en) 2008-07-30 2009-07-30 Compositions containing difluoromethane and fluorine substituted olefins

Country Status (6)

Country Link
US (2) US12195664B2 (enExample)
JP (8) JP5770969B2 (enExample)
KR (4) KR20100013288A (enExample)
CN (5) CN107384323A (enExample)
CA (1) CA2674256C (enExample)
MX (3) MX382469B (enExample)

Families Citing this family (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107384323A (zh) * 2008-07-30 2017-11-24 霍尼韦尔国际公司 含有二氟甲烷和氟取代的烯烃的组合物
FR2936806B1 (fr) * 2008-10-08 2012-08-31 Arkema France Fluide refrigerant
US20100122545A1 (en) 2008-11-19 2010-05-20 E. I. Du Pont De Nemours And Company Tetrafluoropropene compositions and uses thereof
US9845419B2 (en) * 2009-07-29 2017-12-19 Honeywell International Inc. Low GWP heat transfer compositions containing difluoromethane and 1,3,3,3-tetrafluoropropene
FR2950066B1 (fr) 2009-09-11 2011-10-28 Arkema France Refrigeration basse et moyenne temperature
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
FR2950067B1 (fr) * 2009-09-11 2011-10-28 Arkema France Fluide de transfert de chaleur en remplacement du r-410a
FR2950068B1 (fr) 2009-09-11 2012-05-18 Arkema France Procede de transfert de chaleur
FR2950065B1 (fr) * 2009-09-11 2012-02-03 Arkema France Fluide refrigerant binaire
MY158739A (en) * 2009-12-21 2016-11-15 Du Pont Compositions comprising tetrafluoropropene and difluoromethane and uses thereof
DK2528983T3 (da) 2010-01-27 2021-01-11 Daikin Ind Ltd Anvendelse af køleskabssammensætning, der omfatter difluormethan (hfc-32) og 2,3,3,3-tetrafluorpropen (hfo-1234yf)
FR2957083B1 (fr) 2010-03-02 2015-12-11 Arkema France Fluide de transfert de chaleur pour compresseur centrifuge
FR2959999B1 (fr) 2010-05-11 2012-07-20 Arkema France Fluides de transfert de chaleur et leur utilisation dans des echangeurs de chaleur a contre-courant
WO2012021746A1 (en) * 2010-08-13 2012-02-16 Carrier Corporation Fluorinated hydrocarbon composition
US20120119136A1 (en) * 2010-11-12 2012-05-17 Honeywell International Inc. Low gwp heat transfer compositions
JP2012236884A (ja) * 2011-05-10 2012-12-06 Fujitsu General Ltd 混合冷媒とそれを用いた空気調和機
GB2493395B (en) * 2011-08-05 2014-07-23 Mexichem Amanco Holding Sa Heat transfer compositions
CN102635931B (zh) * 2012-02-17 2017-03-22 海尔集团公司 采用混合制冷剂的空调换热器及空调器
CN102746825A (zh) * 2012-06-27 2012-10-24 西安交通大学 含有氟代乙烷的混合工质
JP5937446B2 (ja) * 2012-07-13 2016-06-22 Ｊｘエネルギー株式会社 冷凍機用作動流体組成物
US9783721B2 (en) * 2012-08-20 2017-10-10 Honeywell International Inc. Low GWP heat transfer compositions
RU2015108379A (ru) * 2012-08-20 2016-10-10 Ханивелл Интернешнл Инк. Композиции теплоносителя с низким пгп
TW201410856A (zh) * 2012-08-23 2014-03-16 Du Pont 含四氟丙烯及二氟甲烷的冷媒混合物及其運用
ES2905258T3 (es) 2012-09-04 2022-04-07 Daikin Ind Ltd Método para llenar un refrigerante mixto que contiene 2,3,3,3-tetrafluoropropeno
ES2726535T3 (es) * 2012-12-04 2019-10-07 Honeywell Int Inc Composiciones de transferencia de calor con bajo GWP
WO2014130983A1 (en) * 2013-02-25 2014-08-28 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
US20140264147A1 (en) * 2013-03-15 2014-09-18 Samuel F. Yana Motta Low GWP heat transfer compositions containing difluoromethane, A Fluorinated ethane and 1,3,3,3-tetrafluoropropene
EP2972014A4 (en) * 2013-03-15 2016-10-26 Honeywell Int Inc LOW GWP CALOPOROUS COMPOSITIONS
WO2015022958A1 (ja) 2013-08-14 2015-02-19 セントラル硝子株式会社 熱伝達方法及び高温ヒートポンプ装置
WO2015022959A1 (ja) 2013-08-14 2015-02-19 セントラル硝子株式会社 熱伝達方法および高温ヒートポンプ装置
JP2015158303A (ja) * 2014-02-24 2015-09-03 三菱電機株式会社 熱交換器及び冷凍サイクル装置
JP5861727B2 (ja) 2014-03-04 2016-02-16 ダイキン工業株式会社 トランス−１，３，３，３−テトラフルオロプロペンを含む混合冷媒の充填方法
US10035937B2 (en) * 2014-05-05 2018-07-31 Honeywell International Inc. Low GWP heat transfer compositions
DK3284797T3 (da) * 2014-09-25 2021-02-01 Daikin Ind Ltd Sammensætning, der omfatter hfc og hfo
CN104531079B (zh) * 2014-12-11 2018-04-17 中国科学院理化技术研究所 一种含四氟丙烯的混合制冷剂
JP6208399B2 (ja) * 2015-03-24 2017-10-04 旭化成建材株式会社 フェノール樹脂発泡体及びその製造方法
JP2018535296A (ja) * 2015-10-07 2018-11-29 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． システムを再充填するための方法及び組成物、並びに再充填したシステム
CN108779940A (zh) * 2016-03-25 2018-11-09 霍尼韦尔国际公司 低gwp级联制冷系统
JP6774769B2 (ja) * 2016-03-25 2020-10-28 三菱重工サーマルシステムズ株式会社 冷凍サイクル装置
PL3491094T3 (pl) * 2016-07-29 2023-02-20 Honeywell International Inc. Kompozycje, sposoby oraz systemy do przekazywania ciepła
MX2019001102A (es) * 2016-07-29 2019-06-12 Honeywell Int Inc Composiciones, metodos y sistemas de transferencia de calor.
AU2017302342C1 (en) * 2016-07-29 2021-09-09 Solstice Advanced Materials Us, Inc. Heat transfer compositions, methods and systems
KR101868135B1 (ko) * 2016-10-27 2018-06-18 (주)팀코스파 친환경 냉매가스 조성물 및 그 제조방법
DE102017203043A1 (de) * 2017-02-24 2018-08-30 Siemens Aktiengesellschaft Wärmepumpenanordnung und Verfahren zum Betrieb einer Wärmepumpenanordnung
US20200017743A1 (en) * 2017-03-06 2020-01-16 Arkema Inc. Refrigerants with reduced flammability profile
FR3064275B1 (fr) * 2017-03-21 2019-06-07 Arkema France Procede de chauffage et/ou climatisation d'un vehicule
JP7126517B2 (ja) * 2017-05-05 2022-08-26 ハネウェル・インターナショナル・インコーポレーテッド 熱伝達組成物、方法、及びシステム
JP6443576B2 (ja) * 2017-05-19 2018-12-26 ダイキン工業株式会社 冷媒を含有する組成物、その使用、それを用いた冷凍方法、及びそれを含む冷凍機
CN114644904B (zh) * 2017-10-06 2024-09-13 霍尼韦尔国际公司 热传递组合物、方法和系统
EP3710550A4 (en) * 2017-11-17 2021-09-29 Honeywell International Inc. COMPOSITIONS, METHODS AND SYSTEMS FOR HEAT TRANSFER
US10731066B2 (en) * 2017-11-17 2020-08-04 Honeywell International Inc. Heat transfer compositions, methods and systems
PL3717589T3 (pl) * 2017-11-30 2026-05-11 Honeywell International Inc. Kompozycje, sposoby i układy wymiany ciepła
AU2019214954B2 (en) * 2018-01-30 2024-09-19 Solstice Advanced Materials Us, Inc. Heat transfer compositions, methods, and systems
CN112262196A (zh) * 2018-06-12 2021-01-22 大金工业株式会社 含有制冷剂的组合物、热传递介质和热循环系统
JP6545338B1 (ja) * 2018-08-31 2019-07-17 日立ジョンソンコントロールズ空調株式会社 冷凍サイクル装置
JP6545337B1 (ja) * 2018-08-31 2019-07-17 日立ジョンソンコントロールズ空調株式会社 冷凍サイクル装置
JP7108502B2 (ja) * 2018-09-07 2022-07-28 株式会社ダイゾー 発泡性組成物
CN113383060B (zh) * 2019-02-14 2023-02-21 出光兴产株式会社 冷冻机用组合物
JP6897814B2 (ja) * 2019-06-19 2021-07-07 ダイキン工業株式会社 冷媒を含む組成物、その使用、並びにそれを有する冷凍機及びその冷凍機の運転方法
CN110317574B (zh) * 2019-07-19 2020-10-09 珠海格力电器股份有限公司 混合制冷剂
CN113528091B (zh) * 2020-04-09 2023-03-24 浙江省化工研究院有限公司 一种含hfc-161的环保型制冷组合物
WO2022109217A1 (en) * 2020-11-20 2022-05-27 The Chemours Company Fc, Llc Refrigerant compositions and uses thereof
US20220243106A1 (en) * 2021-02-03 2022-08-04 Honeywell International Inc. Heat transfer compositions, methods, and systems
CN116179162A (zh) * 2022-12-08 2023-05-30 珠海格力电器股份有限公司 一种混合制冷剂及制冷系统
WO2024204451A1 (ja) 2023-03-28 2024-10-03 ダイキン工業株式会社 ＨＦＯ－１１３２（Ｅ）、及びＨＦＯ－１２３４ｙｆを含む混合冷媒の充填方法

