CA2612547C - Isotactic specific catalyst for direct production of highly isotactic poly(propylene oxide) or highly isotactic poly(butylene oxide) - Google Patents
Isotactic specific catalyst for direct production of highly isotactic poly(propylene oxide) or highly isotactic poly(butylene oxide) Download PDFInfo
- Publication number
- CA2612547C CA2612547C CA2612547A CA2612547A CA2612547C CA 2612547 C CA2612547 C CA 2612547C CA 2612547 A CA2612547 A CA 2612547A CA 2612547 A CA2612547 A CA 2612547A CA 2612547 C CA2612547 C CA 2612547C
- Authority
- CA
- Canada
- Prior art keywords
- isotactic
- catalyst
- salph
- ppo
- poly
- 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
- -1 poly(propylene oxide) Polymers 0.000 title claims abstract description 45
- 239000003054 catalyst Substances 0.000 title claims description 47
- 229920001451 polypropylene glycol Polymers 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003446 ligand Substances 0.000 claims abstract description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 28
- 230000000977 initiatory effect Effects 0.000 claims abstract description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 18
- 238000005194 fractionation Methods 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 150000002924 oxiranes Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 239000002262 Schiff base Substances 0.000 claims description 4
- 150000004753 Schiff bases Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000004220 aggregation Methods 0.000 claims description 2
- 230000002776 aggregation Effects 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000004809 Teflon Substances 0.000 description 8
- 229920006362 Teflon® Polymers 0.000 description 8
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- POJVJAYCXBJSCY-UHFFFAOYSA-N 2,4-ditert-butyl-6-[[2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=NC=2C(=CC=CC=2)N=CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O POJVJAYCXBJSCY-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- RRIQVLZDOZPJTH-UHFFFAOYSA-N 3,5-di-tert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=C(O)C(C(C)(C)C)=C1 RRIQVLZDOZPJTH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001443715 Fusarium oxysporum f. sp. conglutinans Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910008046 SnC14 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C08G65/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69223705P | 2005-06-21 | 2005-06-21 | |
| US60/692,237 | 2005-06-21 | ||
| US11/454,945 US7399822B2 (en) | 2005-06-21 | 2006-06-19 | Isotactic specific catalyst for direct production of highly isotactic poly (propylene oxide) or highly isotactic poly (butylene oxide) |
| US11/454,945 | 2006-06-19 | ||
| PCT/US2006/023888 WO2007002023A2 (en) | 2005-06-21 | 2006-06-20 | Isotactic specific catalyst for direct production of highly isotactic poly (propylene oxide) or highly isotactic poly (butylene oxide) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2612547A1 CA2612547A1 (en) | 2007-01-04 |
| CA2612547C true CA2612547C (en) | 2015-03-17 |
Family
ID=37568467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2612547A Expired - Fee Related CA2612547C (en) | 2005-06-21 | 2006-06-20 | Isotactic specific catalyst for direct production of highly isotactic poly(propylene oxide) or highly isotactic poly(butylene oxide) |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US7399822B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1901845A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5113045B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2612547C (cg-RX-API-DMAC7.html) |
| WO (1) | WO2007002023A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8093351B2 (en) * | 2006-08-24 | 2012-01-10 | Cornell Research Foundation, Inc. | Copolymerization of propylene oxide and carbon dioxide and homopolymerization of propylene oxide |
| JP5349806B2 (ja) * | 2007-01-30 | 2013-11-20 | 三洋化成工業株式会社 | ウレタン樹脂組成物 |
| EP2195305A2 (en) | 2007-08-17 | 2010-06-16 | Cornell Research Foundation, Inc. | Isoselective polymerization of epoxides |
| JP5334424B2 (ja) * | 2008-02-15 | 2013-11-06 | 住友化学株式会社 | 安定化ポリ（アルキレンオキシド）の製造方法 |
| PL2966108T3 (pl) | 2008-08-22 | 2021-08-23 | Saudi Aramco Technologies Company | Katalizatory i sposoby syntezy polimerów |
| KR20220018610A (ko) | 2008-09-08 | 2022-02-15 | 사우디 아람코 테크놀로지스 컴퍼니 | 폴리카보네이트 폴리올 조성물 |
| CN101412809B (zh) * | 2008-11-28 | 2011-04-27 | 大连理工大学 | 用于合成聚碳酸酯的单活性点催化剂 |
| WO2010075232A1 (en) | 2008-12-23 | 2010-07-01 | Novomer, Inc. | Tunable polymer compositions |
| US8389660B1 (en) | 2009-06-10 | 2013-03-05 | The Florida State University Research Foundation | Polyolefins having reduced crystallinity |
| JP2011057966A (ja) | 2009-08-12 | 2011-03-24 | Sumitomo Chemical Co Ltd | 高分子量のアイソタクチックポリ（アルキレンオキシド）及びそれを製造する方法 |
| EP2616513B1 (en) | 2010-09-14 | 2019-11-06 | Saudi Aramco Technologies Company | Catalysts and methods for polymer synthesis |
| ES2947327T3 (es) * | 2010-11-23 | 2023-08-04 | Saudi Aramco Tech Co | Composiciones de poli(poliol de carbonato) |
| WO2012166889A2 (en) | 2011-05-31 | 2012-12-06 | Cornell University | Polyethers, methods of making same, and uses thereof |
| EP2734532B1 (en) | 2011-07-18 | 2019-05-01 | Saudi Aramco Technologies Company | Metal complexes |
| KR20240006081A (ko) | 2011-07-25 | 2024-01-12 | 사우디 아람코 테크놀로지스 컴퍼니 | 폴리우레탄에 이용하기 위한 지방족 폴리카보네이트 |
| JP2014529589A (ja) | 2011-08-08 | 2014-11-13 | ノボマー， インコーポレイテッド | ポリマー合成のための触媒および方法 |
| KR101945168B1 (ko) | 2011-11-04 | 2019-02-07 | 사우디 아람코 테크놀로지스 컴퍼니 | 이산화탄소와 에폭사이드의 공중합용의 금속 착체 |
| JP6313305B2 (ja) * | 2012-08-24 | 2018-04-18 | サウジ アラムコ テクノロジーズ カンパニー | 金属錯体 |
| US9512259B2 (en) | 2012-11-07 | 2016-12-06 | Novomer, Inc. | High strength polyurethane foam compositions and methods |
| US20140275433A1 (en) * | 2013-03-14 | 2014-09-18 | Exxonmobil Research And Engineering Company | Amination of polymers terminated with aldehyde group and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes |
| CN109054011B (zh) * | 2018-07-16 | 2021-01-08 | 中国科学院长春应用化学研究所 | 一种席夫碱钴化合物、其制备方法及聚碳酸酯的制备方法 |
| WO2020028606A1 (en) | 2018-08-02 | 2020-02-06 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| TW202302704A (zh) | 2021-06-23 | 2023-01-16 | 沙烏地阿拉伯商沙烏地阿美科技公司 | 多元醇組合物及方法 |
| EP4626445A1 (en) * | 2022-12-02 | 2025-10-08 | University of Maryland, Baltimore | Gallium-salophen antimicrobial compounds and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2706181A (en) * | 1952-06-05 | 1955-04-12 | Dow Chemical Co | Catalysts for the polymerization of olefin oxides |
| US4962281A (en) * | 1985-12-13 | 1990-10-09 | The Dow Chemical Company | Synthesis of stereoregular poly(propylene oxide) |
| US6262278B1 (en) * | 1995-03-14 | 2001-07-17 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| DE60116295D1 (de) * | 2000-05-24 | 2006-02-02 | Rstech Co | Verfahren zur herstellung chiraler verbindungen aus racemischen epoxiden unter verwendung von chiralen salenkatalysatoren |
| JP2004315588A (ja) * | 2003-04-11 | 2004-11-11 | Sanyo Chem Ind Ltd | ヘテロ環状化合物の開環重合用触媒 |
-
2006
- 2006-06-19 US US11/454,945 patent/US7399822B2/en not_active Expired - Fee Related
- 2006-06-20 JP JP2008518292A patent/JP5113045B2/ja not_active Expired - Fee Related
- 2006-06-20 EP EP06785143.6A patent/EP1901845A4/en not_active Withdrawn
- 2006-06-20 CA CA2612547A patent/CA2612547C/en not_active Expired - Fee Related
- 2006-06-20 WO PCT/US2006/023888 patent/WO2007002023A2/en not_active Ceased
-
2008
- 2008-06-12 US US12/155,962 patent/US8026317B2/en not_active Expired - Fee Related
-
2011
- 2011-08-30 US US13/221,631 patent/US20110313128A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7399822B2 (en) | 2008-07-15 |
| JP5113045B2 (ja) | 2013-01-09 |
| EP1901845A4 (en) | 2014-11-19 |
| JP2008546785A (ja) | 2008-12-25 |
| US8026317B2 (en) | 2011-09-27 |
| US20060293501A1 (en) | 2006-12-28 |
| CA2612547A1 (en) | 2007-01-04 |
| EP1901845A2 (en) | 2008-03-26 |
| WO2007002023A2 (en) | 2007-01-04 |
| US20080262164A1 (en) | 2008-10-23 |
| US20110313128A1 (en) | 2011-12-22 |
| WO2007002023A3 (en) | 2007-11-29 |
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