JPH09124750A - 平均粒度が小さい高安定、微細、低粘度ポリマーポリオールの連続製法 - Google Patents
平均粒度が小さい高安定、微細、低粘度ポリマーポリオールの連続製法Info
- Publication number
- JPH09124750A JPH09124750A JP8285938A JP28593896A JPH09124750A JP H09124750 A JPH09124750 A JP H09124750A JP 8285938 A JP8285938 A JP 8285938A JP 28593896 A JP28593896 A JP 28593896A JP H09124750 A JPH09124750 A JP H09124750A
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- reactor
- macromer
- mixture
- weight
- 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.)
- Pending
Links
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- 150000003077 polyols Chemical class 0.000 title claims abstract description 107
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- 238000010924 continuous production Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims abstract description 49
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- 239000000203 mixture Substances 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 239000003607 modifier Substances 0.000 claims abstract description 19
- 239000003999 initiator Substances 0.000 claims abstract description 18
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 12
- 229920005903 polyol mixture Polymers 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 9
- 238000012546 transfer Methods 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 41
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 23
- 229920000570 polyether Polymers 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
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- 150000001875 compounds Chemical class 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 12
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- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ITMIAZBRRZANGB-UHFFFAOYSA-N but-3-ene-1,2-diol Chemical compound OCC(O)C=C ITMIAZBRRZANGB-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- JEVXQVKXMWAWQE-UHFFFAOYSA-N cyclohex-3-en-1-ylidenemethoxymethylbenzene Chemical compound C=1C=CC=CC=1COC=C1CCC=CC1 JEVXQVKXMWAWQE-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FJIKWRGCXUCUIG-UHFFFAOYSA-N lormetazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000004917 polyol method Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/635—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto unsaturated polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- 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
- C08G2110/0016—Foam properties semi-rigid
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95115940A EP0768324B1 (en) | 1995-10-10 | 1995-10-10 | Continuous process for the preparation of highly stable, finely divided, low viscosity polymer polyols of small average particle size |
| DE95115940.9 | 1995-10-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09124750A true JPH09124750A (ja) | 1997-05-13 |
| JPH09124750A5 JPH09124750A5 (enExample) | 2004-10-14 |
Family
ID=8219706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8285938A Pending JPH09124750A (ja) | 1995-10-10 | 1996-10-09 | 平均粒度が小さい高安定、微細、低粘度ポリマーポリオールの連続製法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5814699A (enExample) |
| EP (1) | EP0768324B1 (enExample) |
| JP (1) | JPH09124750A (enExample) |
| KR (1) | KR100433147B1 (enExample) |
| CN (1) | CN1069654C (enExample) |
| BR (1) | BR9605032A (enExample) |
| CA (1) | CA2187125A1 (enExample) |
| DE (1) | DE69518423T2 (enExample) |
| ES (1) | ES2148397T3 (enExample) |
| MX (1) | MX9604686A (enExample) |
| TW (1) | TW375618B (enExample) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002508417A (ja) * | 1997-12-16 | 2002-03-19 | バイエル・アクチエンゲゼルシヤフト | ポリマーポリオールおよび安定化剤システム |
| JP2002327029A (ja) * | 2001-04-27 | 2002-11-15 | Nippon Shokubai Co Ltd | 親水性グラフト重合体の製造方法 |
| JP2006045569A (ja) * | 2004-08-02 | 2006-02-16 | Bayer Material Science Llc | ポリマーポリオール用の安定剤としてのメタクリレート |
| JP2007039677A (ja) * | 2005-07-07 | 2007-02-15 | Sanyo Chem Ind Ltd | 微粒子分散ポリオール組成物およびポリウレタン樹脂の製法 |
| JP2007531809A (ja) * | 2004-04-05 | 2007-11-08 | ビーエーエスエフ アクチェンゲゼルシャフト | ポリウレタンフォームの製造方法 |
| JP2009149895A (ja) * | 2007-12-20 | 2009-07-09 | Bayer Material Science Llc | 改善された特性を有するポリマーポリオールおよびそれらの製造方法 |
| JP2010503743A (ja) * | 2006-09-14 | 2010-02-04 | ビーエーエスエフ ソシエタス・ヨーロピア | グラフトポリオールを形成する方法、及びグラフトポリオールから形成されたポリウレタン製品 |
| US8394899B2 (en) | 2005-07-07 | 2013-03-12 | Sanyo Chemical Industries, Ltd. | Fine particle-dispersed polyol composition, method for producing polymer polyol, and method for producing polyurethane resin |
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| KR20170002494A (ko) * | 2014-04-30 | 2017-01-06 | 바스프 에스이 | 폴리머 폴리올의 제조 방법 |
| JP2023547136A (ja) * | 2020-10-23 | 2023-11-09 | コリア クンホ ペトロケミカル カンパニー リミテッド | ポリマーポリオールの製造方法 |
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| JPH10198539A (ja) * | 1997-01-08 | 1998-07-31 | Fuji Xerox Co Ltd | 画像形成装置および画像形成方法 |
| DE19903390A1 (de) | 1999-01-29 | 2000-08-03 | Bayer Ag | Stabilisierte, feindisperse niedrigviskose Polymerpolyole mit einem hohen Gehalt an Polystyrol oder Polystyrol-Copolymerisaten |
| US6756414B2 (en) * | 1999-07-30 | 2004-06-29 | Sanyo Chemical Industries, Ltd. | Polymer polyol composition, process for producing the same, and process for producing polyurethane resin |
| US6624209B2 (en) | 1999-07-30 | 2003-09-23 | Sanyo Chemical Industries, Ltd. | Polymer polyol composition, process for producing the same, and process for producing polyurethane resin |
| CA2325972A1 (en) * | 1999-11-24 | 2001-05-24 | Dainippon Ink And Chemicals, Inc. | Compatibilizing agent, radical copolymerizable unsaturated resin composition, molding material, and molded article |
| MXPA04008161A (es) * | 2002-03-15 | 2005-05-17 | Basf Ag | Polioles de injerto con una distribucion de tamano de particula bimodal y metodo para producir polioles de injerto de este tipo, ademas del uso de los mismos para producir poliuretanos. |
| US20050245724A1 (en) * | 2002-04-10 | 2005-11-03 | Sanyo Chemical Industries, Ltd. | Process for production of polymer polyol, and polymer polyol |
| US8017664B2 (en) | 2002-05-22 | 2011-09-13 | Shell Oil Company | Process for preparing polymer polyols |
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| KR102832049B1 (ko) * | 2022-06-14 | 2025-07-10 | 금호석유화학 주식회사 | 폴리머 폴리올 및 그 제조방법 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148840A (en) * | 1978-03-29 | 1979-04-10 | Union Carbide Corporation | Polymer/polyol compositions made from preformed polymer/polyols, processes for making same and processes for making polyurethane products therefrom |
| JPS54133582A (en) * | 1978-04-07 | 1979-10-17 | Mitsui Nisso Urethane | Preparation of polymerpolyol |
| US4242249A (en) * | 1979-04-03 | 1980-12-30 | Union Carbide Corporation | Polymer/polyols via non-aqueous dispersion stabilizers |
| US4690956A (en) * | 1982-04-01 | 1987-09-01 | Basf Corporation | Process for the preparation of graft polymer dispersions and flame-retardant polyurethane foams |
| US4550194A (en) * | 1982-04-01 | 1985-10-29 | Basf Wyandotte Corporation | Process for the preparation of polyether-ester polyols |
| US4458038A (en) * | 1982-04-01 | 1984-07-03 | Basf Wyandotte Corporation | Process for the preparation of white graft polymer dispersions and flame-retardant polyurethane foams |
| US4454255A (en) * | 1982-04-01 | 1984-06-12 | Basf Wyandotte Corporation | Process for the preparation of white graft polymer dispersions and flame-retardant polyurethane foams |
| US4689354A (en) * | 1982-04-01 | 1987-08-25 | Basf Corporation | Process for the preparation of white graft polymer dispersions and flame-retardant polyurethane foams |
| USRE33291E (en) * | 1982-04-01 | 1990-08-07 | Basf Corporation | Process for the preparation of white graft polymer dispersions and flame-retardant polyurethane foams |
| DE3612376A1 (de) * | 1986-04-12 | 1987-10-15 | Basf Ag | Verfahren zum herstellen kleinteiliger homo- und copolymerisate des ethens unter verwendung eines fluessigen alkans als reaktionsmedium |
| US4956427A (en) * | 1988-12-23 | 1990-09-11 | Union Carbide Chemicals And Plastics Company Inc. | Process for reducing polymer build-up in polymerization equipment during polymerization of alpha-olefins |
| US4960956A (en) * | 1989-05-09 | 1990-10-02 | Shell Oil Company | Modified bisphenols having at least one arylcyclobutenealkyl moiety and cured products therefrom |
| US5223570A (en) * | 1990-02-07 | 1993-06-29 | Basf Corporation | Method for the preparation of graft polymer dispersions having broad particle size distribution without wildly fluctuating viscosities |
| US5364906A (en) * | 1993-08-20 | 1994-11-15 | Arco Chemical Technology, L.P. | Low viscosity polymer polyols with improved dispersion stability |
| DE4431226A1 (de) * | 1994-09-02 | 1996-03-07 | Bayer Ag | Niedrigviskose, stabile agglomeratfreie Polymerpolyole, ein Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Polyurethankunststoffen |
-
1995
- 1995-10-10 EP EP95115940A patent/EP0768324B1/en not_active Expired - Lifetime
- 1995-10-10 ES ES95115940T patent/ES2148397T3/es not_active Expired - Lifetime
- 1995-10-10 DE DE69518423T patent/DE69518423T2/de not_active Expired - Fee Related
-
1996
- 1996-10-03 US US08/723,659 patent/US5814699A/en not_active Expired - Fee Related
- 1996-10-04 CA CA002187125A patent/CA2187125A1/en not_active Abandoned
- 1996-10-09 KR KR1019960044861A patent/KR100433147B1/ko not_active Expired - Fee Related
- 1996-10-09 TW TW085112322A patent/TW375618B/zh active
- 1996-10-09 JP JP8285938A patent/JPH09124750A/ja active Pending
- 1996-10-09 BR BR9605032A patent/BR9605032A/pt not_active IP Right Cessation
- 1996-10-09 MX MX9604686A patent/MX9604686A/es unknown
- 1996-10-10 CN CN96112759A patent/CN1069654C/zh not_active Expired - Fee Related
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002508417A (ja) * | 1997-12-16 | 2002-03-19 | バイエル・アクチエンゲゼルシヤフト | ポリマーポリオールおよび安定化剤システム |
| JP2002327029A (ja) * | 2001-04-27 | 2002-11-15 | Nippon Shokubai Co Ltd | 親水性グラフト重合体の製造方法 |
| JP2007531809A (ja) * | 2004-04-05 | 2007-11-08 | ビーエーエスエフ アクチェンゲゼルシャフト | ポリウレタンフォームの製造方法 |
| KR101215139B1 (ko) * | 2004-08-02 | 2012-12-24 | 바이엘 머티리얼싸이언스 엘엘씨 | 중합체 폴리올용 안정화제로서의 메타크릴레이트 |
| JP2006045569A (ja) * | 2004-08-02 | 2006-02-16 | Bayer Material Science Llc | ポリマーポリオール用の安定剤としてのメタクリレート |
| US8394899B2 (en) | 2005-07-07 | 2013-03-12 | Sanyo Chemical Industries, Ltd. | Fine particle-dispersed polyol composition, method for producing polymer polyol, and method for producing polyurethane resin |
| JP2007039677A (ja) * | 2005-07-07 | 2007-02-15 | Sanyo Chem Ind Ltd | 微粒子分散ポリオール組成物およびポリウレタン樹脂の製法 |
| US8455591B2 (en) | 2005-07-07 | 2013-06-04 | Sanyo Chemical Industries, Ltd. | Fine particle-dispersed polyol composition, method for producing polymer polyol, and method for producing polyurethane resin |
| JP2010503743A (ja) * | 2006-09-14 | 2010-02-04 | ビーエーエスエフ ソシエタス・ヨーロピア | グラフトポリオールを形成する方法、及びグラフトポリオールから形成されたポリウレタン製品 |
| US8772405B2 (en) | 2007-09-28 | 2014-07-08 | Sanyo Chemical Industries, Ltd. | Polymer polyol, method for producing the same, and method for producing polyurethane resin |
| US9109078B2 (en) | 2007-09-28 | 2015-08-18 | Sanyo Chemical Industries, Ltd. | Polymer polyol, method for producing the same, and method for producing polyurethane resin |
| US9062148B2 (en) | 2007-10-10 | 2015-06-23 | Sanyo Chemical Industries, Ltd. | Method for producing fine-particle-dispersed polyol, and method for producing polyurethane resin |
| JP2009149895A (ja) * | 2007-12-20 | 2009-07-09 | Bayer Material Science Llc | 改善された特性を有するポリマーポリオールおよびそれらの製造方法 |
| KR20170002494A (ko) * | 2014-04-30 | 2017-01-06 | 바스프 에스이 | 폴리머 폴리올의 제조 방법 |
| JP2017514959A (ja) * | 2014-04-30 | 2017-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリマーポリオールの製造方法 |
| JP2023547136A (ja) * | 2020-10-23 | 2023-11-09 | コリア クンホ ペトロケミカル カンパニー リミテッド | ポリマーポリオールの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US5814699A (en) | 1998-09-29 |
| CN1160061A (zh) | 1997-09-24 |
| ES2148397T3 (es) | 2000-10-16 |
| KR100433147B1 (ko) | 2004-09-24 |
| DE69518423T2 (de) | 2000-12-14 |
| TW375618B (en) | 1999-12-01 |
| EP0768324A1 (en) | 1997-04-16 |
| DE69518423D1 (de) | 2000-09-21 |
| CN1069654C (zh) | 2001-08-15 |
| BR9605032A (pt) | 1998-06-30 |
| MX9604686A (es) | 1998-04-30 |
| EP0768324B1 (en) | 2000-08-16 |
| KR970021113A (ko) | 1997-05-28 |
| CA2187125A1 (en) | 1997-04-11 |
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