WO2017198115A1 - A polyurethane foam and a polyurethane composite comprising the same - Google Patents

A polyurethane foam and a polyurethane composite comprising the same Download PDF

Info

Publication number
WO2017198115A1
WO2017198115A1 PCT/CN2017/084139 CN2017084139W WO2017198115A1 WO 2017198115 A1 WO2017198115 A1 WO 2017198115A1 CN 2017084139 W CN2017084139 W CN 2017084139W WO 2017198115 A1 WO2017198115 A1 WO 2017198115A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurethane
polyether polyol
panels
mold
composition
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/CN2017/084139
Other languages
English (en)
French (fr)
Inventor
Wenping WEI
Chunlei Zheng
Yefen WEI
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.)
Covestro Polymers China Co Ltd
Covestro Deutschland AG
Original Assignee
Covestro Polymers China Co Ltd
Covestro Deutschland AG
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 Covestro Polymers China Co Ltd, Covestro Deutschland AG filed Critical Covestro Polymers China Co Ltd
Priority to CN201780031253.7A priority Critical patent/CN109642004B/zh
Priority to JP2018560842A priority patent/JP6893522B2/ja
Priority to EP17798678.3A priority patent/EP3458492A4/en
Priority to KR1020187033077A priority patent/KR20190009748A/ko
Priority to US16/094,524 priority patent/US10793663B2/en
Publication of WO2017198115A1 publication Critical patent/WO2017198115A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

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
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C44/00—Shaping by internal pressure generated in the material, e.g. swelling or foaming ; Producing porous or cellular expanded plastics articles
    • B29C44/02—Shaping by internal pressure generated in the material, e.g. swelling or foaming ; Producing porous or cellular expanded plastics articles for articles of definite length, i.e. discrete articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C44/00—Shaping by internal pressure generated in the material, e.g. swelling or foaming ; Producing porous or cellular expanded plastics articles
    • B29C44/02—Shaping by internal pressure generated in the material, e.g. swelling or foaming ; Producing porous or cellular expanded plastics articles for articles of definite length, i.e. discrete articles
    • B29C44/12—Incorporating or moulding on preformed parts, e.g. inserts or reinforcements
    • B29C44/18—Filling preformed cavities
    • 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
    • C08G18/14—Manufacture of cellular products
    • 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
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4816—Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having 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
    • C08G18/4825—Polyethers containing two 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
    • C08G18/4829—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
    • C08G18/4833—Polyethers containing oxyethylene units
    • 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
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4883—Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring
    • 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
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl 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
    • 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
    • C08J9/125—Water, e.g. hydrated salts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/141—Hydrocarbons
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
    • 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
    • C08G2101/00—Manufacture of cellular products
    • 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
    • C08G2110/005—< 50kg/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
    • 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
    • C08G2120/00—Compositions for reaction injection moulding processes
    • 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
    • C08J2203/10—Water or water-releasing 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
    • C08J2203/144—Perhalogenated saturated hydrocarbons, e.g. F3C-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
    • C08J2203/164—Perhalogenated unsaturated hydrocarbons, e.g. F2C=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
    • 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
    • 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 present invention relates to an isocyanate reactive component comprising a specific polyol mixture useful for the preparation of homogenous reactive polyurethane compositions.
  • the invention further relates to a reactive polyurethane composition comprising such isocyanate reactive component and an isocyanate component. It also relates to a homogeneous polyurethane foam having good mold release property and surface quality prepared from such reactive polyurethane compositions. In a further aspect, it relates to a polyurethane composite comprising such homogenous polyurethane foam and having good and flat surface appearance after processing.
  • the polyurethane composites as they are referred to in this application generally comprise a shell and a polyurethane foam filled therein.
  • a highly flexible and widely applied process for the production of heat insulation systems is a discontinuous process wherein polyurethane composites are prepared in the form of plate parts in a plate-shaped shell, and then these plate parts are assembled to the respective heat insulation system.
  • a prefabricated hollow shell of any geometry e.g. assembled from various panels, may be used.
  • the discontinuous process for the production of the polyurethane composite comprises the following steps: disposing the prefabricated shell in a mold, injecting the reactive polyurethane composition into the mold and closing the mold. Then, the polyurethane resin is foamed. Finally, the polyurethane composite is obtained by releasing from the mold.
  • aknown problem of the polyurethane foam made from the existing reactive polyurethane compositions is the poor mold release property of the composites, that is, an expansion to a certain extent after mold releasing may be observed, which results in the coarse and uneven surface of the polyurethane composites prepared.
  • the polyurethane foams made from the known reactive polyurethane compositions may also show the problem of surface bubbles, which then lead to bulges or even serious quality problems occurring in the polyurethane composites prepared therefrom.
  • a polyurethane composite comprising homogeneous polyurethane foam and having a good and flat surface appearance, which is prepared by a discontinuous process comprising the steps of injecting a reactive polyurethane composition into a shell provided in a mold, and foaming such reactive composition.
  • an isocyanate reactive component B comprising a polyether polyol composition
  • said polyether polyol composition comprising:
  • a first polyether polyol having a functionality of 1.6-2.4, a hydroxyl value of 60-140 mg KOH/g, in an amount of 30-40 mol-%, based on the theoretically calculated total mole number of said polyether polyol composition
  • a second polyether polyol having a functionality of 7.6-8.4, a hydroxyl value of 480-560 mg KOH/g, in an amount of 35–55 mol-%, based on the theoretically calculated total mole number of said polyether polyol composition, and
  • a third polyether polyol selected from polyether polyols derived from diphenylmethane diamine and/or toluenediamine, having a functionality of 3.6-4.4, and a hydroxyl value of 290-370 mg KOH/g, in an amount of 13-27 mol-%based on the theoretically calculated total mole number of said polyether polyol composition.
  • the present invention furthermore provides a reactive polyurethane composition useful for the production of polyurethane foams with good and flat surface appearance, comprising:
  • an isocyanate reactive component comprising a polyether polyol composition, said polyether polyol composition comprising:
  • a first polyether polyol having a functionality of 1.6-2.4, a hydroxyl value of 60-140 mg KOH/g, in an amount of 30-40 mol-%, based on the theoretically calculated total mole number of said polyether polyol composition
  • a second polyether polyol having a functionality of 7.6-8.4, a hydroxyl value of 480-560 mg KOH/g, in an amount of 35–55 mol-%, based on the theoretically calculated total mole number of said polyether polyol composition, and
  • a third polyether polyol selected from polyether polyols derived from diphenylmethane diamine and/or toluenediamine, having a functionality of 3.6-4.4, and a hydroxyl value of 290-370 mg KOH/g, in an amount of 13-27 mol-%based on the theoretically calculated total mole number of said polyether polyol composition; and
  • organic polyisocyanates of component A) which can be used in the preparation of polyurethane foams, include organic diisocyanates which may be any aliphatic-, cycloaliphatic-or aromatic-isocyanates known to be useful in the preparation of polyurethanes.
  • Examples thereof include, but are not limited to, 2, 2’ -, 2, 4-and 4, 4’ -diphenylmethane diisocyanates (monomeric MDI) ; mixtures of monomeric diphenylmethane diisocyanates and diphenylmethane diisocyanate homologs having more rings (polymeric MDI) ; isophorone diisocyanate (IPDI) or oligomers thereof; toluene diisocyanates (TDI) , e.g.
  • toluene diisocyanate isomers such as toluene-2, 4-or 2, 6-diisocyanates, or mixtures thereof; tetramethylene diisocyanate or oligomers thereof; hexamethylene diisocyanate (HDI) or oligomers thereof; naphthalene diisocyanates (NDI) or mixtures thereof.
  • the organic polyisocyanates include isocyanates based on diphenylmethane diisocyanates, especially those comprising polymeric MDI.
  • the organic polyisocyanate preferably has a functionality of 1.9-3.5, particularly preferably 2.0-2.8.
  • the organic polyisocyanate preferably has a viscosity of 100-600 mPas, particularly preferably 150-300 mPas, measured according to GB/T 12008.8-1992 at 25°C.
  • the isocyanate component may be present in an amount of 20-60 wt. %, based on the total weight of said polyurethane composition as 100 wt. %.
  • the organic polyisocyanates also can be used in the form of polyisocyanate prepolymers. These polyisocyanate prepolymers can be obtained by the reaction of an excess of the above-mentioned organic polyisocyanate with a compound having at least two isocyanate-reactive groups at a temperature of, for example, 30-100°C, preferably about 80°C.
  • the NCO content of the polyisocyanate prepolymer of the present invention is preferably 20-33 wt. % (GB 12009.4-1989) , particularly preferably 25-32 wt. %.
  • the compounds with at least two isocyanate-reactive groups are well known to those skilled in the art, for example as illustrated in Chapter 3.1 of the “Plastics Handbook” ( “Kunststoffhandbuch, 7, Polyurethanes” , Carl Hanser-Verlag, 3rd ed., 1993) .
  • the isocyanate-reactive component that can be used to prepare the polyurethane foams provided by the present invention comprises a polyether polyol composition.
  • a polyether polyol has a definition well known to those skilled in the art. It can be prepared by known processes, for example, by the reaction of an alkylene oxide with a starting agent in the presence of a catalyst.
  • the use of the word "a” in conjunction with components according to the invention such as for example certain polyols shall not be understood within the meaning of this application as a numerical value.
  • the term “polyol” may therefore also define a mixture of polyols, in such case the parameters required for the individual polyols (such as functionality, hydroxyl value etc. ) correspond to the average values measured or calculated for the respective polyol mixture.
  • the term "functionality" within the context of the present invention refers to the theoretical functionality calculated from the known components used and the proportions thereof in the polyol mixture.
  • the first polyether polyol b1) which is to be used in the present invention has a functionality of 1.6-2.4, preferably 1.8–2.2, a hydroxyl value of 60-140 mg KOH/g, preferably 80–120 mg KOH/g (measured according to GB/T12008.3-2009) , and is used in an amount of 30–40 mol-%, preferably in an amount of 32 -38 mol-%, based on the theoretically calculated total mole number of the polyether polyol composition.
  • the first polyether polyol is selected from the group consisting of the polyether polyols derived from 1, 2-propanediol and/or 1, 3-propanediol. More preferably, the first polyether polyol is selected from the propylene oxide-based polyether polyols derived from 1, 2-propanediol.
  • the second polyether polyol b2) which is to be used in the present invention has a functionality of 7.6-8.4, preferably 7.8–8.2, a hydroxyl value of 480-560 mg KOH/g, preferably 490–530 mg KOH/g, and is used in an amount of 35–55 mol-%,in preferred embodiments in an amount of 35–50 mol-%or 35-45 mol-%, respectively, even more preferred in an amount of 40–50 mol-%or 38-48 mol-%, respectively, based on the theoretically calculated total mole number of said polyether polyol composition.
  • the first polyether polyol is selected from the polyether polyols derived from saccharose. More preferably, the first polyether polyol is selected from the propylene oxide-based polyether polyols derived from saccharose.
  • the third polyether polyol b3) which is to be used in the present invention, is selected from the polyether polyols derived from diphenylmethane diamine and/or tolylenediamine, and has a functionality of 3.6-4.4, preferably 3, 8–4, 2, and a hydroxyl value of 290-370 mg KOH/g, preferably 320 mg KOH/g–360 mg KOH/g, and is used in an amount of 13-27 mol-%, in preferred embodiments in an amount of 15-25 mol-%, respectively, and particularly preferably 17–23 mol-%, based on the theoretically calculated total mole number of said polyether polyol composition.
  • Ortho-tolylenediamine or diphenylmethane diamines are preferably used as the starter.
  • Ortho-tolylene diamine o-TDA
  • Propylene oxide-based polyether polyols derived from o-TDA are particularly preferred for the third polyether.
  • the third polyether polyol is selected from the propylene oxide-based polyether polyols derived from diphenylmethane diamines.
  • the polyether polyol composition comprising the above-mentioned polyether polyols b1) –b3) exhibits an average functionality of 3.5-6, preferably 4.5-5.5, and an average hydroxyl value of 280-450 mg KOH/g, preferably 300-350 mg KOH/g.
  • the isocyanate reactive composition which is used in the preparation of the polyurethane foams provided by the present invention, further includes a foaming agent C) .
  • Said foaming agent can be selected from various physical foaming agents or chemical foaming agents, preferably but not limited to water, halogenated hydrocarbons, hydrocarbon compounds, and gases, preferabyl n-pentane, isopentane, cyclopentane, butane, isobutane, ethers (e.g. methylal) , halogenated ethers, perfluorinated hydrocarbons having 1 to 8 carbon atoms (e.g. perfluorohexane) , hydroolefins and mixtures thereof with one another.
  • said foaming agent is selected from the group consisting of water, dichlorofluoroethane, cyclopentane, pentafluorobutane, pentafluoropropane, trifluorochloropropylene, hexafluorobutene or the combinations thereof.
  • said foaming agent is present in an amount of 2-30 wt.%, preferably 5-25 wt. %, based on the weight of the isocyanate-reactive component as 100 wt. %.
  • Cyclopentane is exceptionally particularly preferably used as the blowing agent.
  • water or other chemical blowing agents as co-blowing agents is also preferred. If used, it is normally added in an amount of 0–6 wt-%, based on the weight of the total isocyanate reactive component, including and foaming agents, as 100 wt. %.
  • the components which can be used in the preparation of the polyurethane foams according to the present invention, may further comprise other aids or additives commonly used in the art, including but not limited to, catalysts, flame retardants, and foam stabilizers, or the like.
  • the core density of said polyurethane foam is 35-70 kg/m 3 (GB/T 6343-1995) .
  • the closed cell proportion of said polyurethane foam is 85-98% (GB/T 10799-2008) .
  • the isocyanate-reactive component B) has a good compatibility with the foaming agent component C) , thus enable preparing foams with a homogeneous distribution.
  • the polyurethane foams prepared therefrom and the polyurethane composites made with the foam have a good mold release property, as well as a good surface quality.
  • the present invention also provides a polyurethane composite prepared by a discontinuous process comprisingthe steps of:
  • the shell may consist of cover panels which are placed and optionally attached at the inner walls of the mold before closing the mold.
  • ahollow shell part is firstly prefabricated using panel materials, such as metal, plastic and composite plates, etc. ; then the seam portion of the hollow shell part is subjected to a sealing treatment with the injection hole and vent hole remained; and finally the hollow shell part is disposed into the foam molding mold; the inventive reactive polyurethane composition is introduced into the cavity of the hollow shell part through the injection hole of the mold and the hollow shell part; and the polyurethane composite comprising the foam and the shell is removed from the mold after the foaming reaction of the reactive polyurethane composition is completed.
  • said prefabricated shell has a plate-like or hollow cylindrical shape.
  • the present invention also provides polyurethane composites prepared by the inventive discontinuous process.
  • the polyurethane composites prepared by this discontinuous process may advantageously be used for the production of roof panels, side panels, bottom panels, or door panels of a container; roof panels, side panels, or bottom panels, or door panels of a prefabricated house; roof panels, side panels, or bottom panels, or door panels of a refrigerator house; insulation panels of an air-conditioner and insulation pipelines.
  • Polyol 1 a propylene oxide-based polyether polyol with propylene glycol as the initiator, having a functionality of 2 and a hydroxyl value of 100 mg KOH/g;
  • Polyol 2 a propylene oxide-based polyether polyol with saccharose as the initiator, having a functionality of 8 and a hydroxyl value of 525 mg KOH/g;
  • Polyol 3 a propylene oxide-based polyether polyol with o-TDA as the initiator, having a functionality of 4 and a hydroxyl value of 345 mg KOH/g;
  • Yoke TCPP Tris (2-chloroisopropyl) phosphate, a flame retardant, purchased from Jiangsu Yoke Technology Co., Ltd. ;
  • Niax L6920 a foam stabilizer, purchased from Momentive Performance Materials (China) Co., Ltd. ;
  • Dabco Polycat 41 a polyurethane synthesis catalyst, purchased from Air Products and Chemicals (China) Co., Ltd. ;
  • Dabco Polycat PC8 a polyurethane synthesis catalyst, purchased from Air Products and Chemicals (China) Co., Ltd. ;
  • 44V20L polymeric MDI, having an NCO content of 31.5 wt. %, purchased from Covestro Polymers (China) Co., Ltd.
  • the prefabricated hollow shell part (panel shape) was placed in the mold and the mold was closed.
  • the hollow shell member was preheated in the mold until the surface temperature of its surface material reached 30-45°C.
  • the isocyanate reactive mixture and the isocyanate component were introduced and mixed in the mixing head of the high-pressure foaming machine (the mixing head was at a pressure of 100 to 160 bar) .
  • the polyurethane reactive mixture was then injected into the prefabricated hollow shell part in the mold through the mixing head, foamed and expanded in the hollow shell until the hollow shell was fully filled. After the foaming reaction was completed, the foamed article was removed from the mold and the polyurethane composite was obtained.
  • Cyclopentane and combined polyether stock i.e., all components listedin Table 1 except for the isocyanate and cyclopentane
  • the mixing weight ratio of cyclopentane to the combined polyether was 12: 100, 15: 100, 18: 100 and 21: 100.
  • the solution was sealed with the transparent tube and left to stand at room temperature (20°C) for 72 hours to be observed. If the solution within the tube shows clarity, it reveals an excellent compatibility; if the solution within the tube shows slight turbidity, it reveals a good compatibility; whereas, if the solution within the tube shows severe turbidity, two-phase or multi-phase separation, it reveals a poor compatibility.
  • Table 1 show that the compatibility of the formulations 1, 2 and 3 was poor, good and excellent, respectively.
  • a mold of 300 ⁇ 300 ⁇ 100mm was used with the mold temperature controlled at 40°C and the overall foam density of the mold was 55 kg/m 3 .
  • Table 2 The testing results are shown in Table 2 below.
  • An L-shaped mold was used with the mold temperature controlled at 40°C and the inner surface of the mold was evenly coated with a mold release agent.
  • the overall foam density of the mold was 55 kg/m 3 .
  • the formulations in Table 1 were mixed and then disposed into the mold. The mold was closed and the foaming reaction took place in the mold. After 30 minutes starting from the mixing of the components, the mold was opened and the foamed molding product was taken out.

