CA2419375A1 - Antioxidant agent based on phenolic salts - Google Patents
Antioxidant agent based on phenolic salts Download PDFInfo
- Publication number
- CA2419375A1 CA2419375A1 CA002419375A CA2419375A CA2419375A1 CA 2419375 A1 CA2419375 A1 CA 2419375A1 CA 002419375 A CA002419375 A CA 002419375A CA 2419375 A CA2419375 A CA 2419375A CA 2419375 A1 CA2419375 A1 CA 2419375A1
- Authority
- CA
- Canada
- Prior art keywords
- phenolic
- salts
- ageing
- groups
- phenolic compounds
- 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.)
- Abandoned
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000003963 antioxidant agent Substances 0.000 title abstract 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 33
- 150000002989 phenols Chemical class 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 229920000620 organic polymer Polymers 0.000 claims abstract description 10
- 230000003712 anti-aging effect Effects 0.000 claims description 28
- -1 basic metal salts Chemical class 0.000 claims description 14
- 229910052728 basic metal Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 230000032683 aging Effects 0.000 description 19
- 239000005060 rubber Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 229920013648 Perbunan Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920006170 Therban® Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229940010415 calcium hydride Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000899 pressurised-fluid extraction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical class [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000003819 basic metal compounds Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OBIFJJIDQJXRTR-UHFFFAOYSA-N hexa-1,3,5-triene;styrene Chemical compound C=CC=CC=C.C=CC1=CC=CC=C1 OBIFJJIDQJXRTR-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/138—Phenolates
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Cereal-Derived Products (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10039754 | 2000-08-16 | ||
| DE10039754.9 | 2000-08-16 | ||
| PCT/EP2001/008996 WO2002014419A1 (de) | 2000-08-16 | 2001-08-03 | Alterungsschutzmittel auf basis von phenolischen salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2419375A1 true CA2419375A1 (en) | 2002-02-21 |
Family
ID=7652425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002419375A Abandoned CA2419375A1 (en) | 2000-08-16 | 2001-08-03 | Antioxidant agent based on phenolic salts |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20020072557A1 (enExample) |
| EP (1) | EP1311604B1 (enExample) |
| JP (1) | JP2004506769A (enExample) |
| KR (1) | KR100727512B1 (enExample) |
| CN (1) | CN1214063C (enExample) |
| AT (1) | ATE308584T1 (enExample) |
| AU (1) | AU2002213847A1 (enExample) |
| BR (1) | BR0113217B1 (enExample) |
| CA (1) | CA2419375A1 (enExample) |
| DE (1) | DE50107928D1 (enExample) |
| ES (1) | ES2248400T3 (enExample) |
| MX (1) | MXPA03001351A (enExample) |
| TW (1) | TW538085B (enExample) |
| WO (1) | WO2002014419A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006025423A1 (de) * | 2006-05-31 | 2007-12-06 | Siemens Ag | Röntgenanlage mit dual energy Betrieb und Auswertungsverfahren für im dual energy Betrieb erfasste Projektionsbilder |
| EP2065437A1 (en) | 2007-11-30 | 2009-06-03 | Lanxess Deutschland GmbH | Improved polymer vulcanizate and process for the production thereof |
| EP2145920A1 (en) | 2008-07-15 | 2010-01-20 | Lanxess Deutschland GmbH | Vulcanizable polymer compositions |
| CN102257049B (zh) | 2008-09-12 | 2014-09-10 | 朗盛公司 | 具有改进的耐热性、压缩变形性、以及可加工性的新颖的弹性体组合物 |
| EP2199326B1 (en) * | 2008-12-19 | 2014-10-29 | LANXESS Deutschland GmbH | Vulcanizable polymer compositions |
| EP4101884B1 (en) | 2014-02-03 | 2024-11-27 | Aquaspersions Ltd. | Antioxidant stabiliser for polymers |
| EP3102631B1 (en) | 2014-02-03 | 2018-05-16 | ARLANXEO Deutschland GmbH | Stabilized rubbers |
| RU2664145C1 (ru) * | 2014-11-27 | 2018-08-15 | Зэон Корпорейшн | Композиция на основе нитрильного каучука, латексная композиция высоконасыщенного нитрильного каучука и сшитый каучук |
| CN105985833A (zh) * | 2015-01-29 | 2016-10-05 | 中国石油天然气股份有限公司 | 一种无锌液压油添加剂组合物 |
| CN105985832A (zh) * | 2015-01-29 | 2016-10-05 | 中国石油天然气股份有限公司 | 一种具有抗氧化性能的液压油添加剂组合物 |
| JP6987739B2 (ja) | 2015-07-07 | 2022-01-05 | スリーエム イノベイティブ プロパティズ カンパニー | イオン性添加剤を含むポリマーマトリックス |
| WO2017007672A1 (en) | 2015-07-07 | 2017-01-12 | 3M Innovative Properties Company | Substituted benzotriazole phenols |
| WO2017007675A1 (en) | 2015-07-07 | 2017-01-12 | 3M Innovative Properties Company | Electret webs with charge-enhancing additives |
| KR102627554B1 (ko) | 2015-07-07 | 2024-01-22 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 치환된 벤조트라이아졸 페놀레이트 염 및 그로부터 형성된 산화방지제 조성물 |
| CN107556563A (zh) * | 2017-09-11 | 2018-01-09 | 常州市五洲化工有限公司 | 一种用于热塑性弹性体的新型抗氧剂的制备方法 |
| KR102833236B1 (ko) | 2025-03-04 | 2025-07-14 | 주식회사 대성티엠씨 | Its 기반 터널 소방 설비 연계 비상 상황 대응 장치 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2581909A (en) * | 1949-03-30 | 1952-01-08 | Firestone Tire & Rubber Co | Stabilization of acrylonitrile-butadiene-1, 3 copolymers |
| US2560029A (en) * | 1949-10-28 | 1951-07-10 | Firestone Tire & Rubber Co | Butadiene-styrene rubbery copolymer stabilized with antimonyl-4,6 dimethyl catecholate |
| BE517864A (enExample) * | 1952-02-23 | |||
| BE518313A (enExample) * | 1952-03-11 | |||
| CH445110A (de) * | 1954-03-13 | 1967-10-15 | Bayer Ag | Verfahren zum Wärmestabilisieren von Polyamiden |
| BE625285A (enExample) * | 1961-11-30 | |||
| US3723489A (en) * | 1971-02-25 | 1973-03-27 | Ciba Geigy Corp | Metal derivatives of 3,5-di-t-butyl-4-hydroxyphenyl propionic acid |
| US3906055A (en) * | 1973-09-10 | 1975-09-16 | Stanford Research Inst | Epoxy resin with metal salt of bisphenol or novolac as fire resistant composition |
| US4211663A (en) * | 1978-05-01 | 1980-07-08 | Mobil Oil Corporation | Alkali metal containing transition metal complexes of thiobis (alkylphenols) as stabilizers for various organic media |
| EP0068851A1 (en) * | 1981-07-01 | 1983-01-05 | Union Carbide Corporation | Metallic salts of hindered phenolic anti-oxidant as anti-gel component in transition metal-catalyzed olefin polymers containing halide residue |
| US4444929A (en) * | 1982-11-24 | 1984-04-24 | The B. F. Goodrich Company | Unsymmetrical phosphite-phenolic isocyanurate stabilizer combinations |
| IT1190366B (it) * | 1985-06-19 | 1988-02-16 | Bozetto Ind Chim | Composizioni polimeriche stabilizzate e sistemi stabilizzanti adatti allo scopo |
| EP0243319A3 (de) * | 1986-04-25 | 1989-02-15 | Ciba-Geigy Ag | Gegen Lichteinwirkung stabilisierte Thermoplasten |
| DE3743279A1 (de) * | 1987-12-19 | 1989-06-29 | Basf Ag | Heterocyclische bicyclo-(3.3.1)nonanderivate und deren verwendung |
| JPH0360444A (ja) * | 1989-07-28 | 1991-03-15 | Sekisui Chem Co Ltd | 塩化ビニル系合わせガラス用中間膜組成物及びその組成物を用いた合わせガラス用中間膜 |
| TW254955B (enExample) * | 1992-09-25 | 1995-08-21 | Ciba Geigy | |
| KR100320319B1 (ko) * | 1993-07-15 | 2002-07-27 | 시바 스페셜티 케미칼스 홀딩 인크. | 스티렌함유재생플라스틱물질의안정화방법및그를위한안정화제혼합물 |
-
2001
- 2001-08-03 DE DE50107928T patent/DE50107928D1/de not_active Expired - Lifetime
- 2001-08-03 JP JP2002519552A patent/JP2004506769A/ja active Pending
- 2001-08-03 WO PCT/EP2001/008996 patent/WO2002014419A1/de not_active Ceased
- 2001-08-03 CN CNB018174000A patent/CN1214063C/zh not_active Expired - Fee Related
- 2001-08-03 CA CA002419375A patent/CA2419375A1/en not_active Abandoned
- 2001-08-03 ES ES01982201T patent/ES2248400T3/es not_active Expired - Lifetime
- 2001-08-03 EP EP01982201A patent/EP1311604B1/de not_active Expired - Lifetime
- 2001-08-03 AT AT01982201T patent/ATE308584T1/de not_active IP Right Cessation
- 2001-08-03 MX MXPA03001351A patent/MXPA03001351A/es active IP Right Grant
- 2001-08-03 BR BRPI0113217-2A patent/BR0113217B1/pt not_active IP Right Cessation
- 2001-08-03 KR KR1020037002246A patent/KR100727512B1/ko not_active Expired - Fee Related
- 2001-08-03 AU AU2002213847A patent/AU2002213847A1/en not_active Abandoned
- 2001-08-14 US US09/929,190 patent/US20020072557A1/en not_active Abandoned
- 2001-08-14 TW TW090119824A patent/TW538085B/zh not_active IP Right Cessation
-
2003
- 2003-11-06 US US10/702,868 patent/US20040092634A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE50107928D1 (de) | 2005-12-08 |
| AU2002213847A1 (en) | 2002-02-25 |
| CN1469896A (zh) | 2004-01-21 |
| BR0113217B1 (pt) | 2010-12-14 |
| WO2002014419A1 (de) | 2002-02-21 |
| KR20030028810A (ko) | 2003-04-10 |
| EP1311604A1 (de) | 2003-05-21 |
| BR0113217A (pt) | 2003-06-24 |
| JP2004506769A (ja) | 2004-03-04 |
| TW538085B (en) | 2003-06-21 |
| ES2248400T3 (es) | 2006-03-16 |
| ATE308584T1 (de) | 2005-11-15 |
| US20020072557A1 (en) | 2002-06-13 |
| EP1311604B1 (de) | 2005-11-02 |
| US20040092634A1 (en) | 2004-05-13 |
| CN1214063C (zh) | 2005-08-10 |
| MXPA03001351A (es) | 2004-04-05 |
| KR100727512B1 (ko) | 2007-06-14 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |