TWI794523B - 末端（甲基）丙烯酸酯聚碳酸酯寡聚物 - Google Patents

末端（甲基）丙烯酸酯聚碳酸酯寡聚物 Download PDF

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Publication number: TWI794523B
Authority: TW; Taiwan
Prior art keywords: meth; formula; polycarbonate oligomer; terminal; carbon atoms
Prior art date: 2018-07-05

Application number

TW108122614A

Other languages

English (en)

Chinese (zh)

Other versions

TW202006010A (zh

Inventor

尾崎充孝

須藤健

Original Assignee

日商本州化學工業股份有限公司

Priority date (The priority date 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 date listed.)

2018-07-05

Filing date

2019-06-27

Publication date

2023-03-01

2019-06-27 Application filed by 日商本州化學工業股份有限公司 filed Critical 日商本州化學工業股份有限公司

2020-02-01 Publication of TW202006010A publication Critical patent/TW202006010A/zh

2023-03-01 Application granted granted Critical

2023-03-01 Publication of TWI794523B publication Critical patent/TWI794523B/zh

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239000004417 polycarbonate Substances 0.000 title claims abstract description 73
229920000515 polycarbonate Polymers 0.000 title claims abstract description 73
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000002904 solvent Substances 0.000 abstract description 18
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 9
239000002994 raw material Substances 0.000 abstract description 9
239000000178 monomer Substances 0.000 abstract description 8
239000011248 coating agent Substances 0.000 abstract description 7
239000004925 Acrylic resin Substances 0.000 abstract description 2
229920000178 Acrylic resin Polymers 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
-1 specifically Chemical group 0.000 description 27
239000003795 chemical substances by application Substances 0.000 description 23
150000001875 compounds Chemical class 0.000 description 18
238000000034 method Methods 0.000 description 18
239000000243 solution Substances 0.000 description 16
238000005809 transesterification reaction Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
239000000126 substance Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000011347 resin Substances 0.000 description 9
239000003054 catalyst Substances 0.000 description 8
239000000155 melt Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000005227 gel permeation chromatography Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001252 acrylic acid derivatives Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
239000013076 target substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000004606 Fillers/Extenders Substances 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
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 4
238000000576 coating method Methods 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
150000001339 alkali metal compounds Chemical class 0.000 description 3
150000001341 alkaline earth metal compounds Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
229910000024 caesium carbonate Inorganic materials 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 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
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
239000007790 solid phase Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-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
WURUICCPWMHUFA-UHFFFAOYSA-N 2-[4-[2-[4-(2-hydroxyethoxy)-3-methylphenyl]propan-2-yl]-2-methylphenoxy]ethanol Chemical compound C1=C(OCCO)C(C)=CC(C(C)(C)C=2C=C(C)C(OCCO)=CC=2)=C1 WURUICCPWMHUFA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
238000012695 Interfacial polymerization Methods 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000003848 UV Light-Curing Methods 0.000 description 2
XFSBVAOIAHNAPC-WSORPINJSA-N acetylbenzoylaconine Chemical compound O([C@H]1[C@]2(O)C[C@H]3C45[C@@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)C4[C@]([C@@H](C[C@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-WSORPINJSA-N 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
238000011088 calibration curve Methods 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005469 ethylenyl group Chemical group 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000013589 supplement Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
GCLVVFYKIZYIIL-UHFFFAOYSA-N (2-butylphenyl)-diphenylborane Chemical compound CCCCC1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 GCLVVFYKIZYIIL-UHFFFAOYSA-N 0.000 description 1
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
GUFOLAUVJTWOBK-UHFFFAOYSA-N 2-[4-[1-[4-(2-hydroxyethoxy)phenyl]dodecyl]phenoxy]ethanol Chemical compound OCCOC1=CC=C(C=C1)C(CCCCCCCCCCC)C1=CC=C(C=C1)OCCO GUFOLAUVJTWOBK-UHFFFAOYSA-N 0.000 description 1
TZIYYPHSIYMLQN-UHFFFAOYSA-N 2-[4-[1-[4-(2-hydroxyethoxy)phenyl]ethyl]phenoxy]ethanol Chemical compound C=1C=C(OCCO)C=CC=1C(C)C1=CC=C(OCCO)C=C1 TZIYYPHSIYMLQN-UHFFFAOYSA-N 0.000 description 1
ZMKBETOAFQAZNU-UHFFFAOYSA-N 2-[4-[2-[4-(2-hydroxyethoxy)phenyl]-4-methylpentan-2-yl]phenoxy]ethanol Chemical compound C=1C=C(OCCO)C=CC=1C(C)(CC(C)C)C1=CC=C(OCCO)C=C1 ZMKBETOAFQAZNU-UHFFFAOYSA-N 0.000 description 1
MFBRWKCKAGAJAJ-UHFFFAOYSA-N 2-[4-[[4-(2-hydroxyethoxy)phenyl]methyl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1CC1=CC=C(OCCO)C=C1 MFBRWKCKAGAJAJ-UHFFFAOYSA-N 0.000 description 1
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000005010 aminoquinolines Chemical class 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
150000001639 boron compounds Chemical class 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
MYWGVEGHKGKUMM-UHFFFAOYSA-N carbonic acid;ethene Chemical compound C=C.C=C.OC(O)=O MYWGVEGHKGKUMM-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 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
ANHGITKPRSIRHT-UHFFFAOYSA-N cyclohexyl phenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1CCCCC1 ANHGITKPRSIRHT-UHFFFAOYSA-N 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
FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
229920006351 engineering plastic Polymers 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
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238000005259 measurement Methods 0.000 description 1
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150000002736 metal compounds Chemical class 0.000 description 1
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XTBFPVLHGVYOQH-UHFFFAOYSA-N methyl phenyl carbonate Chemical compound COC(=O)OC1=CC=CC=C1 XTBFPVLHGVYOQH-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
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238000000465 moulding Methods 0.000 description 1
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WLFOHIVICZSIKG-UHFFFAOYSA-N n,n-dimethyl-1h-imidazol-2-amine Chemical compound CN(C)C1=NC=CN1 WLFOHIVICZSIKG-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl 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])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 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
235000019260 propionic acid Nutrition 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011002 quantification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000007151 ring opening polymerisation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1

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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/42—Chemical after-treatment

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Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
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General Chemical & Material Sciences (AREA)
Polyesters Or Polycarbonates (AREA)

TW108122614A 2018-07-05 2019-06-27 末端（甲基）丙烯酸酯聚碳酸酯寡聚物 TWI794523B (zh)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6183212A (ja) *	1984-10-01	1986-04-26	Tokuyama Soda Co Ltd	高屈折率樹脂
JP2006028418A (ja) *	2004-07-20	2006-02-02	Japan Composite Co Ltd	ラジカル硬化性樹脂組成物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6155106A (ja) *	1984-08-24	1986-03-19	Tokuyama Soda Co Ltd	液状プレポリマーの製造方法
JPH03217407A (ja) *	1990-01-23	1991-09-25	Mitsubishi Petrochem Co Ltd	高屈折率樹脂の製造法
DE4426129A1 (de) *	1994-07-22	1996-01-25	Bayer Ag	Di(meth)acrylate mit cyclischen Carbonatgruppen
JPH1081720A (ja) *	1996-09-05	1998-03-31	Nof Corp	注型重合用樹脂組成物及び光学材料
JP2000302829A (ja) *	1999-04-23	2000-10-31	Jsr Corp	液状硬化性樹脂組成物およびその硬化物
JP2010024255A (ja)	2008-07-15	2010-02-04	Nippon Synthetic Chem Ind Co Ltd:The	活性エネルギー線硬化型樹脂組成物及びコーティング剤組成物
TWI549986B (zh) *	2011-05-19	2016-09-21	三菱瓦斯化學股份有限公司	A high-flow polycarbonate copolymer, a method for producing a high molecular weight aromatic polycarbonate resin, and an aromatic polycarbonate compound
JP2016011365A (ja)	2014-06-30	2016-01-21	アイカ工業株式会社	紫外線硬化型ハードコート剤
WO2017098945A1 (fr) *	2015-12-08	2017-06-15	本州化学工業株式会社	Oligomère de type polycarbonate aromatique solide

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Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6183212A (ja) *	1984-10-01	1986-04-26	Tokuyama Soda Co Ltd	高屈折率樹脂
JP2006028418A (ja) *	2004-07-20	2006-02-02	Japan Composite Co Ltd	ラジカル硬化性樹脂組成物

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CN112424259A (zh)	2021-02-26
JP7253548B2 (ja)	2023-04-06
TW202006010A (zh)	2020-02-01
CN112424259B (zh)	2022-11-08
JPWO2020008879A1 (ja)	2021-07-08
KR102637355B1 (ko)	2024-02-15
WO2020008879A1 (fr)	2020-01-09
KR20210029159A (ko)	2021-03-15

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