DE197554C - - Google Patents
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- Publication number
- DE197554C DE197554C DENDAT197554D DE197554DA DE197554C DE 197554 C DE197554 C DE 197554C DE NDAT197554 D DENDAT197554 D DE NDAT197554D DE 197554D A DE197554D A DE 197554DA DE 197554 C DE197554 C DE 197554C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- aminoanthraquinone
- diaminoanthraquinones
- dichloroanthraquinone
- diaminoanthraquinone
- 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.)
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- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 claims description 6
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 claims description 2
- 210000004940 Nucleus Anatomy 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In dem Patent 184905 ist ein Verfahren zur Darstellung von roten Küpenfarbstoffen beschrieben, welches darin besteht, daß man Diaminoanthrachinone mit zwei Molekülen 2-Chloranthrachinon kondensiert.In patent 184905 is a method for the preparation of red vat dyes described, which consists in the fact that one diaminoanthraquinones with two molecules 2-chloroanthraquinone condensed.
Es wurde nun gefunden, daß man zu analogen Farbstoffen gelangt, wenn man β · β - Dihalogenanthrachinone, welche die Halogenatome in verschiedenen Kernen enthalten, auf i-Aminoanthrachinon zur Einwirkung bringt. So erhält man z. B. durch Kondensation von 1 Molekül 2«6-Dichloranthrachinon mit 2 Molekülen i-Aminoanthrachinon einen Körper, dessen Analyse Zahlen ergab, die auf nachstehende Formel stimmen:It has now been found that analogous dyes are obtained if β · β -dihaloanthraquinones, which contain the halogen atoms in different nuclei, are brought into action on i-aminoanthraquinone. So you get z. B. by condensation of 1 molecule of 2 «6-dichloroanthraquinone with 2 molecules of i-aminoanthraquinone a body, the analysis of which resulted in numbers that agree with the following formula:
Es dürfte somit ein weiterer Repräsentant der im Hauptpatent beschriebenen ■Körperklasse vorliegen.It should therefore be another representative of the body class described in the main ■ patent are present.
An Stelle von i-Aminoanthrachinon lassen sich auch dessen Derivate sowie Diaminoanthrachinone verwenden, z. B. 1 · 5-Diaminoanthrachinon, 1 · 8-Diaminoanthrachinon und das Gemisch von Diaminoanthrachinonen, welches man durch Reduktion des leicht löslichen a - Dinitroanthrachinons des Patents 72685 erhält.Instead of i-aminoanthraquinone, its derivatives and diaminoanthraquinones can also be used, e.g. B. 1x5-diaminoanthraquinone, 1x8-diaminoanthraquinone and the mixture of diaminoanthraquinones, which is obtained by reducing the easily soluble α - dinitroanthraquinone of the patent 72685.
Die neuen Körper verhalten sich in ihren Reaktionen denen des Hauptpatents sehr ähnlich. Sie sind außerordentlich schwer löslich in den meisten organischen Lösungsmitteln, unlöslich in Wasser, Alkalien undThe reactions of the new bodies are very similar to those of the main patent. They are extremely sparingly soluble in most organic solvents, insoluble in water, alkalis and
verdünnten Säuren. In konzentrierter Schwefelsäure lösen sie sich mi.t grüner Farbe, die beim Erwärmen blauer wird. Mit alkalischer Hydrosulfitlösung erhält man gelb- bis braunrote Küpen, aus denen Baumwolle in roten Nuancen angefärbt wird. Die mit Hilfe von ι - Aminoanthrachinon erhaltenen Farbstoffe ergeben hierbei wesentlich rötere Töne als die aus Diaminoanthrachinonen dargestellten. Die erzielten Färbungen sind in allen Fällen von ganz hervorragender Echtheit.diluted acids. They dissolve in concentrated sulfuric acid with a green color, the becomes bluer when heated. With alkaline hydrosulfite solution yellow to brown-red vats are obtained, from which cotton in red Nuances is stained. The dyes obtained with the aid of ι - aminoanthraquinone result in much redder tones than those made from diamino anthraquinones. The dyeings obtained are in all cases of very excellent fastness.
Von den zur Verwendung kommenden ß'ß-Halogenanthrachinpnen ist die Darstellung des 2 •o-Dibromanthrachinons bereits von Walter Tritsch beschrieben (Inauguraldissertation »Über das 5-Methylnaphtanthrachinon und dessen Derivate. Über die Diazotierung der Brom-i · 5-diamidoanthrachinone«, eingereicht an der Universität Zürich 1907, S. 51). In analoger Weise läßt sich das 2 · 7-Dibromanthrachinon aus dem 1 · 8-Diaminoanthrachinon gewinnen; dasselbe unterscheidet sich von dem 2 · 6 - Derivat durch größere Löslichkeit in organischen Lösungsmitteln. The representation is of the ß'ß-halanthraquinene used of 2 • o-dibromoanthraquinone already described by Walter Tritsch (Inaugural dissertation »About 5-methylnaphtanthraquinone and its derivatives. About the diazotization der Brom-i · 5-diamidoanthraquinones ", submitted to the University of Zurich in 1907, P. 51). The 2 · 7-dibromoanthraquinone can be prepared from the 1 · 8-diaminoanthraquinone in an analogous manner to win; the same differs from the 2 x 6 derivative by greater solubility in organic solvents.
Die analogen Chlorderivate kann man aus den betreffenden Diaminoanthrachinonen durch Ersatz der Aminogruppen durch Chlor mit Hilfe der Sandmeyerschen Reaktion darstellen. Sie sind wie die Bromderivate hellgelb und lösen sich in Schwefelsäure mit gelber Farbe. Das 2 · 7-Derivat ist auch hier in organischen Lösungsmitteln leichter löslich als das 2· 6-Derivat. 2 · 6-Dichloranthrachinon schmilzt bei 280 bis 282°, 2'7-Dichloranthrachinon schmilzt bei 208 bis 2100.The analogous chlorine derivatives can be prepared from the relevant diaminoanthraquinones by replacing the amino groups with chlorine with the aid of Sandmeyer's reaction. Like the bromine derivatives, they are light yellow and dissolve in sulfuric acid with a yellow color. Here, too, the 2 · 7 derivative is more readily soluble in organic solvents than the 2 · 6 derivative. 2 · 6-dichloroanthraquinone melts at 280 to 282 °, 2'7-dichloroanthraquinone melts at 208-210 0th
to Teile 2 · 6-Dichloranthrachinon, 17 Teile ι-Aminoanthrachinon, 15 Teile entwässertes Natriumacetat, 2TeileKupferchlorür, 150 Teile Nitrobenzol werden bis zur beendeten Farbstoffbildung am Rückflußkühler zum Sieden erhitzt. Nach dem Erkalten wird abgesaugt, nacheinander mit Alkohol, Wasser, verdünnter Salzsäure und wieder mit Wasser gewaschen. Der zurückbleibende Farbstoff kann, um ihn in feinere Verteilung zu bringen, in Schwefelsäure gelöst und durch Zusatz von Wasser wieder ausgefällt werden.to parts of 2 · 6-dichloroanthraquinone, 17 parts ι-Aminoanthraquinone, 15 parts of dehydrated sodium acetate, 2 parts of copper chloride, 150 parts Nitrobenzene are boiled on the reflux condenser until the dye formation has ended heated. After cooling, it is suctioned off, one after the other with alcohol, water, diluted Hydrochloric acid and washed again with water. The remaining dye can make it to be brought into finer distribution, dissolved in sulfuric acid and added by adding water to be precipitated again.
10 Teile 2·7-Dibromanthrachinon, i2,2Teile ι - Aminoanthrachinon, 15 Teile entwässertes Natriumacetat, 2TeileKupferchlorür, i5oTeile Naphtalin werden bis zur Beendigung der Farbstoffbildung am Rückflußkühler zum Sieden erhitzt. Die fertige Schmelze wird mit 500 Teilen Toluol verdünnt, nach dem Erkalten abgesaugt und wie im Beispiel I weiterbehandelt.10 parts of 2 x 7-dibromoanthraquinone, i 2.2 parts ι - Aminoanthraquinone, 15 parts dehydrated Sodium acetate, 2 parts, copper chloride, 15 parts Naphthalene is heated to boiling in the reflux condenser until the dye formation has ended. The finished melt will diluted with 500 parts of toluene, filtered off with suction after cooling and as in Example I. further treated.
Beispiel III.Example III.
10 Teile 2 · 6-Dichloranthrachinon, 8,6 Teile ι · 5 - Diaminoanthrachinon, 20 Teile entwässertes Natriumacetat, 2 Teile Kupferchlorür, 200 Teile Nitrobenzol werden bis zur Beendigung der Farbstoffbildung am Rückflußkühler gekocht. Die Aufarbeitung geschieht wie im Beispiel I beschrieben.10 parts of 2 · 6-dichloroanthraquinone, 8.6 parts of ι · 5 - diaminoanthraquinone, 20 parts of dehydrated Sodium acetate, 2 parts of copper chloride, 200 parts of nitrobenzene are up to boiled on the reflux condenser to end the dye formation. The work-up happens as described in Example I.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE197554C true DE197554C (en) |
Family
ID=460434
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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Country Status (1)
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DE (1) | DE197554C (en) |
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- DE DENDAT197554D patent/DE197554C/de active Active
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