DE2805201A1 - Diazo dyes contg. a dioxanyl gp. - imparting red, blue etc. colours to synthetic fibres - Google Patents

Diazo dyes contg. a dioxanyl gp. - imparting red, blue etc. colours to synthetic fibres

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Publication number
DE2805201A1
DE2805201A1 DE19782805201 DE2805201A DE2805201A1 DE 2805201 A1 DE2805201 A1 DE 2805201A1 DE 19782805201 DE19782805201 DE 19782805201 DE 2805201 A DE2805201 A DE 2805201A DE 2805201 A1 DE2805201 A1 DE 2805201A1
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formula
alkyl
hydrogen
chlorine
group
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German (de)
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Klaus Dr Koerte
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Sandoz AG
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Sandoz AG
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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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081—Isothiazoles or condensed isothiazoles
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0092—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group

Abstract

New azo dispersion dyes are of formula (I). In (I) D is a diazo component of the type known in dispersion dyes; K is an opt. substd. 1,4-phenylene or 1,4-naphthylene gp.; R1 is H, 1-4C alkyl or 2-4C alkenylene, or, if K is 1,4-phenylene, R1 may also be 2-4C alkyl or 2-4C alkenyl which may be substd. by a gp. chosen from Cl, Br, OH, CN, 1-4C alkoxy, phenoxy, phenyl, formyloxy, 1-4C alkylcarbonyloxy, benzoyloxy, 1-4C alkoxycarbonyl, 1-4C alkoxycarbonyloxy, 1-4C alkyl or di-(1-4C alkyl)-aminocarbonyloxy gp., or a gp. (II); and R2 is 1-4C alkylene or 2-4C alkylene-O-2-4C alkylene gp. The molecule is free from sulphonic acid-, acetal-, -N (I) are useful red, brown, orange, violet and blue dyes with excellent fastness to light, moisture, heat fixing, sublimation pleating. They are esp. useful for dyeing and printing synthetic or semi-synthetic high molecular organic materials, esp. textiles of aromatic polyesters, cellulose 2 1/2- and 3-acetate, polyamides, etc.

Description

Azo-Dispersionsfarbstoffe, ihre Herstellung undAzo disperse dyes, their manufacture and

Verwendung Gegenstand der Erfindung sind Azo-Dispersionsfarbstoffe, bzw. ein Verfahren zu ihrer Herstellung.use The invention relates to azo disperse dyes, or a process for their production.

Die neuen Farbstoffe entsprechen der Formel I worin D den Rest einer in der Chemie der Dispersionsfarbstoffe üblichen Diazokomponente, K gegebenenfalls weitere Substituenten tragendes 1,4-Phenylen oder 1,4-Naphthylen, R1 Wasserstoff, C1-4-Alkyl oder C 2-4 -Alk enyl oder, wenn K 1,4-Phenylen bedeutet, auch C2-4-Alkyl oder C 2-4 Alkenyl, das einen Substituenten aus der Gruppe Chlor, Brom, Hydroxy, Cyan, C14-Alkoxy, Phenoxy, Phenyl, Formyloxy, C1 -Alkyl-carbonyloxy, Benzoyloxy, C1-4-Alkoxy-carbonyl, C1-4-Alkoxy--carbonyloxy, C1 4-Alkyl- oder Di-(Cl 4--alkyl)-aminocarbonyloxy oder eine Gruppe der Formel und R2 C1-4-Alkylen oder C2-4-Alkylen-O-C2-4-Alkylen bedeuten, wobei das Molekül von Sulfonsäure- und Acetalgruppen, sowie von Gruppen der Formel 2 -N#CH2-N# und -N#CH2-S- frei ist. Jeweils unabhängig von den übrigen Symbolen, bzw. Substituenten am Molekül der Formel I bedeuten vorzugsweise: D Phenyl, das 1, 2 oder 3 Substituenten trägt, darunter je 0, einen oder zwei aus der Gruppe Chlor, Brom, Jod, Nitro, Cyan, Methyl oder Methylsulfonyl und/oder je O oder einen aus der Gruppe Methoxy, Formyl, C1-2-Alkyl--carbonyl, C1-2-Alkoxy-carbonyl, Benzoyl, Rhodan, Toluylsulfonyl, Aminosulfonyl, C1 2-Alkyl- oder Di-(C1-2-alkyl)-aminosulfonyl, Aminocarbonyl, C1 2-Alkyl- oder Di-(C1-2--alkyl)-aminocarbonyl, Phenylaminocarbonyl, N-Aethyl-N--phenylaminocarbonyl, Trifluormethyl, Phenyl, C2 3-Alkanoylamino und Phenylazo, worin der Phenylkern bis zu zwei Substituenten, und zwar Chlor und/oder Nitro tragen kann, Thienyl, das 1, 2 oder 3 Substituenten trägt, darunter je 0, einen oder zwei aus der Gruppe Chlor, Brom, Nitro, Cyan und Methyl und/oder je O oder einen aus der Gruppe Phenyl, C2~3-Alkanoyl und C1-2-Alkoxy-carbonyl, Thiazolyl, Benzthiazolyl oder Benzisothiazolyl, das bis zu zwei Substituenten tragen kann, darunter je 0, einen oder zwei aus der Gruppe Chlor, Brom, Nitro und Cyan und/oder je O oder einen aus der Gruppe Methyl, Rhodan, Aminosulfonyl und C1-2-Alkylsulfonyl oder Phenyl-(1,3,4)-- oder (l,3,5)-thiadiazolyl-2.The new dyes correspond to formula I. where D is the radical of a diazo component customary in the chemistry of disperse dyes, K 1,4-phenylene or 1,4-naphthylene optionally bearing further substituents, R1 is hydrogen, C1-4-alkyl or C 2-4 -alkenyl or, if K 1,4-phenylene means, also C2-4-alkyl or C 2-4 alkenyl, which has a substituent from the group chlorine, bromine, hydroxy, cyano, C14-alkoxy, phenoxy, phenyl, formyloxy, C1-alkyl-carbonyloxy, Benzoyloxy, C1-4-alkoxy-carbonyl, C1-4-alkoxy-carbonyloxy, C1 4-alkyl- or di- (Cl 4-alkyl) -aminocarbonyloxy or a group of the formula and R2 denotes C1-4-alkylene or C2-4-alkylene-O-C2-4-alkylene, the molecule being composed of sulfonic acid and acetal groups, and of groups of the formula 2 -N # CH2-N # and -N # CH2 -S- is free. In each case, independently of the other symbols or substituents on the molecule of the formula I, the following preferably mean: D Phenyl which has 1, 2 or 3 substituents, including 0, one or two from the group chlorine, bromine, iodine, nitro, cyano, Methyl or methylsulfonyl and / or each O or one from the group methoxy, formyl, C1-2-alkyl-carbonyl, C1-2-alkoxycarbonyl, benzoyl, rhodan, toluylsulfonyl, aminosulfonyl, C1 2-alkyl or di- (C1-2-alkyl) -aminosulfonyl, aminocarbonyl, C1 2-alkyl- or di- (C1-2-alkyl) -aminocarbonyl, phenylaminocarbonyl, N-ethyl-N-phenylaminocarbonyl, trifluoromethyl, phenyl, C2 3-alkanoylamino and phenylazo, in which the phenyl nucleus can carry up to two substituents, namely chlorine and / or nitro, thienyl which has 1, 2 or 3 substituents, including 0, one or two from the group consisting of chlorine, bromine, nitro, cyano and Methyl and / or each O or one from the group consisting of phenyl, C2-3-alkanoyl and C1-2-alkoxycarbonyl, thiazolyl, benzthiazolyl or benzisothiazolyl, which is up to can carry two substituents, including 0, one or two from the group chlorine, bromine, nitro and cyano and / or each O or one from the group methyl, rhodan, aminosulfonyl and C1-2-alkylsulfonyl or phenyl- (1,3 , 4) - or (1,3,5) -thiadiazolyl-2.

Besonders bevorzugt ist Phenyl als Diazokomponente, das als Substituenten Chlor, Brom, Jod, Nitro, Cyan, Methyl, Methoxy, Methylsulfonyl, C2 3-Alkanoyl, Aminosulfonyl, C1-2-Alkyl- oder Di-(Cl 2-alkyl)-aminosulfonyl und/oder 2-Chlor-4-nitrophenylazo tragen kann.Phenyl is particularly preferred as the diazo component and that as the substituent Chlorine, bromine, iodine, nitro, cyano, methyl, methoxy, methylsulfonyl, C2 3-alkanoyl, aminosulfonyl, C1-2-alkyl- or di- (Cl 2-alkyl) -aminosulfonyl and / or 2-chloro-4-nitrophenylazo can carry.

Insbesondere bedeutet D einen Rest der Formel V K einen unsubstituierten 1,4-Naphthylenrest oder einen Rest der Formel VI insbesondere 1,4-Naphthylen, R1, wenn K einen Rest der Formel VI bedeutet, Wasserstoff, Allyl oder C24 Alkyl, das einen Substituenten aus der Gruppe Chlor, Brom, Hydroxy, Cyan, C12-Alkoxy, Phenoxy, Phenyl, Formyloxy, C2-4-Alkanoyloxy, Benzoyloxy, C12 -Alkoxy-carbonyl, C1-4-Alkoxy-carbonyloxy, C1-2-Alkyl-und Di-(C1-2 -alkyl)-aminocarbonyloxy traqen kann oder eine Gruppe insbesondere Wasserstoff, Aethyl, Cyanäthyl, Acetoxyäthyl, vor allem Wasserstoff oder Aethyl, oder, wenn K 1,4-Naphthylen ist, Wasserstoff oder C2 4-Alkyl, insbesondere Wasserstoff oder Aethyl, vor allem Wasserstoff; -R2 geradkettiges C1 4-Alkyl oder eine Gruppe der Formel -C(CH3)H-CH2-, -CH2-CH(CH3)- oder -CH2CH2-0-CH2CH2 -, insbesondere 1,2-Aethylen; R3 Wasserstoff, Chlor, Brom, Jod, Methylsulfonyl oder Cyan, insbesondere Wasserstoff, Chlor, Brom oder Methylsulfonyl; R4 Wasserstoff, Chlor, Brom, Methyl, Methoxy, Nitro, Cyan oder Trifluormethyl, insbesondere Chlor, Brom oder Nitro; R5 Wasserstoff, Chlor,Brom, Methyl, Methoxy oder Aethoxy, insbesondere Wasserstoff, Methoxy oder Aethoxy; R6 Wasserstoff, Chlor, Brom, Methyl, C1 2-Alkoxy, C23-Alkanoylamino oder Chloracetylamino, insbesondere Wasserstoff, Chlor, Methyl, Methoxy oder Acetylamino; R7 Nitro, Aminosulfonyl, Methylaminosulfonyl, Dimethylaminosulfonyl, Methylsulfonyl oder 2-Chlor-4--nitrophenylazo, insbesondere Nitro; R8 wenn R3 Wasserstoff bedeutet, Wasserstoff, Chlor, Methyl, Methoxy oder C2~?-Alkanoylamino, vorzugsweise Wasserstoff oder Chlor, sonst Wasserstoff.In particular, D denotes a radical of the formula V K is an unsubstituted 1,4-naphthylene radical or a radical of the formula VI in particular 1,4-naphthylene, R1, when K denotes a radical of the formula VI, hydrogen, allyl or C24-alkyl, which has a substituent from the group consisting of chlorine, bromine, hydroxy, cyano, C12-alkoxy, phenoxy, phenyl, formyloxy, C2 -4-alkanoyloxy, benzoyloxy, C12 -alkoxycarbonyl, C1-4-alkoxycarbonyloxy, C1-2-alkyl- and di- (C1-2-alkyl) -aminocarbonyloxy or a group especially hydrogen, ethyl, cyanoethyl, acetoxyethyl, especially hydrogen or ethyl, or, if K is 1,4-naphthylene, hydrogen or C2-4-alkyl, especially hydrogen or ethyl, especially hydrogen; -R2 straight-chain C1 4-alkyl or a group of the formula -C (CH3) H-CH2-, -CH2-CH (CH3) - or -CH2CH2-0-CH2CH2 -, in particular 1,2-ethylene; R3 is hydrogen, chlorine, bromine, iodine, methylsulfonyl or cyano, in particular hydrogen, chlorine, bromine or methylsulfonyl; R4 is hydrogen, chlorine, bromine, methyl, methoxy, nitro, cyano or trifluoromethyl, in particular chlorine, bromine or nitro; R5 is hydrogen, chlorine, bromine, methyl, methoxy or ethoxy, in particular hydrogen, methoxy or ethoxy; R6 is hydrogen, chlorine, bromine, methyl, C1 2 -alkoxy, C23-alkanoylamino or chloroacetylamino, in particular hydrogen, chlorine, methyl, methoxy or acetylamino; R7 nitro, aminosulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, methylsulfonyl or 2-chloro-4-nitrophenylazo, in particular nitro; R8 when R3 is hydrogen, hydrogen, chlorine, methyl, methoxy or C2 ~? -Alkanoylamino, preferably hydrogen or chlorine, otherwise hydrogen.

Das Verfahren zur Herstellung der neuen Verbindungen der Formel- I ist dadurch gekennzeichnet, dass man, in beliebiger Reihenfolge, eine Verbindung der Formel II worin R = R1 oder R', R' = H 1 oder A- eine Gruppe der Formel -R2-COOH oder ein funktionelles Säurederivat einer solchen Gruppe und n 1 oder 2 bedeuten1 mit ein bis 2 Mol einer Verbindung der Formel III worin B eine Gruppe der Formel -CO-R2-Hal oder -CO-CR" =CHR", die beiden R" Wasserstoff oder das eine Methyl und das andere Wasserstoff und Hal Chlor oder Brom bedeuten, umsetzt und mit der Diazoniumverbindung aus einem Amin der Formel IV D - NH2 (IV) kuppelt.The process for the preparation of the new compounds of the formula I is characterized in that, in any order, a compound of the formula II where R = R1 or R ', R' = H 1 or A- is a group of the formula -R2-COOH or a functional acid derivative of such a group and n is 1 or 2 with one to 2 moles of a compound of the formula III wherein B is a group of the formula -CO-R2-Hal or -CO-CR "= CHR", the two R "are hydrogen or one is methyl and the other is hydrogen and Hal is chlorine or bromine, and reacts with the diazonium compound from an amine of the formula IV D - NH2 (IV) couples.

Die Kondensationen, das Herstellen der Diazoniumverbindungen und das Kuppeln werden analog zu allgemein bekannten Verfahren durchgeführt. Als Säurederivat einer Gruppe A wird vor allem das durch Umsetzung mit Thionylchlorid herstellbare Säurechlorid verwendet.The condensations, the production of the diazonium compounds and that Coupling is carried out analogously to generally known methods. As an acid derivative of a group A is above all that which can be prepared by reaction with thionyl chloride Acid chloride used.

Die Herstellung einer Kupplungskomponente der Formel VII kann durch Kondensation eines Esters der Formel VIII mit einem Amin der Formel IX in Gegenwart eines säurebindenden Mittels, oder durch Kondensation einer Verbindung der Formel X, bzw. X a H - K - N (R2 - CO - OH)2 (X a) mit einem Alkohol der Formel XI durchgeführt werden. An Stelle der Säure der Formel X, bzw. Xa kann auch z.B. das Säurechlorid verwendet werden.The preparation of a coupling component of the formula VII can by condensation of an ester of the formula VIII with an amine of the formula IX in the presence of an acid-binding agent, or by condensation of a compound of the formula X or X a H - K - N (R2 - CO - OH) 2 (X a) with an alcohol of the formula XI be performed. Instead of the acid of the formula X or Xa, it is also possible, for example, to use the acid chloride.

Vorteilhaft ist es auch, die Kupplungskomponente der Formel VII in einem Eintopfverfahren herzustellen, nämlich durch Erhitzen eines Amins der Formel IX mit Acrylsäure oder Crotonsäure, in Gegenwart eines Ueberschusses des Alkohols der Formel XI.It is also advantageous to use the coupling component of the formula VII in a one-pot process, namely by heating an amine of the formula IX with acrylic acid or crotonic acid, in the presence of an excess of the alcohol of formula XI.

Diese Reaktionen gehen in saurem Medium, das heisst, z.B. in Gegenwart von Toluolsulfonsäure, BF3, Schwefelsäure etc. glatt vonstatten.These reactions take place in an acidic medium, i.e. in the presence, for example of toluenesulfonic acid, BF3, sulfuric acid etc. proceed smoothly.

Der Alkohol der Formel XI kann nach bekannter Methode aus Cl-CH2CH2-O-CH2CHOH-CH2Cl durch Erhitzen mit verdünnter Natronlauge hergestellt werden.The alcohol of the formula XI can be prepared from Cl-CH2CH2-O-CH2CHOH-CH2Cl by heating with dilute sodium hydroxide solution.

Die Verarbeitung der neuen Verbindungen der Formel (I) 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. Die Farbstoffe 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 1/2-acetat, Cellulosetriacetat und synthetischen Polyamiden.The processing of the new compounds of the formula (I) into coloring 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. The dyes draw from watery Suspension excellent on textile material made of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing, padding or printing textile material made of linear, aromatic Polyesters, as well as from cellulose-2 1/2 acetate, cellulose triacetate and synthetic Polyamides.

Man färbt oder bedruckt nach an sich bekannten, z.B.One dyes or prints according to known, e.g.

dem in der französischen Patentschrift Nr. 1.445.371 beschriebenen Verfahren.that described in French Patent No. 1.445.371 Procedure.

Die erhaltenen Färbungen besitzen gute Allgemeinechtheiten; hervorzuheben sind die Lichtechtheit, die Thermofixier-, Sublimier- und Plissierechtheit. Sie sind hervorragend nassecht.The dyeings obtained have good all-round fastness properties; to highlight are the lightfastness, the thermosetting, sublimation and pleating fastness. she are excellent wetfast.

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

B e i s p- i e 1 1 Zu einem Gemisch aus 14,3 Teilen a-Naphthylamin und 23,6 Teilen 2-Hydroxymethyl-l , 4-dioxan fügt man im Verlaufe von 15 Minuten bei 85° 7 Teile wasserfreie Acrylsäure zu. Anschliessend wird noch 15 Stunden bei 950 gerührt. Nach Abkühlen des Reaktionsgemisches setzt man 6 Teile p-Toluolsulfonsäure und 30 Teile Toluol zu und erhitzt zum Sieden, wobei ein Azeotrop von Toluol und Wasser abdestilliert. Nach beendeter Reaktion kühlt man ab und wäscht mit verdünnter Natriumbicarbonatlösung und Wasser. Die organische Phase wird abgetrennt und von Toluol befreit, wobei man N-p,4-Dioxanyl~methoxycarbonyl)-äthyl]-α-naphthylamin als Oel erhält, Beispiel 2 Zu 147 Teilen konzentrierter Schwefelsäure werden bei 60°, unter Rühren, langsam 8 Teile kristallisiertes Natriumnitrit gegeben. Man kühlt die Lösung auf 10-200, fügt 10 Teile Eisessig und, nach weiterem Kühlen auf 0-50, 26,2 Teile 2-Brom-4,6-dinitroanilin zu. Man versetzt mit weiteren 10 Teilen Eisessig, rührt 3 Stunden bei 0-5° und zerstört den Ueberschuss an Nitrosylschwefelsäure.mit wenig Harnstoff.B e i s p- i e 1 1 To a mixture of 14.3 parts of a-naphthylamine and 23.6 parts of 2-hydroxymethyl-1,4-dioxane are added over the course of 15 minutes 7 parts of anhydrous acrylic acid were added at 85 °. Then another 15 hours at 950 stirred. After the reaction mixture has cooled, 6 parts of p-toluenesulfonic acid are added and 30 parts of toluene and heated to boiling, an azeotrope of toluene and Distilled off water. When the reaction has ended, the mixture is cooled and washed with dilute Sodium bicarbonate solution and water. The organic phase is separated and from Freed toluene, N-p, 4-Dioxanyl ~ methoxycarbonyl) ethyl] -α-naphthylamine obtained as an oil, Example 2 To 147 parts of concentrated sulfuric acid are added 60 °, slowly added 8 parts of crystallized sodium nitrite with stirring. One cools the solution to 10-200, add 10 parts of glacial acetic acid and, after further cooling to 0-50, 26.2 parts of 2-bromo-4,6-dinitroaniline. Another 10 parts of glacial acetic acid are added, stirs for 3 hours at 0-5 ° and destroys the excess of nitrosylsulfuric acid little urea.

Die so erhaltene Diazoniumsalzlösung wird dann langsam, unter Rühren, zu einer auf 0-5° gekühlten Lösung von 31,5 Teilen N-(1,4-Dioxanylmethoxycarbonyläthyl)-α-naphthylamin in 100. Teilen 3%iger Salzsäure getropft.The diazonium salt solution thus obtained is then slowly, with stirring, to a solution, cooled to 0-5 °, of 31.5 parts of N- (1,4-dioxanylmethoxycarbonylethyl) -α-naphthylamine added dropwise in 100 parts of 3% hydrochloric acid.

Nach beendeter Kupplung wird der Farbstoff mit 500 Teilen Eiswasser vollständig ausgefällt, 1 Stunde gerührt, abfiltriert und säurefrei gewaschen. Zur Verbesserung der färberischen Eigenschaften und der Dispersionsstabilität (bei der darauffolgenden Herstellung eines Färbepräparats) wird der Farbstoff erneut in 100 Teilen Wasser verteilt, während 3 bis 5 Stunden bei ca. 900 gerührt, wieder abfiltriert, mit Wasser nachgewaschen und getrocknet.After coupling has ended, the dye is mixed with 500 parts of ice water completely precipitated, stirred for 1 hour, filtered off and acid free washed. To improve the dyeing properties and the dispersion stability (in the subsequent production of a dye preparation) the dye is used again distributed in 100 parts of water, stirred for 3 to 5 hours at about 900, again filtered off, washed with water and dried.

Er färbt Polyesterfasermaterial in blauen Tönen mit ausgezeichneten Echtheiten.He dyes polyester fiber material in blue tones with excellent Fastnesses.

Häufig ist es möglich, die Farbstoffe durch eine Wärme-, Lösungsmittel- und/oder Mahlbehandlung oder durch Umkristallisation in eine andere, thermisch stabile Modifikation überzuführen. Geeignete Methoden und die dabei erzielbaren Vorteile sind dem Fachmann bekannt.It is often possible to remove the dyes by a heat, solvent and / or milling treatment or by recrystallization into another, thermally stable one Transfer modification. Appropriate methods and the advantages they can achieve are known to the person skilled in the art.

In den folgenden Tabellen sind weitere, analog zu den obigen Angaben hergestellte Dispersionsfarbstoffe und die Nuance ihrer Aus färbungen auf Polyesterfasermaterial angegeben.The following tables contain further information analogous to the above produced disperse dyes and the nuance of their colorations from polyester fiber material specified.

T a b e l l e 1 Farbstoffe der Formel: Bsp. R1 R2 R3 R4 R5 R6 R7 Nuance auf No. Polyester 3 -C2H5 -CH2CH2- H H H -CH3 -NO2 rot 4 -CH2CH2CN -CH2CH2CH2- H Cl H H -SO2CH3 orange 5 H -CH2CH2- Br -NO2 -OC2H5 -NHCOCH3 -NO2 blau 6 H do. do. -CN -OCH3 -NHCOC2H5 do. do. 7 n-C4N9 -CH2-CH(CH3)- -SO2CH3 -NO2 do. -CH3 do. do. 8 H -CH2- H -CN do. do do. violett 9 H -(CH2)4- Cl -NO2 -OC2H5 -NHCOCH3 do. blau 10 -CH2CH2OCOCH3 -(CH2)2- do. Cl H H do. braun 11 -C2H5 do. H H H H C6H5-N=N- scharlach 12 -CH2CH2-OCH3 -(CH2)3- Br Br Cl -CH3 -CONH2 gelbbraun 13 H -CH2- H Cl H -NHCOCH3 -SO2CH3 rot w 4 0> ok 4> b b n b a 4 (U c: 7 =i 4 4> «1 4> r( zu r 4 . o 4> 4 (d ISO0 uo 0, 0 -1 0 0 0 < 0 0 0 0 o o o o o z rd rd z 00, S rd h g -> rd rd rd g g o R g O Q O R rd lo zA ol « m u> Ur o :1: in o loLn U « n m m:1::1: N I v = U N 3; :1: :1: m u u v U u evt in > N :2: . . ... . . . .. z z zu Z Z Z :1: :1: :1:0 « o 0 0 0 0 0 0 0 0 0 o « N es z z z :2: 0:2: z rd rd X rd rd rd rd rd rd ra o o o o o O O 0 u II I vi- vi cri u u U Uu I Z 11111111 1 I m 31 e o .t) Omm rr, m mO O 0 ri O m m mO sr; m m t e g u cd 0:2: 1 t 1 ; :2: 1 1 z <1 m :1: In ri 0000:1: o a; :1: :1:00:1: rd rd rd rd 0:1: :1: w 1 m :1: :1: :1: :1::1::1:0 o o l l õ rd H . . u o ri o h 0 :1:0 rI h -1 0000 1 ffMLrn-rd:1:, i m rd :1: 0 rd rd rd g e rd :1: -:1: in :1: in m """ mN 1e lu° O m m « m iyu u cd u r :1::1: u rd p; cu m r x u u O O u u ~, 000 0 0 0 0 0 0 0 0 OIUUUUOUO tn 1 1 1 1 1 I L I :n 1 u « u . . zu zu zu zu zu zu d to I 0 0 0 0 0 0 O U cV O 0 0 0 0 0 0 0 0 0 0 1 rd rd rd rd rd rd rd rd rd rd rd rd rdrd rd rd u l in cn an m uu u in 0 0 1 0 :1: u tn 00 0 u, uo tn m u in u W R 1 m :11 rl u o X :o u . o o m o z; « :1: 1 1 E s X . 1 0 .0 v u qm v m e v rd o sr v o o 0 0 X 1 :1: = 1 rs m w m m X w5 rd rd:1: m w u u u N cq cm 0 1 1 001 u O u u 1 1 1 1 1 Bq O s o N cn 0 I-r 0' 0 n cv> in 0 ffi O cv> mz I N « N G N « « cv> cv> cv> cv> cv> NO. R R R R R R Nuance auf 4J l 6 Bsp. a o 2R1 m 3 O o 6 3Q z7 Polyester 35 rd 3 > õ 3 Cl -OCH3 g CONC2H5 Õ U U H0 36 3 .. s4 , ulu, m 3 -CH2CH2 - J -NO2 -0C2H5 -N3COC32Cl do blau uN vW N CH2 o o Õ Õ Õ Õ Õ O O O - 0 i a cr 6 a a a ci a a a a 39 -C235 -C32CH2-OC32CH2- 3 3 3 do. do. do. 39a n -C32CH2 - H H 3 Cl do. orange o r X m m m. P; X u u 5: 'I; s: o U 00U 3 do. o Cl o -OCH3 do. rot I aul U I I I 39c -C2H5 do. 3 -CN 3 3 do. rubin n X n n rQ 39e -C235 do. m Cl 3 3 do. rom P; U U <u X X X X X U 3: U O X 1 H do. O Oa n 3 do. Br -NO2 do. do. do. rotstichig- or H h O H H z o H H o H « 3 do. 3 Cl 3 y X do. UUauuzu oSn s: m b $ $ m m m m m m m m e I I I u N « u N U o rs N g t t g g g g lv s Y G O=u O c4 -$ m $ v R uN m $ mN :}: mN m m m y tb . X Q U t O 44 b z AX ur T a b e l l e 2 Farbstoffe der Formel: W 7 dO +r d -rJ 0 O rl O 0 0 0 a)m k 1 a a k a a oa, cdrl 70 -PI UUmm 03 rl r( 00 m N u u n n e H O O = w ,4 p; v« zv R6 x y õ v No. 1 Polyester I I 40 Z -C}32C32- cl -C33 -SO2N(CH32 -Cl rot 41 do. -<CH2)4- Õ Õ O Õ 3 NOZ 2 a -C2H4.-C-C0 -CH2-CH2- -NO2 -0C2H5 do. 43 -c2H4-CO-0C33' do. do. -tCH3 do. do. -£HCOC2H5 do. o m a; -C2H4-O-CO-0-C3 dc. -OCH3 dc. 5 U u X t I -C2H4-O-CO-OC2H dc. Cl dc. do. ao. -Cl tn rZ « x (N v X o O X s cx r) X P; Ú , ZO g X õ u :n U « U N I o o O O 7; n Ú W sV s sU m m 9 '= N O O H U) O O O O O P; ;r: o c ) I I u u «e I O O C) O U V ° ° l l l l l l : C W W N N CM y y y U U te O O ,4 « m :z T a b e l l e 3 Farbstoffe der Formel: Bsp. Nuance auf R1 R2 R3 R4 R7 No. Polyester 47 H -CH2CH2- Br -NO2 -NO2 blau 48 H do. do. -CN do. do. 49 -C2H5 -(CH2)3- Cl -NO2 do. do. 50 H -CH(CH3)-CH2- J do. do. do. 51 H -CH2CH2- -SO2CH3 do. do. do. 52 H -CH2- do. -CN do. do. 53 H -(CH2)4- -CN do. do. do. 54 H -CH2CH2-O-CH2CH2- Br -NO2 do. do. 55 -C4H9 -CH2-CH2- do. do. do. do. Table 1 Colorants of the formula: E.g. R1 R2 R3 R4 R5 R6 R7 Nuance on No. polyester 3 -C2H5 -CH2CH2- HHH -CH3 -NO2 red 4 -CH2CH2CN -CH2CH2CH2- H Cl HH -SO2CH3 orange 5 H -CH2CH2- Br -NO2 -OC2H5 -NHCOCH3 -NO2 blue 6 H do. do. -CN -OCH3 -NHCOC2H5 do. do. 7 n-C4N9 -CH2-CH (CH3) - -SO2CH3 -NO2 do. -CH3 do. do. 8 H -CH2- H -CN do. do do. violet 9 H - (CH2) 4- Cl -NO2 -OC2H5 -NHCOCH3 do. blue 10 -CH2CH2OCOCH3 - (CH2) 2- do. Cl HH do. Brown 11 -C2H5 do. HHHH C6H5-N = N- scarlet 12 -CH2CH2-OCH3 - (CH2) 3- Br Br Cl -CH3 -CONH2 yellow-brown 13 H -CH2- H Cl H -NHCOCH3 -SO2CH3 red w 4 0> ok 4> bbnba 4 (U c: 7 = i 4 4> «1 4> r (to r 4. O 4> 4 (d ISO0 uo 0, 0 -1 0 0 0 <0 0 0 0 oooooz rd rd z 00, S rd hg -> rd rd rd ggo R g OQOR approx lo zA ol « m u> Ur o : 1: in o loLn U «nmm: 1 :: 1: NI v = UN 3; :1: : 1: muuv U u evt in > N: 2:. . ... . . .. zz to ZZZ: 1:: 1:: 1: 0 «O 0 0 0 0 0 0 0 0 0 o« N es zzz: 2: 0: 2: z rd rd X rd rd rd rd rd rd ra ooooo OO 0 u II I vi vi cri uu U Uu IZ 11111111 1 In the 31 e O .t) Omm rr, m mO O 0 ri O mm mO sr; mmtegu cd 0: 2: 1 t 1 ; : 2: 1 1 z <1 m: 1: In ri 0000: 1: o a; : 1:: 1: 00: 1: rd rd rd rd 0: 1:: 1: w 1 m: 1:: 1:: 1:: 1 :: 1 :: 1: 0 oo ll O approx H . . uo ri oh 0: 1: 0 rI h -1 0000 1 ffMLrn-rd: 1 :, im rd: 1: 0 rd rd rd ge rd: 1: -:1: in: 1: in m """mN 1e lu ° O mm «m iyu u cd ur: 1 :: 1: u rd p; cu mrxuu OO uu ~, 000 0 0 0 0 0 0 0 0 OIUUUUOUO tn 1 1 1 1 1 I. L. I. : n 1 u «U. . to to to to to to d to I 0 0 0 0 0 0 OU cV O 0 0 0 0 0 0 0 0 0 0 1 rd rd rd rd rd rd rd rd rd rd rd rd rdrd rd rd u l in cn at m uu u in 0 0 1 0: 1: u tn 00 0 u, uo tn mu in u WR 1 m: 11 rl uo X: ou. oomo z; «: 1: 1 1 E s X. 1 0 .0 BC u qm vmev rd o sr voo 0 0 X 1: 1: = 1 rs mwmm X w5 rd rd: 1: mw uuu N cq cm 0 1 1 001 u O uu 1 1 1 1 1 Bq O so N cn 0 Ir 0 '0 n cv> in 0 ffi O cv> mz IN "NGN""cv>cv>cv>cv>cv> NO. RRRRRR nuance on 4J l 6 E.g. ao 2R1 m 3 O o 6 3Q z7 polyester 35 rd 3> õ 3 Cl -OCH3 g CONC2H5 Õ U U H0 36 3 .. s4, ulu, m 3 -CH2CH2 - J -NO2 -0C2H5 -N3COC32Cl do blue uN vW N CH2 oo Õ Õ Õ Õ Õ OOO - 0 ia cr 6 aaa ci aaaa 39 -C235 -C32CH2-OC32CH2- 3 3 3 do. do. do. 39a n -C32CH2 - HH 3 Cl do. orange or X mm m. P; X uu 5: 'I; s: o U 00U 3 thurs. o Cl o -OCH3 do. Red I aul UIII 39c -C2H5 do. 3 -CN 3 3 do. ruby n X nn rQ 39e -C235 do. m Cl 3 3 do. Rome P; UU <u XXXXXU 3: UOX 1 H do. O Oa n 3 do. Br -NO2 do. do. do. reddish or H h OHH zo HH o H «3 do. 3 Cl 3 y X do. UUauuzu oSn s: mb $ $ mmmmmmmm e III u N «U NU o rs N gttggggg lv s YG O = u O c4 - $ m $ v R uN m $ mN:}: mN mmm y tb . XQU t O 44 or AX ur Table 2 dyes of the formula: W. 7th dO + approx -rJ 0 O rl O 0 0 0 a) mk 1 aakaa oa, cdrl 70 -PI Uum 03 rl r (00 m N uunn e HOO = w, 4 p; v «zv R6 xy õ v No. 1 polyester II 40 Z -C} 32C32- cl -C33 -SO2N (CH32 -Cl red 41 do. - <CH2) 4- Õ Õ O Õ 3 NOZ 2 a -C2H4.-C-C0 -CH2-CH2- -NO2 -0C2H5 do. 43 -c2H4-CO-0C33 'do. do. -tCH3 do. do. - £ HCOC2H5 do. O m a; -C2H4-O-CO-0-C3 dc. -OCH3 dc. 5 U u X t I -C2H4-O-CO-OC2H dc. Cl dc. do. ao. -Cl tn rZ «X (N v X o O X s cx r) X P; Ú, ZO g X õ u : n U «UNI oo OO 7; n Ú W sV s sU mm 9 '= NOO HU) OOOOO P; ; r: oc) II uu «E IOO C) OUV ° ° llllll : CWW NN CM yyy UU te OO, 4 « m: z Table 3 dyes of the formula: E.g. Nuance on R1 R2 R3 R4 R7 No. polyester 47 H -CH2CH2- Br -NO2 -NO2 blue 48 H do. do. -CN do. do. 49 -C2H5 - (CH2) 3- Cl -NO2 do. do. 50 H -CH (CH3) -CH2- J do. do. do. 51 H -CH2CH2- -SO2CH3 do. do. do. 52 H -CH2- do. -CN do. do. 53 H - (CH2) 4- -CN do. do. do. 54 H -CH2CH2-O-CH2CH2- Br -NO2 do. do. 55 -C4H9 -CH2-CH2- do. do. do. do.

T a b e l l e 4 Farbstoffe der Formel tH V a S4 X » rrlO) -CI Q) 4] D GU ~4 P tn +I rd c 0 J ucU O O rl O 0 0 0 7( 0 k 1 9 -rl a cort 3 70 npl a m u X i No. 1 2 O 6 R9 / fs rl XZp 0 a uo i U M -ri 2 Z U r ro N 0 0 01 -CH2CH2 X t 3 -NHCOCH3 Z X X s CN rot rse xo Xt -C32CH2-OCOCN3 -(CH2)3- 3 I v ~ 60 n-C4H9 dc. -OCH3 -CH3 6 - NO2 dc. m -c m m X c X 62 -C32CH2 v m u dc. 3 -NHCOCH3 U 6SO2N32. do. P; OU00000 63 3 dc. -0C2H5 dc. 6 v m t t 64 H2C32-COO-CH2 dc. 3 lz n n m Cs p; w x x x rs r) rs « U rs U rs n rs o O O O O O x V x 5) g g g e g U ~ U l l l rq rn Qç r1 Z oU 1 Z aS a; vl ° w [ mv n Õ rS rs U U rs U x m N I U rs lu U U W gl I W N . I tSU Y U) O ç g~ fo aE O ~l (9 fN £ 4 Z U) 1X) 1 «) t0 t0 t T a b e l l e 5 Farbstoffe der Formel: Bsp. R1 R2 R5 R6 R12 R13 Nuance auf No. Polyester. 65 -C2H5 -CH2-CH2- H -CH3 Cl -Cl blau 66 H do. -OC2H5 -NHCOCH3 Br -Br do. 67 H do. -OCH3 -CH3 Cl -NO2 do. 68 H do. H Cl Br -CN do. 69 H do. H -CH3 H -SO2C2H5 do. 70 H do. -OCH3 do. CN -CN do. Table 4 Colorants of the formula tH V a S4 X » rrlO) -CI Q) 4] D GU ~ 4 P tn + I rd c 0 J ucU OO rl O 0 0 0 7 (0 k 19 -rl a cort 3 70 npl a must X i No. 1 2 O 6 R9 / fs rl XZp 0 a uo i UM -ri 2 ZU r ro N 0 0 01 -CH2CH2 X t 3 -NHCOCH3 ZXX s CN red rse xo Xt -C32CH2-OCOCN3 - (CH2) 3- 3 I. v ~ 60 n-C4H9 dc. -OCH3 -CH3 6 - NO2 dc. m -cmm X c X 62 -C32CH2 vmu dc. 3 -NHCOCH3 U 6SO2N32. do. P; OU00000 63 3 dc. -0C2H5 dc. 6 vmtt 64 H2C32-COO-CH2 dc. 3 lz n nm Cs p; wxxx rs r) rs «U rs U rs n rs o OOOOO x V x 5) vs. U ~ U lll rq rn Qç r1 Z oU 1 Z aS a; vl ° w [mv n Õ rS rs UU rs U xm NIU rs lu UUW gl IWN . I tSU Y U) O ç g ~ fo aE O ~ l (9 fN £ 4 CLOSED) 1X) 1 «) t0 t0 t Table 5 Colorants of the formula: E.g. R1 R2 R5 R6 R12 R13 Nuance No. Polyester. 65 -C2H5 -CH2-CH2- H -CH3 Cl -Cl blue 66 H do. -OC2H5 -NHCOCH3 Br -Br do. 67 H do. -OCH3 -CH3 Cl -NO2 do. 68 H do. H Cl Br -CN do. 69 H do. H -CH3 H -SO2C2H5 do. 70 H do. -OCH3 do. CN -CN do.

T a b e l l e 6 Farbstoffe der Formel: Bsp. R1 R2 R5 R6 R11 R12 R13 Nuance auf No. Polyester 71 -CH2-CH2-OCOCH3 -CH2-CH2- H -NHCOCH3 Br H Br blau 72 -C2H4-O-CO-NHCH3 do. H do. Cl H Cl do. 73 -C2H4-O-CO-NHC2H5 do. H -CH3 do. H CN do. 74 -C2H4-O-CO-N(CH3)2 do. H -NHCOCH2CH2Cl H Br H do. 75 H do. H -CH3 -SO2C2H5 H H do. 76 -C2H4-O-CO-N(C2H5)2 do. -OCH3 -NHCOCH3 -CN H CN do. Table 6 Colorants of the formula: E.g. R1 R2 R5 R6 R11 R12 R13 Nuance No. polyester 71 -CH2-CH2-OCOCH3 -CH2-CH2- H -NHCOCH3 Br H Br blue 72 -C2H4-O-CO-NHCH3 do. H do. Cl H Cl do. 73 -C2H4-O-CO-NHC2H5 do. H -CH3 do. H CN do. 74 -C2H4-O-CO-N (CH3) 2 do. H -NHCOCH2CH2Cl H Br H do. 75 H do. H -CH3 -SO2C2H5 HH do. 76 -C2H4-O-CO-N (C2H5) 2 do. -OCH3 -NHCOCH3 -CN H CN do.

T a b e l l e 7 Farbstoffe der Formel: Bsp. R1 R2 R5 R6 R17 R18 Nuance auf No. Polyester 77 H -C2H4- H Cl Cl Cl rot 78 -C2H5 do. -OCH3 -CH3 H -SO2-C2H5 do. 79 H do. H H Br Cl do. 80 -C2H5 do. H H do. Br do. 81 H do. H Br -CH3 -CN do. 82 -C2H4OH do. H -NHCOCH3 -CN do. do. 83 H do. -OC2H5 do. H -NO2 blaustichig-rot T a b e l l e 8 Farbstoffe der Formel: Bsp. R1 R2 R5 R6 R14 R15 R16 Nuance auf No. Polyester 84 H -CH2-CH2- H H -NO2 H -CN rot 85 H do. -OC2H5 -NHCOCH3 -CN -CH3 do. blau 86 H do. do. Cl -NO2 -C6H5 do. rot 87 -C2H5 do. -OCH3 -CH3 do. -CH3 -NO2 violett 88 -C2H4-OH do. H H H do. -CH3 rot 89 H do. H -CH3 H Cl Cl do. 90 -C2H4Cl do. H do. H Br Br do. 91 H do. H -NHCOCH3 H Cl -COC2H5 do. 92 -C2H5 do. H Cl H Br -COC3H7 do. Table 7 Colorants of the formula: E.g. R1 R2 R5 R6 R17 R18 Nuance on No. polyester 77 H -C2H4- H Cl Cl Cl red 78 -C2H5 do. -OCH3 -CH3 H -SO2-C2H5 do. 79 H do. HH Br Cl do. 80 -C2H5 do. HH do. Br do. 81 H do. H Br -CH3 -CN do. 82 -C2H4OH do. H -NHCOCH3 -CN do. do. 83 H do. -OC2H5 do. H -NO2 bluish red Table 8 Colorants of the formula: E.g. R1 R2 R5 R6 R14 R15 R16 Nuance No. polyester 84 H -CH2-CH2- HH -NO2 H -CN red 85 H do. -OC2H5 -NHCOCH3 -CN -CH3 do. blue 86 H do. do. Cl -NO2 -C6H5 do. Red 87 -C2H5 do. -OCH3 -CH3 do. -CH3 -NO2 purple 88 -C2H4-OH do. HHH do. -CH3 red 89 H do. H -CH3 H Cl Cl do. 90 -C2H4Cl do. H do. H Br Br do. 91 H do. H -NHCOCH3 H Cl -COC2H5 do. 92 -C2H5 do. H Cl H Br -COC3H7 do.

T a b e l l e 5 Bsp. Nuance auf No. H Polyester M3 02 5N= 0 N¼C3 -CH -C-OC3 - blau NHCOC33 2 1 C33 N 0C II 2 0 << -N=N 4 N / -CH blau CH2-CH2 II ea NHCOCH3 CH2 -C-O-CH,- C635 0 95 5N=NQNH-C32-CH2-CH2-C11-0-CH2 rot 96 C635»½N=NNHCH -CH rot 22-C-O-CH 6 2 0 97 0 N)){N½CHs 2 pl blau CH2-CH2-C-0-CH 98 02N S H t -CH -0C"-0-CH <) blaublau 2 0QN-CH2 2 H34 COOC33OC235 0 99 N> N=N 4 NH-CH2-CH2-C-O-CH2 <) blau NHCOC33 Bsp. Nuance auf No. Polyester 100 NN=N NH-CH2-cH2-c-o-cH2= rot S z N NHCOCH3 101 °2 N=@ o' -C-O-C2 blau 2 O ( H2432 0 ANWENDUNGSBEISPIEL 7 Teile des nach Deispiel 1 hergestellten Farbstoffs werden mit 4 Teilen dinaphthylmethandisulfonsaurem Natrium, 4 Teilen Natriumcetylsulfat und 5 Teilen wasserfreiem Natriumsulfat in einer Kugelmühle 48 Stunden zu einen feinen Pulver gemahlen.Table 5 E.g. Nuance on No. H polyester M3 02 5N = 0 N¼C3 -CH -C-OC3 - blue NHCOC33 2 1 C33 N 0C II 2 0 << -N = N 4 N / -CH blue CH2-CH2 II ea NHCOCH3 CH2 -CO-CH, - C635 0 95 5N = NQNH-C32-CH2-CH2-C11-0-CH2 red 96 C635 »½N = NNHCH -CH red 22-CO-CH 6 2 0 97 0 N)) {N½CHs 2 pl blue CH2-CH2-C-0-CH 98 02N SH t -CH -0C "-0-CH <) blue-blue 2 0QN-CH2 2 H34 COOC33OC235 0 99 N> N = N 4 NH-CH2-CH2-CO-CH2 <) blue NHCOC33 E.g. Nuance on No. polyester 100 NN = N NH-CH2-cH2-co-cH2 = red S z N NHCOCH3 101 ° 2 N = @ o '-CO-C2 blue 2 O (H2432 0 APPLICATION EXAMPLE 7 parts of the dye prepared according to Example 1 are ground with 4 parts of sodium dinaphthylmethanedisulphonic acid, 4 parts of sodium cetyl sulphate and 5 parts of anhydrous sodium sulphate in a ball mill for 48 hours to give a fine powder.

1 Teil d.s so erhaltenen Färbepräparats wird mit wenig Wasser angeteigt und die erhaltene Suspension durch ein Sieb einem 2 Teile Natriumlaurylsulfat in 4000 Teilen Wasser enthaltenden Färbebad zugesetzt. Das Flottenverhältnis beträgt 1;40. Nan gibt nun 100 Teile gereinigtes Polyestergewebe bei 40-50° in das Bad, gibt 20 Teile eines chlorierten Benzols in Wasser emulgiert zu, erwärmt das Bad langsam auf 100° und färbt 1 - 2 Stunden bei 95-100t. Das gefärbte Gewebe wird gewaschen, geseift, erneut gewaschen und getrocknet. Die egale, farbstarke, blaue Färbung ist ausgezeichnet licht-, wasch-, sublimier-, thermofixier- und permanent-pressecht.1 part of the dye preparation obtained in this way is made into a paste with a little water and the suspension obtained through a sieve a 2 parts of sodium lauryl sulfate in 4000 parts of water containing dyebath added. The liquor ratio is 1; 40. Nan now puts 100 parts of cleaned polyester fabric into the bath at 40-50 °, adds 20 parts of a chlorinated benzene emulsified in water, heats the bath slowly to 100 ° and stains 1 - 2 hours at 95-100t. The dyed fabric is washed, soaped, washed again and dried. The level, strongly colored, blue coloring is excellent light, wash, sublimation, thermosetting and permanent press-fast.

Claims (9)

