DE697081C - Process for the production of condensation products - Google Patents

Process for the production of condensation products

Info

Publication number
DE697081C
DE697081C DE1937I0058666 DEI0058666D DE697081C DE 697081 C DE697081 C DE 697081C DE 1937I0058666 DE1937I0058666 DE 1937I0058666 DE I0058666 D DEI0058666 D DE I0058666D DE 697081 C DE697081 C DE 697081C
Authority
DE
Germany
Prior art keywords
condensation products
production
nitrobenzene
methylsulfoxide
yellow
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
DE1937I0058666
Other languages
German (de)
Inventor
Dr Heinrich Ritter
Dr Werner Zerweck
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 DE1937I0058666 priority Critical patent/DE697081C/en
Application granted granted Critical
Publication of DE697081C publication Critical patent/DE697081C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00—Nitro or nitroso dyes

Landscapes

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

Description

Verfahren zur Herstellung von Kondensationsprodukten Es wurde gefunden, daß man durch Kondensation von 1-Halogen-2-nitrobenzol-4-alkylsulfoxyden mit aromatischen Aminen, dito keine freien Sulfonsäuregruppen enthalten, Kondensationsprodukte der Diphenylaminremhe erhält, die eich zum Färben von Lacken und Acetatkunstseitde eignen. Wird Acetatkunstseide nach einer der üblichen Methoiden mit den oben genannten Kondensationsprodukten gefärbt, so erhält man lebhaft gelbe bis orangegelbe Farbtöne von. sehr guten Echtheitseigenschaften, insbesondere von hervorragender Lichtechtheit. Beispiel 5 kg 1-Chlor-2-nitrobenzol-4-methylsulfoxyd vom Schmelzpunikt 95° und 5 kg p-Toluidin werden etwa 1/2 Stunde auf 15o bis 16o° erwärmt. Hieraüf wird mit 25 1 Alkohol verdünnt und heiß filtriert, worauf beim Erlaten das Reaktionsprodukt, das 4'-Methyl-2-nitrodiphenylamin-4-methylsulfoxyd, sich in gelben Kristallen vom Schmelzpunkt !43 bis 144° (nach nochmaligem Umkristallisleren aus Methylalkohol) abscheidet.Process for the production of condensation products It has been found that by condensation of 1-halo-2-nitrobenzene-4-alkylsulfoxides with aromatic Amines, ditto contain no free sulfonic acid groups, condensation products of the Diphenylamine cream is obtained, which is suitable for coloring lacquers and acetate art pages. If acetate rayon is made using one of the usual methods with the condensation products mentioned above colored, vivid yellow to orange-yellow shades of. very good fastness properties, especially of excellent lightfastness. Example 5 kg of 1-chloro-2-nitrobenzene-4-methylsulfoxide from the melting point 95 ° and 5 kg p-toluidine are about 1/2 hour to 15o to 16o ° warmed up. This is diluted with 25 liters of alcohol and filtered hot, whereupon the Obtained the reaction product, the 4'-methyl-2-nitrodiphenylamine-4-methylsulfoxide, yellow crystals with a melting point of 43 to 144 ° (after repeated recrystallization from methyl alcohol) separates.

Der Körper färbt Acetatside in gelben Tönen vom hervorragender Lichtechtheit. Bei Verwendutug von Anilin wird das 2-Nitrodiphenylamin-4-methylsulfoxyd vom Schmelzpunkt 131 bis 132° erhalten, das Aoetatseide in grürnstichiggelben Tönen von gleichfalls hervorragender Lichtechtheit färbt.The body colors Acetatside in yellow tones of excellent lightfastness. When aniline is used, 2-nitrodiphenylamine-4-methylsulfoxide has its melting point 131 to 132 ° preserved, the acetate silk in greenish yellow tones of the same colors with excellent lightfastness.

An Stelle von I - Chlor - 2 - nitrobenzol-4-methylsulfoxyd lassen sich mit gleichem Erfolg auch dessen Homologen, Wie 1-Chlor-2-nitrobenzol-4-äthyl- bzw. -4-propylsulfoxyd, verwenden.. Das I-Chlor-2-nitrobenzol-4-methylsulfoxyd und seine Homologen können durch gelinde Oxydation der entsprechenden p-Chlorbenzolthioäther mit der herechneten Menge Wasserstoffsuperoxyd und nachfolgende Nitrierung der so erhaltenen p-Chlorbenzolalkysysulfoxyde in konzentrierter Schwefelsäure mit der berechneten Menge Mischsäure bei 2o bis 3o° erhalten werden.In place of I - chlorine - leave 2 - nitrobenzene-4-methylsulfoxide its homologues, such as 1-chloro-2-nitrobenzene-4-ethyl- or -4-propyl sulfoxide, use .. I-chloro-2-nitrobenzene-4-methylsulfoxide and its homologues can be obtained by mild oxidation of the corresponding p-chlorobenzene thioether with the calculated amount of hydrogen peroxide and subsequent nitration of the so obtained p-Chlorbenzolalkysysulfoxde in concentrated sulfuric acid with the calculated amount of mixed acid can be obtained at 2o to 3o °.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Kondensationsprodukten der Diphenylaminreihe, dadurch gekennzeichnet, daß man I-Halogen-2-nitrobenzol-4-älkylsulfoxyde mit aromatischen Aminen, die keine freien Sulfonsäuregruppen enthalten, gegehenenfalls in Lösungsmitteln erhitzt.;PATENT CLAIM: Process for the production of condensation products of the diphenylamine series, characterized in that I-halo-2-nitrobenzene-4-alkylsulfoxides with aromatic amines that contain no free sulfonic acid groups, if necessary heated in solvents .;
DE1937I0058666 1937-07-28 1937-07-28 Process for the production of condensation products Expired DE697081C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1937I0058666 DE697081C (en) 1937-07-28 1937-07-28 Process for the production of condensation products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1937I0058666 DE697081C (en) 1937-07-28 1937-07-28 Process for the production of condensation products

Publications (1)

Publication Number Publication Date
DE697081C true DE697081C (en) 1940-10-05

Family

ID=7194830

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1937I0058666 Expired DE697081C (en) 1937-07-28 1937-07-28 Process for the production of condensation products

Country Status (1)

Country Link
DE (1) DE697081C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061008B (en) * 1954-02-22 1959-07-09 Sandoz Ag Process for the production of water-insoluble particles of 1-amino-2-nitrobenzene-4-sulfonic acid amide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061008B (en) * 1954-02-22 1959-07-09 Sandoz Ag Process for the production of water-insoluble particles of 1-amino-2-nitrobenzene-4-sulfonic acid amide

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