CH235034A - Process for the production of di (acrylic acid) hexamethylene diamide. - Google Patents
Process for the production of di (acrylic acid) hexamethylene diamide.Info
- Publication number
- CH235034A CH235034A CH235034DA CH235034A CH 235034 A CH235034 A CH 235034A CH 235034D A CH235034D A CH 235034DA CH 235034 A CH235034 A CH 235034A
- Authority
- CH
- Switzerland
- Prior art keywords
- acrylic acid
- production
- hexamethylene diamide
- diamide
- melting point
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
Verfahren zur Herstellung von Di-(aerylsäure)-hexamethylendiamid. Es wurde gefunden, dass man bisher unbekannte Acrylsäurediamide erhält, wenn man Verbindungen folgender Art Cl-CHE-CH@-CO-NH-(CH2)ri NH-CO-CH2-CH2-Cl in geeigneter Weise, zweckmässig in wässeri gem Medium, mit halogenwasserstoffabspal- tenden Mitteln in der Wärme behandelt.
In der Formel bedeutet n die Anzahl der Methy- lengruppen. Es können Polymethylendiamine verwandt werden, die zwei undmehr Methylen- gruppen enthalten. Ferner können diese Methy- lengruppen durch Sauerstoff- oder Schwefel atome unterbrochen sein.
Die als Ausgangsstoffe verwendeten Säure- amide sind durch Einwirkung von P-Chlor- propionsäurechlorid auf aliphatische Diamine leicht zu erhalten. Man kann nun aus diesen halogenhaltigen Säureamiden in einfacher Weise durch halogenwasserstoffabspaltende Mittel, wie z.
B. mit 20 /oiger Kalilauge, die monomeren Diacrylsäurediamide CHz=CH- C O-NH-(CHa) n-NH- CO-CH=CHE erhalten. Es ist aber auch ohne weiteres mög lich, sofort die polymeren Acrylsäureamide durch längeres Erhitzen mit halogenwasser- stoffabspaltenden Mitteln herzustellen.
Die monomeren Produkte lassen sich umkristalli- sieren und zeigen dann einen scharfen Schmelz punkt. Aus ihnen lassen sich die polymeren Produkte leicht, z. B. durch Erhitzen über den Schmelzpunkt, gewinnen. Man kann die isolierten Monomeren auch gemeinsam mit andern Vinylverbindungen in neue hochmolekulare Mischpolymerisate über- führen.
Die polymeren Produkte zeigen keinen Schmelzpunkt und sind unlöslich in organi schen Lösungsmitteln.
Gegenstand der Erfindung ist ein Ver fahren zur Herstellung von Diacry1säure- hexamethylendiamid, welches dadurch gekenn zeichnet ist, dass man Di-(@-chlorpropionyl)- hexamethylendiamid mit halogenwasserstoff- abspaltenden 11itteln in der Wärme behandelt. Das neue Produkt schmilzt bei 138-140 C; es soll zur Herstellung von Kunststoffen ver wendet werden.
Beispiel: 107 Gewichtsteile Di - (3 - chlorpropionyl)- hexamethylendiamid vom Schmelzpunkt<B>1520,</B> dargestellt aus Hexamethylendiamin und @3- Chlorpropionylchlorid in Benzol, werden mit 2140 Gewichtsteilen 20 0%iger wässeriger Kali lauge unter Rühren gerade bis zum Siede punkt der Kalilauge erhitzt. Es scheidet sich auf der Oberfläche ein 01 ab, das beim Er kalten erstarrt. Nach Abheben der festen Schicht wild diese gepulvert und mit Wasser neutral gewaschen.
Nach dem Trocknen wird aus Trichlorbenzol umkristallisiert. Es bleibt eine kleine Menge des schon polymerisierten Produktes zurück, während die Hauptmenge als Monomeres in Nadeln auskristallisiert. Das Di-(acrylsäure)-hexamethylendiamid hat einen Schmelzpunkt von 138-140 . Es geht beim Erhitzen über den Schmelzpunkt in das glasklare Polymerisationsprodukt über.
Process for the preparation of di (aerylic acid) hexamethylene diamide. It has been found that hitherto unknown acrylic acid diamides are obtained if compounds of the following type Cl-CHE-CH @ -CO-NH- (CH2) ri NH-CO-CH2-CH2-Cl are suitably used, advantageously in an aqueous medium, treated in the heat with agents that split off hydrogen halide.
In the formula, n denotes the number of methyl groups. Polymethylenediamines containing two or more methylene groups can be used. Furthermore, these methylene groups can be interrupted by oxygen or sulfur atoms.
The acid amides used as starting materials can easily be obtained by the action of P-chloropropionic acid chloride on aliphatic diamines. You can now from these halogen-containing acid amides in a simple manner by means of hydrogen halide releasing agents, such as.
B. with 20% potassium hydroxide solution to obtain the monomeric diacrylic acid diamide CHz = CH-C O-NH- (CHa) n-NH-CO-CH = CHE. However, it is also possible without further ado to immediately prepare the polymeric acrylic acid amides by prolonged heating with agents which split off hydrogen halide.
The monomeric products can be recrystallized and then show a sharp melting point. From them, the polymeric products can be easily, for. B. by heating above the melting point win. The isolated monomers can also be converted into new, high molecular weight copolymers together with other vinyl compounds.
The polymeric products show no melting point and are insoluble in organic solvents.
The invention relates to a process for the production of diacry1 acid hexamethylenediamide, which is characterized in that di - (@ - chloropropionyl) - hexamethylenediamide is treated with heat using agents which split off hydrogen halide. The new product melts at 138-140 C; it is to be used for the production of plastics.
Example: 107 parts by weight of di (3 - chloropropionyl) hexamethylenediamide with a melting point of 1520, prepared from hexamethylenediamine and 3-chloropropionyl chloride in benzene, are mixed with 2140 parts by weight of 20% aqueous potassium hydroxide solution with stirring heated to the boiling point of the potassium hydroxide solution. An 01 is deposited on the surface, which solidifies when it is cold. After lifting off the solid layer, powder it and wash it neutral with water.
After drying, it is recrystallized from trichlorobenzene. A small amount of the already polymerized product remains, while the main amount crystallizes out as a monomer in needles. The di (acrylic acid) hexamethylene diamide has a melting point of 138-140. When heated above the melting point, it changes into the crystal-clear polymerisation product.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH235034T | 1942-04-10 | ||
| CH237918T | 1942-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235034A true CH235034A (en) | 1944-11-15 |
Family
ID=25727964
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235034D CH235034A (en) | 1942-04-10 | 1942-04-10 | Process for the production of di (acrylic acid) hexamethylene diamide. |
| CH237918D CH237918A (en) | 1942-04-10 | 1942-04-10 | Process for the production of di (acrylic acid) ethylenediamide. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237918D CH237918A (en) | 1942-04-10 | 1942-04-10 | Process for the production of di (acrylic acid) ethylenediamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH235034A (en) |
-
1942
- 1942-04-10 CH CH235034D patent/CH235034A/en unknown
- 1942-04-10 CH CH237918D patent/CH237918A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH237918A (en) | 1945-05-31 |
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