Patentansprüche 1. Azofarbstoffe der Formel worin D den Rest einer in der Chemie der Dispersionsfarbstoffe üblichen Diazokomponente, K gegebenenfalls weitere Substituenten tragendes 1,4-Phenylen oder 1,4-Naphthylen, R1 Wasserstoff, C1-4-Alkyl oder C24-Alkenyl oder, wenn K 1,4-Phenylen bedeutet, auch C2 4-Alkyl oder C2 2-4 Alkenyl, das einen Substituenten aus der Gruppe Chlor, Brom, Hydroxy, Cyan, C1-4-Alkoxy, Phenoxy, Phenyl, Formyloxy, C1-4-Alkyl-carbonyloxy, Benzoyloxy, C1-4-Alkoxy-carbonyl, C1-4-Alkoxy--carbonyloxy, C1 4-Alkyl- oder Di-(Cl 4--alkyl)-aminocarbonyloxy oder eine Gruppe der Formel und R2 C1 -Alkylen oder C2-4-Alkylen-O-C2-4-Alkylen bedeuten, wobei das Molekül von Sulfonsäure- und Acetalgruppen, sowie von Gruppen der Formel -N#CH2-O-, -N#CH2-N# und -N#CH2-S- frei ist.Claims 1. Azo dyes of the formula wherein D is the radical of a diazo component customary in the chemistry of disperse dyes, K optionally carrying further substituents 1,4-phenylene or 1,4-naphthylene, R1 is hydrogen, C1-4-alkyl or C24-alkenyl or, if K 1,4- Phenylene means, also C2 4-alkyl or C2 2-4 alkenyl, which has a substituent from the group chlorine, bromine, hydroxy, cyano, C1-4-alkoxy, phenoxy, phenyl, formyloxy, C1-4-alkyl-carbonyloxy, benzoyloxy , C1-4-alkoxy-carbonyl, C1-4-alkoxy-carbonyloxy, C1 4-alkyl- or di- (Cl 4 -alkyl) -aminocarbonyloxy or a group of the formula and R2 is C1-alkylene or C2-4-alkylene-O-C2-4-alkylene, where the molecule is composed of sulfonic acid and acetal groups, as well as groups of the formula -N # CH2-O-, -N # CH2-N # and -N # CH2-S- is free. 2. Azofarbstoffe der Formel I, gemäss Anspruch 1, worin D Phenyl, das 1, 2 oder 3 Substituenten trägt, darunter je 0, einen oder zwei aus der Gruppe Chlor, Brom, Jod, Nitro, Cyan, Methyl oder Methylsulfonyl und/oder je 0 oder einen aus der Gruppe Methoxy, Formyl, C1-2-Alkyl-carbonyl, C1-2-Alkoxy--carbonyl, Benzoyl, Rhodan, Toluylsulfonyl, Aminosulfonyl, C1 Alkyl oder Di-(Cl 2-alkyl)-aminosulfonyl, Aminocarbonyl, C1-2-Alkyl- oder Di-(C1-2--alkyl)-aminocarbonyl, Phenylaminocarbonyl, N-Aethyl-N-phenylaminocarbonyl, Trifluormethyl, Phenyl, C -Alkanoylamino und 2-3 Phenylazo, worin der Phenylkern bis zu zwei Substituenten, und zwar Chlor und/oder Nitro tragen kann, Thienyl, das 1, 2 oder 3 Substituenten trägt, darunter je 0, einen oder zwei aus der Gruppe Chlor, Brom, Nitro, Cyan und Methyl und/oder je O oder einen aus der Gruppe Phenyl, C2-3-Alkanoyl und C1-2--Alkoxy-carbonyl; Thiazolyl, Benzthiazolyl oder Benzisothiazolyl, das bis zu zwei Substituenten tragen kann, darunter je 0, einen oder zwei aus der Gruppe Chlor, Brom, Nitro und Cyan und/oder je O oder einen aus der Gruppe Methyl, Rhodan, Aminosulfonyl und C1 2-Alkylsulfonyl oder Phenyl-(1,3,4)- oder (1,3,5)-thiadiazolyl-2 bedeutet.2. Azo dyes of the formula I according to claim 1, wherein D is phenyl, which carries 1, 2 or 3 substituents, including 0, one or two from the group Chlorine, bromine, iodine, nitro, cyano, methyl or methylsulfonyl and / or 0 or one each from the group methoxy, formyl, C1-2-alkyl-carbonyl, C1-2-alkoxy-carbonyl, benzoyl, Rhodan, toluylsulfonyl, aminosulfonyl, C1 alkyl or di- (Cl 2-alkyl) -aminosulfonyl, Aminocarbonyl, C1-2-alkyl- or di- (C1-2 - alkyl) -aminocarbonyl, phenylaminocarbonyl, N-ethyl-N-phenylaminocarbonyl, trifluoromethyl, phenyl, C -alkanoylamino and 2-3 Phenylazo, in which the phenyl nucleus has up to two substituents, namely chlorine and / or Can carry nitro, thienyl, which carries 1, 2 or 3 substituents, including 0 each, one or two from the group consisting of chlorine, bromine, nitro, cyano and methyl and / or O each or one from the group consisting of phenyl, C2-3-alkanoyl and C1-2-alkoxycarbonyl; Thiazolyl, Benzthiazolyl or benzisothiazolyl, which can have up to two substituents, including 0, one or two from the group consisting of chlorine, bromine, nitro and cyano and / or each O or one from the group consisting of methyl, rhodan, aminosulfonyl and C1 2-alkylsulfonyl or Denotes phenyl- (1,3,4) - or (1,3,5) -thiadiazolyl-2. 3. Azofarbstoffe der Formel I, gemäss Anspruch 1, worin D Phenyl bedeutet, das einen, zwei oder drei Substituenten und zwar Chlor, Brom, Jod, Nitro, Cyan, Methyl, Methoxy, Methylsulfonyl, C2-3-Alkanoyl, Aminosulfonyl, C1-2-Alkyl- oder Di-(C1-2-alkyl)-aminosulfonyl und/oder 2-Chlor-4-nitrophenylazo tragen kann.3. Azo dyes of the formula I according to claim 1, wherein D is phenyl, one, two or three substituents, namely chlorine, bromine, iodine, nitro, cyano, Methyl, methoxy, methylsulfonyl, C2-3-alkanoyl, aminosulfonyl, C1-2-alkyl or Di- (C1-2-alkyl) -aminosulfonyl and / or 2-chloro-4-nitrophenylazo can carry. 4. Azofarbstoffe der Formel I, gemäss Anspruch 1, worin D ein Rest der Formel V ist, worin R3 Wasserstoff, Chlor, Brom, Jod, Methylsulfonyl oder Cyan, insbesondere Wasserstoff, Chlor, Brom oder Methylsulfonyl, R4 Wasserstoff, Chlor, Brom, Methyl, Methoxy, Nitro, Cyan oder Trifluormethyl, insbesondere Chlor, Brom oder Nitro, R7 Nitro, Aminosulfonyl, Methylaminosulfonyl, Dimethylaminosulfonyl, Methylsulfonyl oder 2-Chlor-4-nitrophenylazo, insbesondere Nitro und R8 wenn R3 Wasserstoff bedeutet, Wasserstoff, Chlor, Methyl, Methoxy oder C2 3-Alkanoylamino, vorzugsweise Wasserstoff oder Chlor, sonst Wasserstoff bedeuten.4. Azo dyes of the formula I according to claim 1, wherein D is a radical of the formula V where R3 is hydrogen, chlorine, bromine, iodine, methylsulfonyl or cyano, especially hydrogen, chlorine, bromine or methylsulfonyl, R4 is hydrogen, chlorine, bromine, methyl, methoxy, nitro, cyano or trifluoromethyl, especially chlorine, bromine or nitro, R7 Nitro, aminosulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, methylsulfonyl or 2-chloro-4-nitrophenylazo, especially nitro and R8 when R3 is hydrogen, hydrogen, chlorine, methyl, methoxy or C2 3-alkanoylamino, preferably hydrogen or chlorine, otherwise hydrogen. 5. Azofarbstoffe der Formel I, gemäss Anspruch 1, worin K ein unsubstituierter 1,4-Naphthylenrest oder ein Rest der Formel VI ist, worin R5 Wasserstoff, Chlor, Brom, Methyl, Methoxy oder Aethoxy, insbesondere Wasserstoff, Methoxy oder Aethoxy und R6 Wasserstoff, Chlor, Brom, Methyl, Methoxy, Aethoxy, C2 3-Alkanoylamino oder Chloracetylamino, insbesondere Wasserstoff, Methyl oder Acetylamino bedeuten.5. Azo dyes of the formula I according to claim 1, wherein K is an unsubstituted 1,4-naphthylene radical or a radical of the formula VI is where R5 is hydrogen, chlorine, bromine, methyl, methoxy or ethoxy, especially hydrogen, methoxy or ethoxy and R6 is hydrogen, chlorine, bromine, methyl, methoxy, ethoxy, C2 is 3-alkanoylamino or chloroacetylamino, especially hydrogen, methyl or acetylamino . 6. Azofarbstoffe der Formel I, gemäss Anspruch 1, worin Rl,wenn K einen Rest der Formel VI bedeutet, Wasserstoff, Allyl oder C2-4-Alkyl, das einen Substituenten aus der Gruppe Chlor, Brom, Hydroxy, Cyan, C1 2-Alkoxy, Phenoxy, Phenyl, Formyloxy, C24-Alkanoyloxy, Benzoyloxy, C 1-2 -Alkoxy-carbonyl, C1 2-Alkoxy-carbonyloxy, C 1-2 -Alkyl-und Di-(C1-2-alkyl)-aminocarbonyloxy tragen kann oder eine Gruppe insbesondere Wasserstoff, Aethyl, Cyanäthyl, Acetoxyäthyl, vor allem Wasserstoff oder Aethyl, oder, wenn K 1,4--Naphthylen ist, Wasserstoff oder C2 4-Alkyl, insbesondere Wasserstoff oder -Aethyl, vor allem Wasserstoff bedeutet.6. Azo dyes of the formula I according to claim 1, wherein Rl, when K denotes a radical of the formula VI, is hydrogen, allyl or C2-4-alkyl, which has a substituent from the group consisting of chlorine, bromine, hydroxy, cyano, C1 2- Alkoxy, phenoxy, phenyl, formyloxy, C24-alkanoyloxy, benzoyloxy, C 1-2 -alkoxycarbonyl, C1 2-alkoxycarbonyloxy, C 1-2 -alkyl and di- (C1-2-alkyl) -aminocarbonyloxy can or a group especially hydrogen, ethyl, cyanoethyl, acetoxyethyl, especially hydrogen or ethyl, or, if K is 1,4-naphthylene, hydrogen or C2-4-alkyl, especially hydrogen or -ethyl, especially hydrogen. 7. Azofarbstoffe der Formel I, gemäss Anspruch 1, worin R2 geradkettiges C1 4-Alkyl oder eine Gruppe der Formel -C(CH3)H-CH2-, -CH2-CH (CH3)-oder -CH2CH2-0-CH2CH2-, insbesondere 12-Aethylen bedeutet.7. Azo dyes of the formula I according to claim 1, wherein R2 is straight-chain C1 4-alkyl or a group of the formula -C (CH3) H-CH2-, -CH2-CH (CH3) -or -CH2CH2-0-CH2CH2-, in particular means 12-ethylene. 8. Verfahren zur Herstellung der Azofarbstoffe der Formel I, gemäss Anspruch 1, dadurch gekennzeichnet.8. Process for the preparation of the azo dyes of the formula I according to Claim 1, characterized. dass man, in beliebiger Reihenfolge, eine Verbindung der Formel II worin R = R1 oder R', R' = Hn-1 oder A A eine Gruppe der Formel -R2-COOH oder ein funktionelles Säurederivat einer solchen Gruppe und n 1 oder 2 bedeuten, mit ein bis 2 Mol einer Verbindung der Formel III worin B eine Gruppe der Formel -CO-R2-Hal oder -CO-CR"=CHR", die beiden R" Wasserstoff oder das eine Methyl und das andere Wasserstoff und Hal Chlor oder Brom bedeuten, umsetzt und mit der Diazoniumverbindung aus einem Amin der Formel IV D - NH2 (IV) kuppelt.that one, in any order, a compound of formula II wherein R = R1 or R ', R' = Hn-1 or AA is a group of the formula -R2-COOH or a functional acid derivative of such a group and n is 1 or 2, with one to 2 moles of a compound of the formula III wherein B is a group of the formula -CO-R2-Hal or -CO-CR "= CHR", the two R "are hydrogen or one is methyl and the other is hydrogen and Hal is chlorine or bromine, and reacts with the diazonium compound from an amine of the formula IV D - NH2 (IV) couples. 9. Verwendung der Azofarbstoffe der Formel I gemäss Anspruch 1, zum Färben oder Bedrucken von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen.9. Use of the azo dyes of the formula I according to claim 1 for Dyeing or printing of fibers or threads or materials made therefrom made of fully or semi-synthetic, hydrophobic, high-molecular organic substances.
DE19782805201 1978-02-08 1978-02-08 Diazo dyes contg. a dioxanyl gp. - imparting red, blue etc. colours to synthetic fibres Withdrawn DE2805201A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2501220A1 (en) * 1980-03-13 1982-09-10 Sandoz Sa

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2501220A1 (en) * 1980-03-13 1982-09-10 Sandoz Sa

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