DE962463C - Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2, 2 ', 1'-dinaphthazine - Google Patents

Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2, 2 ', 1'-dinaphthazine

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Publication number
DE962463C
DE962463C DEF13656A DEF0013656A DE962463C DE 962463 C DE962463 C DE 962463C DE F13656 A DEF13656 A DE F13656A DE F0013656 A DEF0013656 A DE F0013656A DE 962463 C DE962463 C DE 962463C
Authority
DE
Germany
Prior art keywords
dioxy
chlorinated
dinaphthazine
sulfuric acid
preparation
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
DEF13656A
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German (de)
Inventor
Dr H C Dr E H Otto Bayer Dr
Dr Helmut Klappert
Dr Georg Roesch
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF13656A priority Critical patent/DE962463C/en
Application granted granted Critical
Publication of DE962463C publication Critical patent/DE962463C/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
    • C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
    • 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
    • C09B17/04—Azine dyes of the naphthalene series

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Description

Verfahren zur Herstellung des sauren Schwefelsäureesters von chloriertem 8, 8'-Dioxy-1, 2,2', 1'-dinaphthazin Der in der deutschen Patentschrift 481 296 (Beispiel 7) beschriebene Küpenfarbstoff, der durch Chlorieren von 8, 8'-Dioxy-1, 2, 2', 1'-dinaphthazin hergestellt wird, ist als Küpenfarbstoff nicht zu verwenden, da er - nach verschiedenen Verfahren gefärbt - verschiedene Nuancen ergibt. In der französischen Patentschrift 9o6 963 wird die Veresterung dieses Farbstoffs durch Umsetzung mit Carbonsäure-- und Sulfonsäurehalogeniden und die Verwendung der Ester als saure Woll- bzw. Druckfarbstoffe beschrieben. Diese Farbstoffe müssen durch Verkochen mit wäßrigem Alkali entwickelt werden.Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2,2 ', 1'-dinaphthazine The vat dye described in German Patent 481 296 (Example 7), which is obtained by chlorinating 8, 8'-dioxy -1, 2, 2 ', 1'-dinaphthazine is produced, should not be used as a vat dye because it - colored by different processes - gives different shades. The French patent 9o6 963 describes the esterification of this dye by reaction with carboxylic acid and sulfonic acid halides and the use of the esters as acidic wool or printing dyes. These dyes have to be developed by boiling with aqueous alkali.

Die Herstellung der Ester kann jedoch nicht mit Chlorsulfonsäure erfolgen, da bei den erforderlichen hohen Reaktionstemperaturen und längeren Reaktionszeiten die Chlorsulfonsäure mit dem als Lösungsmittel verwendeten Pyridin reagiert.However, the esters cannot be produced with chlorosulfonic acid, because of the required high reaction temperatures and longer reaction times the chlorosulfonic acid reacts with the pyridine used as solvent.

Es wurde nun gefunden, daß sich das Chlorierungsprodukt von 8, K-Dioxy-1, :2,:2', 1'-dinaphthazin in Gegenwart von Eisenpulver mit Chlorsulfansäure in Pyridin mit guter Ausbeute in den entsprechenden sauren Schwefelsäureester überführen läßt. Der auf übliche Weise als Natriums.alz isolierte Schwefelsäureester löst sich in Wasser und kann nach bekannten Verfahren auf die Faser gebracht werden. Er unterscheidet sich von den in der obenerwähnten französischen Patentschrift und von den in den deutschen Patentschriften 564 115, 6o6 563 und 572 032 beschriebenen Estern in vorteilhafter Weise dadurch, daB er durch neutrales oder saures Dämpfen gespalten und in den zugrunde liegenden Farbstoff übergeführt werden kann, ohne daß, wie bei den zuletzt erwähnten drei deutschen Patentschriften, ein Oxydationsmittel zugesetzt werden muß. Der neue Ester kann auch in einem sauren Bad zu dem Farbstoff entwickelt werden, wobei im Gegensatz zu den Leukoestern von Küpenfarbstoffen kein Oxydationsmittel zugefügt zu werden braucht.It has now been found that the chlorination product of 8, K-Dioxy-1, : 2,: 2 ', 1'-dinaphthazine in the presence of iron powder with chlorosulfanic acid in pyridine can be converted into the corresponding acidic sulfuric acid ester with good yield. The sulfuric acid ester isolated in the usual way as sodium salt dissolves in Water and can be applied to the fiber by known methods. He differentiates differ from those in the above-mentioned French patent specification and from those in the German patents 564 115, 6o6 563 and 572 032 are more advantageous way by the fact that it is split by neutral or acidic steaming and is broken down into the lying dye can be transferred without, as with the last-mentioned three German patents, an oxidizing agent must be added. The new Ester can also be developed into the dye in an acidic bath, with im In contrast to the leuco esters of vat dyes, no oxidizing agent is added needs to become.

Die unter Verwendung des neuen Sehwefelsäureesters erzeugten roten Färbungen besitzen sehr gute Licht- und Chlorechtheit. Beispiel In 6oo ccm wasserfreies Pyridin werden 8o g Chlorsulfonsäure eingetropft, wobei die Temperatur unter 70° gehalten wird. Unter heftigem Rühren trägt man bei 5o° eine Mischung von 30 9 Farbstoff (nach der deutschen Patentschrift 481 296, Beispiel 7) und 30 g Nadeleisen ein und rührt Il/2 bis 2 Stunden bei 55 bis 6o°. Dann gießt man das Reaktionsgemisch in 1,51 1o%iger Sololösung und filtriert vom Ungelösten ab. Aus dem Filtrat wird das Pyridin im Vakuum abdestilliert und aus dem Rückstand der Schwefelsäureester mit Natriumchlorid ausgesalzen. Ausbeute: 8o'°/0.The red colorations produced using the new sulfuric acid ester have very good light and chlorine fastness. EXAMPLE 80 g of chlorosulfonic acid are added dropwise to 600 cc of anhydrous pyridine, the temperature being kept below 70 °. With vigorous stirring, a mixture of 30 g of dye (according to German Patent 481 296, Example 7) and 30 g of needle iron is introduced at 50 ° and the mixture is stirred for 2 to 2 hours at 55 to 60 °. The reaction mixture is then poured into 1.51 10% strength solution and the undissolved material is filtered off. The pyridine is distilled off from the filtrate in vacuo and the sulfuric acid ester is salted out from the residue with sodium chloride. Yield: 80 ° / 0.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des sauren Schwefelsäureesters von chloriertem 8, 8'-Dioxy-1, 2,:2', 1'-dinaphthazin, dadurch gekennzeichnet, daß chloriertes 8, 8'-Dioxy-1, 2, 2',1'-dinap'hthazin in Gegenwart von Eisenpulver mit Chlorsulfonsäure in Pyrid.n umgesetzt wird. In Betracht gezogene Druckschriften: Deutsche Patentschriften Nr. 564 115, 572 o32, 6o6563. PATENT CLAIM: Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2,: 2 ', 1'-dinaphthazine, characterized in that chlorinated 8, 8'-dioxy-1, 2, 2', 1 '-dinap'hthazin is reacted with chlorosulfonic acid in Pyrid.n in the presence of iron powder. Considered publications: German Patent Specifications Nos. 564 115, 572 o32, 6o6563.
DEF13656A 1954-01-10 1954-01-10 Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2, 2 ', 1'-dinaphthazine Expired DE962463C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF13656A DE962463C (en) 1954-01-10 1954-01-10 Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2, 2 ', 1'-dinaphthazine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF13656A DE962463C (en) 1954-01-10 1954-01-10 Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2, 2 ', 1'-dinaphthazine

Publications (1)

Publication Number Publication Date
DE962463C true DE962463C (en) 1957-04-25

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ID=7087368

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF13656A Expired DE962463C (en) 1954-01-10 1954-01-10 Process for the preparation of the acid sulfuric acid ester of chlorinated 8, 8'-dioxy-1, 2, 2 ', 1'-dinaphthazine

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DE (1) DE962463C (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE564115C (en) * 1925-03-17 1932-11-14 Scottish Dyes Ltd Process for the preparation of ester derivatives of the leuco compounds of Kuepen dyes
DE572032C (en) * 1930-07-31 1933-03-09 I G Farbenindustrie Akt Ges Process for the preparation of stable, acidic, water-soluble sulfuric acid esters of the leuco compounds of Kuepen dyes
DE606563C (en) * 1931-10-08 1934-12-06 Durand & Huguenin Akt Ges Process for the preparation of sulfuric acid esters of the leuco compounds of Kuepen dyes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE564115C (en) * 1925-03-17 1932-11-14 Scottish Dyes Ltd Process for the preparation of ester derivatives of the leuco compounds of Kuepen dyes
DE572032C (en) * 1930-07-31 1933-03-09 I G Farbenindustrie Akt Ges Process for the preparation of stable, acidic, water-soluble sulfuric acid esters of the leuco compounds of Kuepen dyes
DE606563C (en) * 1931-10-08 1934-12-06 Durand & Huguenin Akt Ges Process for the preparation of sulfuric acid esters of the leuco compounds of Kuepen dyes

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