CA1188040A - Process for making polytetramethyleneadipamide - Google Patents
Process for making polytetramethyleneadipamideInfo
- Publication number
- CA1188040A CA1188040A CA000413215A CA413215A CA1188040A CA 1188040 A CA1188040 A CA 1188040A CA 000413215 A CA000413215 A CA 000413215A CA 413215 A CA413215 A CA 413215A CA 1188040 A CA1188040 A CA 1188040A
- Authority
- CA
- Canada
- Prior art keywords
- polyamide
- weight
- polymer
- solvent
- temperature
- 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
Links
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 24
- 239000004952 Polyamide Substances 0.000 claims abstract description 17
- 229920002647 polyamide Polymers 0.000 claims abstract description 17
- 229920003189 Nylon 4,6 Polymers 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 21
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 8
- 235000011037 adipic acid Nutrition 0.000 claims description 8
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005700 Putrescine Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 abstract description 7
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- -1 poly tetramethylene Polymers 0.000 description 6
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 5
- 230000005494 condensation Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- OECUQWQIGXMPAN-UHFFFAOYSA-N 6-oxo-6-pyrrolidin-1-ylhexanamide Chemical compound NC(=O)CCCCC(=O)N1CCCC1 OECUQWQIGXMPAN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- RVNSAAIWCWTCTJ-ZPQYLTHOSA-N (2s,3s,4r)-2-(1,2-dihydroxyethyl)pyrrolidine-3,4-diol Chemical compound OCC(O)[C@@H]1NC[C@@H](O)[C@H]1O RVNSAAIWCWTCTJ-ZPQYLTHOSA-N 0.000 description 1
- JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-UHFFFAOYSA-N 0.000 description 1
- QVNVGTVAPQGSOF-UHFFFAOYSA-L 3-[4-(9,9-dimethyl-3-aza-9-azoniabicyclo[3.3.1]nonan-3-yl)butyl]-9,9-dimethyl-3-aza-9-azoniabicyclo[3.3.1]nonane;diiodide Chemical compound [I-].[I-].C1C([N+]2(C)C)CCCC2CN1CCCCN(C1)CC2CCCC1[N+]2(C)C QVNVGTVAPQGSOF-UHFFFAOYSA-L 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000037516 chromosome inversion disease Diseases 0.000 description 1
- 238000001704 evaporation 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
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007790 solid phase Substances 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
- C08G69/28—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8104639A NL8104639A (nl) | 1981-10-13 | 1981-10-13 | Werkwijze voor het maken van polytetramethyleenadipamide. |
| NL8104639 | 1981-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1188040A true CA1188040A (en) | 1985-05-28 |
Family
ID=19838209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000413215A Expired CA1188040A (en) | 1981-10-13 | 1982-10-12 | Process for making polytetramethyleneadipamide |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4463166A (forum.php) |
| EP (1) | EP0077106B1 (forum.php) |
| JP (1) | JPS5883029A (forum.php) |
| CA (1) | CA1188040A (forum.php) |
| DE (1) | DE3268581D1 (forum.php) |
| ES (1) | ES516413A0 (forum.php) |
| IN (1) | IN155281B (forum.php) |
| NL (1) | NL8104639A (forum.php) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3407492A1 (de) * | 1984-03-01 | 1985-09-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von copolyamiden aus adipinsaeure, terephthalsaeure und hexamethylendiamin |
| JPS60220731A (ja) * | 1984-04-17 | 1985-11-05 | Unitika Ltd | ポリアミドフィルムおよびその製造方法 |
| NL8401271A (nl) * | 1984-04-19 | 1985-11-18 | Stamicarbon | Werkwijze voor het bereiden van polytetramethyleenadipamide. |
| JPH0781007B2 (ja) * | 1985-05-31 | 1995-08-30 | デーエスエム ナムローゼ フェンノートシャップ | 白色の高分子量ポリ（テトラメチレンアジパミド）の製法 |
| EP0247203A1 (en) * | 1985-11-01 | 1987-12-02 | Teijin Limited | Polyamide packaging material |
| NL8601893A (nl) * | 1986-07-22 | 1988-02-16 | Stamicarbon | Bereiding van hoog-moleculair polytetramethyleenadipamide. |
| JPH0712359A (ja) * | 1993-06-25 | 1995-01-17 | Tomeji Kawasaki | 集合住宅の調理用排気装置 |
| WO2011004138A1 (en) | 2009-07-09 | 2011-01-13 | Invista Technologies S.A.R.L. | Preparation of polyamides |
| TWI563034B (en) * | 2011-05-13 | 2016-12-21 | Dsm Ip Assets Bv | Flame retardant semi-aromatic polyamide composition and moulded products made therefrom |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL49796C (forum.php) * | 1937-08-20 | |||
| US3932364A (en) * | 1972-10-17 | 1976-01-13 | Sumitomo Chemical Company, Limited | Production of polyamides in the presence of a phosphorus acid ester and an organic base |
-
1981
- 1981-10-13 NL NL8104639A patent/NL8104639A/nl not_active Application Discontinuation
-
1982
- 1982-10-06 JP JP57176017A patent/JPS5883029A/ja active Pending
- 1982-10-11 ES ES516413A patent/ES516413A0/es active Granted
- 1982-10-12 EP EP82201262A patent/EP0077106B1/en not_active Expired
- 1982-10-12 CA CA000413215A patent/CA1188040A/en not_active Expired
- 1982-10-12 DE DE8282201262T patent/DE3268581D1/de not_active Expired
- 1982-10-13 IN IN1187/CAL/82A patent/IN155281B/en unknown
- 1982-10-13 US US06/433,879 patent/US4463166A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3268581D1 (en) | 1986-02-27 |
| ES8307267A1 (es) | 1983-06-16 |
| IN155281B (forum.php) | 1985-01-12 |
| ES516413A0 (es) | 1983-06-16 |
| EP0077106B1 (en) | 1986-01-15 |
| NL8104639A (nl) | 1983-05-02 |
| EP0077106A1 (en) | 1983-04-20 |
| JPS5883029A (ja) | 1983-05-18 |
| US4463166A (en) | 1984-07-31 |
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| Publication | Publication Date | Title |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |