TWI252224B - A process for preparing bisphenols - Google Patents
A process for preparing bisphenols Download PDFInfo
- Publication number
- TWI252224B TWI252224B TW090106395A TW90106395A TWI252224B TW I252224 B TWI252224 B TW I252224B TW 090106395 A TW090106395 A TW 090106395A TW 90106395 A TW90106395 A TW 90106395A TW I252224 B TWI252224 B TW I252224B
- Authority
- TW
- Taiwan
- Prior art keywords
- bisphenol
- crystallization
- phenol
- adduct
- preparing
- Prior art date
Links
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 title abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 79
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000013078 crystal Substances 0.000 claims abstract description 38
- 238000002425 crystallisation Methods 0.000 claims description 65
- 230000008025 crystallization Effects 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 10
- 229910052797 bismuth Inorganic materials 0.000 claims description 9
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 229960003742 phenol Drugs 0.000 description 36
- 239000000725 suspension Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000003795 desorption Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 238000011144 upstream manufacturing Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000002079 cooperative effect Effects 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000005501 phase interface Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- -1 thiol compound Chemical class 0.000 description 2
- 241001550224 Apha Species 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 206010011469 Crying Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10015014A DE10015014A1 (de) | 2000-03-27 | 2000-03-27 | Verfahren zur Herstellung von Bisphenolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI252224B true TWI252224B (en) | 2006-04-01 |
Family
ID=7636449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090106395A TWI252224B (en) | 2000-03-27 | 2001-03-20 | A process for preparing bisphenols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6828465B2 (https=) |
| EP (1) | EP1268379B9 (https=) |
| JP (2) | JP5419314B2 (https=) |
| KR (1) | KR100781863B1 (https=) |
| CN (1) | CN1179931C (https=) |
| AU (1) | AU2001248347A1 (https=) |
| BR (1) | BR0109539A (https=) |
| DE (2) | DE10015014A1 (https=) |
| ES (1) | ES2217134T5 (https=) |
| MX (1) | MXPA02009453A (https=) |
| TW (1) | TWI252224B (https=) |
| WO (1) | WO2001072677A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10015014A1 (de) * | 2000-03-27 | 2001-10-04 | Bayer Ag | Verfahren zur Herstellung von Bisphenolen |
| US6703530B2 (en) | 2002-02-28 | 2004-03-09 | General Electric Company | Chemical reactor system and process |
| US7598424B2 (en) * | 2003-03-27 | 2009-10-06 | Mitsui Chemicals, Inc. | Process for production of bisphenol A |
| JP4517656B2 (ja) * | 2004-02-05 | 2010-08-04 | 三菱化学株式会社 | ビスフェノールａの製造方法 |
| DE102004005723A1 (de) * | 2004-02-05 | 2005-08-25 | Bayer Materialscience Ag | Herstellung von Bisphenol A mit verringertem Schwefelgehalt |
| EP2089357B1 (de) * | 2006-12-11 | 2016-09-21 | Basf Se | Verfahren zur herstellung von isocyanaten |
| DE102007001427A1 (de) * | 2007-01-09 | 2008-07-10 | Bayer Materialscience Ag | Kristallisationsverfahren zur Herstellung von Bisphenol A |
| CN101626998B (zh) * | 2007-03-30 | 2013-05-01 | 三菱化学株式会社 | 双酚a的制备方法 |
| DE102007021935A1 (de) * | 2007-05-10 | 2008-11-20 | Bayer Materialscience Ag | Verfahren und Herstellung von Bisphenol A mit verlängerter Standzeit in der Kristallisation |
| JP5655397B2 (ja) * | 2010-07-01 | 2015-01-21 | 三菱化学株式会社 | ビスフェノールａの製造方法 |
| EP3378849B1 (en) * | 2015-11-19 | 2020-07-29 | LG Chem, Ltd. | Bisphenol a preparation apparatus and preparation method |
| US10570076B2 (en) | 2016-07-22 | 2020-02-25 | Sabic Global Technologies B.V. | Method for the continuous manufacture of bisphenol A |
| WO2021037777A1 (en) | 2019-08-27 | 2021-03-04 | Covestro Intellectual Property Gmbh & Co. Kg | Process for preparing bisphenole a (bpa) in the presence of hydroxyacetone |
| WO2022074635A1 (en) | 2020-10-09 | 2022-04-14 | Sabic Global Technologies B.V. | Phenol recovery of bisphenol-a mother liquor purge using purification train in the phenol production unit |
| KR20230149817A (ko) | 2021-02-23 | 2023-10-27 | 코베스트로 도이칠란트 아게 | 벤젠의 존재 하에 비스페놀 a (bpa)를 제조하는 방법 |
| KR20230149816A (ko) | 2021-02-23 | 2023-10-27 | 코베스트로 도이칠란트 아게 | 2-메틸 벤조푸란의 존재 하에 비스페놀 a (bpa)를 제조하는방법 |
| JP2024508776A (ja) | 2021-02-23 | 2024-02-28 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | アセトフェノンの存在下でビスフェノールａ（ｂｐａ）を作製するプロセス |
| CN116897145A (zh) | 2021-02-23 | 2023-10-17 | 科思创德国股份有限公司 | 在α-甲基苯乙烯的存在下制备双酚A(BPA)的方法 |
| ES3029217T3 (en) | 2021-02-23 | 2025-06-23 | Covestro Deutschland Ag | Process for preparing bisphenol a (bpa) in the presence of at least two impurities |
| CN116867760A (zh) | 2021-02-23 | 2023-10-10 | 科思创德国股份有限公司 | 在异丙苯存在下制备双酚a(bpa)的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2775620A (en) | 1954-07-12 | 1956-12-25 | Shell Dev | Production of bis (hydroxyaryl) substituted compounds |
| JPS6236346A (ja) * | 1985-04-24 | 1987-02-17 | Mitsui Toatsu Chem Inc | アクリルアミド結晶の製造方法 |
| US4859803A (en) | 1988-05-16 | 1989-08-22 | Shell Oil Company | Preparation of bisphenols |
| JP3171465B2 (ja) * | 1991-10-25 | 2001-05-28 | 千代田化工建設株式会社 | 色相の良好なビスフェノールａ・フェノール結晶アダクトの製造方法 |
| ES2126977T3 (es) | 1991-07-10 | 1999-04-01 | Chiyoda Chem Eng Construct Co | Procedimento para la produccion de aducto cristalino de bisfenol a y fenol. |
| JP3413497B2 (ja) * | 1991-10-30 | 2003-06-03 | 三菱化学株式会社 | ビスフェノールａの製造方法 |
| DE4408008A1 (de) | 1994-03-10 | 1995-09-14 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von hochreinem Bisphenol-A |
| EP0720976B2 (en) † | 1994-12-09 | 2005-05-18 | The Dow Chemical Company | Process for preparing an adduct of a bisphenol with a phenolic compound |
| DE10015014A1 (de) * | 2000-03-27 | 2001-10-04 | Bayer Ag | Verfahren zur Herstellung von Bisphenolen |
-
2000
- 2000-03-27 DE DE10015014A patent/DE10015014A1/de not_active Withdrawn
-
2001
- 2001-03-14 MX MXPA02009453A patent/MXPA02009453A/es active IP Right Grant
- 2001-03-14 US US10/239,544 patent/US6828465B2/en not_active Expired - Lifetime
- 2001-03-14 EP EP01921334A patent/EP1268379B9/de not_active Expired - Lifetime
- 2001-03-14 DE DE50101607T patent/DE50101607D1/de not_active Expired - Lifetime
- 2001-03-14 JP JP2001570593A patent/JP5419314B2/ja not_active Expired - Fee Related
- 2001-03-14 BR BR0109539-0A patent/BR0109539A/pt not_active Application Discontinuation
- 2001-03-14 KR KR1020027012693A patent/KR100781863B1/ko not_active Expired - Fee Related
- 2001-03-14 AU AU2001248347A patent/AU2001248347A1/en not_active Abandoned
- 2001-03-14 CN CNB018071686A patent/CN1179931C/zh not_active Expired - Lifetime
- 2001-03-14 ES ES01921334T patent/ES2217134T5/es not_active Expired - Lifetime
- 2001-03-14 WO PCT/EP2001/002845 patent/WO2001072677A1/de not_active Ceased
- 2001-03-20 TW TW090106395A patent/TWI252224B/zh not_active IP Right Cessation
-
2013
- 2013-08-09 JP JP2013165930A patent/JP2013249306A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20040030195A1 (en) | 2004-02-12 |
| CN1419530A (zh) | 2003-05-21 |
| EP1268379B1 (de) | 2004-03-03 |
| AU2001248347A1 (en) | 2001-10-08 |
| MXPA02009453A (es) | 2003-04-10 |
| CN1179931C (zh) | 2004-12-15 |
| ES2217134T5 (es) | 2009-11-17 |
| ES2217134T3 (es) | 2004-11-01 |
| JP2003528840A (ja) | 2003-09-30 |
| JP5419314B2 (ja) | 2014-02-19 |
| EP1268379A1 (de) | 2003-01-02 |
| HK1053106A1 (en) | 2003-10-10 |
| US6828465B2 (en) | 2004-12-07 |
| WO2001072677A1 (de) | 2001-10-04 |
| JP2013249306A (ja) | 2013-12-12 |
| DE50101607D1 (de) | 2004-04-08 |
| KR20020084253A (ko) | 2002-11-04 |
| EP1268379B2 (de) | 2009-06-17 |
| BR0109539A (pt) | 2003-06-10 |
| DE10015014A1 (de) | 2001-10-04 |
| KR100781863B1 (ko) | 2007-12-05 |
| EP1268379B9 (de) | 2010-02-24 |
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