EP0051188A1 - Process for improving the light fastness of polyamide dyeings - Google Patents

Process for improving the light fastness of polyamide dyeings Download PDF

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Publication number
EP0051188A1
EP0051188A1 EP81108415A EP81108415A EP0051188A1 EP 0051188 A1 EP0051188 A1 EP 0051188A1 EP 81108415 A EP81108415 A EP 81108415A EP 81108415 A EP81108415 A EP 81108415A EP 0051188 A1 EP0051188 A1 EP 0051188A1
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Prior art keywords
copper complexes
polyamide
light fastness
alkyl
formula
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German (de)
French (fr)
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EP0051188B1 (en
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Reinhard Dr. Preuss
Joachim Dr. Grütze
Ulrich Dr. Beck
Hellmuth Pantke
Karl Vogel
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Bayer AG
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Bayer AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/58—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides
    • D06M11/63—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides with hydroxylamine or hydrazine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6423—Compounds containing azide or oxime groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65112—Compounds containing aldehyde or ketone groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/241—Polyamides; Polyurethanes using acid dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • the present invention relates to a process for the production of polyamide dyeings. improved light fastness, which is characterized in that the polyamide. before, during or after coloring with copper complexes, the reaction products. of optionally substituted salicylaldehydes with alkylamines, aromatic diamines or hydrazine (I) and / or copper complexes of optionally substituted o-hydroxybenzophenones (II).
  • the compounds (I) and (II) are used in amounts of about 0.05-2%, preferably 0.1-0.2%, based on the weight of the polyamide. It is preferably added to the dyebath.
  • the rings A can optionally be substituted, in particular by alkyl (C 1 -C 4 ), cycloalkyl, alkoxy, in particular C 1 -C 4 alkoxy, halogen and OH, and likewise the radicals Ar.
  • optionally further substituted 2- (2'-hydroxyphenyl) benzotriazoles III
  • the compounds (III) and (IV) are used in amounts of 0.5-4%, preferably 1-2%, based on the weight of the polyamide. used.
  • the compounds (I) are obtained in a manner known per se (cf., for example, US Pat. No. 3,336,710) by reacting the corresponding starting compounds with - preferably stoichiometric amounts - a copper salt, in particular a salt of a mineral acid such as copper (II) chloride, preferably in alcoholic or aqueous -alcoholic medium.
  • Polyamide is understood to mean natural and synthetic polyamide.
  • the dyeings can be produced in a conventional manner using both metal complex dyes and acid dyes.
  • the known types in particular the 1: 2 chromium or 1: 2 cobalt complexes of Mono- or disazo dyes used, which are described in large numbers in the literature.
  • the dyes can in particular also contain 1-2 sulfo groups.
  • Suitable acid dyes are commercially available types, which are preferably used in combination with the metal complex dyes.
  • the compounds I and II are of course used in finely divided form, as is obtained by grinding in the presence of customary dispersants.
  • 100 g of polyamide 6 fibers are introduced into 2000 ml of an aqueous dye liquor, which contains 0.1 g of the copper complex of the formula and 0.5 g of the metal complex dye of the formula contains.
  • a pH of 6 is set by adding acetic acid. Then the temperature of the liquor is slowly increased with occasional stirring. It is dyed at 98 ° C for 1 hour.
  • the goods are then removed from the dye bath and rinsed thoroughly.
  • the dyeing produced in this way shows improved lightfastness compared to the dyeing not treated with (1).
  • a further improvement in light fastness is achieved if, in addition to (1), 1.0 g of the compound of the formula be added to the dye bath.
  • the coloring can also be carried out under HT conditions, i.e. at temperatures of 110-130 ° C in an autoclave.
  • a polyamide 6 fabric 100 g of a polyamide 6 fabric are placed in 2000 ml of an aqueous dye liquor containing 0.5 g of the metal complex dye of the formula (2). It is dyed in the usual way at 98 ° C. and pH 6. After rinsing, drying is carried out and the polyamide fabric is impregnated with a liquor on a padder; which contains 1 g of compound (1) in dispersed form per liter of water.
  • the pressure of the foulard rollers is set so that the impregnated polyamide doubles its dry weight when wet.
  • the dyeing treated in this way shows improved lightfastness compared to the dyeing which has not been treated.
  • a further improvement in light fastness can be achieved if an impregnating liquor is used which contains 10.0 g of compound (3) in addition to (1).
  • the dyeing produced in this way shows improved lightfastness compared to the dyeing not treated with (1).
  • a further improvement in light fastness is achieved if, in addition to (1), 1.0 g of compound (3) are added to the liquor.

Abstract

Die Lichtechtheit von Polyamidfärbungen läßt sich dadurch verbessern, daß man Polyamidfasermaterialien vor, während oder nach der Färbung mit Kupferkomplexen der Umsetzungsprodukte von Salicylaldehyden mit Aminen (z.B. Cyclohexylamin) oder mit Kupferkomplexen von o-Hydroxybenzophenonen behandelt.The lightfastness of polyamide dyeings can be improved by treating polyamide fiber materials with copper complexes of the reaction products of salicylaldehydes with amines (e.g. cyclohexylamine) or with copper complexes of o-hydroxybenzophenones before, during or after dyeing.

Description

Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von Polyamidfärbungen mit. verbesserter Lichtechtheit, welches dadurch gekennzeichnet ist, daß man das Polyamid. vor, während oder nach der Färbung mit Kupferkomplexen, der Umsetzungsprodukte. von gegebenenfalls substituierten Salicylaldehyden mit Alkylaminen, aromatischen Diaminen oder Hydrazin (I) und/oder Kupferkomplexen gegebenenfalls substituierter o-Hydroxybenzophenone (II) behandelt.The present invention relates to a process for the production of polyamide dyeings. improved light fastness, which is characterized in that the polyamide. before, during or after coloring with copper complexes, the reaction products. of optionally substituted salicylaldehydes with alkylamines, aromatic diamines or hydrazine (I) and / or copper complexes of optionally substituted o-hydroxybenzophenones (II).

Die Verbindungen (I) und (II) werden dabei in Mengen von etwa 0,05 - 2 %, vorzugsweise 0,1 - 0,2 %, bezogen auf das Gewicht des Polyamids eingesetzt. Vorzugsweise erfolgt ein Zusatz zum Färbebad.The compounds (I) and (II) are used in amounts of about 0.05-2%, preferably 0.1-0.2%, based on the weight of the polyamide. It is preferably added to the dyebath.

Besonders geeignete Verbindungen (I) sind solche der Formeln

Figure imgb0001
worin

  • R = C1-C18-Alkyl oder Cycloalkyl, vorzugsweise C4-C10-Alkyl oder Cyclohexyl,
    Figure imgb0002
    Figure imgb0003
    worin Ar = Arylen, insbesondere gegebenenfalls substituiertes Phenylen-1,4 oder Phenylen-1,2.
    Figure imgb0004
Particularly suitable compounds (I) are those of the formulas
Figure imgb0001
 wherein
  • R = C 1 -C 18 alkyl or cycloalkyl, preferably C 4 -C 10 alkyl or cyclohexyl,
    Figure imgb0002
    Figure imgb0003
     wherein Ar = arylene, in particular optionally substituted phenylene-1,4 or phenylene-1,2.
    Figure imgb0004

Besonders geeignete.Verbindungen (II) sind solche der Formeln:

Figure imgb0005
insbesondere die entsprechenden 4,4'-Dialkoxyverbindungen
Figure imgb0006
worin R = C1-C18-Alkyl oder Cycloalkyl, insbesondere C4-C10-Alkyl oder Cyclohexyl.Particularly suitable compounds (II) are those of the formulas:
Figure imgb0005
 especially the corresponding 4,4'-dialkoxy compounds
Figure imgb0006
 wherein R = C 1 -C 18 alkyl or cycloalkyl, in particular C 4 -C 10 alkyl or cyclohexyl.

Die Ringe A können dabei gegebenenfalls substituiert sein, insbesondere durch Alkyl (C1-C4), Cycloalkyl, Alkoxy, insbesondere C1-C4-Alkoxy, Halogen und OH, ebenso die Reste Ar.The rings A can optionally be substituted, in particular by alkyl (C 1 -C 4 ), cycloalkyl, alkoxy, in particular C 1 -C 4 alkoxy, halogen and OH, and likewise the radicals Ar.

Vorzugsweise werden die Verbindungen (I) und (II) in Kombination mit gegebenenfalls weitersubstituierten 2-(2'-Hydroxyphenyl)-benzotriazolen (III), insbesondere solchen der Formel

Figure imgb0007
worin X = H, Cl R1, R2 = H, Alkyl, insbesondere C1-C4-Alkyl und/oder gegebenenfalls weitersubstituierten 0,0'-Dihydroxybenzophenonen (IV), insbesondere 4,4'-Dialkoxy-2,2'-dihydroxybenzophenonen (IVa) eingesetzt.The compounds (I) and (II) are preferably used in combination with optionally further substituted 2- (2'-hydroxyphenyl) benzotriazoles (III), in particular those of the formula
Figure imgb0007
 wherein X = H, Cl R1 , R2 = H , alkyl, in particular C 1 -C 4 alkyl and / or optionally further substituted 0.0'-dihydroxybenzophenones (IV), in particular 4,4'-dialkoxy-2,2'- dihydroxybenzophenones (IVa) used.

Die Verbindungen (III) und (IV) werden dabei in Mengen von 0,5 - 4, vorzugsweise 1 - 2 %, bezogen auf das Gewicht des Polyamids,. eingesetzt.The compounds (III) and (IV) are used in amounts of 0.5-4%, preferably 1-2%, based on the weight of the polyamide. used.

Die Verbindungen (I) erhält man in an sich bekannter Weise (vgl. z.B. US-PS 3_361 710) durch Umsetzung der entsprechenden Ausgangsverbindungen mit - bevorzugt stöchiometrischen Mengen - eines Kupfersalzes, insbesondere eines Salzes einer Mineralsäure wie Kupfer-IIchlorid in vorzugsweise alkoholischen oder wäßrig-alkoholischen Medium.The compounds (I) are obtained in a manner known per se (cf., for example, US Pat. No. 3,336,710) by reacting the corresponding starting compounds with - preferably stoichiometric amounts - a copper salt, in particular a salt of a mineral acid such as copper (II) chloride, preferably in alcoholic or aqueous -alcoholic medium.

Unter Polyamid wird natürliches und synthetisches Polyamid verstanden.Polyamide is understood to mean natural and synthetic polyamide.

Die Färbungen können in herkömmlicher Weise sowohl mit Metallkomplexfarbstoffen als auch mit Säurefarbstoffen erzeugt werden.The dyeings can be produced in a conventional manner using both metal complex dyes and acid dyes.

Als Metallkomplexfarbstoffe werden die bekannten Typen, insbesondere die 1:2-Chrom- oder 1:2-Kobaltkomplexe von Mono- oder Disazofarbstoffen eingesetzt, die in der Literatur in großer Zahl beschrieben sind. Die Farbstoffe können insbesondere auch 1-2 Sulfogruppen enthalten.The known types, in particular the 1: 2 chromium or 1: 2 cobalt complexes of Mono- or disazo dyes used, which are described in large numbers in the literature. The dyes can in particular also contain 1-2 sulfo groups.

Geeignete Säurefarbstoffe sind handelsübliche Typen, die vorzugsweise in Kombination mit'den Metallkomplexfarbstoffen eingesetzt werden.Suitable acid dyes are commercially available types, which are preferably used in combination with the metal complex dyes.

Die Verbindungen I und II kommen - sofern sie nicht wasserlöslich sind - selbstverständlich in fein verteilter Form, wie sie durch Mahlung in Gegenwart üblicher Dispergiermittel erhalten wird, zum Einsatz.Unless they are water-soluble, the compounds I and II are of course used in finely divided form, as is obtained by grinding in the presence of customary dispersants.

1) Herstellungsbeispiele1) Manufacturing examples a) Herstellung einer Verbindung der Formela) Preparation of a compound of the formula

Figure imgb0008
568 g Cyclohexylamin, 683 g Salicylaldehyd und 2,5 1 Toluol werden am Wasserabscheider unter Stickstoff am Rückfluß gehalten, bis kein Wasser mehr abgeschieden wird. Das Toluol wird unter reduziertem Druck abdestilliert. Der Rückstand wird mit einer Lösung aus 196 g Natriumhydroxyd und 2 1 Methanol versetzt und 30 Min. zum Sieden erhitzt. Dann werden 448 g Kupfer-II-chloriddihydrat gelöst in 2 1 Methanol rasch unter Rühren zugetropft. Nach 30 Min. Rückfluß wird abgesaugt. Das Produkt kann aus DMF umkristallisiert werden. Man erhält braune Kristalle vom Schmelzpunkt 165-168°C.
Figure imgb0008
 568 g of cyclohexylamine, 683 g of salicylaldehyde and 2.5 l of toluene are kept under reflux on a water separator under nitrogen until no more water is separated off. The toluene is distilled off under reduced pressure. A solution of 196 g of sodium hydroxide and 2 l of methanol is added to the residue and the mixture is heated to boiling for 30 minutes. Then 448 g of copper (II) chloride dihydrate dissolved in 2 l of methanol are rapidly added dropwise with stirring. After 30 minutes of reflux, the product is filtered off with suction. The product can be recrystallized from DMF. Brown crystals of melting point 165-168 ° C. are obtained.

b) Herstellung der Verbindung der Formelb) Preparation of the compound of the formula

Figure imgb0009
Figure imgb0009

1100 g 4,4'-Dimethoxy-2,2'-dihydroxybenzophenon 220 g Natriummethylat und 5 1 Ethanol. werden 3 h auf Rückflußtemperatur gehalten.1100 g of 4,4'-dimethoxy-2,2'-dihydroxybenzophenone, 220 g of sodium methylate and 5 l of ethanol. are kept at reflux temperature for 3 h.

Dann werden 340 g Kupfer-II-chloriddihydrat in 3 1 Ethanol gelöst unter Rühren zugegeben. Nach 4-stündigem Kochen am Rückfluß werden 5 1 Ethanol abdestilliert. Der Rückstand wird mit Isopropanol ausgekocht und heiß abgesaugt. Man erhält grün-braune Kristalle mit einem Schmelz- intervall.von 270-280°C.Then 340 g of copper (II) chloride dihydrate dissolved in 3 l of ethanol are added with stirring. After refluxing for 4 hours, 5 liters of ethanol are distilled off. The residue is boiled with isopropanol and suction filtered while hot. Green-brown crystals with a melting interval of 270-280 ° C. are obtained.

2) Applikationsbeispiele2) Application examples a1) Auszieh-Verfahrena 1 ) Pull-out procedure

100 g Polyamid-6-Fasern werden in 2000 ml einer wäßrigen Färbeflotte eingetragen, die 0,1 g des Kupferkomplexes der Formel

Figure imgb0010
und 0,5 g des Metallkomplex-Farbstoffes der Formel
Figure imgb0011
enthält. Durch Zusatz von Essigsäure wird ein pH-Wert.von 6 eingestellt. Dann wird die Temperatur der Flotte bei gelegentlichem Umrühren langsam erhöht. Es wird 1 Stunde bei 98°C gefärbt.100 g of polyamide 6 fibers are introduced into 2000 ml of an aqueous dye liquor, which contains 0.1 g of the copper complex of the formula
Figure imgb0010
 and 0.5 g of the metal complex dye of the formula
Figure imgb0011
 contains. A pH of 6 is set by adding acetic acid. Then the temperature of the liquor is slowly increased with occasional stirring. It is dyed at 98 ° C for 1 hour.

Danach wird die Ware dem Färbebad entnommen und gründlich gespült.The goods are then removed from the dye bath and rinsed thoroughly.

Die so hergestellte Färbung zeigt eine verbesserte Lichtechtheit gegenüber der nicht mit (1) behandelten Färbung.The dyeing produced in this way shows improved lightfastness compared to the dyeing not treated with (1).

Eine weitere Verbesserung der Lichtechtheit wird erreicht, wenn zusätzlich zu (1) noch 1,0 g der Verbindung der Formel

Figure imgb0012
dem Färbebad zugesetzt werden.A further improvement in light fastness is achieved if, in addition to (1), 1.0 g of the compound of the formula
Figure imgb0012
 be added to the dye bath.

Die Färbung kann auch unter HT-Bedingungen, d.h. bei Temperaturen von 110-130°C im Autoklaven, durchgeführt-werden.The coloring can also be carried out under HT conditions, i.e. at temperatures of 110-130 ° C in an autoclave.

Ähnliche Effekte der Lichtechtheitsverbesserung von Färbungen auf Polyamid erhält man, wenn unter den angegebenen Applikationsbedingungen an Stelle von (1) der Kupfer-Komplex der Formel

Figure imgb0013
eingesetzt wird.Similar effects of improving the light fastness of dyeings on polyamide are obtained if, instead of (1), the copper complex of the formula instead of (1) under the specified application conditions
Figure imgb0013
 is used.

Eine weitere Verbesserung der Lichtechtheit tritt ein, wenn zusätzlich zu Substanz (4) die Verbindung (3) zu dem Färbebad gegeben wird.A further improvement in light fastness occurs if, in addition to substance (4), compound (3) is added to the dyebath.

Eine ähnliche Verbesserung der Lichtechtheit wird erreicht, wenn die Färbeflotte anstelle von Verbindung (1) den Kupferkomplex (4) oder (4a) enthält.

Figure imgb0014
A similar improvement in light fastness is achieved if the dye liquor contains the copper complex (4) or (4a) instead of compound (1).
Figure imgb0014

a2) Foulard-Verfahrena 2 ) Foulard procedure

100 g eines Polyamid-6-Gewebes werden in 2000 ml einer wäßrigen Färbeflotte gegeben, die 0,5 g des Metallkomplex-Farbstoffes der Formel (2) enthält. Es wird in üblicher Weise bei 98°C und pH 6 gefärbt. Nach dem Spülen wird getrocknet und das Polyamidgewebe auf einem Foulard mit einer Flotte imprägniert; die pro Liter Wasser 1 g der Verbindung (1) in dispergierter Form enthält.100 g of a polyamide 6 fabric are placed in 2000 ml of an aqueous dye liquor containing 0.5 g of the metal complex dye of the formula (2). It is dyed in the usual way at 98 ° C. and pH 6. After rinsing, drying is carried out and the polyamide fabric is impregnated with a liquor on a padder; which contains 1 g of compound (1) in dispersed form per liter of water.

Der Druck der Foulard-Walzen ist so eingestellt, daß das imprägnierte Polyamid im feuchten Zustand sein Trockengewicht verdoppelt.The pressure of the foulard rollers is set so that the impregnated polyamide doubles its dry weight when wet.

Nach dem Imprägnier-Vorgang wird bei 180°C 30 Sekunden getrocknet und fixiert.After the impregnation process is dried and fixed at 180 ° C for 30 seconds.

Die so behandelte Färbung zeigt gegenüber der nicht behandelten Färbung eine verbesserte Lichtechtheit.The dyeing treated in this way shows improved lightfastness compared to the dyeing which has not been treated.

Eine weitere Verbesserung der Lichtechtheit kann erreicht werden, wenn eine Imprägnierflotte verwendet wird, die zusätzlich zu (1) noch 10,0 g der Verbindung (3) enthält.A further improvement in light fastness can be achieved if an impregnating liquor is used which contains 10.0 g of compound (3) in addition to (1).

Eine ähnliche Verbesserung der Lichtechtheit wird erreicht, wenn die Klotzflotte anstelle von Verbindung (1) den Kupferkomplex (4) enthält.A similar improvement in light fastness is achieved if the padding liquor contains the copper complex (4) instead of compound (1).

b) Säurefarbstoffeb) acid dyes

100 g Polyamid-6-fasern werden in 200 ml einer wäßrigen Färbeflotte gegeben, die 0,1 g der Verbindung (1) und 0,5 g des Farbstoffs der Formel

Figure imgb0015
enthält. Man stellt auf pH 6 ein und färbt 1 Stunde bei 98°C.100 g of polyamide 6 fibers are placed in 200 ml of an aqueous dye liquor containing 0.1 g of compound (1) and 0.5 g of the dye of the formula
Figure imgb0015
 contains. The pH is adjusted to 6 and dyeing at 98 ° C. for 1 hour.

Die so hergestellte Färbung zeigt eine verbesserte Lichtechtheit gegenüber der nicht mit (1) behandelten Färbung.The dyeing produced in this way shows improved lightfastness compared to the dyeing not treated with (1).

Eine weitere Verbesserung der Lichtechtheit wird erreicht, wenn zusätzlich zu (1) noch 1,0 g der Verbindung (3) die Flotte gegeben werden.

Figure imgb0016
A further improvement in light fastness is achieved if, in addition to (1), 1.0 g of compound (3) are added to the liquor.
Figure imgb0016

Claims (7)

1) Verfahren zur Verbesserung der Lichtechtheit von Polyamidfärbungen, dadurch gekennzeichnet, daß man Polyamidfasermaterialien vor, während oder nach der Färbung. mit Kupferkomplexen der Umsetzungsprodukte von gegebenenfalls substituierten Salicylaldehyden mit Alkylaminen, aromatischen Diaminen oder Hydrazin (I) und/oder Kupferkomplexen gegebenenfalls substituierter o-Hydroxybenzophenone (II) behandelt.1) Process for improving the light fastness of polyamide dyeings, characterized in that polyamide fiber materials before, during or after the dyeing. treated with copper complexes of the reaction products of optionally substituted salicylaldehydes with alkylamines, aromatic diamines or hydrazine (I) and / or copper complexes with optionally substituted o-hydroxybenzophenones (II). 2) Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Kupferkomplexe dem Färbebad zusetzt.2) Method according to claim 1, characterized in that the copper complexes are added to the dyebath. 3) Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man 0,05-2 % bezogen auf das Fasergewicht der Kupferkomplexe einsetzt.3) Method according to claim 1, characterized in that one uses 0.05-2% based on the fiber weight of the copper complexes. 4) Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Kupferkomplexe solche der Formel
Figure imgb0017
worin R = C1-C18-Alkyl oder Cycloalkyl bedeutet, einsetzt.4) Method according to claim 1, characterized in that one of those of the formula as copper complexes
Figure imgb0017
 where R = C 1 -C 18 alkyl or cycloalkyl. 5) Verfahren nach Anspruch 1, dadurch gekenn.zeichnet, daß man als Kupferkomplexe solche der Formeln
Figure imgb0018
oder
Figure imgb0019
worin Ar = gegebenenfalls substituiertes Phenylen-1,4 oder Phenylen-1,2 bedeutet, einsetzt.5) Method according to claim 1, characterized in that the copper complexes are those of the formulas
Figure imgb0018
 or
Figure imgb0019
 where Ar = optionally substituted phenylene-1,4 or phenylene-1,2. 6) Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Kupferkomplexe solche der Formel
Figure imgb0020
Figure imgb0021
worin R = C1-C18-Alkyl oder Cycloalkyl und die Ringe A gegebenenfalls weitere Substituenten tragen, einsetzt.6) Process according to claim 1, characterized in that the copper complexes are those of the formula
Figure imgb0020
Figure imgb0021
 where R = C 1 -C 18 alkyl or cycloalkyl and the rings A optionally carry further substituents. 7) Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Kupfer-Komplexe in Kombination mit 2-(2'-Hydroxyphenyl)-benzotriazolen einsetzt.7) Process according to claim 1, characterized in that the copper complexes are used in combination with 2- (2'-hydroxyphenyl) benzotriazoles.
EP81108415A 1980-10-31 1981-10-16 Process for improving the light fastness of polyamide dyeings Expired EP0051188B1 (en)

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EP0185611A1 (en) * 1984-12-21 1986-06-25 Ciba-Geigy Ag Process for the photochemical stabilisation of synthetic fibrous materials containing polyamide fibres
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EP0245204A1 (en) * 1986-05-05 1987-11-11 Ciba-Geigy Ag Process for the photochemical stabilization of undyed and dyed fibrous polyamide material and its mixture with other fibres
EP0255481A1 (en) * 1986-07-29 1988-02-03 Ciba-Geigy Ag Process for the photochemical stabilisation of a fibrous polyamide material and its mixtures with other fibres

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