DE869104C - Process for the production of wool dyes - Google Patents

Process for the production of wool dyes

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Publication number
DE869104C
DE869104C DEE1794A DEE0001794A DE869104C DE 869104 C DE869104 C DE 869104C DE E1794 A DEE1794 A DE E1794A DE E0001794 A DEE0001794 A DE E0001794A DE 869104 C DE869104 C DE 869104C
Authority
DE
Germany
Prior art keywords
dyes
production
wool
wool dyes
weight
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
DEE1794A
Other languages
German (de)
Inventor
Emil Dr Beniers
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.)
Hoechst AG
Original Assignee
Hoechst 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 Hoechst AG filed Critical Hoechst AG
Priority to DEE1794A priority Critical patent/DE869104C/en
Application granted granted Critical
Publication of DE869104C publication Critical patent/DE869104C/en
Expired legal-status Critical Current

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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
    • C09B17/00—Azine dyes
    • C09B17/02—Azine dyes of the benzene series

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

Verfahren zur Herstellung von Wollfarbstoffen In der Patentschrift 545 859 ist ein Verfahren zur Herstellung von braunen Wollfarbstoffen beschrieben, -welches darin besteht, daß man i Mol einer 2, 6-Diamino,diphenylaminsulfonsäure mit i Mol eines 2, 4, 6-Trinitrobenzol,derivates umsetzt, das in i-Stellung ein austauschfähiges Atom oder eine austauschfähige Gruppe enthält, und anschließend durch Erhitzen in alkalischem Medium einenAzinringschlußherbeiführt. Es entstehendabei Farbstoffe von guten Lichtechtheiten. Die Wasser- -, Walk- und Waschechtheiten der erhaltenen Farbstoffe genügen indes nicht allen Anforderungen. - Es wurde nun gefunden, #daß man braune Wollfarbstoffe von sehr guten Echtheitseigenschaften herstellen kann, wenn man an Stelle von z.B. :2,4,6-Trinitrochlorl)en,zol solche Derivate des 3, 5-3', #'-Tetranitrobenzophenons, die in 4, 4'-Stellung austauschfählge Atome oder Gruppen enthalten, für die Kondensationsreaktion verwendet. Diese Komponenten vermögen zweimal mit der 2, 6-Diaminodiphenyl,aminsulfonsäure, zu reagieren, und es entstehen Farbstoffe mit zwei Azinringen beispielsweise nach dem folgenden Reaktionsschenia: In den obigen Formeln kann der Benzolkern Z noch Substituenten enthalten, wie z. B. Halogen, Alkyl-, Alkoxy- oder# Sulfonsäuregruppen.Process for the production of wool dyestuffs In the patent 545 859 a process for the production of brown wool dyestuffs is described, -which consists in that one mole of a 2,6-diamino, diphenylaminesulfonic acid with 1 mole of a 2,4,6-trinitrobenzene derivative which contains an exchangeable atom or group in the i-position, and then brings about an azine ring closure by heating in an alkaline medium. This results in dyes of good lightfastness. The water, boiling and washing fastness properties of the dyes obtained do not, however, meet all requirements. - It has now been found that # brown wool dyes can produce very good fastness properties when instead of, for example: 2,4,6-Trinitrochlorl) s, zol such derivatives of 3, 5-3 ', #' - Tetranitrobenzophenons which contain exchangeable atoms or groups in the 4, 4'-position, are used for the condensation reaction. These components are able to react twice with 2,6-diaminodiphenyl, aminesulfonic acid, and dyes with two azine rings are formed, for example according to the following reaction: In the above formulas, the benzene nucleus Z can also contain substituents, such as. B. halogen, alkyl, alkoxy or sulfonic acid groups.

Das als Komponente beispielsweise verwendete 4, 4'-Dichlor-3, 5-3, 5'-tetranitrobenzophenon kann durch Nitrieren von 4, 4'-Dichlorbenzophenon erhalten werden. The 4,4'-dichloro-3, 5-3, 5'-tetranitrobenzophenone used as a component, for example, can be obtained by nitrating 4,4'-dichlorobenzophenone.

Die neuen braunen Farbstoffe zeichnen sich vor den Farbstoffen Ader Patentschrift 545 859 -neben hervorragenden Naßechtheiten auch noch durch eine bessere Lichtechtheit aus.The new brown dyes are distinguished from the Ader patent 545 859 dyes - in addition to excellent wet fastness properties, they also have better light fastness.

B e i s p i e. 1 e 1 - 43 Gewichtsteile 4, 4'-Dichlor- 3, 5-3, 5'#tetranitro,benzophenon werden bei Gegenwart von Alkohol mit 56 Gewichtsteilen 2, 6-Diaininodiphenylämin-4-sulfons,äure und 66G-ewichtsteilen Natriumtacetat mehrere Stuivden gekocht. Wenn die Kondensation beendet ist, wird abgesaugt, das Zwischenprodukt in Wasser gelöst und nach Zugabe von 13 Ge#wichtsteilen Soda bei -go` ' der Azinringschluß durchgeführt. Der gebildete Farbstoff wird isoliert u-nd umgelöst. Er färbt Wolle in braunen Tönen von hervorragenden Licht- und Naßechtheiten.B ice p i e. 1 e 1 to 43 parts by weight of 4, 4'-dichloro-3, 5-3, 5 '# tetranitro are benzophenone in the presence of alcohol with 56 parts by weight of 2, 6-Diaininodiphenylämin-4-sulfonic, äure and 66G-ewichtsteilen several Natriumtacetat Stuivden cooked. When the condensation is over, it is suctioned off, the intermediate product is dissolved in water and, after adding 13 parts by weight of soda, the azine ring closure is carried out at -go`` ''. The dye formed is isolated and redissolved. It dyes wool in brown shades with excellent light and wet fastness properties.

2. Man kondensiert 40 Gewichtsteile 4, 4'-Dichlor-.3, 5-3, 5"-tetranitrobenzophenon mit 55 Gewichtsteilen 2, 6-Diamiiic#--,41-methyldiphenylamin-4-sulfonsäure bei Gegenwart von Natriumacetat in iol/oiger Butanollösung durch mehrstündiges Erhitzen auf 7o. bis 8o0. Nach Zugabe von 14 Gewichtsteilen Soda wird weiter bei iioo" gerührt, bis ,der Azinringschluß durchgeführt ist. Der- Farbstoff wird wie i ' n Beispiel i iseliert. Er färbt Wolle in braunen Tönen von sehr guten Naßechtheiten und sehr-guter Lichtechtheit.2. 40 parts by weight of 4,4'-dichloro-.3, 5-3, 5 "-tetranitrobenzophenone are condensed with 55 parts by weight of 2,6-diamiiic #, 41-methyldiphenylamine-4-sulfonic acid in the presence of sodium acetate in iol / The above butanol solution by heating for several hours to 70 to 80 degrees. After adding 14 parts by weight of soda, the mixture is stirred further at 100 "until the azine ring has closed. DER dye is as i 'n Example iseliert i. It dyes wool in brown shades with very good wet fastness properties and very good light fastness.

3. Durch Kondensation von äquimolel-,ulart#n Mengen 4, d-Dichlor-3, 5-3, 5'-tetr-anitrobenzophenon und 2, 6-Diamino-2'-chlordiphenylainin-4-sulfonsäure unter ähnlichen Bedingungen in Wasser oder Alkoholen erhält man einen in seinen Echtheitseigenschaften ähnlichen braunen Farbstoff. Ein ebenso echtes Produkt wird durch Kondensation von 4"i!-Dich-lor-3,5#3', 5-tetranitroben-zophenon mit 2, 6-Diamino-:2'-inethoxybenzophenon-47sulfonsäure erhalten. 3. By condensation of equimolel, ulart # n amounts of 4, d-dichloro-3, 5-3, 5'-tetr-anitrobenzophenone and 2,6-diamino-2'-chlorodiphenylamine-4-sulfonic acid under similar conditions in water or alcohols, a brown dye similar in its fastness properties is obtained. An equally genuine product is obtained by condensation of 4 "i! -Dich-lor-3,5 # 3 ', 5-tetranitrobenzophenone with 2,6-diamino-: 2'-ethoxybenzophenone-47sulfonic acid.

Claims (1)

PATENTANSPRUCH. Verfahren zur Herstellung von Wollfarbstoffen, da-durch gekennzeichnet, daß man 3, 5- 3', 5-Tetranitrobenzophenone, ;die in 4,4#-Stellung austauschfähige Atome oder Gruppe#n enthalten, mit 2, 6-Diaminodiphenylaminsulfonsäuren kondensiert und die erhaltenen Kondensati,onsproäukte bei höherer Temperatur mit Alkalien behandelt.PATENT CLAIM. Process for the preparation of wool dyes, characterized in that 3, 5- 3 ', 5-tetranitrobenzophenones, which contain atoms or groups which can be exchanged in the 4,4 # position, are condensed with 2,6-diaminodiphenylamine sulfonic acids and the The condensation products obtained are treated with alkalis at a higher temperature.
DEE1794A 1950-07-15 1950-07-15 Process for the production of wool dyes Expired DE869104C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEE1794A DE869104C (en) 1950-07-15 1950-07-15 Process for the production of wool dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEE1794A DE869104C (en) 1950-07-15 1950-07-15 Process for the production of wool dyes

Publications (1)

Publication Number Publication Date
DE869104C true DE869104C (en) 1953-03-02

Family

ID=7065392

Family Applications (1)

Application Number Title Priority Date Filing Date
DEE1794A Expired DE869104C (en) 1950-07-15 1950-07-15 Process for the production of wool dyes

Country Status (1)

Country Link
DE (1) DE869104C (en)

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