DE719150C - Process for the preparation of monoazo dyes - Google Patents

Process for the preparation of monoazo dyes

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Publication number
DE719150C
DE719150C DEI53388D DEI0053388D DE719150C DE 719150 C DE719150 C DE 719150C DE I53388 D DEI53388 D DE I53388D DE I0053388 D DEI0053388 D DE I0053388D DE 719150 C DE719150 C DE 719150C
Authority
DE
Germany
Prior art keywords
dyes
monoazo dyes
preparation
amino
monoazo
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
DEI53388D
Other languages
German (de)
Inventor
Dr Otto Goll
Dr Heinrich Morschel
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 DEI53388D priority Critical patent/DE719150C/en
Application granted granted Critical
Publication of DE719150C publication Critical patent/DE719150C/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28—Amino naphthols

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

Description

Verfahren zur Herstellung von Monoazofarbstoffen Gegenstand des Hauptpatents 689 9--3 ist ein Verfahren, daxin bestehend, daß man in an sich bekannter Weise auf i-Amino-7-oxY-naphthalin in saurer Lösung Diazoverbindungen aus Aminen, die frei von wasserlöslich machenden Gruppen sind,.,einwirken läßt. Die so erhältlichen Monoazoverbindungen besitzen eine 'gute, Affinität zur Baumwollfaser, so daß sie für die Herstellung von Azofarbstoffen auf der Faser nach Art der Eisfarben besonders geeignet sind.Process for the production of monoazo dyes The subject of the main patent 689 9-3 is a process which consists in a known manner on i-amino-7-oxY-naphthalene in acidic solution diazo compounds from amines which are free of water-solubilizing groups are,., can act. The monoazo compounds obtainable in this way have a 'good affinity for cotton fibers, so that they are particularly suitable for the production of azo dyes on the fiber in the manner of ice colors.

Es wurde nun gefunden, daß man Monoazofarbstoffe von übenfalls guter Affinität zur pflanzlichen Faser erhält, wenn man bei dem Verfahren des Hauptpatents das i-Amino-7-oxynaphtha'än durch dessen N-Alkyl- oder N-Aryl,substitution#sprodukt,a ersetzt.It has now been found that monoazo dyes are also of good quality Affinity for vegetable fiber obtained if one in the process of the main patent the i-amino-7-oxynaphtha'än by its N-alkyl or N-aryl, substitution # product, a replaced.

Es ist bereits bekannt, schwarze bis braunschwarze Disazofarbstoffe auf der Faser durch Aufbringen von f-Amino-7-oxynaphthalin und Kuppeln mit diazotiertem i-Amü-io-2-nitrobenzol oder mit anderen geeigneten Diazoverbindungen herzustellen. Im Gegensatz hierzu werden nach dem vorliegenden Verfahren rote bis blaurote Monoazofarbstoffe erhalten. Der Forts-chritt, der durch das vorliegende Verfahren gegenüber dem bekannten Verfahren erzielt wird, besteht darin, daß bei der Herstellung der Farbstoffe nach dem bekannten Verfahren nach dem Imprägnieren mit i-Aminc)-7-oxynaphthaa wegen der ungenügenden Affinität des i-Amino,-7-oxynaphthalins zur Faser e-iiie Zwischentrocknung erfor-.derlich ist, während die erfindungsgemäß hergestellten N-substituierten i-Amino-4-arylazo-7-oxynaphthaline eine derartige Affinität zur Faser aufweisen, daß sie zur Herstellung von Disazofarbstoffen auf der Faser ohne Zwischentrocknung verwendet werden können. Es sind auch bereits Farbstofie bekannt, die sich von den erfindungsgemäß hergestellten Farbstoffen durch die Anwesenheit einer alkoholischen Hydroxylgruppe und durch das Fehlen eines Substituenten in der Aminogruppe in i-Stellung des Naphthalinkerns unterscheiden. Diesen bekannten Farbstoffengegenüberzeichnen sich die neuen Farbstoffe durch eine hessere Substantivität zur pflanzlichen Faser aus.It is already known that disazo dyes are black to brown-black on the fiber by applying f-amino-7-oxynaphthalene and coupling with diazotized i-Amü-io-2-nitrobenzene or other suitable diazo compounds. In contrast, the present process produces red to bluish-red monoazo dyes obtain. The progress made by the present process over the known Process is achieved is that in the preparation of the dyes after the known process after impregnation with i-Aminc) -7-oxynaphthaa because of the Insufficient affinity of the i-amino, -7-oxynaphthalene for the fibers e-iiie intermediate drying is necessary, while the N-substituted i-amino-4-arylazo-7-oxynaphthalenes prepared according to the invention have such an affinity for fiber that they can be used in the manufacture of disazo dyes can be used on the fiber without intermediate drying. There are already Dyes known which differ from the dyes produced according to the invention the presence of an alcoholic hydroxyl group and the absence of a substituent differ in the amino group in the i-position of the naphthalene nucleus. This well-known In contrast to dyes, the new dyes are characterized by a better substantivity to vegetable fiber.

