WO2020132319A1 - Foaming agent compositions containing 1,2,2-trifluoro-1-trifluoromethylcyclobutane, and methods of foaming - Google Patents

Foaming agent compositions containing 1,2,2-trifluoro-1-trifluoromethylcyclobutane, and methods of foaming Download PDF

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Publication number
WO2020132319A1
WO2020132319A1 PCT/US2019/067602 US2019067602W WO2020132319A1 WO 2020132319 A1 WO2020132319 A1 WO 2020132319A1 US 2019067602 W US2019067602 W US 2019067602W WO 2020132319 A1 WO2020132319 A1 WO 2020132319A1
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WIPO (PCT)
Prior art keywords
blowing agent
foam
hfo
composition
hfc
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/US2019/067602
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English (en)
French (fr)
Inventor
Rajiv Ratna Singh
Ryan J. Hulse
Bin Yu
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
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Priority to CN201980084830.8A priority Critical patent/CN113242876A/zh
Priority to MX2021007416A priority patent/MX2021007416A/es
Priority to EP19900420.1A priority patent/EP3898797A4/en
Priority to JP2021535993A priority patent/JP2022514907A/ja
Priority to CA3122707A priority patent/CA3122707A1/en
Publication of WO2020132319A1 publication Critical patent/WO2020132319A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08J9/141—Hydrocarbons
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    • 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
    • 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
    • C08J9/145—Halogen containing compounds containing carbon, halogen and hydrogen only only chlorine as halogen atoms
    • 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
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    • 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
    • C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
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    • C09D9/00—Chemical paint or ink removers
    • C09D9/005—Chemical paint or ink removers containing organic solvents
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    • 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
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    • C09K5/10—Liquid materials
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0043—For use with aerosol devices
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen
    • C11D7/30—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5018—Halogenated solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
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    • C11D7/5022—Organic solvents containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/5054—Mixtures of (hydro)chlorofluorocarbons and (hydro) fluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/5063—Halogenated hydrocarbons containing heteroatoms, e.g. fluoro alcohols
    • C—CHEMISTRY; METALLURGY
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    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
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    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
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    • F01K—STEAM ENGINE PLANTS; STEAM ACCUMULATORS; ENGINE PLANTS NOT OTHERWISE PROVIDED FOR; ENGINES USING SPECIAL WORKING FLUIDS OR CYCLES
    • F01K25/00—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for
    • F01K25/08—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for using special vapours
    • G—PHYSICS
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    • G06F1/20—Cooling means
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    • G06F1/16—Constructional details or arrangements
    • G06F1/20—Cooling means
    • G06F1/206—Cooling means comprising thermal management
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K7/00—Constructional details common to different types of electric apparatus
    • H05K7/20—Modifications to facilitate cooling, ventilating, or heating
    • H05K7/2029—Modifications to facilitate cooling, ventilating, or heating using a liquid coolant with phase change in electronic enclosures
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    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
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    • H05K7/20709—Modifications to facilitate cooling, ventilating, or heating for server racks or cabinets; for data centers, e.g. 19-inch computer racks
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    • H05K7/20809—Liquid cooling with phase change within server blades for removing heat from heat source
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    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
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    • H05K7/20—Modifications to facilitate cooling, ventilating, or heating
    • H05K7/20845—Modifications to facilitate cooling, ventilating, or heating for automotive electronic casings
    • H05K7/20881—Liquid coolant with phase change
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C08J2203/142—Halogenated saturated hydrocarbons, e.g. H3C-CF3
    • C—CHEMISTRY; METALLURGY
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    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
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    • C08J2203/144—Perhalogenated saturated hydrocarbons, e.g. F3C-CF3
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    • C08J2203/182—Binary blends of expanding agents of physical blowing agents, e.g. acetone and butane
    • C—CHEMISTRY; METALLURGY
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    • C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02—Homopolymers or copolymers of hydrocarbons
    • C08J2325/04—Homopolymers or copolymers of styrene
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    • C09K2205/32—The mixture being azeotropic
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    • G06F2200/201—Cooling arrangements using cooling fluid

Definitions

  • the blowing agent of the invention comprises methylal
  • the blowing agent comprises methylal in an amount of from about 5% by weight to about 50% by weight of the total blowing agent composition, more preferably from about 10% by weight to about 40% by weight, and even more preferably of from about 10% to about 20% by weight of the total blowing agent.
  • the HFC co-blowing agent is preferably present in the composition in amounts of from about 5% by weight to about 80% by weight of the total blowing agent composition, more preferably from about 10% by weight to about 75% by weight, and even more preferably of from about 25% to about 75% by weight of the total blowing agent, more preferably from about 20% by weight to about 60% by weight of the total blowing agent.
  • the blowing agent composition preferably has a GWP of not greater than about 1000, more preferably not greater than about 500, more preferably not greater than about 150.
  • blowing agent mixture may include flame retardants such as tri(2-chloroethyl)phosphate, tri(2-chloropropyl)phosphate, tri(2,3-dibromopropyl)-phosphate, tri(1 ,3-dichloropropyl) phosphate, diammonium phosphate, various halogenated aromatic compounds, antimony oxide, aluminum trihydrate, polyvinyl chloride, and the like.
