DE914253C - Process for the preparation of furylacrylic acid amides substituted on nitrogen - Google Patents

Process for the preparation of furylacrylic acid amides substituted on nitrogen

Info

Publication number
DE914253C
DE914253C DEP6329A DEP0006329A DE914253C DE 914253 C DE914253 C DE 914253C DE P6329 A DEP6329 A DE P6329A DE P0006329 A DEP0006329 A DE P0006329A DE 914253 C DE914253 C DE 914253C
Authority
DE
Germany
Prior art keywords
nitrogen
furylacrylic acid
acid amides
preparation
furylacrylic
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
DEP6329A
Other languages
German (de)
Inventor
Dr Wilhelm Irion
Dr Heinrich Otto Marwitz
Dr Otto Moldenhauer
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.)
Phrix Werke AG
Original Assignee
Phrix Werke 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 Phrix Werke AG filed Critical Phrix Werke AG
Priority to DEP6329A priority Critical patent/DE914253C/en
Application granted granted Critical
Publication of DE914253C publication Critical patent/DE914253C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Description

Verfahren zur Herstellung von am Stickstoff substituierten Furylacrylsäureamiden Es wurde gefunden, daß Furylacrylsäureamide durch Umsetzung mit niederen Aldehyden am Stickstoff zu neuen Verbiindungen oxalkyl'.iert werden, welche beim Erhitzen auf Temperaturen von 120 bis 200°, vorzugsweise 15o bis 17o°, Polymerisate ergeben, die zur Herstellung von Lacken, überzügen, Filmen, Fäden usw. geeignet sind.Process for the preparation of nitrogen-substituted furylacrylic acid amides It has been found that furylacrylic acid amides by reaction with lower aldehydes are oxalkylated on nitrogen to form new compounds, which on heating at temperatures of 120 to 200 °, preferably 15o to 17o °, result in polymers, which are suitable for the production of lacquers, coatings, films, threads, etc.

Die in Frage kommenden Furylacrylsäureami,de müssen wenigstens 1 Wasserstoffatom am Stickstoffatom enthalten. Zur Anlagerung sind- insbesondere Formaldehyd und Acetaldehyd sowie diese abspaltende Stoffe, z. B. Paraformaldehyd und Paraldehyd, geeignet. Die Umsetzung erfolgt zweckmäßig in schwach alkalischer, wäßriger Lösung bei mäßig erhöhter Temperatur, z. B. 40 bis 6o°, und bei normalem Druck; jedoch ist es auch möglich, z. B. bei Verwendung von Formaldehyd, anstatt diesen gasförmig bei Normaldruck in die Lösung des Säurearriides einzuleiten, die Reaktion im geschlossenen Gefäß und bei höheren Drucken vorzunehmen. Beispiel 55 g Furylacrylsäureamid und 16 g Paraformaldehyd werden in 200 g Wasser, dem 1 g Kaliumcarbonat zugesetzt wurde, unter Umschwenken in der Hitze gelöst und 2 Stunden auf 50°' gehalten. Der ausgeschiedene Kristallbrei, welcher 70 g beträgt, wird aus Wasser umkristallisiert und besteht aus Oxymethylfurylacrylsäureamid vom Schmelzpunkt 114 bis 11 T°;: The furylacrylic acid amides in question must contain at least 1 hydrogen atom on the nitrogen atom. In particular, formaldehyde and acetaldehyde as well as substances which split off these, e.g. B. paraformaldehyde and paraldehyde, are suitable. The reaction is expediently carried out in a weakly alkaline, aqueous solution at a moderately elevated temperature, e.g. B. 40 to 60 °, and at normal pressure; however, it is also possible, e.g. B. when using formaldehyde, instead of introducing it in gaseous form at normal pressure into the solution of the acid arrid, carry out the reaction in a closed vessel and at higher pressures. EXAMPLE 55 g of furylacrylic acid amide and 16 g of paraformaldehyde are dissolved in 200 g of water to which 1 g of potassium carbonate has been added while swirling in the heat and kept at 50 ° for 2 hours. The precipitated crystal mass, which is 70 g is recrystallized from water and consists of Oxymethylfurylacrylsäureamid of melting point 114 to 1 1 T ° ;:

Claims (3)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung von am Stickstoff substituierten Furylacrylsäureamiden, dadurch gekennzeichnet, daß ein Furylacrylsäureamid, welches wenigstens i Wasserstoffatom am Stickstoffatom enthält, mit einem niederen Aldehyd oder einer Aldehyd: abspaltenden Substanz umgesetzt wird. PATENT CLAIMS: i. Process for the production of nitrogen-substituted Furylacrylic acid amides, characterized in that a furylacrylic acid amide which contains at least i hydrogen atom on the nitrogen atom, with a lower aldehyde or an aldehyde: is converted into a substance that splits off. 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß die Umsetzung in schwach alkalischer, wäßriger Lösung durchgeführt wird. 2. The method according to claim i, characterized in that the reaction takes place in a weakly alkaline, aqueous solution is carried out. 3. Verfahren nach Anspruch i und 2, dadurch gekennzeichnet, daß Furylacrylsäureamid mit Paraformaldehyd bei erhöhter Temperatur umgesetzt wird. Angezogene Druckschriften: Schweizerische Patentschrift Nr. 255 i02.3. The method according to claim i and 2, characterized in that furylacrylic acid amide is reacted with paraformaldehyde at elevated temperature. Printed publications: Swiss patent specification No. 255 i02.
DEP6329A 1951-10-14 1951-10-14 Process for the preparation of furylacrylic acid amides substituted on nitrogen Expired DE914253C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP6329A DE914253C (en) 1951-10-14 1951-10-14 Process for the preparation of furylacrylic acid amides substituted on nitrogen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP6329A DE914253C (en) 1951-10-14 1951-10-14 Process for the preparation of furylacrylic acid amides substituted on nitrogen

Publications (1)

Publication Number Publication Date
DE914253C true DE914253C (en) 1954-06-28

Family

ID=7360564

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP6329A Expired DE914253C (en) 1951-10-14 1951-10-14 Process for the preparation of furylacrylic acid amides substituted on nitrogen

Country Status (1)

Country Link
DE (1) DE914253C (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH255102A (en) * 1946-11-18 1948-06-15 Ciba Geigy A process for the preparation of a new durable synthetic resin emulsion and a durable emulsion obtained by the process.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH255102A (en) * 1946-11-18 1948-06-15 Ciba Geigy A process for the preparation of a new durable synthetic resin emulsion and a durable emulsion obtained by the process.

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