JP4890727B2 - 制御された異性体分布をもったメタンジフェニルジアミンとその高級同族体の混合物の合成方法 - Google Patents
制御された異性体分布をもったメタンジフェニルジアミンとその高級同族体の混合物の合成方法 Download PDFInfo
- Publication number
- JP4890727B2 JP4890727B2 JP2002525083A JP2002525083A JP4890727B2 JP 4890727 B2 JP4890727 B2 JP 4890727B2 JP 2002525083 A JP2002525083 A JP 2002525083A JP 2002525083 A JP2002525083 A JP 2002525083A JP 4890727 B2 JP4890727 B2 JP 4890727B2
- Authority
- JP
- Japan
- Prior art keywords
- zeolite
- group
- reaction
- aniline
- aromatic
- 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
- 238000000034 method Methods 0.000 title claims description 42
- 238000009826 distribution Methods 0.000 title abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title description 17
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 239000010457 zeolite Substances 0.000 claims abstract description 83
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 81
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 80
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 81
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 150000001412 amines Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 11
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 11
- 238000002444 silanisation Methods 0.000 claims description 11
- 238000006462 rearrangement reaction Methods 0.000 claims description 10
- 150000001448 anilines Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000543 intermediate Substances 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000001354 calcination Methods 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 150000003377 silicon compounds Chemical class 0.000 claims 2
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- -1 methane diphenyl diamine Chemical class 0.000 abstract description 4
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000011521 glass Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 238000004821 distillation Methods 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000007810 chemical reaction solvent Substances 0.000 description 12
- 229910052681 coesite Inorganic materials 0.000 description 12
- 229910052906 cristobalite Inorganic materials 0.000 description 12
- 229910052682 stishovite Inorganic materials 0.000 description 12
- 229910052905 tridymite Inorganic materials 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000013638 trimer Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 8
- 230000009849 deactivation Effects 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000011973 solid acid Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012229 microporous material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 0 C*(CC1=C*(*)C=C(*(C)CC2=CC=CCC=C2)C=C1)C1=CCCC=C1 Chemical compound C*(CC1=C*(*)C=C(*(C)CC2=CC=CCC=C2)C=C1)C1=CCCC=C1 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000007854 aminals Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- 229940095070 tetrapropyl orthosilicate Drugs 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000MI001959A IT1318686B1 (it) | 2000-09-07 | 2000-09-07 | Procedimento per la sintesi di miscele di metilendianilina e suoiomologhi superiori con distribuzione controllata degli isomeri. |
| ITMI2000A001959 | 2000-09-07 | ||
| PCT/EP2001/010369 WO2002020458A1 (en) | 2000-09-07 | 2001-09-07 | Process for the synthesis of mixtures of methane diphenyl diamine and its higher homologues with a controlled isomer distribution |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004513086A JP2004513086A (ja) | 2004-04-30 |
| JP2004513086A5 JP2004513086A5 (enExample) | 2008-10-30 |
| JP4890727B2 true JP4890727B2 (ja) | 2012-03-07 |
Family
ID=11445761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002525083A Expired - Fee Related JP4890727B2 (ja) | 2000-09-07 | 2001-09-07 | 制御された異性体分布をもったメタンジフェニルジアミンとその高級同族体の混合物の合成方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6936737B2 (enExample) |
| EP (1) | EP1355874B1 (enExample) |
| JP (1) | JP4890727B2 (enExample) |
| KR (1) | KR100817008B1 (enExample) |
| CN (1) | CN1257148C (enExample) |
| AT (1) | ATE464282T1 (enExample) |
| AU (1) | AU2001293801A1 (enExample) |
| BR (1) | BR0113790A (enExample) |
| IT (1) | IT1318686B1 (enExample) |
| PT (1) | PT1355874E (enExample) |
| WO (1) | WO2002020458A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010019844A1 (en) | 2008-08-14 | 2010-02-18 | Dow Global Technologies Inc. | Production of mixtures of methylenedianiline and its higher homologues using calcined metal oxide-silica catalysts |
| EP2495032A1 (de) | 2011-03-03 | 2012-09-05 | Umicore Ag & Co. Kg | SCR-Katalysator mit verbesserter Kohlenwasserstoffresistenz |
| JP5972913B2 (ja) * | 2011-03-03 | 2016-08-17 | ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフトＵｍｉｃｏｒｅ ＡＧ ＆ Ｃｏ．ＫＧ | 窒素酸化物の選択的触媒還元を行うための触媒活性材料および触媒コンバータ |
| KR20170031157A (ko) | 2014-07-07 | 2017-03-20 | 코베스트로 도이칠란트 아게 | 디페닐메탄 시리즈의 디아민 및 폴리아민의 제조 방법 |
| US10538480B2 (en) | 2016-06-30 | 2020-01-21 | Covestro Deutschland Ag | Process for the production of di- and polyamines of the diphenylmethane series |
| WO2025086031A1 (zh) * | 2023-10-23 | 2025-05-01 | 万华化学集团股份有限公司 | 一种二苯基甲烷系列二胺和多胺的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442795A (en) * | 1963-02-27 | 1969-05-06 | Mobil Oil Corp | Method for preparing highly siliceous zeolite-type materials and materials resulting therefrom |
| US3728408A (en) * | 1969-05-05 | 1973-04-17 | Mobil Oil Corp | Conversion of polar compounds using highly siliceous zeolite-type catalysts |
| US4039581A (en) * | 1975-06-27 | 1977-08-02 | The Upjohn Company | Process for the preparation of di(amino phenyl)methanes |
| US4039580A (en) * | 1975-07-24 | 1977-08-02 | The Upjohn Company | Process for preparing di(aminophenyl)methanes |
| US4294987A (en) * | 1979-12-31 | 1981-10-13 | The Upjohn Company | Process for preparing methylene dianilines |
| DE3783199T2 (de) * | 1986-10-22 | 1993-04-29 | Enichem Sintesi | Verfahren zur herstellung von 4,4' diaminodiphenylmethan und derivaten davon. |
| US5241119A (en) * | 1986-10-22 | 1993-08-31 | Eniricerche S.P.A. | Process for the preparation of 4,4'-diaminodiphenyl-methane and its derivatives |
| AU612786B2 (en) * | 1988-02-15 | 1991-07-18 | Mitsui Petrochemical Industries, Ltd. | Method of preparing 4,4'-methylenedianiline |
| IT1312331B1 (it) * | 1999-05-27 | 2002-04-15 | Enichem Spa | Procedimento per la produzione di diamminodifenilmetano e suoiomologhi superiori. |
-
2000
- 2000-09-07 IT IT2000MI001959A patent/IT1318686B1/it active
-
2001
- 2001-09-07 CN CNB018152147A patent/CN1257148C/zh not_active Expired - Fee Related
- 2001-09-07 JP JP2002525083A patent/JP4890727B2/ja not_active Expired - Fee Related
- 2001-09-07 US US10/363,881 patent/US6936737B2/en not_active Expired - Fee Related
- 2001-09-07 AU AU2001293801A patent/AU2001293801A1/en not_active Abandoned
- 2001-09-07 KR KR1020037003323A patent/KR100817008B1/ko not_active Expired - Fee Related
- 2001-09-07 WO PCT/EP2001/010369 patent/WO2002020458A1/en not_active Ceased
- 2001-09-07 PT PT01974234T patent/PT1355874E/pt unknown
- 2001-09-07 BR BR0113790-5A patent/BR0113790A/pt not_active Application Discontinuation
- 2001-09-07 EP EP01974234A patent/EP1355874B1/en not_active Expired - Lifetime
- 2001-09-07 AT AT01974234T patent/ATE464282T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100817008B1 (ko) | 2008-03-27 |
| AU2001293801A1 (en) | 2002-03-22 |
| US6936737B2 (en) | 2005-08-30 |
| ITMI20001959A0 (it) | 2000-09-07 |
| ITMI20001959A1 (it) | 2002-03-07 |
| EP1355874A1 (en) | 2003-10-29 |
| ATE464282T1 (de) | 2010-04-15 |
| US20040029971A1 (en) | 2004-02-12 |
| WO2002020458A1 (en) | 2002-03-14 |
| BR0113790A (pt) | 2003-07-15 |
| PT1355874E (pt) | 2010-05-11 |
| EP1355874B1 (en) | 2010-04-14 |
| IT1318686B1 (it) | 2003-08-27 |
| CN1257148C (zh) | 2006-05-24 |
| KR20030090597A (ko) | 2003-11-28 |
| CN1620418A (zh) | 2005-05-25 |
| JP2004513086A (ja) | 2004-04-30 |
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