CA2796656C - Polyols suitable for hot molded foam production with high renewable resource content - Google Patents

Polyols suitable for hot molded foam production with high renewable resource content Download PDF

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Publication number
CA2796656C
CA2796656C CA2796656A CA2796656A CA2796656C CA 2796656 C CA2796656 C CA 2796656C CA 2796656 A CA2796656 A CA 2796656A CA 2796656 A CA2796656 A CA 2796656A CA 2796656 C CA2796656 C CA 2796656C
Authority
CA
Canada
Prior art keywords
polyol
ethylene oxide
polyols
catalyst
foam
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.)
Expired - Fee Related
Application number
CA2796656A
Other languages
English (en)
French (fr)
Other versions
CA2796656A1 (en
Inventor
Stanley L. Hager
Micah N. Moore
Jack R. Reese
Brian L. Neal
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 LLC
Original Assignee
Bayer MaterialScience LLC
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 Bayer MaterialScience LLC filed Critical Bayer MaterialScience LLC
Publication of CA2796656A1 publication Critical patent/CA2796656A1/en
Application granted granted Critical
Publication of CA2796656C publication Critical patent/CA2796656C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • 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
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4072—Mixtures of compounds of group C08G18/63 with other macromolecular compounds
    • 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
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
    • C08G18/4866—Polyethers having a low unsaturation value
    • 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
    • C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular 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
    • C08G65/2603—Macromolecular 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
    • C08G65/2606—Macromolecular 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
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular 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
    • C08G65/2642—Macromolecular 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
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2663—Metal cyanide catalysts, i.e. DMC's
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
    • 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
    • C08G2110/0008—Foam properties flexible
    • 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
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Toxicology (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Casting Or Compression Moulding Of Plastics Or The Like (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyethers (AREA)
CA2796656A 2010-04-23 2011-04-15 Polyols suitable for hot molded foam production with high renewable resource content Expired - Fee Related CA2796656C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US32726210P 2010-04-23 2010-04-23
US61/327,262 2010-04-23
PCT/US2011/000685 WO2011133208A2 (en) 2010-04-23 2011-04-15 Polyols suitable for hot molded foam production with high renewable resource content

Publications (2)

Publication Number Publication Date
CA2796656A1 CA2796656A1 (en) 2011-10-27
CA2796656C true CA2796656C (en) 2018-07-03

Family

ID=44834715

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2796656A Expired - Fee Related CA2796656C (en) 2010-04-23 2011-04-15 Polyols suitable for hot molded foam production with high renewable resource content

Country Status (10)

Country Link
US (1) US10323212B2 (enExample)
EP (1) EP2560944A4 (enExample)
JP (1) JP6038775B2 (enExample)
KR (1) KR20130091631A (enExample)
CN (1) CN102858732B (enExample)
BR (1) BR112012027070A2 (enExample)
CA (1) CA2796656C (enExample)
MX (1) MX2012012117A (enExample)
SG (2) SG10201503146WA (enExample)
WO (1) WO2011133208A2 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8598248B2 (en) * 2010-07-16 2013-12-03 Bayer Materialscience Llc Flexible polyurethane foams made from alkoxylated natural oil
CN102532457B (zh) * 2012-02-09 2013-10-02 中国农业大学 一种利用玉米芯和工业辣椒废渣合成可降解聚氨酯的方法
JP2014125516A (ja) * 2012-12-26 2014-07-07 Kao Corp 硬質ポリウレタンフォーム製造用ポリオール混合物
WO2015143563A1 (en) * 2014-03-27 2015-10-01 Trent University Certain metathesized natural oil triacylglycerol polyols for use in polyurethane applications and their related physical properties
US10000601B2 (en) * 2014-03-27 2018-06-19 Trent University Metathesized triacylglycerol polyols for use in polyurethane applications and their related properties
WO2016119049A1 (en) * 2015-01-26 2016-08-04 Trent University Methods of making triacylglycerol polyols from fractions of metathesized natural oils and uses thereof
US9777245B2 (en) 2015-01-30 2017-10-03 Trent University Methods of fractionating metathesized triacylglycerol polyols and uses thereof
MX2017014405A (es) * 2015-05-15 2018-07-06 Stepan Co Aceites vegetales etoxilados en formulaciones de espuma de atomizacion de baja densidad.
CN106748767B (zh) * 2015-11-19 2020-03-17 中国石油化工股份有限公司 一种低羟值植物油基多元醇及其制备方法
CN108003323B (zh) * 2017-11-20 2021-01-15 万华化学（北京）有限公司 一种减震吸能聚氨酯材料及其制备方法
CN109134841A (zh) * 2018-07-18 2019-01-04 江苏理工学院 一种高活性植物多元醇的制备方法
US11920017B2 (en) * 2018-12-14 2024-03-05 Nanjing Tech University Preparation method of polyurethane foam
US11912814B2 (en) * 2018-12-14 2024-02-27 Nanjing Tech University Preparation method of flexible polyurethane foam
US11613604B2 (en) 2021-06-28 2023-03-28 Covestro Llc Isocyanate-reactive compositions, polyurethane foams formed therefrom, multi-layer composite articles that include such foams, and methods for their preparation

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW307778B (enExample) * 1992-10-28 1997-06-11 Takeda Pharm Industry Co Ltd
JPH09124766A (ja) * 1995-10-27 1997-05-13 Asahi Glass Co Ltd 軟質ポリウレタンフォームの製造方法
DE19903274A1 (de) * 1999-01-28 2000-08-03 Basf Ag Verfahren zur Herstellung von Polyetherpolyolen
DE19928156A1 (de) * 1999-06-19 2000-12-28 Bayer Ag Aus Polyetherpolyolen hergestellte Polyurethan-Weichschäume
DE10240186A1 (de) * 2002-08-28 2004-03-11 Basf Ag Verfahren zur Herstellung von emissionsarmen Polyurethan-Weichschaumstoffen
US20060073321A1 (en) * 2004-10-01 2006-04-06 Kaushiva Bryan D Molded flexible polyurethane foams with reduced flammability and superior durability
US20060229375A1 (en) 2005-04-06 2006-10-12 Yu-Ling Hsiao Polyurethane foams made with alkoxylated vegetable oil hydroxylate
DE102005041142A1 (de) * 2005-08-30 2007-03-01 Basf Ag Verfahren zur Herstellung von Polyetheralkoholen
DE102005056432A1 (de) 2005-11-26 2007-05-31 Bayer Materialscience Ag Verfahren zur Herstellung von Polyolen auf Basis natürlicher Öle
US20070238798A1 (en) * 2006-04-05 2007-10-11 Mcdaniel Kenneth G Flexible polyurethane foams made from vegetable oil alkoxylated via DMC-catalysis
TW200848445A (en) * 2006-12-19 2008-12-16 Asahi Glass Co Ltd Method for producing soft polyurethane foam
EP2563839B1 (de) * 2010-04-30 2014-12-17 Basf Se Polyetherpolyole, verfahren zur herstellung von polyetherpolyolen, sowie deren verwendung zur herstellung von polyurethanen
US9115246B2 (en) * 2010-04-30 2015-08-25 Basf Se Polyether polyols, process for preparing polyether polyols and their use for producing polyurethanes
US8598248B2 (en) * 2010-07-16 2013-12-03 Bayer Materialscience Llc Flexible polyurethane foams made from alkoxylated natural oil

Also Published As

Publication number Publication date
CN102858732A (zh) 2013-01-02
KR20130091631A (ko) 2013-08-19
JP2013530263A (ja) 2013-07-25
MX2012012117A (es) 2012-12-17
US20130210951A1 (en) 2013-08-15
SG184309A1 (en) 2012-11-29
EP2560944A4 (en) 2014-03-26
EP2560944A2 (en) 2013-02-27
CN102858732B (zh) 2015-11-25
WO2011133208A3 (en) 2012-02-23
US10323212B2 (en) 2019-06-18
JP6038775B2 (ja) 2016-12-07
BR112012027070A2 (pt) 2016-07-26
CA2796656A1 (en) 2011-10-27
SG10201503146WA (en) 2015-06-29
WO2011133208A2 (en) 2011-10-27

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