JP4744783B2 - 制御されたラジカル重合によって造られる界面活性ブロックコポリマー - Google Patents
制御されたラジカル重合によって造られる界面活性ブロックコポリマー Download PDFInfo
- Publication number
- JP4744783B2 JP4744783B2 JP2002587483A JP2002587483A JP4744783B2 JP 4744783 B2 JP4744783 B2 JP 4744783B2 JP 2002587483 A JP2002587483 A JP 2002587483A JP 2002587483 A JP2002587483 A JP 2002587483A JP 4744783 B2 JP4744783 B2 JP 4744783B2
- Authority
- JP
- Japan
- Prior art keywords
- block
- copolymer
- block copolymer
- weight
- saturated
- 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
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 32
- 239000004094 surface-active agent Substances 0.000 title claims description 7
- 238000010526 radical polymerization reaction Methods 0.000 title abstract description 13
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 229920001577 copolymer Polymers 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 239000003973 paint Substances 0.000 claims abstract description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 57
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 50
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 47
- 229920000642 polymer Polymers 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 239000012991 xanthate Substances 0.000 claims description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 16
- -1 thioether-thiones Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 10
- 125000002355 alkine group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 230000000873 masking effect Effects 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical group O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 claims description 3
- 239000012988 Dithioester Substances 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000012990 dithiocarbamate Substances 0.000 claims description 3
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 3
- 125000005022 dithioester group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000359 diblock copolymer Polymers 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 229920000428 triblock copolymer Polymers 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 13
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 239000004566 building material Substances 0.000 abstract 1
- 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 88
- 239000011541 reaction mixture Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- 229920002125 Sokalan® Polymers 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000011343 solid material Substances 0.000 description 6
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001735 carboxylic acids Chemical group 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 description 1
- DOGQRRGVLIGIEG-UHFFFAOYSA-N 1-(prop-2-enoylamino)butane-2-sulfonic acid Chemical compound CCC(S(O)(=O)=O)CNC(=O)C=C DOGQRRGVLIGIEG-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical group C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- FXUGUYXCZSDFLG-UHFFFAOYSA-N 2-(ditert-butylamino)ethyl prop-2-enoate Chemical compound CC(C)(C)N(C(C)(C)C)CCOC(=O)C=C FXUGUYXCZSDFLG-UHFFFAOYSA-N 0.000 description 1
- DNLZVNZIAOXDTF-UHFFFAOYSA-N 2-[(dimethylamino)methyl]prop-2-enamide Chemical compound CN(C)CC(=C)C(N)=O DNLZVNZIAOXDTF-UHFFFAOYSA-N 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical group C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CBRIXUYRDNCSBN-UHFFFAOYSA-N N(=C=O)C1=C2C(C(=O)NC2=O)=CC=C1 Chemical compound N(=C=O)C1=C2C(C(=O)NC2=O)=CC=C1 CBRIXUYRDNCSBN-UHFFFAOYSA-N 0.000 description 1
- 240000005428 Pistacia lentiscus Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 239000013033 iniferter Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000004043 oxo group Chemical group O=* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000007332 vesicle formation Effects 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- 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
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
- Detergent Compositions (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28884401P | 2001-05-04 | 2001-05-04 | |
| US60/288,844 | 2001-05-04 | ||
| PCT/FR2002/001349 WO2002090409A2 (fr) | 2001-05-04 | 2002-04-19 | Copolymeres a blocs tensioactifs prepares par polymerisation radicalaire controlee |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005503452A JP2005503452A (ja) | 2005-02-03 |
| JP2005503452A5 JP2005503452A5 (enExample) | 2006-06-15 |
| JP4744783B2 true JP4744783B2 (ja) | 2011-08-10 |
Family
ID=23108901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002587483A Expired - Lifetime JP4744783B2 (ja) | 2001-05-04 | 2002-04-19 | 制御されたラジカル重合によって造られる界面活性ブロックコポリマー |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20020198347A1 (enExample) |
| EP (1) | EP1397403B1 (enExample) |
| JP (1) | JP4744783B2 (enExample) |
| AT (1) | ATE388970T1 (enExample) |
| DE (1) | DE60225550T2 (enExample) |
| WO (1) | WO2002090409A2 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6716948B1 (en) | 1999-07-31 | 2004-04-06 | Symyx Technologies, Inc. | Controlled-architecture polymers and use thereof as separation media |
| 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 |
| MXPA05001005A (es) * | 2002-07-26 | 2005-05-16 | Atofina | Composicion adhesiva para un medio humedo, con base en copolimeros de bloqueo que comprenden por lo menos un bloque hidrofilo. |
| 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 |
| JP4254292B2 (ja) * | 2003-03-24 | 2009-04-15 | 星光Ｐｍｃ株式会社 | 水性顔料分散剤およびその製造方法 |
| 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 |
| US6762257B1 (en) * | 2003-05-05 | 2004-07-13 | 3M Innovative Properties Company | Azlactone chain transfer agents for radical polymerization |
| JP2005002325A (ja) * | 2003-05-19 | 2005-01-06 | Canon Inc | ポリマー、それを含有するポリマー含有組成物、インク組成物、該インク組成物を用いたインク付与方法および装置 |
| DE602004008468T2 (de) | 2003-06-26 | 2008-05-21 | Jsr Corp. | Photoresistzusammensetzungen |
| WO2005000924A1 (en) | 2003-06-26 | 2005-01-06 | Symyx Technologies, Inc. | Photoresist polymers |
| US7250475B2 (en) | 2003-06-26 | 2007-07-31 | Symyx Technologies, Inc. | Synthesis of photoresist polymers |
| US20090018270A1 (en) * | 2003-09-03 | 2009-01-15 | Regan Crooks | Copolymer having a controlled structure and use thereof |
| US7632905B2 (en) * | 2004-04-09 | 2009-12-15 | L'oreal S.A. | Block copolymer, composition comprising it and cosmetic treatment process |
| JP5113988B2 (ja) * | 2005-03-31 | 2013-01-09 | 株式会社日本触媒 | セメント混和剤用ポリカルボン酸系ポリマー |
| FR2885367B1 (fr) * | 2005-05-03 | 2007-07-27 | Rhodia Chimie Sa | Organosol stabilise par des polymeres sequences amphiphiles |
| DE602006006825D1 (de) * | 2006-08-17 | 2009-06-25 | Rhodia Operations | Blockcopolymere, Verfahren zu deren Herstellung und ihre Verwendung in Emulsionen |
| ES2563498T3 (es) | 2007-08-27 | 2016-03-15 | Borealis Technology Oy | Equipo y procedimiento para producir gránulos de polímero |
| FR2965564B1 (fr) * | 2010-09-30 | 2012-10-26 | Rhodia Operations | Preparation de polymeres hydrophiles de haute masse par polymerisation radicalaire controlee |
| FR2975100B1 (fr) * | 2011-05-13 | 2014-09-26 | Oreal | Polymere sequence comprenant de l'acrylate d'isobutyle et de l'acide acry-lique, composition cosmetique et procede de traitement |
| MX354132B (es) * | 2011-10-24 | 2018-02-14 | Rhodia Operations | Preparacion de los polimeros en bloques anfifilicos por medio de la polimerizacion micelar por radicales controlada. |
| FR2986234B1 (fr) * | 2012-01-31 | 2014-06-13 | Rhodia Operations | Stabilisants reactifs poly(n-vinyl lactame) vivants pour polymerisation en phase dispersee |
| FR2986235B1 (fr) * | 2012-01-31 | 2015-02-06 | Rhodia Operations | Stabilisants reactifs poly(n-vinyl lactame) vivants pour polymerisation en phase dispersee |
| JP6550908B2 (ja) * | 2015-05-08 | 2019-07-31 | 国立大学法人福井大学 | アルケニルエーテル系重合体の製造方法 |
| RU2632004C1 (ru) * | 2016-06-06 | 2017-10-02 | Федеральное государственное бюджетное учреждение науки Институт металлоорганической химии им. Г.А. Разуваева Российской академии наук (ИМХ РАН) | Способ получения коллоидного раствора узкодисперсного по молекулярной массе амфифильного блоксополимера бутилакрилата и акриловой кислоты с узким распределением мицелл по размеру |
| WO2019162805A1 (en) * | 2018-02-21 | 2019-08-29 | 3M Innovative Properties Company | Ketone-containing controlled radical initiators for polymerization reactions |
| WO2025205553A1 (ja) * | 2024-03-29 | 2025-10-02 | 富士フイルム株式会社 | 樹脂の製造方法、感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜、パターン形成方法、及び電子デバイスの製造方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPM930394A0 (en) * | 1994-11-09 | 1994-12-01 | Commonwealth Scientific And Industrial Research Organisation | Block copolymer synthesis |
| FR2738573B1 (fr) * | 1995-09-08 | 1997-10-17 | Rhone Poulenc Chimie | Utilisation en tant qu'agents thermoepaississants de copolymeres multiblocs |
| DE19704714A1 (de) * | 1996-01-25 | 1997-07-31 | Basf Ag | Amphiphile Blockcopolymere |
| FR2764892B1 (fr) * | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
| US6111025A (en) * | 1997-06-24 | 2000-08-29 | The Lubrizol Corporation | Block copolymer surfactants prepared by stabilized free-radical polymerization |
| DE19806853A1 (de) * | 1998-02-19 | 1999-09-02 | Basf Ag | Verfahren zur Herstellung von Polymeren aus N-Vinylverbindungen |
| 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 |
| FR2794464B1 (fr) * | 1999-06-04 | 2005-03-04 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs par polymerisation radicalaire controlee a l'aide de thioether-thiones |
| US6437040B2 (en) * | 1999-09-01 | 2002-08-20 | Rhodia Chimie | Water-soluble block copolymers comprising a hydrophilic block and a hydrophobic block |
| BR0013695A (pt) * | 1999-09-01 | 2002-07-16 | Rhodia Chimie Sa | Copolìmero em blocos, processos de preparação dos mesmos, e, de controle de equilìbrio hidrófilo/ hidrófobo, e utilização de copolìmeros em blocos |
| ATE275280T1 (de) * | 2000-03-02 | 2004-09-15 | Lucatron Ag | Elektronisch detektierbare resonanzetikette, insbesondere rfid-labels |
| US6507837B1 (en) * | 2000-06-08 | 2003-01-14 | Hyperphrase Technologies, Llc | Tiered and content based database searching |
| US6410005B1 (en) * | 2000-06-15 | 2002-06-25 | Pmd Holdings Corp. | Branched/block copolymers for treatment of keratinous substrates |
| BR0114371A (pt) * | 2000-10-03 | 2003-12-09 | Unilever Nv | Composição cosmética ou para o cuidado pessoal, método cosmético de tratamento de cabelo, e, uso de uma composição cosmética |
| EP1801129A3 (en) * | 2000-10-06 | 2008-02-20 | Carnegie-Mellon University | Polymerization process for ionic monomers |
| US6559233B2 (en) * | 2001-07-13 | 2003-05-06 | Rhodia Chimie | Composition comprising a copolymer at least two charged blocks and type of opposite charge |
-
2002
- 2002-04-19 WO PCT/FR2002/001349 patent/WO2002090409A2/fr not_active Ceased
- 2002-04-19 DE DE60225550T patent/DE60225550T2/de not_active Expired - Lifetime
- 2002-04-19 AT AT02727681T patent/ATE388970T1/de not_active IP Right Cessation
- 2002-04-19 JP JP2002587483A patent/JP4744783B2/ja not_active Expired - Lifetime
- 2002-04-19 EP EP02727681A patent/EP1397403B1/fr not_active Expired - Lifetime
- 2002-05-02 US US10/137,945 patent/US20020198347A1/en not_active Abandoned
-
2005
- 2005-02-01 US US11/047,940 patent/US20050131144A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005503452A (ja) | 2005-02-03 |
| EP1397403A2 (fr) | 2004-03-17 |
| WO2002090409A2 (fr) | 2002-11-14 |
| US20020198347A1 (en) | 2002-12-26 |
| DE60225550T2 (de) | 2009-04-02 |
| WO2002090409A3 (fr) | 2003-12-04 |
| ATE388970T1 (de) | 2008-03-15 |
| US20050131144A1 (en) | 2005-06-16 |
| DE60225550D1 (de) | 2008-04-24 |
| EP1397403B1 (fr) | 2008-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4744783B2 (ja) | 制御されたラジカル重合によって造られる界面活性ブロックコポリマー | |
| EP1419181B1 (en) | Process for the preparation of latices using block copolymers as surfactants | |
| RU2265615C2 (ru) | Гелеобразная водная композиция, содержащая блок-сополимер, в котором имеется по меньшей мере один водорастворимый блок и один гидрофобный блок | |
| JP3542580B2 (ja) | ハロゲン化されたキサントゲン酸エステルにより制御された遊離ラジカル重合によって重合体を合成するための方法 | |
| US6812291B1 (en) | Method for block polymer synthesis by controlled radical polymerization from dithiocarbamate compounds | |
| JP4439597B2 (ja) | 制御されたラジカル重合によるブロック重合体の合成方法 | |
| JP4711685B2 (ja) | 制御された重合 | |
| US20010044498A1 (en) | Water-soluble block copolymers comprising a hydrophilic block and a hydrophobic block | |
| US20110301298A1 (en) | Acid functionalized gradient block copolymers | |
| CZ2003751A3 (cs) | Způsob syntézy blokového polymeru pomocí kontrolované radikálové polymerace v přítomnosti disulfidové sloučeniny | |
| CN1938338A (zh) | 用水溶性烷氧基胺进行自由基乳液聚合的方法 | |
| US6790908B2 (en) | Block copolymer | |
| JP3454564B2 (ja) | 水性エマルジョン組成物およびその製造方法 | |
| JP4145735B2 (ja) | 水性エマルション組成物の製造方法 | |
| JP2022529256A (ja) | 選択的親水性マクロ－ｒａｆｔ剤を使用する、高い固形分で低い粘度のラテックスの調製方法 | |
| Balgeman | Reversible Addition-Fragmentation Chain-Transfer Emulsion Polymerization and its Application to Waterborne Coatings | |
| US6890980B2 (en) | Synthesis of block polymers obtained by controlled free radical polymerization | |
| JP2007177217A (ja) | アクリル共重合体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20050912 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20051025 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20060125 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20060201 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20060425 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20070424 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070822 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20071011 |
|
| A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20080321 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090930 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20090930 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20091005 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101104 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101109 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110203 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110511 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140520 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4744783 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |