TW538085B - Anti-ageing agents based on phenolic salts - Google Patents
Anti-ageing agents based on phenolic salts Download PDFInfo
- Publication number
- TW538085B TW538085B TW090119824A TW90119824A TW538085B TW 538085 B TW538085 B TW 538085B TW 090119824 A TW090119824 A TW 090119824A TW 90119824 A TW90119824 A TW 90119824A TW 538085 B TW538085 B TW 538085B
- Authority
- TW
- Taiwan
- Prior art keywords
- aging
- phenolic
- aging agent
- scope
- residue
- Prior art date
Links
- 230000003712 anti-aging effect Effects 0.000 title claims abstract description 31
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 150000002989 phenols Chemical class 0.000 claims abstract description 16
- 229920000620 organic polymer Polymers 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- -1 phenol hydrazone Chemical class 0.000 claims description 16
- 230000002079 cooperative effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- NEULNOMQCRVFOQ-UHFFFAOYSA-J C([O-])([O-])=O.[Re+4].C([O-])([O-])=O Chemical class C([O-])([O-])=O.[Re+4].C([O-])([O-])=O NEULNOMQCRVFOQ-UHFFFAOYSA-J 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- RIMXSAKMGZFCDK-UHFFFAOYSA-J C([O-])(O)=O.[Re+4].C([O-])(O)=O.C([O-])(O)=O.C([O-])(O)=O Chemical compound C([O-])(O)=O.[Re+4].C([O-])(O)=O.C([O-])(O)=O.C([O-])(O)=O RIMXSAKMGZFCDK-UHFFFAOYSA-J 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 238000005272 metallurgy Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract 2
- 229920001971 elastomer Polymers 0.000 description 22
- 230000032683 aging Effects 0.000 description 18
- 239000005060 rubber Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 238000011049 filling Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000001875 compounds Chemical class 0.000 description 8
- 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 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 229910052702 rhenium Inorganic materials 0.000 description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000806 elastomer Substances 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910052693 Europium Inorganic materials 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
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 210000003127 knee Anatomy 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 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
- 230000002035 prolonged effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052722 tritium 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
- XAZWIHBIKQEDAO-UHFFFAOYSA-N 2-tert-butyl-4-(9H-fluoren-1-yl)phenol Chemical compound OC1=C(C=C(C=C1)C1=CC=CC=2C3=CC=CC=C3CC1=2)C(C)(C)C XAZWIHBIKQEDAO-UHFFFAOYSA-N 0.000 description 1
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 1
- CGOXUOAIOULNBN-UHFFFAOYSA-N 9h-fluorene;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 CGOXUOAIOULNBN-UHFFFAOYSA-N 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 229920006170 Therban® Polymers 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
- ONJPLECNAPFOJT-UHFFFAOYSA-N [O-2].[Na+].[Os+4] Chemical compound [O-2].[Na+].[Os+4] ONJPLECNAPFOJT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- 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 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000000354 decomposition reaction 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
- 125000000623 heterocyclic group Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002055 nanoplate Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000006104 solid solution Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000013022 venting 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)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Cereal-Derived Products (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10039754 | 2000-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW538085B true TW538085B (en) | 2003-06-21 |
Family
ID=7652425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090119824A TW538085B (en) | 2000-08-16 | 2001-08-14 | Anti-ageing agents 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 |
| US8815984B2 (en) | 2008-09-12 | 2014-08-26 | Lanxess Inc. | Elastomeric compositions with improved heat resistance, compression set, and processability |
| EP2199326B1 (en) * | 2008-12-19 | 2014-10-29 | LANXESS Deutschland GmbH | Vulcanizable polymer compositions |
| EP3102631B1 (en) | 2014-02-03 | 2018-05-16 | ARLANXEO Deutschland GmbH | Stabilized rubbers |
| CN106103565B (zh) | 2014-02-03 | 2019-09-20 | 水史贝瑞森有限公司 | 用于聚合物的抗氧化稳定剂 |
| US10308793B2 (en) | 2014-11-27 | 2019-06-04 | Zeon Corporation | Nitrile rubber composition, latex composition of highly saturated nitrile rubber, and cross-linked rubber |
| 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 |
| 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 |
| US10724171B2 (en) | 2015-07-07 | 2020-07-28 | 3M Innovative Properties Company | Electret webs with charge-enhancing additives |
| US11053373B2 (en) | 2015-07-07 | 2021-07-06 | 3M Innovative Properties Company | Polymeric matrices with ionic additives |
| KR102627554B1 (ko) | 2015-07-07 | 2024-01-22 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 치환된 벤조트라이아졸 페놀레이트 염 및 그로부터 형성된 산화방지제 조성물 |
| WO2017007672A1 (en) | 2015-07-07 | 2017-01-12 | 3M Innovative Properties Company | Substituted benzotriazole phenols |
| 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 |
| NL285901A (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 | |
| AU698316B2 (en) * | 1993-07-15 | 1998-10-29 | Ciba Specialty Chemicals Holding Inc. | Process for stabilising styrene-containing recycled plastic materials and stabiliser mixtures therefor |
-
2001
- 2001-08-03 DE DE50107928T patent/DE50107928D1/de not_active Expired - Lifetime
- 2001-08-03 AT AT01982201T patent/ATE308584T1/de not_active IP Right Cessation
- 2001-08-03 EP EP01982201A patent/EP1311604B1/de not_active Expired - Lifetime
- 2001-08-03 CN CNB018174000A patent/CN1214063C/zh not_active Expired - Fee Related
- 2001-08-03 WO PCT/EP2001/008996 patent/WO2002014419A1/de not_active Ceased
- 2001-08-03 JP JP2002519552A patent/JP2004506769A/ja active Pending
- 2001-08-03 BR BRPI0113217-2A patent/BR0113217B1/pt not_active IP Right Cessation
- 2001-08-03 AU AU2002213847A patent/AU2002213847A1/en not_active Abandoned
- 2001-08-03 MX MXPA03001351A patent/MXPA03001351A/es active IP Right Grant
- 2001-08-03 KR KR1020037002246A patent/KR100727512B1/ko not_active Expired - Fee Related
- 2001-08-03 ES ES01982201T patent/ES2248400T3/es not_active Expired - Lifetime
- 2001-08-03 CA CA002419375A patent/CA2419375A1/en not_active Abandoned
- 2001-08-14 TW TW090119824A patent/TW538085B/zh not_active IP Right Cessation
- 2001-08-14 US US09/929,190 patent/US20020072557A1/en not_active Abandoned
-
2003
- 2003-11-06 US US10/702,868 patent/US20040092634A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE308584T1 (de) | 2005-11-15 |
| ES2248400T3 (es) | 2006-03-16 |
| DE50107928D1 (de) | 2005-12-08 |
| CA2419375A1 (en) | 2002-02-21 |
| US20040092634A1 (en) | 2004-05-13 |
| KR20030028810A (ko) | 2003-04-10 |
| BR0113217B1 (pt) | 2010-12-14 |
| CN1214063C (zh) | 2005-08-10 |
| EP1311604B1 (de) | 2005-11-02 |
| WO2002014419A1 (de) | 2002-02-21 |
| CN1469896A (zh) | 2004-01-21 |
| EP1311604A1 (de) | 2003-05-21 |
| JP2004506769A (ja) | 2004-03-04 |
| BR0113217A (pt) | 2003-06-24 |
| US20020072557A1 (en) | 2002-06-13 |
| AU2002213847A1 (en) | 2002-02-25 |
| KR100727512B1 (ko) | 2007-06-14 |
| MXPA03001351A (es) | 2004-04-05 |
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| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |