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WO2025128192A1 - High-resiliency polyurethane foam and method of making - Google Patents

High-resiliency polyurethane foam and method of making Download PDF

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Publication number
WO2025128192A1
WO2025128192A1 PCT/US2024/051231 US2024051231W WO2025128192A1 WO 2025128192 A1 WO2025128192 A1 WO 2025128192A1 US 2024051231 W US2024051231 W US 2024051231W WO 2025128192 A1 WO2025128192 A1 WO 2025128192A1
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Prior art keywords
making
polyurethane foam
resiliency polyurethane
hydroxyl groups
cell opener
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PCT/US2024/051231
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French (fr)
Inventor
Ana NUNEZ
Richard J. Keaton
Jean-Paul Masy
Alex J. KOSANOVICH
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/161Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • C08G18/165Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/4009Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4072Mixtures of compounds of group C08G18/63 with other macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4804Two or more polyethers of different physical or chemical nature
    • C08G18/4816Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having at least three hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4833Polyethers containing oxyethylene units
    • C08G18/4837Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4866Polyethers having a low unsaturation value
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/63Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
    • C08G18/632Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04Polyurethanes
    • C08L75/08Polyurethanes from polyethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00Foam properties
    • C08G2110/0008Foam properties flexible
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00Foam properties
    • C08G2110/0083Foam properties prepared using water as the sole blowing agent
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645Metals or compounds thereof, e.g. salts
    • C08G65/2663Metal cyanide catalysts, i.e. DMC's

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

High resiliency polyurethane foams are made by reacting a polyisocyanate with a mixture of polyols and water. The polyols include a cell opener. The cell opener is a random copolymer of 60 to 80 wt.-% ethylene oxide and correspondingly 40 to 20 wt.-% propylene oxide having a nominal functionality of 2 to 4 and a hydroxyl number of 25 to 50, wherein 50 to 75% of the hydroxyl groups of polyether polyol are primary hydroxyl groups, which is made using a modified double metal cyanide catalyst.

Description

- - . ,. - . - . , , . - “- ”, ,. . . ., , ,- . , . .. - . . , , ,. . . , , - . -- . . , , . , : , - , , , , - , - - - , , - , ,.-, - .-, 1b2 r1 52413 2 : : tc 6d xy wz1 4+ 6+4 +3+ 4+ 5+ 2+ 4+ 6+ 2+ 2 2+,2+,+2+,2+,2, , ,,,,,, ,+,4+,2+ 2+ 3+ 3+ 3+ 5 , ,3+,2,+,3+,2+,2+,3,2+,3+,3+,2+,3+,2+,4+,5+,2+,2+, 2+ - , – ,1 2 2 5 -- 1 , , ,, , , ,, , , , , 1- ,2 ,4 , , , , , , ,, , , , , , ,, , 3x1y . 3 z 2 z, - , , - -, , ,- , , . : , - , , , ,, -- - -
Figure imgf000005_0001
- - , .- , .- - ,, - 1b2 r1tc526d •4x1y •3w2z: 1 : 4+ 6+4 +3+ 4+ 5+ 2+ 4+ 6+ 2+ 2+ 4 2+,2+,+2+,2+, 2,5, ,,,,,, , ,+,2+,2+,3+, 3+ 3+,2+,3+,3+,2+,3+,2+,4+,5+,2+,2+, 2+3+,2+,3+,2+,2+, 3- , – , 1 2 2 1 , , 5 , , , , , , , ,,1- , , 2 , ,,4 ,, , , , ,, , , , , , , , 3x1y . -- 3 z 2 z, - , , - -, , - , , , . , ,, - , .-., , -, :1b2 r1tc526d •4x1y •3w:2z1 4+ 6+4 +3+ 4+ 5+ 2+ 4+ 6+ 2+ 2 2+,2+,+2+,2+,2, , ,,,,,, ,+,4+,2+ 2+ 3+ 3+ 3+ 5 , ,3+,2,+,3+,2+,2+,3,2+,3+,3+,2+,3+,2+,4+,5+,2+,2+, 2+ - , – ,1 2 2 5 -- 1 , , ,, , , ,, , , , , 1-4 ,2 , , , , , , , , , , , , , , ,, , 3x1y . 3 z 2 z, : - , , , , - , - - , - , - , , - -, , - -- , . . , - . , . ,. , -, , . .-- . , , . - - , , -. , .., - , , . . - . - - , . ,- -, . - ,, , - . , , . -- -. - . , , -, , . , , , --,, ,. , . - “ ” “ ” . , . - - , . , , , , - -, . , - , , . , -- . . , - , .. - . . , , , - , ,, , . - -. , .-, - .-, ,, -- . , . -. . , , , ,,,- , , ,,,- ,,,- , , , , , , . ,, .. ., . - . .. . 2,1,2,1b,,2 r1tc526d •4x1y •3w2z,: 1,2,3,4,5,1, 1 ,4,,,,,, . , .3 .2 5 , , , , .3 , 3 , ,:: , ..3 . :,. , 1 4 . 2 3. .:,: ... 1-5, . 1, . , .2 3 , ,3 -- 3 . ,, 3 3 w 2 z . . 1b 2 r,1 tc 52 6d4 x 1 y3 w.2 z 1b2 r1tc526d,4x1y 3w2z . 32 1b2 r1tc wz .1 b 24x1y r1 tc, , 1. 1,2 1 52 b 2 r 1 tc .b r tc 641 , 41 2 3w2zd x y .x y , , , , ,, , ,,, ,, , , , , , . , , . . 3 . , , ,, , , -- , -- 3, - ,3, , , , ,, , - , 3,--,- 3, , , -, , , , , , , , - -- , ., 3 . , , , , -- , , -- ,3, , , ,3, , - ,, , - -,, , ,,3, , 3, , , , --- , , - 3 .. , , , - , - 3, - ,3, , ,, , , - , -, , ,,3, , 3, , , , , 3--- . - . , , , ,-- , , -- , ,3, , , , , - --3 , - , , , , ,3,,--, 3, , , - , , ,- , ,- ,, ,, , 3 . . , , , - , -, ,3, , 3, , , - , , , , , - , - , , ,3,,-, 3, , - -- . 3 ., , ,. , , ,, ,. ,.... 2 . ,. ,. -...,. - , 2 , ,. . -- ° °. - . , ,° °.., , - , .. , . . . - - , - ,- . , , . , , ., . . - - . - . , , . .. , -,. , . , , . , . ---, -- .. - , - , .-,, , .- 4x1y •3w2z :1b2 r1.tc526d • . . :1 b 2 r,1 tc 52 6d4 x 1 y3 w 2 z . , . . . , . - - , . , ,, , . , , , . - . - ,,, .. . , -,, .. , , , , . . . . . , , -- , . , , , , , , , . ,,- ,,- ,- ,- ,,’- -,,,-,,’, , ,,- '- -,- ,,- ,,, ,,,- -,,- ,- ,,,- - , , , , , , ,,-- , , -. n 4-n,. , , . . . . .. . . , . . , , , . , , -,- , --,- , -,-,- ,, -,- , , , -,-- ,,- ,- - - - -,’ ,- , -,'- , -,,’- ,,’- -,’- ,,'-, -- -,'- -,'- ,,’-,, -,’- ,,'- ,',"--, , -, ,- ,'- -, ',,'- . , '--,- , -,'- , , -,- , - . -,’- , ., ,’- -,- . “ ”, , , -.,- , ., . , , . - ,, ,, , , , , , , , . , , ,, , . , . , . , . . , -- , . , ° . , . ,. , °,. , .. , , . . , . . - ,, - . - , . - . , , , ,. , , , . , , -. -. , ., -- -,. ,. , , . ,3 , ., , , . , ., , . , . . . . : - . ° , . . , - . °.. . . . °. , ..- , .- .- . °. , . -- . ,.. ,. ,.. .. .2 - . : °. . . , . .. . . , - -. - , , . , .- . . , ,. - . . , . . . .- . , . , . . ., , ´ ´ .. -, . , , , - . . -- ., .- - - . . . . -. . ,- ,- . - .. -- .* . .
Figure imgf000022_0001
. - -, . , . ,-, . , - . , -- - . , , .-, ., , . , - . . , . --

Claims

: .: , - , , , , - , - - - , ,, - - , .-.,-, ,, 1b2 r1tc526d •4x13 2 : : y wz1 4+ 6+4 +3+ 4+ 5+ 2+ 4+ 6+ 2+ 2+ 4+ 2+ 2+ 2 3+,2+,+2+,2+,2,5, ,,,,,, , , ,, ,3+ + 2,+ 3+ 3+ 2+ 3+ 3+ 2+ 3+ 2 ,,3+,2+,2+,3, , ,,, ,+,,4+,5+,2+,2+, 2+ - – ,1 2 2 1 , , , , 5 , , , , , , , 1-4 , , 2 , ,, ,, , , , ,, , , , , ,, , 3x 1 y . 3z2z, - , , - -, , ,- , , . .: , - , , , , - , - - - , .- , .-- ,, - 1b2 1 52413 2: : r tc 6d xy wz 1 4 2+,2+,+2+,2+, 24+,6 5+,+3+,4+,5+,2+,4+,6+,2+,2+,4+,2+,2+,3+3+ 2, 3+ 3+ 2+ 3+ 3+ 2+ 3+ 2 ,+,3+,2+,2+, 3, , ,,, ,+,,4+,5+, –2+,2+, 2+ - , 1 2 2 1 , , , , , 5 , , , , , , , 1 ,2 -,4 , , , , , , , , , , , , ,, , , 3x 1 y . 3 z 2 z, - , , - -, , ,- , , . . , , , , .-, , .-, 1b2 r1tc526d •4x1y •3w:2z
Figure imgf000027_0001
4+ 6+ +3+ 4+ 5+ 2+ 4+ 6+ 2+ 2+ 4+ 2+ 2+ 2 3+ +,2+,3++2+,2+,2, 3+ 2+5, ,,,,,, , , ,, , 3+ 3+ 2+ 3+ 2+ 4 3+,2,+,3+,2+,2+,3, , ,,, , ,,+,5+, –2+,2+, 2+ - ,1 2 2 1 , , , , 5 , , , , , , , 1-4 , , 2 , ,, ,, , , , ,, , , , , ,, , 3x 1 y . 3z2z, : - , , , , - , - - - , , - , , - -, , - , . . , . 1 . . - ,2 5 , 4 ., . - 3 , , . .. - - - . . . .- - . ., - . ., -- . . -- - , - , . .. - . -.. , 3,.
PCT/US2024/051231 2023-12-15 2024-10-14 High-resiliency polyurethane foam and method of making Pending WO2025128192A1 (en)

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US63/610,432 2023-12-15

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022722A (en) 1974-06-27 1977-05-10 Union Carbide Corporation Process for preparing shaped, foamed polyurethane articles
US4483894A (en) 1981-06-24 1984-11-20 The Dow Chemical Company Process for applying polyurethane foams to substrates and product made thereby
WO1997027236A1 (en) * 1996-01-26 1997-07-31 Arco Chemical Technology, L.P. Poly(oxypropylene/oxyethylene) random polyols useful in preparing flexible high resilience foam with reduced tendencies toward shrinkage and foam prepared therewith
US6077978A (en) 1997-09-17 2000-06-20 Arco Chemical Technology L.P. Direct polyoxyalkylation of glycerine with double metal cyanide catalysis
US20120252916A1 (en) * 2009-10-05 2012-10-04 Asahi Glass Company, Limited Process for producing flexible polyurethane foam and seat
WO2018209069A1 (en) 2017-05-10 2018-11-15 Dow Global Technologies Llc Catalyst complex
WO2019055177A1 (en) 2017-09-15 2019-03-21 Dow Global Technologies Llc Continuous process for making polyether polyols
WO2023017078A1 (en) * 2021-08-11 2023-02-16 Shell Internationale Research Maatschappij B.V. Process for preparing a high-resilience polyurethane foam

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022722A (en) 1974-06-27 1977-05-10 Union Carbide Corporation Process for preparing shaped, foamed polyurethane articles
US4483894A (en) 1981-06-24 1984-11-20 The Dow Chemical Company Process for applying polyurethane foams to substrates and product made thereby
WO1997027236A1 (en) * 1996-01-26 1997-07-31 Arco Chemical Technology, L.P. Poly(oxypropylene/oxyethylene) random polyols useful in preparing flexible high resilience foam with reduced tendencies toward shrinkage and foam prepared therewith
US6077978A (en) 1997-09-17 2000-06-20 Arco Chemical Technology L.P. Direct polyoxyalkylation of glycerine with double metal cyanide catalysis
US20120252916A1 (en) * 2009-10-05 2012-10-04 Asahi Glass Company, Limited Process for producing flexible polyurethane foam and seat
WO2018209069A1 (en) 2017-05-10 2018-11-15 Dow Global Technologies Llc Catalyst complex
WO2018209075A1 (en) 2017-05-10 2018-11-15 Dow Global Technologies Llc Polyether polymerization process
WO2019055177A1 (en) 2017-09-15 2019-03-21 Dow Global Technologies Llc Continuous process for making polyether polyols
WO2023017078A1 (en) * 2021-08-11 2023-02-16 Shell Internationale Research Maatschappij B.V. Process for preparing a high-resilience polyurethane foam

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