US20100113629A1 - hydrofluoropropene blowing agents for thermoplastics - Google Patents

hydrofluoropropene blowing agents for thermoplastics Download PDF

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Publication number
US20100113629A1
US20100113629A1 US12/532,253 US53225308A US2010113629A1 US 20100113629 A1 US20100113629 A1 US 20100113629A1 US 53225308 A US53225308 A US 53225308A US 2010113629 A1 US2010113629 A1 US 2010113629A1
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United States
Prior art keywords
blowing agent
hfc
agent composition
mixtures
composition
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Abandoned
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US12/532,253
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English (en)
Inventor
Brett L. Van Horn
Maher Y. Elsheikh
Benjamin Bin Chen
Philippe Bonnet
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Arkema Inc
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Arkema Inc
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Application filed by Arkema Inc filed Critical Arkema Inc
Priority to US12/532,253 priority Critical patent/US20100113629A1/en
Assigned to ARKEMA INC. reassignment ARKEMA INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ELSHEIKH, MAHER Y., BONNET, PHILIPPE, CHEN, BENJAMIN BIN, VAN HORN, BRETT L.
Publication of US20100113629A1 publication Critical patent/US20100113629A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • 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
    • C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
    • 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
    • C08J2203/16—Unsaturated hydrocarbons
    • C08J2203/162—Halogenated unsaturated hydrocarbons, e.g. H2C=CF2
    • 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
    • C08J2203/18—Binary blends of expanding agents
    • C08J2203/182—Binary blends of expanding agents of physical blowing agents, e.g. acetone and butane
    • 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
    • C08J2203/20—Ternary blends of expanding agents
    • C08J2203/202—Ternary blends of expanding agents of physical blowing agents
    • 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
    • C08J2205/00—Foams characterised by their properties
    • C08J2205/04—Foams characterised by their properties characterised by the foam pores
    • C08J2205/05—Open cells, i.e. more than 50% of the pores are open
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/249921—Web or sheet containing structurally defined element or component
    • Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]

Definitions

  • the present invention relates to blowing agent compositions comprising at least one hydrochlorofluoroolefin (HCFO) used in the preparation of foamable thermoplastic compositions.
  • HCFOs of the present invention include, but are not limited to, 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), particularly the trans-isomer, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), dichloro-fluorinated propenes, and mixtures thereof.
  • blowing agent compositions of the present invention are preferably used with coblowing agents including carbon dioxide, atmospheric gases, hydrofluorocarbons (HFC), hydrofluoroolefins (HFO), alkanes, hydrofluoroethers (HFE), and mixtures thereof.
  • Preferred HFCs used as coblowing agents in the present invention include, but are not limited too, 1,1,1,2-tetrafluoroethane (HFC-134a); 1,1-difluoroethane (HFC-152a); 1,1,1-trifluoroethane (HFC-143a); pentafluorethane (HFC-125); and difluoromethane (HFC-32).
  • the blowing agent compositions are useful in the production of low density insulating foams with improved k-factor.
  • HFC hydrofluorocarbons
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbons
  • blowing agent compositions comprising a hydrochlorofluorolefin, particularly HCFO-1233zd, HCFO-1233xf, dichloro-fluorinated propenes, and mixtures thereof can permit the production of lower density, closed-cell foam and good k-factor which will be particularly useful for thermal insulating foams.
  • This invention may also permit the production of low density, closed-cell foams with enlarged, controlled cell size.
  • blowing agents comprising halogenated alkenes of generic formula that would include numerous HCFOs, among many other materials including brominated and iodinated compounds and HFOs.
  • Specific HCFOs for use in thermoplastic foaming are not disclosed nor are the benefits of using the HCFOs in terms of increasing the foam cell size as discovered in the present invention.
  • HCFO-1233zd is disclosed for use in polyurethane foaming, however it is not obvious to one skilled in the art that a blowing agent for polyurethane foaming would be particularly good for thermoplastic foaming.
  • GB 950,876 discloses a process for the production of polyurethane foams. It discloses that any suitable halogenated saturated or unsaturated hydrocarbon having a boiling point below 150° C., preferably below 50° C., can be used as the blowing agent. Trichlorofluoroethene, chlorotrifluoroethene, and 1,1-dichloro-2,2-difluoroethene are disclosed in a list of suitable blowing agents. Hydrochlorofluoropropenes are not specifically disclosed nor are longer chain HCFOs. There is no disclosure related to blowing agents for thermoplastic foaming nor are the benefits of HCFOs in thermoplastic foaming mentioned nor preferred combinations of HCFOs with other coblowing agents.
  • CA 2016328 discloses a process for preparing closed-cell, polyisocyanate foam.
  • organic compound blowing agents including halogenated alkanes and alkenes, where the alkene is propylene, and the halogenated hydrocarbons can be chlorofluorocarbons.
  • Hydrochlorofluoropropenes are not specifically disclosed nor are longer chain HCFOs.
  • blowing agents for thermoplastic foaming nor are the benefits of HCFOs in thermoplastic foaming mentioned nor preferred combinations of HCFOs with other coblowing agents.
  • the present invention relates to the use of blowing agents with negligible ozone-depletion and low GWP comprising a hydrochlorofluoroolefin (HCFO) used with an additional blowing agent.
  • HCFO hydrochlorofluoroolefin
  • the present invention discloses blowing agent and foamable resin compositions useful for the production of foams with decreased density, enlarged cell size, and improved k-factor that can be used as insulating foams.
  • the HCFO is 1-chloro-3,3,3-trilfluoropropene (HCFO-1233zd), preferably the trans isomer; 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), and mixtures thereof.
  • Preferred coblowing agents to be used with the HCFO include hydrofluorocarbons (HFC), preferably 1,1,1,2-tetrafluoroethane; 1,1-difluoroethane (HFC-152a); pentafluoroethane (HFC-125); 1,1,1-trifluoroethane (HFC-143a); difluoromethane (HFC-32); hydrofluoroolefins (HFO), preferably 3,3,3-trifluoropropene (HFO-1243zf); 1,3,3,3-tetrafluoropropene (HFO-1234ze), particularly the trans isomer; 2,3,3,3-tetrafluoropropene (HFO-1234yf); (cis and/or trans)-1,2,3,3,3-pentafluoropropene (HFO-1225ye); carbon dioxide; alkanes, preferably a butane or a pentane, and mixtures thereof.
  • HFC hydroflu
  • Another embodiment of this invention are foamable resin compositions containing greater than about 1 parts per hundred (pph) and less than about 100 pph of the blowing agent composition with respect to resin, preferably greater than about 2 pph and less than about 40 pph, more preferably greater than about 3 pph and less than about 25 pph, and even more preferably greater than about 4 pph and less than about 15 pph of the blowing agent composition with respect to resin.
  • the process for preparing a foamed thermoplastic product is as follows: Prepare a foamable polymer composition by blending together components comprising foamable polymer composition in any order. Typically, prepare a foamable polymer composition by plasticizing a polymer resin and then blending in components of a blowing agent composition at an initial pressure.
  • a common process of plasticizing a polymer resin is heat plasticization, which involves heating a polymer resin enough to soften it sufficiently to blend in a blowing agent composition.
  • heat plasticization involves heating a thermoplastic polymer resin near or above its glass transition temperature (Tg), or melt temperature (Tm) for crystalline polymers.
  • a foamable polymer composition can contain additional additives such as nucleating agents, cell-controlling agents, dyes, pigments, fillers, antioxidants, extrusion aids, stabilizing agents, antistatic agents, fire retardants, IR attenuating agents and thermally insulating additives.
  • Nucleating agents can include, among others, materials such as talc, calcium carbonate, sodium benzoate, and chemical blowing agents such azodicarbonamide or sodium bicarbonate and citric acid.
  • IR attenuating agents and thermally insulating additives can include carbon black, graphite, silicon dioxide, metal flake or powder, among others.
  • Flame retardants can include, among others, brominated materials such as hexabromocyclodecane and polybrominated biphenyl ether.
  • Foam preparation processes of the present invention include batch, semi-batch, and continuous processes. Batch processes involve preparation of at least one portion of the foamable polymer composition in a storable state and then using that portion of foamable polymer composition at some future point in time to prepare a foam.
  • a semi-batch process involves preparing at least a portion of a foamable polymer composition and intermittently expanding that foamable polymer composition into a foam all in a single process.
  • U.S. Pat. No. 4,323,528, incorporated herein by reference discloses a process for making polyolefin foams via an accumulating extrusion process.
  • the process comprises: 1) mixing a thermoplastic material and a blowing agent composition to form a foamable polymer composition; 2) extruding the foamable polymer composition into a holding zone maintained at a temperature and pressure which does not allow the foamable polymer composition to foam; the holding zone has a die defining an orifice opening into a zone of lower pressure at which the foamable polymer composition foams and an openable gate closing the die orifice; 3) periodically opening the gate while substantially concurrently applying mechanical pressure by means of a movable ram on the foamable polymer composition to eject it from the holding zone through the die orifice into the zone of lower pressure, and 4) allowing the ejected foamable polymer composition to expand to form the foam.
  • a continuous process involves forming a foamable polymer composition and then expanding that foamable polymer composition in a non-stop manner.
  • prepare a foamable polymer composition in an extruder by heating a polymer resin to form a molten resin, blending into the molten resin a blowing agent composition at an initial pressure to form a foamable polymer composition, and then extruding that foamable polymer composition through a die into a zone at a foaming pressure and allowing the foamable polymer composition to expand into a foam.
  • cool the foamable polymer composition after addition of the blowing agent and prior to extruding through the die in order to optimize foam properties. Cool the foamable polymer composition, for example, with heat exchangers.
  • Foams of the present invention can be of any form imaginable including sheet, plank, rod, tube, beads, or any combination thereof. Included in the present invention are laminate foams that comprise multiple distinguishable longitudinal foam members that are bound to one another.
  • a 15 m long, 0.53 mm diameter GC capillary-column was prepared with a 3 micron thick polystyrene internal film coating.
  • the column was installed into a Hewlet Packard 5890 Series II Gas Chromatograph with flame ionizer detector. Elution profiles for gases being tested were analyzed according the method outlined in the reference, using methane as the reference gas. The results give the diffusion coefficient of the gas through the polymer, Dp, and the solubility of the gas in the polymer in terms of the partition coefficient, K, which is the ratio of the concentration of the gas in the polymer phase to the concentration in the vapor phase. As such, the greater the value of K for a particular gas in the resin the greater its solubility in that resin.
  • Table 1 shows the partition coefficient and diffusivity values for several gases in polystyrene at 140° C. Comparative examples 1-5 show the solubility and diffusivity of HCFC-142b (1-chloro-1,1-difluoroethane), HFC-152a (1,1-difluoroethane), HFC-134a (1,1,1,2-tetrafluoroethane), HFC-32 (difluoromethane), and HFC-245fa (1,1,1,3,3-pentafluoropropane) in polystyrene (PS).
  • HCFO-1233zd and HCFO-1233xf have sufficient solubility and diffusivity in polystyrene resin to be effective blowing agents or as useful coblowing agents with other blowing agents such as HFCs or carbon dioxide.
  • HCFO-1233xf for instance, was found to have a solubility comparable to that of HCFC-142b.
  • the diffusivities of HCFO-1233zd and HCFO-1233xf were found to be low, indicating that should be useful in providing foams with improved k-factor.
  • Extruded polystyrene foam was produced using a counter-rotating twin screw extruder with internal barrel diameters or 27 mm and a barrel length of 40 diameters.
  • the screw design was suitable for foaming applications.
  • the pressure in the extruder barrel was controlled with the gear pump and was set high enough such that the blowing agent dissolved in the extruder.
  • the extruder die for examples 9-20 was an adjustable-lip slot die with a gap width of 6.35 mm. For example 1, the die was a 2 mm diameter strand die with a 1 mm land length.
  • Two grades of general purpose polystyrene were used for the extrusion trials and fed to the extruder at rates of either 2.27 or 4.54 kg/hr (5 or 10 lb/hr).
  • Blowing agents were pumped into the polystyrene resin melt at a controlled rate using high pressure delivery pumps.
  • the blowing agent is mixed and dissolved in the resin melt to produce an expandable resin composition.
  • the expandable resin composition is cooled to an appropriate foaming temperature and then extruded from the die where the drop in pressure initiates foaming.
  • Talc was used as a nucleating agent and was pre-blended with polystyrene to make a masterbatch of 50 wt % talc in polystyrene. Beads of this masterbatch were mixed with polystyrene pellets to achieve 0.5 wt % talc in each experiment.
  • the density, open cell content, and cell size was measured for foam samples collected during each run. Density was measured according to ASTM D792, open cell content was measured using gas pychnometry according to ASTM D285-C, and cell size was measured by averaging the cell diameters from scanning electron microscope (SEM) micrographs of foam sample fracture surfaces. SEM images are also used to observe the cell structure and qualitatively check for open cell content.
  • SEM scanning electron microscope
  • Table 2 shows data for examples 8 through 20, including the loading of each blowing agent in the formulation, the resin feed rate, melt flow index of the resin, the expandable resin melt temperature, and the density, cell size, and open cell content of the resulting foamed product.
  • Comparative example 8 is typical for polystyrene foaming with HFC-134a, where the poor solubility and difficulties in processing tend to lead to higher density foam with smaller size and more open cells.
  • Comparative examples 9 and 10 show results for foaming with 3,3,3-trifluoropene (HFO-1243zf; TFP).
  • blowing agent compositions of TFP (HFO-1243zf) and HCFO-1233zd permitted production of lower density foam than achievable with TFP alone along with a beneficial enlargement in the cell size, where it was possible to produce closed-cell foam product with cell sizes greater than 0.2 mm at densities less than 53 kg/m 3 and even less than 45 kg/m 3 . These foams would be useful as thermal insulating foams with improved k-factor.
  • Examples 13 through 16 were produced during the same extrusion trial.
  • HFC-134a was used as the only blowing agent at a loading of 5.3 wt %.
  • the foamed product had significant defects including blowholes and large voids.
  • HCFO-1233zd predominantly the trans isomer, was added to produce example 14, which resulted in reduction of the popping at the die with a reduction in the die pressure along with reducing the number of defects in the foamed product.
  • the blowing agent feeds were adjusted to generate examples 15 and 16, where there was no popping at the die and only a few defects.
  • HCFO-1233zd improved the processing of the 134a blown foams, improved the general quality of the foamed product, and permitted production of lower density foam.
  • Examples 17 and 18 were produced during using HFO-1234yf (2,3,3,3-tetrafluoroethane) as the only blowing agent.
  • HFO-1234yf (2,3,3,3-tetrafluoroethane)
  • the foamed product had very small cell size, macrovoids, blowholes, high open cell content, and frequent periods of popping at the die caused by undissolved blowing agent. Increasing the content of 1234yf made these problems worse.
  • blowing agent compositions of HFO-1234yf and HCFO-1233zd permitted production of lower density foam than was produced using the HFO-1234yf alone.
  • the foamed samples of examples 19 and 20 were of good quality, with few defects and produced without popping at the die.
  • the HCFO-1233zd was predominantly the trans-isomer.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
US12/532,253 2007-03-29 2008-03-28 hydrofluoropropene blowing agents for thermoplastics Abandoned US20100113629A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/532,253 US20100113629A1 (en) 2007-03-29 2008-03-28 hydrofluoropropene blowing agents for thermoplastics

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US90876207P 2007-03-29 2007-03-29
US12/532,253 US20100113629A1 (en) 2007-03-29 2008-03-28 hydrofluoropropene blowing agents for thermoplastics
PCT/US2008/058596 WO2008121779A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrochlorofluoroolefins

Related Parent Applications (1)

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PCT/US2008/058596 A-371-Of-International WO2008121779A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrochlorofluoroolefins

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US12/532,238 Abandoned US20100105789A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins
US12/532,207 Abandoned US20100112328A1 (en) 2007-03-29 2008-03-28 Hydrofluoropropene blowing agents for thermoplastics
US12/532,253 Abandoned US20100113629A1 (en) 2007-03-29 2008-03-28 hydrofluoropropene blowing agents for thermoplastics
US13/342,247 Active US8648123B2 (en) 2007-03-29 2012-01-03 Hydrofluoropropene blowing agents for thermoplastics
US13/342,307 Abandoned US20120101177A1 (en) 2007-03-29 2012-01-03 Blowing agent compositions of hydrochlorofluoroolefins

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US12/532,238 Abandoned US20100105789A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins
US12/532,207 Abandoned US20100112328A1 (en) 2007-03-29 2008-03-28 Hydrofluoropropene blowing agents for thermoplastics

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US13/342,247 Active US8648123B2 (en) 2007-03-29 2012-01-03 Hydrofluoropropene blowing agents for thermoplastics
US13/342,307 Abandoned US20120101177A1 (en) 2007-03-29 2012-01-03 Blowing agent compositions of hydrochlorofluoroolefins

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US (5) US20100105789A1 (ja)
EP (3) EP2129710B1 (ja)
JP (6) JP5762737B2 (ja)
CN (4) CN105001440A (ja)
AT (2) ATE532818T1 (ja)
CA (3) CA2681605A1 (ja)
ES (3) ES2377420T3 (ja)
PL (3) PL2129710T3 (ja)
WO (3) WO2008121776A1 (ja)

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US20100216904A1 (en) * 2009-02-24 2010-08-26 E. I. Du Pont De Nemours And Company Foam-forming compositions containing mixtures of 2-chloro-3,3,3-trifluoropropene and at least one hydrofluoroolefin and their uses in the preparation of polyisocyanate-based foams
US20110124758A1 (en) * 2008-08-13 2011-05-26 E.I. Du Pont De Nemours And Company Foam-forming compositions containing mixtures of 2-chloro-3,3,3-trifluoropropene and hydrocarbon and their uses in the preparation of polyisocyanate-based foams
US20110175015A1 (en) * 2008-10-28 2011-07-21 Honeywell International Inc. Azeotrope-Like Compositions Comprising Trans-1-Chloro-3,3,3-Trifluoropropene
US20120064014A1 (en) * 2008-10-28 2012-03-15 Honeywell International Inc. Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene
WO2012024252A3 (en) * 2010-08-17 2012-05-31 Honeywell International Inc. Compositions containing 1-chloro-3,3,3 trifluoropropene and 1-fluoro-1,1 dichloroethane
US20120329893A1 (en) * 2010-03-09 2012-12-27 Arkema France Hydrochlorofluoroolefin blowing agent compositions
US8680168B2 (en) 2010-11-17 2014-03-25 Fomo Products, Inc. Method for filling wall cavities with expanding foam insulation
US20160017111A1 (en) * 2014-07-16 2016-01-21 Owens Corning Intellectual Capital, Llc Non-voc processing aids for use in manufacturing foams using low global warming potential blowing agents
US9254468B2 (en) 2008-03-07 2016-02-09 Arkema Inc. Stable formulated systems with chloro-3,3,3-trifluoropropene
US10053549B2 (en) 2011-06-27 2018-08-21 Owens Corning Intellectual Capital, Llc Organic infrared attenuation agents
US10077221B2 (en) 2013-03-20 2018-09-18 Arkema France Composition comprising HF and E-3,3,3-trifluoro-1-chloropropene
US10301236B2 (en) 2015-05-21 2019-05-28 The Chemours Company Fc, Llc Hydrofluorination of a halogenated olefin with SbF5 in the liquid phase
US10669465B2 (en) 2016-09-19 2020-06-02 Arkema France Composition comprising 1-chloro-3,3,3-trifluoropropene
US10676581B2 (en) 2013-03-15 2020-06-09 Owens Corning Intellectual Capital, Llc Processing aids for use in manufacture extruded polystyrene foams using low global warming potential blowing agents
US10858561B2 (en) 2008-10-16 2020-12-08 Arkema France Heat transfer method

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US20090253820A1 (en) * 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US20110037016A1 (en) * 2003-10-27 2011-02-17 Honeywell International Inc. Fluoropropene compounds and compositions and methods using same
US9499729B2 (en) * 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US20110152392A1 (en) * 2009-12-17 2011-06-23 Honeywell International Inc. Catalysts For Polyurethane Foam Polyol Premixes Containing Halogenated Olefin Blowing Agents
TW201815923A (zh) † 2005-06-24 2018-05-01 美商哈尼威爾國際公司 含有經氟取代之烯烴之發泡劑及組合物，及發泡方法
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ATE537209T1 (de) 2011-12-15
EP2129712B1 (en) 2012-08-08
EP2129712A1 (en) 2009-12-09
JP2014196516A (ja) 2014-10-16
US8648123B2 (en) 2014-02-11
US20100112328A1 (en) 2010-05-06
JP6692734B2 (ja) 2020-05-13
ES2377420T3 (es) 2012-03-27
EP2129710A1 (en) 2009-12-09
CA2681605A1 (en) 2008-10-09
WO2008121778A1 (en) 2008-10-09

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