  • flame retardants such as tri(2-chloroethyl)phosphate, tri(2-chloropropyl)phosphate, tri(2,3-dibromopropyl)-phosphate, tri(1 ,3-dichloropropyl) phosphate, diammonium phosphate, various halogenated aromatic compounds, antimony oxide, aluminum trihydrate, polyvinyl chloride, and the like.
  • the one or more components capable of forming foam may be a composition capable for forming a thermoplastic foam.
  • the one or more components capable of forming foam may be a thermoplastic polymer and/or resin.
  • thermoplastic foams include polyolefins, such as for example monovinyl aromatic compounds of the formula Ar-CHCH2 wherein Ar is an aromatic hydrocarbon radical of the benzene series such as polystyrene (PS).
  • suitable polyolefin resins in accordance with the invention include the various ethylene resins including the ethylene homopolymers such as polyethylene and ethylene copolymers, polypropylene (PP) and polyethyleneterepthalate (PET).
  • the thermoplastic foam may be a polyethylene (PE), polypropylene (PP), polystyrene (PS) or polyethyleneterepthalate (PET) foam.
  • the foam is a phenolic foam
  • it can be produced by foaming and curing a foamable phenolic resin composition comprising a phenolic resin, a catalyst, and optionally an inorganic filler with a blowing agent of the claimed invention.
  • the foam of the present invention can be a block, a slab, a laminate, a panel, such as a pour-in-place panel, a spray applied foam, a froth, and the like
  • thermoplastic foam is preferably polyethylene (PE), polypropylene (PP), polystyrene (PS) or polyethyleneterepthalate (PET).
  • PE polyethylene
  • PP polypropylene
  • PS polystyrene
  • PET polyethyleneterepthalate
  • the thermoplastic foam is an extruded thermoplastic foam. More particularly the foam is an extruded polystyrene foam.
  • the blowing agent of the present invention preferably comprises TFMCB either alone or in combination with one or more of water, C02, methyl formate, methylal, HFO-1234ze(E), HFO-1234yf, HFO-1336mzz(E), HFO-1336mzz(Z), HFO-1233zd(E), HFO-1233zd(Z), HFO-1224yd(E), H FO-1224yd (Z), HFC-152a, formic acid, n-pentane, isopentane, cyclopentane, trans 1 ,2-dichloroethylene, HFC-245fa, HFC-365 fc, HFC-134a and HFC-134a.
  • the phenolic foam can be a resole resin obtained from the chemical reaction of an aldehyde and a phenol or phenol based compound.
  • blowing agent in accordance with the present invention into a foamable composition and then foaming the composition, preferably by a step or series of steps which include causing volumetric expansion of the blowing agent in accordance with the present invention.
  • presently used systems and devices for incorporation of blowing agent and for foaming can readily be used in accordance with the present invention.
  • one advantage of the present invention is the provision of an improved blowing agent which is generally compatible with existing foaming methods and systems.
  • the step of introducing the blowing agent into the thermoplastic material may comprise introducing the blowing agent into an extruder (e.g. a screw extruder) containing the thermoplastic, and the step of causing foaming may comprise lowering the pressure on the thermoplastic material and thereby causing expansion of the blowing agent and contributing to the foaming of the material.
  • an extruder e.g. a screw extruder
  • blowing agent it may be desired to introduce one or more components of the blowing agent at first location in the extruder, which is upstream of the place of addition of one or more other components of the blowing agent, with the expectation that the components will come together in the extruder and/or operate more effectively in this manner. Nevertheless, it may be preferred that two or more components of the blowing agent are combined in advance and introduced together into the foamable composition, either directly or as part of premix which is then further added to other parts of the foamable composition.
  • Such one component systems are typically and preferably packaged in a container, such as an aerosol type can, and the blowing agent of the present invention thus preferably provides for expansion of the foam and/or the energy to transport the foam/foamable material from the package, and preferably both.
  • Such systems and methods may comprise charging the package with a fully formulated system (preferably isocyanate/polyol system) and incorporating a gaseous blowing agent in accordance with the present invention into the package, preferably an aerosol type can.
  • the blowing agent composition including TFMCB as a nucleating agent may comprise the TFMCB in an amount as low as about 0.5, about 1 wt.%, about 1.5 wt.%, about 2 wt.%, about 2.5 wt.%, about 3 wt.%, or about 3.5 wt.%, or as high as about 4 wt.%, about 4.5 wt.%, about 5 wt.%, about 5.5 wt.%, about 6 wt.%, about 6.5 wt.% or about 7 wt.%, or any value between any two of the forgoing values, such as about 0.5 wt.% to about 7 wt.%, about 1 wt.% to about 6.5 wt.
  • the thermoplastic foam is preferably polyethylene (PE), polypropylene (PP), polystyrene (PS) or polyethyleneterepthalate (PET).
  • PE polyethylene
  • PP polypropylene
  • PS polystyrene
  • PET polyethyleneterepthalate
  • the thermoplastic foam is an extruded thermoplastic foam. More particularly the foam is an extruded polystyrene foam.
  • a polyurethane foam was prepared from the following composition: Stepanpol
  • compositions including TFMCB as a blowing agent and nucleating agent are shown in Table 1.
  • the polyol preblend was allowed to react with an isocyanate to produce a polyurethane foam.
  • the foam sample was allowed to cure for 24hrs before cutting.
  • the thermal conductivity value was recorded using the LaserComp FOX50 Heat Flow Meter on a 12”x 2”x” sample.
  • 245fa surprisingly show a decreased thermal conductivity below about 7 wt.% TFMCB as the TFMCB functions as a nucleating agent. Above about 7 wt.%, the thermal conductivity increases as TFMCB functions as more of a blowing agent, replacing the R245fa.
  • the nucleating effect is not as dramatic as in Example 2 due to the lower thermal conductivity of the R245fa, compared to cP. This effect is found at 50°F and 75°F and indicates better thermal insulation properties of the foam with TFMCB used as a nucleating agent.
  • a polyurethane foam was prepared from the following composition: Stepanpol
  • the extruder is divided into 10 sections, each representing a L:D of 4:1.
  • the polystyrene resin was introduced into the first section, the blowing agent was introduced into the sixth section, with the extrudate exiting the tenth section.
  • the extruder operated primarily as a melt /mixing extruder.
  • a subsequent cooling extruder is connected in tandem, for which the design characteristics were:
  • Polystyrene resin namely Nova Chemical - general extrusion grade polystyrene, identified as Nova 1600, is feed to the extruder under the conditions indicated above.
  • the resin has a recommended melt temperature of 375 °F - 525 °F.
  • the pressure of the extruder at the die is about 1320 pounds per square inch (psi), and the temperature at the die is about 115 °C.
  • a polyurethane foam is prepared and is adapted for use as a commercial “appliance type” polyurethane formulation.
  • the same foam formulation described in Example 1 is used in connection with the same standard commercial polyurethane processing equipment is used in the foam forming process.
  • Several systems are prepared, with each system using identical components, systems, and equipment, with the exception of the blowing agent.
  • HFC-134a, HFC-245fa, and cyclopentane are each also tested as the blowing agent.
  • the blowing agent is added in substantially the same molar concentration into the polyol blend.
  • the polyol blend consists of commercial polyol(s), catalyst(s), and surfactant(s).
  • the foams are prepared in accordance with standard commercial manufacturing operations, for example a commercial operation for making foam for refrigeration applications.
  • blowing agent compositions including TFMCB as a nucleating agent and a blowing agent including cyclopentane, HFC-245fa, R- 1233zd(E), or HFO-1336mzz(Z)
  • cyclopentane, HFC-245fa, R-1233zd(E), or HFO-1336mzz(Z) are each also tested as the blowing agent without TFMCB as a nucleating agent.
  • the blowing agent composition is added in substantially the same molar concentration into the polyol blend.
  • the polyol blend consists of commercial polyol(s), catalyst(s), and surfactant(s).
  • the foams are prepared in accordance with standard commercial manufacturing operations, for example a commercial operation for making foam for refrigeration applications.
  • Aspect 3 is the blowing agent composition of Aspect 2, wherein the blowing agent comprises cyclopentane, HFC-245fa, R-1233zd(E), HFO-1336mzz(Z), or
  • Aspect 6 is the blowing agent composition of Aspect 3, wherein the blowing agent consists of R-1233zd(E).
  • Aspect 7 is the blowing agent composition of Aspect 3, wherein the blowing agent consists of HFO-1336mzz(Z).
  • Aspect 11 is the blowing agent composition of any of Aspects 1 to 8, wherein the TFMCB present in the composition in an amount from about 3 wt.% to about 5 wt.% of the blowing agent composition
  • Aspect 18 is the use of the blowing agent composition of any of Aspects 1 to 17 in the production of a thermoset foam.
  • Aspect 20 is a foamable composition comprising a foam forming agent and a blowing agent composition.
  • the blowing agent comprises a blowing agent and a nucleating agent.
  • the nucleating agent includes 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane (TFMCB).
  • TFMCB is present in the blowing agent composition in an amount from about 0.5 wt.% to about 7 wt.% of the blowing agent composition.
  • Aspect 21 is the foamable composition of Aspect 20, wherein the foam forming agent comprises at least one thermoset foam component.
  • Aspect 26 is the foamable composition of Aspect 25, wherein the blowing agent comprises cyclopentane, HFC-245fa, R-1233zd(E), HFO-1336mzz(Z), or
  • Aspect 27 is the foamable composition of Aspect 26, wherein the blowing agent consists of cyclopentane.
  • Aspect 30 is the foamable composition of Aspect 256 wherein the blowing agent consist of HFO-1336mzz(Z)
  • Aspect 31 is a foam comprising a plurality of polymeric cells and a
  • composition contained in at least one of the cells comprises a blowing agent and a nucleating agent.
  • the nucleating agent includes 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane (TFMCB).
  • TFMCB is present in the cell in an amount from about 0.1 wt.% to about 3 wt.% of the composition.
  • Aspect 33 is the foam composition of Aspect 21 , wherein the TFMCB is present in the cell in an amount from about 0.6 wt.% to about 2 wt.% of the composition.
  • Aspect 34 is the foam composition of Aspect 21 , wherein the TFMCB is present in the cell in an amount from about 0.8 wt.% to about 1.2 wt.% of the composition.
  • Aspect 35 is the foam of any of Aspects 31 to 34 in the form of a rigid foam.
  • Aspect 36 is the foam of any of Aspects 31 to 34 in the form of a flexible foam.
  • Aspect 37 is the foam of any of Aspects 31 to 34 in the form of an integral skin foam.
  • Aspect 38 is the foam of any of Aspects 31 to 37 in the form of an open cell foam.
  • Aspect 39 is the foam of any of Aspects 31 to 37 in the form of a closed cell foam.
  • Aspect 44 is the foam of Aspects 31-42 which is an extruded polystyrene foam.
  • Aspect 46 is a freezer comprising the foam of any of Aspects 31-44.
  • Aspect 48 is the method of Aspect 47, further comprising providing the foam forming agent, wherein providing the foam forming agent comprises mixing a polyol and an isocyanate together, and reacting the polyol and the isocyanate together.

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MX2021007416A MX2021007416A (es) 2018-12-21 2019-12-19 Composiciones de agente espumante que contienen 1,2,2-trifluoro-1-trifluorometilciclobutano y metodos de espumado.
EP19900420.1A EP3898797A4 (en) 2018-12-21 2019-12-19 EXPANSION AGENT COMPOSITIONS CONTAINING 1,2,2-TRIFLUORO-1-TRIFLUOROMETHYLCYCLOBUTANE, AND METHODS OF EXPANSION
JP2021535993A JP2022514907A (ja) 2018-12-21 2019-12-19 １，２，２－トリフルオロ－１－トリフルオロメチルシクロブタンを含有する起泡剤組成物、及び発泡方法
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025183994A1 (en) * 2024-02-26 2025-09-04 Honeywell International Inc. Low gwp fluids for high temperature heat pump applications
EP4506400A4 (en) * 2022-06-01 2025-09-10 Jsp Corp POLYOLEFIN RESIN FOAM PARTICLES AND PROCESS FOR THEIR MANUFACTURE

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020115602A1 (en) * 2018-12-03 2020-06-11 3M Innovative Properties Company Visually distinguishable working fluids
CN113242876A (zh) 2018-12-21 2021-08-10 霍尼韦尔国际公司 包含1,2,2-三氟-1-三氟甲基环丁烷的发泡剂组合物及发泡方法
JP7156262B2 (ja) * 2019-12-19 2022-10-19 トヨタ自動車株式会社 電池搭載車両
FR3106347B1 (fr) * 2020-01-20 2023-07-07 Arkema France Régulation thermique d’équipements électriques
FR3115287B1 (fr) * 2020-10-19 2023-11-24 Arkema France Refroidissement d’une batterie par immersion dans une composition avec changement d’état
FR3115290B1 (fr) * 2020-10-19 2023-11-17 Arkema France Régulation thermique d’une batterie par immersion dans une composition liquide
EP4235702A4 (en) * 2020-10-22 2024-07-24 Agc Inc. ELECTRICAL EQUIPMENT
US12054596B2 (en) 2020-11-30 2024-08-06 Honeywell International Inc. Azeotrope or azeotrope-like compositions of Z-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z))
JP7568523B2 (ja) * 2021-01-20 2024-10-16 株式会社ジェイエスピー ポリスチレン系樹脂押出発泡板の製造方法
US11812589B2 (en) * 2021-05-12 2023-11-07 Nvidia Corporation Intelligent refrigerant distribution unit for datacenter cooling systems
US11765859B2 (en) * 2021-10-12 2023-09-19 The Chemours Company Fc, Llc Methods of immersion cooling with low-GWP fluids in immersion cooling systems
US20230247795A1 (en) 2022-01-28 2023-08-03 The Research Foundation For The State University Of New York Regenerative preheater for phase change cooling applications
CN114828548B (zh) * 2022-03-10 2025-08-05 北京比特大陆科技有限公司 机箱、电子设备和机箱排气方法
US12185497B2 (en) * 2022-08-19 2024-12-31 Super Micro Computer, Inc. Fluid immersion cooling system with low flash point hydrocarbon dielectric fluid
WO2024081394A1 (en) * 2022-10-13 2024-04-18 Honeywell International Inc. Compositions comprising fluorine substituted ethers and methods and uses including same
EP4606188A1 (en) * 2022-10-17 2025-08-27 Trane International Inc. Cooling systems and methods with radiative cooling
IT202200022353A1 (it) * 2022-10-31 2024-05-01 Ferrari Spa Autoveicolo con un apparecchio di condizionamento per raffreddare dispositivi elettrici dell'autoveicolo
JP7620051B1 (ja) * 2023-07-07 2025-01-22 美浜株式会社 被膜形成用材料、及び洗浄剤
US12114465B1 (en) * 2023-07-25 2024-10-08 Marathon Digital Holdings, Inc. Conversion of immersion cooling systems for use with single-phase operating fluids
US20250043817A1 (en) * 2023-08-03 2025-02-06 Garrett Transportation I Inc. Airfoil bearing arrangement and method for making the same
