JP5542667B2 - ポリアミドの製造方法 - Google Patents
ポリアミドの製造方法 Download PDFInfo
- Publication number
- JP5542667B2 JP5542667B2 JP2010512647A JP2010512647A JP5542667B2 JP 5542667 B2 JP5542667 B2 JP 5542667B2 JP 2010512647 A JP2010512647 A JP 2010512647A JP 2010512647 A JP2010512647 A JP 2010512647A JP 5542667 B2 JP5542667 B2 JP 5542667B2
- Authority
- JP
- Japan
- Prior art keywords
- diamine
- dicarboxylic acid
- mixture
- acid
- separator
- 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.)
- Expired - Fee Related
Links
- 229920002647 polyamide Polymers 0.000 title claims description 27
- 239000004952 Polyamide Substances 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 62
- 150000004985 diamines Chemical class 0.000 claims description 55
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 23
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000001704 evaporation Methods 0.000 claims description 21
- 230000008020 evaporation Effects 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 21
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 13
- 230000007812 deficiency Effects 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 238000005469 granulation Methods 0.000 claims description 5
- 230000003179 granulation Effects 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- 238000001125 extrusion Methods 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 238000011144 upstream manufacturing Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- -1 for example Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 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
- 230000000996 additive effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229920006345 thermoplastic polyamide Polymers 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
-
- 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
-
- 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
-
- 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
- C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07110656 | 2007-06-20 | ||
| EP07110656.1 | 2007-06-20 | ||
| PCT/EP2008/057360 WO2008155281A1 (de) | 2007-06-20 | 2008-06-12 | Verfahren zur herstellung von polyamiden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010530459A JP2010530459A (ja) | 2010-09-09 |
| JP2010530459A5 JP2010530459A5 (enExample) | 2014-02-20 |
| JP5542667B2 true JP5542667B2 (ja) | 2014-07-09 |
Family
ID=39712356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010512647A Expired - Fee Related JP5542667B2 (ja) | 2007-06-20 | 2008-06-12 | ポリアミドの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8759476B2 (enExample) |
| EP (1) | EP2160432B1 (enExample) |
| JP (1) | JP5542667B2 (enExample) |
| KR (1) | KR101538813B1 (enExample) |
| CN (2) | CN101687989A (enExample) |
| BR (1) | BRPI0812711B1 (enExample) |
| ES (1) | ES2392572T3 (enExample) |
| PL (1) | PL2160432T3 (enExample) |
| WO (1) | WO2008155281A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101679626B (zh) * | 2007-06-20 | 2011-12-21 | 巴斯夫欧洲公司 | 在挤出机中制备聚酰胺的方法 |
| ATE540072T1 (de) * | 2008-06-20 | 2012-01-15 | Basf Se | Kontinuierliches verfahren zur mehrstufigen trocknung und nachkondensation von polyamidgranulat |
| KR101183393B1 (ko) * | 2008-07-11 | 2012-09-14 | 상하이 킹파 사이언스 앤 테크놀로지 컴퍼니 리미티드 | 세미-방향족 폴리아미드 및 그 폐수 배출량을 낮추는 제조 방법 |
| EP2315794B1 (de) * | 2008-08-14 | 2019-02-06 | Basf Se | Batch-verfahren zur herstellung von polyamiden |
| DE102009025537A1 (de) | 2009-06-19 | 2010-12-30 | Basf Se | Copolyamide |
| US9315626B2 (en) | 2009-12-08 | 2016-04-19 | Basf Se | Process for preparing polyamides |
| US9890247B2 (en) * | 2010-04-29 | 2018-02-13 | Dsm Ip Assets B.V. | Semi-aromatic polyamide |
| JP5892065B2 (ja) | 2012-06-19 | 2016-03-23 | 東レ株式会社 | ポリアミドの製造方法 |
| BR112015004454B1 (pt) * | 2012-09-03 | 2021-03-23 | Basf Se | Método para produção de poliamidas por meio de policondensação de monômeros e/ou oligômeros formadores de poliamida |
| CN110938205A (zh) * | 2013-05-01 | 2020-03-31 | 英威达纺织（英国）有限公司 | 包括多个后端的聚酰胺合成 |
| CN104129880B (zh) * | 2013-05-01 | 2018-11-23 | 英威达纺织（英国）有限公司 | 用于从聚酰胺合成工艺回收水的方法和系统 |
| CN113830951A (zh) * | 2013-05-01 | 2021-12-24 | 英威达纺织（英国）有限公司 | 用于从聚酰胺合成工艺回收水的方法和系统 |
| WO2014198764A1 (de) * | 2013-06-12 | 2014-12-18 | Basf Se | Verfahren zur herstellung teilaromatischer copolyamide mit hohem diaminüberschuss |
