CA2578826C - Methode de preparation de dispersions polymeriques de polyols - Google Patents

Methode de preparation de dispersions polymeriques de polyols Download PDF

Info

Publication number: CA2578826C
Authority: CA; Canada
Prior art keywords: polyol; polymer; metal cyanide; catalyst; double metal
Prior art date: 1995-11-30
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

CA2578826A

Other languages

English (en)

Other versions

CA2578826A1 (fr

Inventor

Donald W. Simroth

Xinhua Zhou

Charles V. Rose

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.)

Bayer Antwerpen NV

Original Assignee

Bayer Antwerpen NV

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.)

1995-11-30

Filing date

1996-10-28

Publication date

2011-01-25

1995-11-30 Priority claimed from US08/565,516 external-priority patent/US5688861A/en

1996-10-28 Application filed by Bayer Antwerpen NV filed Critical Bayer Antwerpen NV

1997-05-31 Publication of CA2578826A1 publication Critical patent/CA2578826A1/fr

2011-01-25 Application granted granted Critical

2011-01-25 Publication of CA2578826C publication Critical patent/CA2578826C/fr

2016-10-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920005862 polyol Polymers 0.000 title claims abstract description 342
150000003077 polyols Chemical class 0.000 title claims abstract description 340
229920000642 polymer Polymers 0.000 title claims abstract description 96
238000000034 method Methods 0.000 title claims description 46
239000006185 dispersion Substances 0.000 title description 31
238000002360 preparation method Methods 0.000 title description 17
230000008569 process Effects 0.000 title description 14
239000003054 catalyst Substances 0.000 claims abstract description 181
229910052751 metal Inorganic materials 0.000 claims abstract description 110
239000002184 metal Substances 0.000 claims abstract description 110
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 95
229910052723 transition metal Inorganic materials 0.000 claims abstract description 51
150000003624 transition metals Chemical class 0.000 claims abstract description 51
238000006116 polymerization reaction Methods 0.000 claims abstract description 46
239000000178 monomer Substances 0.000 claims abstract description 43
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 35
229920000570 polyether Polymers 0.000 claims abstract description 35
238000011065 in-situ storage Methods 0.000 claims abstract description 33
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 55
239000011701 zinc Substances 0.000 claims description 50
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 36
229910052725 zinc Inorganic materials 0.000 claims description 35
239000007787 solid Substances 0.000 claims description 30
229920002554 vinyl polymer Polymers 0.000 claims description 30
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 26
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 26
239000000047 product Substances 0.000 claims description 24
239000003999 initiator Substances 0.000 claims description 21
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239000011496 polyurethane foam Substances 0.000 claims description 17
229920005830 Polyurethane Foam Polymers 0.000 claims description 16
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
239000004815 dispersion polymer Substances 0.000 claims description 14
239000005056 polyisocyanate Substances 0.000 claims description 14
229920001228 polyisocyanate Polymers 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 13
241001425800 Pipa Species 0.000 claims description 10
238000002441 X-ray diffraction Methods 0.000 claims description 10
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
239000004604 Blowing Agent Substances 0.000 claims description 3
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230000001747 exhibiting effect Effects 0.000 claims description 3
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150000002009 diols Chemical class 0.000 description 18
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 17
239000000306 component Substances 0.000 description 17
230000000052 comparative effect Effects 0.000 description 14
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JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
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238000007792 addition Methods 0.000 description 11
239000006260 foam Substances 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
239000003381 stabilizer Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 7
238000012360 testing method Methods 0.000 description 7
239000012974 tin catalyst Substances 0.000 description 7
238000004458 analytical method Methods 0.000 description 6
RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 6
238000010924 continuous production Methods 0.000 description 6
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239000003795 chemical substances by application Substances 0.000 description 5
229910017052 cobalt Inorganic materials 0.000 description 5
239000010941 cobalt Substances 0.000 description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000002685 polymerization catalyst Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
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PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical class C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
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239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
238000001514 detection method Methods 0.000 description 4
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239000004814 polyurethane Substances 0.000 description 4
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DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
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150000004985 diamines Chemical class 0.000 description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
230000006698 induction Effects 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
125000006353 oxyethylene group Chemical group 0.000 description 3
239000002243 precursor Substances 0.000 description 3
238000012545 processing Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical class COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
229920002396 Polyurea Polymers 0.000 description 2
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239000012975 dibutyltin dilaurate Substances 0.000 description 2
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238000007710 freezing Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
238000009616 inductively coupled plasma Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000007870 radical polymerization initiator Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000004062 sedimentation Methods 0.000 description 2
241000894007 species Species 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 1
PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 1
JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
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229910052794 bromium Inorganic materials 0.000 description 1
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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125000005442 diisocyanate group Chemical group 0.000 description 1
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125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

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CA2578826A 1995-11-30 1996-10-28 Methode de preparation de dispersions polymeriques de polyols Expired - Fee Related CA2578826C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/565,516		1995-11-30
US08/565,516 US5688861A (en)	1995-11-30	1995-11-30	Process for the preparation of polyol polymer dispersions
CA002188965A CA2188965C (fr)	1995-11-30	1996-10-28	Methode de preparation de dispersions polymeriques de polyols

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002188965A Division CA2188965C (fr)	1995-11-30	1996-10-28	Methode de preparation de dispersions polymeriques de polyols

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Publication Number	Publication Date
CA2578826A1 CA2578826A1 (fr)	1997-05-31
CA2578826C true CA2578826C (fr)	2011-01-25

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US11952454B2 (en)	2021-10-18	2024-04-09	Covestro Llc	Processes and production plants for producing polymer polyols

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Publication	Publication Date	Title
CA2188965C (fr)	2007-05-15	Methode de preparation de dispersions polymeriques de polyols
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RU2177828C2 (ru)	2002-01-10	Высокоактивные двойные металлоцианидные катализаторы
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US6762278B2 (en)	2004-07-13	Process for the copolymerization of alkylene oxides and carbon dioxide using suspensions of multi-metal cyanide compounds
TW460324B (en)	2001-10-21	Double metal cyanide catalysts containing cyclic, bidentate complexing agents and method for producing the same and polyether polyol prepared from the same
KR19990071642A (ko)	1999-09-27	이중 금속 시아나이드 착물 촉매를 사용하여 제조된 전이금속을저 수준으로 함유하는 폴리옥시알킬렌 폴리에테르 폴리올의 제조방법
EP1409567B1 (fr)	2007-01-24	Catalyseur de complexes de metallisation a deux niveaux
KR100346929B1 (ko)	2002-11-04	폴리올합성용발포체지지형이중금속시안화물촉매및그제조방법
US5891818A (en)	1999-04-06	Cyanide complex catalyst manufacturing process
CA2578826C (fr)	2011-01-25	Methode de preparation de dispersions polymeriques de polyols
HK1033289A (en)	2001-08-24	Improved double metal cyanide complex catalysts