DE451734C - Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde - Google Patents

Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde

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Publication number
DE451734C
DE451734C DEF58879D DEF0058879D DE451734C DE 451734 C DE451734 C DE 451734C DE F58879 D DEF58879 D DE F58879D DE F0058879 D DEF0058879 D DE F0058879D DE 451734 C DE451734 C DE 451734C
Authority
DE
Germany
Prior art keywords
crotonaldehyde
preparation
parts
aromatic amines
condensation 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
DEF58879D
Other languages
German (de)
Inventor
Dr Walter Kropp
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
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEF58879D priority Critical patent/DE451734C/en
Application granted granted Critical
Publication of DE451734C publication Critical patent/DE451734C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06Amines
    • C08G12/08Amines aromatic

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Description

Verfahren zur Darstellung von harzartigen Kondensationsprodukten aus aromatischen Aminen und Crotonaldehyd. In der Patentschrift 372 855, K1. 22h, ist ein Verfahren zur Darstellung von Kunstharzen beschrieben. Es besteht darin, daß man unter Zusatz von sauren Kondensationsmitteln aromatische Basen, wie Anilin, Toluidin, Xylidin oder a-Naphthylamin, mit verschiedenen Aldehyden, u. a. mit Crotonaldehyd, kondensiert.Process for the preparation of resinous condensation products aromatic amines and crotonaldehyde. In the patent 372 855, K1. 22h, is a method for the preparation of synthetic resins is described. It is that aromatic bases, such as aniline, are added with the addition of acidic condensing agents, Toluidine, xylidine or a-naphthylamine, with various aldehydes, i.a. with crotonaldehyde, condensed.

ES wurde nun die bemerkenswerte Beobachtung gemacht, daß man auch durch Kondensation von Crotonaldehyd mit aromatischen Aminen ohne Zusatz eines sauren Kondensationsmittels in außerordentlich glatter und einfacher Weise zu Produkten gelangen kann, die nach verschiedenen Richtungen hin technisch wertvoll sind. Die Weglassung des Kondensationsmittels bietet den Vorteil einer vereinfachten Arbeitsweise und Aufarbeitung, weil es sich auf diese Weise erübrigt, aus dem Reaktionsprodukt das saure Kondensationsmittel, das bei vielen Verwendungszwecken recht störend ist, aus der Reaktionsmasse zu entfernen. Die Kondensation kann in Anwesenheit oder Abwesenheit eines Lösungs- oder Verdünnungsmittels vorgenommen werden.The remarkable observation has now been made that one too by condensation of crotonaldehyde with aromatic amines without the addition of an acidic one Condensation agent into products in an extraordinarily smooth and simple manner that are technically valuable in different directions. the Omission of the condensing agent offers the advantage of a simplified mode of operation and work-up, because it is unnecessary in this way, from the reaction product the acidic condensation agent, which is quite annoying for many purposes, to remove from the reaction mass. The condensation can be in the presence or absence a solvent or diluent.

Beispiel i.Example i.

Zu 56 Gewichtsteilen Crotonaldehyd werden unter starkem Rühren langsam 6o Gewichtsteile Anilin zugegeben. Dabei soll die Temperatur nicht über 50° steigen. Nach dem Eintragen des Anilins wird noch 3 Stunden bei dieser Temperatur weitergerührt. Dann läßt man über Nacht stehen und erhitzt im Vakuum schließlich bis auf i25°, bis die leichtflüchtigen Stoffe entfernt sind. Es bleibt ein springhartes Harz zurück. Dieses ist in Wasser unlöslich, löslich dagegen in Äther, Benzol, Essigester, Solventnaphtha, Terpentinöl und Leinöl. Der Schmelzpunkt des Harzes liegt bei etwa. 83°. Doch läßt sich durch Erhitzen im Vakuum bei höherer Temperatur der Schmelzpunkt leicht auf iio° erhöhen. Beispiel 2.Add 56 parts by weight of crotonaldehyde slowly with vigorous stirring 60 parts by weight of aniline were added. The temperature should not rise above 50 °. After the aniline has been introduced, stirring is continued for 3 hours at this temperature. Then it is left to stand overnight and finally heated in a vacuum to 25 °, until the volatile substances are removed. A hard resin remains behind. This is insoluble in water, but soluble in ether, benzene, ethyl acetate, solvent naphtha, Turpentine oil and linseed oil. The melting point of the resin is around. 83 °. But lets The melting point increases slightly by heating in a vacuum at a higher temperature increase iio °. Example 2.

