JP2015502440A - 塩化ビニリデンポリマーコンポジットの調製方法 - Google Patents
塩化ビニリデンポリマーコンポジットの調製方法 Download PDFInfo
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- JP2015502440A JP2015502440A JP2014547928A JP2014547928A JP2015502440A JP 2015502440 A JP2015502440 A JP 2015502440A JP 2014547928 A JP2014547928 A JP 2014547928A JP 2014547928 A JP2014547928 A JP 2014547928A JP 2015502440 A JP2015502440 A JP 2015502440A
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- Prior art keywords
- vinylidene chloride
- optionally substituted
- acid
- chloride polymer
- raft
- 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.)
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 229920000642 polymer Polymers 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 62
- 239000002131 composite material Substances 0.000 title claims abstract description 48
- 239000000178 monomer Substances 0.000 claims abstract description 76
- 239000007787 solid Substances 0.000 claims abstract description 61
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 45
- 239000011236 particulate material Substances 0.000 claims abstract description 43
- 239000007791 liquid phase Substances 0.000 claims abstract description 31
- 239000006185 dispersion Substances 0.000 claims abstract description 17
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 239000010419 fine particle Substances 0.000 claims abstract 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 230000002209 hydrophobic effect Effects 0.000 claims description 18
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims description 8
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical group CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- DUDCYUDPBRJVLG-UHFFFAOYSA-N ethoxyethane methyl 2-methylprop-2-enoate Chemical compound CCOCC.COC(=O)C(C)=C DUDCYUDPBRJVLG-UHFFFAOYSA-N 0.000 claims description 6
- DOMLXBPXLNDFAB-UHFFFAOYSA-N ethoxyethane;methyl prop-2-enoate Chemical compound CCOCC.COC(=O)C=C DOMLXBPXLNDFAB-UHFFFAOYSA-N 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 5
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 230000007246 mechanism Effects 0.000 claims description 5
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 4
- 239000011147 inorganic material Substances 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000011859 microparticle Substances 0.000 claims description 3
- 239000013618 particulate matter Substances 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 2
- 230000005593 dissociations Effects 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- -1 cerium dioxide core Chemical group 0.000 description 29
- 239000012987 RAFT agent Substances 0.000 description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 23
- 239000002245 particle Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- 239000003999 initiator Substances 0.000 description 16
- AISZNMCRXZWVAT-UHFFFAOYSA-N 2-ethylsulfanylcarbothioylsulfanyl-2-methylpropanenitrile Chemical compound CCSC(=S)SC(C)(C)C#N AISZNMCRXZWVAT-UHFFFAOYSA-N 0.000 description 15
- 229910000420 cerium oxide Inorganic materials 0.000 description 14
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 12
- 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 11
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 238000010526 radical polymerization reaction Methods 0.000 description 10
- 239000002243 precursor Substances 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- LAKYXBYUROTWBI-UHFFFAOYSA-N bis(benzylsulfanyl)methanethione Chemical compound C=1C=CC=CC=1CSC(=S)SCC1=CC=CC=C1 LAKYXBYUROTWBI-UHFFFAOYSA-N 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- 229920000126 latex Polymers 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 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 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
- 239000012966 redox initiator Substances 0.000 description 5
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- 238000013467 fragmentation Methods 0.000 description 4
- 238000006062 fragmentation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 238000002296 dynamic light scattering Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000004627 transmission electron microscopy Methods 0.000 description 3
- 229920001959 vinylidene polymer Polymers 0.000 description 3
- 239000012991 xanthate Substances 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 239000007771 core particle Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000005499 phosphonyl group Chemical group 0.000 description 2
- WDHYRUBXLGOLKR-UHFFFAOYSA-N phosphoric acid;prop-2-enoic acid Chemical class OC(=O)C=C.OP(O)(O)=O WDHYRUBXLGOLKR-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000010420 shell particle Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000004094 surface-active agent Substances 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
- 238000011282 treatment Methods 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical group OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- FQOWJGGXNSRNJS-YFKPBYRVSA-N (2s)-2-(2-methylprop-2-enoylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)C(C)=C FQOWJGGXNSRNJS-YFKPBYRVSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- DHBIJBUUMSDQMR-UHFFFAOYSA-N 1,4-dioxane prop-2-enoic acid Chemical compound O1CCOCC1.C(C=C)(=O)O DHBIJBUUMSDQMR-UHFFFAOYSA-N 0.000 description 1
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- ZIRURAJAJIQZFG-UHFFFAOYSA-N 1-aminopropane-1-sulfonic acid Chemical compound CCC(N)S(O)(=O)=O ZIRURAJAJIQZFG-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F114/02—Monomers containing chlorine
- C08F114/04—Monomers containing two carbon atoms
- C08F114/08—Vinylidene chloride
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08J2327/08—Homopolymers or copolymers of vinylidene chloride
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/221—Oxides; Hydroxides of metals of rare earth metal
- C08K2003/2213—Oxides; Hydroxides of metals of rare earth metal of cerium
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Abstract
Description
− 液相中固体微粒子物質の分散液を準備するステップであって、前記分散液はRAFT/MADIX剤を含むステップ;
− 前記分散液に、塩化ビニリデンおよび任意選択的に、それと共重合可能な少なくとも1種のエチレン性不飽和モノマーを供給するステップ;ならびに
− 塩化ビニリデンおよび任意選択的に、それと共重合可能な少なくとも1種のエチレン性不飽和モノマーをRAFT/MADIX剤の制御下で重合させて、固体微粒子物質の表面で塩化ビニリデンポリマーを形成するステップ
を含む方法が提供される。
CH2=CR1R2(I)
[式中、R1は、水素および−CH3から選択され、R2は、−CNおよび−COR3[ここで、R3は、−OH、−OR4(ここで、R4は、1個以上の−OH基を任意選択的に有するC1〜C18直鎖または分岐アルキル基、C2〜C10エポキシアルキル基およびC2〜C10アルコキシアルキル基である)から選択され、かつR3はまた、−NR5R6ラジカル(ここで、R5およびR6は、同じかまたは異なっていて、水素、および1個以上の−OH基を任意選択的に有するC1〜C10アルキル基から選択される]、上述の共重合可能な界面活性剤、およびメタクリレート末端ポリプロピレングリコールのリン酸エステルまたはその塩の一つ、ポリ(エチレンオキシド)メチルエーテルアクリレート(PEOA)、ポリ(エチレンオキシド)メチルエーテルメタクリレート(PEOMA)からも選択される]に対応するアクリルまたはメタクリルモノマーからなる群から選択される。
(式中、Raは、1個以上の親水性基で任意選択的に置換された有機基であり、Zは、ラジカル付加に向けてチオカルボニル基の十分な反応性を促進し得る任意の基である)
のものを含む。
(式中、eは、2〜4の整数である)
からなる群から選択される。
(式中、H1は、親水性特性(h1)を有する少なくとも1種のエチレン性不飽和モノマーに由来する繰り返し単位を含む親水性ブロックを表し;H2は、疎水性特性(h2)を有する少なくとも1種のエチレン性不飽和モノマーに由来する繰り返し単位を含む疎水性ブロックを表し;αおよびβは、独立して1〜99、典型的には1〜50、好ましくは1〜30、さらに好ましくは1〜20、より好ましくは1〜15の整数である)
で表されるとおりの親水性および疎水性繰り返し単位のブロック配置を有することができる。
(式中、H1、H2、αおよびβは、上に定義されたとおりであり、δおよびεは、独立して1〜10、好ましくは1〜5の整数であり、それぞれの繰り返し単位γは、同じかまたは異なっていてもよく、γは、1〜10、好ましくは1〜5、より好ましくは1〜3の整数である)
で表されるとおりの親水性および疎水性繰り返し単位のランダム配置を特徴とすることができる。
(式中、H1、H2、αおよびβは、上に定義されたとおりであり、ζは、1〜50、好ましくは2〜25、より好ましくは2〜10の整数である)
を有する。
アクリル酸(AA、Aldrich、99%)は、禁止剤除去カラムを通して精製した。アクリル酸ブチル(BA、Aldrich、≧99%)、塩化ビニリデン(VDC、Aldrich、99%)およびアクリル酸メチル(MA、Aldrich、99%)は、減圧下で蒸留して、禁止剤を除去した。2−アクリルアミド−2−メチルプロパンスルホン酸(AMPS、Aldrich 99%)およびスチレン(Aldrich>99%)は、受け入れたまま使用した。
ポリ(VDC−co−MA)コポリマーの分子量は、300mmの2つのカラム(mixed−C PL−gel5μm、Polymer Laboratories)および屈折率検出器を備えたPL−GPC50プラス(Varian)を用いてTHF中ゲル透過クロマトグラフィー(流量1mL,分−1)により決定した。CeO2/ポリ(VDC−co−MA)ハイブリッドラテックスの凍結乾燥試料をTHFに溶解させ、0.2mmPTFEフィルタ上でろ過し、その後、SEC装置において自動注入した。ポリスチレン標準(K=14.1×10−5dL/gおよびa=0.7、S.Mori et al.,“Size Exclusion Chromatography”,Springer Verlag,1999に従って)による較正を、80:20VDC:MA質量比を有するポリ(VDC−co−MA)コポリマー(K=35×10−5dL/gおよびa=0.57、A.Revillon et al.,J.Polym.Sci.,PartA:Polym.Chem.1976,14.2263)について決定したMark−Houwink係数と組み合わせて用いて、ポリマー分子量を計算した。
パート(a):ジベンジルトリチオカーボネート(式(II)(Z=−SCH2(C6H5)およびRa=−CH2(C6H5))を用いる、ポリ[(アクリル酸ブチル)p−co−(アクリル酸)q]−RAFT剤(2≦p≦20および2≦q≦20)の調製
ポリ(BAp−co−AAq)−DBTTC RAFTの調製のための通常の製法において、1,4−ジオキサン中アクリル酸、アクリル酸ブチル、アゾビスイソブチロニトリルおよびDBTTCの溶液を100ml丸底フラスコ中で調製した。これを磁気的に撹拌し、窒素で30分間パージした。次いで、フラスコを70℃で5時間加熱した(BA96%転化率、AA96%転化率)。
パート(a)で調製したポリ(BAp−co−AAq)−DBTTC RAFT剤を、pHを水酸化ナトリウムで調整することによって脱イオン水に溶解させ、透析酸化セリウム分散液に添加した。この溶液を一晩撹拌した。
塩化ビニリデンとアクリル酸メチルとの(9:1質量比での)エマルション共重合を、パート(b)で得た酸化セリウム粒子の表面に吸着させたポリ(BA5−co−AA5)−DBTTCの存在下で行った。
塩化ビニリデンとアクリル酸メチルとの(9:1質量比での)エマルション共重合を、レドックス開始剤(KPS/Na2S2O5)を55℃で用いる以外は、パート(c)で記載した手順に従って、パート(b)で開示した手順に従って得た酸化セリウム粒子の表面で吸着させたポリ(BA5−co−AA5)−DBTTCの存在下で行った。実験データを表4に報告する。
パート(a):ジベンジルトリチオカーボネート(式(II)(式中、Z=−SCH2(C6H5)およびRa=−CH2(C6H5))を用いる、ポリ[(アクリル酸ブチル)p’−co−(アクリル酸)q’−co−AMPSr]−RAFT剤(2≦p’≦10、2≦q’≦15および1≦r≦8)の調製
開始剤としてAIBNおよびRAFT剤としてDBTTCを用いて、ジメチルスルホキシド中アクリル酸ブチル、アクリル酸および2−アクリルアミド−2−メチルプロパン硫酸(AMPS)を70℃で共重合することによって、種々の組成を有するポリ(BAp’−co−AAq’−co−AMPSr)−DBTTCランダムコポリマーを合成した。DBTTC:AIBNモル比3.3を用いた。反応の最後に、ポリ(BAp’−co−AAq’−co−AMPSr)−DBTTC RAFT剤を乾燥形態で単離した。
熱フリーラジカル開始剤(VA−057)を用いて、酸化セリウムの表面に吸着されたポリ(BAp’−co−AAq’−AMPSr)−DBTTC RAFTの存在下で、実施例1−パート(b)およびパート(c)に記載した同じ手順に従って、塩化ビニリデンとアクリル酸メチルとの(9:1質量比での)エマルション重合を行った。表7により、エマルション重合についての実験データを報告する。
パート(a):ジベンジルトリチオカーボネート(式(II)(式中、Z=−SCH2(C6H5)およびRa=−CH2(C6H5))を用いる、ポリ[(ビニルベンジルホスホン二酸)s−co−(スチレン)t]−RAFT剤(2≦s≦10および1≦t≦8)の調製
開始剤としてAIBNおよびRAFT剤としてDBTTCを用いて、α,α,α−トリフルオロトルエン(TFT)中ビニルベンジルホスホニルジエチルエステル(VBPDE)、ベニルベンジルホスホン二酸への前駆体、およびスチレン(Sty)を75℃で共重合させることによって、種々の組成を有するポリ[(ビニルベンジルホスホニルジエチルエステル)s−co−(スチレン)t]−DBTTCランダムコポリマーを合成した。反応の最後に、ポリ(VBPDEs−co−Styt)−DBTTC RAFT剤を乾燥形態で得た。
熱フリーラジカル開始剤(VA−057)を用いて、酸化セリウムの表面に吸着されたポリ(VBPDA10−co−Sty2.5)−DBTTC RAFTの存在下で、実施例1−パート(b)およびパート(c)に記載した同じ手順に従って、塩化ビニリデンとアクリル酸メチルとの(9:1質量比での)エマルション共重合を行った。表10により、エマルション重合についての実験データを報告する。
Claims (15)
- 液相中固体微粒子物質の分散液を供給するステップであって、前記分散液はRAFT/MADIX剤を含むステップ;前記分散液に、塩化ビニリデンおよび任意選択的に、それと共重合可能な少なくとも1種のエチレン性不飽和モノマーを供給するステップ;ならびに塩化ビニリデンおよび任意選択的に、前記少なくとも1種のエチレン性不飽和モノマーをRAFT/MADIX剤の制御下で重合させて、前記固体微粒子物質の表面で塩化ビニリデンポリマーを形成するステップを含む、塩化ビニリデンポリマーコンポジットを調製する方法。
- 前記固体微粒子物質が、二酸化セリウム、二酸化チタン、二酸化ケイ素およびそれらの組合せからなる群から選択される無機物質を含む、請求項1に記載の方法。
- 前記固体微粒子が、二酸化セリウムである、請求項2に記載の方法。
- 前記液相が、水である、請求項1〜3のいずれか一項に記載の方法。
- 前記RAFT/MADIX剤が、式(III):
[式中、Raは、C1〜C6アルキル、C1〜C6アルコキシ、アリールまたはヘテロアリールから選択されてもよく、これらのそれぞれは、−CO2H、−CO2R、−CN、−SO3H、−OSO3H、−SOR、−SO2R、−OP(OH)2、−P(OH)2、−PO(OH)2、−OH、−OR、−(OCH2−CHR0)w−OH、−(OCH2−CHR0)w−OR、−CONH2、CONHR1、CONR1R2、−NR1R2、−NR1R2R3[ここで、Rは、C1〜C6アルキルから選択され、R0は、水素またはRから選択され、wは、1〜10の整数であり、R1、R2およびR3は、−CO2H、−SO3H、−OSO3H、−OH、−(OCH2CHR0)w−OH、−CONH2、−SORおよびSO2R、ならびにそれらの塩(ここで、R、R0およびwは、上に定義されたとおりである)から選択される1種以上の親水性置換基で任意選択的に置換されていてもよいC1〜C6アルキルおよびアリールから独立して選択される]から選択される1種以上の親水性基で置換されていてもよく;Zは、任意選択的に置換されたアルコキシ、任意選択的に置換されたアリールオキシ、任意選択的に置換されたアルキル、任意選択的に置換されたアリール、任意選択的に置換されたヘテロシクリル、任意選択的に置換されたアリールアルキル、任意選択的に置換されたアルキルチオ、任意選択的に置換されたアリールアルキルチオ、ジアルコキシ−またはジアリールオキシホスフィニル[−P(=O)(OR4)2]、ジアルキル−またはジアリールホスフィニル[−P(=O)R4 2](ここで、R4は、任意選択的に置換されたC1〜C18アルキル、任意選択的に置換されたC2〜C18アルケニル、任意選択的に置換されたアリール、任意選択的に置換されたヘテロシクリル、任意選択的に置換されたアリールアルキル、任意選択的に置換されたアルキルアリール、任意選択的に置換されたアシルアミノ、任意選択的に置換されたアシルイミノ、任意選択的に置換されたアミノ、任意の機構で形成されたポリマー鎖からなる群から選択される)のうちで選択され;それぞれのHは、独立してエチレン性不飽和モノマーの重合残基であり、nは、1〜300の整数である]のものである、請求項1〜4のいずれか一項に記載の方法。 - −(H)n−が、親水性特性(h1)を有する少なくとも1種のエチレン性不飽和モノマーおよび疎水性特性(h2)を有する少なくとも1種のエチレン性不飽和モノマーに由来する繰り返し単位を含む、請求項5に記載の方法。
- 前記親水性特性(h1)を有する少なくとも1種のエチレン性不飽和モノマーが、その対応する酸が6未満の酸解離定数pKaを有する官能基を有する、請求項6に記載の方法。
- Raが、−CH(CH3)CO2H、−CH(CO2H)CH2CO2H、−C(CH3)2CO2H、−CH2(C6H5)、−C(CN)(CH3)CO2H、−C(CN)(CH3)(CH2)2CO2Hからなる群から選択され、Zが、−SCH2(C6H5)、−S(CH2)uCO2H(ここで、uは、2〜11の整数である)、−SCzH2z+1、−OCzH2z+1(ここで、zは、1〜12、好ましくは2〜12の整数である)、−SCH2CH2OH、−OCH2CF3、−N(C6H5)(CH3)からなる群から選択される、請求項5〜7のいずれか一項に記載の方法。
- 請求項1〜8のいずれか一項に記載の方法によって得ることができる、塩化ビニリデンポリマー中に被包された固体微粒子を含む塩化ビニリデンポリマーコンポジット。
- 前記固体微粒子物質の含有量が、前記コンポジットの全重量に対して、少なくとも0.05重量%、かつ最大で50重量%である、請求項9に記載の塩化ビニリデンポリマーコンポジット。
- 前記塩化ビニリデンポリマーが、塩化ビニリデンに由来する少なくとも50重量%の繰り返し単位、およびアクリル酸メチル、メタクリル酸メチル、アクリル酸エチル、メタクリル酸エチル、アクリル酸n−ブチル、メタクリル酸n−ブチル、アクリル酸2−エチルヘキシル、メタクリル酸2−エチルヘキシル、アクリル酸2−ヒドロキシエチル、メタクリル酸2−ヒドロキシエチル、メタクリル酸グリシジル、アクリル酸グリシジル、アクリロニトリル、メタクリロニトリル、アクリル酸、メタクリル酸、アクリルアミド、N−メチロールアクリルアミド、N,N−ジ(アルキル)アクリルアミド、ポリ(エチレンオキシド)メチルエーテルアクリレート(PEOA)、ポリ(エチレンオキシド)メチルエーテルメタクリレート(PEOMA)からなる群から選択される1種以上のエチレン性不飽和モノマーに由来する最大で50重量%の繰り返し単位を含む、請求項9または10に記載の塩化ビニリデンポリマーコンポジット。
- 前記固体微粒子が、二酸化セリウムを含む、請求項9〜11のいずれか一項に記載の塩化ビニリデンポリマーコンポジット。
- 請求項9〜12のいずれか一項に記載の塩化ビニリデンポリマーコンポジット、およびポリマーまたは液相を含む組成物。
- フィルムの調製のための、請求項9〜12のいずれか一項に記載の塩化ビニリデンポリマーコンポジット、または請求項13に記載の組成物の使用。
- 請求項9〜12のいずれか一項に記載の塩化ビニリデンポリマーコンポジット、または請求項13に記載の組成物を含むフィルム。
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JP2008516017A (ja) * | 2004-10-04 | 2008-05-15 | ザ ユニバーシティ オブ シドニー | 表面重合プロセスおよびraft剤を使用するポリマー生成物 |
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BR112014015406B1 (pt) | 2020-12-29 |
JP6314330B2 (ja) | 2018-04-25 |
EP2794694A1 (en) | 2014-10-29 |
US20140371370A1 (en) | 2014-12-18 |
CN104302680B (zh) | 2016-12-14 |
BR112014015406A8 (pt) | 2017-07-04 |
BR112014015406A2 (pt) | 2017-06-13 |
US9850364B2 (en) | 2017-12-26 |
JP2017226842A (ja) | 2017-12-28 |
WO2013092588A1 (en) | 2013-06-27 |
CN104302680A (zh) | 2015-01-21 |
EP2794694B1 (en) | 2016-03-30 |
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