DE60024605T2 - Katalytische prozesse für die kontrollierte polymerisation von freiradikalischen, copolymerisierbaren monomeren und funktionellpolymersysteme hergestellt davon - Google Patents
Katalytische prozesse für die kontrollierte polymerisation von freiradikalischen, copolymerisierbaren monomeren und funktionellpolymersysteme hergestellt davon Download PDFInfo
- Publication number
- DE60024605T2 DE60024605T2 DE60024605T DE60024605T DE60024605T2 DE 60024605 T2 DE60024605 T2 DE 60024605T2 DE 60024605 T DE60024605 T DE 60024605T DE 60024605 T DE60024605 T DE 60024605T DE 60024605 T2 DE60024605 T2 DE 60024605T2
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- polymer
- transition metal
- atrp
- initiator
- 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
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 336
- 239000000178 monomer Substances 0.000 title claims description 238
- 238000000034 method Methods 0.000 title claims description 183
- 230000008569 process Effects 0.000 title description 63
- 230000003197 catalytic effect Effects 0.000 title description 27
- 229920001002 functional polymer Polymers 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 225
- 239000003999 initiator Substances 0.000 claims description 215
- 239000003054 catalyst Substances 0.000 claims description 181
- 229910052723 transition metal Inorganic materials 0.000 claims description 146
- 239000003446 ligand Substances 0.000 claims description 141
- 239000010949 copper Substances 0.000 claims description 122
- -1 transition metal salt Chemical class 0.000 claims description 116
- 150000003624 transition metals Chemical class 0.000 claims description 101
- 239000000463 material Substances 0.000 claims description 92
- 150000003254 radicals Chemical class 0.000 claims description 90
- 229920001577 copolymer Polymers 0.000 claims description 74
- 239000002904 solvent Substances 0.000 claims description 65
- 230000002441 reversible effect Effects 0.000 claims description 57
- 125000000524 functional group Chemical group 0.000 claims description 51
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 47
- 238000012546 transfer Methods 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 230000003647 oxidation Effects 0.000 claims description 24
- 238000007254 oxidation reaction Methods 0.000 claims description 24
- 229910052802 copper Inorganic materials 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 22
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 20
- 239000011572 manganese Substances 0.000 claims description 20
- 239000002798 polar solvent Substances 0.000 claims description 18
- 229910052742 iron Inorganic materials 0.000 claims description 17
- 150000004820 halides Chemical class 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 150000003926 acrylamides Chemical class 0.000 claims description 8
- 229910052748 manganese Inorganic materials 0.000 claims description 5
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 346
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 248
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 158
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 153
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 141
- 230000015572 biosynthetic process Effects 0.000 description 115
- 125000004429 atom Chemical group 0.000 description 109
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 92
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 87
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 82
- 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 82
- 239000002245 particle Substances 0.000 description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 229920001400 block copolymer Polymers 0.000 description 77
- 238000003786 synthesis reaction Methods 0.000 description 69
- 239000003456 ion exchange resin Substances 0.000 description 68
- 229920003303 ion-exchange polymer Polymers 0.000 description 68
- 238000005859 coupling reaction Methods 0.000 description 67
- 238000007792 addition Methods 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000011347 resin Substances 0.000 description 59
- 229920005989 resin Polymers 0.000 description 59
- 238000010168 coupling process Methods 0.000 description 56
- 238000002474 experimental method Methods 0.000 description 56
- 239000000203 mixture Substances 0.000 description 53
- 238000001542 size-exclusion chromatography Methods 0.000 description 52
- 238000005755 formation reaction Methods 0.000 description 48
- 230000000977 initiatory effect Effects 0.000 description 47
- 230000008878 coupling Effects 0.000 description 44
- 150000001336 alkenes Chemical class 0.000 description 41
- 238000009826 distribution Methods 0.000 description 40
- 150000003839 salts Chemical class 0.000 description 40
- 239000007787 solid Substances 0.000 description 39
- 230000000694 effects Effects 0.000 description 37
- 229920000578 graft copolymer Polymers 0.000 description 37
- 239000004094 surface-active agent Substances 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 36
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 34
- 238000013459 approach Methods 0.000 description 32
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 30
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 29
- 238000004519 manufacturing process Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 28
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- 150000003623 transition metal compounds Chemical class 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 26
- 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 description 25
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 24
- 239000004342 Benzoyl peroxide Substances 0.000 description 23
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 23
- 235000019400 benzoyl peroxide Nutrition 0.000 description 23
- 239000000839 emulsion Substances 0.000 description 23
- 239000004793 Polystyrene Substances 0.000 description 22
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 22
- 125000006414 CCl Chemical group ClC* 0.000 description 21
- 238000007306 functionalization reaction Methods 0.000 description 21
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 20
- 238000010526 radical polymerization reaction Methods 0.000 description 20
- 241000894007 species Species 0.000 description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 19
- 230000009849 deactivation Effects 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 18
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 18
- 239000007822 coupling agent Substances 0.000 description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 18
- 229920002223 polystyrene Polymers 0.000 description 18
- 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 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 17
- 230000007246 mechanism Effects 0.000 description 17
- 238000012662 bulk polymerization Methods 0.000 description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 230000007306 turnover Effects 0.000 description 16
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 238000001556 precipitation Methods 0.000 description 15
- 230000035484 reaction time Effects 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 14
- 238000004817 gas chromatography Methods 0.000 description 14
- 238000010348 incorporation Methods 0.000 description 14
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 14
- WEIVEBIRFQGROM-UHFFFAOYSA-N 1-n-(2-aminoethyl)propane-1,2-diamine Chemical compound CC(N)CNCCN WEIVEBIRFQGROM-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 12
- 230000001419 dependent effect Effects 0.000 description 12
- 238000011068 loading method Methods 0.000 description 12
- 230000000379 polymerizing effect Effects 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 11
- 238000007334 copolymerization reaction Methods 0.000 description 11
- 229920001519 homopolymer Polymers 0.000 description 11
- 230000003993 interaction Effects 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 230000004048 modification Effects 0.000 description 11
- 238000012986 modification Methods 0.000 description 11
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
- 229920000428 triblock copolymer Polymers 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 10
- 238000007720 emulsion polymerization reaction Methods 0.000 description 10
- 230000006872 improvement Effects 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- 230000009257 reactivity Effects 0.000 description 10
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 10
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 9
- 125000002521 alkyl halide group Chemical group 0.000 description 9
- 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 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000011324 bead Substances 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 9
- 230000003247 decreasing effect Effects 0.000 description 9
- 230000000670 limiting effect Effects 0.000 description 9
- 230000001404 mediated effect Effects 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 230000002085 persistent effect Effects 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- 229920002689 polyvinyl acetate Polymers 0.000 description 9
- 239000011118 polyvinyl acetate Substances 0.000 description 9
- 238000007342 radical addition reaction Methods 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- 238000004064 recycling Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000003643 water by type Substances 0.000 description 9
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 238000012661 block copolymerization Methods 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 238000003379 elimination reaction Methods 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 229910052736 halogen Chemical group 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 230000002902 bimodal effect Effects 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- 150000001879 copper Chemical class 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 6
- MUUOUUYKIVSIAR-UHFFFAOYSA-N 2-but-3-enyloxirane Chemical compound C=CCCC1CO1 MUUOUUYKIVSIAR-UHFFFAOYSA-N 0.000 description 6
- MHXMVFDLNGKBSR-UHFFFAOYSA-N 2-hydroxyethyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCO MHXMVFDLNGKBSR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229920000028 Gradient copolymer Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 150000002505 iron Chemical class 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000005267 main chain polymer Substances 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940078552 o-xylene Drugs 0.000 description 6
- 229920005604 random copolymer Polymers 0.000 description 6
- 238000006479 redox reaction Methods 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 235000012431 wafers Nutrition 0.000 description 6
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 5
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 239000012190 activator Substances 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical group OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 229920000587 hyperbranched polymer Polymers 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 5
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 5
- 239000002071 nanotube Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 5
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 5
- 238000004260 weight control Methods 0.000 description 5
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000005345 coagulation Methods 0.000 description 4
- 230000015271 coagulation Effects 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 229920000359 diblock copolymer Polymers 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical class N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 3
- 229960001950 benzethonium chloride Drugs 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 229940106681 chloroacetic acid Drugs 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000002270 exclusion chromatography Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229920000592 inorganic polymer Polymers 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 3
- 239000002114 nanocomposite Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 230000001902 propagating effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- YVWBWDZQFGXBOT-UHFFFAOYSA-N 1,3-bis(1-phenylethenyl)benzene Chemical compound C=1C=CC(C(=C)C=2C=CC=CC=2)=CC=1C(=C)C1=CC=CC=C1 YVWBWDZQFGXBOT-UHFFFAOYSA-N 0.000 description 2
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 2
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 2
- DUFCPZLMEULRED-UHFFFAOYSA-N 2-[bis(pyridin-2-ylmethyl)amino]ethanol Chemical compound C=1C=CC=NC=1CN(CCO)CC1=CC=CC=N1 DUFCPZLMEULRED-UHFFFAOYSA-N 0.000 description 2
- PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 description 2
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 238000004400 29Si cross polarisation magic angle spinning Methods 0.000 description 2
- PBHIWZGFSZBQJV-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-bromo-2-methylpropanoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)(C)Br PBHIWZGFSZBQJV-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 108010057081 Merozoite Surface Protein 1 Proteins 0.000 description 2
- 229920001367 Merrifield resin Polymers 0.000 description 2
- 241000425347 Phyla <beetle> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005411 Van der Waals force Methods 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- AOIQHKQLNIFAMJ-UHFFFAOYSA-N bromo 2-methylpropanoate Chemical compound CC(C)C(=O)OBr AOIQHKQLNIFAMJ-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- ZBTZNGUECMERJR-UHFFFAOYSA-N but-3-enyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCC=C ZBTZNGUECMERJR-UHFFFAOYSA-N 0.000 description 2
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 2
- 238000010888 cage effect Methods 0.000 description 2
- 230000003047 cage effect Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229940089960 chloroacetate Drugs 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000001246 colloidal dispersion Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 2
- AWWJYEJSCIDADZ-UHFFFAOYSA-N dimethyl 2,6-dibromoheptanedioate Chemical compound COC(=O)C(Br)CCCC(Br)C(=O)OC AWWJYEJSCIDADZ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000000132 electrospray ionisation Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229920006252 heterotelechelic polymer Polymers 0.000 description 2
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 2
- 238000010505 homolytic fission reaction Methods 0.000 description 2
- 230000005660 hydrophilic surface Effects 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 125000001905 inorganic group Chemical group 0.000 description 2
- 229910003480 inorganic solid Inorganic materials 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 238000010551 living anionic polymerization reaction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 2
- OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 description 2
- COCAUCFPFHUGAA-MGNBDDOMSA-N n-[3-[(1s,7s)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=C(F)C([C@@]23N=C(SCC[C@@H]2C3)N)=CC=1NC(=O)C1=CC=C(Cl)C=N1 COCAUCFPFHUGAA-MGNBDDOMSA-N 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 230000006855 networking Effects 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000011049 pearl Substances 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 238000004375 physisorption Methods 0.000 description 2
- 229920002627 poly(phosphazenes) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000012673 precipitation polymerization Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 230000005588 protonation Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000010107 reaction injection moulding Methods 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229920006301 statistical copolymer Polymers 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000003797 telogen phase Effects 0.000 description 2
- 230000002277 temperature effect Effects 0.000 description 2
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 description 2
- 238000006276 transfer reaction Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- BHGQSXUNEGPBCB-UHFFFAOYSA-N 1,2,3-tris(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1C(C)=C BHGQSXUNEGPBCB-UHFFFAOYSA-N 0.000 description 1
- HRFJEOWVAGSJNW-UHFFFAOYSA-N 1,4,8,11-tetramethyl-1,4,8,11-tetrazacyclotetradecane Chemical compound CN1CCCN(C)CCN(C)CCCN(C)CC1 HRFJEOWVAGSJNW-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MTIWAKNWUCCBRG-UHFFFAOYSA-N 1-(1-phenylethenyl)-4-[2-[4-(1-phenylethenyl)phenyl]propan-2-yl]benzene Chemical group C=1C=C(C(=C)C=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1C(=C)C1=CC=CC=C1 MTIWAKNWUCCBRG-UHFFFAOYSA-N 0.000 description 1
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 1
- BTMMOQRXYJBZFT-UHFFFAOYSA-N 1-phenylethyl 2-bromo-2-methylpropanoate Chemical compound BrC(C(=O)OC(C)C1=CC=CC=C1)(C)C BTMMOQRXYJBZFT-UHFFFAOYSA-N 0.000 description 1
- GJIZTHRAQWTRCF-UHFFFAOYSA-N 1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanimine Chemical compound C=1C=CC=NC=1CN=CC1=CC=CC=N1 GJIZTHRAQWTRCF-UHFFFAOYSA-N 0.000 description 1
- COUNGVKBYIDUNU-UHFFFAOYSA-N 2,2,2-trifluoroethyl dihydrogen phosphite Chemical compound OP(O)OCC(F)(F)F COUNGVKBYIDUNU-UHFFFAOYSA-N 0.000 description 1
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 1
- XXSPGBOGLXKMDU-UHFFFAOYSA-M 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C([O-])=O XXSPGBOGLXKMDU-UHFFFAOYSA-M 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-M 2-bromopropanoate Chemical compound CC(Br)C([O-])=O MONMFXREYOKQTI-UHFFFAOYSA-M 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- BSZGXCFUKRLAAN-UHFFFAOYSA-N 2-phenylprop-2-en-1-ol Chemical compound OCC(=C)C1=CC=CC=C1 BSZGXCFUKRLAAN-UHFFFAOYSA-N 0.000 description 1
- FKTLISWEAOSVBS-UHFFFAOYSA-N 2-prop-1-en-2-yloxyprop-1-ene Chemical class CC(=C)OC(C)=C FKTLISWEAOSVBS-UHFFFAOYSA-N 0.000 description 1
- YOGWMNBVPWGQRK-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OCCOC(=O)C=C YOGWMNBVPWGQRK-UHFFFAOYSA-N 0.000 description 1
- QUKRIOLKOHUUBM-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C QUKRIOLKOHUUBM-UHFFFAOYSA-N 0.000 description 1
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 1
- VJJZJBUCDWKPLC-UHFFFAOYSA-N 3-methoxyapigenin Chemical compound O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C=C1 VJJZJBUCDWKPLC-UHFFFAOYSA-N 0.000 description 1
- BLDQUHPMDSICNF-UHFFFAOYSA-N 4-nonan-5-yl-2-(4-nonan-5-ylpyridin-2-yl)pyridine Chemical compound CCCCC(CCCC)C1=CC=NC(C=2N=CC=C(C=2)C(CCCC)CCCC)=C1 BLDQUHPMDSICNF-UHFFFAOYSA-N 0.000 description 1
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical group CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 description 1
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- ZHBOFZNNPZNWGB-UHFFFAOYSA-N 9,10-bis(phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 ZHBOFZNNPZNWGB-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VVBXKASDRZXWON-UHFFFAOYSA-N N=[PH3] Chemical group N=[PH3] VVBXKASDRZXWON-UHFFFAOYSA-N 0.000 description 1
- PVCCCRBYVNROKV-UHFFFAOYSA-N OC1(C(=C)CC)CC=CC=C1 Chemical compound OC1(C(=C)CC)CC=CC=C1 PVCCCRBYVNROKV-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 238000005275 alloying Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 229920000469 amphiphilic block copolymer Polymers 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000004064 cosurfactant Substances 0.000 description 1
- 238000009402 cross-breeding Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- SYGAXBISYRORDR-UHFFFAOYSA-N ethyl 2-(hydroxymethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CO SYGAXBISYRORDR-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229940046149 ferrous bromide Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 239000003622 immobilized catalyst Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- LQBLTEFMUAASOG-UHFFFAOYSA-N lithium oxido(oxo)silane Chemical group [Li+].[O-][SiH]=O LQBLTEFMUAASOG-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000001254 matrix assisted laser desorption--ionisation time-of-flight mass spectrum Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- UAELKGDBIZQDKE-UHFFFAOYSA-N n,n-bis(pyridin-2-ylmethyl)octan-1-amine Chemical compound C=1C=CC=NC=1CN(CCCCCCCC)CC1=CC=CC=N1 UAELKGDBIZQDKE-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000004172 nitrogen cycle Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000012776 robust process Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000002109 single walled nanotube Substances 0.000 description 1
- 238000011172 small scale experimental method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- PGQNYIRJCLTTOJ-UHFFFAOYSA-N trimethylsilyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)O[Si](C)(C)C PGQNYIRJCLTTOJ-UHFFFAOYSA-N 0.000 description 1
- 238000010396 two-hybrid screening Methods 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- 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
- 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
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12580999P | 1999-03-23 | 1999-03-23 | |
| US125809P | 1999-03-23 | ||
| US14298099P | 1999-07-12 | 1999-07-12 | |
| US142980P | 1999-07-12 | ||
| PCT/US2000/007905 WO2000056795A1 (en) | 1999-03-23 | 2000-03-23 | Catalytic processes for the controlled polymerization of free radically (co)polymerizable monomers and functional polymeric systems prepared thereby |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60024605D1 DE60024605D1 (de) | 2006-01-12 |
| DE60024605T2 true DE60024605T2 (de) | 2006-08-24 |
Family
ID=26823972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60024605T Expired - Lifetime DE60024605T2 (de) | 1999-03-23 | 2000-03-23 | Katalytische prozesse für die kontrollierte polymerisation von freiradikalischen, copolymerisierbaren monomeren und funktionellpolymersysteme hergestellt davon |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7825199B1 (https=) |
| EP (1) | EP1171496B1 (https=) |
| JP (2) | JP5264030B2 (https=) |
| AU (1) | AU3919500A (https=) |
| DE (1) | DE60024605T2 (https=) |
| TW (1) | TWI291472B (https=) |
| WO (1) | WO2000056795A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007051694A1 (de) | 2007-10-26 | 2009-04-30 | Justus-Liebig-Universität Giessen | Kupfer-Sauerstoff-Adduktkomplexe |
| DE102008002016A1 (de) * | 2008-05-28 | 2009-12-03 | Evonik Röhm Gmbh | Verfahren zur Herstellung von silyl-funktionalisierten ABA-Triblockcopolymeren auf (Meth)acrylatbasis |
Families Citing this family (132)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7125938B2 (en) | 1997-03-11 | 2006-10-24 | Carnegie Mellon University | Atom or group transfer radical polymerization |
| WO2000056795A1 (en) | 1999-03-23 | 2000-09-28 | Carnegie Mellon University | Catalytic processes for the controlled polymerization of free radically (co)polymerizable monomers and functional polymeric systems prepared thereby |
| US7049373B2 (en) | 1999-08-06 | 2006-05-23 | Carnegie Mellon University | Process for preparation of graft polymers |
| US7141646B2 (en) | 2000-05-12 | 2006-11-28 | Kaneka Corporation | Method of purifying vinyl polymer |
| US7332550B2 (en) | 2000-10-06 | 2008-02-19 | Carnegie Mellon University | Stabilization of transition metal complexes for catalysis in diverse environments |
| US6790919B2 (en) | 2000-10-06 | 2004-09-14 | Carnegie Mellon University | Catalyst system for controlled polymerization |
| WO2002068485A1 (en) * | 2000-12-22 | 2002-09-06 | Carnegie Mellon University | Process for preparation of graft polymers |
| ATE470647T1 (de) | 2001-04-06 | 2010-06-15 | Univ Carnegie Mellon | Verfahren zur herstellung von nanostrukturierten materialien |
| US6716949B2 (en) * | 2001-09-20 | 2004-04-06 | Hewlett-Packard Development Company, L.P. | Amphipathic polymer particles and methods of manufacturing the same |
| US6723299B1 (en) | 2001-05-17 | 2004-04-20 | Zyvex Corporation | System and method for manipulating nanotubes |
| EP1440988A4 (en) * | 2001-08-31 | 2005-08-31 | Kaneka Corp | POLYOLEFINPROPOPOPOLYMER MADE IN THE PRESENCE OF A COORDINATION POLYMERIZATION CATALYST BASED ON A COMPLEX OF A LATE TRANSITION METAL AND METHOD FOR THE PRODUCTION THEREOF |
| AU2002351471A1 (en) | 2001-10-12 | 2003-04-22 | Carnegie Mellon University | Process for monomer sequence control in polymerizations |
| US6759491B2 (en) | 2001-10-12 | 2004-07-06 | Carnegie Mellon University | Simultaneous reverse and normal initiation of ATRP |
| EP1449855A4 (en) * | 2001-10-17 | 2006-06-07 | Kaneka Corp | PROCESS FOR PREPARING VINYL POLYMER |
| EP1449222B1 (en) | 2001-10-29 | 2011-08-31 | Hyperion Catalysis International, Inc. | Polymer containing functionalized carbon nanotubes |
| US6905667B1 (en) | 2002-05-02 | 2005-06-14 | Zyvex Corporation | Polymer and method for using the polymer for noncovalently functionalizing nanotubes |
| US20040034177A1 (en) | 2002-05-02 | 2004-02-19 | Jian Chen | Polymer and method for using the polymer for solubilizing nanotubes |
| US6942120B2 (en) | 2002-06-07 | 2005-09-13 | S.C. Johnson & Son, Inc. | Disposable bakeware with improved drip resistance at elevated temperatures |
| ATE443116T1 (de) * | 2002-07-26 | 2009-10-15 | Arkema France | Verwendung eines blockpolymeres mit mindestens einem hydrophilenblock |
| WO2004014963A2 (en) | 2002-08-09 | 2004-02-19 | Carnegie Mellon University | Polymers, supersoft elastomers and methods for preparing the same |
| US6992156B2 (en) * | 2002-12-31 | 2006-01-31 | The Goodyear Tire & Rubber Company | Controlled polymerization |
| JP2004240114A (ja) * | 2003-02-05 | 2004-08-26 | Fuji Photo Film Co Ltd | 表面機能性部材 |
| DE10312278A1 (de) | 2003-03-19 | 2004-09-30 | Röhm GmbH & Co. KG | Verfahren zur Abrennung von Übergangsmetallen aus Polymeren |
| KR100827861B1 (ko) | 2003-05-22 | 2008-05-07 | 지벡스 퍼포먼스 머티리얼즈, 엘엘씨 | 나노복합물 및 이의 제조 방법 |
| GB0314472D0 (en) * | 2003-06-20 | 2003-07-23 | Warwick Effect Polymers Ltd | Polymer |
| US7226957B1 (en) | 2003-11-03 | 2007-06-05 | University Of Iowa Research Foundation | Method for producing polymers with controlled molecular weight and end group functionality using photopolymerization in microemulsions |
| WO2005087818A1 (en) | 2004-03-05 | 2005-09-22 | Carnegie Mellon University | Preparation of functional polymers |
| US7893174B2 (en) | 2004-03-05 | 2011-02-22 | Carnegie Mellon University | Atom transfer radical polymerization process |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7244867B2 (en) * | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| WO2005112150A1 (ja) * | 2004-05-14 | 2005-11-24 | Matsushita Electric Industrial Co., Ltd. | リチウムイオン二次電池とその製造法 |
| FR2870245B1 (fr) * | 2004-05-14 | 2008-08-22 | Rhodia Chimie Sa | Synthese de copolymeres en forme d'etoile mikto par polymerisation radicalaire controlee |
| US7296576B2 (en) | 2004-08-18 | 2007-11-20 | Zyvex Performance Materials, Llc | Polymers for enhanced solubility of nanomaterials, compositions and methods therefor |
| AU2005277275B2 (en) * | 2004-08-20 | 2011-10-20 | Chevron Oronite Company Llc | Method for preparation of polyolefins containing exo-olefin chain ends |
| ATE509966T1 (de) * | 2004-08-20 | 2011-06-15 | Chevron Oronite Co | Verfahren zur herstellung von polyolefinen mit exo-olefin-kettenenden |
| US7705090B2 (en) * | 2004-08-20 | 2010-04-27 | Chevron Oronite Company Llc | Method for preparing polyolefins containing a high percentage of exo-olefin chain ends |
| JP4645103B2 (ja) * | 2004-08-30 | 2011-03-09 | チッソ株式会社 | ケイ素化合物 |
| US8986780B2 (en) * | 2004-11-19 | 2015-03-24 | Massachusetts Institute Of Technology | Method and apparatus for depositing LED organic film |
| WO2006063606A1 (en) * | 2004-12-16 | 2006-06-22 | Pirelli & C. S.P.A. | Process for manufacturing a thermoplastic elastomeric material |
| WO2006090688A1 (ja) | 2005-02-25 | 2006-08-31 | Mitsui Chemicals, Inc. | 重合触媒組成物およびポリマーの製造方法 |
| JP4543151B2 (ja) * | 2005-03-17 | 2010-09-15 | 株式会社産学連携機構九州 | 重合体およびブロック共重合体の製造方法 |
| US8153435B1 (en) | 2005-03-30 | 2012-04-10 | Tracer Detection Technology Corp. | Methods and articles for identifying objects using encapsulated perfluorocarbon tracers |
| US20060264590A1 (en) * | 2005-05-20 | 2006-11-23 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
| US20060260677A1 (en) * | 2005-05-23 | 2006-11-23 | Cornell Research Foundation, Inc. | Polypropylene silicate nanocomposites |
| US8273823B2 (en) | 2005-08-23 | 2012-09-25 | Carnegie Mellon University | Atom transfer radical polymerization in microemulsion and true emulsion polymerization processes |
| US20100311920A1 (en) * | 2005-08-26 | 2010-12-09 | Cid Centro De Investigacion Y Desarrollo Tecnologico Sa De Cv | Using Reactive Block Copolymers as Chain Extenders and Surface Modifiers |
| WO2007025310A1 (en) | 2005-08-26 | 2007-03-01 | Carnegie Mellon University | Polymerization process with catalyst reactivation |
| US20090156763A1 (en) * | 2005-08-30 | 2009-06-18 | Roberta Sulcis | Process for manufacturing a thermoplastic elastomeric material |
| EP1923418B1 (en) | 2005-09-07 | 2016-11-09 | Nippon Soda Co., Ltd. | Star polymer and process for production thereof |
| US7674866B2 (en) | 2005-09-14 | 2010-03-09 | Kyushu University, National University Corporation | Method of producing polymer using iron complex as catalyst |
| EP1767564B2 (en) * | 2005-09-26 | 2013-09-25 | Nippon Shokubai Co., Ltd. | Polymer, a method for producing the polymer, and a cement admixture using the same |
| US7723422B2 (en) | 2005-12-23 | 2010-05-25 | Boston Scientific Scimed, Inc. | Functionalized block copolymers |
| US7470466B2 (en) | 2005-12-23 | 2008-12-30 | Boston Scientific Scimed, Inc. | Nanoparticle structures and composite materials comprising a silicon-containing compound having a chemical linker that forms a non-covalent bond with a polymer |
| US8455088B2 (en) | 2005-12-23 | 2013-06-04 | Boston Scientific Scimed, Inc. | Spun nanofiber, medical devices, and methods |
| WO2007114134A1 (ja) | 2006-03-29 | 2007-10-11 | Mitsui Chemicals, Inc. | オレフィン系ブロックポリマーを含んでなる樹脂組成物およびその用途 |
| WO2007139463A1 (en) * | 2006-05-29 | 2007-12-06 | Ge Healthcare Bio-Sciences Ab | Preparation of monolithic articles |
| CN101484488B (zh) | 2006-07-11 | 2012-02-01 | 日本曹达株式会社 | 星形聚合物及其制造方法 |
| US8349410B2 (en) | 2006-08-17 | 2013-01-08 | University of Pittsburgh—of the Commonwealth System of Higher Education | Modification of surfaces with polymers |
| US20100311849A1 (en) * | 2006-08-23 | 2010-12-09 | Cid Centro De Investigacion Y Desarrollo Tecnologico Sa De Cv | Using Reactive Block Copolymers as Chain Extenders and Surface Modifiers |
| WO2008057163A2 (en) | 2006-10-09 | 2008-05-15 | Carnegie Mellon University | Preparation of functional gel particles with a dual crosslink network |
| EP2092590A4 (en) * | 2006-11-10 | 2011-01-12 | Univ California | ATMOSPHERE PRESSURE PLASMA-INDUCED POLYMERIZATION |
| AU2007341256B2 (en) * | 2006-12-28 | 2012-09-20 | Allnex Netherlands B.V. | Waterborne polymeric dispersions |
| JP4344779B2 (ja) * | 2007-03-20 | 2009-10-14 | 国立大学法人九州大学 | 鉄錯体及び該鉄錯体を触媒とする重合体の製造方法 |
| US8865797B2 (en) | 2007-05-23 | 2014-10-21 | Carnegie Mellon University | Hybrid particle composite structures with reduced scattering |
| US8252880B2 (en) | 2007-05-23 | 2012-08-28 | Carnegie Mellon University | Atom transfer dispersion polymerization |
| TW200911355A (en) * | 2007-07-25 | 2009-03-16 | Dsm Ip Assets Bv | Hydrophilic membrane |
| WO2009033974A1 (de) * | 2007-09-12 | 2009-03-19 | Construction Research & Technology Gmbh | Verfahren zur herstellung von silanmodifizierten copolymeren |
| EP2055720A1 (en) * | 2007-11-05 | 2009-05-06 | Total Petrochemicals Research Feluy | Predictive model for density and melt index of polymer leaving loop reactor |
| JP2009215373A (ja) * | 2008-03-07 | 2009-09-24 | Sumitomo Chemical Co Ltd | ブロック共重合体、およびその製造方法 |
| US20090311540A1 (en) * | 2008-06-11 | 2009-12-17 | Yoram Cohen | Highly Sensitive and Selective Nano-Structured Grafted Polymer Layers |
| US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
| US20090312586A1 (en) * | 2008-06-13 | 2009-12-17 | Marathon Gtf Technology, Ltd. | Hydrogenation of multi-brominated alkanes |
| DE102008043669A1 (de) * | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem breit verteilten B-Block |
| DE102008043658A1 (de) * | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem breit verteilten A-Block |
| DE102008043668A1 (de) * | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem bimodalen B-Block |
| JP5495736B2 (ja) * | 2008-12-11 | 2014-05-21 | 三菱レイヨン株式会社 | 改良された重合方法 |
| WO2010081132A1 (en) | 2009-01-12 | 2010-07-15 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
| US8962764B2 (en) | 2009-03-27 | 2015-02-24 | Carnegie Mellon University | Preparation of functional star macromolecules |
| US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8816001B2 (en) | 2010-09-10 | 2014-08-26 | Franklin And Marshall College | Genetically encoded initiator for polymer growth from proteins |
| US9644042B2 (en) | 2010-12-17 | 2017-05-09 | Carnegie Mellon University | Electrochemically mediated atom transfer radical polymerization |
| JP5890324B2 (ja) * | 2011-01-27 | 2016-03-22 | 東亞合成株式会社 | カルボキシル基含有重合体の製造方法 |
| US8815050B2 (en) | 2011-03-22 | 2014-08-26 | Marathon Gtf Technology, Ltd. | Processes and systems for drying liquid bromine |
| CN102286112B (zh) * | 2011-05-12 | 2012-10-17 | 北京化工大学 | 一种水溶性单体可控/活性自由基聚合的方法 |
| US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
| US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
| US20140275420A1 (en) | 2011-08-22 | 2014-09-18 | Carnegie Mellon University | Atom transfer radical polymerization under biologically compatible conditions |
| RU2014111849A (ru) | 2011-08-30 | 2015-10-10 | Басф Се | Получение полимеров контролируемой радикальной полимеризацией |
| US9790305B2 (en) | 2011-09-09 | 2017-10-17 | Franklin And Marshall College | Site specifically incorporated initiator for growth of polymers from proteins |
| US9090765B2 (en) | 2011-09-19 | 2015-07-28 | Henkel IP & Holding GmbH | Highly functionalized resin blends |
| US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
| US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
| WO2013158183A2 (en) | 2012-01-27 | 2013-10-24 | Carnegie Mellon University | Processable self-organizing nanoparticles |
| US9533297B2 (en) | 2012-02-23 | 2017-01-03 | Carnegie Mellon University | Ligands designed to provide highly active catalyst complexes |
| EP2935348A4 (en) * | 2012-12-18 | 2016-06-29 | Henkel IP & Holding GmbH | METHOD FOR CONTROLLED RADICAL POLYMERIZATION OF BRANCHED POLYACRYLATES |
| WO2014116672A1 (en) | 2013-01-22 | 2014-07-31 | Carnegie Mellon University | Lignin-containing polymers and compositions including lignin-containing polymers |
| US8883941B2 (en) * | 2013-03-18 | 2014-11-11 | Henkel Corporation | Methods and apparatus for controlled single electron transfer living radical polymerization |
| KR101466479B1 (ko) * | 2013-04-12 | 2014-12-02 | 영남대학교 산학협력단 | 원자이동라디칼중합(atrp)을 이용한 폴리비닐아세테이트 합성방법 및 상기 합성방법에 따라 얻어진 폴리비닐아세테이트 |
| US9765169B2 (en) | 2013-04-18 | 2017-09-19 | Carnegie Mellon University | Functionalized polymer hybrids |
| US9782727B2 (en) | 2014-07-14 | 2017-10-10 | International Business Machines Corporation | Filtration membranes with functionalized star polymers |
| KR101652176B1 (ko) * | 2014-10-22 | 2016-08-30 | 영남대학교 산학협력단 | 초임계이산화탄소 내에서 전자이동활성제 재생 원자이동라디칼중합을 이용한 폴리비닐아세테이트 합성방법 |
| US9982070B2 (en) | 2015-01-12 | 2018-05-29 | Carnegie Mellon University | Aqueous ATRP in the presence of an activator regenerator |
| US9931598B2 (en) | 2015-02-16 | 2018-04-03 | International Business Machines Corporation | Anti-fouling coatings with star polymers for filtration membranes |
| US10005042B2 (en) | 2015-02-16 | 2018-06-26 | International Business Machines Corporation | Thin film composite forward osmosis membranes with performance enhancing layers |
| PL3313896T3 (pl) * | 2015-06-26 | 2020-03-31 | Fischerwerke Gmbh & Co. Kg | Aldiminy i ketiminy jako inicjatory w układach utwardzaczy i odpowiednie kompozycje żywic między innymi dla techniki mocowania |
| WO2017118544A1 (en) | 2016-01-05 | 2017-07-13 | Sabic Global Technologies B.V. | Method for preparing ethylene copolymer |
| WO2017132137A1 (en) | 2016-01-25 | 2017-08-03 | Carnegie Mellon University | Composite composition and modification of inorganic particles for use in composite compositions |
| AU2017346582B2 (en) * | 2016-10-17 | 2021-10-21 | Orthobond Corporation | Surfaces with oligomeric or polymeric antimicrobials |
| US10982266B2 (en) | 2016-11-03 | 2021-04-20 | Carnegie Mellon University | Nucleic acid-polymer conjugates for bright fluorescent tags |
| JP6965703B2 (ja) | 2016-11-28 | 2021-11-10 | 東洋インキＳｃホールディングス株式会社 | （メタ）アクリル系重合体、（メタ）アクリル系ブロック共重合体、顔料分散体、感光性着色組成物、カラーフィルタ、インキ組成物、複合ブロック共重合体、顔料分散剤。 |
| WO2018132582A1 (en) | 2017-01-12 | 2018-07-19 | Carnegie Mellon University | Surfactant assisted formation of a catalyst complex for emulsion atom transfer radical polymerization processes |
| WO2018132696A2 (en) | 2017-01-12 | 2018-07-19 | Russell Alan J | Stomach acid-stable and mucin-binding protein-polymer conjugates |
| CN110382568B (zh) | 2017-03-07 | 2022-03-04 | 心脏起搏器股份公司 | 烯丙基封端的聚异丁烯的硼氢化/氧化 |
| KR101893690B1 (ko) * | 2017-05-12 | 2018-08-31 | 부산대학교 산학협력단 | 에폭시 접착제용 첨가제 및 이를 포함하는 구조용 에폭시 접착제 조성물 |
| CN107056976B (zh) * | 2017-05-31 | 2019-05-21 | 华中科技大学 | 一种碱活化卤代烃作用的反向原子转移自由基聚合方法 |
| KR102649181B1 (ko) * | 2017-12-06 | 2024-03-20 | 디디피 스페셜티 일렉트로닉 머티리얼즈 유에스, 엘엘씨 | 산화주석 (ii)을 함유하는 음이온 교환기에 의한 크롬 (iv) 함유 물의 처리 |
| WO2019143629A1 (en) | 2018-01-17 | 2019-07-25 | Cardiac Pacemakers, Inc. | End-capped polyisobutylene polyurethane |
| US11857634B2 (en) | 2018-04-20 | 2024-01-02 | University of Pittsburgh—of the Commonwealth System of Higher Education | Cationic amphiphilic polymers for codelivery of hydrophobic agents and nucleic acids |
| US20210237002A1 (en) * | 2018-06-05 | 2021-08-05 | Rensselaer Polytechnic Institute | Rapid and facile membrane adsorber fabrication with ultra high binding capacity |
| 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 |
| WO2020077170A1 (en) | 2018-10-12 | 2020-04-16 | University Of Pittsburgh- Of The Commonwealth System Of Higher Education | Small polymeric carriers for delivery of agents |
| JP7846630B2 (ja) * | 2020-04-30 | 2026-04-15 | ダウ グローバル テクノロジーズ エルエルシー | Ａｔｒｐによりオレフィン－アクリレートブロックコポリマーを調製するための方法 |
| JP2025097474A (ja) | 2023-12-19 | 2025-07-01 | Dic株式会社 | 重合体の製造方法、重合体、組成物、レジスト組成物およびレジストパターン |
| CN119751751B (zh) * | 2024-12-30 | 2025-10-31 | 齐鲁工业大学(山东省科学院) | 一种耐高温高盐聚合物及其制备与应用 |
| CN119978251B (zh) * | 2025-04-14 | 2025-07-11 | 山东三润助剂科技股份有限公司 | 一种透明型pvc加工改性剂及其制备方法 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183217A (en) | 1961-03-01 | 1965-05-11 | Exxon Research Engineering Co | Copolymerization of polar with nonpolar monomers in the presence of a friedel-craftsand a free radical initator |
| US4007165A (en) | 1971-06-01 | 1977-02-08 | Pennwalt Corporation | Unsymmetrical tertiary-aliphatic azoalkanes |
| US3959225A (en) | 1974-03-20 | 1976-05-25 | Exxon Research And Engineering Company | Thermally-staged polymer process |
| US4374751A (en) | 1980-08-08 | 1983-02-22 | General Electric Company | Polymerization initiator compositions |
| US4728706A (en) | 1986-08-29 | 1988-03-01 | E. I. Du Pont De Nemours And Company | Titanium, zirconium- and hafnium containing initiators in the polymerization of acrylic monomers to "living" polymers |
| US5089135A (en) | 1988-01-20 | 1992-02-18 | Mitsubishi Rayon Co., Ltd. | Carbon based porous hollow fiber membrane and method for producing same |
| US4940648A (en) | 1988-02-12 | 1990-07-10 | Hoechst Celanese Corporation | Increased sensitivity photoinitiation compositions |
| US5169914A (en) | 1988-05-03 | 1992-12-08 | Edison Polymer Innovation Corporation | Uniform molecular weight polymers |
| CA1326322C (en) | 1988-05-03 | 1994-01-18 | Gabor Kaszas | Uniform molecular weight polymers |
| US4954416A (en) | 1988-12-21 | 1990-09-04 | Minnesota Mining And Manufacturing Company | Tethered sulfonium salt photoinitiators for free radical polymerization |
| ATE161021T1 (de) | 1991-07-15 | 1997-12-15 | Exxon Chemical Patents Inc | Lebendes karbokationisches polymerisationsverfahren |
| US5405913A (en) | 1993-03-22 | 1995-04-11 | The University Of Akron | Free radical copper(II)-enolate polymerization initiators |
| US5510307A (en) | 1993-04-08 | 1996-04-23 | Isp Investments Inc. | Free radical initiator delivery system |
| US5312871A (en) | 1993-07-27 | 1994-05-17 | Carnegie Mellon University | Free radical polymerization process |
| 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 |
| US6541580B1 (en) | 1995-03-31 | 2003-04-01 | Carnegie Mellon University | 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 |
| US5789487A (en) * | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
| US5910549A (en) | 1996-08-22 | 1999-06-08 | Carnegie-Mellon University | Method for preparation of alkoxyamines from nitroxyl radicals |
| TW593347B (en) * | 1997-03-11 | 2004-06-21 | Univ Carnegie Mellon | Improvements in atom or group transfer radical polymerization |
| JP3946309B2 (ja) | 1997-04-10 | 2007-07-18 | 富士フイルム株式会社 | 着色感光性組成物 |
| US5986015A (en) | 1997-05-16 | 1999-11-16 | The Procter & Gamble Company | Method of making graft polymers |
| US5891971A (en) * | 1997-08-15 | 1999-04-06 | Xerox Corporation | Polymerization processes |
| JP3620248B2 (ja) * | 1997-12-01 | 2005-02-16 | 財団法人化学技術戦略推進機構 | リビングラジカル重合開始剤系及びそれを用いる重合体の製造方法 |
| US6121371A (en) | 1998-07-31 | 2000-09-19 | Carnegie Mellon University | Application of atom transfer radical polymerization to water-borne polymerization systems |
| JP3832133B2 (ja) * | 1999-03-16 | 2006-10-11 | 財団法人化学技術戦略推進機構 | リビングラジカル重合開始剤系及びそれを用いる重合体の製造方法 |
| WO2000056795A1 (en) | 1999-03-23 | 2000-09-28 | Carnegie Mellon University | Catalytic processes for the controlled polymerization of free radically (co)polymerizable monomers and functional polymeric systems prepared thereby |
| EP1337563B1 (en) | 2000-10-06 | 2006-12-20 | Carnegie-Mellon University | Polymerization process for ionic monomers |
| WO2002028912A2 (en) | 2000-10-06 | 2002-04-11 | Carnegie Mellon University | Preparation of nanocomposite structures by controlled polymerization |
-
2000
- 2000-03-23 WO PCT/US2000/007905 patent/WO2000056795A1/en not_active Ceased
- 2000-03-23 EP EP00918372A patent/EP1171496B1/en not_active Expired - Lifetime
- 2000-03-23 TW TW089105534A patent/TWI291472B/zh not_active IP Right Cessation
- 2000-03-23 US US09/534,827 patent/US7825199B1/en not_active Expired - Fee Related
- 2000-03-23 AU AU39195/00A patent/AU3919500A/en not_active Abandoned
- 2000-03-23 JP JP2000606655A patent/JP5264030B2/ja not_active Expired - Lifetime
- 2000-03-23 DE DE60024605T patent/DE60024605T2/de not_active Expired - Lifetime
-
2004
- 2004-02-27 US US10/788,995 patent/US20040171779A1/en not_active Abandoned
-
2011
- 2011-05-09 JP JP2011104381A patent/JP2011202169A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007051694A1 (de) | 2007-10-26 | 2009-04-30 | Justus-Liebig-Universität Giessen | Kupfer-Sauerstoff-Adduktkomplexe |
| US8338600B2 (en) | 2007-10-26 | 2012-12-25 | Justus-Liebig-Universitat Giessen | Copper-oxygen adduct complexes, and methods of making and use |
| DE102008002016A1 (de) * | 2008-05-28 | 2009-12-03 | Evonik Röhm Gmbh | Verfahren zur Herstellung von silyl-funktionalisierten ABA-Triblockcopolymeren auf (Meth)acrylatbasis |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60024605D1 (de) | 2006-01-12 |
| AU3919500A (en) | 2000-10-09 |
| US20040171779A1 (en) | 2004-09-02 |
| EP1171496A1 (en) | 2002-01-16 |
| JP2011202169A (ja) | 2011-10-13 |
| US7825199B1 (en) | 2010-11-02 |
| EP1171496B1 (en) | 2005-12-07 |
| JP2002540234A (ja) | 2002-11-26 |
| JP5264030B2 (ja) | 2013-08-14 |
| WO2000056795A1 (en) | 2000-09-28 |
| TWI291472B (en) | 2007-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60024605T2 (de) | Katalytische prozesse für die kontrollierte polymerisation von freiradikalischen, copolymerisierbaren monomeren und funktionellpolymersysteme hergestellt davon | |
| DE69636326T2 (de) | Verbesserte verfahren basierend auf atom (oder gruppen) übertragungs-radikalpolymerisation und neue (co)polymere mit nützlichen strukturen und eigenschaften | |
| DE69836419T2 (de) | Verbesserungen bei der atom- oder gruppenübertragungsradikalpolymerisation | |
| Hojjati et al. | Synthesis of TiO2/PAA nanocomposite by RAFT polymerization | |
| DE60125409T2 (de) | Polymerisationsverfahren für ionische monomere | |
| DE69917311T2 (de) | Mikrogele und verfahren zu deren herstellung | |
| JP3476016B2 (ja) | 二酸化炭素中における不均質重合 | |
| DE69635802T2 (de) | Polymerisationsverfahren basierend auf atom (oder gruppen) übertragungsradikalpolymerisation | |
| Pyun et al. | Synthesis and characterization of organic/inorganic hybrid nanoparticles: kinetics of surface-initiated atom transfer radical polymerization and morphology of hybrid nanoparticle ultrathin films | |
| DE60311291T2 (de) | Polymerfestelektrolyt | |
| EP2046849B1 (de) | Verfahren zur herstellung von aba-triblockcopolymeren auf (meth)acrylatbasis | |
| DE60305978T2 (de) | Kontrollierte polymerisation | |
| WO2000011043A1 (de) | Verfahren zur herstellung von definierten schichten oder schichtsystemen | |
| Hojjati et al. | Synthesis and kinetics of graft polymerization of methyl methacrylate from the RAFT coordinated surface of nano‐TiO2 | |
| DE60306957T2 (de) | Azlacton -initiatoren für atomtransferradikalpolymerisation | |
| LaNasa et al. | Surface-initiated ring-opening metathesis polymerization: a method for synthesizing polymer-functionalized nanoparticles exhibiting semicrystalline properties and diverse macromolecular architectures | |
| EP1637550B1 (en) | Catalytic processes for the controlled polymerization of free radically (co) polymerizable monomers and functional polymeric systems prepared thereby | |
| DE69932049T2 (de) | Anwendung von atomübertragungs-radikalpolymerisation auf wässrige polymerisationssysteme | |
| Gu et al. | Synthesis of double hydrophilic graft copolymer containing poly (ethylene glycol) and poly (methacrylic acid) side chains via successive ATRP | |
| Ghasemi et al. | PdNPs@ thermo-responsive block copolymers composed of PNIPAM and poly (ionic liquid) via RAFT polymerization | |
| DE112006000410B4 (de) | Pfropf-Copolymer und Verfahren zum Herstellen desselben | |
| Sun et al. | Isolated In Situ Cross-Linking-Assisted Polymerization-Induced Self-Assembly to Polymer Cubosomes with Enhanced Stability | |
| Deane et al. | Synthesis and characterization of all-acrylic tetrablock copolymer nanoparticles: waterborne thermoplastic elastomers via one-pot RAFT aqueous emulsion polymerization | |
| Li et al. | Functional Nano-Objects Prepared via Living Anionic Polymerization-Induced Self-Assembly (LAPISA) of Polar Vinyl Monomers | |
| Lahmar et al. | 1, 2, 3-triazole functionalized polystyrene and perdeuterated polystyrene chelating latexes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |