[go: up one dir, main page]

WO2009089400A1 - Compositions et utilisation d'une composition moussante à base de 2-chloro-3,3,3-trifluoropropène dans la préparation de mousses à base de polyisocyanate - Google Patents

Compositions et utilisation d'une composition moussante à base de 2-chloro-3,3,3-trifluoropropène dans la préparation de mousses à base de polyisocyanate Download PDF

Info

Publication number
WO2009089400A1
WO2009089400A1 PCT/US2009/030514 US2009030514W WO2009089400A1 WO 2009089400 A1 WO2009089400 A1 WO 2009089400A1 US 2009030514 W US2009030514 W US 2009030514W WO 2009089400 A1 WO2009089400 A1 WO 2009089400A1
Authority
WO
WIPO (PCT)
Prior art keywords
foam
polyisocyanate
forming composition
polyol
chloro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2009/030514
Other languages
English (en)
Inventor
Gary Loh
Joseph Anthony Creazzo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO2009089400A1 publication Critical patent/WO2009089400A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy groups
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/0058—≥50 and <150kg/m3
    • 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
    • C08G2115/00—Oligomerisation
    • C08G2115/02—Oligomerisation to isocyanurate groups
    • 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
    • C08J2205/052—Closed cells, i.e. more than 50% of the pores are closed
    • 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
    • C08J2375/08—Polyurethanes from polyethers

Definitions

  • the disclosure herein relates to foam-forming compositions comprising a chlorofluoroolefin blowing agent and an active hydrogen- containing compounds, and using such compositions for producing polyurethane and polyisocyanurate foams. More particularly, the disclosure herein relates to foam-forming compositions comprising 2- chloro-3,3,3-trifluoropropene and an active hydrogen-containing compound having two or more active hydrogens, and using such compositions for producing polyurethane and polyisocyanurate foams.
  • Closed-cell polyisocyanate-based foams are widely used for insulation purposes, for example, in building construction and in the manufacture of energy efficient electrical appliances.
  • polyurethane/polyisocyanurate board stock is used in roofing and siding for its insulation and load-carrying capabilities.
  • Poured and sprayed polyurethane foams are widely used for a variety of applications including insulating roofs, insulating large structures such as storage tanks, insulating appliances such as refrigerators and freezers, insulating refrigerated trucks and railcars, etc.
  • blowing agents also known as foam expansion agents or foam expansion compositions
  • Insulating foams depend on the use of halocarbon blowing agents, not only to foam the polymer, but primarily for their low vapor thermal conductivity, a very important characteristic for insulation value.
  • hydrofluorocarbons HFCs
  • HFC-245fa 1 ,1 ,1 ,3,3-pentafluoropropane
  • HFCs are of concern due to their contribution to the "greenhouse effect", i.e., they contribute to global warming. As a result of their contribution to global warming, the HFCs have come under scrutiny, and their widespread use may also be limited in the future.
  • Hydrocarbons have also been proposed as foam blowing agents.
  • VOCs volatile organic compounds
  • This disclosure provides a foam-forming composition comprising 2- chloro-3,3,3-trifluoropropene and an active hydrogen-containing compound having two or more active hydrogens.
  • This disclosure also provides a closed-cell polyurethane or polyisocyanurate polymer foam prepared from reaction of effective amounts of the foam-forming composition and a suitable polyisocyanate.
  • This disclosure also provides a method for producing a closed-cell polyurethane or polyisocyanurate polymer foam.
  • the method comprises reacting an effective amount of the foam-forming composition and a suitable polyisocyanate.
  • composition of this disclosure is a foam-forming composition comprising 2-chloro-3,3,3-thfluoropropene (HCFC-1233xf) and an active hydrogen-containing compound having two or more active hydrogens, in the form of hydroxyl groups.
  • HCFC-1233xf is used as a blowing agent.
  • HCFC-1233xf is a known compound which is available from
  • cream time it is meant to refer to the time period starting from the mixing of the active hydrogen-containing compound with polyisocyanate, and ending at when the foaming starts to occur and color of the mixture starts to change.
  • rise time it is meant to refer to the time period starting from the mixing of the active hydrogen-containing compound with polyisocyanate, and ending at when the foam rising stops.
  • tacky free time it is meant to refer to the time period starting from the mixing of the active hydrogen-containing compound with polyisocyanate, and ending at when the surface of the foam is no longer tacky.
  • initial R-value it is meant to refer to the polymer foam's insulation value (thermal resistance) measured at a mean temperature of 75 0 F within 24 hours after the foam is formed and becomes tack free.
  • the active hydrogen-containing compounds of this invention can comprise compounds having two or more groups that contain an active hydrogen atom reactive with an isocyanate group, such as described in U.S. Patent No. 4,394,491 ; hereby incorporated by reference.
  • Examples of such compounds have at least two hydroxyl groups per molecule, and more specifically comprise polyols, such as polyether or polyester polyols.
  • polyols such as polyether or polyester polyols.
  • polyols are those which have an equivalent weight of about 50 to about 700, normally of about 70 to about 300, more typically of about 90 to about 270, and carry at least 2 hydroxyl groups, usually 3 to 8 such groups.
  • polyester polyols such as aromatic polyester polyols, e.g., those made by transesterifying polyethylene terephthalate (PET) scrap with a glycol such as diethylene glycol, or made by reacting phthalic anhydride with a glycol.
  • PET polyethylene terephthalate
  • the resulting polyester polyols may be reacted further with ethylene - and/or propylene oxide - to form an extended polyester polyol containing additional internal alkyleneoxy groups.
  • suitable polyols also comprise polyether polyols such as polyethylene oxides, polypropylene oxides, mixed polyethylene- propylene oxides with terminal hydroxyl groups, among others.
  • Suitable polyols can be prepared by reacting ethylene and/or propylene oxide with an initiator having 2 to 16, generally 3 to 8 hydroxyl groups as present, for example, in glycerol, pentaerythhtol and carbohydrates such as sorbitol, glucose, sucrose and the like polyhydroxy compounds.
  • Suitable polyether polyols can also include alaphatic or aromatic amine- based polyols.
  • the present invention also relates to processes for producing a closed-cell polyurethane or polyisocyanurate polymer foam by reacting an effective amount of the foam-forming compositions with a suitable polyisocyanate.
  • foam-forming composition typically known in the art as an isocyanate-reactive preblend, or B-side composition.
  • the foam-forming composition of this invention can be prepared in any manner convenient to one skilled in this art, including simply weighing desired quantities of each component and, thereafter, combining them in an appropriate container at appropriate temperatures and pressures.
  • the polyisocyanate reactant is normally selected in such proportion relative to that of the active hydrogen-containing compound that the ratio of the equivalents of isocyanate groups to the equivalents of active hydrogen groups, i.e., the foam index, is from about 0.9 to about 10 and in most cases from about 1 to about 4. While any suitable polyisocyanate can be employed in the instant process, examples of suitable polyisocyanates useful for making polyisocyanate-based foam comprise at least one of aromatic, aliphatic and cycloaliphatic polyisocyanates, among others.
  • Representative members of these compounds comprise diisocyanates such as meta- or paraphenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6- diisocyanate, hexamethylene-1 ,6-diisocyanate, tetramethylene-1 ,4- diisocyanate, cyclohexane-1 ,4-diisocyanate, hexahydrotoluene diisocyanate (and isomers), napthylene-1 ,5-diisocyanate, 1-methylphenyl- 2,4-phenyldiisocyanate, diphenylmethane-4,4-diisocyanate, diphenylmethane-2,4-diissocyanate, 4,4 -biphenylenediisocyanate and 3,3-dimethyoxy-4,4 biphenylenediisocyanate and 3,3- dimethyldiphenylpropane
  • a crude polyisocyanate may also be used in the practice of this invention, such as the crude toluene diisocyanate obtained by the phosgenating a mixture comprising toluene diamines, or the crude diphenylmethane diisocyanate obtained by the phosgenating crude diphenylmethanediamine.
  • Specific examples of such compounds comprise methylene-bhdged polyphenylpolyisocyanat.es, due to their ability to crosslink the polyurethane.
  • additives comprise one or more members from the group consisting of catalysts, surfactants, flame retardants, preservatives, colorants, antioxidants, reinforcing agents, filler, antistatic agents, among others well known in this art.
  • a surfactant can be employed to stabilize the foaming reaction mixture while curing.
  • Such surfactants normally comprise a liquid or solid organosilicone compound. The surfactants are employed in amounts sufficient to stabilize the foaming reaction mixture against collapse and to prevent the formation of large, uneven cells.
  • 0.1 % to about 5% by weight of surfactant based on the total weight of all foaming ingredients are used.
  • about 1.5% to about 3% by weight of surfactant based on the total weight of all foaming ingredients are used.
  • One or more catalysts for the reaction of the active hydrogen- containing compounds, e.g. polyols, with the polyisocyanate may be also employed. While any suitable urethane catalyst may be employed, specific catalyst comprise tertiary amine compounds and organometallic compounds. Exemplary such catalysts are disclosed, for example, in U.S. Patent No. 5,164,419, which disclosure is incorporated herein by reference. For example, a catalyst for the thmerization of polyisocyanates, such as an alkali metal alkoxide, alkali metal carboxylate, or quaternary amine compound, may also optionally be employed herein. Such catalysts are used in an amount which measurably increases the rate of reaction of the polyisocyanate.
  • Typical amounts of catalysts are about 0.1 % to about 5% by weight based on the total weight of all foaming ingredients.
  • the active hydrogen-containing compound e.g. polyol
  • polyisocyanate and other components are contacted, thoroughly mixed, and permitted to expand and cure into a cellular polymer.
  • the mixing apparatus is not critical, and various conventional types of mixing head and spray apparatus are used.
  • conventional apparatus is meant apparatus, equipment, and procedures conventionally employed in the preparation of isocyanate-based foams in which conventional isocyanate-based foam blowing agents, such as fluorothchloromethane (CCI3F, CFC- 11 ), are employed.
  • conventional apparatus are discussed by: H.
  • a preblend of certain raw materials is prepared prior to reacting the polyisocyanate and active hydrogen-containing components.
  • all the foaming ingredients may be introduced individually to the mixing zone where the polyisocyanate and polyol(s) are contacted. It is also possible to pre-react all or a portion of the polyol(s) with the polyisocyanate to form a prepolymer.
  • composition and processes are applicable to the production of all kinds of expanded polyurethane foams, including, for example, integral skin, RIM and flexible foams, and in particular rigid closed-cell polymer foams useful in spray insulation, as pour-in-place appliance foams, or as rigid insulating board stock and laminates.
  • the present invention also relates to the closed-cell polyurethane or polyisocyanurate polymer foams prepared from reaction of effective amounts of the foam-forming composition of this disclosure and a suitable polyisocyanate.
  • Polyol A used in this Example is a sucrose/glycerine initiated polyether polyol (Voranol 360) purchased from Dow Chemicals Inc. at Midland, Ml, 49641 -1206. Polyol in this Example has viscosity of 3,600 centerpoise at 25 0 C. The content of hydroxyl groups in Polyol of this Example is equivalent to 360 mg KOH per gram of Polyol.
  • Polyol B is a toluene diamine (o-TDA) initiated aromatic polyether polyol (VORANOL 391 ) purchased from Dow Chemicals Inc. at Midland, Ml, 49641 -1206. Polyol B has viscosity of 4740 centerpoise at 25 0 C. The content of hydroxyl groups in Polyol B is equivalent to 391 mg KOH per gram of Polyol B.
  • o-TDA toluene diamine
  • VORANOL 391 toluene diamine
  • Polyol C is an aromatic polyester polyol (Stepanpol PS2502-A) purchased from STEPAN Inc. at 22W Frontage Road, Northfield, IL 60093. Polyol C has viscosity of 3,000 centerpoise at 25 0 C. The content of hydroxyl groups in Polyol C is equivalent to 240 mg KOH per gram of Polyol C.
  • Silicon type surfactant A (Niax Silicone L-6900) and B (Niax Silicone L-5440) are mixtures of polyalkyleneoxidemethylsiloxane and polyalkylene oxide purchased from Momentive Performance Materials at 187 Danbury Road, Wilton, CT 06897 USA.
  • Silicon type surfactant C is a polysiloxane (Dabco DC193) purchased from Air Products Inc. at 7201 Hamilton Boulevard, Allentown PA 18195.
  • Amine catalyst A (Polycat 8) is N,N-dimethylcyclohexylamine purchased from Air Products Inc. at 7201 Hamilton Boulevard, Allentown PA 18195.
  • Amine catalyst B (Polycat 5) is Pentamethyldiethylenethamine purchased from Air Products Inc. at 7201 Hamilton Boulevard, Allentown PA 18195.
  • Co-catalyst (Curithane 52) is 2-methyl(n-nnethyl amino b-sodium acetate nonyl phenol) purchased from Air Products Inc. at 7201 Hamilton BI vd, Allentown PA 18195.
  • Potassium catalyst (Potassium HEX-CEM 977) contains 25 wt% diethylene glycol and 75 wt% potassium 2-ethylhexanoate, and is purchased from OMG Americas Inc. at 127 Public Square, 1500 Key Tower, Cleveland, OH 44114.
  • Amine catalyst C (Dabco TMR-30) is Tris-2,4,6- (dimethylaminomethyl)phenol purchased from Air Products Inc. at 7201 Hamilton Boulevard, Allentown PA 18195.
  • Polymethylene polyphenyl isocyanate A (PAPI 27) and B (PAPI 580N) are purchased from Dow Chemicals, Inc. at Midland, Ml, 49641 - 1206.
  • EXAMPLE 1 Polyol A, surfactant, catalysts, water and 2-chloro-3,3,3- thfluoropropene were pre-mixed by hand in a container with known volume. Polyisocyanate was added to the container to form the polyurethane foam. The foam was cut along the edge of the container to check the cell structure and density. The foam showed uniform cell structure. The formulation and properties of the foam are shown in Table 1 below. Table 1 Polyurethane foam formulation and properties - Polvol A
  • Polyol A, surfactant, catalysts, water and 2-chloro-3,3,3- trifluoropropene were pre-mixed by hand and then mixed with polyisocyanate. The resulting mixture was poured into a 8"x8"x2.5" paper box to form the polyurethane foam.
  • the formulation and properties of the foam are shown in Tables 2 and 3 below.
  • Polyol B, surfactant B, catalysts, water and 2-chloro-3,3,3- trifluoropropene were pre-mixed by hand and then mixed with polyisocyanate. The resulting mixture was poured into a 8"x8"x2.5" paper box to form the polyurethane foam.
  • the formulation and properties of the foam are shown in Tables 4 and 5 below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne une composition moussante qui comprend du 2-chloro-3,3,3-trifluoropropène ainsi qu'un composé actif contenant de l'hydrogène et comportant deux atomes d'hydrogène actifs ou plus. L'invention concerne également une mousse polymère de polyuréthane ou de polyisocyanurate à alvéoles fermés préparée à partir d'une réaction de quantités efficaces de la composition moussante et d'un polyisocyanate approprié. L'invention concerne également un procédé pour produire une mousse polymère de polyuréthane ou de polyisocyanurate à alvéoles fermés préparée par réaction d'une quantité efficace de la composition moussante avec un polyisocyanate approprié.
PCT/US2009/030514 2008-01-11 2009-01-09 Compositions et utilisation d'une composition moussante à base de 2-chloro-3,3,3-trifluoropropène dans la préparation de mousses à base de polyisocyanate Ceased WO2009089400A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US2046508P 2008-01-11 2008-01-11
US61/020,465 2008-01-11
US10767908P 2008-10-23 2008-10-23
US61/107,679 2008-10-23

