TW548292B - Extrusion method for making polycarbonate - Google Patents
Extrusion method for making polycarbonate Download PDFInfo
- Publication number
- TW548292B TW548292B TW091116165A TW91116165A TW548292B TW 548292 B TW548292 B TW 548292B TW 091116165 A TW091116165 A TW 091116165A TW 91116165 A TW91116165 A TW 91116165A TW 548292 B TW548292 B TW 548292B
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- Taiwan
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- patent application
- item
- polycarbonate
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- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 165
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 165
- 238000001125 extrusion Methods 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 96
- -1 diaryl carbonate Chemical compound 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 239000002243 precursor Substances 0.000 claims abstract description 60
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 57
- 239000000047 product Substances 0.000 claims abstract description 56
- 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 45
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 32
- TZSMWSKOPZEMAJ-UHFFFAOYSA-N bis[(2-methoxyphenyl)methyl] carbonate Chemical compound COC1=CC=CC=C1COC(=O)OCC1=CC=CC=C1OC TZSMWSKOPZEMAJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000006227 byproduct Substances 0.000 claims abstract description 21
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 121
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 71
- 238000011049 filling Methods 0.000 claims description 57
- 229930185605 Bisphenol Natural products 0.000 claims description 41
- 239000007858 starting material Substances 0.000 claims description 40
- 230000002079 cooperative effect Effects 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004185 ester group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 12
- 238000012546 transfer Methods 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 101150010802 CVC2 gene Proteins 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000004679 hydroxides Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 150000001449 anionic compounds Chemical class 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000005587 carbonate group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 6
- 229960001047 methyl salicylate Drugs 0.000 claims description 6
- 150000002891 organic anions Chemical class 0.000 claims description 6
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000008247 solid mixture Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000003871 sulfonates Chemical class 0.000 claims description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- VWEMVBHVVPCHLV-UHFFFAOYSA-N bis[(2-propoxyphenyl)methyl] carbonate Chemical compound CCCOC1=CC=CC=C1COC(=O)OCC1=CC=CC=C1OCCC VWEMVBHVVPCHLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- IHHCJKNEVHNNMW-UHFFFAOYSA-N methane;phenol Chemical compound C.OC1=CC=CC=C1 IHHCJKNEVHNNMW-UHFFFAOYSA-N 0.000 claims description 2
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 claims description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001948 sodium oxide Inorganic materials 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims 4
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 3
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 2
- RYEFAALGACYGMB-UHFFFAOYSA-N COc1ccccc1COC(O)=O Chemical compound COc1ccccc1COC(O)=O RYEFAALGACYGMB-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims 2
- 239000004575 stone Substances 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- BYXHQHMMUSOVDQ-UHFFFAOYSA-N C(C)(=O)O.C(CCC)[Fe](CCCC)(CCCC)CCCC Chemical compound C(C)(=O)O.C(CCC)[Fe](CCCC)(CCCC)CCCC BYXHQHMMUSOVDQ-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000004982 aromatic amines Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 1
- 210000000078 claw Anatomy 0.000 claims 1
- 229910052906 cristobalite Inorganic materials 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 210000005069 ears Anatomy 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 238000003801 milling Methods 0.000 claims 1
- PLXPTFQGYWXIEA-UHFFFAOYSA-N nitroformonitrile Chemical compound [O-][N+](=O)C#N PLXPTFQGYWXIEA-UHFFFAOYSA-N 0.000 claims 1
- 150000002976 peresters Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 49
- 150000002989 phenols Chemical class 0.000 abstract description 15
- 238000005618 Fries rearrangement reaction Methods 0.000 abstract description 4
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 102100029290 Transthyretin Human genes 0.000 description 7
- 108050000089 Transthyretin Proteins 0.000 description 7
- 238000013461 design Methods 0.000 description 7
- 238000004898 kneading Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- 239000000463 material Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JEUFWFJKIXMEEK-UHFFFAOYSA-N carboxy-[2-(dicarboxyamino)ethyl]carbamic acid Chemical compound OC(=O)N(C(O)=O)CCN(C(O)=O)C(O)=O JEUFWFJKIXMEEK-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229930184652 p-Terphenyl Natural products 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur Chemical group 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
- YLHAQKVIXLQIFW-UHFFFAOYSA-N (2-methoxyphenyl)methyl 2-hydroxybenzoate Chemical compound COC1=CC=CC=C1COC(=O)C1=CC=CC=C1O YLHAQKVIXLQIFW-UHFFFAOYSA-N 0.000 description 1
- VRXQOCASOOBADQ-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[2-(2,3,5,6-tetrabromo-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound BrC=1C(Br)=C(O)C(Br)=C(Br)C=1C(C)(C)C1=C(Br)C(Br)=C(O)C(Br)=C1Br VRXQOCASOOBADQ-UHFFFAOYSA-N 0.000 description 1
- DNFSJFZWNDZYHA-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[3,3,5-trimethyl-1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(Br)C(O)=C(Br)C=1Br)Br)C1=C(Br)C(Br)=C(O)C(Br)=C1Br DNFSJFZWNDZYHA-UHFFFAOYSA-N 0.000 description 1
- PBYLGADGYCTQOT-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-[1-(2,3,5,6-tetrachloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound ClC1=C(Cl)C(O)=C(Cl)C(Cl)=C1C1(C=2C(=C(Cl)C(O)=C(Cl)C=2Cl)Cl)CCCCC1 PBYLGADGYCTQOT-UHFFFAOYSA-N 0.000 description 1
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- 239000012760 heat stabilizer Substances 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- AWNVVAMWLMUZOZ-UHFFFAOYSA-J magnesium;disodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Mg+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O AWNVVAMWLMUZOZ-UHFFFAOYSA-J 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229930006728 pinane Natural products 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
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 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
- 239000011044 quartzite Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- HIXGHAJPFNFWOD-UHFFFAOYSA-M sodium;phenol;hydroxide Chemical compound [OH-].[Na+].OC1=CC=CC=C1.OC1=CC=CC=C1 HIXGHAJPFNFWOD-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000013022 venting 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
-
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW548292B true TW548292B (en) | 2003-08-21 |
Family
ID=26863580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091116165A TW548292B (en) | 2001-07-24 | 2002-07-19 | Extrusion method for making polycarbonate |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6506871B1 (enExample) |
| EP (1) | EP1414888B1 (enExample) |
| JP (1) | JP2004536917A (enExample) |
| KR (1) | KR100874297B1 (enExample) |
| CN (2) | CN102702499A (enExample) |
| AT (1) | ATE328025T1 (enExample) |
| DE (1) | DE60211914T2 (enExample) |
| ES (1) | ES2265046T3 (enExample) |
| TW (1) | TW548292B (enExample) |
| WO (1) | WO2003010220A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7365149B2 (en) | 2005-12-12 | 2008-04-29 | Hans-Peter Brack | Equipment cleaning in the manufacture of polycarbonates |
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| US7041775B2 (en) | 2004-04-20 | 2006-05-09 | General Electric Company | Method for preparing a polycarbonate oligomer mixture at low temperature for manufacturing polycarbonate |
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| US20070123655A1 (en) * | 2005-11-30 | 2007-05-31 | Gaggar Satish K | Weatherable, high modulus polymer compositions and method |
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| US7645851B2 (en) * | 2006-06-30 | 2010-01-12 | Sabic Innovative Plastics Ip B.V. | Polycarbonate with reduced color |
| US7541420B2 (en) * | 2006-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method for making molded polycarbonate articles with improved color |
| US20080287640A1 (en) * | 2007-05-15 | 2008-11-20 | General Electric Company | Process for the production of polycarbonate using an ester substituted diaryl carbonate |
| JP5380934B2 (ja) * | 2007-07-31 | 2014-01-08 | 三菱化学株式会社 | ポリカーボネート樹脂の製造方法 |
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| JP5407207B2 (ja) * | 2007-08-01 | 2014-02-05 | 三菱化学株式会社 | ポリカーボネート樹脂およびその製造方法 |
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| US7674872B2 (en) * | 2008-06-17 | 2010-03-09 | Sabic Innovative Plastics Ip B.V. | Method of producing high molecular weight polymer |
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| US8058469B2 (en) * | 2008-11-03 | 2011-11-15 | Sabic Innovative Plastics Ip B.V. | Method for making carbamates, ureas and isocyanates |
| US7659359B1 (en) | 2008-11-18 | 2010-02-09 | Sabic Innovative Plastics Ip B.V. | Stabilization of isosorbide-based polycarbonate |
| US7977447B2 (en) * | 2008-11-18 | 2011-07-12 | Sabic Innovative Plastics Ip B.V. | Method for making carbonates and esters |
| CN101856874B (zh) * | 2010-06-03 | 2013-01-02 | 浙江富源再生资源有限公司 | 一种利用废弃纯涤纶服装生产纤维级聚酯切片的方法 |
| US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
| US8669314B2 (en) | 2012-02-03 | 2014-03-11 | Sabic Innovative Plastics Ip B.V. | Hydrolytic stability in polycarbonate compositions |
| EP3036279B1 (en) | 2013-10-08 | 2019-05-08 | Momentive Performance Materials GmbH | Reactive functional siloxane compositions |
| CA3146618A1 (en) * | 2018-12-20 | 2020-06-25 | Steerlife India Private Limited | A process for preparing chemically modified bicarbonate salt particles |
| CN109955458A (zh) * | 2019-04-09 | 2019-07-02 | 合肥工业大学 | 一种低挥发性树脂的制备装置及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232668A (en) | 1979-02-28 | 1980-11-11 | Strupat John P | Gas ventilating device |
| US4323668A (en) * | 1980-12-03 | 1982-04-06 | General Electric Company | (Ortho-alkoxycarbonyaryl)-carbonate transesterification |
| 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 |
| DE69605167T2 (de) | 1995-09-19 | 2000-09-14 | Teijin Ltd., Osaka | Verfahren zur Herstellung von Polycarbonat |
| US6410777B1 (en) | 1997-04-04 | 2002-06-25 | Teijin Limited | Salicylic acid ester derivative and its production |
| JP4286914B2 (ja) * | 1998-03-17 | 2009-07-01 | 帝人株式会社 | 芳香族ポリカーボネートの製造方法 |
| 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 |
| EP1114841B1 (en) | 1999-04-20 | 2003-10-08 | 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 ES ES02747077T patent/ES2265046T3/es not_active Expired - Lifetime
- 2002-07-17 AT AT02747077T patent/ATE328025T1/de not_active IP Right Cessation
- 2002-07-17 CN CN2012101956615A patent/CN102702499A/zh active Pending
- 2002-07-17 JP JP2003515578A patent/JP2004536917A/ja not_active Ceased
- 2002-07-17 KR KR1020047000963A patent/KR100874297B1/ko not_active Expired - Fee Related
- 2002-07-17 EP EP02747077A patent/EP1414888B1/en not_active Expired - Lifetime
- 2002-07-17 DE DE60211914T patent/DE60211914T2/de not_active Expired - Lifetime
- 2002-07-17 CN CN028186176A patent/CN1556826B/zh not_active Expired - Fee Related
- 2002-07-17 WO PCT/US2002/023310 patent/WO2003010220A1/en not_active Ceased
- 2002-07-19 TW TW091116165A patent/TW548292B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7365149B2 (en) | 2005-12-12 | 2008-04-29 | Hans-Peter Brack | Equipment cleaning in the manufacture of polycarbonates |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102702499A (zh) | 2012-10-03 |
| US6506871B1 (en) | 2003-01-14 |
| ATE328025T1 (de) | 2006-06-15 |
| KR100874297B1 (ko) | 2008-12-18 |
| JP2004536917A (ja) | 2004-12-09 |
| KR20040030839A (ko) | 2004-04-09 |
| ES2265046T3 (es) | 2007-02-01 |
| CN1556826B (zh) | 2012-07-18 |
| WO2003010220A1 (en) | 2003-02-06 |
| EP1414888B1 (en) | 2006-05-31 |
| EP1414888A1 (en) | 2004-05-06 |
| DE60211914D1 (de) | 2006-07-06 |
| CN1556826A (zh) | 2004-12-22 |
| DE60211914T2 (de) | 2007-01-25 |
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| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |