TW512153B - Process for producing a polymer, polymer made therefrom, coating composition comprising the polymer and chain transfer agent used therefor - Google Patents
Process for producing a polymer, polymer made therefrom, coating composition comprising the polymer and chain transfer agent used therefor Download PDFInfo
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- TW512153B TW512153B TW087121227A TW87121227A TW512153B TW 512153 B TW512153 B TW 512153B TW 087121227 A TW087121227 A TW 087121227A TW 87121227 A TW87121227 A TW 87121227A TW 512153 B TW512153 B TW 512153B
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- 229920000642 polymer Polymers 0.000 title claims abstract description 131
- 238000000034 method Methods 0.000 title claims abstract description 75
- 239000012986 chain transfer agent Substances 0.000 title claims abstract description 66
- 239000008199 coating composition Substances 0.000 title claims description 4
- 230000008569 process Effects 0.000 title abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 137
- -1 carbonylphenyl Chemical group 0.000 claims abstract description 136
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 111
- 238000012546 transfer Methods 0.000 claims abstract description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 52
- 150000003254 radicals Chemical class 0.000 claims abstract description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 15
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- 125000005059 halophenyl group Chemical group 0.000 claims abstract 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 251
- 239000000126 substance Substances 0.000 claims description 134
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 96
- 239000000203 mixture Substances 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
- 238000007142 ring opening reaction Methods 0.000 claims description 11
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- WJKYOQDIQYJXSD-UHFFFAOYSA-N propan-1-imine Chemical compound CCC=N WJKYOQDIQYJXSD-UHFFFAOYSA-N 0.000 claims description 3
- OAPFBXRHYINFDV-MDZDMXLPSA-N (e)-bis[(2-methylpropan-2-yl)oxy]diazene Chemical compound CC(C)(C)O\N=N\OC(C)(C)C OAPFBXRHYINFDV-MDZDMXLPSA-N 0.000 claims description 2
- PIMKIZUVIMAVSF-UHFFFAOYSA-N 1-(2-phenylethyl)-9h-fluorene Chemical compound C=1C=CC=2C3=CC=CC=C3CC=2C=1CCC1=CC=CC=C1 PIMKIZUVIMAVSF-UHFFFAOYSA-N 0.000 claims description 2
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 claims description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- OUHFEIMFMIYFPH-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C(=C(C=2CC3=CC=CC=C3C2C1)OOC1=C(C(=CC=2C3=CC=CC=C3CC12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C=1C(=C(C=2CC3=CC=CC=C3C2C1)OOC1=C(C(=CC=2C3=CC=CC=C3CC12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 OUHFEIMFMIYFPH-UHFFFAOYSA-N 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012935 ammoniumperoxodisulfate Substances 0.000 claims description 2
- 150000004683 dihydrates Chemical class 0.000 claims description 2
- 235000013847 iso-butane Nutrition 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229950010765 pivalate Drugs 0.000 claims description 2
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 claims description 2
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 claims 1
- AZCYBBHXCQYWTO-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methoxy]benzaldehyde Chemical compound FC1=CC=CC(Cl)=C1COC1=CC=CC=C1C=O AZCYBBHXCQYWTO-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- AZYYVEADDFAFPU-UHFFFAOYSA-N 2-tert-butyl-7,7-dimethyloctaneperoxoic acid Chemical compound CC(C)(C)CCCCC(C(C)(C)C)C(=O)OO AZYYVEADDFAFPU-UHFFFAOYSA-N 0.000 claims 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 238000012661 block copolymerization Methods 0.000 claims 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- FYLJKQFMQFOLSZ-UHFFFAOYSA-N cyclohexylperoxycyclohexane Chemical group C1CCCCC1OOC1CCCCC1 FYLJKQFMQFOLSZ-UHFFFAOYSA-N 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 238000012675 gradient copolymerization Methods 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- KDSNLYIMUZNERS-UHFFFAOYSA-N isobutyl amine Natural products CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- YFYSUAZHCKSLCV-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxobutan-2-yl)diazenyl]-2-methylbutanoate Chemical compound COC(=O)C(C)(CC)N=NC(C)(CC)C(=O)OC YFYSUAZHCKSLCV-UHFFFAOYSA-N 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 125000005545 phthalimidyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 123
- 239000000243 solution Substances 0.000 description 112
- 235000019439 ethyl acetate Nutrition 0.000 description 82
- 239000011550 stock solution Substances 0.000 description 62
- 238000002360 preparation method Methods 0.000 description 60
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical class CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 58
- 238000010968 computed tomography angiography Methods 0.000 description 57
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
- 238000011049 filling Methods 0.000 description 47
- 239000012991 xanthate Substances 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 35
- 239000003708 ampul Substances 0.000 description 33
- 239000012990 dithiocarbamate Substances 0.000 description 33
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 29
- 238000005227 gel permeation chromatography Methods 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 230000002079 cooperative effect Effects 0.000 description 26
- 101150041968 CDC13 gene Proteins 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000003860 storage Methods 0.000 description 23
- 239000004793 Polystyrene Substances 0.000 description 21
- 229920002223 polystyrene Polymers 0.000 description 21
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 229920002689 polyvinyl acetate Polymers 0.000 description 14
- 239000011118 polyvinyl acetate Substances 0.000 description 14
- KOQQFZSGVDYJLH-UHFFFAOYSA-N 2-cyanopropan-2-yl pyrrole-1-carbodithioate Chemical compound N#CC(C)(C)SC(=S)N1C=CC=C1 KOQQFZSGVDYJLH-UHFFFAOYSA-N 0.000 description 13
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- AGCPVOYGTAIJAP-UHFFFAOYSA-N benzyl pyrrole-1-carbodithioate Chemical compound C1=CC=CN1C(=S)SCC1=CC=CC=C1 AGCPVOYGTAIJAP-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 229940017219 methyl propionate Drugs 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 10
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 10
- 150000004659 dithiocarbamates Chemical class 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
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- RFUCOAQWQVDBEU-UHFFFAOYSA-N methyl 2-(hydroxymethyl)prop-2-enoate Chemical compound COC(=O)C(=C)CO RFUCOAQWQVDBEU-UHFFFAOYSA-N 0.000 description 1
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- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
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- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
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- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 230000000191 radiation effect Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- DUVOKRXITKPPPE-UHFFFAOYSA-N s-phenylsulfanylthiohydroxylamine Chemical compound NSSC1=CC=CC=C1 DUVOKRXITKPPPE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 125000005323 thioketone group Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
- C07C325/02—Thioketones; Oxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/36—Esters of dithiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/16—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
- C07C333/20—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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- Polymerisation Methods In General (AREA)
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- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
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US6815797P | 1997-12-18 | 1997-12-18 | |
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TW087121227A TW512153B (en) | 1997-12-18 | 1999-02-06 | Process for producing a polymer, polymer made therefrom, coating composition comprising the polymer and chain transfer agent used therefor |
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US (2) | US6642318B1 (en, 2012) |
EP (1) | EP1054906B2 (en, 2012) |
JP (2) | JP4886109B2 (en, 2012) |
KR (1) | KR100589073B1 (en, 2012) |
AU (1) | AU1911399A (en, 2012) |
BR (1) | BR9815179A (en, 2012) |
CA (1) | CA2309279C (en, 2012) |
DE (1) | DE69836501T3 (en, 2012) |
DK (1) | DK1054906T3 (en, 2012) |
ES (1) | ES2277678T3 (en, 2012) |
IL (1) | IL136389A0 (en, 2012) |
IN (2) | IN2000MU00034A (en, 2012) |
MX (1) | MXPA00005653A (en, 2012) |
NZ (1) | NZ505654A (en, 2012) |
TW (1) | TW512153B (en, 2012) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113980486A (zh) * | 2021-11-18 | 2022-01-28 | 浙江理工大学 | 一种无皂化学交联型共聚物纳米粒子包覆有机颜料杂化胶乳的制备方法 |
Families Citing this family (271)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2773161B1 (fr) | 1997-12-31 | 2000-01-21 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
WO1999035177A1 (fr) | 1997-12-31 | 1999-07-15 | Rhodia Chimie | Procede de synthese de polymeres a blocs par polymerisation radicalaire controlee a partir de composes dithiocarbamates |
FR2794463B1 (fr) * | 1999-06-04 | 2005-02-25 | Rhodia Chimie Sa | Procede de synthese de polymeres par polymerisation radicalaire controlee a l'aide de xanthates halogenes |
FR2802209B1 (fr) | 1999-12-10 | 2002-03-01 | Rhodia Chimie Sa | Latex a chimie de surface modifiee et poudres redispersables , leur obtention et leurs utilisations |
US7557235B2 (en) | 2000-02-16 | 2009-07-07 | Lubrizol Advanced Materials, Inc. | Hydroxyl-terminated thiocarbonate containing compounds, polymers, and copolymers, and polyurethanes and urethane acrylics made therefrom |
US7335788B2 (en) | 2000-02-16 | 2008-02-26 | Lubrizol Advanced Materials, Inc. | S-(α, α′-disubstituted-α″-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom |
US7495050B2 (en) | 2000-02-16 | 2009-02-24 | Lubrizol Advanced Materials, Inc. | Associative thickeners for aqueous systems |
US7205368B2 (en) | 2000-02-16 | 2007-04-17 | Noveon, Inc. | S-(α, α′-disubstituted-α′ ′-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom |
US6596899B1 (en) | 2000-02-16 | 2003-07-22 | Noveon Ip Holdings Corp. | S,S′BIS-(α, α′-DISUBSTITUTED-α″-ACETIC ACID)- TRITHIOCARBONATES AND DERIVATIVES AS INITIATOR-CHAIN TRANSFER AGENT-TERMINATOR FOR CONTROLLED RADICAL POLYMERIZATIONS AND THE PROCESS FOR MAKING THE SAME |
AUPQ679400A0 (en) * | 2000-04-07 | 2000-05-11 | Commonwealth Scientific And Industrial Research Organisation | Microgel synthesis |
US7064151B1 (en) | 2000-04-07 | 2006-06-20 | E. I. Du Pont De Nemours And Company | Process of microgel synthesis and products produced therefrom |
US6500871B1 (en) | 2000-06-08 | 2002-12-31 | Rhodia Chimie | Process for preparing colloids of particles coming from the hydrolysis of a salt of a metal cation |
DE10030217A1 (de) | 2000-06-20 | 2002-01-03 | Beiersdorf Ag | Verfahren zur Herstellung von Polyacrylaten |
DE10036801A1 (de) | 2000-07-28 | 2002-02-07 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
FR2814168B1 (fr) * | 2000-09-18 | 2006-11-17 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs par polymerisation radicalaire controlee en presence d'un compose disulfure |
US6380335B1 (en) | 2000-09-28 | 2002-04-30 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
US6569969B2 (en) | 2000-09-28 | 2003-05-27 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
US6518364B2 (en) | 2000-09-28 | 2003-02-11 | Symyx Technologies, Inc. | Emulsion living-type free radical polymerization, methods and products of same |
US6395850B1 (en) * | 2000-09-28 | 2002-05-28 | Symyx Technologies, Inc. | Heterocycle containing control agents for living-type free radical polymerization |
US6767968B1 (en) | 2000-10-03 | 2004-07-27 | Symyx Technologies, Inc. | ABA-type block copolymers having a random block of hydrophobic and hydrophilic monomers and methods of making same |
US6579947B2 (en) | 2001-02-20 | 2003-06-17 | Rhodia Chimie | Hydraulic fracturing fluid comprising a block copolymer containing at least one water-soluble block and one hydrophobic block |
