KR101404702B1 - 에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법 - Google Patents
에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법 Download PDFInfo
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- KR101404702B1 KR101404702B1 KR1020110020143A KR20110020143A KR101404702B1 KR 101404702 B1 KR101404702 B1 KR 101404702B1 KR 1020110020143 A KR1020110020143 A KR 1020110020143A KR 20110020143 A KR20110020143 A KR 20110020143A KR 101404702 B1 KR101404702 B1 KR 101404702B1
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- atom
- alkyl
- halogen
- nitrogen
- oxygen
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 82
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 41
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 41
- 229920001577 copolymer Polymers 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 2
- -1 epoxide compound Chemical class 0.000 claims abstract description 78
- 239000003054 catalyst Substances 0.000 claims abstract description 55
- 229910052751 metal Inorganic materials 0.000 claims abstract description 28
- 239000002184 metal Substances 0.000 claims abstract description 28
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 229910052717 sulfur Inorganic materials 0.000 claims description 58
- 229910052698 phosphorus Inorganic materials 0.000 claims description 56
- 229910052710 silicon Inorganic materials 0.000 claims description 56
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
- 239000011574 phosphorus Substances 0.000 claims description 32
- 239000010703 silicon Substances 0.000 claims description 32
- 239000011593 sulfur Substances 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 26
- 125000004434 sulfur atom Chemical group 0.000 claims description 26
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- 125000004437 phosphorous atom Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 150000001450 anions Chemical class 0.000 claims description 14
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052752 metalloid Inorganic materials 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 5
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 description 20
- 238000007334 copolymerization reaction Methods 0.000 description 15
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 12
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- 238000006116 polymerization reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 229920000379 polypropylene carbonate Polymers 0.000 description 4
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000012648 alternating copolymerization Methods 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- SFJRUJUEMVAZLM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxymethyl]oxirane Chemical compound CC(C)(C)OCC1CO1 SFJRUJUEMVAZLM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
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- 125000001033 ether group Chemical group 0.000 description 2
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- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
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- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
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- VLJLXEKIAALSJE-UHFFFAOYSA-N 13-oxabicyclo[10.1.0]tridecane Chemical compound C1CCCCCCCCCC2OC21 VLJLXEKIAALSJE-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
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- NQFUSWIGRKFAHK-BDNRQGISSA-N alpha-Pinene epoxide Natural products C([C@@H]1O[C@@]11C)[C@@H]2C(C)(C)[C@H]1C2 NQFUSWIGRKFAHK-BDNRQGISSA-N 0.000 description 1
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- XTUSLLYSMVWGPS-UHFFFAOYSA-N carbonic acid;cyclohexene Chemical compound OC(O)=O.C1CCC=CC1 XTUSLLYSMVWGPS-UHFFFAOYSA-N 0.000 description 1
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- COCAUCFPFHUGAA-MGNBDDOMSA-N n-[3-[(1s,7s)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=C(F)C([C@@]23N=C(SCC[C@@H]2C3)N)=CC=1NC(=O)C1=CC=C(Cl)C=N1 COCAUCFPFHUGAA-MGNBDDOMSA-N 0.000 description 1
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- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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Images
Classifications
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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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Toxicology (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (7)
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| KR1020110020143A KR101404702B1 (ko) | 2011-03-08 | 2011-03-08 | 에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법 |
| TW101106186A TW201242990A (en) | 2011-03-08 | 2012-02-24 | Method for preparing carbon dioxide/epoxide copolymers containing ether linkages |
| US13/406,065 US8871898B2 (en) | 2011-03-08 | 2012-02-27 | Method for preparing carbon dioxide/epoxide copolymers containing ether linkages |
| PCT/KR2012/001528 WO2012121508A2 (en) | 2011-03-08 | 2012-02-29 | Method for preparing carbon dioxide/epoxide copolymers containing ether linkages |
| JP2013557642A JP2014508836A (ja) | 2011-03-08 | 2012-02-29 | エーテル結合単位体を含有する二酸化炭素/エポキシド共重合体の製造方法 |
| CN201280011890.5A CN103403059B (zh) | 2011-03-08 | 2012-02-29 | 制备包含醚键的二氧化碳/环氧化物共聚物的方法 |
| EP12754366.8A EP2683757A4 (en) | 2011-03-08 | 2012-02-29 | Method for preparing carbon dioxide/epoxide copolymers containing ether linkages |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020110020143A KR101404702B1 (ko) | 2011-03-08 | 2011-03-08 | 에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법 |
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| KR20120102183A KR20120102183A (ko) | 2012-09-18 |
| KR101404702B1 true KR101404702B1 (ko) | 2014-06-17 |
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| EP (1) | EP2683757A4 (enExample) |
| JP (1) | JP2014508836A (enExample) |
| KR (1) | KR101404702B1 (enExample) |
| CN (1) | CN103403059B (enExample) |
| TW (1) | TW201242990A (enExample) |
| WO (1) | WO2012121508A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101449127B1 (ko) * | 2012-09-28 | 2014-10-13 | 부산대학교 산학협력단 | 폴리카보네이트 수지 조성물 및 그 제조 방법 |
| GB201308978D0 (en) | 2013-05-17 | 2013-07-03 | Imp Innovations Ltd | Method for producing polymers and block copolymers |
| WO2016203408A1 (en) | 2015-06-15 | 2016-12-22 | King Abdullah University Of Science And Technology | Use of additives to fine-tune the composition of carbonate units in the polymer formed by copolymerization of co2 with epoxide: application to the synthesis of polycarbonate-based block copolymers and of telechelics |
| GB201514506D0 (en) | 2015-08-14 | 2015-09-30 | Imp Innovations Ltd | Multi-block copolymers |
| GB201515350D0 (en) * | 2015-08-28 | 2015-10-14 | Econic Technologies Ltd | Method for preparing polyols |
| CN105482093B (zh) * | 2016-01-21 | 2017-11-14 | 中国科学院长春应用化学研究所 | 一种二氧化碳‑环氧丙烷改性共聚物及其制备方法和二氧化碳基生物降解地膜 |
| KR102409995B1 (ko) * | 2016-02-26 | 2022-06-15 | 에스케이이노베이션 주식회사 | 폴리(알킬렌 카보네이트)폴리올의 제조방법 |
| CN107793557B (zh) * | 2016-08-31 | 2020-06-09 | 中国石油化工股份有限公司 | 一种蒽醌类聚合物的制备方法和应用 |
| KR101804762B1 (ko) * | 2017-02-16 | 2017-12-05 | 한국과학기술연구원 | 알킬렌 카보네이트 제조용 촉매, 그 제조 방법 및 상기 촉매를 이용한 알킬렌 카보네이트 제조 방법 및 장치 |
| GB201703323D0 (en) * | 2017-03-01 | 2017-04-12 | Econic Tech Ltd | Method for preparing polyols |
| GB201703324D0 (en) * | 2017-03-01 | 2017-04-12 | Econic Tech Ltd | Method for preparing polyether carbonates |
| GB201703331D0 (en) * | 2017-03-01 | 2017-04-12 | Econic Tech Ltd | Method for preparing polycarbonate ether polyols |
| GB201717459D0 (en) * | 2017-10-24 | 2017-12-06 | Econic Tech Limited | Methods for forming polycarbonate ether polyols and high molecular weight polyether carbonates |
| CN108772102B (zh) * | 2018-04-16 | 2021-04-23 | 兰州大学 | 高效催化二氧化碳合成环碳酸酯的杂多金属高效催化剂 |
| GB201814526D0 (en) | 2018-09-06 | 2018-10-24 | Econic Tech Ltd | Methods for forming polycarbonate ether polyols and high molecular weight polyether carbonates |
| CN111303217B (zh) * | 2020-04-03 | 2023-04-11 | 陕西煤业化工技术研究院有限责任公司 | 一种salen型席夫碱改性DMC催化剂的制备及其应用 |
| CN114790285A (zh) * | 2021-01-26 | 2022-07-26 | 万华化学集团股份有限公司 | 一种用于环氧化物连续聚合的诱导体系、诱导剂以及环氧化物连续聚合的方法 |
| GB202115335D0 (en) * | 2021-10-25 | 2021-12-08 | Econic Tech Ltd | Surface-active agent |
| CN113801314B (zh) * | 2021-11-03 | 2023-01-10 | 中国科学院过程工程研究所 | 一种聚碳酸酯的制备方法 |
| CN115612085B (zh) * | 2022-12-05 | 2023-03-31 | 山东联欣环保科技有限公司 | 一种合成二氧化碳基多元共聚物同时联产pc的方法 |
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| US6133402A (en) * | 1998-08-04 | 2000-10-17 | Cornell Research Foundation, Inc. | Polycarbonates made using high activity catalysts |
| US20040220430A1 (en) | 2002-06-14 | 2004-11-04 | Eleveld Michiel Barend | Preparation of a double metal cyanide catalyst |
| US20080167502A1 (en) | 2005-03-10 | 2008-07-10 | Basf Aktiengesellschaft | Method For Producing an Dmc Catalyst |
| WO2008136591A1 (en) | 2007-05-04 | 2008-11-13 | Sk Energy Co., Ltd. | A process for producing polycarbonates and a coordination complex used therefor |
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| US6077978A (en) | 1997-09-17 | 2000-06-20 | Arco Chemical Technology L.P. | Direct polyoxyalkylation of glycerine with double metal cyanide catalysis |
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| DE19817676A1 (de) | 1998-04-21 | 1999-10-28 | Bayer Ag | Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole |
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-
2011
- 2011-03-08 KR KR1020110020143A patent/KR101404702B1/ko active Active
-
2012
- 2012-02-24 TW TW101106186A patent/TW201242990A/zh unknown
- 2012-02-27 US US13/406,065 patent/US8871898B2/en active Active
- 2012-02-29 EP EP12754366.8A patent/EP2683757A4/en not_active Withdrawn
- 2012-02-29 CN CN201280011890.5A patent/CN103403059B/zh active Active
- 2012-02-29 JP JP2013557642A patent/JP2014508836A/ja not_active Withdrawn
- 2012-02-29 WO PCT/KR2012/001528 patent/WO2012121508A2/en not_active Ceased
Patent Citations (4)
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| US6133402A (en) * | 1998-08-04 | 2000-10-17 | Cornell Research Foundation, Inc. | Polycarbonates made using high activity catalysts |
| US20040220430A1 (en) | 2002-06-14 | 2004-11-04 | Eleveld Michiel Barend | Preparation of a double metal cyanide catalyst |
| US20080167502A1 (en) | 2005-03-10 | 2008-07-10 | Basf Aktiengesellschaft | Method For Producing an Dmc Catalyst |
| WO2008136591A1 (en) | 2007-05-04 | 2008-11-13 | Sk Energy Co., Ltd. | A process for producing polycarbonates and a coordination complex used therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103403059B (zh) | 2015-03-25 |
| KR20120102183A (ko) | 2012-09-18 |
| US8871898B2 (en) | 2014-10-28 |
| EP2683757A4 (en) | 2015-04-29 |
| WO2012121508A2 (en) | 2012-09-13 |
| JP2014508836A (ja) | 2014-04-10 |
| EP2683757A2 (en) | 2014-01-15 |
| WO2012121508A3 (en) | 2012-10-26 |
| TW201242990A (en) | 2012-11-01 |
| CN103403059A (zh) | 2013-11-20 |
| US20120232245A1 (en) | 2012-09-13 |
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