US20100105789A1 - Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins - Google Patents

Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins Download PDF

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Publication number
US20100105789A1
US20100105789A1 US12/532,238 US53223808A US2010105789A1 US 20100105789 A1 US20100105789 A1 US 20100105789A1 US 53223808 A US53223808 A US 53223808A US 2010105789 A1 US2010105789 A1 US 2010105789A1
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Prior art keywords
blowing agent
agent composition
hfc
mixtures
composition
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Abandoned
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US12/532,238
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English (en)
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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 US12/532,238 priority Critical patent/US20100105789A1/en
Assigned to ARKEMA INC. reassignment ARKEMA INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BONNET, PHILIPPE, ELSHEIKH, MAHER Y., CHEN, BENJAMIN BIN, VAN HORN, BRETT L.
Publication of US20100105789A1 publication Critical patent/US20100105789A1/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 (1) at least one hydrofluoroolefin (HFO) and (2) at least one hydrochlorofluoroolefin (HCFO) used in the preparation of foamable thermoplastic compositions.
  • HFOs of component (1) include, but are not limited too, 3,3,3-trifluoropropene (HFO-1243zf), 1,2,3,3,3-pentafluoropropene (HFO-1225ye), cis- and/or trans-1,3,3,3-tetrafluoropropene (HFO-1234ze), and 2,3,3,3-tetrafluoropropene (HFO 1234yf), and mixtures thereof.
  • the HCFOs of component (2) include, but are not limited to, 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), dichlorofluorinated propenes, and mixtures thereof.
  • the blowing agent compositions are useful in the production of low density insulating foams with improved k-factor.
  • HFC hydrofluorocarbons
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbons
  • Hydrofloroolefins such as HFO-1243zf, (cis/trans)-HFO-1234ze, HFO-1234yf, and (E/Z)-HFO-1225ye, have been identified as potential low GWP blowing agents for the production of thermoplastic foams, including extruded polystyrene foams for thermal insulation.
  • blowing agent compositions comprising at least one hydrofluorolefin with at least one hydrochlorofluoroolefin can permit the production of lower density, closed-cell foam with 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 HFOs and HCFOs, among many other materials including brominated and iodinated compounds.
  • the specific combination of HFOs with HCFOs in blowing agent compositions is not disclosed.
  • Specific examples are shown for blowing agent compositions for foaming polystyrene comprising HFOs, specifically HFO-1234ze and HFO-1234yf, either alone or in combination with an HFC, and blowing agent compositions for PUR foaming comprising HCFO-1233zd. No examples of blowing agents combinations comprising HFOs and HCFOs are disclosed.
  • 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 along with 3,3,3-trifluoropropene. Hydrochlorofluoropropenes are not specifically disclosed nor are longer chain HCFOs nor other HFOs besides 3,3,3-trifluoropropene. There is no disclosure related to blowing agents for thermoplastic foaming, nor are the benefits of HCFOs in thermoplastic foaming mentioned, nor are the benefits of blowing agent combinations comprising HCFOs and HFOs.
  • 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 are the benefits of blowing agent combinations comprising HCFOs and HFOs.
  • the present invention relates to the use of blowing agents with negligible ozone-depletion and low GWP comprising (1) at least one hydrofluoroolefin (HFO) and (2) at least on hydrochlorofluoroolefin (HCFO).
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • the HFO in component (1) is 3,3,3-trifluoropropene (HFO-1243zf); (cis and/or trans)-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) and mixtures thereof.
  • HFO-1243zf 3,3,3-trifluoropropene
  • HFO-1234ze 1,3,3,3-tetrafluoropropene
  • HFO-1234yf 2,3,3,3-tetrafluoropropene
  • HFO-1225ye 1,2,3,3,3-pentafluoropropene
  • the HCFO of component (2) is preferably (cis and/or trans)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), particularly the trans isomer, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1,1-dicloro-3,3,3-trifluoropropene, 1,2-dichloro-3,3,3-trifluoropropene, and mixtures thereof.
  • 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 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, herein incorporated 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 15m 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 and 2 show the solubility and diffusivity of two well studied blowing agents in polystyrene: HCFC-142b (1-chloro-1,1-difluoroethane) and HFC-134a (1,1,1,2-tetrafluoroethane).
  • Examples 3-6 show the solubility and diffusivity of selected HFOs in polystyrene: HFO-1243zf (3,3,3-trifluoropropene), HFO-1234ze (1,3,3,3-tetrafluoropropene), HFO-1234yf (2,3,3,3-tetrafluoropropene), HFO-1225ye (1,2,3,3,3-pentafluoropropene).
  • Examples 7 and 8 show the solubility and diffusivity of trans-HCFO-1233zd (1-chloro-3,3,3-trifluoropropene) and HCFO-1233xf (2-chloro-3,3,3-trifluoropropene),
  • the good solubility and favorable diffusivity of the HCFOs in polystyrene indicate that they should be effective coblowing agents and/or processing aids for the production of thermoplastic foams using HFO blowing agents.
  • the solubility of the HCFOs in polystyrene is sufficient to provide useful plasticization of the thermoplastic resin to assist in foaming.
  • HCFO-1233xf has a solubility in polystyrene comparable to that of HCFC-142b.
  • 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 10-18 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 9 through 14, 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 9 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 10 through 12 show results for foaming with 3,3,3-trifluoropene (HFO-1243zf; TFP). At a loading of 8.5 wt % TFP the resulting foam had smaller cell size while comparative density to examples 10 and 11.
  • 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 . These foams would be useful as thermal insulating foams with improved k-factor.
  • the HCFO-1233zd was predominantly the trans-isomer.
  • Examples 15 and 16 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 17 and 18 were of good quality, with few defects and produced without popping at the die.

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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)
US12/532,238 2007-03-29 2008-03-28 Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins Abandoned US20100105789A1 (en)

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Application Number Priority Date Filing Date Title
US12/532,238 US20100105789A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins

Applications Claiming Priority (3)

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US90876207P 2007-03-29 2007-03-29
US12/532,238 US20100105789A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins
PCT/US2008/058594 WO2008121778A1 (en) 2007-03-29 2008-03-28 Blowing agent compositions of hydrofluoroolefins and hydrochlorofluoroolefins

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

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US12/532,253 Abandoned US20100113629A1 (en) 2007-03-29 2008-03-28 hydrofluoropropene blowing agents for thermoplastics
US12/532,207 Abandoned US20100112328A1 (en) 2007-03-29 2008-03-28 Hydrofluoropropene blowing agents for thermoplastics

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

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US (5) US20100113629A1 (de)
EP (3) EP2129710B1 (de)
JP (6) JP5763338B2 (de)
CN (4) CN101652414B (de)
AT (2) ATE537209T1 (de)
CA (3) CA2681825C (de)
ES (3) ES2377420T3 (de)
PL (3) PL2129711T5 (de)
WO (3) WO2008121779A1 (de)

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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
US20120101177A1 (en) * 2007-03-29 2012-04-26 Arkema Inc. Blowing agent compositions of hydrochlorofluoroolefins
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US8895635B2 (en) 2007-03-29 2014-11-25 Arkema Inc. Blowing agent compositions of hydrochlorofluoroolefins
US9206297B2 (en) 2007-03-29 2015-12-08 Arkema Inc. Blowing agent compositions of hydrochlorofluoroolefins
US9254468B2 (en) 2008-03-07 2016-02-09 Arkema Inc. Stable formulated systems with chloro-3,3,3-trifluoropropene
US20160347922A1 (en) * 2015-05-29 2016-12-01 Owens Corning Intellectual Capital, Llc Extruded polystyrene foam
US10053549B2 (en) 2011-06-27 2018-08-21 Owens Corning Intellectual Capital, Llc Organic infrared attenuation agents
US10301236B2 (en) 2015-05-21 2019-05-28 The Chemours Company Fc, Llc Hydrofluorination of a halogenated olefin with SbF5 in the liquid phase
US10308778B2 (en) * 2014-11-25 2019-06-04 Crecimento Industrial Co., Ltd. Preparation and application of dynamic non-wicking PU foam
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
US12006274B2 (en) 2022-11-03 2024-06-11 The Chemours Company Fc, Llc Compositions including olefin and hydrofluoroalkane

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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
US9499729B2 (en) * 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
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