DE2156723A1 - Transparente polyamide und verfahren zu ihrer herstellung - Google Patents
Transparente polyamide und verfahren zu ihrer herstellungInfo
- Publication number
- DE2156723A1 DE2156723A1 DE2156723A DE2156723A DE2156723A1 DE 2156723 A1 DE2156723 A1 DE 2156723A1 DE 2156723 A DE2156723 A DE 2156723A DE 2156723 A DE2156723 A DE 2156723A DE 2156723 A1 DE2156723 A1 DE 2156723A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- diamines
- carbon atoms
- acids
- aliphatic
- 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- Withdrawn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
- 229920002647 polyamide Polymers 0.000 title claims description 34
- 239000004952 Polyamide Substances 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 28
- 150000004985 diamines Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 4
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 3
- ABPUBUORTRHHDZ-UHFFFAOYSA-N [4-(aminomethyl)-3-bicyclo[2.2.1]heptanyl]methanamine Chemical class C1CC2(CN)C(CN)CC1C2 ABPUBUORTRHHDZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- 150000004984 aromatic diamines Chemical class 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 description 10
- 238000007710 freezing Methods 0.000 description 8
- 230000008014 freezing Effects 0.000 description 8
- -1 aliphatic diamines Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- DGNHGRLDBKAPEH-UHFFFAOYSA-N 3-azaniumyl-2,2-dimethylpropanoate Chemical compound NCC(C)(C)C(O)=O DGNHGRLDBKAPEH-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ZBLACDIKXKCJGF-WDSKDSINSA-N [(1r,2r)-2-(aminomethyl)cyclobutyl]methanamine Chemical compound NC[C@@H]1CC[C@H]1CN ZBLACDIKXKCJGF-WDSKDSINSA-N 0.000 description 1
- QWBXSHYNFZGYAM-UHFFFAOYSA-N [3-(aminomethyl)-2,4-dimethylphenyl]methanamine Chemical compound CC1=CC=C(CN)C(C)=C1CN QWBXSHYNFZGYAM-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
- AJSMFLLYPNSHIV-UHFFFAOYSA-N [4-(aminomethyl)-2,5-dimethylphenyl]methanamine Chemical compound CC1=CC(CN)=C(C)C=C1CN AJSMFLLYPNSHIV-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
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LNGJOYPCXLOTKL-UHFFFAOYSA-N cyclopentane-1,3-dicarboxylic acid Chemical class OC(=O)C1CCC(C(O)=O)C1 LNGJOYPCXLOTKL-UHFFFAOYSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 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 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic 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
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE791468D BE791468A (fr) | 1971-11-16 | Polyamides transparents et leur preparation | |
| DE2156723A DE2156723A1 (de) | 1971-11-16 | 1971-11-16 | Transparente polyamide und verfahren zu ihrer herstellung |
| BR704872A BR7207048D0 (pt) | 1971-10-15 | 1972-10-11 | Rede de comutacao em combinacao com conjunto de comutacao processo para obtencao de poliamidas transparentes |
| ES408487A ES408487A1 (es) | 1971-11-16 | 1972-11-10 | Procedimiento de obtencion de poliamidas transparentes. |
| NL7215250A NL7215250A (enExample) | 1971-11-16 | 1972-11-10 | |
| CH1649572A CH572499A5 (enExample) | 1971-11-16 | 1972-11-13 | |
| IT31649/72A IT970493B (it) | 1971-11-16 | 1972-11-14 | Poliamidi trasparenti e procedi mento per la loro preparazione |
| CA156,298A CA979589A (en) | 1971-11-16 | 1972-11-14 | Transparent polyamides and process for their preparation |
| AU48828/72A AU470916B2 (en) | 1971-11-16 | 1972-11-14 | Transparent polyamides and process for their preparation |
| US306202A US3876585A (en) | 1971-11-16 | 1972-11-14 | Transparent polyamides from a mixture of bis-(aminomethyl) norbornanes |
| JP11358872A JPS5550054B2 (enExample) | 1971-11-16 | 1972-11-14 | |
| ZA728092A ZA728092B (en) | 1971-11-16 | 1972-11-15 | Transparent polyamides and process for their preparation |
| DK567872AA DK130745B (da) | 1971-11-16 | 1972-11-15 | Fremgangsmåde til fremstilling af transparente copolyamider. |
| SE7214822A SE380815B (sv) | 1971-11-16 | 1972-11-15 | Forfarande for framstellning av transparenta sampolyamider |
| GB5273872A GB1395595A (en) | 1971-11-16 | 1972-11-15 | Polyamides |
| AT968972A AT320982B (de) | 1971-11-16 | 1972-11-15 | Verfahren zur Herstellung transparenter Polyamide |
