DE2133648A1 - Polyamid und Verfahren zu seiner Herstellung - Google Patents
Polyamid und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2133648A1 DE2133648A1 DE19712133648 DE2133648A DE2133648A1 DE 2133648 A1 DE2133648 A1 DE 2133648A1 DE 19712133648 DE19712133648 DE 19712133648 DE 2133648 A DE2133648 A DE 2133648A DE 2133648 A1 DE2133648 A1 DE 2133648A1
- Authority
- DE
- Germany
- Prior art keywords
- polyamide
- diamino
- polycondensation
- polyamide according
- dicarboxylic acid
- 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.)
- Withdrawn
Links
- 239000004952 Polyamide Substances 0.000 title claims description 50
- 229920002647 polyamide Polymers 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims description 42
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 30
- 238000006068 polycondensation reaction Methods 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- 238000002844 melting Methods 0.000 claims description 17
- 230000008018 melting Effects 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QFMSQSOYTFZACB-UHFFFAOYSA-N docosane-1,22-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCN QFMSQSOYTFZACB-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- POIZGMCHYSVWDU-UHFFFAOYSA-N icosane-1,20-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCN POIZGMCHYSVWDU-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000003022 phthalic acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- CYBQOEBIIKKSSY-UHFFFAOYSA-N henicosane-1,21-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCN CYBQOEBIIKKSSY-UHFFFAOYSA-N 0.000 claims description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- OCJLSVQJNZKGKL-UHFFFAOYSA-N tricosane-1,23-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCCN OCJLSVQJNZKGKL-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 150000005840 aryl radicals Chemical class 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000004455 differential thermal analysis Methods 0.000 description 17
- 239000000155 melt Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 6
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010406 interfacial reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- IAFYEFQPNIPAGF-UHFFFAOYSA-N tetracosane-1,24-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCCCN IAFYEFQPNIPAGF-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7025505A FR2123565A5 (enrdf_load_stackoverflow) | 1970-07-09 | 1970-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2133648A1 true DE2133648A1 (de) | 1972-01-13 |
Family
ID=9058515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712133648 Withdrawn DE2133648A1 (de) | 1970-07-09 | 1971-07-06 | Polyamid und Verfahren zu seiner Herstellung |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1109059C (zh) * | 2000-03-30 | 2003-05-21 | 上海杰事杰新材料股份有限公司 | 一种长链尼龙及其制备工艺 |
| WO2021049503A1 (ja) * | 2019-09-13 | 2021-03-18 | 岡村製油株式会社 | ジアミン化合物およびその製造方法 |
-
1970
- 1970-07-09 FR FR7025505A patent/FR2123565A5/fr not_active Expired
-
1971
- 1971-07-06 NL NL7109294A patent/NL7109294A/xx not_active Application Discontinuation
- 1971-07-06 DE DE19712133648 patent/DE2133648A1/de not_active Withdrawn
- 1971-07-06 CH CH990171A patent/CH530432A/fr not_active IP Right Cessation
- 1971-07-07 GB GB3193571A patent/GB1339853A/en not_active Expired
- 1971-07-07 LU LU63483D patent/LU63483A1/xx unknown
- 1971-07-08 BE BE769720A patent/BE769720A/xx unknown
- 1971-07-08 CA CA117,786A patent/CA987834A/en not_active Expired
- 1971-07-08 JP JP46050628A patent/JPS5112674B1/ja active Pending
- 1971-07-08 DD DD15636671A patent/DD94896A5/xx unknown
- 1971-07-09 SU SU1678080A patent/SU378021A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1339853A (en) | 1973-12-05 |
| CH530432A (fr) | 1972-11-15 |
| CA987834A (en) | 1976-04-20 |
| JPS5112674B1 (enrdf_load_stackoverflow) | 1976-04-21 |
| SU378021A3 (enrdf_load_stackoverflow) | 1973-04-17 |
| NL7109294A (enrdf_load_stackoverflow) | 1972-01-11 |
| LU63483A1 (enrdf_load_stackoverflow) | 1971-11-15 |
| BE769720A (fr) | 1971-11-16 |
| FR2123565A5 (enrdf_load_stackoverflow) | 1972-09-15 |
| DD94896A5 (enrdf_load_stackoverflow) | 1973-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |