CA2326444A1 - Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof - Google Patents

Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof Download PDF

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Publication number
CA2326444A1
CA2326444A1 CA002326444A CA2326444A CA2326444A1 CA 2326444 A1 CA2326444 A1 CA 2326444A1 CA 002326444 A CA002326444 A CA 002326444A CA 2326444 A CA2326444 A CA 2326444A CA 2326444 A1 CA2326444 A1 CA 2326444A1
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CA
Canada
Prior art keywords
polyol
comonomer
dmc
catalysed
mixture
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.)
Granted
Application number
CA002326444A
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French (fr)
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CA2326444C (en
Inventor
Andrew M. Thompson
Wolfgang Schmidt
Donald F. Rohr
Jack R. Reese
Mark R. Kinkelaar
Daniel Frich
Thomas P. Farrell
Chiu Yan Chan
Robert W. Beisner
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Bayer Antwerpen NV
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Individual
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Publication of CA2326444A1 publication Critical patent/CA2326444A1/en
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Publication of CA2326444C publication Critical patent/CA2326444C/en
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    • 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
    • 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
    • C08G65/2609—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 containing aliphatic 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
    • 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
    • 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
    • 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

Abstract

Copolymer DMC-catalyzed polyoxypropylene polyols which exhibit processing latitude similar to base-catalyzed copolymer analogs and homopolyoxypropylene analogs may be prepared by oxyalkylation with a mixture of propylene oxide and ethylene oxide such that a finite ethylene oxide content is maintained in the oxyalkylation reactor for the most substantial part of the oxyalkylation, the polyoxypropylene polyol having randomly distributed oxyethylene moieties which constitute 1.5 weight percent or more of the polyol product. Block copolymer polyols having external blocks containing lesser oxyethylene content than internal blocks and bicompositional compositions containing discrete multimodal and dissimilar and optionally multimodal polyols produced by a continuous addition of starter process are useful as polyols exhibiting greater processing latitude.

Claims (10)

1. A multiblock DMC-catalysed polyol comprising oxypropylene units which comprises:
i) an internal block comprising oxypropylene units and comonomer units copolymerised therewith which internal block is preparable by oxyalkylating one or more initiators, in the presence of a DMC-catalyst or a non-DMC catalyst, with a first oxyalkylation mixture comprising propylene oxide and at least one comonomer copolymerisable therewith; and ii) at least one external block comprising oxypropylene units and comonomer units copolymerised therewith which external block is preparable by oxyalkylating in the presence of a DMC-catalyst i) with a second oxyalkylation mixture comprising propylene oxide and at least one comonomer copolymerisable therewith such that:
~ the concentration and/or nature of the at least one comonomer in the second mixture differs from that in the first mixture; and ~ at least 95 wt% of the polymerised oxypropylene units are randomly copolymerised into the comonomer units in bock the internal and the external locks; and ~ the copolymerised comonomer content in the external block is less than that in the internal block.
2. A bicompositional DMC-catalysed polyol comprising:
a) a first, multiblock polyol, said polyol having a first block comprising:
i) a non-DMC-catalysed oxypropylene-containing block; or ii) a DMC-catalysed, oxypropylene-containing block further comprising copolymerized comonomers selected from the group consisting of ethylene oxide, stabilization-modifying comonomers, and mixtures thereof, with the proviso that when only oxyethylene moieties are present as comonomers, they are present in an amount greater than about 1.5 wt%, and at least a second, external block comprising:
iii) a DMC-catalysed mixture of propylene oxide and an effective stabilizing amount of one or both of ethylene oxide and a stabilization-modifying comonomer; and b) a random polyoxypropylene copolymer polyol having no internal block derived from an oligomeric starter molecule with equivalent with greater than 200 Da, and containing a monomer distribution which is the same as the monomer distribution of a)iii).
3. A bicompositional DMC-catalysed polyol according to Claim 2, wherein the weight ratio of the copolymerised comonomer in the oligomeric initiator to the total copolymerised comonomer content in the polyol is at least 0.3.
4. A bicompositional DMC-catalysed polyol according to Claims 2 or 3, wherein the oligomeric initiator has an equivalent weight from 200 to 700 Da.
5. A bicompositional DMC-catalysed polyol according to any of Claims 2 to 4, wherein the first, multiblock polyol comprises from 1 to 60 wt% of the bicompositional polyol.
6. A polyol according to any preceding claim wherein from 5 to 40 wt% of the total copolymerised comonomer is located in internal blocks.
7. A polyol according to any preceding claim, wherein the comonomer comprises a substituted or unsubstituted C4 to C20 alkylene oxide, oxetane, methyl oxetane, a copolymerisable internal carboxylic ester or inner carboxylic anhydride; or a mixture thereof.
8. A process for the preparation of a DMC-catalysed polyol according to any preceding claim, which process comprises:
a) supplying an activated DMC catalyst/initiator mixture to a reactor;
b) polyoxyalkylating said initiator with an oxyalkylation mixture containing propylene oxide and at least one comonomer polymerisable therewith such that the concentration of the comonomer during the oxyalkylation is above zero for at least 95 % of the total oxyalkylation to produce an intermediate copolymer polyol;
c) polyoxyalkylating the intermediate copolymer polyol with an oxyalkylation mixture containing propylene oxide and at least one comonomer polymerisable therewith such that the concentration and/or nature of the at least one comonomer in step (c) differs from that in step (b);
d) recovering a polyol in which the copolymerised comonomer content is at least 1.5 wt%.
9. A process according to Claim 8, which is a continuous process wherein additional initiator molecules are continually or incrementally added to said reactor.
10. A process for the preparation of a polyurethane slab or molded foam by the reaction of a di- or polyisocyanate with a polyether polyol in the presence of customary blowing agent(s), additives and auxiliaries, which process comprises:
selecting as at least a portion of said polyol component a polyol according to any of Claims 1 to 7 and reacting the polyol with a di- or polyisocyanate to produce polyurethane slab or molded foam.
CA002326444A 1998-04-03 1999-03-31 Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof Expired - Fee Related CA2326444C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/054,554 US6008263A (en) 1998-04-03 1998-04-03 Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof
US09/054,554 1998-04-03
PCT/EP1999/002229 WO1999051657A1 (en) 1998-04-03 1999-03-31 Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof

Publications (2)

Publication Number Publication Date
CA2326444A1 true CA2326444A1 (en) 1999-10-14
CA2326444C CA2326444C (en) 2010-03-09

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CA002326444A Expired - Fee Related CA2326444C (en) 1998-04-03 1999-03-31 Molded and slab polyurethane foam prepared from double metal cyanide complex-catalyzed polyoxyalkylene polyols and polyols suitable for the preparation thereof

Country Status (17)

Country Link
US (1) US6008263A (en)
EP (1) EP1082372B1 (en)
JP (1) JP4931278B2 (en)
KR (1) KR100556181B1 (en)
CN (1) CN1152902C (en)
AR (1) AR014816A1 (en)
AU (1) AU3603899A (en)
BR (1) BR9909907B1 (en)
CA (1) CA2326444C (en)
DE (1) DE69922805T2 (en)
ES (1) ES2235477T3 (en)
HK (1) HK1038762B (en)
HU (1) HU227437B1 (en)
ID (1) ID28736A (en)
PT (1) PT1082372E (en)
TW (1) TW444028B (en)
WO (1) WO1999051657A1 (en)

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Also Published As

Publication number Publication date
ID28736A (en) 2001-06-28
EP1082372B1 (en) 2004-12-22
HK1038762B (en) 2005-03-18
ES2235477T3 (en) 2005-07-01
JP4931278B2 (en) 2012-05-16
TW444028B (en) 2001-07-01
BR9909907B1 (en) 2008-11-18
WO1999051657A1 (en) 1999-10-14
EP1082372A1 (en) 2001-03-14
HU227437B1 (en) 2011-06-28
PT1082372E (en) 2005-05-31
DE69922805D1 (en) 2005-01-27
HUP0101583A2 (en) 2001-10-28
HK1038762A1 (en) 2002-03-28
CN1152902C (en) 2004-06-09
KR100556181B1 (en) 2006-03-03
DE69922805T2 (en) 2005-12-08
KR20010042408A (en) 2001-05-25
BR9909907A (en) 2000-12-26
US6008263A (en) 1999-12-28
AU3603899A (en) 1999-10-25
AR014816A1 (en) 2001-03-28
CA2326444C (en) 2010-03-09
CN1304422A (en) 2001-07-18
JP2002510724A (en) 2002-04-09
HUP0101583A3 (en) 2002-03-28

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