FR3140088A1 (fr) * 2023-09-28 2024-03-29 Arkema France Refroidissement d’une batterie par immersion dans une composition avec changement d’état
US12321209B1 (en) * 2024-04-05 2025-06-03 MARA Holdings, Inc. Method of subsidizing cost of providing information
CN119325209A (zh) * 2024-09-06 2025-01-17 上海航天控制技术研究所 一种飞行器控制设备热管理装置及热控方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993007201A2 (en) * 1991-10-04 1993-04-15 Minnesota Mining And Manufacturing Company Fine-celled plastic foam containing halogenated blowing agent
JPH06329826A (ja) * 1993-05-17 1994-11-29 Daikin Ind Ltd フルオロシクロブタン化合物からなる発泡剤
EP0427533B1 (en) * 1989-11-08 1997-07-16 The Dow Chemical Company Use of nucleating blowing agents in the preparation of insulating alkenyl aromatic polymer foams
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20120043492A1 (en) * 2010-08-17 2012-02-23 Honeywell International Inc. Compositions Containing 1-Chloro-3,3,3 Trifluoropropene And 1-Fluoro-1,1 Dichloroethane

Family Cites Families (126)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2462345A (en) 1943-04-23 1949-02-22 Du Pont Monomeric fluorine compounds containing a four-carbon atom ring
US2441128A (en) 1943-09-03 1948-05-11 Du Pont Polyfluoro four-carbon atom ring carboxylic acids and derivatives
US2427116A (en) 1945-05-22 1947-09-09 Du Pont Heptafluoromonochlorocyclobutane and process of making same
BE536296A (https=) 1954-03-22
IT535373A (https=) 1954-06-10
US2848504A (en) 1954-07-21 1958-08-19 Du Pont Alkyl hexafluorocyclobutanes and process for preparing them
US2846458A (en) 1956-05-23 1958-08-05 Dow Corning Organosiloxane ethers
US2982786A (en) 1958-07-09 1961-05-02 Du Pont Novel cyclic dimers of perfluorovinyl ethers
US2931840A (en) 1958-11-25 1960-04-05 Du Pont Process for preparing 2, 3, 3, 3-tetrafluoropropene
NL121693C (https=) 1959-05-22
US3996301A (en) 1972-09-22 1976-12-07 Phillips Petroleum Company Producing vinylidene fluoride substantially free from tetrafluoroethylene
US3996299A (en) 1973-02-08 1976-12-07 Phillips Petroleum Company Fluoro compound preparation
JPS5171188A (en) * 1974-12-17 1976-06-19 Osaka Prefecture Kitaichuno kitaijo oyobi ryushijoioto sonokagobutsuo dojinibunsekisuru hoho narabini sono sochi
EP0127365A3 (en) 1983-05-20 1988-03-16 Imperial Chemical Industries Plc Heat pumps
US5035830A (en) 1990-03-21 1991-07-30 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of hexafluoropropylene/ethylene cyclic dimer with methanol or ethanol
US5026499A (en) * 1990-03-21 1991-06-25 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions of hexafluoropropylene/ethylene cyclic dimer with trans-1,2-dichloroethylene and methanol
US4986928A (en) * 1990-03-21 1991-01-22 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of 1-chloro-1,2,2-trifluorocyclobutane and methanol
US5196137A (en) 1991-10-01 1993-03-23 E. I. Du Pont De Nemours And Company Azeotropic composition of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene, cis-1,2-dichloroethylene or 1,1-dichlorethane
US5210106A (en) 1991-10-04 1993-05-11 Minnesota Mining And Manufacturing Company Fine-celled plastic foam containing fluorochemical blowing agent
US5221493A (en) 1991-10-18 1993-06-22 E. I. Du Pont De Nemours And Company Azeotropic compositions of 1,1,2,2,3,3,4,4-octafluorobutane and alcohols or ketones
US5159527A (en) 1991-12-05 1992-10-27 Minnesota Mining And Manufacturing Company Dielectric liquids
JPH05171188A (ja) * 1991-12-25 1993-07-09 Asahi Glass Co Ltd 洗浄に用いる組成物
JPH05168810A (ja) 1991-12-25 1993-07-02 Asahi Glass Co Ltd 付着水除去のための組成物
US5182342A (en) 1992-02-28 1993-01-26 E. I. Du Pont De Nemours And Company Hydrofluorocarbon solvents for fluoromonomer polymerization
US5194170A (en) 1992-04-02 1993-03-16 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of 1,1,2,2,3,3,4,4-octafluorobutane and either tran-1,2-dichloroethylene, cis 1,2-dichloroethylene, or 1-1 dichloroethane
US5250208A (en) 1992-04-02 1993-10-05 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions
JPH0649490A (ja) * 1992-07-29 1994-02-22 Asahi Glass Co Ltd 洗浄剤組成物
US5310870A (en) 1992-08-13 1994-05-10 E. I. Du Pont De Nemours And Company Fluoroalkene/hydrofluorocarbon telomers and their synthesis
JP2651652B2 (ja) * 1993-05-07 1997-09-10 工業技術院長 フッ素化アルコール系洗浄剤
JP3500617B2 (ja) 1993-08-27 2004-02-23 ダイキン工業株式会社 ヘキサフルオロシクロブタンの製造方法
US5336696A (en) * 1993-12-10 1994-08-09 Nisshinbo Industries, Inc. Halogen-free blowing agents that include cycloaliphatic hydrocarbons and are suitable for isocyanate-based polymeric foams
US5434195A (en) 1994-06-23 1995-07-18 The Dow Chemical Company Extruded, open-cell alkenyl aromatic polymer foam and process for making
US5564447A (en) * 1995-01-13 1996-10-15 Awn Technologies Inc. Vapor contact lost core meltout method
US5925611A (en) * 1995-01-20 1999-07-20 Minnesota Mining And Manufacturing Company Cleaning process and composition
US5580906A (en) 1995-05-19 1996-12-03 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions
JPH0977698A (ja) * 1995-09-13 1997-03-25 Asahi Chem Ind Co Ltd ３−トリフルオロメチル−１，１，１，２，２−ペンタフルオロブタンの製造方法
AU5797296A (en) 1995-12-15 1997-07-14 Minnesota Mining And Manufacturing Company Cleaning process and composition
US5977237A (en) 1996-03-08 1999-11-02 E. I. Du Pont De Nemours And Company Flash-spinning solution
US5762817A (en) 1996-04-12 1998-06-09 E. I. Du Pont De Nemours And Company Decafluoropentane compositions
US5759986A (en) 1997-03-03 1998-06-02 Merchant; Abid Nazarali Decafluoropentane compositions
US5897809A (en) 1996-05-30 1999-04-27 E. I. Du Pont De Nemours And Company Decafluoropentane compositions
DE19640972A1 (de) 1996-10-04 1998-04-16 Bayer Ag Flüssig-Fluorkautschuk, ein Verfahren zu seiner Herstellung und seine Verwendung
US6552090B1 (en) * 1997-09-15 2003-04-22 3M Innovative Properties Company Perfluoroalkyl haloalkyl ethers and compositions and applications thereof
DE19844188A1 (de) 1998-09-28 2000-03-30 Bayer Ag Verfahren zur Herstellung eines schnellvernetzbaren Fluorkautschukes
US6159917A (en) * 1998-12-16 2000-12-12 3M Innovative Properties Company Dry cleaning compositions containing hydrofluoroether
US6127430A (en) 1998-12-16 2000-10-03 3M Innovative Properties Company Microemulsions containing water and hydrofluroethers
DE19924439A1 (de) 1999-05-28 2000-11-30 Bayer Ag Schnell vernetzendes Fluorpolymer
CN1213974C (zh) 1999-06-04 2005-08-10 纳幕尔杜邦公司 生产氟代烯烃的方法
US6516837B2 (en) 2000-09-27 2003-02-11 Honeywell International Inc. Method of introducing refrigerants into refrigeration systems
JP3996509B2 (ja) * 2000-12-21 2007-10-24 ダウ グローバル テクノロジーズ インコーポレイティド 常態では液体のヒドロフルオロカーボンと二酸化炭素を含む発泡剤組成物及びポリマーフォーム
US6423673B1 (en) * 2001-09-07 2002-07-23 3M Innovation Properties Company Azeotrope-like compositions and their use
US20090253820A1 (en) * 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US7022658B2 (en) 2003-09-29 2006-04-04 3M Innovative Properties Company Azeotrope-like compositions containing hexafluoropropylene dimer and use thereof
US9499729B2 (en) * 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US7276177B2 (en) 2004-01-14 2007-10-02 E.I. Dupont De Nemours And Company Hydrofluorocarbon refrigerant compositions and uses thereof
US8058486B2 (en) 2004-04-29 2011-11-15 Honeywell International Inc. Integrated process to produce 2,3,3,3-tetrafluoropropene
US8084653B2 (en) 2004-04-29 2011-12-27 Honeywell International, Inc. Method for producing fluorinated organic compounds
US8383867B2 (en) 2004-04-29 2013-02-26 Honeywell International Inc. Method for producing fluorinated organic compounds
US7674939B2 (en) 2004-04-29 2010-03-09 Honeywell International Inc. Method for producing fluorinated organic compounds
US7153448B2 (en) * 2004-05-26 2006-12-26 E.I. Du Pont De Nemours And Company 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof
JP4729040B2 (ja) 2004-06-25 2011-07-20 エクソンモービル・ケミカル・パテンツ・インク ハイドロフルオロカーボンを用いる重合プロセス
US7428816B2 (en) 2004-07-16 2008-09-30 Honeywell International Inc. Working fluids for thermal energy conversion of waste heat from fuel cells using Rankine cycle systems
ES2314713T3 (es) * 2004-10-05 2009-03-16 Asahi Glass Company, Limited Composicion disolvente de tipo azeotropico y composicion disolvente mixta.
