JP5770625B2 - ビニルエーテル系星型ポリマーおよびその製造方法 - Google Patents
ビニルエーテル系星型ポリマーおよびその製造方法 Download PDFInfo
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- JP5770625B2 JP5770625B2 JP2011505905A JP2011505905A JP5770625B2 JP 5770625 B2 JP5770625 B2 JP 5770625B2 JP 2011505905 A JP2011505905 A JP 2011505905A JP 2011505905 A JP2011505905 A JP 2011505905A JP 5770625 B2 JP5770625 B2 JP 5770625B2
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- Prior art keywords
- group
- vinyl ether
- carbon atoms
- polymer
- star polymer
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- 229920000642 polymer Polymers 0.000 title claims description 212
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims description 91
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- -1 divinyl compound Chemical class 0.000 claims description 55
- 238000005227 gel permeation chromatography Methods 0.000 claims description 45
- 239000000178 monomer Substances 0.000 claims description 44
- 239000002841 Lewis acid Substances 0.000 claims description 42
- 150000007517 lewis acids Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 12
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 229910001507 metal halide Inorganic materials 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000012544 monitoring process Methods 0.000 claims description 3
- 230000006911 nucleation Effects 0.000 claims description 3
- 238000010899 nucleation Methods 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 123
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 229960000834 vinyl ether Drugs 0.000 description 77
- 239000000243 solution Substances 0.000 description 60
- 238000006116 polymerization reaction Methods 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 36
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 24
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YYQXLHNYOMWHEL-UHFFFAOYSA-N 1-(2-methylpropoxy)ethyl acetate Chemical compound CC(C)COC(C)OC(C)=O YYQXLHNYOMWHEL-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 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 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000012300 argon atmosphere Substances 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003729 cation exchange resin Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 3
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- QIUCYKBVFAPWRR-UHFFFAOYSA-N 1-ethenoxy-3-methylbutane Chemical compound CC(C)CCOC=C QIUCYKBVFAPWRR-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 3
- GRFNSWBVXHLTCI-UHFFFAOYSA-N 1-ethenyl-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=C(C=C)C=C1 GRFNSWBVXHLTCI-UHFFFAOYSA-N 0.000 description 3
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 3
- PIUJWWBOMGMSAY-UHFFFAOYSA-N 2-ethenoxybutane Chemical compound CCC(C)OC=C PIUJWWBOMGMSAY-UHFFFAOYSA-N 0.000 description 3
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 3
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101001074954 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 5-phosphatase A Proteins 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 102100035985 Phosphatidylinositol 4,5-bisphosphate 5-phosphatase A Human genes 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000010552 living cationic polymerization reaction Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 2
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 2
- PNSAKLKMKPWBIC-UHFFFAOYSA-N 1-[2-(2-ethenoxyethoxy)ethoxy]-2-ethoxyethane Chemical compound CCOCCOCCOCCOC=C PNSAKLKMKPWBIC-UHFFFAOYSA-N 0.000 description 2
- RJTJPFYIGZWFMK-UHFFFAOYSA-N 1-[2-(2-ethenoxyethoxy)ethoxy]-2-methoxyethane Chemical compound COCCOCCOCCOC=C RJTJPFYIGZWFMK-UHFFFAOYSA-N 0.000 description 2
- UVMBRRGVNABPCP-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)OC=C UVMBRRGVNABPCP-UHFFFAOYSA-N 0.000 description 2
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910018287 SbF 5 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- DLEGDLSLRSOURQ-UHFFFAOYSA-N fluroxene Chemical compound FC(F)(F)COC=C DLEGDLSLRSOURQ-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001374 small-angle light scattering Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- PTVAFUMXLZLZEZ-UHFFFAOYSA-N tert-butyl 2-(3-ethenylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=CC(C=C)=C1 PTVAFUMXLZLZEZ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FPDZOFFZSWSOSL-UHFFFAOYSA-N trifluoromethoxyethene Chemical compound FC(F)(F)OC=C FPDZOFFZSWSOSL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- FPWPIVJXMURJKK-UHFFFAOYSA-N (3-ethenylphenoxy)-trimethylsilane Chemical compound C[Si](C)(C)OC1=CC=CC(C=C)=C1 FPWPIVJXMURJKK-UHFFFAOYSA-N 0.000 description 1
- QBKXNEUPNQWVFZ-UHFFFAOYSA-N (3-ethenylphenyl) 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC=CC(C=C)=C1 QBKXNEUPNQWVFZ-UHFFFAOYSA-N 0.000 description 1
- OWTJYMHZFCHOBI-UHFFFAOYSA-N (3-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C=C)=C1 OWTJYMHZFCHOBI-UHFFFAOYSA-N 0.000 description 1
- SOSNAIPTFXTNRU-UHFFFAOYSA-N (4-ethenylphenoxy)-trimethylsilane Chemical compound C[Si](C)(C)OC1=CC=C(C=C)C=C1 SOSNAIPTFXTNRU-UHFFFAOYSA-N 0.000 description 1
- ZRVLZJPJKUNCAC-UHFFFAOYSA-N (4-ethenylphenyl) 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC=C(C=C)C=C1 ZRVLZJPJKUNCAC-UHFFFAOYSA-N 0.000 description 1
- VHWMDPDYPIZKQS-UHFFFAOYSA-N (4-ethenylphenyl) methyl carbonate Chemical compound COC(=O)OC1=CC=C(C=C)C=C1 VHWMDPDYPIZKQS-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- USUVZXVXRBAIEE-UHFFFAOYSA-N 1,4-bis(2-ethenoxyethoxy)benzene Chemical compound C=COCCOC1=CC=C(OCCOC=C)C=C1 USUVZXVXRBAIEE-UHFFFAOYSA-N 0.000 description 1
- MBQIGVLDESBKFG-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-methoxyethane Chemical compound COCCOCCOC=C MBQIGVLDESBKFG-UHFFFAOYSA-N 0.000 description 1
- BBMXNOISXHLMAT-UHFFFAOYSA-N 1-(ethenoxymethyl)-4-fluorobenzene Chemical compound FC1=CC=C(COC=C)C=C1 BBMXNOISXHLMAT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- HWCLMKDWXUGDKL-UHFFFAOYSA-N 1-ethenoxy-2-ethoxyethane Chemical compound CCOCCOC=C HWCLMKDWXUGDKL-UHFFFAOYSA-N 0.000 description 1
- ZZAYVPYTPKHWOI-UHFFFAOYSA-N 1-ethenoxy-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(OC=C)C=C1 ZZAYVPYTPKHWOI-UHFFFAOYSA-N 0.000 description 1
- YXHRYLHTQVXZIK-UHFFFAOYSA-N 1-ethenoxy-4-methylbenzene Chemical compound CC1=CC=C(OC=C)C=C1 YXHRYLHTQVXZIK-UHFFFAOYSA-N 0.000 description 1
- MFKVIGSGQLMCIG-UHFFFAOYSA-N 1-ethenoxyadamantane Chemical compound C1C(C2)CC3CC2CC1(OC=C)C3 MFKVIGSGQLMCIG-UHFFFAOYSA-N 0.000 description 1
- UKPZKFBBVPKVIC-UHFFFAOYSA-N 1-ethenyl-3-(1-ethoxyethoxy)benzene Chemical compound CCOC(C)OC1=CC=CC(C=C)=C1 UKPZKFBBVPKVIC-UHFFFAOYSA-N 0.000 description 1
- BNKQWLUYZRSVOT-UHFFFAOYSA-N 1-ethenyl-3-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=CC(C=C)=C1 BNKQWLUYZRSVOT-UHFFFAOYSA-N 0.000 description 1
- YYRGFWRHEKGYOX-UHFFFAOYSA-N 1-ethenyl-3-(methoxymethoxy)benzene Chemical compound COCOC1=CC=CC(C=C)=C1 YYRGFWRHEKGYOX-UHFFFAOYSA-N 0.000 description 1
- LTGJSMARDKHZOY-UHFFFAOYSA-N 1-ethenyl-3-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC(C=C)=C1 LTGJSMARDKHZOY-UHFFFAOYSA-N 0.000 description 1
- LXOOIXRLEJSMKX-UHFFFAOYSA-N 1-ethenyl-3-ethoxybenzene Chemical compound CCOC1=CC=CC(C=C)=C1 LXOOIXRLEJSMKX-UHFFFAOYSA-N 0.000 description 1
- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- OFCRXVIOIFVHFG-UHFFFAOYSA-N 1-ethenyl-3-propoxybenzene Chemical compound CCCOC1=CC=CC(C=C)=C1 OFCRXVIOIFVHFG-UHFFFAOYSA-N 0.000 description 1
- DTNCNFLLRLHPNJ-UHFFFAOYSA-N 1-ethenyl-4-(1-ethoxyethoxy)benzene Chemical compound CCOC(C)OC1=CC=C(C=C)C=C1 DTNCNFLLRLHPNJ-UHFFFAOYSA-N 0.000 description 1
- SOXFPOYICGTMQC-UHFFFAOYSA-N 1-ethenyl-4-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=C(C=C)C=C1 SOXFPOYICGTMQC-UHFFFAOYSA-N 0.000 description 1
- OBRYRJYZWVLVLF-UHFFFAOYSA-N 1-ethenyl-4-ethoxybenzene Chemical compound CCOC1=CC=C(C=C)C=C1 OBRYRJYZWVLVLF-UHFFFAOYSA-N 0.000 description 1
- MEPWMZKEADGNEO-UHFFFAOYSA-N 1-ethenyl-4-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(C=C)C=C1 MEPWMZKEADGNEO-UHFFFAOYSA-N 0.000 description 1
- HYKOKFYURVJHKT-UHFFFAOYSA-N 1-ethenyl-4-propoxybenzene Chemical compound CCCOC1=CC=C(C=C)C=C1 HYKOKFYURVJHKT-UHFFFAOYSA-N 0.000 description 1
- OGUXYWOIPQQGKA-UHFFFAOYSA-N 1-methoxy-4-(2-methoxyethenyl)benzene Chemical compound COC=CC1=CC=C(OC)C=C1 OGUXYWOIPQQGKA-UHFFFAOYSA-N 0.000 description 1
- XIUHYXJWUMGXQC-UHFFFAOYSA-N 2-(3-ethenylphenoxy)oxane Chemical compound C=CC1=CC=CC(OC2OCCCC2)=C1 XIUHYXJWUMGXQC-UHFFFAOYSA-N 0.000 description 1
- OODGPKJPJBOZQL-UHFFFAOYSA-N 2-(4-ethenylphenoxy)oxane Chemical compound C1=CC(C=C)=CC=C1OC1OCCCC1 OODGPKJPJBOZQL-UHFFFAOYSA-N 0.000 description 1
- KJHFNHVFNLOTEH-UHFFFAOYSA-N 2-ethenoxyadamantane Chemical compound C1C(C2)CC3CC1C(OC=C)C2C3 KJHFNHVFNLOTEH-UHFFFAOYSA-N 0.000 description 1
- BYUNYALHUMSCSA-UHFFFAOYSA-N 2-ethenoxyoxane Chemical compound C=COC1CCCCO1 BYUNYALHUMSCSA-UHFFFAOYSA-N 0.000 description 1
- ZNYVTSYLHMCSSI-UHFFFAOYSA-N 2-ethenoxyoxolane Chemical compound C=COC1CCCO1 ZNYVTSYLHMCSSI-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 1
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- QNBBNFVOYOKALV-UHFFFAOYSA-N 3-ethenoxybicyclo[2.2.1]heptane Chemical compound C1CC2C(OC=C)CC1C2 QNBBNFVOYOKALV-UHFFFAOYSA-N 0.000 description 1
- HHLGHULPTMLMBH-UHFFFAOYSA-N 3-ethenoxybicyclo[2.2.2]octane Chemical compound C1CC2C(OC=C)CC1CC2 HHLGHULPTMLMBH-UHFFFAOYSA-N 0.000 description 1
- YNGIFMKMDRDNBQ-UHFFFAOYSA-N 3-ethenylphenol Chemical compound OC1=CC=CC(C=C)=C1 YNGIFMKMDRDNBQ-UHFFFAOYSA-N 0.000 description 1
- REWLXMVGEZMKSG-UHFFFAOYSA-N 3-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC(O)=C1 REWLXMVGEZMKSG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- NAAFUPBXVBAGSC-UHFFFAOYSA-N [SiH3]OC=Cc1ccccc1 Chemical compound [SiH3]OC=Cc1ccccc1 NAAFUPBXVBAGSC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NPEFICOHWIZPMC-UHFFFAOYSA-L dichloroalumanylium;ethanolate Chemical compound [Cl-].[Cl-].CCO[Al+2] NPEFICOHWIZPMC-UHFFFAOYSA-L 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- IHYWHVQKHIWVBX-UHFFFAOYSA-N ethenoxycycloheptane Chemical compound C=COC1CCCCCC1 IHYWHVQKHIWVBX-UHFFFAOYSA-N 0.000 description 1
- ORAFCUXGWRDXAC-UHFFFAOYSA-N ethenoxycyclooctane Chemical compound C=COC1CCCCCCC1 ORAFCUXGWRDXAC-UHFFFAOYSA-N 0.000 description 1
- HJVKTYVDOZVQPA-UHFFFAOYSA-N ethenoxycyclopentane Chemical compound C=COC1CCCC1 HJVKTYVDOZVQPA-UHFFFAOYSA-N 0.000 description 1
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- JFICPAADTOQAMU-UHFFFAOYSA-L ethylaluminum(2+);dibromide Chemical compound CC[Al](Br)Br JFICPAADTOQAMU-UHFFFAOYSA-L 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- UGUZZPBNTADPIT-UHFFFAOYSA-L ethylaluminum(2+);difluoride Chemical compound [F-].[F-].CC[Al+2] UGUZZPBNTADPIT-UHFFFAOYSA-L 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- OBHGHWZEROPLSC-UHFFFAOYSA-N methyl 2-phenylethenyl carbonate Chemical compound COC(=O)OC=CC1=CC=CC=C1 OBHGHWZEROPLSC-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- RBLGTYCOUOIUNY-UHFFFAOYSA-L octylaluminum(2+);dichloride Chemical compound CCCCCCCC[Al](Cl)Cl RBLGTYCOUOIUNY-UHFFFAOYSA-L 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BPQPJXCUBLCZIB-UHFFFAOYSA-L phenylaluminum(2+);dichloride Chemical compound [Cl-].[Cl-].[Al+2]C1=CC=CC=C1 BPQPJXCUBLCZIB-UHFFFAOYSA-L 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GJWMYLFHBXEWNZ-UHFFFAOYSA-N tert-butyl (4-ethenylphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(C=C)C=C1 GJWMYLFHBXEWNZ-UHFFFAOYSA-N 0.000 description 1
- QVPBMCKCBQURHP-UHFFFAOYSA-N tert-butyl-(4-ethenylphenoxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=C(C=C)C=C1 QVPBMCKCBQURHP-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
で表されるものであり、アーム部のオキシスチレン系繰り返し単位が、次の一般式(2)
で表されるものである前記ビニルエーテル系星型ポリマーである。
で表されるビニルエーテル系単量体をリビングカチオン重合させ、次いで、一般式(3)
で表されるジビニル化合物を添加して側鎖にビニル基を導入し、当該ビニル基の分子間架橋により核を生成させた後、一般式(5)
で表されるオキシスチレン系単量体およびオキシスチレン系単量体のカチオン重合に適するルイス酸を添加することを特徴とする前記ビニルエーテル系星型ポリマーの製造方法である。
で表される有機ハロゲン化アルミニウム化合物またはハロゲン化アルミニウム化合物が挙げられる。
(Mw/Mn):
ゲルパーミエーションクロマトグラフィー(GPC)法により標準ポリスチレン検量線から求めた[RI検出器;カラムはShodex社製LF−804×3本;溶離液はテトラヒドロフラン]。
ゲルパーミエーションクロマトグラフィー(GPC)−粘度法により絶対分子量を求めた〔RI検出器;粘度計;カラムはShodex社製KF−800D+KF−805L×2本;溶離液はテトラヒドロフラン〕。
枝数(f)は、次式に従って算出した。
f = A × B /C
A:アーム形成モノマーの重量画分
B:Mwabsolute(星)
C:Mw(枝)
粒径は、動的光散乱(DLS)(大塚電子(株)製)により解析した〔溶離液はテトラヒドロフラン〕。
エチルビニルエーテル−核−p−tert−ブトキシスチレン系星型 ポリマーの製造(1):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にエチルビニルエーテル(以下、「EVE」と記載する。)0.18モーラー(以下、「M」と略記する)、酢酸エチル 3.9M、1−イソブトキシエチルアセテート 15ミリモーラー(以下、「mM」と略記する)、トルエン 222mlを入れ、冷却した。系内温度が−10℃に達したところでEt1.5AlCl1.5のトルエン溶液(12mM)を加えて重合を開始した。EVEの転換が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させ、ゲルパーミエーションクロマトグラフィー(以下、「GPC」と略記する)により分析したところ、得られたEVEポリマーは、Mw=1,500、Mw/Mn=1.12の単分散ポリマーであった。
エチルビニルエーテル−核−p−tert−ブトキシスチレン系星型 ポリマーの製造(2):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にEVE0.18M、酢酸エチル3.9M、1−イソブトキシエチルアセテート15mM、トルエン222mlを入れ、冷却した。系内温度が−20℃に達したところでEt1.5AlCl1.5のトルエン溶液(12mM)を加えて重合を開始した。EVEの転換が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させ、GPCにより分析したところ、得られたEVEポリマーは、Mw=1,500、Mw/Mn=1.11の単分散ポリマーであった。
エチルビニルエーテル−核−p−tert−ブトキシスチレン系星型 ポリマーの製造(3):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にEVE 0.18M、酢酸エチル 3.9M、1−イソブトキシエチルアセテート 15mM、トルエン 222mlを入れ、冷却を行った。系内温度が0℃に達したところでEt1.5AlCl1.5のトルエン溶液(12mM)を加えて重合を開始した。EVEの転換が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたEVEポリマーは、Mw=1,700、Mw/Mn=1.20の単分散ポリマーであった。
エチルビニルエーテル−核−p−イソプロペニルフェノール系星型ポ リマーの製造(1):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にEVE 0.19M、酢酸エチル 4.3M、1−イソブトキシエチルアセテート 17mM、トルエン 222mlを入れ、冷却を行った。系内温度が−20℃に達したところでEt1.5AlCl1.5のトルエン溶液(13mM)を加えて重合を開始した。EVEの転化が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたEVEポリマーは、Mw=1,700、Mw/Mn=1.10の単分散ポリマーであった。
エチルビニルエーテル−核−p−イソプロペニルフェノール系星型ポ リマーの製造(2):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にEVE 0.36M、酢酸エチル 4.0M、1−イソブトキシエチルアセテート 32mM、トルエン 222mlを入れ、冷却を行った。系内温度が−20℃に達したところでEt1.5AlCl1.5のトルエン溶液(25mM)を加えて重合を開始した。EVEの転化が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたEVEポリマーは、Mw=1,600、Mw/Mn=1.15の単分散ポリマーであった。
メトキシエチルビニルエーテル−核−p−tert−ブトキシスチレ ン系星型ポリマーの製造(1):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にメトキシエチルビニルエーテル(以下、「MOVE」と記載する)0.17M、酢酸エチル 4.0M、1−イソブトキシエチルアセテート 15mM、トルエン 222mlを入れ、冷却を行った。系内温度が−10℃に達したところでEt1.5AlCl1.5のトルエン溶液(12mM)を加えて重合を開始した。MOVEの転化が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたMOVEポリマーは、Mw=1,700、Mw/Mn=1.19の単分散ポリマーであった。
2−(2−(2−メトキシエトキシ)エトキシ)エチルビニルエーテ ル−核−p−イソプロペニルフェノール系星型ポリマーの製造:
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内に2−(2−(2−メトキシエトキシ)エトキシ)エチルビニルエーテル(以下、「MOEOEOVE」と記載する)0.18M、酢酸エチル4.26M、1−イソブトキシエチルアセテート16.9mMおよびトルエン222mlを入れ、系内温度が−10℃に達したところでEt1.5AlCl1.5のトルエン溶液(13.2mM)を加えて重合を開始した。MOEOEOVEの転化が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたMOEOEOVEポリマーは、Mw=3800,Mw/Mn=1.18の単分散ポリマーであった。
エチルビニルエーテル−核−p−tert−ブトキシスチレン系星型 ポリマーの製造(4):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にEVE 0.18M、酢酸エチル 3.9M、1−イソブトキシエチルアセテート15mM、トルエン222mlを入れ、冷却を行った。系内温度が−10℃に達したところでEt1.5AlCl1.5のトルエン溶液(12mM)を加えて重合を開始した。EVEの転換が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたEVEポリマーは、Mw=1,400、Mw/Mn=1.15の単分散ポリマーであった。
エチルビニルエーテル−核−p−tert−ブトキシスチレン系星型 ポリマーの製造(5):
三方活栓をつけたガラス容器を準備し、アルゴン置換後、アルゴン雰囲気下で加熱してガラス容器内の吸着水を除いた。容器内にEVE 0.18M、酢酸エチル 3.9M、1−イソブトキシエチルアセテート 15mM、トルエン 222mlを入れ、冷却を行った。系内温度が0℃に達したところでEt1.5AlCl1.5のトルエン溶液(12mM)を加えて重合を開始した。EVEの転化が終了した時点で反応溶液を少量採取し、ナトリウムメトキシドを含むメタノールで反応を停止させた後、GPCにより分析したところ、得られたEVEポリマーは、Mw=1,500、Mw/Mn=1.12の単分散ポリマーであった。
Claims (6)
- 中心核と中心核より伸びるポリマー鎖からなるアーム部を有するビニルエーテル系星型ポリマーであって、ビニルエーテル系繰り返し単位からなるアーム部とオキシスチレン系繰り返し単位からなるアーム部を有し、中心核が下記一般式(3)
で表されるジビニル化合物の架橋により形成されたものであることを特徴とするビニルエーテル系星型ポリマー。 - アーム部のビニルエーテル系繰り返し単位が、次の一般式(1)
で表されるものであり、アーム部のオキシスチレン系繰り返し単位が、次の一般式(2)
で表されるものであることを特徴とする請求項1に記載のビニルエーテル系星型ポリマー。 - ゲルパーミエーションクロマトグラフィー(GPC)で測定されたポリスチレン換算重量平均分子量(Mw)が5,000〜200,000の範囲であり、重量平均分子量(Mw)と数平均分子量(Mn)の比(Mw/Mn)が1〜2であることを特徴とする請求項1又は2に記載のビニルエーテル系星型ポリマー。
- 開始種、ビニルエーテル系単量体のカチオン重合に適したルイス酸および溶媒の存在下、一般式(4)
で表されるビニルエーテル系単量体をリビングカチオン重合させ、次いで、一般式(3)
で表されるジビニル化合物を添加して側鎖にビニル基を導入し、当該ビニル基の分子間架橋により核を生成させた後、一般式(5)
で表されるオキシスチレン系単量体およびオキシスチレン系単量体のカチオン重合に適するルイス酸を添加して核からオキシスチレン系アームを伸長させることを特徴とするビニルエーテル系星型ポリマーの製造方法。 - 分子間架橋による核の生成を、GPCチャートの波形をモニタリングすることにより確認する請求項4又は5に記載のビニルエーテル系星型ポリマーの製造方法。
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