WO2008121790A1 - Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin - Google Patents

Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin Download PDF

Info

Publication number
WO2008121790A1
WO2008121790A1 PCT/US2008/058607 US2008058607W WO2008121790A1 WO 2008121790 A1 WO2008121790 A1 WO 2008121790A1 US 2008058607 W US2008058607 W US 2008058607W WO 2008121790 A1 WO2008121790 A1 WO 2008121790A1
Authority
WO
WIPO (PCT)
Prior art keywords
isomers
hcfo
blowing agent
agent composition
hfo
Prior art date
Application number
PCT/US2008/058607
Other languages
French (fr)
Inventor
Benjamin B. Chen
Joseph S. Costa
Philippe Bonnet
Maher Y. Elsheikh
Brett L. Van Horn
Original Assignee
Arkema 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39808678&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2008121790(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Arkema Inc. filed Critical Arkema Inc.
Priority to AT08744563T priority Critical patent/ATE528341T1/en
Priority to PL08744563T priority patent/PL2129715T3/en
Priority to US12/532,202 priority patent/US9279039B2/en
Priority to CA2681872A priority patent/CA2681872C/en
Priority to EP08744563A priority patent/EP2129715B1/en
Priority to JP2010501249A priority patent/JP5539854B2/en
Publication of WO2008121790A1 publication Critical patent/WO2008121790A1/en
Priority to US15/015,184 priority patent/US9914815B2/en

Links

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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of 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
    • 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
    • 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
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/10—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08J2300/104—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen 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
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/10—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08J2300/106—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen 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
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the present invention relates to blowing agents for thermosetting foams. More particularly, the present invention relates to the use of at least one hydrofluoroolefin such as HFO-1234yf in combination with at least one hydrochlorofluoroolefin (HCFO) such as HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof as a blowing agent in the manufacture of thermosetting foams.
  • HFO-1234yf hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • thermoset foams include HFC- 134a, HFC-245fa, HFC-365mfc that have relatively high global warming potential, and hydrocarbons such as pentane isomers flammable and have low energy efficiency. Therefore, new alternative blowing agents are being sought.
  • Halogenated hydroolef ⁇ nic materials such as hydrofluoropropenes and/or hydrochlorofluoropropenes have generated interest as replacements for HFCs. The inherent chemical instability of these materials in the lower atmosphere provides the low global warning potential and zero or near zero ozone depletion properties desired.
  • the object of the present invention is to provide novel compositions that can serve as blowing agents for thermosetting foams that provide unique characteristics to meet the demands of low or zero ozone depletion potential, lower global warming potential and exhibit low toxicity.
  • the present invention relates to the use of blowing agents with negligible (low or zero) ozone-depletion and low global warming potential based upon unsaturated halogenated hydroolefms.
  • the blowing agents comprise at least one hydrofluoroolefm preferably (HFO) HFO-1234yf in a combination with at least one hydrochlorofluoroolefin (HCFO) such as HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof.
  • HFO- 1234yf is 2,3,3,3-tetrafluoropropene; HCFO 1223 is dichlorotrifluoropropene; HCFO- 1233zd is l-chloro-3, 3,3-trifluoropropene; HCFO1233xf is 2-chloro-3,3,3-trifluoropropene.
  • the composition can further comprise an additional hydrofluoroolefm (HFO), a hydro fluorocarbon, a hydrocarbon, an alcohol, an ester, an aldehyde, a ketone ether/diether, carbon dioxide and mixtures thereof.
  • HFO hydrofluoroolefm
  • Hydrofluoroolefm (HFO) materials have been proposed as blowing agents which exhibit a low global warming potential and a low ozone depletion value.
  • the low global warming potential and a low ozone depletion value are a result of the atmospheric degradation of the hydro fluoroolefins.
  • the hydro fluoroolefin preferably HFO-1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof combination can be used as a foaming agent for thermosetting foams by being mixed in a polyols mixture.
  • HCFO hydrochlorofluoroolefin
  • the resulted products show superior quality including decreased density and improved k-factor.
  • the foaming agent dissolves in thermosetting polymers, and provides a degree of plasticization sufficient to produce acceptable foams.
  • the preferred blowing agent composition hydro fluoroolefin, preferably HFO- 1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO-1233xf and mixtures thereof of the present invention exhibits good solubility in polyol mixture used in producing polyurethane and polyisocyanurate foams.
  • HCFO hydrochlorofluoroolefin
  • a preferred ratio of the hydrofluoroolefm, preferably HFO-1234yf component in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO-1233xf and mixtures thereof is more than about 5 wt% hydro fluoroolefin.
  • HCFO hydrochlorofluoroolefin
  • hydrofluoroolefm preferably HFO-1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof composition of the present invention
  • HCFO hydrochlorofluoroolefin
  • low or zero ozone depletion value materials including but not limited to: (a) hydro fluorocarbons including but not limited to difluoromethane (HFC32); 1,1,1- trifluoroethane (143a); 1,1,1,2,2-pentafluoroethane (HFC125); 1,1,2,2-tetrafluoroethane (HFC 134); 1,1,1,2-tetrafluoroethane (HFC 134a); 1,1-difluoroethane (HFC 152a); 1,1,1,2,3,3,3-heptafluoropropane (HFC227ea); 1,1,1,3,3-p
  • hydro fluoroolefins other than HFO-1234yf, including but not limited to tetrafluoropropenes such as HFO1234ze; trifluoropropenes such as HFO1243zf, all tetrafluorobutene isomers (HFOl 354), all pentafluorobutene isomers (HFO1345), all hexafluorobutene isomers (HFOl 336), all heptafluorobutene isomers (HFO 1327), all heptafiuoropentene isomers (HFO 1447) all octafluoropentene isomers (HFO 1438), all nonafluoropentene (HFOl 429) (c) hydrocarbons including but not limited to, pentane isomers, butane isomers, (d) Cl to C5 alcohols, Cl to C4 aldehydes, Cl to C4 esters, Cl
  • the foamable compositions of the present invention generally includes one or more components capable of forming foam having a generally cellular structure and a blowing agent, typically in a combination, in accordance with the present invention.
  • the one or more components comprise a thermosetting composition capable of forming foam and/or foamable compositions.
  • thermosetting compositions include polyurethane and polyisocyanurate foam compositions, and also phenolic foam compositions, hi such thermosetting foam embodiments, one or more of the present compositions are included as or part of a blowing agent in a foamable composition, or as a part of a two or more part foamable composition, which preferably includes one or more of the components capable of reacting and/or foaming under the proper conditions to form a foam or cellular structure.
  • the invention also relates to foam, and preferably closed cell foam, prepared from a polymer foam formulation containing a blowing agent comprising the compositions of the invention.
  • the invention provides foamable compositions comprising thermosetting foams, such as polyurethane and polyisocyanurate foams, preferably low-density foams, flexible or rigid. It will be appreciated by those skilled in the art that the order and manner in which the blowing agent combination of the present invention is formed and/or added to the foamable composition does not generally affect the operability of the present invention.
  • the various components of the blowing agent combination, and even the components of the present composition not be mixed in advance of introduction to the foaming equipment, or even that the components are not added to the same location in the foaming equipment.
  • two or more components of the blowing agent combination are combined in advance and introduced together into the foamable composition, either directly or as part of premix that is then further added to other parts of the foamable composition.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A blowing agent for thermosetting foams is disclosed. The blowing agent is a hydrofluoroolefin (HCFO), preferably HFCO-1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably one selected from HCFO-1233zd, HCFO-1223, HCFO-1233xf and mixtures thereof. The blowing agent is effective as a blowing agent in the manufacture of thermosetting foams.

Description

Blowing Agent Composition of Hydrochlorofluoroolefin and Hydrofluoroolefin
FIELD OF THE INVENTION
The present invention relates to blowing agents for thermosetting foams. More particularly, the present invention relates to the use of at least one hydrofluoroolefin such as HFO-1234yf in combination with at least one hydrochlorofluoroolefin (HCFO) such as HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof as a blowing agent in the manufacture of thermosetting foams.
BACKGROUND OF THE INVENTION
The Montreal Protocol for the protection of the ozone layer, signed in October 1987, mandated the phase out of the use of chlorofluorocarbons (CFCs). Materials more "friendly" to the ozone layer, such as hydro fluorocarbons (HFCs) eg HFC- 134a replaced chlorofluorocarbons. The latter compounds have proven to be green house gases, causing global warming and were regulated by the Kyoto Protocol on Climate Change, signed in 1998. The emerging replacement materials, hydro fluoropropenes, were shown to be environmentally acceptable i.e. has zero ozone depletion potential (ODP) and acceptable low global warming potential (GWP).
Currently used blowing agents for thermoset foams include HFC- 134a, HFC-245fa, HFC-365mfc that have relatively high global warming potential, and hydrocarbons such as pentane isomers flammable and have low energy efficiency. Therefore, new alternative blowing agents are being sought. Halogenated hydroolefϊnic materials such as hydrofluoropropenes and/or hydrochlorofluoropropenes have generated interest as replacements for HFCs. The inherent chemical instability of these materials in the lower atmosphere provides the low global warning potential and zero or near zero ozone depletion properties desired.
The object of the present invention is to provide novel compositions that can serve as blowing agents for thermosetting foams that provide unique characteristics to meet the demands of low or zero ozone depletion potential, lower global warming potential and exhibit low toxicity.
SUMMARY OF THE INVENTION The present invention relates to the use of blowing agents with negligible (low or zero) ozone-depletion and low global warming potential based upon unsaturated halogenated hydroolefms. The blowing agents comprise at least one hydrofluoroolefm preferably (HFO) HFO-1234yf in a combination with at least one hydrochlorofluoroolefin (HCFO) such as HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof. HFO- 1234yf is 2,3,3,3-tetrafluoropropene; HCFO 1223 is dichlorotrifluoropropene; HCFO- 1233zd is l-chloro-3, 3,3-trifluoropropene; HCFO1233xf is 2-chloro-3,3,3-trifluoropropene. The composition can further comprise an additional hydrofluoroolefm (HFO), a hydro fluorocarbon, a hydrocarbon, an alcohol, an ester, an aldehyde, a ketone ether/diether, carbon dioxide and mixtures thereof.
Hydrofluoroolefm (HFO) materials have been proposed as blowing agents which exhibit a low global warming potential and a low ozone depletion value. The low global warming potential and a low ozone depletion value are a result of the atmospheric degradation of the hydro fluoroolefins.
The hydro fluoroolefin, preferably HFO-1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof combination can be used as a foaming agent for thermosetting foams by being mixed in a polyols mixture. The resulted products show superior quality including decreased density and improved k-factor. The foaming agent dissolves in thermosetting polymers, and provides a degree of plasticization sufficient to produce acceptable foams.
The preferred blowing agent composition, hydro fluoroolefin, preferably HFO- 1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO-1233xf and mixtures thereof of the present invention exhibits good solubility in polyol mixture used in producing polyurethane and polyisocyanurate foams. A preferred ratio of the hydrofluoroolefm, preferably HFO-1234yf component in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO-1233xf and mixtures thereof is more than about 5 wt% hydro fluoroolefin.
The hydrofluoroolefm, preferably HFO-1234yf in combination with a hydrochlorofluoroolefin (HCFO) preferably selected from HCFO-1223, HCFO-1233zd, HCFO- 1233xf and mixtures thereof composition of the present invention may be used in combination with low or zero ozone depletion value materials including but not limited to: (a) hydro fluorocarbons including but not limited to difluoromethane (HFC32); 1,1,1- trifluoroethane (143a); 1,1,1,2,2-pentafluoroethane (HFC125); 1,1,2,2-tetrafluoroethane (HFC 134); 1,1,1,2-tetrafluoroethane (HFC 134a); 1,1-difluoroethane (HFC 152a); 1,1,1,2,3,3,3-heptafluoropropane (HFC227ea); 1,1,1,3,3-pentafluoropropane (HFC245fa); 1,1,1,3,3-pentafluorobutane (HFC365mfc) and 1,1,1,2,2,3,4,5,5,5-decafluoropentane (HFC4310mee). (b) additional hydro fluoroolefins, other than HFO-1234yf, including but not limited to tetrafluoropropenes such as HFO1234ze; trifluoropropenes such as HFO1243zf, all tetrafluorobutene isomers (HFOl 354), all pentafluorobutene isomers (HFO1345), all hexafluorobutene isomers (HFOl 336), all heptafluorobutene isomers (HFO 1327), all heptafiuoropentene isomers (HFO 1447) all octafluoropentene isomers (HFO 1438), all nonafluoropentene (HFOl 429) (c) hydrocarbons including but not limited to, pentane isomers, butane isomers, (d) Cl to C5 alcohols, Cl to C4 aldehydes, Cl to C4 esters, Cl to C4 ketones, Cl to C4 ethers and diethers and carbon dioxide
The foamable compositions of the present invention generally includes one or more components capable of forming foam having a generally cellular structure and a blowing agent, typically in a combination, in accordance with the present invention. In certain embodiments, the one or more components comprise a thermosetting composition capable of forming foam and/or foamable compositions. Examples of thermosetting compositions include polyurethane and polyisocyanurate foam compositions, and also phenolic foam compositions, hi such thermosetting foam embodiments, one or more of the present compositions are included as or part of a blowing agent in a foamable composition, or as a part of a two or more part foamable composition, which preferably includes one or more of the components capable of reacting and/or foaming under the proper conditions to form a foam or cellular structure.
The invention also relates to foam, and preferably closed cell foam, prepared from a polymer foam formulation containing a blowing agent comprising the compositions of the invention. In yet other embodiments, the invention provides foamable compositions comprising thermosetting foams, such as polyurethane and polyisocyanurate foams, preferably low-density foams, flexible or rigid. It will be appreciated by those skilled in the art that the order and manner in which the blowing agent combination of the present invention is formed and/or added to the foamable composition does not generally affect the operability of the present invention. For example, in the case of polyurethane foams, it is possible that the various components of the blowing agent combination, and even the components of the present composition, not be mixed in advance of introduction to the foaming equipment, or even that the components are not added to the same location in the foaming equipment. Thus, in certain embodiments it may be desired to introduce one or more components of the blowing agent combination in a blender with the expectation that the components will come together in the foaming equipment and/or operate more effectively in this manner. Nevertheless, in certain embodiments, two or more components of the blowing agent combination are combined in advance and introduced together into the foamable composition, either directly or as part of premix that is then further added to other parts of the foamable composition.
Although the invention is illustrated and described herein with reference to specific embodiments, it is not intended that the appended claims be limited to the details shown. Rather, it is expected that various modifications may be made in these details by those skilled in the art, which modifications may still be within the spirit and scope of the claimed subject matter and it is intended that these claims be construed accordingly.

Claims

1. A polymer blowing agent composition for thermosetting foams comprising (a) HFO-1234yf in combination with (b) at least one hydrochlorofluoroolefin (HCFO).
2. The polymer blowing agent composition of claim 1 wherein said hydrochlorofluoroolefin is selected from the group consisting of HCFO-1233zd, HCFO- 1223, HCFO-1233xf and mixtures thereof and further wherein said HFO- 1234yf comprises about 5 wt% or more of said polymer blowing agent composition.
3. The polymer blowing agent composition of claim 2, further comprising a hydro fluorocarbon. 4. The polymer blowing agent compositoin of claim 3 wherein said hydro fluorocarbon is sleeted from the group consisting of difiuoromethane (HFC32); 1,1,1,2,2-pentafluoroethane (HFC125); 1,1,1-trifluoroethane (143a); 1,1,2,2- tetrafluoroethane (HFC134); 1,1,1,2-tetrafluoroethane (HFC134a); 1,1-difluoroethane (HFC152a); 1,1,1,2,3,3,3-heptafluoropropane (HFC227ea); 1,1,1,3,3-pentafluoropropane (HFC245fa); 1,1,1,3,3-pentafluorobutane (HFC365mfc) and 1,1,1,2,2,3,
4,5,5,5- decafluoropentane (HFC431 Omee).
5. The polymer blowing agent composition of claim 2, further comprising a second hydrofluoroolefm selected from the group consisting of tetrafluoropropenes (HFO1234ze); trifluoropropenes (HFO1243zf); tetrafluorobutene isomers (HFO1354); pentafluorobutene isomers (HFO1345); hexafluorobutene isomers (HFO1336); heptafluorobutene isomers (HFO1327); heptafluoropentene isomers (HFO1447); octafluoropentene isomers (HFO1438) and nonafluoropentene isomers (HFO1429).
6. The polymer blowing agent composition of claim 1 further comprising a component selected from the group consisting of a second hydro fluoroolefin (HFO), a hydro fluorocarbon, a hydrocarbon, an alcohol, an ester, an aldehyde, a ketone ether/di ether, carbon dioxide and mixtures thereof.
7. A process of foaming a polyurethane foam comprising mixing polymer foam components with a foam blowing agent comprising (a) HFO-1234yf in combination with (b) at least one hydrochlorofluoroolefin (HCFO).
8. The process of claim 7 wherein said hydrochlorofluoroolefin is selected from the group consisting of HCFO-1233zd, HCFO-1223, HCFO-1233xf and mixtures and further wherein said HFO- 1234yf comprises about 5 wt% or more of said polymer blowing agent composition.
9. The process of claim 8, wherein said polymer blowing agent composition further comprising a hydrofluorocarbon.
10. The process of claim 9 wherein said hydrofluorocarbon is sleeted from the group consisting of difluoromethane (HFC32); 1,1,1,2,2-pentafluoroethane (HFC 125); 1,1,1-trifluoroethane (HFC143a); 1,1,2,2-tetrafluorothane (HFC134); 1,1,1,2- tetrafluoroethane (HFC134a); 1,1-difluoroethane (HFC152a); 1,1,1,2,3,3,3- heptafluoropropane (HFC227ea); 1,1,1,3,3-pentafluoropropane (HFC245fa); 1,1,1,3,3- pentafluorobutane (HFC365mfc) and 1,1,1,2,2,3,4,5,5,5-decafluoropentane (HFC4310mee).
11. The process of claim 8, further comprising a second hydro fluoroolefin selected form the group consisting of tetrafluoropropenes (HFO1234ze); trifluoropropenes (HFOl 243zf); tetrafluorobutene isomers (HFOl 354); pentafluorobutene isomers (HFO1345); hexafluorobutene isomers (HFO1336); heptafluorobutene isomers (HFO1327); heptafluoropentene isomers (HFO1447); octafluoropentene isomers (HFP1438) and nonafluoropentene isomers (HFP 1429).
PCT/US2008/058607 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin WO2008121790A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AT08744563T ATE528341T1 (en) 2007-03-29 2008-03-28 BLOWING AGENT COMPOSITION OF HYDROCHLORFLUOROLEFIN AND HYDROFLUOROLEFIN
PL08744563T PL2129715T3 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
US12/532,202 US9279039B2 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
CA2681872A CA2681872C (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
EP08744563A EP2129715B1 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
JP2010501249A JP5539854B2 (en) 2007-03-29 2008-03-28 Hydrochlorofluoroolefin and hydrofluoroolefin blowing agent composition
US15/015,184 US9914815B2 (en) 2007-03-29 2016-02-04 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90875107P 2007-03-29 2007-03-29
US60/908,751 2007-03-29

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/532,202 A-371-Of-International US9279039B2 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
US15/015,184 Division US9914815B2 (en) 2007-03-29 2016-02-04 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin

Publications (1)

Publication Number Publication Date
WO2008121790A1 true WO2008121790A1 (en) 2008-10-09

Family

ID=39808678

Family Applications (3)

Application Number Title Priority Date Filing Date
PCT/US2008/058607 WO2008121790A1 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
PCT/US2008/058602 WO2008121785A1 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
PCT/US2008/058604 WO2008121787A1 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrofluoropropene and hydrochlorofluoroolefin

Family Applications After (2)

Application Number Title Priority Date Filing Date
PCT/US2008/058602 WO2008121785A1 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
PCT/US2008/058604 WO2008121787A1 (en) 2007-03-29 2008-03-28 Blowing agent composition of hydrofluoropropene and hydrochlorofluoroolefin

Country Status (9)

Country Link
US (8) US20100087557A1 (en)
EP (3) EP2129715B1 (en)
JP (3) JP5539854B2 (en)
CN (6) CN101652413A (en)
AT (3) ATE528341T1 (en)
CA (3) CA2681838C (en)
ES (3) ES2367542T3 (en)
PL (3) PL2129713T3 (en)
WO (3) WO2008121790A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137658A2 (en) * 2008-05-07 2009-11-12 E. I. Du Pont De Nemours And Company Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
WO2011012390A1 (en) 2009-07-29 2011-02-03 Evonik Goldschmidt Gmbh Method for producing polyurethane foam
WO2012087667A1 (en) 2010-12-21 2012-06-28 Dow Global Technologies Llc Polyol formulations for improved cold temperature skin cure of polyurethane rigid foams
WO2013017554A1 (en) 2011-08-01 2013-02-07 Basf Se Hfo-/water-blown rigid-foam systems
JP2013508512A (en) * 2009-10-23 2013-03-07 アーケマ・インコーポレイテッド Tetrafluorobutene blowing agent composition for polyurethane foam
WO2013053555A2 (en) 2011-10-14 2013-04-18 Dow Global Technologies Llc Hybrid polyester-polyether polyols for improved demold expansion in polyurethane rigid foams
WO2013174844A1 (en) 2012-05-25 2013-11-28 Dow Global Technologies Llc Production of polyisocyanurate foam panels
EP2768893B1 (en) 2011-10-20 2016-04-06 E. I. du Pont de Nemours and Company Azeotrope-like compositions of e-1-chloro-2,3,3,3-tetrafluoropropene and uses thereof
US9896558B2 (en) 2011-08-01 2018-02-20 Basf Se HFO/water-blown rigid foam systems
US10301236B2 (en) 2015-05-21 2019-05-28 The Chemours Company Fc, Llc Hydrofluorination of a halogenated olefin with SbF5 in the liquid phase
JP2020063454A (en) * 2010-04-26 2020-04-23 ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー Azeotropic or azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene

Families Citing this family (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
TW201815923A (en) † 2005-06-24 2018-05-01 美商哈尼威爾國際公司 Foaming agents and compositions containing fluorine substituted olefins, and methods of foaming
US9695267B2 (en) * 2009-08-11 2017-07-04 Honeywell International Inc. Foams and foamable compositions containing halogenated olefin blowing agents
CA2681602C (en) * 2007-03-29 2014-10-28 Arkema Inc. Hydrofluoropropene blowing agents for thermoplastics
CA2693203A1 (en) * 2007-07-20 2009-01-29 E.I. Du Pont De Nemours And Company Compositions and use of trans-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based foams
US8333901B2 (en) 2007-10-12 2012-12-18 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
GB201002625D0 (en) 2010-02-16 2010-03-31 Ineos Fluor Holdings Ltd Heat transfer compositions
US8512591B2 (en) 2007-10-12 2013-08-20 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8628681B2 (en) 2007-10-12 2014-01-14 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
WO2009047542A1 (en) 2007-10-12 2009-04-16 Ineos Fluor Holdings Limited Heat transfer compositions
WO2009089400A1 (en) * 2008-01-11 2009-07-16 E. I. Du Pont De Nemours And Company Compositions and use of 2-chloro-3,3,3-trifluoropropene foam-forming composition in the preparation of polyisocyanate-based foams
JP6134470B2 (en) 2008-03-07 2017-05-24 アーケマ・インコーポレイテッド Stable formulation system with chloro-3,3,3-trifluoropropene
JP2011530646A (en) * 2008-08-13 2011-12-22 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Foam-forming composition containing a mixture of 2-chloro-3,3,3-trifluoropropene and hydrocarbon and its use in the production of polyisocyanate based foam
US8163196B2 (en) * 2008-10-28 2012-04-24 Honeywell International Inc. Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene
MX2011005358A (en) * 2008-12-02 2011-06-24 Mexichem Amanco Holding Sa De Capital Variable Heat transfer compositions.
US9815955B2 (en) * 2009-01-29 2017-11-14 Arkema Inc. Tetrafluoropropene based blowing agent compositions
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
TW201103972A (en) 2009-04-01 2011-02-01 Solvay Fluor Gmbh Process for the manufacture of etched items
US8541478B2 (en) 2009-05-21 2013-09-24 Huntsman International Llc Rigid polyurethane foam and system and method for making the same
SG176231A1 (en) * 2009-06-02 2011-12-29 Du Pont Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
CA2769337A1 (en) * 2009-07-27 2011-02-03 Arkema Inc. Composition of hcfo-1233zd and polyol blends for use in polyurethane foam
EP4324901A3 (en) * 2009-09-09 2024-04-24 Honeywell International, Inc. Monochlorotrifluoropropene compounds and compositions and methods using same
US8846754B2 (en) * 2009-12-16 2014-09-30 Honeywell International Inc. Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene
KR20210064415A (en) 2009-12-22 2021-06-02 더 케무어스 컴퍼니 에프씨, 엘엘씨 Compositions comprising 2,3,3,3-tetrafluoropropene, 1,1,2,3-tetrachloropropene, 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1,2-tetrafluoropropane
GB201002622D0 (en) 2010-02-16 2010-03-31 Ineos Fluor Holdings Ltd Heat transfer compositions
GB2480513B (en) 2010-05-20 2013-01-02 Mexichem Amanco Holding Sa Heat transfer compositions
KR20130082095A (en) 2010-05-20 2013-07-18 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. Heat transfer compositions
GB2481443B (en) 2010-06-25 2012-10-17 Mexichem Amanco Holding Sa Heat transfer compositions
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
US20120046372A1 (en) * 2010-08-18 2012-02-23 Honeywell International Inc. Blowing agents, foamable compositions and foams
US9145480B2 (en) * 2010-10-28 2015-09-29 Honeywell International Inc. Mixtures containing 1,1,1,3,3,3-hexafluorobutene and 1-chloro-3,3,3-trifluoropropene
CA2817556C (en) 2010-11-17 2014-12-30 Fomo Products, Inc. Method for filling wall cavities with expanding foam insulation
US8734671B2 (en) * 2010-11-19 2014-05-27 Honeywell International Inc. Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene
US9157018B2 (en) * 2010-11-25 2015-10-13 Arkema France Compositions of chloro-trifluoropropene and hexafluorobutene
FR2968310B1 (en) * 2010-12-03 2012-12-07 Arkema France COMPOSITIONS BASED ON 1,1,1,4,4,4-HEXAFLUOROBUT-2-ENE AND 3,3,4,4,4-PENTAFLUOROBUT-1-ENE
US9724684B2 (en) * 2011-02-21 2017-08-08 The Chemours Company Fc, Llc Selective catalytical dehydrochlorination of hydrochlorofluorocarbons
FR2977256B1 (en) * 2011-07-01 2013-06-21 Arkema France COMPOSITIONS OF 2,4,4,4-TETRAFLUOROBUT-1-ENE AND CIS-1,1,1,4,4,4-HEXAFLUOROBUT-2-ENE
CN103814108B (en) * 2011-07-28 2016-08-24 霍尼韦尔国际公司 Foam containing 1-chloro-3,3,3-trifluoro propene (1233ZD) and the fire-retardant product being made up of the foam containing 1-chloro-3,3,3-trifluoro propene (1233ZD)
WO2013082964A1 (en) * 2011-12-09 2013-06-13 Honeywell International Inc. Foams and articles made from foams containing hcfo or hfo blowing agents
JP2015507039A (en) * 2011-12-22 2015-03-05 ハネウェル・インターナショナル・インコーポレーテッド An azeotrope-like composition comprising cis-1-chloro-3,3,3-trifluoropropene
US8921621B2 (en) 2012-02-15 2014-12-30 Honeywell International Inc. Process for the production of HCFC-1233zd
US9000239B2 (en) * 2012-05-15 2015-04-07 Honeywell International Inc. Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene
CN104781315B (en) * 2012-09-07 2019-03-08 巴斯夫欧洲公司 Reduce the hard polyurethane foams shunk
CN102850571A (en) * 2012-09-28 2013-01-02 关志强 Foaming agent of heat insulation polyurethane plastics
FR3000094B1 (en) * 2012-12-26 2019-10-18 Arkema France COMPOSITION COMPRISING 1,1-DIFLUOROETHANE AND 3,3,3-TRIFLUOROPROPENE
CN104046331A (en) * 2013-03-14 2014-09-17 霍尼韦尔国际公司 Low GWP fluids for high temperature heat pump applications
FI3495407T3 (en) 2013-03-15 2024-02-22 Owens Corning Intellectual Capital Llc Processing aids for use in manufacturing extruded polystyrene foams using low global warming potential blowing agents
US20150210818A1 (en) * 2014-01-27 2015-07-30 E I Du Pont De Nemours And Company Cryogenic insulation foam
CN103881131A (en) * 2014-03-17 2014-06-25 浙江衢化氟化学有限公司 Environment-friendly foaming agent composition
MX2016014167A (en) * 2014-04-30 2017-02-22 Honeywell Int Inc Flexible, open-cell thermoset foams and blowing agents and methods for making same.
US10330364B2 (en) 2014-06-26 2019-06-25 Hudson Technologies, Inc. System and method for retrofitting a refrigeration system from HCFC to HFC refrigerant
CN104119490A (en) * 2014-07-10 2014-10-29 合肥美的电冰箱有限公司 A composition, a foam material prepared from the composition, a preparing method of the foam material and applications of the foam material
MX2017000515A (en) * 2014-07-16 2017-08-18 Owens Corning Intellectual Capital Llc Non-voc processing aids for use in manufacturing foams using low global warming potential blowing agents.
JP6626674B2 (en) * 2014-10-08 2019-12-25 積水ソフランウイズ株式会社 Polyol composition for rigid polyurethane foam, and method for producing rigid polyurethane foam
EP3677623A1 (en) * 2015-03-24 2020-07-08 Asahi Kasei Construction Materials Corporation Phenolic resin foam and method of producing same
JP6725494B2 (en) * 2015-03-24 2020-07-22 積水化学工業株式会社 Phenolic resin foam and method for producing phenolic resin foam
CN107849500B (en) * 2015-07-27 2020-11-06 Ａｇｃ株式会社 Solvent composition, cleaning method, method for forming coating film, heat transfer medium, and heat cycle system
CN105885080A (en) * 2016-05-05 2016-08-24 巨化集团技术中心 Foamer composition and preparation method thereof
CH712779A1 (en) * 2016-07-20 2018-01-31 Brugg Rohr Ag Holding Barrier layers.
US10131758B2 (en) 2016-07-25 2018-11-20 Accella Polyurethane Systems, Llc Polyurethane foam-forming compositions, methods of making low density foams using such compositions, and foams formed therefrom
CN106750488B (en) * 2016-12-26 2019-05-17 浙江衢化氟化学有限公司 A kind of low-carbon environment-friendly foaming agent
CN108727551A (en) * 2017-04-19 2018-11-02 科思创德国股份有限公司 A kind of hard polyurethane foams and the preparation method and application thereof
CN108102333A (en) * 2017-12-27 2018-06-01 上海东大聚氨酯有限公司 A kind of ultralow temperature incubator combined polyether, polyurethane raw material composition, polyurethane foam and preparation method thereof
EP3831918A4 (en) * 2018-07-27 2022-04-13 Central Glass Company, Limited Solvent composition
CN110105520B (en) * 2019-05-05 2021-09-21 深圳市盈石科技有限公司 Heat-insulating rigid polyurethane foam and preparation method thereof
WO2021158649A1 (en) * 2020-02-04 2021-08-12 The Chemours Company Fc, Llc Nucleating agents for pir foams
JPWO2022009801A1 (en) * 2020-07-08 2022-01-13
CN114149790B (en) * 2021-11-10 2023-09-05 浙江巨化新材料研究院有限公司 Azeotropic or azeotrope-like compositions and methods of making same
CN117940474A (en) * 2022-05-20 2024-04-26 海信容声(广东)冰箱有限公司 Polyurethane foam material and preparation method thereof, refrigerator and freezer

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006069362A2 (en) * 2004-12-21 2006-06-29 Honeywell International Inc. Stabilized iodocarbon compositions

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2039008A (en) 1932-07-28 1936-04-28 Burgess Lab Inc C F Method of making a material for absorbing sound
JPH02221388A (en) 1989-02-23 1990-09-04 Asahi Glass Co Ltd Degreasing detergent
JP2751428B2 (en) 1989-06-30 1998-05-18 旭硝子株式会社 3,3-dichloro-1,1,1,2,2-pentafluoropropane-based composition
JPH05179042A (en) * 1991-11-18 1993-07-20 Daikin Ind Ltd Blowing agent comprising fluoropropene and production of plastic foam
US5710352A (en) 1996-09-19 1998-01-20 Alliedsignal Inc. Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene
DE69807962T2 (en) 1997-03-11 2003-01-30 Central Glass Co Ltd Process for the purification of crude 1,1,1,3,3-pentafluoropropane
US6013846A (en) * 1998-03-05 2000-01-11 Elf Atochem North America, Inc. Azeotrope of HF and 1233zd
US20050096246A1 (en) * 2003-11-04 2005-05-05 Johnson Robert C. Solvent compositions containing chlorofluoroolefins
US20090253820A1 (en) 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US9796848B2 (en) * 2002-10-25 2017-10-24 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
US7279451B2 (en) * 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
CN1732243A (en) * 2002-10-25 2006-02-08 霍尼韦尔国际公司 Compositions containing fluorine substituted olefins
US9499729B2 (en) 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US7098176B2 (en) 2004-04-16 2006-08-29 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and pentafluoropropene
US20060243945A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
TWI558685B (en) 2005-06-24 2016-11-21 哈尼威爾國際公司 Compositions containing fluorine substituted olefins
TW201815923A (en) * 2005-06-24 2018-05-01 美商哈尼威爾國際公司 Foaming agents and compositions containing fluorine substituted olefins, and methods of foaming
EP2412753B1 (en) 2007-03-29 2016-10-19 Arkema Inc. Closed cell foam and process
CN100488925C (en) 2007-04-11 2009-05-20 西安近代化学研究所 Method for producing 1,1,1,3-tetrafluoroethylene

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006069362A2 (en) * 2004-12-21 2006-06-29 Honeywell International Inc. Stabilized iodocarbon compositions

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8877086B2 (en) 2008-05-07 2014-11-04 E I Du Pont De Nemours And Company Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
WO2009137658A3 (en) * 2008-05-07 2009-12-30 E. I. Du Pont De Nemours And Company Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
US9486657B2 (en) 2008-05-07 2016-11-08 The Chemours Company Fc, Llc Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
US10214669B2 (en) 2008-05-07 2019-02-26 The Chemours Company Fc, Llc Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
US11512239B2 (en) 2008-05-07 2022-11-29 The Chemours Company Fc, Llc Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
US11312890B2 (en) 2008-05-07 2022-04-26 The Chemours Company Fc, Llc Compositions comprising 2,3-dichloro-1,1,1 -trifluoropropane, 2-chloro-1,1,1 -trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
US10584270B2 (en) 2008-05-07 2020-03-10 The Chemours Company Fc, Llc Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
US11001738B2 (en) 2008-05-07 2021-05-11 The Chemours Company Fc, Llc Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
WO2009137658A2 (en) * 2008-05-07 2009-11-12 E. I. Du Pont De Nemours And Company Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
AU2009244265B2 (en) * 2008-05-07 2014-06-26 The Chemours Company Fc, Llc. Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
DE102009028061A1 (en) 2009-07-29 2011-02-10 Evonik Goldschmidt Gmbh Process for the production of polyurethane foam
US8906974B2 (en) 2009-07-29 2014-12-09 Evonik Degussa Gmbh Method for producing polyurethane foam
WO2011012390A1 (en) 2009-07-29 2011-02-03 Evonik Goldschmidt Gmbh Method for producing polyurethane foam
JP2013508512A (en) * 2009-10-23 2013-03-07 アーケマ・インコーポレイテッド Tetrafluorobutene blowing agent composition for polyurethane foam
JP2020063454A (en) * 2010-04-26 2020-04-23 ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー Azeotropic or azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene
WO2012087667A1 (en) 2010-12-21 2012-06-28 Dow Global Technologies Llc Polyol formulations for improved cold temperature skin cure of polyurethane rigid foams
US9896558B2 (en) 2011-08-01 2018-02-20 Basf Se HFO/water-blown rigid foam systems
WO2013017554A1 (en) 2011-08-01 2013-02-07 Basf Se Hfo-/water-blown rigid-foam systems
WO2013053555A2 (en) 2011-10-14 2013-04-18 Dow Global Technologies Llc Hybrid polyester-polyether polyols for improved demold expansion in polyurethane rigid foams
EP2768893B1 (en) 2011-10-20 2016-04-06 E. I. du Pont de Nemours and Company Azeotrope-like compositions of e-1-chloro-2,3,3,3-tetrafluoropropene and uses thereof
WO2013174844A1 (en) 2012-05-25 2013-11-28 Dow Global Technologies Llc Production of polyisocyanurate foam panels
US10301236B2 (en) 2015-05-21 2019-05-28 The Chemours Company Fc, Llc Hydrofluorination of a halogenated olefin with SbF5 in the liquid phase
US10988422B2 (en) 2015-05-21 2021-04-27 The Chemours Company Fc, Llc Hydrofluoroalkane composition
US11008267B2 (en) 2015-05-21 2021-05-18 The Chemours Company Fc, Llc Hydrofluoroalkane composition
US11572326B2 (en) 2015-05-21 2023-02-07 The Chemours Company Fc, Llc Method for preparing 1,1,1,2,2-pentafluoropropane
US12006274B2 (en) 2015-05-21 2024-06-11 The Chemours Company Fc, Llc Compositions including olefin and hydrofluoroalkane

Also Published As

Publication number Publication date
EP2129714B1 (en) 2011-08-03
US20160152787A1 (en) 2016-06-02
WO2008121785A1 (en) 2008-10-09
EP2129713B1 (en) 2012-02-29
ES2367542T3 (en) 2011-11-04
US9914815B2 (en) 2018-03-13
CN101646722A (en) 2010-02-10
CN103992498A (en) 2014-08-20
US20160090462A1 (en) 2016-03-31
CN101652412A (en) 2010-02-17
CN101652413A (en) 2010-02-17
WO2008121787A1 (en) 2008-10-09
CA2681642C (en) 2015-05-26
ATE518905T1 (en) 2011-08-15
EP2129715A4 (en) 2010-03-24
CA2681642A1 (en) 2008-10-09
US20160362531A1 (en) 2016-12-15
ATE528341T1 (en) 2011-10-15
US20100056657A1 (en) 2010-03-04
PL2129713T3 (en) 2012-10-31
US9228071B2 (en) 2016-01-05
CN101652412B (en) 2012-07-25
CA2681872A1 (en) 2008-10-09
CN104962070B (en) 2018-06-01
ES2372785T3 (en) 2012-01-26
EP2129714A4 (en) 2010-03-24
PL2129714T3 (en) 2012-04-30
US20100087557A1 (en) 2010-04-08
US9279039B2 (en) 2016-03-08
US20140296360A1 (en) 2014-10-02
CN104962070A (en) 2015-10-07
EP2129713A4 (en) 2010-03-31
EP2129713A1 (en) 2009-12-09
JP5416087B2 (en) 2014-02-12
CA2681838C (en) 2015-05-26
PL2129715T3 (en) 2012-02-29
JP2010522821A (en) 2010-07-08
JP2010522820A (en) 2010-07-08
CN101646723A (en) 2010-02-10
CA2681838A1 (en) 2008-10-09
JP2010522822A (en) 2010-07-08
JP5539854B2 (en) 2014-07-02
US20100076100A1 (en) 2010-03-25
CA2681872C (en) 2015-06-09
JP5416086B2 (en) 2014-02-12
ES2380080T3 (en) 2012-05-08
EP2129715A1 (en) 2009-12-09
US20140336293A1 (en) 2014-11-13
ATE547459T1 (en) 2012-03-15
CN103992498B (en) 2017-11-07
EP2129715B1 (en) 2011-10-12
EP2129714A1 (en) 2009-12-09

Similar Documents

Publication Publication Date Title
US9914815B2 (en) Blowing agent composition of hydrochlorofluoroolefin and hydrofluoroolefin
JP6441983B2 (en) Hydrochlorofluoroolefin blowing agent composition

Legal Events

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

Ref document number: 200880010511.4

Country of ref document: CN

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

Ref document number: 08744563

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008744563

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 12532202

Country of ref document: US

ENP Entry into the national phase

Ref document number: 2681872

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 2010501249

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE