KR950704398A - 선택된 금속 화합물 촉매를 이용한 시클릭 에테르의 중합 및 해중합(Polymerization of, and Depolymerization to, Cyclic Ethers Using Selected Metal Compound Catalysts) - Google Patents
선택된 금속 화합물 촉매를 이용한 시클릭 에테르의 중합 및 해중합(Polymerization of, and Depolymerization to, Cyclic Ethers Using Selected Metal Compound Catalysts)Info
- Publication number
- KR950704398A KR950704398A KR1019950701508A KR19950701508A KR950704398A KR 950704398 A KR950704398 A KR 950704398A KR 1019950701508 A KR1019950701508 A KR 1019950701508A KR 19950701508 A KR19950701508 A KR 19950701508A KR 950704398 A KR950704398 A KR 950704398A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- group
- gold
- acid
- rhenium
- Prior art date
Links
- 150000004292 cyclic ethers Chemical class 0.000 title claims 4
- 150000002736 metal compounds Chemical class 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 title 1
- 238000006116 polymerization reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 5
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims abstract 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims abstract 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract 2
- 229920000642 polymer Polymers 0.000 claims abstract 2
- 230000000379 polymerizing effect Effects 0.000 claims abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 8
- 229910052737 gold Inorganic materials 0.000 claims 8
- 239000010931 gold Substances 0.000 claims 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 7
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 7
- 229910052797 bismuth Inorganic materials 0.000 claims 7
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 7
- 229910052735 hafnium Inorganic materials 0.000 claims 7
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 7
- 229910052742 iron Inorganic materials 0.000 claims 7
- 229910052750 molybdenum Inorganic materials 0.000 claims 7
- 239000011733 molybdenum Substances 0.000 claims 7
- 229910052763 palladium Inorganic materials 0.000 claims 7
- 229910052761 rare earth metal Inorganic materials 0.000 claims 7
- 150000002910 rare earth metals Chemical class 0.000 claims 7
- 229910052702 rhenium Inorganic materials 0.000 claims 7
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 7
- 229910052707 ruthenium Inorganic materials 0.000 claims 7
- 229910052712 strontium Inorganic materials 0.000 claims 7
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 7
- 229910052715 tantalum Inorganic materials 0.000 claims 7
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 7
- 229910052718 tin Inorganic materials 0.000 claims 7
- 229910052719 titanium Inorganic materials 0.000 claims 7
- 239000010936 titanium Substances 0.000 claims 7
- 229910052727 yttrium Inorganic materials 0.000 claims 7
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims 7
- 229910052725 zinc Inorganic materials 0.000 claims 7
- 239000011701 zinc Substances 0.000 claims 7
- 229910052726 zirconium Inorganic materials 0.000 claims 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 6
- 150000001450 anions Chemical class 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910052804 chromium Inorganic materials 0.000 claims 6
- 239000011651 chromium Substances 0.000 claims 6
- 229910052706 scandium Inorganic materials 0.000 claims 6
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims 6
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 6
- 229910052721 tungsten Inorganic materials 0.000 claims 6
- 239000010937 tungsten Substances 0.000 claims 6
- 229910052787 antimony Inorganic materials 0.000 claims 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 5
- 229910052785 arsenic Inorganic materials 0.000 claims 5
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 5
- 229910052788 barium Inorganic materials 0.000 claims 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 5
- 229910052793 cadmium Inorganic materials 0.000 claims 5
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 5
- 229910052732 germanium Inorganic materials 0.000 claims 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 5
- 229910052741 iridium Inorganic materials 0.000 claims 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 5
- 229910052753 mercury Inorganic materials 0.000 claims 5
- 229910052758 niobium Inorganic materials 0.000 claims 5
- 239000010955 niobium Chemical group 0.000 claims 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical group [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 5
- 229910052762 osmium Inorganic materials 0.000 claims 5
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 5
- 229910052703 rhodium Inorganic materials 0.000 claims 5
- 239000010948 rhodium Substances 0.000 claims 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 5
- 229910052720 vanadium Inorganic materials 0.000 claims 5
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 4
- 229910052775 Thulium Inorganic materials 0.000 claims 4
- 229910052782 aluminium Inorganic materials 0.000 claims 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 4
- 229910017052 cobalt Inorganic materials 0.000 claims 4
- 239000010941 cobalt Substances 0.000 claims 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 4
- -1 crochet Chemical compound 0.000 claims 4
- 229910052733 gallium Inorganic materials 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229910052738 indium Inorganic materials 0.000 claims 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052697 platinum Inorganic materials 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 229910052709 silver Inorganic materials 0.000 claims 3
- 239000004332 silver Substances 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Chemical group 0.000 claims 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- 229920000570 polyether Polymers 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 239000010703 silicon Substances 0.000 claims 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 2
- 239000011135 tin Chemical group 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- PTYVBEKOPJHZLJ-UHFFFAOYSA-N 2-nitropropanoic acid Chemical compound OC(=O)C(C)[N+]([O-])=O PTYVBEKOPJHZLJ-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 102000011782 Keratins Human genes 0.000 claims 1
- 108010076876 Keratins Proteins 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- DZTHIGRZJZPRDV-LBPRGKRZSA-N N-acetyl-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-LBPRGKRZSA-N 0.000 claims 1
- DZTHIGRZJZPRDV-UHFFFAOYSA-N Nalpha-Acetyltryptophan Natural products C1=CC=C2C(CC(NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 claims 1
- 229920002313 fluoropolymer Polymers 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
- 229940116191 n-acetyltryptophan Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 229920000909 polytetrahydrofuran Polymers 0.000 abstract 1
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
- 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
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- 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
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
- C08G63/58—Cyclic ethers; Cyclic carbonates; Cyclic sulfites ; Cyclic orthoesters
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
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- 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
- C08G65/16—Cyclic ethers having four or more ring atoms
-
- 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
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/20—Tetrahydrofuran
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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Abstract
본 발명은, 옥시란, 옥세탄, 옥세판, 디옥솔란, 트리옥산, 및 테트라히드로퓨란을 선택된 금속 화합물과 접촉시킴으로써 각각의 중합체로 중합시키는 방법에 관한 것이다. 본 발명은 또한 폴리테트라히드로퓨란을 약 100℃내지 약 250℃의 온도에서 선택된 금속 화합물과 접촉시킴으로써 테트라히드로퓨란 단량체로 해중합시키는 방법에 관한 것이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (20)
- 하나 이상의 옥시란, 옥세탄, 테트라히드로퓨란, 옥세판, 1,3-디옥슬란 또는 1,3,5-트리옥산을 일반식이 MZs·Qt인 화합물, 및 물 중에서의 pKa가 6이하인 카르복실산, 카르복실산 무수물 및 아실 할라이드로 구성된 군 중에서 선택된 가속제와 접촉시킴으로써 시클릭 에테르를 중합시키는 방법.(상기식에서, M은 코발트, 비나듐, 비오븀, 텅스텐, 스트론튬, 바륨, 스칸듐, 이트륨, 회토류 금속들, 티타늄, 지르코늄, 하프늄, 크로윰, 몰리브데늄, 탄탈륨, 레늄, 철, 루테늄, 오스뮴, 로듐, 이리듐, 팔라듐, 백금, 은, 금, 아연, 카드륨, 수은, 알루미늄, 갈륨, 인듐, 툴륨, 게르마늄, 주석, 납, 비소, 안티몬 및 비스무트로 구성된 군 중에서 선택된 금속이고; Z중에서 적어도 하나는 일반식 -OS02R5인 음이온(여기에서, R5는 1 내지 12개의 탄소 원자를 가지는 퍼플로로알킬 또는 설포네이트기에 대하여 알파 및 베타 위치에서 있는 탄소 원자가 함께 적어도 4개의 불소 원자에 결합되어 있는 불소화된 중합체의 일부분이다.), 또는 테트라페닐보레이트이고, 나머지의 Z는 옥소 또는 하나 이상의 1가 음이온이며; M이 스트론튬, 바륨, 코발트, 로듐, 이리듐, 팔라듐, 백금, 크로뮴, 아연, 카드뮴 또는 수은 일 때 s는 2이고; M이 스칸튬, 이트륨, 희토류 금속, 비소, 안티몬, 비스무트, 금, 철, 루테늄, 오스뮴, 알루미늄, 갈륨, 인듐, 또는 툴륨일 때 s는 3이며; M이 티타늄, 지르코늄, 하프늄, 몰리브데늄, 게르마늄, 주석, 또는 납일때 s는 4이고; M이 레늄, 바나듐, 니오븀 또는 탄탈륨일 때 s는 -5이며; M이 텅스텐일 때 s는 6이고; Q는 중성 리간드이며; t는 0 또는 1 내지 6의 정수이고; Z의 일부로 존재하는 각 옥소기는 s중 2로 계산된다.)
- 제1항에 있어서, 상기 시클릭 에테르가 상기 테트라히드로퓨란, 옥세판, 1,3-디옥솔란 또는 1,3,5-트리옥산 중의 하나 이상인 것을 특징으로 하는 방법.
- 제2항에 있어서, M이 스트론튬, 바륨, 스칸듐, 이트륨, 희토류 금속들, 티타늄, 지르코늄, 하프늄, 크로뮴, 몰리브데늄, 탄탈륨, 레늄, 철, 루테늄, 오스뮴, 로듐, 이리듐, 팔라듐, 려금, 은, 금, 아연, 카드뮴, 수은, 게르마늄, 주석, 납, 비소, 안티몬 및 비스무트로 구성된 군 중에서 선택된 금속인 것을 특징으로 하는 방법.
- 제3항에 있어서, 상기 시클릭 에테르가 다음의 구조식을 가지는 것을 특징으로 하는 방법.상기식에서, R1, R2, R3및 R4는 각각 독립적으로 수소 또는 1 내지 20개의 탄소 원자를 가지는 하이드로카빌기이고, n은 2 또는 4이다.)
- 제4항에 있어서, n이 2이고, R1, R4및 모든 R2및 R3가 수소인 것을 특징으로 하는 방법.
- 제4항에 있어서, n이 2 이고, R1및 R4는 각각 수소이며, 하나의 R2는 수소이고 다른 하나의 R2는 메틸기이며, R3는 모두 수소인 것을 특징으로 하는 방법.
- 제3항에 있어서, R5가 트리플로로메틸기 또는 퍼플로로알킬기인 것을 특징으로 하는 방법.
- 제5항에 있어서, M이 스트론튬, 스칸듐, 이트륨, 희토류 금속들, 티타늄, 지르코늄, 하프늄, 바나듐, 니오븀, 탄탈륨, 크로뮴, 몰리브데늄, 텅스텐, 레늄, 철, 루테늄, 팔라듐, 구리, 금, 아연, 주석, 비스무트 또는 미쉬메틸인 것을 특징으로 하는 방법.
- 제1항에 있어서, 반응이 약 -8O℃ 내지 약 130℃트의 온도에서 수행되는 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 카르복실산이 트리플로로아세트산, 포름산, 아세트산, 시아노아세트산, 니트로프로피온산, 아크릴산, 메타크릴산, N-아세틸글리신 또는 N-아세틸트립토판인 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 카르복실산 무수물이 아세트산 무수물 또는 트리플로로아세트산 무수물인 것을 특징으로 하는 방법.
- 필수적으로 하나 이상의 일반식-[CHR1CR2R3CR2R3CHR4O]-의 반복 단위로 이루어지는 중합체를 약 100℃ 내지 약 250℃의 온도에서 일반식이 MZs·Qt인 화합물과 접촉시킴으로써 폴리에테르를 테트라히드로퓨란으로 해중합하는 방법.(상기 식에서, R1, R2, R3 및 R4는 각각 독립적으로 수소 또는 1 내지 20개의 탄소 원자를 가지고 하이드로카빌이고; M은 코발트, 바나듐, 니오븀, 텅스텐, 스트론튬, 바륨, 스칸듐, 이트륨, 희토류 금속들, 티타늄, 지르코늄, 하프늄, 크로뮴, 몰리브데늄, 탄탈륨, 레늄, 철, 루테늄, 오스뮴, 로듐, 이리듐, 팔라듐, 백금, 은, 금, 아연, 카드뮴, 수은, 알류미늄, 갈륨, 인듐, 툴륨, 실리콘, 게르마늄, 주석, 납, 비소, 안티몬 및 비스무트로 구성된 군 중에서 선택된 금속이며; Z중에서 적어도 하나는 일반식이 -OS02R5인 음이온(여기에서, R5는 1 내지 12개의 탄소 원자를 가지는 퍼플로로알킬 또는 설포네이트기에 대하여 알파 및 베타 위치에 있는 탄소 원자가 함께 적어도 4개의 불소 원자에 결합되어 있는 불소화된 중합체의 일부분이다.) 또는 테트라페닐보레이트이고, 나머지의 Z는 옥소 또는 하나 이상의 1가 음이온이고; M이 스트론튬, 바륨, 코발트, 로듐, 이리듐, 팔라듐, 백금, 크로뮴, 아연, 카드뮴 또는 수은일 때 s는 2이며; M이 스칸듐, 이트륨, 희토류 금속 비소, 안티몬, 비스무트, 금, 철, 루테늄, 오스뮴, 알루미늄, 갈륨, 인듐 또는 툴륨일 때 s는 3이고; M이 티타늄, 지르코늄, 하프늄, 몰리브데늄, 실리콘, 게르마늄, 주석, 또는 납일 때 s는 4이며; M이 레늄, 바나듐, 니오뮴 또는 탄탈륨일 때 s는 5이고; M이 텅스텐일 때 s는 6이며; Q는 중성 리간드이고; t는 0또는 1 내지 6의 정수이며; Z의 일부로서 존재하는 각옥소기는 s중 2로 계산된다.)
- 제12항에 있어서, R1및 R4가 각각 수소이고 모든 R2및 R3가 수소인 것을 특징으로 하는 방법.
- 제12항에 있어서, R1및 R4는 각각 수소이고, 하나의 R2는 수소이며 다른 하나의 R2는 메틸기이고, R3는 모두 수소인 것을 특징으로 하는 방법.
- 제12항에 있어서, R5가 트리플로로메틸기인 것을 특징으로 하는 방법.
- 제12항에 있어서, 반응이 약 130℃ 내지 약 200℃의 온도에서 수행되는 것을 특징으로 하는 방법.
- 제12항에 있어서, 상기 일반식 MZs·Qt의 화합물이 상기 폴리에테르의 약 1 내지 약 2중량%인 것을 특징으로 하는 방법.
- 제12항에 있어서, M이 스트론륨, 스칸듐, 이트륨, 희토류 금속들, 티타늄, 지르코늄, 하프늄, 바나듐, 니오븀, 탄탈륨, 크로뮴, 몰리브데늄, 텅스텐, 레늄, 철, 루테늄, 팔라듐, 구리, 금, 아연, 주석, 비스무트 또는 미쉬메탈인 것을 특징으로 하는 방법.
- 제1항에 있어서, 모든 Z가 R5가 트리플로로메틸기인 일반식-0S02R5의 음이온인 것을 특징으로 하는 방법.
- 제12항에 있어서, 모든 Z가 R5가 트리플로로메틸기인 일반식-OS02R5의 음이온인 것을 특징으로 하는 방법.※ 참고사항 :최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
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| US96431392A | 1992-10-21 | 1992-10-21 | |
| US07/964313 | 1992-10-21 | ||
| US7/964313 | 1992-10-21 | ||
| US2136893A | 1993-02-23 | 1993-02-23 | |
| US8/021368 | 1993-02-23 | ||
| US08/021368 | 1993-02-23 | ||
| US9324393A | 1993-07-16 | 1993-07-16 | |
| US8/093243 | 1993-07-16 | ||
| US08/093243 | 1993-07-16 | ||
| PCT/US1993/009808 WO1994009055A2 (en) | 1992-10-21 | 1993-10-20 | Polymerization of, and depolymerization to, cyclic ethers using selected metal compound catalysts |
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| KR1020007009496A Division KR100283271B1 (ko) | 1992-10-21 | 2000-08-26 | 선택된 금속 화합물 촉매를 이용한 폴리에테르의 해중합 |
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| KR950704398A true KR950704398A (ko) | 1995-11-20 |
| KR100283272B1 KR100283272B1 (ko) | 2001-03-02 |
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| EP (2) | EP0665859B1 (ko) |
| JP (1) | JP3310292B2 (ko) |
| KR (1) | KR100283272B1 (ko) |
| DE (2) | DE69333518T2 (ko) |
| ES (2) | ES2166765T3 (ko) |
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| WO1995002625A2 (en) * | 1993-07-16 | 1995-01-26 | E.I. Du Pont De Nemours And Company | Polymerization/depolymerization catalyst for polyethers |
| ES2200778T3 (es) * | 1994-10-28 | 2004-03-16 | E.I. Dupont De Nemours And Company | Polimerizacion de eteres ciclicos usando catalizadores de compuestos metalicos seleccionados. |
| US6072021A (en) * | 1997-10-24 | 2000-06-06 | E. I. Du Pont De Nemours And Company | Copolymerization of formaldehyde and cyclic ethers using initiators based upon tetraphenyl borates |
| DE19757709A1 (de) * | 1997-12-23 | 1999-07-01 | Basf Ag | Verfahren zur Herstellung oxalkylierter Amine |
| JP4786847B2 (ja) | 1999-12-17 | 2011-10-05 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリトリメチレンエーテルグリコールおよびそのコポリマーの生成 |
| WO2001044150A2 (en) | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| US6599625B2 (en) | 2001-10-31 | 2003-07-29 | E. I. Du Pont De Nemours And Company | Polyether ester elastomer comprising polytrimethylene ether ester soft segment and trimethylene ester hard segment |
| US6562457B1 (en) | 2001-10-31 | 2003-05-13 | E. I. Du Pont De Nemours And Company | Polyether ester elastomer comprising polytrimethylene ether ester soft segment and tetramethylene ester hard segment |
| DE10215973A1 (de) | 2002-04-11 | 2003-10-23 | Basf Ag | Herstellung von Polyoxymethylen und dafür geeignete Katalysatoren II |
| DE10215978A1 (de) | 2002-04-11 | 2003-10-23 | Basf Ag | Herstellung von Polyoxymethylen und dafür geeignete Katalysatoren |
| US6852823B2 (en) | 2002-08-09 | 2005-02-08 | E. I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea elastomers from polytrimethylene ether glycol |
| AU2003268646A1 (en) * | 2002-10-09 | 2004-05-04 | Mitsubishi Chemical Corporation | Polyurethane resin and elastic polyurethane fiber |
| US8809491B2 (en) | 2009-12-11 | 2014-08-19 | INVISTA North America S.à r.l. | Depolymerization of oligomeric cyclic ethers |
| WO2013092680A1 (en) | 2011-12-22 | 2013-06-27 | Akzo Nobel Chemicals International B.V. | Catalyst used for the production of addition products of epoxides and compounds having active hydrogen atoms |
| ES2772299T3 (es) * | 2014-11-20 | 2020-07-07 | Mitsubishi Chem Corp | Politetrametileno éter glicol, método para su producción, elastómero de poliéster y poliuretano |
| CN114605621B (zh) * | 2022-03-25 | 2024-01-30 | 中国科学院长春应用化学研究所 | 一种氢键给体-硼有机催化剂及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4153786A (en) * | 1977-03-30 | 1979-05-08 | E. I. Du Pont De Nemours And Company | Method for preparing ester end-capped copolyether glycols |
| US4115408A (en) * | 1977-08-05 | 1978-09-19 | E.I. Dupont De Nemours And Company | Conversion of poly(tetramethylene ether) glycol in aqueous effluent stream to tetrahydrofuran |
| JPS61120832A (ja) * | 1984-11-16 | 1986-06-07 | Asahi Chem Ind Co Ltd | ポリアルキレンエ−テルの解重合方法 |
| JPH0794547B2 (ja) * | 1986-04-10 | 1995-10-11 | 三菱化学株式会社 | ポリテトラメチレンエーテルグリコールの改質法 |
| US4721559A (en) * | 1986-10-17 | 1988-01-26 | Olah George A | Boron, aluminum and gallium perfluoro alkanesulfonate and resinsulfonate catalysts |
| JPH07231438A (ja) * | 1994-02-16 | 1995-08-29 | Miharu Tsushin Kk | Ｃａｔｖ用増幅器 |
-
1993
- 1993-10-20 EP EP93924316A patent/EP0665859B1/en not_active Expired - Lifetime
- 1993-10-20 DE DE69333518T patent/DE69333518T2/de not_active Expired - Lifetime
- 1993-10-20 ES ES93924316T patent/ES2166765T3/es not_active Expired - Lifetime
- 1993-10-20 KR KR1019950701508A patent/KR100283272B1/ko not_active IP Right Cessation
- 1993-10-20 WO PCT/US1993/009808 patent/WO1994009055A2/en active IP Right Grant
- 1993-10-20 DE DE69331442T patent/DE69331442T2/de not_active Expired - Lifetime
- 1993-10-20 EP EP00201220A patent/EP1029881B1/en not_active Expired - Lifetime
- 1993-10-20 JP JP51025294A patent/JP3310292B2/ja not_active Expired - Fee Related
- 1993-10-20 ES ES00201220T patent/ES2220334T3/es not_active Expired - Lifetime
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2000
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1029881A3 (en) | 2001-07-04 |
| DE69331442T2 (de) | 2002-10-24 |
| WO1994009055A3 (en) | 1994-07-21 |
| DE69333518D1 (de) | 2004-06-17 |
| DE69331442D1 (de) | 2002-02-14 |
| JP3310292B2 (ja) | 2002-08-05 |
| EP1029881A2 (en) | 2000-08-23 |
| WO1994009055A2 (en) | 1994-04-28 |
| EP0665859A1 (en) | 1995-08-09 |
| HK1027584A1 (en) | 2001-01-19 |
| ES2220334T3 (es) | 2004-12-16 |
| JPH08502531A (ja) | 1996-03-19 |
| DE69333518T2 (de) | 2005-04-07 |
| KR100283272B1 (ko) | 2001-03-02 |
| ES2166765T3 (es) | 2002-05-01 |
| EP1029881B1 (en) | 2004-05-12 |
| EP0665859B1 (en) | 2002-01-09 |
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