DE192970C - - Google Patents
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- Publication number
- DE192970C DE192970C DENDAT192970D DE192970DA DE192970C DE 192970 C DE192970 C DE 192970C DE NDAT192970 D DENDAT192970 D DE NDAT192970D DE 192970D A DE192970D A DE 192970DA DE 192970 C DE192970 C DE 192970C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- halogen
- acetyl derivatives
- products
- added
- 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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- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- WDJHNJSBPXRITJ-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)acetamide Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C WDJHNJSBPXRITJ-UHFFFAOYSA-N 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/14—Benz-azabenzanthrones (anthrapyridones)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
■-M 192970 KLASSE 22 ö. GRUPPE ■ -M 192970 CLASS 22 Ö. GROUP
Zusatz zum Patente 191111 vom 3. Juni 1906.Addendum to patent 191111 of June 3, 1906.
Patentiert im Deutschen Reiche vom 6. November 1906 ab. Längste Dauer: 2. Juni 1921.Patented in the German Empire on November 6, 1906. Longest duration: June 2, 1921.
In der Patentschrift 191111 ist ein Verfahren zur Darstellung von gelben Küpenfarbstoffen der Anthracenreihe aus halogensubstituierten ι-Acetaminoanthrachinonen beschrieben. In the 191111 patent is a method for the representation of yellow vat dyes of the anthracene series from halogen-substituted ι-Acetaminoanthraquinones described.
Es wurde nun gefunden, daß man zu gleichen oder zu ähnlichen Farbstoffen gelangt, wenn man an Stelle der halogensubstituierten I-Acetaminoanthrachinone die aus diesen Körpern oder aus halogenfreien 1-Acetaminoanthrachinonen durch Behandlung mit Säurechloriden wie Phosphoroxychlorid, Phosphorpentachlorid oder Sulfurylchlorid erhältlichen Produkte in dem Verfahren des Hauptpatents verwendet.It has now been found that the same or similar dyes are obtained if you replace the halogen-substituted I-acetaminoanthraquinones with those from these bodies or from halogen-free 1-acetaminoanthraquinones by treatment with acid chlorides such as phosphorus oxychloride, phosphorus pentachloride or sulfuryl chloride available Products used in the process of the main patent.
Die genannten Einwirkungsprodukte sind schwache Basen, die sich in Schwefelsäure mit roter Farbe lösen; sie unterscheiden sich hierdurch von den Acetylaminoanthrachinonen, deren Lös.ungsfarbe in Schwefelsäure gelb ist. Verdünnt man die schwefelsaure Lösung langsam mit Wasser, so fallen aus ersteren Lösungen die Basen unverändert aus, während man aus den Lösungen der Acetylderivate infolge von Verseifung die Aminoanthrachinone erhält'. Ferner zeichnen sich die erwähnten Produkte vor den Acetylderivaten ■ durch ihre viel geringere Löslichkeit in organischen Lösungsmitteln aus.The mentioned action products are weak bases, which are in sulfuric acid solve with red paint; they differ in this way from the acetylaminoanthraquinones, whose solution color in sulfuric acid is yellow. Dilute the sulfuric acid solution slowly with water, the bases precipitate unchanged from the former solutions, while from the solutions of the acetyl derivatives as a result of saponification, the aminoanthraquinones are retained '. Furthermore, the mentioned Products ahead of the acetyl derivatives ■ due to their much lower solubility in organic ones Solvents.
Die Darstellung dieser Körper kann auch 35 The representation of this body can also be 35
in der Weise erfolgen, daß man die Acetylierung und Säurechloridbehandlung zu einer Operation vereinigt, indem man z. B. das i-Aminoanthrachinon oder dessen Halogenderivate mit Phosphoroxychlorid anrührt, Essigsäureanhydrid hinzufügt und erwärmt, bis die Reaktion beendigt ist.be carried out in such a way that the acetylation and acid chloride treatment to one Operation united by z. B. the i-aminoanthraquinone or its halogen derivatives stirred with phosphorus oxychloride, acetic anhydride added and heated until the reaction is complete.
Die Umwandlung der beschriebenen Einwirkungsprodukte von Säurechloriden auf Acetaminoanthrachinone, die wir in den Beispielen der Kürze halber als »Produkte« aus den betreffenden Aminoanthrachinonen bezeichnen, in Farbstoffe erfolgt analog wie im Hauptpatent beschrieben.The conversion of the described action products of acid chlorides on Acetaminoanthraquinones, which we refer to as "products" in the examples for the sake of brevity denote the aminoanthraquinones in question, in dyes is carried out analogously to in Main patent described.
4545
10 Teile Produkt aus i-Aminoanthrachinon werden in 150 Teile siedendes Nitrobenzol eingetragen, 4 Teile Aluminiumchlorid hinzugefügt und die Mischung 1 Stunde im Sieden erhalten. Nach dem Erkalten werden 150 Teile Alkohol hinzugefügt, der abgeschiedene Farbstoff wird abgesaugt, mit Alkohol gewaschen und getrocknet. Er färbt Baumwolle aus der Hydrosulfitküpe in orangegelben Tönen an.10 parts of i-aminoanthraquinone product are dissolved in 150 parts of boiling nitrobenzene entered, 4 parts of aluminum chloride added and the mixture at the boil for 1 hour obtain. After cooling, 150 parts of alcohol are added, the deposited dye is filtered off with suction, washed with alcohol and dried. He dyes cotton from the Hydrosulfite vat in orange-yellow tones.
10 Teile Produkt aus i-Amino-2 · 4-dichloranthrachinon werden in 150 Teile siedendes Nitrobenzol eingetragen, 4 Teile Eisenchlorid10 parts of i-amino-2 · 4-dichloroanthraquinone product are introduced into 150 parts of boiling nitrobenzene, 4 parts of iron chloride
hinzugefügt, worauf noch ι Stunde im Sieden erhalten wird. Die Aufarbeitung geschieht wie in Beispiel I. Der Farbstoff ist dem in jenem Beispiel beschriebenen ähnlich.added, whereupon another ι hour is kept in the boil. The work-up is done as in Example I. The dye is similar to that described in that example.
Beispiel III.Example III.
IO Teile Produkt aus i-Amino-2 · 4-dibromanthrachinon werden in 200 Teile siedendes Nitrobenzol eingetragen, <2 Teile Kupferchlorür hinzugefügt, worauf 2 Stunden im Sieden erhalten wird. Die Aufarbeitung erfolgt wie in Beispiel I. Der Farbstoff besitzt ähnliche Eigenschaften wie die nach den obigen Beispielen erhaltenen Produkte.IO parts of product from i-amino-2 · 4-dibromoanthraquinone are added to 200 parts of boiling nitrobenzene, <2 parts of copper chloride added, whereupon 2 hours of boiling is obtained. The work-up is carried out as in Example I. The dye has properties similar to those of the above examples received products.
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