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)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/CN2017/084139 2016-05-20 2017-05-12 A polyurethane foam and a polyurethane composite comprising the same Ceased WO2017198115A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201780031253.7A CN109642004B (zh) 2016-05-20 2017-05-12 聚氨酯泡沫和包含其的聚氨酯复合材料
JP2018560842A JP6893522B2 (ja) 2016-05-20 2017-05-12 ポリウレタンフォームおよびそれを含むポリウレタン複合材
EP17798678.3A EP3458492A4 (en) 2016-05-20 2017-05-12 POLYURETHANE FOAM AND POLYURETHANE COMPOSITE CONTAINING THE SAME
KR1020187033077A KR20190009748A (ko) 2016-05-20 2017-05-12 폴리우레탄 발포체 및 그를 포함하는 폴리우레탄 복합체
US16/094,524 US10793663B2 (en) 2016-05-20 2017-05-12 Polyurethane foam and a polyurethane composite comprising the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610370868 2016-05-20
CN201610370868.X 2016-05-20

Publications (1)

Publication Number Publication Date
WO2017198115A1 true WO2017198115A1 (en) 2017-11-23

Family

ID=60324831

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2017/084139 Ceased WO2017198115A1 (en) 2016-05-20 2017-05-12 A polyurethane foam and a polyurethane composite comprising the same

Country Status (6)

Country Link
US (1) US10793663B2 (enExample)
EP (1) EP3458492A4 (enExample)
JP (1) JP6893522B2 (enExample)
KR (1) KR20190009748A (enExample)
CN (1) CN109642004B (enExample)
WO (1) WO2017198115A1 (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106243304A (zh) * 2015-06-11 2016-12-21 科思创聚合物（中国）有限公司 粘弹性网状聚氨酯泡沫及其制备方法
CN111349206B (zh) * 2020-04-14 2022-02-08 万华节能科技(烟台)有限公司 一种冷库用高强度聚氨酯保温垫块双组分原料及制备方法
JP2024510397A (ja) 2021-03-10 2024-03-07 ダウ グローバル テクノロジーズ エルエルシー 製品をポッティングするためのポリウレタンフォーム組成物及びその使用
CN113929852B (zh) * 2021-09-18 2023-05-30 红宝丽集团股份有限公司 聚氨酯组合物、组合聚醚、聚氨酯硬泡及其制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040176495A1 (en) * 2003-03-07 2004-09-09 Lg Electronics Inc. Raw composition for preparing polyurethane foam having improved adhesive and demolding properties, polyurethane foam made therefrom, and preparation method thereof
US20060229371A1 (en) * 2003-01-17 2006-10-12 Lg Electronics Inc. Composition for preparing rigid polyurethane foam and rigid polyurethane foam made therefrom
CN101035826A (zh) * 2004-10-05 2007-09-12 巴斯福股份公司 生产硬聚氨酯泡沫材料的方法
CN101289530A (zh) * 2008-06-04 2008-10-22 常熟一统聚氨酯制品有限公司 聚氨酯硬质泡沫组合料
CN103709367A (zh) * 2012-09-29 2014-04-09 拜耳材料科技(中国)有限公司 聚氨酯组合物以及聚氨酯道碴道床的维修方法
CN104072717A (zh) * 2013-03-25 2014-10-01 拜耳材料科技股份有限公司 具有均匀的泡孔尺寸分布和均匀的开孔含量的硬质聚氨酯泡沫

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3509077A (en) * 1966-07-07 1970-04-28 Allied Chem Rigid polyurethane foams from certain polyether mixtures
US4742089A (en) * 1987-08-12 1988-05-03 Hitachi, Ltd. Rigid polyurethane foam and process for producing the same
JPH02284912A (ja) * 1989-04-27 1990-11-22 Hitachi Ltd 硬質ポリウレタンフォーム及びその製造方法と断熱材並びにそれを用いた冷蔵庫
JP3283616B2 (ja) * 1993-02-12 2002-05-20 住化バイエルウレタン株式会社 硬質ポリウレタンフォームの製造法
JP3618791B2 (ja) * 1994-09-06 2005-02-09 住化バイエルウレタン株式会社 硬質ポリウレタンフォーム用のポリオール組成物およびその用途
DE19611367A1 (de) * 1996-03-22 1997-09-25 Bayer Ag Verfahren zur Herstellung Kohlenwasserstoff-getriebener Polyurethan-Hartschaumstoffe
DE19723193A1 (de) * 1997-06-03 1998-12-10 Bayer Ag Verfahren zur Herstellung von geschlossenzelligen Polyurethan-Hartschaumstoffen mit geringer Wärmeleitfähigkeit
ES2165194T3 (es) * 1997-09-25 2002-03-01 Huntsman Int Llc Procedimiento para la preparacion de espumas rigidas de poliuretano.
JP3808991B2 (ja) * 1997-11-07 2006-08-16 住化バイエルウレタン株式会社 硬質ポリウレタンフォームの製造方法及び硬質ポリウレタンフォーム用組成物
EP1100838A1 (en) * 1998-07-23 2001-05-23 Huntsman International Llc Blends of sucrose- and aromatic amine initiated polyether polyols and their use in rigid polyurethane foam manufacture
US6005016A (en) * 1998-10-06 1999-12-21 Bayer Corporation Rigid polyurethane foam based on polyethers of TDA
JP2001329036A (ja) * 2000-05-19 2001-11-27 Toho Chem Ind Co Ltd 硬質ポリウレタンフォームの製造方法
EP1167414A1 (en) * 2000-06-29 2002-01-02 Huntsman International Llc Process for making rigid polyurethane foams having high adhesion
DE102004051102A1 (de) 2004-10-19 2006-04-27 Basf Ag Verfahren zur Herstellung von Polyurethan-Hartschaumstoffen
CN1908028B (zh) * 2006-08-18 2010-05-12 南京红宝丽股份有限公司 低密度低热导率聚氨酯硬质泡沫
CN1986593B (zh) * 2006-08-18 2010-05-12 南京红宝丽股份有限公司 一种具有快速脱模性能的硬质聚氨酯泡沫组成物
ES2447292T3 (es) * 2009-09-29 2014-03-11 Dow Global Technologies Llc Mezclas de polioles que contienen un poliol iniciado por 1,3 - y/o 1,4 - bis(aminometil) ciclohexano y al menos uno de un poliol iniciado por metilen - bis - (ciclohexilamina) y un poliol iniciado por ciclohexanodiamina, y poliuretanos preparados a partir de las mismas
EP2683755B1 (de) * 2011-03-08 2015-05-13 Basf Se Verfahren zur herstellung von polyurethan-hartschaumstoffen
CN102432794A (zh) * 2011-09-14 2012-05-02 可利亚多元醇（南京）有限公司 低导热系数快速脱模的硬质聚氨酯组合物及其制备方法
CN102391466B (zh) * 2011-09-14 2013-03-13 可利亚多元醇（南京）有限公司 低粘度快速脱模的硬质聚氨酯组合物及其制备方法
CN103642026A (zh) * 2013-11-28 2014-03-19 山东蓝星东大化工有限责任公司 喷涂用硬泡聚醚多元醇的制备方法
CN105199071B (zh) * 2015-09-16 2018-06-12 万华化学（广东）有限公司 一种聚氨酯组合料、其制备聚氨酯复合材料的方法及制得产品的用途
CN105367742B (zh) * 2015-12-10 2018-04-24 上海东大聚氨酯有限公司 组合聚醚、聚氨酯泡沫及其制备方法和应用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060229371A1 (en) * 2003-01-17 2006-10-12 Lg Electronics Inc. Composition for preparing rigid polyurethane foam and rigid polyurethane foam made therefrom
US20040176495A1 (en) * 2003-03-07 2004-09-09 Lg Electronics Inc. Raw composition for preparing polyurethane foam having improved adhesive and demolding properties, polyurethane foam made therefrom, and preparation method thereof
CN101035826A (zh) * 2004-10-05 2007-09-12 巴斯福股份公司 生产硬聚氨酯泡沫材料的方法
CN101289530A (zh) * 2008-06-04 2008-10-22 常熟一统聚氨酯制品有限公司 聚氨酯硬质泡沫组合料
CN103709367A (zh) * 2012-09-29 2014-04-09 拜耳材料科技(中国)有限公司 聚氨酯组合物以及聚氨酯道碴道床的维修方法
CN104072717A (zh) * 2013-03-25 2014-10-01 拜耳材料科技股份有限公司 具有均匀的泡孔尺寸分布和均匀的开孔含量的硬质聚氨酯泡沫

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3458492A4 *

Also Published As

Publication number Publication date
US20190119430A1 (en) 2019-04-25
EP3458492A1 (en) 2019-03-27
JP6893522B2 (ja) 2021-06-23
CN109642004A (zh) 2019-04-16
US10793663B2 (en) 2020-10-06
KR20190009748A (ko) 2019-01-29
CN109642004B (zh) 2021-08-17
EP3458492A4 (en) 2020-02-19
JP2019516843A (ja) 2019-06-20

Similar Documents

Publication Publication Date Title
US11505670B2 (en) Polyurethane foams co-blown with a mixture of a hydrocarbon and a halogenated olefin
WO2019038289A1 (en) RIGID POLYURETHANE FOAM SYSTEM AND CORRESPONDING APPLICATION
US8318826B2 (en) Ortho-cyclohexanediamine-initiated polyols and rigid polyurethane foam made therefrom
EP3470446A1 (en) Rigid polyurethane foam system and application thereof
CN109983050B (zh) 聚氨酯硬质泡沫材料、其制备方法及其用途
CN113557255A (zh) 多元醇共混物及其在生产pur-pir泡沫形成组合物中的用途
US10793663B2 (en) Polyurethane foam and a polyurethane composite comprising the same
EP3115389A1 (de) Herstellung von polyurethanschaum
EP3957669A1 (de) Herstellung von polyurethanschaum
KR20100100951A (ko) 경질 폴리우레탄폼의 제조 방법
US12540214B2 (en) HCFO-containing isocyanate-reactive compositions, related foam-forming compositions and polyurethane foams
CN109422862A (zh) 聚氨酯硬质泡沫体系及其应用
US11767407B1 (en) HCFO-containing polyurethane foam-forming compositions, related foams and methods for their production
WO2022260859A1 (en) Hcfo-containing isocyanate-reactive compositions, related foam-forming compositions and flame retardant pur-pir foams
US10793665B2 (en) Polyurethane foam from high functionality polyisocyanate
JP2019026834A (ja) ポリウレタン樹脂組成物
US11827735B1 (en) HFO-containing isocyanate-reactive compositions, related foam-forming compositions and flame retardant PUR-PIR foams
US11753516B2 (en) HFO-containing compositions and methods of producing foams
JP3665621B2 (ja) 硬質ポリウレタンフォームの製造方法
US20250145786A1 (en) Hcfo-containing polyurethane foam-forming compositions, related foams and methods for their production
JP2024158563A (ja) ポリオールプレミックス、発泡体、及び、保温庫
CN117209706A (zh) 聚氨酯发泡体系及由其制备的硬质泡沫
JP2005139468A (ja) 硬質ポリウレタンフォームの製造方法

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 20187033077

Country of ref document: KR

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2018560842

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

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

Ref document number: 17798678

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2017798678

Country of ref document: EP

Effective date: 20181220