EP1527228B1 - Procede de teinture au moyen de colorants au soufre et de colorants au soufre de cuve - Google Patents

Procede de teinture au moyen de colorants au soufre et de colorants au soufre de cuve Download PDF

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Publication number
EP1527228B1
EP1527228B1 EP03766263A EP03766263A EP1527228B1 EP 1527228 B1 EP1527228 B1 EP 1527228B1 EP 03766263 A EP03766263 A EP 03766263A EP 03766263 A EP03766263 A EP 03766263A EP 1527228 B1 EP1527228 B1 EP 1527228B1
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EP
European Patent Office
Prior art keywords
dyeing
dyebath
dye
sulfur
cell
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
EP03766263A
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German (de)
English (en)
Other versions
EP1527228A1 (fr
Inventor
Thomas Bechtold
Wolfgang Schrott
Thorsten HÜLS
Marc-Steffen Muche
Bertram Wendt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Textilfarben GmbH and Co Deutschland KG
Original Assignee
Dystar Textilfarben GmbH and Co Deutschland KG
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Publication date
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Publication of EP1527228A1 publication Critical patent/EP1527228A1/fr
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Publication of EP1527228B1 publication Critical patent/EP1527228B1/fr
Anticipated expiration legal-status Critical
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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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/243—Polyamides; Polyurethanes using vat or sulfur dyes, indigo
    • 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
    • D06P1/22—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 vat dyestuffs including indigo
    • 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
    • D06P1/22—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 vat dyestuffs including indigo
    • D06P1/221—Reducing systems; Reducing catalysts
    • 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
    • D06P1/30—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 sulfur dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/523—Polyesters using vat or sulfur dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/6025—Natural or regenerated cellulose using vat or sulfur dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
    • D06P5/2016—Application of electric energy

Definitions

  • the present invention relates to a process for dyeing fiber materials with sulfur and sulfur vat dyes
  • the group of sulfur or sulfur vat dyestuffs comprises dyestuffs of the same production principle and the same dyeing proof.
  • the sulfur dyes are formed by reacting suitable organic substances with sulfur, alkali metal sulfides or alkali metal polysulfides.
  • the resulting products contain repeating organic structural elements linked by disulfide groups. The chemical constitution is not known for sure in most cases.
  • the sulfur dyes are reduced using different reduction techniques, with part of the disulfide bridges being cleaved reductively (see Equation 1).
  • the resulting products have lower molar masses, are soluble in aqueous alkaline solution, and can be used for the purpose of dyeing, as they also have an affinity for fibers, e.g. Cellulosic fibers.
  • Such a procedure is particularly suitable for the production of relatively concentrated products or dye liquors, which are also exposed to the oxidative action of atmospheric oxygen for a short time during continuous dyeing.
  • a content of the dyeing chassis of 25 l at a standard product speed of 60 m / min, a running weight of 200 g / m and a liquor pick-up of 80%, the chassis volume is replaced within less than 3 minutes.
  • the present invention is based on the surprising finding that sulfur dyes can take over the task of a mediator even in Ausziehfärbungen and sufficient bath stability can be achieved if a continuous regeneration of the reduction state can be achieved. This is achieved according to the present invention in that during the dyeing process a sufficient circulation of the dyeing bath is made possible by a suitably coupled electrolysis cell.
  • the present invention thus relates to a process for dyeing fiber materials with sulfur dyes with regeneration of kaurbebadredoxpotentials, which is characterized in that the dyeing liquor between dyeing plant and a coupled electrolytic cell circulates during the dyeing process and the dye bath undesirable oxidized sulfur dye is reduced cathodically in the electrolysis cell.
  • the process according to the invention can be carried out, for example, as an exhaust process, but also according to the continuous process. Accordingly, dyeing apparatuses, such as, for example, yarn dyeing apparatus, winch skid, tree dyeing apparatus, jet or overflow dyeing plant, are used as dyeing plants in the exhaust process. For the continuous process, however, the usual for this process dyeing systems are used.
  • the circulation of the dyebath between dyeing plant and electrolysis cell has to be carried out according to the dye concentration and the oxidative load. At high oxidative load and low dye concentration, the circulation has to achieve larger volume flows than at high dye concentration and low oxygen load.
  • the cathodically reduced dye passes from the electrolysis cell to the dyeing plant, the partially oxidized dyebath flows from the dyeing plant to the electrolysis cell.
  • the required liquor exchange in l / min between electrolysis cell and dyeing plant depends on several conditions. These include, for example, dye concentration, the desired degree of reduction in the dyeing plant, maximum degree of reduction which can be achieved by cathodic reduction in a sulfur dye, color reduction required of the sulfur dye, cell-technically applicable current density and also the oxygen input into the dyeing plant (oxidative load).
  • oxidative load oxygen input into the dyeing plant
  • the required mass transfer between cell and dyeing apparatus can also be easily calculated by one of ordinary skill in the art. For example, assuming a current of 10A per kg of material to be incorporated to compensate for the oxygen input and starting at 0.01 mol / l of dye available in the dye bath circulation, a dyebath circulation of 5 l / min is required to reach the 5 l / min the cell reached sales did not rise above 10% of the existing dye concentration. At a circulation capacity of 10 l / min kg, the dye solution only changes by 5% in the reduction state.
  • the liquor exchange based on one kg of dyed material, is between 0.5 l / min kg and 100 l / min kg, preferably between 1 and 50 l / min kg and very particularly preferably between 5 and 301 / min kg.
  • the dye concentration in the dyebath in the process according to the invention is preferably from 0.5 to 100 g / l of pure dye, particularly preferably from 5 to 50 g / l of pure dyestuff.
  • the inventive method is advantageously carried out at temperatures of 20 to 135 ° C, with 60 to 95 ° C are particularly preferred.
  • the dyeing process is influenced by controlling the redox potential. This is done by adjusting the cell current, whereby the redox potential in the dyebath can be changed or regulated within certain potential limits.
  • the adjustable potential range is determined by the sulfur dye used, its concentration, as well as by the pH and dyeing temperature.
  • the cell flow is defined in particular by the oxygen input and moves in conventional dyeing systems between 0.5 and 50 A / kg, preferably between 1 and 10 A / kg. By applying suitable measures, such as a protective gas atmosphere of, for example, nitrogen, the values can be lowered.
  • the pH of the dyebath is, for example, between 9 and 14, preferably between 11 and 13.
  • the redox potential in the dyebath is defined by the dye and the desired dyeing failure and is between-300mV and -900mV, preferably between -400mV and -700mV.
  • an electrolytic cell is coupled with a liquor circulation.
  • electrolysis cells it is possible to use customary electrolysis cells available from cell manufacturers or commercially available. Normal or multi-cathode cells can be used.
  • the electrolysis cell is preferably designed as a divided cell, again using a membrane electrolysis cell being particularly preferred. Most preferably, a cation exchange membrane serves as a separator.
  • Alkaline solutions preferably alkaline solutions of alkali metal salts, in particular of sodium hydroxide, potassium hydroxide, sodium carbonate, common salt or Glauber's salt, are preferably used as the conducting electrolyte.
  • the liquor added to the dyebath advantageously sodium hydroxide solution, potassium hydroxide solution or soda, is used.
  • the salts added during the dyeing, preferably common salt or Glauber's salt can also improve the conductivity as electrolytes.
  • this is carried out under an inert atmosphere.
  • the dyebath in the dyeing apparatus with nitrogen or a noble gas, more preferably argon, superimposed. Since the oxidative base load is reduced by reducing the partial pressure of the atmospheric oxygen, thus the required electrolysis cells can be dimensioned with smaller cell currents and thus more economical.
  • the process according to the invention can be used without restriction for all sulfur dyes. It is possible to use both oxidized dyes, filter cakes from the synthesis, as well as cathodically or chemically prereduced dyes and dye preparations. Particular preference is given to sulfur dyes produced by cathodic reduction, as described, for example, in US Pat DE-A 1 906 083 or WO 99/11716 are used.
  • fiber materials which are basically dyeable with sulfur dyes.
  • fiber materials made of cellulose and polyamide, and of cellulose / polyester and cellulose / polyamide mixtures.
  • Fiber materials preferably mean textile fiber materials.
  • the low concentrations of sulfur dye, as used in exhaust processes are very particularly advantageous for dyeing on a standing bath, where only the sulfur dye discharged with the product has to be added to the dyebath.
  • a cell divided by a cation exchange membrane is used as the electrolytic cell.
  • Cathode stainless steel cathodes, total area (surface area) cathode 0.43 m 2 area, total volume 2 l.
  • Anode Stainless steel plate with 0.01 m 2 surface. Volume 0.3 l.
  • the anolyte used is 0.1 M NaOH.
  • Cell current 0.9 A, cell voltage between 2.7 V and 4.1 V
  • the dyebath (2 l total volume) is pumped through the cathode compartment at 150 ml / min so that a continuous regeneration of the dyebath takes place by exchange with the catholyte.
  • the dyebath contains a bleached cotton knitted fabric (sample 1) with a mass of 6.9 g.
  • the liquor circulation and heating takes place by means of a magnetic stirrer.
  • the Katholyttemperatur is brought to 70 ° C.
  • the redox potential drops from - 259 mV (vs. Ag / AgCl, 3 M KCl reference) to - 499 mV.
  • the dyed pattern 1 is removed, rinsed with water and oxidized according to the usual methods with peroxide / acetic acid.
  • another pattern (pattern 2, mass 6.9 g) is introduced and dyed for 30 minutes while continuing the electrolysis process.
  • the redox potential drops to - 545 mV.
  • the pattern 2 is removed after 30 minutes and completed as already described.
  • the pH of the dyebath is about 12.2
  • the color depth can be described by color location measurement.
  • a cell divided by a cation exchange membrane is used as the electrolytic cell.
  • Cathode stainless steel cathodes, total area (surface area) cathode 0.43 m 2 area, total volume 2 I.
  • Anode Stainless steel plate with 0.01 m 2 surface. Volume 0.3 I.
  • the anolyte used is 0.1 M NaOH.
  • Cell current 0.9 A, cell voltage between 3.0 V and 4.7 V
  • the dyebath (2 l total volume) is pumped through the cathode compartment at 150 ml / min so that a continuous regeneration of the dyebath takes place by exchange with the catholyte.
  • the colored pattern 3 becomes removed, rinsed with water and oxidized according to the usual methods with peroxide / acetic acid.
  • another pattern (pattern 4, mass 7.0 g) is introduced and stained for 80 min while continuing the electrolysis process.
  • the redox potential during this time is at - 437 - -431 mV.
  • the pattern 4 is removed after 80 minutes and finished as already described.
  • the pH of the dyebath is about 12.1-12.2.
  • the color depth can be described by color location measurement.
  • a cell divided by a cation exchange membrane is used as the electrolytic cell.
  • Cathode stainless steel cathodes, total area (surface area) cathode 1 m 2 , total volume of catholyte 10 l.
  • Anode Ti electrode with mixed oxide coating, expanded metal with 0.04 m 2 geometric area. Volume 1.5l.
  • the anolyte used is 1 M NaOH.
  • Cell current 10 A, cell voltage between 3.0 V and 4.7 V
  • a looptex laboratory dyeing plant for denim dyeings is coupled to the cell as a dyeing plant. After an electrolysis time of 17.5 hours at 10 A (75 Ah) to reach the dyeing potential, a portion of the catholyte (4 I) is pumped from the cell to the dyeing plant and at a temperature of 50 ° C (-491 mV) Sample 5 or dyed at 80 ° C (-567 mV) Sample 6 (yarn strand with a length of 150 m, cotton yarn raw).
  • Dyeing program Prewetting (3 g / l wetting agent), squeezing, immersion in sulfur chick, squeezing, air oxidation, followed by rinsing in cold water.
  • a solution of 20 ml / l Cassulfon ® Carbon CMR from DyStar textile colors GmbH & Co. KG Germany (30-40% solution of Leuco Sulfur Black 1) is free from water in the presence of 20 g / l Na 2 SO 4 at pH 12 and room temperature in a plant according to application example 1 electrolyzed.
  • Sodium hydroxide solution 40 g / l NaOH
  • the solution of the reduced sulfur dye has a content of reducing agent equivalents of 0.075 mol / l at the beginning of the electrolysis in the iodometric titration.
  • the cathodic reduction is carried out according to the low content of sulfur dye in the catholyte at a current density of 0.26 mA / cm 2 .
  • the electrolysis is terminated at an analytically determined content of 0.125 mol / l.
  • the solution now has a content of reducing agent equivalents of 335 Ah based on 1 kg of solid sulfur dye.
  • the solution of the sulfur dye prepared in this way can be used directly for dyeing, for example as described in Application Example 1.
  • Electrolytic cell a cell divided by a cation exchange membrane is used.
  • Cathode Three-dimensional stainless steel cathodes, viewing area cathode 60x55 cm, 0.33 m 2 area, total volume of cathode chamber 100 I.
  • Anode Titanium electrode with Pt mixed oxide coating with 0.3 m 2 area. The anolyte used is 0.1 M NaOH.
  • Cell current 85 A, cell voltage between 5.3 V and 5.7 V
  • the dyebath (230 l total volume) is pumped through the cathode space so that a continuous regeneration of the dyebath or the reduced dyestuff takes place by exchange with the catholyte.
  • the dyebath contains a pre-washed, bleached cotton knit with a weight of 8 kg. Flottenumnachlzung and goods movement done by the existing jet in the pump. An indirect steam heating is used for heating. The dyeing takes place under a protective gas atmosphere (nitrogen) to minimize the admission of air. For this purpose, a volume flow of 10 i / min nitrogen is continuously fed into the apparatus. The goods speed is 50 m / min.
  • the liquor circulation through the cell is 30 l / min.
  • the catholyte temperature is brought to about 55 ° C, then the coupling of the cell circulation and further heating to 76 ° C takes place.
  • the redox potential is measured in the cell between -630 mV and -720 mV and measured in the jet dyeing plant between -460 mV and -432 mV (vs. Ag / AgCl, 3 M KCl reference).
  • the pH of the dyebath is about 12.1-12.2.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Treatment Of Fiber Materials (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Claims (8)

  1. Procédé pour la teinture de matériaux fibreux au moyen de colorants au soufre, avec régénération du potentiel redox du bain de teinture, caractérisé en ce que pendant le processus de teinture on fait circuler le bain de teinture entre l'unité de teinture et une cellule électrolytique couplée à celle-ci et le colorant au soufre indésirablement oxydé est soumis à une réduction cathodique dans la cellule électrolytique.
  2. Procédé selon la revendication 1, caractérisé en ce que le potentiel redox du bain de teinture est réglé par le courant de la cellule.
  3. Procédé selon la revendication 1 et/ou la revendication 2, caractérisé en ce qu'on utilise comme cellule électrolytique une cellule électrolytique divisée, de façon particulièrement avantageuse une cellule électrolytique à membrane.
  4. Procédé selon une ou plusieurs des revendications 1 à 3, caractérisé en ce qu'on utilise comme électrolyte conducteur des solutions alcalines, de façon particulièrement préférée des solutions alcalines de sels alcalins, en particulier d'hydroxyde de sodium, d'hydroxyde de potassium, de carbonate de sodium, de chlorure de sodium ou de sel de Glauber.
  5. Procédé selon une ou plusieurs des revendications 1 à 4, caractérisé en ce que la concentration de colorant dans le bain de teinture va de 0,5 à 100 g/l de colorant pur, de façon particulièrement préférée de 5 à 50 g/l de colorant pur.
  6. Procédé selon une ou plusieurs des revendications 1 à 5, caractérisé en ce qu'il est effectué à des températures de 20 à 135 °C, de façon particulièrement préférée de 60 à 95 °C.
  7. Procédé selon une ou plusieurs des revendications 1 à 6, caractérisé en ce qu'il est effectué sous une atmosphère inerte.
  8. Procédé selon une ou plusieurs des revendications 1 à 7, caractérisé en ce qu'on utilise en tant que matériaux fibreux ceux à base de cellulose ou polyamide ou de mélanges de cellulose/polyéther ou cellulose/polyamide.
EP03766263A 2002-07-31 2003-07-23 Procede de teinture au moyen de colorants au soufre et de colorants au soufre de cuve Expired - Fee Related EP1527228B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10234825 2002-07-31
DE10234825A DE10234825A1 (de) 2002-07-31 2002-07-31 Verfahren zum Färben mit Schwefel- und Schwefelküpenfarbstoffen
PCT/EP2003/008050 WO2004013406A1 (fr) 2002-07-31 2003-07-23 Procede de teinture au moyen de colorants au soufre et de colorants au soufre de cuve

Publications (2)

Publication Number Publication Date
EP1527228A1 EP1527228A1 (fr) 2005-05-04
EP1527228B1 true EP1527228B1 (fr) 2009-05-06

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EP03766263A Expired - Fee Related EP1527228B1 (fr) 2002-07-31 2003-07-23 Procede de teinture au moyen de colorants au soufre et de colorants au soufre de cuve

Country Status (14)

Country Link
US (1) US20050257327A1 (fr)
EP (1) EP1527228B1 (fr)
JP (1) JP2005534820A (fr)
KR (1) KR20050026542A (fr)
CN (1) CN100351459C (fr)
AT (1) ATE430831T1 (fr)
AU (1) AU2003250143A1 (fr)
BR (1) BR0312606B1 (fr)
DE (1) DE10234825A1 (fr)
ES (1) ES2326315T3 (fr)
MX (1) MXPA05001097A (fr)
TW (1) TWI276722B (fr)
WO (1) WO2004013406A1 (fr)
ZA (1) ZA200409847B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004040601A1 (de) * 2004-08-21 2006-03-02 Dystar Textilfarben Gmbh & Co. Deutschland Kg Neuartige flüssige Chinonimin-Schwefelfarbstoff-Zusammensetzungen sowie Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von cellulosehaltigem Material
CN108642760A (zh) * 2018-05-24 2018-10-12 武汉纺织大学 一种石墨烯电化学还原染色装置及方法
CN108716138A (zh) * 2018-05-24 2018-10-30 武汉纺织大学 一种单溶质间接电化学还原靛蓝的染液及染色方法
CN108754915A (zh) * 2018-05-24 2018-11-06 武汉纺织大学 电化学染料染色装置及方法
CN108642780A (zh) * 2018-05-24 2018-10-12 武汉纺织大学 一种以纱线染色辊为阴极的电化学染色装置及方法
CN108708100A (zh) * 2018-05-24 2018-10-26 武汉纺织大学 一种电化学还原染色装置及方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1906083A1 (de) * 1969-02-07 1970-08-13 Cassella Farbwerke Mainkur Ag Verfahren zur Herstellung reduzierter Schwefelfarbstoffe
GB1359275A (en) * 1972-11-30 1974-07-10 Bombay Textile Research Ass Vat dye reduction process
DE2263138C3 (de) * 1972-12-22 1978-06-29 The Bombay Textile Research Association, Bombay (Indien) Verfahren zum Färben von Textilmaterial mit Küpenfarbstoffen und Vorrichtung hierfür
JPS5239951B2 (fr) * 1974-05-28 1977-10-07
AT398316B (de) * 1989-06-01 1994-11-25 Verein Zur Foerderung Der Fors Verfahren zur reduktion von farbstoffen
US5632782A (en) * 1994-09-01 1997-05-27 Clariant Finance (Bvi) Ltd. Exhaust dyeing process for sulphur dyes
JPH1136173A (ja) * 1997-07-15 1999-02-09 Nishie Denimu:Kk 着色衣料の脱色方法
AT408455B (de) * 1997-09-04 2001-12-27 Basf Ag Verfahren zur reduktion von schwefelfarbstoffen
CA2318796A1 (fr) * 1998-11-24 2000-06-02 Walter Marte Procede et appareil pour la reduction de colorants de cuve et de colorants au soufre
DE19962155A1 (de) * 1999-12-22 2001-06-28 Basf Ag Verfahren zur elektrochemischen Reduktion von Küpenfarbstoffen
DE10010059A1 (de) * 2000-03-02 2001-09-06 Dystar Textilfarben Gmbh & Co Mediatorsysteme auf Basis gemischter Metallkomplexe zur Reduktion von Farbstoffen

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Publication number Publication date
CN100351459C (zh) 2007-11-28
EP1527228A1 (fr) 2005-05-04
MXPA05001097A (es) 2005-05-27
DE10234825A1 (de) 2004-02-19
WO2004013406A1 (fr) 2004-02-12
BR0312606B1 (pt) 2012-11-27
AU2003250143A1 (en) 2004-02-23
ES2326315T3 (es) 2009-10-07
ZA200409847B (en) 2006-07-26
TW200407485A (en) 2004-05-16
BR0312606A (pt) 2005-04-19
JP2005534820A (ja) 2005-11-17
US20050257327A1 (en) 2005-11-24
CN1665983A (zh) 2005-09-07
TWI276722B (en) 2007-03-21
KR20050026542A (ko) 2005-03-15
ATE430831T1 (de) 2009-05-15

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