DE678908C - Process for the production of insoluble products containing nitrogen and sulfur - Google Patents

Process for the production of insoluble products containing nitrogen and sulfur

Info

Publication number
DE678908C
DE678908C DEI57565D DEI0057565D DE678908C DE 678908 C DE678908 C DE 678908C DE I57565 D DEI57565 D DE I57565D DE I0057565 D DEI0057565 D DE I0057565D DE 678908 C DE678908 C DE 678908C
Authority
DE
Germany
Prior art keywords
sulfur
production
containing nitrogen
products containing
insoluble products
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
DEI57565D
Other languages
German (de)
Inventor
Dr Joseph Duesing
Dr Paul Esselmann
Dipl-Ing Karl Koesslinger
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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
Priority to DEI56786D priority Critical patent/DE676197C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI57565D priority patent/DE678908C/en
Priority to DE1937I0062013 priority patent/DE688337C/en
Priority to DE1937I0062012 priority patent/DE692695C/en
Priority to DE1937I0062014 priority patent/DE688380C/en
Priority to DE1937I0057587 priority patent/DE688379C/en
Priority to GB14300/37A priority patent/GB496052A/en
Priority to FR49310D priority patent/FR49310E/en
Priority to FR835387D priority patent/FR835387A/en
Priority to NL86951A priority patent/NL49778C/en
Priority to NL86950A priority patent/NL49679C/en
Priority to NL86984A priority patent/NL48276C/en
Priority to NL92542A priority patent/NL48331C/xx
Application granted granted Critical
Publication of DE678908C publication Critical patent/DE678908C/en
Expired legal-status Critical Current

Links

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
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)

Description

Verfahren zur Herstellung von Stickstoff- und schwefelhaltigen unlöslichen Erzeugnissen Es wurde gefunden, daß die Kondensation zwischen Schwefelkohlenstoff und Äthylenimin, dessen Polymeren öder deren Homologen in anderer als der aus dem Hauptpatent ersichtlichen Richtung verläuft, wenn sie in Gegenwart von Natronlauge oder Kalilauge durchgeführt wird.Process for the production of nitrogen and sulfur-containing insolubles Products It has been found that the condensation between carbon disulfide and ethyleneimine, whose polymers or their homologues in other than that of the Main patent direction is evident when in the presence of caustic soda or potassium hydroxide is carried out.

Man gelangt bei sonst gleichem Ansatz zu Kondensationsprodukten, die erheblich höheren Schmelzpunkt haben, vorzugsweise bei geringemZusatz von polymeremÄthylenimin. Sie liefern kochbeständigere Fasern, wenn sie zum Animalisieren von Wollersatzfasern verwendet werden. Auch bei Durchführung der Kondensation im alkalischen Medium kann Schwefel mitverwendet werden. Die hierbei erzielten Harzprodukte weisen wieder entsprechend veränderte Eigenschaften auf; sie sind thermoplastisch und können zur Formung von Kunstharzgegenständen oder zur Lackherstellung verwendet werden. Beispiel i. In eine Lösung von 2 1 5oprozentigem Äthylenimin und i 19prozentiger Natronlauge läßt man unter Rühren 1,8 kg Schwefelkohlenstoff eintropfen. Man läßt das Gemisch über Nacht stehen und erhitzt es dann ¢ Stünden läng unter Rückfluß nochmals mit 500 ccm Schwefelkohlenstoff auf dem Wasserbad. Das gelbe Endprodukt wird wiederholt mit heißem Wasser ausgekocht. Das gereinigte Harz hat nach .dem Trocknen einen Schmelzpunkt von' 136'. Das mit sauren Farbstoffen angefärbte Produkt zeichnet sich durch besonders gute Waschechtheit aus.Otherwise the same approach leads to condensation products which have a considerably higher melting point, preferably with a small addition of polymeric ethyleneimine. They provide more boil-resistant fibers when used to animalize wool substitute fibers. Sulfur can also be used when the condensation is carried out in an alkaline medium. The resin products obtained in this way again have correspondingly changed properties; they are thermoplastic and can be used to mold synthetic resin articles or to make paint. Example i. 1.8 kg of carbon disulfide are added dropwise with stirring into a solution of 2 1 5% ethyleneimine and 19% sodium hydroxide solution. The mixture is left to stand overnight and is then refluxed again for hours with 500 cc of carbon disulfide on a water bath. The yellow end product is repeatedly boiled with hot water. The cleaned resin has a melting point of '136' after drying. The product dyed with acidic dyes is distinguished by its particularly good washfastness.

2. Ein Gemisch von 11/21 5oprozentigem monomerem Äthylenimin und 650 ccm 3öprozentigem Kohlensäure-Äthyleniminpolymerisat überläßt man 24 Stunden der Weiterpolymerisation. Zu der sirupartigen Lösung wird 11 ioprozentige Kalilauge und anschließend tropfenweise eine Lösung von 396:g Schwefel in 1,8 kg Schwefelkohlenstoff zugesetzt. Nach '4tägigem Stehen wird abgedampft und nach der Reinigung das Endprodukt vorsichtig umgeschmolzen. Das gelbe Harz mit einem Stickstoffgehalt von 11,501o ist gegenüber verdünnten Säuren und Alkalien besonders beständig. Anstatt von dem Gemisch aus Äthyleniminbase und Polymerisat kann man auch von reinem Kohlensäurepolymerisat ausgehen; man erhält dann Harze mit j e nach dem Polymerisationsgrad verschiedenen Schmelzpunkten. 3. Zu einem Gemisch von i 2o g einer 50prozentigen i,2-Propyleniminlösüng und 500 ccm 9prozentiger Natronlauge läßt man langsam unter Rückfluß und Kühlung ioo .g Schwefelkohlenstoff zutropfen. Die sich abscheidende feste Mässe wird von .der Flüssigkeit getrennt und mit verdünnter Schwefelsäure wiederholt gekocht. Das gelbe Harz wird beim Umschmelzen braun. Es ist in verdünnten Säuren und Laugen unlöslich und mit sauren Wollfarbstoffen gut anfärbbar.2. A mixture of 11/21 5% monomeric ethyleneimine and 650 ccm of 3o% carbonic acid-ethyleneimine polymer is left to polymerize further for 24 hours. To the syrupy solution, 11% potassium hydroxide solution and then a solution of 396: g sulfur in 1.8 kg carbon disulfide are added dropwise. After standing for 4 days, it is evaporated and, after cleaning, the end product is carefully remelted. The yellow resin with a nitrogen content of 11.501o is particularly resistant to dilute acids and alkalis. Instead of the mixture of ethyleneimine base and polymer, it is also possible to start from pure carbonic acid polymer; resins are then obtained with different melting points depending on the degree of polymerization. 3. To a mixture of 12o g of a 50% i, 2-propylenimine solution and 500 cc of 9% sodium hydroxide solution, 100 g of carbon disulfide are slowly added dropwise under reflux and cooling. The solid mass that separates is separated from the liquid and repeatedly boiled with dilute sulfuric acid. The yellow resin turns brown when remelted. It is insoluble in dilute acids and alkalis and can be easily dyed with acidic wool dyes.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung von stickstöff-- und schwefelhaltigen unlöslichen Erzeugnissen, da-durch gekennzeichnet, daß in weiterer Ausbildung des Verfahrens des Hauptpatents 676197 die Einwirkung von Schwefelkohlenstoff auf cyclisches Äthylenimin, die Polymeren desselben oder deren Homologen in Gegenwart von Natron- oder Kalilauge durchgeführt wird: . PATENT CLAIMS: i. Process for the production of nitrogenous and sulfur-containing insoluble products, characterized in that, in a further development of the process of main patent 676197, the action of carbon disulfide on cyclic ethyleneimine, the polymers of the same or their homologues is carried out in the presence of sodium or potassium hydroxide solution: . 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß zur Herstellung der Erzeugnisse noch Schwefel mitverwendet wird.2. The method according to claim i, characterized characterized in that sulfur is also used to manufacture the products.
DEI57565D 1937-01-05 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur Expired DE678908C (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DEI56786D DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DEI57565D DE678908C (en) 1937-03-27 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur
DE1937I0062012 DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062014 DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062013 DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
GB14300/37A GB496052A (en) 1937-01-05 1937-05-22 Manufacture of products containing nitrogen and sulphur
FR49310D FR49310E (en) 1937-01-05 1938-03-17 Process for the production of insoluble reaction products containing nitrogen and sulfur
FR835387D FR835387A (en) 1937-01-05 1938-03-17 Process for the production of insoluble reaction products containing nitrogen and sulfur
NL86951A NL49778C (en) 1937-03-27 1938-03-18 Process for preparing nitrogen and sulfur-containing insoluble resinous products.
NL86950A NL49679C (en) 1937-03-27 1938-03-18 Process for the preparation of nitrogen and sulfur-containing insoluble, resinous reaction products.
NL86984A NL48276C (en) 1937-01-05 1938-03-19 Process for preparing nitrogen and sulfur-containing resins
NL92542A NL48331C (en) 1937-01-05 1939-03-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI57565D DE678908C (en) 1937-03-27 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur

Publications (1)

Publication Number Publication Date
DE678908C true DE678908C (en) 1939-07-24

Family

ID=41647866

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI57565D Expired DE678908C (en) 1937-01-05 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur

Country Status (2)

Country Link
DE (1) DE678908C (en)
NL (2) NL49778C (en)

Also Published As

Publication number Publication date
NL49679C (en) 1940-12-16
NL49778C (en) 1941-01-15

Similar Documents

Publication Publication Date Title
DE678908C (en) Process for the production of insoluble products containing nitrogen and sulfur
DE857960C (en) Process for the preparation of cyclohexenyl-cyclohexanone by condensation of cyclohexanone
DE678907C (en) Process for the production of insoluble products containing nitrogen and sulfur
DE688380C (en) Process for the production of nitrogen- and sulfur-containing resins
DE686988C (en) e soluble condensation products from phenols
DE805568C (en) Process for the production of polythioureas
AT158197B (en) Process for the production of nitrogen and sulfur containing products.
DE1770052A1 (en) Process for the production of sulfonic acids from styrene-phenolic resins
DE2530042B2 (en) Process for the preparation of linear polyethyleneimine
CH235190A (en) Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
DE616429C (en) Process for the production of condensation products
DE813210C (en) Process for the manufacture of a thermosetting resinous product
DE960181C (en) Process for the production of positively selective membranes by condensation of compounds containing tertiary sulfonium groups
AT220821B (en) Process for the production of plastics by reacting polyvalent aldehydes with diamines
AT141687B (en) Process for converting refining waste from mineral oil processing into varnish, resin and varnish-like products.
DE715605C (en) Process for the production of nitrogenous products
CH180872A (en) Process for the preparation of a hardenable condensation product.
DE529320C (en) Process for the preparation of condensation products from amines and aldehydes
DE560604C (en) Process for the production of paints from phenol-formaldehyde condensation products
DE1168882B (en) Process for absorbing formaldehyde from gases containing formaldehyde
DE966124C (en) Process for the production of resinous condensation products from melamine
DE1720606A1 (en) Process for the production of high molecular weight polyamides
DE954918C (en) Process for the production of sulfur-containing polycondensation products
DE737543C (en) Plasticizers
AT136993B (en) Process for the production of resinous condensation products.