Publications (1)

Publication Number Publication Date
WO2009089400A1 true WO2009089400A1 (fr) 2009-07-16

Family

ID=40566132

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/030514 Ceased WO2009089400A1 (fr) 2008-01-11 2009-01-09 Compositions et utilisation d'une composition moussante à base de 2-chloro-3,3,3-trifluoropropène dans la préparation de mousses à base de polyisocyanate

Country Status (1)

Country Link
WO (1) WO2009089400A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011012390A1 (fr) 2009-07-29 2011-02-03 Evonik Goldschmidt Gmbh Procédé pour produire de la mousse de polyuréthane
WO2012031868A1 (fr) * 2010-09-09 2012-03-15 Evonik Goldschmidt Gmbh Procédé de production d'éléments composites à base de mousse de polyuréthane
WO2013017554A1 (fr) 2011-08-01 2013-02-07 Basf Se Systèmes de mousse rigide gonflée par un mélange hfo/eau
JP2014505782A (ja) * 2011-02-21 2014-03-06 ハネウェル・インターナショナル・インコーポレーテッド ハロゲン化オレフィン発泡剤を含むポリウレタンフォームポリオールプレミックスのための触媒
JP2014506947A (ja) * 2011-02-21 2014-03-20 ハネウェル・インターナショナル・インコーポレーテッド ハロゲン化オレフィン発泡剤を含むポリウレタンフォームプレミックス及びそれから製造されるフォーム
EP2513227A4 (fr) * 2009-12-17 2014-12-03 Honeywell Int Inc Catalyseurs pour des prémélanges de polyol de mousse de polyuréthane contenant des agents gonflants d'oléfine halogénés
WO2018022405A1 (fr) * 2016-07-25 2018-02-01 Covestro Llc Compositions formant des mousses de polyuréthane, procédés de fabrication de mousses de faible densité à l'aide de telles compositions et mousses formées à partir de celles-ci
US9896558B2 (en) 2011-08-01 2018-02-20 Basf Se HFO/water-blown rigid foam systems
WO2018192990A1 (fr) * 2017-04-19 2018-10-25 Covestro Deutschland Ag Mousse de polyuréthane rigide, procédé de préparation et application associés
JP2023500909A (ja) * 2019-11-06 2023-01-11 ハネウェル・インターナショナル・インコーポレーテッド ２－クロロ－３，３，３－トリフルオロプロペン（ｈｃｆｏ－１２３３ｘｆ）および水の共沸混合物または共沸混合物様組成物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070010592A1 (en) * 2002-10-25 2007-01-11 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
WO2008121785A1 (fr) * 2007-03-29 2008-10-09 Arkema Inc. Composition d'agent d'expansion à base d'hydrochlorofluooléfine et d'hydrofluorooléfine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070010592A1 (en) * 2002-10-25 2007-01-11 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
WO2008121785A1 (fr) * 2007-03-29 2008-10-09 Arkema Inc. Composition d'agent d'expansion à base d'hydrochlorofluooléfine et d'hydrofluorooléfine

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102471446B (zh) * 2009-07-29 2014-08-06 赢创高施米特有限公司 聚氨酯泡沫的制备方法
KR101752933B1 (ko) * 2009-07-29 2017-07-03 에보니크 데구사 게엠베하 폴리우레탄 발포체를 제조하는 방법
CN102471446A (zh) * 2009-07-29 2012-05-23 赢创高施米特有限公司 聚氨酯泡沫的制备方法
US8906974B2 (en) 2009-07-29 2014-12-09 Evonik Degussa Gmbh Method for producing polyurethane foam
WO2011012390A1 (fr) 2009-07-29 2011-02-03 Evonik Goldschmidt Gmbh Procédé pour produire de la mousse de polyuréthane
EP2513227A4 (fr) * 2009-12-17 2014-12-03 Honeywell Int Inc Catalyseurs pour des prémélanges de polyol de mousse de polyuréthane contenant des agents gonflants d'oléfine halogénés
CN103097439A (zh) * 2010-09-09 2013-05-08 赢创高施米特有限公司 基于聚氨酯泡沫的复合物元件的制备方法
CN103097439B (zh) * 2010-09-09 2016-01-13 赢创德固赛有限公司 基于聚氨酯泡沫的复合物元件的制备方法
WO2012031868A1 (fr) * 2010-09-09 2012-03-15 Evonik Goldschmidt Gmbh Procédé de production d'éléments composites à base de mousse de polyuréthane
JP2014506947A (ja) * 2011-02-21 2014-03-20 ハネウェル・インターナショナル・インコーポレーテッド ハロゲン化オレフィン発泡剤を含むポリウレタンフォームプレミックス及びそれから製造されるフォーム
JP2014505782A (ja) * 2011-02-21 2014-03-06 ハネウェル・インターナショナル・インコーポレーテッド ハロゲン化オレフィン発泡剤を含むポリウレタンフォームポリオールプレミックスのための触媒
WO2013017554A1 (fr) 2011-08-01 2013-02-07 Basf Se Systèmes de mousse rigide gonflée par un mélange hfo/eau
US9896558B2 (en) 2011-08-01 2018-02-20 Basf Se HFO/water-blown rigid foam systems
WO2018022405A1 (fr) * 2016-07-25 2018-02-01 Covestro Llc Compositions formant des mousses de polyuréthane, procédés de fabrication de mousses de faible densité à l'aide de telles compositions et mousses formées à partir de celles-ci
WO2018192990A1 (fr) * 2017-04-19 2018-10-25 Covestro Deutschland Ag Mousse de polyuréthane rigide, procédé de préparation et application associés
CN108727551A (zh) * 2017-04-19 2018-11-02 科思创德国股份有限公司 一种硬质聚氨酯泡沫及其制备方法与应用
JP2023500909A (ja) * 2019-11-06 2023-01-11 ハネウェル・インターナショナル・インコーポレーテッド ２－クロロ－３，３，３－トリフルオロプロペン（ｈｃｆｏ－１２３３ｘｆ）および水の共沸混合物または共沸混合物様組成物

Similar Documents

Publication Publication Date Title
CA2705271C (fr) Compositions et utilisation d&#39;une composition moussante a base de cis-1,1,1,4,4,4-hexafluoro-2-butene pour la preparation de mousses a base de polyisocyanate
EP2170980B1 (fr) Compositions et utilisation d&#39;une composition moussante de cis-1,1,1,4,4,4-hexafluoro-2-butène dans la préparation de mousses à base de polyisocyanate
EP2222746B1 (fr) Compositions moussantes contenant un mélange azéotropique ou de type azéotropique contenant du z-1,1,1,4,4,4-hexafluoro-2-butène et du methyl formate et leurs applications dans la préparation de mousses à base de polyisocyanate
US20100210747A1 (en) Compositions and use of trans-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based foams
US20110124758A1 (en) Foam-forming compositions containing mixtures of 2-chloro-3,3,3-trifluoropropene and hydrocarbon and their uses in the preparation of polyisocyanate-based foams
WO2010098936A1 (fr) Compositions moussantes contenant des mélanges de 2-chloro-3,3,3-trifluoropropène et au moins une hydrofluorooléfine et leurs utilisations dans la préparation de mousses à base de polyisocyanate
US20110269860A1 (en) Foam expansion agent compositions containing hydrohaloolefin butene and water and their uses in the preparation of polyurethane and polyisocyanurate polymer foams
WO2009089400A1 (fr) Compositions et utilisation d&#39;une composition moussante à base de 2-chloro-3,3,3-trifluoropropène dans la préparation de mousses à base de polyisocyanate
EP2393862B1 (fr) Compositions formant une mousse contenant des mélanges de cis-1,1,1,4,4,4-hexafluoro-2-butène et de 1,1,1,3,3-pentafluoropropane et leurs utilisations dans la préparation de mousses à base de polyisocyanate

Legal Events

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

Ref document number: 09700698

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 09700698

Country of ref document: EP

Kind code of ref document: A1