JP5650211B2 - ホスフィンが初期装入される超分岐ポリオールの製造方法 - Google Patents
ホスフィンが初期装入される超分岐ポリオールの製造方法 Download PDFInfo
- Publication number
- JP5650211B2 JP5650211B2 JP2012518893A JP2012518893A JP5650211B2 JP 5650211 B2 JP5650211 B2 JP 5650211B2 JP 2012518893 A JP2012518893 A JP 2012518893A JP 2012518893 A JP2012518893 A JP 2012518893A JP 5650211 B2 JP5650211 B2 JP 5650211B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- phosphine
- production method
- polyol
- solvent
- 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.)
- Expired - Fee Related
Links
- 229920005862 polyol Polymers 0.000 title claims description 31
- 150000003077 polyols Chemical class 0.000 title claims description 31
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims description 12
- 239000002904 solvent Substances 0.000 claims description 24
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 16
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000000034 method Methods 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 14
- 238000005227 gel permeation chromatography Methods 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 150000003003 phosphines Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000412 dendrimer Substances 0.000 description 7
- 229920000736 dendritic polymer Polymers 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- -1 diaryl phosphines Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LOHJQYQXEMXLBA-UHFFFAOYSA-N 1-(oxiran-2-yl)propan-2-ol Chemical compound CC(O)CC1CO1 LOHJQYQXEMXLBA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920000587 hyperbranched polymer Polymers 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000000075 primary alcohol group Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000003198 secondary alcohol group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010414 supernatant solution Substances 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-GSVOUGTGSA-N (R)-Glycidol Chemical compound OC[C@@H]1CO1 CTKINSOISVBQLD-GSVOUGTGSA-N 0.000 description 1
- CTKINSOISVBQLD-VKHMYHEASA-N (S)-Glycidol Chemical compound OC[C@H]1CO1 CTKINSOISVBQLD-VKHMYHEASA-N 0.000 description 1
- ATPOZSUPSQATIN-UHFFFAOYSA-N 1-(oxiran-2-yl)butan-1-ol Chemical compound CCCC(O)C1CO1 ATPOZSUPSQATIN-UHFFFAOYSA-N 0.000 description 1
- HUUXOKLITMBBCB-UHFFFAOYSA-N 1-(oxiran-2-yl)butan-2-ol Chemical compound CCC(O)CC1CO1 HUUXOKLITMBBCB-UHFFFAOYSA-N 0.000 description 1
- LEJLUUHSOFWJSW-UHFFFAOYSA-N 1-(oxiran-2-yl)ethanol Chemical compound CC(O)C1CO1 LEJLUUHSOFWJSW-UHFFFAOYSA-N 0.000 description 1
- DVPPDGQNQQRLMF-UHFFFAOYSA-N 1-(oxiran-2-yl)hexan-3-ol Chemical compound CCCC(O)CCC1CO1 DVPPDGQNQQRLMF-UHFFFAOYSA-N 0.000 description 1
- SDKHBZKOZOCRHK-UHFFFAOYSA-N 1-(oxiran-2-yl)pentan-2-ol Chemical compound CCCC(O)CC1CO1 SDKHBZKOZOCRHK-UHFFFAOYSA-N 0.000 description 1
- WFHGHKCHDDNVOS-UHFFFAOYSA-N 1-(oxiran-2-yl)pentan-3-ol Chemical compound CCC(O)CCC1CO1 WFHGHKCHDDNVOS-UHFFFAOYSA-N 0.000 description 1
- HJCWXVWXDOBZTQ-UHFFFAOYSA-N 1-(oxiran-2-yl)propan-1-ol Chemical compound CCC(O)C1CO1 HJCWXVWXDOBZTQ-UHFFFAOYSA-N 0.000 description 1
- AVSUMWIDHQEMPD-UHFFFAOYSA-N 2-(oxiran-2-yl)ethanol Chemical compound OCCC1CO1 AVSUMWIDHQEMPD-UHFFFAOYSA-N 0.000 description 1
- SOGGLVJYVOCYTB-UHFFFAOYSA-N 3-(oxiran-2-yl)propan-1-ol Chemical compound OCCCC1CO1 SOGGLVJYVOCYTB-UHFFFAOYSA-N 0.000 description 1
- RYBPVYPKDOBJQK-UHFFFAOYSA-N 4-(oxiran-2-yl)butan-1-ol Chemical compound OCCCCC1CO1 RYBPVYPKDOBJQK-UHFFFAOYSA-N 0.000 description 1
- OYPVNGBBFLDVJH-UHFFFAOYSA-N 4-(oxiran-2-yl)butan-2-ol Chemical compound CC(O)CCC1CO1 OYPVNGBBFLDVJH-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QHRVFPPZMPHYHA-UHFFFAOYSA-N bis(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1PC1=CC=CC=C1C QHRVFPPZMPHYHA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
- WYLIVCZUBWFLDH-UHFFFAOYSA-N dinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(PC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 WYLIVCZUBWFLDH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FVWCDFMLOYFXCE-UHFFFAOYSA-N naphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P)=CC=CC2=C1 FVWCDFMLOYFXCE-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- 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
- C08G65/04—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 only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- 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
- C08G65/04—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 only
-
- 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
- C08G65/04—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 only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
-
- 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
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2675—Phosphorus or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09164094 | 2009-06-30 | ||
| EP09164094.6 | 2009-06-30 | ||
| PCT/EP2010/059253 WO2011000854A1 (de) | 2009-06-30 | 2010-06-30 | Verfahren zur phosphin-initialisierten herstellung von hyperverzweigten polyolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012531511A JP2012531511A (ja) | 2012-12-10 |
| JP2012531511A5 JP2012531511A5 (enExample) | 2013-08-15 |
| JP5650211B2 true JP5650211B2 (ja) | 2015-01-07 |
Family
ID=42938358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012518893A Expired - Fee Related JP5650211B2 (ja) | 2009-06-30 | 2010-06-30 | ホスフィンが初期装入される超分岐ポリオールの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9096713B2 (enExample) |
| EP (1) | EP2448994B1 (enExample) |
| JP (1) | JP5650211B2 (enExample) |
| KR (1) | KR20120047921A (enExample) |
| CN (1) | CN102471476B (enExample) |
| SG (1) | SG176903A1 (enExample) |
| WO (1) | WO2011000854A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5502349B2 (ja) * | 2009-03-13 | 2014-05-28 | 出光興産株式会社 | 水系潤滑剤 |
| US9184057B2 (en) | 2011-03-18 | 2015-11-10 | Basf Se | Method for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices having patterned material layers with line-space dimensions of 50 nm and less |
| KR102124607B1 (ko) * | 2019-10-31 | 2020-06-18 | 한국화학연구원 | 폴리에테르 폴리올, 이의 제조방법, 및 이의 용도 |
| KR102124605B1 (ko) * | 2019-10-31 | 2020-06-18 | 한국화학연구원 | 폴리에테르 폴리올의 제조방법 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB477843A (en) * | 1936-07-03 | 1938-01-03 | Ig Farbenindustrie Ag | The manufacture of new polymerisation products |
| GB1236848A (en) * | 1968-09-12 | 1971-06-23 | Kalk Chemische Fabrik Gmbh | Method of preparing transparent products consisting largely of polyepibromohydrin |
| JPS58157784A (ja) * | 1982-03-16 | 1983-09-19 | Kaken Pharmaceut Co Ltd | 光学活性な〔ｓ〕−（＋）−２−アセチル−７−（２，３−エポキシプロポキシ）ベンゾフランの製造法 |
| CN1283691C (zh) * | 1998-02-20 | 2006-11-08 | 花王株式会社 | 新型聚醚 |
| JP2000234020A (ja) * | 1998-12-17 | 2000-08-29 | Nisshinbo Ind Inc | 高分子電解質用ポリマー及びイオン導電性高分子電解質用組成物 |
| JP2002533495A (ja) * | 1998-12-22 | 2002-10-08 | バイエル アクチェンゲゼルシャフト | グリシドールに基づく高分岐ポリオールの製造方法 |
| DE19947631A1 (de) | 1998-12-22 | 2000-06-29 | Bayer Ag | Verfahren zur Herstellung von hochverzweigten Polyolen auf der Basis von Glycidol |
| US6822068B2 (en) | 1998-12-22 | 2004-11-23 | Bayer Aktiengesellschaft | Method for producing highly-branched glycidol-based polyols |
| KR100823972B1 (ko) * | 2001-03-26 | 2008-04-22 | 닛신보세키 가부시키 가이샤 | 이온성 액체, 축전 디바이스용 전해질염, 축전 디바이스용전해액, 전기 2중층 캐패시터, 및 2차 전지 |
| DE10211664A1 (de) * | 2002-03-15 | 2003-10-02 | Hyperpolymers Gmbh | Verfahren zur Herstellung hochverzweigter Polymere |
| JP4198935B2 (ja) * | 2002-05-13 | 2008-12-17 | 新日鐵化学株式会社 | 二官能性エポキシ樹脂及びエポキシ樹脂組成物 |
| JP4540482B2 (ja) * | 2002-11-28 | 2010-09-08 | ダイセル化学工業株式会社 | ポリグリセリン、ポリグリセリン脂肪酸エステル、それらの製造方法 |
| US6974728B2 (en) * | 2003-12-08 | 2005-12-13 | Intel Corporation | Encapsulant mixture having a polymer bound catalyst |
| US7985424B2 (en) * | 2004-04-20 | 2011-07-26 | Dendritic Nanotechnologies Inc. | Dendritic polymers with enhanced amplification and interior functionality |
| US7300993B2 (en) * | 2004-06-03 | 2007-11-27 | Shell Oil Company | Process for the preparation of polyether polyols |
| DE602004011919T2 (de) * | 2004-07-15 | 2009-02-26 | Agfa Graphics N.V. | Neue Polymerisationsinitiatoren |
| US7795324B2 (en) * | 2004-07-15 | 2010-09-14 | Agfa Graphics, N.V. | Radiation curable compositions |
| ES2397531T3 (es) | 2005-12-09 | 2013-03-07 | Kao Corporation | Procedimiento de producción de derivado de poligliceril éter |
| HUE044019T2 (hu) | 2008-09-02 | 2019-09-30 | Construction Research & Technology Gmbh | Eljárás lágyítószert tartalmazó, keményedést gyorsító készítmény elõállítására |
| CN102630245B (zh) | 2009-11-27 | 2014-10-08 | 巴斯夫欧洲公司 | 生产含聚合物涂层的方法 |
-
2010
- 2010-06-30 EP EP10730144.2A patent/EP2448994B1/de not_active Not-in-force
- 2010-06-30 WO PCT/EP2010/059253 patent/WO2011000854A1/de not_active Ceased
- 2010-06-30 US US13/380,470 patent/US9096713B2/en not_active Expired - Fee Related
- 2010-06-30 JP JP2012518893A patent/JP5650211B2/ja not_active Expired - Fee Related
- 2010-06-30 KR KR1020127002309A patent/KR20120047921A/ko not_active Ceased
- 2010-06-30 CN CN201080029230.0A patent/CN102471476B/zh not_active Expired - Fee Related
- 2010-06-30 SG SG2011093721A patent/SG176903A1/en unknown
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|---|---|
| CN102471476B (zh) | 2014-05-21 |
| CN102471476A (zh) | 2012-05-23 |
| US9096713B2 (en) | 2015-08-04 |
| EP2448994A1 (de) | 2012-05-09 |
| EP2448994B1 (de) | 2013-08-14 |
| US20120101308A1 (en) | 2012-04-26 |
| JP2012531511A (ja) | 2012-12-10 |
| SG176903A1 (en) | 2012-01-30 |
| WO2011000854A1 (de) | 2011-01-06 |
| KR20120047921A (ko) | 2012-05-14 |
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