JP2004536918A - 結晶性ポリカーボネートオリゴマーを調製する方法 - Google Patents
結晶性ポリカーボネートオリゴマーを調製する方法 Download PDFInfo
- Publication number
- JP2004536918A JP2004536918A JP2003515579A JP2003515579A JP2004536918A JP 2004536918 A JP2004536918 A JP 2004536918A JP 2003515579 A JP2003515579 A JP 2003515579A JP 2003515579 A JP2003515579 A JP 2003515579A JP 2004536918 A JP2004536918 A JP 2004536918A
- Authority
- JP
- Japan
- Prior art keywords
- crystallization
- fugitive
- nucleating agent
- polycarbonate
- polycarbonate oligomer
- 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.)
- Pending
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 93
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 66
- 238000002425 crystallisation Methods 0.000 claims abstract description 95
- 230000008025 crystallization Effects 0.000 claims abstract description 93
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 239000002667 nucleating agent Substances 0.000 claims abstract description 33
- 238000002844 melting Methods 0.000 claims abstract description 24
- 230000008018 melting Effects 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- 239000002245 particle Substances 0.000 claims description 48
- 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 description 12
- 230000009477 glass transition Effects 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- -1 diaryl carbonate Chemical compound 0.000 claims description 7
- 239000010419 fine particle Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000011859 microparticle Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims 1
- 150000008366 benzophenones Chemical class 0.000 claims 1
- 150000004074 biphenyls Chemical class 0.000 claims 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 239000003623 enhancer Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 37
- 239000003795 chemical substances by application Substances 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000004014 plasticizer Substances 0.000 description 10
- 239000007790 solid phase Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000002076 thermal analysis method Methods 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- ULBTUVJTXULMLP-UHFFFAOYSA-N butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCC ULBTUVJTXULMLP-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000012296 anti-solvent Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000004781 supercooling Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- SUOOZFRDMVSBLL-KSBRXOFISA-L (z)-but-2-enedioate;tetramethylazanium Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]C(=O)\C=C/C([O-])=O SUOOZFRDMVSBLL-KSBRXOFISA-L 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-MICDWDOJSA-N chloro(deuterio)methane Chemical compound [2H]CCl NEHMKBQYUWJMIP-MICDWDOJSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000000196 viscometry 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
- C08G64/40—Post-polymerisation treatment
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/912,482 US6534623B1 (en) | 2001-07-25 | 2001-07-25 | Process for the preparation of crystalline polycarbonate oligomers |
| PCT/US2002/023588 WO2003010221A1 (en) | 2001-07-25 | 2002-07-25 | Process for the preparation of crystalline polycarbonate oligomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004536918A true JP2004536918A (ja) | 2004-12-09 |
| JP2004536918A5 JP2004536918A5 (enExample) | 2006-01-05 |
Family
ID=25432000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515579A Pending JP2004536918A (ja) | 2001-07-25 | 2002-07-25 | 結晶性ポリカーボネートオリゴマーを調製する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6534623B1 (enExample) |
| EP (1) | EP1440104A1 (enExample) |
| JP (1) | JP2004536918A (enExample) |
| CA (1) | CA2449088A1 (enExample) |
| WO (1) | WO2003010221A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015105330A (ja) * | 2013-11-29 | 2015-06-08 | チェイル インダストリーズ インコーポレイテッド | ポリアミド樹脂およびその製造方法 |
| US10287395B2 (en) | 2013-11-29 | 2019-05-14 | Lotte Advanced Materials Co., Ltd. | Polyamide resin and method for manufacturing same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7504472B2 (en) * | 2005-06-02 | 2009-03-17 | E. I. Du Pont De Nemours + Company | Rapidly crystallizing polycarbonate composition |
| US8236904B2 (en) | 2005-12-28 | 2012-08-07 | Ethicon, Inc. | Bioabsorbable polymer compositions exhibiting enhanced crystallization and hydrolysis rates |
| US20070149640A1 (en) * | 2005-12-28 | 2007-06-28 | Sasa Andjelic | Bioabsorbable polymer compositions exhibiting enhanced crystallization and hydrolysis rates |
| JP2010232895A (ja) * | 2009-03-26 | 2010-10-14 | Fuji Xerox Co Ltd | 通信制御装置及び情報処理装置 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2219195A2 (en) * | 1972-02-28 | 1974-09-20 | Unibra Sa | Crystalline polycarbonate polymers - by adding finely divided seeding agents and heating above glass transit |
| FR2173681A1 (en) * | 1972-02-28 | 1973-10-12 | Mercier Jean Pierre | Crystalline polycarbonate polymers - by heating mixture of polycarbonate, seeding agent and plasticiser above glass |
| US5214073A (en) | 1989-10-17 | 1993-05-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Porous, crystallized, aromatic polycarbonate prepolymer, a porous, crystallized aromatic polycarbonate, and production methods |
| DE4032924A1 (de) | 1990-10-17 | 1992-04-23 | Bayer Ag | Verfahren zur herstellung von loesungsmittelfreiem polycarbonat |
| JP3097969B2 (ja) | 1991-12-26 | 2000-10-10 | 旭化成工業株式会社 | 芳香族ポリカーボネートの製法 |
| JP3619579B2 (ja) | 1995-08-31 | 2005-02-09 | 出光興産株式会社 | ポリカーボネート固相重合用オリゴマー粒状体の製造方法 |
| ES2172691T3 (es) | 1995-11-27 | 2002-10-01 | Idemitsu Petrochemical Co | Procedimientos de produccion de policarbonato. |
| US5717056A (en) | 1996-05-24 | 1998-02-10 | General Electric Company | Method for preparing polycarbonate by solid state polymerization |
| US6140461A (en) * | 1999-08-10 | 2000-10-31 | General Electric Company | Method for preparing solid state polycarbonates in a unitary series of operations |
-
2001
- 2001-07-25 US US09/912,482 patent/US6534623B1/en not_active Expired - Fee Related
-
2002
- 2002-07-25 CA CA002449088A patent/CA2449088A1/en not_active Abandoned
- 2002-07-25 JP JP2003515579A patent/JP2004536918A/ja active Pending
- 2002-07-25 EP EP02756640A patent/EP1440104A1/en not_active Withdrawn
- 2002-07-25 WO PCT/US2002/023588 patent/WO2003010221A1/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015105330A (ja) * | 2013-11-29 | 2015-06-08 | チェイル インダストリーズ インコーポレイテッド | ポリアミド樹脂およびその製造方法 |
| US10287395B2 (en) | 2013-11-29 | 2019-05-14 | Lotte Advanced Materials Co., Ltd. | Polyamide resin and method for manufacturing same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003010221A1 (en) | 2003-02-06 |
| US6534623B1 (en) | 2003-03-18 |
| CA2449088A1 (en) | 2003-02-06 |
| EP1440104A1 (en) | 2004-07-28 |
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