EP0379954A2 - Carrier for dyeing hydrophobic fibre materials - Google Patents
Carrier for dyeing hydrophobic fibre materials Download PDFInfo
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- 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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Classifications
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- 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)
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- 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.
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Abstract
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
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
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
X C₁-C₇-Alkyl bedeutet.Suitable phthalimides are those of the formula
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.
- 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
- 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.
- 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.
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
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
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.
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
- 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.
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
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
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).
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.
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
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
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.
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)
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.
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
X C₁-C₇-Alkyl bedeutet,
enthalten sind2. Carrier according to claim 1, characterized in that as the alkoxybenzoic acid ester of the formula
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
X is C₁-C₇ alkyl,
are included
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.
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.
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.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3902052 | 1989-01-25 | ||
DE3902052A DE3902052A1 (en) | 1989-01-25 | 1989-01-25 | CARRIER FOR DYING HYDROPHOBIC FIBER MATERIALS |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0379954A2 true EP0379954A2 (en) | 1990-08-01 |
EP0379954A3 EP0379954A3 (en) | 1991-08-14 |
EP0379954B1 EP0379954B1 (en) | 1993-08-18 |
Family
ID=6372701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90100893A Expired - Lifetime EP0379954B1 (en) | 1989-01-25 | 1990-01-17 | Carrier for dyeing hydrophobic fibre materials |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0379954B1 (en) |
JP (1) | JP2612945B2 (en) |
DE (2) | DE3902052A1 (en) |
Cited By (1)
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 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
ES2565302T3 (en) * | 2011-09-29 | 2016-04-01 | Dow Global Technologies Llc | Formulations with benzoate-based dye carriers for meta-aramid articles |
Citations (4)
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 |
-
1989
- 1989-01-25 DE DE3902052A patent/DE3902052A1/en not_active Withdrawn
-
1990
- 1990-01-17 DE DE9090100893T patent/DE59002352D1/en not_active Expired - Fee Related
- 1990-01-17 EP EP90100893A patent/EP0379954B1/en not_active Expired - Lifetime
- 1990-01-22 JP JP2010766A patent/JP2612945B2/en not_active Expired - Lifetime
Patent Citations (4)
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 |
Non-Patent Citations (2)
Title |
---|
Chemical Abstracts Band 98, Nr.16, 1983, Zusammenfassung Nr. 127634p. * |
Chemical Abstracts Band 98, Nr.16, 1983, Zusammenfassung Nr.127632m. * |
Cited By (2)
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 |
Also Published As
Publication number | Publication date |
---|---|
JPH02229280A (en) | 1990-09-12 |
EP0379954A3 (en) | 1991-08-14 |
JP2612945B2 (en) | 1997-05-21 |
DE59002352D1 (en) | 1993-09-23 |
EP0379954B1 (en) | 1993-08-18 |
DE3902052A1 (en) | 1990-07-26 |
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