CN1556826A - 制备聚碳酸酯的挤出方法 - Google Patents
制备聚碳酸酯的挤出方法 Download PDFInfo
- Publication number
- CN1556826A CN1556826A CNA028186176A CN02818617A CN1556826A CN 1556826 A CN1556826 A CN 1556826A CN A028186176 A CNA028186176 A CN A028186176A CN 02818617 A CN02818617 A CN 02818617A CN 1556826 A CN1556826 A CN 1556826A
- Authority
- CN
- China
- Prior art keywords
- polycarbonate
- mixture
- cycloalkyl
- forcing machine
- alkyl
- 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.)
- Granted
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 167
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 167
- 238000001125 extrusion Methods 0.000 title abstract description 11
- -1 diaryl carbonate Chemical compound 0.000 claims abstract description 121
- 239000003054 catalyst Substances 0.000 claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 69
- 239000000047 product Substances 0.000 claims abstract description 68
- 239000002243 precursor Substances 0.000 claims abstract description 65
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 43
- 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 claims abstract description 41
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 26
- 239000006227 byproduct Substances 0.000 claims abstract description 19
- 150000002989 phenols Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 138
- 150000002148 esters Chemical class 0.000 claims description 87
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 239000007858 starting material Substances 0.000 claims description 37
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 29
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 26
- 229930185605 Bisphenol Natural products 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- XUNCVWQATLFOFE-UHFFFAOYSA-N butylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[PH3+] XUNCVWQATLFOFE-UHFFFAOYSA-N 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 12
- 150000002500 ions Chemical class 0.000 claims description 11
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000036961 partial effect Effects 0.000 claims description 8
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 8
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 5
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000002441 reversible effect Effects 0.000 claims description 5
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 239000008247 solid mixture Substances 0.000 claims description 4
- 240000000203 Salix gracilistyla Species 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 8
- 150000003818 basic metals Chemical class 0.000 claims 4
- 229910052728 basic metal Inorganic materials 0.000 claims 2
- 229910001038 basic metal oxide Inorganic materials 0.000 claims 2
- 150000004714 phosphonium salts Chemical class 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 45
- 238000005618 Fries rearrangement reaction Methods 0.000 abstract description 3