12o Gewichtsteile Anilin werden in 25o Raumteilen Alkohol gelöst. Zu dieser Lösung gibt man langsam eine Lösung von i io Gewichtsteilen Crotonaldehyd in 250 Raumteilen Alkohol, so daß die Temperatur allmählich auf 6o bis 70° steigt. Man kocht dann noch 2 bis 3 Stunden, verdunstet den Alkohol und erwärmt im Vakuum auf i35°. Der Rückstand ist springhart und läßt sich leicht pulvern. Den abdestillierten Alkohol kann man wieder zu einem neuen Ansatz verwenden.120 parts by weight of aniline are dissolved in 250 parts by volume of alcohol. A solution of 10 parts by weight of crotonaldehyde in 250 parts by volume of alcohol is slowly added to this solution, so that the temperature gradually rises to 60 ° to 70 °. The mixture is then boiled for a further 2 to 3 hours, the alcohol is evaporated and heated to 135 ° in a vacuum. The residue is hard as a spring and can easily be powdered. The alcohol that has been distilled off can be used again for a new approach.

Beispiel 3.Example 3.

65 Gewichtsteile Anilin werden in i 5o Raumteilen Benzol gelöst. Dazu gibt man unter Kühlen 7 5 Gewichtsteile Crotonaldehyd in iooRaumteile Benzol, so daß die Temperatur nicht über 3o bis 35° steigt. Dann läßt man 3o Stunden stehen und entfernt das Benzol und die leichtflüchtigen Bestandteile im Vakuum zum Schluß bei i2o bis i3o°.65 parts by weight of aniline are dissolved in 15 parts by volume of benzene. In addition 7 5 parts by weight of crotonaldehyde are added with cooling in ioo room parts Benzene, so that the temperature does not rise above 30 to 35 °. Then leave for 30 hours stand and remove the benzene and the volatile components in a vacuum End at i2o to i3o °.

An Stelle von Benzol kann man auch Aceton oder andere Lösungsmittel verwenden. Beispiel ¢.Instead of benzene, acetone or other solvents can also be used use. Example ¢.

Zu 36 Gewichtsteilen Crotonaldshyd werden langsam unter Rühren 69 Geavicht-teile o-Toluidin. zugegeben, so daß die Temperatur bei 4o bis 50° stehenbleibt. Nach mehrstündigem Rühren bei dieser Temperatur wird -im Vakuum bei i3o° erhitzt. Der Rückstand läßt sich pulvern. Er löst sich in Benzol, Solventnaphtha usw.69 parts by weight of crotonald's hydrate are slowly added with stirring Geavicht-parts o-toluidine. added so that the temperature remains at 40 to 50 °. After several hours of stirring at this temperature, it is heated in vacuo at 130 °. The residue can be powdered. It dissolves in benzene, solvent naphtha, etc.

Beispiel 5.Example 5.

In ioo Gewichtsteile Crotonaldehyd trägt man i 4o Gewichtsteile [3-Naphthylamin ein. Dieses löst sich in der Flüssigkeit. Es tritt Erwärmung ein und nach kurzer Zeit Trübung unter Wasserabscheidung. Es wird einige Stunden am Rückfluß auf dem Wasserbad erwärmt und schließlich im Vakuum bei 14o bis 145', Das zurückbleibende Harz löst sich leicht in Benzol, Aceton und Leinöl. Der Schmelzpunkt liegt bei etwa 70° nach vorherigem Erweichen. In analoger Weise kann man das Produkt aus a-Naphthylamin. .erhalten. Es ist gleichfalls ein rötlich gelbes Harz, von ähnlichen Lösungseigenschaften.I 40 parts by weight of [3-naphthylamine are carried in 100 parts by weight of crotonaldehyde a. This dissolves in the liquid. Warming occurs and after a short time Time turbidity with water separation. It will be refluxed on the for a few hours Heated water bath and finally in a vacuum at 14o to 145 ', the remaining Resin dissolves easily in benzene, acetone, and linseed oil. The melting point is around 70 ° after previous softening. The product can be obtained from α-naphthylamine in an analogous manner. .obtain. It is also a reddish yellow resin with similar dissolving properties.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von harzartigen Kondensationsprodukten aus aromatischen Aminen und Crotonaldehyd, dadurch gekennzeichnet, daß man Crotonaldehyd bei An- oder Abwesenheit eines Lösungs- oder Verdünnungsmittels auf primäre aromatische Amine einwirken läßt.PATENT CLAIM: Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde, characterized in that one crotonaldehyde in the presence or absence of a solvent or diluent to primary aromatic Allow amines to act.
DEF58879D 1925-05-15 1925-05-15 Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde Expired DE451734C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF58879D DE451734C (en) 1925-05-15 1925-05-15 Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF58879D DE451734C (en) 1925-05-15 1925-05-15 Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde

Publications (1)

Publication Number Publication Date
DE451734C true DE451734C (en) 1927-10-28

Family

ID=7108666

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF58879D Expired DE451734C (en) 1925-05-15 1925-05-15 Process for the preparation of resinous condensation products from aromatic amines and crotonaldehyde

Country Status (1)

Country Link
DE (1) DE451734C (en)

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