EP0379954A2 - Carrier for dyeing hydrophobic fibre materials - Google Patents

Carrier for dyeing hydrophobic fibre materials Download PDF

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Publication number
EP0379954A2
EP0379954A2 EP90100893A EP90100893A EP0379954A2 EP 0379954 A2 EP0379954 A2 EP 0379954A2 EP 90100893 A EP90100893 A EP 90100893A EP 90100893 A EP90100893 A EP 90100893A EP 0379954 A2 EP0379954 A2 EP 0379954A2
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Prior art keywords
alkyl
carrier
weight
esters
acid
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EP90100893A
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German (de)
French (fr)
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EP0379954A3 (en
EP0379954B1 (en
Inventor
Frank Dr. Bartkowiak
Hans Dr. Schulze
Willi Dr. Schössler
Heinz Ulrich Dr. Blank
Karlhans Dipl.-Ing. Jakobs
Klaus-Dieter Schultz
Karl-Heinz Dr. Passon
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Bayer AG
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Bayer AG
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Classifications

    • 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
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
    • 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
    • D06P1/65125—Compounds containing ester groups

Definitions

  • the invention relates to carriers, their preparations and processes for dyeing preferably polyester materials with disperse dyes in the presence of these carriers.
  • Known carriers used in textile practice in dyeing polyester include halogenobenzenes, halogen toluenes, N-alkylphthalimides, aromatic carboxylic esters, methylnaphthalene, diphenyl, diphenyl ether, naphthol ether, phenol ether and oxydiphenyls.
  • these connections have disadvantages.
  • the carrier types mentioned - with the exception of N-alkylphthalimides - have a strong intrinsic odor. Methylnaphthalene and the oxydiphenyls adversely affect the lightfastness of the dyeings.
  • Diphenyl ether has the disadvantage that its carrier activity depends strongly on the constitution of the disperse dye used and therefore often no reproducible colorations are obtained.
  • N-alkylphthalimides show a strong drop in the carrier effect at dyeing temperatures below 98 ° C., which indicates their use in higher regions, in the open regions Dyeing equipment limits this temperature is not reached.
  • Phthalic acid esters and benzoic acid esters have only a limited carrier effect and a limited leveling capacity and therefore require high amounts.
  • the object of the present invention is to provide highly effective, halogen-free carriers which bring about the most level possible coloring with a small amount used.
  • the dyeing achieved should meet high authenticity standards, and when dyeing mixed fibers, the accompanying fiber should not be soiled.
  • Suitable alkoxybenzoic acid esters are those of the formula wherein R C1-C7-alkyl, which may be substituted by phenyl, or phenyl, which may be substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl and R1 is C1-C4 alkyl, which may be substituted by OH.
  • the substituent -OR1 is preferably in the o- or p-position.
  • Suitable phthalimides are those of the formula wherein X is C1-C7 alkyl.
  • the preferred weight ratio of N-alkylphthalimides to the benzoic acid esters is 0.5-12: 1.
  • the carriers according to the invention are water-insoluble, they are preferably added to the dyeing liquors in the form of preparations which contain emulsifiers or dispersants and, if appropriate, solvents.
  • components 1.) - 4.) can also be used as mixtures.
  • Examples of preferred compounds (I) are: o / p-methoxybenzoic acid-n-C1-C4-alkyl esters, o / p-ethoxybenzoic acid-n-C1-C4-alkyl esters and o / p-Hydroxyethoxybenzoic acid n-C1-C4 alkyl ester.
  • Examples of preferred compounds (II) are straight-chain or branched C3-C5-N-alkylphthalimides.
  • Nonionic and anionic emulsifiers are preferred as emulsifiers 3.).
  • emulsifiers are mixtures of a) ethoxylated oils, such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali metal, alkaline earth metal and / or ammonium salts of organic sulfonic acids containing at least 10 carbon atoms, such as dodecylbenzenesulfonic acid, Sulfo fatty acids and ricinoleyl methyl tauride.
  • ethoxylated oils such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers
  • z. B. alkanols, glycols, ketones, N-substituted caprolactams or ethers can be used.
  • the carrier mixtures according to the invention are well compatible with other carriers, they can also be used in a mixture with known other carriers.
  • the disperse dyes used for dyeing are the disperse dyes usually used for dyeing polyesters, as described, for example, in "Color Index” Vol. 2, pp. 2483-2741, 3rd edition (1971).
  • the dyeing in the presence of the carriers according to the invention is carried out according to the batchwise methods customary for dyeing with disperse dyes; the usual process operating at 98 ° C. and the high-temperature process may be mentioned as such.
  • the carrier blends according to the invention are also suitable for dyeing polyester / wool and polyester / cotton blended fabrics, because when they are used the soiling of the wool and cotton content is avoided by the disperse dyes.
  • the coloring can be carried out at temperatures of 90-140 ° C, the preferred industrial use being at 90-105 ° C.
  • An additional advantage of the carrier settings described is the very good effectiveness below the cooking temperature, which pure N-alkylphthalimide carriers do not show, e.g. B. at 95 ° C, which are often not exceeded under practical conditions with open dyeing equipment.
  • the amounts of the mixture of carriers (I) and (II) required to carry out the dyeing can easily be determined from case to case by preliminary tests. In general, amounts of 1 to 7 g per liter of dye liquor have proven themselves in the usual liquor ratios of 1: 5 to 1:40.
  • N-alkylphthalimides as carriers in dyeing polyester is known and is described in DE-PS 1 769 210.
  • DE-PS 1 769 210 also discloses the use of mixtures of N-alkylphthalimides with disubstituted benzoic acid esters.
  • the mixtures according to the invention have a higher color-accelerating effect than the sum of the individual effects.
  • This synergistic increase in the effectiveness is not shown by the mixtures known hitherto (for example the mixtures of N-alkylphthalimides with alkyl group-containing salicylic acid compounds described in DE-PS 1 769 210).
  • the mixing ratio at which the synergistic optimum is present depends on the components of the carrier mixtures and can easily be determined in individual cases by preliminary tests.
  • Yarns made of polyester fibers are placed in a liquor ratio of 1:40 in a bath heated to 60 ° C, containing 0.25 g of a dye of the formula per liter 2 g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3 g of a carrier setting contains the following composition: 2.55 g of ethyl 4-methoxybenzoate 0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO 0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid.
  • the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
  • the bath is then heated to 98 ° C. and held at this temperature for 60 minutes. A uniform blue color is obtained.
  • the carrier effectiveness of the carrier mixtures of Examples 6-11 is determined by comparing the color depths achieved.
  • the small amounts of the mixtures demonstrate their more advantageous carrier activity compared to the individual components. example % By weight of the components in the mixture required amount of mixture Component I 6 30 I 80 90 55 II 7 35 I 90 120 50 II 8th 35 I 90 120 50 II 9 17 I 90 100 68 II 10th 35 I 90 100 50 II 11 52 I 80 90 40 II
  • Example 12 comparative example to DE-PS 1 769 210)
  • this mixture shows no synergistic increase in carrier effectiveness compared to the individual components.
  • the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
  • the dye liquor is then brought to the boiling temperature and held at this temperature for one hour. A full, even red color is achieved.
  • Polyester staple fibers are introduced in a liquor ratio of 1:15 into a dyeing liquor containing 1 g of a disperse dye according to Example 14 per liter, 0.03 g of a dye according to the Color Index, 2nd edition (1956) Volume 3, No. 12790, 2nd g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3.5 g of a carrier setting of Example 13.
  • the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
  • the liquor is slowly heated to 98 ° C. and treated at this temperature for one hour. A dark reddish brown color is obtained.

Abstract

Highly active and halogen-free carriers for dyeing polyester fibres contain alkyl esters of alkoxybenzoic acid or mixtures thereof with N-alkylphthalimides or mixtures of aryl esters of alkoxybenzoic acid with N-alkylphthalimides, where the said alkyl, aryl and alkoxy radicals can carry further substituents customary in textile auxiliary chemistry.

Description

Die Erfindung betrifft Carrier, ihre Zubereitungen und Verfahren zum Färben von vorzugsweise Polyestermateria­lien mit Dispersionsfarbstoffen in Gegenwart dieser Carrier.The invention relates to carriers, their preparations and processes for dyeing preferably polyester materials with disperse dyes in the presence of these carriers.

Zu den bekannten Carriern, die in der textilen Praxis beim Färben von Polyester verwendet werden, gehören Halogenbenzole, Halogentoluole, N-Alkylphthalimide, aromatische Carbonsäureester, Methylnaphthalin, Di­phenyl, Diphenylether, Naphtholether, Phenolether und Oxydiphenyle. Diese Verbindungen haben jedoch Nachteile. Beispielsweise besitzen die genannten Carriertypen - mit Ausnahme der N-Alkylphthalimide - einen starken Eigen­geruch. Methylnaphthalin und die Oxydiphenyle beein­flussen nachteilig die Lichtechtheit der Färbungen. Diphenylether hat den Nachteil, daß seine Carrierwirk­samkeit stark von der Konstitution des verwendeten Dispersionsfarbstoffes abhängt und deshalb oft keine reproduzierbaren Färbungen erhalten werden. N-Alkyl­phthalimide zeigen bei Färbetemperaturen unterhalb 98°C einen starken Abfall der Carrierwirkung, was ihre Ver­wendung in höher gelegenen Regionen, in den bei offenen Färbeapparaturen diese Temperatur nicht erreicht wird, einschränkt. Phthalsäureester und Benzoesäureester besitzen nur eine begrenzte Carrierwirkung und ein begrenztes Egalisiervermögen und erfordern deshalb hohe Einsatzmengen.Known carriers used in textile practice in dyeing polyester include halogenobenzenes, halogen toluenes, N-alkylphthalimides, aromatic carboxylic esters, methylnaphthalene, diphenyl, diphenyl ether, naphthol ether, phenol ether and oxydiphenyls. However, these connections have disadvantages. For example, the carrier types mentioned - with the exception of N-alkylphthalimides - have a strong intrinsic odor. Methylnaphthalene and the oxydiphenyls adversely affect the lightfastness of the dyeings. Diphenyl ether has the disadvantage that its carrier activity depends strongly on the constitution of the disperse dye used and therefore often no reproducible colorations are obtained. N-alkylphthalimides show a strong drop in the carrier effect at dyeing temperatures below 98 ° C., which indicates their use in higher regions, in the open regions Dyeing equipment limits this temperature is not reached. Phthalic acid esters and benzoic acid esters have only a limited carrier effect and a limited leveling capacity and therefore require high amounts.

Aufgabe der vorliegenden Erfindung ist es, hochwirksame, halogenfreie Carrier zur Verfügung zu stellen, die mit geringer Einsatzmenge eine möglichst egale Färbung be­wirken. Gleichzeitig soll die erzielte Färbung hohen Echtheitsansprüchen genügen, und bei der Färbung von Mischfasern soll keine Anschmutzung der Begleitfaser erfolgen.The object of the present invention is to provide highly effective, halogen-free carriers which bring about the most level possible coloring with a small amount used. At the same time, the dyeing achieved should meet high authenticity standards, and when dyeing mixed fibers, the accompanying fiber should not be soiled.

Es wurde nun gefunden, daß man diese Aufgabe dadurch lösen kann, daß man als Carrier Alkoxybenzoesäureal­kylester oder deren Mischungen mit N-Alkylphthalimiden oder Mischungen von Alkoxybenzoesäurearylestern mit N-­Alkylphthalimiden verwendet, wobei die genannten Alkyl-, Aryl- und Alkoxyreste weitere in der Textilhilfsmittel­chemie übliche Substituenten tragen können.It has now been found that this object can be achieved by using alkyl alkoxybenzoic acid esters or their mixtures with N-alkylphthalimides or mixtures of aryl alkoxybenzoates with N-alkylphthalimides as carriers, the alkyl, aryl and alkoxy radicals mentioned further being customary in textile auxiliary chemistry Can carry substituents.

Geeignete Alkoxybenzoesäureester sind solche der Formel

Figure imgb0001
worin
R C₁-C₇-Alkyl, das durch Phenyl substituiert sein kann, oder Phenyl, das durch C₁-C₄-Alkyl, C₁-­C₄-Alkoxy oder C₁-C₄-Alkoxycarbonyl substituiert sein kann und
R¹ C₁-C₄-Alkyl, das durch OH substituiert sein kann, bedeuten.Suitable alkoxybenzoic acid esters are those of the formula
Figure imgb0001
 wherein
R C₁-C₇-alkyl, which may be substituted by phenyl, or phenyl, which may be substituted by C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkoxycarbonyl and
R¹ is C₁-C₄ alkyl, which may be substituted by OH.

Vorzugsweise steht der Substituent -OR₁ in o- oder p-­Stellung.The substituent -OR₁ is preferably in the o- or p-position.

Geeignete Phthalimide sind solche der Formel

Figure imgb0002
worin
X C₁-C₇-Alkyl bedeutet.Suitable phthalimides are those of the formula
Figure imgb0002
 wherein
X is C₁-C₇ alkyl.

Das bevorzugte Gewichtsverhältnis von N-Alkylphthalimi­den zu den Benzoesäureestern liegt bei 0,5 - 12 : 1.The preferred weight ratio of N-alkylphthalimides to the benzoic acid esters is 0.5-12: 1.

Da die erfindungsgemäßen Carrier wasserunlöslich sind, werden sie vorzugsweise in Form von Zubereitungen, die Emulgier- oder Dispergiermittel und gegebenenfalls Lösungsmittel enthalten, den Färbeflotten zugesetzt.Since the carriers according to the invention are water-insoluble, they are preferably added to the dyeing liquors in the form of preparations which contain emulsifiers or dispersants and, if appropriate, solvents.

Werden die Alkoxybenzoesäureester (I) in Form ihrer Alkylester eingesetzt, so weisen die daraus herge­stellten Zubereitungen folgende bevorzugte Zusammen­setzung auf:

  • 1.) 40-98, insbesondere 60-90 Gew.-% (I) (als Alkylester)
  • 2.) 2-30, insbesondere 10-20 Gew.- % eines Emulgators und
  • 3.) 0-10 Gew.- % eines Lösungsmittels.
If the alkoxybenzoic acid esters (I) are used in the form of their alkyl esters, the preparations prepared therefrom have the following preferred composition:
  • 1.) 40-98, in particular 60-90% by weight (I) (as alkyl ester)
  • 2.) 2-30, in particular 10-20% by weight of an emulsifier and
  • 3.) 0-10% by weight of a solvent.

Bevorzugte Zubereitungen von Carriermischungen sind:

  • 1.) 8-58, insbesondere 10-45 Gew.-% (I),
  • 2.) 40-90, insbesondere 45-80 Gew.-% (II),
  • 3.) 2-30, insbesondere 10-20 Gew.-% eines Emulgators und
  • 4.) 0-10 Gew.-% eines Lösungsmittels
Preferred preparations of carrier mixtures are:
  • 1.) 8-58, in particular 10-45% by weight (I),
  • 2.) 40-90, in particular 45-80% by weight (II),
  • 3.) 2-30, in particular 10-20 wt .-% of an emulsifier and
  • 4.) 0-10% by weight of a solvent

Im übrigen können die Komponenten 1.) - 4.) auch als Mischungen eingesetzt werden.Otherwise, components 1.) - 4.) can also be used as mixtures.

Beispiele für bevorzugte Verbindungen (I) sind:
o/p-Methoxybenzoesäure-n-C₁-C₄-alkylester,
o/p-Ethoxybenzoesäure-n-C₁-C₄-alkylester und
o/p-Hydroxyethoxybenzoesäure-n-C₁-C₄-alkylester.Examples of preferred compounds (I) are:
o / p-methoxybenzoic acid-n-C₁-C₄-alkyl esters,
o / p-ethoxybenzoic acid-n-C₁-C₄-alkyl esters and
o / p-Hydroxyethoxybenzoic acid n-C₁-C₄ alkyl ester.

Beispiele für bevorzugte Verbindungen (II) sind grad­kettige oder verzweigte C₃-C₅-N-Alkylphthalimide.Examples of preferred compounds (II) are straight-chain or branched C₃-C₅-N-alkylphthalimides.

Als Emulgatoren 3.) werden nichtionische und anionische Emulgatoren bevorzugt.Nonionic and anionic emulsifiers are preferred as emulsifiers 3.).

Beispiele geeigneter Emulgatoren, sind Gemische aus a) oxethylierten Ölen, wie Rizinusöl oder Sojaöl, oxethy­lierten Alkoholen, Alkylphenolpolyglykolethern oder Phenylalkylphenolpolyglykolethern, b) Alkali-, Erd­alkali- und/oder Ammoniumsalzen organischer, mindestens 10 Kohlenstoffatome aufweisender Sulfonsäuren, wie Do­decylbenzolsulfonsäure, Diisobutylnaphthalinsulfonsäure, alpha-Sulfofettsäuren und Rizinoleylmethyltaurid.Examples of suitable emulsifiers are mixtures of a) ethoxylated oils, such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali metal, alkaline earth metal and / or ammonium salts of organic sulfonic acids containing at least 10 carbon atoms, such as dodecylbenzenesulfonic acid, Sulfo fatty acids and ricinoleyl methyl tauride.

Als Lösungsmittel 4.), die gegebenenfalls die Viskosität der Formulierung verbessern, können z. B. Alkanole, Gly­kole, Ketone, N-substituierte Caprolactame oder Ether verwendet werden.As a solvent 4.), which may improve the viscosity of the formulation, z. B. alkanols, glycols, ketones, N-substituted caprolactams or ethers can be used.

Besonders bevorzugte Carrier-Zubereitungen enthalten entweder

  • 1.) 70-90 Gew.-% (I) oder 10-40 Gew.-% (I) und 50-75 Gew.-% (II) sowie
  • 2.) 5-20 Gew.-% eines Additionsproduktes von 15-30 mol Ethylenoxid an Rizinus- oder Sojaöl, von 5-50 mol Ethylenoxid und/oder Propylenoxid an C₁₆-C₂₂-Fett­alkohole, Octyl- oder Nonylphenol oder Phenylethyl­phenol, Alkali-, Erdalkali-, Ammonium- oder Mono-, Di- oder Triethanolaminsalze der Dodecylbenzolsul­fonsäure.
Particularly preferred carrier preparations contain either
  • 1.) 70-90 wt .-% (I) or 10-40 wt .-% (I) and 50-75 wt .-% (II) as well
  • 2.) 5-20% by weight of an addition product of 15-30 mol ethylene oxide with castor or soybean oil, with 5-50 mol ethylene oxide and / or propylene oxide with C₁₆-C₂₂ fatty alcohols, octyl or nonylphenol or phenylethylphenol, alkali , Alkaline earth metal, ammonium or mono-, di- or triethanolamine salts of dodecylbenzenesulfonic acid.

Da die erfindungsgemäßen Carrier-Mischungen gut ver­träglich mit anderen Carriern sind, können sie auch in Mischung mit bekannten anderen Carriern verwendet werden.Since the carrier mixtures according to the invention are well compatible with other carriers, they can also be used in a mixture with known other carriers.

Die zur Färbung verwendeten Dispersionsfarbstoffe sind die üblicherweise zum Färben von Polyestern verwendeten Dispersionsfarbstoffe, wie sie beispielsweise im "Colour Index" Vol. 2, S. 2483-2741, 3. Edition (1971) be­schrieben sind. Das Färben in Gegenwart der erfindungs­gemäßen Carrier wird nach den für das Färben mit Dis­persionsfarbstoffen üblichen diskontinuierlichen Ver­fahren durchgeführt; als solche seien das übliche bei 98°C arbeitende Verfahren und das Hochtemperatur-Ver­fahren genannt.The disperse dyes used for dyeing are the disperse dyes usually used for dyeing polyesters, as described, for example, in "Color Index" Vol. 2, pp. 2483-2741, 3rd edition (1971). The dyeing in the presence of the carriers according to the invention is carried out according to the batchwise methods customary for dyeing with disperse dyes; the usual process operating at 98 ° C. and the high-temperature process may be mentioned as such.

Die erfindungsgemäßen Carrier-Mischungen eignen sich auch zum Färben von Polyester/Wolle- und Polyester/Baum­wolle-Mischgeweben, weil bei ihrer Verwendung die An­schmutzung des Woll- und Baumwolleanteils durch die Dis­persionsfarbstoffe vermieden wird.The carrier blends according to the invention are also suitable for dyeing polyester / wool and polyester / cotton blended fabrics, because when they are used the soiling of the wool and cotton content is avoided by the disperse dyes.

Mit Hilfe der Carrier-Mischungen gelingt es, Gebilde, z. B. Fäden, Fasern, Gewebe, Gewirke, Filme und Folien aus Polyestern, wie Polyterephthalsäureglykolestern, oder Polyester-Mischgewebe mit Dispersionsfarbstoffen in tiefen Tönen und hervorragend gleichmäßig zu färben. Die Färbung kann bei Temperaturen von 90-140°C durch­geführt werden, wobei die bevorzugte technische Verwen­dung bei 90-105°C erfolgt. Ein zusätzlicher Vorteil der beschriebenen Carrier-Einstellungen ist die sehr gute Wirksamkeit unterhalb Kochtemperatur, die reine N-­Alkylphthalimid-Carrier nicht zeigen, z. B. bei 95°C, die häufig unter Praxisbedingungen bei offenen Färbe­apparaturen nicht überschritten werden.With the help of carrier mixtures, it is possible to form, z. B. threads, fibers, fabrics, knitted fabrics, films and foils made of polyesters, such as polyterephthalic acid glycol esters, or polyester blended fabrics with disperse dyes in deep shades and excellent to dye evenly. The coloring can be carried out at temperatures of 90-140 ° C, the preferred industrial use being at 90-105 ° C. An additional advantage of the carrier settings described is the very good effectiveness below the cooking temperature, which pure N-alkylphthalimide carriers do not show, e.g. B. at 95 ° C, which are often not exceeded under practical conditions with open dyeing equipment.

Die zur Durchführung der Färbung erforderlichen Mengen der Mischung der Carrier (I) und (II) lassen sich durch Vorversuche von Fall zu Fall leicht ermitteln. Im all­gemeinen haben sich Mengen von 1 bis 7 g je Liter Färbe­flotte bei den üblichen Flottenverhältnissen von 1:5 bis 1:40 bewährt.The amounts of the mixture of carriers (I) and (II) required to carry out the dyeing can easily be determined from case to case by preliminary tests. In general, amounts of 1 to 7 g per liter of dye liquor have proven themselves in the usual liquor ratios of 1: 5 to 1:40.

Die Verwendung von N-Alkylphthalimiden als Carrier beim Färben von Polyester ist bekannt und in DE-PS 1 769 210 beschrieben.The use of N-alkylphthalimides as carriers in dyeing polyester is known and is described in DE-PS 1 769 210.

Aus der DE-PS 1 769 210 ist auch die Verwendung von Mi­schungen von N-Alkylphthalimiden mit disubstituierten Benzoesäureestern bekannt.DE-PS 1 769 210 also discloses the use of mixtures of N-alkylphthalimides with disubstituted benzoic acid esters.

Es ist als ausgesprochen überraschend zu bezeichnen, daß die erfindungsgemäßen Mischungen eine höhere färbebe­schleunigende Wirkung aufweisen, als es der Summe der Einzelwirkungen entspricht. Diese synergistische Erhö­hung der Wirksamkeiten zeigen die bisher bekannten Mischungen (z. B. die in der DE-PS 1 769 210 beschrie­benen Mischungen von N-Alkylphthalimiden mit alkyl­gruppenhaltigen Salicylsäure-Verbindungen) nicht. Das Mischungsverhältnis, bei dem das synergistische Optimum vorliegt, ist dabei von den Komponenten der Carrier-­Mischungen abhängig und ist im Einzelfall durch Vorver­suche leicht zu ermitteln.It can be described as extremely surprising that the mixtures according to the invention have a higher color-accelerating effect than the sum of the individual effects. This synergistic increase in the effectiveness is not shown by the mixtures known hitherto (for example the mixtures of N-alkylphthalimides with alkyl group-containing salicylic acid compounds described in DE-PS 1 769 210). The mixing ratio at which the synergistic optimum is present depends on the components of the carrier mixtures and can easily be determined in individual cases by preliminary tests.

Beispiel 1example 1

Garne aus Polyesterfasern werden im Flottenverhältnis von 1:40 in ein auf 60°C erwärmtes Bad eingebracht, das je Liter 0,25 g eines Farbstoffes der Formel

Figure imgb0003
2 g eines Kondensationsprodukts aus Naphthalinsulfonat und Formaldehyd, 2 g Natriumdihydrogenphosphat und 3 g einer Carrier-Einstellung folgender Zusammensetzung ent­hält:
2,55 g 4-Methoxybenzoesäureethylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure.Yarns made of polyester fibers are placed in a liquor ratio of 1:40 in a bath heated to 60 ° C, containing 0.25 g of a dye of the formula per liter
Figure imgb0003
 2 g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3 g of a carrier setting contains the following composition:
2.55 g of ethyl 4-methoxybenzoate
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid.

Der pH-Wert des Bades wird mit Essigsäure auf pH 4,5-5 eingestellt. Dann wird das Bad auf 98°C erhitzt und 60 Minuten bei dieser Temperatur gehalten. Man erhält eine gleichmäßige Blaufärbung.The pH of the bath is adjusted to pH 4.5-5 with acetic acid. The bath is then heated to 98 ° C. and held at this temperature for 60 minutes. A uniform blue color is obtained.

Beispiel 2-11Example 2-11

Die Färbung wird wie in Beispiel 1 beschrieben durchge­führt, wobei man Carrier-Einstellungen folgender Zu­sammensetzungen verwendet:

  • Bspl. 2: 2,55 g 4-Methoxybenzoesäure-n-propylester
    0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
  • Bspl. 3: 2,50 g 3-Methoxybenzoesäureethylester
    0,29 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,21 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
  • Bspl. 4: 2,55 g 2-Methoxybenzoesäurephenylester
    0,27 g Tri-(methylphenylethyl)-phenol mit ca. 50 mol EO
    0,18 g Calciumdodecylbenzolsulfonat (70 % in Butanol)
  • Bspl. 5: 2,50 g 4-Ethoxybenzoesauremethylester
    0,28 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,22 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
  • Bspl. 6: 0,90 g 4-Methoxybenzoesäureethylester
    1,65 g N-Butylphthalimid
    0,22 g Rizinusöl mit ca. 30 mol EO
    0,18 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
    0,05 g Stearylalkohol mit ca. 8 mol EO
  • Bspl. 7: 1,05 g 4-Ethoxybenzoesäure-n-butylester
    1,50 g N-Butylphthalimid
    0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
  • Bspl. 8: 1,05 g 4-Methoxybenzoesäurekresylester
    1,50 g N-Alkylphthalimide (Alkyl = 50 % n-­Butyl, 30 % Propyl, 20 % Ethyl)
    0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
  • Bspl. 9: 0,50 g 2-Methoxybenzoesäuremethylester
    2,05 g N-Butylphthalimid
    0,30 g Rizinusöl mit ca. 30 mol EO
    0,15 g Calciumdodecylbenzolsulfonat (70 % in Butanol)
  • Bspl. 10: 1,05 g 2-Methoxybenzoesäureethylester
    1,50 g N-Alkylphthalimide (Alkyl = 50 % n-­Butyl, 30 % Propyl, 20 % Ethyl)
    0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
  • Bspl. 11: 1,55 g 4-Ethoxybenzoesäureethylester
    1,20 g N-Alkylphthalimide (Alkyl = 70 % n-­Butyl, 30 % n-Propyl)
    0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
    0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure
The dyeing is carried out as described in Example 1, using carrier settings of the following compositions:
  • Ex. 2: 2.55 g n-propyl 4-methoxybenzoate
    0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
  • Ex. 3: 2.50 g of ethyl 3-methoxybenzoate
    0.29 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.21 g monoethanolamine salt of dodecylbenzenesulfonic acid
  • Ex. 4: 2.55 g of phenyl 2-methoxybenzoate
    0.27 g tri- (methylphenylethyl) phenol with approx. 50 mol EO
    0.18 g calcium dodecylbenzenesulfonate (70% in butanol)
  • Ex. 5: 2.50 g of methyl 4-ethoxybenzoate
    0.28 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.22 g monoethanolamine salt of dodecylbenzenesulfonic acid
  • Ex. 6: 0.90 g of ethyl 4-methoxybenzoate
    1.65 g of N-butyl phthalimide
    0.22 g castor oil with approx. 30 mol EO
    0.18 g monoethanolamine salt of dodecylbenzenesulfonic acid
    0.05 g stearyl alcohol with approx. 8 mol EO
  • Ex. 7: 1.05 g of n-butyl 4-ethoxybenzoate
    1.50 g of N-butyl phthalimide
    0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
  • Ex. 8: 1.05 g of 4-methoxybenzoic acid
    1.50 g N-alkylphthalimide (alkyl = 50% n-butyl, 30% propyl, 20% ethyl)
    0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
  • Ex. 9: 0.50 g of methyl 2-methoxybenzoate
    2.05 g of N-butyl phthalimide
    0.30 g castor oil with approx. 30 mol EO
    0.15 g calcium dodecylbenzenesulfonate (70% in butanol)
  • Ex. 10: 1.05 g of 2-methoxybenzoic acid ethyl ester
    1.50 g N-alkylphthalimide (alkyl = 50% n-butyl, 30% propyl, 20% ethyl)
    0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
  • Ex. 11: 1.55 g of ethyl 4-ethoxybenzoate
    1.20 g of N-alkylphthalimides (alkyl = 70% n-butyl, 30% n-propyl)
    0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
    0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid

Man erhält jeweils eine gleichmäßige Blaufärbung.A uniform blue color is obtained in each case.

Die Bestimmung der Carrierwirksamkeit der Carrier­mischungen der Beispiele 6-11 erfolgt durch Vergleich der erzielten Farbtiefen. In der folgenden Tabelle wird die Menge an Carriermischung und an Alkoxybenzoesäure­ester (I) angegeben, die zur Erzielung gleicher Farb­tiefen erforderlich ist. Die Mengenangabe ist bezogen auf die Menge an N-Alkylphthalimid (II) = 100. Die ge­ringen Mengen der Mischungen belegen ihre vorteilhaftere Carrierwirksamkeit gegenüber den Einzelkomponenten. Beispiel Gew.-% der Komponenten in der Mischung erforderliche Menge an Mischung Komponente I 6 30 I 80 90 55 II 7 35 I 90 120 50 II 8 35 I 90 120 50 II 9 17 I 90 100 68 II 10 35 I 90 100 50 II 11 52 I 80 90 40 II The carrier effectiveness of the carrier mixtures of Examples 6-11 is determined by comparing the color depths achieved. The following table shows the amount of carrier mixture and of alkoxybenzoic acid ester (I) required to achieve the same depth of color. The amount is based on the amount of N-alkylphthalimide (II) = 100. The small amounts of the mixtures demonstrate their more advantageous carrier activity compared to the individual components. example % By weight of the components in the mixture required amount of mixture Component I 6 30 I 80 90 55 II 7 35 I 90 120 50 II 8th 35 I 90 120 50 II 9 17 I 90 100 68 II 10th 35 I 90 100 50 II 11 52 I 80 90 40 II

Beispiel 12 (Vergleichsbeispiel zu DE-PS 1 769 210)Example 12 (comparative example to DE-PS 1 769 210)

Garne aus Polyesterfasern werden im Flottenverhältnis von 1:40 in ein auf 60°C erwärmtes Bad eingebracht, das je Liter 0,25 g eines Farbstoffs der Formel

Figure imgb0004
2 g eines Kondensationsprodukts aus Naphthalinsulfonat und Formaldehyd, 2 g Natriumhydrogenphosphat und 3 g einer Carrier-Einstellung folgender Zusammensetzung ent­hält:
1,80 g N-Alkylphthalimide (Alkyl = 60 % Butyl, 40 % Propyl)
0,75 g o-Kresotinsäureethylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure.Yarns made of polyester fibers are placed in a liquor ratio of 1:40 in a bath heated to 60 ° C, which contains 0.25 g of a dye of the formula per liter
Figure imgb0004
 2 g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium hydrogen phosphate and 3 g of a carrier setting contains the following composition:
1.80 g of N-alkylphthalimides (alkyl = 60% butyl, 40% propyl)
0.75 g of ethyl o-cresotate
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid.

Der pH-Wert des Bades wird mit Essigsäure auf pH 4,5-5 eingestellt. Dann wird das Bad auf 98°C erhitzt und 60 Minuten bei dieser Temperatur gehalten. Man erhält eine gleichmäßige Blaufärbung. Die Bestimmung der Carrierwirksamkeit erfolgte wie vorstehend beschrieben (N-Alkylphthalimide (II) = 100). Gew.-% der Komponenten in der Mischung erforderliche Menge an Mischung/Alkoxybenzoesäureester (I) 60 II 100 100 25 Ester nach DE-PS 1 769 210 The pH of the bath is adjusted to pH 4.5-5 with acetic acid. The bath is then heated to 98 ° C. and held at this temperature for 60 minutes. You get an even blue color. The carrier effectiveness was determined as described above (N-alkylphthalimide (II) = 100). % By weight of the components in the mixture required amount of mixture / alkoxybenzoic acid ester (I) 60 II 100 100 25 esters according to DE-PS 1 769 210

Diese Mischung zeigt im Gegensatz zu den beanspruchten Carriermischungen keine synergistische Erhöhung der Carrierwirksamkeit im Vergleich zu den Einzelkompo­nenten.In contrast to the carrier mixtures claimed, this mixture shows no synergistic increase in carrier effectiveness compared to the individual components.

Beispiel 13Example 13

Stückware, die in Kette und Schuß aus Polyester-Spinn­faser besteht, wird im Flottenverhältnis von 1:40 in ein auf 50°C erwärmtes Bad gegeben, das je Liter 0,2 g eines Farbstoffs der Formel

Figure imgb0005
2 g eines Kondensationsprodukts aus Naphthalinsulfonat und Formaldehyd, 2 g Natriumdihydrogenphosphat und 2,5 g einer Carrier-Einstellung folgender Zusammensetzung ent­hält:
1,65 g N-Alkylphthalimide (Alkyl = 60 % Butyl, 40 % Propyl)
0,90 g 4-Methoxybenzoesäureethylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzol­sulfonsäure.Piece goods consisting of polyester spun fiber in warp and weft are placed in a liquor ratio of 1:40 in a bath heated to 50 ° C, containing 0.2 g of a dye of the formula per liter
Figure imgb0005
 2 g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 2.5 g a carrier setting with the following composition:
1.65 g N-alkylphthalimide (alkyl = 60% butyl, 40% propyl)
0.90 g of 4-methoxybenzoic acid ethyl ester
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid.

Der pH-Wert des Bades wird mit Essigsäure auf pH 4,5-5 eingestellt. Die Färbeflotte wird dann auf Kochtempera­tur gebracht und eine Stunde bei dieser Temperatur ge­halten. Es wird eine volle, gleichmäßige Rotfärbung er­zielt.The pH of the bath is adjusted to pH 4.5-5 with acetic acid. The dye liquor is then brought to the boiling temperature and held at this temperature for one hour. A full, even red color is achieved.

Beispiel 14Example 14

Polyester-Spinnfasern werden im Flottenverhältnis von 1:15 in eine Färbeflotte eingebracht, die je Liter 1 g eines Dispersionsfarbstoffs nach Beispiel 14, 0,03 g eines Farbstoffs gemäß Colour Index, 2. Auflage (1956) Band 3, Nr. 12790, 2 g eines Kondensationsprodukts aus Naphthalinsulfonat und Formaldehyd, 2 g Natriumdihydro­genphosphat und 3,5 g einer Carrier-Einstellung des Bei­spiels 13 enthält. Der pH-Wert des Bades wird mit Essig­säure auf pH 4,5-5 eingestellt. Man erhitzt die Flotte langsam auf 98°C und behandelt eine Stunde bei dieser Temperatur. Man erhält eine dunkle Rotbraunfärbung.Polyester staple fibers are introduced in a liquor ratio of 1:15 into a dyeing liquor containing 1 g of a disperse dye according to Example 14 per liter, 0.03 g of a dye according to the Color Index, 2nd edition (1956) Volume 3, No. 12790, 2nd g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3.5 g of a carrier setting of Example 13. The pH of the bath is adjusted to pH 4.5-5 with acetic acid. The liquor is slowly heated to 98 ° C. and treated at this temperature for one hour. A dark reddish brown color is obtained.

Claims (7)

1. Carrier zum Färben von hydrophoben Fasermaterialien enthaltend
Alkoxybenzoesäurealkylester oder deren Mischungen mit N-Alkylphthalimiden oder Mischungen von Alkoxy­benzoesäurearylestern mit N-Alkylphthalimiden, wobei die genannten Alkyl-, Aryl- und Alkoxyreste weitere in der Textilhilfsmittelchemie übliche Substituenten tragen können.1. Carrier for dyeing hydrophobic fiber materials containing
Alkyl alkoxybenzoic acid esters or mixtures thereof with N-alkylphthalimides or mixtures of alkoxybenzoic acid aryl esters with N-alkylphthalimides, it being possible for the alkyl, aryl and alkoxy radicals mentioned to carry further substituents customary in textile assistant chemistry. 2. Carrier gemäß Anspruch 1, dadurch gekennzeichnet, daß als Alkoxybenzoesäureester solche der Formel
Figure imgb0006
 worin
R C₁-C₇-Alkyl, das durch Phenyl substituiert sein kann, oder Phenyl, das durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy, oder C₁-C₄-Alkoxycarbonyl sub­stituiert sein kann, und
R₁ C₁-C₄-Alkyl, das durch OH substituiert sein kann, bedeuten,
und als Phthalimide solche der Formel
Figure imgb0007
 worin
X C₁-C₇-Alkyl bedeutet,
enthalten sind2. Carrier according to claim 1, characterized in that as the alkoxybenzoic acid ester of the formula
Figure imgb0006
 wherein
R is C₁-C₇-alkyl which may be substituted by phenyl or phenyl which may be substituted by C₁-C₄-alkyl, C₁-C₁-alkoxy, or C₁-C₄-alkoxycarbonyl, and
R₁ is C₁-C Alkyl-alkyl, which may be substituted by OH,
and as phthalimides those of the formula
Figure imgb0007
 wherein
X is C₁-C₇ alkyl,
are included 3. Carrier gemäß Anspruch 1, dadurch gekennzeichnet, daß als Alkoxybenzoesäurealkylester
o/p-Methoxybenzoesäure-n-C₁-C₄-alkylester,
o/p-Ethoxybenzoesäure-n-C₁-C₄-alkylester und
o/p-Hydroxybenzoesäure-n-C₁-C₄-alkylester,
enthalten sind.3. Carrier according to claim 1, characterized in that as alkyl alkoxybenzoate
o / p-methoxybenzoic acid-n-C₁-C₄-alkyl esters,
o / p-ethoxybenzoic acid-n-C₁-C₄-alkyl esters and
o / p-hydroxybenzoic acid-n-C₁-C₄-alkyl esters,
are included. 4. Carrier gemäß Anspruch 1, dadurch gekennzeichnet, daß das Gewichtsverhältnis der Phthalimide zu den Alkoxybenzoesäureestern 0,5-12:1 beträgt.4. Carrier according to claim 1, characterized in that the weight ratio of the phthalimides to the alkoxybenzoic acid esters is 0.5-12: 1. 5. Carrierzubereitungen, dadurch gekennzeichnet, daß sie
8-58 Gew.- % Alkoxybenzoesäureester,
40-90 Gew.- % N-Alkylphthalimid,
2-30 Gew.- % Emulgator und
0-10 Gew.- % Lösungsmittel
enthalten.5. Carrier preparations, characterized in that they
8-58% by weight alkoxybenzoic acid ester,
40-90% by weight of N-alkylphthalimide,
2-30% by weight of emulsifier and
0-10% by weight of solvent
contain. 6. Carrierzubereitungen gemäß Anspruch 1, dadurch gekennzeichnet, daß sie
40-98 Gew.- % Alkoxybenzoesäurealkylester,
2-30 Gew.- % Emulgator und
0-10 Gew.- % Lösungsmittel
enthalten.6. Carrier preparations according to claim 1, characterized in that they
40-98% by weight alkyl alkoxybenzoate,
2-30% by weight of emulsifier and
0-10% by weight of solvent
contain. 7. Verfahren zum Färben von hydrophoben Fasermateri­alien, dadurch gekennzeichnet, daß man in Gegenwart von Carriern gemäß Anspruch 1 färbt.7. A method for dyeing hydrophobic fiber materials, characterized in that dyeing according to claim 1 in the presence of carriers.
EP90100893A 1989-01-25 1990-01-17 Carrier for dyeing hydrophobic fibre materials Expired - Lifetime EP0379954B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3902052A DE3902052A1 (en) 1989-01-25 1989-01-25 CARRIER FOR DYING HYDROPHOBIC FIBER MATERIALS
DE3902052 1989-01-25

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
GB2247470A (en) * 1990-08-27 1992-03-04 Sandoz Ltd N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brightening

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JPH09319104A (en) * 1996-05-24 1997-12-12 Ricoh Co Ltd Electrophotographic photoreceptor
JP5629104B2 (en) * 2010-03-24 2014-11-19 株式会社クラレ Method for dyeing polyetherimide fiber and dyed product thereof
JP6042894B2 (en) * 2011-09-29 2016-12-14 ダウ グローバル テクノロジーズ エルエルシー Formulations with benzoate dye carriers for meta-aramid products

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Publication number Priority date Publication date Assignee Title
FR1140000A (en) * 1955-01-05 1957-07-09 Hoechst Ag Process for dyeing articles made of polyester fibers with a high degree of polymerization
US2881045A (en) * 1954-06-17 1959-04-07 American Cyanamid Co Method of dyeing synthetic fibrous materials
GB1193948A (en) * 1968-04-20 1970-06-03 Bayer Ag Printing and Dyeing Process
LU67468A1 (en) * 1972-09-08 1973-07-06

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Publication number Priority date Publication date Assignee Title
US2881045A (en) * 1954-06-17 1959-04-07 American Cyanamid Co Method of dyeing synthetic fibrous materials
FR1140000A (en) * 1955-01-05 1957-07-09 Hoechst Ag Process for dyeing articles made of polyester fibers with a high degree of polymerization
GB1193948A (en) * 1968-04-20 1970-06-03 Bayer Ag Printing and Dyeing Process
LU67468A1 (en) * 1972-09-08 1973-07-06

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2247470A (en) * 1990-08-27 1992-03-04 Sandoz Ltd N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brightening
GB2247470B (en) * 1990-08-27 1994-07-13 Sandoz Ltd N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brighting

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JP2612945B2 (en) 1997-05-21
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DE59002352D1 (en) 1993-09-23
DE3902052A1 (en) 1990-07-26
JPH02229280A (en) 1990-09-12

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