CH317129A - Process for the production of polycondensates - Google Patents
Process for the production of polycondensatesInfo
- Publication number
- CH317129A CH317129A CH317129DA CH317129A CH 317129 A CH317129 A CH 317129A CH 317129D A CH317129D A CH 317129DA CH 317129 A CH317129 A CH 317129A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- compounds
- production
- polycondensates
- nitrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- -1 diamine compounds Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012265 solid product 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
verfahren zur Herstellung von Polykondensaten Die Erfindung betrifft ein Verfahren zur Herstellung von Polykondensaten, das dadurch gekennzeichnet ist, @diass man Verbindungen der Formel
EMI0001.0007
in der R Wasserstoff oder einen Kohlenwas- serstoffrest (z.
B. eine Alkyl- oder Aryl- gruppe), Ha.l Halogen und n eine ganze Zahl grösser als 0 bedeutet, mit, flüssigem Ammo niak umsetzt und die gewonnenen Amine im Stickstoffstrom bei erhöhter, nicht, über 250 C liegender Temperatur zur Kondensation bringt.
Die erfindungsgemäss hergestellten Poly kondensate kann man für plastische Massen verwenden. Die Zwischenprodukte sind ent- weder Mono- oder Diaminverbindungen. Ihr Entstehen ist von den jeweils herrschenden Reaktionsbedingungen abhängig.
Lässt man z. B. auf Xethylen-bis-ss-chlor- propionsäureamid bei Raumtemperatur im Autoklaven bis zu 20 Stunden flüssiges Ammoniak einwirken, wobei sieh ein dieser Temperatur entsprechender Druck von etwa 8-10 Atm. einstiellt, so erhält man eine ent- sprechende Monoaminverb.indung folgender Formel:
Cl - (C112)2' CO - NH - C112 # NH - CO * (C112)2 * N112 Diese Verbindung hat einen Schmelzpunkt von 240 C.
Wird dieses Monoamin inv Vakuum bei 0,5 mm Hg und bei einer Temperatur von 115 C im Stickstoffstrom behandelt., so erhält man unter quantitativer HCl-Abspaltung im Destilliergefäss ein hell gefärbtes Polykonden- sationsprodukt, das man für plastische Massen verwenden kann.
Verwendet man als Ausgangsprodukt Me- thylen-bis-ss-chlorpropionsäureamid und setzt dieses im Autoklaven bei einem Druck bis etwa 20 Atm. und. bei einer Temperatur von, etwa 60 C mit flüssigem Ammoniak innerhalb etwa 20 Stunden um, so bildet sich ein ent- sprechendes Diamin gemäss folgender Glei chung:
EMI0001.0087
<B>Cl</B> <SEP> - <SEP> (C112)2 <SEP> - <SEP> <B>CO</B> <SEP> - <SEP> NH <SEP> - <SEP> C112 <SEP> - <SEP> <B>NH</B> <SEP> - <SEP> <B>CO</B> <SEP> - <SEP> (C112)2 <SEP> - <SEP> Cl <SEP> -I- <SEP> 2 <SEP> N113
<tb> N112 <SEP> - <SEP> (C112)2 <SEP> - <SEP> CO <SEP> - <SEP> NH <SEP> - <SEP> C112 <SEP> # <SEP> NH <SEP> - <SEP> CO <SEP> - <SEP> <B>(C112)2'</B> <SEP> N112 <SEP> -I- <SEP> 2 <SEP> HCl Das so gebildete Diamin weist einen Schmelz- punkt von 1$0 C auf und ergibt, durch Er- Kitzen im hohen Vakuiun (0,1-0,5 mm Hg) auf 170 C,
und zwar im Stickstoffstrom un- ter Abspaltung von N113 ein linear gebautes Polykondensat. Es eignet sich zur Herstellung von plastischen Massen.
<I>Beispiel 1</I> 200 g Methylen-bis-ss-chlorpropionsäure- amid werden mit 1000 cm3 flüssigem Ammo niak im Autoklaven bei gewöhnlicher Tempe- ratur behandelt. Die Reaktionsdauer beträgt bis zu 20 Stunden.
Es bildet sich eine homo gene Lösung, die nach dem Verdunsten des überschüssigen Ammoniaks eine halbfeste Masse hint:erlässt. Nach Aufarbeitung und Rei nigung erhält man die entsprechende Mono aminverbindung folgender Struktur: Cl-(C112)2-CO -NH-CHz-NH-CO'(C112)2'N112 Dieses Monoamin hat einen Schmelzpunkt von 240 C.
Diese Verbindung wird unter Stickstoff- einleitung bei normalem Druck durch Erhit zen auf 240 C aufgeschmolzen und. dann im Vakuum (2 mm Hg) unter Einleitung von Stickstoff zwei Stunden lang auf 180-190 C gehalten. Es spaltet sich im Laufe der Kon densation Chlorwasserstoff ab.
Das nach der beendeten Reaktion im Destilliergefäss zurück bleibende hell gefärbte Kondensationsprodukt eignet sich für die Herstellung von plastischen Massen. Beispiel <I>2</I> 100 g Äthyliden-bis-ss-chlorpropionsäure- amid werden mit 1000 cm3 flüssigen Anuno- niaks bis zu 20 Stunden bei Raumtemperatur im
Autoklaven (bei 8-10 Atm.) behandelt. Es bildet sich eine homogene Flüssigkeit, wel- ehe nach dem Verdampfen des überschüssigen Ammoniaks eine halbfeste Masse hinterlässt. Hieraus lässt sich ein bei 18.5-190 C schmel zendes festes Produkt isolieren.
Es ist das Monoamin folgender Formel:
EMI0002.0066
20 g dieser gewonnenen Verbindung werden unter Stickstoffeinleitung bei normalem Druck durch Erhitzen auf 190 C aufgeschmolzen, sodann unter vermindertem Druck (0.5 mm Hg) unter Stickstoffeinleitung bei 120-130 C weiter kondensiert. Nach einer Reaktionszeit von 3-5 Stunden bleibt im Destillationsgefäss ein hellgefärbtes Polykondensationsprodukt zurück,
das gleichfalls für plastische Massen verwendet werden kann.
Process for the production of polycondensates The invention relates to a process for the production of polycondensates, which is characterized in that compounds of the formula are used
EMI0001.0007
in which R is hydrogen or a hydrocarbon residue (e.g.
B. an alkyl or aryl group), Hal is halogen and n is an integer greater than 0, reacts with liquid ammonia and condenses the amines obtained in a nitrogen stream at an elevated temperature not above 250 C. .
The poly condensates produced according to the invention can be used for plastic masses. The intermediates are either mono- or diamine compounds. Their formation depends on the respective prevailing reaction conditions.
If you let z. B. act on xethylene-bis-ss-chloropropionic acid amide at room temperature in the autoclave for up to 20 hours of liquid ammonia, with a pressure of about 8-10 atm. Corresponding to this temperature. one obtains a corresponding monoamine compound with the following formula:
Cl - (C112) 2 'CO - NH - C112 # NH - CO * (C112) 2 * N112 This compound has a melting point of 240 C.
If this monoamine is treated in a vacuum at 0.5 mm Hg and at a temperature of 115 ° C. in a stream of nitrogen, a light-colored polycondensation product is obtained with quantitative elimination of HCl in the distillation vessel, which can be used for plastic masses.
If you use methylene-bis-ss-chloropropionic acid amide as the starting product and place this in the autoclave at a pressure of up to about 20 atm. and. at a temperature of about 60 C with liquid ammonia within about 20 hours, a corresponding diamine is formed according to the following equation:
EMI0001.0087
<B> Cl </B> <SEP> - <SEP> (C112) 2 <SEP> - <SEP> <B> CO </B> <SEP> - <SEP> NH <SEP> - <SEP> C112 <SEP> - <SEP> <B> NH </B> <SEP> - <SEP> <B> CO </B> <SEP> - <SEP> (C112) 2 <SEP> - <SEP> Cl < SEP> -I- <SEP> 2 <SEP> N113
<tb> N112 <SEP> - <SEP> (C112) 2 <SEP> - <SEP> CO <SEP> - <SEP> NH <SEP> - <SEP> C112 <SEP> # <SEP> NH <SEP> - <SEP> CO <SEP> - <SEP> <B> (C112) 2 '</B> <SEP> N112 <SEP> -I- <SEP> 2 <SEP> HCl The diamine thus formed has a melting point of 1 $ 0 C and results, by heating in a high vacuum (0.1-0.5 mm Hg) to 170 C,
namely a linear polycondensate in a stream of nitrogen with elimination of N113. It is suitable for the production of plastic masses.
<I> Example 1 </I> 200 g of methylene-bis-ss-chloropropionic acid amide are treated with 1000 cm3 of liquid ammonia in an autoclave at normal temperature. The reaction time is up to 20 hours.
A homogeneous solution is formed which, after the excess ammonia has evaporated, leaves a semi-solid mass. After working up and purification, the corresponding monoamine compound of the following structure is obtained: Cl- (C112) 2-CO -NH-CHz-NH-CO '(C112) 2'N112 This monoamine has a melting point of 240 C.
This compound is melted and heated to 240 ° C. under nitrogen at normal pressure. then held at 180-190 ° C. for two hours in vacuo (2 mm Hg) while introducing nitrogen. Hydrogen chloride is split off in the course of the condensation.
The light-colored condensation product that remains in the distillation vessel after the reaction has ended is suitable for the production of plastic masses. Example <I> 2 </I> 100 g of ethylidene-bis-s-chloropropionic acid amide are mixed with 1000 cm3 of liquid ammonia for up to 20 hours at room temperature
Autoclave (at 8-10 atm.) Treated. A homogeneous liquid forms which, after the evaporation of the excess ammonia, leaves a semi-solid mass. A solid product that melts at 18.5-190 ° C can be isolated from this.
It is the monoamine of the following formula:
EMI0002.0066
20 g of this compound obtained are melted by heating to 190 ° C. under nitrogen at normal pressure, then further condensed under reduced pressure (0.5 mm Hg) at 120-130 ° C. under nitrogen. After a reaction time of 3-5 hours, a light-colored polycondensation product remains in the distillation vessel.
which can also be used for plastic masses.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE317129X | 1951-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH317129A true CH317129A (en) | 1956-11-15 |
Family
ID=29421272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH317129D CH317129A (en) | 1951-07-26 | 1952-07-24 | Process for the production of polycondensates |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH317129A (en) |
-
1952
- 1952-07-24 CH CH317129D patent/CH317129A/en unknown
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