DE2942645A1 - Inorganic acid N-alkylamide dimer(s) and oligomer(s) - prepd. by heating with organic peroxide are useful as antistatic and flame retarding finishes for plastics and fibres - Google Patents
Inorganic acid N-alkylamide dimer(s) and oligomer(s) - prepd. by heating with organic peroxide are useful as antistatic and flame retarding finishes for plastics and fibresInfo
- Publication number
- DE2942645A1 DE2942645A1 DE19792942645 DE2942645A DE2942645A1 DE 2942645 A1 DE2942645 A1 DE 2942645A1 DE 19792942645 DE19792942645 DE 19792942645 DE 2942645 A DE2942645 A DE 2942645A DE 2942645 A1 DE2942645 A1 DE 2942645A1
- Authority
- DE
- Germany
- Prior art keywords
- plastics
- antistatic
- organic peroxide
- dimer
- fibres
- 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- Withdrawn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
- 150000007522 mineralic acids Chemical class 0.000 title claims abstract description 8
- 239000004033 plastic Substances 0.000 title claims abstract description 5
- 229920003023 plastic Polymers 0.000 title claims abstract description 5
- 150000001451 organic peroxides Chemical class 0.000 title abstract description 4
- 238000010438 heat treatment Methods 0.000 title abstract 2
- 230000000979 retarding effect Effects 0.000 title abstract 2
- 239000000539 dimer Substances 0.000 title description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 238000006384 oligomerization reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 alkyl radical Chemical class 0.000 claims description 6
- 239000002216 antistatic agent Substances 0.000 claims description 4
- 239000003063 flame retardant Substances 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000011261 inert gas Substances 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 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
- DUNFIZRDIMDMIH-UHFFFAOYSA-N ethyl hydrogen diethylamidophosphate Chemical compound CCO[P@](O)(=O)N(CC)CC DUNFIZRDIMDMIH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000000214 vapour pressure osmometry Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Fireproofing Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Di- und/oder Oligomerisierung von N-Alkylamiden anorga-Di- and / or oligomerization of N-alkylamides inorga-
nischer Säuren und Verwendung der entstandenen Produkte als Flammschutzmittel und/oder Antistatika Die Erfindung betrifft ein Verfahren zur Di- und/oder Oligomerisierung von N-Alkylamiden anorganischer Säuren und die Verwendung der erhaltenen Produkte als Flammschutzmittel und/oder Antistatika.acids and use of the resulting products as flame retardants and / or antistatic agents The invention relates to a method for di- and / or oligomerization of N-alkylamides of inorganic acids and the use of the products obtained as flame retardants and / or antistatic agents.
Es ist bereits bekannt, durch oxidative Kupplung, z.B.It is already known to use oxidative coupling, e.g.
von Isopropylgruppen enthaltenden aromatischen Verbindungen mit Hilfe von Sauerstoff oder Peroxiden Di- bzw. Oligomere herzustellen. Derartige Reaktionen sind in den Publikationen von V.V. Korshak et al in Polymer Science USSR 1 (1962), 925 bis 935 beschrieben. Ahnliche Systeme, aber immer auf Basis von aromatischen Isopropylderivaten, sind in den DE-AS 12 44 395, DE-AS 12 55 302, DE-OS 25 25 697 und DE-OS 20 50 009 erwähnt. Von L. Friedman und H. Shechter wird im Zusammenhang der onylamidmodifizierung von Olefinen die Reaktion von N,N'-Dimethyl- und N-Methylacetamid mit Di-tert.-butylperoxid erwähnt (vgl. Tetrahedron Letters 1961, 238 bis 242).of aromatic compounds containing isopropyl groups with the help of to produce di- or oligomers of oxygen or peroxides. Such reactions are in the publications of V.V. Korshak et al in Polymer Science USSR 1 (1962), 925 to 935. Similar systems, but always based on aromatic Isopropyl derivatives are in DE-AS 12 44 395, DE-AS 12 55 302, DE-OS 25 25 697 and DE-OS 20 50 009 mentioned. By L. Friedman and H. Shechter is related the onylamide modification of olefins, the reaction of N, N'-dimethyl and N-methylacetamide mentioned with di-tert-butyl peroxide (cf. Tetrahedron Letters 1961, 238 to 242).
Aufgabe der vorliegenden Patentanmeldung war es, ein Verfahren zur Herstellung von di- und/oder oligomeren Produkten von N-Alkylamiden anorganischer Säuren aufzufinden.The object of the present patent application was to provide a method for Production of di- and / or oligomeric products of inorganic N-alkylamides To find acids.
Eine weitere Aufgabe bestand darin, Flammschutzmittel und Antistatika auf der Basis von obigen N-Alkylamiden anorganischer Säuren aufzuzeigen, die für Kunststoffe geeignet sind und nicht ausschwitzen.Another task was to provide flame retardants and antistatic agents to show on the basis of the above N-alkylamides of inorganic acids, which for Plastics are suitable and do not sweat out.
Diese Aufgaben wurden erfindungsgemäß durch ein Verfahren gelöst, bei dem N-Alkylamide anorganischer Säuren der allgemeinen Formeln (I) oder (II) worin sein können R : N(R1R2), Aryl, Alkylaryl- oder Alkylrest R1 = H, CH3 oder 0 2H5 R2 = roh3, O2H5 und X = SO, SO2 oder SeO, mit organischen Peroxiden bei Temperaturen von 130 bis 2000C in Schutzgasatomosphäre umsetzt.These objects were achieved according to the invention by a process in which N-alkylamides of inorganic acids of the general formulas (I) or (II) in which R: N (R1R2), aryl, alkylaryl or alkyl radical R1 = H, CH3 or 0 2H5 R2 = raw3, O2H5 and X = SO, SO2 or SeO, reacted with organic peroxides at temperatures from 130 to 2000C in a protective gas atmosphere .
Unter Di- und/oder Oligomerisierung obiger N-Alkylamide wird eine Reaktion verstanden, bei der zwei oder mehrere, maximal zehn Moleküle der gleichen Verbindung zusammengelagert werden. Diese Reaktion ist an sich bekannt und braucht hier nicht weiter erläutert zu werden.With di- and / or oligomerization of the above N-alkylamides is a Understood reaction in which two or more, a maximum of ten molecules of the same Compound are stored together. This reaction is known per se and needs not to be further explained here.
Auch die gemäß Erfindung einzusetzenden Verbindungen der allgemeinen Formeln (I) oder (II) sind an sich bekannt.Also the compounds of the general to be used according to the invention Formulas (I) or (II) are known per se.
Als erfindungsgemäße N-Alkylamide anorganischer Säuren kommen insbesondere
die Verbindungen (III) bis X in Frage:
Tris(N-dimethyl)phosphorsäureamid
p-Toluolsulfonsäure -N-methy lamid
Tris (N-Tripropyl )phosphorsäureamid
N(Trisäthyl)phosphorsäureamid
Zur Durchführung der Dimerisierungs- bzw. Oligomerisierungsreaktion werden die N-Alkylamide
der allgemeinen Formeln (I) oder (II) mit einem organischen Peroxid, vorzugsweise
mit Di-tert.-butylperoxid, im molaren Verhältnis 1 : 1, bei Temperaturen zwischen
130 und 200, vorzugsweise 150 und 1800C, erhitzt. Als Schutzatmosphäre dient ein
Inertgas, vorzugsweise Stickstoff. Die erfindungsgemäusen Produkte werden durch
fraktionierte Destillation bzw. Umkristallisation gereinigt. Die erhaltenen Di-und/oder
Oligomerisierungsprodukte der Verbindungen III und IV weisen die folgenden Strukturformeln
auf:
Die neuen Verbindungen sind für den Flammschutz sowie zur antistatischen Ausrüstung von Kunststoffen und Fasern geeignet. Sie sind außerdem als Lösungsmittel und C-C-labile synergistische Verbindungen verwendbar.The new compounds are for flame retardancy as well as for antistatic Suitable for finishing plastics and fibers. They are also used as solvents and C-C labile synergistic compounds can be used.