| SU1848417A SU437305A3 (ru) | 1971-11-16 | 1972-11-16 | Способ получения прозрачных полиамидов |
| FR7240693A FR2160527B1 (enExample) | 1971-11-16 | 1972-11-16 | |
| US05/519,244 US4001192A (en) | 1971-11-16 | 1974-10-30 | Transparent polyamides from bis(aminomethyl)-norbornanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156723A DE2156723A1 (de) | 1971-11-16 | 1971-11-16 | Transparente polyamide und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2156723A1 true DE2156723A1 (de) | 1973-05-24 |
Family
ID=5825203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2156723A Withdrawn DE2156723A1 (de) | 1971-10-15 | 1971-11-16 | Transparente polyamide und verfahren zu ihrer herstellung |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3876585A (enExample) |
| JP (1) | JPS5550054B2 (enExample) |
| AT (1) | AT320982B (enExample) |
| AU (1) | AU470916B2 (enExample) |
| BE (1) | BE791468A (enExample) |
| CA (1) | CA979589A (enExample) |
| CH (1) | CH572499A5 (enExample) |
| DE (1) | DE2156723A1 (enExample) |
| DK (1) | DK130745B (enExample) |
| ES (1) | ES408487A1 (enExample) |
| FR (1) | FR2160527B1 (enExample) |
| GB (1) | GB1395595A (enExample) |
| IT (1) | IT970493B (enExample) |
| NL (1) | NL7215250A (enExample) |
| SE (1) | SE380815B (enExample) |
| SU (1) | SU437305A3 (enExample) |
| ZA (1) | ZA728092B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2715413A1 (de) * | 1977-04-06 | 1978-10-12 | Bayer Ag | Transparente copolyamide |
| US4398012A (en) * | 1982-01-19 | 1983-08-09 | Allied Corporation | Transparent copolyamide from caprolactam, cyclic diamine and cyclic dicarboxylic acid |
| CN102762636B (zh) * | 2009-12-28 | 2014-02-19 | 三菱瓦斯化学株式会社 | 聚酰胺化合物 |
| JP7272008B2 (ja) * | 2019-02-26 | 2023-05-12 | 三菱瓦斯化学株式会社 | アミン組成物、アミン化合物、製造方法およびその応用 |
| JP7391225B2 (ja) | 2020-07-16 | 2023-12-04 | 三井化学株式会社 | 結晶性ポリアミド樹脂、樹脂組成物および成形体 |
| CN118525060A (zh) | 2022-01-12 | 2024-08-20 | 三井化学株式会社 | 聚酰胺树脂组合物和聚酰胺成型体 |
| EP4464746A4 (en) | 2022-01-12 | 2025-12-24 | Mitsui Chemicals Inc | POLYAMIDE RESIN COMPOSITION, AND POLYAMIDE MOLDED BODY |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3301827A (en) * | 1965-05-07 | 1967-01-31 | Du Pont | Polymers from polycyclic reactants having functional substituents on bridgehead carbon atoms |
| DE2060703A1 (de) * | 1970-12-10 | 1972-06-22 | Hoechst Ag | Glasklare Polyamide |
-
0
- BE BE791468D patent/BE791468A/xx unknown
-
1971
- 1971-11-16 DE DE2156723A patent/DE2156723A1/de not_active Withdrawn
-
1972
- 1972-11-10 NL NL7215250A patent/NL7215250A/xx not_active Application Discontinuation
- 1972-11-10 ES ES408487A patent/ES408487A1/es not_active Expired
- 1972-11-13 CH CH1649572A patent/CH572499A5/xx not_active IP Right Cessation
- 1972-11-14 AU AU48828/72A patent/AU470916B2/en not_active Expired
- 1972-11-14 US US306202A patent/US3876585A/en not_active Expired - Lifetime
- 1972-11-14 IT IT31649/72A patent/IT970493B/it active
- 1972-11-14 CA CA156,298A patent/CA979589A/en not_active Expired
- 1972-11-14 JP JP11358872A patent/JPS5550054B2/ja not_active Expired
- 1972-11-15 SE SE7214822A patent/SE380815B/xx unknown
- 1972-11-15 DK DK567872AA patent/DK130745B/da unknown
- 1972-11-15 GB GB5273872A patent/GB1395595A/en not_active Expired
- 1972-11-15 ZA ZA728092A patent/ZA728092B/xx unknown
- 1972-11-15 AT AT968972A patent/AT320982B/de active
- 1972-11-16 SU SU1848417A patent/SU437305A3/ru active
- 1972-11-16 FR FR7240693A patent/FR2160527B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE380815B (sv) | 1975-11-17 |
| CA979589A (en) | 1975-12-09 |
| ZA728092B (en) | 1973-08-29 |
| CH572499A5 (enExample) | 1976-02-13 |
| US3876585A (en) | 1975-04-08 |
| DK130745B (da) | 1975-04-07 |
| GB1395595A (en) | 1975-05-29 |
| AT320982B (de) | 1975-03-10 |
| BE791468A (fr) | 1973-05-16 |
| AU470916B2 (en) | 1976-04-01 |
| ES408487A1 (es) | 1975-11-01 |
| FR2160527A1 (enExample) | 1973-06-29 |
| JPS5550054B2 (enExample) | 1980-12-16 |
| JPS4860193A (enExample) | 1973-08-23 |
| NL7215250A (enExample) | 1973-05-18 |
| DK130745C (enExample) | 1975-09-08 |
| IT970493B (it) | 1974-04-10 |
| FR2160527B1 (enExample) | 1976-06-04 |
| SU437305A3 (ru) | 1974-07-25 |
| AU4882872A (en) | 1974-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |