DE1644632A1 - Process for the production of basic anthraquinone dyes - Google Patents

Process for the production of basic anthraquinone dyes

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Publication number
DE1644632A1
DE1644632A1 DE19641644632 DE1644632A DE1644632A1 DE 1644632 A1 DE1644632 A1 DE 1644632A1 DE 19641644632 DE19641644632 DE 19641644632 DE 1644632 A DE1644632 A DE 1644632A DE 1644632 A1 DE1644632 A1 DE 1644632A1
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Germany
Prior art keywords
formula
parts
anthraquinone dyes
dyes
production
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Pending
Application number
DE19641644632
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German (de)
Inventor
Roland Entschel
Curt Mueller
Walter Wehrli
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Sandoz AG
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Sandoz AG
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Filing date
Publication date
Priority claimed from CH489862A external-priority patent/CH496765A/en
Priority claimed from CH470961A external-priority patent/CH435495A/en
Priority claimed from CH35962A external-priority patent/CH462348A/en
Priority claimed from CH1501362A external-priority patent/CH461664A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of DE1644632A1 publication Critical patent/DE1644632A1/en
Pending 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
    • C09B69/002—Hydrazinium group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B21—MECHANICAL METAL-WORKING WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
    • B21D—WORKING OR PROCESSING OF SHEET METAL OR METAL TUBES, RODS OR PROFILES WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
    • B21D53/00—Making other particular articles
    • B21D53/02—Making other particular articles heat exchangers or parts thereof, e.g. radiators, condensers fins, headers
    • B21D53/04—Making other particular articles heat exchangers or parts thereof, e.g. radiators, condensers fins, headers of sheet metal
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • 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
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • 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
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • 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
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/501—Amino-hydroxy-anthraquinones; Ethers and esters thereof containing onium groups
    • 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
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • 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
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
    • C09B1/542—Anthraquinones with aliphatic, cycloaliphatic, araliphatic or aromatic ether groups
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • 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
    • C09B51/00—Nitro or nitroso dyes
    • 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
    • C09B55/00—Azomethine dyes
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
    • C09B62/66—Azo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Coloring (AREA)

Description

FrfetifafiwSlt*FrfetifafiwSlt *

Dr. W. Schalk, Dipl.-lng. P.,Wtrtli Dr. W. Schalk, Dipl.-Ing. P., Wtrtli

Dipl.-lng. G. DannenbdrgDipl.-Ing. G. Dannenbdrg

Dr. V. Schmied. KowarzikDr. V. blacksmith. Kowarzik

Dr. P. Weinhold, Dr. D. GudelDr. P. Weinhold, Dr. D. Gudel

S Frankfurt/M., Gr. Eschenheimer Str.S Frankfurt / M., Gr. Eschenheimer Str.

.3 A N D O Z AG Basel / Schweiz.3 A N D O Z AG Basel / Switzerland

Case 1778/A Verfahren zur Herstellung von basischen AnthrachinonfarbstoffenCase 1778 / A Process for the production of basic anthraquinone dyes

Gegenstand der Erfindung ist ein Verfahen zur Herstellung von basischen Farbstoffen der Anthrachinoneine frei von Carbonsäure- und Su If ons äure gruppen entsprechend der Formel ("I).The invention is a process for the production of basic dyes of the anthraquinones free of carboxylic acid and Su If onic acid groups corresponding to the formula ("I).

Diese Farbstoffe dienen vorzugsweise zum Färben, Klotzen oder Bedrucken von Acrylnitrllpolymerisatiorisprodukten aber auch zum Färben, Klotzen oder Bedrucken von durcn saure Gruppen modifizierten Polyestern oder Polyolefinen. In der Formel (l)These dyes are preferably used for dyeing, padding or Printing of acrylonitrile polymer products, but also for dyeing, padding or printing of acidic groups modified polyesters or polyolefins. In the formula (l)

009883/1755009883/1755

O NH,O NH,

O WO W

0-Z-CH2-K1 0-Z-CH 2 -K 1

bedeuten,mean,

W Amino, einen gegebenenfalls substituierten Alkylamino- oder Phenylaminorest,W amino, an optionally substituted alkylamino or phenylamino radical,

CH0-NfI-CO-, oderCH 0 -NfI-CO-, or

Z -CH2-, Λ „ K, die GruppierungZ -CH 2 -, Λ "K, the grouping

CILCIL

-N-NfL-N-NfL

undand

CHCH

X ein Anion.X is an anion.

Die Alkylaminoreste sind vorzugzsweise niedrigmolekulare Alkylaminoreste mit 1 bis 4 Kohlenstoffatomen. Gegebenenfalls substituierte AIkylaminores's sind beispielsweise durch Halogenatome (Chlor, Brom oder Fluor), oder durch Hydroxyl oder Cyangruppen substituiert. Gegebenenfalls substituierte Pheny1-amlnoreste sind beispielsweise durch Alkyl- oder Alkoxygruppen oder durch Halogenatome, wie Chlor, Brom oder Fluor, substituiert.The alkylamino radicals are preferably low molecular weight Alkylamino radicals having 1 to 4 carbon atoms. Possibly substituted alkylaminores are, for example, by halogen atoms (Chlorine, bromine or fluorine), or substituted by hydroxyl or cyano groups. Optionally substituted phenyl-amino radicals are, for example, substituted by alkyl or alkoxy groups or by halogen atoms, such as chlorine, bromine or fluorine.

Unter AnionUnder anion

sind sowohl organische wie anorganische Ionen 009883/1755 are both organic and inorganic ions 009883/1755

zu verstehen, wie z.B. Methylsulfat-, Sulfat-, Disulfat-, Perchlorat-, Phosphat-, Chlorid-, Broraid-, Iodid-, Phosphormolybdat-, Phosphorwolframmolybdat-, Benzolsulfonat-, 4-Chlorbenzolsulfonat-, Oxalat- oder Maleinationen.to understand, such as methyl sulfate, sulfate, disulfate, Perchlorate, phosphate, chloride, broraide, iodide, phosphomolybdate, Phosphotungsten molybdate, benzenesulfonate, 4-chlorobenzenesulfonate, Oxalate or maleinate ions.

Das Verfahren zur Herstellung der neuen Farbstoffe ist dadurch gekennzeichnet, dass man eine von Carbonsäure- und Sulfonsäuregruppen freie Verbindung der Formel, vorzugsweise 1 Mol einer Verbindung der FormelThe process for preparing the new dyes is characterized in that one of carboxylic acid and sulfonic acid groups is used free compound of the formula, preferably 1 mole of a compound of the formula

0-Z-CH2-E0-Z-CH 2 -E

worin E den Säurerest eines Esters bedeutet, mit dem Dimethyl· hydrazin der Formel, vorzugsweise mit 1 Mol Dimethylhydrazin der Formelwhere E is the acid residue of an ester with the dimethylhydrazine of the formula, preferably with 1 mol of dimethylhydrazine the formula

N-NH.N-NH.

(III)(III)

umsetzt.implements.

Als Säurereste E kommen beispielsweise diejenigen der Schwefel-The acid residues E include, for example, those of the sulfur

009883/1755009883/1755

säure (E steht für SO^H), einer Sulfonsäure (E steht für SO^R, worin R einen gegebenenfalls substituierten Kohlenwasserstoffrest bedeutet), des Schwefelwasserstoffs (E steht für SH), vorzugsweise aber diejenigen der Halogenwasserstoffsäuren (E steht für Cl oder Br) in Betracht.acid (E stands for SO ^ H), a sulfonic acid (E stands for SO ^ R, in which R denotes an optionally substituted hydrocarbon radical) of hydrogen sulfide (E denotes SH), preferably but those of the hydrohalic acids (E stands for Cl or Br) into consideration.

Die Umsetztung einer Verbindung der Formel (II) mit dem DimethyI-' hydrazin der Formel (ill) erfolgt vorzugsweise in einem orga- ^ nischen Lösungsmittel und bei Temperaturen von -50° bis + 250°. Man kann die Umsetzung aber auch in wässrigen Mittel, gegebenenfalls unter Zusatz eines organischen Lösungsmittels, oder aber ganz ohne Lösungsmittel bei den obengenannten Temperaturen durchführen. The reaction of a compound of the formula (II) with the DimethyI- ' hydrazine of the formula (III) is preferably carried out in an organic solvent and at temperatures from -50 ° to + 250 °. However, the reaction can also be carried out in aqueous media, if appropriate with the addition of an organic solvent, or else Carry out completely without solvents at the above-mentioned temperatures.

Die erhaltenen Farbstoffe können z.B. durch Filtrieren, gegebenenfalls nach Eindampfen oder Ausfällen abgetrennt werden.The dyes obtained can, for example, by filtering, optionally be separated after evaporation or precipitation.

ψ Sie dienen vorzugsweise zum Färben und Bedrucken von Formkörpern, insbesondere Fasern und Fäden, aus Polymerisationsprodukten aus mehr als 80 % Acrylnitril, beispielsweise aus Polyacrylnitril oder Mischpolymerisaten. ψ They are preferably used for dyeing and printing moldings, in particular fibers and threads, made from polymerization products made from more than 80 % acrylonitrile, for example from polyacrylonitrile or copolymers.

Diese Fasern können im Gemisch mit anderen gefärbt werden. Man erhält kräftige egale Färbungen mit guter Licht- oder Nassechtheit und besonders guter Wasch-, S chweiss-^Sublimier-, Plissier-, Bügel-, Wasser-, Meerwasser-, Bleich-, Trockenreinigungs-Uberfärbe- und Lösungsmittelechtheit. Ferner sind die FarbstoffeThese fibers can be colored in a mixture with others. Man receives strong level dyeings with good light or wet fastness and particularly good washing, welding, subliming, pleating, Fastness to ironing, water, seawater, bleaching, dry cleaning, dyeing and solvents. Also are the dyes

009883/ 1755009883/1755

zum Färben oder Bedrucken von durch saure Gruppen modifizierten Polyester- oder Polyolefinfasern geeignet.suitable for dyeing or printing polyester or polyolefin fibers modified by acidic groups.

Man färbt meist in wässrigem, neutralem oder saurem Mittel bei Kochtemperatur unter Atmosphärendruck öder in geschlossenem Gefäss bei erhöhter Temperatur unter erhöhtem Druck. HändeIsüblische Retarder stören nicht, sind jedoch nicht erforderlich. Die Farbstoffe eignen sich auch zum Färben von Acrylnitrilpolymerisationsprodukten und anderen, gegebenenfalls gelösten Kunststoffen in der Masse in licht- und nassechten Tönen, zum Färben von Oelen oder Lacken oder auch zum Färben von Baumwolle, besonders tannierter Baumwolle, Wolle, Seide, Cellulose, regenerierter Cellulose, synthetischen Polyamiden und von Papier in jedem Herstellungsstadium. Es hat sich gezeigt dass man auch vorteilhaft Gemische aus zwei oder mehreren Farbstoffen der Formel (i) einsetzten kann.You usually dye in aqueous, neutral or acidic agents at boiling temperature under atmospheric pressure or in a closed vessel at elevated temperature under elevated pressure. Hands Retarders do not interfere, but are not required. The dyes are also suitable for coloring acrylonitrile polymerization products and other, possibly dissolved plastics in the mass in light- and wet-fast tones, for coloring oils or lacquers or for coloring Cotton, especially tannin cotton, wool, silk, cellulose, regenerated cellulose, synthetic polyamides and of paper at every stage of manufacture. It has been shown that it is also advantageous to use mixtures of two or more Can use dyes of the formula (i).

Gegenüber den aus der französichen Patentschrift Nr. 1 277 bekannten, nächstvergleichbaren Anthrachinonfarbstoffen zeichnen sich die verfahrensgemäss erhältlichen Anthrachinonfarbstoffe durch ihre bessere Kombinierbarkeit aus.Compared to that from French patent specification No. 1 277 known, closest comparable anthraquinone dyes are characterized by the anthraquinone dyes obtainable according to the process by their better combinability.

In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind In Celsiusgraden angegeben.In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.

009883/1755009883/1755

Beispiel 1example 1

Eine Suspension von 15 Teilen l,4-Diamino-2-(2l-chlor)-äthoxyanthrachinon in Wasser wird mit 7 Teilen asymmetrischen Dimethylhydrazin versetzt und bis zur vollständigen Lösung bei 6O-630 gerührt· Der entstandene, wasserlösliche Farbstoff wird durch Zugabe von Kochsalz gefällt, abgesaugt und bei 60° im Vakuum getrocknet. Das dunkelrote Pulver färbt Textilgut aus Polyacrylnitril in violett-roten Tönen.A suspension of 15 parts of l, 4-diamino-2- (2-chloro l) -äthoxyanthrachinon in water is mixed with 7 parts of asymmetric dimethylhydrazine and stirred until completely dissolved at 6O-63 0 · The resulting water-soluble dye is prepared by adding precipitated from sodium chloride, filtered off with suction and dried at 60 ° in a vacuum. The dark red powder colors textiles made of polyacrylonitrile in violet-red tones.

FärbebeipsielStaining example

20 Teile des nach Beispiel 1 erhaltenen Farbstoffes werden zunächst mit 80 Teilen Dextrin in einer Kugelmühle während 4& Stunden innig vermischt.20 parts of the dye obtained according to Example 1 are first mixed with 80 parts of dextrin in a ball mill during Intimately mixed for 4 & hours.

Dann wird 1 Teil des so gewonnenen Präparates mit 1 Teil Essigsäure 40 % angesteigt, der Brei unter ständigem Schütteln mit 400 Teilen destilliertem Wasser von 6o° übergössen und das Ganze kurz aufgekocht. Man verdünnt nochmals mit 76OO Teilen destilliertem Wasser, setzt 2 Teile Eisessig zu und geht bei 60° mit 100 Teilen Textilgut aus Polyacrylnitril in das Färbebad ein. Das Material wurde 10 bis 15 Minuten lang bei 60° in einem Bad von 8OOO Teilen Wasser und 2 Teilen Eisessig vorbehandelt. Man erwärmt nun innerhalb von 30 Minuten auf 100°, kocht 1 Stunde lang und spült. Man erhält eine egale blaustichig rote Färbung von ausgezeichneter Lichtechtheit und sehr guten Nasse chtheiten.Then 1 part of the preparation obtained in this way is made stronger with 1 part 40% acetic acid, 400 parts of distilled water at 60 ° are poured over the pulp while shaking constantly and the whole thing is briefly boiled. It is diluted again with 7600 parts of distilled water, 2 parts of glacial acetic acid are added and 100 parts of textile material made of polyacrylonitrile are added to the dyebath at 60 °. The material was pretreated for 10 to 15 minutes at 60 ° in a bath of 800 parts of water and 2 parts of glacial acetic acid. It is then heated to 100 ° within 30 minutes, boiled for 1 hour and rinsed. A level, bluish red dyeing of excellent lightfastness and very good wetness properties is obtained.

009883/1755009883/1755

16U63.216U63.2

Beispiel für die Foulard-FärbungExample of the foulard dyeing

Zum Herstellan der Klotzpaste verwendet man :To produce the block paste you use:

50 gr / Liter Farbstoffpräparat
3 gr / Liter Natriumalginat
5 gr / Liter konzentrierte Essigsäure50 gr / liter dye preparation
3 gr / liter sodium alginate
5 gr / liter concentrated acetic acid

20 gr / Liter Natriumsulfat20 gr / liter sodium sulfate

Polyacrylnitrilfasermaterial wird auf einem 2- oder J5-Walzenfoulard kalt foulardiert. Der Abpresseffekt beträgt 80 #. Nach einer Zwischentrocknung bei 90° im Spannrahmen, Hotflue oder mit Hilfe eines Infrarot-Strahlers wird im Düsemspannrahmen bei 170-190° während 1-3 Minuten mit trockener Luft fixiert, anschliessend gespült, geseift und nochmals gespült. Man erhält eine blaustichig-rote Färbung mit hervorragenden Lichtechtheitseigenschaften.Polyacrylonitrile fiber material is placed on a 2 or J5 roll pad cold padded. The squeeze effect is 80 #. After intermediate drying at 90 ° in a stenter, hot flue or with the help of an infrared radiator, dry air is used in the nozzle clamping frame at 170-190 ° for 1-3 minutes fixed, then rinsed, soaped and rinsed again. A bluish red coloration with excellent results is obtained Lightfastness properties.

DruckbeispielPrint sample

Mit einer Druckpaste, die aus
75 Teilen Farbstoffpräparat
10 Teilen konzentrierter Essigsäure 450 Teilen eines kationaktiven Weichmachers, z.B. einesWith a printing paste that made
75 parts of dye preparation
10 parts of concentrated acetic acid 450 parts of a cationic plasticizer, for example one

Kondensationsproduktes aus 1 Mol Stearinsäure und 1 Mol Triäthanolamin
25 Teilen Natriumsulfat
4 Teilen WasserCondensation product of 1 mole of stearic acid and 1 mole of triethanolamine
25 parts of sodium sulfate
4 parts of water

1000 Teile
besteht,1000 parts
consists,

09 883/175509 883/1755

wird Polyacrylnitrilfasermaterial nach dem Handdruckverfahren bedruckt, das Fasermaterial anschliessend an der Luft getrocknet, in einem Sterndämpfer mit Sattdampf während 20-30 Minuten gedämpft, sodann gespült, geseift und nochmals gespült. Es wird ein blaustichig-roter Druck mit sehr guten Echtheitseigenschaften erhalten. polyacrylonitrile fiber material is printed using the hand printing process, the fiber material is then dried in the air, in a star steamer with saturated steam for 20-30 minutes steamed, then rinsed, soaped and rinsed again. A bluish-red print with very good fastness properties is obtained.

Weitere wertvolle Farbstoffe der Anthrachinonreihe, welche nach den Angaben des Beispiele 1 hergestellt werden können, werden in der folgenden Tabelle beschrieben.Other valuable dyes of the anthraquinone series, which can be prepared according to the information in Example 1, are described in the following table.

