DE10027907A1 - Verfahren zur Herstellung von aliphatischen Oligocarbanatdiolen - Google Patents
Verfahren zur Herstellung von aliphatischen OligocarbanatdiolenInfo
- Publication number
- DE10027907A1 DE10027907A1 DE10027907A DE10027907A DE10027907A1 DE 10027907 A1 DE10027907 A1 DE 10027907A1 DE 10027907 A DE10027907 A DE 10027907A DE 10027907 A DE10027907 A DE 10027907A DE 10027907 A1 DE10027907 A1 DE 10027907A1
- Authority
- DE
- Germany
- Prior art keywords
- dmc
- diols
- stage
- reaction
- oligocarbonate
- 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.)
- Withdrawn
Links
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 title claims abstract description 350
- 150000002009 diols Chemical class 0.000 title claims abstract description 113
- 238000000034 method Methods 0.000 title claims abstract description 85
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 76
- -1 aliphatic diols Chemical class 0.000 title claims abstract description 47
- 230000008569 process Effects 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 12
- 238000000576 coating method Methods 0.000 title claims description 5
- 239000000853 adhesive Substances 0.000 title claims description 4
- 230000001070 adhesive effect Effects 0.000 title claims description 4
- 239000004033 plastic Substances 0.000 title claims description 4
- 229920003023 plastic Polymers 0.000 title claims description 4
- 239000000835 fiber Substances 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 263
- 239000000203 mixture Substances 0.000 claims abstract description 125
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 239000000047 product Substances 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 238000013459 approach Methods 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 21
- 238000005809 transesterification reaction Methods 0.000 claims description 21
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 16
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 16
- 238000012937 correction Methods 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 239000011261 inert gas Substances 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 239000011527 polyurethane coating Substances 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 238000007172 homogeneous catalysis Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 229940057952 methanol Drugs 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003345 natural gas Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229920001748 polybutylene Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims 2
- 239000004575 stone Substances 0.000 claims 2
- GJAARPKBDFKHFS-UHFFFAOYSA-N Gerin Natural products COC(=O)C(=C)C1CC2C(=C)C(=O)C=CC2(C)CC1OC(=O)C GJAARPKBDFKHFS-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000007210 heterogeneous catalysis Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000013008 moisture curing Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000010936 titanium Substances 0.000 description 36
- 230000035484 reaction time Effects 0.000 description 32
- 229910052719 titanium Inorganic materials 0.000 description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 13
- 238000005086 pumping Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- NGCDGPPKVSZGRR-UHFFFAOYSA-J 1,4,6,9-tetraoxa-5-stannaspiro[4.4]nonane-2,3,7,8-tetrone Chemical class [Sn+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O NGCDGPPKVSZGRR-UHFFFAOYSA-J 0.000 description 1
- GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- YZDAAZDHEWALAB-UHFFFAOYSA-N 2,3,5-trimethylhexane-1,6-diol Chemical compound OCC(C)CC(C)C(C)CO YZDAAZDHEWALAB-UHFFFAOYSA-N 0.000 description 1
- XACKQJURAZIUES-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diol Chemical compound OCC(C)CC(C)(C)CCO XACKQJURAZIUES-UHFFFAOYSA-N 0.000 description 1
- ACOQOLIJGGKILA-UHFFFAOYSA-N 2-methylpentane-1,1-diol Chemical compound CCCC(C)C(O)O ACOQOLIJGGKILA-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 229910000831 Steel Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical class [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Steroid Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10027907A DE10027907A1 (de) | 2000-06-06 | 2000-06-06 | Verfahren zur Herstellung von aliphatischen Oligocarbanatdiolen |
| EP01955289A EP1292630B1 (de) | 2000-06-06 | 2001-05-25 | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen |
| CA2411709A CA2411709C (en) | 2000-06-06 | 2001-05-25 | Method for producing aliphatic oligocarbonate diols |
| AU2001277493A AU2001277493A1 (en) | 2000-06-06 | 2001-05-25 | Method for producing aliphatic oligocarbonate diols |
| AT01955289T ATE263797T1 (de) | 2000-06-06 | 2001-05-25 | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen |
| PT01955289T PT1292630E (pt) | 2000-06-06 | 2001-05-25 | Processo para preparacao de oligocarbonatodiois alifaticos |
| DE50101922T DE50101922D1 (de) | 2000-06-06 | 2001-05-25 | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen |
| HK04101886.1A HK1059089B (en) | 2000-06-06 | 2001-05-25 | Method for producing aliphatic oligocarbonate diols |
| PCT/EP2001/005966 WO2001094444A1 (de) | 2000-06-06 | 2001-05-25 | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen |
| US10/297,542 US6833433B1 (en) | 2000-06-06 | 2001-05-25 | Method for producing aliphatic oligocarbonate diols |
| ES01955289T ES2218433T3 (es) | 2000-06-06 | 2001-05-25 | Procedimiento para la fabricacion de oligocarbonatodioles alifaticos. |
| CNB018135447A CN1250604C (zh) | 2000-06-06 | 2001-05-25 | 生产脂肪族低聚碳酸酯二醇的方法 |
| JP2002501991A JP2003535936A (ja) | 2000-06-06 | 2001-05-25 | 脂肪族オリゴカーボネートジオールの製造法 |
| TW90113635A TW575603B (en) | 2000-06-06 | 2001-06-06 | Process for the production of aliphatic oligocarbonate diols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10027907A DE10027907A1 (de) | 2000-06-06 | 2000-06-06 | Verfahren zur Herstellung von aliphatischen Oligocarbanatdiolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10027907A1 true DE10027907A1 (de) | 2001-12-13 |
Family
ID=7644813
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10027907A Withdrawn DE10027907A1 (de) | 2000-06-06 | 2000-06-06 | Verfahren zur Herstellung von aliphatischen Oligocarbanatdiolen |
| DE50101922T Expired - Lifetime DE50101922D1 (de) | 2000-06-06 | 2001-05-25 | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50101922T Expired - Lifetime DE50101922D1 (de) | 2000-06-06 | 2001-05-25 | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6833433B1 (enExample) |
| EP (1) | EP1292630B1 (enExample) |
| JP (1) | JP2003535936A (enExample) |
| CN (1) | CN1250604C (enExample) |
| AT (1) | ATE263797T1 (enExample) |
| AU (1) | AU2001277493A1 (enExample) |
| CA (1) | CA2411709C (enExample) |
| DE (2) | DE10027907A1 (enExample) |
| ES (1) | ES2218433T3 (enExample) |
| PT (1) | PT1292630E (enExample) |
| TW (1) | TW575603B (enExample) |
| WO (1) | WO2001094444A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6767986B2 (en) | 2002-04-29 | 2004-07-27 | Bayer Aktiengesellschaft | Production and use of high molecular weight aliphatic polycarbonates |
| EP1520869A1 (de) * | 2003-09-19 | 2005-04-06 | Bayer MaterialScience AG | Verfahren zur Herstellung von aliphatischen Oligocarbonatpolyolen |
| WO2013076099A1 (de) | 2011-11-24 | 2013-05-30 | Bayer Intellectual Property Gmbh | Herstellung und verwendung von hochmolekularen aliphatischen polycarbonaten |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10343471A1 (de) * | 2003-09-19 | 2005-05-12 | Bayer Materialscience Ag | Verfahren zur Herstellung von aliphatischen Oligocarbonatdiolen |
| JP4604531B2 (ja) * | 2004-03-23 | 2011-01-05 | 宇部興産株式会社 | 環状カーボネート類及びオキセタン類の製造方法。 |
| DE102004031900A1 (de) * | 2004-07-01 | 2006-02-16 | Bayer Materialscience Ag | Oligocarbonatpolyole mit endständig sekundären Hydroxylgruppen |
| DE102004054632A1 (de) * | 2004-11-11 | 2006-05-18 | Basf Ag | Polymerblends aus Polyestern und linearen oligomeren Polycarbonaten |
| DE102005026863A1 (de) * | 2005-06-10 | 2006-12-14 | Bayer Materialscience Ag | Oligocarbonat-haltige Beschichtungsmittel für kratzfeste Decklacke |
| JP5304003B2 (ja) * | 2008-04-11 | 2013-10-02 | 日本ポリウレタン工業株式会社 | ポリカーボネートポリオールの製造方法 |
| CN101643542B (zh) * | 2008-08-05 | 2012-01-11 | 中国科学院化学研究所 | 一种高分子量的脂肪族聚碳酸酯的制备方法 |
| CN103987692B (zh) * | 2011-12-07 | 2016-06-22 | 国际壳牌研究有限公司 | 生产芳族碳酸酯的方法 |
| JP2013216841A (ja) * | 2012-04-12 | 2013-10-24 | Ube Industries Ltd | ポリカーボネートジオール及びその製造方法 |
| CN103923307B (zh) * | 2014-05-05 | 2015-08-12 | 李亮 | 聚碳酸酯二醇的制备方法 |
| BR112017024762A2 (pt) * | 2015-05-21 | 2018-07-31 | Basf Corp | ?processo para preparar um policarbonato poliol hiper-ramificado e policarbonato poliol hiper- ramificado? |
| CN109957101B (zh) * | 2017-12-21 | 2020-07-28 | 万华化学集团股份有限公司 | 一种聚碳酸酯多元醇及其合成方法和应用 |
| CN109107207B (zh) * | 2018-07-18 | 2021-07-23 | 万华化学集团股份有限公司 | 一种带有外循环系统的反应精馏装置及其应用 |
| CN110951031B (zh) * | 2019-12-15 | 2021-12-17 | 安徽匠星联创新材料科技有限公司 | 一种高耐水解性聚氨酯阻尼材料及其制备方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2210817A (en) | 1939-04-19 | 1940-08-06 | Du Pont | Superpolycarbonate |
| DE857948C (de) | 1943-12-25 | 1952-12-04 | Basf Ag | Verfahren zur Herstellung von neutralen Estern der Kohlensaeure |
| US2787632A (en) | 1954-07-07 | 1957-04-02 | Columbia Southern Chem Corp | Polycarbonates |
| DE1568248A1 (de) | 1966-02-11 | 1970-02-05 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Carbonatgruppen enthaltenden Dihydroxyverbindungen |
| DE1694080B1 (de) | 1966-10-13 | 1971-09-30 | Bayer Ag | Verfahren zur herstellung von vernetzten polyurethanen auf grundlage von hydroxylpolykohlensaeureestern |
| CH525920A (de) | 1969-03-28 | 1972-07-31 | Bayer Ag | Verfahren zur Herstellung difunktioneller aliphatischer endständige Hydroxylgruppen aufweisender Polycarbonate |
| FR2294199A1 (fr) | 1974-12-11 | 1976-07-09 | Poudres & Explosifs Ste Nale | Procede perfectionne de preparation de polycarbonates en deux etapes |
| US4105641A (en) | 1975-05-27 | 1978-08-08 | Bayer Aktiengesellschaft | Process for the preparation of aliphatic polycarbonates and polyurethanes therefrom |
| US4463141A (en) | 1981-11-30 | 1984-07-31 | E. I. Du Pont De Nemours And Company | Polyether carbonate diols and polyurethanes prepared therefrom |
| DE3717060A1 (de) | 1987-05-21 | 1988-12-01 | Bayer Ag | Polyether-polycarbonat-diole, ihre herstellung und verwendung als ausgangsprodukte fuer polyurethankunststoffe |
| EP0358555A3 (en) | 1988-09-06 | 1991-05-08 | Daicel Chemical Industries, Ltd. | Polycarbonatediol composition and polyurethane resin |
| IT1227136B (it) | 1988-10-14 | 1991-03-19 | Enichem Sintesi | Policarbonati copoliesteri dioli, procedimento per la loro produzione e loro impiego. |
| JPH02284918A (ja) * | 1989-04-27 | 1990-11-22 | Mitsui Petrochem Ind Ltd | 脂肪族ポリカーボネートジオールの製造方法 |
| JPH04239024A (ja) * | 1991-01-11 | 1992-08-26 | Asahi Chem Ind Co Ltd | 末端ヒドロキシル基を有するポリカーボネートの製法 |
| US5171830A (en) * | 1991-08-16 | 1992-12-15 | Arco Chemical Technology, L.P. | Catalytic process for the preparation of polyalkylene carbonates |
| IT1251489B (it) * | 1991-09-17 | 1995-05-15 | Enichem Sintesi | Policarbonati dioloterminati |
| IT1269916B (it) | 1994-03-25 | 1997-04-16 | Enichem Spa | Procedimento migliorato per la sintesi di dimetilcarbonato |
| US5703196A (en) * | 1994-04-08 | 1997-12-30 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polycarbonate having terminal hydroxyl groups |
| JP3528997B2 (ja) * | 1995-12-15 | 2004-05-24 | 日本ジーイープラスチックス株式会社 | ポリカーボネートの製造方法 |
| IT1283314B1 (it) | 1996-03-28 | 1998-04-16 | Enichem Spa | Processo per la preparazione di policarbonati copolieteri polioli |
| IT1283315B1 (it) | 1996-03-28 | 1998-04-16 | Enichem Spa | Processo a due stadi per la preparazione di policarbonati copolieteridioli. |
| JPH10251398A (ja) * | 1997-03-14 | 1998-09-22 | Ube Ind Ltd | ポリカーボネートジオールの製造法 |
| DE19829593A1 (de) * | 1998-07-02 | 2000-01-05 | Henkel Kgaa | Verfahren zur Herstellung von Verbindungen mit terminalen OH-Gruppen |
| DE19900554A1 (de) * | 1999-01-09 | 2000-07-13 | Bayer Ag | Verfahren zur Herstellung von aliphatischen Oligocarbonatdiolen aus Dimethylcarbonat und aliphatischen Diolen |
-
2000
- 2000-06-06 DE DE10027907A patent/DE10027907A1/de not_active Withdrawn
-
2001
- 2001-05-25 AT AT01955289T patent/ATE263797T1/de not_active IP Right Cessation
- 2001-05-25 WO PCT/EP2001/005966 patent/WO2001094444A1/de not_active Ceased
- 2001-05-25 JP JP2002501991A patent/JP2003535936A/ja active Pending
- 2001-05-25 EP EP01955289A patent/EP1292630B1/de not_active Expired - Lifetime
- 2001-05-25 US US10/297,542 patent/US6833433B1/en not_active Expired - Lifetime
- 2001-05-25 DE DE50101922T patent/DE50101922D1/de not_active Expired - Lifetime
- 2001-05-25 CA CA2411709A patent/CA2411709C/en not_active Expired - Fee Related
- 2001-05-25 PT PT01955289T patent/PT1292630E/pt unknown
- 2001-05-25 CN CNB018135447A patent/CN1250604C/zh not_active Expired - Fee Related
- 2001-05-25 AU AU2001277493A patent/AU2001277493A1/en not_active Abandoned
- 2001-05-25 ES ES01955289T patent/ES2218433T3/es not_active Expired - Lifetime
- 2001-06-06 TW TW90113635A patent/TW575603B/zh not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6767986B2 (en) | 2002-04-29 | 2004-07-27 | Bayer Aktiengesellschaft | Production and use of high molecular weight aliphatic polycarbonates |
| EP1520869A1 (de) * | 2003-09-19 | 2005-04-06 | Bayer MaterialScience AG | Verfahren zur Herstellung von aliphatischen Oligocarbonatpolyolen |
| KR101124906B1 (ko) * | 2003-09-19 | 2012-03-27 | 바이엘 머티리얼사이언스 아게 | 지방족 올리고카르보네이트 폴리올의 제법 |
| WO2013076099A1 (de) | 2011-11-24 | 2013-05-30 | Bayer Intellectual Property Gmbh | Herstellung und verwendung von hochmolekularen aliphatischen polycarbonaten |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1292630A1 (de) | 2003-03-19 |
| WO2001094444A1 (de) | 2001-12-13 |
| TW575603B (en) | 2004-02-11 |
| AU2001277493A1 (en) | 2001-12-17 |
| US6833433B1 (en) | 2004-12-21 |
| PT1292630E (pt) | 2004-07-30 |
| ES2218433T3 (es) | 2004-11-16 |
| JP2003535936A (ja) | 2003-12-02 |
| HK1059089A1 (en) | 2004-06-18 |
| CN1250604C (zh) | 2006-04-12 |
| DE50101922D1 (de) | 2004-05-13 |
| CA2411709A1 (en) | 2001-12-13 |
| CN1444618A (zh) | 2003-09-24 |
| EP1292630B1 (de) | 2004-04-07 |
| ATE263797T1 (de) | 2004-04-15 |
| CA2411709C (en) | 2010-02-16 |
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| Date | Code | Title | Description |
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| 8139 | Disposal/non-payment of the annual fee |