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 abstract 3
- TZSMWSKOPZEMAJ-UHFFFAOYSA-N bis[(2-methoxyphenyl)methyl] carbonate Chemical compound COC1=CC=CC=C1COC(=O)OCC1=CC=CC=C1OC TZSMWSKOPZEMAJ-UHFFFAOYSA-N 0.000 abstract 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 48
- 239000001294 propane Substances 0.000 description 24
- 238000013022 venting Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 102100029290 Transthyretin Human genes 0.000 description 8
- 108050000089 Transthyretin Proteins 0.000 description 8
- 230000008707 rearrangement Effects 0.000 description 8
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 238000013461 design Methods 0.000 description 6
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000004898 kneading Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- 125000005587 carbonate group Chemical group 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000009637 wintergreen oil Substances 0.000 description 3
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 2
- DHQDZRSUSKLFBZ-UHFFFAOYSA-N C(=O)(O)C1=C(C=CC=C1)C(CC)(O)O Chemical compound C(=O)(O)C1=C(C=CC=C1)C(CC)(O)O DHQDZRSUSKLFBZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000007600 charging Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 229930184652 p-Terphenyl Natural products 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SBCZJQDTHTUBRP-UHFFFAOYSA-N (2-hydroxyphenyl)methyl methyl carbonate Chemical group COC(=O)OCC1=CC=CC=C1O SBCZJQDTHTUBRP-UHFFFAOYSA-N 0.000 description 1
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- ZPBYCSQKDDZPGO-UHFFFAOYSA-N 2-phenyl-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C=2C=CC=CC=2)=C1 ZPBYCSQKDDZPGO-UHFFFAOYSA-N 0.000 description 1
- ZNVLKMKGFWEUPV-UHFFFAOYSA-N 2-propan-2-yl-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C(C)C)=C1 ZNVLKMKGFWEUPV-UHFFFAOYSA-N 0.000 description 1
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 1
- WUGKVYDVIGOPSI-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-2-methylphenol Chemical group C1=C(O)C(C)=CC(C=2C=C(C)C(O)=CC=2)=C1 WUGKVYDVIGOPSI-UHFFFAOYSA-N 0.000 description 1
- BIOIMCYUMXGFMM-UHFFFAOYSA-N 4-(4-hydroxy-3-octylphenyl)-2-octylphenol Chemical group C1=C(O)C(CCCCCCCC)=CC(C=2C=C(CCCCCCCC)C(O)=CC=2)=C1 BIOIMCYUMXGFMM-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 1
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- AJBXRBRVQMZREG-UHFFFAOYSA-N OC(CC)(C1=CC=CC=C1)O.OC1=CC=C(C=C1)CCC Chemical compound OC(CC)(C1=CC=CC=C1)O.OC1=CC=C(C=C1)CCC AJBXRBRVQMZREG-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 230000009286 beneficial effect Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- GFVMLYBCWPLMTF-UHFFFAOYSA-N disodiomagnesium Chemical compound [Na][Mg][Na] GFVMLYBCWPLMTF-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
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- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- 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
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
实施例 | DAC/BPA | Mw | Mn | %EC | Tg℃ |
实施例1 | 1.017 | 21489 | 9410 | 96.3 | 147 |
实施例2 | 1.017 | 23789 | 9937 | 76.2 | |
CE-1 | 1.08 | 2369 | 1797 | 115 |
实施例 | DAC/BPA | Mw | Mn | %EC | %ESEG |
实施例3 | 1.017 | 16566 | 7592 | 75 | 75% |
实施例4 | 1.017 | 16784 | 7519 | 75 | 75% |
实施例5 | 1.017 | 14022 | 6774 | 66 | 33% |
实施例 | TBPA | Mw前体 | Mw产物 | 弗利斯含量 | [OH] | %EC |
实施例6 | 0 | 16566 | 26820 | n.d. | 157 | 94.6 |
实施例7 | 0 | 16566 | 32395 | n.d. | 40 | 98.4 |
实施例8 | 0 | 16784 | 31561 | n.d. | 45 | 98.2 |
实施例9 | 150 | 16784 | 32980 | n.d. | 38 | 98.4 |
实施例10 | 0 | 14022 | 16852 | - | 863 | 80.2 |
CE-2 | 0 | 6535 | 10467 | - | 813 | 75.5 |
实施例 | 排气口真空(in.Hg.) | 质量流率(lb/hr) | 扭矩(%) | 熔点(℃) | 螺杆速度(rpm) | |||||
V1 | V2 | V3 | V4 | V5 | V6 | |||||
11 | Atm | V | 20 | 20 | 20 | 20 | 20 | 8 | 311 | 210 |
12 | Atm | E | 20 | 20 | 20 | 20 | 18 | 6 | 309 | 203 |
13 | Atm | N | 20 | 20 | 20 | 20 | 16 | 10 | 313 | 174 |
14 | Atm | T | 20 | 20 | 20 | 20 | 15 | 6 | 320 | 151 |
15 | Atm | 20 | 20 | 20 | 20 | 13 | 17 | 316 | 125 | |
16 | Atm | C | 20 | 20 | 20 | 20 | 13 | 11 | 310 | 100 |
17 | Atm | L | 20 | 20 | 20 | 20 | 22 | 9 | 319 | 206 |
18 | Atm | O | 20 | 20 | 20 | 20 | 24 | 8 | 317 | 206 |
19 | Atm | S | 20 | 20 | 20 | 20 | 28 | 6 | 316 | 206 |
20 | Atm | E | 20 | 20 | 20 | 20 | 28 | 7 | 320 | 299 |
21 | Atm | D | 20 | 20 | 20 | 20 | 35 | 5 | 316 | 299 |
实施例 | 模头压力(psi) | 实际机筒温度(℃) | 分子量Mw/Mn/PDI |
11 | 106 | 215/268/271/319/320/322/323/323/271 | 19900/8300/2.4 |
12 | 60 | 210/271/276/322/322/320/321/321/270 | 17500/7500/2.3 |
13 | 111 | 210/271/276/321/321/320/337/333/270 | 21400/9400/2.3 |
14 | 46 | 211/271/276/320/321/320/350/348/270 | 15700/6600/2.3 |
15 | 288 | 215/271/274/320/320/320/331/330/269 | 29000/12200/2.4 |
16 | 188 | 215/270/274/320/320/320/328/329/270 | 22800/9600/2.4 |
17 | 135 | 206/266/272/318/319/320/329/330/271 | 21000/9200/2.3 |
18 | 120 | 202/266/271/318/319/320/329/330/270 | 20800/9100/2.3 |
19 | 84 | 198/265/270/319/320/320/330/330/270 | 19300/8500/2.3 |
20 | 74 | 196/267/272/320/320/320/330/330/270 | 18700/8400/2.2 |
21 | 46 | 193/263/270/318/319/320/330/329/269 | 16400/7000/2.3 |
实施例 | 排气口真空(in.Hg.) | 质量流率(lb/hr) | 扭矩(%) | 熔融温度(℃) | 螺杆速度(rpm) | |||||
V1 | V2 | V3 | V4 | V5 | V6 | |||||
22 | Atm | V | 20 | 20 | 20 | 20 | 13 | 14 | 317 | 115 |
23 | Atm | E | 15 | 15 | 15 | 15 | 13 | 13 | 314 | 115 |
24 | Atm | N | 20 | 20 | 20 | 20 | 13 | 13 | 314 | 115 |
25 | Atm | T | 20 | 20 | 20 | 20 | 13 | 14 | 313 | 115 |
26 | Atm | 20 | 20 | 20 | 20 | 13 | 16 | 314 | 115 | |
27 | Atm | 20 | 20 | 20 | 20 | 13 | 16 | 313 | 115 | |
28 | Atm | C | 20 | 20 | 20 | 20 | 13 | 15 | 314 | 115 |
29 | Atm | L | 20 | 20 | 20 | 20 | 13 | 17 | 314 | 115 |
30 | Atm | O | 20 | 20 | 20 | 20 | 13 | 16 | 314 | 115 |
31 | Atm | S | 20 | 20 | 20 | 20 | 13 | 15 | 313 | 115 |
32 | Atm | E | 20 | 20 | 20 | 20 | 13 | 15 | 313 | 115 |
33 | Atm | D | 20 | 20 | 20 | 20 | 13 | 14 | 313 | 115 |
实施例 | 模头压力(psi) | 实际机筒温度(℃) | Mw/Mn/PDI |
22 | 234 | 211/268/267/322/324/330/337/336/271 | 26100/10800/2.4 |
23 | 138 | 210/269/266/320/324/330/334/333/270 | 24400/10400/2.3 |
24 | 216 | 212/270/268/323/323/330/330/331/270 | 25600/10900/2.3 |
25 | 220 | 212/270/268/322/322/322/330/329/269 | 27800/11700/2.4 |
26 | 256 | 213/270/269/321/321/330/329/330/270 | 27200/11800/2.3 |
27 | 301 | 2183/271/270/320/320/330/330/330/270 | 29000/12000/2.4 |
28 | 301 | 214/270/269/320/320/330/330/330/270 | 28400/11700/2.4 |
29 | 296 | 215/270/270/320/320/330/330/330/270 | 27900/11800/2.4 |
30 | 252 | 216/270/270/320/320/330/330/330/270 | 27000/11100/2.4 |
31 | 294 | 215/270/270/320/320/330/330/330/270 | 27700/11600/2.4 |
32 | 230 | 216/270/269/320/320/330/330/330/270 | 26000/10800/2.4 |
33 | 288 | 216/270/269/320/320/330/330/330/270 | 28400/11700/2.4 |
实施例 | 排气口真空(in.Hg.) | 质量流率(lb/hr) | 扭矩(%) | 熔融温度(℃) | 螺杆速度(rpm) | |||||
V1 | V2 | V3 | V4 | V5 | V6 | |||||
34 | Atm | 15 | 15 | 18 | 15 | 12 | 5 | 308 | 84 | |
35 | Atm | 20 | 20 | 20 | 20 | 13 | 4 | 307 | 94 |
实施例 | 模头压力(psi) | 实际机筒温度(℃) | 分子量Mw/Mn/PDI |
34 | 41 | 218/270/364/309/310/330/331/330/270 | 22200/10300/2.1 |
35 | 38 | 229/289/279/329/330/330/330/331/271 | 13300/5800/2.3 |
实施例 | 排气口真空(in.Hg.) | 质量流率(lb/hr) | 扭矩(%) | 熔融温度(℃) | 螺杆速度(rpm) | |||||
V1 | V2 | V3 | V4 | V5 | V6 | |||||
36 | Atm | 20 | 20 | 20 | 18 | 13 | 18 | 315 | 109 | |
37 | Atm | 20 | 20 | 20 | 22 | 18 | 28 | 323 | 118 | |
38 | Atm | 21 | 21 | 21 | 23 | 18 | 38 | 341 | 154 |
实施例 | 模头压力(psi) | 实际机筒温度(℃) | 分子量Mw/Mn/PDI |
36 | 232 | 211/271/270/320/320/330/331/331/271 | 28000/11800/2.4 |
37 | 646 | 205/269/270/320/320/330/331/330/270 | 39400/12700/3.1 |
38 | 204/270/270/320/320/330/330/330/290 | 43000/11700/3.7 |
实施例 | 排气口真空(in.Hg.) | 质量流率(lb/hr) | 扭矩(%) | 熔融温度(℃) | 螺杆速度(rpm) | |||||
V1 | V2 | V3 | V4 | V5 | V6 | |||||
39 | Atm | Atm | 10 | 10 | 10 | 25 | 20 | 40 | 230 | |
40 | Atm | Atm | 20 | 20 | 20 | 20 | 22 | 75 | 322 | 432 |
实施例 | 模头压力(psi) | 实际机筒温度(℃) | 分子量Mw/Mn/PDI |
39 | 137 | 236/316/317/320/322/300/303/272 | 16100/7024/2.29 |
40 | 190 | 240/260/280/297/301/300/300/299/269 | 24500/10100/2.42 |
实施例 | 排气口真空(in.Hg.) | 质量流率(lb/hr) | 扭矩(%) | 熔融温度(℃) | 螺杆速度(rpm) | |||||
V1 | V2 | V3 | V4 | V5 | V6 | |||||
41 | Atm | X | 19 | 19 | 19 | 19 | 15 | 6 | 307 | 107 |
实施例 | 模头压力(psi) | 实际机筒温度(℃) | 分子量Mw/Mn/PDI |
41 | 38 | 208/264/242/321/301/320/313/324/271 | 18498/8078/2.29 |
Claims (77)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/911,439 | 2001-07-24 | ||
US09/911,439 US6420512B1 (en) | 2001-07-24 | 2001-07-24 | Extrusion method for making polycarbonate |
US10/167,903 US6506871B1 (en) | 2001-07-24 | 2002-06-12 | Extrusion method for making polycarbonate |
US10/167,903 | 2002-06-12 | ||
PCT/US2002/023310 WO2003010220A1 (en) | 2001-07-24 | 2002-07-17 | Extrusion method for making polycarbonate |