| CN106700064B (zh) * | 2016-12-28 | 2019-01-08 | 浙江新和成特种材料有限公司 | 一种半芳香族聚酰胺生产方法及半芳香族聚酰胺 |
| PL233020B1 (pl) * | 2017-09-29 | 2019-08-30 | Grupa Azoty Spolka Akcyjna | Sposób wytwarzania poliftalamidów |
| PL240713B1 (pl) * | 2017-12-07 | 2022-05-23 | Grupa Azoty Spolka Akcyjna | Sposób otrzymywania kompozytów poliftalamidów z nanonapełniaczem krzemionkowym |
| CN112262171B (zh) | 2018-11-05 | 2023-04-28 | 株式会社Lg化学 | 聚酰胺树脂和使用其的聚合物膜、树脂层合体 |
| WO2022248262A1 (en) | 2021-05-26 | 2022-12-01 | Basf Se | Process for preparing polyamides |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1720349A1 (de) | 1968-02-22 | 1971-06-09 | Basf Ag | Verfahren und Vorrichtung zum kontinuierlichen Herstellen von hoehermolekularem Polyamid 6,6 |
| US4617342A (en) * | 1983-02-16 | 1986-10-14 | Amoco Corporation | Crystalline copolyamide from terephthalic acid, isophthalic acid and C.sub.6 |
| DE3321581A1 (de) | 1983-06-15 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von polyamiden |
| AT377276B (de) | 1983-06-20 | 1985-02-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von haerterkomponenten fuer lackbindemittel |
| US5298595A (en) * | 1987-07-17 | 1994-03-29 | Basf Aktiengesellschaft | Partly aromatic copolyamides of reduced triamine content |
| FR2637901B1 (fr) * | 1988-10-13 | 1990-12-14 | Rhone Poulenc Chimie | Procede de preparation de polyamides amorphes a base d'acides dicarboxyliques aromatiques et de diamines aliphatiques |
| GB8917093D0 (en) | 1989-07-26 | 1989-09-13 | Bp Chem Int Ltd | High molecular weight polyamides production |
| JPH0726015A (ja) * | 1993-07-15 | 1995-01-27 | Toray Ind Inc | ポリアミド樹脂の製造方法 |
| JPH07165911A (ja) * | 1993-12-16 | 1995-06-27 | Mitsui Petrochem Ind Ltd | 芳香族ポリアミド樹脂の製造方法 |
| DE4404250A1 (de) | 1994-02-10 | 1995-08-17 | Basf Ag | Teilaromatische Copolyamidformmassen mit hoher Kristallinität |
| DE19513940A1 (de) * | 1994-07-14 | 1996-01-18 | Inventa Ag | Verfahren zur Herstellung von Vorkondensaten teilkristalliner oder amorpher, thermoplastisch verarbeitbarer teilaromatischer Polyamide bzw. Copolyamide |
| DE19501998A1 (de) * | 1995-01-24 | 1996-07-25 | Basf Ag | Thermoplastische Polyamidformmassen |
| DE19514145A1 (de) | 1995-04-15 | 1996-10-17 | Basf Ag | Verfahren zur Herstellung eines Polyamids auf der Basis einer Dicarbonsäure und eines Diamins |
| FR2873380B1 (fr) * | 2004-07-20 | 2006-11-03 | Arkema Sa | Poudres de polyamides ignifuges et leur utilisation dans un procede d'agglomeration par fusion |
| CN101679626B (zh) | 2007-06-20 | 2011-12-21 | 巴斯夫欧洲公司 | 在挤出机中制备聚酰胺的方法 |
| ATE540072T1 (de) | 2008-06-20 | 2012-01-15 | Basf Se | Kontinuierliches verfahren zur mehrstufigen trocknung und nachkondensation von polyamidgranulat |
| EP2315794B1 (de) | 2008-08-14 | 2019-02-06 | Basf Se | Batch-verfahren zur herstellung von polyamiden |
| FR2939075B1 (fr) * | 2008-12-01 | 2010-12-17 | Rhodia Operations | Realisation d'article par fusion selective de couches de poudre de polymere |
-
2008
- 2008-06-12 BR BRPI0812711A patent/BRPI0812711B1/pt not_active IP Right Cessation
- 2008-06-12 CN CN200880020794A patent/CN101687989A/zh active Pending
- 2008-06-12 JP JP2010512647A patent/JP5542667B2/ja not_active Expired - Fee Related
- 2008-06-12 WO PCT/EP2008/057360 patent/WO2008155281A1/de not_active Ceased
- 2008-06-12 KR KR1020097026454A patent/KR101538813B1/ko not_active Expired - Fee Related
- 2008-06-12 CN CN201510977668.6A patent/CN105418914A/zh active Pending
- 2008-06-12 EP EP08760905A patent/EP2160432B1/de active Active
- 2008-06-12 US US12/665,564 patent/US8759476B2/en active Active
- 2008-06-12 PL PL08760905T patent/PL2160432T3/pl unknown
- 2008-06-12 ES ES08760905T patent/ES2392572T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008155281A1 (de) | 2008-12-24 |
| KR20100033970A (ko) | 2010-03-31 |
| BRPI0812711A2 (pt) | 2014-12-23 |
| EP2160432A1 (de) | 2010-03-10 |
| JP2010530459A (ja) | 2010-09-09 |
| BRPI0812711B1 (pt) | 2018-12-18 |
| US20100190934A1 (en) | 2010-07-29 |
| PL2160432T3 (pl) | 2013-03-29 |
| EP2160432B1 (de) | 2012-10-24 |
| CN105418914A (zh) | 2016-03-23 |
| ES2392572T3 (es) | 2012-12-11 |
| US8759476B2 (en) | 2014-06-24 |
| BRPI0812711A8 (pt) | 2018-04-03 |
| KR101538813B1 (ko) | 2015-07-22 |
| CN101687989A (zh) | 2010-03-31 |
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