DE10109067A1 (de) | 2001-02-24 | 2002-09-12 | Tesa Ag | Haftklebemasse mit geringem Ausgasungsverhalten |
FR2821620B1 (fr) * | 2001-03-02 | 2003-06-27 | Coatex Sas | Procede de polymerisation radicalaire controlee de l'acide acrylique et de ses sels, les polymeres de faible polydispersite obtenus, et leurs applications |
JP4889867B2 (ja) * | 2001-03-13 | 2012-03-07 | 株式会社カネカ | 末端にアルケニル基を有するビニル系重合体の製造方法、ビニル系重合体および硬化性組成物 |
JP3971705B2 (ja) * | 2001-04-04 | 2007-09-05 | 株式会社カネカ | 熱可塑性樹脂組成物およびエラストマー組成物 |
WO2002090397A1 (fr) * | 2001-05-04 | 2002-11-14 | Rhodia Chimie | Procede de reduction radicalaire de fonctions dithiocarbonylees ou dithiophosphorylees portees par un polymere |
DE10129608A1 (de) | 2001-06-20 | 2003-05-28 | Tesa Ag | Stripfähige Systeme auf Basis von Acrylatblockcopolymeren |
FR2826658B1 (fr) * | 2001-06-29 | 2003-09-05 | Rhodia Chimie Sa | Synthese de polymeres par voie radicalaire controlee en miniemulsion |
FR2829494B1 (fr) | 2001-07-13 | 2005-10-28 | Rhodia Chimie Sa | Compositions aqueuses comprenant un microgel chimique associe a un polymere pontant, preparation et utilisation |
US7094833B2 (en) * | 2001-07-16 | 2006-08-22 | Kaneka Corporation | Block copolymer |
US6596809B2 (en) | 2001-07-20 | 2003-07-22 | Symyx Technologies, Inc. | Cellulose copolymers that modify fibers and surfaces and methods of making same |
FR2829137B1 (fr) * | 2001-08-28 | 2003-12-19 | Rhodia Chimie Sa | Procede de polymerisation radicalaire realise en presence de composes disulfures |
DE10149083A1 (de) | 2001-10-05 | 2003-04-17 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
DE10149084A1 (de) | 2001-10-05 | 2003-06-18 | Tesa Ag | UV-vernetzbare Acrylathaftschmelzhaftkleber mit enger Molekulargewichtsverteilung |
JP4242283B2 (ja) * | 2001-10-30 | 2009-03-25 | 株式会社カネカ | シリコーン含有ブロック共重合体 |
JPWO2003042256A1 (ja) * | 2001-11-14 | 2005-03-10 | 株式会社カネカ | 硬化性組成物 |
DE10156088A1 (de) | 2001-11-16 | 2003-06-05 | Tesa Ag | Orientierte Acrylatblockcopolymere |
US7271203B2 (en) | 2001-11-24 | 2007-09-18 | Tesa Aktiengesellschaft | Crosslinking of photoiniator-initialized polyacrylates |
KR20100109960A (ko) * | 2001-12-21 | 2010-10-11 | 유니버시티 오브 시드니 | 중합체 입자의 수성 분산액 |
JP2005515261A (ja) | 2002-01-25 | 2005-05-26 | エルジー ケミカル エルティーディー. | 水溶性ジチオエステル系化合物およびその製造方法 |
AU2003206170A1 (en) | 2002-02-04 | 2003-09-02 | Lg Chem, Ltd. | Organic-inorganic nanocomposite and preparation thereof |
EP1483362B2 (en) | 2002-02-11 | 2012-12-26 | Rhodia Chimie | Dishwashing detergent composition comprising a block copolymer |
US6855840B2 (en) * | 2002-02-11 | 2005-02-15 | University Of Southern Mississippi | Chain transfer agents for raft polymerization in aqueous media |
US6667376B2 (en) | 2002-03-22 | 2003-12-23 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization and methods of polymerizing |
US7138468B2 (en) | 2002-03-27 | 2006-11-21 | University Of Southern Mississippi | Preparation of transition metal nanoparticles and surfaces modified with (CO)polymers synthesized by RAFT |
DE10227338B4 (de) | 2002-06-19 | 2006-05-24 | Byk-Chemie Gmbh | Verwendung von Polyacrylat-modifizierten Polysiloxanen als Verlaufmittel in Beschichtungsmitteln |
FR2842814B1 (fr) * | 2002-07-26 | 2004-10-22 | Coatex Sas | Procede de polymerisation radicalaire controlee de l'acide acrylique et de ses sels, les polymeres obtenus, et leurs applications. |
DE10234246A1 (de) | 2002-07-27 | 2004-02-05 | Tesa Ag | Haftklebemassen mit hohem Brechungsindex auf Basis von Acrylatblockcopolymeren |
FR2843314B1 (fr) | 2002-08-06 | 2004-09-24 | Rhodia Chimie Sa | Synthese de microgels statistiques par polymerisation radicalaire controlee |
DE10237000A1 (de) | 2002-08-13 | 2004-02-26 | Tesa Ag | Verfahren zur Herstellung von Acrylathaftklebemassen unter Nutzung von Metall-Schwefel-Verbindungen |
FR2844264B1 (fr) * | 2002-09-11 | 2006-10-20 | Rhodia Chimie Sa | Nouveaux composes comprenant un groupement thiocarbonylsulfanyle utiles pour la synthese de composes alpha-perfluoroalkylamines par voie radicalaire |
DE10243666A1 (de) * | 2002-09-20 | 2004-04-01 | Bayer Ag | Dithiocarbaminsäureester |
FR2846973B1 (fr) | 2002-11-07 | 2004-12-17 | Rhodia Chimie Sa | Composition d'antifroissage comprenant un copolymere a architecture controlee, pour articles en fibres textiles |
DE10256782A1 (de) * | 2002-12-05 | 2004-08-05 | Tesa Ag | Haftklebeartikel |
US6992217B2 (en) | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
US6894133B2 (en) | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
FR2848557B1 (fr) * | 2002-12-13 | 2006-07-07 | Atofina | Copolymeres a gradient solubles ou du moins dispersibles dans l'eau comme dans les solvants organiques |
FR2848556B1 (fr) | 2002-12-13 | 2006-06-16 | Bio Merieux | Procede de polymerisation radicalaire controlee |
KR101119783B1 (ko) | 2002-12-28 | 2012-03-23 | 제이에스알 가부시끼가이샤 | 감방사선성 수지 조성물 |
GB0301014D0 (en) * | 2003-01-16 | 2003-02-19 | Biocompatibles Ltd | Conjugation reactions |
DE10314898A1 (de) * | 2003-01-29 | 2004-08-12 | Tesa Ag | Haftklebebänder zur Verklebung von Druckplatten und Verfahren zu deren Herstellung |
US6680362B1 (en) | 2003-02-05 | 2004-01-20 | 3M Innovative Properties Company | Ring-opened azlactone initiators for nitroxide-mediated polymerization |
US6677413B1 (en) | 2003-02-05 | 2004-01-13 | 3M Innovative Properties Company | Azlactone initiators for nitroxide-mediated polymerization |
US6747104B1 (en) * | 2003-03-21 | 2004-06-08 | 3M Innovative Properties Company | Azlactone photoiniferters for radical polymerization |
US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened azlactone photoiniferters for radical polymerization |
US6919409B2 (en) | 2003-06-26 | 2005-07-19 | Symyx Technologies, Inc. | Removal of the thiocarbonylthio or thiophosphorylthio end group of polymers and further functionalization thereof |
US6753391B1 (en) | 2003-05-05 | 2004-06-22 | 3M Innovative Properties Company | Ring-opened azlactone chain transfer agents for radical polymerization |
US6762257B1 (en) | 2003-05-05 | 2004-07-13 | 3M Innovative Properties Company | Azlactone chain transfer agents for radical polymerization |
US7834113B2 (en) | 2003-05-08 | 2010-11-16 | E. I. Du Pont De Nemours And Company | Photoresist compositions and processes for preparing the same |
DE10322830A1 (de) * | 2003-05-19 | 2004-12-09 | Tesa Ag | Verfahren zur kontinuierlichen Herstellung von Polymeren aus vinylischen Verbindungen durch Substanz-beziehungsweise Lösungsmittelpolymerisation |
DE10327198A1 (de) | 2003-06-17 | 2005-01-13 | Tesa Ag | Repulpierbare Haftklebemassen |
US6969744B2 (en) * | 2003-06-19 | 2005-11-29 | University Of Southern Mississippi | Living and quasiliving cationic telechelic polymers quenched by N-substituted pyrrole and methods for their preparation |
GB0314472D0 (en) | 2003-06-20 | 2003-07-23 | Warwick Effect Polymers Ltd | Polymer |
BRPI0411903A (pt) | 2003-06-24 | 2006-08-08 | Polymers Australia Pty Ltd | agentes de dispersão acrìlicos em nanocompostos |
WO2005000924A1 (en) | 2003-06-26 | 2005-01-06 | Symyx Technologies, Inc. | Photoresist polymers |
WO2005000923A1 (en) * | 2003-06-26 | 2005-01-06 | Symyx Technologies, Inc. | Photoresist polymers and compositions having acrylic- or methacrylic-based polymeric resin prepared by a living free radical process |
US7250475B2 (en) | 2003-06-26 | 2007-07-31 | Symyx Technologies, Inc. | Synthesis of photoresist polymers |
JP4725739B2 (ja) | 2003-06-26 | 2011-07-13 | Jsr株式会社 | フォトレジストポリマー組成物 |
FR2859728B1 (fr) * | 2003-09-15 | 2008-07-11 | Oreal | Copolymeres ethyleniques sequences comprenant une sequence vinyllactame, compositions cosmetiques ou pharmaceutiques les contenant, et utilisation de ces copolymeres en cosmetique |
US20050238594A1 (en) * | 2003-09-15 | 2005-10-27 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic or pharmaceutical compositions comprising them and cosmetic use of these copolymers |
US7696292B2 (en) * | 2003-09-22 | 2010-04-13 | Commonwealth Scientific And Industrial Research Organisation | Low-polydispersity photoimageable acrylic polymers, photoresists and processes for microlithography |
US7408013B2 (en) | 2003-09-23 | 2008-08-05 | Commonwealth Scientific And Industrial Research Organization | Low-polydispersity photoimageable polymers and photoresists and processes for microlithography |
DE10357323A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Haftklebemasse |
DE10357322A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Zweischichtige Haftklebemasse |
DE10359973A1 (de) | 2003-12-18 | 2005-07-21 | Tesa Ag | Haftklebemasse auf Basis von Acrylatblockcopolymeren |
DE102004001412A1 (de) | 2004-01-09 | 2005-08-25 | Tesa Ag | Haftklebemasse auf Basis eines Acrylatpolymerblends |
US7468413B2 (en) | 2004-01-30 | 2008-12-23 | Khodia Inc. | Rare earth aggregate formulation using di-block copolmers |
US7632905B2 (en) | 2004-04-09 | 2009-12-15 | L'oreal S.A. | Block copolymer, composition comprising it and cosmetic treatment process |
DK1733211T3 (da) * | 2004-04-08 | 2012-04-16 | Univ Johns Hopkins | Forarbejdelige molekylære prægede polymerer |
US7407816B2 (en) | 2004-05-07 | 2008-08-05 | Gentius, Inc | Isoelectric particles and uses thereof |
FR2871470B1 (fr) | 2004-06-11 | 2007-01-12 | Oreal | Copolymere a gradient, composition et procede cosmetique de maquillage ou de soin |
DE502005007001D1 (de) | 2004-06-23 | 2009-05-14 | Tesa Ag | Medizinischer biosensor, mittels dem biologische flussigkeiten untersucht werden |
FR2872039B1 (fr) * | 2004-06-23 | 2006-08-04 | Rhodia Chimie Sa | Composition cosmetique comprenant un polyorganosiloxane et ses utilisations |
JP2008504411A (ja) | 2004-07-01 | 2008-02-14 | ウニベルズィタイト・ヘント | (アルキル)アクリル酸部分を含有する単分散性ポリマー、前駆体およびその作製方法ならびにその適用 |
DE102004033242A1 (de) * | 2004-07-08 | 2006-02-02 | Tesa Ag | Haftklebemasse |
US7851572B2 (en) * | 2004-07-28 | 2010-12-14 | Coatex S.A.S. | Polymers produced by using sulphur compounds in the form of transfer agents for controlled radical polymerisation of acrylic acid and the use thereof |
FR2868072B1 (fr) * | 2004-07-28 | 2006-06-30 | Coatex Soc Par Actions Simplif | Polymeres obtenus par l'utilisation de composes soufres comme agents de transfert pour la polymerisation radicalaire controlee de l'acide acrylique et leurs applications |
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 |
WO2006023742A2 (en) * | 2004-08-20 | 2006-03-02 | Chevron Oronite Company Llc | Method for preparation of polyolefins containing exo-olefin chain ends |
WO2006027385A1 (de) | 2004-09-09 | 2006-03-16 | Tesa Ag | Funktionalisierte polymere bzw. haftklebemassen |
CA2584744C (en) | 2004-10-25 | 2013-09-24 | The Lubrizol Corporation | Star polymers and compositions thereof |
EP2292668B1 (en) * | 2004-10-25 | 2019-03-20 | The Lubrizol Corporation | Process for preparing polymers and compositions thereof |
US7279446B2 (en) | 2004-11-15 | 2007-10-09 | Rhodia Inc. | Viscoelastic surfactant fluids having enhanced shear recovery, rheology and stability performance |
BRPI0606305A2 (pt) | 2005-01-11 | 2009-06-16 | Ciba Sc Holding Inc | processo para preparação de um polìmero ou copolìmero modificado, bem como uso concentrado de pigmento e composição compreendendo o polìmero ou copolìmero assim obtido |
US7345186B2 (en) | 2005-01-18 | 2008-03-18 | The Goodyear Tire & Rubber Company | Oxathiazaphospholidine free radical control agent |
US7947421B2 (en) | 2005-01-24 | 2011-05-24 | Fujifilm Corporation | Positive resist composition for immersion exposure and pattern-forming method using the same |
US8877830B2 (en) | 2005-02-10 | 2014-11-04 | The Regents Of The University Of Colorado, A Body Corporate | Stress relief for crosslinked polymers |
US7943680B2 (en) * | 2005-02-10 | 2011-05-17 | The Regents Of The University Of Colorado | Stress relaxation in crosslinked polymers |
US7410694B2 (en) | 2005-04-11 | 2008-08-12 | Tesa Aktiengesellschaft | Adhesive |
US20080319131A1 (en) * | 2005-08-26 | 2008-12-25 | Mccullough Richard D | Electrically Conductive Polymers and Raft Polymerization |
JP4961707B2 (ja) * | 2005-09-29 | 2012-06-27 | Jsr株式会社 | 樹脂の合成法 |
US7816459B2 (en) * | 2005-12-30 | 2010-10-19 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using polymeric nitrogen compounds |
US8013073B2 (en) * | 2005-12-30 | 2011-09-06 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using nonaromatic heterocyclic compounds |
JP5000904B2 (ja) * | 2006-03-15 | 2012-08-15 | 株式会社クラレ | 末端にメルカプト基を有するポリビニルアルコール系重合体の製造方法 |
DE102006021200A1 (de) | 2006-05-06 | 2007-11-15 | Byk-Chemie Gmbh | Verwendung von Copolymeren als Haftvermittler in Lacken |
US8034534B2 (en) | 2006-08-14 | 2011-10-11 | E.I. Du Pont De Nemours And Company | Fluorinated polymers for use in immersion lithography |
DE102006062441A1 (de) | 2006-12-27 | 2008-07-03 | Byk-Chemie Gmbh | Modifizierte Kammcopolymere |
FR2923487B1 (fr) * | 2007-11-09 | 2009-12-04 | Rhodia Operations | Copolymere ampholyte a architecture controlee |
EP1972645B1 (en) * | 2007-03-21 | 2009-11-11 | E.I. Du Pont De Nemours And Company | Fluorobetaine copolymer and fire fighting foam concentrates therefrom |
FI122734B (fi) | 2007-05-21 | 2012-06-15 | Kemira Oyj | Prosessikemikaali käytettäväksi paperin tai kartongin valmistuksessa |
JP2009001776A (ja) * | 2007-06-11 | 2009-01-08 | Rohm & Haas Co | 水性エマルジョンポリマー会合性増粘剤 |
FR2917415B1 (fr) * | 2007-06-14 | 2012-10-12 | Rhodia Recherches Et Tech | Microgel polymerique comprenant des unites cationiques |
JP2010533586A (ja) | 2007-07-13 | 2010-10-28 | ケミラ オイ | 鉱物質分散剤、およびそれを使用して鉱物質スラリーを調製するための方法 |
DE102007038458A1 (de) | 2007-08-14 | 2009-02-19 | Tesa Ag | Verbundelement |
DE102007043048A1 (de) | 2007-09-11 | 2009-03-12 | Byk-Chemie Gmbh | Polypropylenoxid-haltige Polyether und deren Mischungen mit Poly(meth)acrylaten als Pulverlackverlaufmittel |
WO2009035042A1 (ja) | 2007-09-12 | 2009-03-19 | Nissan Chemical Industries, Ltd. | ハイパーブランチポリマーの製造方法 |
FR2921663A1 (fr) | 2007-10-02 | 2009-04-03 | Bluestar Silicones France Soc | Polyorganosiloxanes a fonction piperidine depourvus de toxicite par contact cutane et utilisation de ces derniers dans des compositions cosmetiques |
EP2205826A4 (en) * | 2007-10-31 | 2011-06-29 | Rhodia | ADDITION OF A ZWITTERIONIC TENSID TO A WATER-SOLUBLE POLYMER TO INCREASE THE STABILITY OF POLYMERS IN AQUEOUS SOLUTIONS WITH SALTS AND / OR TENSIDES |
US7789160B2 (en) | 2007-10-31 | 2010-09-07 | Rhodia Inc. | Addition of nonionic surfactants to water soluble block copolymers to increase the stability of the copolymer in aqueous solutions containing salt and/or surfactants |
DE102008007713A1 (de) | 2008-02-04 | 2009-08-06 | Byk-Chemie Gmbh | Netz- und Dispergiermittel |
CN102037091B (zh) | 2008-03-20 | 2014-09-03 | 艾利丹尼森公司 | 具有官能团的控制位置的丙烯酸聚合物 |
US8394897B2 (en) * | 2008-03-25 | 2013-03-12 | Chevron Oronite Company Llc | Production of vinylidene-terminated polyolefins via quenching with monosulfides |
EP2109005A1 (en) | 2008-04-07 | 2009-10-14 | Stichting Dutch Polymer Institute | Process for preparing a polymeric relief structure |
US8912273B2 (en) * | 2008-06-17 | 2014-12-16 | Basf Se | Process for the preparation of an aqueous polymer dispersion |
EP2291422B1 (en) | 2008-06-23 | 2015-10-21 | Basf Se | Pigment dispersants with modified copolymers |
US8063154B2 (en) * | 2008-06-24 | 2011-11-22 | The University Of Southern Mississippi | Preparation of exo-olefin terminated polyolefins via quenching with alkoxysilanes or ethers |
FR2934154B1 (fr) * | 2008-07-23 | 2010-08-13 | Rhodia Operations | Emulsions thermosensibles |
FR2934861B1 (fr) | 2008-08-05 | 2012-12-28 | Arkema France | Nouveaux modifiants chocs du type coeur-ecorce pour matrices polymeres transparentes. |
EP2160946A1 (en) | 2008-09-09 | 2010-03-10 | Polymers CRC Limited | Process for the preparation of an antimicrobial article |
EP2160945A1 (en) | 2008-09-09 | 2010-03-10 | Polymers CRC Limited | Antimicrobial Article |
DE102008042629A1 (de) * | 2008-10-06 | 2010-04-08 | Wacker Chemie Ag | RAFT-Polymere und RAFT Reagenzien |
FR2937336B1 (fr) | 2008-10-22 | 2011-06-10 | Rhodia Operations | Composition pour les soins menagers comprenant un nanogel cationique |
US8133954B2 (en) | 2008-10-22 | 2012-03-13 | Chevron Oronite Company Llc | Production of vinylidene-terminated and sulfide-terminated telechelic polyolefins via quenching with disulfides |
US8344073B2 (en) | 2009-01-16 | 2013-01-01 | The University Of Southern Mississippi | Functionalization of polyolefins with phenoxy derivatives |
DE102009006593A1 (de) | 2009-01-29 | 2010-08-05 | Tesa Se | Verfahren zur Korrosionsschutzbehandlung von Metalloberflächen |
WO2010101252A1 (ja) * | 2009-03-06 | 2010-09-10 | 日産化学工業株式会社 | ハイパーブランチポリマーの製造方法 |
JP5552153B2 (ja) | 2009-03-25 | 2014-07-16 | ビック−ケミー ゲゼルシャフト ミット ベシュレンクテル ハフツング | 安定なポリオール混合物を含む組成物 |
US8552122B2 (en) * | 2009-03-31 | 2013-10-08 | The University Of Southern Mississippi | Amine-terminated telechelic polymers and precursors thereto and methods for their preparation |
DE102009021913A1 (de) | 2009-05-19 | 2010-12-02 | Byk-Chemie Gmbh | Terminal ungesättigte, oxetan-basierte Makromonomere und Verfahren zu deren Herstellung |
DE102009021912A1 (de) | 2009-05-19 | 2010-12-02 | Byk-Chemie Gmbh | Aus oxetan-basierten Makromonomeren erhältliche Polymere, Verfahren zu deren Herstellung und deren Verwendung als Additive in Beschichtungsmitteln und Kunststoffen |
CN102803303A (zh) * | 2009-06-16 | 2012-11-28 | 电气化学工业株式会社 | 聚氯丁二烯及其制造方法以及粘接剂 |
EP2264082A1 (de) | 2009-06-19 | 2010-12-22 | BYK-Chemie GmbH | Terminal ungesättigte, glycidol-basierte Markomonomere, daraus erhältliche Polymere, Herstellung und Verwendung |
US8394898B2 (en) * | 2009-07-31 | 2013-03-12 | The University Of Southern Mississippi | In situ formation of hydroxy chain end functional polyolefins |
FR2948932B1 (fr) | 2009-08-05 | 2012-08-17 | Lafarge Sa | Superplastifiant pour composition hydraulique |
JP5690355B2 (ja) | 2009-12-22 | 2015-03-25 | ビック−ケミー ゲゼルシャフト ミット ベシュレンクテル ハフツング | 安定なポリオール混合物を含む組成物 |
US20110224377A1 (en) * | 2010-03-11 | 2011-09-15 | Mahesh Kalyana Mahanthappa | Poly(vinyl ester) block copolymers |
US9376523B2 (en) | 2010-03-19 | 2016-06-28 | Wisconsin Alumni Research Foundation | Poly(vinyl alcohol)-poly(vinyl ester) block copolymers |
KR101524342B1 (ko) | 2010-03-30 | 2015-07-06 | 바스프 에스이 | 말단-관능화 중합체 |
AU2011256318B2 (en) | 2010-05-19 | 2015-11-19 | Avery Dennison Corporation | Ordered architectures in acrylic polymers |
US8492491B2 (en) | 2010-06-10 | 2013-07-23 | Chevron Oronite Company Llc | Methods for producing telechelic polyolefins from terpene initiators |
US8592527B2 (en) | 2010-06-14 | 2013-11-26 | University Of Southern Mississippi | Vinyl ether end-functionalized polyolefins |
AU2011305043B2 (en) | 2010-09-22 | 2016-09-15 | Commonwealth Scientific And Industrial Research Organisation | Continuous flow polymerisation process |
FR2965264B1 (fr) * | 2010-09-27 | 2013-11-29 | Rhodia Operations | Polymerisation radicalaire controlee de n-vinyl lactames en milieu aqueux |
FR2965564B1 (fr) | 2010-09-30 | 2012-10-26 | Rhodia Operations | Preparation de polymeres hydrophiles de haute masse par polymerisation radicalaire controlee |
US9115242B2 (en) | 2010-11-17 | 2015-08-25 | Byk-Chemie Gmbh | Copolymers which can be obtained from urethane-based, polysiloxane-containing macromonomers, processes for the preparation thereof and their use |
EP2655444B2 (en) * | 2010-12-22 | 2018-11-21 | Basell Polyolefine GmbH | Process for the preparation of ethylene copolymers in the presence of free-radical polymerization initiator by copolymerizing ethylene, a bi- or multifunctional comonomer and optionally further comonomers |
US9840568B2 (en) | 2011-05-30 | 2017-12-12 | Mitsubishi Chemical Corporation | Polymer and method for producing same |
DE102011077927A1 (de) | 2011-06-21 | 2012-12-27 | Tesa Se | Verfahren zur reversiblen kovalenten Vernetzung von Klebemassen |
WO2012175158A1 (de) | 2011-06-22 | 2012-12-27 | Byk-Chemie Gmbh | Oberflächenaktive kammcopolymere |
US8969484B2 (en) | 2011-07-08 | 2015-03-03 | Chevron Oronite Company Llc | Methods of producing mono- and multi-functional polymers from terpene-based initiators |
EP2551338A1 (en) | 2011-07-27 | 2013-01-30 | Henkel AG & Co. KGaA | Laundry detergent compositions with stain removal properties |
US9758597B2 (en) | 2011-08-05 | 2017-09-12 | The Regents Of The University Of Colorado, A Body Corporate | Reducing polymerization-induced shrinkage stress by reversible addition-fragmentation chain transfer |
US9907733B2 (en) | 2011-08-23 | 2018-03-06 | 3M Innovative Properties Company | Dental compositions comprising addition-fragmentation agents |
US8932572B2 (en) | 2011-08-26 | 2015-01-13 | Arrowhead Madison Inc. | Poly(vinyl ester) polymers for in vivo nucleic acid delivery |
CN103998481B (zh) | 2011-10-14 | 2018-02-06 | 艾利丹尼森公司 | 可控构造聚合物 |
CA2852104C (fr) | 2011-10-24 | 2019-09-10 | Rhodia Operations | Preparation de polymeres sequences amphiphiles par polymerisation radicalaire micellaire a caractere controle |
US20130109816A1 (en) | 2011-10-28 | 2013-05-02 | E.I. Du Pont De Nemours And Company | Processes for removing sulfur-containing end groups from polymers |
DE102011086502A1 (de) | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung ungefärbter Polyacrylatklebemassen mit enger Molmassenverteilung |
DE102011086503A1 (de) | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung von kohäsiven Polyacrylatklebemassen mit enger Molmassenverteilung |
WO2013086585A1 (en) | 2011-12-14 | 2013-06-20 | Commonwealth Scientific And Industrial Research Organisation | Raft polymers |
MX350257B (es) | 2012-01-18 | 2017-08-31 | Univ Iowa State Res Found Inc | Elastomeros termoplasticos mediante polimerizacion de radicales de transferencia de atomos de aceite vegetal. |
EP2809698B1 (fr) | 2012-01-31 | 2016-01-27 | Rhodia Operations | Polymérisation en phase dispersée de monomères vinyliques halogénés en présence de stabilisants réactifs vivants |
US9487598B2 (en) | 2012-01-31 | 2016-11-08 | Rhodia Operations | Live poly(n-vinyl lactam) reactive stabilizers for dispersed phase polymerization |
EP2817370B1 (en) | 2012-02-23 | 2020-08-19 | Basf Se | Fluorinated acrylate block copolymers with low dynamic surface tension |
FR2987837B1 (fr) | 2012-03-09 | 2014-03-14 | Rhodia Operations | Polymerisation radicalaire controlee en dispersion eau-dans-l'eau |
AU2012377385A1 (en) | 2012-04-18 | 2014-01-23 | Arrowhead Research Corporation | Poly(acrylate) polymers for in vivo nucleic acid delivery |
US20150126680A1 (en) | 2012-05-14 | 2015-05-07 | Merck Patent Gmbh | Particles for electrophoretic displays |
DE102012212883A1 (de) | 2012-07-23 | 2014-05-15 | Tesa Se | Geschäumtes Klebeband zur Verklebung auf unpolaren Oberflächen |
EP2916801B1 (en) | 2012-11-12 | 2017-02-22 | 3M Innovative Properties Company | Dental compositions comprising addition-fragmentation agents |
US9731456B2 (en) | 2013-03-14 | 2017-08-15 | Sabic Global Technologies B.V. | Method of manufacturing a functionally graded article |
WO2014150700A1 (en) | 2013-03-15 | 2014-09-25 | E. I. Du Pont De Nemours And Company | Polymerization process protection means |
FR3004458A1 (fr) | 2013-04-11 | 2014-10-17 | Rhodia Operations | Fluides de fracturation a base de polymeres associatifs et de tensioactifs labiles |
HK1220219A1 (zh) | 2013-05-20 | 2017-04-28 | 爱荷华州立大学研究基金会有限公司 | 經由甘油三酯的可逆加成-斷裂鏈轉移聚合的熱塑性彈性體 |
WO2014206962A1 (de) | 2013-06-24 | 2014-12-31 | Byk-Chemie Gmbh | Haftungs-verstärkendes additiv und dieses enthaltende beschichtungszusammensetzung |
FR3011555A1 (fr) | 2013-10-04 | 2015-04-10 | Rhodia Operations | Polymeres sequences pour le controle du filtrat |
DE102013224774A1 (de) | 2013-12-03 | 2015-06-03 | Tesa Se | Mehrschichtiges Produkt |
EP2896637A1 (en) | 2014-01-21 | 2015-07-22 | Rhodia Operations | Copolymer comprising units of type A deriving from carboxylic acid monomers and units of type B deriving from sulfonic acid monomers |
US10377843B2 (en) * | 2014-05-12 | 2019-08-13 | Solvay Specialty Polymers Italy S.P.A. | Method for the controlled polymerization of fluoromonomers |
EP3204353A4 (en) * | 2014-10-09 | 2018-04-18 | Commonwealth Scientific and Industrial Research Organisation | All purpose raft agent |
FR3027309B1 (fr) | 2014-10-17 | 2018-08-10 | Rhodia Operations | Polymeres polyfonctionnels a base d'unites phosphonates et d'unites amines |
EP3018151A1 (en) | 2014-11-06 | 2016-05-11 | Universiteit Gent | Process for preparing inert raft polymers |
EP3034573A1 (en) | 2014-12-16 | 2016-06-22 | ALLNEX AUSTRIA GmbH | Flow modifier for coating compositions |
FR3034777A1 (fr) | 2015-04-07 | 2016-10-14 | Rhodia Operations | Polymeres sequences pour le controle du filtrat et de la rheologie |
FR3034776A1 (fr) | 2015-04-07 | 2016-10-14 | Rhodia Operations | Polymeres sequences pour le controle du filtrat |
FR3034768B1 (fr) | 2015-04-07 | 2017-05-05 | Rhodia Operations | Polymeres sequences pour le controle du filtrat |
EP3292189A2 (fr) | 2015-05-04 | 2018-03-14 | Rhodia Operations | Copolymères pour la lubrification des métaux |
FR3037074B1 (fr) | 2015-06-03 | 2017-07-14 | Rhodia Operations | Agents de suspension obtenus par polymerisation micellaire |
JP7101615B2 (ja) | 2015-08-31 | 2022-07-15 | ビイク-ヒエミー ゲゼルシャフト ミツト ベシユレンクテル ハフツング | ポリシロキサンマクロモノマー単位を有するコポリマー、該コポリマーの製造方法、ならびに該コポリマーの、コーティング組成物およびポリマー成形コンパウンドにおける使用 |
CN107849358B (zh) | 2015-08-31 | 2021-05-07 | 毕克化学有限公司 | 含有聚醚-聚硅氧烷大分子单体单元的共聚物、其制备方法以及其在涂料组合物和聚合物模塑料中的用途 |
FR3043083B1 (fr) | 2015-10-30 | 2019-04-19 | Rhodia Operations | Polymeres sequences amphiphiles solubles en milieu fortement salin |
DE102015222028A1 (de) | 2015-11-09 | 2017-05-11 | Tesa Se | Kationisch polymerisierbare Polyacrylate enthaltend Alkoxysilangruppen und deren Verwendung |
BR112018011501B1 (pt) | 2015-12-10 | 2022-05-31 | Rhodia Operations | Composição de material agrícola, seu processo de preparação e métodos para controlar e prevenir peste e para aperfeiçoar o crescimento de planta |
WO2017103635A1 (en) | 2015-12-16 | 2017-06-22 | Rhodia Poliamida E Especialidades Ltda | Emulsifier system for explosive emulsions |
DE102016207550A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Funktionalisierte (Co)Polymere für Klebesysteme und Klebebänder |
DE102016207548A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
DE102016207540A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Wasserdampfsperrende Klebemasse mit hochfunktionalisiertem Poly(meth)acrylat |
CA3043623A1 (en) | 2016-11-29 | 2018-06-07 | Lingjuan SHEN | Polymeric systems for particle dispersion |
EP3577175B1 (en) | 2017-02-01 | 2023-05-24 | 3D Systems, Inc. | Method of 3d printing using 3d printing ink containing a cyclopolymerizable monomer |
FR3064641A1 (fr) | 2017-04-03 | 2018-10-05 | Rhodia Operations | Association pour le controle du filtrat et la migration de gaz |
CN110945037B (zh) | 2017-07-21 | 2022-11-11 | 电化株式会社 | 氯丁二烯系聚合物和其制造方法 |
WO2019026914A1 (ja) | 2017-07-31 | 2019-02-07 | デンカ株式会社 | ブロック共重合体及びブロック共重合体の製造方法 |
FR3070043B1 (fr) | 2017-08-09 | 2019-08-16 | Rhodia Operations | Formulation contenant un polymere associatif |
MX2020002862A (es) | 2017-09-14 | 2020-11-06 | Chemetall Gmbh | Metodo para el pre-tratado de materiales de aluminio, especificamente ruedas de aluminio. |
FR3071850B1 (fr) | 2017-10-02 | 2020-06-12 | Total Marketing Services | Composition d’additifs pour carburant |
FR3072095B1 (fr) | 2017-10-06 | 2020-10-09 | Total Marketing Services | Composition d'additifs pour carburant |
WO2019081277A1 (en) | 2017-10-23 | 2019-05-02 | Basf Se | AQUEOUS SILICONE POLYMER EMULSION |
FR3073522B1 (fr) | 2017-11-10 | 2019-12-13 | Total Marketing Services | Nouveau copolymere et son utilisation comme additif pour carburant |
FR3074499B1 (fr) | 2017-12-06 | 2020-08-28 | Total Marketing Services | Utilisation d'un copolymere particulier pour prevenir les depots sur les soupapes des moteurs a injection indirecte essence |
FR3074498B1 (fr) | 2017-12-06 | 2020-09-11 | Total Marketing Services | Composition d’additifs pour carburant |
FR3074497B1 (fr) | 2017-12-06 | 2020-09-11 | Total Marketing Services | Composition d’additifs pour carburant |
US11421147B2 (en) | 2017-12-19 | 2022-08-23 | Rhodia Operations | Aqueous formulations of surfactants and associative polymers for the assisted recovery of petroleum |
DE102017223147A1 (de) | 2017-12-19 | 2019-06-19 | Tesa Se | Oberflächenschutzfolie mit Schaumschicht |
CN111492035B (zh) | 2017-12-20 | 2023-05-02 | 罗地亚经营管理公司 | 用于颗粒分散的聚合物体系 |
FR3075813B1 (fr) | 2017-12-21 | 2021-06-18 | Total Marketing Services | Utilisation de polymeres reticules pour ameliorer les proprietes a froid de carburants ou combustibles |
EP3733722A4 (en) | 2017-12-27 | 2021-09-08 | National University Corporation Yamagata University | ZWITTERIONIC POLYMER, ITS PRODUCTION PROCESS AND PROTEIN STABILIZER CONTAINING IT |
AR114185A1 (es) | 2018-01-23 | 2020-07-29 | Adama Makhteshim Ltd | Síntesis de 5-cloro-2-[(3,4,4-trifluoro-3-buten-1-il)tio]-tiazol |
FR3079833B1 (fr) | 2018-04-10 | 2020-10-09 | Rhodia Operations | Composition aqueuse gelifiee pour l'extraction petroliere |
FR3083238A1 (fr) | 2018-07-02 | 2020-01-03 | Rhodia Operations | Relargage progressif de chaines polymeres en milieu liquide |
EP3818191A1 (en) | 2018-07-05 | 2021-05-12 | Chemetall GmbH | Method for treating metallic surfaces with an acidic aqueous composition and a post rinsing composition to improve corrosion resistance |
US12043758B2 (en) | 2018-07-05 | 2024-07-23 | Specialty Operations France | Method for treating metallic surfaces with an acidic aqueous composition to improve corrosion resistance |
EP3783040B1 (en) | 2018-08-31 | 2024-08-21 | Denka Company Limited | Copolymer of chloroprene monomer and unsaturated nitrile compound, composition containing copolymer, vulcanization molded body of composition, and use of vulcanization molded body |
KR20210046796A (ko) | 2018-09-07 | 2021-04-28 | 케메탈 게엠베하 | 알루미늄 함유 기판의 표면을 처리하는 방법 |
ES2970992T3 (es) | 2018-09-07 | 2024-06-03 | Chemetall Gmbh | Método para tratar superficies de sustratos que contienen aluminio |
DE102018216868A1 (de) | 2018-10-01 | 2020-04-02 | Tesa Se | Latent reaktiver Klebefilm |
WO2020074529A1 (en) | 2018-10-08 | 2020-04-16 | Chemetall Gmbh | Method for ni-free phosphatizing of metal surfaces and composition for use in such a method |
WO2020074527A1 (en) | 2018-10-08 | 2020-04-16 | Chemetall Gmbh | Method for ni-free phosphatizing of metal surfaces and composition for use in such a method |
FR3087788B1 (fr) | 2018-10-24 | 2021-06-25 | Total Marketing Services | Association d'additifs pour carburant |
EP3898810A1 (en) | 2018-12-20 | 2021-10-27 | Avery Dennison Corporation | Adhesive with high filler content |
JP2022522446A (ja) | 2019-02-28 | 2022-04-19 | ローディア オペレーションズ | エマルジョンの高安定化のための組成物 |
FR3093514A1 (fr) | 2019-03-05 | 2020-09-11 | Rhodia Operations | Suspension de polymères associatifs pour le traitement de formations souterraines |
WO2020182919A1 (en) | 2019-03-12 | 2020-09-17 | Rhodia Operations | Stabilized friction reducer emulsions |
WO2020190622A1 (en) | 2019-03-15 | 2020-09-24 | Rhodia Operations | Polymer compositions and use of the same |
KR20210142203A (ko) | 2019-04-16 | 2021-11-24 | 로디아 오퍼레이션스 | 선택적 친수성 매크로-raft제를 사용하여 고-고형물 저점도 라텍스를 제조하기 위한 공정 |
GB2587330B (en) | 2019-09-12 | 2024-04-10 | Design Blue Ltd | Protective cover for a 5G wireless telecommunications device and methods for reducing signal attenuation using the same |
FR3101882B1 (fr) | 2019-10-14 | 2022-03-18 | Total Marketing Services | Utilisation de polymères cationiques particuliers comme additifs pour carburants et combustibles |
DE102019215890A1 (de) | 2019-10-16 | 2021-04-22 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
DE102019219166B4 (de) | 2019-12-09 | 2023-08-24 | Tesa Se | Strukturelle Haftklebemasse und ihre Verwendung |
JP7439493B2 (ja) * | 2019-12-18 | 2024-02-28 | 住友ゴム工業株式会社 | ジチオエステル化合物 |
DE102020203952A1 (de) | 2020-03-26 | 2021-09-30 | Tesa Se | Latent reaktiver Klebefilm |
DE102020205568B4 (de) | 2020-04-30 | 2022-10-06 | Tesa Se | Blockcopolymer-basierende Haftklebmasse und Verfahren zu ihrer Herstellung |
EP4143248A1 (en) | 2020-04-30 | 2023-03-08 | Dow Global Technologies LLC | Process for preparing olefin-acrylate block copolymers by raft polyerization |
MX2023004398A (es) | 2020-10-23 | 2023-07-11 | Energy Solutions Us Llc | Sistemas polimericos que tienen viscosidad mejorada y propiedades de transporte de apuntalantes. |
CN117321151A (zh) | 2021-05-12 | 2023-12-29 | 巴斯夫欧洲公司 | 包含片状过渡金属颗粒的组合物 |
JPWO2023276937A1 (en, 2012) | 2021-06-30 | 2023-01-05 | ||
FR3125296A1 (fr) | 2021-07-13 | 2023-01-20 | Rhodia Operations | Préparation de polymères séquencés amphiphiles par polymérisation radicalaire micellaire inverse |
WO2023007131A1 (en) | 2021-07-27 | 2023-02-02 | Convatec Limited | Intermittent catheters |
WO2023007128A1 (en) | 2021-07-27 | 2023-02-02 | Convatec Limited | Intermittent catheters |
US20250002614A1 (en) * | 2021-07-29 | 2025-01-02 | Evonik Operations Gmbh | Process for preparing low molecular weight polyacrylates and products thereof |
EP4423176A1 (en) | 2021-10-26 | 2024-09-04 | Basf Se | A method for producing interference elements |
WO2024052192A1 (en) | 2022-09-07 | 2024-03-14 | Unomedical A/S | Fluoropolymer medical devices |
WO2024052193A1 (en) | 2022-09-07 | 2024-03-14 | Unomedical A/S | Medical devices |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2553134B2 (ja) * | 1987-04-07 | 1996-11-13 | 三菱化学株式会社 | Aba型ブロック共重合体 |
FR2629826B1 (fr) * | 1988-04-08 | 1991-01-18 | Distugil | Procede de fabrication de polychloroprene |
MX173261B (es) * | 1988-06-28 | 1994-02-14 | Minnesota Mining & Mfg | Copolimeros acrilicos y metodo para su fabricacion |
DE69009380T2 (de) * | 1989-09-07 | 1994-09-15 | Tosoh Corp | Chloroprenpolymerisat. |
CA2038117A1 (en) * | 1990-03-29 | 1991-09-30 | Mahfuza B. Ali | Controllable radiation curable photoiniferter prepared adhesives for attachment of microelectronic devices and a method of attaching microelectronic devices therewith |
JPH04198303A (ja) † | 1990-11-27 | 1992-07-17 | Sanyo Chem Ind Ltd | 重合開始剤および重合方法 |
JP3363478B2 (ja) † | 1991-08-15 | 2003-01-08 | 三菱製紙株式会社 | 静電写真用液体現像剤 |
WO1993020164A1 (en) * | 1992-03-31 | 1993-10-14 | Minnesota Mining And Manufacturing Company | Ultraviolet radiation curable acrylate pressure-sensitive adhesive compositions |
US5264530A (en) | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
JPH06100609A (ja) * | 1992-09-22 | 1994-04-12 | Japan Synthetic Rubber Co Ltd | 共重合体ラテックスの製造方法 |
FR2696468B1 (fr) * | 1992-10-06 | 1994-11-04 | Atochem Elf Sa | Polymères téléchéliques hydroxylés, leur procédé de fabrication et leurs utilisations. |
TW316266B (en, 2012) | 1993-07-30 | 1997-09-21 | Commw Scient Ind Res Org | |
AUPM930394A0 (en) | 1994-11-09 | 1994-12-01 | Commonwealth Scientific And Industrial Research Organisation | Block copolymer synthesis |
DE19611968A1 (de) † | 1995-03-31 | 1996-10-02 | Sumitomo Chemical Co | Verfahren zur Herstellung von Styrolpolymeren |
JP3344201B2 (ja) † | 1996-03-27 | 2002-11-11 | 住友化学工業株式会社 | スチレン系重合体の製造方法 |
ATE210684T1 (de) | 1996-07-10 | 2001-12-15 | Du Pont | POLYMERISATION MIT ßLIVINGß KENNZEICHEN |
FR2764892B1 (fr) * | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
-
1998
- 1998-12-11 IL IL13638998A patent/IL136389A0/xx unknown
- 1998-12-11 US US09/581,953 patent/US6642318B1/en not_active Expired - Lifetime
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- 1998-12-11 AU AU19113/99A patent/AU1911399A/en not_active Abandoned
- 1998-12-11 BR BR9815179-7A patent/BR9815179A/pt not_active Application Discontinuation
- 1998-12-11 JP JP2000539065A patent/JP4886109B2/ja not_active Expired - Lifetime
- 1998-12-11 KR KR20007006738A patent/KR100589073B1/ko not_active Expired - Lifetime
- 1998-12-11 CA CA002309279A patent/CA2309279C/en not_active Expired - Lifetime
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- 1998-12-11 WO PCT/US1998/026428 patent/WO1999031144A1/en active IP Right Grant
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113980486A (zh) * | 2021-11-18 | 2022-01-28 | 浙江理工大学 | 一种无皂化学交联型共聚物纳米粒子包覆有机颜料杂化胶乳的制备方法 |
CN113980486B (zh) * | 2021-11-18 | 2023-10-20 | 浙江理工大学 | 一种无皂化学交联型共聚物纳米粒子包覆有机颜料杂化胶乳的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
DK1054906T3 (da) | 2007-03-26 |
JP2009167421A (ja) | 2009-07-30 |
CA2309279A1 (en) | 1999-06-24 |
IN2005MU00441A (en, 2012) | 2005-12-02 |
IN2000MU00034A (en, 2012) | 2007-07-06 |
DE69836501T3 (de) | 2013-07-18 |
NZ505654A (en) | 2002-03-28 |
MXPA00005653A (es) | 2001-05-01 |
MX226742B (en, 2012) | 2005-03-16 |
KR100589073B1 (ko) | 2006-06-13 |
JP4886109B2 (ja) | 2012-02-29 |
BR9815179A (pt) | 2000-10-10 |
EP1054906B1 (en) | 2006-11-22 |
ES2277678T3 (es) | 2007-07-16 |
WO1999031144A1 (en) | 1999-06-24 |
US20040024132A1 (en) | 2004-02-05 |
AU1911399A (en) | 1999-07-05 |
KR20010033296A (ko) | 2001-04-25 |
CA2309279C (en) | 2009-07-14 |
IL136389A0 (en) | 2001-06-14 |
EP1054906B2 (en) | 2013-04-10 |
JP2002508409A (ja) | 2002-03-19 |
US6642318B1 (en) | 2003-11-04 |
DE69836501D1 (de) | 2007-01-04 |
DE69836501T2 (de) | 2007-09-20 |
US6747111B2 (en) | 2004-06-08 |
EP1054906A1 (en) | 2000-11-29 |
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