DE2127025A1 - 2,4-bismaleimdothioluene - for homo - and copolymers and for cross-linking elastomers - Google Patents
2,4-bismaleimdothioluene - for homo - and copolymers and for cross-linking elastomersInfo
- Publication number
- DE2127025A1 DE2127025A1 DE19712127025 DE2127025A DE2127025A1 DE 2127025 A1 DE2127025 A1 DE 2127025A1 DE 19712127025 DE19712127025 DE 19712127025 DE 2127025 A DE2127025 A DE 2127025A DE 2127025 A1 DE2127025 A1 DE 2127025A1
- Authority
- DE
- Germany
- Prior art keywords
- cross
- bismaleimdothioluene
- homo
- copolymers
- parts
- 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.)
- Pending
Links
- 229920001971 elastomer Polymers 0.000 title abstract description 3
- 239000000806 elastomer Substances 0.000 title abstract description 3
- 238000004132 cross linking Methods 0.000 title abstract 2
- 229920001577 copolymer Polymers 0.000 title 1
- FJKKJQRXSPFNPM-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)-4-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC=C(N2C(C=CC2=O)=O)C=C1N1C(=O)C=CC1=O FJKKJQRXSPFNPM-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 9
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 abstract description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
2 4-Bismaleinimidotoluol Die Erfindung betrifft das bisher nicht bekannte 2, 4-Bismaleinimidotoluol (I). Seinen Aufbau zeigt die folgende Formel Die neue Verbindung kann hergestellt werden, indem man 2 Mol Maleinsäureanhydrid mit einem Mol 2, 4-Diaminotoluol in einem zweistufigen Verfahren umsetzt In der ersten Stufe (1) wird eine Lösung von 1 Mol 2, 4-Diaminotoluol, zum Beispiel in Tetrahydrofuran, in eine Lösung von 2 Mol Maleinsäureanhydrid - ebenfalls in Tetrahydrofuran - bei Raumtemperatur eingerührt. Als Zwischenstufe fällt hierbei die 2, 4-Bismaleinamidsäure (11) aus. 2 4-Bismaleimidotoluene The invention relates to the previously unknown 2,4-bismaleimidotoluene (I). The following formula shows its structure The new compound can be prepared by reacting 2 moles of maleic anhydride with one mole of 2,4-diaminotoluene in a two-stage process. In the first stage (1), a solution of 1 mole of 2,4-diaminotoluene, for example in tetrahydrofuran, in a solution of 2 moles of maleic anhydride - also in tetrahydrofuran - stirred in at room temperature. The 2,4-bismaleamic acid (11) precipitates here as an intermediate stage.
Die Bismaleinamidsäure (II) wird dann in Essigsäureanhydrid in Gegenwart von wasserfreiem Natriumacetat etwa eine Stunde auf 60 - 70°C erhitzt. Dabei fällt nach-dem Erkalten auf Raumtemperatur 2, 4-Bismaleinimidotoluol aus. Es wird abfiltriert und durch Umkristallisation aus Toluol gereinigt. 2, 4-Bismaleinimidotoluol ist gelb, kristallin und schmilzt bei 174 - 1760C.The bismaleamic acid (II) is then dissolved in acetic anhydride in the presence heated by anhydrous sodium acetate to 60 - 70 ° C for about an hour. It falls after cooling to room temperature 2,4-bismaleimidotoluene from. It is filtered off and purified by recrystallization from toluene. 2,4-bismaleimidotoluene is yellow, crystalline and melts at 174 - 1760C.
Die in der Verbindung vorhandenen beiden Doppelbindungen in den Maleinsäureresten machen sie polymerisierbar. Man erhält daraus durch Erhitzen auf 220 C Poly (2 , 4 - (2,4-Bismaleinimido)toluol.The two double bonds in the maleic acid residues present in the compound make them polymerizable. Poly (2, 4 - (2,4-bismaleimido) toluene.
2 ,4-Bismaleinimidotoluol eignet einet sich ferner als Vernetzungsmittel für Elastomere und zur Copolymerisation mit Vinylverbindungen, beispielsweise Styrol.2,4-Bismaleimidotoluene is also suitable as a crosslinking agent for elastomers and for copolymerization with vinyl compounds, for example styrene.
Beispiel: Zu einer Lösung von 392, 24 Teile Maleinsäureanhydrid, 2200 Raumteilen trockenem Tetrahydrofuran werden 244, 34 Teile 2, 4-Diaminotoluol, gelöst in 800 Raumteilen Tetrahydrofuran, so zugetropft, dass die Temperatur nicht über 30 C steigt. Dann wird noch 3 Stunden bei Raumtemperatur gerührt, die ausgefallene Bismaleinamidsäure abfiltriert und bei 60 C im Vacuum getrocknet.Example: To a solution of 392, 24 parts of maleic anhydride, 2200 Parts by volume of dry tetrahydrofuran are dissolved 244.34 parts of 2,4-diaminotoluene in 800 parts by volume of tetrahydrofuran, added dropwise so that the temperature does not exceed 30 C rises. The precipitated one is then stirred for a further 3 hours at room temperature Bismaleamic acid is filtered off and dried at 60 C in a vacuum.
286, 2 Teile getrocknetes 2, 4-Bismaleinamidotoluol, 612 Teile Essigsäureanhydrid und 58,95 Teile wasserfreies Natriumacetat werden in einem Rührgefäß auf 60 - 70 0C erhitzt und bei dieser Temperatur über eine Stunde unter gutem Rühren gehalten.286, 2 parts of dried 2,4-bismaleinamidotoluene, 612 parts of acetic anhydride and 58.95 parts of anhydrous sodium acetate are brought to 60-70 in a stirred vessel 0C heated and at this Temperature over an hour under good Stirring kept.
Nach dem Erkalten wird abfiltriert, der Filterrückstand aus Toluol umkristallisiert und bei 60 0C im Vacuum getrocknet.After cooling, it is filtered off, the filter residue from toluene recrystallized and dried at 60 ° C. in a vacuum.
Die Ausbeute an 2, 4-Bismaleinimidotoluol beträgt 165 Teile entsprechend 65 o/o der Theorie. Schmelzpunkt 174 - 1760C.The yield of 2,4-bismaleimidotoluene is 165 parts accordingly 65 o / o of theory. Melting point 174-1760C.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712127025 DE2127025A1 (en) | 1971-06-01 | 1971-06-01 | 2,4-bismaleimdothioluene - for homo - and copolymers and for cross-linking elastomers |
| DE19712165979 DE2165979A1 (en) | 1971-06-01 | 1971-06-01 | Poly-2,4-bis maleinimidotoluene - used for mechanically strong mouldings and in fibre reinforced windings |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712127025 DE2127025A1 (en) | 1971-06-01 | 1971-06-01 | 2,4-bismaleimdothioluene - for homo - and copolymers and for cross-linking elastomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2127025A1 true DE2127025A1 (en) | 1973-01-04 |
Family
ID=5809446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712127025 Pending DE2127025A1 (en) | 1971-06-01 | 1971-06-01 | 2,4-bismaleimdothioluene - for homo - and copolymers and for cross-linking elastomers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2127025A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0367599A1 (en) * | 1988-11-03 | 1990-05-09 | BP Chemicals Limited | Synthesis of bisimides |
| US5994561A (en) * | 1998-07-28 | 1999-11-30 | Rhein Chemie Rheinau Gmbh | Process for the preparation of aromatic maleimides |
-
1971
- 1971-06-01 DE DE19712127025 patent/DE2127025A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0367599A1 (en) * | 1988-11-03 | 1990-05-09 | BP Chemicals Limited | Synthesis of bisimides |
| US5994561A (en) * | 1998-07-28 | 1999-11-30 | Rhein Chemie Rheinau Gmbh | Process for the preparation of aromatic maleimides |
| EP0976730A1 (en) * | 1998-07-28 | 2000-02-02 | RHEIN-CHEMIE RHEINAU GmbH | Process for the production of aromatic maleimides |
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