WO2003020787A1 - Integriertes verfahren zur herstellung von polyurethan-schäumen - Google Patents

Integriertes verfahren zur herstellung von polyurethan-schäumen Download PDF

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Publication number
WO2003020787A1
WO2003020787A1 PCT/EP2002/009781 EP0209781W WO03020787A1 WO 2003020787 A1 WO2003020787 A1 WO 2003020787A1 EP 0209781 W EP0209781 W EP 0209781W WO 03020787 A1 WO03020787 A1 WO 03020787A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurethane
propylene oxide
polyether alcohol
oxide
catalysts
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/EP2002/009781
Other languages
German (de)
English (en)
French (fr)
Inventor
Ulrich Müller
Joaquim Henrique Teles
Edward Bohres
Stephan Bauer
Raimund Ruppel
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP02797662A priority Critical patent/EP1440102B1/de
Priority to US10/488,522 priority patent/US20040249107A1/en
Priority to JP2003525054A priority patent/JP2005501942A/ja
Priority to DE50213298T priority patent/DE50213298D1/de
Priority to MXPA04001787 priority patent/MX266186B/es
Priority to CA002459139A priority patent/CA2459139A1/en
Publication of WO2003020787A1 publication Critical patent/WO2003020787A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D301/00Preparation of oxiranes
    • C07D301/02Synthesis of the oxirane ring
    • C07D301/03Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • 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
    • C08G18/4845Polyethers containing oxyethylene units and other oxyalkylene units containing oxypropylene or higher oxyalkylene 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
    • 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/10Process efficiency

Definitions

  • the properties of the polyurethane such as mechanical properties, odor, depend particularly strongly on the isocyanates and polyether alcohols used for the preparation and, if appropriate, on the blowing agents used.
  • the structure of the polyether alcohols in particular has a major influence on the properties of the polyurethanes obtained.
  • the properties of the polyether alcohols are influenced by the production process of the polyether alcohols and in particular by the properties and the production process of the starting materials.
  • Propylene oxide produced by known processes for the production, which are described, for example, in Weissermel, Arpe "Industrial Organic Chemistry", VCH-Verlag, Weinheim, 4th edition, pages 288 to 318, has the disadvantage that significant impurities are contained in the propylene oxide , The contamination is in a range from 5 to 100 ppm.
  • Multimetal cyanide compounds are known from the prior art as catalysts for polyadditions, in particular for ring-opening polymerizations of alkylene oxides, as described, for example, in EP-A 0 892 002, EP-1 0 862 977 and in EP-A 0 755 716 described.
  • the propylene oxide obtained in step (1) may also contain up to 100 ppm, in particular up to 40 ppm of methanol and up to 10 ppm, preferably up to 4 ppm, of acetaldehyde as further secondary components.
  • propylene oxide is obtained by means of step (1) according to the invention contains very low impurities on C6 components and no chlorine-organic impurities.
  • the present invention therefore relates to an integrated process for producing a polyurethane, the epoxidation according to step (1) being carried out in the presence of a zeolite catalyst, in particular a titanium-containing zeolite catalyst.
  • k is a fractional or whole number greater than or equal to zero
  • multimetal cyanide catalysts made of metal [hexacyanometalate-hexanitrometalate] which are suitable according to the invention are mentioned in the application WO 01/04182.
  • the starting compounds mentioned there are less expensive than the zinc hexacyanocobaltates generally used.
  • the catalysts show shorter induction times and in some cases they show moderate exotherm.
  • the multimetal cyanide catalysts prepared in this way can, however, also be supported, as described in the applications WO 01/04180 (polycarboxylic acids) and WO 01/04177 (zeolites). A simple removal of the catalyst can thereby be achieved.
  • Suitable polyester polyols can be obtained, for example, from organic dicarboxylic acids with 2 to 12 carbon atoms, preferably aliphatic dicarboxylic acids with 4 to 6 carbon atoms, and polyhydric alcohols, preferably diols, with 2 to 12 carbon atoms, preferably 2 to 6 carbon atoms getting produced.
  • suitable dicarboxylic acids are: succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid and terephthalic acid.
  • the dicarboxylic acids can be used both individually and in a mixture with one another.
  • modified polyisocyanates can be used together or with unmodified organic polyisocyanates such as. B. 2,4'-, 4,4'-diphenylmethane diisocyanate, crude MDI, 2,4- and / or 2,6-tolylene diisocyanate are optionally mixed.
  • these are ethylamine, n- Propylamine, i-propylamine, sec-propylamine, tert-butylamine, 1-aminoisobutane, substituted amines with two to about 20 carbon atoms such as 2- (N, N-dimethylamino) -1-aminoethane, aminomercaptans such as l-amino -2-mercaptoethane, diamines, aliphatic amino alcohols having 2 to about 20, preferably 2 to about 12 carbon atoms, for example methanolamine, l-amino-3,3-dimethyl-pentan-5-ol, 2-aminohexan-2 ', 2 "diethanolamine, 1-amino-2,5-dimethylcyclohexan-4-ol, 2-aminopropanol, 2-aminobutanol, 3-aminopropanol, l-amino-2-propanol, 2-amino-2-prop
  • customary substances can be used as auxiliaries and / or additives in the process according to the invention.
  • examples include surface-active substances, internal release agents (IMR), fillers, dyes, pigments, flame retardants, hydrolysis protection agents, fungistatic and bacteriostatic substances as well as UV stabilizers and antioxidants s. It is also possible to use pigments and / or dyes to obtain tinted / colored moldings.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Toxicology (AREA)
  • Inorganic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/EP2002/009781 2001-09-04 2002-09-02 Integriertes verfahren zur herstellung von polyurethan-schäumen Ceased WO2003020787A1 (de)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP02797662A EP1440102B1 (de) 2001-09-04 2002-09-02 Integriertes verfahren zur herstellung von polyurethan-schäumen
US10/488,522 US20040249107A1 (en) 2001-09-04 2002-09-02 Intergrated method for the production of polyurethane foams
JP2003525054A JP2005501942A (ja) 2001-09-04 2002-09-02 ポリウレタンフォームの製造方法
DE50213298T DE50213298D1 (de) 2001-09-04 2002-09-02 Integriertes verfahren zur herstellung von polyurethan-schäumen
MXPA04001787 MX266186B (es) 2001-09-04 2002-09-02 Metodo integrado para la produccion de espumas de poliuretano.
CA002459139A CA2459139A1 (en) 2001-09-04 2002-09-02 Integrated method for the production of polyurethane foams

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10143195A DE10143195A1 (de) 2001-09-04 2001-09-04 Integriertes Verfahren zur Herstellung von Polyurethan-Schäumen
DE10143195.3 2001-09-04

Publications (1)

Publication Number Publication Date
WO2003020787A1 true WO2003020787A1 (de) 2003-03-13

Family

ID=7697597

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/009781 Ceased WO2003020787A1 (de) 2001-09-04 2002-09-02 Integriertes verfahren zur herstellung von polyurethan-schäumen

Country Status (14)

Country Link
US (1) US20040249107A1 (enExample)
EP (1) EP1440102B1 (enExample)
JP (1) JP2005501942A (enExample)
KR (1) KR100854059B1 (enExample)
CN (1) CN1261478C (enExample)
AR (1) AR036416A1 (enExample)
AT (1) ATE423155T1 (enExample)
CA (1) CA2459139A1 (enExample)
DE (2) DE10143195A1 (enExample)
ES (1) ES2319973T3 (enExample)
MX (1) MX266186B (enExample)
PT (1) PT1440102E (enExample)
RU (1) RU2004110235A (enExample)
WO (1) WO2003020787A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007508406A (ja) * 2003-10-10 2007-04-05 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ ポリエーテルポリオールの製造方法
WO2010101700A1 (en) 2009-03-05 2010-09-10 Dow Global Technologies Inc. Polyols from hppo and polyurethane products made therefrom
EP1942051A3 (en) * 2007-01-02 2011-05-11 In novo d.o.o. Depth buoy for maritime applications and process for making it

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WO2002088148A1 (en) 2001-04-30 2002-11-07 The Regents Of The University Of Michigan Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein,with application for gas storage
US20030078311A1 (en) 2001-10-19 2003-04-24 Ulrich Muller Process for the alkoxylation of organic compounds in the presence of novel framework materials
ATE466865T1 (de) 2003-05-09 2010-05-15 Univ Michigan Mofs mit einer hohen oberfläche und methode zu deren herstellung
CN101189244A (zh) 2004-10-22 2008-05-28 密歇根大学董事会 共价连接的有机骨架和多面体
DE102005008263A1 (de) * 2005-02-22 2006-08-24 Basf Ag Verfahren zur Herstellung von zylindrischen Formkörpern auf der Basis von zelligen Polyurethanelastomeren
PT1874459E (pt) 2005-04-07 2016-02-08 Univ Michigan Alta adsorção de gás numa estrutura microporosa organometálica com locais metálicos abertos
AU2006266874B2 (en) * 2005-07-01 2011-04-14 Mitsubishi Gas Chemical Company, Inc. Process for producing glycidyl 2-hydroxyisobutyrate and composition containing the product
WO2007038508A2 (en) 2005-09-26 2007-04-05 The Regents Of The University Of Michigan Metal-organic frameworks with exceptionally high capacity for storage of carbon dioxide at room-temperature
PT1984438E (pt) * 2006-02-07 2010-05-17 Basf Se Poliuretano antiestático
PL1988996T3 (pl) 2006-02-28 2018-01-31 Univ Michigan Regents Otrzymywanie szkieletów zeolitu z grupami funkcyjnymi
US8692030B1 (en) * 2006-04-20 2014-04-08 Pittsburg State University Biobased-petrochemical hybrid polyols
JP5371881B2 (ja) * 2009-12-10 2013-12-18 三井化学株式会社 カバー材の製造方法およびカバー材
SG181448A1 (en) * 2010-01-15 2012-08-30 Basf Se "process for the dmc-catalyzed preparation of polyols"
BR112016014640B1 (pt) * 2013-12-23 2021-09-14 Shell Internationale Research Maatschappij B.V Processo para fazer uma espuma de poliuretano retardante de chama, espuma de poliuretano, artigo conformado, e, uso de um poliol
US20180186921A1 (en) 2015-07-02 2018-07-05 Shell Oil Company Improvements relating to polyurethanes
JP7719411B1 (ja) * 2024-07-12 2025-08-06 Agc株式会社 ポリエーテル化合物の製造方法

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US5599956A (en) * 1996-02-22 1997-02-04 Uop Integrated process for the production of propylene oxide
WO1999051661A1 (en) * 1998-04-03 1999-10-14 Bayer Antwerpen N.V. Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof
EP1022300A1 (en) * 1998-07-10 2000-07-26 Asahi Glass Company Ltd. Catalyst for ring-opening polymerization of alkylene oxide, method for preparation thereof and use thereof

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US5627122A (en) * 1995-07-24 1997-05-06 Arco Chemical Technology, L.P. Highly active double metal cyanide complex catalysts
DE19723950A1 (de) * 1997-06-06 1998-12-10 Basf Ag Verfahren zur Oxidation einer mindestens eine C-C-Doppelbindung aufweisenden organischen Verbindung
US5912367A (en) * 1997-07-01 1999-06-15 Arco Chemical Technology, L.P. High efficiency epoxidation process
DE19730467A1 (de) * 1997-07-16 1999-01-21 Bayer Ag Neue Zink/Metall-Hexacyanocobaltat-Katalysatoren für die Herstellung von Polyetherpolyolen
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US6613714B2 (en) * 1999-06-02 2003-09-02 Basf Aktiengesellschaft Multimetal cyanide compounds, their preparation and their use
DE19928156A1 (de) * 1999-06-19 2000-12-28 Bayer Ag Aus Polyetherpolyolen hergestellte Polyurethan-Weichschäume
DE19936547A1 (de) * 1999-08-04 2001-02-15 Basf Ag Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid
US6365761B1 (en) * 1999-08-18 2002-04-02 Shell Oil Company Process for preparing alkylene oxide
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DE10015246A1 (de) * 2000-03-28 2001-10-04 Basf Ag Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid
DE10032885A1 (de) * 2000-07-06 2002-01-17 Basf Ag Verfahren zur Herstellung von Propylenoxid
DE10032884A1 (de) * 2000-07-06 2002-01-24 Basf Ag Verfahren zur Herstellung von Propylenoxid
JP2004530681A (ja) * 2001-05-08 2004-10-07 シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー アルキレンオキシド(エポキシド、オキシラン)を調製する方法

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US5599956A (en) * 1996-02-22 1997-02-04 Uop Integrated process for the production of propylene oxide
WO1999051661A1 (en) * 1998-04-03 1999-10-14 Bayer Antwerpen N.V. Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof
EP1022300A1 (en) * 1998-07-10 2000-07-26 Asahi Glass Company Ltd. Catalyst for ring-opening polymerization of alkylene oxide, method for preparation thereof and use thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007508406A (ja) * 2003-10-10 2007-04-05 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ ポリエーテルポリオールの製造方法
EP1942051A3 (en) * 2007-01-02 2011-05-11 In novo d.o.o. Depth buoy for maritime applications and process for making it
WO2010101700A1 (en) 2009-03-05 2010-09-10 Dow Global Technologies Inc. Polyols from hppo and polyurethane products made therefrom

Also Published As

Publication number Publication date
MX266186B (es) 2009-04-21
CN1564836A (zh) 2005-01-12
MXPA04001787A (es) 2004-07-08
DE10143195A1 (de) 2003-03-20
EP1440102B1 (de) 2009-02-18
PT1440102E (pt) 2009-03-06
JP2005501942A (ja) 2005-01-20
EP1440102A1 (de) 2004-07-28
DE50213298D1 (de) 2009-04-02
KR20040029144A (ko) 2004-04-03
RU2004110235A (ru) 2005-10-20
CN1261478C (zh) 2006-06-28
ATE423155T1 (de) 2009-03-15
US20040249107A1 (en) 2004-12-09
AR036416A1 (es) 2004-09-08
CA2459139A1 (en) 2003-03-13
KR100854059B1 (ko) 2008-08-26
ES2319973T3 (es) 2009-05-18

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