In den nachfolgenden Beispielen 1 und 2 wird die Versuchsdurchführung erläutert. Die in den Beispielen genannten Teile und Prozente beziehen sich jeweils auf das Gewicht.In the following examples 1 and 2, the experiment is carried out explained. The parts and percentages given in the examples relate in each case on weight.
Beispiel 1 Dimerisierung von Verbindung III 10 Teile (III) und 2 Teile Di-tert.-butylperoxid werden im Autoklaven unter Stickstoff 8 Stunden auf 16500 erhitzt.Example 1 Dimerization of Compound III 10 parts (III) and 2 parts Di-tert-butyl peroxide are heated to 16,500 for 8 hours in an autoclave under nitrogen heated.
Nach dem Abkühlen werden tert.-Butanol, sowie nicht umge-0 setztes Peroxid im Vakuum bei 50°C/10 Torr abgezogen. Nicht umgesetztes (III) werden bei 155°C/1 Torr abgezogen. Es verbleibt ein Rückstand von 6,3 Teilen Dimeres Kp 180 - 195°C/ 0,2 Torr (Molgewicht 380, dampfdruckosmometrisch bestimmt) Beispiel 2 18,5 Teile Verbindung IV und 2,5 Teile Di-tert.-butylperoxid werden im Autoklaven unter Stickstoff 14 Stunden auf 1600C erhitzt. Nach dem beziehen von nicht umgesetztem Peroxid und tert.-Butanol werden nach dem Umkristallisieren aus Eisessig 10,3 Teile eines Dimeren mit dem Molgewicht 405 (dampfdruckosmometrisch bestimmt) erhalten. Das theoretische Molgewicht für das Dimere beträgt 372.After cooling, tert-butanol and unreacted are added Peroxide stripped off in vacuo at 50 ° C / 10 Torr. Not implemented (III) will be in 155 ° C / 1 torr subtracted. A residue of 6.3 parts of dimer, boiling point 180, remains - 195 ° C / 0.2 Torr (molecular weight 380, determined by vapor pressure osmometry) Example 2 18.5 Parts of compound IV and 2.5 parts of di-tert-butyl peroxide are placed in the autoclave Nitrogen heated to 160.degree. C. for 14 hours. After obtaining something that has not been converted Peroxide and tert-butanol are after recrystallization the end Glacial acetic acid 10.3 parts of a dimer with a molecular weight of 405 (vapor pressure osmometric certain) received. The theoretical molecular weight for the dimer is 372.
S gef. 8,5 %, S theoret. 8,7 % Das Dimere hat einen Schmelzbereich von 118 - 125°C, das Ausgangsmonomere schmilzt bei 76 - 790C. ~S found. 8.5%, S theor. 8.7% The dimer has a melting range from 118 - 125 ° C, the starting monomer melts at 76 - 790 ° C. ~
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792942645 DE2942645A1 (en) | 1979-10-22 | 1979-10-22 | Inorganic acid N-alkylamide dimer(s) and oligomer(s) - prepd. by heating with organic peroxide are useful as antistatic and flame retarding finishes for plastics and fibres |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792942645 DE2942645A1 (en) | 1979-10-22 | 1979-10-22 | Inorganic acid N-alkylamide dimer(s) and oligomer(s) - prepd. by heating with organic peroxide are useful as antistatic and flame retarding finishes for plastics and fibres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2942645A1 true DE2942645A1 (en) | 1981-04-30 |
Family
ID=6084080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792942645 Withdrawn DE2942645A1 (en) | 1979-10-22 | 1979-10-22 | Inorganic acid N-alkylamide dimer(s) and oligomer(s) - prepd. by heating with organic peroxide are useful as antistatic and flame retarding finishes for plastics and fibres |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2942645A1 (en) |
-
1979
- 1979-10-22 DE DE19792942645 patent/DE2942645A1/en not_active Withdrawn
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |