DE673589C - Process for the production of quaternary ammonium compounds - Google Patents

Process for the production of quaternary ammonium compounds

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Publication number
DE673589C
DE673589C DEF82684D DEF0082684D DE673589C DE 673589 C DE673589 C DE 673589C DE F82684 D DEF82684 D DE F82684D DE F0082684 D DEF0082684 D DE F0082684D DE 673589 C DE673589 C DE 673589C
Authority
DE
Germany
Prior art keywords
parts
quaternary ammonium
ammonium compounds
production
hexamethylenetetramine
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.)
Expired
Application number
DEF82684D
Other languages
German (de)
Inventor
Edgar Wolf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Farberei Ges Flores & Co Vorma
Original Assignee
Farberei Ges Flores & Co Vorma
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Farberei Ges Flores & Co Vorma filed Critical Farberei Ges Flores & Co Vorma
Priority to DEF82684D priority Critical patent/DE673589C/en
Application granted granted Critical
Publication of DE673589C publication Critical patent/DE673589C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/18—Bridged systems

Description

Verfahren zur Herstellung quartärer Ammoniumverbindungen Es wurde gefunden, daß durch Umsetzung von höheren Fettsäurechloriden oder Chlorkohlensäureestern mit Hexamethylentetramin und anschließender Behandlung der Umsetzungsprodukte mit tertiären Basen wasserlösliche quartäre Ammoniumverbindungen erhalten werden.Process for the preparation of quaternary ammonium compounds It has been found that by reacting higher fatty acid chlorides or chlorocarbonic acid esters with hexamethylenetetramine and subsequent treatment of the reaction products with tertiary bases water-soluble quaternary ammonium compounds are obtained.

DieUmsetzung der Säurechloride mit Hexamethylentetramin wird in dem Molverhältnis 3 bis q. Teile Säurechlorid auf 1 Teil Hexamethylentetramin vorgenommen.The reaction of the acid chlorides with hexamethylenetetramine is carried out in the Molar ratio 3 to q. Parts of acid chloride to 1 part of hexamethylenetetramine.

Die Erzeugnisse sollen zur Imprägnierung von Textilien verwendet werden. Sie haben die Eigenschaft, dem behandelten Textilgut wasserabweisende Eigenschaften zu verleihen, wobei der wasserabweisende Effekt beständig gegen Benzin- und Seifenwäsche ist. Weiterhin wird die Waschechtheit substantiver Färbungen des behandeltenTextilgutes verbessert und bei aus Cellulose hergestellten Kunstseiden eine Steigerung der Naß- und Trockenfestigkeit erzielt.The products are intended to be used for the impregnation of textiles. They have the property that the treated textile material has water-repellent properties to give, with the water-repellent effect resistant to petrol and soap washing is. Furthermore, the washing fastness of substantive dyeings of the treated textile goods is increased improved and in the case of rayon made from cellulose an increase in the wet and dry strength achieved.

Beispiele 1. 1q.oTeile fein pulverisiertes Hexamethylentetramin werden in 1q.oo Teile Chloroform eingetragen, mit i2o8 Teilen Stearinsäurechlorid versetzt und 1 Stunde lang am Rückflußkühler erhitzt. Das Chloroform wird alsdann abgesaugt und das Umsetzungsgut mit 32o Teilen Pyridin verrührt.Examples 1. 1q.o parts of finely powdered hexamethylenetetramine are registered in 1q.oo parts of chloroform, mixed with 12o8 parts of stearic acid chloride and refluxed for 1 hour. The chloroform is then filtered off with suction and stirred the reaction mixture with 320 parts of pyridine.

Unter Wärmeentwicklung tritt Bildung der quartären Pyridiniumverbindung ein. Die erhaltene weiße, wachsartige Masse ist nunmehr in heißem Wasser löslich, Schmelzpunkt etwa I15° unter Zersetzung (Formaldehydabspaltung). 2. 14oTeile fein pulverisiertes Hexamethylentetramin werden in 140o Teilen Benzol eingetragen, sodann 1768 Teile Montansäurechlorid hinzugefügt und das Ganze i Stunde lang am Rückflußkühler erhitzt. Das Benzol wird sodann abgesaugt und das Umsetzungs= gut mit 32o Teilen Py ridin verrührt. Die erhaltene wachsartige Verbindung zeigt einen Schmelzpunkt von 95°.The quaternary pyridinium compound is formed with the development of heat a. The white, waxy mass obtained is now soluble in hot water, Melting point about 15 ° with decomposition (elimination of formaldehyde). 2. 14o parts of finely powdered hexamethylenetetramine are added to 140o parts of benzene, then 1768 parts of montanic acid chloride were added and the whole thing lasted for one hour on Heated reflux condenser. The benzene is then sucked off and the conversion = good stirred with 32o parts of pyridine. The waxy compound obtained shows one Melting point of 95 °.

3. i4oTeile fein pulverisiertes Hexamethylentetramin werden mit 12o8 Teilen Stearinsäurechlorid verrührt und unter ständigem Rühren i Stunde lang auf etwa iio° erhitzt. Sodann wird mit 32o Teilen Pyridin verrührt.3. 14o parts of finely powdered hexamethylenetetramine are mixed with 12o8 Parts of stearic acid chloride are stirred up and stirred for 1 hour heated to about 10 °. It is then stirred with 320 parts of pyridine.

4. 1350 g des gemäß Beispiel i erhaltenen Umsetzungsproduktes aus Stearinsäurechlorid und Hexarnethylentetramin werden mit 372 g 2-Methylpyridin verrührt. Unter Wärmeentwicklung entsteht die quartäre Ammoniumverbindung des J--I\Iethylpyridins.4. 1350 g of the reaction product obtained according to Example i Stearic acid chloride and hexamethylene tetramine are stirred with 372 g of 2-methylpyridine. The quaternary ammonium compound of methylpyridine is formed with the development of heat.

5. 1350 g des gemäß Beispiels i erhaltenen Umsetzungsproduktes aus Stearinsäurechlorid und Hexamethylentetraminwerden mit 4o4 g Triäthylamin verrührt. Unter Wärmeentwicklung entsteht die quartäre Ammoniumverbindung des Triäthylamins. 6. 14o Teile fein pulverisiertes Hexamethylentetramin werden in 140o Teilen Chloroform gelöst und 134o Teile Chlorkohlensäureoctadecylesterhinzugefügt, i Stunde amRückflußkühler erhitzt, das Lösungsmittel abgesaugt und der Rückstand mit 32o Teilen Pyridin verrührt.5. 1350 g of the reaction product obtained according to Example i Stearic acid chloride and hexamethylenetetramine are stirred with 404 g of triethylamine. The quaternary ammonium compound of triethylamine is formed with the development of heat. 6. 14o parts of finely powdered hexamethylenetetramine are added to 140o parts of chloroform and 1340 parts of octadecyl chlorocarbonate were added, 1 hour on the reflux condenser heated, the solvent is filtered off with suction and the residue is stirred with 320 parts of pyridine.

7. 14o Teile Hexamethylentetramin «-erden in 140o Teilen Chloroform gelöst, mit 88o Teilen Undecylsäurechlori dversetzt und das Ganze i Stunde lang am Rückflußkühler erhitzt. Das Chloroform wird alsdann abgesaugt und das Umsetzungsprodukt mit 32o Teilen Pyridin verrührt.7. 140 parts of hexamethylenetetramine "earths" in 140 ° parts of chloroform dissolved, 880 parts of undecylic acid chloride were added, and the whole thing lasted for one hour heated on the reflux condenser. The chloroform is then suctioned off and the reaction product stirred with 32o parts of pyridine.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung quartärer Ammoniumverbindungen, dadurch gekennzeichnet, daß Säurechloride oder Chlorkohlensäureester, die einen aliphatischen Rest von wenigstens io C-Atomen enthalten, mitHexamethylentetramin im Molverhältnis 3 : i bis 4 : i kondensiert und die entstandenen Produkte mit tertiären Basen, wie Pyridin, zu quartären Ammoniumverbindungen umgesetzt werden. PATENT CLAIM: Process for the production of quaternary ammonium compounds, characterized in that acid chlorides or chlorocarbonic acid esters, which contain an aliphatic radical of at least 10 carbon atoms, are condensed with hexamethylenetetramine in a molar ratio of 3: i to 4: i and the products formed with tertiary bases such as pyridine, are converted to quaternary ammonium compounds.
DEF82684D 1937-03-16 1937-03-16 Process for the production of quaternary ammonium compounds Expired DE673589C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF82684D DE673589C (en) 1937-03-16 1937-03-16 Process for the production of quaternary ammonium compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF82684D DE673589C (en) 1937-03-16 1937-03-16 Process for the production of quaternary ammonium compounds

Publications (1)

Publication Number Publication Date
DE673589C true DE673589C (en) 1939-03-24

Family

ID=7113945

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF82684D Expired DE673589C (en) 1937-03-16 1937-03-16 Process for the production of quaternary ammonium compounds

Country Status (1)

Country Link
DE (1) DE673589C (en)

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