TWI247738B - Polymerization inhibitor for vinyl-containing materials - Google Patents
Polymerization inhibitor for vinyl-containing materials Download PDFInfo
- Publication number
- TWI247738B TWI247738B TW090118057A TW90118057A TWI247738B TW I247738 B TWI247738 B TW I247738B TW 090118057 A TW090118057 A TW 090118057A TW 90118057 A TW90118057 A TW 90118057A TW I247738 B TWI247738 B TW I247738B
- Authority
- TW
- Taiwan
- Prior art keywords
- vinyl
- composition
- benzoquinone
- phenyl
- diimine
- Prior art date
Links
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 42
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 30
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 24
- 239000003112 inhibitor Substances 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 23
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 18
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 quinone diimine compound Chemical class 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002683 reaction inhibitor Substances 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- IYXBYADMMGNDIK-UHFFFAOYSA-N 5,6-diiminocyclohex-2-ene-1,4-dione Chemical compound N=C1C(=N)C(=O)C=CC1=O IYXBYADMMGNDIK-UHFFFAOYSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 238000012545 processing Methods 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229960000964 phenelzine Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- DTNMLFOXJUUMQV-UHFFFAOYSA-N 1-ethyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(CC)=CC=C2 DTNMLFOXJUUMQV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 208000001613 Gambling Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- HXYXTCJDWHHCBW-UHFFFAOYSA-N acetonitrile;toluene Chemical compound CC#N.CC1=CC=CC=C1 HXYXTCJDWHHCBW-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ACFNYGLBKAZUDY-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-diimine Chemical compound N=C1C=CC(=N)C=C1 ACFNYGLBKAZUDY-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical group CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification 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
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
- C07C251/22—Quinone imines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/22—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing an amide or imide moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/625,617 US6447649B1 (en) | 2000-07-24 | 2000-07-24 | Polymerization inhibitor for vinyl-containing materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI247738B true TWI247738B (en) | 2006-01-21 |
Family
ID=24506878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090118057A TWI247738B (en) | 2000-07-24 | 2001-07-24 | Polymerization inhibitor for vinyl-containing materials |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6447649B1 (enExample) |
| EP (1) | EP1305279B1 (enExample) |
| JP (1) | JP4672963B2 (enExample) |
| KR (1) | KR100730847B1 (enExample) |
| AU (1) | AU2001275287A1 (enExample) |
| BR (1) | BR0112727B1 (enExample) |
| DE (1) | DE60109040T2 (enExample) |
| ES (1) | ES2236244T3 (enExample) |
| MX (1) | MXPA03000704A (enExample) |
| TW (1) | TWI247738B (enExample) |
| WO (1) | WO2002008161A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0309629A (pt) * | 2002-05-01 | 2005-03-08 | Ciba Sc Holding Ag | Processo para término de cadeia na polimerização de pvc |
| JP5450300B2 (ja) * | 2009-07-31 | 2014-03-26 | 富士フイルム株式会社 | 放射線硬化性塩化ビニル系樹脂組成物およびその製造方法、塩化ビニル系樹脂、磁気記録媒体、ならびに放射線硬化性塩化ビニル系樹脂用保存安定剤 |
| US8691994B2 (en) * | 2011-02-03 | 2014-04-08 | Nalco Company | Multi-component polymerization inhibitors for ethylenically unsaturated monomers |
| US9090526B2 (en) | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
| US9206268B2 (en) | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
| JP5752579B2 (ja) * | 2011-12-09 | 2015-07-22 | 伯東株式会社 | 安定化された４−オキソ−２，２，６，６−テトラメチルピペリジン−１−オキシル含有組成物、ビニル化合物の重合禁止剤組成物、及びこれを用いたビニル化合物の重合禁止方法 |
| US9944577B2 (en) | 2012-10-25 | 2018-04-17 | Baker Hughes, A Ge Company, Llc | Hydroquinone compounds for inhibiting monomer polymerization |
| US9611336B2 (en) | 2012-10-25 | 2017-04-04 | Baker Hughes Incorporated | Quinone compounds for inhibiting monomer polymerization |
| US10782541B2 (en) | 2015-11-23 | 2020-09-22 | Carl Zeiss Vision International Gmbh | Method for designing a lens shape and spectacle lens |
| EP3738951B1 (en) * | 2018-11-27 | 2022-09-14 | Boai NKY Medical Holdings Ltd. | Use of a polymerization inhibitor for n-vinyl pyrrolidone monomer |
| ES3002772T3 (en) * | 2018-12-20 | 2025-03-07 | Ecolab Usa Inc | Hydroxylated quinone antipolymerants and methods of using |
| EP4036074A1 (en) * | 2021-01-27 | 2022-08-03 | Evonik Operations GmbH | Method for suppressing the polymerization of unsaturated aromatic monomers |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR7602313A (pt) * | 1975-04-17 | 1976-10-12 | Felt Products Mfg Co | Composicao anaerobica de cola e processo para sua preparacao |
| US4166169A (en) * | 1976-03-05 | 1979-08-28 | Felt Products Mfg. Co. | High-strength anaerobic sealants containing n-nitrosoamine modifier |
| JPS604194A (ja) * | 1983-06-21 | 1985-01-10 | Kanegafuchi Chem Ind Co Ltd | アクリルオキシシラン用安定剤 |
| JP3045175B2 (ja) * | 1990-10-04 | 2000-05-29 | 三井化学株式会社 | 発色性記録材料 |
| US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5470440A (en) * | 1994-04-19 | 1995-11-28 | Betz Laboratories, Inc. | Method for inhibiting vinyl aromatic monomer polymerization |
| US5728872A (en) * | 1994-06-27 | 1998-03-17 | Lutz Riemenschneider | Stabilized acrylic acid compositions |
| DE4437667A1 (de) * | 1994-10-21 | 1996-04-25 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N,N'-disubstituierten p-Chinondiiminen, deren Verwendung und Methacryloxy- oder Acryloxy-Gruppen enthaltende Organosilane, Verfahren zu deren Stabilisierung und deren Herstellung |
| DE4437666A1 (de) * | 1994-10-21 | 1996-04-25 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N,N-disubstituierten p-Chinondiiminen und deren Verwendung |
| US5583247A (en) | 1995-04-14 | 1996-12-10 | Ciba-Geigy Corporation | 7-substituted quinone methides as inhibitors for unsaturated monomers |
| US5648573A (en) | 1995-06-12 | 1997-07-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US5756870A (en) | 1996-05-03 | 1998-05-26 | Betzdearborn Inc. | Methods for inhibiting the polymerization of ethylenically unsaturated monomers |
| US5877344A (en) | 1997-06-13 | 1999-03-02 | Ciba Specialty Chemicals Corporation | Polymerization inhibition of acrylates using blends of nitroxides |
| US5859280A (en) * | 1997-07-01 | 1999-01-12 | Betzdearborn Inc. | Methods for inhibiting the polymerization of vinyl monomers |
| ES2192798T3 (es) * | 1997-10-20 | 2003-10-16 | Flexsys America Lp | Quinonadiimina como aditivo para el caucho. |
-
2000
- 2000-07-24 US US09/625,617 patent/US6447649B1/en not_active Expired - Fee Related
-
2001
- 2001-06-04 DE DE60109040T patent/DE60109040T2/de not_active Expired - Lifetime
- 2001-06-04 EP EP01941980A patent/EP1305279B1/en not_active Expired - Lifetime
- 2001-06-04 BR BRPI0112727-6A patent/BR0112727B1/pt not_active IP Right Cessation
- 2001-06-04 KR KR1020037001027A patent/KR100730847B1/ko not_active Expired - Fee Related
- 2001-06-04 WO PCT/US2001/018259 patent/WO2002008161A2/en not_active Ceased
- 2001-06-04 AU AU2001275287A patent/AU2001275287A1/en not_active Abandoned
- 2001-06-04 ES ES01941980T patent/ES2236244T3/es not_active Expired - Lifetime
- 2001-06-04 MX MXPA03000704A patent/MXPA03000704A/es active IP Right Grant
- 2001-06-04 JP JP2002514071A patent/JP4672963B2/ja not_active Expired - Fee Related
- 2001-07-24 TW TW090118057A patent/TWI247738B/zh not_active IP Right Cessation
-
2002
- 2002-09-04 US US10/235,009 patent/US6592722B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030020403A (ko) | 2003-03-08 |
| MXPA03000704A (es) | 2004-11-01 |
| JP4672963B2 (ja) | 2011-04-20 |
| DE60109040D1 (de) | 2005-03-31 |
| DE60109040T2 (de) | 2006-04-13 |
| WO2002008161A3 (en) | 2002-06-13 |
| BR0112727A (pt) | 2003-06-24 |
| US6592722B2 (en) | 2003-07-15 |
| AU2001275287A1 (en) | 2002-02-05 |
| EP1305279A2 (en) | 2003-05-02 |
| US20030030035A1 (en) | 2003-02-13 |
| JP2004504369A (ja) | 2004-02-12 |
| WO2002008161A2 (en) | 2002-01-31 |
| EP1305279B1 (en) | 2005-02-23 |
| US6447649B1 (en) | 2002-09-10 |
| ES2236244T3 (es) | 2005-07-16 |
| KR100730847B1 (ko) | 2007-06-20 |
| BR0112727B1 (pt) | 2012-03-20 |
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