DE4200601A1 - New phenoxy:carbonyl:alkyl-substd. dispersion dyes - used for dyeing (semi)-synthetic fibres e.g. polyester or cellulose acetate with good fastness - Google Patents

New phenoxy:carbonyl:alkyl-substd. dispersion dyes - used for dyeing (semi)-synthetic fibres e.g. polyester or cellulose acetate with good fastness

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Publication number
DE4200601A1
DE4200601A1 DE4200601A DE4200601A DE4200601A1 DE 4200601 A1 DE4200601 A1 DE 4200601A1 DE 4200601 A DE4200601 A DE 4200601A DE 4200601 A DE4200601 A DE 4200601A DE 4200601 A1 DE4200601 A1 DE 4200601A1
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DE
Germany
Prior art keywords
formula
dyeing
fastness
alkyl
pts
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Withdrawn
Application number
DE4200601A
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German (de)
Inventor
Ruedi Altermatt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Sandoz Patent GmbH
Original Assignee
Sandoz AG
Sandoz Patent GmbH
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Application filed by Sandoz AG, Sandoz Patent GmbH filed Critical Sandoz AG
Priority to DE4200601A priority Critical patent/DE4200601A1/en
Publication of DE4200601A1 publication Critical patent/DE4200601A1/en
Withdrawn legal-status Critical Current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
    • 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
    • C09B1/02—Hydroxy-anthraquinones; Ethers or 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
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
    • C09B1/5155—N-alkyl, N-aralkyl or N-cycloalkyl derivatives only amino and hydroxy 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
    • C09B1/56—Mercapto-anthraquinones
    • C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
    • C09B1/60—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aliphatic, cycloaliphatic or araliphatic radicals
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • 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
    • C09B25/00—Quinophthalones
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/02—Coumarine dyes

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

Abstract

Phenoxycarbonylalkyl-substd. dispersion dyes of formula (I) are new. In (I) F' = residue of a non-azo dispersion dye, and Y = 1-3C alkylene. Ring A opt. has 1 or 2 substits. selected from (i) 1 or 2 of halogen, alkyl and alkoxy; and (ii) one of CF3, OH, NO2, CHO, CN, thiocyanate; 1-4C alkylcarbonyl, 1-2C alkylcarbonyloxy, aminocarbonyl, 1-3C alkoxycarbonyl, (1-2C) alkoxy-(2-3C) alkoxycarbonyl, 1-4C acylamino and phenyl. USE/ADVANTAGE - The use of (I) is claimed for dyeing, pad-dyeing or printing of fibres or filaments (or derived materials) of (semi)synthetic hydrophobic organic polymers. (I) are esp. for dyeing aromatic polyester or cellulose 2 1/2 or triacetate, giving e.g. violet, greenish yellow, greenish blue, blue orange or luminescent red shades. The dyeing have good general fastness, esp. excellent thermomigration fastness, good fastness to light, thermofixing, sublimation and pleating, and excellent wet-fastness, esp. after permanent press finishing. In an example, 12 pts. 1-amino-4-hydroxyanthraquinone, 9 pts. 2-methoxyphenyl acrylate, 0.1 pts. ZnCl2 and 50 pts. glacial acetic acid were refluxed for 10 hrs. at 119-121 deg. C. Work-up gave 1-(2-(2-methoxyphenoxycarbonyl) -ethylamino)-4-hydroxyanthraquinone, which dyed polyester fibres violet with excellent fastness.

Description

Gegenstand der Erfindung sind die Dispersionsfarbstoffe der Formel IThe invention relates to the disperse dyes of the formula I.

worin F den Rest eines nichtazoiden Dispersionsfarbstoffs und Y einen C1-3-Alkylenrest bedeuten
und der Kern A bis zu zwei Substituenten tragen kann, darunter bis zu zwei aus der Gruppe Halogen, Alkyl und Alkoxy und einen Substituenten aus der Gruppe Trifluormethyl, Hydroxy, Nitro, Formyl, Cyan, Rhodan, C1-4-Alkylcarbonyl, C1-2-Alkylcarbonyloxy, Aminocarbonyl, C1-3-Alkoxy­ carbonyl, C1-3-Alkoxy-C2-3-alkoxycarbonyl, C1-4-Acylamino oder Phenyl.wherein F is the residue of a nontazoic disperse dye and Y is a C 1-3 alkylene residue
and the core A can carry up to two substituents, including up to two from the group halogen, alkyl and alkoxy and one substituent from the group trifluoromethyl, hydroxy, nitro, formyl, cyano, rhodane, C 1-4 alkylcarbonyl, C 1 -2- alkylcarbonyloxy, aminocarbonyl, C 1-3 -alkoxy carbonyl, C 1-3 -alkoxy-C 2-3 -alkoxycarbonyl, C 1-4 -acylamino or phenyl.

Bevorzugte Reste F sind solche der Anthrachinon-, Styryl-, Chino­ phthalon-, Perylen- und Cumarinreihe, insbesondere solche der Anthrachinon- und Styrylreihe.Preferred radicals F are those of the anthraquinone, styryl and chino phthalone, perylene and coumarin series, especially those of Anthraquinone and styryl series.

Das C1-3-Zwischenglied Y entspricht vorzugsweise einer der folgenden Formeln:The C 1-3 link Y preferably corresponds to one of the following formulas:

insbesondere -CH₂CH₂- und trägt keine Substituenten.in particular -CH₂CH₂- and carries no substituents.

Diese Farbstoffe zeichnen sich gegenüber den nächstvergleichbaren, bekannten Dispersionsfarbstoffen vor allem durch ihr ausgezeichnetes Thermomigrationsverhalten (Haushaltwäsche M C4A 60°C) aus. These dyes stand out from the closest comparable well-known disperse dyes especially because of their excellent Thermomigration behavior (household laundry M C4A 60 ° C).  

Vorzugsweise trägt der Benzolkern A Substituenten entsprechend der FormelThe benzene nucleus A preferably carries substituents corresponding to that formula

worin
die beiden R1,2 unabhängig voneinander Wasserstoff, Fluor, Methyl, C1-2-Alkoxycarbonyl, Methoxy oder Aethoxy,
R₁₃ Wasserstoff, Fluor, Chlor, Brom, Methyl, C1-2-Alkoxycarbonyl, Methoxy, Aethoxy oder Phenyl und
R₁₄ Wasserstoff, Methyl, Methoxy oder Aethoxy bedeuten.wherein
the two R 1,2 independently of one another are hydrogen, fluorine, methyl, C 1-2 alkoxycarbonyl, methoxy or ethoxy,
R₁₃ hydrogen, fluorine, chlorine, bromine, methyl, C 1-2 alkoxycarbonyl, methoxy, ethoxy or phenyl and
R₁₄ represent hydrogen, methyl, methoxy or ethoxy.

Die neuen Farbstoffe können vorzugsweise nach den folgenden drei allgemein bekannten Verfahren hergestellt werden:The new dyes may preferably be in the following three generally known methods can be produced:

  • I. Addition einer Verbindung der Formel II an einen aminogruppenhaltigen Farbstoff der Formel III worin
    R Wasserstoff, Alkyl, Alkenyl, Halogenalkenyl, Alkinyl, Cyanalkyl, Benzyl, Phenyläthyl, Phenylpropyl, Hydroxyalkyl, Alkoxyalkyl, Alkoxycarbonylalkyl, Alkylcarbonyloxyalkyl oder Alkoxycarbonyloxyalkyl bedeutet,    I. Addition of a compound of formula II to an amino group-containing dye of the formula III wherein
    R denotes hydrogen, alkyl, alkenyl, haloalkenyl, alkynyl, cyanoalkyl, benzyl, phenylethyl, phenylpropyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylcarbonyloxyalkyl or alkoxycarbonyloxyalkyl,
  • II. Kondensation eines Farbstoffs der Formel IV F-XH (IV)worin X = -N(R)-, -O- oder -S- und R die oben angegebene Bedeutung besitzt,
    mit einer Verbindung der Formel V worin Hal Chlor oder Brom bedeutet,    II. Condensation of a dye of the formula IV F-XH (IV) in which X = -N (R) -, -O- or -S- and R has the meaning given above,
    with a compound of formula V where Hal is chlorine or bromine,
  • III. Kondensation einer Verbindung der Formel VI F-Y-CO-Hal (VI)worin Hal Chlor oder Brom bedeutet, mit einer Verbindung der Formel VII III. Condensation of a compound of formula VI FY-CO-Hal (VI) wherein Hal is chlorine or bromine, with a compound of formula VII

Diese Reaktionen sind dem Fachmann geläufig.These reactions are familiar to the person skilled in the art.

Alle Alkyl- und Alkoxyreste enthalten vorzugsweise 1 bis 4, ins­ besondere 1 oder 2 Kohlenstoffatome.All alkyl and alkoxy radicals preferably contain 1 to 4 ins special 1 or 2 carbon atoms.

Die Verarbeitung der neuen Verbindungen der Formel I zu Färbepräpa­ raten erfolgt auf allgemein bekannte Weise, z. B. durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum, durch Zerstäuben oder im Wirbelschichtgranulator getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken.The processing of the new compounds of formula I to dye preparation guessing is done in a well known manner, e.g. B. by grinding in Presence of dispersants and / or fillers. With the if necessary in a vacuum, by atomization or in a fluidized bed granulator Preparations can, after adding more or less water, in so-called long or short liquor dye, pad or print.

Die Farbstoffe ziehen aus wäßriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern sowie aus Cellulose-2½-acetat und Cellulosetriacetat.The dyes are excellently absorbed from an aqueous suspension Textile material made from fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. Especially They are suitable for dyeing or printing textile material linear, aromatic polyesters and cellulose-2½-acetate and cellulose triacetate.

Man färbt oder bedruckt nach an sich bekannten, z. B. den in der französischen Patentschrift Nr. 14 45 371 beschriebenen Verfahren.You dye or print according to known, z. B. in the French Patent No. 14 45 371 described method.

Die erhaltenen Färbungen besitzen gute Allgemeinechtheiten; hervor­ zuheben sind neben der guten Thermomigrierechtheit, die Lichtechtheit, Thermofixier-, Sublimier- und Plissierechtheit sowie die ausgezeichneten Naßechtheiten, insbesondere nach Permanentpreß-Ausrüstung.The dyeings obtained have good general fastness properties; forth in addition to good thermal migration resistance, lightfastness, Thermosetting, sublimation and pleating fastness as well as the excellent Wet fastness properties, especially after permanent press finishing.

Beispiel 1Example 1

12 Teile 1-Amino-4-hydroxyanthrachinon, 9 Teile Acrylsäure-2′- methoxyphenylester, 0,1 Teil Zinkchlorid und 50 Teile Eisessig werden zusammen 10 Stunden am Rückfluß bei 119-121°C gekocht. Man läßt das Reaktionsgemisch abkühlen und verdünnt es gleichzeitig langsam mit 100 Teilen Aethanol. Der ausgefallene Farbstoff wird abfiltriert und an­ schließend aus einem Gemisch aus Aethanol und Dioxan umkristallisiert. Der so erhaltene Farbstoff entspricht der Formel12 parts of 1-amino-4-hydroxyanthraquinone, 9 parts of acrylic acid-2'- methoxyphenyl ester, 0.1 part of zinc chloride and 50 parts of glacial acetic acid boiled together at reflux at 119-121 ° C for 10 hours. You leave that Cool the reaction mixture and simultaneously dilute it slowly with 100 Parts of ethanol. The precipitated dye is filtered off and on finally recrystallized from a mixture of ethanol and dioxane. The dye thus obtained corresponds to the formula

Er färbt Polyesterfasermaterial in violetten Tönen mit ausgezeichneten Echtheiten.It dyes polyester fiber material in violet tones with excellent Fastness.

µmax. 556 nm.µ max. 556 nm.

Beispiel 2Example 2

Man verfährt wie im Beispiel 1 beschrieben, ersetzt jedoch die 9 Teile Acrylsäure-2′-methoxyphenylester durch 10,3 Teile Acrylsäure-4′- methoxycarbonylphenylester. Der resultierende Farbstoff entspricht der FormelThe procedure is as described in Example 1, but the 9 parts are replaced Acrylic acid 2'-methoxyphenyl ester by 10.3 parts of acrylic acid 4'- methoxycarbonylphenyl ester. The resulting dye corresponds to the formula

Er färbt Polyesterfasermaterialien in violetten Tönen mit ausgezeich­ neten Echtheiten.It dyes polyester fiber materials in violet tones with excellent neten fastness.

Analog zu den Angaben in den obigen Beispielen werden auch die in der folgenden Tabelle formelmäßig angegebenen Farbstoffe hergestellt. Analogous to the information in the examples above, the information in the following table formulated dyes produced.  

Tabelle table

Tabelle (Fortsetzung) Table (continued)

Claims (3)

1. Die Dispersionsfarbstoffe der Formel I worin F den nichtazoiden Rest eines Dispersionsfarbstoffes und Y einen C₁-C₃-Alkylrest bedeuten, wobei der Phenylkern A bis zu zwei Substituenten tragen kann, und zwar bis zu zwei aus der Gruppe Halogen, Alkyl und Alkoxy und einen Substituenten aus der Gruppe Trifluormethyl, Hydroxy, Nitro, Formyl, Cyan, Rhodan, C1-4-Alkylcarbonyl, C1-2-Alkylcarbonyloxy, Aminocarbonyl, C1-3-Alkoxycarbonyl, C1-2- Alkoxy-C2-3-Alkoxycarbonyl, C1-4-Acylamino oder Phenyl.1. The disperse dyes of the formula I wherein F is the non-azoid radical of a disperse dye and Y is a C₁-C₃-alkyl radical, where the phenyl nucleus A can carry up to two substituents, namely up to two from the group halogen, alkyl and alkoxy and a substituent from the group trifluoromethyl, hydroxy , Nitro, formyl, cyan, rhodan, C 1-4 alkylcarbonyl, C 1-2 alkylcarbonyloxy, aminocarbonyl, C 1-3 alkoxycarbonyl, C 1-2 - alkoxy-C 2-3 alkoxycarbonyl, C 1-4 -Acylamino or phenyl. 2. Die Herstellung der Dispersionsfarbstoffe der Formel I, gemäß Anspruch 1, dadurch gekennzeichnet, daß man
  • I. eine Verbindung der Formel II an einen aminogruppenhaltigen Farbstoff der Formel III worin
    R Wasserstoff, Alkyl, Alkenyl, Halogenalkenyl, Alkinyl, Cyanalkyl, Benzyl, Phenyläthyl, Phenylpropyl, Hydroxyalkyl, Alkoxyalkyl, Alkoxycarbonylalkyl, Alkylcarbonyloxyalkyl oder Alkoxycarbonyloxyalkyl bedeutet,
    addiert, oder
  • II. einen Farbstoff der Formel IV F-XH (IV)worin X = -N(R)-, -O- oder -S- und R die oben angegebene Bedeutung besitzt,
    mit einer Verbindung der Formel V worin Hal Chlor oder Brom bedeutet, oder
  • III. eine Verbindung der Formel VI F-Y-CO-Hal (VI)worin Hal Chlor oder Brom bedeutet, mit einer Verbindung der Formel VII bedeutet, kondensiert.
2. The preparation of the disperse dyes of the formula I, according to claim 1, characterized in that
  • I. a compound of formula II to an amino group-containing dye of the formula III wherein
    R denotes hydrogen, alkyl, alkenyl, haloalkenyl, alkynyl, cyanoalkyl, benzyl, phenylethyl, phenylpropyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylcarbonyloxyalkyl or alkoxycarbonyloxyalkyl,
    added, or
  • II. A dye of the formula IV F-XH (IV) in which X = -N (R) -, -O- or -S- and R has the meaning given above,
    with a compound of formula V wherein Hal is chlorine or bromine, or
  • III. a compound of the formula VI FY-CO-Hal (VI) in which Hal is chlorine or bromine, with a compound of the formula VII means condensed.
3. Verwendung der Dispersionsfarbstoffe der Formel I gemäß Anspruch 1 zum Färben, Klotzfärben oder Bedrucken von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen.3. Use of the disperse dyes of the formula I according to claim 1 for dyeing, block dyeing or printing on fibers or threads or materials made from it from fully or semi-synthetic, hydrophobic, high-molecular organic substances.
DE4200601A 1992-01-13 1992-01-13 New phenoxy:carbonyl:alkyl-substd. dispersion dyes - used for dyeing (semi)-synthetic fibres e.g. polyester or cellulose acetate with good fastness Withdrawn DE4200601A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE4200601A DE4200601A1 (en) 1992-01-13 1992-01-13 New phenoxy:carbonyl:alkyl-substd. dispersion dyes - used for dyeing (semi)-synthetic fibres e.g. polyester or cellulose acetate with good fastness

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE4200601A DE4200601A1 (en) 1992-01-13 1992-01-13 New phenoxy:carbonyl:alkyl-substd. dispersion dyes - used for dyeing (semi)-synthetic fibres e.g. polyester or cellulose acetate with good fastness

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DE4200601A1 true DE4200601A1 (en) 1993-07-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019099772A (en) * 2017-12-08 2019-06-24 株式会社リコー Active energy ray-curable composition, active energy ray-curable ink, composition storage container, two-dimensional or three-dimensional image formation device, two-dimensional or three-dimensional image forming method, and method for producing cured product

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019099772A (en) * 2017-12-08 2019-06-24 株式会社リコー Active energy ray-curable composition, active energy ray-curable ink, composition storage container, two-dimensional or three-dimensional image formation device, two-dimensional or three-dimensional image forming method, and method for producing cured product

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