DE3300914A1 - Thiocyanatophenyl azo dyes, their preparation and their use - Google Patents

Thiocyanatophenyl azo dyes, their preparation and their use

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Publication number
DE3300914A1
DE3300914A1 DE19833300914 DE3300914A DE3300914A1 DE 3300914 A1 DE3300914 A1 DE 3300914A1 DE 19833300914 DE19833300914 DE 19833300914 DE 3300914 A DE3300914 A DE 3300914A DE 3300914 A1 DE3300914 A1 DE 3300914A1
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formula
alkyl
alkoxy
bromine
azo compounds
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German (de)
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Werner Dr. 4106 Therwil Baumann
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Sandoz AG
Sandoz Patent GmbH
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Sandoz AG
Sandoz Patent GmbH
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Priority to DE19833300914 priority Critical patent/DE3300914A1/en
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    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • 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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3643—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from quinolines or hydrogenated quinolines
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3686—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and oxygen as heteroatom
    • 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
    • C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms

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

Abstract

The invention relates to the azo compounds of the formula <IMAGE> in which K is the radical of a coupling component customary in dye chemistry, to their preparation and to their use as textile dyes.

Description

RHODARPHENYL-AZOFARBSTOFFE, IHRE HERSTELLUNG UND IHRE VER-RHODARPHENYL AZO DYES, THEIR MANUFACTURING AND THEIR

WENDUNG Gegenstand der Erfindung sind die Azoverbindungen der Formel I worin K der Rest einer in der Farbstoffchemie ueblichen Kupplungskomponente ist.APPLICATION The invention relates to the azo compounds of the formula I where K is the radical of a coupling component customary in dye chemistry.

Diese Verbindungen sind sehr wertvolle Farbstoffe und vor allem als Textil farbstoffe sehr gut verwendbar. Bevorzugt sind die Azoverbindungen der Formel I, worin K der Rest einer in der Chemie der Dispersionsfarbstoffe üblichen Kupplungskomponente ist, vorzugsweise der Benzol- oder l-Aminonaphthalinreihe, sie eignen sich hervorragend zum Färben und Bedrucken von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen, vor allem solchen aus Celluloseacetaten, synthetischen Polyamiden und insbesondere solchen aus linearen, aromatischen Polyestern.These compounds are very valuable dyes and especially as Textile dyes can be used very well. The azo compounds of the formula are preferred I, where K is the radical of a coupling component customary in the chemistry of disperse dyes is, preferably of the benzene or l-aminonaphthalene series, they are excellent for dyeing and printing fibers or threads or materials made from them made of fully or semi-synthetic, hydrophobic, high molecular weight organic substances, especially those made from cellulose acetates, synthetic polyamides and in particular those made from linear, aromatic polyesters.

Besonders bevorzugt sind die Verbindungen der Formel I worin K ein Rest der Formel II oder II a ist worin R1 Wasserstoff, Chlor, Brom, C1-2-Alkyl, C1-4-Alkoxy, C1-4-Alkoxyäthoxy oder Benzyloxy, R2 Wasserstoff, Chlor, Brom, C1-2-Alkyl, C1-4-Alkoxy, Phenyl-C1-3-alkoxy, Acyloxy oder Acylamino und R3 und R4 unabhängig voneinander Wasserstoff, C1-12 Alkyl, C3-4-Alkenyl, C34-Alkinyl , Benzyl oder C2 6-Alkyl, das einen oder zwei Substituenten aus der Gruppe Hydroxy, C1-4 Alkoxy, Acyloxy, Chlor, Brom, Cyan, Phenyl, Phenoxy oder C1-3-Alkoxy-carbonyl trägt und R5 geradkettiges oder verzweigtes C3 7-Alkylen oder eie Gruppe der Formel -O-(C2~4)-Alkylen, wobei das Stickstoffatom der Gruppe der Formel IIa an ein Kohlenstoffatom gebunden ist, bedeuten.The compounds of the formula I in which K is a radical of the formula II or II a are particularly preferred where R1 is hydrogen, chlorine, bromine, C1-2-alkyl, C1-4-alkoxy, C1-4-alkoxyethoxy or benzyloxy, R2 is hydrogen, chlorine, bromine, C1-2-alkyl, C1-4-alkoxy, phenyl-C1 -3-alkoxy, acyloxy or acylamino and R3 and R4 independently of one another are hydrogen, C1-12 alkyl, C3-4 alkenyl, C34 alkynyl, benzyl or C2 6 alkyl, the one or two substituents from the group hydroxy, C1- 4 carries alkoxy, acyloxy, chlorine, bromine, cyano, phenyl, phenoxy or C1-3-alkoxycarbonyl and R5 carries straight-chain or branched C3-7 alkylene or a group of the formula -O- (C2-4) -alkylene, where the Nitrogen atom of the group of the formula IIa is bonded to a carbon atom.

Bevorzugte Acylreste sind solche aus der Carbonyl- oder Sulfonylreihe, insbesondere, als Acyioxyreste, solche der Formeln -O-CO-R, -O-CO-OR, -O-CO-NR'R", -O-SO2R und -O-SO2-NR'R", und als Acylaminoreste solche der Formeln -NH-CO-R, -NH-CO-OR, -HN-CO-NH2, -NH-CO-NHR, -HN-CO-NR'R", -HN-SO2R und -NH-SO2NR'R", worin R gegebenenfalls einmal durch Chlor, Brom, Hydroxyl, C1 3-Alkoxy oder Phenoxy substituiertes C1-6-Alkyl, C5 6-Cycloalkyl, gegebenenfalls durch Chlor oder Brom substituiertes C3 4-Alkenyl, oder gegebenenfalls im Kern bis zu dreimal durch Chlor, Brom, C1 2-Alkyl und/oder C1 2-Alkoxy substituiertes Phenyl oder Phenyl-C1-2-alkyl, R' und R", unabhängig voneinander gegebenenfalls einmal durch Chlor, Brom, Hydroxyl oder C1 3-Alkoxy substituiertes C1-4-Alkyl oder gegebenenfalls bis zu dreimal durch Chlor, Brom, C1 2-Alkyl und/oder C1-2-Alkoxy substituiertes Phenyl oder R' und R" gemeinsam mit dem an sie gebundenen Stickstoffatom ein heterocyclischer Ring, vorzugsweise ein Pyrrolidinyl-, Piperid0no- oder Morpholinorest ist.Preferred acyl radicals are those from the carbonyl or sulfonyl series, in particular, as acyioxy radicals, those of the formulas -O-CO-R, -O-CO-OR, -O-CO-NR'R ", -O-SO2R and -O-SO2-NR'R ", and as acylamino radicals those of the formulas -NH-CO-R, -NH-CO-OR, -HN-CO-NH2, -NH-CO-NHR, -HN-CO-NR'R ", -HN-SO2R and -NH-SO2NR'R", where R is optionally C1-6-alkyl substituted once by chlorine, bromine, hydroxyl, C1-3-alkoxy or phenoxy, C5 6-Cycloalkyl, optionally substituted by chlorine or bromine C3 4-alkenyl, or optionally in the nucleus up to three times by chlorine, bromine, C1 2 -alkyl and / or C1 2-alkoxy substituted phenyl or phenyl-C1-2-alkyl, R 'and R ", independently each other optionally once by chlorine, bromine, hydroxyl or C1 3-alkoxy-substituted C1-4-alkyl or optionally up to three times by chlorine, Bromine, C1-2-alkyl and / or C1-2-alkoxy-substituted phenyl or R 'and R "together with the nitrogen atom attached to it a heterocyclic ring, preferably is a pyrrolidinyl, piperido or morpholino radical.

Insbesondere bevorzugt sind Reste von Kupplunqskomponenten K der Formel II, worin R1 Wasserstoff oder C1 2-Alkoxy, R2 Wasserstoff, Methyl, C1-2-Alkyl-carbonylamino oder C1-2-Alkoxycarbonylamino und R3 und R4 unabhängig voneinander C1 8-Alkyl, C3-4-Alkenyl oder einmal durch Hydroxyl, C1-2-Alkyl-carbonyloxy, C1-2-Alkoxy-carbonyloxy, C1-3-Alkoxy-carbonyl oder Cyan substituiertes C2 4-Alkyl bedeuten.Residues of coupling components K of the formula are particularly preferred II, in which R1 is hydrogen or C1 2-alkoxy, R2 is hydrogen, methyl, C1-2-alkyl-carbonylamino or C1-2-alkoxycarbonylamino and R3 and R4 independently of one another C1-8-alkyl, C3-4-alkenyl or once by hydroxyl, C1-2-alkyl-carbonyloxy, C1-2-alkoxy-carbonyloxy, C1-3-alkoxycarbonyl or C2 4 alkyl substituted by cyano.

