JP5095942B2 - 制御したラジカル重合用のS−(α,α’−二置換−α”−酢酸)置換ジチオカーボネート誘導体、方法およびそれから製造したポリマー - Google Patents
制御したラジカル重合用のS−(α,α’−二置換−α”−酢酸)置換ジチオカーボネート誘導体、方法およびそれから製造したポリマー Download PDFInfo
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- JP5095942B2 JP5095942B2 JP2005501651A JP2005501651A JP5095942B2 JP 5095942 B2 JP5095942 B2 JP 5095942B2 JP 2005501651 A JP2005501651 A JP 2005501651A JP 2005501651 A JP2005501651 A JP 2005501651A JP 5095942 B2 JP5095942 B2 JP 5095942B2
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- 229920000642 polymer Polymers 0.000 title claims description 146
- 238000000034 method Methods 0.000 title claims description 67
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- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical class O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 title claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 104
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- 150000002576 ketones Chemical class 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 24
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- 239000007795 chemical reaction product Substances 0.000 claims description 9
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
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- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
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- HUMLQUKVJARKRN-UHFFFAOYSA-M sodium;n,n-dibutylcarbamodithioate Chemical compound [Na+].CCCCN(C([S-])=S)CCCC HUMLQUKVJARKRN-UHFFFAOYSA-M 0.000 description 1
- VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- KHJNXCATZZIGAX-UHFFFAOYSA-N tert-butyl 2-ethyl-2-methylheptaneperoxoate Chemical compound CCCCCC(C)(CC)C(=O)OOC(C)(C)C KHJNXCATZZIGAX-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 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
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/194—Radicals derived from thio- or thiono carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/16—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/18—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
- C07C333/20—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
- C07C333/24—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/28—Polythiocarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/278,335 | 2002-10-23 | ||
| US10/278,335 US7205368B2 (en) | 2000-02-16 | 2002-10-23 | S-(α, α′-disubstituted-α′ ′-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom |
| US10/681,679 US7335788B2 (en) | 2000-02-16 | 2003-10-08 | S-(α, α′-disubstituted-α″-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom |
| US10/681,679 | 2003-10-08 | ||
| PCT/US2003/033476 WO2004037780A1 (en) | 2002-10-23 | 2003-10-21 | S-(a, a’ -DISUBSTITUTED-a” -ACETIC ACID) SUBSTITUTED DITHIOCARBONATE DERIVATIVES FOR CONTROLLED RADICAL POLYMERIZATIONS, PROCESS AND POLYMERS MADE THEREFROM |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006503971A JP2006503971A (ja) | 2006-02-02 |
| JP2006503971A5 JP2006503971A5 (enExample) | 2007-01-25 |
| JP5095942B2 true JP5095942B2 (ja) | 2012-12-12 |
Family
ID=32179472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005501651A Expired - Fee Related JP5095942B2 (ja) | 2002-10-23 | 2003-10-21 | 制御したラジカル重合用のS−(α,α’−二置換−α”−酢酸)置換ジチオカーボネート誘導体、方法およびそれから製造したポリマー |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7335788B2 (enExample) |
| EP (1) | EP1554241B1 (enExample) |
| JP (1) | JP5095942B2 (enExample) |
| AU (1) | AU2003280005A1 (enExample) |
| WO (1) | WO2004037780A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7495050B2 (en) * | 2000-02-16 | 2009-02-24 | Lubrizol Advanced Materials, Inc. | Associative thickeners for aqueous systems |
| US7557235B2 (en) | 2000-02-16 | 2009-07-07 | Lubrizol Advanced Materials, Inc. | Hydroxyl-terminated thiocarbonate containing compounds, polymers, and copolymers, and polyurethanes and urethane acrylics made therefrom |
| FR2868072B1 (fr) * | 2004-07-28 | 2006-06-30 | Coatex Soc Par Actions Simplif | Polymeres obtenus par l'utilisation de composes soufres comme agents de transfert pour la polymerisation radicalaire controlee de l'acide acrylique et leurs applications |
| US8137754B2 (en) * | 2004-08-06 | 2012-03-20 | Lubrizol Advanced Materials, Inc. | Hydroxyl-terminated thiocarbonate containing compounds, polymers, and copolymers, and polyurethanes and urethane acrylics made therefrom |
| WO2006020281A1 (en) | 2004-08-06 | 2006-02-23 | Noveon, Inc. | Polyurethanes and urethane acrylics made from hydroxyl-terminated thiocarbonate containing compounds |
| WO2006023790A1 (en) * | 2004-08-20 | 2006-03-02 | Noveon, Inc. | Curable thiocarbonate compounds and compositions |
| US7671152B2 (en) * | 2005-12-22 | 2010-03-02 | The Goodyear Tire & Rubber Company | Surfactantless synthesis of amphiphilic cationic block copolymers |
| US20080153982A1 (en) * | 2006-12-20 | 2008-06-26 | John Ta-Yuan Lai | Vinyl-Thiocarbonate and Polyol Containing Block Copolymers |
| WO2009012202A1 (en) | 2007-07-13 | 2009-01-22 | Kemira Oyj | Mineral dispersants and methods for preparing mineral slurries using the same |
| CN104059006A (zh) * | 2007-08-09 | 2014-09-24 | 卢布里佐尔公司 | 制备取代的三硫代碳酸酯衍生物的方法 |
| FR2931154B1 (fr) * | 2008-05-14 | 2011-04-08 | Univ Paris Curie | Copolymere amphiphile a blocs, procede pour sa preparation |
| NZ594255A (en) * | 2009-01-23 | 2013-09-27 | Commw Scient Ind Res Org | RAFT polymerisation |
| FR2962441A1 (fr) | 2010-07-08 | 2012-01-13 | Arkema France | Agents raft a odeur amelioree et polymeres a odeur amelioree obtenus a l'aide de ces agents |
| CN103880995B (zh) * | 2014-04-10 | 2016-09-28 | 苏州大学 | 一种活性可控自由基聚合的方法和乙烯基聚合物 |
| CN106631882B (zh) * | 2016-09-01 | 2020-02-07 | 吕梁学院 | 多氨类二硫代甲酸亚硫酸盐衍生物及其制备方法和应用 |
| CN111378366B (zh) * | 2018-12-27 | 2022-11-18 | 安集微电子(上海)有限公司 | 一种化学机械抛光液及其应用 |
| CN119176890B (zh) * | 2024-11-19 | 2025-03-21 | 湖南福尔程科技股份有限公司 | 乳液丁苯橡胶聚合体系的环保型终止剂、预制剂、制备及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3285945A (en) | 1966-11-15 | Process for the production of ester salts | ||
| US3285949A (en) | 1964-04-17 | 1966-11-15 | Goodrich Co B F | Carboxyl-terminated butadiene polymers prepared in tertiary butanol with bis-azocyano acid initiation |
| US3992432A (en) | 1967-04-05 | 1976-11-16 | Continental Oil Company | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
| FI42085B (enExample) | 1968-05-20 | 1970-02-02 | Laeaeketehdas Orion Oy | |
| US3770698A (en) | 1971-12-17 | 1973-11-06 | C Riew | Phenol terminated carboxy containing diene elastomers |
| US3860641A (en) | 1972-10-21 | 1975-01-14 | Akzo Nv | Process for the production of thioglycolic acid, beta-mercaptopropionic acid or salts thereof |
| US3928491A (en) | 1973-12-26 | 1975-12-23 | Youngstown Sheet And Tube Co | Modified vinyl ester resin and pipe made therefrom |
| US4769419A (en) | 1986-12-01 | 1988-09-06 | Dawdy Terrance H | Modified structural adhesives |
| US5055515A (en) | 1988-09-09 | 1991-10-08 | The B. F. Goodrich Company | Flexible overpolymers of vinyl chloride polymers on ethylene copolymers |
| US5258445A (en) | 1990-03-08 | 1993-11-02 | The B. F. Goodrich Company | Fiber-reinforced thermoplastic molding compositions using a copolyester |
| US5198510A (en) | 1990-04-27 | 1993-03-30 | The B. F. Goodrich Company | Modification of vinyl ester resins with reactive liquid polymers |
| CA2040035A1 (en) | 1990-04-27 | 1991-10-28 | Robert J. Bertsch | Synthesis of low viscosity non-functional terminated polymers |
| US5157077A (en) | 1990-04-27 | 1992-10-20 | The B. F. Goodrich Company | Epoxy resin systems modified with statistical monofunctional reactive polymers |
| US5140068A (en) | 1990-04-27 | 1992-08-18 | The B. F. Goodrich Company | Epoxy resin systems modified with low viscosity statistical monofunctional reactive polymers |
| JPH05155950A (ja) * | 1991-12-09 | 1993-06-22 | Mitsubishi Petrochem Co Ltd | アニオン系高分子界面活性剤およびその利用 |
| US5385963A (en) | 1992-01-30 | 1995-01-31 | Gencorp Inc. | Unsaturated polyester-modified flexible copolymers for use in sheet molding compositions |
| JP3312552B2 (ja) * | 1995-03-31 | 2002-08-12 | 住友化学工業株式会社 | スチレン系重合体の製造方法 |
| ATE210684T1 (de) | 1996-07-10 | 2001-12-15 | Du Pont | POLYMERISATION MIT ßLIVINGß KENNZEICHEN |
| US5789357A (en) * | 1997-01-10 | 1998-08-04 | Uniroyal Chemical Company, Inc. | Dithiocarbamyl carboxylic acids and their use as multifunctional additives for lubricating oils |
| FR2764892B1 (fr) | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
| DE69840423D1 (de) | 1997-07-21 | 2009-02-12 | Commw Scient Ind Res Org | Synthese von dithioester-kettentransferagentien |
| BR9815179A (pt) | 1997-12-18 | 2000-10-10 | Du Pont | Processo para produzir um polìmero, polìmero, composição de revestimento e agente de transferência de cadeia. |
| AU1883199A (en) | 1997-12-31 | 1999-07-26 | Rhodia Chimie | Method for block polymer synthesis by controlled radical polymerisation from dithiocarbamate compounds |
| US6596899B1 (en) * | 2000-02-16 | 2003-07-22 | Noveon Ip Holdings Corp. | S,S′BIS-(α, α′-DISUBSTITUTED-α″-ACETIC ACID)- TRITHIOCARBONATES AND DERIVATIVES AS INITIATOR-CHAIN TRANSFER AGENT-TERMINATOR FOR CONTROLLED RADICAL POLYMERIZATIONS AND THE PROCESS FOR MAKING THE SAME |
| US6395850B1 (en) | 2000-09-28 | 2002-05-28 | Symyx Technologies, Inc. | Heterocycle containing control agents for living-type free radical polymerization |
| US6380335B1 (en) | 2000-09-28 | 2002-04-30 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
-
2003
- 2003-10-08 US US10/681,679 patent/US7335788B2/en not_active Expired - Lifetime
- 2003-10-21 EP EP03773311.0A patent/EP1554241B1/en not_active Expired - Lifetime
- 2003-10-21 AU AU2003280005A patent/AU2003280005A1/en not_active Abandoned
- 2003-10-21 WO PCT/US2003/033476 patent/WO2004037780A1/en not_active Ceased
- 2003-10-21 JP JP2005501651A patent/JP5095942B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20040073056A1 (en) | 2004-04-15 |
| EP1554241B1 (en) | 2015-03-18 |
| AU2003280005A1 (en) | 2004-05-13 |
| WO2004037780A1 (en) | 2004-05-06 |
| EP1554241A1 (en) | 2005-07-20 |
| US7335788B2 (en) | 2008-02-26 |
| JP2006503971A (ja) | 2006-02-02 |
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