DE1720884B2 - Verfahren zur herstellung stickstoffhaltiger polykondensate - Google Patents
Verfahren zur herstellung stickstoffhaltiger polykondensateInfo
- Publication number
- DE1720884B2 DE1720884B2 DE1968G0052088 DEG0052088A DE1720884B2 DE 1720884 B2 DE1720884 B2 DE 1720884B2 DE 1968G0052088 DE1968G0052088 DE 1968G0052088 DE G0052088 A DEG0052088 A DE G0052088A DE 1720884 B2 DE1720884 B2 DE 1720884B2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- compound
- polycondensation
- acid
- polycondensates
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title 2
- 229910052757 nitrogen Inorganic materials 0.000 title 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000006068 polycondensation reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 229920000137 polyphosphoric acid Polymers 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- -1 phenyl ether diamine Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000006198 methoxylation reaction Methods 0.000 description 3
- 230000010355 oscillation Effects 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- LHAYYSWHQVZWSC-UHFFFAOYSA-N 26-oxahexacyclo[25.4.0.02,7.08,13.014,19.020,25]hentriaconta-1(31),2,4,6,8,10,12,14,16,18,20,22,24,27,29-pentadecaene Chemical group C12=C(C=CC=C1)C1=C(C=CC=C1)C1=C(C=CC=C1)OC1=C(C=CC=C1)C1=C2C=CC=C1 LHAYYSWHQVZWSC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OVFKPOZIUBFQMK-UHFFFAOYSA-N 3,3-dichloro-1h-quinoline-2,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)(Cl)C(=O)NC2=C1 OVFKPOZIUBFQMK-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- DJEOQLAWTUKCCA-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=CC=1NCC(=O)O)C1=CC(=C(NCC(=O)O)C=C1)C(=O)O Chemical compound C(=O)(O)C=1C=C(C=CC=1NCC(=O)O)C1=CC(=C(NCC(=O)O)C=C1)C(=O)O DJEOQLAWTUKCCA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1968G0052088 DE1720884B2 (de) | 1968-01-08 | 1968-01-08 | Verfahren zur herstellung stickstoffhaltiger polykondensate |
| GB1238675D GB1238675A (en, 2012) | 1968-01-08 | 1968-11-26 | |
| AT11812/68A AT284459B (de) | 1968-01-08 | 1968-12-04 | Verfahren zur herstellung von hochtemperaturbestaendigen polymeren |
| BE725122D BE725122A (en, 2012) | 1968-01-08 | 1968-12-09 | |
| SE17042/68A SE336904B (en, 2012) | 1968-01-08 | 1968-12-12 | |
| LU57580D LU57580A1 (en, 2012) | 1968-01-08 | 1968-12-17 | |
| US788931A US3577387A (en) | 1968-01-08 | 1969-01-03 | Process of preparing heat-resistant polymers |
| NL6900181A NL6900181A (en, 2012) | 1968-01-08 | 1969-01-06 | |
| FR6900095A FR2000055A1 (en, 2012) | 1968-01-08 | 1969-01-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1968G0052088 DE1720884B2 (de) | 1968-01-08 | 1968-01-08 | Verfahren zur herstellung stickstoffhaltiger polykondensate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1720884A1 DE1720884A1 (de) | 1971-08-05 |
| DE1720884B2 true DE1720884B2 (de) | 1976-06-16 |
Family
ID=7130065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1968G0052088 Granted DE1720884B2 (de) | 1968-01-08 | 1968-01-08 | Verfahren zur herstellung stickstoffhaltiger polykondensate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3577387A (en, 2012) |
| AT (1) | AT284459B (en, 2012) |
| BE (1) | BE725122A (en, 2012) |
| DE (1) | DE1720884B2 (en, 2012) |
| FR (1) | FR2000055A1 (en, 2012) |
| GB (1) | GB1238675A (en, 2012) |
| LU (1) | LU57580A1 (en, 2012) |
| NL (1) | NL6900181A (en, 2012) |
| SE (1) | SE336904B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1199699A (en) * | 1968-01-08 | 1970-07-22 | Glanzstoff Ag | Process for the Production of Condensed Aromatic Bis-(2,4-Dihydroxypyridine) Derivatives |
| US3961009A (en) * | 1970-04-22 | 1976-06-01 | Toray Industries, Inc. | Process for the production of a shaped article of a heat resistant polymer |
| US3985934A (en) * | 1974-07-26 | 1976-10-12 | The Upjohn Company | Polyimide fiber having a serrated surface and a process of producing same |
| US4299787A (en) * | 1978-10-19 | 1981-11-10 | International Harvester Company | Melt spinning polyimide fibers |
-
1968
- 1968-01-08 DE DE1968G0052088 patent/DE1720884B2/de active Granted
- 1968-11-26 GB GB1238675D patent/GB1238675A/en not_active Expired
- 1968-12-04 AT AT11812/68A patent/AT284459B/de not_active IP Right Cessation
- 1968-12-09 BE BE725122D patent/BE725122A/xx unknown
- 1968-12-12 SE SE17042/68A patent/SE336904B/xx unknown
- 1968-12-17 LU LU57580D patent/LU57580A1/xx unknown
-
1969
- 1969-01-03 US US788931A patent/US3577387A/en not_active Expired - Lifetime
- 1969-01-06 NL NL6900181A patent/NL6900181A/xx unknown
- 1969-01-07 FR FR6900095A patent/FR2000055A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| SE336904B (en, 2012) | 1971-07-19 |
| AT284459B (de) | 1970-09-10 |
| FR2000055A1 (en, 2012) | 1969-08-29 |
| GB1238675A (en, 2012) | 1971-07-07 |
| NL6900181A (en, 2012) | 1969-07-10 |
| US3577387A (en) | 1971-05-04 |
| LU57580A1 (en, 2012) | 1969-04-08 |
| DE1720884A1 (de) | 1971-08-05 |
| BE725122A (en, 2012) | 1969-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |