EP0364792B1 - Carrier for dyeing polyester materials - Google Patents
Carrier for dyeing polyester materials Download PDFInfo
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- EP0364792B1 EP0364792B1 EP89118113A EP89118113A EP0364792B1 EP 0364792 B1 EP0364792 B1 EP 0364792B1 EP 89118113 A EP89118113 A EP 89118113A EP 89118113 A EP89118113 A EP 89118113A EP 0364792 B1 EP0364792 B1 EP 0364792B1
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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
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl groups
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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
-
- 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
- D06P1/65131—Compounds containing ether or acetal groups
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- 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
- Y10S8/922—Polyester fiber
Definitions
- the invention relates to carriers, their preparations and processes for dyeing polyester materials with disperse dyes in the presence of these carriers.
- Known carriers used in textile practice for dyeing polyester include halogenobenzenes, halogen toluenes, N-alkylphthalimides, aromatic carboxylic acid esters, methylnaphthalene, diphenyl, diphenyl ether, naphthol ether, phenol ether and oxydiphenyls.
- these connections have disadvantages. All compounds, with the exception of the 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 sharp drop in the dyeing temperature below 98 ° C. Carrier effect, which limits their use in higher regions, where this temperature is not reached with open dyeing machines. 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 obtained should meet high authenticity requirements, and the dyeing of mixed fibers should not result in soiling of the accompanying fiber.
- the carriers according to the invention are a mixture of N-alkylphthalimides (I) and compounds of the general formula wherein R is C1-C7 alkyl; Phenyl, benzyl or phenylethyl, which can be substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl.
- R1 is hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyloxy, hydroxy or C1-C4-alkoxycarbonyl, m 0 or 1, n is 0 or 1, where m and n are not simultaneously 0, contain, is solved.
- These mixtures of carrier active substances show a synergistic increase in the color-accelerating effect compared to the individual components.
- the preferred weight ratio of N-alkylphthalimides (I) to the compounds (II) is 0.5-12: 1.
- the carrier mixtures 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.
- N-alkylphthalimides (I) are understood to mean, in particular, straight-chain or branched alkyl radicals (C1-C6) on the nitrogen-substituted phthalimides or mixtures thereof which, for. B. can be prepared by the reaction of phthalic anhydride or phthalic acid esters with amines.
- the carriers can therefore contain phthalic acid amides and esters due to the manufacturing process.
- Examples of the compounds (II) are aromatic monocarboxylic acid esters (e.g. esters of benzoic acid, methylbenzoic acid, salicylic acid), dicarboxylic acid esters (e.g. esters of terephthalic acid or phthalic acid), carbonates (e.g. diphenyl carbonate) and ethers (e.g. B. diphenyl ether or ditolyether).
- aromatic monocarboxylic acid esters e.g. esters of benzoic acid, methylbenzoic acid, salicylic acid
- dicarboxylic acid esters e.g. esters of terephthalic acid or phthalic acid
- carbonates e.g. diphenyl carbonate
- ethers e.g. B. diphenyl ether or ditolyether.
- alcohol components of the esters such. B. C1-C6 alkanols, phenols and benzyl alcohol.
- 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 sulphonic acids having at least 10 carbon atoms, such as dodecylbenzenesulfonic acid, diodecylbenzenesulphonic acid, and dodecylbenzenesulphonic 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 dyeing can be carried out at temperatures of 90-140 ° C, the preferred industrial application being at 90-150 ° C.
- An additional advantage of the carrier settings described is the very good effectiveness below cooking temperature, which pure N-alkyl phthalimide carriers do not show, e.g. B. at 95 ° C, which is often not exceeded under practical conditions with open dyeing machines.
- 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.
- components (I) and (II) as carriers in dyeing polyester are known.
- DE-C-1 769 210 So z. B. the use of N-alkylphthalimides in DE-C-1 769 210, the use of phthalic acid esters in US-A-4 032 291 and the use of benzoic acid esters in DE-A-2 348 363.
- DE-C-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 corresponds to 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 described in DE-C-1 769 210 with salicylic acid compounds containing alkyl groups).
- 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.
- 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 1-12 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.
- 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 kept 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 14.
- 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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- Textile Engineering (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
Description
Die Erfindung betrifft Carrier, ihre Zubereitungen und Verfahren zum Färben von Polyestermaterialien mit Dispersionsfarbstoffen in Gegenwart dieser Carrier.The invention relates to carriers, their preparations and processes for dyeing 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. Alle Verbindungen, bis auf die N-Alkylphthalimide, besitzen 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 denen 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 for dyeing polyester include halogenobenzenes, halogen toluenes, N-alkylphthalimides, aromatic carboxylic acid esters, methylnaphthalene, diphenyl, diphenyl ether, naphthol ether, phenol ether and oxydiphenyls. However, these connections have disadvantages. All compounds, with the exception of the 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 sharp drop in the dyeing temperature below 98 ° C. Carrier effect, which limits their use in higher regions, where this temperature is not reached with open dyeing machines. 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 obtained should meet high authenticity requirements, and the dyeing of mixed fibers should not result in soiling of the accompanying fiber.
Es wurde nun gefunden, daß diese Aufgabe mit den erfindungsgemäßen Carriern, die eine Mischung von N-Alkylphthalimiden (I) und Verbindungen der allgemeinen Formel
worin
R C₁-C₇-Alkyl; Phenyl, Benzyl oder Phenylethyl, die durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder C₁-C₄-Alkoxycarbonyl substituiert sein können.
R¹ Wasserstoff, C₁-C₄-Alkyl, C₁-C₄-Alkylcarbonyloxy, Hydroxy oder C₁-C₄-Alkoxycarbonyl,
m 0 oder 1,
n 0 oder 1, wobei m und n nicht gleichzeitig 0 sind,
enthalten,
gelöst wird. Diese Mischungen von Carrierwirkstoffen zeigen gegenüber den Einzelkomponenten eine synergistische Erhöhung der färbebeschleunigenden Wirkung.It has now been found that this object is achieved with the carriers according to the invention, which are a mixture of N-alkylphthalimides (I) and compounds of the general formula
wherein
R is C₁-C₇ alkyl; Phenyl, benzyl or phenylethyl, which can be substituted by C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkoxycarbonyl.
R¹ is hydrogen, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyloxy, hydroxy or C₁-C₄-alkoxycarbonyl,
m 0 or 1,
n is 0 or 1, where m and n are not simultaneously 0,
contain,
is solved. These mixtures of carrier active substances show a synergistic increase in the color-accelerating effect compared to the individual components.
Das bevorzugte Gewichtsverhältnis von N-Alkylphthalimiden (I) zu den Verbindungen (II) liegt bei 0,5 - 12 : 1.The preferred weight ratio of N-alkylphthalimides (I) to the compounds (II) is 0.5-12: 1.
Da die erfindungsgemäßen Carriermischungen wasserunlöslich sind, werden sie vorzugsweise in Form von Zubereitungen, die Emulgier- oder Dispergiermittel und gegebenenfalls Lösungsmittel enthalten, den Färbeflotten zugesetzt.Since the carrier mixtures 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.
Bevorzugt werden Carriermischungen, die
- 1.) 40-90, insbesondere 45-80 Gew.-% (I),
- 2.) 8-58, insbesondere 10-45 Gew.-% (II),
- 3.) 2-30, insbesondere 10-20 Gew.-% eines Emulgators und
- 4.) 0-10 Gew.-% eines Lösungsmittels
enthalten. Dabei können die Komponenten 1.) - 4.) auch als Mischungen eingesetzt werden.Carrier mixtures which are preferred
- 1.) 40-90, in particular 45-80% by weight (I),
- 2.) 8-58, in particular 10-45% by weight (II),
- 3.) 2-30, in particular 10-20 wt .-% of an emulsifier and
- 4.) 0-10% by weight of a solvent
contain. Components 1.) - 4.) can also be used as mixtures.
Unter N-Alkylphthalimiden (I) versteht man insbesondere mit gradkettigen oder verzweigten Alkylresten (C1-C6) am Stickstoff substituierte Phthalimide oder deren Gemische, die z. B. durch die Umsetzung von Phthalsäureanhydrid oder Phthalsäureestern mit Aminen hergestellt werden können. Die Carrier können deshalb herstellungsbedingt Phthalsäureamide und -ester enthalten.N-alkylphthalimides (I) are understood to mean, in particular, straight-chain or branched alkyl radicals (C1-C6) on the nitrogen-substituted phthalimides or mixtures thereof which, for. B. can be prepared by the reaction of phthalic anhydride or phthalic acid esters with amines. The carriers can therefore contain phthalic acid amides and esters due to the manufacturing process.
Beispiele für die Verbindungen (II) sind aromatische Monocarbonsäureester (z. B. Ester der Benzoesäure, Methylbenzoesäure, Salicylsäure), Dicarbonsäureester (z. B. Ester der Terephthalsäure oder Phthalsäure), Carbonate (z. B. Diphenylcarbonat) und Ether (z. B. Diphenylether oder Ditolyether). Als Alkoholkomponenten der Ester sind z. B. C₁-C₆-Alkanole, Phenole und Benzylalkohol zu nennen.Examples of the compounds (II) are aromatic monocarboxylic acid esters (e.g. esters of benzoic acid, methylbenzoic acid, salicylic acid), dicarboxylic acid esters (e.g. esters of terephthalic acid or phthalic acid), carbonates (e.g. diphenyl carbonate) and ethers (e.g. B. diphenyl ether or ditolyether). As alcohol components of the esters such. B. C₁-C₆ alkanols, phenols and benzyl alcohol.
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-, Erd- alkali 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 sulphonic acids having at least 10 carbon atoms, such as dodecylbenzenesulfonic acid, diodecylbenzenesulphonic acid, and dodecylbenzenesulphonic 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 enthalten
- 1.) 50-75 Gew.-% eines N-Alkylphthalimids mit gradkettigem oder verzweigtem Alkylrest mit 3-5 C-Atomen,
- 2.) 10-40 Gew.-% eines C₁-C₄-Alkyl-, Phenyl- oder Benzylesters der Benzoe-, Methylbenzoe-, Terephthal-, Phthal- oder Salicylsäure oder Diphenylcarbonat, Diphenylether oder Ditolylether und
- 3.) 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.) 50-75% by weight of an N-alkylphthalimide with a straight-chain or branched alkyl radical with 3-5 C atoms,
- 2.) 10-40 wt .-% of a C₁-C₄ alkyl, phenyl or benzyl ester of benzoic, methylbenzoic, terephthalic, phthalic or salicylic acid or diphenyl carbonate, diphenyl ether or ditolyl ether and
- 3.) 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 verwendten 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 Polyterephtalsäureglykolestern, 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 Anwendung bei 90-150°C erfolgt. Ein zusätzlicher Vorteil der beschriebenen Carrier-Einstellungen ist die sehr gute Wirksamkeit unterhalb Kochtemperatur, die reine N-Alkyl-phthalimid-Carrier nicht zeigen, z. B. bei 95°C, die häufig unter Praxisbedingungen bei offenen Färbeapparaten nicht überschritten wird.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 dyeing can be carried out at temperatures of 90-140 ° C, the preferred industrial application being at 90-150 ° C. An additional advantage of the carrier settings described is the very good effectiveness below cooking temperature, which pure N-alkyl phthalimide carriers do not show, e.g. B. at 95 ° C, which is often not exceeded under practical conditions with open dyeing machines.
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 der Komponenten (I) und (II) als Carrier beim Färben von Polyester ist bekannt.The use of components (I) and (II) as carriers in dyeing polyester is known.
So ist z. B. die Verwendung von N-Alkylphthalimiden in der DE-C-1 769 210, die Verwendung von Phthalsäureestern in der US-A-4 032 291 und die Verwendung von Benzoesäureestern in DE-A-2 348 363 beschrieben. Aus der DE-C-1 769 210 ist auch die Verwendung von Mischungen von N-Alkylphthalimiden mit disubstituierten Benzoesäureestern bekannt.So z. B. the use of N-alkylphthalimides in DE-C-1 769 210, the use of phthalic acid esters in US-A-4 032 291 and the use of benzoic acid esters in DE-A-2 348 363. DE-C-1 769 210 also discloses the use of mixtures of N-alkylphthalimides with disubstituted benzoic acid esters.
Überraschend wurde nun gefunden, 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-C-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.Surprisingly, it has now been found that the mixtures according to the invention have a higher color-accelerating effect than corresponds to 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 described in DE-C-1 769 210 with salicylic acid compounds containing alkyl groups). 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 g eines Kondensationsprodukts aus Naphthalinsulfonat und Formaldehyd, 2 g Natriumdihydrogenphosphat und 3 g einer Carrier-Einstellung folgender Zusammensetzung enthält:
1,80 g N-Alkylphthalimide (Alkyl= 50 % n-Butyl, 50 % n-Propyl)
0,75 g 4-Methylbenzoesäuremethylester
0,25 g eines Additionsprodukts von 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 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:
1.80 g N-alkylphthalimides (alkyl = 50% n-butyl, 50% n-propyl)
0.75 g of methyl 4-methylbenzoate
0.25 g of an addition product of 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:The dyeing is carried out as described in Example 1, using carrier settings of the following compositions:
1,65 g N-Butylphthalimid
0,90 g 4-Methylbenzoesäureethylester
0,20 g Calciumdodecylbenzolsulfonat (70 % in Butanol)
0,20 g Rizinusöl mit ca. 30 mol EO
0,05 g Stearylalkoholhexaethylenglykolether1.65 g of N-butyl phthalimide
0.90 g of 4-methylbenzoic acid ethyl ester
0.20 g calcium dodecylbenzenesulfonate (70% in butanol)
0.20 g castor oil with approx. 30 mol EO
0.05 g stearyl alcohol hexaethylene glycol ether
2,25 g N-Butylphthalimid
0,30 g Terephthalsäuredimethylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure2.25 g of N-butyl phthalimide
0.30 g dimethyl terephthalate
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
1,50 g N-Butylphtalimid
1,05 g Salicylsäuremethylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure1.50 g of N-butyl phthalimide
1.05 g of methyl salicylic acid
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
1,50 g N-Alkylphthalimide (Alkyl = 50 % n-Butyl, 30 % Propyl, 20 % Ethyl)
1,05 g Benzoesäurebenzylester
0,25 g Di-(phenylethyl)-phenol mit ca. 10 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure1.50 g N-alkylphthalimide (alkyl = 50% n-butyl, 30% propyl, 20% ethyl)
1.05 g benzyl benzoate
0.25 g di- (phenylethyl) phenol with approx. 10 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
1,80 g N-Alkylphthalimide (Alkyl = 70 % Butyl, 30 % Propyl)
0,75 g Benzoesäure-n-butylester
0,30 g Rizinusöl mit ca. 30 mol EO
0,15 g Calciumdodecylbenzolsulfonat (70 % in Butanol)1.80 g N-alkylphthalimide (alkyl = 70% butyl, 30% propyl)
0.75 g n-butyl benzoate
0.30 g castor oil with approx. 30 mol EO
0.15 g calcium dodecylbenzenesulfonate (70% in butanol)
2,10 g N-Butylphthalimid
0,45 g Benzoesäurephenylester
0,30 g Di-(methylphenylethyl)-phenol mit ca. 12 mol EO
0,15 g Calciumdodecylbenzolsulfonat (70 % in Butanol)2.10 g of N-butyl phthalimide
0.45 g phenyl benzoate
0.30 g di- (methylphenylethyl) phenol with approx. 12 mol EO
0.15 g calcium dodecylbenzenesulfonate (70% in butanol)
1,50 g N-Butylphthalimid
1,05 g Diphenylether
0,30 g Di-(phenylethyl)-phenol mit ca. 10 mol EO
0,15 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure1.50 g of N-butyl phthalimide
1.05 g diphenyl ether
0.30 g di- (phenylethyl) phenol with approx. 10 mol EO
0.15 g monoethanolamine salt of dodecylbenzenesulfonic acid
1,90 g N-Alkylphthalimide (Alkyl = 50 % Butyl, 30 % Propyl, 20 % Ethyl)
0,65 g Diphenylcarbonat
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure1.90 g N-alkylphthalimide (alkyl = 50% butyl, 30% propyl, 20% ethyl)
0.65 g diphenyl carbonate
