DE456236C - Process for the preparation of Kuepen dyes - Google Patents

Process for the preparation of Kuepen dyes

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Publication number
DE456236C
DE456236C DEI27333D DEI0027333D DE456236C DE 456236 C DE456236 C DE 456236C DE I27333 D DEI27333 D DE I27333D DE I0027333 D DEI0027333 D DE I0027333D DE 456236 C DE456236 C DE 456236C
Authority
DE
Germany
Prior art keywords
weight
parts
preparation
acid
dyes
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
DEI27333D
Other languages
German (de)
Inventor
Dr Wilhelm Eckert
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 DEI27333D priority Critical patent/DE456236C/en
Application granted granted Critical
Publication of DE456236C publication Critical patent/DE456236C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00Other synthetic dyes of known constitution
    • C09B57/12Perinones, i.e. naphthoylene-aryl-imidazoles

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

Description

Verfahren zur Darstellung von-Küpenfarbstoffen. Zusatz zum Patent 43o632"*). Gegenstand des Patents q.3o 632 ist die Darstellung von neuen Küpenfarbstoffen durch Kondensation des Dianhydrids der t # q. # 5 # 8-Naphthaäntetraca.rbons,äure oder dieser Säure selbst mit o-Diaminen oder deren Salzen bei An- oder Abwesenheit von Lösungs- oder Verdünnungsmitteln.Process for the preparation of vat dyes. Addition to the patent 43o632 "*). The subject of the patent q.3o 632 is the representation of new vat dyes by condensation of the dianhydride of t # q. # 5 # 8-Naphtha tetracarbons, acid or this acid itself with o-diamines or their salts in the presence or absence of solvents or thinners.

Bei der weiteren Bearbeitung dieses Gebiets wurde nun gefunden, daß man zu den gleichen Farbstoffen gelangt, wenn man das Dianhydrid der r # ¢ # 5 # 8-Naphthalintetracarbons.äure oder dieser Säure selbst mit den entsprechenden o-Nitroaminoverbindungen kondensiert und diese Kondensationsprodukte dann reduziert, wobei gleichzeitig Ringschluß zu den entsprechenden Imidazolderivaten erfolgt, z. B.: Die Reduktion kann sowohl alkalisch, wie mit Schwefelnatrium, Hydrosulfit usw., aber auch sauer, wie beispielsweise mit Eisen, in Eisessiglösung ausgeführt werden. **) Früheres Zusatzpatent 438 1 o7. Die so entstehenden Farbstoffe stimmen mit denen gemäß dem Hauptpatent überein. Beispiele. i. 15 Gewichtsteile Dianhydrid der i # ¢ # 5 # 8-Naphthalintetracarbonsäure und 3o Gewichtsteile 3-Nitro-4-anino-i-phenetol werden in i 5o Gewichtsteilen Nitrobenzol 6 bis 7 Stunden zum Sieden erhitzt. Beim Erkalten scheidet sich das i # 4 # 5 # 8-Naphthalintetracarbonsäure-di-(o-nitro-p-phenetidid) ab, wird abgesaugt, mit Sprit gewaschen und getrocknet.In further processing of this area, it has now been found that the same dyes are obtained if the dianhydride of r # ¢ # 5 # 8-naphthalenetetracarboxylic acid or this acid itself is condensed with the corresponding o-nitroamino compounds and these condensation products are then reduced , at the same time ring closure to the corresponding imidazole derivatives takes place, z. B .: The reduction can be carried out alkaline, such as with sodium sulphide, hydrosulfite, etc., but also acidic, such as, for example, with iron, in glacial acetic acid solution. **) Former additional patent 438 1 o7. The dyes produced in this way agree with those according to the main patent. Examples. i. 15 parts by weight of dianhydride of i # ¢ # 5 # 8-naphthalenetetracarboxylic acid and 3o parts by weight of 3-nitro-4-anino-i-phenetol are heated to boiling in i 50 parts by weight of nitrobenzene for 6 to 7 hours. On cooling, the i # 4 # 5 # 8-naphthalenetetracarboxylic acid-di- (o-nitro-p-phenetidide) separates out, is filtered off with suction, washed with fuel and dried.

io Gewichtsteile dieses Kondensationsprodukts werden in zoo ccm Eisessig heiß gelöst und mit i z g Eisenpulver zweckmäßig unter Zufügen von einigen Kubikzentimetern konzentrierter Salzsäure ungefähr i Stunde zum gelinden Sieden erhitzt. Nach dem Erkalten scheidet sich der Farbstoff ab. Er wird abgesaugt, vom nicht verbrauchten Eisenpulver befreit und getrocknet. Er stellt ein braunes Pulver dar und färbt aus olivgrüner, stark rot fluoreszierender Küpe Baumwolle nach dem Verhängen rotbraun.10 parts by weight of this condensation product are dissolved in zoo cc of glacial acetic acid Dissolved hot and with i z g iron powder, expediently with the addition of a few cubic centimeters concentrated hydrochloric acid heated to gentle boiling for about 1 hour. After this The dye separates out when it cools. It is sucked off from the unused Iron powder freed and dried. It is a brown powder and colors Olive-green, strongly fluorescent red vat. Cotton red-brown after hanging.

z. i o Gewichtsteile Dianhydrid der i # 4 # 5 # 8-Naphthalintetraca.rbonsäure werden in ioo Gewichtsteilen Nitrobenzol mit zo Gewichtsteilen o-Nitraniln 5 bis 6 Stunden zum Sieden erhitzt. Nach dem Erkalten kristallisiert das Kondensationsprodukt in braunen Nadeln aus, die über 28o° schmelzen und sich in konzentrierter Schwefelsäure mit gelber Farbe lösen.z. 10 parts by weight of dianhydride of i # 4 # 5 # 8-naphthalenetetracarboxylic acid are in 100 parts by weight of nitrobenzene with zo parts by weight of o-Nitraniln 5 bis Heated to the boil for 6 hours. After cooling, the condensation product crystallizes in brown needles that melt above 28o ° and are immersed in concentrated sulfuric acid solve with yellow paint.

8 Gewichtsteile dieses i # 4 # 5 # 8-Naphthalin.-tetracarbonsäure-di-(o-nitranilids) werden mit einer Lösung von 5o Gewichtsteilen kristallisiertem Schwefelnatrium in 5o Gewichtsteilen Wasser zum Sieden erhitzt, bis kein unverändertes Ausgangsmaterial mehr nachweisbar ist. Dann wird mit Wasser verdünnt, einige Zeit Luft eingeblasen, abgesaugt und mit Wasser gewaschen. Der so ierhaltene Farbstoff stimmt mit seinen Eigenschaften mit denjenigen des Hauptpatents überein. Er färbt _ aus grüner, stark rot fluoreszierender Küpe Baumwolle nach dem Verhängen in einem leuchtenden Rot.8 parts by weight of this i # 4 # 5 # 8-naphthalene-tetracarboxylic acid-di- (o-nitranilids) are with a solution of 5o parts by weight of crystallized sodium sulphide in 5o parts by weight of water heated to boiling until no unchanged starting material is more detectable. Then it is diluted with water, air is blown in for a while, suctioned off and washed with water. The dye obtained in this way agrees with his Properties match those of the main patent. He colors _ out green, strong red fluorescent vat of cotton after hanging in a bright red.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Küpenfarbstoffen nach Patent 43o 632, darin bestehend, daß man die Kondensationsprodukte des Dianhydrids der i # 4 # 5 # 8-Naphthalintetracarbonsäure oder dieser Säure selbst mit o-Nitroaminen mit Reduktionsmitteln behandelt. Claim: Process for the preparation of vat dyes according to Patent 43o 632, consisting in treating the condensation products of the dianhydride of i # 4 # 5 # 8-naphthalenetetracarboxylic acid or this acid itself with o-nitroamines with reducing agents.
DEI27333D 1926-01-30 1926-01-30 Process for the preparation of Kuepen dyes Expired DE456236C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI27333D DE456236C (en) 1926-01-30 1926-01-30 Process for the preparation of Kuepen dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI27333D DE456236C (en) 1926-01-30 1926-01-30 Process for the preparation of Kuepen dyes

Publications (1)

Publication Number Publication Date
DE456236C true DE456236C (en) 1928-02-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEI27333D Expired DE456236C (en) 1926-01-30 1926-01-30 Process for the preparation of Kuepen dyes

Country Status (1)

Country Link
DE (1) DE456236C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007012611A1 (en) * 2005-07-25 2007-02-01 Ciba Specialty Chemicals Holding Inc. Naphthalene amidine imides
WO2010099223A1 (en) * 2009-02-27 2010-09-02 Nitto Denko Corporation Lyotropic liquid crystal systems based on aromatic tetracarboxylic bisbenzoimidazole derivatives and methods for making

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007012611A1 (en) * 2005-07-25 2007-02-01 Ciba Specialty Chemicals Holding Inc. Naphthalene amidine imides
AU2006274083B2 (en) * 2005-07-25 2012-03-15 Basf Se Naphthalene amidine imides
US8404705B2 (en) 2005-07-25 2013-03-26 Basf Se Naphthalene amidine imides
WO2010099223A1 (en) * 2009-02-27 2010-09-02 Nitto Denko Corporation Lyotropic liquid crystal systems based on aromatic tetracarboxylic bisbenzoimidazole derivatives and methods for making
CN102361871A (en) * 2009-02-27 2012-02-22 日东电工株式会社 Lyotropic liquid crystal systems based on aromatic tetracarboxylic bisbenzoimidazole derivatives and methods for making
US8674103B2 (en) 2009-02-27 2014-03-18 Nitto Denko Corporation Lyotropic liquid crystal systems based on aromatic tetracarboxylic bisbenzoimidazole derivatives and methods for making

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