CA2585469C - Procedes ameliores, fondes sur la polymerisation de radicaux par transfert d'atomes (ou de groupements) et (co)polymeres nouveaux ayant des structures et des proprietes utiles - Google Patents

Procedes ameliores, fondes sur la polymerisation de radicaux par transfert d'atomes (ou de groupements) et (co)polymeres nouveaux ayant des structures et des proprietes utiles Download PDF

Info

Publication number: CA2585469C
Authority: CA; Canada
Prior art keywords: alkyl; carbon atoms; group; aryl; polymer
Prior art date: 1995-11-15
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.): Expired - Lifetime

Application number

CA2585469A

Other languages

English (en)

Other versions

CA2585469A1 (fr

Inventor

Krzysztof Matyjaszewski

Simion Coca

Scott G. Gaynor

Dorota Greszta

Timothy E. Patten

Jin-Shan Wang

Jianhui Xia

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Carnegie Mellon University

Original Assignee

Carnegie Mellon University

Priority date (The priority date 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 date listed.)

1995-11-15

Filing date

1996-11-15

Publication date

2010-07-13

1995-11-15 Priority claimed from US08/559,309 external-priority patent/US5807937A/en

1996-11-15 Application filed by Carnegie Mellon University filed Critical Carnegie Mellon University

1997-05-22 Publication of CA2585469A1 publication Critical patent/CA2585469A1/fr

2010-07-13 Application granted granted Critical

2010-07-13 Publication of CA2585469C publication Critical patent/CA2585469C/fr

2016-11-15 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 204
238000000034 method Methods 0.000 title abstract description 112
230000008569 process Effects 0.000 title abstract description 62
238000010526 radical polymerization reaction Methods 0.000 title abstract description 48
238000012546 transfer Methods 0.000 title abstract description 28
239000000178 monomer Substances 0.000 claims abstract description 187
229920000642 polymer Polymers 0.000 claims abstract description 158
150000003623 transition metal compounds Chemical class 0.000 claims abstract description 45
230000000977 initiatory effect Effects 0.000 claims abstract description 26
238000007334 copolymerization reaction Methods 0.000 claims abstract description 15
238000006243 chemical reaction Methods 0.000 claims description 124
238000006116 polymerization reaction Methods 0.000 claims description 114
125000004432 carbon atom Chemical group C* 0.000 claims description 110
239000003999 initiator Substances 0.000 claims description 99
125000000217 alkyl group Chemical group 0.000 claims description 72
239000003446 ligand Substances 0.000 claims description 64
125000003118 aryl group Chemical group 0.000 claims description 63
-1 aralkenyl Chemical group 0.000 claims description 47
229910052723 transition metal Inorganic materials 0.000 claims description 43
229910052799 carbon Inorganic materials 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 40
150000003624 transition metals Chemical class 0.000 claims description 39
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 33
125000004429 atom Chemical group 0.000 claims description 31
229910052801 chlorine Inorganic materials 0.000 claims description 28
125000005843 halogen group Chemical group 0.000 claims description 27
125000001424 substituent group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 20
229910052794 bromium Inorganic materials 0.000 claims description 20
125000003710 aryl alkyl group Chemical group 0.000 claims description 19
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 16
229920005603 alternating copolymer Polymers 0.000 claims description 16
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 15
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150000004820 halides Chemical class 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 13
230000009257 reactivity Effects 0.000 claims description 12
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230000002441 reversible effect Effects 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 10
230000007423 decrease Effects 0.000 claims description 10
150000001340 alkali metals Chemical class 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 8
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 8
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
102220517591 Methyl-CpG-binding domain protein 3-like 2B_R11C_mutation Human genes 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 13
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
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241000682622 Andracantha sigma Species 0.000 claims 1
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229920001002 functional polymer Polymers 0.000 abstract description 7
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238000010560 atom transfer radical polymerization reaction Methods 0.000 description 78
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239000000203 mixture Substances 0.000 description 63
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229910021589 Copper(I) bromide Inorganic materials 0.000 description 42
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
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230000015572 biosynthetic process Effects 0.000 description 36
238000005227 gel permeation chromatography Methods 0.000 description 35
239000000047 product Substances 0.000 description 35
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 34
239000000460 chlorine Substances 0.000 description 34
229910021591 Copper(I) chloride Inorganic materials 0.000 description 33
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
238000003786 synthesis reaction Methods 0.000 description 29
229920001400 block copolymer Polymers 0.000 description 28
239000002904 solvent Substances 0.000 description 28
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
239000004793 Polystyrene Substances 0.000 description 25
229920002223 polystyrene Polymers 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 23
239000003054 catalyst Substances 0.000 description 20
ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 19
229920001971 elastomer Polymers 0.000 description 19
229910052786 argon Inorganic materials 0.000 description 18
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 17
239000011521 glass Substances 0.000 description 17
230000009849 deactivation Effects 0.000 description 16
238000007792 addition Methods 0.000 description 15
238000009826 distribution Methods 0.000 description 15
239000005060 rubber Substances 0.000 description 15
OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 14
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 14
238000005259 measurement Methods 0.000 description 14
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OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 13
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 13
230000009477 glass transition Effects 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
238000001542 size-exclusion chromatography Methods 0.000 description 13
239000007787 solid Substances 0.000 description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 12
229920002521 macromolecule Polymers 0.000 description 12
229920005604 random copolymer Polymers 0.000 description 12
238000001226 reprecipitation Methods 0.000 description 12
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 12
GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 11
238000001556 precipitation Methods 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
241001077660 Molo Species 0.000 description 10
239000012300 argon atmosphere Substances 0.000 description 10
CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 8
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
150000001350 alkyl halides Chemical group 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
239000010949 copper Substances 0.000 description 8
XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
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241000894007 species Species 0.000 description 8
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 8
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229910052748 manganese Inorganic materials 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000126 substance Substances 0.000 description 5
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QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 4
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FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
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239000002841 Lewis acid Substances 0.000 description 3
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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239000012190 activator Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 3
125000002091 cationic group Chemical group 0.000 description 3
238000010538 cationic polymerization reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
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CA2585469A 1995-11-15 1996-11-15 Procedes ameliores, fondes sur la polymerisation de radicaux par transfert d'atomes (ou de groupements) et (co)polymeres nouveaux ayant des structures et des proprietes utiles Expired - Lifetime CA2585469C (fr)

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Application Number	Priority Date	Filing Date	Title
US08/559,309		1995-11-15
US08/559,309 US5807937A (en)	1995-11-15	1995-11-15	Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties
CA002237055A CA2237055C (fr)	1995-11-15	1996-11-15	Procedes ameliores, fondes sur la polymerisation de radicaux par transfert d'atomes (ou de groupements) et (co)polymeres nouveaux ayant des structures et des proprietes utiles

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CA002237055A Division CA2237055C (fr)	1995-11-15	1996-11-15	Procedes ameliores, fondes sur la polymerisation de radicaux par transfert d'atomes (ou de groupements) et (co)polymeres nouveaux ayant des structures et des proprietes utiles

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CA2585469A1 CA2585469A1 (fr)	1997-05-22
CA2585469C true CA2585469C (fr)	2010-07-13

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Publication	Publication Date	Title
US5807937A (en)	1998-09-15	Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties
MXPA98003888A (en)	1999-07-06	Improved processes based on polymerization of radical transfer of atomo (or group) and novedosos (c0) polymers that have uti properties and structures
US6162882A (en)	2000-12-19	Preparation of novel homo- and copolymers using atom transfer radical polymerization
CA2216853C (fr)	2005-10-25	Nouveaux copolymeres et un nouveau procede de polymerisation base sur une polymerisation radicalaire par transfert d'atome (ou de groupe)
US20050090632A1 (en)	2005-04-28	Noel (co) polymers and a novel polymerization process based on atom (or group) transfer radical polymerization
CA2585469C (fr)	2010-07-13	Procedes ameliores, fondes sur la polymerisation de radicaux par transfert d'atomes (ou de groupements) et (co)polymeres nouveaux ayant des structures et des proprietes utiles
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