DE60306957T2 - Azlacton -initiatoren für atomtransferradikalpolymerisation - Google Patents
Azlacton -initiatoren für atomtransferradikalpolymerisation Download PDFInfo
- Publication number
- DE60306957T2 DE60306957T2 DE60306957T DE60306957T DE60306957T2 DE 60306957 T2 DE60306957 T2 DE 60306957T2 DE 60306957 T DE60306957 T DE 60306957T DE 60306957 T DE60306957 T DE 60306957T DE 60306957 T2 DE60306957 T2 DE 60306957T2
- Authority
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- Germany
- Prior art keywords
- group
- initiator
- transition metal
- carbon
- monomer
- 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.)
- Expired - Lifetime
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- 239000003999 initiator Substances 0.000 title claims abstract description 87
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 title abstract description 17
- 229920001577 copolymer Polymers 0.000 claims abstract description 40
- 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 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims description 71
- 229920000642 polymer Polymers 0.000 claims description 44
- 239000003446 ligand Substances 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229910052723 transition metal Inorganic materials 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 29
- 150000003624 transition metals Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 150000003623 transition metal compounds Chemical class 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 238000010526 radical polymerization reaction Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 11
- 125000002577 pseudohalo group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 7
- 230000002441 reversible effect Effects 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 238000012644 addition polymerization Methods 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000007870 radical polymerization initiator Substances 0.000 claims description 2
- -1 acyclic hydrocarbon radicals Chemical class 0.000 description 37
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 238000002360 preparation method Methods 0.000 description 11
- 125000006413 ring segment Chemical group 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 9
- 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 230000009257 reactivity Effects 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
- 238000007792 addition Methods 0.000 description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 230000002829 reductive effect Effects 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 0 CCN(C1NC1*C(C)(*)*)C(*)(*)C*CN*(**)=O Chemical compound CCN(C1NC1*C(C)(*)*)C(*)(*)C*CN*(**)=O 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 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
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 230000007704 transition Effects 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
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- 150000003141 primary amines Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
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- 239000010703 silicon Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052714 tellurium Inorganic materials 0.000 description 3
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
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- ICOBVAUUTLLSTD-UHFFFAOYSA-N 2-(2-bromopropanoylamino)-2-methylpropanoic acid Chemical compound CC(Br)C(=O)NC(C)(C)C(O)=O ICOBVAUUTLLSTD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DDTDSRVXVCCMSS-UHFFFAOYSA-N 2-[(2-bromo-2-methylpropanoyl)amino]-2-methylpropanoic acid Chemical compound CC(C)(Br)C(=O)NC(C)(C)C(O)=O DDTDSRVXVCCMSS-UHFFFAOYSA-N 0.000 description 2
- PSFZNYTZFAOCFH-UHFFFAOYSA-N 2-[(2-chloroacetyl)amino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)CCl PSFZNYTZFAOCFH-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- Chemical & Material Sciences (AREA)
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- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US316336 | 2002-12-11 | ||
| 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 |
|---|---|
| DE60306957D1 DE60306957D1 (de) | 2006-08-31 |
| DE60306957T2 true DE60306957T2 (de) | 2007-03-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60306957T Expired - Lifetime DE60306957T2 (de) | 2002-12-11 | 2003-10-20 | Azlacton -initiatoren für atomtransferradikalpolymerisation |
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) |
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| 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 |
| US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened 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 |
| 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 |
| WO2007068453A2 (en) * | 2005-12-14 | 2007-06-21 | 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 |
| US9695273B2 (en) * | 2011-10-28 | 2017-07-04 | 3M Innovative Properties Company | Amine/epoxy curing of benzoxazines |
| FR2997082B1 (fr) | 2012-10-18 | 2015-02-13 | Centre Nat Rech Scient | Reactifs de couplage multifonctionnels a fonction azlactone. |
| US10617607B2 (en) | 2015-11-06 | 2020-04-14 | 3M Innovative Properties Company | Redox polymerizable dental composition with photolabile transition metal complexes |
| CN108348403B (zh) | 2015-11-06 | 2021-06-18 | 3M创新有限公司 | 含有光不稳定过渡金属络合物的氧化还原可聚合组合物 |
| EP3383924B1 (en) | 2015-12-03 | 2021-04-14 | 3M Innovative Properties Company | Redox polymerizable composition with photolabile reducing agents |
| JP6938794B2 (ja) * | 2018-01-31 | 2021-09-22 | 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 |
| US11472894B2 (en) | 2018-07-23 | 2022-10-18 | Carnegie Mellon University | Enzyme-assisted ATRP procedures |
| US12053529B2 (en) | 2018-08-01 | 2024-08-06 | Carnegie Mellon University | Amino-reactive positively charged ATRP initiators that maintain their positive charge during synthesis of biomacro-initiators |
| WO2020123023A2 (en) * | 2018-10-13 | 2020-06-18 | Carnegie Mellon University | Protein-polymer conjugates and methods for their preparation |
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| 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 |
| US6310149B1 (en) | 1996-06-12 | 2001-10-30 | University Of Warwick | Polymerization 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 |
| CA2309279C (en) | 1997-12-18 | 2009-07-14 | E.I. Du Pont De Nemours And Company | 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 |
| WO2002028914A2 (en) | 2000-10-06 | 2002-04-11 | 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 |
| 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 |
| US6680362B1 (en) | 2003-02-05 | 2004-01-20 | 3M Innovative Properties Company | Ring-opened azlactone initiators for nitroxide-mediated polymerization |
| US6677413B1 (en) | 2003-02-05 | 2004-01-13 | 3M Innovative Properties Company | Azlactone initiators for nitroxide-mediated polymerization |
| US6747104B1 (en) | 2003-03-21 | 2004-06-08 | 3M Innovative Properties Company | 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 |
-
2002
- 2002-12-11 US US10/316,336 patent/US6894133B2/en not_active Expired - Lifetime
-
2003
- 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 AT AT03796352T patent/ATE333472T1/de not_active IP Right Cessation
- 2003-10-20 AU AU2003298601A patent/AU2003298601A1/en not_active Abandoned
- 2003-10-20 WO PCT/US2003/033335 patent/WO2004052943A1/en not_active Ceased
-
2004
- 2004-09-29 US US10/953,001 patent/US6969749B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004052943A1 (en) | 2004-06-24 |
| AU2003298601A1 (en) | 2004-06-30 |
| DE60306957D1 (de) | 2006-08-31 |
| JP2006509860A (ja) | 2006-03-23 |
| US6894133B2 (en) | 2005-05-17 |
| EP1569967A1 (en) | 2005-09-07 |
| US20050065300A1 (en) | 2005-03-24 |
| US6969749B2 (en) | 2005-11-29 |
| US20040116616A1 (en) | 2004-06-17 |
| ATE333472T1 (de) | 2006-08-15 |
| EP1569967B1 (en) | 2006-07-19 |
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