CA2574588A1 - Anti-oxidant macromonomers and polymers and methods of making and using the same - Google Patents
Anti-oxidant macromonomers and polymers and methods of making and using the same Download PDFInfo
- Publication number
- CA2574588A1 CA2574588A1 CA002574588A CA2574588A CA2574588A1 CA 2574588 A1 CA2574588 A1 CA 2574588A1 CA 002574588 A CA002574588 A CA 002574588A CA 2574588 A CA2574588 A CA 2574588A CA 2574588 A1 CA2574588 A1 CA 2574588A1
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- Prior art keywords
- polymer
- compound
- alkyl
- aryl
- antioxidant
- 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.)
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- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 119
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229920000642 polymer Polymers 0.000 title claims description 158
- 235000006708 antioxidants Nutrition 0.000 title claims description 115
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 239000000126 substance Substances 0.000 claims abstract description 22
- 230000003647 oxidation Effects 0.000 claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 48
- -1 araikyl Chemical group 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 44
- 150000002148 esters Chemical class 0.000 claims description 42
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 14
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- 150000001555 benzenes Chemical group 0.000 claims description 12
- 235000013305 food Nutrition 0.000 claims description 11
- 239000005022 packaging material Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
- 229920003023 plastic Polymers 0.000 claims description 8
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- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 6
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 6
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
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- 150000003722 vitamin derivatives Chemical class 0.000 claims description 4
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- 229920001169 thermoplastic Polymers 0.000 claims description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
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- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 2
- 229930003268 Vitamin C Natural products 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 2
- 235000015173 baked goods and baking mixes Nutrition 0.000 claims description 2
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- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000012495 crackers Nutrition 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 235000013365 dairy product Nutrition 0.000 claims description 2
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- 239000002283 diesel fuel Substances 0.000 claims description 2
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
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- 239000006210 lotion Substances 0.000 claims description 2
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- 235000013622 meat product Nutrition 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims description 2
- 229920001194 natural rubber Polymers 0.000 claims description 2
- 235000014571 nuts Nutrition 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
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- 239000000123 paper Substances 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 229920001713 poly(ethylene-co-vinyl alcohol) Polymers 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 239000008159 sesame oil Substances 0.000 claims description 2
- 235000011803 sesame oil Nutrition 0.000 claims description 2
- 238000004904 shortening Methods 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
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- 229920003051 synthetic elastomer Polymers 0.000 claims description 2
- 239000005061 synthetic rubber Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 235000019155 vitamin A Nutrition 0.000 claims description 2
- 239000011719 vitamin A Substances 0.000 claims description 2
- 235000019154 vitamin C Nutrition 0.000 claims description 2
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- 235000019165 vitamin E Nutrition 0.000 claims description 2
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- 229940045997 vitamin a Drugs 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 claims 1
- 239000000828 canola oil Substances 0.000 claims 1
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- 230000005764 inhibitory process Effects 0.000 claims 1
- 229920005604 random copolymer Polymers 0.000 claims 1
- 229920000231 antioxidant polymer Polymers 0.000 abstract description 47
- 102000004190 Enzymes Human genes 0.000 description 31
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- 230000015572 biosynthetic process Effects 0.000 description 27
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- 239000000463 material Substances 0.000 description 20
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- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 230000002255 enzymatic effect Effects 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
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- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
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- 125000000753 cycloalkyl group Chemical group 0.000 description 11
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical group C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
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- 230000010933 acylation Effects 0.000 description 3
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- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
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- C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
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- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
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- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
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- C12P13/00—Preparation of nitrogen-containing organic compounds
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- C12P7/00—Preparation of oxygen-containing organic compounds
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Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1492856A4 (en) * | 2002-04-05 | 2010-11-10 | Univ Massachusetts Lowell | POLYMER ANTIOXIDANTS |
US7595074B2 (en) * | 2002-04-05 | 2009-09-29 | University Of Massachusetts Lowell | Polymeric antioxidants |
EP1846460A2 (en) * | 2004-01-21 | 2007-10-24 | University Of Massachusetts Lowell | Post-coupling synthetic approach for polymeric antioxidants |
AU2005269780A1 (en) * | 2004-07-23 | 2006-02-09 | Polnox Corporation | Anti-oxidant macromonomers and polymers and methods of making and using the same |
US20060128939A1 (en) * | 2004-12-03 | 2006-06-15 | Vijayendra Kumar | One pot process for making polymeric antioxidants |
CA2589883A1 (en) | 2004-12-03 | 2006-06-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
EP1817393A2 (en) * | 2004-12-03 | 2007-08-15 | Polnox Corporation | Process for the synthesis of polyalkylphenol antioxidants |
WO2006060802A1 (en) * | 2004-12-03 | 2006-06-08 | Polnox Corporation | Synthesis of sterically hindered phenol based macromolecular antioxidants |
CA2598703A1 (en) | 2005-02-22 | 2006-08-31 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
EP1866279A2 (en) * | 2005-03-25 | 2007-12-19 | Polnox Corporation | Alkylated and polymeric macromolecular antioxidants and methods of making and using the same |
US20070149660A1 (en) * | 2005-10-27 | 2007-06-28 | Vijayendra Kumar | Stabilized polyolefin compositions |
US7705176B2 (en) * | 2005-10-27 | 2010-04-27 | Polnox Corporation | Macromolecular antioxidants based on sterically hindered phenols and phosphites |
US20070106059A1 (en) * | 2005-10-27 | 2007-05-10 | Cholli Ashok L | Macromolecular antioxidants and polymeric macromolecular antioxidants |
US20070161522A1 (en) * | 2005-12-02 | 2007-07-12 | Cholli Ashok L | Lubricant oil compositions |
WO2008005358A2 (en) * | 2006-07-06 | 2008-01-10 | Polnox Corporation | Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same |
US7767853B2 (en) | 2006-10-20 | 2010-08-03 | Polnox Corporation | Antioxidants and methods of making and using the same |
US8864958B2 (en) * | 2007-03-13 | 2014-10-21 | Jds Uniphase Corporation | Method and sputter-deposition system for depositing a layer composed of a mixture of materials and having a predetermined refractive index |
US8206825B2 (en) * | 2008-01-03 | 2012-06-26 | Equistar Chemicals, Lp | Preparation of wires and cables |
US8234248B2 (en) * | 2008-01-24 | 2012-07-31 | Oracle International Corporation | Tracking changes to a business object |
US8402065B2 (en) * | 2008-01-24 | 2013-03-19 | Oracle International Corporation | Electronic control batch record |
JP5403332B2 (ja) * | 2009-03-10 | 2014-01-29 | 長岡香料株式会社 | バニラ豆のリパーゼ阻害活性増強方法、およびリパーゼ阻害剤 |
ITCS20110009A1 (it) * | 2011-03-21 | 2012-09-22 | Univ Calabria | Formulazione cosmetica, farmaceutica o nutraceutica contenente molecole antiossidanti coniugate |
US9808675B2 (en) | 2012-09-13 | 2017-11-07 | Acushnet Company | Golf ball compositions |
US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
KR101781509B1 (ko) | 2016-05-19 | 2017-09-26 | 한국화학연구원 | 하이퍼브랜치 고분자를 함유하는 유동성이 향상된 폴리아미드계 고분자 조성물 및 이의 제조방법 |
KR101815577B1 (ko) | 2016-11-18 | 2018-01-05 | 한국화학연구원 | 하이퍼브랜치 폴리아미드를 함유하는 유동성이 향상된 폴리아미드계 고분자 조성물 및 이의 제조방법 |
US10035043B2 (en) | 2016-12-15 | 2018-07-31 | Acushnet Company | Golf ball incorporating highly crosslinked thermoset fluorescent microspheres and methods of making same |
US20180251695A1 (en) | 2017-03-01 | 2018-09-06 | Polnox Corporation | Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same |
US10252112B2 (en) | 2017-03-20 | 2019-04-09 | Acushnet Company | Golf ball composition |
CN109279800A (zh) * | 2018-11-19 | 2019-01-29 | 河海大学 | 一种基于萝卜提取液的钢筋阻锈剂及制备方法与应用 |
CN111559962B (zh) * | 2020-07-14 | 2020-10-30 | 江西中医药大学 | 一种具有抗氧化活性的新酚酸类化合物的制备方法及应用 |
CN113801260A (zh) * | 2021-08-04 | 2021-12-17 | 吉林奥来德光电材料股份有限公司 | 一种薄膜封装用化合物、光固化组合物和薄膜封装层 |
IT202100021686A1 (it) * | 2021-08-10 | 2023-02-10 | Elettrogalvanica Settimi Srl | Polietilentereftalato (PET) funzionalizzato con attività antiossidante |
US11697048B2 (en) | 2021-08-12 | 2023-07-11 | Acushnet Company | Colored golf ball and method of making same |
CN115784891A (zh) * | 2022-12-14 | 2023-03-14 | 吉林化工学院 | 一种受阻酚类抗氧剂及其制备方法和应用 |
Family Cites Families (186)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3116305A (en) * | 1960-02-18 | 1963-12-31 | Shell Oil Co | Hydroxybenzyl esters |
US3294836A (en) * | 1962-09-17 | 1966-12-27 | Geigy Chem Corp | Stabilization of organic material with certain esters of substituted hydroquinones and organic acids |
US3441545A (en) * | 1963-11-01 | 1969-04-29 | Du Pont | Modification of olefin-carboxylic acid halide copolymers |
GB1161909A (en) | 1966-09-12 | 1969-08-20 | Mini Of Technology | Polymeric Antioxidands for Elastomers and Rubbers |
CA969192A (en) * | 1968-06-21 | 1975-06-10 | Ciba-Geigy Corporation | Polymeric antioxidants |
US3516963A (en) * | 1968-07-22 | 1970-06-23 | Weston Chemical Corp | Phenolic phosphites used as stabilizers |
US3632785A (en) * | 1969-02-19 | 1972-01-04 | Georgia Pacific Corp | Method of forming shell molds |
US3907939A (en) | 1969-06-16 | 1975-09-23 | Ashland Oil Inc | Phosphite esters of hindered phenols |
US3645970A (en) * | 1969-10-01 | 1972-02-29 | Ciba Geigy Corp | Benzoate homopolymers hindered phenolic groups as stabilizers |
US3649667A (en) * | 1970-06-24 | 1972-03-14 | American Cyanamid Co | Aryl polyesters of 3 5-dialkyl-4-hydroxy-phenyl-alkanoic acids |
US3953402A (en) * | 1970-07-20 | 1976-04-27 | The Goodyear Tire & Rubber Company | Age resistant polymers of ditertiary alkyl-4-hydroxyaryl acrylate and dienes |
CH547335A (de) | 1970-10-13 | 1974-03-29 | Sandoz Ag | Stabilisierte, nicht-textile kunststoffe und spinnmassen. |
GB1389442A (en) | 1971-03-02 | 1975-04-03 | Kodak Ltd | P-phenylene-diamine derivatives and uses therefor |
CH564047A5 (US07923587-20110412-C00022.png) | 1972-05-09 | 1975-07-15 | Sandoz Ag | |
JPS5328944B2 (US07923587-20110412-C00022.png) | 1972-07-18 | 1978-08-17 | ||
US3994828A (en) | 1973-06-07 | 1976-11-30 | Dynapol Corporation | Nonabsorbable antioxidant |
US3870680A (en) * | 1973-10-19 | 1975-03-11 | Edward Schurdak | Copper inhibitors for polyolefins |
CA1053832A (en) | 1973-11-08 | 1979-05-01 | Polysar Limited | Polymeric antioxidants |
US4317933A (en) * | 1974-01-22 | 1982-03-02 | The Goodyear Tire & Rubber Company | Preparation of antioxidants |
DE2509654C2 (de) * | 1974-03-06 | 1985-08-29 | Gerald Birmingham Scott | Verfahren zur Herstellung gegen Oxidation stabiler Polymere |
US4136055A (en) * | 1974-06-21 | 1979-01-23 | Raychem Corporation | Compositions of antioxidants of reduced volatility |
GB1469245A (en) | 1974-10-24 | 1977-04-06 | Kodak Ltd | Substituted p-phenylenediamines |
US3965039A (en) | 1974-11-19 | 1976-06-22 | Chaplits Donat N | Ion-exchange molded catalyst and method of its preparation |
US4054676A (en) * | 1974-12-04 | 1977-10-18 | Dynapol | Edible with polymeric hydroquinone antioxidant |
US3951831A (en) * | 1975-01-17 | 1976-04-20 | Rohm And Haas Company | Antioxidant-containing viscosity index improvers for high temperature service |
US3996198A (en) * | 1975-02-24 | 1976-12-07 | Dynapol | One step preparation of linear antioxidant phenolic polymers involving use of impure diolefin feedstock and aluminum catalyst under ortho alkylation conditions |
US3996160A (en) * | 1975-02-24 | 1976-12-07 | Dynapol Corporation | Hydroquinonoid ortho-alkylation polymers and the process of their production |
US4205151A (en) * | 1975-04-04 | 1980-05-27 | Dynapol | Polymeric N-substituted maleimide antioxidants |
US4202816A (en) * | 1975-06-19 | 1980-05-13 | Ciba-Geigy Corporation | Novel light stabilizers |
US3983091A (en) | 1975-07-25 | 1976-09-28 | The Goodyear Tire & Rubber Company | Phenolic antioxidants prepared from tricyclopentadiene and stabilized compositions |
US4097464A (en) * | 1975-11-03 | 1978-06-27 | The Goodyear Tire & Rubber Company | 2,6-Di-tert-alkyl-4-vinylphenols as polymerizable antioxidants |
CA1093248A (en) * | 1976-05-20 | 1981-01-06 | Kenneth E. Russell | Phenolic antioxidants with polymer tails |
US4094857A (en) * | 1977-09-01 | 1978-06-13 | E. I. Du Pont De Nemours And Company | Copolymerizable phenolic antioxidant |
JPS5933138B2 (ja) * | 1977-09-22 | 1984-08-14 | 旭化成株式会社 | 無機充填剤配合フイルム |
NL7905000A (nl) * | 1978-09-25 | 1980-03-27 | Cincinnati Milacron Chem | Gehinderde fenolverbindingen, alsmede organische mate- rialen die met behulp daarvan gestabiliseerd zijn tegen oxydatieve aantasting. |
FR2439769A1 (fr) * | 1978-10-26 | 1980-05-23 | Oreal | N-(dihydroxy-2,5 trimethyl-3,4,6) benzyl acrylamide et methacrylamide, leur procede de preparation et leur utilisation pour la realisation de polymeres antioxydants |
US4297358A (en) * | 1979-01-16 | 1981-10-27 | Ciba-Geigy Corporation | Novel 4,7-phenanthroline derivatives and pharmaceutical compositions containing them and their use |
US4380554A (en) | 1979-06-25 | 1983-04-19 | Standard Oil Company (Indiana) | Polymeric monohydroxybenzenoid hydroquinoid antioxidants |
US4283572A (en) * | 1979-12-27 | 1981-08-11 | Borg-Warner Corporation | Conversion of alkyl phenyl ether to alkylphenol |
US4267358A (en) * | 1980-03-13 | 1981-05-12 | Borg-Warner Corporation | Phenolic ester inhibitor |
US4341879A (en) * | 1980-03-17 | 1982-07-27 | Mitsubishi Gas Chemical Company, Inc. | Polyphenylene ether resin composition having improved heat stability and impact strength |
US4355148A (en) * | 1980-09-18 | 1982-10-19 | The B. F. Goodrich Company | Norbornene polymers containing bound phenolic antioxidant |
JPS5785366A (en) | 1980-11-14 | 1982-05-28 | Sankyo Co Ltd | 2-mercaptoquinone derivative |
US4377666A (en) * | 1981-08-17 | 1983-03-22 | Phillips Petroleum Company | Age-resistant polymers containing chemically bound antioxidant functional groups |
US4511491A (en) * | 1982-07-26 | 1985-04-16 | Sumitomo Chemical Co., Ltd. | Stabilizers for synthetic resins |
JPS5925814A (ja) | 1982-08-04 | 1984-02-09 | Dainippon Ink & Chem Inc | ポリ(ジアルコキシフエニレン)の製造法 |
US4465871A (en) * | 1982-11-10 | 1984-08-14 | Uop Inc. | Preparation of 2-t-butyl-4-alkoxy- and 4-hydroxyphenols |
US4447657A (en) * | 1982-11-10 | 1984-05-08 | Uop Inc. | Preparation of ortho-alkylated phenols |
JPS59197447A (ja) * | 1983-04-26 | 1984-11-09 | Mitsui Petrochem Ind Ltd | 耐塩素水性ポリオレフイン組成物 |
JPS60199832A (ja) | 1984-03-22 | 1985-10-09 | Nitto Electric Ind Co Ltd | 抗酸化性外用製剤 |
US4510296A (en) * | 1984-05-10 | 1985-04-09 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Phenoxy resins containing pendent ethynyl groups and cured resins obtained therefrom |
IT1177022B (it) | 1984-10-24 | 1987-08-26 | Anic Spa | Composizione stabilizzanti per polimeri organici e composizioni polimeriche stabilizzate che li contengono |
US4634728A (en) | 1985-01-17 | 1987-01-06 | Mallinckrodt, Inc. | Polyol carboxyalkylthioalkanoamidophenol compounds and organic material stabilized therewith |
KR930012016B1 (ko) * | 1985-03-26 | 1993-12-23 | 도오요오 보오세끼 가부시끼가이샤 | 고분자형 산화방지제 및 그의 제조방법 |
US4690995A (en) * | 1985-06-06 | 1987-09-01 | The Dow Chemical Company | Copolymers containing high concentrations of phenol antioxidant units |
JPS6245658A (ja) | 1985-08-22 | 1987-02-27 | Hitachi Chem Co Ltd | 安定化された合成樹脂組成物 |
JPS6245546A (ja) * | 1985-08-22 | 1987-02-27 | Hitachi Chem Co Ltd | フエノ−ル系重合体の製造方法 |
US5102962A (en) | 1985-08-22 | 1992-04-07 | Hitachi Chemical Company, Ltd. | Phenolic polymer and production thereof |
US4647952A (en) * | 1985-11-13 | 1987-03-03 | The Mead Corporation | Phenolic developer resins |
FR2597109B1 (fr) * | 1986-04-15 | 1988-06-17 | Thomson Csf | Materiau polymerique mesomorphe utilisable en optique non lineaire |
GB2192189B (en) * | 1986-06-06 | 1990-08-22 | Canon Kk | Polymer of vinyl-biphenyl derivative adapted for optical use |
US4855345A (en) * | 1986-06-19 | 1989-08-08 | Ciba-Geigy Corporation | Stabilizers for organic polymers |
US4761247A (en) * | 1987-03-06 | 1988-08-02 | Morton Thiokol, Inc. | Phenol-stabilized microbiocidal compositions |
GB8710171D0 (en) | 1987-04-29 | 1987-06-03 | Shell Int Research | Copolymer composition |
US4981917A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Process for preparing polymer bound antioxidant stabilizers |
US4857596A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound antioxidant stabilizers |
US4977004A (en) * | 1987-09-28 | 1990-12-11 | Tropicana Products, Inc. | Barrier structure for food packages |
US4849503A (en) * | 1987-12-21 | 1989-07-18 | Amoco Corporation | Novel poly(aryl ethers) |
DE3875461T2 (de) | 1987-12-22 | 1993-05-13 | Mitsubishi Rayon Co | Mesomorphe verbindung, die eine beta-hydroxycarbonsaeuregruppe als chirales zentrum enthaelt und fluessigkristall-zusammensetzung. |
IT1215943B (it) | 1988-02-24 | 1990-02-22 | Enichem Sintesi | Composizione stabilizzante per polimeri organici. |
US4870214A (en) * | 1988-05-20 | 1989-09-26 | Ethyl Corporation | Antioxidant |
US5051531A (en) * | 1988-05-31 | 1991-09-24 | Atochem North America, Inc. | Antioxidant-peroxides |
DE68911436T2 (de) | 1988-09-07 | 1994-06-09 | Yoshitomi Pharmaceutical | Individuelle Partikelkristalle in alpha-Form von Tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy]methan und Verfahren zu seiner Herstellung. |
US5320889A (en) * | 1989-01-17 | 1994-06-14 | Tropicana Products, Inc. | Plastic bottle for food |
US5196142A (en) * | 1989-03-17 | 1993-03-23 | Ciba-Geigy Corporation | Aqueous antioxidant emulsions |
DE3920616A1 (de) * | 1989-06-23 | 1991-01-03 | Boehringer Mannheim Gmbh | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate |
US4994628A (en) * | 1989-09-25 | 1991-02-19 | Ethyl Corporation | Phenolic antioxidant process |
US5013470A (en) * | 1989-10-10 | 1991-05-07 | Texaco Inc. | Antioxidant VII lubricant additive |
GB9001367D0 (en) | 1990-01-20 | 1990-03-21 | Bp Chem Int Ltd | Oxidatively stable polymers and processes for preparing said polymers |
JP2761786B2 (ja) * | 1990-02-01 | 1998-06-04 | 富士写真フイルム株式会社 | ポジ型フオトレジスト組成物 |
US5017727A (en) * | 1990-07-10 | 1991-05-21 | Copolymer Rubber & Chemical Corporation | Polymerizable antioxidant composition |
US5207939A (en) * | 1990-08-23 | 1993-05-04 | Mobil Oil Corporation | Dihydrocarbyl substituted phenylenediamine-derived phenolic products as antioxidants |
US5188953A (en) * | 1990-10-18 | 1993-02-23 | The Mead Corporation | Biocatalytic oxidation using soybean peroxidase |
US5574118A (en) * | 1990-11-02 | 1996-11-12 | Dsm Copolymer, Inc. | Olefin polymers containing bound antioxidant |
US5206303A (en) * | 1990-12-27 | 1993-04-27 | Exxon Chemical Patents Inc. | Entanglement-inhibited macromolecules |
EP0502819A1 (de) * | 1991-03-01 | 1992-09-09 | Ciba-Geigy Ag | Säurekatalytisch vernetzbare Copolymere |
CA2102699A1 (en) | 1991-05-13 | 1992-11-14 | Stephen M. Hoenig | Carbon monoxide interpolymers stabilized against viscosity changes with hindered phenols |
US5652201A (en) | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
US5117063A (en) | 1991-06-21 | 1992-05-26 | Monsanto Company | Method of preparing 4-aminodiphenylamine |
US5869592A (en) * | 1991-08-19 | 1999-02-09 | Maxdem Incorporated | Macromonomers having reactive side groups |
JPH05199858A (ja) | 1991-08-23 | 1993-08-10 | Kaiyo Bio Technol Kenkyusho:Kk | フレキシキサンチンを有効成分とする酸化防止剤及び フレキシキサンチンの製造法 |
US5185407A (en) * | 1991-08-29 | 1993-02-09 | Shell Oil Company | Polymeric phenolic esters |
US5449715A (en) * | 1991-09-17 | 1995-09-12 | Isp Investments Inc. | Colorless, non-toxic, stabilized aqueous solution of a C1-C5 alkyl vinyl ether and maleic acid copolymers |
US5191008A (en) * | 1991-10-21 | 1993-03-02 | The Goodyear Tire & Rubber Company | Process for the production of latexes by the selective monomer addition |
US5185391A (en) * | 1991-11-27 | 1993-02-09 | The Dow Chemical Company | Oxidation inhibited arylcyclobutene polymers |
US5143828A (en) * | 1991-12-31 | 1992-09-01 | The United States Of America As Represented By The Secretary Of The Army | Method for synthesizing an enzyme-catalyzed polymerized monolayer |
ES2101994T3 (es) * | 1992-04-08 | 1997-07-16 | Ciba Geigy Ag | Antioxidantes liquidos como estabilizadores. |
US5278055A (en) | 1992-06-09 | 1994-01-11 | The Mead Corporation | Biocatalytic production of phenolic resins with ramped peroxide addition |
JPH06135876A (ja) | 1992-10-23 | 1994-05-17 | Mitsui Toatsu Chem Inc | フェノール化合物 |
IL107927A0 (en) | 1992-12-17 | 1994-04-12 | Exxon Chemical Patents Inc | Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same |
JP3509891B2 (ja) | 1993-02-24 | 2004-03-22 | サントリー株式会社 | フラボノイド重合物およびこれを有効成分とするグルコシルトランスフェラーゼ阻害剤 |
JP3165279B2 (ja) | 1993-03-29 | 2001-05-14 | 三井農林株式会社 | 3−アシル化カテキンを含有する油溶性抗酸化剤 |
JP3377833B2 (ja) * | 1993-08-06 | 2003-02-17 | 三井化学株式会社 | 環状オレフィン系樹脂からなる成形体およびその製造方法 |
US5618984A (en) | 1994-06-24 | 1997-04-08 | Mitsui Toatsu Chemicals, Inc. | Phenol aralkyl resins, preparation process thereof and epoxy resin compositions |
JP3404132B2 (ja) | 1994-07-12 | 2003-05-06 | 株式会社 伊藤園 | アクリルアミドメチルポリフェノール重合体及びその製造法 |
US5541091A (en) * | 1995-04-05 | 1996-07-30 | Enzymol International, Inc. | Process for the biocatalytic coupling of aromatic compounds in the presence of a radical transfer agent |
US5911937A (en) * | 1995-04-19 | 1999-06-15 | Capitol Specialty Plastics, Inc. | Desiccant entrained polymer |
US5837798A (en) | 1995-07-12 | 1998-11-17 | Georgia-Pacific Resins | Phenolic polymers made by aralkylation reactions |
US6096859A (en) * | 1996-01-16 | 2000-08-01 | The United States Of America As Represented By The Secretary Of The Army | Process to control the molecular weight and polydispersity of substituted polyphenols and polyaromatic amines by enzymatic synthesis in organic solvents, microemulsions, and biphasic systems |
JPH09262069A (ja) | 1996-03-27 | 1997-10-07 | Yanagiya Honten:Kk | ヘテロサイクリックアミン類の生成抑制方法およびこれを利用する節類の製造方法 |
AUPN977296A0 (en) * | 1996-05-10 | 1996-06-06 | Monash University | Pharmaceutical agents |
US6096695A (en) * | 1996-06-03 | 2000-08-01 | Ethyl Corporation | Sulfurized phenolic antioxidant composition, method of preparing same, and petroleum products containing same |
JP3320307B2 (ja) | 1996-06-06 | 2002-09-03 | 株式会社エス・ディー・エス バイオテック | フェノール性化合物等の高分子化方法及びその利用 |
JPH09328521A (ja) | 1996-06-07 | 1997-12-22 | Toppan Printing Co Ltd | L−アスコルビン酸変性ポリビニルアルコール及びその製造方法 |
JPH09328519A (ja) | 1996-06-07 | 1997-12-22 | Toppan Printing Co Ltd | 酸素還元性ポリビニルアルコール誘導体及びその製造方法 |
US6046263A (en) * | 1997-05-26 | 2000-04-04 | Ciba Specialty Chemicals Corporation | Liquid antioxidants as stabilizers |
US6018018A (en) * | 1997-08-21 | 2000-01-25 | University Of Massachusetts Lowell | Enzymatic template polymerization |
US5994498A (en) * | 1997-08-21 | 1999-11-30 | Massachusetts Lowell, University Of Lowell | Method of forming water-soluble, electrically conductive and optically active polymers |
JP2920522B2 (ja) | 1997-09-04 | 1999-07-19 | 工業技術院長 | エーテル類の製造法 |
US6207842B1 (en) | 1997-10-09 | 2001-03-27 | Mars Incorporated | Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives |
US5834544A (en) * | 1997-10-20 | 1998-11-10 | Uniroyal Chemical Company, Inc. | Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities |
DE19747644C2 (de) | 1997-10-29 | 2001-02-22 | Inst Polymerforschung Dresden | Sterisch gehinderte Phenole und Verfahren zu ihrer Herstellung |
JP4078695B2 (ja) | 1997-11-25 | 2008-04-23 | 東ソー株式会社 | 芳香族性エーテルの製造方法 |
US6444450B2 (en) * | 1998-01-28 | 2002-09-03 | The United States Of America As Represented By The Secretary Of The Army | Large-scale production of polyphenols or polyaromatic amines using enzyme-mediated reactions |
US6800228B1 (en) * | 1998-09-22 | 2004-10-05 | Albemarle Corporation | Sterically hindered phenol antioxidant granules having balanced hardness |
DE19843875A1 (de) | 1998-09-25 | 2000-03-30 | Basf Ag | Verfahren zur Herstellung von Metallsalenen |
US6150491A (en) * | 1998-11-06 | 2000-11-21 | The United States Of America As Represented By The Secretary Of The Army | Polyaromatic compounds and method for their production |
WO2000039064A1 (en) | 1998-12-29 | 2000-07-06 | Ciba Specialty Chemicals Holding Inc. | New hydroquinone derivatives as scavengers for oxidised developer |
DE19919708A1 (de) | 1999-04-30 | 2001-03-01 | Univ Stuttgart | Stufenweise Alkylierung von polymeren Aminen |
JP3816697B2 (ja) | 1999-07-07 | 2006-08-30 | 大日精化工業株式会社 | 重合体が結合した機能剤、その製造方法、それらの使用方法及びそれらを使用した物品 |
US7176252B2 (en) * | 1999-07-29 | 2007-02-13 | Dover Chemical Corporation | Solid melt blended phosphite composites |
US6723815B2 (en) * | 1999-09-02 | 2004-04-20 | Alcon, Inc. | Covalently-bound, hydrophilic coating compositions for surgical implants |
ITMI991896A1 (it) | 1999-09-09 | 2001-03-09 | Carlo Ghisalberti | Melanine e pigmenti vegetali |
NL1013942C2 (nl) | 1999-12-23 | 2001-06-26 | Dsm Nv | Multifunctionele thermisch-oxidatieve stabilisator. |
JP4094850B2 (ja) * | 1999-12-30 | 2008-06-04 | ユニロイヤル ケミカル カンパニー インコーポレイテッド | n−(4−アニリノフェニル)アミド類の酸化防止剤アミンを含む組成物 |
CA2399871A1 (en) * | 2000-02-22 | 2001-08-30 | Ciba Specialty Chemicals Holding Inc. | Romp with oligomeric uv-absorbers |
JP2003524035A (ja) * | 2000-02-23 | 2003-08-12 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | アリール置換ポリ−p−アリーレンビニレン |
GB0004437D0 (en) * | 2000-02-25 | 2000-04-12 | Clariant Int Ltd | Synergistic combinations of phenolic antioxidants |
US6559105B2 (en) * | 2000-04-03 | 2003-05-06 | The Lubrizol Corporation | Lubricant compositions containing ester-substituted hindered phenol antioxidants |
US6383636B2 (en) * | 2000-04-04 | 2002-05-07 | Director-General Of National Institute Of Advanced Industrial Science And Technology, Ministry Of Economy, Trade And Industry | (2,5-disubstituted-1,4-phenylene oxide) block or graft copolymer |
EP1142491A3 (en) * | 2000-04-06 | 2002-04-03 | Kyowa Hakko Kogyo Co., Ltd. | Method of removing off-flavor from foods and deodorizer |
WO2002000683A2 (en) * | 2000-06-23 | 2002-01-03 | Vanderbilt University | Novel chain-breaking antioxidants |
US6384176B1 (en) * | 2000-07-10 | 2002-05-07 | General Electric Co. | Composition and process for the manufacture of functionalized polyphenylene ether resins |
US6828364B2 (en) * | 2000-07-14 | 2004-12-07 | Ciba Specialty Chemicals Corporation | Stabilizer mixtures |
US20020183470A1 (en) * | 2000-11-27 | 2002-12-05 | Sukant Tripathy | Polymerization of aromatic monomers using derivatives of hematin |
JP3698067B2 (ja) * | 2001-03-30 | 2005-09-21 | Jsr株式会社 | 電子吸引性基および電子供与性基を有するモノマー、それを用いた共重合体、ならびにプロトン伝導膜 |
GB2378441B (en) | 2001-03-30 | 2004-09-22 | Council Scient Ind Res | A process for preparing alkylated dihydroxybenzene |
WO2003016388A1 (en) | 2001-08-15 | 2003-02-27 | Ciba Specialty Chemicals Holding Inc. | Flame retardant compositions |
JP4784720B2 (ja) * | 2001-09-25 | 2011-10-05 | 信越化学工業株式会社 | 粘着テープ |
JP2003138258A (ja) | 2001-11-07 | 2003-05-14 | Univ Kyoto | 抗酸化剤 |
JP2003212951A (ja) * | 2002-01-23 | 2003-07-30 | Daicel Chem Ind Ltd | 酸化防止機能性樹脂およびそのエマルション |
ES2256724T5 (es) * | 2002-03-21 | 2009-11-27 | Basf Se | Dispersiones acuosas para antioxidantes. |
EP1492856A4 (en) * | 2002-04-05 | 2010-11-10 | Univ Massachusetts Lowell | POLYMER ANTIOXIDANTS |
US7595074B2 (en) | 2002-04-05 | 2009-09-29 | University Of Massachusetts Lowell | Polymeric antioxidants |
DE60306371T2 (de) | 2002-05-30 | 2007-06-21 | Ciba Speciality Chemicals Holding Inc. | Amorphe feste modifikation von bis(2,4-dicumylphenyl) pentaerythritdiphosphit |
US7271209B2 (en) | 2002-08-12 | 2007-09-18 | Exxonmobil Chemical Patents Inc. | Fibers and nonwovens from plasticized polyolefin compositions |
CA2498225A1 (en) | 2002-09-10 | 2004-03-25 | Joel Moss | Factors that bind intestinal toxins |
BR0316567A (pt) * | 2002-11-26 | 2005-10-04 | Ciba Sc Holding Ag | Antioxidantes fenólicos na forma cristalina |
US20070010632A1 (en) * | 2002-11-27 | 2007-01-11 | Kaplan David L | Antioxidant-functionalized polymers |
GB0228647D0 (en) * | 2002-12-09 | 2003-01-15 | Ciba Sc Holding Ag | Polyeric material containing a latent acid |
US7358383B2 (en) * | 2003-01-24 | 2008-04-15 | University Of South Florida | Polyphenol proteasome inhibitors, synthesis, and methods of use |
US20040180994A1 (en) | 2003-03-05 | 2004-09-16 | Pearson Jason Clay | Polyolefin compositions |
US6770785B1 (en) * | 2003-03-25 | 2004-08-03 | Council Of Scientific And Industrial Research | Antiozonant cum antioxidant, process for preparation |
EP1612254A4 (en) * | 2003-04-02 | 2007-07-18 | Idemitsu Kosan Co | ANTIOXIDANE AND BISAMINOPHENOL DERIVATIVE |
EP1468968A1 (de) | 2003-04-18 | 2004-10-20 | Technische Universitat, Institut fur Mikrobiologie und Abfalltechnologie | Eine Laccase enthaltender Biokatalysator |
WO2005025646A2 (en) | 2003-09-08 | 2005-03-24 | U.S. Government As Represented By The Secretary Of The Army | System and method for providing servo-controlled resuscitation |
US8071535B2 (en) | 2003-09-12 | 2011-12-06 | The Regents Of The University Of California | Guanidinium derivatives for improved cellular transport |
US7342060B2 (en) | 2003-12-11 | 2008-03-11 | Dover Chemical Corporation | Process for manufacture of pentaerythritol diphosphites |
EP1846460A2 (en) | 2004-01-21 | 2007-10-24 | University Of Massachusetts Lowell | Post-coupling synthetic approach for polymeric antioxidants |
US7494960B2 (en) * | 2004-02-03 | 2009-02-24 | Crompton Corporation | Lubricant compositions comprising an antioxidant blend |
US7291669B2 (en) | 2004-03-16 | 2007-11-06 | Ciba Specialty Chemicals Corporation | Stabilized polyolefin compositions |
US7329772B2 (en) * | 2004-04-29 | 2008-02-12 | Crompton Corporation | Method for the preparation of a hydroxyalkyl hindered phenolic antioxidant |
AU2005269780A1 (en) | 2004-07-23 | 2006-02-09 | Polnox Corporation | Anti-oxidant macromonomers and polymers and methods of making and using the same |
JP5078614B2 (ja) | 2004-08-18 | 2012-11-21 | チバ ホールディング インコーポレーテッド | 改善された性能を有する潤滑油組成物 |
WO2006060802A1 (en) * | 2004-12-03 | 2006-06-08 | Polnox Corporation | Synthesis of sterically hindered phenol based macromolecular antioxidants |
CA2589883A1 (en) * | 2004-12-03 | 2006-06-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
EP1817393A2 (en) | 2004-12-03 | 2007-08-15 | Polnox Corporation | Process for the synthesis of polyalkylphenol antioxidants |
US20060128939A1 (en) * | 2004-12-03 | 2006-06-15 | Vijayendra Kumar | One pot process for making polymeric antioxidants |
CA2598703A1 (en) * | 2005-02-22 | 2006-08-31 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
EP1866279A2 (en) * | 2005-03-25 | 2007-12-19 | Polnox Corporation | Alkylated and polymeric macromolecular antioxidants and methods of making and using the same |
US7705176B2 (en) * | 2005-10-27 | 2010-04-27 | Polnox Corporation | Macromolecular antioxidants based on sterically hindered phenols and phosphites |
US20070149660A1 (en) * | 2005-10-27 | 2007-06-28 | Vijayendra Kumar | Stabilized polyolefin compositions |
US20070106059A1 (en) * | 2005-10-27 | 2007-05-10 | Cholli Ashok L | Macromolecular antioxidants and polymeric macromolecular antioxidants |
US20070161522A1 (en) * | 2005-12-02 | 2007-07-12 | Cholli Ashok L | Lubricant oil compositions |
WO2008005358A2 (en) | 2006-07-06 | 2008-01-10 | Polnox Corporation | Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same |
US7767853B2 (en) | 2006-10-20 | 2010-08-03 | Polnox Corporation | Antioxidants and methods of making and using the same |
-
2005
- 2005-07-19 AU AU2005269780A patent/AU2005269780A1/en not_active Abandoned
- 2005-07-19 CA CA002574581A patent/CA2574581A1/en not_active Abandoned
- 2005-07-19 AU AU2005269754A patent/AU2005269754A1/en not_active Abandoned
- 2005-07-19 US US11/184,724 patent/US20060041094A1/en not_active Abandoned
- 2005-07-19 EP EP05772822A patent/EP1771530B1/en not_active Not-in-force
- 2005-07-19 WO PCT/US2005/025513 patent/WO2006014605A2/en active Application Filing
- 2005-07-19 JP JP2007522638A patent/JP2008507276A/ja active Pending
- 2005-07-19 JP JP2007522671A patent/JP2008507613A/ja active Pending
- 2005-07-19 DE DE602005016559T patent/DE602005016559D1/de not_active Expired - Fee Related
- 2005-07-19 CA CA002574588A patent/CA2574588A1/en not_active Abandoned
- 2005-07-19 WO PCT/US2005/025646 patent/WO2006014674A2/en active Application Filing
- 2005-07-19 EP EP05773305A patent/EP1776394A2/en not_active Withdrawn
- 2005-07-19 AT AT05772822T patent/ATE442426T1/de not_active IP Right Cessation
- 2005-07-19 US US11/184,716 patent/US20060041087A1/en not_active Abandoned
-
2008
- 2008-05-28 US US12/154,911 patent/US7923587B2/en not_active Expired - Fee Related
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2010
- 2010-01-04 AU AU2010200011A patent/AU2010200011A1/en not_active Abandoned
Also Published As
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AU2010200011A1 (en) | 2010-01-28 |
WO2006014605A2 (en) | 2006-02-09 |
WO2006014605A3 (en) | 2006-05-04 |
ATE442426T1 (de) | 2009-09-15 |
JP2008507613A (ja) | 2008-03-13 |
US20080311065A1 (en) | 2008-12-18 |
US20060041087A1 (en) | 2006-02-23 |
AU2005269780A1 (en) | 2006-02-09 |
AU2005269754A1 (en) | 2006-02-09 |
JP2008507276A (ja) | 2008-03-13 |
US7923587B2 (en) | 2011-04-12 |
DE602005016559D1 (de) | 2009-10-22 |
WO2006014674A2 (en) | 2006-02-09 |
EP1771530A2 (en) | 2007-04-11 |
EP1776394A2 (en) | 2007-04-25 |
WO2006014674A3 (en) | 2006-04-20 |
EP1771530B1 (en) | 2009-09-09 |
CA2574581A1 (en) | 2006-02-09 |
US20060041094A1 (en) | 2006-02-23 |
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