JP2006509860A - 原子移動ラジカル重合のためのアズラクトン開始剤 - Google Patents
原子移動ラジカル重合のためのアズラクトン開始剤 Download PDFInfo
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- JP2006509860A JP2006509860A JP2004559076A JP2004559076A JP2006509860A JP 2006509860 A JP2006509860 A JP 2006509860A JP 2004559076 A JP2004559076 A JP 2004559076A JP 2004559076 A JP2004559076 A JP 2004559076A JP 2006509860 A JP2006509860 A JP 2006509860A
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- 239000003999 initiator Substances 0.000 title claims abstract description 94
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 title abstract description 20
- 229920001577 copolymer Polymers 0.000 claims abstract description 46
- 239000000178 monomer Substances 0.000 claims description 76
- 229920000642 polymer Polymers 0.000 claims description 51
- -1 vinyl halide Chemical class 0.000 claims description 46
- 239000003446 ligand Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 229910052723 transition metal Inorganic materials 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 29
- 150000003624 transition metals Chemical class 0.000 claims description 29
- 125000005282 allenyl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 150000003623 transition metal compounds Chemical class 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 125000002577 pseudohalo group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 229920001400 block copolymer Polymers 0.000 claims description 10
- 230000009257 reactivity Effects 0.000 claims description 10
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- 230000002441 reversible effect Effects 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
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- 238000012644 addition polymerization Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007870 radical polymerization initiator Substances 0.000 claims 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims 1
- 229910017489 Cu I Inorganic materials 0.000 claims 1
- 150000003926 acrylamides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
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- 239000002904 solvent Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000010526 radical polymerization reaction Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000006413 ring segment Chemical group 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012876 carrier material Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 238000007142 ring opening reaction Methods 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000007306 functionalization reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229920000578 graft copolymer Polymers 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- UPBQIWUJMNGWHR-UHFFFAOYSA-N 2-(2-bromopropan-2-yl)-4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC(C)(Br)C1=NC(C)(C)C(=O)O1 UPBQIWUJMNGWHR-UHFFFAOYSA-N 0.000 description 3
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C)(C(O)=O)NC(C(*)(*)*)=O Chemical compound CC(C)(C(O)=O)NC(C(*)(*)*)=O 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Graft Or Block Polymers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/316,336 US6894133B2 (en) | 2002-12-11 | 2002-12-11 | Azlactone initiators for atom transfer radical polymerization |
| PCT/US2003/033335 WO2004052943A1 (en) | 2002-12-11 | 2003-10-20 | Azlactone initiators for atom transfer radical polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006509860A true JP2006509860A (ja) | 2006-03-23 |
| JP2006509860A5 JP2006509860A5 (enExample) | 2006-12-07 |
Family
ID=32505921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004559076A Pending JP2006509860A (ja) | 2002-12-11 | 2003-10-20 | 原子移動ラジカル重合のためのアズラクトン開始剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6894133B2 (enExample) |
| EP (1) | EP1569967B1 (enExample) |
| JP (1) | JP2006509860A (enExample) |
| AT (1) | ATE333472T1 (enExample) |
| AU (1) | AU2003298601A1 (enExample) |
| DE (1) | DE60306957T2 (enExample) |
| WO (1) | WO2004052943A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021507976A (ja) * | 2018-01-31 | 2021-02-25 | スリーエム イノベイティブ プロパティズ カンパニー | 光解離性β−ジカルボニル化合物 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6894133B2 (en) * | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
| US6992217B2 (en) * | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
| US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened azlactone photoiniferters for radical polymerization |
| US6753391B1 (en) * | 2003-05-05 | 2004-06-22 | 3M Innovative Properties Company | Ring-opened azlactone chain transfer agents for radical polymerization |
| US6762257B1 (en) * | 2003-05-05 | 2004-07-13 | 3M Innovative Properties Company | Azlactone chain transfer agents for radical polymerization |
| US8267210B2 (en) | 2003-10-08 | 2012-09-18 | Pride Mobility Products Corporation | Power supply assembly for motorized vehicles |
| US7919570B2 (en) | 2004-08-13 | 2011-04-05 | Nippon Soda Co., Ltd. | Multibranched polymer and method for producing the same |
| US7556858B2 (en) * | 2004-09-30 | 2009-07-07 | 3M Innovative Properties Company | Substrate with attached dendrimers |
| WO2007029794A1 (ja) | 2005-09-07 | 2007-03-15 | Nippon Soda Co., Ltd. | スターポリマー及びその製造方法 |
| EP1969397B1 (en) * | 2005-12-14 | 2017-11-08 | Novartis AG | Method for preparing silicone hydrogels |
| CN100422228C (zh) * | 2006-08-01 | 2008-10-01 | 苏州大学 | 含氟超支化-接枝嵌段聚合物及其制备 |
| US7666973B2 (en) * | 2007-07-30 | 2010-02-23 | Tyco Healthcare Group Lp | Carbonate copolymers |
| CN104024331B (zh) * | 2011-10-28 | 2016-10-19 | 3M创新有限公司 | 苯并噁嗪的胺/环氧树脂固化 |
| FR2997082B1 (fr) | 2012-10-18 | 2015-02-13 | Centre Nat Rech Scient | Reactifs de couplage multifonctionnels a fonction azlactone. |
| US10758456B2 (en) | 2015-11-06 | 2020-09-01 | 3M Innovative Properties Company | Redox polymerizable composition with photolabile transition metal complexes |
| WO2017079189A1 (en) | 2015-11-06 | 2017-05-11 | 3M Innovative Properties Company | Redox polymerizable dental composition with photolabile transition metal complexes |
| WO2017095704A1 (en) | 2015-12-03 | 2017-06-08 | 3M Innovative Properties Company | Redox polymerizable composition with photolabile reducing agents |
| US11472894B2 (en) | 2018-07-23 | 2022-10-18 | Carnegie Mellon University | Enzyme-assisted ATRP procedures |
| WO2020028715A1 (en) | 2018-08-01 | 2020-02-06 | Russell Alan J | Amino-reactive positively charged atrp initiators that maintain their positive charge during synthesis of biomacro-initiators |
| US20210388337A1 (en) * | 2018-10-13 | 2021-12-16 | Carnegie Mellon University | Protein-polymer conjugates and methods for their preparation |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3488327A (en) * | 1967-06-30 | 1970-01-06 | Roehm & Haas Gmbh | Preparation of coating materials |
| US4485236A (en) * | 1982-09-27 | 1984-11-27 | Minnesota Mining And Manufacturing Company | Azlactone-functional compounds |
| US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5807937A (en) | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| AU735085B2 (en) | 1996-06-12 | 2001-06-28 | Warwick Effect Polymers Limited | Polymerisation catalyst and process |
| US6169102B1 (en) * | 1996-06-25 | 2001-01-02 | Takeda Chemical Industries, Ltd. | Oxazolone derivatives and their use as anti-Helicobacter pylori agent |
| WO1998022449A1 (en) * | 1996-11-15 | 1998-05-28 | Ube Industries, Ltd. | 5-alkoxy-2(3h)-oxazolone compounds and process for the preparation thereof |
| US6566403B1 (en) * | 1997-06-16 | 2003-05-20 | Dow Agrosciences Llc | N-acetonylbenzamide fungicides |
| WO1999003114A2 (en) | 1997-07-11 | 1999-01-21 | Bc Components Holdings B.V. | High-voltage resistor and high-voltage supply comprising such a high-voltage resistor |
| US6143848A (en) | 1997-10-23 | 2000-11-07 | The B.F.Goodrich Company | End-functionalized polymers by controlled free-radical polymerization process and polymers made therefrom |
| EP1054906B2 (en) | 1997-12-18 | 2013-04-10 | Commonwealth Scientific and Industrial Research Organisation | Polymerization process with living characteristics and polymers made therefrom |
| TW574236B (en) | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
| US6569969B2 (en) | 2000-09-28 | 2003-05-27 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
| AU2001296670A1 (en) | 2000-10-06 | 2002-04-15 | Carnegie-Mellon University | A catalyst system for controlled polymerization |
| JP2002128748A (ja) * | 2000-10-23 | 2002-05-09 | Kumiai Chem Ind Co Ltd | カルボン酸アミド誘導体及び農園芸用殺菌剤 |
| US6992217B2 (en) | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
| US6894133B2 (en) * | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
| US6677413B1 (en) | 2003-02-05 | 2004-01-13 | 3M Innovative Properties Company | Azlactone initiators for nitroxide-mediated polymerization |
| US6680362B1 (en) * | 2003-02-05 | 2004-01-20 | 3M Innovative Properties Company | Ring-opened azlactone initiators for nitroxide-mediated polymerization |
| US6747104B1 (en) * | 2003-03-21 | 2004-06-08 | 3M Innovative Properties Company | Azlactone photoiniferters for radical polymerization |
| US6762257B1 (en) * | 2003-05-05 | 2004-07-13 | 3M Innovative Properties Company | Azlactone chain transfer agents for radical polymerization |
| US6753391B1 (en) * | 2003-05-05 | 2004-06-22 | 3M Innovative Properties Company | Ring-opened azlactone chain transfer agents for radical polymerization |
-
2002
- 2002-12-11 US US10/316,336 patent/US6894133B2/en not_active Expired - Lifetime
-
2003
- 2003-10-20 AU AU2003298601A patent/AU2003298601A1/en not_active Abandoned
- 2003-10-20 JP JP2004559076A patent/JP2006509860A/ja active Pending
- 2003-10-20 EP EP03796352A patent/EP1569967B1/en not_active Expired - Lifetime
- 2003-10-20 DE DE60306957T patent/DE60306957T2/de not_active Expired - Lifetime
- 2003-10-20 WO PCT/US2003/033335 patent/WO2004052943A1/en not_active Ceased
- 2003-10-20 AT AT03796352T patent/ATE333472T1/de not_active IP Right Cessation
-
2004
- 2004-09-29 US US10/953,001 patent/US6969749B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021507976A (ja) * | 2018-01-31 | 2021-02-25 | スリーエム イノベイティブ プロパティズ カンパニー | 光解離性β−ジカルボニル化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1569967B1 (en) | 2006-07-19 |
| AU2003298601A1 (en) | 2004-06-30 |
| US6894133B2 (en) | 2005-05-17 |
| US20040116616A1 (en) | 2004-06-17 |
| DE60306957D1 (de) | 2006-08-31 |
| ATE333472T1 (de) | 2006-08-15 |
| US20050065300A1 (en) | 2005-03-24 |
| DE60306957T2 (de) | 2007-03-01 |
| EP1569967A1 (en) | 2005-09-07 |
| WO2004052943A1 (en) | 2004-06-24 |
| US6969749B2 (en) | 2005-11-29 |
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