CN1069654C - 制备小平均粒度、高稳定性、细碎的、低粘度聚合物多元醇的连续方法 - Google Patents
制备小平均粒度、高稳定性、细碎的、低粘度聚合物多元醇的连续方法 Download PDFInfo
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- CN1069654C CN1069654C CN96112759A CN96112759A CN1069654C CN 1069654 C CN1069654 C CN 1069654C CN 96112759 A CN96112759 A CN 96112759A CN 96112759 A CN96112759 A CN 96112759A CN 1069654 C CN1069654 C CN 1069654C
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- BRWZYZWZBMGMMG-UHFFFAOYSA-J dodecanoate tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BRWZYZWZBMGMMG-UHFFFAOYSA-J 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 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
- 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
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 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
- 239000011368 organic material Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 229960004793 sucrose Drugs 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
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- 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 |
| EP95115940.9 | 1995-10-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1160061A CN1160061A (zh) | 1997-09-24 |
| CN1069654C true CN1069654C (zh) | 2001-08-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96112759A Expired - Fee Related CN1069654C (zh) | 1995-10-10 | 1996-10-10 | 制备小平均粒度、高稳定性、细碎的、低粘度聚合物多元醇的连续方法 |
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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104053692A (zh) * | 2011-12-16 | 2014-09-17 | 拜尔材料科学有限公司 | 用于聚氨酯泡沫材料应用的混合phd/pmpo多元醇 |
| CN108559033A (zh) * | 2018-04-10 | 2018-09-21 | 长华化学科技股份有限公司 | 大分子稳定剂预聚体的制备方法 |
| CN108570130A (zh) * | 2018-04-10 | 2018-09-25 | 长华化学科技股份有限公司 | 高性能聚合物多元醇的制备方法 |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6013731A (en) * | 1997-12-16 | 2000-01-11 | Arco Chemical Technology L.P. | Stabilizer based on high molecular weight polyols having low monol content for polymer polyol production |
| 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 |
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| 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 |
| JP4782940B2 (ja) * | 2001-04-27 | 2011-09-28 | 株式会社日本触媒 | 親水性グラフト重合体の製造方法 |
| 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 |
| US7148288B2 (en) * | 2003-06-27 | 2006-12-12 | Basf Corporation | Process for formation of preformed stabilizer polyols |
| US8470927B2 (en) * | 2004-02-26 | 2013-06-25 | Bayer Materialscience Llc | Process for production of polymer polyols |
| DE102004017294A1 (de) * | 2004-04-05 | 2005-10-20 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Schaumstoffen |
| US20050239968A1 (en) * | 2004-04-23 | 2005-10-27 | Heyman Duane A | Process for preparing graft polyols using enol ethers as reaction moderators |
| US7759423B2 (en) * | 2004-08-02 | 2010-07-20 | Bayer Materialscience Llc | Polymer polyols with ultra-high solids contents |
| US7160975B2 (en) * | 2004-08-02 | 2007-01-09 | Bayer Materialscience Llc | Methacrylates as stabilizers for polymer polyols |
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| JP5177614B2 (ja) * | 2005-07-07 | 2013-04-03 | 三洋化成工業株式会社 | 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 |
| RU2380388C2 (ru) | 2005-07-07 | 2010-01-27 | Санио Кемикал Индастриз, Лтд. | Полиольная композиция, содержащая диспергированные мелкие частицы, способ получения полимерного полиола и способ получения полиуретановой смолы |
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| EP3938415A1 (en) | 2019-03-15 | 2022-01-19 | Basf Se | Lignocellulosic composite articles |
| WO2021071808A1 (en) | 2019-10-09 | 2021-04-15 | Covestro Llc | Methods, systems and computer program products for producing polyurethane foam products using optical and infrared imaging |
| US11421063B2 (en) | 2019-10-10 | 2022-08-23 | Covestro Llc | Preformed stabilizers with improved stability |
| ES2919658T3 (es) | 2020-02-25 | 2022-07-27 | Repsol Sa | Procedimiento para preparar polioles poliméricos |
| CN113557251B (zh) * | 2020-02-25 | 2024-02-20 | 雷普索尔有限公司 | 用于制备聚合物多元醇的方法 |
| KR102401573B1 (ko) * | 2020-10-23 | 2022-05-25 | 금호석유화학 주식회사 | 폴리머 폴리올의 제조방법 |
| CN112851878A (zh) * | 2021-01-08 | 2021-05-28 | 福建省天骄化学材料有限公司 | 一种高固含量聚合物多元醇及其制备方法 |
| US11572433B2 (en) | 2021-03-12 | 2023-02-07 | Covestro Llc | In-situ formed polyols, a process for their preparation, foams prepared from these in-situ formed polyols and a process for their preparation |
| US11866543B2 (en) | 2021-05-06 | 2024-01-09 | Covestro Llc | Glycidyl (meth)acrylate polymer polyol stabilizers |
| US11718705B2 (en) | 2021-07-28 | 2023-08-08 | Covestro Llc | In-situ formed polyether polyols, a process for their preparation, and a process for the preparation of polyurethane foams |
| US11952454B2 (en) | 2021-10-18 | 2024-04-09 | Covestro Llc | Processes and production plants for producing polymer polyols |
| CN114644733B (zh) * | 2022-02-16 | 2024-11-12 | 万华化学集团股份有限公司 | 一种聚合物多元醇制备方法 |
| KR102832049B1 (ko) * | 2022-06-14 | 2025-07-10 | 금호석유화학 주식회사 | 폴리머 폴리올 및 그 제조방법 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960956A (en) * | 1989-05-09 | 1990-10-02 | Shell Oil Company | Modified bisphenols having at least one arylcyclobutenealkyl moiety and cured products therefrom |
| US5364906A (en) * | 1993-08-20 | 1994-11-15 | Arco Chemical Technology, L.P. | Low viscosity polymer polyols with improved dispersion stability |
Family Cites Families (13)
| 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 |
| 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 |
| 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960956A (en) * | 1989-05-09 | 1990-10-02 | Shell Oil Company | Modified bisphenols having at least one arylcyclobutenealkyl moiety and cured products therefrom |
| US5364906A (en) * | 1993-08-20 | 1994-11-15 | Arco Chemical Technology, L.P. | Low viscosity polymer polyols with improved dispersion stability |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104053692A (zh) * | 2011-12-16 | 2014-09-17 | 拜尔材料科学有限公司 | 用于聚氨酯泡沫材料应用的混合phd/pmpo多元醇 |
| CN104053692B (zh) * | 2011-12-16 | 2017-02-22 | 拜尔材料科学有限公司 | 用于聚氨酯泡沫材料应用的混合phd/pmpo多元醇 |
| CN108559033A (zh) * | 2018-04-10 | 2018-09-21 | 长华化学科技股份有限公司 | 大分子稳定剂预聚体的制备方法 |
| CN108570130A (zh) * | 2018-04-10 | 2018-09-25 | 长华化学科技股份有限公司 | 高性能聚合物多元醇的制备方法 |
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 |
| JPH09124750A (ja) | 1997-05-13 |
| TW375618B (en) | 1999-12-01 |
| EP0768324A1 (en) | 1997-04-16 |
| DE69518423D1 (de) | 2000-09-21 |
| 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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