CN101056921A (zh) 2004-11-08 2007-10-17 3M创新有限公司 使用氢氟醚成核剂制备聚合物泡沫
CA2621520C (en) 2005-09-08 2014-03-11 Kingspan Holdings (Irl) Limited A phenolic foam
KR101350620B1 (ko) * 2005-11-01 2014-02-06 이 아이 듀폰 디 네모아 앤드 캄파니 플루오로올레핀을 포함하는 조성물 및 그의 용도
US7708903B2 (en) 2005-11-01 2010-05-04 E.I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US8324436B2 (en) 2006-01-03 2012-12-04 Honeywell International Inc. Gas phase synthesis of 2,3,3,3-tetrafluoro-1-propene from 2-chloro-3,3,3-trifluoro-1-propene
US7420094B2 (en) 2006-09-05 2008-09-02 E.I. Du Pont De Nemours And Company Catalytic isomerization processes of 1,3,3,3-tetrafluoropropene for making 2,3,3,3-tetrafluoropropene
WO2008038682A1 (fr) 2006-09-28 2008-04-03 Asahi Glass Company, Limited Nouveau polymère fluoré
WO2008121776A1 (en) * 2007-03-29 2008-10-09 Arkema Inc. Hydrofluoropropene blowing agents for thermoplastics
GB0709033D0 (en) 2007-05-11 2007-06-20 3M Innovative Properties Co Melt-Processible fluoropolymers having long-chain branches, Methods of preparing them and uses thereof
WO2009003085A1 (en) 2007-06-27 2008-12-31 Arkema Inc. Process for the manufacture of hydrofluoroolefins via metathesis
US9079818B2 (en) 2007-10-15 2015-07-14 Honeywell International Inc. Process for synthesis of fluorinated olefins
WO2009085937A1 (en) 2007-12-20 2009-07-09 E. I. Du Pont De Nemours And Company Secondary loop cooling system having a bypass and a method for bypassing a reservoir in the system
US7442321B1 (en) * 2008-03-07 2008-10-28 Arkema Inc. Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and trans-1,2-dichloroethylene
CN105669891A (zh) 2008-07-07 2016-06-15 阿科玛股份有限公司 偏二氟乙烯/2,3,3,3-四氟丙烯共聚物
JP5348240B2 (ja) 2008-07-30 2013-11-20 ダイキン工業株式会社 ２，３，３，３−テトラフルオロプロペンの製造方法
US8975454B2 (en) 2008-07-31 2015-03-10 Honeywell International Inc. Process for producing 2,3,3,3-tetrafluoropropene
US8198491B2 (en) 2008-08-06 2012-06-12 Daikin Industries, Ltd. Process for preparing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene
US8163196B2 (en) * 2008-10-28 2012-04-24 Honeywell International Inc. Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene
US7935268B2 (en) 2008-10-28 2011-05-03 Honeywell International Inc. Azeotrope-like compositions comprising trans-1-chloro-3,3,3-trifluoropropene
US20100113691A1 (en) 2008-11-06 2010-05-06 E. I. Du Pont De Nemours And Company Fluoro olefin polymerization
CN102227395A (zh) 2008-11-13 2011-10-26 苏威氟有限公司 氢氟烯烃、氢氟烯烃的制造以及使用氢氟烯烃的方法
CN102405203B (zh) 2009-04-23 2015-04-08 大金工业株式会社 制备2,3,3,3-四氟丙烯的方法
US20110147638A1 (en) 2009-06-26 2011-06-23 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene, trans-1,2-dichloroethylene, and cyclopentane
GB0918069D0 (en) 2009-10-15 2009-12-02 Ineos Fluor Holdings Ltd Process
US20120216551A1 (en) 2009-11-03 2012-08-30 E.I. Du Pont De Nemours And Company Cascade refrigeration system with fluoroolefin refrigerant
US8618340B2 (en) 2009-11-03 2013-12-31 Honeywell International Inc. Integrated process for fluoro-olefin production
FR2954342B1 (fr) 2009-12-18 2012-03-16 Arkema France Fluides de transfert de chaleur a inflammabilite reduite
WO2012102915A1 (en) 2011-01-25 2012-08-02 3M Innovative Properties Company Fluorinated oxiranes as dielectric fluids
JP5682381B2 (ja) 2011-03-09 2015-03-11 日本ゼオン株式会社 含ハロゲノフッ素化シクロアルカン、及び含水素フッ素化シクロアルカンの製造方法
EP2688973A1 (en) * 2011-03-25 2014-01-29 3M Innovative Properties Company Fluorinated oxiranes as heat transfer fluids
US20140058003A1 (en) * 2011-05-19 2014-02-27 3M Innovative Properties Company Polymeric foams including fluorinated oxiranes, methods of preparation, and use of same
US20150083979A1 (en) * 2012-04-04 2015-03-26 3M Innovative Properties Company Fluorinated Nitriles as Dielectric Gases
US9532567B2 (en) 2012-11-29 2017-01-03 Honeywell International Inc. Synthesis and use of trans-1,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers
US9321867B2 (en) 2012-12-21 2016-04-26 Honeywell International Inc. Synthesis of 2,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers
WO2014140779A2 (en) 2013-03-15 2014-09-18 Preciflex Sa Temperature driven winding system