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04110388A (ja) 1990-08-31 1992-04-10 Daikin Ind Ltd 熱伝達用流体
JP2000125226A (ja) * 1998-10-13 2000-04-28 Sanyo Electric Co Ltd 電源コントロール回路
KR20010057158A (ko) * 1999-12-18 2001-07-04 구자홍 전자기기의 원격 온오프 제어 장치 및 방법
JP4848576B2 (ja) 2000-04-19 2011-12-28 ダイキン工業株式会社 冷凍装置
US7279451B2 (en) * 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US20080121837A1 (en) 2003-10-27 2008-05-29 Honeywell International, Inc. Compositions containing fluorine substituted olefins
ATE556124T1 (de) * 2002-10-25 2012-05-15 Honeywell Int Inc Fluorsubstituierte olefine enthaltendezusammensetzungen
US8444874B2 (en) 2002-10-25 2013-05-21 Honeywell International Inc. Heat transfer methods using heat transfer compositions containing trans-1,3,3,3-tetrafluoropropene
US6844475B1 (en) 2003-08-08 2005-01-18 Honeywell International Business Machines Low temperature production of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd)
US10676656B2 (en) * 2003-10-27 2020-06-09 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
US7524805B2 (en) * 2004-04-29 2009-04-28 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
EP1735399A1 (en) * 2004-04-16 2006-12-27 Honeywell International, Inc. Stabilized trifluoroiodmethane compositions
US7074751B2 (en) * 2004-04-16 2006-07-11 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20060243945A1 (en) 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US7569170B2 (en) * 2005-03-04 2009-08-04 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
GB0611740D0 (en) 2006-06-14 2006-07-26 Ineos Fluor Holdings Ltd Refrigerant compositions
DE202007008291U1 (de) 2006-06-17 2007-10-18 Ineos Fluor Holdings Ltd., Runcorn Wärmeübertragungszusammensetzungen
JP2010513827A (ja) * 2006-09-01 2010-04-30 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 閉ループ・サイクル中の選択された伝熱流体の循環方法
US20080110833A1 (en) * 2006-11-14 2008-05-15 Samuels George J Iodine removal with activated carbon
FR2910016B1 (fr) * 2006-12-19 2009-02-20 Arkema France Compositions utilisables comme fluide frigorigene
US7661293B2 (en) * 2007-02-06 2010-02-16 Cosense, Inc. Ultrasonic system for detecting and quantifying of air bubbles/particles in a flowing liquid
EP2171012A1 (en) * 2007-07-27 2010-04-07 E. I. du Pont de Nemours and Company Compositions comprising fluoroolefins and uses thereof
JP2009257652A (ja) 2008-02-29 2009-11-05 Daikin Ind Ltd 冷凍装置
JP5535908B2 (ja) * 2008-03-07 2014-07-02 アーケマ・インコーポレイテッド 油リターンが改善されたハロゲン化アルケン冷媒組成物及びこれらを用いた方法
CN107384323A (zh) * 2008-07-30 2017-11-24 霍尼韦尔国际公司 含有二氟甲烷和氟取代的烯烃的组合物
US11214720B2 (en) * 2009-07-29 2022-01-04 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
FR2936806B1 (fr) 2008-10-08 2012-08-31 Arkema France Fluide refrigerant
FR2950065B1 (fr) 2009-09-11 2012-02-03 Arkema France Fluide refrigerant binaire

Also Published As

Publication number Publication date
KR101823955B1 (ko) 2018-01-31
CA2674256A1 (en) 2010-01-30
JP2021036045A (ja) 2021-03-04
JP2022184930A (ja) 2022-12-13
KR20170081148A (ko) 2017-07-11
US20250101285A1 (en) 2025-03-27
KR20160053854A (ko) 2016-05-13
MX340764B (es) 2016-07-26
CN107739594A (zh) 2018-02-27
CN101665681A (zh) 2010-03-10
JP2019031677A (ja) 2019-02-28
JP2024026168A (ja) 2024-02-28
KR20100013288A (ko) 2010-02-09
CN107739594B (zh) 2023-07-25
JP2017036452A (ja) 2017-02-16
JP5770969B2 (ja) 2015-08-26
MX2019009273A (es) 2020-01-15
JP6133921B2 (ja) 2017-05-24
CN107384322A (zh) 2017-11-24
US12195664B2 (en) 2025-01-14
CN107384323A (zh) 2017-11-24
KR101754657B1 (ko) 2017-07-06
JP2010047754A (ja) 2010-03-04
CN101665681B (zh) 2014-06-25
CN104059613A (zh) 2014-09-24
MX382469B (es) 2025-03-13
JP6799039B2 (ja) 2020-12-09
MX2021005417A (es) 2022-05-18
KR20180018601A (ko) 2018-02-21
JP2015163700A (ja) 2015-09-10
US20240263060A1 (en) 2024-08-08
MX2009008204A (es) 2010-03-22
JP2026016457A (ja) 2026-02-03

Similar Documents

Publication Publication Date Title
US12195664B2 (en) Compositions containing difluoromethane and fluorine substituted olefins
EP3473691B1 (en) Compositions containing difluoromethane and fluorine substituted olefins
US20100044619A1 (en) Compositions Containing Difluoromethane and Fluorine Substituted Olefins
US12203028B2 (en) Compositions containing difluoromethane and fluorine substituted olefins
CN103396766B (zh) 四氟丙烯和氟代烃的类共沸物组合物
US20190153281A1 (en) Compositions containing difluoromethane and fluorine substituted olefins
US20140166923A1 (en) Compositions containing difluoromethane and fluorine substituted olefins
US10676656B2 (en) Compositions containing difluoromethane and fluorine substituted olefins
WO2014130983A1 (en) Compositions containing difluoromethane and fluorine substituted olefins

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20140723

MKLA Lapsed

Effective date: 20220301

MKLA Lapsed

Effective date: 20200831