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
2,10 g N-Butylphthalimid
0,45 g 2-Methylbenzoesäurebutylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure2.10 g of N-butyl phthalimide
0.45 g of 2-methylbenzoic acid butyl ester
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
1,50 g N-Alkylphthalimide (Alkyl = 60 % n-Butyl, 40 % n-Propyl)
1,05 g 3-Methylbenzoesäureethylester
0,25 g Tri-(methylphenylethyl)-phenol mit ca. 15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure1.50 g N-alkylphthalimide (alkyl = 60% n-butyl, 40% n-propyl)
1.05 g of 3-methylbenzoic acid ethyl ester
0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO
0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid
1,50 g N-Butylphthalimid
1,05 g Ditolylether
0,25 g Tri-(methylphenylethyl)-phenol mit ca.15 mol EO
0,20 g Monoethanolaminsalz der Dodecylbenzolsulfonsäure1.50 g of N-butyl phthalimide
1.05 g ditolyl ether
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 1-12 erfolgt durch Vergleich der erzielten Farbtiefen. In der folgenden Tabelle wird die Menge an Carriermischung und an Ester/Ether (II) angegeben, die zur Erzielung gleicher Farbtiefen erforderlich ist. Die Mengenangabe ist bezogen auf die Menge an N-Alkylphthalimid (I) = 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
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
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 ((I) = 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
2 g eines Kondensationsprodukts aus Naphthalinsulfonat und Formaldehyd, 2 g Natriumdihydrogenphosphat und 2,5 g einer Carrier-Einstellung folgender Zusammensetzung enthält:
1,80 g N-alkylphthalimide (Alkyl = 60 % Butyl, 40 % Propyl)
0,75 g 4-Methylbenzoesäuremethylester
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
2 g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 2.5 g of a carrier setting contains the following composition:
1.80 g N-alkylphthalimide (alkyl = 60% butyl, 40% propyl)
0.75 g of methyl 4-methylbenzoate
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 kept 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 14 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 14. 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 (5)
- Carrier mixture containing N-alkylphthalimides (1) and compounds of the general formula
R denotes C₁-C₇-alkyl; phenyl, benzyl or phenylethyl, which can be substituted by C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkoxy- carbonyl,
R¹ denotes hydrogen, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyloxy, hydroxyl or C₁-C₄-alkoxycarbonyl,
m denotes 0 or 1,
n denotes 0 or 1, m and n not being 0 at the same time. - Carrier mixture according to Claim 1, containing components (I) and (II) in a weight ratio of 0.5 - 12 : 1.
- Carrier mixture according to Claim 1, containing1.) 40-90% by weight of (I),2.) 8-58% by weight of (II),3.) 2-30% by weight of an emulsifier and4.) 0-10% by weight of a solvent.
- Carrier mixture according to Claim 1, containing1.) 50-75% by weight of an N-alkylphthalimide which has a straight-chain or branched alkyl radical of 3-5 C atoms,2.) 10-40% by weight of a C₁-C₄-alkyl, phenyl or benzyl ester of benzoic, methylbenzoic, terephthalic, phthalic or salicylic acid or diphenyl carbonate, diphenyl ether or ditolyl ether and3.) 5-20% by weight of an addition product of 15-30 mol of ethylene oxide with castor oil or soya bean oil, of 5-50 mol of ethylene oxide and/or propylene oxide with C₁₆-C₂₂-fatty alcohols, octylphenol or nonylphenol or phenylethylphenol, alkali metal salts, alkaline earth metal salts, ammonium salts or (di)ethanolamine salts of dodecylbenzenesulfonic acid.
- Process for dyeing polyester materials with disperse dyestuffs in the presence of carrier mixtures of Claim 1.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3834737 | 1988-10-12 | ||
DE3834737A DE3834737A1 (en) | 1988-10-12 | 1988-10-12 | CARRIER FOR DYING POLYESTER MATERIALS |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0364792A2 EP0364792A2 (en) | 1990-04-25 |
EP0364792A3 EP0364792A3 (en) | 1991-08-14 |
EP0364792B1 true EP0364792B1 (en) | 1993-02-03 |
Family
ID=6364951
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP89118113A Expired - Lifetime EP0364792B1 (en) | 1988-10-12 | 1989-09-29 | Carrier for dyeing polyester materials |
Country Status (7)
Country | Link |
---|---|
US (1) | US4994089A (en) |
EP (1) | EP0364792B1 (en) |
JP (1) | JPH02169778A (en) |
AU (1) | AU615581B2 (en) |
CA (1) | CA2000411A1 (en) |
DE (2) | DE3834737A1 (en) |
PT (1) | PT91875B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011012598A1 (en) | 2009-07-31 | 2011-02-03 | Basf Se | Method for producing spinnable and dyeable polyester fibers |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2037597B1 (en) * | 1990-08-27 | 1994-03-16 | Sandoz Ag | IMPROVEMENTS IN OR RELATED TO ORGANIC COMPOUNDS. |
WO1998038275A1 (en) * | 1997-02-28 | 1998-09-03 | Sybron Chemicals Inc. | Clay-containing textile material treating composition and method |
US5972049A (en) * | 1998-01-28 | 1999-10-26 | Sybron Chemicals Inc. | Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles |
JP4721532B2 (en) * | 2001-02-21 | 2011-07-13 | 東レ株式会社 | Colored polyphenylene sulfide fiber and method for producing the same |
US6652602B2 (en) * | 2001-12-21 | 2003-11-25 | N.V. Bekaert S.A. | Color dyeing system for plastic films |
EP1348800B1 (en) * | 2002-03-19 | 2004-07-07 | Dr. Th. Böhme KG Chem. Fabrik GmbH & Co. | Use of alkyl benzoates as leveling agents for the dyeing of polyester fibrous materials |
ATE305532T1 (en) * | 2003-02-28 | 2005-10-15 | Boehme Chem Fab Kg | EQUALIZING AGENTS |
US7095877B2 (en) * | 2003-07-30 | 2006-08-22 | Xerox Corporation | System and method for measuring and quantizing document quality |
JP4810224B2 (en) * | 2005-12-28 | 2011-11-09 | 共栄社化学株式会社 | Textile product cleaner |
JP5629104B2 (en) * | 2010-03-24 | 2014-11-19 | 株式会社クラレ | Method for dyeing polyetherimide fiber and dyed product thereof |
JP5928333B2 (en) * | 2010-12-16 | 2016-06-01 | 東レ株式会社 | Processing agent for polyester fiber structure and method for producing polyester fiber structure using the same |
CN107541968B (en) * | 2016-06-29 | 2020-04-24 | 苏州联胜化学有限公司 | Polyester dyeing carrier and preparation method thereof |
Family Cites Families (5)
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 |
DE1769210A1 (en) * | 1968-04-20 | 1970-12-17 | Bayer Ag | Printing and coloring processes |
US4032291A (en) * | 1976-01-12 | 1977-06-28 | Ciba-Geigy Corporation | Phenyl phthalate carriers in dyeing and printing synthetic fibers |
EP0033715A1 (en) * | 1980-01-31 | 1981-08-12 | Ciba-Geigy Ag | Auxiliary and its use in the dyeing or optical brightening of polyester fibre materials |
-
1988
- 1988-10-12 DE DE3834737A patent/DE3834737A1/en not_active Withdrawn
-
1989
- 1989-09-28 US US07/414,051 patent/US4994089A/en not_active Expired - Lifetime
- 1989-09-29 DE DE8989118113T patent/DE58903445D1/en not_active Expired - Fee Related
- 1989-09-29 EP EP89118113A patent/EP0364792B1/en not_active Expired - Lifetime
- 1989-10-02 PT PT91875A patent/PT91875B/en not_active IP Right Cessation
- 1989-10-10 CA CA002000411A patent/CA2000411A1/en not_active Abandoned
- 1989-10-11 AU AU42889/89A patent/AU615581B2/en not_active Ceased
- 1989-10-12 JP JP1264106A patent/JPH02169778A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011012598A1 (en) | 2009-07-31 | 2011-02-03 | Basf Se | Method for producing spinnable and dyeable polyester fibers |
Also Published As
Publication number | Publication date |
---|---|
PT91875A (en) | 1990-04-30 |
AU615581B2 (en) | 1991-10-03 |
CA2000411A1 (en) | 1990-04-12 |
EP0364792A3 (en) | 1991-08-14 |
DE3834737A1 (en) | 1990-04-19 |
JPH02169778A (en) | 1990-06-29 |
US4994089A (en) | 1991-02-19 |
EP0364792A2 (en) | 1990-04-25 |
DE58903445D1 (en) | 1993-03-18 |
PT91875B (en) | 1995-07-06 |
AU4288989A (en) | 1990-04-26 |
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