WO2015054110A1 (en) 2013-10-10 2015-04-16 E. I. Du Pont De Nemours And Company Compositions comprising difluoromethane, pentafluoroethane, tetrafluoroethane and tetrafluoropropene and uses thereof
EP2886591A1 (de) * 2013-12-19 2015-06-24 Evonik Industries AG Zusammensetzung, geeignet zur Herstellung von Polyurethanschäumen, enthaltend mindestens ein Nukleierungsmittel
WO2015095285A1 (en) * 2013-12-20 2015-06-25 3M Innovative Properties Company Fluorinated olefins as working fluids and methods of using same
JP6657957B2 (ja) 2014-01-31 2020-03-04 Ａｇｃ株式会社 熱サイクル用作動媒体、熱サイクルシステム用組成物および熱サイクルシステム
CN103804890B (zh) * 2014-02-18 2016-01-27 山东美瑞新材料有限公司 一种挤出发泡热塑性聚氨酯弹性体粒子及其制备方法
US20150315935A1 (en) * 2014-04-30 2015-11-05 General Electric Company System and method for inductor cooling
CN106574172B (zh) 2014-07-16 2018-11-02 3M创新有限公司 氢氟醚烯烃及其使用方法
WO2016048808A1 (en) 2014-09-23 2016-03-31 3M Innovative Properties Company Nitrogen containing hydrofluoroethers and methods of using same
WO2016064585A1 (en) 2014-10-24 2016-04-28 3M Innovative Properties Company Segregated fluorinated esters
WO2016196242A1 (en) 2015-06-05 2016-12-08 3M Innovative Properties Company Hydrofluoroolefins and methods of using same
JP6749347B2 (ja) 2015-06-05 2020-09-02 スリーエム イノベイティブ プロパティズ カンパニー ハイドロフルオロオレフィン及びその使用方法
EP3306737B1 (en) 2015-07-20 2019-05-15 Microvast Power Systems Co., Ltd. Battery pack and battery pack system
CN107922832B (zh) 2015-08-19 2021-05-25 3M创新有限公司 全氟醚稳定化量子点
US9790151B2 (en) 2015-11-12 2017-10-17 Honeywell International Inc. Process for making 2,3,3,3-tetrafluoropropene and/or vinylidine fluoride
US9856193B2 (en) * 2015-11-12 2018-01-02 Honeywell International Inc. Process for the production of fluorinated cyclobutane
US10005705B2 (en) * 2015-11-12 2018-06-26 Honeywell International Inc. Process for the production of fluorinated cyclobutane
JP6868623B2 (ja) 2015-12-02 2021-05-12 スリーエム イノベイティブ プロパティズ カンパニー アリル末端不飽和ヒドロフルオロアミン及びアリル末端不飽和ヒドロフルオロエーテル化合物並びにこれらの使用方法
EP3426651A4 (en) 2016-03-11 2019-08-21 3M Innovative Properties Company AMINO-CONTAINING CYCLIC HYDROFLUOROETHERS AND METHODS OF USE THEREOF
KR20180128956A (ko) 2016-04-01 2018-12-04 쓰리엠 이노베이티브 프로퍼티즈 컴파니 플루오로케미칼 안정화제를 갖는 양자점
US10020242B2 (en) 2016-04-14 2018-07-10 Hamilton Sundstrand Corporation Immersion cooling arrangements for electronic devices
US11479525B2 (en) 2016-08-22 2022-10-25 3M Innovative Properties Company Propenylamines and methods of making and using same
EP3515886A4 (en) 2016-09-26 2020-05-06 3M Innovative Properties Company HYDROFLUOROLEFINS CONTAINING NITROGEN AND / OR OXYGEN AND METHOD FOR THE PRODUCTION AND USE THEREOF
BR112019009013A2 (pt) * 2016-11-08 2019-07-16 Honeywell Int Inc processo para a produção de ciclobutano fluorado
WO2018116159A1 (en) 2016-12-21 2018-06-28 3M Innovative Properties Company Hydrofluoroolefins and methods of using same
CN110036087B (zh) 2017-01-13 2021-08-17 霍尼韦尔国际公司 制冷剂、热传递组合物、方法和系统
CN207491429U (zh) * 2017-03-06 2018-06-12 达纳加拿大公司 用于冷却电子模块的多个层的热交换器组件和热交换器模组
KR102387580B1 (ko) * 2017-03-28 2022-04-19 한온시스템 주식회사 전기소자 냉각용 열교환기
CN113242876A (zh) 2018-12-21 2021-08-10 霍尼韦尔国际公司 包含1,2,2-三氟-1-三氟甲基环丁烷的发泡剂组合物及发泡方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0427533B1 (en) * 1989-11-08 1997-07-16 The Dow Chemical Company Use of nucleating blowing agents in the preparation of insulating alkenyl aromatic polymer foams
WO1993007201A2 (en) * 1991-10-04 1993-04-15 Minnesota Mining And Manufacturing Company Fine-celled plastic foam containing halogenated blowing agent
JPH06329826A (ja) * 1993-05-17 1994-11-29 Daikin Ind Ltd フルオロシクロブタン化合物からなる発泡剤
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20120043492A1 (en) * 2010-08-17 2012-02-23 Honeywell International Inc. Compositions Containing 1-Chloro-3,3,3 Trifluoropropene And 1-Fluoro-1,1 Dichloroethane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4506400A4 (en) * 2022-06-01 2025-09-10 Jsp Corp POLYOLEFIN RESIN FOAM PARTICLES AND PROCESS FOR THEIR MANUFACTURE
WO2025183994A1 (en) * 2024-02-26 2025-09-04 Honeywell International Inc. Low gwp fluids for high temperature heat pump applications

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