Sie entsprechen der FormelThey correspond to the formula

fc wobei die Symbole R1, Rp, R, und R2, die in der Tabelle angegebenen Bedeutung besitzen. Als Anion x^ kommen die in der Beschreibung aufgeführten in Frage.fc where the symbols R 1 , Rp, R and R 2 have the meanings given in the table. As the anion x ^ those listed in the description come into question.

Das Symbol K1 steht für die DimethylhydrazingruppierungThe symbol K 1 stands for the dimethylhydrazine grouping

NHNH

009833/ 1755009833/1755

RR. NH2 NH 2 R3 R 3 R2 R 2 Rl R l Nuance der FärbungShade of coloring NH-NH- auf Textilguton textile goods Bsp.E.g. NHCH,NHCH, HH OCH2CH2K1 OCH 2 CH 2 K 1 NH2 NH 2 aus Polyacrylnimade of polyacrylic Nr.No. HH OCH2CH2-K1 OCH 2 CH 2 -K 1 NH2 NH 2 triltril 22 HH OCH2CH2-K1 OCH 2 CH 2 -K 1 NH2 NH 2 rotRed 33 violettviolet dodo

009883/1755009883/1755

Claims (1)

. <to . <to PatentanspruchClaim Verfahren zur Herstellung von basischen Anthrachinonfarbstoffen der FormelProcess for the preparation of basic anthraquinone dyes of the formula 0 NIL0 NIL (D(D worin W Amino, einen gegebenenfalls substituierten Alkyl-wherein W is amino, an optionally substituted alkyl amifto- oder Phenylaminorest, Z -CH2-, -\T/) oderamifto- or phenylamino radical, Z -CH 2 -, - \ T /) or H.H. K, die Gruppierung -N-K, the grouping -N- CHCH X ein Anion bedeuten, X mean an anion, dadurch gekennzeichnet, dass man eine von Carbonsäure- und Sulfonsäuregruppe freie Verbindung der Formelcharacterized in that a compound of the formula which is free of carboxylic acid and sulfonic acid groups 0 NH.0 NH. 0-Z-CH2-E0-Z-CH 2 -E (XVII)(XVII) 009883/ 1755009883/1755 worin E den Säurerest eines Esters bedeutet, mit dem Dimethylhydrazin der Formel (III) umsetzt. in which E is the acid residue of an ester with which the dimethylhydrazine of the formula (III) is reacted. OerPatcntanwaltiOerPatcntanwalti 009883/1755009883/1755
DE19641644632 1961-04-21 1964-03-13 Process for the production of basic anthraquinone dyes Pending DE1644632A1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH489862A CH496765A (en) 1961-04-21 1961-04-21 Basic anthraquinone dyes for polymers of - acrylonitrile and copolymers of acrylonitrile and vinyl ace
CH470961A CH435495A (en) 1961-04-21 1961-04-21 Process for the preparation of hydrazine derivatives
CH35962A CH462348A (en) 1962-01-12 1962-01-12 Process for the preparation of hydrazine derivatives
CH1501362A CH461664A (en) 1962-12-21 1962-12-21 Process for the production of hydrozine derivatives
CH558863 1963-05-03
CH322563 1964-02-25

Publications (1)

Publication Number Publication Date
DE1644632A1 true DE1644632A1 (en) 1971-01-14

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Family Applications (3)

Application Number Title Priority Date Filing Date
DE19641644643 Granted DE1644643A1 (en) 1961-04-21 1964-03-13 Process for the production of basic dyes
DE19641644632 Pending DE1644632A1 (en) 1961-04-21 1964-03-13 Process for the production of basic anthraquinone dyes
DE19641644642 Pending DE1644642A1 (en) 1961-04-21 1964-03-13 Process for the production of basic anthraquinone dyes

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE19641644643 Granted DE1644643A1 (en) 1961-04-21 1964-03-13 Process for the production of basic dyes

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE19641644642 Pending DE1644642A1 (en) 1961-04-21 1964-03-13 Process for the production of basic anthraquinone dyes

Country Status (4)

Country Link
DE (3) DE1644643A1 (en)
FR (1) FR86220E (en)
GB (1) GB1061461A (en)
NL (1) NL6402587A (en)

Also Published As

Publication number Publication date
NL6402587A (en) 1964-11-10
DE1644642A1 (en) 1970-01-29
FR86220E (en) 1966-03-23
GB1061461A (en) 1967-03-15
DE1644643A1 (en) 1972-02-10

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