Die Herstellung der neuen Verbindungen der Formel 1 erfolgt entweder durch Kuppeln des diazotierten Amins der Formel III mit einer Verbindung der Formel IV H - K (IV), oder durch Umsetzung einer Azoverbindung der Formel V worin X ein Halogenatom, vorzugsweise ein Chlor oder Bromatom bedeutet, mit einem Salz der Rhodanwasserstoffsä.ure.The new compounds of formula 1 are prepared either by coupling the diazotized amine of formula III with a compound of the formula IV H - K (IV), or by reacting an azo compound of the formula V in which X is a halogen atom, preferably a chlorine or bromine atom, with a salt of hydrohalic acid.

Die Verbindung der Formel III ist bekannt (Russ. Pat. 436.817).The compound of the formula III is known (Russ. Pat. 436.817).

Diazotieren und Kuppeln erfolgen analog zu allgemein bekannten Methoden.Diazotization and coupling are carried out analogously to generally known methods.

Die Verbindungen der Formel V lassen sich, sofern sie nicht ebenfalls bekannt sind, leicht in Analogie zu bekannten Verfahren herstellen.The compounds of the formula V can, provided they are not also are known, easily prepared in analogy to known processes.

Die Umsetzung einer Verbindung der Formel V mit einem Salz der Rhodanwasserstoffsäure, vorzugsweise einem Alkali- oder dem Ammoniumsalz, geht ohne Schwierigkeiten vor sich, sie wird im allgemeinen ìn einem polaren, aprotischen Lösungsmittel, z.B.The reaction of a compound of the formula V with a salt of hydrofluoric acid, preferably an alkali or the ammonium salt, proceeds without difficulty it is generally dissolved in a polar, aprotic solvent, e.g.

Dimethylformamid, N-Methylpyrrolidon, Sulfolan oder Dimethylsulfoxid, durchgeführt, läs&t sich aber auch in anderen Lösungsmitteln z,B. Alkoholen oder Gemischen aus Wasser und organischen Lösungsmitteln und unter Phasentransfer-Bedingungen durchführen.Dimethylformamide, N-methylpyrrolidone, sulfolane or dimethyl sulfoxide, carried out, but can also be used in other solvents, e.g. Alcohols or mixtures of water and organic solvents and under phase transfer conditions carry out.

Die von wasserlöslich machenden Gruppen freien Azofarbstoffe der Formel I ziehen aus wässriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben, Klotzen oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern, sowie aus Cellulose-2 ll2-acetat, Cellulosetriacetat und synthetischen Polyamiden. Die Verarbeitung dieser Farbstoffe zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z.B. durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken.The azo dyes of the formula which are free from water-solubilizing groups I pull from aqueous suspension excellent on textile material made of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. Particularly they are suitable for dyeing, padding or printing textile material made of linear, aromatic polyesters, as well as from cellulose-2 ll2-acetate, cellulose triacetate and synthetic polyamides. The processing of these dyes into dye preparations takes place in a generally known manner, e.g. by grinding in the presence of dispersing agents and / or fillers. With the optionally dried in a vacuum or by atomization After adding more or less water, preparations can be made for a long time or short liquor dyeing, padding or printing.

Man färbt, klotzt oder bedruckt nach an sich bekannten, z.B.It is colored, padded or printed according to known methods, e.g.

den in der französischen Patentschrift Nr. 1.445,371 beschriebenen Verfahren Die neuen Farbstoffe besitzen ausgezeichnete Echtheitseigenschaften; vor allem ist die hervorragende Lichtechtheit bemerkenswert, Hervorzuheben sind auch die gute Sublimierechtheit und die grosse Farbstärke der neuen Verbindungen.those described in French Patent No. 1,445,371 procedure The new dyes have excellent fastness properties; Above all, the excellent lightfastness is noteworthy, to be emphasized also the good fastness to sublimation and the great color strength of the new compounds.

In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozcnte. Die Temperaturen sind in Celsiusgraden angegeben, B e i s p i e 1 la 10 Teile 2,4-Dinitro-5-thiocyananilin in 120 Teilen 85«, ortho-Phosphorsäure werden bei -10° mit 13,5 Teilen einer 40%,-igen Lösung von Nitrosylschwefelsäure in konzentrierter Schwefelsäure versetzt. Man rührt 6 Stunden bei dieser Temperatur nach und lässt dann die erhaltene Suspension langsam zu einer Mischung aus 6,3 Teilen N,N-Diethyl-m-toluidin, 70 Teilen konz. Salzsäure und 70 Teilen Eis laufen. Man lässt die Reaktionsmischung auf 10° erwärmen und rührt 16 Stunden nach. Der gebildete Farbstoff der Formel a wird abfiltriert, mit Wasser gewaschen und im Vakuum getrocknet.In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius, for example 10 parts of 2,4-dinitro-5-thiocyananiline in 120 parts of 85 ", orthophosphoric acid at -10 ° with 13.5 parts of a 40% solution of Nitrosylsulfuric acid is added to concentrated sulfuric acid. The mixture is stirred for 6 hours at this temperature and then the suspension obtained is slowly added to a mixture of 6.3 parts of N, N-diethyl-m-toluidine, 70 parts of conc. Hydrochloric acid and 70 parts of ice. The reaction mixture is allowed to warm to 10 ° and stirred for 16 hours. The resulting dye of the formula a is filtered off, washed with water and dried in vacuo.

#max dieses Farbstoffs (Methylenchlorid) = 602 nm, 8 e i s p i e 1 lb 10 Teile des Farbstoffs der Formel b den Cyan erhält, wenn man gemNss oben beschriebenem Verfahren 5-Chlor-2,4-dinitroanilin diazotiert und auf N,N-Diethyl-mtoluidin kuppelt, und 2,5 Teile Kaliumrhodanid in 100 Teilen Dimethylformamid werden während 16 Stunden bei 80° gerührt.#max of this dye (methylene chloride) = 602 nm, 8 ice pieces 1 lb 10 parts of the dye of the formula b the cyan is obtained when 5-chloro-2,4-dinitroaniline is diazotized according to the process described above and coupled to N, N-diethyl-mtoluidine, and 2.5 parts of potassium thiocyanate in 100 parts of dimethylformamide are stirred at 80 ° for 16 hours.

Das Reaktionsgemisch wird dann auf Raumtemperatur abgekühlt und mit 1500 Teilen Wasser versetzt. Der ausgefallene Farbstoff der Formel a) wird abfiltriert, mit Wasser gewaschen und im Vakuum getrocknet, F A E R 8 E B E I S P I E L 7 Teile des gemäss Beispiel la, bzw. 1b erhaltenen Farbstoffs werden mit 13 Teilen ligninsulfonsaurem Natrium, 25 Teilen Wasser und 100 Teilen Siliquarzitperlen gemahlen, bis der Durchmesser der Farbstoffteilchen im Mittel unter 1 µ liegt.The reaction mixture is then cooled to room temperature and with 1500 parts of water are added. The precipitated dye of the formula a) is filtered off, washed with water and dried in vacuo, F A E R 8 E B E I S P I E L 7 parts of the dye obtained according to Example la or 1b are mixed with 13 parts of lignosulfonic acid Sodium, 25 parts of water and 100 parts of silica quartzite beads ground up the diameter the mean of the dye particles is below 1 µ.

Die Suspension wird von den Siliquarzitperlen abfiltriert und unter milden Bedingungen getrocknet und zerstäubt. 1 Teil des so erhaltenen Farbstoffpräparates wird mit 4000 Teilen 60° warmem, auf pH 5 abgepuffertem Wasser verrührt. Mit dieser Färbeflotte werden 100 Teile Polyesterfasergewebe 1 Stunde bei 1300 unter erhöhtem Druck gefärbt. Nach dem Abkühlen, Spülen, Seifen, nochmaligem Spülen und Trocknen erhält man eine egale blaue Färbung von hohem Echtheitsniveau.The suspension is filtered off from the siliquarzite beads and taken under dried and atomized in mild conditions. 1 part of the dye preparation thus obtained is stirred with 4000 parts of 60 ° warm, pH 5 buffered water. With this Dye liquor are 100 parts of polyester fiber fabric for 1 hour at 1300 under increased Colored print. After cooling down, rinsing, soaking, rinsing again and drying a level blue dyeing with a high level of fastness is obtained.

In den folgenden Tabellen sind weitere, gemäss den Vorschriften des Beispiels la und lb herstellbare Farbstoffe angegeben, sie entsprechen der Formel (Tabelle 1) (Tabelle 2).In the following tables, further dyes which can be prepared according to the instructions of Examples 1 a and 1 b are given; they correspond to the formula (Table 1) (Table 2).

T a b e l l e 1 Bsp. R1 ; R2 R3 R4 Nuance Nr. auf PES 2 -H -H tC2H5 -C2H5 blau 3 -CH3 44 do, do. do. 4 -C2H5 -H do, do. do. 5 -OCH3 -NHCOCH3 -CH2CH20C0CH3 -CH2CH,OCOCH, grünblau 6 -OC2H5 do. do. do. do. 7 -OCH2CH20C2H5 do. do. do. do. 8 -°CH2c6H5 do. ; do. do. do. 9 -H -C2H5 -C2H5 -C 2H5 do. 10 -H -Cl -CH3 -CH3 violett 11 -H -Br i do. do. do. 12 -H -OCH3 . -C2H5 -c2H5 blau 13 -H °(CH2)3CH3 do. do. do. 14 -H -O-CH2C6H5 do. do. I do. 15 -H -O(CH2)3c6HS do. do. do. 16 -H -OCOCH3 do. do. do. 17 -H -OCOC6H5 do. do. do. 18 -H -OCOOC2H5 do. do. do. 19 -H -OCON(CH3)2 do. do. do. 20 -H -OS02CH3 do. do. do. 21 -H -OS02(CH2)3CH3 do. do. do. 22 -H -OS02CH3 do, do. do. 23 -H -OSO,- i do. do. do. 24 -H - -NHCOCH3 do, do. do. 25 -H -NHCOC2H5 do, do. do. 26 -H -NHCO(CH2)5CH3 do. do. do. Nuance Bsp. R1 R2 R3 R4 auf PES Nr. 27 1 -H -NHCOCH2C1 -C2H5 -C2H5 blau 28 1 -H -NHCOCH2Br da. do. do. 29 -H -NHCOCH2CIS2C1 da. da. do. 30 -H -NHCO(CH2)30H do. do. do. 31 -H -0HC0CR2-CH=CH2 do. do. do. 32 -H -NHCO 4 do. do. do. 33 -H -NHCOCH20C6H5 do. do. do. 34 -H -NHCOOCH3 do. do. do. 35 -H -NHCOOC2H5 do. do. do. 36 1 -H -NHCoOCH2CH(CH3)2 do. do. do. 37 -H -NHCOOC6H5 do. do. do. 38 -H -NHCOOCH2C6H5 do. do. do. 39 -H -NHCOOCH2-CH=CH2 do. do. do. 40 H -NHC0OCH2CH20C2H5 dc. do. do. 41 -H -NHCONH2 do. do. do. 42 -H -NHCONHCH3 do. do. do. 43 -H -NHCoNH(CH2)3CH3 dc. do. do. 44 -H -NHCONHC6H5 do. do. do. 45 -H -NHCON(C2Hs) do. do. do. 46 -H -CH3 do. -H violett 47 -H do. do. -CH3 blau 48 -H do. do. -(CH2)3CH3 do. 49 1 -H do. do. -CH2CH2CH(CH3)2 do. 50 -H do do. i -(CH2)5cH3 do. 51 -H do. do. -(CH2)9CH3 do. 52 -H do. do. -(CH2)11CH3 do. 53 -H i do. do. -CH2C6H5 do. Nuance XrP I R2 R3 R4 auf PES ~ . . 54 -H -CH3 -C2H5 -CH2CH2C6H5 blau 55 -H do. da. -(CH2)3C6H5 do. 56 -H do. da. -CH2CH2C1 violett 57 -H do. da. -CH2CH2CN do. 58 -H do. do. -CH2CH20H do. 59 -H da. do, -CH2CH20COCH3 da. 60 -H do. do. -CH2CH20COC6H5 do. 61 -H do. da. -CH2CH20C0NHC6H5 da. 62 -H do. do. } -CH2CH20C2H5 do. 63 -H do. do. -CH2CH2OC6H5 da 64 -H do. da. -(CF<2)30C6H5 do. 65 -H do. do. -(CH2)4°c6H5 do. 66 -H do. do. | -(CH2)50C6H5 do. 67 -H do. da. -(CH2)60C6H5 do. 68 -H do. 1 do. t -CH2-CH=CH2 do. 69 -H i do. do. -CH2-CH=CH-CH3 do. 70 -H do. do. -CH2-C ~ CH do. 71 -H do. do. -CH2CH2-COOC2Hs da. 72 -H do. do. -CH2CH(O)CH20C6H5 do. 73 -OCH3 -NHCOCH3 -C2H5 -C2H5 grün 74 -OC2H5 da. do. da. do. 75 -H -NHC0C6H5 da. do. blau 76 -H -NHCO e CH3 da, do. do. 77 -H -NHCO(CH2)2CH3 do. do. do. 78 -H -NHCOCH(CH3)2 do. do. do. 79 -H -NHCOCH2CH(CH3)2 do. do. Ja. 80 -H -NHCO(CH2)4CH3 do do. da. 81 -H -NHCOC(CH3)3 do. do. da. 82 -H -CH3 -(CH2)3C43 -(CH2)3CH3 da. 83 -H do, /-CH2CH2CH(CH3)2 -CH2CH2CH(CH3)2 do. Bsp. R1 R2 R3 R4 Nuance Nr. auf PES 84 -H -CH3 -(CH2)5CH3 -(CH2)5CH3 blau 85 -H -H -C2H5 -CH2CH2-0-C6H5 violett 86 -H -H -CH2CH2CN -CH2CH2-OCOCH3 rot 87 -H | -H -CH2CH2OCOCH3 do. - violett 88 -CH3 -CH3 -H -(CH2)5CH3 do. 89 -OCH3 -CH3 CH3 -CH2CH-CH2-O-C6H5 OH blau Tabelle 2 Bsp. R2 R4 R5 Nuance NR. @ 4 @ auf PES 90 H -(CH2)5CH3 -(CH2)3- blau 91 H do. -CH(CH3)CH2C(CH3)2- do. 92 H -H do. do. 93 -CH3 -H do. da. 94 -CH3 -(CH2)5CH3 do. do. 95 -H do. -O-CH2-CH(CH3)- do. Table 1 Ex. R1; R2 R3 R4 nuance No. on PES 2 -H -H tC2H5 -C2H5 blue 3 -CH3 44 do, do. do. 4 -C2H5 -H do, do. do. 5 -OCH3 -NHCOCH3 -CH2CH20C0CH3 -CH2CH, OCOCH, green-blue 6 -OC2H5 do. do. do. do. 7 -OCH2CH20C2H5 do. do. do. do. 8 - ° CH2c6H5 do. ; do. do. do. 9 -H -C2H5 -C2H5 -C 2H5 do. 10 -H -Cl -CH3 -CH3 purple 11 -H -Br i do. do. do. 12 -H -OCH3. -C2H5 -c2H5 blue 13 -H ° (CH2) 3CH3 do. do. do. 14 -H -O-CH2C6H5 do. do. I do. 15 -H-O (CH2) 3c6HS do. do. do. 16 -H -OCOCH3 do. do. do. 17 -H -OCOC6H5 do. do. do. 18 -H -OCOOC2H5 do. do. do. 19 -H-OCON (CH3) 2 do. do. do. 20 -H -OS02CH3 do. do. do. 21 -H -OS02 (CH2) 3CH3 do. do. do. 22 -H -OS02CH3 do, do. do. 23 -H -OSO, - i do. do. do. 24 -H - -NHCOCH3 do, do. do. 25 -H -NHCOC2H5 do, do. do. 26 -H -NHCO (CH2) 5CH3 do. do. do. nuance E.g. R1 R2 R3 R4 on PES No. 27 1 -H -NHCOCH2C1 -C2H5 -C2H5 blue 28 1 -H -NHCOCH2Br da. do. do. 29 -H -NHCOCH2CIS2C1 da. there. do. 30 -H -NHCO (CH2) 30H do. do. do. 31 -H -0HC0CR2-CH = CH2 do. do. do. 32 -H -NHCO 4 do. do. do. 33 -H -NHCOCH20C6H5 do. do. do. 34 -H -NHCOOCH3 do. do. do. 35 -H -NHCOOC2H5 do. do. do. 36 1 -H -NHCoOCH2CH (CH3) 2 do. do. do. 37 -H -NHCOOC6H5 do. do. do. 38 -H -NHCOOCH2C6H5 do. do. do. 39 -H -NHCOOCH2-CH = CH2 do. do. do. 40 H -NHC0OCH2CH20C2H5 dc. do. do. 41 -H -NHCONH2 do. do. do. 42 -H -NHCONHCH3 do. do. do. 43 -H -NHCoNH (CH2) 3CH3 dc. do. do. 44 -H -NHCONHC6H5 do. do. do. 45 -H -NHCON (C2Hs) do. do. do. 46 -H -CH3 do. -H purple 47 -H do. do. -CH3 blue 48 -H do. do. - (CH2) 3CH3 do. 49 1 -H do. do. -CH2CH2CH (CH3) 2 do. 50 -H do do. i - (CH2) 5cH3 do. 51 -H do. do. - (CH2) 9CH3 do. 52 -H do. do. - (CH2) 11CH3 do. 53 -H i do. do. -CH2C6H5 do. nuance XrP I R2 R3 R4 on PES ~. . 54 -H -CH3 -C2H5 -CH2CH2C6H5 blue 55 -H do. there. - (CH2) 3C6H5 do. 56 -H do. there. -CH2CH2C1 purple 57 -H do. there. -CH2CH2CN do. 58 -H do. do. -CH2CH20H do. 59 -H there. do, -CH2CH20COCH3 there. 60 -H do. do. -CH2CH20COC6H5 do. 61 -H do. there. -CH2CH20C0NHC6H5 there. 62 -H do. do. } -CH2CH20C2H5 do. 63 -H do. do. -CH2CH2OC6H5 there 64 -H do. there. - (CF <2) 30C6H5 do. 65 -H do. do. - (CH2) 4 ° c6H5 do. 66 -H do. do. | - (CH2) 50C6H5 do. 67 -H do. there. - (CH2) 60C6H5 do. 68 -H do. 1 do. t -CH2-CH = CH2 do. 69 -H i do. do. -CH2-CH = CH-CH3 do. 70 -H do. do. -CH2-C ~ CH do. 71 -H do. do. -CH2CH2-COOC2Hs there. 72 -H do. do. -CH2CH (O) CH20C6H5 do. 73 -OCH3 -NHCOCH3 -C2H5 -C2H5 green 74 -OC2H5 there. do. there. do. 75 -H -NHC0C6H5 there. do. blue 76 -H -NHCO e CH3 da, do. do. 77 -H -NHCO (CH2) 2CH3 do. do. do. 78 -H -NHCOCH (CH3) 2 do. do. do. 79 -H -NHCOCH2CH (CH3) 2 do. do. Yes. 80 -H -NHCO (CH2) 4CH3 do do. there. 81 -H -NHCOC (CH3) 3 do. do. there. 82 -H -CH3 - (CH2) 3C43 - (CH2) 3CH3 da. 83 -H do, / -CH2CH2CH (CH3) 2 -CH2CH2CH (CH3) 2 do. Ex. R1 R2 R3 R4 Nuance No. on PES 84 -H -CH3 - (CH2) 5CH3 - (CH2) 5CH3 blue 85 -H -H -C2H5 -CH2CH2-0-C6H5 purple 86 -H -H -CH2CH2CN -CH2CH2-OCOCH3 red 87 -H | -H -CH2CH2OCOCH3 do. - purple 88 -CH3 -CH3 -H - (CH2) 5CH3 do. 89 -OCH3 -CH3 CH3 -CH2CH-CH2-O-C6H5 OH blue Table 2 Ex. R2 R4 R5 Nuance NO. @ 4 @ on PES 90 H - (CH2) 5CH3 - (CH2) 3- blue 91 H do. -CH (CH3) CH2C (CH3) 2- do. 92 H -H do. do. 93 -CH3 -H do. there. 94 -CH3 - (CH2) 5CH3 do. do. 95 -H do. -O-CH2-CH (CH3) - do.

Claims (7)

RHODANPHENYL-AZOFARBSTOFFE, I@RE HERSTELLUNG UND IHRE VER-WENDUNG P a t e n t a n s p r ü c h e 1. Die Azoverbindungen der Formel worin K der Rest einer in der Farbstoffchemie üblichen Kupplungskomponente ist.RHODANPHENYL AZO DYES, I @ RE MANUFACTURING AND THEIR USE P atent claims 1. The azo compounds of the formula where K is the radical of a coupling component customary in dye chemistry. 2. Die Azoverbindungen der Fonnel I, gemass Anspruch 1 worin K der Rest einer in der Chemie der Dispersionsfarbstoffe übliche Kupplungskomponente ist.2. The azo compounds of Fonnel I, according to claim 1 wherein K is the The remainder is a coupling component customary in the chemistry of disperse dyes. 3, Die Azoverbindungen der Formel I, gemäss Anspruch 1, worin K der Rest einer von wasserlöslich machenden Gruppen freien Kupplungskomponente der Benzol-oder l-Aminonaphthalinreihe ist.3, The azo compounds of the formula I according to claim 1, wherein K is the Remainder of a coupling component of the benzene or benzene or coupling component which is free from water-solubilizing groups is l-aminonaphthalene series. 4, Die Azoverbindungen der Formel I, gemass Anspruch 1, 2 oder 3, worin K ein Rest der Formel I1 oder IIa ist worin R1 Wasserstoff, Chlor, Brom, C1-2-Alkyl, C1-4-Alkoxy, C1 4-Alkoxyäthoxy oder Benzyloxy, R2 Wasserstoff, Chlor, Brom, C1-2-Alkyl, C1-4-Alkoxy, Phenyl-C1-3-alkoxy, Acyloxy oder Acylamino, R3 und R4 unabhängig voneinander Wasserstoff, C1 12-Alkyl, C3 4-Alkenyl, C3-4-Alkinyl, Benzyl oder C2-6-Alkyl, das einen oder zwei Substituenten aus der Gruppe Hydroxy, C1 4-Alkoxy, Acyloxy, Chlor, Brom, Cyan, Phenyl, Phenoxy oder C1-3 Alkoxy-carbonyl trägt und R5 geradkettiges oder verzweigtes C3 7-Alkylen oder eine Gruppe der Formel -0-(C2-4)-Alkylen, wohei das Stickstoffatom an ein Kohlenstoffatom gebunden ist, bedeuten.4. The azo compounds of the formula I according to claim 1, 2 or 3, in which K is a radical of the formula I1 or IIa where R1 is hydrogen, chlorine, bromine, C1-2-alkyl, C1-4-alkoxy, C1-4-alkoxyethoxy or benzyloxy, R2 is hydrogen, chlorine, bromine, C1-2-alkyl, C1-4-alkoxy, phenyl-C1- 3-alkoxy, acyloxy or acylamino, R3 and R4 independently of one another are hydrogen, C1-12-alkyl, C3-4-alkenyl, C3-4-alkynyl, benzyl or C2-6-alkyl, one or two substituents from the group hydroxy, C1 4-alkoxy, acyloxy, chlorine, bromine, cyano, phenyl, phenoxy or C1-3 alkoxycarbonyl carries and R5 straight-chain or branched C3 7-alkylene or a group of the formula -0- (C2-4) -alkylene, where the Nitrogen atom is bonded to a carbon atom, mean. 5. Verfahren zur Herstellung der Azoverbindungen der Formel I, gemäss Anspruch 1, dadurch gekennzeichnet, dass man ein diazotiertes Amin der Formel III mit einer Verbindung der Formel IV H - K (IV) kuppelt.5. Process for the preparation of the azo compounds of the formula I according to Claim 1, characterized in that a diazotized amine of the formula III with a compound of the formula IV H - K (IV). 6. Verfahren zur Herstellung der Azoverbindungen der Formel I, gemäss Anspruch 1, dadurch gekennzeichnet, dass man eine Azoverbindung der Formel V worin X Halogen , vorzugsweise Chlor oder Brom bedeutet, mit einem Salz der Rhodanwasserstoffsäure umsetzt.6. Process for the preparation of the azo compounds of the formula I according to claim 1, characterized in that an azo compound of the formula V is used wherein X is halogen, preferably chlorine or bromine, is reacted with a salt of hydrofluoric acid. 7. Verwendung der Verbindungen der Formel I, gemäss Anspruch 1, als Textilfarbstoffe.7. Use of the compounds of formula I according to claim 1 as Textile dyes.
DE19833300914 1982-01-23 1983-01-13 Thiocyanatophenyl azo dyes, their preparation and their use Withdrawn DE3300914A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1013717A1 (en) * 1998-12-21 2000-06-28 DyStar Textilfarben GmbH &amp; Co. Deutschland KG Thermomigration-fast azo dyes
CN114402039A (en) * 2019-03-27 2022-04-26 德司达染料分销有限公司 High wet fastness disperse dye mixtures of N- [4- (5-thiocyano-2, 4-dinitro-phenylazo) -phenyl ] -amine derivatives and N- [4- (4-nitro-phenylazo) -phenyl ] -amine derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1013717A1 (en) * 1998-12-21 2000-06-28 DyStar Textilfarben GmbH &amp; Co. Deutschland KG Thermomigration-fast azo dyes
US6191265B1 (en) 1998-12-21 2001-02-20 Dystar Textilfarben Gmbh & Co. Deutschland Kg Thermomigrationfast azo dyes
CN114402039A (en) * 2019-03-27 2022-04-26 德司达染料分销有限公司 High wet fastness disperse dye mixtures of N- [4- (5-thiocyano-2, 4-dinitro-phenylazo) -phenyl ] -amine derivatives and N- [4- (4-nitro-phenylazo) -phenyl ] -amine derivatives

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