TWI491642B - 聚醯胺之製造方法 - Google Patents
聚醯胺之製造方法 Download PDFInfo
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- TWI491642B TWI491642B TW099140905A TW99140905A TWI491642B TW I491642 B TWI491642 B TW I491642B TW 099140905 A TW099140905 A TW 099140905A TW 99140905 A TW99140905 A TW 99140905A TW I491642 B TWI491642 B TW I491642B
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- Taiwan
- Prior art keywords
- pressure
- diamine
- dicarboxylic acid
- component
- temperature
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 239000004952 Polyamide Substances 0.000 title claims description 8
- 229920002647 polyamide Polymers 0.000 title claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 167
- 150000004985 diamines Chemical class 0.000 claims description 110
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 72
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- 238000000034 method Methods 0.000 claims description 33
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- 239000002904 solvent Substances 0.000 claims description 9
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- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
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- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 15
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- 230000008018 melting Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 238000009833 condensation Methods 0.000 description 13
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
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- 238000006386 neutralization reaction Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
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- XXSPKSHUSWQAIZ-UHFFFAOYSA-L 36026-88-7 Chemical compound [Ni+2].[O-]P=O.[O-]P=O XXSPKSHUSWQAIZ-UHFFFAOYSA-L 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
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- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
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- ZBDSFTZNNQNSQM-UHFFFAOYSA-H cobalt(2+);diphosphate Chemical compound [Co+2].[Co+2].[Co+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O ZBDSFTZNNQNSQM-UHFFFAOYSA-H 0.000 description 1
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- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
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- YXXXKCDYKKSZHL-UHFFFAOYSA-M dipotassium;dioxido(oxo)phosphanium Chemical compound [K+].[K+].[O-][P+]([O-])=O YXXXKCDYKKSZHL-UHFFFAOYSA-M 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
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- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
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- SEQVSYFEKVIYCP-UHFFFAOYSA-L magnesium hypophosphite Chemical compound [Mg+2].[O-]P=O.[O-]P=O SEQVSYFEKVIYCP-UHFFFAOYSA-L 0.000 description 1
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- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
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- FLFJVPPJGJSHMF-UHFFFAOYSA-L manganese hypophosphite Chemical compound [Mn+2].[O-]P=O.[O-]P=O FLFJVPPJGJSHMF-UHFFFAOYSA-L 0.000 description 1
- GQYGRYMNLHLHNK-UHFFFAOYSA-N manganese(2+);diphosphite Chemical compound [Mn+2].[Mn+2].[Mn+2].[O-]P([O-])[O-].[O-]P([O-])[O-] GQYGRYMNLHLHNK-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 229910000159 nickel phosphate Inorganic materials 0.000 description 1
- JOCJYBPHESYFOK-UHFFFAOYSA-K nickel(3+);phosphate Chemical compound [Ni+3].[O-]P([O-])([O-])=O JOCJYBPHESYFOK-UHFFFAOYSA-K 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- CSWFWSPPZMEYAY-UHFFFAOYSA-N octadecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(O)O CSWFWSPPZMEYAY-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910001380 potassium hypophosphite Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 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 1
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- XWKBMOUUGHARTI-UHFFFAOYSA-N tricalcium;diphosphite Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])[O-].[O-]P([O-])[O-] XWKBMOUUGHARTI-UHFFFAOYSA-N 0.000 description 1
- VMFOHNMEJNFJAE-UHFFFAOYSA-N trimagnesium;diphosphite Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])[O-].[O-]P([O-])[O-] VMFOHNMEJNFJAE-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009269761 | 2009-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201130887A TW201130887A (en) | 2011-09-16 |
| TWI491642B true TWI491642B (zh) | 2015-07-11 |
Family
ID=44066451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099140905A TWI491642B (zh) | 2009-11-27 | 2010-11-26 | 聚醯胺之製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9260563B2 (enExample) |
| EP (1) | EP2505598B1 (enExample) |
| JP (1) | JP5633519B2 (enExample) |
| KR (1) | KR101764900B1 (enExample) |
| CN (1) | CN102639601B (enExample) |
| MY (1) | MY172071A (enExample) |
| PH (1) | PH12012501042A1 (enExample) |
| RU (1) | RU2560164C2 (enExample) |
| SG (1) | SG180968A1 (enExample) |
| TW (1) | TWI491642B (enExample) |
| WO (1) | WO2011065346A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101339321B1 (ko) | 2011-09-12 | 2013-12-10 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 박막 성형품 |
| WO2014065594A1 (ko) * | 2012-10-23 | 2014-05-01 | 제일모직 주식회사 | 폴리아미드의 제조방법 |
| JP5956903B2 (ja) * | 2012-10-23 | 2016-07-27 | チェイル インダストリーズ インコーポレイテッド | ポリアミドの製造方法 |
| JP2017110101A (ja) * | 2015-12-16 | 2017-06-22 | 三菱瓦斯化学株式会社 | ポリアミド樹脂および成形品 |
| EA202192368A1 (ru) * | 2019-05-17 | 2022-03-02 | Чэнду 401 Текнолоджи Ко., Лтд | Способ получения экологически безопасной полиамидной смолы |
| KR102525718B1 (ko) | 2019-12-12 | 2023-04-25 | 한화솔루션 주식회사 | 폴리아마이드 제조 장치 및 방법 |
| CN112062950B (zh) * | 2020-03-28 | 2021-06-29 | 成都肆零壹科技有限公司 | 一种连续化尼龙聚合工艺 |
| CN118515458B (zh) * | 2024-05-11 | 2025-01-21 | 江苏南普地坪工程有限公司 | 一种金刚砂耐磨地坪材料及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002060486A (ja) * | 2000-08-24 | 2002-02-26 | Mitsubishi Gas Chem Co Inc | ポリアミドの製造方法 |
| US20080262193A1 (en) * | 2007-04-11 | 2008-10-23 | Hideyuki Kurose | Production method of polyamide |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4322874Y1 (enExample) | 1965-02-06 | 1968-09-26 | ||
| JPS4812390U (enExample) | 1971-06-29 | 1973-02-10 | ||
| JPS57200420A (en) * | 1981-06-04 | 1982-12-08 | Mitsubishi Gas Chem Co Inc | Production of polyamide |
| JPS58111829A (ja) * | 1981-12-25 | 1983-07-04 | Mitsubishi Gas Chem Co Inc | ポリアミドの製造方法 |
| JPH0322874A (ja) | 1989-06-16 | 1991-01-31 | Nissan Motor Co Ltd | 超音波モータ駆動装置 |
| BE1006314A3 (fr) | 1992-11-04 | 1994-07-19 | Solvay | Procede de synthese de polyamides. |
| JP3528875B2 (ja) | 1994-04-07 | 2004-05-24 | 三菱瓦斯化学株式会社 | 共重合ポリアミドの製造法 |
| JPH0812390A (ja) | 1994-06-22 | 1996-01-16 | Sumitomo Metal Mining Co Ltd | 人工軽量骨材の製造方法 |
| CA2333260A1 (en) * | 1998-05-29 | 1999-12-02 | Solutia, Inc. | Continuous polyamidation process |
| FR2794760B1 (fr) * | 1999-06-11 | 2001-08-17 | Rhodianyl | Procede de fabrication de polyamides |
| JP2001200053A (ja) | 2000-01-21 | 2001-07-24 | Mitsubishi Gas Chem Co Inc | ポリアミドの製造方法 |
| EP1118630B1 (en) | 2000-01-21 | 2006-05-17 | Mitsubishi Gas Chemical Company, Inc. | Process for producing polyamide |
| JP4168233B2 (ja) | 2002-05-10 | 2008-10-22 | 三菱瓦斯化学株式会社 | ポリアミド製造法 |
| JP2005139219A (ja) * | 2003-11-04 | 2005-06-02 | Mitsubishi Gas Chem Co Inc | ポリアミドの製造方法 |
| JP5343704B2 (ja) | 2008-05-29 | 2013-11-13 | 三菱瓦斯化学株式会社 | ポリアミドの製造方法 |
| CN101591433B (zh) | 2008-05-29 | 2013-05-01 | 三菱瓦斯化学株式会社 | 聚酰胺的制造方法 |
-
2010
- 2010-11-24 PH PH1/2012/501042A patent/PH12012501042A1/en unknown
- 2010-11-24 RU RU2012121840/04A patent/RU2560164C2/ru active
- 2010-11-24 EP EP10833192.7A patent/EP2505598B1/en active Active
- 2010-11-24 MY MYPI2012002254A patent/MY172071A/en unknown
- 2010-11-24 KR KR1020127013180A patent/KR101764900B1/ko active Active
- 2010-11-24 JP JP2011543252A patent/JP5633519B2/ja active Active
- 2010-11-24 SG SG2012037131A patent/SG180968A1/en unknown
- 2010-11-24 US US13/512,179 patent/US9260563B2/en active Active
- 2010-11-24 CN CN2010800538033A patent/CN102639601B/zh active Active
- 2010-11-24 WO PCT/JP2010/070857 patent/WO2011065346A1/ja not_active Ceased
- 2010-11-26 TW TW099140905A patent/TWI491642B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002060486A (ja) * | 2000-08-24 | 2002-02-26 | Mitsubishi Gas Chem Co Inc | ポリアミドの製造方法 |
| US20080262193A1 (en) * | 2007-04-11 | 2008-10-23 | Hideyuki Kurose | Production method of polyamide |
Also Published As
| Publication number | Publication date |
|---|---|
| SG180968A1 (enExample) | 2012-06-28 |
| RU2560164C2 (ru) | 2015-08-20 |
| RU2012121840A (ru) | 2014-01-10 |
| CN102639601A (zh) | 2012-08-15 |
| US20120271031A1 (en) | 2012-10-25 |
| KR20120102055A (ko) | 2012-09-17 |
| US9260563B2 (en) | 2016-02-16 |
| WO2011065346A1 (ja) | 2011-06-03 |
| EP2505598A4 (en) | 2014-08-13 |
| KR101764900B1 (ko) | 2017-08-03 |
| TW201130887A (en) | 2011-09-16 |
| PH12012501042A1 (en) | 2017-04-12 |
| EP2505598A1 (en) | 2012-10-03 |
| EP2505598B1 (en) | 2017-10-04 |
| CN102639601B (zh) | 2013-12-25 |
| JP5633519B2 (ja) | 2014-12-03 |
| MY172071A (en) | 2019-11-13 |
| JPWO2011065346A1 (ja) | 2013-04-11 |
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