TWI291472B

TWI291472B - Catalytic processes for the controlled polymerization of free radically (co)polymerizable monomers and functional polymeric systems prepared thereby

Catalytic processes for the controlled polymerization of free radically (co)polymerizable monomers and functional polymeric systems prepared thereby Download PDF

Info

Publication number: TWI291472B
Authority: TW; Taiwan
Prior art keywords: transition metal; polymerization; polymer; group; initiator
Prior art date: 1999-03-23

Application number

TW089105534A

Other languages

English (en)

Chinese (zh)

Inventor

Krzysztof Matyjaszewski

Scott G Gaynor

Hyun-Jong Paik

Tomislav Pintauer

Jeff Pyun

Original Assignee

Univ Carnegie Mellon

Priority date

1999-03-23

Filing date

2000-03-23

Publication date

2007-12-21

2000-03-23 Application filed by Univ Carnegie Mellon filed Critical Univ Carnegie Mellon

2007-12-21 Application granted granted Critical

2007-12-21 Publication of TWI291472B publication Critical patent/TWI291472B/zh

Links

238000006116 polymerization reaction Methods 0.000 title claims abstract description 354
239000000178 monomer Substances 0.000 title claims abstract description 216
238000000034 method Methods 0.000 title claims abstract description 207
230000003197 catalytic effect Effects 0.000 title abstract description 29
230000008569 process Effects 0.000 title abstract description 29
229920000642 polymer Polymers 0.000 claims abstract description 342
239000003999 initiator Substances 0.000 claims abstract description 187
229910052723 transition metal Inorganic materials 0.000 claims abstract description 164
239000003054 catalyst Substances 0.000 claims abstract description 161
239000003446 ligand Substances 0.000 claims abstract description 151
150000003624 transition metals Chemical class 0.000 claims abstract description 123
239000000463 material Substances 0.000 claims abstract description 61
238000012546 transfer Methods 0.000 claims abstract description 55
150000003839 salts Chemical class 0.000 claims abstract description 40
239000007787 solid Substances 0.000 claims abstract description 39
238000006479 redox reaction Methods 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims description 273
150000003254 radicals Chemical class 0.000 claims description 218
-1 transition metal salt Chemical class 0.000 claims description 163
239000007858 starting material Substances 0.000 claims description 84
229920001577 copolymer Polymers 0.000 claims description 79
230000002441 reversible effect Effects 0.000 claims description 71
239000003456 ion exchange resin Substances 0.000 claims description 70
229920003303 ion-exchange polymer Polymers 0.000 claims description 70
239000002904 solvent Substances 0.000 claims description 63
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 58
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 57
239000010949 copper Substances 0.000 claims description 52
125000000524 functional group Chemical group 0.000 claims description 50
239000002245 particle Substances 0.000 claims description 48
150000002500 ions Chemical class 0.000 claims description 42
229910052757 nitrogen Inorganic materials 0.000 claims description 40
150000003623 transition metal compounds Chemical group 0.000 claims description 38
239000003795 chemical substances by application Substances 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 35
239000000126 substance Substances 0.000 claims description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
229910052802 copper Inorganic materials 0.000 claims description 24
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 23
230000003647 oxidation Effects 0.000 claims description 23
238000007254 oxidation reaction Methods 0.000 claims description 23
239000000839 emulsion Substances 0.000 claims description 21
229910052742 iron Inorganic materials 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
229910052751 metal Inorganic materials 0.000 claims description 16
239000002184 metal Substances 0.000 claims description 16
230000000379 polymerizing effect Effects 0.000 claims description 13
150000004820 halides Chemical class 0.000 claims description 12
239000002798 polar solvent Substances 0.000 claims description 12
150000002978 peroxides Chemical class 0.000 claims description 11
238000000354 decomposition reaction Methods 0.000 claims description 9
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
239000000725 suspension Substances 0.000 claims description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
125000002843 carboxylic acid group Chemical group 0.000 claims description 6
229910000420 cerium oxide Inorganic materials 0.000 claims description 6
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 6
230000036961 partial effect Effects 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
150000003926 acrylamides Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
238000001179 sorption measurement Methods 0.000 claims description 4
229910052785 arsenic Inorganic materials 0.000 claims description 3
239000011651 chromium Substances 0.000 claims description 3
239000002905 metal composite material Substances 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
239000012530 fluid Substances 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
150000003003 phosphines Chemical class 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims 1
238000011437 continuous method Methods 0.000 claims 1
RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
125000005497 tetraalkylphosphonium group Chemical group 0.000 claims 1
238000005859 coupling reaction Methods 0.000 abstract description 60
238000002360 preparation method Methods 0.000 abstract description 38
230000003993 interaction Effects 0.000 abstract description 13
230000006872 improvement Effects 0.000 abstract description 10
238000011161 development Methods 0.000 abstract description 7
230000006870 function Effects 0.000 abstract description 7
229920001002 functional polymer Polymers 0.000 abstract description 3
238000011084 recovery Methods 0.000 abstract description 2
230000019771 cognition Effects 0.000 abstract 1
230000001404 mediated effect Effects 0.000 abstract 1
238000010560 atom transfer radical polymerization reaction Methods 0.000 description 226
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 148
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229910021589 Copper(I) bromide Inorganic materials 0.000 description 107
125000004429 atom Chemical group 0.000 description 102
239000011572 manganese Substances 0.000 description 93
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 85
UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 81
239000000243 solution Substances 0.000 description 79
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 78
230000015572 biosynthetic process Effects 0.000 description 74
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238000002474 experimental method Methods 0.000 description 57
238000005755 formation reaction Methods 0.000 description 51
230000000694 effects Effects 0.000 description 50
238000007792 addition Methods 0.000 description 49
239000000203 mixture Substances 0.000 description 47
238000010168 coupling process Methods 0.000 description 46
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
238000009826 distribution Methods 0.000 description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
238000001542 size-exclusion chromatography Methods 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
150000001336 alkenes Chemical class 0.000 description 35
230000008878 coupling Effects 0.000 description 35
239000004094 surface-active agent Substances 0.000 description 35
101150084548 Cubn gene Proteins 0.000 description 34
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 34
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 30
229920000578 graft copolymer Polymers 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
238000003786 synthesis reaction Methods 0.000 description 28
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230000001276 controlling effect Effects 0.000 description 26
230000002079 cooperative effect Effects 0.000 description 26
239000012071 phase Substances 0.000 description 25
239000007822 coupling agent Substances 0.000 description 24
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 23
239000002131 composite material Substances 0.000 description 23
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 22
239000012967 coordination catalyst Substances 0.000 description 22
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 21
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238000007306 functionalization reaction Methods 0.000 description 20
241000894007 species Species 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
230000009849 deactivation Effects 0.000 description 19
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 19
ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 19
238000007639 printing Methods 0.000 description 19
238000010526 radical polymerization reaction Methods 0.000 description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 18
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
229910052794 bromium Inorganic materials 0.000 description 18
238000010586 diagram Methods 0.000 description 18
230000007246 mechanism Effects 0.000 description 18
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 18
229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 17
239000004793 Polystyrene Substances 0.000 description 16
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230000035484 reaction time Effects 0.000 description 15
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 15
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
230000000977 initiatory effect Effects 0.000 description 14
238000003756 stirring Methods 0.000 description 14
229920002319 Poly(methyl acrylate) Polymers 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
239000000523 sample Substances 0.000 description 13
VHJFWJXYEWHCGD-UHFFFAOYSA-N 4-nonyl-2-(4-nonylpyridin-2-yl)pyridine Chemical compound CCCCCCCCCC1=CC=NC(C=2N=CC=C(CCCCCCCCC)C=2)=C1 VHJFWJXYEWHCGD-UHFFFAOYSA-N 0.000 description 12
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
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238000004132 cross linking Methods 0.000 description 12
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 12
229920001467 poly(styrenesulfonates) Polymers 0.000 description 12
238000011069 regeneration method Methods 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
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150000001450 anions Chemical class 0.000 description 11
125000001246 bromo group Chemical group Br* 0.000 description 11
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 11
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238000004458 analytical method Methods 0.000 description 10
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238000012360 testing method Methods 0.000 description 10
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RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
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SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 8
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238000005481 NMR spectroscopy Methods 0.000 description 6
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229910052786 argon Inorganic materials 0.000 description 6
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
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150000004699 copper complex Chemical class 0.000 description 6
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