WO2009146122A1 - Refrigerant composition - Google Patents

Refrigerant composition Download PDF

Info

Publication number
WO2009146122A1
WO2009146122A1 PCT/US2009/039423 US2009039423W WO2009146122A1 WO 2009146122 A1 WO2009146122 A1 WO 2009146122A1 US 2009039423 W US2009039423 W US 2009039423W WO 2009146122 A1 WO2009146122 A1 WO 2009146122A1
Authority
WO
WIPO (PCT)
Prior art keywords
refrigerant composition
refrigerant
siloxane
acid scavenger
lubricant
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/US2009/039423
Other languages
English (en)
French (fr)
Inventor
Myrna Serrano
John W. Sherman
Oscar D. Redwine
Aaron W. Sanders
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.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to CN2009801202826A priority Critical patent/CN102046752B/zh
Priority to BRPI0906547A priority patent/BRPI0906547A2/pt
Priority to EP09755484.4A priority patent/EP2285931B1/en
Priority to JP2011503201A priority patent/JP5774981B2/ja
Publication of WO2009146122A1 publication Critical patent/WO2009146122A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • 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
    • 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
    • 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
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only 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
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C10M2209/1075—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106 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
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/042—Siloxanes with specific structure containing aromatic substituents
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • a new refrigerant material besides having low impact on the environment, should also have one or more of the following characteristics: capability of functioning in many existing refrigerant systems, relatively low flammability, relatively low toxicity, have minimal or no reaction (e.g. corrosion) with aluminum, copper and iron at temperatures below 175°C, or good thermal stability as tested using ANSI ASHRAE 97.
  • the present invention includes improved compositions, methods and systems for cooling and/or refrigeration.
  • the compositions and methods may be used in stationary or mobile systems for producing cooling.
  • the compositions and methods may be used in air conditioning systems for commercial, industrial or residential buildings.
  • the compositions and methods may also be used in refrigerators or freezers (stationary and mobile), whether commercial, industrial or residential.
  • the present inventions find their preferred application in auto vehicles (e.g., vehicle air conditioning systems) or other portable cooling systems.
  • Leek et al. (US Patent Application Publication No. 2007/0187639, paragraph 10, hereby incorporated by reference) further lists examples of unsaturated fluorocarbon refrigerants which may be used as the fluoroolefins in the present invention.
  • the refrigerant may include one or a combination of the above individual refrigerants.
  • the lubricants may be selected to have a viscosity of between about 10 and about 460 cSt at 40 0 C, preferably between about 22 and about 220 cSt at 4O 0 C and most preferably between about 40 and about 150 cSt at 40°C.
  • the wt % of the lubricant will typically affect the mutual solubility of the refrigerant and lubricant and thus the available operating temperatures for the refrigeration device.
  • the refrigerant makes up greater than about 50 percent by weight ("wt %"), preferably greater than 70 wt % and more preferably greater than 80 wt% of the total refrigerant composition at the time the composition is charged into a system.
  • the refrigerant may be less than about 99 wt %, preferably less than 98 wt % and more preferably less than about 95 wt % of the total refrigerant composition at the time the composition is charged into a system.
  • siloxane may consist essentially of polydimethylsiloxane, hexamethyldisoloxane, or a combination thereof.
  • preferable siloxanes also include siloxane capped polyalkylene glycols, such as an adduct of a second polyalkylene glycol and a siloxane.
  • R 3 , R 4 , R 5 are alkyl, aromatic, allylic, or hydrogen (preferably R 3 , R 4 , R 5 are alkyl, aromatic, or allylic).
  • the silylchloride may have the structure of Formula Il where R 3 , R 4 , R 5 are alkyl, or hydrogen and each contain from about 0 to about 4 carbon atoms (preferably from 1 to 4 carbon atoms).
  • Exemplary silylchlorides include trialkylsilylchlorides (for example, trimethylsilylchloride).
  • the acid scavenger preferably is not a fluoralkyl polysiloxane, such as the anti- load additive described by Kawaguchi et al. (US Patent No. 6,475,405 issued November 5, 2002), column 8, line 63 to column 9 line 18.
  • suitable acid scavenger may be free of fluorine atoms, free of Si-O-Si groups, or both.
  • the activated aromatic compound may be any aromatic molecule activated towards a Friedel-Crafts addition reaction, or mixtures thereof.
  • An aromatic molecule activated towards a Friedel-Crafts addition reaction is defined to be any aromatic molecule capable of an addition reaction with mineral acids. Especially aromatic molecules capable of addition reactions with mineral acids either in the application environment (AC system) or during the ASHRAE Standard 97-199 thermal stability test.
  • the acid scavenger e.g., the activated aromatic compound, the siloxane, or both
  • the acid scavenger may be present in any concentration that results in a relatively low total acid number, a relatively low total halides concentration, a relatively low total organic acid concentratioin, or any combination thereof.
  • the acid scavenger is present at a concentration greater than about 0.0050 wt %, more preferably greater than about 0.05 wt % and even more preferably greater than about 0.1 wt % (e.g. greater than about 0.5 wt %) based on the total weight of the refrigerant composition.
  • acid scavengers which may be included in the refrigerant composition and preferably are excluded from the refrigerant composition include those described by Kaneko (US Patent Application No. 11/575256, published as 20070290164, paragraph 42, expressly incorporated herein by reference), such as one or more of: phenyl glycidyl ethers, alkyl glycidyl ethers, alkyleneglycolglycidylethers, cyclohexeneoxides, ⁇ - olefinoxides, or epoxy compounds such as epoxidized soybean oil, and those described by Singh et al. (US Patent Application No. 11/250219, published as 20060116310, paragraphs 34-42, expressly incorporated herein by reference).
  • the overall resulting refrigerant composition may exhibit a relatively low total halides concentration (or more specifically, a relatively low fluorine ion concentration) of less than about 240 ppm, preferably less than about 40 ppm, more preferably less than about 10 ppm, and most preferably less than about 5 ppm after aging per ANSI ASHRAE 97 for 14 days at 175°C with aluminum, copper and iron metal strips, as measured by ion chromatography.
  • a relatively low total halides concentration or more specifically, a relatively low fluorine ion concentration
  • the overall resulting refrigerant compositions of the present invention may also include an additive or an additives package with one or any combination of the following: an extreme pressure additive, an anti-wear additive, an antioxidant, a high-temperature stabilizer, a lubricity additive, a viscosity index improver, a metal deactivator, a corrosion inhibitor, a detergent, a dispersant or an anti-foaming agent.
  • Extreme pressure additives improve the lubricity and load bearing characteristics of the refrigerant composition.
  • Preferred additives include those described in U.S. Pat. Nos. 5,152,926; 4,755,316, which are hereby incorporated by reference.
  • the refrigerant composition may be supplied as a kit.
  • the refrigerant composition may be supplied as a kit comprising a refrigerant component (which may contain most or all of the refrigerant) and a lubricant component (which may contain most or all of the lubricant), with each additive added to the refrigerant component, the lubricant component or both.
  • all of the additives are added to either the refrigerant component or the lubricant component.
  • essentially all of the additives may be in the lubricant component and the refrigerant component may consist essentially of the refrigerant.
  • any numerical values recited herein include all values from the lower value to the upper value in increments of one unit provided that there is a separation of at least 2 units between any lower value and any higher value.
  • the amount of a component or a value of a process variable such as, for example, temperature, pressure, time and the like is, for example, from 1 to 90, preferably from 20 to 80, more preferably from 30 to 70, it is intended that values such as 15 to 85, 22 to 68, 43 to 51, 30 to 32 etc. are expressly enumerated in this specification.
  • one unit is considered to be 0.0001 , 0.001 , 0.01 or 0.1 as appropriate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
PCT/US2009/039423 2008-04-04 2009-04-03 Refrigerant composition Ceased WO2009146122A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN2009801202826A CN102046752B (zh) 2008-04-04 2009-04-03 制冷剂组合物
BRPI0906547A BRPI0906547A2 (pt) 2008-04-04 2009-04-03 composição refrigerante e kit para uma composição refrigerante
EP09755484.4A EP2285931B1 (en) 2008-04-04 2009-04-03 Refrigerant composition
JP2011503201A JP5774981B2 (ja) 2008-04-04 2009-04-03 冷媒組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4239208P 2008-04-04 2008-04-04
US61/042,392 2008-04-04

Publications (1)

Publication Number Publication Date
WO2009146122A1 true WO2009146122A1 (en) 2009-12-03

Family

ID=41377493

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/039423 Ceased WO2009146122A1 (en) 2008-04-04 2009-04-03 Refrigerant composition

Country Status (7)

Country Link
US (2) US8003003B2 (enExample)
EP (1) EP2285931B1 (enExample)
JP (1) JP5774981B2 (enExample)
KR (1) KR101593716B1 (enExample)
CN (1) CN102046752B (enExample)
BR (1) BRPI0906547A2 (enExample)
WO (1) WO2009146122A1 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102115662A (zh) * 2010-03-11 2011-07-06 濮阳市中炜精细化工有限公司 替代二氟一氯甲烷用新型环保制冷剂组成物
WO2019147364A1 (en) * 2018-01-23 2019-08-01 The Chemours Company Fc, Llc Compositions, system and methods for introducing poe lubricant into an electric (hev, phev, ev) automotive air-conditioning/heating system or stationary air-conditioning/heating system or stationary refrigeration system using lower or low gwp refrigerant or refrigerant blends
US11453834B2 (en) 2018-01-23 2022-09-27 The Chemours Company Fc, Llc Compositions, system and methods for introducing POE lubricant into an air-conditioning or a refrigeration system
US12351772B2 (en) 2018-01-23 2025-07-08 The Chemours Company Fc, Llc Compositions, system and methods for introducing PAG lubricant or refrigerant into an air-conditioning or system using lower or low GWP refrigerant or refrigerant blends

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8038899B2 (en) 2008-04-28 2011-10-18 Honeywell International Inc. Refrigerant compositions having a siloxane solubilizing agent
US20100205980A1 (en) * 2008-12-23 2010-08-19 Shrieve Chemical Products, Inc. Refrigerant lubricant composition
FR2948679B1 (fr) * 2009-07-28 2011-08-19 Arkema France Procede de transfert de chaleur
US9157018B2 (en) 2010-11-25 2015-10-13 Arkema France Compositions of chloro-trifluoropropene and hexafluorobutene
FR2968009B1 (fr) 2010-11-25 2012-11-16 Arkema France Fluides frigorigenes contenant du (e)-1,1,1,4,4,4-hexafluorobut-2-ene
FR2968310B1 (fr) 2010-12-03 2012-12-07 Arkema France Compositions a base de 1,1,1,4,4,4-hexafluorobut-2-ene et de 3,3,4,4,4-pentafluorobut-1-ene
FR2971512B1 (fr) 2011-02-10 2013-01-18 Arkema France Compositions binaires de 2,3,3,3-tetrafluoropropene et d'ammoniac
FR2977256B1 (fr) 2011-07-01 2013-06-21 Arkema France Compositions de 2,4,4,4-tetrafluorobut-1-ene et de cis-1,1,1,4,4,4-hexafluorobut-2-ene
US9638343B2 (en) * 2011-12-12 2017-05-02 Massachusetts Institute Of Technology Sharp-phase change shape memory alloy thermal actuator
FR2986007B1 (fr) * 2012-01-25 2015-01-23 Arkema France Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification
FR2986236B1 (fr) * 2012-01-26 2014-01-10 Arkema France Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification
FR2989084B1 (fr) 2012-04-04 2015-04-10 Arkema France Compositions a base de 2,3,3,4,4,4-hexafluorobut-1-ene
FR3008419B1 (fr) 2013-07-11 2015-07-17 Arkema France Compositions a base de 2,3,3,3-tetrafluoropropene presentant une miscibilite amelioree
US10386099B2 (en) 2014-01-16 2019-08-20 Shrieve Chemical Products, Inc. Desicating synthetic refrigeration oil composition for fluoro-olefin refrigeration systems
EP3278038A1 (en) 2015-03-30 2018-02-07 Carrier Corporation Low-oil refrigerants and vapor compression systems
US10641529B2 (en) 2015-06-16 2020-05-05 Carrier Corporation Heat transfer system with tribofilm on bearing surface
CN105647480A (zh) * 2016-01-22 2016-06-08 杨超 一种具有堵漏功能的制冷剂及其制备方法
CN105925248A (zh) * 2016-04-29 2016-09-07 成都蓉阳科技有限公司 一种用于替代二氟一氯甲烷的环保混合制冷剂
US10612825B2 (en) * 2016-05-10 2020-04-07 Trane International Inc. Lubricant blends to reduce refrigerant solubility
KR102442032B1 (ko) * 2017-10-13 2022-09-07 주식회사 엘지에너지솔루션 방열 특성이 우수한 전지모듈 및 이를 포함하는 전지팩
US10883063B2 (en) * 2018-01-23 2021-01-05 The Chemours Company Fc, Llc Compositions, system and methods for introducing PAG lubricant or refrigerant into an air-conditioning or system using lower or low GWP refrigerant or refrigerant blends
PT3775091T (pt) 2018-04-30 2023-05-12 Chemours Co Fc Llc Composições de fluoro-olefinas estabilizadas e métodos para a sua produção, armazenamento e utilização
KR102873781B1 (ko) * 2018-12-31 2025-10-20 허니웰 인터내셔날 인코포레이티드 안정화된 열 전달 조성물, 방법 및 시스템
FR3092585B1 (fr) * 2019-02-05 2021-02-12 Total Marketing Services Composition lubrifiante pour compresseur
JP7690563B2 (ja) * 2021-03-03 2025-06-10 Ｅｎｅｏｓ株式会社 ポリアルキレンジオール変性物
JPWO2022186251A1 (enExample) * 2021-03-03 2022-09-09
WO2022192212A1 (en) 2021-03-08 2022-09-15 The Chemours Company Fc, Llc Compositions comprising 2,3,3,3-tetrafluoropropene and oxygen-derived oligomers
KR20230154966A (ko) 2021-03-08 2023-11-09 더 케무어스 컴퍼니 에프씨, 엘엘씨 2,3,3,3-테트라플루오로프로펜 및 산화 생성물을 포함하는 조성물
MX2023014167A (es) 2021-07-12 2024-01-10 Chemours Co Fc Llc Composiciones de fluoroetileno estabilizadas y metodos para su almacenamiento y uso.
JP7348535B2 (ja) * 2021-07-15 2023-09-21 ダイキン工業株式会社 アルケンの製造方法
AU2022370363A1 (en) 2021-10-21 2024-04-18 The Chemours Company Fc, Llc Compositions comprising 2,3,3,3-tetrafluoropropene
AU2022373456A1 (en) 2021-10-21 2024-04-18 The Chemours Company Fc, Llc Stabilized blend compositions comprising 2,3,3,3-tetrafluoropropene
KR20240093643A (ko) 2021-10-21 2024-06-24 더 케무어스 컴퍼니 에프씨, 엘엘씨 2,3,3,3-테트라플루오로프로펜을 포함하는 안정화된 조성물
AU2023210179A1 (en) 2022-01-18 2024-06-13 The Chemours Company Fc, Llc Fluoroolefin compositions containing a dye and methods for their production, storage and usage
JP2025508250A (ja) 2022-03-18 2025-03-21 ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー １２３４ｙｆ組成物のための炭化水素添加剤、並びにそれらの生成、保管、及び使用のための方法
US20250230351A1 (en) 2022-04-22 2025-07-17 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and hexafluorobutene
WO2024211642A1 (en) 2023-04-06 2024-10-10 The Chemours Company Fc, Llc Refrigerant compositions comprising z-1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof
WO2025019188A1 (en) 2023-07-17 2025-01-23 The Chemours Company Fc, Llc Methods and equipment for transporting, transferring, storing and using refrigerants
WO2025019197A1 (en) 2023-07-17 2025-01-23 The Chemours Company Fc, Llc Methods of treating difluoropropene compositions
CN117222189B (zh) * 2023-09-08 2025-04-04 超聚变数字技术有限公司 氢氟烯烃化合物在两相浸没式冷却系统中的应用
TW202513517A (zh) 2023-09-29 2025-04-01 美商科慕Ｆｃ有限責任公司 含氟乙烯之穩定化組成物、用於其儲存及／或運輸之方法
WO2025096368A2 (en) 2023-10-30 2025-05-08 The Chemours Company Fc, Llc Compositions comprising 1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof
TW202528277A (zh) 2023-10-30 2025-07-16 美商科慕Ｆｃ有限責任公司 包含１，３，３，３－四氟丙烯的組成物、其製造方法、及其用途
WO2025165956A1 (en) 2024-01-31 2025-08-07 The Chemours Company Fc, Llc Recovered and reclaimed thermal management fluid compositions
WO2025165958A1 (en) 2024-01-31 2025-08-07 The Chemours Company Fc, Llc Recovered and reclaimed thermal management fluid compositions

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4359394A (en) 1978-10-30 1982-11-16 Thermo King Corporation Thermally stable lubricants for refrigerator systems
US4707280A (en) 1985-05-20 1987-11-17 Nippon Mining Co., Ltd. Lubricating oil for use in Flon atmosphere
US20010019120A1 (en) 1999-06-09 2001-09-06 Nicolas E. Schnur Method of improving performance of refrigerant systems
US6475405B1 (en) 1988-12-06 2002-11-05 Idemitsu Kosan Co., Ltd. Lubricating oil for refrigerator with compressor
US20060022166A1 (en) * 2004-04-16 2006-02-02 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and pentafluoropropene
US20060116310A1 (en) 2004-04-16 2006-06-01 Honeywell International Inc. Compositions of HFC-152a and CF3I
WO2006069362A2 (en) 2004-12-21 2006-06-29 Honeywell International Inc. Stabilized iodocarbon compositions
US20070187639A1 (en) 2006-01-13 2007-08-16 Leck Thomas J Refrigerant additive compositions containing perfluoropolethers
WO2007105452A1 (ja) 2006-03-10 2007-09-20 Idemitsu Kosan Co., Ltd. 冷凍機油組成物
WO2007126760A2 (en) 2006-03-30 2007-11-08 E. I. Du Pont De Nemours And Company Compositions comprising iodotrifluoromethane and stabilizers
US20070290164A1 (en) 2004-09-14 2007-12-20 Idemitsu Kosan Co., Ltd. Refrigerator Oil Composition
WO2008027595A1 (en) 2006-09-01 2008-03-06 E. I. Du Pont De Nemours And Company Alkyl silane stabilizers for fluoroolefins

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4755316A (en) * 1987-10-23 1988-07-05 Allied-Signal Inc. Refrigeration lubricants
US4851144A (en) * 1989-01-10 1989-07-25 The Dow Chemical Company Lubricants for refrigeration compressors
US4971712A (en) * 1989-06-02 1990-11-20 E. I. Du Pont De Nemours And Company Compositions for compression refrigeration and methods of using them
US5384057A (en) * 1990-08-09 1995-01-24 E. I. Du Pont De Nemours And Company Compositions and process of using in refrigeration
US5976399A (en) * 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5370812A (en) * 1993-06-28 1994-12-06 Union Carbide Chemicals & Plastics Technology Corporation Lubricant compositions for refrigerators comprising polyalkylene glycol and a hydrocarbon solvent
AU8065594A (en) * 1993-11-06 1995-05-23 Castrol Limited Lubrication of refrigeration compressors
US5595678A (en) * 1994-08-30 1997-01-21 Cpi Engineering Services, Inc. Lubricant composition for ammonia refrigerants used in compression refrigeration systems
JPH09208980A (ja) * 1996-02-02 1997-08-12 Nippon Oil Co Ltd 冷凍機油組成物および冷凍機用流体組成物
US5900185A (en) * 1996-09-27 1999-05-04 University Of New Mexico Tropodegradable bromine-containing halocarbon additives to decrease flammability of refrigerants, foam blowing agents, solvents, aerosol propellants, and sterilants
WO1999036485A1 (en) * 1998-01-16 1999-07-22 E.I. Du Pont De Nemours And Company Halogenated hydrocarbon refrigerant compositions containing polymeric oil-return agents
US6467279B1 (en) * 1999-05-21 2002-10-22 Thomas J. Backman Liquid secondary cooling system
US7279451B2 (en) * 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US7560045B2 (en) * 2003-10-21 2009-07-14 Dow Global Technologies, Inc. Refrigerant composition
US7276177B2 (en) * 2004-01-14 2007-10-02 E.I. Dupont De Nemours And Company Hydrofluorocarbon refrigerant compositions and uses thereof
US7628933B2 (en) * 2005-08-19 2009-12-08 Glenn D. Short Lubricating oil compositions using polyalkylene glycol derivatives
US7708903B2 (en) * 2005-11-01 2010-05-04 E.I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
EP1951838B1 (en) * 2005-11-01 2013-07-17 E.I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US8188323B2 (en) * 2006-01-13 2012-05-29 E.I. Du Pont De Nemours And Company Refrigerant compositions containing perfluoropolyethers
US7759532B2 (en) * 2006-01-13 2010-07-20 E.I. Du Pont De Nemours And Company Refrigerant additive compositions containing perfluoropolyethers
US7563384B2 (en) * 2006-07-28 2009-07-21 Honeywell International Inc. Essentially non-flammable low global warming compositions

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4359394A (en) 1978-10-30 1982-11-16 Thermo King Corporation Thermally stable lubricants for refrigerator systems
US4707280A (en) 1985-05-20 1987-11-17 Nippon Mining Co., Ltd. Lubricating oil for use in Flon atmosphere
US6475405B1 (en) 1988-12-06 2002-11-05 Idemitsu Kosan Co., Ltd. Lubricating oil for refrigerator with compressor
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems
US20010019120A1 (en) 1999-06-09 2001-09-06 Nicolas E. Schnur Method of improving performance of refrigerant systems
US20060116310A1 (en) 2004-04-16 2006-06-01 Honeywell International Inc. Compositions of HFC-152a and CF3I
US20060022166A1 (en) * 2004-04-16 2006-02-02 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and pentafluoropropene
US20070290164A1 (en) 2004-09-14 2007-12-20 Idemitsu Kosan Co., Ltd. Refrigerator Oil Composition
WO2006069362A2 (en) 2004-12-21 2006-06-29 Honeywell International Inc. Stabilized iodocarbon compositions
US20070187639A1 (en) 2006-01-13 2007-08-16 Leck Thomas J Refrigerant additive compositions containing perfluoropolethers
WO2007105452A1 (ja) 2006-03-10 2007-09-20 Idemitsu Kosan Co., Ltd. 冷凍機油組成物
WO2007126760A2 (en) 2006-03-30 2007-11-08 E. I. Du Pont De Nemours And Company Compositions comprising iodotrifluoromethane and stabilizers
WO2008027595A1 (en) 2006-09-01 2008-03-06 E. I. Du Pont De Nemours And Company Alkyl silane stabilizers for fluoroolefins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2285931A4

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102115662A (zh) * 2010-03-11 2011-07-06 濮阳市中炜精细化工有限公司 替代二氟一氯甲烷用新型环保制冷剂组成物
WO2019147364A1 (en) * 2018-01-23 2019-08-01 The Chemours Company Fc, Llc Compositions, system and methods for introducing poe lubricant into an electric (hev, phev, ev) automotive air-conditioning/heating system or stationary air-conditioning/heating system or stationary refrigeration system using lower or low gwp refrigerant or refrigerant blends
KR20200111212A (ko) * 2018-01-23 2020-09-28 더 케무어스 컴퍼니 에프씨, 엘엘씨 더 낮은 또는 낮은 gwp의 냉매 또는 냉매 블렌드를 사용하여 전기(hev, phev, ev) 자동차 공조/난방 시스템 또는 고정식 공조/난방 시스템 또는 고정식 냉장 시스템 내에 poe 윤활제를 도입하기 위한 조성물, 시스템 및 방법
US11453834B2 (en) 2018-01-23 2022-09-27 The Chemours Company Fc, Llc Compositions, system and methods for introducing POE lubricant into an air-conditioning or a refrigeration system
EP4194532A1 (en) * 2018-01-23 2023-06-14 The Chemours Company FC, LLC Compositions, system and methods for introducing poe lubricant into an electric (hev, phev, ev) automotive air-conditioning/heating system or stationary air-conditioning/heating system or stationary refrigeration system using lower or low gwp refrigerant blends
AU2018405230B2 (en) * 2018-01-23 2023-11-30 The Chemours Company Fc, Llc Compositions, system and methods for introducing poe lubricant into an electric (HEV, PHEV, EV) automotive air-conditioning/heating system or stationary air-conditioning/heating system or stationary refrigeration system using lower or low GWP refrigerant or refrigerant blends
EP4306878A3 (en) * 2018-01-23 2024-03-20 The Chemours Company FC, LLC Compositions, system and methods for introducing poe lubricant into an electric (hev, phev, ev) automotive air-conditioning/heating system or stationary air-conditioning/heating system or stationary refrigeration system using lower or low gwp refrigerant
KR102774566B1 (ko) 2018-01-23 2025-03-04 더 케무어스 컴퍼니 에프씨, 엘엘씨 더 낮은 또는 낮은 gwp의 냉매 또는 냉매 블렌드를 사용하여 전기(hev, phev, ev) 자동차 공조/난방 시스템 또는 고정식 공조/난방 시스템 또는 고정식 냉장 시스템 내에 poe 윤활제를 도입하기 위한 조성물, 시스템 및 방법
US12351772B2 (en) 2018-01-23 2025-07-08 The Chemours Company Fc, Llc Compositions, system and methods for introducing PAG lubricant or refrigerant into an air-conditioning or system using lower or low GWP refrigerant or refrigerant blends
US12441949B2 (en) 2018-01-23 2025-10-14 The Chemours Company Fc, Llc Compositions, system and methods for introducing POE lubricant into an electric (HEV, PHEV, EV) automotive air-conditioning/heating system or stationary air-conditioning/heating system or stationary refrigeration system using lower or low GWP refrigerant or refrigerant blends

Also Published As

Publication number Publication date
KR20110007162A (ko) 2011-01-21
US20110272624A1 (en) 2011-11-10
CN102046752B (zh) 2013-07-31
KR101593716B1 (ko) 2016-02-12
EP2285931A1 (en) 2011-02-23
EP2285931A4 (en) 2014-11-19
JP2011516671A (ja) 2011-05-26
US8003003B2 (en) 2011-08-23
EP2285931B1 (en) 2017-11-08
CN102046752A (zh) 2011-05-04
BRPI0906547A2 (pt) 2017-10-10
US20090302264A1 (en) 2009-12-10
US8246852B2 (en) 2012-08-21
JP5774981B2 (ja) 2015-09-09

Similar Documents

Publication Publication Date Title
US8003003B2 (en) Refrigerant composition
US10450488B2 (en) Heat transfer compositions having improved miscibility with lubricating oil
US20100012882A1 (en) Refrigerant compositions including silyl terminated polyalkylene glycols as lubricants and methods for making the same
US9518204B2 (en) HFO refrigerant composition having improved slidability
US11427777B2 (en) Compositions, system and methods for introducing PAG lubricant or refrigerant into an air-conditioning or system using lower or low GWP refrigerant or refrigerant blends
KR100292371B1 (ko) 냉동기오일, 냉동기작동유체, 및, 냉동시스템의 윤활방법
CN105916958A (zh) 干燥的合成制冷润滑剂组合物
JP7612792B2 (ja) より低又は低ｇｗｐの冷媒又は冷媒ブレンドを用いて、ｐａｇ潤滑油又は冷媒を空調又はシステムに導入するための組成物、システム、及び方法
JP3347614B2 (ja) 冷凍機油組成物及び該組成物を用いた潤滑方法
EP4603566A1 (en) Working fluid composition, refrigeration oil, and refrigerator
US11535809B2 (en) Compressor lubricant composition

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200980120282.6

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09755484

Country of ref document: EP

Kind code of ref document: A1

REEP Request for entry into the european phase

Ref document number: 2009755484

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2009755484

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2011503201

Country of ref document: JP

Ref document number: 6304/CHENP/2010

Country of ref document: IN

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20107024668

Country of ref document: KR

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: PI0906547

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20101004