DE2053153B2 - Process for the preparation of poly cyclotnphosphazenamiden - Google Patents
Process for the preparation of poly cyclotnphosphazenamidenInfo
- Publication number
- DE2053153B2 DE2053153B2 DE2053153A DE2053153A DE2053153B2 DE 2053153 B2 DE2053153 B2 DE 2053153B2 DE 2053153 A DE2053153 A DE 2053153A DE 2053153 A DE2053153 A DE 2053153A DE 2053153 B2 DE2053153 B2 DE 2053153B2
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- cyclotnphosphazenamiden
- poly
- polymers
- pyridine
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229920000642 polymer Polymers 0.000 claims description 8
- 150000004984 aromatic diamines Chemical class 0.000 claims description 3
- YAIZWYHCIXKPTA-UHFFFAOYSA-N NC(N(P(N1)Cl)P=NP1Cl)=O Chemical class NC(N(P(N1)Cl)P=NP1Cl)=O YAIZWYHCIXKPTA-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000007731 hot pressing Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000010425 asbestos 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZHDTXTDHBRADLM-UHFFFAOYSA-N hydron;2,3,4,5-tetrahydropyridin-6-amine;chloride Chemical compound Cl.NC1=NCCCC1 ZHDTXTDHBRADLM-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000126 substance 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/025—Polyphosphazenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
R,N NR,R, N NR,
R2N N N NR, '5 R 2 NNN NR, ' 5
\l II/ *\ l II / *
P PP P
N NH-Ar—NH-N NH-Ar — NH-
(R = Alkylrest mit 1 bis 5 C-Atomen; Ar = zweiwertiger aromatischer Rest) polykondensiert.(R = alkyl radical with 1 to 5 carbon atoms; Ar = divalent aromatic residue) polycondensed.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Phosphazenamid 1,1,3,5-Tetrakis - (dimethylamido) - 3,5 - dichlorocyclotriphosphazen verwendet und die Umsetzung in siedendem Pyridin vornimmt.2. The method according to claim 1, characterized in that the phosphazenamide 1,1,3,5-tetrakis - (dimethylamido) - 3,5 - dichlorocyclotriphosphazene used and the reaction in boiling Pyridine makes.
3. Verwendung der nach Anspruch 1 oder 2 hergestellten Polycyclotriphosphazenamide zur Herstellung von Schaumkörpern.3. Use of the polycyclotriphosphazenamides prepared according to claim 1 or 2 for Manufacture of foam bodies.
Die Erfindung betrifft die Herstellung von PoIycyclotriphosphazenamiden mit besonderen Eigenschaften. Diese Polymeren sind nämlich bei Raumtemperatur lagerstabil und lassen sich durch Erhitzen ohne Zusatz weiterer Stoffe zu thermostabilen Produkten aufschäumen.The invention relates to the production of polycyclotriphosphazenamides with special properties. This is because these polymers are stable in storage at room temperature and can be removed by heating Foam to form thermally stable products without adding any other substances.
Es ist bereits ein Verfahren zur Herstellung von Phosphonitrilpolymeren bekannt, bei dem 2,4-Diamino-2,4,6,6-tetraphe:iyltriphosphonitril so lange auf Temperaturen von 250 bis 365° C erhitzt wird, bis die Ammoniakentwicklung beendet ist (deutsche Patentschrift 1 222 499). Die auf diese Weise gewonnenen, für Überzugsmassen vorgesehenen Polymeren sind jedoch ohne weiteres nicht schäumbar.A process for the production of phosphonitrile polymers is already known in which 2,4-diamino-2,4,6,6-tetraphe: iyltriphosphonitrile is heated to temperatures of 250 to 365 ° C until the evolution of ammonia has ended (German Patent 1,222,499). The polymers obtained in this way and intended for coating compounds however, are not readily foamable.
Zur Herstellung von Schaumstoffen mußte man bisher stets flüssige oder feste Kunststoffe mit Luft oder einem gasabspaltenden Treibmittel vermischen und durch Erwärmen oder durch Zusatz von weiteren Reagenzien in Schaumstoffe überführen. Auf diese Weise gebildete Schaumstoffe besitzen außerdem meist eine für viele Anwendungszwecke unzureichende thermische Stabilität.In the past, liquid or solid plastics had to be mixed with air to produce foams or a gas-releasing propellant and mix by heating or by adding more Transfer reagents into foams. Foams formed in this way also have usually insufficient thermal stability for many applications.
Erfindungsgemäß wurde nun ein Verfahren zur Herstellung von Polycyclotriphosphazenamiden gefunden, das dadurch gekennzeichnet ist, daß man Dichlorcyclotriphosphazenamidverbindungen (A) mit aromatischen Diaminen (B) in Lösung bei 50 bis 2003C zu Polymeren (C) mit der wiederkehrenden StrukturAccording to the invention, a process for the preparation of polycyclotriphosphazenamides has now been found, which is characterized in that dichlorocyclotriphosphazenamide compounds (A) with aromatic diamines (B) in solution at 50 to 200 3 C to form polymers (C) with the repeating structure
R,N NR,R, N NR,
R,N N N NR-,R, N N N NR-,
" \l II/
ρ ρ "\ l II /
ρ ρ
N NH-Ar-NH--N NH-Ar-NH--
(R = Alkylrest mit 1 bis 5 C-Atomen; Ar = zweiwertiger aromatischer Rest) polykondensiert.(R = alkyl radical with 1 to 5 carbon atoms; Ar = divalent aromatic residue) polycondensed.
Die Polykondensation verläuft dabei nach der folgenden Gleichung:The polycondensation proceeds according to the following equation:
R1NR 1 N
nR,N NnR, N N
NR,NO,
N NR2 + nH2N—Ar—NH,N NR 2 + nH 2 N — Ar — NH,
CLCL
N
(A)N
(A)
CLCL
(B)(B)
40 R,N 40 R, N
R2N N PR 2 NNP
(C)(C)
NR,NO,
N NR2 N NR 2
P
\P.
\
NH-Ar—NH-NH-Ar — NH-
+ 2nHCl+ 2nHCl
ss Eine vorteilhafte Ausfuhrungsart des erfindungsgemäßen Verfahrens besteht darin, daß man als Phosphazenamid 1,1,3,5 - Tetrakis - (dimethylamido)-3,5-dichlorocyclotriphosphazen verwendet und die Umsetzung in siedendem Pyridin vornimmt.ss An advantageous embodiment of the invention The process consists in that 1,1,3,5-tetrakis (dimethylamido) -3,5-dichlorocyclotriphosphazene is used as the phosphazenamide used and carries out the reaction in boiling pyridine.
Die erfindungsgemäß hergestellten Polymeren sind unter anderem zur Herstellung von thermostabilen Schaumkörpern geeignet.The polymers produced according to the invention are used, inter alia, for the production of thermally stable ones Foam bodies suitable.
Das erfindungsgemäße Verfahren führt zu einem chemisch und physikalisch vollkommen homogenen Feststoff, der durch Kalt- oder Heißpressen zu beliebig geformten Körpern weiterverarbeitet werden kann. Bei Raumtemperaturen sind die Polymeren völlig frei von Zersetzungserscheinungen und praktisch unbegrenzt haltbar.The method according to the invention leads to a chemically and physically completely homogeneous one Solid that can be processed into any shape by cold or hot pressing. At room temperature the polymers are completely free from decomposition and are practical Shelf life indefinitely.
Erst beim Erwärmen auf Temperaturen \on 150 bis 2000C oder höher wird durch die Abspaltung von Dimethylamin ein Schaumstoff gebildet. Hin Zusatzstoff ist dazu nicht erforderlich, weil vor dem Schäumen das Treibmittel in chemisch fester Bindung Bestandteil des Polymeren ist; die bereits erwähnte hohe Lagerstabilität und außerdem eine sehr homogene Verschäumung sind hierauf zurückzuführen. Die Schaumkörper selbst besitzen eine ausgezeichnete thermische Stabilität. Sie sind kurzzeitig bis 8000C, für längere Zeitspannen bis 600°C wärmebeständig.Only when heated to temperatures from 150 to 200 ° C. or higher is a foam formed as a result of the elimination of dimethylamine. No additive is required for this because, prior to foaming, the blowing agent is part of the polymer in a chemically solid bond; the already mentioned high storage stability and also a very homogeneous foaming are due to this. The foam bodies themselves have excellent thermal stability. They are short-term up to 800 0 C, for extended periods up to 600 ° C heat resistant.
Zur Durchführung des erfindungsgemäßen Verfahrens sind als aromatische Diamine z. B. die Phe-Bylendiamine, Benzidin, 4,4-Diaminodiphenyläther, 4,4'-Diaminodiphenylmethan u. ä. geeignet.To carry out the process according to the invention, aromatic diamines such. B. the Phe-Bylenediamines, Benzidine, 4,4-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane and the like are suitable.
Die Polykondensation erfolgt unter Atmosphärendruck in aprotonischen basischen Lösungsmitteln bei Temperaturen von 50 bis 2000C, vorzugsweise in liedendem Pyridin.The polycondensation is carried out under atmospheric pressure in basic aprotic solvents at temperatures of 50 to 200 0 C, preferably in liedendem pyridine.
Die Primärkondensate (C in Gleichung 1) lösen lieh in organischen Lösungsmitteln, wie z. B. Methanol, Chloroform, Pyridin, Dimethylformamid, Dimethylsulfoxyd u. ä. Sie können durch Kaltpressen bei Raumtemperatur oder durch Heißpressen bei 150 bis 200°C zu Formkörpern verarbeitet werden.The primary condensates (C in equation 1) dissolve borrowed in organic solvents, such as. B. methanol, Chloroform, pyridine, dimethylformamide, dimethyl sulfoxide u. Ä. You can by cold pressing at room temperature or by hot pressing at 150 to 200 ° C can be processed into moldings.
Beim Erhitzen der Primärkondensate auf Temperaturen über 2000C erfolgt durch Abspaltung von Dialkylamin eine Schaumbildung und gleichzeitig eine Vernetzung, wodurch thermostabile, unlösliche und unschmelzbare hart-spröde Schaumkörper erhalten werden.When the primary condensates are heated to temperatures above 200 ° C., the elimination of dialkylamine results in foam formation and, at the same time, crosslinking, as a result of which thermally stable, insoluble and infusible, hard-brittle foam bodies are obtained.
Die Primärkondensate können 7. B. als flammschützende überzüge oder als Hitzeschutzschilde in wiedereintretenden Raumfahrzeugen eingesetzt werden. Die geschäumten Polykondensate sind als thermostabile Isolationsmaterialien verwendbar.The primary condensates can be 7. B. as flame-retardant coatings or as heat shields in re-entering spacecraft. The foamed polycondensates are considered to be thermostable Isolation materials can be used.
Es ist weiterhin möglich, die erfindungsgemäßen Produkte durch den Zusatz von Füllstoffen wie Glasoder Asbestfasern zu modifizieren.It is also possible to use the products according to the invention by adding fillers such as glass or Modify asbestos fibers.
Das folgende Beispiel soll die Erfindung näherThe following example is intended to further illustrate the invention
erläutern (die reduzierte Viskosität wurde an 0,5%igenexplain (the reduced viscosity was at 0.5% igen
Lösungen in Methanol bei 300C gemessen; dieSolutions in methanol measured at 30 ° C .; the
thermogravimetrische Analyse (TGA) wurde mit einerthermogravimetric analysis (TGA) was performed with a
Aufheizgeschwindigkeit von 5°C/min ausgeführt).Heating rate of 5 ° C / min carried out).
76,6 g 1,1,3,5 - Tetrakis - (dimethy lamido) - 3,5 - dichlorocyclotriphosphazen wurden im Stickstoffstrom mit 42,0 g 4,4'-Diaminodiphenylmethan in 800 ml76.6 g 1,1,3,5 - tetrakis - (dimethylamido) - 3,5 - dichlorocyclotriphosphazene were in a stream of nitrogen with 42.0 g of 4,4'-diaminodiphenylmethane in 800 ml
Pyridin zum Sieden erhitzt Nach 6 Stunden wurde aus dem viskosen Reaktionsgemisch das Polykondensat mit Wasser ausgefällt, abgesaugt und mehrmals mit Wasser gründlich gewaschen. Nach dem Trocknen bei 105° C im Vakuum ergab sich eine Aus-Pyridine heated to the boil. After 6 hours, the viscous reaction mixture became the polycondensate precipitated with water, filtered off with suction and washed thoroughly several times with water. After this Drying at 105 ° C in vacuo resulted in an
beute von 93%; das Polymere hatte eine reduzierte Viskosität von 0,8 dl/g.prey of 93%; the polymer had a reduced viscosity of 0.8 dl / g.
Bei der TGA-Messung verlor das Polykondensat bis 500° C 25% an Gewicht, der Rückstand war bis 8000C nahezu thermostabil, danach erfolgte bis 9000C ein schneller quantitativer Abbau.In the TGA measurement, the polycondensate lost to 500 ° C 25% weight, the residue was 800 0 C almost thermostable, then carried up to 900 0 C a rapid quantitative degradation.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2053153A DE2053153B2 (en) | 1970-10-29 | 1970-10-29 | Process for the preparation of poly cyclotnphosphazenamiden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2053153A DE2053153B2 (en) | 1970-10-29 | 1970-10-29 | Process for the preparation of poly cyclotnphosphazenamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2053153A1 DE2053153A1 (en) | 1972-05-10 |
| DE2053153B2 true DE2053153B2 (en) | 1973-10-31 |
Family
ID=5786542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2053153A Pending DE2053153B2 (en) | 1970-10-29 | 1970-10-29 | Process for the preparation of poly cyclotnphosphazenamiden |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2053153B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4282901A4 (en) * | 2021-03-02 | 2024-12-25 | Nippon Shokubai Co., Ltd. | POLYMER CONTAINING A PHOSPHAZENE BOND |
-
1970
- 1970-10-29 DE DE2053153A patent/DE2053153B2/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2053153A1 (en) | 1972-05-10 |
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