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CN2012101956615A Division CN102702499A (zh) | 2001-07-24 | 2002-07-17 | 制备聚碳酸酯的挤出方法 |
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CN1556826B CN1556826B (zh) | 2012-07-18 |
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CN028186176A Expired - Fee Related CN1556826B (zh) | 2001-07-24 | 2002-07-17 | 制备聚碳酸酯的挤出方法 |
CN2012101956615A Pending CN102702499A (zh) | 2001-07-24 | 2002-07-17 | 制备聚碳酸酯的挤出方法 |
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Country Status (10)
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US (1) | US6506871B1 (zh) |
EP (1) | EP1414888B1 (zh) |
JP (1) | JP2004536917A (zh) |
KR (1) | KR100874297B1 (zh) |
CN (2) | CN1556826B (zh) |
AT (1) | ATE328025T1 (zh) |
DE (1) | DE60211914T2 (zh) |
ES (1) | ES2265046T3 (zh) |
TW (1) | TW548292B (zh) |
WO (1) | WO2003010220A1 (zh) |
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JPH0699552B2 (ja) * | 1986-07-16 | 1994-12-07 | ダイセル化学工業株式会社 | カ−ボネ−ト結合含有重合物の製造方法 |
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JP2000044669A (ja) * | 1998-08-04 | 2000-02-15 | Teijin Ltd | 芳香族ポリカーボネートの製造方法および真空捕集系 |
WO2000063274A1 (en) | 1999-04-20 | 2000-10-26 | Teijin Limited | Process for producing polyarylate |
TW500741B (en) | 2000-03-22 | 2002-09-01 | Teijin Ltd | Polycarbonate, a method for preparing thereof and molded products thereof |
-
2002
- 2002-06-12 US US10/167,903 patent/US6506871B1/en not_active Expired - Lifetime
- 2002-07-17 CN CN028186176A patent/CN1556826B/zh not_active Expired - Fee Related
- 2002-07-17 ES ES02747077T patent/ES2265046T3/es not_active Expired - Lifetime
- 2002-07-17 JP JP2003515578A patent/JP2004536917A/ja not_active Ceased
- 2002-07-17 WO PCT/US2002/023310 patent/WO2003010220A1/en active IP Right Grant
- 2002-07-17 DE DE60211914T patent/DE60211914T2/de not_active Expired - Lifetime
- 2002-07-17 KR KR1020047000963A patent/KR100874297B1/ko active IP Right Grant
- 2002-07-17 EP EP02747077A patent/EP1414888B1/en not_active Expired - Lifetime
- 2002-07-17 CN CN2012101956615A patent/CN102702499A/zh active Pending
- 2002-07-17 AT AT02747077T patent/ATE328025T1/de not_active IP Right Cessation
- 2002-07-19 TW TW091116165A patent/TW548292B/zh not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101346411B (zh) * | 2005-12-21 | 2011-05-18 | 沙伯基础创新塑料知识产权有限公司 | 在反应性挤出机中通过熔体聚合制得的包含少量水杨酸甲酯的聚碳酸酯 |
CN101541856B (zh) * | 2007-07-31 | 2012-09-05 | 三菱化学株式会社 | 聚碳酸酯树脂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
KR100874297B1 (ko) | 2008-12-18 |
ATE328025T1 (de) | 2006-06-15 |
WO2003010220A1 (en) | 2003-02-06 |
EP1414888B1 (en) | 2006-05-31 |
KR20040030839A (ko) | 2004-04-09 |
DE60211914T2 (de) | 2007-01-25 |
US6506871B1 (en) | 2003-01-14 |
TW548292B (en) | 2003-08-21 |
CN102702499A (zh) | 2012-10-03 |
CN1556826B (zh) | 2012-07-18 |
ES2265046T3 (es) | 2007-02-01 |
EP1414888A1 (en) | 2004-05-06 |
JP2004536917A (ja) | 2004-12-09 |
DE60211914D1 (de) | 2006-07-06 |
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