Beispiel i In eine eiskalte Lösung von 18 2 1 -iMethylamin0-7-oxynaphthalin in verdünnter Salzsäure wird die in bekannter Weise -2us 138 ei-Aminü-2-nitrabenzol hergestellte Diazolösung einge.rührt. Bei schwach kongo.saurer Reaktion erfolgt schnelle Farbstoffbildung. Der in Wasser unlösliche braunrote Monoazofarb,stoff wird in üblich#er Weise abgeschieden. Beispiel 2 Zu einer Lösung von 280 g I-(4#-MetlIOXY-phenylamina)-7-oxynaphthalin in iooo - Eisessig läßt man bei ioo eine Diazolösung einlaufen, die durch Diazotieren von 138 9 i-Arnino-4-nitrobenzol in 5oo ccm Eisessig und 280 ccm 3oprozentiger Salzsäure mit 6gg Natriumnitrit bereitet ist. Nach beendeter Kupplung -iv-ird der Farbstaff abgesaugt, mit Z, C 5oprozentiger Essigsäure gewaschen und getrocknet. Der Farbstoff stellt ein schwarzbraunes Pulver dar -, das in Pyridin mit blauer Farbe löslich ist. In gleicher Weise wurden die folgenden .-,arb,stoff,c hergestellt: i - Methylamino - 51 - chld-r-2'-methoxybenzol- 4, i'-a7o-7-oxynaphtbalin, i -.'#thylamino-2'-chlorbenz01-4, i'-az0-7-Oxv- naphthalin, i-Plieiiyiamino-2'-nitrobenzol-4, l-azo-7-Oxv- naphthalin, i -Äthylamino-2'-m,ethyl-Y-chlorbenzol - 4, 1,*- az0-7-oxvnaphtlialin. Example I Into an ice cold solution of 1 8 2 1 -iMethylamin0-7-oxynaphthalene in dilute hydrochloric acid, the ei-Aminü-2-nitrate benzene einge.rührt diazo solution prepared in a known manner -2us 138th If the reaction is weakly acidic to the Congo, dye is formed quickly. The red-brown monoazo dye, which is insoluble in water, is deposited in the usual way. Example 2 To a solution of 280 g of I- (4 # -MetlIOXY-phenylamina) -7-oxynaphthalene in iooo - glacial acetic acid is allowed to run in at ioo a diazo solution obtained by diazotizing 138 9 i-Arnino-4-nitrobenzene in 5oo cc Glacial acetic acid and 280 ccm 3 percent hydrochloric acid with 6 g sodium nitrite is prepared. After coupling has ended, the dye is filtered off with suction, washed with Z, C 5% acetic acid and dried. The dye is a black-brown powder - which is soluble in pyridine with a blue color. In the same way, the following were made .-, color, fabric, c made: i - methylamino - 51 - chld-r-2'-methoxybenzene- 4, i'-a7o-7-oxynaphtbalin, i -. '# thylamino-2'-chlorobenz01-4, i'-az0-7-Oxv- naphthalene, i-Plieiiyiamino-2'-nitrobenzene-4, l-azo-7-Oxv- naphthalene, i -ethylamino-2'-m, ethyl-Y-chlorobenzene - 4, 1, * - az0-7-oxvnaphtlialin.

Claims (1)

PATENTANSPRUCII: Abänderung des Verfahrens zur Her-.stellung von Monoazofarbstoffen nach Patent 689 923, dadurch gekennzeichnet, daß man Diazoverbindungen aus Aminen, die keine wasserlöslich machenden Gruppen enthalteh, hier mit i-.#,11,-ylarnino- oder i-Aryl-amino-7-oxynaphtbali,nen in saurer Lösung kuppelt.PATENT CLAIM: Modification of the process for the production of monoazo dyes according to patent 689 923, characterized in that diazo compounds from amines which do not contain any water-solubilizing groups, here with i -. #, 11, -ylarnino- or i-aryl- amino-7-oxynaphtbali, nen in acidic solution couples.
DEI53388D 1935-10-12 1935-10-12 Process for the preparation of monoazo dyes Expired DE719150C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI53388D DE719150C (en) 1935-10-12 1935-10-12 Process for the preparation of monoazo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI53388D DE719150C (en) 1935-10-12 1935-10-12 Process for the preparation of monoazo dyes

Publications (1)

Publication Number Publication Date
DE719150C true DE719150C (en) 1942-03-31

Family

ID=7193593

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI53388D Expired DE719150C (en) 1935-10-12 1935-10-12 Process for the preparation of monoazo dyes

Country Status (1)

Country Link
DE (1) DE719150C (en)

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